# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_ADTA_2-27_THF_oX_100K_2-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915299'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2019-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H20 O8, 8.75(O)'
_chemical_formula_sum 'C14 H20 O16.75'
_chemical_formula_weight 456.30
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system cubic
_space_group_IT_number 201
_space_group_name_H-M_alt 'P n -3'
_space_group_name_Hall '-P 2ab 2bc 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x, y'
'z, -x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y'
'-z+1/2, x, -y+1/2'
'y, z, x'
'-y+1/2, z, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y+1/2, -z+1/2, x'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'
'-z, -x, -y'
'-z, x-1/2, y-1/2'
'z-1/2, x-1/2, -y'
'z-1/2, -x, y-1/2'
'-y, -z, -x'
'y-1/2, -z, x-1/2'
'-y, z-1/2, x-1/2'
'y-1/2, z-1/2, -x'
_cell_length_a 11.4074(5)
_cell_length_b 11.4074(5)
_cell_length_c 11.4074(5)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1484.4(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 6150
_cell_measurement_temperature 200
_cell_measurement_theta_max 29.768
_cell_measurement_theta_min 2.525
_shelx_estimated_absorpt_T_max 0.964
_shelx_estimated_absorpt_T_min 0.963
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.4751
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.021
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 476
_exptl_crystal_size_max 0.397
_exptl_crystal_size_mid 0.385
_exptl_crystal_size_min 0.379
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0579
_diffrn_reflns_av_unetI/netI 0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 15739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 30.472
_diffrn_reflns_theta_min 1.785
_diffrn_ambient_temperature 200
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 656
_reflns_number_total 761
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.338
_refine_diff_density_min -0.420
_refine_diff_density_rms 0.110
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.196
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 76
_refine_ls_number_reflns 761
_refine_ls_number_restraints 36
_refine_ls_R_factor_all 0.0928
_refine_ls_R_factor_gt 0.0859
_refine_ls_restrained_S_all 1.271
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1422P)^2^+0.1067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2151
_refine_ls_wR_factor_ref 0.2255
_refine_special_details
;
Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.506(13)
0.494(13)
2. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All O(H) groups
3. Restrained distances
H1-H2_$1
2.1 with sigma of 0.04
H2-H1_$2
2.1 with sigma of 0.04
4. Restrained planarity
H2_$1, O2_$1, C3, O1, H1
with sigma of 0.001
H2, O2, C3, O1_$2, H1_$2
with sigma of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(O5S) \\sim Ueq, Uanis(O4S) \\sim Ueq, Uanis(O2S) \\sim Ueq, Uanis(O3S)
\\sim Ueq, Uanis(O1S) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
6. Others
Fixed Sof: O1(0.33333) H1(0.33333) O2(0.33333) H2(0.33333) H1A(0.5) H1B(0.5)
O1S(0.125) O2S(0.125) O3S(0.125) O4S(0.25) O5S(0.04167) O6S(0.0625)
7.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B)
7.b Idealised tetrahedral OH refined as rotating group:
O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6142(7) 0.5875(7) 0.4913(4) 0.073(2) Uani 0.3333 1 d . . . A 1
H1 H 0.5647 0.5420 0.4612 0.110 Uiso 0.3333 1 calc DGR . . A 1
O2 O 0.5430(8) 0.6449(5) 0.5151(7) 0.101(4) Uani 0.3333 1 d . . . A 2
H2 H 0.5031 0.5952 0.4781 0.151 Uiso 0.3333 1 calc DGR . . A 2
C1 C 0.7500 0.7500 0.59417(12) 0.0307(5) Uani 1 2 d S T P . .
H1A H 0.7997 0.7003 0.5433 0.037 Uiso 0.5 1 calc R . . . .
H1B H 0.7003 0.7997 0.5433 0.037 Uiso 0.5 1 calc R . . . .
C2 C 0.67231(8) 0.67231(8) 0.67231(8) 0.0289(5) Uani 1 3 d S T P . .
C3 C 0.59580(9) 0.59580(9) 0.59580(9) 0.0339(5) Uani 1 3 d S T P . .
O1S O 0.357(4) 0.811(4) 0.460(4) 0.142(13) Uani 0.125 1 d . U . B 5
O2S O 0.420(3) 0.854(2) 0.429(3) 0.093(7) Uani 0.125 1 d . U . C 3
O3S O 0.389(3) 0.868(3) 0.4776(19) 0.078(6) Uani 0.125 1 d . U . D 4
O4S O 0.5146(14) 0.9500(11) 0.4279(11) 0.101(4) Uani 0.25 1 d . U . . 2
O5S O 0.5000 1.0000 0.5000 0.092(6) Uani 0.25 6 d S TU P E 1
O6S O 0.7500 0.881(4) 0.2500 0.26(4) Uani 0.125 2 d S T P F 6
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.100(5) 0.087(5) 0.0327(17) -0.021(2) 0.017(3) -0.060(4)
O2 0.158(9) 0.049(2) 0.095(5) 0.025(3) -0.100(6) -0.033(4)
C1 0.0290(9) 0.0361(11) 0.0269(7) 0.000 0.000 -0.0018(5)
C2 0.0289(5) 0.0289(5) 0.0289(5) -0.0022(3) -0.0022(3) -0.0022(3)
C3 0.0339(5) 0.0339(5) 0.0339(5) -0.0029(3) -0.0029(3) -0.0029(3)
O1S 0.15(2) 0.125(18) 0.15(2) 0.032(15) -0.024(15) 0.066(15)
O2S 0.094(13) 0.105(13) 0.080(13) 0.045(12) -0.004(9) 0.017(12)
O3S 0.092(13) 0.089(13) 0.055(10) 0.015(9) -0.014(10) 0.026(11)
O4S 0.087(7) 0.098(7) 0.119(8) 0.062(6) -0.021(7) 0.003(6)
O5S 0.092(6) 0.092(6) 0.092(6) 0.023(5) -0.023(5) 0.023(5)
O6S 0.59(13) 0.15(3) 0.047(13) 0.000 -0.06(4) 0.000
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C3 1.215(5) . ?
O2 H2 0.8400 . ?
O2 C3 1.235(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5380(10) . ?
C1 C2 1.5380(10) 2_665 ?
C2 C1 1.5380(10) 5 ?
C2 C1 1.5380(10) 9 ?
C2 C3 1.512(2) . ?
C3 O1 1.215(5) 5 ?
C3 O1 1.215(5) 9 ?
C3 O2 1.235(5) 5 ?
C3 O2 1.235(5) 9 ?
O4S O4S 1.019(14) 18_665 ?
O4S O4S 1.76(2) 12_665 ?
O4S O4S 1.76(2) 6_566 ?
O4S O4S 1.019(14) 24_566 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 2_665 . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 2_665 . ?
C2 C1 H1B 109.8 . . ?
C2 C1 C2 109.16(13) 2_665 . ?
C1 C2 C1 109.63(7) . 9 ?
C1 C2 C1 109.63(7) . 5 ?
C1 C2 C1 109.63(7) 9 5 ?
C3 C2 C1 109.32(7) . 5 ?
C3 C2 C1 109.32(7) . . ?
C3 C2 C1 109.32(7) . 9 ?
O1 C3 O1 96.1(3) 9 . ?
O1 C3 O1 96.1(3) . 5 ?
O1 C3 O1 96.1(3) 9 5 ?
O1 C3 C2 120.8(2) . . ?
O1 C3 C2 120.8(2) 5 . ?
O1 C3 C2 120.8(2) 9 . ?
O2 C3 O2 101.3(3) . 5 ?
O2 C3 O2 101.3(3) 5 9 ?
O2 C3 O2 101.3(3) . 9 ?
O2 C3 C2 116.8(2) . . ?
O2 C3 C2 116.8(2) 9 . ?
O2 C3 C2 116.8(2) 5 . ?
O4S O4S O4S 119.1(5) 18_665 24_566 ?
O4S O4S O4S 30.5(2) 24_566 6_566 ?
O4S O4S O4S 90.002(5) 18_665 6_566 ?
O4S O4S O4S 30.5(2) 18_665 12_665 ?
O4S O4S O4S 60.001(4) 12_665 6_566 ?
O4S O4S O4S 90.002(2) 24_566 12_665 ?
_shelx_res_file
;
pc_thf_ox_100k.res created by SHELXL-2014/7
TITL pc_thf_ox_100k_a.res in Pn-3
REM Old TITL PC_THF_oX_100K in P2(1)3
REM SHELXT solution in Pn-3
REM R1 0.388, Rweak 0.024, Alpha 0.082, Orientation as input
REM Formula found by SHELXT: C8 O6S
CELL 0.71073 11.4074 11.4074 11.4074 90 90 90
ZERR 2 0.0005 0.0005 0.0005 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,+Z
SYMM 0.5-X,+Y,0.5-Z
SYMM +X,0.5-Y,0.5-Z
SYMM +Z,+X,+Y
SYMM +Z,0.5-X,0.5-Y
SYMM 0.5-Z,0.5-X,+Y
SYMM 0.5-Z,+X,0.5-Y
SYMM +Y,+Z,+X
SYMM 0.5-Y,+Z,0.5-X
SYMM +Y,0.5-Z,0.5-X
SYMM 0.5-Y,0.5-Z,+X
SFAC C H O
UNIT 28 40 33.5
EQIV $1 +Z,+X,+Y
EQIV $2 +Y,+Z,+X
DANG 2.1 H1 H2_$1
DANG 2.1 H2 H1_$2
FLAT 0.001 H2_$1 O2_$1 C3 O1 H1
FLAT 0.001 H2 O2 C3 O1_$2 H1_$2
ISOR 0.01 0.02 O5S O4S O2S O3S O1S
L.S. 20
PLAN 20
SIZE 0.397 0.385 0.379
TEMP -173.15
FREE O1 O1_$1
FREE O1 O1_$2
BOND $H
list 4
fmap 2 53
acta
TWIN -1 0 0 0 0 1 0 1 0 2
REM
REM
REM
WGHT 0.142200 0.106700
BASF 0.49416
FVAR 1.29704
PART 1
O1 3 0.614197 0.587487 0.491257 10.33333 0.09958 0.08738 =
0.03272 -0.02117 0.01687 -0.05971
AFIX 147
H1 2 0.564723 0.541999 0.461166 10.33333 -1.50000
AFIX 0
PART 0
PART 2
O2 3 0.542987 0.644856 0.515067 10.33333 0.15772 0.04863 =
0.09547 0.02493 -0.09960 -0.03262
AFIX 147
H2 2 0.503086 0.595220 0.478100 10.33333 -1.50000
AFIX 0
PART 0
C1 1 0.750000 0.750000 0.594171 10.50000 0.02904 0.03605 =
0.02686 0.00000 0.00000 -0.00182
AFIX 23
H1A 2 0.799734 0.700266 0.543329 10.50000 -1.20000
H1B 2 0.700266 0.799734 0.543329 10.50000 -1.20000
AFIX 0
C2 1 0.672308 0.672308 0.672308 10.33333 0.02894 0.02894 =
0.02894 -0.00217 -0.00217 -0.00217
C3 1 0.595798 0.595798 0.595798 10.33333 0.03389 0.03389 =
0.03389 -0.00294 -0.00294 -0.00294
PART 5
O1S 3 0.357342 0.811336 0.460193 10.12500 0.15030 0.12455 =
0.15018 0.03222 -0.02377 0.06622
PART 0
PART 3
O2S 3 0.420354 0.854244 0.429138 10.12500 0.09352 0.10462 =
0.07980 0.04518 -0.00371 0.01724
PART 0
PART 4
O3S 3 0.389230 0.868489 0.477571 10.12500 0.09213 0.08883 =
0.05451 0.01519 -0.01446 0.02650
PART 0
PART 2
O4S 3 0.514583 0.950000 0.427851 10.25000 0.08697 0.09767 =
0.11945 0.06172 -0.02103 0.00295
PART 0
PART 1
O5S 3 0.500000 1.000000 0.500000 10.04167 0.09157 0.09157 =
0.09157 0.02349 -0.02349 0.02349
PART 0
PART 6
O6S 3 0.750000 0.880549 0.250000 10.06250 0.58716 0.14944 =
0.04712 0.00000 -0.06026 0.00000
HKLF 4
REM pc_thf_ox_100k_a.res in Pn-3
REM R1 = 0.0859 for 656 Fo > 4sig(Fo) and 0.0928 for all 761 data
REM 76 parameters refined using 36 restraints
END
WGHT 0.1433 0.1239
REM Highest difference peak 0.338, deepest hole -0.420, 1-sigma level 0.110
Q1 1 0.7500 1.0036 0.2500 10.50000 0.05 0.34
Q2 1 0.7994 0.9660 0.2530 11.00000 0.05 0.32
Q3 1 0.8560 0.8583 0.2562 11.00000 0.05 0.22
Q4 1 0.3201 0.7243 0.4197 11.00000 0.05 0.21
Q5 1 0.4634 0.8115 0.3985 11.00000 0.05 0.17
Q6 1 0.4393 0.7973 0.4157 11.00000 0.05 0.17
Q7 1 0.4501 0.8717 0.4518 11.00000 0.05 0.17
Q8 1 0.3551 0.8140 0.5190 11.00000 0.05 0.16
Q9 1 0.4031 0.8194 0.4788 11.00000 0.05 0.15
Q10 1 0.4718 0.8395 0.4909 11.00000 0.05 0.15
Q11 1 0.3724 0.8048 0.4939 11.00000 0.05 0.13
Q12 1 0.3033 0.8973 0.4239 11.00000 0.05 0.13
Q13 1 0.3978 0.8981 0.5031 11.00000 0.05 0.12
Q14 1 0.6320 0.7283 0.4032 11.00000 0.05 0.09
Q15 1 0.6765 0.9049 0.5949 11.00000 0.05 0.08
Q16 1 0.2765 0.8739 0.3420 11.00000 0.05 0.08
Q17 1 0.7293 0.8415 0.3730 11.00000 0.05 0.08
Q18 1 0.3980 0.8060 0.5579 11.00000 0.05 0.08
Q19 1 0.5625 0.8344 0.5548 11.00000 0.05 0.07
Q20 1 0.7098 0.7959 0.1609 11.00000 0.05 0.07
;
_shelx_res_checksum 59100
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.506(13)
2 0.494(13)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
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data_ADTA_2-2_THF_4-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915301'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H16 O8, 0.25(C4 H8 O)'
_chemical_formula_sum 'C15 H18 O8.25'
_chemical_formula_weight 330.29
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system tetragonal
_space_group_IT_number 88
_space_group_name_H-M_alt 'I 41/a'
_space_group_name_Hall '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
_cell_length_a 16.4008(15)
_cell_length_b 16.4008(15)
_cell_length_c 22.397(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 6024.5(13)
_cell_formula_units_Z 16
_cell_measurement_reflns_used 9946
_cell_measurement_temperature 100
_cell_measurement_theta_max 29.134
_cell_measurement_theta_min 2.484
_shelx_estimated_absorpt_T_max 0.987
_shelx_estimated_absorpt_T_min 0.985
_exptl_absorpt_coefficient_mu 0.120
_exptl_absorpt_correction_T_max 0.7458
_exptl_absorpt_correction_T_min 0.4879
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.6542.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.457
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 2784
_exptl_crystal_size_max 0.124
_exptl_crystal_size_mid 0.118
_exptl_crystal_size_min 0.106
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0493
_diffrn_reflns_av_unetI/netI 0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_number 40618
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.134
_diffrn_reflns_theta_min 2.484
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3187
_reflns_number_total 4055
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.485
_refine_diff_density_min -0.271
_refine_diff_density_rms 0.061
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 238
_refine_ls_number_reflns 4055
_refine_ls_number_restraints 14
_refine_ls_R_factor_all 0.0686
_refine_ls_R_factor_gt 0.0549
_refine_ls_restrained_S_all 1.058
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+8.5815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1517
_refine_ls_wR_factor_ref 0.1635
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
2. Restrained distances
O7-H7 = O5-H5 = O2-H2 = O4-H4
0.82 with sigma of 0.01
C16-C16_$3
1.51 with sigma of 0.01
3. Rigid body (RIGU) restrains
O9, C15, C16
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
Fixed Sof: O9(0.25) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5)
5.a Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
C15(H15A,H15B), C16(H16A,H16B)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.60206(8) 0.71971(7) 0.50630(5) 0.0256(3) Uani 1 1 d . . . . .
O7 O 0.64225(8) 0.78721(7) 0.42456(5) 0.0247(3) Uani 1 1 d D . . . .
O3 O 0.77747(7) 0.58178(8) 0.24742(5) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.59538(9) 0.34945(7) 0.42386(6) 0.0307(3) Uani 1 1 d D . . . .
O6 O 0.62549(9) 0.41762(7) 0.50713(5) 0.0298(3) Uani 1 1 d . . . . .
O4 O 0.84384(7) 0.54642(9) 0.33048(5) 0.0309(3) Uani 1 1 d D . . . .
O1 O 0.47472(7) 0.55365(9) 0.24134(5) 0.0318(3) Uani 1 1 d . . . . .
O2 O 0.40596(7) 0.59421(9) 0.32177(6) 0.0333(3) Uani 1 1 d D . . . .
C8 C 0.61757(8) 0.56819(8) 0.45455(6) 0.0158(3) Uani 1 1 d . . . . .
H8A H 0.6646 0.5654 0.4822 0.019 Uiso 1 1 calc R . . . .
H8B H 0.5670 0.5708 0.4787 0.019 Uiso 1 1 calc R . . . .
C5 C 0.61600(8) 0.49213(8) 0.41473(6) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.54739(8) 0.57276(8) 0.33399(6) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.61254(9) 0.41616(9) 0.45368(7) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.70013(8) 0.56474(9) 0.33761(6) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.54962(8) 0.64934(8) 0.37357(6) 0.0163(3) Uani 1 1 d . . . . .
H9A H 0.4990 0.6528 0.3976 0.020 Uiso 1 1 calc R . . . .
H9B H 0.5532 0.6987 0.3483 0.020 Uiso 1 1 calc R . . . .
C2 C 0.62546(8) 0.56936(9) 0.29624(6) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.6291 0.6186 0.2708 0.020 Uiso 1 1 calc R . . . .
H2B H 0.6241 0.5209 0.2699 0.020 Uiso 1 1 calc R . . . .
C14 C 0.62288(9) 0.72062(9) 0.45395(7) 0.0174(3) Uani 1 1 d . . . . .
C10 C 0.62447(8) 0.64466(8) 0.41536(6) 0.0152(3) Uani 1 1 d . . . . .
C4 C 0.54150(9) 0.49564(9) 0.37330(6) 0.0168(3) Uani 1 1 d . . . . .
H4A H 0.4909 0.4973 0.3973 0.020 Uiso 1 1 calc R . . . .
H4B H 0.5399 0.4464 0.3477 0.020 Uiso 1 1 calc R . . . .
C6 C 0.69493(9) 0.48791(9) 0.37693(6) 0.0173(3) Uani 1 1 d . . . . .
H6A H 0.7431 0.4849 0.4035 0.021 Uiso 1 1 calc R . . . .
H6B H 0.6942 0.4386 0.3515 0.021 Uiso 1 1 calc R . . . .
C7 C 0.70301(8) 0.64133(9) 0.37784(6) 0.0169(3) Uani 1 1 d . . . . .
H7A H 0.7512 0.6388 0.4044 0.020 Uiso 1 1 calc R . . . .
H7B H 0.7075 0.6910 0.3529 0.020 Uiso 1 1 calc R . . . .
C12 C 0.77749(9) 0.56451(9) 0.30020(7) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.47299(9) 0.57386(9) 0.29368(7) 0.0185(3) Uani 1 1 d . . . . .
O9 O 0.5000 0.7500 0.2291(3) 0.0850(19) Uani 0.5 2 d S TU P . .
C15 C 0.5688(5) 0.7532(4) 0.1904(3) 0.0836(18) Uani 0.5 1 d . U . . .
H15A H 0.5969 0.6998 0.1904 0.100 Uiso 0.5 1 calc R . . . .
H15B H 0.6076 0.7950 0.2047 0.100 Uiso 0.5 1 calc R . . . .
C16 C 0.5412(4) 0.7741(6) 0.1270(4) 0.0810(18) Uani 0.5 1 d D U . . .
H16A H 0.5797 0.7533 0.0964 0.097 Uiso 0.5 1 calc R . . . .
H16B H 0.5330 0.8334 0.1214 0.097 Uiso 0.5 1 calc R . . . .
H5 H 0.5935(18) 0.3098(12) 0.4465(11) 0.067(9) Uiso 1 1 d D . . . .
H7 H 0.642(2) 0.8242(14) 0.4497(11) 0.083(10) Uiso 1 1 d D . . . .
H2 H 0.3695(14) 0.5948(19) 0.2960(10) 0.073(9) Uiso 1 1 d D . . . .
H4 H 0.8828(13) 0.545(2) 0.3069(11) 0.078(10) Uiso 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0361(6) 0.0186(5) 0.0220(6) -0.0036(4) 0.0049(5) -0.0015(5)
O7 0.0352(6) 0.0158(5) 0.0232(6) -0.0008(4) -0.0017(5) -0.0031(4)
O3 0.0198(5) 0.0396(7) 0.0211(6) 0.0033(5) 0.0030(4) 0.0016(5)
O5 0.0524(8) 0.0144(5) 0.0252(6) 0.0020(4) -0.0058(5) -0.0031(5)
O6 0.0503(8) 0.0185(5) 0.0207(6) 0.0025(4) -0.0034(5) -0.0020(5)
O4 0.0165(5) 0.0512(8) 0.0250(6) 0.0068(5) 0.0027(4) 0.0062(5)
O1 0.0210(6) 0.0509(8) 0.0234(6) -0.0090(5) -0.0044(4) 0.0072(5)
O2 0.0167(6) 0.0567(9) 0.0266(6) -0.0111(6) -0.0034(5) 0.0050(5)
C8 0.0173(6) 0.0146(6) 0.0156(7) -0.0005(5) 0.0002(5) 0.0007(5)
C5 0.0163(6) 0.0135(6) 0.0167(7) 0.0006(5) -0.0001(5) 0.0003(5)
C3 0.0142(6) 0.0158(6) 0.0168(7) -0.0003(5) -0.0016(5) 0.0006(5)
C13 0.0183(7) 0.0154(6) 0.0215(7) 0.0010(5) 0.0008(5) 0.0015(5)
C1 0.0141(6) 0.0185(6) 0.0169(7) 0.0002(5) 0.0009(5) 0.0015(5)
C9 0.0157(6) 0.0150(6) 0.0183(7) -0.0016(5) -0.0016(5) 0.0020(5)
C2 0.0153(6) 0.0197(7) 0.0161(7) -0.0001(5) -0.0003(5) 0.0026(5)
C14 0.0166(6) 0.0155(6) 0.0201(7) -0.0015(5) -0.0034(5) 0.0009(5)
C10 0.0156(6) 0.0135(6) 0.0166(7) -0.0010(5) -0.0010(5) 0.0003(5)
C4 0.0170(6) 0.0149(6) 0.0185(7) -0.0010(5) -0.0012(5) -0.0017(5)
C6 0.0165(6) 0.0169(6) 0.0186(7) 0.0006(5) 0.0006(5) 0.0037(5)
C7 0.0151(6) 0.0171(6) 0.0186(7) 0.0005(5) 0.0001(5) -0.0011(5)
C12 0.0164(6) 0.0212(7) 0.0217(7) -0.0010(5) 0.0003(5) 0.0014(5)
C11 0.0170(6) 0.0187(7) 0.0198(7) -0.0009(5) -0.0013(5) 0.0007(5)
O9 0.111(4) 0.074(4) 0.070(3) 0.000 0.000 -0.046(3)
C15 0.104(4) 0.061(4) 0.086(3) 0.019(3) -0.001(3) -0.023(3)
C16 0.081(5) 0.079(5) 0.083(3) 0.005(3) 0.007(3) -0.003(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C14 1.2213(19) . ?
O7 C14 1.3140(18) . ?
O7 H7 0.827(10) . ?
O3 C12 1.2155(19) . ?
O5 C13 1.3123(18) . ?
O5 H5 0.825(10) . ?
O6 C13 1.2162(19) . ?
O4 C12 1.3161(18) . ?
O4 H4 0.830(10) . ?
O1 C11 1.2184(19) . ?
O2 C11 1.3100(18) . ?
O2 H2 0.832(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C5 1.5336(19) . ?
C8 C10 1.5351(19) . ?
C5 C13 1.5220(19) . ?
C5 C4 1.5355(19) . ?
C5 C6 1.5483(19) . ?
C3 C9 1.5378(19) . ?
C3 C2 1.5353(19) . ?
C3 C4 1.5440(19) . ?
C3 C11 1.5180(19) . ?
C1 C2 1.5376(19) . ?
C1 C6 1.5397(19) . ?
C1 C7 1.547(2) . ?
C1 C12 1.520(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5456(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 C10 1.5165(19) . ?
C10 C7 1.5389(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O9 C15 1.424(8) . ?
O9 C15 1.424(8) 6_564 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(11) . ?
C16 C16 1.566(8) 6_564 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O7 H7 106(2) . . ?
C13 O5 H5 111(2) . . ?
C12 O4 H4 108(2) . . ?
C11 O2 H2 106(2) . . ?
H8A C8 H8B 108.2 . . ?
C5 C8 H8A 109.8 . . ?
C5 C8 H8B 109.8 . . ?
C5 C8 C10 109.47(11) . . ?
C10 C8 H8A 109.8 . . ?
C10 C8 H8B 109.8 . . ?
C8 C5 C4 109.53(11) . . ?
C8 C5 C6 109.90(11) . . ?
C13 C5 C8 109.47(11) . . ?
C13 C5 C4 110.32(11) . . ?
C13 C5 C6 107.94(11) . . ?
C4 C5 C6 109.66(11) . . ?
C9 C3 C4 109.99(11) . . ?
C2 C3 C9 109.09(11) . . ?
C2 C3 C4 109.66(11) . . ?
C11 C3 C9 110.63(11) . . ?
C11 C3 C2 110.07(11) . . ?
C11 C3 C4 107.37(11) . . ?
O5 C13 C5 113.51(13) . . ?
O6 C13 O5 123.70(14) . . ?
O6 C13 C5 122.78(13) . . ?
C2 C1 C6 109.93(11) . . ?
C2 C1 C7 109.59(11) . . ?
C6 C1 C7 109.46(11) . . ?
C12 C1 C2 109.43(11) . . ?
C12 C1 C6 111.06(11) . . ?
C12 C1 C7 107.32(11) . . ?
C3 C9 H9A 109.9 . . ?
C3 C9 H9B 109.9 . . ?
C3 C9 C10 109.12(11) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C3 C2 C1 109.53(11) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O8 C14 O7 123.96(13) . . ?
O8 C14 C10 122.82(13) . . ?
O7 C14 C10 113.14(13) . . ?
C8 C10 C9 109.17(11) . . ?
C8 C10 C7 110.18(11) . . ?
C14 C10 C8 110.12(11) . . ?
C14 C10 C9 106.90(11) . . ?
C14 C10 C7 110.78(11) . . ?
C7 C10 C9 109.62(11) . . ?
C5 C4 C3 109.00(11) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C1 C6 C5 108.82(11) . . ?
C1 C6 H6A 109.9 . . ?
C1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C10 C7 C1 108.75(11) . . ?
C10 C7 H7A 109.9 . . ?
C10 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O3 C12 O4 123.63(14) . . ?
O3 C12 C1 122.35(13) . . ?
O4 C12 C1 113.98(13) . . ?
O1 C11 O2 123.43(14) . . ?
O1 C11 C3 123.39(13) . . ?
O2 C11 C3 113.07(13) . . ?
C15 O9 C15 104.9(7) 6_564 . ?
O9 C15 H15A 109.7 . . ?
O9 C15 H15B 109.7 . . ?
O9 C15 C16 109.9(6) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 C16 98.2(4) . 6_564 ?
C15 C16 H16A 112.1 . . ?
C15 C16 H16B 112.1 . . ?
C16 C16 H16A 112.1 6_564 . ?
C16 C16 H16B 112.1 6_564 . ?
H16A C16 H16B 109.8 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O8 0.825(10) 1.822(11) 2.6431(16) 173(3) 14_546
O7 H7 O6 0.827(10) 1.832(12) 2.6440(16) 167(3) 14_556
O2 H2 O3 0.832(10) 1.807(12) 2.6236(16) 167(3) 10_556
O4 H4 O1 0.830(10) 1.860(11) 2.6851(17) 172(3) 10_656
_shelx_res_file
;
pc_ht_8_i22_100k.res created by SHELXL-2014/7
TITL pc_ht_8_i22_100k_a.res in I4(1)/a
REM Old TITL PC_HT_8_i22_100K in I4(1)/a
REM SHELXT solution in I4(1)/a
REM R1 0.230, Rweak 0.003, Alpha 0.020, Orientation as input
REM Formula found by SHELXT: C22
CELL 0.71073 16.4008 16.4008 22.3972 90 90 90
ZERR 16 0.0015 0.0015 0.0022 0 0 0
LATT 2
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.75-Y,0.25+X,0.25+Z
SYMM 0.75+Y,0.75-X,0.75+Z
SFAC C H O
UNIT 240 288 132
EQIV $1 -0.25+Y,1.25-X,0.25-Z
EQIV $2 1.25-Y,0.25+X,0.25-Z
EQIV $3 1-X,1.5-Y,+Z
EQIV $4 +X,0.5+Y,1-Z
EQIV $5 +X,-0.5+Y,1-Z
EQIV $6 0.5+X,+Y,0.5-Z
EQIV $7 -0.5+X,+Y,0.5-Z
DFIX 0.82 0.01 O7 H7 O5 H5 O2 H2 O4 H4
DFIX 1.51 0.01 C16 C16_$3
RIGU 0.002 0.002 O9 C15 C16
L.S. 15
PLAN 20
SIZE 0.106 0.118 0.124
TEMP -173.15
HTAB O7 O6_$4
HTAB O5 O8_$5
HTAB O4 O1_$6
HTAB O2 O3_$7
FREE C15 C16_$1
FREE C15 H16b_$1
FREE C16 C16_$1
FREE C16 C16_$2
FREE C16 H16a_$2
FREE C16 H16b_$1
FREE C16 C15_$2
BOND $H
list 4
fmap 2 53
ACTA
REM
REM
REM
WGHT 0.072500 8.581500
FVAR 0.20385
O8 3 0.602064 0.719714 0.506303 11.00000 0.03614 0.01861 =
0.02202 -0.00362 0.00492 -0.00154
O7 3 0.642246 0.787206 0.424564 11.00000 0.03521 0.01580 =
0.02315 -0.00079 -0.00174 -0.00309
O3 3 0.777475 0.581784 0.247424 11.00000 0.01984 0.03957 =
0.02110 0.00330 0.00300 0.00157
O5 3 0.595381 0.349447 0.423859 11.00000 0.05242 0.01438 =
0.02524 0.00201 -0.00584 -0.00313
O6 3 0.625490 0.417616 0.507131 11.00000 0.05030 0.01847 =
0.02067 0.00253 -0.00335 -0.00202
O4 3 0.843836 0.546418 0.330482 11.00000 0.01650 0.05121 =
0.02499 0.00680 0.00271 0.00624
O1 3 0.474721 0.553647 0.241342 11.00000 0.02103 0.05086 =
0.02337 -0.00896 -0.00437 0.00717
O2 3 0.405956 0.594209 0.321769 11.00000 0.01674 0.05672 =
0.02658 -0.01114 -0.00340 0.00504
C8 1 0.617568 0.568189 0.454552 11.00000 0.01727 0.01459 =
0.01562 -0.00051 0.00025 0.00066
AFIX 23
H8A 2 0.664594 0.565355 0.482186 11.00000 -1.20000
H8B 2 0.567049 0.570797 0.478669 11.00000 -1.20000
AFIX 0
C5 1 0.616001 0.492133 0.414735 11.00000 0.01630 0.01349 =
0.01669 0.00056 -0.00014 0.00029
C3 1 0.547387 0.572756 0.333990 11.00000 0.01424 0.01575 =
0.01684 -0.00026 -0.00159 0.00061
C13 1 0.612537 0.416155 0.453675 11.00000 0.01832 0.01544 =
0.02152 0.00096 0.00084 0.00154
C1 1 0.700131 0.564743 0.337610 11.00000 0.01406 0.01853 =
0.01693 0.00016 0.00086 0.00148
C9 1 0.549625 0.649342 0.373565 11.00000 0.01565 0.01504 =
0.01827 -0.00163 -0.00163 0.00201
AFIX 23
H9A 2 0.499043 0.652805 0.397554 11.00000 -1.20000
H9B 2 0.553232 0.698714 0.348272 11.00000 -1.20000
AFIX 0
C2 1 0.625457 0.569364 0.296242 11.00000 0.01526 0.01972 =
0.01607 -0.00014 -0.00030 0.00259
AFIX 23
H2A 2 0.629146 0.618599 0.270813 11.00000 -1.20000
H2B 2 0.624063 0.520929 0.269883 11.00000 -1.20000
AFIX 0
C14 1 0.622879 0.720624 0.453951 11.00000 0.01664 0.01551 =
0.02013 -0.00155 -0.00344 0.00086
C10 1 0.624469 0.644664 0.415359 11.00000 0.01560 0.01353 =
0.01655 -0.00098 -0.00103 0.00026
C4 1 0.541498 0.495643 0.373296 11.00000 0.01696 0.01485 =
0.01847 -0.00100 -0.00118 -0.00170
AFIX 23
H4A 2 0.490856 0.497286 0.397321 11.00000 -1.20000
H4B 2 0.539884 0.446414 0.347744 11.00000 -1.20000
AFIX 0
C6 1 0.694927 0.487912 0.376931 11.00000 0.01646 0.01689 =
0.01863 0.00060 0.00065 0.00367
AFIX 23
H6A 2 0.743087 0.484860 0.403485 11.00000 -1.20000
H6B 2 0.694170 0.438552 0.351494 11.00000 -1.20000
AFIX 0
C7 1 0.703009 0.641334 0.377842 11.00000 0.01512 0.01713 =
0.01858 0.00048 0.00009 -0.00105
AFIX 23
H7A 2 0.751175 0.638833 0.404422 11.00000 -1.20000
H7B 2 0.707476 0.690957 0.352887 11.00000 -1.20000
AFIX 0
C12 1 0.777489 0.564511 0.300201 11.00000 0.01635 0.02120 =
0.02170 -0.00098 0.00031 0.00144
C11 1 0.472995 0.573855 0.293676 11.00000 0.01697 0.01870 =
0.01983 -0.00087 -0.00132 0.00065
O9 3 0.500000 0.750000 0.229108 10.25000 0.11140 0.07364 =
0.06995 0.00000 0.00000 -0.04567
C15 1 0.568756 0.753176 0.190357 10.50000 0.10366 0.06148 =
0.08568 0.01904 -0.00108 -0.02333
AFIX 23
H15A 2 0.596938 0.699796 0.190400 10.50000 -1.20000
H15B 2 0.607602 0.795001 0.204730 10.50000 -1.20000
AFIX 0
C16 1 0.541244 0.774054 0.126959 10.50000 0.08055 0.07947 =
0.08307 0.00542 0.00678 -0.00348
AFIX 23
H16A 2 0.579661 0.753325 0.096430 10.50000 -1.20000
H16B 2 0.532978 0.833369 0.121427 10.50000 -1.20000
AFIX 0
H5 2 0.593536 0.309766 0.446455 11.00000 0.06684
H7 2 0.642080 0.824212 0.449659 11.00000 0.08294
H2 2 0.369474 0.594819 0.295962 11.00000 0.07347
H4 2 0.882834 0.544707 0.306893 11.00000 0.07847
HKLF 4
REM pc_ht_8_i22_100k_a.res in I4(1)/a
REM R1 = 0.0549 for 3187 Fo > 4sig(Fo) and 0.0686 for all 4055 data
REM 238 parameters refined using 14 restraints
END
WGHT 0.0725 8.5808
REM Highest difference peak 0.485, deepest hole -0.271, 1-sigma level 0.061
Q1 1 0.6144 0.4568 0.4318 11.00000 0.05 0.48
Q2 1 0.6237 0.6807 0.4366 11.00000 0.05 0.46
Q3 1 0.7339 0.5638 0.3181 11.00000 0.05 0.44
Q4 1 0.5092 0.5738 0.3142 11.00000 0.05 0.41
Q5 1 0.6612 0.5642 0.3193 11.00000 0.05 0.40
Q6 1 0.6242 0.6055 0.4306 11.00000 0.05 0.40
Q7 1 0.6531 0.4889 0.3936 11.00000 0.05 0.38
Q8 1 0.5751 0.4922 0.3989 11.00000 0.05 0.38
Q9 1 0.6148 0.5272 0.4366 11.00000 0.05 0.38
Q10 1 0.5520 0.8053 0.1012 11.00000 0.05 0.38
Q11 1 0.5487 0.6124 0.3559 11.00000 0.05 0.37
Q12 1 0.5469 0.5317 0.3522 11.00000 0.05 0.36
Q13 1 0.6957 0.5255 0.3563 11.00000 0.05 0.35
Q14 1 0.5590 0.3678 0.4484 11.00000 0.05 0.34
Q15 1 0.5640 0.7294 0.4865 11.00000 0.05 0.34
Q16 1 0.5851 0.5705 0.3104 11.00000 0.05 0.34
Q17 1 0.6878 0.7684 0.4496 11.00000 0.05 0.34
Q18 1 0.4658 0.6591 0.2659 11.00000 0.05 0.34
Q19 1 0.6625 0.6433 0.3958 11.00000 0.05 0.33
Q20 1 0.7000 0.6024 0.3578 11.00000 0.05 0.33
;
_shelx_res_checksum 10859
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_ADTA_2-34_THF-1-2-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915303'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C14 H16 O8), 4(C8 H10 O2)'
_chemical_formula_sum 'C60 H72 O24'
_chemical_formula_weight 1177.17
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system tetragonal
_space_group_IT_number 88
_space_group_name_H-M_alt 'I 41/a'
_space_group_name_Hall '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
_cell_length_a 16.2380(2)
_cell_length_b 16.2380(2)
_cell_length_c 22.3825(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 5901.65(17)
_cell_formula_units_Z 4
_cell_measurement_temperature 100.01(10)
_cell_measurement_reflns_used 8969
_cell_measurement_theta_min 2.4890
_cell_measurement_theta_max 30.0790
_shelx_estimated_absorpt_T_max 0.993
_shelx_estimated_absorpt_T_min 0.989
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_T_min 0.71430
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.643
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.325
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 2496
_exptl_crystal_size_max 0.11
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.07
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0789
_diffrn_reflns_av_unetI/netI 0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_number 45910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.360
_diffrn_reflns_theta_min 2.509
_diffrn_ambient_temperature 100.0
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0227345000
_diffrn_orient_matrix_UB_12 -0.0050706000
_diffrn_orient_matrix_UB_13 -0.0267912000
_diffrn_orient_matrix_UB_21 -0.0353263000
_diffrn_orient_matrix_UB_22 -0.0107974000
_diffrn_orient_matrix_UB_23 0.0168476000
_diffrn_orient_matrix_UB_31 -0.0119427000
_diffrn_orient_matrix_UB_32 0.0419919000
_diffrn_orient_matrix_UB_33 0.0011003000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -109.00 16.00 1.00 10.00 -- -20.00 -68.00 0.00 125
2 \w -109.00 16.00 1.00 10.00 -- -20.00 -68.00 120.00 125
3 \w -109.00 16.00 1.00 10.00 -- -20.00 -68.00 240.00 125
4 \w -109.00 16.00 1.00 10.00 -- -20.00 -30.00 90.00 125
5 \w -90.00 90.00 1.00 1.00 -- 0.00 0.00 0.00 180
;
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2383
_reflns_number_total 3006
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_computing_data_collection
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_computing_data_reduction
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution ?
_refine_diff_density_max 0.330
_refine_diff_density_min -0.250
_refine_diff_density_rms 0.049
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.064
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 195
_refine_ls_number_reflns 3006
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0639
_refine_ls_R_factor_gt 0.0511
_refine_ls_restrained_S_all 1.064
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+4.1353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1334
_refine_ls_wR_factor_ref 0.1421
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Others
Fixed Sof: H9A(0.5) H9B(0.5) H14A(0.5) H14B(0.5)
3.a Secondary CH2 refined with riding coordinates:
C9(H9A,H9B), C14(H14A,H14B), C11(H11A,H11B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
C6(H6), C5(H5), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
3.d Idealised tetrahedral OH refined as rotating group:
O4(H4A), O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.29084(7) 0.80209(7) 0.19561(5) 0.0294(3) Uani 1 1 d . . . . .
O4 O 0.34305(8) 0.69253(8) 0.24158(6) 0.0346(3) Uani 1 1 d . . . . .
H4A H 0.2987 0.6954 0.2608 0.052 Uiso 1 1 calc GR . . . .
O1 O 0.45331(8) 0.58832(8) 0.50700(6) 0.0345(3) Uani 1 1 d . . . . .
O2 O 0.55998(8) 0.54210(7) 0.55886(6) 0.0351(3) Uani 1 1 d . . . . .
H2 H 0.5526 0.5005 0.5372 0.053 Uiso 1 1 calc GR . . . .
O5 O 0.35617(10) 0.78393(10) 0.40124(7) 0.0516(4) Uani 1 1 d . . . . .
O6 O 0.30306(10) 0.92945(10) 0.42300(9) 0.0617(5) Uani 1 1 d . . . . .
C13 C 0.34585(9) 0.75214(10) 0.20227(6) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.5000 0.7500 0.54559(9) 0.0185(5) Uani 1 2 d S T P . .
H9A H 0.4507 0.7468 0.5197 0.022 Uiso 0.5 1 calc R . . . .
H9B H 0.5493 0.7532 0.5197 0.022 Uiso 0.5 1 calc R . . . .
C14 C 0.5000 0.7500 0.20463(9) 0.0183(4) Uani 1 2 d S T P . .
H14A H 0.5012 0.7994 0.2305 0.022 Uiso 0.5 1 calc R . . . .
H14B H 0.4988 0.7006 0.2305 0.022 Uiso 0.5 1 calc R . . . .
C15 C 0.42280(9) 0.75183(9) 0.16441(6) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.42707(9) 0.66840(9) 0.62481(6) 0.0180(3) Uani 1 1 d . . . . .
H11A H 0.3775 0.6655 0.5992 0.022 Uiso 1 1 calc R . . . .
H11B H 0.4288 0.6183 0.6500 0.022 Uiso 1 1 calc R . . . .
C12 C 0.50521(9) 0.59658(9) 0.54674(6) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.50500(9) 0.67292(9) 0.58553(6) 0.0180(3) Uani 1 1 d . . . . .
C16 C 0.42372(9) 0.82878(9) 0.12489(6) 0.0181(3) Uani 1 1 d . . . . .
H16A H 0.4236 0.8789 0.1501 0.022 Uiso 1 1 calc R . . . .
H16B H 0.3740 0.8298 0.0993 0.022 Uiso 1 1 calc R . . . .
C1 C 0.30447(13) 0.79022(13) 0.44919(9) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.27880(13) 0.72547(13) 0.48469(9) 0.0422(5) Uani 1 1 d . . . . .
H6 H 0.2969 0.6711 0.4761 0.051 Uiso 1 1 calc R . . . .
C2 C 0.27657(13) 0.87009(13) 0.46177(11) 0.0453(5) Uani 1 1 d . . . . .
C5 C 0.22670(13) 0.73933(15) 0.53280(10) 0.0481(6) Uani 1 1 d . . . . .
H5 H 0.2089 0.6944 0.5567 0.058 Uiso 1 1 calc R . . . .
C3 C 0.22591(13) 0.88302(14) 0.51021(11) 0.0500(6) Uani 1 1 d . . . . .
H3 H 0.2080 0.9373 0.5193 0.060 Uiso 1 1 calc R . . . .
C4 C 0.20066(13) 0.81773(16) 0.54602(11) 0.0515(6) Uani 1 1 d . . . . .
H4 H 0.1657 0.8273 0.5793 0.062 Uiso 1 1 calc R . . . .
C8 C 0.38648(16) 0.70448(15) 0.38680(10) 0.0538(6) Uani 1 1 d . . . . .
H8A H 0.4218 0.7081 0.3514 0.081 Uiso 1 1 calc GR . . . .
H8B H 0.3401 0.6675 0.3786 0.081 Uiso 1 1 calc GR . . . .
H8C H 0.4185 0.6830 0.4205 0.081 Uiso 1 1 calc GR . . . .
C7 C 0.26800(16) 1.00885(15) 0.42766(18) 0.0743(9) Uani 1 1 d . . . . .
H7A H 0.2916 1.0448 0.3969 0.111 Uiso 1 1 calc GR . . . .
H7B H 0.2798 1.0317 0.4673 0.111 Uiso 1 1 calc GR . . . .
H7C H 0.2083 1.0052 0.4220 0.111 Uiso 1 1 calc GR . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0265(6) 0.0314(7) 0.0304(6) 0.0094(5) 0.0083(5) 0.0068(5)
O4 0.0291(7) 0.0422(8) 0.0326(7) 0.0186(6) 0.0144(5) 0.0116(6)
O1 0.0419(7) 0.0298(7) 0.0318(7) -0.0115(5) -0.0161(6) 0.0083(6)
O2 0.0409(8) 0.0280(7) 0.0363(7) -0.0137(5) -0.0144(6) 0.0116(6)
O5 0.0561(10) 0.0487(9) 0.0498(9) 0.0045(7) -0.0047(7) 0.0048(8)
O6 0.0502(10) 0.0371(9) 0.0977(14) 0.0093(9) 0.0012(9) -0.0013(7)
C13 0.0204(8) 0.0222(8) 0.0155(7) -0.0012(6) -0.0002(6) -0.0010(6)
C9 0.0204(11) 0.0210(11) 0.0140(10) 0.000 0.000 0.0007(9)
C14 0.0213(11) 0.0210(11) 0.0127(9) 0.000 0.000 0.0018(9)
C15 0.0186(8) 0.0206(8) 0.0135(7) -0.0002(6) 0.0009(6) 0.0006(6)
C11 0.0189(7) 0.0190(7) 0.0160(7) -0.0002(6) 0.0004(6) -0.0012(6)
C12 0.0220(8) 0.0204(8) 0.0156(7) 0.0008(6) 0.0025(6) 0.0004(6)
C10 0.0197(7) 0.0204(8) 0.0138(7) -0.0001(6) -0.0002(6) -0.0007(6)
C16 0.0188(7) 0.0200(8) 0.0155(7) 0.0004(6) 0.0001(6) 0.0007(6)
C1 0.0359(11) 0.0429(11) 0.0431(11) -0.0005(9) -0.0152(9) -0.0010(9)
C6 0.0410(11) 0.0406(11) 0.0451(11) 0.0000(9) -0.0162(9) 0.0014(9)
C2 0.0318(11) 0.0406(12) 0.0633(14) -0.0007(10) -0.0143(10) -0.0031(9)
C5 0.0377(11) 0.0568(14) 0.0499(13) 0.0081(11) -0.0147(10) -0.0033(10)
C3 0.0357(11) 0.0450(12) 0.0693(15) -0.0121(11) -0.0167(11) 0.0005(10)
C4 0.0302(11) 0.0716(16) 0.0526(13) -0.0070(12) -0.0113(10) 0.0021(11)
C8 0.0671(15) 0.0565(14) 0.0377(11) -0.0040(10) -0.0119(11) 0.0133(12)
C7 0.0449(14) 0.0378(13) 0.140(3) 0.0081(15) 0.0001(16) -0.0022(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C13 1.2159(19) . ?
O4 H4A 0.8400 . ?
O4 C13 1.3088(19) . ?
O1 C12 1.2325(19) . ?
O2 H2 0.8400 . ?
O2 C12 1.2834(19) . ?
O5 C1 1.366(3) . ?
O5 C8 1.418(3) . ?
O6 C2 1.366(3) . ?
O6 C7 1.413(3) . ?
C13 C15 1.510(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5402(18) 6_564 ?
C9 C10 1.5402(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5435(18) . ?
C14 C15 1.5435(18) 6_564 ?
C15 C16 1.544(2) 12_766 ?
C15 C16 1.531(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.530(2) 15_566 ?
C11 C10 1.543(2) . ?
C12 C10 1.514(2) . ?
C10 C11 1.530(2) 12_767 ?
C16 C15 1.544(2) 15_565 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C1 C6 1.382(3) . ?
C1 C2 1.402(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C2 C3 1.377(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 H4A 109.5 . . ?
C12 O2 H2 109.5 . . ?
C1 O5 C8 117.40(18) . . ?
C2 O6 C7 118.0(2) . . ?
O3 C13 O4 123.39(14) . . ?
O3 C13 C15 122.78(14) . . ?
O4 C13 C15 113.80(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 6_564 . ?
C10 C9 H9B 109.9 6_564 . ?
C10 C9 H9B 109.9 . . ?
C10 C9 C10 109.04(16) . 6_564 ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 110.0 6_564 . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 6_564 . ?
C15 C14 C15 108.66(16) 6_564 . ?
C13 C15 C14 110.18(12) . . ?
C13 C15 C16 107.99(12) . 12_766 ?
C13 C15 C16 109.25(12) . . ?
C14 C15 C16 109.27(11) . 12_766 ?
C16 C15 C14 110.16(11) . . ?
C16 C15 C16 109.96(10) . 12_766 ?
H11A C11 H11B 108.3 . . ?
C10 C11 H11A 109.8 15_566 . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 15_566 . ?
C10 C11 C10 109.16(14) 15_566 . ?
O1 C12 O2 123.46(14) . . ?
O1 C12 C10 120.09(13) . . ?
O2 C12 C10 116.42(13) . . ?
C9 C10 C11 109.04(11) . . ?
C11 C10 C9 110.11(11) 12_767 . ?
C11 C10 C11 109.78(10) 12_767 . ?
C12 C10 C9 109.44(12) . . ?
C12 C10 C11 111.54(12) . 12_767 ?
C12 C10 C11 106.85(12) . . ?
C15 C16 C15 108.89(14) . 15_565 ?
C15 C16 H16A 109.9 15_565 . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 15_565 . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O5 C1 C6 125.4(2) . . ?
O5 C1 C2 115.17(19) . . ?
C6 C1 C2 119.4(2) . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
O6 C2 C1 115.0(2) . . ?
O6 C2 C3 125.5(2) . . ?
C3 C2 C1 119.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O3 0.84 1.75 2.5905(16) 176.5 13_565
O2 H2 O1 0.84 1.75 2.5893(16) 174.8 9_666
_shelx_res_file
;
pc_ht_8_i234_100k.res created by SHELXL-2014/7
TITL exp_18_a.res in I4(1)/a
REM Old TITL exp_18 in I4(1)/a
REM SHELXT solution in I4(1)/a
REM R1 0.201, Rweak 0.057, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C16 N O4
CELL 0.71073 16.238 16.238 22.3825 90 90 90
ZERR 4 0.0002 0.0002 0.0003 0 0 0
LATT 2
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.75-Y,0.25+X,0.25+Z
SYMM 0.75+Y,0.75-X,0.75+Z
SFAC C H O
UNIT 240 288 96
EQIV $1 0.5-X,1.5-Y,0.5-Z
EQIV $2 1-X,1-Y,1-Z
L.S. 99
PLAN 20
SIZE 0.11 0.09 0.07
TEMP -173.15
HTAB O4 O3_$1
HTAB O2 O1_$2
BOND $H
list 4
fmap 2 53
acta
SHEL 999 0.8
OMIT 0 1 1
REM
REM
REM
WGHT 0.069200 4.135300
FVAR 0.18721
O3 3 0.290837 0.802095 0.195610 11.00000 0.02647 0.03141 =
0.03044 0.00935 0.00831 0.00684
O4 3 0.343046 0.692526 0.241576 11.00000 0.02907 0.04224 =
0.03262 0.01858 0.01440 0.01160
AFIX 147
H4A 2 0.298696 0.695361 0.260785 11.00000 -1.50000
AFIX 0
O1 3 0.453308 0.588324 0.507004 11.00000 0.04186 0.02982 =
0.03179 -0.01150 -0.01608 0.00830
O2 3 0.559978 0.542095 0.558858 11.00000 0.04091 0.02797 =
0.03628 -0.01372 -0.01437 0.01158
AFIX 147
H2 2 0.552605 0.500506 0.537190 11.00000 -1.50000
AFIX 0
O5 3 0.356172 0.783926 0.401237 11.00000 0.05614 0.04871 =
0.04983 0.00449 -0.00469 0.00478
O6 3 0.303060 0.929446 0.422995 11.00000 0.05022 0.03712 =
0.09770 0.00929 0.00122 -0.00128
C13 1 0.345849 0.752136 0.202273 11.00000 0.02040 0.02225 =
0.01555 -0.00122 -0.00019 -0.00104
C9 1 0.500000 0.750000 0.545590 10.50000 0.02037 0.02099 =
0.01402 0.00000 0.00000 0.00072
AFIX 23
H9A 2 0.450688 0.746805 0.519683 10.50000 -1.20000
H9B 2 0.549312 0.753196 0.519683 10.50000 -1.20000
AFIX 0
C14 1 0.500000 0.750000 0.204629 10.50000 0.02128 0.02097 =
0.01273 0.00000 0.00000 0.00182
AFIX 23
H14A 2 0.501168 0.799418 0.230520 10.50000 -1.20000
H14B 2 0.498830 0.700583 0.230521 10.50000 -1.20000
AFIX 0
C15 1 0.422800 0.751826 0.164415 11.00000 0.01863 0.02062 =
0.01350 -0.00018 0.00087 0.00064
C11 1 0.427067 0.668400 0.624813 11.00000 0.01889 0.01898 =
0.01604 -0.00016 0.00038 -0.00119
AFIX 23
H11A 2 0.377458 0.665463 0.599190 11.00000 -1.20000
H11B 2 0.428840 0.618291 0.649975 11.00000 -1.20000
AFIX 0
C12 1 0.505207 0.596576 0.546736 11.00000 0.02205 0.02044 =
0.01562 0.00083 0.00248 0.00038
C10 1 0.504995 0.672922 0.585526 11.00000 0.01975 0.02037 =
0.01379 -0.00014 -0.00023 -0.00067
C16 1 0.423719 0.828781 0.124887 11.00000 0.01884 0.01999 =
0.01548 0.00039 0.00011 0.00067
AFIX 23
H16A 2 0.423592 0.878851 0.150124 11.00000 -1.20000
H16B 2 0.374004 0.829838 0.099295 11.00000 -1.20000
AFIX 0
C1 1 0.304472 0.790218 0.449188 11.00000 0.03592 0.04290 =
0.04311 -0.00047 -0.01522 -0.00099
C6 1 0.278799 0.725467 0.484686 11.00000 0.04096 0.04060 =
0.04509 -0.00004 -0.01623 0.00139
AFIX 43
H6 2 0.296939 0.671121 0.476094 11.00000 -1.20000
AFIX 0
C2 1 0.276571 0.870087 0.461766 11.00000 0.03182 0.04062 =
0.06334 -0.00066 -0.01431 -0.00314
C5 1 0.226697 0.739329 0.532796 11.00000 0.03766 0.05685 =
0.04992 0.00809 -0.01469 -0.00327
AFIX 43
H5 2 0.208945 0.694369 0.556706 11.00000 -1.20000
AFIX 0
C3 1 0.225909 0.883016 0.510207 11.00000 0.03566 0.04500 =
0.06927 -0.01211 -0.01669 0.00049
AFIX 43
H3 2 0.207956 0.937272 0.519288 11.00000 -1.20000
AFIX 0
C4 1 0.200663 0.817725 0.546019 11.00000 0.03015 0.07157 =
0.05265 -0.00703 -0.01127 0.00207
AFIX 43
H4 2 0.165710 0.827269 0.579343 11.00000 -1.20000
AFIX 0
C8 1 0.386481 0.704483 0.386801 11.00000 0.06710 0.05654 =
0.03766 -0.00400 -0.01188 0.01328
AFIX 137
H8A 2 0.421774 0.708064 0.351379 11.00000 -1.50000
H8B 2 0.340134 0.667528 0.378571 11.00000 -1.50000
H8C 2 0.418482 0.682952 0.420478 11.00000 -1.50000
AFIX 0
C7 1 0.268002 1.008851 0.427658 11.00000 0.04490 0.03777 =
0.14012 0.00807 0.00011 -0.00223
AFIX 137
H7A 2 0.291637 1.044765 0.396931 11.00000 -1.50000
H7B 2 0.279790 1.031686 0.467275 11.00000 -1.50000
H7C 2 0.208269 1.005160 0.422002 11.00000 -1.50000
AFIX 0
HKLF 4
REM exp_18_a.res in I4(1)/a
REM R1 = 0.0511 for 2383 Fo > 4sig(Fo) and 0.0639 for all 3006 data
REM 195 parameters refined using 0 restraints
END
WGHT 0.0691 4.1380
REM Highest difference peak 0.330, deepest hole -0.250, 1-sigma level 0.049
Q1 1 0.5043 0.7060 0.5681 11.00000 0.05 0.33
Q2 1 0.4573 0.7468 0.1830 11.00000 0.05 0.30
Q3 1 0.2758 1.0192 0.4801 11.00000 0.05 0.29
Q4 1 0.4169 0.7172 0.1431 11.00000 0.05 0.28
Q5 1 0.5051 0.6413 0.5713 11.00000 0.05 0.28
Q6 1 0.5390 0.6748 0.6011 11.00000 0.05 0.28
Q7 1 0.3875 0.7479 0.1801 11.00000 0.05 0.28
Q8 1 0.4685 0.6720 0.6034 11.00000 0.05 0.26
Q9 1 0.4229 0.7868 0.1452 11.00000 0.05 0.23
Q10 1 0.2910 0.9400 0.4645 11.00000 0.05 0.22
Q11 1 0.5150 0.5266 0.5821 11.00000 0.05 0.22
Q12 1 0.2701 0.8701 0.4916 11.00000 0.05 0.20
Q13 1 0.3555 0.7475 0.2616 11.00000 0.05 0.20
Q14 1 0.5023 0.5959 0.4911 11.00000 0.05 0.19
Q15 1 0.2871 0.7583 0.1758 11.00000 0.05 0.19
Q16 1 0.3012 0.8276 0.4591 11.00000 0.05 0.18
Q17 1 0.2167 0.8658 0.5406 11.00000 0.05 0.18
Q18 1 0.3116 1.0431 0.4450 11.00000 0.05 0.17
Q19 1 0.2142 0.7821 0.5328 11.00000 0.05 0.17
Q20 1 0.2075 1.0045 0.4364 11.00000 0.05 0.17
;
_shelx_res_checksum 16830
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_ADTA_3-38_ethanol-tetradecane_3-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915300'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date 2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H16 O8, 0.43(C14 H30)'
_chemical_formula_sum 'C20 H28.9 O8'
_chemical_formula_weight 397.29
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 70
_space_group_name_H-M_alt 'F d d d'
_space_group_name_Hall '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'
_cell_length_a 7.3713(11)
_cell_length_b 22.951(4)
_cell_length_c 23.585(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3990.0(11)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 1322
_cell_measurement_temperature 200
_cell_measurement_theta_max 25.694
_cell_measurement_theta_min 2.477
_shelx_estimated_absorpt_T_max 0.995
_shelx_estimated_absorpt_T_min 0.989
_exptl_absorpt_coefficient_mu 0.102
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4564
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0979 before and 0.0743 after correction. The Ratio of minimum to maximum transmission is 0.6123. The \l/2 correction factor is 0.00150.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.323
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1703
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.11
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0818
_diffrn_reflns_av_unetI/netI 0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_number 8009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.377
_diffrn_reflns_theta_min 2.477
_diffrn_ambient_temperature 200
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 628
_reflns_number_total 1028
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.332
_refine_diff_density_min -0.260
_refine_diff_density_rms 0.063
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 67
_refine_ls_number_reflns 1028
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.1034
_refine_ls_R_factor_gt 0.0634
_refine_ls_restrained_S_all 1.044
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1230P)^2^+3.7672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1830
_refine_ls_wR_factor_ref 0.2143
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All O(H) groups
2. Rigid body (RIGU) restrains
C7, C6
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
Fixed Sof: H4A(0.5) H4B(0.5) H3A(0.5) H3B(0.5) H1A(0.5) H1B(0.5)
4.a Secondary CH2 refined with riding coordinates:
C4(H4A,H4B), C3(H3A,H3B), C1(H1A,H1B)
4.b Idealised tetrahedral OH refined as rotating group:
O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2324(3) 0.48604(10) 0.48359(9) 0.0519(7) Uani 1 1 d . . . . .
O1 O -0.0263(3) 0.45076(11) 0.44997(9) 0.0514(8) Uani 1 1 d . . . . .
C4 C 0.3750 0.3750 0.45035(13) 0.0267(9) Uani 1 2 d S T P . .
C5 C 0.1395(3) 0.45206(12) 0.45024(10) 0.0302(7) Uani 1 1 d . . . . .
C2 C 0.2539(3) 0.41363(11) 0.41262(9) 0.0272(7) Uani 1 1 d . . . . .
C3 C 0.3750 0.45273(16) 0.3750 0.0293(9) Uani 1 2 d S T P . .
C1 C 0.1335(5) 0.3750 0.3750 0.0272(8) Uani 1 2 d S T P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0281(11) 0.0662(16) 0.0614(14) -0.0346(11) 0.0023(10) -0.0012(11)
O1 0.0195(11) 0.0728(17) 0.0618(14) -0.0323(12) 0.0020(9) 0.0017(10)
C4 0.0192(18) 0.034(2) 0.0264(17) 0.000 0.000 -0.0021(15)
C5 0.0221(13) 0.0362(16) 0.0324(14) -0.0024(10) -0.0003(10) -0.0012(12)
C2 0.0165(12) 0.0329(14) 0.0322(13) -0.0017(10) 0.0007(10) 0.0007(11)
C3 0.0226(18) 0.031(2) 0.0341(19) 0.000 -0.0004(14) 0.000
C1 0.0193(18) 0.0321(19) 0.0302(17) -0.0025(15) 0.000 0.000
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.302(3) . ?
O1 C5 1.222(3) . ?
C4 C2 1.541(3) . ?
C4 C2 1.541(3) 2 ?
C5 C2 1.508(3) . ?
C2 C3 1.546(3) . ?
C2 C1 1.536(3) . ?
C3 C2 1.546(3) 3 ?
C1 C2 1.536(3) 4 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C4 C2 109.5(3) 2 . ?
O2 C5 C2 114.3(2) . . ?
O1 C5 O2 122.9(3) . . ?
O1 C5 C2 122.8(2) . . ?
C4 C2 C3 109.30(16) . . ?
C5 C2 C4 108.70(19) . . ?
C5 C2 C3 108.7(2) . . ?
C5 C2 C1 110.8(2) . . ?
C1 C2 C4 109.64(17) . . ?
C1 C2 C3 109.69(16) . . ?
C2 C3 C2 109.0(3) . 3 ?
C2 C1 C2 109.5(3) 4 . ?
_shelx_res_file
;
pc_8_338_200k_fddd.res created by SHELXL-2014/7
TITL pc_8_338_200k_fddd_a.res in Fddd
REM Old TITL PC_8_338_200K_Fddd in Fddd
REM SHELXT solution in Fddd
REM R1 0.266, Rweak 0.008, Alpha 0.030, Orientation as input
REM Formula found by SHELXT: C7 O4
CELL 0.71073 7.3713 22.9506 23.5851 90 90 90
ZERR 8 0.0011 0.0038 0.0039 0 0 0
LATT 4
SYMM 0.75-X,0.75-Y,+Z
SYMM 0.75-X,+Y,0.75-Z
SYMM +X,0.75-Y,0.75-Z
SFAC C H O
UNIT 160 230.86 64
EQIV $1 -X,1-Y,1-Z
RIGU 0.002 0.002 C7 C6
L.S. 50
PLAN 20
SIZE 0.11 0.08 0.05
TEMP -73.15
HTAB O2 O1_$1
BOND $H
list 4
fmap 2
acta
REM
REM
REM
WGHT 0.123000 3.767200
FVAR 0.21648
O2 3 0.232440 0.486039 0.483586 11.00000 0.02813 0.06615 =
0.06137 -0.03464 0.00230 -0.00122
AFIX 147
H2 2 0.161253 0.504428 0.504875 11.00000 -1.50000
AFIX 0
O1 3 -0.026267 0.450756 0.449972 11.00000 0.01953 0.07276 =
0.06182 -0.03231 0.00199 0.00169
C4 1 0.375000 0.375000 0.450348 10.50000 0.01921 0.03436 =
0.02639 0.00000 0.00000 -0.00207
AFIX 23
H4A 2 0.451662 0.399803 0.474952 10.50000 -1.20000
H4B 2 0.298337 0.350196 0.474951 10.50000 -1.20000
AFIX 0
C5 1 0.139514 0.452057 0.450237 11.00000 0.02211 0.03623 =
0.03239 -0.00237 -0.00034 -0.00121
C2 1 0.253850 0.413628 0.412622 11.00000 0.01650 0.03290 =
0.03223 -0.00168 0.00071 0.00070
C3 1 0.375000 0.452728 0.375000 10.50000 0.02256 0.03116 =
0.03414 0.00000 -0.00042 0.00000
AFIX 23
H3A 2 0.451728 0.477993 0.399134 10.50000 -1.20000
H3B 2 0.298275 0.477994 0.350866 10.50000 -1.20000
AFIX 0
C1 1 0.133534 0.375000 0.375000 10.50000 0.01929 0.03211 =
0.03021 -0.00253 0.00000 0.00000
AFIX 23
H1A 2 0.054818 0.350274 0.399037 10.50000 -1.20000
H1B 2 0.054813 0.399724 0.350963 10.50000 -1.20000
AFIX 0
C7 1 0.375000 0.375000 0.610638 10.50000 0.22734 0.15391 =
0.11124 0.00000 0.00000 -0.04155
C6 1 0.206145 0.378764 0.646050 11.00000 0.22972 0.16679 =
0.11996 0.03044 0.00396 0.00099
HKLF 4
REM pc_8_338_200k_fddd_a.res in Fddd
REM R1 = 0.0634 for 628 Fo > 4sig(Fo) and 0.1034 for all 1028 data
REM 67 parameters refined using 3 restraints
END
WGHT 0.1229 3.7791
REM Highest difference peak 0.332, deepest hole -0.260, 1-sigma level 0.063
Q1 1 0.1751 0.3317 0.6730 11.00000 0.05 0.33
Q2 1 0.3560 0.4214 0.5783 11.00000 0.05 0.27
Q3 1 0.2662 0.4112 0.6206 11.00000 0.05 0.26
Q4 1 0.2436 0.4215 0.6796 11.00000 0.05 0.24
Q5 1 0.0011 0.4176 0.4829 11.00000 0.05 0.20
Q6 1 0.3750 0.3750 0.6851 10.50000 0.05 0.19
Q7 1 0.3139 0.4266 0.3989 11.00000 0.05 0.18
Q8 1 0.2067 0.4283 0.4245 11.00000 0.05 0.18
Q9 1 0.2796 0.4103 0.5714 11.00000 0.05 0.18
Q10 1 0.5165 0.4376 0.5680 11.00000 0.05 0.16
Q11 1 0.3217 0.4302 0.6420 11.00000 0.05 0.16
Q12 1 0.3379 0.4190 0.6516 11.00000 0.05 0.16
Q13 1 0.1559 0.4505 0.5062 11.00000 0.05 0.15
Q14 1 0.0850 0.4292 0.6495 11.00000 0.05 0.14
Q15 1 0.1277 0.4086 0.6849 11.00000 0.05 0.14
Q16 1 0.1107 0.4155 0.4893 11.00000 0.05 0.14
Q17 1 0.2890 0.3695 0.7227 11.00000 0.05 0.14
Q18 1 0.1250 0.4381 0.6250 10.50000 0.05 0.13
Q19 1 0.4763 0.4168 0.5993 11.00000 0.05 0.13
Q20 1 0.2495 0.4481 0.6420 11.00000 0.05 0.12
;
_shelx_res_checksum 26456
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT043_ADTA_3-38_ethanol-tetradecane_3-fold_publ
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 12.96 Check
RESPONSE: Due to disorder, the tetradecane solvent molecule
was modelled without riding H-atoms. However, H-atoms
for this molecule were included in the refined formula_sum.
;
_vrf_PLAT260_ADTA_3-38_ethanol-tetradecane_3-fold_publ
;
PROBLEM: Large Average Ueq of Residue Including C6 0.168 Check
RESPONSE: C6 was modelled as a tetradecane solvent molecule that
was disordered in the 1-D voids in the crystal structure.
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_1-12_MeOH-Acetone_P-1_publ
_database_code_depnum_ccdc_archive 'CCDC 1915305'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_TMA_1-12_MeOH-Acetone_P-1_publ
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 2.52 Check
RESPONSE: Disordered solvent in large 1-D pores in the structure
could not be resolved and was tentatively modelled at disordered
H2O. H atoms for these molecules were only added to the unit
cell atom count, but not refined as part of the structure.
;
# end Validation Reply Form
_audit_creation_date 2018-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6, 2.25(H2 O)'
_chemical_formula_sum 'C9 H10.50 O8.25'
_chemical_formula_weight 250.67
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 3.5960(9)
_cell_length_b 8.934(2)
_cell_length_c 17.937(4)
_cell_angle_alpha 77.839(7)
_cell_angle_beta 86.729(7)
_cell_angle_gamma 88.967(7)
_cell_volume 562.4(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 903
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.265
_cell_measurement_theta_min 2.326
_shelx_estimated_absorpt_T_max 0.988
_shelx_estimated_absorpt_T_min 0.971
_exptl_absorpt_coefficient_mu 0.134
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4925
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.6607.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.480
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 261
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.176
_exptl_crystal_size_min 0.09
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0655
_diffrn_reflns_av_unetI/netI 0.1317
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_h_min -3
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 5370
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.659
_diffrn_reflns_theta_min 2.327
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1156
_reflns_number_total 2353
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.374
_refine_diff_density_min -0.380
_refine_diff_density_rms 0.086
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.916
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 196
_refine_ls_number_reflns 2353
_refine_ls_number_restraints 30
_refine_ls_R_factor_all 0.1470
_refine_ls_R_factor_gt 0.0676
_refine_ls_restrained_S_all 0.931
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0991P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1598
_refine_ls_wR_factor_ref 0.1898
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1S) \\sim Ueq, Uanis(O2S) \\sim Ueq, Uanis(O3S) \\sim Ueq, Uanis(O4S)
\\sim Ueq, Uanis(O5S) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
Fixed Sof: O5S(0.25) O3S(0.25) O2S(0.25) O1S(0.25) O4S(0.25)
4.a Free rotating group:
O7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
C2(H2), C6(H6), C4(H4A)
4.c Idealised tetrahedral OH refined as rotating group:
O1(H1), O5(H5), O4(H4)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.3009(8) 0.9394(3) 0.60273(16) 0.0274(7) Uani 1 1 d . . . . .
O1 O 0.7608(8) 0.4231(3) 0.57737(15) 0.0299(7) Uani 1 1 d . . . . .
H1 H 0.7978 0.3485 0.5561 0.045 Uiso 1 1 calc GR . . . .
O2 O 1.0249(8) 0.2674(3) 0.67501(16) 0.0312(7) Uani 1 1 d . . . . .
O5 O 0.3510(8) 1.0012(3) 0.71606(15) 0.0328(8) Uani 1 1 d . . . . .
H5 H 0.2486 1.0826 0.6941 0.049 Uiso 1 1 calc GR . . . .
O7 O 0.9844(9) 0.2043(3) 0.50979(16) 0.0313(8) Uani 1 1 d . . . . .
H7A H 1.0863 0.1357 0.5427 0.047 Uiso 1 1 d G . . . .
H7B H 0.8439 0.1624 0.4837 0.047 Uiso 1 1 d G . . . .
O3 O 1.0305(8) 0.4242(3) 0.92410(15) 0.0313(7) Uani 1 1 d . . . . .
O4 O 0.7563(8) 0.6464(3) 0.93541(15) 0.0327(8) Uani 1 1 d . . . . .
H4 H 0.8417 0.6238 0.9790 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.8637(11) 0.3860(4) 0.6478(2) 0.0226(9) Uani 1 1 d . . . . .
C9 C 0.3882(11) 0.9068(4) 0.6689(2) 0.0204(9) Uani 1 1 d . . . . .
C3 C 0.7682(10) 0.5799(4) 0.8153(2) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.8412(11) 0.4708(4) 0.7708(2) 0.0223(9) Uani 1 1 d . . . . .
H2 H 0.9405 0.3736 0.7933 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7697(10) 0.5032(4) 0.6939(2) 0.0202(8) Uani 1 1 d . . . . .
C6 C 0.6214(11) 0.6456(4) 0.6606(2) 0.0217(9) Uani 1 1 d . . . . .
H6 H 0.5695 0.6677 0.6081 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5492(10) 0.7560(4) 0.7050(2) 0.0193(8) Uani 1 1 d . . . . .
C8 C 0.8605(11) 0.5439(4) 0.8970(2) 0.0234(9) Uani 1 1 d . . . . .
C4 C 0.6254(10) 0.7225(4) 0.7819(2) 0.0226(9) Uani 1 1 d . . . . .
H4A H 0.5794 0.7975 0.8119 0.027 Uiso 1 1 calc R . . . .
O5S O 1.148(12) 0.017(3) 0.9684(18) 0.111(9) Uani 0.25 1 d . U P A 5
O3S O 1.770(15) 0.038(3) 0.945(2) 0.144(10) Uani 0.25 1 d . U P B 3
O2S O 1.710(9) 0.070(2) 0.8737(14) 0.122(8) Uani 0.25 1 d . U P C 2
O1S O 2.194(11) 0.054(3) 0.8948(16) 0.144(9) Uani 0.25 1 d . U P D 1
O4S O 1.431(16) 0.021(3) 0.965(2) 0.138(12) Uani 0.25 1 d . U P E 4
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O6 0.0327(18) 0.0253(13) 0.0237(17) -0.0045(11) -0.0046(13) 0.0094(12)
O1 0.0429(19) 0.0252(13) 0.0236(17) -0.0097(11) -0.0063(14) 0.0119(13)
O2 0.0364(18) 0.0213(12) 0.0369(19) -0.0081(11) -0.0062(14) 0.0121(12)
O5 0.045(2) 0.0214(13) 0.0345(18) -0.0089(11) -0.0129(14) 0.0128(12)
O7 0.044(2) 0.0241(13) 0.0270(18) -0.0069(11) -0.0103(14) 0.0100(13)
O3 0.0370(19) 0.0299(13) 0.0260(18) -0.0035(11) -0.0081(14) 0.0126(12)
O4 0.042(2) 0.0320(14) 0.0264(18) -0.0095(12) -0.0099(15) 0.0132(13)
C7 0.019(2) 0.0183(16) 0.030(2) -0.0043(14) 0.0001(18) 0.0020(15)
C9 0.018(2) 0.0217(17) 0.022(2) -0.0062(15) 0.0022(18) 0.0004(15)
C3 0.013(2) 0.0248(17) 0.021(2) -0.0036(14) -0.0004(16) 0.0004(15)
C2 0.018(2) 0.0213(16) 0.027(2) -0.0025(15) -0.0004(17) 0.0020(15)
C1 0.013(2) 0.0203(16) 0.027(2) -0.0031(14) 0.0002(17) -0.0008(14)
C6 0.017(2) 0.0211(16) 0.026(2) -0.0044(15) -0.0007(17) 0.0004(15)
C5 0.013(2) 0.0205(16) 0.023(2) -0.0023(14) 0.0003(17) -0.0008(14)
C8 0.015(2) 0.0240(17) 0.031(3) -0.0056(16) 0.0019(18) 0.0028(15)
C4 0.018(2) 0.0230(17) 0.029(2) -0.0097(15) -0.0003(18) 0.0016(15)
O5S 0.135(18) 0.073(11) 0.135(18) -0.049(12) -0.003(14) 0.012(14)
O3S 0.171(19) 0.076(12) 0.21(2) -0.071(14) -0.025(17) -0.004(14)
O2S 0.197(19) 0.060(10) 0.125(15) -0.049(11) -0.029(14) -0.025(11)
O1S 0.22(2) 0.107(13) 0.121(16) -0.071(13) 0.032(15) 0.003(14)
O4S 0.15(2) 0.076(13) 0.19(2) -0.052(15) 0.005(18) 0.001(15)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 C9 1.220(4) . ?
O1 H1 0.8400 . ?
O1 C7 1.309(4) . ?
O2 C7 1.220(4) . ?
O5 H5 0.8400 . ?
O5 C9 1.314(4) . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8503 . ?
O3 C8 1.243(4) . ?
O4 H4 0.8400 . ?
O4 C8 1.296(4) . ?
C7 C1 1.488(5) . ?
C9 C5 1.488(4) . ?
C3 C2 1.397(5) . ?
C3 C8 1.487(5) . ?
C3 C4 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(5) . ?
C1 C6 1.397(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.404(5) . ?
C5 C4 1.392(5) . ?
C4 H4A 0.9500 . ?
O5S O5S 1.49(7) 2_757 ?
O4S O4S 1.35(7) 2_857 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
C9 O5 H5 109.5 . . ?
H7A O7 H7B 109.5 . . ?
C8 O4 H4 109.5 . . ?
O1 C7 C1 114.1(3) . . ?
O2 C7 O1 124.6(3) . . ?
O2 C7 C1 121.3(4) . . ?
O6 C9 O5 123.6(3) . . ?
O6 C9 C5 123.6(3) . . ?
O5 C9 C5 112.8(3) . . ?
C2 C3 C8 119.3(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C8 121.0(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C2 C1 C7 118.9(3) . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 C7 121.2(3) . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C9 119.3(3) . . ?
C4 C5 C9 121.0(3) . . ?
C4 C5 C6 119.7(3) . . ?
O3 C8 O4 124.1(4) . . ?
O3 C8 C3 120.8(3) . . ?
O4 C8 C3 115.1(3) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
_shelx_res_file
;
pc_ht_1_i112.res created by SHELXL-2014/7
TITL pc_ht_1_i112_a.res in P-1
REM Old TITL PC_HT_1_i112 in P-1
REM SHELXT solution in P-1
REM R1 0.197, Rweak 0.010, Alpha 0.050, Orientation as input
REM Formula found by SHELXT: C9 O7
CELL 0.71073 3.596 8.9338 17.9368 77.839 86.729 88.967
ZERR 2 0.0009 0.0022 0.0044 0.007 0.007 0.007
LATT 1
SFAC C H O
UNIT 18 21 16.5
ISOR 0.01 0.02 O1S O2S O3S O4S O5S
L.S. 20 0 0
PLAN 20
SIZE 0.09 0.176 0.22
TEMP -173.15
BOND $H
list 4
fmap 2 53
acta
OMIT 0 1 2
REM
REM
REM
WGHT 0.099100
FVAR 0.74760
O6 3 0.300912 0.939423 0.602728 11.00000 0.03270 0.02534 =
0.02372 -0.00449 -0.00457 0.00944
O1 3 0.760820 0.423097 0.577367 11.00000 0.04291 0.02523 =
0.02362 -0.00967 -0.00630 0.01190
AFIX 147
H1 2 0.797774 0.348515 0.556080 11.00000 -1.50000
AFIX 0
O2 3 1.024916 0.267408 0.675009 11.00000 0.03641 0.02132 =
0.03692 -0.00814 -0.00620 0.01212
O5 3 0.350969 1.001190 0.716058 11.00000 0.04466 0.02137 =
0.03446 -0.00889 -0.01290 0.01277
AFIX 147
H5 2 0.248616 1.082614 0.694135 11.00000 -1.50000
AFIX 6
O7 3 0.984415 0.204336 0.509786 11.00000 0.04389 0.02413 =
0.02702 -0.00688 -0.01027 0.00999
H7A 2 1.086264 0.135673 0.542671 11.00000 -1.50000
H7B 2 0.843892 0.162359 0.483681 11.00000 -1.50000
AFIX 0
O3 3 1.030453 0.424240 0.924099 11.00000 0.03701 0.02991 =
0.02604 -0.00346 -0.00814 0.01260
O4 3 0.756279 0.646409 0.935408 11.00000 0.04155 0.03203 =
0.02645 -0.00954 -0.00989 0.01324
AFIX 147
H4 2 0.841662 0.623797 0.979020 11.00000 -1.50000
AFIX 0
C7 1 0.863651 0.385993 0.647790 11.00000 0.01937 0.01828 =
0.02959 -0.00427 0.00014 0.00204
C9 1 0.388201 0.906804 0.668944 11.00000 0.01791 0.02170 =
0.02194 -0.00616 0.00223 0.00041
C3 1 0.768234 0.579852 0.815301 11.00000 0.01272 0.02484 =
0.02132 -0.00363 -0.00043 0.00039
C2 1 0.841188 0.470757 0.770763 11.00000 0.01778 0.02130 =
0.02650 -0.00248 -0.00037 0.00202
AFIX 43
H2 2 0.940546 0.373585 0.793341 11.00000 -1.20000
AFIX 0
C1 1 0.769700 0.503231 0.693897 11.00000 0.01289 0.02030 =
0.02658 -0.00314 0.00023 -0.00084
C6 1 0.621382 0.645644 0.660605 11.00000 0.01745 0.02114 =
0.02609 -0.00436 -0.00070 0.00036
AFIX 43
H6 2 0.569460 0.667742 0.608059 11.00000 -1.20000
AFIX 0
C5 1 0.549229 0.756028 0.704965 11.00000 0.01334 0.02047 =
0.02300 -0.00234 0.00032 -0.00077
C8 1 0.860506 0.543901 0.896954 11.00000 0.01477 0.02405 =
0.03077 -0.00561 0.00192 0.00277
C4 1 0.625350 0.722479 0.781938 11.00000 0.01794 0.02305 =
0.02859 -0.00972 -0.00029 0.00158
AFIX 43
H4A 2 0.579446 0.797464 0.811904 11.00000 -1.20000
AFIX 0
PART 5
O5S 3 1.147507 0.016808 0.968406 10.25000 0.13497 0.07270 =
0.13530 -0.04944 -0.00285 0.01187
PART 0
PART 3
O3S 3 1.769584 0.038046 0.944813 10.25000 0.17110 0.07628 =
0.20548 -0.07063 -0.02466 -0.00407
PART 0
PART 2
O2S 3 1.709858 0.070026 0.873692 10.25000 0.19691 0.06016 =
0.12542 -0.04895 -0.02872 -0.02457
PART 0
PART 1
O1S 3 2.194117 0.053677 0.894813 10.25000 0.22103 0.10700 =
0.12107 -0.07106 0.03250 0.00313
PART 0
PART 4
O4S 3 1.430710 0.021240 0.965023 10.25000 0.15253 0.07644 =
0.19317 -0.05220 0.00467 0.00083
HKLF 4
REM pc_ht_1_i112_a.res in P-1
REM R1 = 0.0676 for 1156 Fo > 4sig(Fo) and 0.1470 for all 2353 data
REM 196 parameters refined using 30 restraints
END
WGHT 0.0991 0.0000
REM Highest difference peak 0.374, deepest hole -0.380, 1-sigma level 0.086
Q1 1 1.5332 0.0721 0.8937 11.00000 0.05 0.37
Q2 1 1.5118 0.0980 0.8842 11.00000 0.05 0.37
Q3 1 1.9226 0.0639 0.8888 11.00000 0.05 0.37
Q4 1 1.6660 0.0075 0.9834 11.00000 0.05 0.37
Q5 1 2.3314 -0.0331 0.9026 11.00000 0.05 0.37
Q6 1 1.8131 0.0757 0.8409 11.00000 0.05 0.30
Q7 1 0.8334 0.2799 0.5249 11.00000 0.05 0.30
Q8 1 1.2550 0.0646 1.0052 11.00000 0.05 0.28
Q9 1 0.8865 0.3200 0.6831 11.00000 0.05 0.28
Q10 1 1.4305 0.0000 1.0055 11.00000 0.05 0.28
Q11 1 1.4336 0.1536 0.8585 11.00000 0.05 0.27
Q12 1 0.9762 0.2849 0.6249 11.00000 0.05 0.26
Q13 1 0.5714 0.6233 0.5323 11.00000 0.05 0.25
Q14 1 0.9582 0.0402 0.9663 11.00000 0.05 0.25
Q15 1 2.0462 0.0746 0.8426 11.00000 0.05 0.25
Q16 1 1.9178 0.0045 0.9780 11.00000 0.05 0.25
Q17 1 1.2596 0.4891 0.9021 11.00000 0.05 0.24
Q18 1 0.1813 1.0251 0.6183 11.00000 0.05 0.23
Q19 1 0.8269 0.4434 0.6756 11.00000 0.05 0.23
Q20 1 1.1545 0.2635 0.5400 11.00000 0.05 0.23
;
_shelx_res_checksum 9699
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_ADTA_7-38_dioxane-tetradecane_3-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915302'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ADTA_7-38_dioxane-tetradecane_3-fold_publ
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 12.79 Check
RESPONSE: Due to disorder, the tetradecane solvent molecule
was modelled without riding H-atoms. However, H-atoms
for this molecule were included in the refined formula_sum.
;
# end Validation Reply Form
_audit_creation_date 2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C14 H16 O8, 0.43(C14 H30)'
_chemical_formula_sum 'C20.02 H28.86 O8'
_chemical_formula_weight 397.50
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system tetragonal
_space_group_IT_number 141
_space_group_name_H-M_alt 'I 41/a m d'
_space_group_name_Hall '-I 4bd 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z+1/2'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z-1/2'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'
_cell_length_a 16.429(3)
_cell_length_b 16.429(3)
_cell_length_c 7.3580(12)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1986.0(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2537
_cell_measurement_temperature 200
_cell_measurement_theta_max 25.936
_cell_measurement_theta_min 2.478
_shelx_estimated_absorpt_T_max 0.987
_shelx_estimated_absorpt_T_min 0.985
_exptl_absorpt_coefficient_mu 0.102
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4644
_exptl_absorpt_correction_type ?
_exptl_absorpt_process_details
;
Reflections not merged
7998 Corrected reflections written to file PC_8_638_200K_0m.hkl
Estimated minimum and maximum transmission: 0.4644 0.7454
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r = 0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.329
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 852
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.13
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0598
_diffrn_reflns_av_unetI/netI 0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 6
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_number 7390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.377
_diffrn_reflns_theta_min 2.479
_diffrn_ambient_temperature 200
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 407
_reflns_number_total 554
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.241
_refine_diff_density_min -0.242
_refine_diff_density_rms 0.060
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.135
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 47
_refine_ls_number_reflns 554
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0842
_refine_ls_R_factor_gt 0.0650
_refine_ls_restrained_S_all 1.134
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+3.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1850
_refine_ls_wR_factor_ref 0.1993
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
2. Restrained distances
O2-H2
0.82 with sigma of 0.02
3. Others
Fixed Sof: H3A(0.5) H3B(0.5) H1A(0.25) H1B(0.25)
4.a Secondary CH2 refined with riding coordinates:
C3(H3A,H3B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65056(17) 0.2500 0.2242(3) 0.0489(10) Uani 1 2 d S T P . .
O2 O 0.71998(17) 0.2500 0.4818(4) 0.0515(10) Uani 1 2 d DS T P . .
C4 C 0.6520(2) 0.2500 0.3892(4) 0.0275(8) Uani 1 2 d S T P . .
C2 C 0.57633(19) 0.2500 0.5038(4) 0.0235(8) Uani 1 2 d S T P . .
C3 C 0.57611(14) 0.32611(14) 0.6250 0.0255(8) Uani 1 2 d S T P . .
H3A H 0.6256 0.3266 0.7018 0.031 Uiso 0.5 1 calc R . . . .
H3B H 0.5766 0.3756 0.5482 0.031 Uiso 0.5 1 calc R . . . .
C1 C 0.5000 0.2500 0.3834(6) 0.0244(11) Uani 1 4 d S T P . .
H1A H 0.5000 0.2988 0.3046 0.029 Uiso 0.5 2 calc RS T P . .
H1B H 0.5000 0.2012 0.3046 0.029 Uiso 0.5 2 calc RS T P . .
C5 C 0.7653(7) 0.0196(7) 0.560(3) 0.195(10) Uani 0.754(18) 1 d . . . . .
H2 H 0.760(3) 0.2500 0.413(8) 0.10(2) Uiso 1 2 d DS T P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0335(15) 0.095(3) 0.0180(13) 0.000 0.0020(11) 0.000
O2 0.0288(15) 0.102(3) 0.0241(14) 0.000 0.0009(12) 0.000
C4 0.0277(18) 0.0368(19) 0.0180(15) 0.000 -0.0002(13) 0.000
C2 0.0228(17) 0.0331(17) 0.0146(14) 0.000 0.0017(13) 0.000
C3 0.0304(12) 0.0304(12) 0.0157(14) 0.0004(9) -0.0004(9) -0.0038(14)
C1 0.027(2) 0.033(3) 0.0129(19) 0.000 0.000 0.000
C5 0.190(14) 0.094(11) 0.30(3) -0.002(9) -0.085(16) -0.003(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.214(4) . ?
O2 C4 1.309(4) . ?
O2 H2 0.84(2) . ?
C4 C2 1.502(4) . ?
C2 C3 1.536(3) 27_566 ?
C2 C3 1.536(3) . ?
C2 C1 1.535(4) . ?
C3 C2 1.536(3) 20_657 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 C2 1.535(4) 10_554 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 C5 1.09(3) 6_556 ?
C5 C5 1.928(6) 12_554 ?
C5 C5 1.928(6) 11_534 ?
C5 C5 1.25(4) 16 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 H2 111(5) . . ?
O1 C4 O2 122.5(3) . . ?
O1 C4 C2 123.1(3) . . ?
O2 C4 C2 114.4(3) . . ?
C4 C2 C3 109.15(18) . 27_566 ?
C4 C2 C3 109.15(18) . . ?
C4 C2 C1 110.6(3) . . ?
C3 C2 C3 109.0(2) . 27_566 ?
C1 C2 C3 109.45(16) . 27_566 ?
C1 C2 C3 109.45(16) . . ?
C2 C3 C2 109.9(3) 20_657 . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 20_657 . ?
C2 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 20_657 . ?
H3A C3 H3B 108.2 . . ?
C2 C1 C2 109.5(4) 10_554 . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 10_554 . ?
C2 C1 H1B 109.8 10_554 . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C5 C5 C5 110.3(17) 6_556 16 ?
C5 C5 C5 125.2(17) 16 11_534 ?
C5 C5 C5 37.6(15) 6_556 11_534 ?
C5 C5 C5 127(2) 6_556 12_554 ?
C5 C5 C5 155.5(7) 12_554 11_534 ?
C5 C5 C5 32.1(12) 16 12_554 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84(2) 1.78(2) 2.612(4) 177(8) 5_655
_shelx_res_file
;
pc_8_638_i41amd_200k.res created by SHELXL-2014/7
TITL pc_8_638_i41amd_200k_a.res in I4(1)/amd
REM Old TITL PC_8_638_I41amd_200K in I4(1)/amd
REM SHELXT solution in I4(1)/amd
REM R1 0.258, Rweak 0.007, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C7 O4
CELL 0.71073 16.429 16.429 7.358 90 90 90
ZERR 4 0.0026 0.0026 0.0012 0 0 0
LATT 2
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.25-Y,0.75+X,0.25+Z
SYMM 0.25+Y,0.25-X,0.75+Z
SYMM 0.5-X,+Y,0.5-Z
SYMM +X,-Y,-Z
SYMM 0.25+Y,0.75+X,0.25-Z
SYMM 0.25-Y,0.25-X,0.75-Z
SFAC C H O
UNIT 80.07 115.43 32
EQIV $1 1.5-X,+Y,0.5-Z
DFIX 0.82 O2 H2
L.S. 50
PLAN 20
SIZE 0.15 0.15 0.13
TEMP -73.15
HTAB O2 O1_$1
BOND $H
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.093500 3.570500
FVAR 0.43736
O1 3 0.650564 0.250000 0.224154 10.50000 0.03353 0.09506 =
0.01803 0.00000 0.00204 0.00000
O2 3 0.719977 0.250000 0.481802 10.50000 0.02880 0.10160 =
0.02411 0.00000 0.00087 0.00000
C4 1 0.651969 0.250000 0.389160 10.50000 0.02772 0.03679 =
0.01803 0.00000 -0.00016 0.00000
C2 1 0.576334 0.250000 0.503796 10.50000 0.02278 0.03311 =
0.01456 0.00000 0.00167 0.00000
C3 1 0.576113 0.326113 0.625000 10.50000 0.03041 0.03041 =
0.01574 0.00035 -0.00035 -0.00376
AFIX 23
H3A 2 0.625578 0.326636 0.701836 10.50000 -1.20000
H3B 2 0.576634 0.375578 0.548165 10.50000 -1.20000
AFIX 0
C1 1 0.500000 0.250000 0.383449 10.25000 0.02738 0.03274 =
0.01293 0.00000 0.00000 0.00000
AFIX 23
H1A 2 0.500000 0.298820 0.304578 10.25000 -1.20000
H1B 2 0.499999 0.201180 0.304578 10.25000 -1.20000
AFIX 0
C5 1 0.765299 0.019582 0.559946 0.75358 0.18987 0.09363 =
0.30284 -0.00155 -0.08522 -0.00284
H2 2 0.760297 0.250000 0.412634 10.50000 0.10418
HKLF 4
REM pc_8_638_i41amd_200k_a.res in I4(1)/amd
REM R1 = 0.0650 for 407 Fo > 4sig(Fo) and 0.0842 for all 554 data
REM 47 parameters refined using 1 restraints
END
WGHT 0.1038 3.5757
REM Highest difference peak 0.241, deepest hole -0.242, 1-sigma level 0.060
Q1 1 0.8494 0.0000 0.5000 10.50000 0.05 0.24
Q2 1 0.7703 0.0889 0.6223 11.00000 0.05 0.19
Q3 1 0.6106 0.2500 0.4597 10.50000 0.05 0.19
Q4 1 0.6955 0.2992 0.4300 11.00000 0.05 0.19
Q5 1 0.8479 0.1084 0.4032 11.00000 0.05 0.18
Q6 1 0.7480 0.0885 0.5076 11.00000 0.05 0.17
Q7 1 0.6678 0.1976 0.2823 11.00000 0.05 0.17
Q8 1 0.5000 0.3780 0.2980 10.50000 0.05 0.16
Q9 1 0.7692 0.0855 0.5035 11.00000 0.05 0.16
Q10 1 0.8451 0.0167 0.5762 11.00000 0.05 0.15
Q11 1 0.7298 0.2500 0.3050 10.50000 0.05 0.14
Q12 1 0.7240 0.2020 0.4091 11.00000 0.05 0.14
Q13 1 0.5467 0.2500 0.4447 10.50000 0.05 0.14
Q14 1 0.7909 0.0826 0.5033 11.00000 0.05 0.14
Q15 1 0.5000 0.2500 0.3180 10.25000 0.05 0.13
Q16 1 0.8503 0.0613 0.4986 11.00000 0.05 0.13
Q17 1 0.7869 0.2500 0.3619 10.50000 0.05 0.13
Q18 1 0.5000 0.3368 0.3963 10.50000 0.05 0.12
Q19 1 0.5943 0.2500 0.1470 10.50000 0.05 0.11
Q20 1 0.7644 0.0251 0.5156 11.00000 0.05 0.11
;
_shelx_res_checksum 58809
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_3-31_EtOH-cyclohexanone_publ
_database_code_depnum_ccdc_archive 'CCDC 1915304'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT922_TMA_3-31_EtOH-cyclohexanone_publ
;
PROBLEM: wR2 in the CIF and FCF Differ by ............... 0.0064 Check
RESPONSE: The following WGHT scheme was used during refinement:
'w=1/[\s^2^(Fo^2^)+(0.1529P)^2^+3.7273P] where P=(Fo^2^+2Fc^2^)/3'
;
# end Validation Reply Form
_audit_creation_date 2018-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6, C6 H10 O'
_chemical_formula_sum 'C15 H16 O7'
_chemical_formula_weight 308.28
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 27.254(3)
_cell_length_b 16.7260(16)
_cell_length_c 6.7365(6)
_cell_angle_alpha 90
_cell_angle_beta 100.207(3)
_cell_angle_gamma 90
_cell_volume 3022.3(5)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 4792
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.390
_cell_measurement_theta_min 2.436
_shelx_estimated_absorpt_T_max 0.995
_shelx_estimated_absorpt_T_min 0.991
_exptl_absorpt_coefficient_mu 0.109
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.5145
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0862 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.6902. The \l/2 correction factor is 0.00150.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.355
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1296
_exptl_crystal_size_max 0.085
_exptl_crystal_size_mid 0.058
_exptl_crystal_size_min 0.047
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0463
_diffrn_reflns_av_unetI/netI 0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 34
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 6
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 16923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.450
_diffrn_reflns_theta_min 1.435
_diffrn_ambient_temperature 100.0
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2261
_reflns_number_total 3117
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.767
_refine_diff_density_min -0.485
_refine_diff_density_rms 0.082
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 257
_refine_ls_number_reflns 3117
_refine_ls_number_restraints 116
_refine_ls_R_factor_all 0.0943
_refine_ls_R_factor_gt 0.0731
_refine_ls_restrained_S_all 1.121
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1529P)^2^+3.7273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2250
_refine_ls_wR_factor_ref 0.2492
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
At 1.5 times of:
All O(H) groups
2. Restrained distances
C13-C14 = C15-C14 = C10-C15 = C11-C10 = C12-C11 = C16-C11 = C13-C12 = C17-C16
= C17-C18 = C19-C18 = C19-C10
1.52 with sigma of 0.02
O9-C19
1.23 with sigma of 0.02
C10-C18
2.56 with sigma of 0.04
C17-C11
2.56 with sigma of 0.04
C15-C13
2.56 with sigma of 0.04
C12-C10
2.56 with sigma of 0.04
C19-C17
2.56 with sigma of 0.04
C10-O9 \\sim O9-C18
with sigma of 0.02
3. Restrained planarity
H5, O5, C8, O6, H6
with sigma of 0.01
4. Rigid body (RIGU) restrains
C13, O8, C14, C15, C10, C12, O7, C11, C19, C16, C18, C17, O9
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
Fixed Sof: H5(0.5) H6(0.5) O8(0.6) O7(0.25) C14(0.75) C15(0.75) H15A(0.75)
H15B(0.75) H10A(0.75) H10B(0.75) H11A(0.75) H11B(0.75) H11C(0.25) H11D(0.25)
C12(0.75) H12A(0.75) H12B(0.75) C13(0.75) H13A(0.75) H13B(0.75) C18(0.25)
H18A(0.25) H18B(0.25) C19(0.25) C17(0.25) H17A(0.25) H17B(0.25) C16(0.25)
H16A(0.25) H16B(0.25) O9(0.15)
6.a Secondary CH2 refined with riding coordinates:
C15(H15A,H15B), C10(H10A,H10B), C11(H11A,H11B), C11(H11C,H11D), C12(H12A,
H12B), C13(H13A,H13B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
C1(H1), C3(H3A), C5(H5A)
6.c Idealised tetrahedral OH refined as rotating group:
O2(H2), O3(H3), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30334(6) 0.32744(10) 0.3622(3) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.23521(6) 0.39558(10) 0.2201(3) 0.0301(5) Uani 1 1 d . . . . .
H2 H 0.2227 0.3496 0.2059 0.045 Uiso 1 1 calc GR . . . .
O3 O 0.23591(6) 0.68559(10) 0.2090(3) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.2230 0.7313 0.1981 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.30315(7) 0.75388(10) 0.3594(3) 0.0335(5) Uani 1 1 d . . . . .
O5 O 0.45521(7) 0.60751(10) 0.6428(3) 0.0347(5) Uani 1 1 d . . . . .
H5 H 0.4846 0.6004 0.7032 0.052 Uiso 0.5 1 calc GR . P . .
O6 O 0.45582(7) 0.47351(10) 0.6382(3) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.4852 0.4807 0.6986 0.044 Uiso 0.5 1 calc GR . P . .
C1 C 0.28170(9) 0.54060(13) 0.3100(3) 0.0216(5) Uani 1 1 d . . . . .
H1 H 0.2475 0.5405 0.2490 0.026 Uiso 1 1 calc R . . . .
C2 C 0.30713(9) 0.61243(13) 0.3534(3) 0.0221(5) Uani 1 1 d . . . . .
C3 C 0.35739(9) 0.61288(14) 0.4433(3) 0.0226(5) Uani 1 1 d . . . . .
H3A H 0.3746 0.6621 0.4722 0.027 Uiso 1 1 calc R . . . .
C4 C 0.38213(9) 0.54080(13) 0.4904(4) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.35720(9) 0.46847(13) 0.4467(3) 0.0213(5) Uani 1 1 d . . . . .
H5A H 0.3743 0.4193 0.4779 0.026 Uiso 1 1 calc R . . . .
C6 C 0.30701(9) 0.46885(13) 0.3571(3) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.28155(9) 0.69073(14) 0.3059(4) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.43476(9) 0.54069(13) 0.5974(4) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.28115(9) 0.39055(13) 0.3132(4) 0.0223(5) Uani 1 1 d . . . . .
O8 O 0.3407(5) 0.0427(6) 0.466(2) 0.192(5) Uani 0.6 1 d . U P A 1
O7 O 0.4349(9) 0.2514(14) 0.800(3) 0.148(7) Uani 0.25 1 d . U P B 2
C14 C 0.3785(4) 0.0880(5) 0.4798(13) 0.113(2) Uani 0.75 1 d D U P A 1
C15 C 0.3999(4) 0.1277(5) 0.6726(13) 0.110(3) Uani 0.75 1 d D U P A 1
H15A H 0.3738 0.1318 0.7575 0.132 Uiso 0.75 1 calc R . P A 1
H15B H 0.4273 0.0943 0.7457 0.132 Uiso 0.75 1 calc R . P A 1
C10 C 0.4184(3) 0.2045(4) 0.6443(11) 0.131(2) Uani 1 1 d D U . . .
H10A H 0.4441 0.2157 0.7646 0.157 Uiso 0.75 1 calc R . P B 1
H10B H 0.3906 0.2421 0.6501 0.157 Uiso 0.75 1 calc R . P B 1
C11 C 0.4398(3) 0.2281(5) 0.4715(11) 0.133(2) Uani 1 1 d D U . . .
H11A H 0.4408 0.2872 0.4623 0.160 Uiso 0.75 1 calc R . P C 1
H11B H 0.4744 0.2078 0.4857 0.160 Uiso 0.75 1 calc R . P C 1
H11C H 0.4189 0.2727 0.4077 0.160 Uiso 0.25 1 calc R . P D 2
H11D H 0.4727 0.2518 0.5274 0.160 Uiso 0.25 1 calc R . P D 2
C12 C 0.4104(3) 0.1964(5) 0.2964(13) 0.105(2) Uani 0.75 1 d D U P A 1
H12A H 0.4285 0.2057 0.1834 0.126 Uiso 0.75 1 calc R . P A 1
H12B H 0.3794 0.2283 0.2679 0.126 Uiso 0.75 1 calc R . P A 1
C13 C 0.3957(4) 0.1106(5) 0.2901(13) 0.125(3) Uani 0.75 1 d D U P A 1
H13A H 0.3686 0.1012 0.1738 0.149 Uiso 0.75 1 calc R . P A 1
H13B H 0.4245 0.0769 0.2725 0.149 Uiso 0.75 1 calc R . P A 1
C18 C 0.4391(16) 0.0650(14) 0.481(3) 0.145(10) Uani 0.25 1 d D U P B 2
H18A H 0.4622 0.0211 0.5323 0.174 Uiso 0.25 1 calc R . P B 2
H18B H 0.4063 0.0394 0.4338 0.174 Uiso 0.25 1 calc R . P B 2
C19 C 0.4326(13) 0.1119(11) 0.664(3) 0.125(7) Uani 0.25 1 d D U P B 2
C17 C 0.456(2) 0.0924(14) 0.294(5) 0.195(18) Uani 0.25 1 d D U P B 2
H17A H 0.4910 0.0791 0.2953 0.233 Uiso 0.25 1 calc R . P B 2
H17B H 0.4348 0.0696 0.1723 0.233 Uiso 0.25 1 calc R . P B 2
C16 C 0.4483(11) 0.1775(14) 0.309(3) 0.113(6) Uani 0.25 1 d D U P B 2
H16A H 0.4778 0.2012 0.2641 0.135 Uiso 0.25 1 calc R . P B 2
H16B H 0.4198 0.1891 0.1991 0.135 Uiso 0.25 1 calc R . P B 2
O9 O 0.4587(13) 0.0919(17) 0.831(4) 0.157(10) Uani 0.15 1 d D U P B 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0285(9) 0.0199(8) 0.0351(10) 0.0012(7) 0.0008(7) -0.0001(7)
O2 0.0242(9) 0.0233(9) 0.0395(11) 0.0018(7) -0.0032(8) -0.0031(7)
O3 0.0255(9) 0.0225(9) 0.0387(10) -0.0004(7) -0.0027(8) 0.0044(7)
O4 0.0303(10) 0.0213(9) 0.0437(11) -0.0036(7) -0.0074(8) 0.0029(7)
O5 0.0268(9) 0.0271(10) 0.0462(12) -0.0054(8) -0.0051(8) -0.0020(7)
O6 0.0242(9) 0.0274(9) 0.0349(10) 0.0034(7) 0.0000(7) 0.0029(7)
C1 0.0208(11) 0.0254(12) 0.0182(11) -0.0003(9) 0.0020(9) 0.0005(9)
C2 0.0237(12) 0.0214(11) 0.0204(11) -0.0006(8) 0.0021(9) 0.0011(9)
C3 0.0257(12) 0.0210(11) 0.0206(11) -0.0013(8) 0.0026(9) 0.0002(9)
C4 0.0219(12) 0.0241(11) 0.0196(11) -0.0005(8) 0.0035(9) 0.0010(9)
C5 0.0247(12) 0.0204(11) 0.0188(11) -0.0002(8) 0.0041(9) 0.0019(9)
C6 0.0234(12) 0.0223(12) 0.0186(11) 0.0001(8) 0.0042(9) -0.0003(9)
C7 0.0255(12) 0.0224(12) 0.0231(12) -0.0016(9) 0.0030(9) 0.0005(9)
C8 0.0239(12) 0.0219(11) 0.0234(12) -0.0015(9) 0.0031(9) -0.0005(9)
C9 0.0236(12) 0.0215(12) 0.0217(11) 0.0008(8) 0.0040(9) -0.0003(9)
O8 0.167(8) 0.131(8) 0.263(13) 0.014(6) -0.002(8) -0.014(6)
O7 0.174(17) 0.154(12) 0.124(9) -0.034(9) 0.046(10) -0.028(12)
C14 0.125(6) 0.086(5) 0.115(5) 0.017(4) -0.009(4) 0.000(4)
C15 0.120(6) 0.111(5) 0.110(5) 0.014(4) 0.055(5) -0.006(4)
C10 0.159(6) 0.132(5) 0.106(4) -0.004(4) 0.035(4) -0.020(5)
C11 0.153(6) 0.136(5) 0.117(4) 0.020(4) 0.041(4) 0.000(4)
C12 0.104(5) 0.105(5) 0.105(5) 0.023(4) 0.020(4) 0.028(4)
C13 0.162(8) 0.102(5) 0.103(5) -0.009(4) 0.006(5) 0.042(5)
C18 0.23(3) 0.117(11) 0.094(11) 0.010(8) 0.050(14) -0.011(12)
C19 0.161(19) 0.133(8) 0.088(10) 0.004(7) 0.043(11) -0.034(8)
C17 0.31(5) 0.159(12) 0.142(16) 0.035(9) 0.10(3) 0.017(13)
C16 0.096(16) 0.145(11) 0.101(10) 0.019(8) 0.029(10) 0.006(11)
O9 0.18(2) 0.195(19) 0.102(12) 0.016(10) 0.038(13) -0.028(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.232(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.300(3) . ?
O3 H3 0.8400 . ?
O3 C7 1.301(3) . ?
O4 C7 1.232(3) . ?
O5 H5 0.8400 . ?
O5 C8 1.262(3) . ?
O6 H6 0.8400 . ?
O6 C8 1.270(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.492(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.390(3) . ?
C4 C5 1.393(3) . ?
C4 C8 1.487(3) . ?
C5 H5A 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C9 1.492(3) . ?
O8 C14 1.269(14) . ?
O7 C10 1.32(2) . ?
C14 C15 1.483(11) . ?
C14 C13 1.485(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C10 1.406(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.447(8) . ?
C10 C19 1.597(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C12 1.408(10) . ?
C11 C16 1.436(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.489(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.500(17) . ?
C18 C17 1.479(18) . ?
C19 O9 1.264(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.443(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C7 O3 H3 109.5 . . ?
C8 O5 H5 109.5 . . ?
C8 O6 H6 109.5 . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.2(2) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 C7 121.1(2) . . ?
C3 C2 C7 118.3(2) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C8 119.9(2) . . ?
C5 C4 C8 119.6(2) . . ?
C4 C5 H5A 120.3 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 C9 120.9(2) . . ?
C5 C6 C9 118.3(2) . . ?
O3 C7 C2 114.7(2) . . ?
O4 C7 O3 124.6(2) . . ?
O4 C7 C2 120.6(2) . . ?
O5 C8 O6 124.6(2) . . ?
O5 C8 C4 117.6(2) . . ?
O6 C8 C4 117.8(2) . . ?
O1 C9 O2 124.7(2) . . ?
O1 C9 C6 120.5(2) . . ?
O2 C9 C6 114.8(2) . . ?
O8 C14 C15 121.2(11) . . ?
O8 C14 C13 117.7(11) . . ?
C15 C14 C13 120.3(8) . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C10 C15 C14 112.7(7) . . ?
C10 C15 H15A 109.1 . . ?
C10 C15 H15B 109.1 . . ?
O7 C10 C11 110.3(11) . . ?
O7 C10 C19 117.7(16) . . ?
C15 C10 H10A 106.2 . . ?
C15 C10 H10B 106.2 . . ?
C15 C10 C11 124.4(7) . . ?
H10A C10 H10B 106.4 . . ?
C11 C10 H10A 106.2 . . ?
C11 C10 H10B 106.2 . . ?
C11 C10 C19 101.8(10) . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
C10 C11 H11C 105.7 . . ?
C10 C11 H11D 105.7 . . ?
H11A C11 H11B 108.3 . . ?
H11C C11 H11D 106.1 . . ?
C12 C11 C10 108.7(7) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C16 C11 C10 126.6(12) . . ?
C16 C11 H11C 105.7 . . ?
C16 C11 H11D 105.7 . . ?
C11 C12 H12A 107.3 . . ?
C11 C12 H12B 107.3 . . ?
C11 C12 C13 119.9(7) . . ?
H12A C12 H12B 106.9 . . ?
C13 C12 H12A 107.3 . . ?
C13 C12 H12B 107.3 . . ?
C14 C13 C12 110.2(7) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
H18A C18 H18B 105.8 . . ?
C19 C18 H18A 105.0 . . ?
C19 C18 H18B 105.0 . . ?
C17 C18 H18A 105.0 . . ?
C17 C18 H18B 105.0 . . ?
C17 C18 C19 129(2) . . ?
C18 C19 C10 120.1(17) . . ?
O9 C19 C10 114.9(17) . . ?
O9 C19 C18 118(2) . . ?
C18 C17 H17A 111.7 . . ?
C18 C17 H17B 111.7 . . ?
H17A C17 H17B 109.4 . . ?
C16 C17 C18 101(2) . . ?
C16 C17 H17A 111.7 . . ?
C16 C17 H17B 111.7 . . ?
C11 C16 C17 132(2) . . ?
C11 C16 H16A 104.1 . . ?
C11 C16 H16B 104.1 . . ?
C17 C16 H16A 104.1 . . ?
C17 C16 H16B 104.1 . . ?
H16A C16 H16B 105.5 . . ?
_shelx_res_file
;
pc_ht_1_i331_100k.res created by SHELXL-2014/7
TITL pc_ht_1_i331_100k_a.res in C2/c
REM Old TITL PC_HT_1_i331_100K in C2/c
REM SHELXT solution in C2/c
REM R1 0.161, Rweak 0.002, Alpha 0.076, Orientation as input
REM Formula found by SHELXT: C13 O6
CELL 0.71073 27.2542 16.726 6.7365 90 100.207 90
ZERR 8 0.0027 0.0016 0.0006 0 0.003 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O
UNIT 120 128 56
DFIX 1.52 C13 C14 C15 C14 C10 C15 C11 C10 C12 C11 C16 C11 C13 C12 C17 C16 =
C17 C18 C19 C18 C19 C10
DFIX 1.23 O9 C19
SADI C10 O9 O9 C18
DANG 2.56 C10 C18
DANG 2.56 C17 C11
DANG 2.56 C15 C13
DANG 2.56 C12 C10
DANG 2.56 C19 C17
FLAT 0.01 H5 O5 C8 O6 H6
RIGU C13 O8 C14 C15 C10 C12 O7 C11 C19 C16 C18 C17 O9
L.S. 50
PLAN 20
SIZE 0.047 0.058 0.085
TEMP -173.15
BOND $H
list 4
fmap 2
acta
OMIT 2 2 2
REM
REM
REM
WGHT 0.152900 3.727300
FVAR 0.34623
O1 3 0.303341 0.327444 0.362172 11.00000 0.02845 0.01990 =
0.03507 0.00116 0.00079 -0.00006
O2 3 0.235206 0.395577 0.220105 11.00000 0.02421 0.02331 =
0.03945 0.00179 -0.00318 -0.00305
AFIX 147
H2 2 0.222665 0.349605 0.205942 11.00000 -1.50000
AFIX 0
O3 3 0.235912 0.685593 0.209000 11.00000 0.02552 0.02249 =
0.03870 -0.00044 -0.00267 0.00439
AFIX 147
H3 2 0.222962 0.731314 0.198055 11.00000 -1.50000
AFIX 0
O4 3 0.303148 0.753877 0.359435 11.00000 0.03029 0.02135 =
0.04369 -0.00364 -0.00742 0.00291
O5 3 0.455208 0.607510 0.642790 11.00000 0.02680 0.02706 =
0.04616 -0.00544 -0.00508 -0.00203
AFIX 147
H5 2 0.484589 0.600356 0.703196 10.50000 -1.50000
AFIX 0
O6 3 0.455822 0.473513 0.638170 11.00000 0.02421 0.02738 =
0.03485 0.00340 0.00002 0.00294
AFIX 147
H6 2 0.485194 0.480720 0.698610 10.50000 -1.50000
AFIX 0
C1 1 0.281698 0.540603 0.309981 11.00000 0.02082 0.02535 =
0.01817 -0.00028 0.00197 0.00050
AFIX 43
H1 2 0.247485 0.540528 0.248980 11.00000 -1.20000
AFIX 0
C2 1 0.307126 0.612426 0.353353 11.00000 0.02373 0.02144 =
0.02036 -0.00064 0.00212 0.00106
C3 1 0.357388 0.612881 0.443341 11.00000 0.02569 0.02102 =
0.02058 -0.00127 0.00261 0.00023
AFIX 43
H3A 2 0.374560 0.662106 0.472227 11.00000 -1.20000
AFIX 0
C4 1 0.382128 0.540804 0.490374 11.00000 0.02191 0.02411 =
0.01965 -0.00050 0.00351 0.00102
C5 1 0.357198 0.468472 0.446745 11.00000 0.02474 0.02037 =
0.01878 -0.00017 0.00406 0.00191
AFIX 43
H5A 2 0.374266 0.419288 0.477854 11.00000 -1.20000
AFIX 0
C6 1 0.307010 0.468846 0.357080 11.00000 0.02341 0.02228 =
0.01863 0.00006 0.00425 -0.00029
C7 1 0.281550 0.690733 0.305906 11.00000 0.02546 0.02238 =
0.02306 -0.00156 0.00300 0.00052
C8 1 0.434764 0.540694 0.597382 11.00000 0.02390 0.02192 =
0.02343 -0.00150 0.00307 -0.00050
C9 1 0.281151 0.390551 0.313238 11.00000 0.02364 0.02150 =
0.02166 0.00077 0.00401 -0.00028
PART 1
O8 3 0.340747 0.042662 0.466163 10.60000 0.16697 0.13104 =
0.26335 0.01410 -0.00183 -0.01403
PART 0
PART 2
O7 3 0.434902 0.251373 0.800016 10.25000 0.17401 0.15351 =
0.12435 -0.03425 0.04585 -0.02840
PART 0
PART 1
C14 1 0.378545 0.087960 0.479762 10.75000 0.12532 0.08633 =
0.11474 0.01727 -0.00937 0.00023
C15 1 0.399900 0.127704 0.672603 10.75000 0.12030 0.11134 =
0.11016 0.01359 0.05468 -0.00612
AFIX 23
H15A 2 0.373842 0.131788 0.757505 10.75000 -1.20000
H15B 2 0.427261 0.094312 0.745652 10.75000 -1.20000
AFIX 0
PART 0
C10 1 0.418396 0.204532 0.644270 11.00000 0.15896 0.13205 =
0.10613 -0.00362 0.03544 -0.02008
PART 1
AFIX 23
H10A 2 0.444056 0.215697 0.764597 10.75000 -1.20000
H10B 2 0.390614 0.242094 0.650096 10.75000 -1.20000
AFIX 0
PART 0
C11 1 0.439846 0.228147 0.471532 11.00000 0.15264 0.13624 =
0.11678 0.01985 0.04129 0.00000
PART 1
AFIX 23
H11A 2 0.440790 0.287183 0.462332 10.75000 -1.20000
H11B 2 0.474396 0.207765 0.485718 10.75000 -1.20000
AFIX 23
PART 0
PART 2
H11C 2 0.418874 0.272719 0.407745 10.25000 -1.20000
H11D 2 0.472694 0.251788 0.527429 10.25000 -1.20000
AFIX 0
PART 0
PART 1
C12 1 0.410444 0.196373 0.296396 10.75000 0.10426 0.10506 =
0.10515 0.02261 0.02027 0.02796
AFIX 23
H12A 2 0.428536 0.205664 0.183368 10.75000 -1.20000
H12B 2 0.379421 0.228342 0.267936 10.75000 -1.20000
AFIX 0
C13 1 0.395703 0.110576 0.290135 10.75000 0.16229 0.10186 =
0.10291 -0.00908 0.00575 0.04229
AFIX 23
H13A 2 0.368579 0.101161 0.173802 10.75000 -1.20000
H13B 2 0.424504 0.076927 0.272499 10.75000 -1.20000
AFIX 0
PART 0
PART 2
C18 1 0.439053 0.065017 0.480587 10.25000 0.23215 0.11713 =
0.09353 0.00977 0.04989 -0.01066
AFIX 23
H18A 2 0.462160 0.021089 0.532317 10.25000 -1.20000
H18B 2 0.406287 0.039430 0.433837 10.25000 -1.20000
AFIX 0
C19 1 0.432641 0.111920 0.663977 10.25000 0.16072 0.13290 =
0.08786 0.00361 0.04279 -0.03430
C17 1 0.455613 0.092443 0.294459 10.25000 0.30680 0.15854 =
0.14160 0.03543 0.10365 0.01699
AFIX 23
H17A 2 0.491035 0.079086 0.295272 10.25000 -1.20000
H17B 2 0.434775 0.069628 0.172261 10.25000 -1.20000
AFIX 0
C16 1 0.448250 0.177529 0.308601 10.25000 0.09635 0.14528 =
0.10066 0.01918 0.02880 0.00551
AFIX 23
H16A 2 0.477796 0.201180 0.264136 10.25000 -1.20000
H16B 2 0.419816 0.189147 0.199070 10.25000 -1.20000
AFIX 0
O9 3 0.458705 0.091883 0.830831 10.15000 0.17924 0.19544 =
0.10174 0.01619 0.03821 -0.02754
HKLF 4
REM pc_ht_1_i331_100k_a.res in C2/c
REM R1 = 0.0731 for 2261 Fo > 4sig(Fo) and 0.0943 for all 3117 data
REM 257 parameters refined using 116 restraints
END
WGHT 0.1533 3.5663
REM Highest difference peak 0.767, deepest hole -0.485, 1-sigma level 0.082
Q1 1 0.4703 0.0447 0.8392 11.00000 0.05 0.77
Q2 1 0.3549 0.0575 0.1430 11.00000 0.05 0.69
Q3 1 0.4477 0.0739 0.6839 11.00000 0.05 0.50
Q4 1 0.3731 0.1399 0.5916 11.00000 0.05 0.50
Q5 1 0.4591 0.1286 0.3685 11.00000 0.05 0.50
Q6 1 0.4253 0.1344 0.2901 11.00000 0.05 0.45
Q7 1 0.4524 0.0626 0.4867 11.00000 0.05 0.32
Q8 1 0.2977 0.6390 0.3317 11.00000 0.05 0.29
Q9 1 0.2957 0.4462 0.3322 11.00000 0.05 0.26
Q10 1 0.4859 0.0231 0.6188 11.00000 0.05 0.26
Q11 1 0.4916 0.0148 0.5107 11.00000 0.05 0.24
Q12 1 0.4705 0.0597 0.1726 11.00000 0.05 0.23
Q13 1 0.4066 0.2208 0.3770 11.00000 0.05 0.21
Q14 1 0.4119 0.0936 0.6188 11.00000 0.05 0.21
Q15 1 0.2821 0.7975 0.3727 11.00000 0.05 0.20
Q16 1 0.2977 0.5825 0.3138 11.00000 0.05 0.20
Q17 1 0.4098 0.5398 0.5180 11.00000 0.05 0.20
Q18 1 0.3418 0.1518 0.5142 11.00000 0.05 0.19
Q19 1 0.3827 0.0983 0.8748 11.00000 0.05 0.17
Q20 1 0.3820 0.1601 0.4415 11.00000 0.05 0.17
;
_shelx_res_checksum 17080
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_2-33_Pentane_Activated_C2c_200K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915307'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT602_TMA_2-33_Pentane_Activated_C2c_200K_publ
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: There are large 1-D voids in the crystal structure which contain
no ordered electron density.
;
_vrf_PLAT049_TMA_2-33_Pentane_Activated_C2c_200K_publ
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 ......... 0.8872 Check
RESPONSE: There are large 1-D voids in the crystal structure which contain
no ordered electron density, accounting a crystal density < 1 g/cm3.
;
# end Validation Reply Form
_audit_creation_date 2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6'
_chemical_formula_sum 'C9 H6 O6'
_chemical_formula_weight 210.14
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 12
_space_group_name_H-M_alt 'C 1 2/m 1'
_space_group_name_Hall '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 26.075(2)
_cell_length_b 16.4837(12)
_cell_length_c 3.6749(3)
_cell_angle_alpha 90
_cell_angle_beta 95.076(2)
_cell_angle_gamma 90
_cell_volume 1573.3(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3425
_cell_measurement_temperature 200
_cell_measurement_theta_max 26.318
_cell_measurement_theta_min 2.471
_shelx_estimated_absorpt_T_max 0.993
_shelx_estimated_absorpt_T_min 0.989
_exptl_absorpt_coefficient_mu 0.077
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4499
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0920 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.6036. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 0.887
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description hexagonal
_exptl_crystal_F_000 432
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.09
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0430
_diffrn_reflns_av_unetI/netI 0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max 31
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 3
_diffrn_reflns_limit_l_min -4
_diffrn_reflns_number 8938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.686
_diffrn_reflns_theta_min 2.471
_diffrn_ambient_temperature 200
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1324
_reflns_number_total 1723
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.209
_refine_diff_density_min -0.230
_refine_diff_density_rms 0.034
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 75
_refine_ls_number_reflns 1723
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0547
_refine_ls_R_factor_gt 0.0406
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.2903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1101
_refine_ls_wR_factor_ref 0.1206
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All O(H) groups
2. Others
Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
C3(H3), C5(H5)
3.b Idealised tetrahedral OH refined as rotating group:
O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45408(4) 0.56771(6) 0.8196(3) 0.0555(3) Uani 1 1 d . . . . .
H1 H 0.4848 0.5606 0.9035 0.083 Uiso 0.5 1 calc GR . . . .
O2 O 0.30489(4) 0.28432(5) 0.2673(3) 0.0534(3) Uani 1 1 d . . . . .
H2 H 0.2882 0.2439 0.1835 0.080 Uiso 1 1 calc GR . . . .
O3 O 0.24020(3) 0.35097(6) -0.0406(3) 0.0502(3) Uani 1 1 d . . . . .
C1 C 0.43358(6) 0.5000 0.7390(5) 0.0355(4) Uani 1 2 d S T P . .
C2 C 0.38121(6) 0.5000 0.5399(4) 0.0337(4) Uani 1 2 d S T P . .
C3 C 0.35689(5) 0.42658(7) 0.4486(3) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.3736 0.3767 0.5117 0.042 Uiso 1 1 calc R . . . .
C4 C 0.30786(4) 0.42702(7) 0.2640(3) 0.0341(3) Uani 1 1 d . . . . .
C5 C 0.28330(6) 0.5000 0.1725(4) 0.0342(4) Uani 1 2 d S T P . .
H5 H 0.2498 0.5000 0.0476 0.041 Uiso 1 2 calc RS T P . .
C6 C 0.28199(5) 0.34918(7) 0.1551(3) 0.0373(3) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0394(5) 0.0516(6) 0.0708(7) -0.0006(5) -0.0208(5) -0.0069(4)
O2 0.0536(6) 0.0341(5) 0.0679(7) -0.0003(4) -0.0200(5) -0.0008(4)
O3 0.0442(5) 0.0431(5) 0.0589(6) -0.0013(4) -0.0198(4) -0.0052(4)
C1 0.0320(8) 0.0383(9) 0.0349(8) 0.000 -0.0039(7) 0.000
C2 0.0298(8) 0.0397(8) 0.0305(8) 0.000 -0.0041(6) 0.000
C3 0.0337(6) 0.0358(6) 0.0332(6) 0.0011(5) -0.0040(5) 0.0026(4)
C4 0.0338(6) 0.0358(6) 0.0315(6) -0.0007(5) -0.0038(5) -0.0011(4)
C5 0.0298(8) 0.0390(8) 0.0324(8) 0.000 -0.0058(6) 0.000
C6 0.0354(6) 0.0353(6) 0.0392(6) -0.0001(5) -0.0069(5) 0.0000(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.2615(12) . ?
O2 H2 0.8400 . ?
O2 C6 1.2753(14) . ?
O3 C6 1.2516(15) . ?
C1 O1 1.2615(12) 6_565 ?
C1 C2 1.491(2) . ?
C2 C3 1.3934(14) . ?
C2 C3 1.3934(14) 6_565 ?
C3 H3 0.9500 . ?
C3 C4 1.3933(16) . ?
C4 C5 1.3901(14) . ?
C4 C6 1.4878(16) . ?
C5 C4 1.3902(14) 6_565 ?
C5 H5 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
O1 C1 O1 124.45(15) . 6_565 ?
O1 C1 C2 117.77(8) . . ?
O1 C1 C2 117.77(8) 6_565 . ?
C3 C2 C1 119.72(7) 6_565 . ?
C3 C2 C1 119.71(7) . . ?
C3 C2 C3 120.57(15) 6_565 . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.42(11) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C6 120.08(10) . . ?
C5 C4 C3 120.36(11) . . ?
C5 C4 C6 119.54(11) . . ?
C4 C5 C4 119.86(15) . 6_565 ?
C4 C5 H5 120.1 6_565 . ?
C4 C5 H5 120.1 . . ?
O2 C6 C4 116.60(10) . . ?
O3 C6 O2 124.37(11) . . ?
O3 C6 C4 119.02(10) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.84 1.82 2.6325(17) 163.1 2_657
O2 H2 O3 0.84 1.79 2.6222(13) 171.5 7
_shelx_res_file
;
pc_ht_1_i233_pentane_200k.res created by SHELXL-2014/7
TITL pc_ht_1_i233_pentane_200k_a.res in C2/m
REM Old TITL PC_HT_1_i233_pentane_200K in C2/m #12
REM SHELXT solution in C2/m
REM R1 0.169, Rweak 0.005, Alpha 0.043, Orientation as input
REM Formula found by SHELXT: C9 O6
CELL 0.71073 26.0746 16.4837 3.6749 90 95.076 90
ZERR 4 0.002 0.0012 0.0003 0 0.002 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O
UNIT 36 24 24
EQIV $1 0.5-X,0.5-Y,-Z
EQIV $2 1-X,+Y,2-Z
L.S. 20
PLAN 20
SIZE 0.09 0.14 0.15
TEMP -73.15
HTAB O2 O3_$1
HTAB O1 O1_$2
BOND $H
list 4
fmap 2 53
acta
OMIT 2 0 0
OMIT 1 1 0
REM
REM
REM
WGHT 0.063300 0.290300
FVAR 0.77772
O1 3 0.454080 0.567713 0.819642 11.00000 0.03943 0.05158 =
0.07077 -0.00063 -0.02080 -0.00687
AFIX 147
H1 2 0.484775 0.560625 0.903532 10.50000 -1.50000
AFIX 0
O2 3 0.304888 0.284317 0.267291 11.00000 0.05363 0.03410 =
0.06794 -0.00033 -0.02004 -0.00081
AFIX 147
H2 2 0.288152 0.243891 0.183450 11.00000 -1.50000
AFIX 0
O3 3 0.240202 0.350974 -0.040623 11.00000 0.04418 0.04315 =
0.05891 -0.00133 -0.01982 -0.00524
C1 1 0.433581 0.500000 0.738966 10.50000 0.03198 0.03833 =
0.03493 0.00000 -0.00392 0.00000
C2 1 0.381208 0.500000 0.539927 10.50000 0.02980 0.03970 =
0.03045 0.00000 -0.00414 0.00000
C3 1 0.356889 0.426581 0.448623 11.00000 0.03372 0.03579 =
0.03317 0.00106 -0.00404 0.00258
AFIX 43
H3 2 0.373592 0.376668 0.511717 11.00000 -1.20000
AFIX 0
C4 1 0.307861 0.427016 0.263983 11.00000 0.03382 0.03583 =
0.03148 -0.00066 -0.00382 -0.00112
C5 1 0.283300 0.500000 0.172457 10.50000 0.02978 0.03898 =
0.03236 0.00000 -0.00579 0.00000
AFIX 43
H5 2 0.249800 0.500000 0.047629 10.50000 -1.20000
AFIX 0
C6 1 0.281989 0.349182 0.155055 11.00000 0.03545 0.03535 =
0.03920 -0.00009 -0.00690 -0.00001
HKLF 4
REM pc_ht_1_i233_pentane_200k_a.res in C2/m
REM R1 = 0.0406 for 1324 Fo > 4sig(Fo) and 0.0547 for all 1723 data
REM 75 parameters refined using 0 restraints
END
WGHT 0.0633 0.2903
REM Highest difference peak 0.209, deepest hole -0.230, 1-sigma level 0.034
Q1 1 0.2989 0.3947 0.2079 11.00000 0.05 0.21
Q2 1 0.3991 0.5000 0.6060 10.50000 0.05 0.19
Q3 1 0.3212 0.4240 0.4076 11.00000 0.05 0.14
Q4 1 0.2247 0.3098 -0.1268 11.00000 0.05 0.14
Q5 1 0.2998 0.4595 0.1773 11.00000 0.05 0.12
Q6 1 0.3634 0.4603 0.5248 11.00000 0.05 0.12
Q7 1 0.3327 0.4274 0.2816 11.00000 0.05 0.12
Q8 1 0.4798 0.5796 0.9272 11.00000 0.05 0.12
Q9 1 0.3738 0.4672 0.4498 11.00000 0.05 0.11
Q10 1 0.4627 0.5404 0.6689 11.00000 0.05 0.10
Q11 1 0.3647 0.2597 0.4605 11.00000 0.05 0.09
Q12 1 0.4635 0.7458 0.8363 11.00000 0.05 0.09
Q13 1 0.3980 0.3356 0.5704 11.00000 0.05 0.08
Q14 1 0.4541 0.6724 0.8120 11.00000 0.05 0.08
Q15 1 0.4436 0.6594 0.7782 11.00000 0.05 0.08
Q16 1 0.3206 0.2583 0.5870 11.00000 0.05 0.08
Q17 1 0.2403 0.5000 0.1675 10.50000 0.05 0.08
Q18 1 0.1853 0.4180 -0.2345 11.00000 0.05 0.08
Q19 1 0.2789 0.4598 0.5449 11.00000 0.05 0.07
Q20 1 0.2346 0.4012 0.3600 11.00000 0.05 0.07
;
_shelx_res_checksum 98835
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_2-33_Pentane_Activated_C2c_350K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915306'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT602_TMA_2-33_Pentane_Activated_C2c_350K_publ
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: There are large 1-D voids in the crystal structure which contain
no ordered electron density.
;
_vrf_PLAT049_TMA_2-33_Pentane_Activated_C2c_350K_publ
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 ......... 0.8645 Check
RESPONSE: There are large 1-D voids in the crystal structure which contain
no ordered electron density, accounting a crystal density < 1 g/cm3.
;
# end Validation Reply Form
_audit_creation_date 2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6'
_chemical_formula_sum 'C9 H6 O6'
_chemical_formula_weight 210.14
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 12
_space_group_name_H-M_alt 'C 1 2/m 1'
_space_group_name_Hall '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 26.240(5)
_cell_length_b 16.529(3)
_cell_length_c 3.7452(7)
_cell_angle_alpha 90
_cell_angle_beta 96.283(6)
_cell_angle_gamma 90
_cell_volume 1614.6(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3253
_cell_measurement_temperature 350
_cell_measurement_theta_max 25.796
_cell_measurement_theta_min 2.465
_shelx_estimated_absorpt_T_max 0.993
_shelx_estimated_absorpt_T_min 0.989
_exptl_absorpt_coefficient_mu 0.075
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4607
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0824 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.6181. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 0.864
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description hexagonal
_exptl_crystal_F_000 432
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.09
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0379
_diffrn_reflns_av_unetI/netI 0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 31
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 3
_diffrn_reflns_limit_l_min -4
_diffrn_reflns_number 9783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.472
_diffrn_reflns_theta_min 2.464
_diffrn_ambient_temperature 350
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1183
_reflns_number_total 1731
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution ?
_refine_diff_density_max 0.148
_refine_diff_density_min -0.158
_refine_diff_density_rms 0.026
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 75
_refine_ls_number_reflns 1731
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0622
_refine_ls_R_factor_gt 0.0423
_refine_ls_restrained_S_all 1.020
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.2603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1190
_refine_ls_wR_factor_ref 0.1342
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All O(H) groups
2. Others
Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
C3(H3), C5(H5)
3.b Idealised tetrahedral OH refined as rotating group:
O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45376(4) 0.56714(6) 0.8205(4) 0.0937(5) Uani 1 1 d . . . . .
H1 H 0.4837 0.5600 0.9032 0.141 Uiso 0.5 1 calc GR . . . .
O2 O 0.30475(4) 0.28517(6) 0.2582(4) 0.0960(4) Uani 1 1 d . . . . .
H2 H 0.2893 0.2462 0.1635 0.144 Uiso 1 1 calc GR . . . .
O3 O 0.23986(4) 0.35158(7) -0.0385(3) 0.0904(4) Uani 1 1 d . . . . .
C1 C 0.43317(7) 0.5000 0.7387(5) 0.0624(5) Uani 1 2 d S T P . .
C2 C 0.38097(7) 0.5000 0.5387(5) 0.0574(5) Uani 1 2 d S T P . .
C3 C 0.35674(5) 0.42702(8) 0.4468(4) 0.0602(4) Uani 1 1 d . . . . .
H3 H 0.3731 0.3783 0.5091 0.072 Uiso 1 1 calc R . . . .
C4 C 0.30778(5) 0.42719(8) 0.2608(4) 0.0590(4) Uani 1 1 d . . . . .
C5 C 0.28344(7) 0.5000 0.1686(5) 0.0597(5) Uani 1 2 d S T P . .
H5 H 0.2507 0.5000 0.0448 0.072 Uiso 1 2 calc RS T P . .
C6 C 0.28211(5) 0.34957(8) 0.1527(4) 0.0662(4) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0638(7) 0.0787(8) 0.1280(11) -0.0011(6) -0.0373(7) -0.0084(5)
O2 0.0882(8) 0.0564(6) 0.1315(10) -0.0011(6) -0.0416(7) -0.0019(5)
O3 0.0746(7) 0.0678(7) 0.1175(9) -0.0018(6) -0.0405(6) -0.0080(5)
C1 0.0518(10) 0.0611(11) 0.0700(12) 0.000 -0.0120(9) 0.000
C2 0.0482(9) 0.0614(10) 0.0592(10) 0.000 -0.0094(8) 0.000
C3 0.0544(7) 0.0581(7) 0.0644(8) 0.0009(6) -0.0102(6) 0.0038(6)
C4 0.0544(7) 0.0577(8) 0.0613(8) -0.0011(6) -0.0101(6) -0.0025(6)
C5 0.0495(9) 0.0633(11) 0.0621(11) 0.000 -0.0128(8) 0.000
C6 0.0595(8) 0.0567(8) 0.0771(9) -0.0008(7) -0.0170(7) -0.0006(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.2574(13) . ?
O2 H2 0.8200 . ?
O2 C6 1.2613(16) . ?
O3 C6 1.2528(16) . ?
C1 O1 1.2574(13) 6_565 ?
C1 C2 1.487(2) . ?
C2 C3 1.3892(16) . ?
C2 C3 1.3892(16) 6_565 ?
C3 H3 0.9300 . ?
C3 C4 1.3929(18) . ?
C4 C5 1.3882(15) . ?
C4 C6 1.4845(18) . ?
C5 C4 1.3882(16) 6_565 ?
C5 H5 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
O1 C1 O1 123.91(17) . 6_565 ?
O1 C1 C2 118.04(9) 6_565 . ?
O1 C1 C2 118.04(9) . . ?
C3 C2 C1 119.74(8) . . ?
C3 C2 C1 119.74(8) 6_565 . ?
C3 C2 C3 120.52(16) 6_565 . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.63(13) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C6 120.06(12) . . ?
C5 C4 C3 120.00(13) . . ?
C5 C4 C6 119.92(12) . . ?
C4 C5 C4 120.22(16) . 6_565 ?
C4 C5 H5 119.9 . . ?
C4 C5 H5 119.9 6_565 . ?
O2 C6 C4 117.38(12) . . ?
O3 C6 O2 123.95(13) . . ?
O3 C6 C4 118.66(11) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.82 1.85 2.642(2) 163.4 2_657
O2 H2 O3 0.82 1.83 2.6354(15) 168.0 7
_shelx_res_file
;
pc_ht_1_i233_pentane_activated.res created by SHELXL-2014/7
TITL PC_HT_1_i233_pentane_activated.res in C2/m
REM Old TITL PC_HT_1_i233_pentane_200K in C2/m #12
REM SHELXT solution in C2/m
REM R1 0.169, Rweak 0.005, Alpha 0.043, Orientation as input
REM Formula found by SHELXT: C9 O6
CELL 0.71073 26.24 16.5291 3.7452 90 96.283 90
ZERR 8 0.0053 0.0033 0.0007 0 0.006 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O
UNIT 36 24 24
EQIV $1 0.5-X,0.5-Y,-Z
EQIV $2 1-X,+Y,2-Z
L.S. 20
PLAN 20
SIZE 0.09 0.14 0.15
TEMP 76.85
HTAB O2 O3_$1
HTAB O1 O1_$2
BOND $H
list 4
fmap 2 53
acta
OMIT 2 0 0
OMIT 1 1 0
REM
REM
REM
WGHT 0.065400 0.260300
FVAR 0.81303
O1 3 0.453757 0.567137 0.820539 11.00000 0.06382 0.07869 =
0.12802 -0.00112 -0.03729 -0.00839
AFIX 147
H1 2 0.483663 0.560018 0.903233 10.50000 -1.50000
AFIX 0
O2 3 0.304750 0.285166 0.258195 11.00000 0.08823 0.05637 =
0.13150 -0.00112 -0.04158 -0.00191
AFIX 147
H2 2 0.289315 0.246241 0.163468 11.00000 -1.50000
AFIX 0
O3 3 0.239856 0.351584 -0.038540 11.00000 0.07458 0.06776 =
0.11746 -0.00177 -0.04054 -0.00799
C1 1 0.433166 0.500000 0.738716 10.50000 0.05180 0.06113 =
0.07003 0.00000 -0.01203 0.00000
C2 1 0.380972 0.500000 0.538747 10.50000 0.04825 0.06138 =
0.05916 0.00000 -0.00942 0.00000
C3 1 0.356743 0.427024 0.446782 11.00000 0.05444 0.05811 =
0.06443 0.00087 -0.01024 0.00381
AFIX 43
H3 2 0.373122 0.378334 0.509070 11.00000 -1.20000
AFIX 0
C4 1 0.307779 0.427187 0.260756 11.00000 0.05439 0.05774 =
0.06133 -0.00110 -0.01010 -0.00253
C5 1 0.283442 0.500000 0.168647 10.50000 0.04947 0.06335 =
0.06208 0.00000 -0.01284 0.00000
AFIX 43
H5 2 0.250725 0.499999 0.044820 10.50000 -1.20000
AFIX 0
C6 1 0.282108 0.349573 0.152722 11.00000 0.05949 0.05666 =
0.07714 -0.00082 -0.01701 -0.00056
HKLF 4
REM PC_HT_1_i233_pentane_activated.res in C2/m
REM R1 = 0.0423 for 1183 Fo > 4sig(Fo) and 0.0622 for all 1731 data
REM 75 parameters refined using 0 restraints
END
WGHT 0.0666 0.2507
REM Highest difference peak 0.148, deepest hole -0.158, 1-sigma level 0.026
Q1 1 0.2224 0.3081 -0.1193 11.00000 0.05 0.15
Q2 1 0.2982 0.3999 0.2112 11.00000 0.05 0.14
Q3 1 0.3937 0.5000 0.6157 10.50000 0.05 0.13
Q4 1 0.4643 0.5406 0.6445 11.00000 0.05 0.12
Q5 1 0.4821 0.5770 0.9402 11.00000 0.05 0.12
Q6 1 0.3015 0.4557 0.2095 11.00000 0.05 0.10
Q7 1 0.3799 0.3563 0.5524 11.00000 0.05 0.09
Q8 1 0.4398 0.6568 0.7394 11.00000 0.05 0.09
Q9 1 0.3787 0.5190 0.4574 11.00000 0.05 0.08
Q10 1 0.2255 0.3528 0.1898 11.00000 0.05 0.08
Q11 1 0.2474 0.5000 -0.0716 10.50000 0.05 0.07
Q12 1 0.4499 0.5571 0.8747 11.00000 0.05 0.06
Q13 1 0.4574 0.6688 0.8338 11.00000 0.05 0.06
Q14 1 0.2081 0.4202 -0.1584 11.00000 0.05 0.06
Q15 1 0.3485 0.5000 0.7476 10.50000 0.05 0.06
Q16 1 0.2124 0.4297 -0.1282 11.00000 0.05 0.06
Q17 1 0.2280 0.5000 0.1964 10.50000 0.05 0.06
Q18 1 0.4430 0.5400 0.9939 11.00000 0.05 0.06
Q19 1 0.3567 0.5000 0.8557 10.50000 0.05 0.05
Q20 1 0.3571 0.2750 0.4645 11.00000 0.05 0.05
;
_shelx_res_checksum 38008
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_7-35_Dioxane-1-3-dimethoxybenzene_C2m_100K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915308'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2019-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O0, 7.5(O)'
_chemical_formula_sum 'C9 H6 O13.50'
_chemical_formula_weight 330.14
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 12
_space_group_name_H-M_alt 'C 1 2/m 1'
_space_group_name_Hall '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 25.869(4)
_cell_length_b 16.419(3)
_cell_length_c 3.6060(6)
_cell_angle_alpha 90
_cell_angle_beta 93.617(4)
_cell_angle_gamma 90
_cell_volume 1528.6(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 5675
_cell_measurement_temperature 100
_cell_measurement_theta_max 27.495
_cell_measurement_theta_min 2.481
_shelx_estimated_absorpt_T_max 0.987
_shelx_estimated_absorpt_T_min 0.976
_exptl_absorpt_coefficient_mu 0.143
_exptl_absorpt_correction_T_max 0.745552
_exptl_absorpt_correction_T_min 0.461222
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
Final HKLF 4 output contains 16286 reflections, Rint = 0.0561
(11151 with I > 3sig(I), Rint = 0.0547)
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.435
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 672
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.09
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents ?
_diffrn_reflns_av_unetI/netI 0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max 32
_diffrn_reflns_limit_h_min -31
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 4
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 1664
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 2.481
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1533
_reflns_number_total 1664
_reflns_special_details
;
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution ?
_refine_diff_density_max 0.317
_refine_diff_density_min -0.415
_refine_diff_density_rms 0.072
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 137
_refine_ls_number_reflns 1664
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0727
_refine_ls_R_factor_gt 0.0688
_refine_ls_restrained_S_all 1.069
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1231P)^2^+2.1499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1992
_refine_ls_wR_factor_ref 0.2049
_refine_special_details
;
Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.930(4)
0.070(4)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups
3. Restrained distances
O2-H2
0.83 with sigma of 0.01
4. Others
Fixed Sof: O1S(0.25) O9S(0.5) O2S(0.25) O8S(0.5) O3S(0.25) O6S(0.25)
O15S(0.25) O10S(0.25) O7S(0.25) O5S(0.25) H3(0.5) O4S(0.25) O13S(0.125)
O14S(0.125) O11S(0.125) O12S(0.125)
5.a Aromatic/amide H refined with riding coordinates:
C3(H3A), C1(H1)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75944(6) 0.65018(9) 1.0312(4) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.69473(6) 0.71677(9) 0.7191(4) 0.0323(5) Uani 1 1 d D . . . .
O3 O 0.54555(7) 0.43169(10) 0.1814(5) 0.0364(5) Uani 1 1 d . . . . .
C6 C 0.71836(8) 0.65127(11) 0.8362(5) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.69222(8) 0.57340(11) 0.7248(5) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.64285(8) 0.57376(11) 0.5452(5) 0.0221(5) Uani 1 1 d . . . . .
H3A H 0.6260 0.6238 0.4845 0.027 Uiso 1 1 calc R . . . .
C1 C 0.71705(10) 0.5000 0.8140(7) 0.0213(6) Uani 1 2 d S T P . .
H1 H 0.7507 0.5000 0.9351 0.026 Uiso 1 2 calc RS T P . .
C4 C 0.61844(10) 0.5000 0.4556(7) 0.0220(6) Uani 1 2 d S T P . .
C5 C 0.56603(11) 0.5000 0.2605(7) 0.0221(6) Uani 1 2 d S T P . .
O1S O 0.8486(9) 0.5000 0.524(6) 0.183(7) Uiso 0.5 2 d S T P A 1
O9S O 0.5669(6) 0.7705(10) 0.551(6) 0.196(6) Uiso 0.5 1 d . . . B 10
O2S O 0.8523(9) 0.5000 0.948(6) 0.184(7) Uiso 0.5 2 d S T P C 2
O8S O 0.5789(10) 0.7824(16) 0.196(9) 0.247(8) Uiso 0.5 1 d . . . D 13
O3S O 0.6319(19) 0.088(3) 0.416(13) 0.237(16) Uiso 0.25 1 d . . . E 4
O6S O 0.4090(17) 0.189(3) 0.147(15) 0.235(15) Uiso 0.25 1 d . . . F 6
O15S O 0.5030(15) 1.0000 0.722(9) 0.290(16) Uiso 0.5 2 d S T P G 15
O10S O 0.5604(11) 0.7649(17) 0.927(10) 0.159(8) Uiso 0.25 1 d . . . H 8
O7S O 0.6034(15) 0.863(2) 0.531(13) 0.202(12) Uiso 0.25 1 d . . . I 12
H2 H 0.7086(13) 0.7597(14) 0.801(10) 0.067(11) Uiso 1 1 d D . . . .
O5S O 0.3936(15) 0.857(3) 0.778(13) 0.208(13) Uiso 0.25 1 d . . . J 5
H3 H 0.517(2) 0.430(3) 0.082(17) 0.038(16) Uiso 0.5 1 d . . . . .
O4S O 0.3790(14) 0.910(2) 0.104(11) 0.210(12) Uiso 0.25 1 d . . . K 3
O13S O 0.556(3) 0.956(4) 0.08(2) 0.23(3) Uiso 0.125 1 d . . . L 16
O14S O 0.477(4) 0.907(7) 0.57(4) 0.31(5) Uiso 0.125 1 d . . . M 14
O11S O 0.5139(18) 0.768(3) 0.646(11) 0.143(13) Uiso 0.125 1 d . . . N 9
O12S O 0.5000 0.760(4) 1.0000 0.24(2) Uiso 0.25 2 d S T P O 7
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0294(9) 0.0249(8) 0.0352(8) -0.0001(6) -0.0106(6) -0.0024(5)
O2 0.0350(9) 0.0192(8) 0.0409(9) -0.0002(6) -0.0114(6) 0.0002(6)
O3 0.0279(9) 0.0359(10) 0.0436(10) 0.0001(6) -0.0117(7) -0.0063(6)
C6 0.0252(9) 0.0209(10) 0.0221(9) -0.0005(6) -0.0020(7) 0.0003(7)
C2 0.0242(10) 0.0214(11) 0.0191(8) -0.0003(6) -0.0007(7) -0.0012(7)
C3 0.0249(10) 0.0217(10) 0.0195(8) 0.0001(7) -0.0007(7) 0.0020(7)
C1 0.0195(12) 0.0240(13) 0.0198(12) 0.000 -0.0025(9) 0.000
C4 0.0212(13) 0.0263(14) 0.0183(12) 0.000 -0.0002(10) 0.000
C5 0.0220(13) 0.0233(13) 0.0209(12) 0.000 -0.0004(10) 0.000
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.237(3) . ?
O2 C6 1.295(2) . ?
O2 H2 0.836(10) . ?
O3 C5 1.265(2) . ?
O3 H3 0.80(6) . ?
C6 C2 1.490(3) . ?
C2 C3 1.395(3) . ?
C2 C1 1.394(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.394(2) . ?
C1 C2 1.394(2) 6_565 ?
C1 H1 0.9500 . ?
C4 C3 1.394(2) 6_565 ?
C4 C5 1.488(4) . ?
C5 O3 1.265(2) 6_565 ?
O15S O15S 1.60(6) 5_676 ?
O13S O13S 1.44(14) 6_575 ?
O14S O14S 1.3(2) 2_656 ?
O11S O11S 1.24(8) 2_656 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2 114(3) . . ?
C5 O3 H3 120(4) . . ?
O1 C6 O2 124.65(18) . . ?
O1 C6 C2 120.01(17) . . ?
O2 C6 C2 115.33(17) . . ?
C3 C2 C6 120.56(17) . . ?
C1 C2 C6 119.01(18) . . ?
C1 C2 C3 120.39(18) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.47(18) . . ?
C4 C3 H3A 120.3 . . ?
C2 C1 C2 119.7(2) 6_565 . ?
C2 C1 H1 120.2 6_565 . ?
C2 C1 H1 120.2 . . ?
C3 C4 C3 120.6(2) . 6_565 ?
C3 C4 C5 119.71(12) 6_565 . ?
C3 C4 C5 119.70(12) . . ?
O3 C5 O3 124.9(3) . 6_565 ?
O3 C5 C4 117.57(13) 6_565 . ?
O3 C5 C4 117.57(13) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.836(10) 1.782(11) 2.618(2) 178(4) 7_667
O3 H3 O3 0.80(6) 1.83(6) 2.622(3) 175(6) 2_655
_shelx_res_file
;
tma_7-36_dioxane-1,3-dimethoxybenzene__c2c_100k.res created by SHELXL-2014/7
TITL TMA_7-36_Dioxane-dimethoxybenzene_C2c_100K_TWIN5.res in C2/m
REM Old TITL TMA_Diox_DMB_100K_C2-c in C2/m
REM SHELXT solution in C2/m
REM R1 0.177, Rweak 0.013, Alpha 0.062, Orientation as input
REM Formula found by SHELXT: C9 O6
CELL 0.71073 25.869 16.4191 3.606 90 93.617 90
ZERR 4 0.0044 0.0028 0.0006 0 0.004 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O
UNIT 36 24 54
EQIV $1 1.5-X,1.5-Y,2-Z
EQIV $2 1-X,+Y,-Z
DFIX 0.83 0.01 O2 H2
L.S. 20 0 0
PLAN 20
SIZE 0.17 0.11 0.09
TEMP -173.15
HTAB O2 O1_$1
HTAB O3 O3_$2
BOND $H
list 4
fmap 2 53
acta
SHEL 999 0.8
OMIT 1 1 0
REM
REM
REM
WGHT 0.123100 2.149900
BASF 0.07013
FVAR 0.74707
O1 3 0.759437 0.650179 1.031229 11.00000 0.02938 0.02494 =
0.03520 -0.00011 -0.01065 -0.00242
O2 3 0.694731 0.716773 0.719112 11.00000 0.03499 0.01916 =
0.04092 -0.00016 -0.01136 0.00021
O3 3 0.545547 0.431689 0.181425 11.00000 0.02789 0.03595 =
0.04365 0.00014 -0.01171 -0.00634
C6 1 0.718364 0.651272 0.836230 11.00000 0.02518 0.02093 =
0.02210 -0.00052 -0.00198 0.00032
C2 1 0.692217 0.573405 0.724750 11.00000 0.02423 0.02140 =
0.01910 -0.00033 -0.00065 -0.00123
C3 1 0.642847 0.573757 0.545218 11.00000 0.02489 0.02173 =
0.01953 0.00009 -0.00073 0.00204
AFIX 43
H3A 2 0.625990 0.623850 0.484521 11.00000 -1.20000
AFIX 0
C1 1 0.717051 0.500000 0.813975 10.50000 0.01946 0.02402 =
0.01984 0.00000 -0.00255 0.00000
AFIX 43
H1 2 0.750748 0.500001 0.935057 10.50000 -1.20000
AFIX 0
C4 1 0.618443 0.500000 0.455578 10.50000 0.02119 0.02629 =
0.01826 0.00000 -0.00018 0.00000
C5 1 0.566029 0.500000 0.260517 10.50000 0.02202 0.02325 =
0.02094 0.00000 -0.00043 0.00000
PART 1
O1S 3 0.848568 0.500000 0.524368 10.25000 0.18289
PART 0
PART 10
O9S 3 0.566912 0.770521 0.550656 10.50000 0.19566
PART 0
PART 2
O2S 3 0.852309 0.500000 0.948212 10.25000 0.18424
PART 0
PART 13
O8S 3 0.578916 0.782370 0.195642 10.50000 0.24688
PART 0
PART 4
O3S 3 0.631905 0.087813 0.416225 10.25000 0.23747
PART 0
PART 6
O6S 3 0.408952 0.189066 0.147165 10.25000 0.23510
PART 0
PART 15
O15S 3 0.502955 1.000000 0.721917 10.25000 0.29040
PART 0
PART 8
O10S 3 0.560397 0.764918 0.926681 10.25000 0.15899
PART 0
PART 12
O7S 3 0.603391 0.863331 0.531228 10.25000 0.20163
PART 0
H2 2 0.708595 0.759703 0.800726 11.00000 0.06678
PART 5
O5S 3 0.393552 0.857498 0.778398 10.25000 0.20837
PART 0
H3 2 0.517213 0.429778 0.081527 10.50000 0.03785
PART 3
O4S 3 0.378969 0.910163 0.103784 10.25000 0.20958
PART 0
PART 16
O13S 3 0.556368 0.956061 0.081979 10.12500 0.22516
PART 0
PART 14
O14S 3 0.477147 0.907171 0.574020 10.12500 0.31082
PART 0
PART 9
O11S 3 0.513934 0.767557 0.645789 10.12500 0.14337
PART 0
PART 7
O12S 3 0.500000 0.760277 1.000000 10.12500 0.23780
HKLF 5
REM TMA_7-36_Dioxane-dimethoxybenzene_C2c_100K_TWIN5.res in C2/m
REM R1 = 0.0688 for 1533 Fo > 4sig(Fo) and 0.0727 for all 1664 data
REM 137 parameters refined using 1 restraints
END
WGHT 0.1229 2.1521
REM Highest difference peak 0.317, deepest hole -0.415, 1-sigma level 0.072
Q1 1 0.8596 0.5333 0.2636 11.00000 0.05 0.32
Q2 1 0.6018 0.5000 0.3588 10.50000 0.05 0.30
Q3 1 0.5823 0.7962 0.6641 11.00000 0.05 0.30
Q4 1 0.3808 0.9118 -0.1086 11.00000 0.05 0.29
Q5 1 0.6143 0.8796 0.6705 11.00000 0.05 0.28
Q6 1 0.5000 1.0000 0.5000 10.25000 0.05 0.28
Q7 1 0.7037 0.6101 0.7817 11.00000 0.05 0.27
Q8 1 0.5790 0.7801 0.1036 11.00000 0.05 0.26
Q9 1 0.5625 0.9683 0.3894 11.00000 0.05 0.26
Q10 1 0.4009 0.1605 -0.0153 11.00000 0.05 0.25
Q11 1 0.8596 0.5255 0.8657 11.00000 0.05 0.24
Q12 1 0.5070 1.0000 0.9038 10.50000 0.05 0.22
Q13 1 0.4193 0.9147 0.6728 11.00000 0.05 0.20
Q14 1 0.4752 0.7579 0.7326 11.00000 0.05 0.20
Q15 1 0.6804 0.5760 0.6631 11.00000 0.05 0.18
Q16 1 0.4814 0.8422 0.6766 11.00000 0.05 0.17
Q17 1 0.7018 0.5441 0.7705 11.00000 0.05 0.16
Q18 1 0.7264 0.7984 0.8985 11.00000 0.05 0.16
Q19 1 0.6585 0.7172 0.5266 11.00000 0.05 0.14
Q20 1 0.7426 0.5761 0.8885 11.00000 0.05 0.14
;
_shelx_res_checksum 9493
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.930(4)
2 0.070(4)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_tma_6-18
_database_code_depnum_ccdc_archive 'CCDC 1915310'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2019-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6, C3 H8 O'
_chemical_formula_sum 'C12 H14 O7'
_chemical_formula_weight 270.23
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.1671(17)
_cell_length_b 9.4589(18)
_cell_length_c 9.6179(17)
_cell_angle_alpha 93.220(5)
_cell_angle_beta 116.280(5)
_cell_angle_gamma 118.728(5)
_cell_volume 616.2(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2579
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 31.078
_cell_measurement_theta_min 2.514
_shelx_estimated_absorpt_T_max 0.990
_shelx_estimated_absorpt_T_min 0.952
_exptl_absorpt_coefficient_mu 0.121
_exptl_absorpt_correction_T_max 0.7462
_exptl_absorpt_correction_T_min 0.4729
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0821 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.6337. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.457
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 284
_exptl_crystal_size_max 0.408
_exptl_crystal_size_mid 0.315
_exptl_crystal_size_min 0.079
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0833
_diffrn_reflns_av_unetI/netI 0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 8579
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 31.139
_diffrn_reflns_theta_min 2.513
_diffrn_ambient_temperature 100.0
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2510
_reflns_number_total 3929
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max 0.302
_refine_diff_density_min -0.330
_refine_diff_density_rms 0.066
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.912
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 189
_refine_ls_number_reflns 3929
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0759
_refine_ls_R_factor_gt 0.0486
_refine_ls_restrained_S_all 0.914
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1107
_refine_ls_wR_factor_ref 0.1203
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Restrained distances
O3-H3 = O1-H1 = O6-H6
0.83 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
C2(H2), C4(H4), C6(H6A)
3.c Idealised Me refined as rotating group:
C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24490(14) 0.24062(13) 0.71886(12) 0.0244(2) Uani 1 1 d D . . . .
H1 H 0.301(2) 0.262(2) 0.8234(12) 0.049(6) Uiso 1 1 d D . . . .
O2 O 0.54398(13) 0.34081(13) 0.76165(11) 0.0255(2) Uani 1 1 d . . . . .
O3 O 0.59758(14) 0.35982(13) 0.26695(12) 0.0261(2) Uani 1 1 d D . . . .
H3 H 0.655(3) 0.374(3) 0.214(2) 0.073(8) Uiso 1 1 d D . . . .
O4 O 0.33042(14) 0.27029(13) 0.01930(11) 0.0253(2) Uani 1 1 d . . . . .
O5 O -0.32876(14) 0.04364(13) 0.18307(11) 0.0247(2) Uani 1 1 d . . . . .
O6 O -0.29773(14) 0.06839(13) -0.03488(11) 0.0235(2) Uani 1 1 d D . . . .
H6 H -0.4167(15) 0.034(2) -0.080(2) 0.057(6) Uiso 1 1 d D . . . .
C1 C 0.36937(19) 0.28164(17) 0.66983(16) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.38515(18) 0.28727(16) 0.41815(15) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.521698 0.333085 0.484952 0.023 Uiso 1 1 calc R . . . .
C3 C 0.27292(18) 0.24904(16) 0.48894(15) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.07292(18) 0.18181(16) 0.39097(16) 0.0190(3) Uani 1 1 d . . . . .
H4 H -0.003870 0.154872 0.438988 0.023 Uiso 1 1 calc R . . . .
C5 C -0.01457(18) 0.15405(17) 0.22225(16) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.09619(18) 0.19124(16) 0.15145(15) 0.0190(3) Uani 1 1 d . . . . .
H6A H 0.035756 0.171220 0.036240 0.023 Uiso 1 1 calc R . . . .
C7 C 0.29670(18) 0.25817(16) 0.24927(15) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.40951(19) 0.29612(17) 0.16745(15) 0.0193(3) Uani 1 1 d . . . . .
C9 C -0.22916(19) 0.08376(17) 0.12112(16) 0.0199(3) Uani 1 1 d . . . . .
O7 O -0.22770(14) 0.41116(14) 0.10713(12) 0.0260(2) Uani 1 1 d . . . . .
H7 H -0.304(3) 0.385(2) 0.005(2) 0.041(5) Uiso 1 1 d . . . . .
C10 C 0.2554(2) 0.81948(19) 0.42380(19) 0.0317(4) Uani 1 1 d . . . . .
H10A H 0.329965 0.831078 0.372124 0.048 Uiso 1 1 calc GR . . . .
H10B H 0.340794 0.852270 0.543348 0.048 Uiso 1 1 calc GR . . . .
H10C H 0.208782 0.894445 0.400714 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.0788(2) 0.63314(18) 0.35389(17) 0.0243(3) Uani 1 1 d . . . . .
H11A H 0.125633 0.557767 0.382306 0.029 Uiso 1 1 calc R . . . .
H11B H 0.000848 0.621716 0.403328 0.029 Uiso 1 1 calc R . . . .
C12 C -0.04883(19) 0.57898(18) 0.16944(17) 0.0248(3) Uani 1 1 d . . . . .
H12A H -0.081703 0.662935 0.140333 0.030 Uiso 1 1 calc R . . . .
H12B H 0.023182 0.575548 0.118634 0.030 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0247(5) 0.0378(6) 0.0152(4) 0.0119(4) 0.0139(4) 0.0174(4)
O2 0.0201(4) 0.0344(6) 0.0160(4) 0.0081(4) 0.0095(4) 0.0118(4)
O3 0.0193(4) 0.0376(6) 0.0176(5) 0.0088(4) 0.0114(4) 0.0122(4)
O4 0.0254(5) 0.0379(6) 0.0157(4) 0.0109(4) 0.0133(4) 0.0176(4)
O5 0.0218(4) 0.0369(6) 0.0190(5) 0.0122(4) 0.0127(4) 0.0170(4)
O6 0.0203(4) 0.0368(6) 0.0152(4) 0.0094(4) 0.0100(4) 0.0167(4)
C1 0.0215(6) 0.0210(6) 0.0170(6) 0.0068(5) 0.0126(5) 0.0103(5)
C2 0.0189(6) 0.0207(6) 0.0159(6) 0.0066(5) 0.0097(5) 0.0100(5)
C3 0.0196(6) 0.0193(6) 0.0152(6) 0.0058(5) 0.0101(5) 0.0100(5)
C4 0.0200(6) 0.0224(6) 0.0166(6) 0.0068(5) 0.0115(5) 0.0117(5)
C5 0.0194(6) 0.0218(6) 0.0169(6) 0.0068(5) 0.0104(5) 0.0118(5)
C6 0.0213(6) 0.0215(6) 0.0146(5) 0.0070(5) 0.0103(5) 0.0118(5)
C7 0.0208(6) 0.0200(6) 0.0157(6) 0.0068(5) 0.0109(5) 0.0111(5)
C8 0.0202(6) 0.0217(6) 0.0161(6) 0.0061(5) 0.0106(5) 0.0111(5)
C9 0.0220(6) 0.0242(7) 0.0164(6) 0.0082(5) 0.0118(5) 0.0135(5)
O7 0.0207(5) 0.0344(6) 0.0168(5) 0.0078(4) 0.0105(4) 0.0113(4)
C10 0.0289(7) 0.0296(8) 0.0299(8) 0.0075(6) 0.0156(6) 0.0125(6)
C11 0.0248(6) 0.0278(7) 0.0210(6) 0.0094(6) 0.0128(5) 0.0148(6)
C12 0.0229(6) 0.0309(7) 0.0218(6) 0.0107(6) 0.0144(5) 0.0135(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3214(16) . ?
O2 C1 1.2194(16) . ?
O3 C8 1.3141(16) . ?
O4 C8 1.2212(15) . ?
O5 C9 1.2274(15) . ?
O6 C9 1.3115(16) . ?
C1 C3 1.4897(18) . ?
C2 C3 1.3940(18) . ?
C2 C7 1.3930(17) . ?
C3 C4 1.3913(18) . ?
C4 C5 1.3937(18) . ?
C5 C6 1.3836(18) . ?
C5 C9 1.4945(18) . ?
C6 C7 1.3956(18) . ?
C7 C8 1.4876(18) . ?
O7 C12 1.4451(17) . ?
C10 C11 1.530(2) . ?
C11 C12 1.5041(19) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 112.40(11) . . ?
O2 C1 O1 124.18(12) . . ?
O2 C1 C3 123.42(12) . . ?
C7 C2 C3 119.87(12) . . ?
C2 C3 C1 119.39(11) . . ?
C4 C3 C1 120.59(12) . . ?
C4 C3 C2 120.02(12) . . ?
C3 C4 C5 119.89(12) . . ?
C4 C5 C9 118.45(12) . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 C9 121.29(12) . . ?
C5 C6 C7 120.00(12) . . ?
C2 C7 C6 119.97(12) . . ?
C2 C7 C8 122.04(12) . . ?
C6 C7 C8 117.99(11) . . ?
O3 C8 C7 114.77(11) . . ?
O4 C8 O3 123.78(12) . . ?
O4 C8 C7 121.46(12) . . ?
O5 C9 O6 124.47(12) . . ?
O5 C9 C5 121.03(12) . . ?
O6 C9 C5 114.50(11) . . ?
C12 C11 C10 109.95(13) . . ?
O7 C12 C11 109.47(12) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.858(9) 1.773(11) 2.5951(14) 159.8(18) 1_556 yes
O3 H3 O7 0.857(10) 1.729(10) 2.5847(14) 178(2) 1_655 yes
O6 H6 O5 0.841(9) 1.786(9) 2.6266(15) 178(2) 2_455 yes
O7 H7 O2 0.85(2) 2.01(2) 2.8493(15) 173.0(17) 1_454 yes
_shelx_res_file
;
TITL TMA_6-18.res in P-1
tma_6-18.res
created by SHELXL-2018/3 at 11:11:05 on 17-Feb-2019
REM Old TITL test in P-1
REM SHELXT solution in P-1: R1 0.120, Rweak 0.003, Alpha 0.019
REM 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C12 O7
CELL 0.71073 9.1671 9.4589 9.6179 93.22 116.28 118.728
ZERR 2 0.0017 0.0018 0.0017 0.005 0.005 0.005
LATT 1
SFAC C H O
UNIT 24 28 14
EQIV $1 -1-X,-Y,-Z
EQIV $2 1+X,+Y,+Z
EQIV $3 +X,+Y,1+Z
EQIV $4 -1+X,+Y,-1+Z
DFIX 0.83 0.01 O3 H3 O1 H1 O6 H6
L.S. 40
PLAN 20
SIZE 0.408 0.315 0.079
TEMP -173.15
HTAB O6 O5_$1
HTAB O3 O7_$2
HTAB O1 O4_$3
HTAB O7 O2_$4
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.055900
FVAR 0.62355
O1 3 0.244904 0.240618 0.718860 11.00000 0.02466 0.03785 =
0.01523 0.01193 0.01390 0.01737
H1 2 0.301182 0.261892 0.823434 11.00000 0.04861
O2 3 0.543981 0.340810 0.761646 11.00000 0.02008 0.03439 =
0.01601 0.00811 0.00949 0.01181
O3 3 0.597579 0.359818 0.266952 11.00000 0.01926 0.03759 =
0.01757 0.00878 0.01142 0.01218
H3 2 0.654594 0.373849 0.213512 11.00000 0.07279
O4 3 0.330418 0.270294 0.019303 11.00000 0.02538 0.03786 =
0.01567 0.01090 0.01326 0.01756
O5 3 -0.328756 0.043640 0.183070 11.00000 0.02180 0.03689 =
0.01903 0.01221 0.01274 0.01703
O6 3 -0.297730 0.068388 -0.034877 11.00000 0.02031 0.03683 =
0.01523 0.00935 0.01005 0.01672
H6 2 -0.416704 0.034183 -0.080294 11.00000 0.05708
C1 1 0.369368 0.281639 0.669828 11.00000 0.02150 0.02101 =
0.01704 0.00682 0.01258 0.01035
C2 1 0.385155 0.287273 0.418152 11.00000 0.01893 0.02074 =
0.01588 0.00657 0.00973 0.01002
AFIX 43
H2 2 0.521698 0.333085 0.484952 11.00000 -1.20000
AFIX 0
C3 1 0.272920 0.249044 0.488939 11.00000 0.01961 0.01932 =
0.01515 0.00576 0.01009 0.00998
C4 1 0.072923 0.181811 0.390968 11.00000 0.02002 0.02242 =
0.01658 0.00683 0.01152 0.01172
AFIX 43
H4 2 -0.003870 0.154872 0.438988 11.00000 -1.20000
AFIX 0
C5 1 -0.014569 0.154051 0.222253 11.00000 0.01942 0.02180 =
0.01690 0.00683 0.01042 0.01181
C6 1 0.096194 0.191242 0.151445 11.00000 0.02130 0.02153 =
0.01462 0.00701 0.01026 0.01180
AFIX 43
H6A 2 0.035756 0.171220 0.036240 11.00000 -1.20000
AFIX 0
C7 1 0.296701 0.258167 0.249268 11.00000 0.02076 0.02004 =
0.01565 0.00682 0.01091 0.01107
C8 1 0.409510 0.296124 0.167449 11.00000 0.02020 0.02167 =
0.01605 0.00608 0.01058 0.01106
C9 1 -0.229161 0.083765 0.121125 11.00000 0.02196 0.02416 =
0.01644 0.00824 0.01176 0.01346
O7 3 -0.227698 0.411160 0.107126 11.00000 0.02067 0.03443 =
0.01679 0.00782 0.01053 0.01132
H7 2 -0.304309 0.385282 0.004733 11.00000 0.04112
C10 1 0.255450 0.819475 0.423801 11.00000 0.02888 0.02956 =
0.02990 0.00750 0.01564 0.01254
AFIX 137
H10A 2 0.329965 0.831078 0.372124 11.00000 -1.50000
H10B 2 0.340794 0.852270 0.543348 11.00000 -1.50000
H10C 2 0.208782 0.894445 0.400714 11.00000 -1.50000
AFIX 0
C11 1 0.078758 0.633144 0.353894 11.00000 0.02481 0.02779 =
0.02104 0.00941 0.01280 0.01475
AFIX 23
H11A 2 0.125633 0.557767 0.382306 11.00000 -1.20000
H11B 2 0.000848 0.621716 0.403328 11.00000 -1.20000
AFIX 0
C12 1 -0.048829 0.578983 0.169441 11.00000 0.02286 0.03093 =
0.02179 0.01074 0.01445 0.01353
AFIX 23
H12A 2 -0.081703 0.662935 0.140333 11.00000 -1.20000
H12B 2 0.023182 0.575548 0.118634 11.00000 -1.20000
AFIX 0
HKLF 4
REM TMA_6-18.res in P-1
REM wR2 = 0.1203, GooF = S = 0.912, Restrained GooF = 0.914 for all data
REM R1 = 0.0486 for 2510 Fo > 4sig(Fo) and 0.0759 for all 3929 data
REM 189 parameters refined using 3 restraints
END
WGHT 0.0559 0.0000
REM Highest difference peak 0.302, deepest hole -0.330, 1-sigma level 0.066
Q1 1 0.3559 0.2804 0.3410 11.00000 0.05 0.30
Q2 1 0.2085 0.2510 0.1965 11.00000 0.05 0.30
Q3 1 0.0241 0.1752 0.2986 11.00000 0.05 0.30
Q4 1 0.3029 0.2640 0.5570 11.00000 0.05 0.28
Q5 1 -0.3753 -0.0768 -0.1013 11.00000 0.05 0.25
Q6 1 0.1640 0.1753 0.4424 11.00000 0.05 0.25
Q7 1 0.2185 0.2026 -0.0228 11.00000 0.05 0.25
Q8 1 0.3012 0.3579 0.0005 11.00000 0.05 0.24
Q9 1 -0.2169 0.1200 -0.1194 11.00000 0.05 0.24
Q10 1 -0.2385 0.1971 0.0197 11.00000 0.05 0.24
Q11 1 0.4788 0.4592 0.2195 11.00000 0.05 0.23
Q12 1 0.2967 0.1454 -0.0159 11.00000 0.05 0.23
Q13 1 0.3208 0.1366 0.0800 11.00000 0.05 0.23
Q14 1 -0.2280 0.5242 0.1060 11.00000 0.05 0.22
Q15 1 0.1409 0.7363 0.3831 11.00000 0.05 0.22
Q16 1 0.3441 0.3658 0.1133 11.00000 0.05 0.22
Q17 1 0.4788 0.4051 0.7181 11.00000 0.05 0.22
Q18 1 0.5238 0.2345 0.1992 11.00000 0.05 0.22
Q19 1 0.1875 0.2629 0.4343 11.00000 0.05 0.21
Q20 1 0.1594 0.2982 0.6613 11.00000 0.05 0.21
;
_shelx_res_checksum 5598
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_3-36_EtOH_Ph2O_publ
_database_code_depnum_ccdc_archive 'CCDC 1915309'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '3(C9 H6 O6), 2(C12 H10 O)'
_chemical_formula_sum 'C51 H38 O20'
_chemical_formula_weight 970.81
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0028 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.50240(6)
_cell_length_b 15.88590(7)
_cell_length_c 16.60930(7)
_cell_angle_alpha 113.7260(4)
_cell_angle_beta 98.4480(4)
_cell_angle_gamma 106.8020(4)
_cell_volume 2316.46(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 21452
_cell_measurement_temperature 200
_cell_measurement_theta_max 35.6992161017
_cell_measurement_theta_min 1.35437565248
_shelx_estimated_absorpt_T_max 0.998
_shelx_estimated_absorpt_T_min 0.992
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_T_max 1.0
_exptl_absorpt_correction_T_min 0.995896160689
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.392
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1008
_exptl_crystal_size_max 0.078
_exptl_crystal_size_mid 0.028
_exptl_crystal_size_min 0.024
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0281
_diffrn_reflns_av_unetI/netI 0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 36998
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 24.415
_diffrn_reflns_theta_max 28.152
_diffrn_reflns_theta_min 1.361
_diffrn_ambient_temperature 200
_diffrn_detector 'Photon counting pixel array'
_diffrn_detector_area_resol_mean PILATUS_2M_S_N_24_0107_Diamond
_diffrn_detector_type PILATUS_2M_S_N_24_0107_Diamond
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device 'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type 'Fluid Film Devices'
_diffrn_measurement_method 'shutterless scans'
_diffrn_radiation_collimation '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator 'Silicon 111'
_diffrn_radiation_source 'Diamond Light Source Beamline I19-1'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type ?
_diffrn_radiation_wavelength 0.6889
_diffrn_source Synchrotron
_diffrn_source_type 'Undulator, I19, DLS, RAL'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 8999
_reflns_number_total 12320
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_collection 'Diamond I19 GDA, (Diamond, RAL, Didcot, UK)'
_computing_data_reduction
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2014)'
_computing_structure_solution 'XT (Sheldrick, 2014)'
_refine_diff_density_max 0.306
_refine_diff_density_min -0.380
_refine_diff_density_rms 0.110
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.100
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 700
_refine_ls_number_reflns 12320
_refine_ls_number_restraints 196
_refine_ls_R_factor_all 0.0559
_refine_ls_R_factor_gt 0.0429
_refine_ls_restrained_S_all 1.113
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1345
_refine_ls_wR_factor_ref 0.1429
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
2. Restrained distances
O17-H17 = O14-H14 = O1-H1 = O16-H16 = O8-H8 = O9-H9 = O3-H3 = O12-H12 = O6-H6
0.82 with sigma of 0.02
C16-H8
1.79 with sigma of 0.04
3. Rigid body (RIGU) restrains
O20, C40, C46, C41, C45, C47, C51, C42, C44, C48, C50, C43, C49
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
O19, C28, C34, C29, C33, C35, C39, C30, C32, C36, C38, C31, C37
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
C37(H37), C38(H38), C39(H39), C45(H45), C44(H44), C43(H43), C42(H42), C41(H41),
C47(H47), C48(H48), C49(H49), C50(H50), C51(H51)
4.b Fitted hexagon refined as free rotating group:
C40(C45,C44,C43,C42,C41)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25801(8) 0.57341(5) 0.54135(5) 0.04235(18) Uani 1 1 d D . . . .
O2 O 0.10812(8) 0.44126(6) 0.54189(5) 0.0470(2) Uani 1 1 d . . . . .
O3 O 0.10033(8) 0.43518(5) 0.83190(5) 0.04244(18) Uani 1 1 d D . . . .
O4 O 0.25003(8) 0.56189(5) 0.96519(5) 0.04090(18) Uani 1 1 d . . . . .
O5 O 0.53110(8) 0.87065(5) 0.96739(5) 0.04156(18) Uani 1 1 d . . . . .
O6 O 0.54199(8) 0.87047(5) 0.83362(5) 0.03993(17) Uani 1 1 d D . . . .
C1 C 0.25567(9) 0.57752(7) 0.68467(6) 0.02832(18) Uani 1 1 d . . . . .
C2 C 0.20907(9) 0.52540(7) 0.73197(6) 0.02850(18) Uani 1 1 d . . . . .
C3 C 0.25462(9) 0.57341(6) 0.82783(6) 0.02687(17) Uani 1 1 d . . . . .
C4 C 0.34808(9) 0.67258(6) 0.87663(6) 0.02744(18) Uani 1 1 d . . . . .
C5 C 0.39438(9) 0.72371(6) 0.82848(6) 0.02682(17) Uani 1 1 d . . . . .
C6 C 0.34838(9) 0.67695(7) 0.73288(6) 0.02839(18) Uani 1 1 d . . . . .
C7 C 0.20324(10) 0.52678(7) 0.58217(6) 0.03074(19) Uani 1 1 d . . . . .
C8 C 0.20104(9) 0.52140(6) 0.88053(6) 0.02857(18) Uani 1 1 d . . . . .
C9 C 0.49595(9) 0.82943(6) 0.88263(6) 0.02862(18) Uani 1 1 d . . . . .
O7 O 0.62380(8) 0.60519(5) 0.58729(5) 0.04253(18) Uani 1 1 d . . . . .
O8 O 0.47613(8) 0.47564(5) 0.59321(5) 0.04299(19) Uani 1 1 d D . . . .
O9 O 0.48372(8) 0.47075(5) 0.88187(5) 0.04130(18) Uani 1 1 d D . . . .
O10 O 0.61357(8) 0.60638(5) 1.01624(4) 0.04148(18) Uani 1 1 d . . . . .
O11 O 0.89943(8) 0.91133(5) 1.01300(5) 0.04050(18) Uani 1 1 d . . . . .
O12 O 0.91164(8) 0.90681(5) 0.87789(5) 0.03699(16) Uani 1 1 d D . . . .
C10 C 0.62547(9) 0.61354(6) 0.73299(6) 0.02575(17) Uani 1 1 d . . . . .
C11 C 0.57933(9) 0.56276(6) 0.78152(6) 0.02654(17) Uani 1 1 d . . . . .
C12 C 0.62454(9) 0.61288(6) 0.87737(6) 0.02586(17) Uani 1 1 d . . . . .
C13 C 0.71615(9) 0.71260(6) 0.92497(6) 0.02592(17) Uani 1 1 d . . . . .
C14 C 0.76342(9) 0.76194(6) 0.87585(6) 0.02492(17) Uani 1 1 d . . . . .
C15 C 0.71815(9) 0.71299(6) 0.77980(6) 0.02637(17) Uani 1 1 d . . . . .
C16 C 0.57421(9) 0.56301(6) 0.63053(6) 0.02870(18) Uani 1 1 d D . . . .
C17 C 0.57290(9) 0.56191(6) 0.93128(6) 0.02850(18) Uani 1 1 d . . . . .
C18 C 0.86452(9) 0.86752(6) 0.92867(6) 0.02687(17) Uani 1 1 d . . . . .
O13 O 0.00803(8) 0.35640(5) -0.06402(5) 0.04282(18) Uani 1 1 d . . . . .
O14 O 0.15207(8) 0.48760(5) 0.06888(5) 0.04148(18) Uani 1 1 d D . . . .
O15 O 0.15080(8) 0.48565(5) 0.36168(5) 0.04171(18) Uani 1 1 d . . . . .
O16 O 0.01252(9) 0.34936(6) 0.36295(5) 0.04576(19) Uani 1 1 d D . . . .
O17 O -0.28777(8) 0.05573(5) 0.07374(5) 0.04145(18) Uani 1 1 d D . . . .
O18 O -0.26623(8) 0.04966(5) -0.06065(5) 0.04480(19) Uani 1 1 d . . . . .
C19 C 0.00457(9) 0.34806(6) 0.07480(6) 0.02694(17) Uani 1 1 d . . . . .
C20 C -0.09069(9) 0.24953(6) 0.02752(6) 0.02841(18) Uani 1 1 d . . . . .
C21 C -0.13669(9) 0.19972(6) 0.07653(6) 0.02754(18) Uani 1 1 d . . . . .
C22 C -0.08882(9) 0.24749(6) 0.17221(6) 0.02828(18) Uani 1 1 d . . . . .
C23 C 0.00654(9) 0.34641(6) 0.21927(6) 0.02734(17) Uani 1 1 d . . . . .
C24 C 0.05309(9) 0.39681(6) 0.17050(6) 0.02749(18) Uani 1 1 d . . . . .
C25 C 0.05554(9) 0.39872(6) 0.02063(6) 0.02874(18) Uani 1 1 d . . . . .
C26 C -0.23778(10) 0.09394(6) 0.02355(6) 0.03033(19) Uani 1 1 d . . . . .
C27 C 0.06058(10) 0.39771(7) 0.32142(6) 0.02985(18) Uani 1 1 d . . . . .
O19 O 0.35697(17) 0.90722(9) 0.67133(8) 0.1064(5) Uani 1 1 d . U . . .
C28 C 0.29553(16) 0.87566(10) 0.57951(9) 0.0616(3) Uani 1 1 d . U . . .
C29 C 0.30960(17) 0.93773(10) 0.53983(9) 0.0629(4) Uani 1 1 d . U . . .
H29 H 0.3657 1.0068 0.5755 0.075 Uiso 1 1 calc R . . . .
C30 C 0.24087(17) 0.89807(12) 0.44737(10) 0.0694(4) Uani 1 1 d . U . . .
H30 H 0.2483 0.9404 0.4196 0.083 Uiso 1 1 calc R . . . .
C31 C 0.16127(16) 0.79720(13) 0.39500(11) 0.0743(4) Uani 1 1 d . U . . .
H31 H 0.1142 0.7702 0.3314 0.089 Uiso 1 1 calc R . . . .
C32 C 0.15093(15) 0.73697(11) 0.43539(12) 0.0732(4) Uani 1 1 d . U . . .
H32 H 0.0982 0.6674 0.3992 0.088 Uiso 1 1 calc R . . . .
C33 C 0.21543(15) 0.77528(10) 0.52742(11) 0.0681(4) Uani 1 1 d . U . . .
H33 H 0.2050 0.7329 0.5552 0.082 Uiso 1 1 calc R . . . .
C34 C 0.44349(19) 1.00698(11) 0.72701(9) 0.0728(4) Uani 1 1 d . U . . .
C35 C 0.5784(2) 1.04051(13) 0.72622(11) 0.0792(4) Uani 1 1 d . U . . .
H35 H 0.6128 0.9962 0.6866 0.095 Uiso 1 1 calc R . . . .
C36 C 0.66357(19) 1.13793(13) 0.78262(11) 0.0807(4) Uani 1 1 d . U . . .
H36 H 0.7571 1.1617 0.7818 0.097 Uiso 1 1 calc R . . . .
C37 C 0.6147(2) 1.20129(13) 0.84024(10) 0.0805(5) Uani 1 1 d . U . . .
H37 H 0.6746 1.2690 0.8795 0.097 Uiso 1 1 calc R . . . .
C38 C 0.4792(2) 1.16792(15) 0.84207(11) 0.0848(5) Uani 1 1 d . U . . .
H38 H 0.4463 1.2126 0.8825 0.102 Uiso 1 1 calc R . . . .
C39 C 0.39026(19) 1.06868(15) 0.78473(11) 0.0808(5) Uani 1 1 d . U . . .
H39 H 0.2966 1.0444 0.7853 0.097 Uiso 1 1 calc R . . . .
O20 O 0.75604(13) 0.74226(8) 0.28618(8) 0.0871(4) Uani 1 1 d . U . . .
C40 C 0.70607(10) 0.75272(7) 0.35964(6) 0.0642(4) Uani 1 1 d . U . . .
C45 C 0.58124(10) 0.76650(8) 0.35952(7) 0.0811(4) Uani 1 1 d G U . . .
H45 H 0.5316 0.7696 0.3088 0.097 Uiso 1 1 calc R . . . .
C44 C 0.52912(10) 0.77573(9) 0.43355(9) 0.0927(6) Uani 1 1 d G U . . .
H44 H 0.4438 0.7852 0.4335 0.111 Uiso 1 1 calc R . . . .
C43 C 0.60182(13) 0.77119(8) 0.50770(7) 0.0859(5) Uani 1 1 d G U . . .
H43 H 0.5662 0.7775 0.5583 0.103 Uiso 1 1 calc R . . . .
C42 C 0.72665(11) 0.75741(7) 0.50782(6) 0.0805(5) Uani 1 1 d G U . . .
H42 H 0.7763 0.7543 0.5585 0.097 Uiso 1 1 calc R . . . .
C41 C 0.77877(8) 0.74817(7) 0.43379(8) 0.0698(4) Uani 1 1 d G U . . .
H41 H 0.8641 0.7388 0.4339 0.084 Uiso 1 1 calc R . . . .
C46 C 0.84611(14) 0.82709(10) 0.28982(9) 0.0574(3) Uani 1 1 d . U . . .
C47 C 0.89302(14) 0.92053(9) 0.36457(8) 0.0577(3) Uani 1 1 d . U . . .
H47 H 0.8637 0.9296 0.4179 0.069 Uiso 1 1 calc R . . . .
C48 C 0.98282(18) 1.00046(11) 0.36088(10) 0.0724(4) Uani 1 1 d . U . . .
H48 H 1.0145 1.0652 0.4117 0.087 Uiso 1 1 calc R . . . .
C49 C 1.02746(19) 0.98765(15) 0.28409(12) 0.0814(5) Uani 1 1 d . U . . .
H49 H 1.0908 1.0430 0.2825 0.098 Uiso 1 1 calc R . . . .
C50 C 0.97931(18) 0.89401(15) 0.21009(11) 0.0770(5) Uani 1 1 d . U . . .
H50 H 1.0090 0.8849 0.1569 0.092 Uiso 1 1 calc R . . . .
C51 C 0.88900(16) 0.81361(12) 0.21221(9) 0.0676(4) Uani 1 1 d . U . . .
H51 H 0.8561 0.7491 0.1608 0.081 Uiso 1 1 calc R . . . .
H15 H 0.7477(12) 0.7484(9) 0.7432(8) 0.036(3) Uiso 1 1 d . . . . .
H6A H 0.3790(12) 0.7127(8) 0.6992(8) 0.035(3) Uiso 1 1 d . . . . .
H13 H 0.7461(11) 0.7466(8) 0.9925(8) 0.037(3) Uiso 1 1 d . . . . .
H24 H 0.1156(13) 0.4635(10) 0.2013(8) 0.043(3) Uiso 1 1 d . . . . .
H11 H 0.5158(13) 0.4945(9) 0.7504(8) 0.039(3) Uiso 1 1 d . . . . .
H2 H 0.1482(12) 0.4561(9) 0.6969(8) 0.037(3) Uiso 1 1 d . . . . .
H4 H 0.3792(12) 0.7063(9) 0.9441(8) 0.037(3) Uiso 1 1 d . . . . .
H20 H -0.1240(12) 0.2161(9) -0.0408(9) 0.042(3) Uiso 1 1 d . . . . .
H22 H -0.1153(13) 0.2148(9) 0.2077(9) 0.046(3) Uiso 1 1 d . . . . .
H12 H 0.9759(15) 0.9723(10) 0.9126(10) 0.064(4) Uiso 1 1 d D . . . .
H9 H 0.4566(15) 0.4454(11) 0.9187(9) 0.058(4) Uiso 1 1 d D . . . .
H6 H 0.6025(17) 0.9345(11) 0.8741(11) 0.081(5) Uiso 1 1 d D . . . .
H17 H -0.3486(16) -0.0102(11) 0.0358(11) 0.085(5) Uiso 1 1 d D . . . .
H3 H 0.0737(18) 0.4118(13) 0.8677(11) 0.085(5) Uiso 1 1 d D . . . .
H14 H 0.1819(15) 0.5123(10) 0.0323(9) 0.073(5) Uiso 1 1 d D . . . .
H8 H 0.464(6) 0.448(3) 0.5341(14) 0.41(3) Uiso 1 1 d D . . . .
H1 H 0.216(3) 0.5414(19) 0.4788(12) 0.163(10) Uiso 1 1 d D . . . .
H16 H 0.048(3) 0.380(2) 0.4184(12) 0.178(12) Uiso 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0559(4) 0.0391(4) 0.0228(3) 0.0158(3) 0.0109(3) 0.0045(3)
O2 0.0508(4) 0.0396(4) 0.0248(3) 0.0111(3) 0.0029(3) -0.0070(3)
O3 0.0484(4) 0.0345(4) 0.0304(3) 0.0172(3) 0.0076(3) -0.0037(3)
O4 0.0533(4) 0.0367(4) 0.0241(3) 0.0166(3) 0.0083(3) 0.0040(3)
O5 0.0518(4) 0.0308(3) 0.0246(3) 0.0099(3) 0.0058(3) -0.0001(3)
O6 0.0502(4) 0.0290(3) 0.0308(3) 0.0149(3) 0.0116(3) 0.0011(3)
C1 0.0289(4) 0.0301(4) 0.0207(4) 0.0110(3) 0.0071(3) 0.0060(3)
C2 0.0289(4) 0.0279(4) 0.0235(4) 0.0116(3) 0.0069(3) 0.0050(3)
C3 0.0279(4) 0.0280(4) 0.0235(4) 0.0136(3) 0.0078(3) 0.0068(3)
C4 0.0293(4) 0.0291(4) 0.0211(4) 0.0118(3) 0.0067(3) 0.0077(3)
C5 0.0274(4) 0.0254(4) 0.0239(4) 0.0113(3) 0.0071(3) 0.0060(3)
C6 0.0306(4) 0.0297(4) 0.0227(4) 0.0138(3) 0.0082(3) 0.0066(3)
C7 0.0333(4) 0.0316(4) 0.0219(4) 0.0127(3) 0.0074(3) 0.0056(3)
C8 0.0320(4) 0.0279(4) 0.0241(4) 0.0135(3) 0.0088(3) 0.0070(3)
C9 0.0316(4) 0.0261(4) 0.0241(4) 0.0117(3) 0.0074(3) 0.0063(3)
O7 0.0512(4) 0.0386(4) 0.0235(3) 0.0162(3) 0.0069(3) -0.0020(3)
O8 0.0498(4) 0.0312(3) 0.0242(3) 0.0085(3) 0.0047(3) -0.0064(3)
O9 0.0515(4) 0.0286(3) 0.0285(3) 0.0148(3) 0.0087(3) -0.0055(3)
O10 0.0518(4) 0.0351(4) 0.0234(3) 0.0149(3) 0.0080(3) -0.0024(3)
O11 0.0515(4) 0.0263(3) 0.0240(3) 0.0083(3) 0.0063(3) -0.0037(3)
O12 0.0467(4) 0.0240(3) 0.0287(3) 0.0127(3) 0.0098(3) -0.0017(3)
C10 0.0278(4) 0.0248(4) 0.0197(4) 0.0102(3) 0.0059(3) 0.0043(3)
C11 0.0285(4) 0.0232(4) 0.0230(4) 0.0112(3) 0.0064(3) 0.0037(3)
C12 0.0275(4) 0.0240(4) 0.0232(4) 0.0126(3) 0.0071(3) 0.0042(3)
C13 0.0282(4) 0.0246(4) 0.0206(4) 0.0106(3) 0.0064(3) 0.0048(3)
C14 0.0263(4) 0.0210(4) 0.0224(4) 0.0095(3) 0.0063(3) 0.0038(3)
C15 0.0293(4) 0.0243(4) 0.0229(4) 0.0123(3) 0.0072(3) 0.0052(3)
C16 0.0326(4) 0.0254(4) 0.0204(4) 0.0099(3) 0.0054(3) 0.0033(3)
C17 0.0317(4) 0.0259(4) 0.0239(4) 0.0135(3) 0.0076(3) 0.0034(3)
C18 0.0297(4) 0.0220(4) 0.0236(4) 0.0105(3) 0.0066(3) 0.0039(3)
O13 0.0539(4) 0.0413(4) 0.0245(3) 0.0176(3) 0.0105(3) 0.0042(3)
O14 0.0541(4) 0.0311(3) 0.0304(4) 0.0170(3) 0.0112(3) 0.0015(3)
O15 0.0513(4) 0.0339(3) 0.0235(3) 0.0092(3) 0.0055(3) 0.0037(3)
O16 0.0517(4) 0.0494(4) 0.0251(3) 0.0208(3) 0.0072(3) 0.0019(3)
O17 0.0499(4) 0.0304(3) 0.0324(4) 0.0147(3) 0.0121(3) 0.0002(3)
O18 0.0560(4) 0.0315(3) 0.0266(3) 0.0076(3) 0.0108(3) -0.0006(3)
C19 0.0312(4) 0.0277(4) 0.0227(4) 0.0132(3) 0.0098(3) 0.0096(3)
C20 0.0327(4) 0.0289(4) 0.0218(4) 0.0119(3) 0.0089(3) 0.0091(3)
C21 0.0303(4) 0.0243(4) 0.0243(4) 0.0107(3) 0.0082(3) 0.0067(3)
C22 0.0318(4) 0.0288(4) 0.0241(4) 0.0139(3) 0.0093(3) 0.0090(3)
C23 0.0308(4) 0.0295(4) 0.0207(4) 0.0121(3) 0.0082(3) 0.0096(3)
C24 0.0316(4) 0.0255(4) 0.0229(4) 0.0111(3) 0.0079(3) 0.0083(3)
C25 0.0345(4) 0.0276(4) 0.0235(4) 0.0129(3) 0.0101(3) 0.0092(3)
C26 0.0345(5) 0.0272(4) 0.0257(4) 0.0122(3) 0.0091(3) 0.0073(3)
C27 0.0337(4) 0.0306(4) 0.0219(4) 0.0126(3) 0.0073(3) 0.0079(3)
O19 0.1539(12) 0.0685(7) 0.0637(7) 0.0427(6) -0.0065(7) 0.0007(7)
C28 0.0739(9) 0.0527(7) 0.0560(7) 0.0293(6) 0.0129(6) 0.0191(6)
C29 0.0904(10) 0.0439(6) 0.0518(7) 0.0239(5) 0.0161(7) 0.0227(6)
C30 0.0875(10) 0.0698(9) 0.0586(8) 0.0369(7) 0.0195(7) 0.0318(8)
C31 0.0629(9) 0.0796(10) 0.0561(8) 0.0216(7) 0.0047(6) 0.0161(7)
C32 0.0510(7) 0.0558(8) 0.0847(10) 0.0235(7) 0.0082(7) 0.0029(6)
C33 0.0620(8) 0.0535(7) 0.0866(10) 0.0400(7) 0.0135(7) 0.0132(6)
C34 0.0977(12) 0.0656(8) 0.0451(7) 0.0316(6) 0.0064(7) 0.0175(8)
C35 0.1077(13) 0.0756(10) 0.0561(8) 0.0299(8) 0.0272(8) 0.0378(10)
C36 0.0855(11) 0.0853(11) 0.0596(9) 0.0317(8) 0.0125(8) 0.0252(9)
C37 0.0983(12) 0.0708(9) 0.0436(7) 0.0165(7) -0.0090(7) 0.0240(9)
C38 0.1124(15) 0.1014(13) 0.0434(7) 0.0273(8) 0.0127(8) 0.0599(12)
C39 0.0821(11) 0.1141(14) 0.0546(8) 0.0491(9) 0.0150(8) 0.0380(10)
O20 0.1037(9) 0.0487(5) 0.0750(7) 0.0077(5) 0.0375(6) 0.0098(5)
C40 0.0671(8) 0.0393(6) 0.0725(9) 0.0207(6) 0.0216(7) 0.0098(6)
C45 0.0782(10) 0.0804(11) 0.0960(12) 0.0504(9) 0.0231(9) 0.0339(9)
C44 0.0856(12) 0.0928(13) 0.1267(16) 0.0622(12) 0.0532(12) 0.0443(10)
C43 0.0998(13) 0.0627(9) 0.1001(13) 0.0459(9) 0.0487(11) 0.0174(9)
C42 0.0850(11) 0.0513(8) 0.0922(11) 0.0441(8) 0.0137(9) 0.0001(7)
C41 0.0583(8) 0.0446(7) 0.0961(11) 0.0344(7) 0.0157(8) 0.0074(6)
C46 0.0575(7) 0.0557(7) 0.0473(7) 0.0172(6) 0.0122(5) 0.0182(6)
C47 0.0640(8) 0.0528(7) 0.0410(6) 0.0173(5) 0.0145(5) 0.0096(6)
C48 0.0830(10) 0.0609(8) 0.0512(7) 0.0246(6) 0.0143(7) 0.0035(7)
C49 0.0814(11) 0.0957(12) 0.0712(10) 0.0529(10) 0.0267(8) 0.0179(9)
C50 0.0877(11) 0.1139(14) 0.0562(9) 0.0506(9) 0.0331(8) 0.0535(10)
C51 0.0793(10) 0.0810(10) 0.0421(7) 0.0220(6) 0.0159(6) 0.0416(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2695(11) . ?
O1 H1 0.917(17) . ?
O2 C7 1.2566(11) . ?
O3 C8 1.2917(11) . ?
O3 H3 0.859(14) . ?
O4 C8 1.2345(11) . ?
O5 C9 1.2299(11) . ?
O6 C9 1.2969(11) . ?
O6 H6 0.917(14) . ?
C1 C2 1.3945(12) . ?
C1 C6 1.3957(12) . ?
C1 C7 1.4882(12) . ?
C2 C3 1.3905(12) . ?
C2 H2 0.963(12) . ?
C3 C4 1.3953(12) . ?
C3 C8 1.4912(11) . ?
C4 C5 1.3944(11) . ?
C4 H4 0.979(12) . ?
C5 C6 1.3873(12) . ?
C5 C9 1.4947(11) . ?
C6 H6A 0.971(12) . ?
O7 C16 1.2375(11) . ?
O8 C16 1.2904(11) . ?
O8 H8 0.870(19) . ?
O9 C17 1.2967(11) . ?
O9 H9 0.894(12) . ?
O10 C17 1.2325(11) . ?
O11 C18 1.2239(11) . ?
O12 C18 1.3090(10) . ?
O12 H12 0.932(13) . ?
C10 C11 1.3955(11) . ?
C10 C15 1.3957(11) . ?
C10 C16 1.4872(12) . ?
C11 C12 1.3903(12) . ?
C11 H11 0.958(13) . ?
C12 C13 1.3956(11) . ?
C12 C17 1.4912(11) . ?
C13 C14 1.3911(11) . ?
C13 H13 0.979(12) . ?
C14 C15 1.3931(12) . ?
C14 C18 1.4909(11) . ?
C15 H15 1.006(12) . ?
O13 C25 1.2318(11) . ?
O14 C25 1.2988(11) . ?
O14 H14 0.893(13) . ?
O15 C27 1.2623(11) . ?
O16 C27 1.2748(11) . ?
O16 H16 0.812(17) . ?
O17 C26 1.3002(11) . ?
O17 H17 0.931(13) . ?
O18 C26 1.2265(11) . ?
C19 C20 1.3936(12) . ?
C19 C24 1.3890(12) . ?
C19 C25 1.4894(11) . ?
C20 C21 1.3912(12) . ?
C20 H20 0.991(13) . ?
C21 C22 1.3886(12) . ?
C21 C26 1.4932(12) . ?
C22 C23 1.3982(12) . ?
C22 H22 0.951(13) . ?
C23 C24 1.3957(11) . ?
C23 C27 1.4839(12) . ?
C24 H24 0.937(13) . ?
O19 C28 1.3792(17) . ?
O19 C34 1.3906(18) . ?
C28 C29 1.3769(18) . ?
C28 C33 1.3782(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.362(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.369(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.366(2) . ?
C34 C39 1.382(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.363(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.364(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.394(3) . ?
C39 H39 0.9500 . ?
O20 C40 1.3665(13) . ?
O20 C46 1.3765(17) . ?
C40 C45 1.3900 . ?
C40 C41 1.3900 . ?
C45 H45 0.9500 . ?
C45 C44 1.3900 . ?
C44 H44 0.9500 . ?
C44 C43 1.3900 . ?
C43 H43 0.9500 . ?
C43 C42 1.3900 . ?
C42 H42 0.9500 . ?
C42 C41 1.3900 . ?
C41 H41 0.9500 . ?
C46 C47 1.3792(18) . ?
C46 C51 1.3836(19) . ?
C47 H47 0.9500 . ?
C47 C48 1.376(2) . ?
C48 H48 0.9500 . ?
C48 C49 1.382(2) . ?
C49 H49 0.9500 . ?
C49 C50 1.375(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.370(2) . ?
C51 H51 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 113.7(18) . . ?
C8 O3 H3 109.3(12) . . ?
C9 O6 H6 106.9(11) . . ?
C2 C1 C6 120.44(8) . . ?
C2 C1 C7 119.37(8) . . ?
C6 C1 C7 120.18(8) . . ?
C1 C2 H2 118.7(7) . . ?
C3 C2 C1 119.55(8) . . ?
C3 C2 H2 121.7(7) . . ?
C2 C3 C4 120.44(8) . . ?
C2 C3 C8 120.85(8) . . ?
C4 C3 C8 118.67(7) . . ?
C3 C4 H4 120.2(7) . . ?
C5 C4 C3 119.43(8) . . ?
C5 C4 H4 120.4(7) . . ?
C4 C5 C9 118.19(8) . . ?
C6 C5 C4 120.64(8) . . ?
C6 C5 C9 121.16(8) . . ?
C1 C6 H6A 119.6(7) . . ?
C5 C6 C1 119.49(8) . . ?
C5 C6 H6A 120.9(7) . . ?
O1 C7 C1 117.38(8) . . ?
O2 C7 O1 124.42(8) . . ?
O2 C7 C1 118.19(8) . . ?
O3 C8 C3 115.45(7) . . ?
O4 C8 O3 124.24(8) . . ?
O4 C8 C3 120.29(8) . . ?
O5 C9 O6 124.89(8) . . ?
O5 C9 C5 120.06(8) . . ?
O6 C9 C5 115.05(7) . . ?
C16 O8 H8 108(3) . . ?
C17 O9 H9 109.8(9) . . ?
C18 O12 H12 113.0(9) . . ?
C11 C10 C16 120.42(7) . . ?
C15 C10 C11 120.58(8) . . ?
C15 C10 C16 118.99(7) . . ?
C10 C11 H11 121.6(7) . . ?
C12 C11 C10 119.28(8) . . ?
C12 C11 H11 119.1(7) . . ?
C11 C12 C13 120.67(8) . . ?
C11 C12 C17 120.60(7) . . ?
C13 C12 C17 118.71(7) . . ?
C12 C13 H13 119.3(7) . . ?
C14 C13 C12 119.54(8) . . ?
C14 C13 H13 121.2(7) . . ?
C13 C14 C15 120.47(7) . . ?
C13 C14 C18 118.26(7) . . ?
C15 C14 C18 121.27(7) . . ?
C10 C15 H15 119.0(7) . . ?
C14 C15 C10 119.45(8) . . ?
C14 C15 H15 121.5(7) . . ?
O7 C16 O8 124.65(8) . . ?
O7 C16 C10 120.33(8) . . ?
O8 C16 C10 115.01(7) . . ?
O9 C17 C12 114.82(7) . . ?
O10 C17 O9 124.70(8) . . ?
O10 C17 C12 120.47(8) . . ?
O11 C18 O12 124.31(8) . . ?
O11 C18 C14 120.92(8) . . ?
O12 C18 C14 114.77(7) . . ?
C25 O14 H14 110.9(9) . . ?
C27 O16 H16 113(2) . . ?
C26 O17 H17 109.4(11) . . ?
C20 C19 C25 118.69(7) . . ?
C24 C19 C20 120.33(8) . . ?
C24 C19 C25 120.97(8) . . ?
C19 C20 H20 119.1(7) . . ?
C21 C20 C19 119.74(8) . . ?
C21 C20 H20 121.2(7) . . ?
C20 C21 C26 118.27(8) . . ?
C22 C21 C20 120.53(8) . . ?
C22 C21 C26 121.20(8) . . ?
C21 C22 C23 119.46(8) . . ?
C21 C22 H22 122.7(8) . . ?
C23 C22 H22 117.8(8) . . ?
C22 C23 C27 120.00(8) . . ?
C24 C23 C22 120.29(8) . . ?
C24 C23 C27 119.70(8) . . ?
C19 C24 C23 119.65(8) . . ?
C19 C24 H24 119.3(7) . . ?
C23 C24 H24 121.0(7) . . ?
O13 C25 O14 124.12(8) . . ?
O13 C25 C19 120.59(8) . . ?
O14 C25 C19 115.28(7) . . ?
O17 C26 C21 114.77(8) . . ?
O18 C26 O17 125.16(8) . . ?
O18 C26 C21 120.06(8) . . ?
O15 C27 O16 124.15(8) . . ?
O15 C27 C23 118.49(8) . . ?
O16 C27 C23 117.36(8) . . ?
C28 O19 C34 118.44(11) . . ?
C29 C28 O19 124.06(12) . . ?
C29 C28 C33 120.42(13) . . ?
C33 C28 O19 115.52(12) . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.01(13) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.53(14) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.40(14) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 120.91(14) . . ?
C33 C32 H32 119.5 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.70(14) . . ?
C32 C33 H33 120.1 . . ?
C35 C34 O19 120.00(16) . . ?
C35 C34 C39 121.94(16) . . ?
C39 C34 O19 118.01(17) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.64(16) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.16(18) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.57(17) . . ?
C38 C37 H37 119.7 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.21(17) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 C38 117.46(17) . . ?
C34 C39 H39 121.3 . . ?
C38 C39 H39 121.3 . . ?
C40 O20 C46 117.56(9) . . ?
O20 C40 C45 119.86(9) . . ?
O20 C40 C41 120.14(9) . . ?
C45 C40 C41 120.0 . . ?
C40 C45 H45 120.0 . . ?
C40 C45 C44 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C44 H44 120.0 . . ?
C45 C44 C43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C43 H43 120.0 . . ?
C44 C43 C42 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 C43 120.0 . . ?
C41 C42 H42 120.0 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0 . . ?
C42 C41 H41 120.0 . . ?
O20 C46 C47 123.84(12) . . ?
O20 C46 C51 115.57(12) . . ?
C47 C46 C51 120.59(14) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 C46 119.09(13) . . ?
C48 C47 H47 120.5 . . ?
C47 C48 H48 119.6 . . ?
C47 C48 C49 120.77(15) . . ?
C49 C48 H48 119.6 . . ?
C48 C49 H49 120.3 . . ?
C50 C49 C48 119.34(15) . . ?
C50 C49 H49 120.3 . . ?
C49 C50 H50 119.6 . . ?
C51 C50 C49 120.72(14) . . ?
C51 C50 H50 119.6 . . ?
C46 C51 H51 120.3 . . ?
C50 C51 C46 119.48(14) . . ?
C50 C51 H51 120.3 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O11 0.932(13) 1.716(13) 2.6426(9) 172.7(15) 2_777
O9 H9 O10 0.894(12) 1.729(12) 2.6196(9) 174.0(14) 2_667
O6 H6 O18 0.917(14) 1.712(14) 2.6205(10) 170.6(17) 1_666
O17 H17 O5 0.931(13) 1.713(14) 2.6426(9) 176.4(16) 1_444
O3 H3 O13 0.859(14) 1.793(14) 2.6506(9) 176.1(18) 1_556
O14 H14 O4 0.893(13) 1.729(13) 2.6213(9) 176.4(14) 1_554
O8 H8 O7 0.870(19) 1.81(3) 2.6338(10) 158(6) 2_666
O1 H1 O15 0.917(17) 1.706(17) 2.6218(10) 176(3) .
O16 H16 O2 0.812(17) 1.791(17) 2.5993(10) 173(3) .
_shelx_res_file
;
pc_ht_1_ii329_etoh_ph2o.res created by SHELXL-2014/7
TITL PC_HT_1_ii329.res in P-1
REM Old TITL shelxt in P -1
REM SHELXT solution in P-1
REM R1 0.167, Rweak 0.002, Alpha 0.063, Orientation as input
REM Formula found by SHELXT: C53 O18
CELL 0.6889 10.5024 15.8859 16.6093 113.726 98.448 106.802
ZERR 2 0.000056 0.000074 0.000071 0.000376 0.000425 0.00042
LATT 1
SFAC C H O
DISP C 0.0028 0.0015 10.64
DISP H -0 0 0.67
DISP O 0.0101 0.0057 29.59
UNIT 102 76 40
EQIV $1 +X,+Y,1+Z
EQIV $2 1+X,1+Y,1+Z
EQIV $3 1-X,1-Y,1-Z
EQIV $4 1-X,1-Y,2-Z
EQIV $5 2-X,2-Y,2-Z
EQIV $6 +X,+Y,-1+Z
EQIV $7 -1+X,-1+Y,-1+Z
DFIX 0.82 O17 H17 O14 H14 O1 H1 O16 H16 O8 H8 O9 H9 O3 H3 O12 H12 O6 H6
DANG 1.79 C16 H8
RIGU O20 C40 C46 C41 C45 C47 C51 C42 C44 C48 C50 C43 C49
RIGU O19 C28 C34 C29 C33 C35 C39 C30 C32 C36 C38 C31 C37
L.S. 30
PLAN 20
SIZE 0.078 0.028 0.024
TEMP -73.15
HTAB O1 O15
HTAB O3 O13_$1
HTAB O6 O18_$2
HTAB O8 O7_$3
HTAB O9 O10_$4
HTAB O12 O11_$5
HTAB O14 O4_$6
HTAB O16 O2
HTAB O17 O5_$7
BOND $H
LIST 6
fmap 2
acta
SHEL 999 0.73
OMIT -1 -2 6
OMIT -2 -1 5
REM
REM
REM
WGHT 0.090000
FVAR 0.30138
O1 3 0.258007 0.573410 0.541348 11.00000 0.05586 0.03909 =
0.02282 0.01581 0.01090 0.00448
O2 3 0.108120 0.441257 0.541889 11.00000 0.05082 0.03965 =
0.02478 0.01112 0.00289 -0.00699
O3 3 0.100326 0.435175 0.831898 11.00000 0.04837 0.03446 =
0.03040 0.01722 0.00758 -0.00372
O4 3 0.250032 0.561889 0.965195 11.00000 0.05332 0.03667 =
0.02406 0.01662 0.00826 0.00400
O5 3 0.531100 0.870653 0.967390 11.00000 0.05180 0.03081 =
0.02459 0.00989 0.00575 -0.00010
O6 3 0.541994 0.870471 0.833621 11.00000 0.05018 0.02895 =
0.03082 0.01494 0.01158 0.00105
C1 1 0.255674 0.577521 0.684668 11.00000 0.02892 0.03012 =
0.02073 0.01101 0.00707 0.00598
C2 1 0.209068 0.525402 0.731972 11.00000 0.02890 0.02790 =
0.02346 0.01164 0.00694 0.00501
C3 1 0.254620 0.573415 0.827829 11.00000 0.02789 0.02800 =
0.02347 0.01361 0.00780 0.00682
C4 1 0.348080 0.672583 0.876634 11.00000 0.02926 0.02909 =
0.02108 0.01184 0.00669 0.00772
C5 1 0.394380 0.723714 0.828484 11.00000 0.02743 0.02543 =
0.02388 0.01125 0.00706 0.00600
C6 1 0.348380 0.676949 0.732882 11.00000 0.03064 0.02974 =
0.02273 0.01379 0.00817 0.00665
C7 1 0.203242 0.526784 0.582170 11.00000 0.03327 0.03164 =
0.02189 0.01266 0.00737 0.00557
C8 1 0.201040 0.521396 0.880531 11.00000 0.03200 0.02785 =
0.02406 0.01348 0.00880 0.00704
C9 1 0.495946 0.829431 0.882631 11.00000 0.03162 0.02608 =
0.02406 0.01166 0.00744 0.00627
O7 3 0.623804 0.605189 0.587291 11.00000 0.05121 0.03860 =
0.02349 0.01618 0.00692 -0.00201
O8 3 0.476129 0.475644 0.593214 11.00000 0.04982 0.03123 =
0.02415 0.00849 0.00469 -0.00640
O9 3 0.483719 0.470749 0.881870 11.00000 0.05149 0.02858 =
0.02846 0.01476 0.00871 -0.00547
O10 3 0.613568 0.606383 1.016237 11.00000 0.05177 0.03506 =
0.02339 0.01486 0.00804 -0.00235
O11 3 0.899427 0.911334 1.013002 11.00000 0.05151 0.02631 =
0.02401 0.00828 0.00634 -0.00368
O12 3 0.911640 0.906811 0.877895 11.00000 0.04670 0.02397 =
0.02869 0.01271 0.00983 -0.00167
C10 1 0.625471 0.613541 0.732988 11.00000 0.02779 0.02477 =
0.01969 0.01022 0.00593 0.00435
C11 1 0.579326 0.562762 0.781524 11.00000 0.02853 0.02322 =
0.02302 0.01119 0.00644 0.00365
C12 1 0.624538 0.612881 0.877372 11.00000 0.02752 0.02403 =
0.02320 0.01259 0.00713 0.00420
C13 1 0.716155 0.712600 0.924971 11.00000 0.02822 0.02455 =
0.02062 0.01057 0.00644 0.00483
C14 1 0.763416 0.761939 0.875848 11.00000 0.02632 0.02097 =
0.02241 0.00954 0.00626 0.00379
C15 1 0.718154 0.712991 0.779801 11.00000 0.02925 0.02426 =
0.02289 0.01234 0.00722 0.00515
C16 1 0.574212 0.563012 0.630534 11.00000 0.03263 0.02536 =
0.02037 0.00990 0.00543 0.00330
C17 1 0.572904 0.561909 0.931276 11.00000 0.03169 0.02590 =
0.02392 0.01354 0.00762 0.00344
C18 1 0.864516 0.867519 0.928669 11.00000 0.02972 0.02198 =
0.02361 0.01047 0.00657 0.00390
O13 3 0.008029 0.356399 -0.064025 11.00000 0.05395 0.04132 =
0.02451 0.01759 0.01054 0.00423
O14 3 0.152073 0.487597 0.068882 11.00000 0.05406 0.03106 =
0.03040 0.01699 0.01115 0.00150
O15 3 0.150799 0.485648 0.361679 11.00000 0.05129 0.03394 =
0.02355 0.00916 0.00551 0.00370
O16 3 0.012521 0.349358 0.362952 11.00000 0.05175 0.04937 =
0.02506 0.02084 0.00716 0.00189
O17 3 -0.287769 0.055728 0.073742 11.00000 0.04995 0.03037 =
0.03242 0.01469 0.01207 0.00017
O18 3 -0.266225 0.049657 -0.060654 11.00000 0.05600 0.03154 =
0.02660 0.00757 0.01078 -0.00056
C19 1 0.004572 0.348062 0.074798 11.00000 0.03124 0.02774 =
0.02268 0.01322 0.00981 0.00964
C20 1 -0.090686 0.249533 0.027516 11.00000 0.03266 0.02887 =
0.02185 0.01185 0.00887 0.00911
C21 1 -0.136694 0.199719 0.076530 11.00000 0.03032 0.02432 =
0.02428 0.01067 0.00815 0.00666
C22 1 -0.088824 0.247490 0.172209 11.00000 0.03181 0.02882 =
0.02410 0.01387 0.00934 0.00896
C23 1 0.006536 0.346409 0.219267 11.00000 0.03077 0.02952 =
0.02075 0.01208 0.00824 0.00964
C24 1 0.053094 0.396809 0.170502 11.00000 0.03160 0.02551 =
0.02293 0.01109 0.00793 0.00830
C25 1 0.055536 0.398718 0.020633 11.00000 0.03451 0.02760 =
0.02351 0.01286 0.01007 0.00923
C26 1 -0.237782 0.093936 0.023552 11.00000 0.03450 0.02717 =
0.02569 0.01217 0.00914 0.00731
C27 1 0.060580 0.397707 0.321421 11.00000 0.03369 0.03056 =
0.02187 0.01256 0.00730 0.00795
O19 3 0.356967 0.907215 0.671334 11.00000 0.15395 0.06847 =
0.06367 0.04274 -0.00650 0.00067
C28 1 0.295527 0.875662 0.579511 11.00000 0.07392 0.05273 =
0.05600 0.02929 0.01294 0.01914
C29 1 0.309600 0.937731 0.539828 11.00000 0.09038 0.04386 =
0.05177 0.02389 0.01610 0.02275
AFIX 43
H29 2 0.365727 1.006791 0.575487 11.00000 -1.20000
AFIX 0
C30 1 0.240873 0.898074 0.447374 11.00000 0.08746 0.06975 =
0.05855 0.03692 0.01950 0.03182
AFIX 43
H30 2 0.248343 0.940419 0.419552 11.00000 -1.20000
AFIX 0
C31 1 0.161274 0.797203 0.394996 11.00000 0.06286 0.07958 =
0.05607 0.02158 0.00472 0.01611
AFIX 43
H31 2 0.114247 0.770180 0.331426 11.00000 -1.20000
AFIX 0
C32 1 0.150927 0.736974 0.435386 11.00000 0.05105 0.05583 =
0.08474 0.02350 0.00817 0.00288
AFIX 43
H32 2 0.098231 0.667429 0.399203 11.00000 -1.20000
AFIX 0
C33 1 0.215428 0.775281 0.527418 11.00000 0.06201 0.05350 =
0.08657 0.03996 0.01346 0.01323
AFIX 43
H33 2 0.205017 0.732860 0.555240 11.00000 -1.20000
AFIX 0
C34 1 0.443485 1.006983 0.727007 11.00000 0.09769 0.06557 =
0.04513 0.03159 0.00640 0.01746
C35 1 0.578436 1.040513 0.726216 11.00000 0.10769 0.07558 =
0.05613 0.02989 0.02715 0.03782
AFIX 43
H35 2 0.612757 0.996190 0.686580 11.00000 -1.20000
AFIX 0
C36 1 0.663566 1.137925 0.782618 11.00000 0.08546 0.08532 =
0.05958 0.03173 0.01251 0.02516
AFIX 43
H36 2 0.757147 1.161723 0.781781 11.00000 -1.20000
AFIX 0
C37 1 0.614692 1.201288 0.840241 11.00000 0.09826 0.07084 =
0.04365 0.01648 -0.00898 0.02401
AFIX 43
H37 2 0.674639 1.269033 0.879451 11.00000 -1.20000
AFIX 0
C38 1 0.479235 1.167917 0.842072 11.00000 0.11240 0.10141 =
0.04343 0.02726 0.01274 0.05989
AFIX 43
H38 2 0.446280 1.212646 0.882528 11.00000 -1.20000
AFIX 0
C39 1 0.390265 1.068677 0.784734 11.00000 0.08210 0.11414 =
0.05456 0.04911 0.01497 0.03804
AFIX 43
H39 2 0.296632 1.044392 0.785325 11.00000 -1.20000
AFIX 0
O20 3 0.756039 0.742263 0.286176 11.00000 0.10372 0.04870 =
0.07505 0.00775 0.03745 0.00977
AFIX 66
C40 1 0.706066 0.752715 0.359642 11.00000 0.06706 0.03926 =
0.07247 0.02072 0.02164 0.00984
C45 1 0.581241 0.766497 0.359523 11.00000 0.07816 0.08041 =
0.09598 0.05041 0.02307 0.03393
AFIX 43
H45 2 0.531551 0.769602 0.308846 11.00000 -1.20000
AFIX 65
C44 1 0.529119 0.775735 0.433554 11.00000 0.08557 0.09276 =
0.12670 0.06218 0.05318 0.04428
AFIX 43
H44 2 0.443807 0.785154 0.433472 11.00000 -1.20000
AFIX 65
C43 1 0.601823 0.771191 0.507703 11.00000 0.09980 0.06273 =
0.10010 0.04587 0.04871 0.01740
AFIX 43
H43 2 0.566200 0.777505 0.558299 11.00000 -1.20000
AFIX 65
C42 1 0.726648 0.757410 0.507823 11.00000 0.08496 0.05130 =
0.09217 0.04408 0.01365 0.00006
AFIX 43
H42 2 0.776337 0.754305 0.558501 11.00000 -1.20000
AFIX 65
C41 1 0.778771 0.748172 0.433793 11.00000 0.05825 0.04462 =
0.09605 0.03442 0.01572 0.00739
AFIX 43
H41 2 0.864084 0.738753 0.433874 11.00000 -1.20000
AFIX 0
C46 1 0.846106 0.827086 0.289816 11.00000 0.05747 0.05574 =
0.04729 0.01723 0.01216 0.01823
C47 1 0.893020 0.920527 0.364573 11.00000 0.06396 0.05276 =
0.04100 0.01730 0.01448 0.00958
AFIX 43
H47 2 0.863736 0.929574 0.417886 11.00000 -1.20000
AFIX 0
C48 1 0.982821 1.000464 0.360879 11.00000 0.08299 0.06087 =
0.05124 0.02461 0.01431 0.00350
AFIX 43
H48 2 1.014508 1.065226 0.411709 11.00000 -1.20000
AFIX 0
C49 1 1.027461 0.987647 0.284093 11.00000 0.08144 0.09566 =
0.07120 0.05293 0.02668 0.01786
AFIX 43
H49 2 1.090793 1.042987 0.282457 11.00000 -1.20000
AFIX 0
C50 1 0.979306 0.894008 0.210088 11.00000 0.08771 0.11395 =
0.05616 0.05057 0.03313 0.05347
AFIX 43
H50 2 1.008961 0.884948 0.156902 11.00000 -1.20000
AFIX 0
C51 1 0.888999 0.813608 0.212214 11.00000 0.07928 0.08101 =
0.04208 0.02197 0.01593 0.04160
AFIX 43
H51 2 0.856106 0.749126 0.160813 11.00000 -1.20000
AFIX 0
H15 2 0.747651 0.748381 0.743205 11.00000 0.03611
H6A 2 0.379029 0.712660 0.699173 11.00000 0.03545
H13 2 0.746101 0.746575 0.992480 11.00000 0.03657
H24 2 0.115624 0.463518 0.201342 11.00000 0.04322
H11 2 0.515805 0.494512 0.750413 11.00000 0.03900
H2 2 0.148178 0.456072 0.696939 11.00000 0.03681
H4 2 0.379207 0.706272 0.944113 11.00000 0.03655
H20 2 -0.123973 0.216061 -0.040805 11.00000 0.04190
H22 2 -0.115336 0.214833 0.207707 11.00000 0.04633
H12 2 0.975887 0.972347 0.912616 11.00000 0.06416
H9 2 0.456571 0.445405 0.918661 11.00000 0.05835
H6 2 0.602480 0.934476 0.874088 11.00000 0.08134
H17 2 -0.348562 -0.010224 0.035809 11.00000 0.08455
H3 2 0.073689 0.411772 0.867726 11.00000 0.08549
H14 2 0.181862 0.512325 0.032315 11.00000 0.07276
H8 2 0.464121 0.447910 0.534148 11.00000 0.40577
H1 2 0.216325 0.541417 0.478839 11.00000 0.16307
H16 2 0.048330 0.379953 0.418445 11.00000 0.17773
HKLF 4
REM PC_HT_1_ii329.res in P-1
REM R1 = 0.0429 for 8999 Fo > 4sig(Fo) and 0.0559 for all 12320 data
REM 700 parameters refined using 196 restraints
END
WGHT 0.0885 0.0273
REM Highest difference peak 0.306, deepest hole -0.380, 1-sigma level 0.110
Q1 1 0.4350 0.9191 0.6481 11.00000 0.05 0.31
Q2 1 0.6375 0.7700 0.5011 11.00000 0.05 0.30
Q3 1 0.4368 0.7714 0.8516 11.00000 0.05 0.27
Q4 1 0.5991 0.5856 0.9028 11.00000 0.05 0.26
Q5 1 0.9762 0.8496 0.2334 11.00000 0.05 0.26
Q6 1 0.6425 0.7719 0.3669 11.00000 0.05 0.25
Q7 1 0.5081 1.0321 0.6996 11.00000 0.05 0.25
Q8 1 0.6059 0.5902 0.7561 11.00000 0.05 0.24
Q9 1 0.8087 0.8102 0.8967 11.00000 0.05 0.24
Q10 1 0.5963 1.0997 0.7387 11.00000 0.05 0.24
Q11 1 0.5588 0.7473 0.3957 11.00000 0.05 0.24
Q12 1 -0.1840 0.1506 0.0509 11.00000 0.05 0.23
Q13 1 0.3035 0.8076 0.5379 11.00000 0.05 0.23
Q14 1 0.8038 0.9507 0.4253 11.00000 0.05 0.23
Q15 1 0.1544 0.6473 0.3861 11.00000 0.05 0.22
Q16 1 0.6452 0.8031 0.6095 11.00000 0.05 0.22
Q17 1 0.5854 0.7779 0.4583 11.00000 0.05 0.22
Q18 1 0.2365 0.5483 0.8558 11.00000 0.05 0.21
Q19 1 0.9421 1.0970 0.3034 11.00000 0.05 0.21
Q20 1 0.3601 0.8875 0.5586 11.00000 0.05 0.21
;
_shelx_res_checksum 8088
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_8-35_butanol-1-3-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915314'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2018-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6, 5.38(H2 O)'
_chemical_formula_sum 'C9 H16.75 O11.38'
_chemical_formula_weight 306.97
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 12
_space_group_name_H-M_alt 'C 1 2/m 1'
_space_group_name_Hall '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
_cell_length_a 25.768(4)
_cell_length_b 16.425(2)
_cell_length_c 3.6006(5)
_cell_angle_alpha 90
_cell_angle_beta 93.333(4)
_cell_angle_gamma 90
_cell_volume 1521.3(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3371
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.450
_cell_measurement_theta_min 2.480
_shelx_estimated_absorpt_T_max 0.987
_shelx_estimated_absorpt_T_min 0.974
_exptl_absorpt_coefficient_mu 0.127
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4482
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1020 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.6013. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.340
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 647
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0521
_diffrn_reflns_av_unetI/netI 0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 4
_diffrn_reflns_limit_l_min -4
_diffrn_reflns_number 8267
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.371
_diffrn_reflns_theta_min 2.480
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1293
_reflns_number_total 1618
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.588
_refine_diff_density_min -0.433
_refine_diff_density_rms 0.118
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.785
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 115
_refine_ls_number_reflns 1618
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1014
_refine_ls_R_factor_gt 0.0887
_refine_ls_restrained_S_all 1.785
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2374
_refine_ls_wR_factor_ref 0.2458
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All O(H) groups
2. Others
Fixed Sof: H1(0.5) O1W(0.25) O2W(0.25) O3W(0.25) O4W(0.25) O5W(0.5) O6W(0.25)
O7W(0.5) O8W(0.25) O9W(0.125) O10W(0.0625)
3.a Aromatic/amide H refined with riding coordinates:
C3(H3), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45458(7) 0.56825(12) 0.8180(6) 0.0373(6) Uani 1 1 d . . . . .
H1 H 0.4855 0.5613 0.8999 0.056 Uiso 0.5 1 calc GR . . . .
O2 O 0.30514(7) 0.71676(11) 0.2787(5) 0.0335(6) Uani 1 1 d . . . . .
H2 H 0.2902 0.7575 0.1808 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.23999(6) 0.65025(11) -0.0300(5) 0.0311(6) Uani 1 1 d . . . . .
C1 C 0.43416(12) 0.5000 0.7382(9) 0.0236(8) Uani 1 2 d S T P . .
C2 C 0.38133(12) 0.5000 0.5434(9) 0.0238(8) Uani 1 2 d S T P . .
C3 C 0.35683(10) 0.57359(15) 0.4546(7) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.3737 0.6237 0.5155 0.030 Uiso 1 1 calc R . . . .
C4 C 0.30752(9) 0.57324(14) 0.2761(7) 0.0227(6) Uani 1 1 d . . . . .
C5 C 0.28131(9) 0.65110(15) 0.1646(7) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.28262(13) 0.5000 0.1860(9) 0.0227(7) Uani 1 2 d S T P . .
H6 H 0.2489 0.5000 0.0639 0.027 Uiso 1 2 calc RS T P . .
O1W O 0.1500(12) 0.5000 0.498(9) 0.289(19) Uani 0.5 2 d S T P A 1
O2W O 0.1465(6) 0.5000 0.056(10) 0.225(11) Uani 0.5 2 d S T P B 2
O3W O 0.1182(19) 0.581(3) -0.014(12) 0.233(15) Uiso 0.25 1 d . . . C 3
O4W O 0.489(2) 0.763(4) 1.249(13) 0.30(2) Uiso 0.25 1 d . . . D 4
O5W O 0.4202(13) 0.783(2) 0.809(13) 0.307(15) Uiso 0.5 1 d . . . E 5
O6W O 0.4270(12) 0.774(2) 1.059(14) 0.171(10) Uiso 0.25 1 d . . . F 6
O7W O 0.4300(7) 0.7760(12) 0.419(8) 0.212(6) Uiso 0.5 1 d . . . G 7
O8W O 0.3949(16) 0.877(2) 0.581(11) 0.217(13) Uiso 0.25 1 d . . . H 8
O9W O 0.4963(17) 1.0000 0.345(9) 0.178(15) Uiso 0.25 2 d S T P I 9
O10W O 0.5000 1.0000 0.0000 0.22(3) Uiso 0.25 4 d S T P J 10
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0269(10) 0.0407(13) 0.0425(12) 0.0004(9) -0.0147(8) -0.0063(8)
O2 0.0348(10) 0.0219(11) 0.0418(11) 0.0008(8) -0.0135(8) -0.0013(8)
O3 0.0277(10) 0.0274(11) 0.0365(10) -0.0001(7) -0.0136(7) 0.0022(7)
C1 0.0204(15) 0.0274(19) 0.0224(16) 0.000 -0.0031(12) 0.000
C2 0.0196(16) 0.0306(19) 0.0205(15) 0.000 -0.0039(12) 0.000
C3 0.0254(12) 0.0269(14) 0.0210(11) -0.0011(9) -0.0037(9) -0.0035(9)
C4 0.0243(12) 0.0224(14) 0.0209(11) -0.0008(9) -0.0038(9) 0.0007(9)
C5 0.0239(12) 0.0242(14) 0.0244(12) 0.0002(9) -0.0045(9) -0.0010(9)
C6 0.0217(15) 0.0254(18) 0.0204(15) 0.000 -0.0058(12) 0.000
O1W 0.17(2) 0.48(6) 0.20(3) 0.000 -0.07(2) 0.000
O2W 0.060(7) 0.24(3) 0.37(4) 0.000 -0.016(13) 0.000
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.264(2) . ?
O2 H2 0.8400 . ?
O2 C5 1.296(3) . ?
O3 C5 1.240(3) . ?
C1 O1 1.264(2) 6_565 ?
C1 C2 1.495(4) . ?
C2 C3 1.392(3) 6_565 ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C5 1.490(3) . ?
C4 C6 1.393(3) . ?
C6 C4 1.393(3) 6_565 ?
C6 H6 0.9500 . ?
O9W O9W 1.12(7) 5_676 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
O1 C1 O1 124.9(3) . 6_565 ?
O1 C1 C2 117.53(16) . . ?
O1 C1 C2 117.54(16) 6_565 . ?
C3 C2 C1 119.75(15) . . ?
C3 C2 C1 119.76(15) 6_565 . ?
C3 C2 C3 120.5(3) . 6_565 ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 C6 120.5(2) . . ?
C6 C4 C5 118.9(2) . . ?
O2 C5 C4 115.5(2) . . ?
O3 C5 O2 124.3(2) . . ?
O3 C5 C4 120.2(2) . . ?
C4 C6 C4 119.5(3) . 6_565 ?
C4 C6 H6 120.3 6_565 . ?
C4 C6 H6 120.3 . . ?
_shelx_res_file
;
pc_ht_1_i836.res created by SHELXL-2014/7
TITL pc_ht_1_i836_a.res in C2/m
REM Old TITL pc_ht_1_i836_a.res in C2/m
REM SHELXT solution in C2/m
REM R1 0.195, Rweak 0.008, Alpha 0.072, Orientation as input
REM Formula found by SHELXT: C9 O6
CELL 0.71073 25.7678 16.4251 3.6006 90 93.333 90
ZERR 4 0.0035 0.0024 0.0005 0 0.004 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O
UNIT 36 67 45.5
L.S. 20
PLAN 20
SIZE 0.21 0.1 0.11
TEMP -173.15
BOND $H
list 4
fmap 2 53
acta
SHEL 999 0.8
OMIT 9 3 0
OMIT 1 1 0
REM
REM
REM
WGHT 0.100000
FVAR 0.60450
O1 3 0.454584 0.568245 0.817966 11.00000 0.02689 0.04069 =
0.04247 0.00042 -0.01466 -0.00632
AFIX 147
H1 2 0.485460 0.561343 0.899898 10.50000 -1.50000
AFIX 0
O2 3 0.305137 0.716759 0.278668 11.00000 0.03478 0.02192 =
0.04184 0.00081 -0.01355 -0.00134
AFIX 147
H2 2 0.290180 0.757542 0.180822 11.00000 -1.50000
AFIX 0
O3 3 0.239992 0.650254 -0.030038 11.00000 0.02766 0.02739 =
0.03648 -0.00008 -0.01356 0.00216
C1 1 0.434162 0.500000 0.738236 10.50000 0.02043 0.02744 =
0.02235 0.00000 -0.00305 0.00000
C2 1 0.381332 0.500000 0.543415 10.50000 0.01962 0.03065 =
0.02050 0.00000 -0.00387 0.00000
C3 1 0.356829 0.573590 0.454605 11.00000 0.02536 0.02691 =
0.02103 -0.00105 -0.00368 -0.00349
AFIX 43
H3 2 0.373685 0.623678 0.515517 11.00000 -1.20000
AFIX 0
C4 1 0.307517 0.573239 0.276146 11.00000 0.02430 0.02236 =
0.02087 -0.00081 -0.00381 0.00068
C5 1 0.281308 0.651105 0.164638 11.00000 0.02385 0.02421 =
0.02437 0.00016 -0.00450 -0.00098
C6 1 0.282615 0.500000 0.185951 10.50000 0.02167 0.02536 =
0.02036 0.00000 -0.00577 0.00000
AFIX 43
H6 2 0.248922 0.500001 0.063907 10.50000 -1.20000
AFIX 0
PART 1
O1W 3 0.150037 0.500000 0.497519 10.25000 0.17023 0.48241 =
0.20470 0.00000 -0.06766 0.00000
PART 0
PART 2
O2W 3 0.146535 0.500000 0.055983 10.25000 0.05978 0.24479 =
0.36678 0.00000 -0.01572 0.00000
PART 0
PART 3
O3W 3 0.118191 0.580645 -0.014114 10.25000 0.23279
PART 0
PART 4
O4W 3 0.489455 0.762799 1.248613 10.25000 0.29628
PART 0
PART 5
O5W 3 0.420217 0.783336 0.809377 10.50000 0.30704
PART 0
PART 6
O6W 3 0.427021 0.774464 1.059245 10.25000 0.17091
PART 0
PART 7
O7W 3 0.430014 0.776043 0.418899 10.50000 0.21234
PART 0
PART 8
O8W 3 0.394916 0.876548 0.581461 10.25000 0.21720
PART 0
PART 9
O9W 3 0.496335 1.000000 0.345431 10.12500 0.17819
PART 0
PART 10
O10W 3 0.500000 1.000000 0.000000 10.06250 0.22186
HKLF 4
REM pc_ht_1_i836_a.res in C2/m
REM R1 = 0.0887 for 1293 Fo > 4sig(Fo) and 0.1014 for all 1618 data
REM 115 parameters refined using 0 restraints
END
WGHT 0.1853 1.4093
REM Highest difference peak 0.588, deepest hole -0.433, 1-sigma level 0.118
Q1 1 0.5210 0.7615 1.0541 11.00000 0.05 0.53
Q2 1 0.0994 0.5000 0.4017 10.50000 0.05 0.51
Q3 1 0.3776 0.9152 0.5009 11.00000 0.05 0.46
Q4 1 0.3381 0.5000 0.3476 10.50000 0.05 0.46
Q5 1 0.4236 0.7822 0.6993 11.00000 0.05 0.45
Q6 1 0.3888 0.8847 0.3062 11.00000 0.05 0.45
Q7 1 0.4014 0.8484 0.6102 11.00000 0.05 0.44
Q8 1 0.4217 0.9205 0.6913 11.00000 0.05 0.43
Q9 1 0.3969 0.8538 0.7763 11.00000 0.05 0.43
Q10 1 0.3991 0.8393 0.9886 11.00000 0.05 0.43
Q11 1 0.3032 0.5935 0.2216 11.00000 0.05 0.42
Q12 1 0.2786 0.8053 0.1269 11.00000 0.05 0.40
Q13 1 0.4786 1.0734 -0.0933 11.00000 0.05 0.36
Q14 1 0.2587 0.5776 0.0361 11.00000 0.05 0.34
Q15 1 0.3830 0.6559 0.5548 11.00000 0.05 0.34
Q16 1 0.4517 1.0000 -0.1702 10.50000 0.05 0.32
Q17 1 0.4374 0.9623 0.6595 11.00000 0.05 0.31
Q18 1 0.3783 0.9057 0.7442 11.00000 0.05 0.31
Q19 1 0.3374 0.6527 0.3657 11.00000 0.05 0.30
Q20 1 0.3605 0.7198 0.4339 11.00000 0.05 0.29
;
_shelx_res_checksum 97662
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_tma_8-32_butanol_mesitylene_100k
_database_code_depnum_ccdc_archive 'CCDC 1915313'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C9 H6 O6), 8(O)'
_chemical_formula_sum 'C18 H12 O20'
_chemical_formula_weight 548.28
_chemical_absolute_configuration ?
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system trigonal
_space_group_IT_number 154
_space_group_name_H-M_alt 'P 32 2 1'
_space_group_name_Hall 'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'
_cell_length_a 16.5230(16)
_cell_length_b 16.5230(16)
_cell_length_c 19.400(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 4586.9(10)
_cell_formula_units_Z 6
_cell_measurement_reflns_used 7663
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.13
_cell_measurement_theta_min 2.47
_shelx_estimated_absorpt_T_max 0.996
_shelx_estimated_absorpt_T_min 0.985
_exptl_absorpt_coefficient_mu 0.113
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4679
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS
Estimated minimum and maximum transmission: 0.4679 0.7454
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r = 0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.191
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1680
_exptl_crystal_size_max 0.134
_exptl_crystal_size_mid 0.063
_exptl_crystal_size_min 0.039
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0919
_diffrn_reflns_av_unetI/netI 0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 25344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.373
_diffrn_reflns_theta_min 1.050
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.809
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 1.000
_reflns_number_gt 3656
_reflns_number_total 6239
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution ?
_refine_diff_density_max 0.379
_refine_diff_density_min -0.312
_refine_diff_density_rms 0.071
_refine_ls_abs_structure_details
;
Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -0.3(10)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.981
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 363
_refine_ls_number_reflns 6239
_refine_ls_number_restraints 230
_refine_ls_R_factor_all 0.1344
_refine_ls_R_factor_gt 0.0777
_refine_ls_restrained_S_all 0.977
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1325P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1893
_refine_ls_wR_factor_ref 0.2266
_refine_special_details
;
Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.541(4)
0.459(4)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
3. Restrained distances
O10-H10
0.83 with sigma of 0.01
O4-H4 = O1-H1
0.83 with sigma of 0.01
O6-H6
0.83 with sigma of 0.01
H11-O12
2.25 with sigma of 0.02
C17-H10
1.84 with sigma of 0.02
H12-C18
1.84 with sigma of 0.02
C16-H7
1.84 with sigma of 0.02
4. Restrained planarity
O9, O10, C17, H10
with sigma of 0.001
O11, O12, C18, H11, H12
with sigma of 0.001
O7, O8, C16, H7
with sigma of 0.001
O3, O4, C8, H4, H3
with sigma of 0.001
5. Rigid body (RIGU) restrains
All non-hydrogen atoms
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
Fixed Sof: H3(0.5) H4(0.5) O1S(0.5) O2S(0.5) O3S(0.5) O4S(0.5) O5S(0.5)
O6S(0.25) O7S(0.5) H11(0.5) H12(0.5) O8S(0.5) O9S(0.5) O10S(0.5) O11S(0.5)
O12S(0.25) O13S(0.25) O14S(0.5) O15S(0.5) O16S(0.5) O17S(0.25) O18S(0.25)
O19S(0.25)
7.a Aromatic/amide H refined with riding coordinates:
C2(H2), C4(H4A), C6(H6A), C11(H11A), C13(H13), C15(H15)
7.b Idealised tetrahedral OH refined as rotating group:
O3(H3), O7(H7), O11(H11), O12(H12)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0224(4) 0.4998(5) 0.5061(4) 0.0291(16) Uani 1 1 d D U . . .
O2 O -0.0254(4) 0.3635(5) 0.5022(5) 0.046(2) Uani 1 1 d . U . . .
O3 O 0.2727(5) 0.3637(5) 0.5046(4) 0.0351(16) Uani 1 1 d . U . . .
H3 H 0.3098 0.3430 0.5014 0.053 Uiso 0.5 1 calc GR . . . .
O4 O 0.4073(5) 0.4996(5) 0.5049(4) 0.0357(19) Uani 1 1 d D U . . .
O5 O 0.4072(4) 0.7957(4) 0.4994(4) 0.0238(13) Uani 1 1 d . U . . .
O6 O 0.2718(5) 0.7927(5) 0.5008(5) 0.0390(19) Uani 1 1 d D U . . .
C1 C 0.1212(5) 0.5025(7) 0.5063(5) 0.0232(16) Uani 1 1 d . U . . .
C2 C 0.1687(7) 0.4533(6) 0.5073(4) 0.0236(16) Uani 1 1 d . U . . .
H2 H 0.1356 0.3869 0.5088 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2666(7) 0.5034(6) 0.5062(4) 0.0210(16) Uani 1 1 d . U . . .
C4 C 0.3157(6) 0.5972(7) 0.5049(4) 0.0218(16) Uani 1 1 d . U . . .
H4A H 0.3821 0.6293 0.5052 0.026 Uiso 1 1 calc R . . . .
C5 C 0.2669(6) 0.6478(6) 0.5029(4) 0.0203(16) Uani 1 1 d . U . . .
C6 C 0.1700(7) 0.6010(7) 0.5019(5) 0.0256(19) Uani 1 1 d . U . . .
H6A H 0.1372 0.6344 0.4984 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0165(6) 0.4512(8) 0.5051(4) 0.0234(16) Uani 1 1 d . U . . .
C8 C 0.3178(8) 0.4505(7) 0.5070(4) 0.0274(19) Uani 1 1 d . U . . .
C9 C 0.3184(7) 0.7525(5) 0.4999(4) 0.0186(14) Uani 1 1 d . U . . .
H1 H -0.079(2) 0.479(6) 0.497(5) 0.028 Uiso 1 1 d DR . . . .
H4 H 0.440(9) 0.475(10) 0.5017(9) 0.028 Uiso 0.5 1 d DR . . . .
H6 H 0.310(5) 0.8489(19) 0.493(5) 0.028 Uiso 1 1 d DR . . . .
O1S O 0.7593(19) 0.5898(19) 0.4658(14) 0.126(9) Uiso 0.5 1 d . U . A 1
O2S O 0.749(3) 0.623(3) 0.511(2) 0.177(12) Uiso 0.5 1 d . U . B 2
O3S O 0.777(2) 0.673(2) 0.5845(14) 0.151(9) Uiso 0.5 1 d . U . C 3
O4S O 0.811(3) 0.764(3) 0.706(2) 0.222(17) Uiso 0.5 1 d . U . D 4
O5S O 0.7661(18) 0.7225(19) 0.6400(15) 0.130(9) Uiso 0.5 1 d . U . E 5
O6S O 0.6762(14) 0.6762(14) 0.5000 0.068(6) Uiso 0.5 2 d S TU P F 6
O7S O 0.708(3) 0.649(3) 0.457(2) 0.181(13) Uiso 0.5 1 d . U . G 7
O7 O 0.4217(4) 0.3890(5) 0.6560(4) 0.0347(17) Uani 1 1 d . U . . .
H7 H 0.4004 0.4256 0.6589 0.052 Uiso 1 1 calc DGR . . . .
O8 O 0.5572(5) 0.5222(5) 0.6659(4) 0.0399(19) Uani 1 1 d . U . . .
O9 O 0.8533(4) 0.5223(5) 0.6671(3) 0.0275(14) Uani 1 1 d . U . . .
O10 O 0.8503(5) 0.3851(5) 0.6599(4) 0.0400(18) Uani 1 1 d D U . . .
O11 O 0.5577(5) 0.0914(4) 0.6677(4) 0.0351(17) Uani 1 1 d . U . . .
H11 H 0.5211 0.0334 0.6658 0.053 Uiso 0.5 1 calc DGR . . . .
O12 O 0.4213(5) 0.0917(5) 0.6665(5) 0.051(2) Uani 1 1 d D U . . .
H12 H 0.4002 0.0338 0.6648 0.076 Uiso 0.5 1 calc DGR . . . .
C10 C 0.5602(7) 0.3823(7) 0.6597(5) 0.0275(18) Uani 1 1 d . U . . .
C11 C 0.6586(7) 0.4313(6) 0.6585(4) 0.0231(15) Uani 1 1 d . U . . .
H11A H 0.6922 0.4976 0.6565 0.028 Uiso 1 1 calc R . . . .
C12 C 0.7067(6) 0.3811(7) 0.6603(4) 0.0203(15) Uani 1 1 d . U . . .
C13 C 0.6587(7) 0.2860(7) 0.6623(4) 0.0224(17) Uani 1 1 d . U . . .
H13 H 0.6923 0.2532 0.6610 0.027 Uiso 1 1 calc R . . . .
C14 C 0.5614(7) 0.2358(6) 0.6660(4) 0.0235(15) Uani 1 1 d . U . . .
C15 C 0.5123(6) 0.2840(6) 0.6622(4) 0.0193(16) Uani 1 1 d . U . . .
H15 H 0.4459 0.2502 0.6612 0.023 Uiso 1 1 calc R . . . .
C16 C 0.5117(7) 0.4361(7) 0.6594(4) 0.0228(17) Uani 1 1 d D U . . .
C17 C 0.8106(6) 0.4326(7) 0.6629(4) 0.0223(17) Uani 1 1 d D U . . .
C18 C 0.5102(7) 0.1340(6) 0.6684(4) 0.0260(17) Uani 1 1 d D U . . .
H10 H 0.9084(12) 0.409(3) 0.6605(9) 0.03(3) Uiso 1 1 d D . . . .
O8S O 0.931(3) 0.893(3) 0.514(3) 0.27(2) Uiso 0.5 1 d . U . H 8
O9S O 0.234(3) 0.121(3) 0.616(2) 0.226(18) Uiso 0.5 1 d . U . I 9
O10S O 0.731(4) 0.793(4) 0.700(2) 0.238(17) Uiso 0.5 1 d . U . J 10
O11S O 0.024(4) 0.726(4) 0.385(3) 0.29(2) Uiso 0.5 1 d . U . K 11
O12S O 0.012(7) 0.179(6) 0.381(4) 0.20(3) Uiso 0.25 1 d . U . L 12
O13S O 0.134(3) 0.165(3) 0.383(2) 0.087(11) Uiso 0.25 1 d . U . M 13
O14S O 0.152(3) 0.237(3) 0.314(2) 0.193(14) Uiso 0.5 1 d . U . N 14
O15S O 0.285(2) 0.225(2) 0.7875(17) 0.141(9) Uiso 0.5 1 d . U . O 15
O16S O 0.286(3) 0.231(3) 0.871(2) 0.195(14) Uiso 0.5 1 d . U . P 16
O17S O 0.142(3) 0.924(3) 0.580(2) 0.101(13) Uiso 0.25 1 d . U . Q 17
O18S O 0.111(5) 0.889(5) 0.498(4) 0.19(3) Uiso 0.25 1 d . U . R 18
O19S O 0.835(5) 0.826(5) 0.345(4) 0.19(3) Uiso 0.25 1 d . U . S 19
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.019(3) 0.033(4) 0.035(4) -0.001(3) -0.003(3) 0.013(3)
O2 0.027(4) 0.025(3) 0.075(5) -0.004(3) 0.006(4) 0.005(3)
O3 0.036(4) 0.030(3) 0.045(4) 0.001(3) 0.007(4) 0.020(2)
O4 0.022(3) 0.037(4) 0.048(5) 0.004(4) 0.001(3) 0.015(3)
O5 0.023(3) 0.017(3) 0.026(3) 0.000(3) 0.003(3) 0.006(2)
O6 0.028(3) 0.021(3) 0.070(5) 0.010(4) 0.010(4) 0.015(3)
C1 0.023(3) 0.024(3) 0.022(4) 0.005(3) 0.003(3) 0.012(3)
C2 0.027(3) 0.026(3) 0.015(4) 0.005(3) 0.004(3) 0.011(3)
C3 0.024(3) 0.021(3) 0.016(4) -0.001(3) 0.001(3) 0.010(3)
C4 0.020(3) 0.021(3) 0.020(4) -0.001(3) -0.002(3) 0.007(3)
C5 0.020(3) 0.019(3) 0.018(4) 0.001(2) 0.003(3) 0.007(2)
C6 0.022(3) 0.024(3) 0.030(5) 0.003(3) 0.002(3) 0.011(3)
C7 0.023(3) 0.026(3) 0.019(4) -0.001(3) 0.001(3) 0.010(3)
C8 0.021(3) 0.026(3) 0.036(5) -0.003(3) 0.002(3) 0.012(3)
C9 0.022(3) 0.021(3) 0.013(3) -0.002(2) 0.004(3) 0.011(3)
O7 0.024(3) 0.035(3) 0.051(5) -0.009(3) -0.007(3) 0.019(2)
O8 0.037(4) 0.027(3) 0.059(5) -0.004(3) -0.011(4) 0.019(3)
O9 0.029(3) 0.023(3) 0.028(3) 0.001(3) -0.004(3) 0.011(2)
O10 0.025(3) 0.035(4) 0.061(5) -0.003(4) -0.003(3) 0.016(3)
O11 0.042(4) 0.025(3) 0.037(4) 0.002(3) -0.003(3) 0.016(3)
O12 0.028(3) 0.025(3) 0.091(6) -0.004(4) 0.002(3) 0.007(2)
C10 0.028(3) 0.027(3) 0.031(5) -0.001(3) -0.003(3) 0.016(3)
C11 0.029(3) 0.023(3) 0.019(4) -0.001(3) -0.001(3) 0.014(3)
C12 0.023(3) 0.023(3) 0.015(4) -0.004(3) -0.003(2) 0.012(2)
C13 0.025(3) 0.025(3) 0.017(4) -0.004(3) -0.009(3) 0.013(3)
C14 0.022(3) 0.028(3) 0.018(3) 0.000(2) -0.007(3) 0.011(3)
C15 0.021(3) 0.027(3) 0.009(3) 0.000(3) -0.003(3) 0.011(3)
C16 0.025(3) 0.023(3) 0.021(4) -0.002(3) -0.006(3) 0.013(2)
C17 0.021(3) 0.020(3) 0.022(4) -0.001(3) -0.001(3) 0.008(3)
C18 0.026(3) 0.028(3) 0.021(4) 0.001(3) 0.000(3) 0.012(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.254(12) . ?
O1 H1 0.833(14) . ?
O2 C7 1.257(13) . ?
O3 H3 0.8400 . ?
O3 C8 1.244(12) . ?
O4 C8 1.284(13) . ?
O4 H4 0.832(14) . ?
O5 C9 1.271(11) . ?
O6 C9 1.244(12) . ?
O6 H6 0.834(14) . ?
C1 C2 1.384(14) . ?
C1 C6 1.412(14) . ?
C1 C7 1.499(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(13) . ?
C3 C4 1.343(13) . ?
C3 C8 1.489(12) . ?
C4 H4A 0.9500 . ?
C4 C5 1.424(13) . ?
C5 C6 1.387(12) . ?
C5 C9 1.500(10) . ?
C6 H6A 0.9500 . ?
O7 H7 0.8400 . ?
O7 C16 1.290(11) . ?
O8 C16 1.239(12) . ?
O9 C17 1.286(11) . ?
O10 C17 1.252(12) . ?
O10 H10 0.836(14) . ?
O11 H11 0.8400 . ?
O11 C18 1.290(13) . ?
O12 H12 0.8400 . ?
O12 C18 1.274(12) . ?
C10 C11 1.407(13) . ?
C10 C15 1.408(13) . ?
C10 C16 1.465(11) . ?
C11 H11A 0.9500 . ?
C11 C12 1.407(12) . ?
C12 C13 1.362(12) . ?
C12 C17 1.487(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(13) . ?
C14 C15 1.394(13) . ?
C14 C18 1.458(11) . ?
C15 H15 0.9500 . ?
O8S O8S 1.24(9) 6_556 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 124(7) . . ?
C8 O3 H3 109.5 . . ?
C8 O4 H4 121(10) . . ?
C9 O6 H6 106(6) . . ?
C2 C1 C6 121.0(8) . . ?
C2 C1 C7 120.1(10) . . ?
C6 C1 C7 118.9(10) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C8 118.7(9) . . ?
C4 C3 C2 122.3(8) . . ?
C4 C3 C8 119.0(9) . . ?
C3 C4 H4A 120.5 . . ?
C3 C4 C5 119.1(8) . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C9 121.1(9) . . ?
C6 C5 C4 120.5(8) . . ?
C6 C5 C9 118.3(8) . . ?
C1 C6 H6A 120.8 . . ?
C5 C6 C1 118.4(9) . . ?
C5 C6 H6A 120.8 . . ?
O1 C7 O2 125.1(7) . . ?
O1 C7 C1 117.0(10) . . ?
O2 C7 C1 117.9(10) . . ?
O3 C8 O4 124.3(8) . . ?
O3 C8 C3 119.2(10) . . ?
O4 C8 C3 116.3(9) . . ?
O5 C9 C5 118.6(9) . . ?
O6 C9 O5 123.4(7) . . ?
O6 C9 C5 118.0(9) . . ?
C16 O7 H7 109.5 . . ?
C17 O10 H10 123(3) . . ?
C18 O11 H11 109.5 . . ?
C18 O12 H12 109.5 . . ?
C11 C10 C15 119.0(8) . . ?
C11 C10 C16 118.4(9) . . ?
C15 C10 C16 122.5(9) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C17 119.6(9) . . ?
C13 C12 C11 120.4(9) . . ?
C13 C12 C17 119.9(8) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(9) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C18 121.3(10) . . ?
C15 C14 C13 119.0(8) . . ?
C15 C14 C18 119.6(10) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(8) . . ?
C14 C15 H15 119.7 . . ?
O7 C16 C10 116.7(9) . . ?
O8 C16 O7 123.6(8) . . ?
O8 C16 C10 119.6(9) . . ?
O9 C17 C12 118.3(9) . . ?
O10 C17 O9 124.6(7) . . ?
O10 C17 C12 117.2(8) . . ?
O11 C18 C14 118.0(10) . . ?
O12 C18 O11 123.4(7) . . ?
O12 C18 C14 118.4(10) . . ?
_shelx_res_file
;
tma_8-32_butanol_mesitylene_100k.res created by SHELXL-2014/7
TITL trig_a.res in P3(2)21
REM Old TITL Trig in P-3
REM SHELXT solution in P3(2)21
REM R1 0.406, Rweak 0.031, Alpha 0.371, Orientation as input
REM Flack x = 0.466 ( 0.070 ) from Parsons' quotients
REM Formula found by SHELXT: C36 Cl
CELL 0.71073 16.523 16.523 19.4003 90 90 120
ZERR 6 0.0016 0.0016 0.002 0 0 0
LATT -1
SYMM -Y,+X-Y,0.667+Z
SYMM +Y-X,-X,0.333+Z
SYMM -Y+X,-Y,0.333-Z
SYMM -X,-X+Y,0.667-Z
SYMM +Y,+X,-Z
SFAC C H O
UNIT 108 72 120
DFIX 0.83 0.01 O10 H10
DFIX 0.83 0.01 O4 H4 O1 H1
DFIX 0.83 0.01 O6 H6
DANG 2.25 0.02 H11 O12
DANG 1.84 0.02 C17 H10
DANG 1.84 0.02 H12 C18
DANG 1.84 0.02 C16 H7
FLAT 0.001 O9 O10 C17 H10
FLAT 0.001 O11 O12 C18 H11 H12
FLAT 0.001 O7 O8 C16 H7
FLAT 0.001 O3 O4 C8 H4 H3
RIGU 0.002 0.002
L.S. 99
PLAN 20
SIZE 0.134 0.063 0.039
TEMP -173.15
BOND $H
list 4
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 1 2
OMIT 0 1 0
OMIT 0 1 1
REM
REM
REM
WGHT 0.132500
BASF 0.45906
FVAR 0.33006
O1 3 -0.022366 0.499804 0.506142 11.00000 0.01948 0.03320 =
0.03507 -0.00084 -0.00319 0.01347
O2 3 -0.025416 0.363513 0.502184 11.00000 0.02716 0.02460 =
0.07460 -0.00352 0.00564 0.00503
O3 3 0.272685 0.363669 0.504570 11.00000 0.03552 0.02992 =
0.04501 0.00138 0.00675 0.02011
AFIX 147
H3 2 0.309815 0.343036 0.501371 10.50000 -1.50000
AFIX 0
O4 3 0.407301 0.499587 0.504877 11.00000 0.02203 0.03708 =
0.04820 0.00446 0.00054 0.01494
O5 3 0.407207 0.795737 0.499419 11.00000 0.02328 0.01691 =
0.02600 0.00011 0.00283 0.00607
O6 3 0.271780 0.792699 0.500799 11.00000 0.02845 0.02146 =
0.06991 0.00976 0.01011 0.01468
C1 1 0.121246 0.502533 0.506308 11.00000 0.02297 0.02405 =
0.02230 0.00459 0.00276 0.01155
C2 1 0.168717 0.453282 0.507346 11.00000 0.02693 0.02585 =
0.01541 0.00452 0.00442 0.01114
AFIX 43
H2 2 0.135622 0.386922 0.508807 11.00000 -1.20000
AFIX 0
C3 1 0.266595 0.503371 0.506198 11.00000 0.02411 0.02127 =
0.01593 -0.00144 0.00134 0.01011
C4 1 0.315713 0.597189 0.504879 11.00000 0.02038 0.02090 =
0.01990 -0.00112 -0.00164 0.00717
AFIX 43
H4A 2 0.382090 0.629307 0.505238 11.00000 -1.20000
AFIX 0
C5 1 0.266868 0.647814 0.502937 11.00000 0.02044 0.01852 =
0.01810 0.00110 0.00270 0.00690
C6 1 0.169965 0.601015 0.501918 11.00000 0.02182 0.02439 =
0.03021 0.00326 0.00180 0.01127
AFIX 43
H6A 2 0.137165 0.634428 0.498353 11.00000 -1.20000
AFIX 0
C7 1 0.016532 0.451222 0.505141 11.00000 0.02281 0.02575 =
0.01853 -0.00119 0.00144 0.00987
C8 1 0.317778 0.450529 0.507008 11.00000 0.02080 0.02570 =
0.03581 -0.00262 0.00150 0.01161
C9 1 0.318430 0.752531 0.499948 11.00000 0.02228 0.02088 =
0.01270 -0.00189 0.00351 0.01073
H1 2 -0.078667 0.479256 0.497320 11.00000 -1.50000
H4 2 0.440163 0.474675 0.501671 10.50000 -1.50000
H6 2 0.309556 0.848914 0.492910 11.00000 -1.50000
PART 1
O1S 3 0.759316 0.589796 0.465785 10.50000 0.12635
PART 0
PART 2
O2S 3 0.749311 0.622565 0.510914 10.50000 0.17662
PART 0
PART 3
O3S 3 0.776711 0.672626 0.584534 10.50000 0.15073
PART 0
PART 4
O4S 3 0.810600 0.764064 0.706423 10.50000 0.22241
PART 0
PART 5
O5S 3 0.766140 0.722470 0.639997 10.50000 0.12956
PART 0
PART 6
O6S 3 0.676157 0.676157 0.500000 10.25000 0.06828
PART 0
PART 7
O7S 3 0.707576 0.648552 0.456852 10.50000 0.18136
PART 0
O7 3 0.421720 0.388980 0.655999 11.00000 0.02409 0.03459 =
0.05114 -0.00926 -0.00670 0.01903
AFIX 147
H7 2 0.400403 0.425570 0.658868 11.00000 -1.50000
AFIX 0
O8 3 0.557235 0.522230 0.665861 11.00000 0.03724 0.02718 =
0.05867 -0.00445 -0.01064 0.01864
O9 3 0.853343 0.522300 0.667135 11.00000 0.02874 0.02336 =
0.02798 0.00078 -0.00399 0.01123
O10 3 0.850286 0.385052 0.659918 11.00000 0.02488 0.03511 =
0.06118 -0.00317 -0.00279 0.01595
O11 3 0.557743 0.091384 0.667661 11.00000 0.04217 0.02482 =
0.03674 0.00186 -0.00263 0.01560
AFIX 147
H11 2 0.521052 0.033413 0.665825 10.50000 -1.50000
AFIX 0
O12 3 0.421275 0.091698 0.666540 11.00000 0.02771 0.02482 =
0.09077 -0.00425 0.00154 0.00685
AFIX 147
H12 2 0.400180 0.033751 0.664834 10.50000 -1.50000
AFIX 0
C10 1 0.560249 0.382327 0.659734 11.00000 0.02755 0.02714 =
0.03138 -0.00063 -0.00329 0.01626
C11 1 0.658581 0.431294 0.658541 11.00000 0.02872 0.02316 =
0.01881 -0.00147 -0.00112 0.01407
AFIX 43
H11A 2 0.692167 0.497627 0.656549 11.00000 -1.20000
AFIX 0
C12 1 0.706695 0.381146 0.660323 11.00000 0.02327 0.02338 =
0.01454 -0.00395 -0.00253 0.01177
C13 1 0.658746 0.286015 0.662258 11.00000 0.02499 0.02547 =
0.01711 -0.00411 -0.00863 0.01297
AFIX 43
H13 2 0.692268 0.253169 0.661006 11.00000 -1.20000
AFIX 0
C14 1 0.561420 0.235818 0.666039 11.00000 0.02219 0.02836 =
0.01789 0.00008 -0.00690 0.01110
C15 1 0.512322 0.283982 0.662196 11.00000 0.02074 0.02664 =
0.00904 -0.00005 -0.00277 0.01074
AFIX 43
H15 2 0.445948 0.250172 0.661230 11.00000 -1.20000
AFIX 0
C16 1 0.511700 0.436139 0.659374 11.00000 0.02510 0.02268 =
0.02148 -0.00214 -0.00623 0.01265
C17 1 0.810554 0.432634 0.662881 11.00000 0.02096 0.02025 =
0.02247 -0.00101 -0.00095 0.00797
C18 1 0.510233 0.133958 0.668393 11.00000 0.02637 0.02764 =
0.02143 0.00135 -0.00025 0.01154
H10 2 0.908373 0.408929 0.660523 11.00000 0.02937
PART 8
O8S 3 0.931324 0.892726 0.514487 10.50000 0.27086
PART 0
PART 9
O9S 3 0.234127 0.121184 0.615810 10.50000 0.22637
PART 0
PART 10
O10S 3 0.730726 0.792610 0.699501 10.50000 0.23809
PART 0
PART 11
O11S 3 0.024484 0.725755 0.385041 10.50000 0.28716
PART 0
PART 12
O12S 3 0.012093 0.178675 0.380776 10.25000 0.19937
PART 0
PART 13
O13S 3 0.134080 0.164940 0.382618 10.25000 0.08688
PART 0
PART 14
O14S 3 0.151786 0.236602 0.313851 10.50000 0.19292
PART 0
PART 15
O15S 3 0.284519 0.225302 0.787501 10.50000 0.14065
PART 0
PART 16
O16S 3 0.285687 0.231179 0.870527 10.50000 0.19497
PART 0
PART 17
O17S 3 0.141790 0.924349 0.579884 10.25000 0.10127
PART 0
PART 18
O18S 3 0.110738 0.888721 0.497991 10.25000 0.18789
PART 0
PART 19
O19S 3 0.835189 0.826192 0.345262 10.25000 0.19080
HKLF 4
REM trig_a.res in P3(2)21
REM R1 = 0.0777 for 3656 Fo > 4sig(Fo) and 0.1344 for all 6239 data
REM 363 parameters refined using 230 restraints
END
WGHT 0.1302 0.0000
REM Highest difference peak 0.379, deepest hole -0.312, 1-sigma level 0.071
Q1 1 0.6966 0.7526 0.6133 11.00000 0.05 0.38
Q2 1 0.8961 0.8964 0.2771 11.00000 0.05 0.31
Q3 1 0.1114 0.1496 0.4469 11.00000 0.05 0.31
Q4 1 0.0586 0.2000 0.4326 11.00000 0.05 0.27
Q5 1 0.1237 0.8719 0.4485 11.00000 0.05 0.27
Q6 1 0.0992 0.7087 0.3363 11.00000 0.05 0.26
Q7 1 0.7085 0.6466 0.5003 11.00000 0.05 0.25
Q8 1 0.8799 0.7703 0.6822 11.00000 0.05 0.25
Q9 1 0.8033 0.7170 0.6830 11.00000 0.05 0.25
Q10 1 0.8238 0.2774 0.6806 11.00000 0.05 0.24
Q11 1 0.8419 0.6497 0.4809 11.00000 0.05 0.24
Q12 1 1.0103 0.9978 0.5748 11.00000 0.05 0.24
Q13 1 0.7882 0.6754 0.7535 11.00000 0.05 0.24
Q14 1 1.0000 0.8803 0.3333 10.50000 0.05 0.24
Q15 1 0.0939 0.3141 0.5013 11.00000 0.05 0.24
Q16 1 0.1160 0.0635 0.3897 11.00000 0.05 0.23
Q17 1 0.1324 0.9427 0.5340 11.00000 0.05 0.23
Q18 1 0.1800 1.0099 0.5293 11.00000 0.05 0.23
Q19 1 0.1468 0.2591 0.4883 11.00000 0.05 0.23
Q20 1 0.7514 0.6604 0.5452 11.00000 0.05 0.23
;
_shelx_res_checksum 92153
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.541(4)
2 0.459(4)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_ADTA_2-35_THF-1-3-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915312'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2019-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '(C14 H20 O8), 17.5(O)'
_chemical_formula_sum 'C14 H20 O25.50'
_chemical_formula_weight 596.30
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system tetragonal
_space_group_IT_number 134
_space_group_name_H-M_alt 'P 42/n n m'
_space_group_name_Hall '-P 4ac 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z+1/2'
'y, -x+1/2, z+1/2'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'y, x, -z'
'-y+1/2, -x+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z-1/2'
'-y, x-1/2, -z-1/2'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'
'-y, -x, z'
'y-1/2, x-1/2, z'
_cell_length_a 11.4331(8)
_cell_length_b 11.4331(8)
_cell_length_c 11.4312(8)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1494.2(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5245
_cell_measurement_temperature 200
_cell_measurement_theta_max 26.358
_cell_measurement_theta_min 2.519
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.134
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4951
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
Estimated minimum and maximum transmission: 0.4951 0.7454
Additional spherical absorption correction applied with mu*r = 0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.325
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 616
_exptl_crystal_size_max 0.135
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.11
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0453
_diffrn_reflns_av_unetI/netI 0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 17215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.360
_diffrn_reflns_theta_min 1.781
_diffrn_ambient_temperature 200
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 682
_reflns_number_total 829
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.177
_refine_diff_density_min -0.398
_refine_diff_density_rms 0.084
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.142
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 98
_refine_ls_number_reflns 829
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0860
_refine_ls_R_factor_gt 0.0760
_refine_ls_restrained_S_all 1.148
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1228P)^2^+0.2939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1852
_refine_ls_wR_factor_ref 0.2009
_refine_special_details
;
Refined as a 2-component twin with the TWINLAW
TWIN -1 0 0 0 0 1 0 1 0 2
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.532(12)
0.468(12)
2. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
Fixed Sof: O1(0.16667) H1(0.16667) O2(0.33333) H2(0.33333) O3(0.33333)
H3(0.33333) O4(0.16667) H4(0.16667) H1A(0.5) H1B(0.5) H3B(0.25) H3A(0.25)
O1S(0.125) O3S(0.125) O4S(0.25) O6S(0.125) O7S(0.0625) O5S(0.125) O9S(0.25)
O10S(0.25) O11S(0.25) O12S(0.125) O13S(0.25) O8S(0.125) O2S(0.125)
Fixed X: H1(0.443999) H2(0.402549) H3(0.44502) H4(0.516469)
Fixed Y: H1(0.556009) H2(0.497789) H3(0.45899) H4(0.499439)
Fixed Z: H1(0.45728) H2(0.486819) H3(0.55843) H4(0.60143)
5.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C3(H3B,H3A)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3989(7) 0.6011(7) 0.4880(6) 0.066(4) Uani 0.3333 2 d S TU P A 1
H1 H 0.4440 0.5560 0.4573 0.099 Uiso 0.3333 2 d RS T P B 1
O2 O 0.3518(8) 0.5322(14) 0.5257(13) 0.088(3) Uani 0.3333 1 d . . . A 3
H2 H 0.4025 0.4978 0.4868 0.132 Uiso 0.3333 1 d R . . C 3
O3 O 0.3992(12) 0.4883(7) 0.6025(10) 0.073(3) Uani 0.3333 1 d . . . A 2
H3 H 0.4450 0.4590 0.5584 0.109 Uiso 0.3333 1 d R . . D 2
O4 O 0.4691(6) 0.5309(6) 0.6451(8) 0.079(6) Uani 0.3333 2 d S T P A 1
H4 H 0.5165 0.4994 0.6014 0.118 Uiso 0.1667 1 d R . . E 1
C1 C 0.4062(3) 0.7500 0.7500 0.0308(9) Uani 1 2 d S T P . .
H1A H 0.4568 0.7003 0.7996 0.037 Uiso 0.5 1 calc R . . . .
H1B H 0.4568 0.7996 0.7004 0.037 Uiso 0.5 1 calc R . . . .
C2 C 0.3275(2) 0.6725(2) 0.6725(2) 0.0298(8) Uani 1 2 d S T P A .
C3 C 0.2500 0.7500 0.5951(3) 0.0323(13) Uani 1 4 d S T P . .
H3B H 0.2004 0.7004 0.5444 0.039 Uiso 0.5 2 calc RS T P . .
H3A H 0.2996 0.7996 0.5444 0.039 Uiso 0.5 2 calc RS T P . .
C4 C 0.4047(2) 0.5953(2) 0.5966(3) 0.0354(9) Uani 1 2 d S T P . .
O1S O 0.647(5) 0.787(5) 0.422(4) 0.139(14) Uiso 0.125 1 d . . . F 1
O3S O 0.517(7) 0.806(5) 0.329(5) 0.166(15) Uiso 0.125 1 d . . . G 3
O4S O 0.463(2) 0.887(2) 0.3526(18) 0.132(5) Uiso 0.25 1 d . . . H 4
O6S O 0.630(3) 0.370(3) 0.787(3) 0.173(13) Uiso 0.25 2 d S T P I 6
O7S O 0.319(7) 0.681(7) 0.263(12) 0.23(4) Uiso 0.125 2 d S T P J 7
O5S O 0.5373(13) 0.4627(13) 0.9147(16) 0.086(5) Uiso 0.25 2 d S T P K 5
O9S O 0.5170(13) 0.9573(13) 0.4718(11) 0.096(4) Uiso 0.25 1 d . . . L 9
O10S O 0.5216(14) 0.8957(13) 0.4242(12) 0.089(4) Uiso 0.25 1 d . . . M 10
O11S O 0.580(4) 0.834(4) 0.414(3) 0.191(11) Uiso 0.25 1 d . . . N 11
O12S O 0.708(4) 0.792(4) 0.5000 0.26(3) Uiso 0.25 2 d S T P O 12
O13S O 0.6051(16) 0.8949(16) 0.5000 0.188(7) Uiso 0.5 2 d S T P P 13
O8S O 0.422(6) 0.774(10) 0.272(9) 0.22(3) Uiso 0.125 1 d . . . Q 8
O2S O 0.759(10) 0.613(6) 0.692(5) 0.23(3) Uiso 0.125 1 d . . . R 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.093(6) 0.093(6) 0.012(3) -0.007(2) 0.007(2) 0.042(8)
O2 0.052(6) 0.118(10) 0.094(7) -0.082(6) -0.002(4) 0.003(5)
O3 0.104(8) 0.046(6) 0.068(6) -0.009(3) 0.054(4) -0.005(4)
O4 0.107(9) 0.107(9) 0.022(4) -0.006(2) 0.006(2) 0.075(11)
C1 0.028(2) 0.039(2) 0.0252(19) 0.0001(8) 0.000 0.000
C2 0.0339(18) 0.0339(18) 0.0217(18) -0.0024(5) 0.0024(5) -0.0017(13)
C3 0.037(2) 0.037(2) 0.022(2) 0.000 0.000 0.0058(18)
C4 0.041(2) 0.041(2) 0.025(2) -0.0002(6) 0.0002(6) 0.0041(15)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.809(10) . ?
O1 C4 1.245(8) . ?
O2 H2 0.830(8) . ?
O2 C4 1.242(7) . ?
O3 H3 0.800(6) . ?
O3 C4 1.228(8) . ?
O4 H4 0.821(9) . ?
O4 C4 1.180(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.542(2) . ?
C1 C2 1.542(2) 12_667 ?
C2 C1 1.542(2) 11_567 ?
C2 C3 1.533(5) . ?
C2 C4 1.520(3) . ?
C3 C2 1.533(5) 2_565 ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 O2 1.242(7) 15_665 ?
C4 O3 1.228(8) 15_665 ?
O4S O4S 1.22(4) 16_565 ?
O7S O7S 1.60(14) 11_566 ?
O7S O7S 1.60(14) 12_666 ?
O9S O9S 0.77(3) 8_666 ?
O9S O9S 1.233(18) 9_676 ?
O9S O9S 0.97(3) 16_565 ?
O12S O12S 1.35(12) 2_665 ?
O8S O8S 0.74(19) 6_565 ?
O2S O2S 1.35(13) 5_656 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 111.5(10) . . ?
C4 O2 H2 106.6(8) . . ?
C4 O3 H3 110.5(7) . . ?
C4 O4 H4 113.6(9) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 110.0 12_667 . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 12_667 . ?
C2 C1 H1B 110.0 . . ?
C2 C1 C2 108.6(3) 12_667 . ?
C1 C2 C1 109.9(2) . 11_567 ?
C3 C2 C1 109.66(17) . 11_567 ?
C3 C2 C1 109.66(17) . . ?
C4 C2 C1 108.83(19) . . ?
C4 C2 C1 108.83(19) . 11_567 ?
C4 C2 C3 110.0(3) . . ?
C2 C3 C2 109.6(3) . 2_565 ?
C2 C3 H3B 109.8 2_565 . ?
C2 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 2_565 . ?
H3B C3 H3A 108.2 . . ?
O1 C4 C2 120.5(6) . . ?
O2 C4 O2 98.0(17) 15_665 . ?
O2 C4 C2 115.3(5) . . ?
O2 C4 C2 115.3(5) 15_665 . ?
O3 C4 O3 95.7(13) 15_665 . ?
O3 C4 C2 121.2(3) . . ?
O3 C4 C2 121.2(3) 15_665 . ?
O4 C4 O1 122.3(7) . . ?
O4 C4 C2 117.2(5) . . ?
O7S O7S O7S 88(4) 11_566 12_666 ?
O9S O9S O9S 89.997(3) 8_666 16_565 ?
O9S O9S O9S 38.4(15) 16_565 9_676 ?
O9S O9S O9S 51.6(15) 8_666 9_676 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.809(10) 1.830(9) 2.622(13) 165.9(7) 7_556
O2 H2 O2 0.830(8) 2.237(12) 2.98(2) 148.3(12) 7_556
O3 H3 O3 0.800(6) 2.024(7) 2.750(14) 150.8(10) 7_556
O4 H4 O1 0.821(9) 1.817(9) 2.622(13) 166.4(2) 7_556
_shelx_res_file
;
pc_8_235_200k_tetp.res created by SHELXL-2014/7
TITL pc_8_235_200k_tetp_a.res in P4(2)/nnm
REM Old TITL PC_8_235_200K_TetP in P4(2)/nnm
REM SHELXT solution in P4(2)/nnm
REM R1 0.457, Rweak 0.034, Alpha 0.073, Orientation as input
REM Formula found by SHELXT: C7
CELL 0.71073 11.4331 11.4331 11.4312 90 90 90
ZERR 2 0.0008 0.0008 0.0008 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,+Z
SYMM 0.5-Y,+X,0.5+Z
SYMM +Y,0.5-X,0.5+Z
SYMM 0.5-X,+Y,0.5-Z
SYMM +X,0.5-Y,0.5-Z
SYMM +Y,+X,-Z
SYMM 0.5-Y,0.5-X,-Z
SFAC C H O
UNIT 28 40 51
EQIV $1 1-Y,1-X,+Z
EQIV $2 +Y,+X,1-Z
ISOR 0.01 0.02 O1
L.S. 10
PLAN 20
TEMP -73.15
HTAB O1 O4_$2
HTAB O2 O2_$2
HTAB O3 O3_$2
HTAB O4 O1_$2
FREE O3 O3_$1
BOND $H
list 4
fmap 2 53
acta
TWIN -1 0 0 0 0 1 0 1 0 2
REM
REM
REM
WGHT 0.122800 0.293900
BASF 0.46779
FVAR 1.13976
PART 1
O1 3 0.398908 0.601092 0.488017 10.16667 0.09307 0.09307 =
0.01234 -0.00712 0.00712 0.04164
H1 2 10.443999 10.556009 10.457280 10.16667 -1.50000
PART 0
PART 3
O2 3 0.351811 0.532176 0.525737 10.33333 0.05248 0.11846 =
0.09370 -0.08245 -0.00220 0.00264
H2 2 10.402549 10.497789 10.486819 10.33333 -1.50000
PART 0
PART 2
O3 3 0.399168 0.488276 0.602470 10.33333 0.10432 0.04643 =
0.06795 -0.00921 0.05433 -0.00542
H3 2 10.445020 10.458990 10.558430 10.33333 -1.50000
PART 0
PART 1
O4 3 0.469050 0.530950 0.645140 10.16667 0.10660 0.10660 =
0.02250 -0.00594 0.00594 0.07471
H4 2 10.516469 10.499439 10.601430 10.16667 -1.50000
PART 0
C1 1 0.406156 0.750000 0.750000 10.50000 0.02800 0.03908 =
0.02522 0.00013 0.00000 0.00000
AFIX 23
H1A 2 0.456841 0.700350 0.799645 10.50000 -1.20000
H1B 2 0.456843 0.799650 0.700356 10.50000 -1.20000
AFIX 0
C2 1 0.327479 0.672521 0.672486 10.50000 0.03393 0.03393 =
0.02169 -0.00241 0.00241 -0.00175
C3 1 0.250000 0.750000 0.595120 10.25000 0.03741 0.03741 =
0.02194 0.00000 0.00000 0.00580
AFIX 23
H3B 2 0.200394 0.700395 0.544352 10.25000 -1.20000
H3A 2 0.299605 0.799606 0.544352 10.25000 -1.20000
AFIX 0
C4 1 0.404650 0.595350 0.596620 10.50000 0.04055 0.04055 =
0.02508 -0.00015 0.00015 0.00413
PART 1
O1S 3 0.647261 0.786513 0.422333 10.12500 0.13887
PART 0
PART 3
O3S 3 0.516990 0.805944 0.328985 10.12500 0.16625
PART 0
PART 4
O4S 3 0.463224 0.887471 0.352628 10.25000 0.13176
PART 0
PART 6
O6S 3 0.629946 0.370054 0.787388 10.12500 0.17301
PART 0
PART 7
O7S 3 0.318935 0.681065 0.262990 10.06250 0.23238
PART 0
PART 5
O5S 3 0.537334 0.462666 0.914687 10.12500 0.08568
PART 0
PART 9
O9S 3 0.517038 0.957291 0.471848 10.25000 0.09640
PART 0
PART 10
O10S 3 0.521624 0.895687 0.424198 10.25000 0.08898
PART 0
PART 11
O11S 3 0.580121 0.834152 0.414071 10.25000 0.19127
PART 0
PART 12
O12S 3 0.708380 0.791620 0.500000 10.12500 0.25771
PART 0
PART 13
O13S 3 0.605133 0.894867 0.500000 10.25000 0.18827
PART 0
PART 8
O8S 3 0.421938 0.773877 0.271902 10.12500 0.22473
PART 0
PART 2
O2S 3 0.758613 0.613008 0.691524 10.12500 0.22880
HKLF 4
REM pc_8_235_200k_tetp_a.res in P4(2)/nnm
REM R1 = 0.0760 for 682 Fo > 4sig(Fo) and 0.0860 for all 829 data
REM 98 parameters refined using 6 restraints
END
WGHT 0.1214 0.3053
REM Highest difference peak 0.177, deepest hole -0.398, 1-sigma level 0.084
Q1 1 0.8205 0.5790 0.7493 11.00000 0.05 0.18
Q2 1 0.7500 0.6610 0.7500 10.50000 0.05 0.17
Q3 1 0.8466 0.6106 0.7541 11.00000 0.05 0.17
Q4 1 0.8061 0.7271 0.7311 11.00000 0.05 0.16
Q5 1 0.8154 0.7289 0.7392 11.00000 0.05 0.16
Q6 1 0.7500 0.7500 0.6651 10.50000 0.05 0.16
Q7 1 0.3760 0.8760 0.6252 10.50000 0.05 0.15
Q8 1 0.8701 0.7500 0.7500 10.50000 0.05 0.14
Q9 1 0.2965 0.6394 0.6995 11.00000 0.05 0.13
Q10 1 0.5852 0.7983 0.7600 11.00000 0.05 0.13
Q11 1 0.5252 0.7434 0.7869 11.00000 0.05 0.12
Q12 1 0.3568 0.6432 0.6549 10.50000 0.05 0.12
Q13 1 0.8661 0.6989 0.6838 11.00000 0.05 0.12
Q14 1 0.5021 0.8229 0.1969 11.00000 0.05 0.12
Q15 1 0.5193 0.7500 0.2500 10.50000 0.05 0.12
Q16 1 0.7949 0.6335 0.6600 11.00000 0.05 0.12
Q17 1 0.4384 0.4593 0.7457 11.00000 0.05 0.12
Q18 1 0.5163 0.9085 0.2552 11.00000 0.05 0.12
Q19 1 0.3016 0.6625 0.6825 11.00000 0.05 0.11
Q20 1 0.7585 0.5858 0.6685 11.00000 0.05 0.11
;
_shelx_res_checksum 73584
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.532(12)
2 0.468(12)
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_TMA_2-33_THF-butylbenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915315'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_TMA_2-33_THF-bultybenzene_publ
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 4.03 Check
RESPONSE: Disordered electron density was tentatively modelled as disordered
H2O, these were refined without H-atoms, however, H-atoms for these were
still included in the unit cell atom count.
;
_vrf_PLAT601_TMA_2-33_THF-bultybenzene_publ
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of . 150 Ang**3
RESPONSE: These are likely to contain disordered solvent molecules which
could not be resolved during refinement.
;
# end Validation Reply Form
_audit_creation_date 2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C9 H6 O6, 2(H2 O)'
_chemical_formula_sum 'C9 H10 O8'
_chemical_formula_weight 246.17
_chemical_absolute_configuration ?
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system trigonal
_space_group_IT_number 152
_space_group_name_H-M_alt 'P 31 2 1'
_space_group_name_Hall 'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'
_cell_length_a 16.5141(6)
_cell_length_b 16.5141(6)
_cell_length_c 9.7096(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 2293.20(19)
_cell_formula_units_Z 6
_cell_measurement_reflns_used 9919
_cell_measurement_temperature 100
_cell_measurement_theta_max 29.105
_cell_measurement_theta_min 2.535
_shelx_estimated_absorpt_T_max 0.996
_shelx_estimated_absorpt_T_min 0.987
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_T_max 0.7458
_exptl_absorpt_correction_T_min 0.4428
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0968 before and 0.0703 after correction. The Ratio of minimum to maximum transmission is 0.5937. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.070
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 768
_exptl_crystal_size_max 0.134
_exptl_crystal_size_mid 0.063
_exptl_crystal_size_min 0.039
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0516
_diffrn_reflns_av_unetI/netI 0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 24980
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 2.535
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.813
_reflns_Friedel_fraction_full 0.992
_reflns_Friedel_fraction_max 0.993
_reflns_number_gt 2533
_reflns_number_total 3095
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.405
_refine_diff_density_min -0.272
_refine_diff_density_rms 0.074
_refine_ls_abs_structure_details
;
Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack -2.0(10)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.062
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 174
_refine_ls_number_reflns 3095
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0740
_refine_ls_R_factor_gt 0.0638
_refine_ls_restrained_S_all 1.061
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1641P)^2^+0.3647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2062
_refine_ls_wR_factor_ref 0.2217
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All O(H) groups
2. Restrained planarity
H5, C9, O6, O5, H6
with sigma of 0.001
H4, O4, C8, O3, H3
with sigma of 0.1
O1, C7, O2, H2, H1
with sigma of 0.001
3. Others
Fixed Sof: H5(0.5) H1(0.5) H4(0.5) H3(0.5) H2(0.5) H6(0.5) O1W(0.125)
O7W(0.25) O2W(0.25) O6W(0.25) O5W(0.125) O3W(0.25) O4W(0.25) O8W(0.25)
O9W(0.25)
4.a Aromatic/amide H refined with riding coordinates:
C4(H4A), C2(H2A), C6(H6A)
4.b Idealised tetrahedral OH refined as rotating group:
O5(H5), O1(H1), O4(H4), O3(H3), O2(H2), O6(H6)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.85082(19) 0.4629(2) 0.4973(2) 0.0299(8) Uani 1 1 d . . . . .
H5 H 0.9088 0.4842 0.4945 0.045 Uiso 0.5 1 calc GR . . A 1
O1 O 0.5555(2) 0.0327(2) 0.5151(3) 0.0352(8) Uani 1 1 d . . . . .
H1 H 0.5200 -0.0255 0.5140 0.053 Uiso 0.5 1 calc GR . . B 2
O4 O 0.5553(2) 0.4641(2) 0.5092(3) 0.0301(8) Uani 1 1 d . . . . .
H4 H 0.5193 0.4862 0.5142 0.045 Uiso 0.5 1 calc GR . . C 1
O3 O 0.4193(2) 0.3287(2) 0.5068(3) 0.0382(8) Uani 1 1 d . . . . .
H3 H 0.3976 0.3651 0.5081 0.057 Uiso 0.5 1 calc GR . . D 2
O2 O 0.4195(2) 0.0320(2) 0.5054(3) 0.0396(9) Uani 1 1 d . . . . .
H2 H 0.3980 -0.0261 0.5053 0.059 Uiso 0.5 1 calc GR . . E 2
O6 O 0.8492(2) 0.3263(2) 0.5041(3) 0.0347(8) Uani 1 1 d . . . . .
H6 H 0.9074 0.3617 0.5006 0.052 Uiso 0.5 1 calc GR . . F 2
C3 C 0.5599(3) 0.3235(3) 0.5124(3) 0.0242(7) Uani 1 1 d . . . . .
C7 C 0.5065(3) 0.0729(2) 0.5106(3) 0.0244(6) Uani 1 1 d . . . . .
C4 C 0.6569(3) 0.37205(19) 0.5099(3) 0.0214(7) Uani 1 1 d . . . . .
H4A H 0.6905 0.4385 0.5102 0.026 Uiso 1 1 calc R . . . .
C5 C 0.70469(19) 0.3225(3) 0.5071(3) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.5101(2) 0.2260(3) 0.5127(3) 0.0245(7) Uani 1 1 d . . . . .
H2A H 0.4436 0.1931 0.5137 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8093(2) 0.3750(3) 0.5029(3) 0.0233(6) Uani 1 1 d . . . . .
C8 C 0.5076(3) 0.3757(3) 0.5097(3) 0.0243(7) Uani 1 1 d . . . . .
C6 C 0.6569(3) 0.2253(3) 0.5082(3) 0.0244(8) Uani 1 1 d . . . . .
H6A H 0.6900 0.1920 0.5066 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5590(3) 0.17750(19) 0.5115(3) 0.0229(6) Uani 1 1 d . . . . .
O1W O 0.218(2) 0.0000 0.3333 0.117(10) Uiso 0.25 2 d S T P G 1
O7W O 0.7470(16) 0.0411(15) 0.268(2) 0.098(6) Uiso 0.25 1 d . . . H 7
O2W O 0.232(2) 0.058(2) 0.347(2) 0.117(7) Uiso 0.25 1 d . . . I 2
O6W O 0.076(3) 0.023(3) 0.414(5) 0.218(18) Uiso 0.25 1 d . . . J 6
O5W O 0.278(3) 0.0000 0.8333 0.128(12) Uiso 0.25 2 d S T P K 5
O3W O 0.335(2) 0.133(2) 0.882(3) 0.126(8) Uiso 0.25 1 d . . . L 3
O4W O 0.320(2) 0.127(2) 0.800(4) 0.145(10) Uiso 0.25 1 d . . . M 4
O8W O 0.771(2) 0.036(2) 0.140(3) 0.147(10) Uiso 0.25 1 d . . . N 8
O9W O 0.791(2) 0.105(2) 0.343(3) 0.141(9) Uiso 0.25 1 d . . . O 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0249(16) 0.0282(18) 0.0332(13) -0.0002(11) -0.0007(10) 0.0107(13)
O1 0.0329(18) 0.0267(17) 0.0462(16) 0.0025(12) 0.0031(13) 0.0149(13)
O4 0.0353(18) 0.0242(17) 0.0358(14) -0.0001(10) -0.0015(12) 0.0185(15)
O3 0.0256(17) 0.0301(17) 0.0592(19) 0.0010(14) -0.0021(13) 0.0141(15)
O2 0.0275(18) 0.0219(16) 0.0591(18) -0.0013(13) -0.0060(13) 0.0045(13)
O6 0.0241(16) 0.0355(17) 0.0484(17) 0.0049(13) 0.0037(12) 0.0177(14)
C3 0.0241(19) 0.029(2) 0.0193(12) -0.0006(14) -0.0014(13) 0.0130(13)
C7 0.027(2) 0.0229(14) 0.0243(13) -0.0010(10) -0.0009(14) 0.0131(18)
C4 0.020(2) 0.0204(14) 0.0182(11) -0.0002(9) 0.0014(13) 0.0054(17)
C5 0.0217(15) 0.0240(19) 0.0175(11) 0.0003(12) -0.0002(9) 0.0098(17)
C2 0.0232(14) 0.030(2) 0.0223(13) 0.0019(16) -0.0013(10) 0.0143(19)
C9 0.0233(14) 0.027(2) 0.0196(12) 0.0011(15) 0.0003(10) 0.0131(18)
C8 0.024(2) 0.025(2) 0.0225(14) 0.0002(14) -0.0012(14) 0.0114(12)
C6 0.031(2) 0.026(2) 0.0190(13) -0.0030(14) -0.0024(15) 0.0161(13)
C1 0.026(2) 0.0204(13) 0.0220(13) -0.0006(10) -0.0003(14) 0.0113(18)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 H5 0.8400 . ?
O5 C9 1.259(6) . ?
O1 H1 0.8400 . ?
O1 C7 1.278(6) . ?
O4 H4 0.8400 . ?
O4 C8 1.266(6) . ?
O3 H3 0.8400 . ?
O3 C8 1.265(6) . ?
O2 H2 0.8400 . ?
O2 C7 1.246(6) . ?
O6 H6 0.8400 . ?
O6 C9 1.271(6) . ?
C3 C4 1.388(6) . ?
C3 C2 1.395(7) . ?
C3 C8 1.494(4) . ?
C7 C1 1.496(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.392(6) . ?
C5 C9 1.497(4) . ?
C5 C6 1.390(6) . ?
C2 H2A 0.9500 . ?
C2 C1 1.394(6) . ?
C6 H6A 0.9500 . ?
C6 C1 1.401(7) . ?
O7W O7W 1.73(4) 4 ?
O2W O2W 1.67(6) 4 ?
O6W O6W 1.70(9) 4 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O5 H5 109.5 . . ?
C7 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C8 O3 H3 109.5 . . ?
C7 O2 H2 109.5 . . ?
C9 O6 H6 109.5 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 C8 120.0(4) . . ?
C2 C3 C8 119.2(4) . . ?
O1 C7 C1 116.5(4) . . ?
O2 C7 O1 125.3(3) . . ?
O2 C7 C1 118.2(4) . . ?
C3 C4 H4A 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C9 119.2(3) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 C9 119.6(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2A 120.4 . . ?
O5 C9 O6 125.1(3) . . ?
O5 C9 C5 118.4(4) . . ?
O6 C9 C5 116.5(4) . . ?
O4 C8 C3 117.4(4) . . ?
O3 C8 O4 124.7(3) . . ?
O3 C8 C3 117.9(4) . . ?
C5 C6 H6A 120.7 . . ?
C5 C6 C1 118.7(3) . . ?
C1 C6 H6A 120.7 . . ?
C2 C1 C7 119.7(4) . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 C7 119.3(4) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O1 0.84 1.78 2.605(4) 166.2 6_656
O4 H4 O4 0.84 1.79 2.613(5) 164.3 6_556
O2 H2 O6 0.84 1.79 2.615(5) 166.2 6_546
_shelx_res_file
;
pc_ht_1_i233_100k.res created by SHELXL-2014/7
TITL pc_ht_1_i233_100k_a.res in P3(2)21
REM Old TITL PC_HT_1_i233_100k in P3221 #154
REM SHELXT solution in P3(2)21
REM R1 0.206, Rweak 0.006, Alpha 0.056, Orientation as input
REM Flack x = -0.002 ( 0.549 ) from Parsons' quotients
REM Formula found by SHELXT: C7 O1W
CELL 0.71073 16.5141 16.5141 9.7096 90 90 120
ZERR 6 0.0006 0.0006 0.0004 0 0 0
LATT -1
SYMM -Y,+X-Y,0.333+Z
SYMM +Y-X,-X,0.667+Z
SYMM -Y+X,-Y,0.667-Z
SYMM -X,-X+Y,0.333-Z
SYMM +Y,+X,-Z
SFAC C H O
UNIT 54 60 48
EQIV $1 1+Y,+X,1-Z
EQIV $2 +Y,+X,1-Z
EQIV $3 +Y,-1+X,1-Z
FLAT 0.001 H5 C9 O6 O5 H6
FLAT H4 O4 C8 O3 H3
FLAT 0.001 O1 C7 O2 H2 H1
L.S. 20
PLAN 20
SIZE 0.134 0.063 0.039
TEMP -173.15
HTAB O5 O1_$1
HTAB O4 O4_$2
HTAB O2 O6_$3
BOND $H
list 4
fmap 2
acta
SHEL 11 0.8
OMIT 0 3 1
OMIT 0 5 0
OMIT 2 2 0
OMIT -2 4 0
OMIT 2 3 0
OMIT -2 5 0
OMIT 2 3 1
OMIT -2 5 1
OMIT -2 3 1
REM
REM
REM
WGHT 0.164100 0.364700
FVAR 0.91261
O5 3 0.850820 0.462920 0.497324 11.00000 0.02486 0.02824 =
0.03319 -0.00019 -0.00072 0.01072
PART 1
AFIX 147
H5 2 0.908837 0.484180 0.494499 10.50000 -1.50000
AFIX 0
PART 0
O1 3 0.555504 0.032746 0.515088 11.00000 0.03287 0.02667 =
0.04616 0.00248 0.00308 0.01495
PART 2
AFIX 147
H1 2 0.519996 -0.025520 0.513970 10.50000 -1.50000
AFIX 0
PART 0
O4 3 0.555284 0.464136 0.509222 11.00000 0.03526 0.02421 =
0.03578 -0.00012 -0.00154 0.01852
PART 1
AFIX 147
H4 2 0.519273 0.486206 0.514216 10.50000 -1.50000
AFIX 0
PART 0
O3 3 0.419260 0.328681 0.506831 11.00000 0.02561 0.03011 =
0.05923 0.00102 -0.00214 0.01412
PART 2
AFIX 147
H3 2 0.397608 0.365132 0.508126 10.50000 -1.50000
AFIX 0
PART 0
O2 3 0.419464 0.031963 0.505448 11.00000 0.02748 0.02191 =
0.05908 -0.00128 -0.00596 0.00453
PART 2
AFIX 147
H2 2 0.397996 -0.026117 0.505324 10.50000 -1.50000
AFIX 0
PART 0
O6 3 0.849227 0.326262 0.504097 11.00000 0.02410 0.03548 =
0.04843 0.00488 0.00372 0.01775
PART 2
AFIX 147
H6 2 0.907450 0.361746 0.500566 10.50000 -1.50000
AFIX 0
PART 0
C3 1 0.559888 0.323546 0.512399 11.00000 0.02415 0.02888 =
0.01927 -0.00062 -0.00138 0.01296
C7 1 0.506477 0.072898 0.510638 11.00000 0.02693 0.02286 =
0.02435 -0.00099 -0.00091 0.01310
C4 1 0.656928 0.372051 0.509937 11.00000 0.01952 0.02042 =
0.01821 -0.00021 0.00139 0.00539
AFIX 43
H4A 2 0.690457 0.438476 0.510181 11.00000 -1.20000
AFIX 0
C5 1 0.704686 0.322478 0.507107 11.00000 0.02171 0.02401 =
0.01746 0.00034 -0.00021 0.00982
C2 1 0.510056 0.226023 0.512694 11.00000 0.02317 0.02955 =
0.02232 0.00191 -0.00129 0.01435
AFIX 43
H2A 2 0.443635 0.193103 0.513715 11.00000 -1.20000
AFIX 0
C9 1 0.809286 0.375024 0.502922 11.00000 0.02333 0.02731 =
0.01964 0.00112 0.00031 0.01306
C8 1 0.507600 0.375704 0.509668 11.00000 0.02410 0.02520 =
0.02246 0.00017 -0.00124 0.01140
C6 1 0.656894 0.225295 0.508151 11.00000 0.03087 0.02577 =
0.01899 -0.00303 -0.00243 0.01606
AFIX 43
H6A 2 0.689971 0.191954 0.506643 11.00000 -1.20000
AFIX 0
C1 1 0.558995 0.177504 0.511471 11.00000 0.02590 0.02039 =
0.02198 -0.00057 -0.00028 0.01132
PART 1
O1W 3 0.217776 0.000000 0.333333 10.12500 0.11714
PART 0
PART 7
O7W 3 0.747047 0.041087 0.267665 10.25000 0.09843
PART 0
PART 2
O2W 3 0.232468 0.057763 0.347260 10.25000 0.11691
PART 0
PART 6
O6W 3 0.076315 0.022829 0.414153 10.25000 0.21788
PART 0
PART 5
O5W 3 0.278488 0.000000 0.833333 10.12500 0.12844
PART 0
PART 3
O3W 3 0.334999 0.133304 0.881746 10.25000 0.12625
PART 0
PART 4
O4W 3 0.319537 0.126807 0.800434 10.25000 0.14462
PART 0
PART 8
O8W 3 0.770773 0.036011 0.139671 10.25000 0.14693
PART 0
PART 1
O9W 3 0.790590 0.104557 0.343328 10.25000 0.14065
HKLF 4
REM pc_ht_1_i233_100k_a.res in P3(2)21
REM R1 = 0.0638 for 2533 Fo > 4sig(Fo) and 0.0740 for all 3095 data
REM 174 parameters refined using 6 restraints
END
WGHT 0.1641 0.3647
REM Highest difference peak 0.405, deepest hole -0.272, 1-sigma level 0.074
Q1 1 0.2955 0.1742 0.7360 11.00000 0.05 0.40
Q2 1 0.5368 0.1313 0.5064 11.00000 0.05 0.36
Q3 1 0.2026 0.0961 0.2750 11.00000 0.05 0.31
Q4 1 0.7458 0.3419 0.5075 11.00000 0.05 0.30
Q5 1 0.1987 0.0489 0.2397 11.00000 0.05 0.29
Q6 1 0.5365 0.3418 0.5053 11.00000 0.05 0.29
Q7 1 0.3109 0.0711 0.7958 11.00000 0.05 0.26
Q8 1 0.2475 0.0617 0.8574 11.00000 0.05 0.26
Q9 1 0.2519 -0.0334 0.7823 11.00000 0.05 0.26
Q10 1 0.6091 0.2013 0.5040 11.00000 0.05 0.25
Q11 1 0.8011 0.1386 0.2831 11.00000 0.05 0.24
Q12 1 0.1937 0.0332 0.4284 11.00000 0.05 0.23
Q13 1 0.6157 0.3519 0.5029 11.00000 0.05 0.22
Q14 1 0.7948 0.0796 0.2232 11.00000 0.05 0.21
Q15 1 0.2971 0.1245 0.9760 11.00000 0.05 0.21
Q16 1 0.8558 0.4729 0.6314 11.00000 0.05 0.20
Q17 1 0.2370 0.1081 0.8275 11.00000 0.05 0.20
Q18 1 0.5717 0.5511 0.4448 11.00000 0.05 0.20
Q19 1 0.6150 0.4916 0.4862 11.00000 0.05 0.20
Q20 1 0.7427 0.0297 0.3645 11.00000 0.05 0.19
;
_shelx_res_checksum 54663
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_pc_ht_1_i418_100k
_database_code_depnum_ccdc_archive 'CCDC 1915311'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record
;
2019-05-10 deposited with the CCDC. 2019-08-20 downloaded from the CCDC.
;
_audit_creation_date 2018-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C9 H6 O6), 2(C3 H8 O)'
_chemical_formula_sum 'C24 H28 O14'
_chemical_formula_weight 540.46
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 19.0126(17)
_cell_length_b 9.6004(8)
_cell_length_c 27.383(2)
_cell_angle_alpha 90
_cell_angle_beta 90.563(2)
_cell_angle_gamma 90
_cell_volume 4998.0(8)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 7992
_cell_measurement_temperature 100
_cell_measurement_theta_max 26.369
_cell_measurement_theta_min 2.487
_shelx_estimated_absorpt_T_max 0.991
_shelx_estimated_absorpt_T_min 0.978
_exptl_absorpt_coefficient_mu 0.120
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.4737
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.6355.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.437
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 2272
_exptl_crystal_size_max 0.188
_exptl_crystal_size_mid 0.101
_exptl_crystal_size_min 0.079
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0488
_diffrn_reflns_av_unetI/netI 0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 23
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 23878
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.446
_diffrn_reflns_theta_min 1.487
_diffrn_ambient_temperature 100
_diffrn_detector CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type 'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation 0.3
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Rotating Anode'
_diffrn_source_current 24.0
_diffrn_source_power 1.2
_diffrn_source_target Mo
_diffrn_source_type 'Rotating Anode'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4122
_reflns_number_total 5145
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.651
_refine_diff_density_min -0.317
_refine_diff_density_rms 0.072
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 373
_refine_ls_number_reflns 5145
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0687
_refine_ls_R_factor_gt 0.0564
_refine_ls_restrained_S_all 1.039
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+4.7971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1501
_refine_ls_wR_factor_ref 0.1624
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All H(H) groups, All C(H,H,H) groups, All O(H) groups
2. Restrained distances
O1-H1 = O11-H11
0.82 with sigma of 0.02
H11-C17
1.85 with sigma of 0.02
3. Others
Fixed Sof: H5(0.5) H6(0.5) H7(0.5) H8(0.5)
4.a Ternary CH refined with riding coordinates:
C20(H20), C23(H23)
4.b Aromatic/amide H refined with riding coordinates:
C2(H2), C4(H4), C6(H6A), C11(H11A), C13(H13), C15(H15)
4.c Idealised Me refined as rotating group:
C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
H24C)
4.d Idealised tetrahedral OH refined as rotating group:
O5(H5), O6(H6), O7(H7), O8(H8)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69648(8) 0.36151(14) 0.55617(5) 0.0267(3) Uani 1 1 d D . . . .
O2 O 0.71555(8) 0.44888(14) 0.63107(5) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.71761(7) 0.96892(14) 0.64556(5) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.69764(8) 1.09830(14) 0.57887(5) 0.0267(3) Uani 1 1 d . . . . .
O5 O 0.63354(7) 0.87680(14) 0.42412(4) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.6264 0.8704 0.3939 0.034 Uiso 0.5 1 calc GR . P A 1
O6 O 0.63714(7) 0.64380(14) 0.41790(5) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.6269 0.6627 0.3887 0.037 Uiso 0.5 1 calc GR . P B 2
C1 C 0.68848(9) 0.60339(19) 0.56528(6) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.66979(9) 0.61385(19) 0.51612(6) 0.0177(4) Uani 1 1 d . . . . .
H2 H 0.6643 0.5321 0.4969 0.021 Uiso 1 1 calc R . . . .
C3 C 0.65911(9) 0.74486(19) 0.49505(6) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.66828(9) 0.86457(19) 0.52286(6) 0.0173(4) Uani 1 1 d . . . . .
H4 H 0.6613 0.9537 0.5085 0.021 Uiso 1 1 calc R . . . .
C5 C 0.68773(9) 0.85356(19) 0.57194(6) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.69699(9) 0.72309(19) 0.59357(6) 0.0178(4) Uani 1 1 d . . . . .
H6A H 0.7090 0.7159 0.6272 0.021 Uiso 1 1 calc R . . . .
C7 C 0.70166(9) 0.46362(19) 0.58799(6) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.64173(9) 0.75493(19) 0.44223(6) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.70145(9) 0.9855(2) 0.59939(6) 0.0189(4) Uani 1 1 d . . . . .
O7 O 0.61573(7) 1.34422(14) 0.82386(5) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.6200 1.3376 0.8543 0.036 Uiso 0.5 1 calc GR . P C 2
O8 O 0.61683(7) 1.11103(14) 0.82912(4) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.6246 1.1295 0.8587 0.033 Uiso 0.5 1 calc GR . P D 1
O9 O 0.55576(8) 0.83243(14) 0.68981(5) 0.0284(3) Uani 1 1 d . . . . .
O10 O 0.53336(7) 0.92163(14) 0.61570(5) 0.0248(3) Uani 1 1 d . . . . .
O11 O 0.53088(8) 1.44126(14) 0.60270(5) 0.0252(3) Uani 1 1 d D . . . .
O12 O 0.54648(8) 1.56819(14) 0.67016(5) 0.0264(3) Uani 1 1 d . . . . .
C10 C 0.59063(9) 1.21422(19) 0.75269(6) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.57868(9) 1.33437(18) 0.72549(6) 0.0165(4) Uani 1 1 d . . . . .
H11A H 0.5836 1.4232 0.7404 0.020 Uiso 1 1 calc R . . . .
C12 C 0.55949(9) 1.32448(19) 0.67633(6) 0.0172(4) Uani 1 1 d . . . . .
C13 C 0.55156(9) 1.19518(19) 0.65422(6) 0.0169(4) Uani 1 1 d . . . . .
H13 H 0.5393 1.1889 0.6206 0.020 Uiso 1 1 calc R . . . .
C14 C 0.56178(9) 1.07457(19) 0.68186(6) 0.0170(4) Uani 1 1 d . . . . .
C15 C 0.58206(9) 1.08374(18) 0.73074(6) 0.0157(4) Uani 1 1 d . . . . .
H15 H 0.5901 1.0013 0.7492 0.019 Uiso 1 1 calc R . . . .
C16 C 0.60917(9) 1.22306(18) 0.80543(6) 0.0160(4) Uani 1 1 d . . . . .
C17 C 0.54518(9) 1.45685(18) 0.64924(6) 0.0184(4) Uani 1 1 d D . . . .
C18 C 0.54894(9) 0.93554(19) 0.65871(6) 0.0185(4) Uani 1 1 d . . . . .
O13 O 0.75891(7) 0.70756(14) 0.81418(5) 0.0236(3) Uani 1 1 d . . . . .
C19 C 0.63194(11) 0.7285(2) 0.80337(7) 0.0286(5) Uani 1 1 d . . . . .
H19A H 0.6247 0.6397 0.8203 0.043 Uiso 1 1 calc GR . . . .
H19B H 0.5947 0.7417 0.7788 0.043 Uiso 1 1 calc GR . . . .
H19C H 0.6306 0.8049 0.8271 0.043 Uiso 1 1 calc GR . . . .
C20 C 0.70270(10) 0.7270(2) 0.77855(6) 0.0222(4) Uani 1 1 d . . . . .
H20 H 0.7097 0.8183 0.7617 0.027 Uiso 1 1 calc R . . . .
C21 C 0.70957(11) 0.6120(2) 0.74193(7) 0.0289(5) Uani 1 1 d . . . . .
H21A H 0.7562 0.6159 0.7271 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.6734 0.6227 0.7165 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.7035 0.5220 0.7583 0.043 Uiso 1 1 calc GR . . . .
O14 O 0.50478(7) 0.67657(14) 0.56196(5) 0.0255(3) Uani 1 1 d . . . . .
C22 C 0.46024(11) 0.8183(2) 0.49502(7) 0.0332(5) Uani 1 1 d . . . . .
H22A H 0.4668 0.9041 0.5139 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.4205 0.8298 0.4723 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.5030 0.7985 0.4766 0.050 Uiso 1 1 calc GR . . . .
C23 C 0.44554(10) 0.6992(2) 0.52922(6) 0.0231(4) Uani 1 1 d . . . . .
H23 H 0.4388 0.6131 0.5092 0.028 Uiso 1 1 calc R . . . .
C24 C 0.37896(11) 0.7241(2) 0.55774(7) 0.0313(5) Uani 1 1 d . . . . .
H24A H 0.3716 0.6467 0.5805 0.047 Uiso 1 1 calc GR . . . .
H24B H 0.3388 0.7304 0.5351 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.3833 0.8113 0.5761 0.047 Uiso 1 1 calc GR . . . .
H14 H 0.5145(9) 0.766(2) 0.5742(6) 0.003(4) Uiso 1 1 d . . . . .
H3 H 0.7268(15) 1.052(3) 0.6574(10) 0.054(8) Uiso 1 1 d . . . . .
H13A H 0.7657(16) 0.784(3) 0.8298(11) 0.057(9) Uiso 1 1 d . . . . .
H9 H 0.547(2) 0.744(4) 0.6802(13) 0.085 Uiso 1 1 d R . . . .
H1 H 0.7013(16) 0.279(2) 0.5683(10) 0.051(8) Uiso 1 1 d D . . . .
H11 H 0.5194(17) 1.526(2) 0.5908(8) 0.077 Uiso 1 1 d DR . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0452(9) 0.0133(7) 0.0215(7) 0.0005(5) -0.0048(6) 0.0013(6)
O2 0.0410(8) 0.0181(7) 0.0194(7) 0.0028(5) -0.0052(6) 0.0019(6)
O3 0.0338(8) 0.0172(7) 0.0182(6) -0.0014(5) -0.0036(5) 0.0006(6)
O4 0.0402(8) 0.0143(7) 0.0256(7) -0.0001(5) -0.0059(6) -0.0010(6)
O5 0.0307(7) 0.0214(7) 0.0167(6) 0.0052(5) -0.0041(5) 0.0022(6)
O6 0.0308(8) 0.0235(7) 0.0201(6) -0.0013(5) -0.0060(6) -0.0006(6)
C1 0.0170(9) 0.0164(9) 0.0189(8) 0.0022(7) 0.0011(6) 0.0003(7)
C2 0.0158(9) 0.0184(9) 0.0189(8) 0.0008(7) 0.0003(6) -0.0005(7)
C3 0.0156(9) 0.0194(9) 0.0164(8) 0.0019(7) -0.0014(7) -0.0002(7)
C4 0.0155(9) 0.0188(9) 0.0175(8) 0.0014(7) 0.0010(6) 0.0012(7)
C5 0.0177(9) 0.0162(9) 0.0183(8) 0.0002(7) 0.0000(7) -0.0002(7)
C6 0.0169(9) 0.0196(9) 0.0171(8) 0.0016(7) 0.0013(7) 0.0007(7)
C7 0.0186(9) 0.0160(9) 0.0184(8) 0.0004(7) 0.0001(7) -0.0007(7)
C8 0.0136(9) 0.0187(9) 0.0175(8) 0.0022(7) -0.0004(6) -0.0001(7)
C9 0.0194(9) 0.0199(9) 0.0173(8) 0.0002(7) -0.0005(7) 0.0023(7)
O7 0.0323(8) 0.0176(7) 0.0215(6) -0.0053(5) -0.0067(6) -0.0017(5)
O8 0.0296(7) 0.0197(7) 0.0160(6) 0.0028(5) -0.0040(5) 0.0016(5)
O9 0.0492(9) 0.0122(7) 0.0235(7) -0.0011(5) -0.0072(6) -0.0036(6)
O10 0.0363(8) 0.0174(7) 0.0208(6) -0.0029(5) -0.0042(5) -0.0005(6)
O11 0.0394(8) 0.0155(7) 0.0205(7) 0.0016(5) -0.0053(6) 0.0024(6)
O12 0.0406(8) 0.0116(7) 0.0268(7) 0.0001(5) -0.0067(6) 0.0009(6)
C10 0.0150(9) 0.0174(9) 0.0162(8) 0.0004(7) -0.0009(6) -0.0009(7)
C11 0.0168(9) 0.0128(8) 0.0198(8) 0.0001(6) 0.0000(6) -0.0015(7)
C12 0.0157(8) 0.0159(9) 0.0202(8) 0.0043(7) 0.0007(7) 0.0010(7)
C13 0.0183(9) 0.0158(9) 0.0166(8) 0.0010(7) 0.0003(7) 0.0001(7)
C14 0.0172(9) 0.0157(9) 0.0181(8) -0.0015(7) 0.0004(6) -0.0001(7)
C15 0.0160(9) 0.0136(8) 0.0175(8) 0.0013(6) 0.0005(6) 0.0003(6)
C16 0.0155(9) 0.0150(9) 0.0174(8) 0.0010(6) -0.0011(6) -0.0008(6)
C17 0.0194(9) 0.0132(9) 0.0226(8) 0.0019(7) -0.0004(7) -0.0005(7)
C18 0.0175(9) 0.0162(9) 0.0217(9) -0.0040(7) 0.0008(7) -0.0006(7)
O13 0.0319(8) 0.0168(7) 0.0220(7) -0.0010(5) -0.0082(6) -0.0003(6)
C19 0.0322(12) 0.0274(11) 0.0261(10) -0.0018(8) -0.0007(8) 0.0079(9)
C20 0.0303(11) 0.0181(9) 0.0182(8) 0.0018(7) -0.0057(7) -0.0016(8)
C21 0.0274(11) 0.0334(12) 0.0258(10) -0.0076(8) 0.0009(8) -0.0035(9)
O14 0.0358(8) 0.0150(7) 0.0255(7) 0.0011(5) -0.0099(6) 0.0010(6)
C22 0.0292(11) 0.0416(13) 0.0286(10) 0.0109(9) -0.0013(8) -0.0015(10)
C23 0.0291(10) 0.0229(10) 0.0172(8) -0.0005(7) -0.0061(7) 0.0006(8)
C24 0.0319(12) 0.0340(12) 0.0280(10) -0.0027(9) 0.0015(8) -0.0018(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.315(2) . ?
O1 H1 0.859(17) . ?
O2 C7 1.214(2) . ?
O3 C9 1.308(2) . ?
O3 H3 0.88(3) . ?
O4 C9 1.222(2) . ?
O5 H5 0.8400 . ?
O5 C8 1.280(2) . ?
O6 H6 0.8400 . ?
O6 C8 1.260(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.394(3) . ?
C1 C7 1.499(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.484(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 C6 1.396(3) . ?
C5 C9 1.495(2) . ?
C6 H6A 0.9500 . ?
O7 H7 0.8400 . ?
O7 C16 1.274(2) . ?
O8 H8 0.8400 . ?
O8 C16 1.264(2) . ?
O9 C18 1.311(2) . ?
O9 H9 0.90(4) . ?
O10 C18 1.219(2) . ?
O11 C17 1.309(2) . ?
O11 H11 0.901(17) . ?
O12 C17 1.213(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.398(2) . ?
C10 C16 1.486(2) . ?
C11 H11A 0.9500 . ?
C11 C12 1.394(2) . ?
C12 C13 1.389(2) . ?
C12 C17 1.495(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(2) . ?
C14 C15 1.392(2) . ?
C14 C18 1.497(2) . ?
C15 H15 0.9500 . ?
O13 C20 1.452(2) . ?
O13 H13A 0.86(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.513(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.499(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O14 C23 1.449(2) . ?
O14 H14 0.940(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C23 1.506(3) . ?
C23 H23 1.0000 . ?
C23 C24 1.513(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 115(2) . . ?
C9 O3 H3 107.0(19) . . ?
C8 O5 H5 109.5 . . ?
C8 O6 H6 109.5 . . ?
C2 C1 C6 120.31(17) . . ?
C2 C1 C7 120.38(16) . . ?
C6 C1 C7 119.29(15) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.90(16) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C8 119.41(16) . . ?
C4 C3 C2 120.10(16) . . ?
C4 C3 C8 120.41(16) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.76(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.55(16) . . ?
C4 C5 C9 117.64(16) . . ?
C6 C5 C9 121.75(15) . . ?
C1 C6 C5 119.35(16) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
O1 C7 C1 112.41(15) . . ?
O2 C7 O1 124.83(17) . . ?
O2 C7 C1 122.76(16) . . ?
O5 C8 C3 117.55(16) . . ?
O6 C8 O5 124.17(16) . . ?
O6 C8 C3 118.28(16) . . ?
O3 C9 C5 114.92(16) . . ?
O4 C9 O3 124.38(17) . . ?
O4 C9 C5 120.70(16) . . ?
C16 O7 H7 109.5 . . ?
C16 O8 H8 109.5 . . ?
C18 O9 H9 120(2) . . ?
C17 O11 H11 107.2(16) . . ?
C11 C10 C15 119.68(15) . . ?
C11 C10 C16 120.62(16) . . ?
C15 C10 C16 119.64(15) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 C12 120.03(16) . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C17 117.76(16) . . ?
C13 C12 C11 120.53(16) . . ?
C13 C12 C17 121.67(15) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.42(16) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C18 119.27(15) . . ?
C15 C14 C13 120.31(16) . . ?
C15 C14 C18 120.40(16) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.99(16) . . ?
C14 C15 H15 120.0 . . ?
O7 C16 C10 117.31(15) . . ?
O8 C16 O7 124.30(15) . . ?
O8 C16 C10 118.39(15) . . ?
O11 C17 C12 114.89(15) . . ?
O12 C17 O11 124.31(16) . . ?
O12 C17 C12 120.79(16) . . ?
O9 C18 C14 112.55(15) . . ?
O10 C18 O9 124.49(17) . . ?
O10 C18 C14 122.96(17) . . ?
C20 O13 H13A 109(2) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
O13 C20 C19 110.55(15) . . ?
O13 C20 H20 108.8 . . ?
O13 C20 C21 106.64(15) . . ?
C19 C20 H20 108.8 . . ?
C21 C20 C19 113.01(16) . . ?
C21 C20 H20 108.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 O14 H14 103.4(11) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
O14 C23 C22 110.53(16) . . ?
O14 C23 H23 108.1 . . ?
O14 C23 C24 110.71(15) . . ?
C22 C23 H23 108.1 . . ?
C22 C23 C24 111.24(17) . . ?
C24 C23 H23 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O8 0.84 1.79 2.6202(18) 169.5 6_575
O6 H6 O7 0.84 1.79 2.6056(18) 163.8 6_575
O7 H7 O6 0.84 1.78 2.6056(18) 168.8 6_576
O8 H8 O5 0.84 1.80 2.6202(19) 165.1 6_576
O14 H14 O10 0.940(19) 1.909(19) 2.8251(19) 164.2(16) .
O3 H3 O13 0.88(3) 1.70(3) 2.5795(19) 174(3) 4_656
O13 H13A O2 0.86(3) 1.94(3) 2.7993(19) 176(3) 4_656
O9 H9 O12 0.90(4) 1.71(4) 2.5989(19) 167(4) 1_545
O1 H1 O4 0.859(17) 1.765(19) 2.6023(19) 164(3) 1_545
O11 H11 O14 0.901(17) 1.671(16) 2.5658(18) 172(3) 1_565
_shelx_res_file
;
pc_ht_1_i418_100k.res created by SHELXL-2014/7
TITL pc_ht_1_i418_100k_a.res in C2/c
REM Old TITL PC_HT_1_i418_100K in C2/c
REM SHELXT solution in C2/c
REM R1 0.125, Rweak 0.002, Alpha 0.022, Orientation as input
REM Formula found by SHELXT: C24 O14
CELL 0.71073 19.0126 9.6004 27.3832 90 90.563 90
ZERR 8 0.0017 0.0008 0.0024 0 0.002 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O
UNIT 192 224 112
EQIV $1 +X,-1+Y,+Z
EQIV $2 1.5-X,0.5+Y,1.5-Z
EQIV $3 +X,2-Y,-0.5+Z
EQIV $4 +X,2-Y,0.5+Z
EQIV $5 +X,1+Y,+Z
DFIX 0.82 O1 H1 O11 H11
DANG 1.85 0.02 H11 C17
L.S. 20
PLAN 20
SIZE 0.079 0.101 0.188
TEMP -173.15
HTAB O1 O4_$1
HTAB O3 O13_$2
HTAB O5 O8_$3
HTAB O6 O7_$3
HTAB O7 O6_$4
HTAB O8 O5_$4
HTAB O9 O12_$1
HTAB O11 O14_$5
HTAB O13 O2_$2
HTAB O14 O10
BOND $H
list 4
fmap 2 53
ACTA
REM
REM
REM
WGHT 0.093900 4.797100
FVAR 0.16667
O1 3 0.696477 0.361507 0.556165 11.00000 0.04516 0.01331 =
0.02153 0.00047 -0.00481 0.00131
O2 3 0.715548 0.448880 0.631070 11.00000 0.04096 0.01806 =
0.01938 0.00276 -0.00517 0.00190
O3 3 0.717611 0.968922 0.645557 11.00000 0.03376 0.01721 =
0.01824 -0.00145 -0.00359 0.00061
O4 3 0.697645 1.098299 0.578872 11.00000 0.04017 0.01427 =
0.02564 -0.00008 -0.00591 -0.00101
O5 3 0.633536 0.876798 0.424121 11.00000 0.03067 0.02145 =
0.01670 0.00521 -0.00407 0.00219
PART 1
AFIX 147
H5 2 0.626366 0.870427 0.393885 10.50000 -1.50000
AFIX 0
PART 0
O6 3 0.637136 0.643798 0.417900 11.00000 0.03082 0.02353 =
0.02012 -0.00128 -0.00599 -0.00059
PART 2
AFIX 147
H6 2 0.626869 0.662747 0.388743 10.50000 -1.50000
AFIX 0
PART 0
C1 1 0.688477 0.603387 0.565284 11.00000 0.01696 0.01644 =
0.01890 0.00222 0.00106 0.00025
C2 1 0.669789 0.613851 0.516119 11.00000 0.01578 0.01839 =
0.01895 0.00077 0.00029 -0.00049
AFIX 43
H2 2 0.664311 0.532064 0.496926 11.00000 -1.20000
AFIX 0
C3 1 0.659106 0.744859 0.495052 11.00000 0.01556 0.01936 =
0.01642 0.00188 -0.00136 -0.00017
C4 1 0.668279 0.864575 0.522860 11.00000 0.01549 0.01884 =
0.01750 0.00137 0.00102 0.00119
AFIX 43
H4 2 0.661325 0.953655 0.508498 11.00000 -1.20000
AFIX 0
C5 1 0.687733 0.853557 0.571938 11.00000 0.01772 0.01621 =
0.01830 0.00019 0.00000 -0.00023
C6 1 0.696990 0.723091 0.593575 11.00000 0.01689 0.01960 =
0.01706 0.00162 0.00129 0.00071
AFIX 43
H6A 2 0.708973 0.715926 0.627243 11.00000 -1.20000
AFIX 0
C7 1 0.701664 0.463624 0.587995 11.00000 0.01857 0.01601 =
0.01837 0.00040 0.00008 -0.00071
C8 1 0.641726 0.754930 0.442230 11.00000 0.01356 0.01871 =
0.01748 0.00216 -0.00036 -0.00011
C9 1 0.701449 0.985494 0.599393 11.00000 0.01942 0.01987 =
0.01730 0.00022 -0.00048 0.00226
O7 3 0.615727 1.344215 0.823864 11.00000 0.03234 0.01763 =
0.02149 -0.00528 -0.00666 -0.00168
PART 2
AFIX 147
H7 2 0.620033 1.337649 0.854336 10.50000 -1.50000
AFIX 0
PART 0
O8 3 0.616833 1.111027 0.829122 11.00000 0.02958 0.01968 =
0.01603 0.00283 -0.00404 0.00162
PART 1
AFIX 147
H8 2 0.624577 1.129477 0.858675 10.50000 -1.50000
AFIX 0
PART 0
O9 3 0.555761 0.832435 0.689809 11.00000 0.04922 0.01223 =
0.02353 -0.00112 -0.00718 -0.00356
O10 3 0.533360 0.921631 0.615704 11.00000 0.03628 0.01735 =
0.02078 -0.00287 -0.00423 -0.00051
O11 3 0.530877 1.441262 0.602695 11.00000 0.03937 0.01548 =
0.02050 0.00157 -0.00528 0.00239
O12 3 0.546480 1.568190 0.670164 11.00000 0.04063 0.01164 =
0.02682 0.00015 -0.00667 0.00093
C10 1 0.590633 1.214218 0.752690 11.00000 0.01501 0.01737 =
0.01615 0.00036 -0.00085 -0.00093
C11 1 0.578684 1.334367 0.725485 11.00000 0.01677 0.01280 =
0.01982 0.00012 0.00001 -0.00150
AFIX 43
H11A 2 0.583600 1.423228 0.740397 11.00000 -1.20000
AFIX 0
C12 1 0.559493 1.324482 0.676332 11.00000 0.01566 0.01585 =
0.02024 0.00434 0.00068 0.00099
C13 1 0.551563 1.195178 0.654223 11.00000 0.01832 0.01583 =
0.01659 0.00100 0.00031 0.00006
AFIX 43
H13 2 0.539294 1.188861 0.620581 11.00000 -1.20000
AFIX 0
C14 1 0.561775 1.074572 0.681863 11.00000 0.01721 0.01569 =
0.01806 -0.00145 0.00039 -0.00007
C15 1 0.582065 1.083737 0.730744 11.00000 0.01602 0.01361 =
0.01751 0.00127 0.00047 0.00028
AFIX 43
H15 2 0.590087 1.001345 0.749188 11.00000 -1.20000
AFIX 0
C16 1 0.609169 1.223057 0.805432 11.00000 0.01553 0.01503 =
0.01735 0.00097 -0.00110 -0.00084
C17 1 0.545184 1.456854 0.649242 11.00000 0.01939 0.01321 =
0.02256 0.00194 -0.00044 -0.00054
C18 1 0.548944 0.935540 0.658713 11.00000 0.01750 0.01620 =
0.02169 -0.00397 0.00084 -0.00057
O13 3 0.758905 0.707561 0.814184 11.00000 0.03194 0.01677 =
0.02197 -0.00096 -0.00819 -0.00031
C19 1 0.631935 0.728482 0.803369 11.00000 0.03215 0.02742 =
0.02612 -0.00179 -0.00071 0.00792
AFIX 137
H19A 2 0.624735 0.639746 0.820290 11.00000 -1.50000
H19B 2 0.594663 0.741703 0.778832 11.00000 -1.50000
H19C 2 0.630582 0.804927 0.827059 11.00000 -1.50000
AFIX 0
C20 1 0.702699 0.727045 0.778550 11.00000 0.03029 0.01806 =
0.01822 0.00178 -0.00568 -0.00157
AFIX 13
H20 2 0.709718 0.818261 0.761652 11.00000 -1.20000
AFIX 0
C21 1 0.709568 0.611956 0.741929 11.00000 0.02741 0.03341 =
0.02582 -0.00759 0.00091 -0.00346
AFIX 137
H21A 2 0.756243 0.615930 0.727123 11.00000 -1.50000
H21B 2 0.673403 0.622717 0.716460 11.00000 -1.50000
H21C 2 0.703549 0.521966 0.758256 11.00000 -1.50000
AFIX 0
O14 3 0.504780 0.676567 0.561955 11.00000 0.03577 0.01499 =
0.02547 0.00108 -0.00988 0.00098
C22 1 0.460239 0.818317 0.495020 11.00000 0.02924 0.04159 =
0.02864 0.01085 -0.00130 -0.00149
AFIX 137
H22A 2 0.466768 0.904125 0.513912 11.00000 -1.50000
H22B 2 0.420502 0.829793 0.472310 11.00000 -1.50000
H22C 2 0.503013 0.798542 0.476583 11.00000 -1.50000
AFIX 0
C23 1 0.445535 0.699200 0.529223 11.00000 0.02915 0.02285 =
0.01722 -0.00048 -0.00613 0.00060
AFIX 13
H23 2 0.438776 0.613064 0.509185 11.00000 -1.20000
AFIX 0
C24 1 0.378962 0.724111 0.557744 11.00000 0.03188 0.03399 =
0.02795 -0.00269 0.00151 -0.00181
AFIX 137
H24A 2 0.371603 0.646726 0.580467 11.00000 -1.50000
H24B 2 0.338839 0.730429 0.535112 11.00000 -1.50000
H24C 2 0.383319 0.811317 0.576129 11.00000 -1.50000
AFIX 0
H14 2 0.514460 0.766160 0.574164 11.00000 0.00282
H3 2 0.726791 1.051913 0.657432 11.00000 0.05436
H13A 2 0.765667 0.783725 0.829840 11.00000 0.05677
H9 2 0.547086 0.744383 0.680236 11.00000 -1.50000
H1 2 0.701316 0.279455 0.568252 11.00000 0.05143
H11 2 0.519436 1.525831 0.590786 11.00000 -1.50000
HKLF 4
REM pc_ht_1_i418_100k_a.res in C2/c
REM R1 = 0.0564 for 4122 Fo > 4sig(Fo) and 0.0687 for all 5145 data
REM 373 parameters refined using 3 restraints
END
WGHT 0.0939 4.7697
REM Highest difference peak 0.651, deepest hole -0.317, 1-sigma level 0.072
Q1 1 0.5545 1.6262 0.6998 11.00000 0.05 0.65
Q2 1 0.5357 1.5490 0.6214 11.00000 0.05 0.51
Q3 1 0.5368 1.0247 0.6049 11.00000 0.05 0.49
Q4 1 0.4631 0.6053 0.4858 11.00000 0.05 0.45
Q5 1 0.5820 1.1553 0.7397 11.00000 0.05 0.41
Q6 1 0.4568 0.7764 0.5252 11.00000 0.05 0.37
Q7 1 0.5994 1.2191 0.7780 11.00000 0.05 0.37
Q8 1 0.7184 0.5571 0.6537 11.00000 0.05 0.36
Q9 1 0.6164 1.1435 0.8256 11.00000 0.05 0.34
Q10 1 0.5597 1.1264 0.6802 11.00000 0.05 0.34
Q11 1 0.4609 0.9087 0.4985 11.00000 0.05 0.33
Q12 1 0.5497 1.2750 0.6619 11.00000 0.05 0.33
Q13 1 0.7165 0.8043 0.7440 11.00000 0.05 0.32
Q14 1 0.5457 0.8842 0.6811 11.00000 0.05 0.32
Q15 1 0.6951 0.6706 0.5811 11.00000 0.05 0.31
Q16 1 0.5569 1.5642 0.6616 11.00000 0.05 0.29
Q17 1 0.5904 1.2516 0.7429 11.00000 0.05 0.29
Q18 1 0.7619 0.8198 0.7981 11.00000 0.05 0.29
Q19 1 0.5492 1.0148 0.6623 11.00000 0.05 0.28
Q20 1 0.5156 0.7994 0.5581 11.00000 0.05 0.28
;
_shelx_res_checksum 5461
_olex2_submission_special_instructions 'No special instructions were received'