# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# 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_is_mha60
_database_code_depnum_ccdc_archive 'CCDC 1914143'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;
_audit_update_record
;
2019-05-06 deposited with the CCDC. 2020-03-18 downloaded from the CCDC.
;
_publcif_datablock.id {fa114a63-126e-4870-b3f2-316102250e96}
_audit_creation_method SHELXL-2013
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
'N-(Phenyl-6-deoxy-2,3,4-tri-O-methyl-\b-D-glucopyranosid-6-yl)-pyridinium trifluoromethanesulfonate'
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H26 N O5 +, C F3 O3 S -'
_chemical_formula_sum 'C21 H26 F3 N O8 S'
_chemical_formula_weight 509.49
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_H-M_alt 'P 21 21 21'
_space_group_name_Hall 'P 2ac 2ab'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.1908(4)
_cell_length_b 15.8291(8)
_cell_length_c 20.6394(11)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 2349.3(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 3926
_cell_measurement_theta_min 2.57
_cell_measurement_theta_max 23.23
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.440
_exptl_crystal_F_000 1064
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.600
_exptl_crystal_size_mid 0.120
_exptl_crystal_size_min 0.100
_exptl_absorpt_coefficient_mu 0.208
_shelx_estimated_absorpt_T_min 0.885
_shelx_estimated_absorpt_T_max 0.979
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6800
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details ?
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 33895
_diffrn_reflns_av_unetI/netI 0.0714
_diffrn_reflns_av_R_equivalents 0.0687
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 1.621
_diffrn_reflns_theta_max 29.997
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total 6841
_reflns_number_gt 4103
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.771
_reflns_Friedel_fraction_max 1.000
_reflns_Friedel_fraction_full 1.000
_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.
;
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material SHELXL-2013
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model, with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0638P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack 0.01(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns 6841
_refine_ls_number_parameters 310
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1011
_refine_ls_R_factor_gt 0.0499
_refine_ls_wR_factor_ref 0.1178
_refine_ls_wR_factor_gt 0.1001
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_restrained_S_all 1.022
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
N1 N 0.7795(4) 0.42133(15) 0.31722(13) 0.0343(6) Uani 1 1 d . . . . .
O1 O 0.5145(3) 0.46987(11) 0.40507(10) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.2792(3) 0.40575(12) 0.46049(10) 0.0372(5) Uani 1 1 d . . . . .
O3 O 0.5587(3) 0.67541(13) 0.32851(13) 0.0499(7) Uani 1 1 d . . . . .
O4 O 0.3205(4) 0.70437(14) 0.43761(13) 0.0569(8) Uani 1 1 d . . . . .
O5 O 0.0624(3) 0.55617(14) 0.44899(12) 0.0432(6) Uani 1 1 d . . . . .
C1 C 0.5569(4) 0.52756(16) 0.35451(15) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.4730 0.5167 0.3168 0.037 Uiso 1 1 calc R U . . .
C2 C 0.5256(5) 0.61722(18) 0.37924(17) 0.0378(8) Uani 1 1 d . . . . .
H2 H 0.6128 0.6290 0.4159 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3258(5) 0.62668(17) 0.40253(16) 0.0356(8) Uani 1 1 d . . . . .
H3 H 0.2422 0.6314 0.3640 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2603(4) 0.55350(18) 0.44441(16) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.3149 0.5593 0.4887 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3186(5) 0.46870(17) 0.41563(15) 0.0320(7) Uani 1 1 d . . . . .
H5 H 0.2512 0.4579 0.3741 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7569(5) 0.51149(18) 0.33464(16) 0.0382(7) Uani 1 1 d . . . . .
H6A H 0.7894 0.5475 0.2971 0.046 Uiso 1 1 calc R U . . .
H6B H 0.8414 0.5260 0.3708 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8667(5) 0.3686(2) 0.35852(17) 0.0419(8) Uani 1 1 d . . . . .
H7 H 0.9168 0.3900 0.3978 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8836(5) 0.2850(2) 0.3444(2) 0.0503(10) Uani 1 1 d . . . . .
H8 H 0.9485 0.2482 0.3728 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8048(6) 0.2543(2) 0.2880(2) 0.0572(11) Uani 1 1 d . . . . .
H9 H 0.8123 0.1958 0.2780 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7162(6) 0.3084(2) 0.24671(18) 0.0524(9) Uani 1 1 d . . . . .
H10 H 0.6635 0.2878 0.2076 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7036(5) 0.3925(2) 0.26193(16) 0.0423(8) Uani 1 1 d . . . . .
H11 H 0.6414 0.4303 0.2335 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7131(7) 0.7293(3) 0.3380(3) 0.0940(18) Uani 1 1 d . . . . .
H12A H 0.8281 0.6961 0.3359 0.141 Uiso 1 1 calc R U . . .
H12B H 0.7036 0.7564 0.3805 0.141 Uiso 1 1 calc R U . . .
H12C H 0.7148 0.7726 0.3041 0.141 Uiso 1 1 calc R U . . .
C13 C 0.1546(6) 0.7504(2) 0.4342(2) 0.0625(12) Uani 1 1 d . . . . .
H13A H 0.0585 0.7218 0.4597 0.094 Uiso 1 1 calc R U . . .
H13B H 0.1143 0.7544 0.3890 0.094 Uiso 1 1 calc R U . . .
H13C H 0.1749 0.8073 0.4516 0.094 Uiso 1 1 calc R U . . .
C14 C -0.0108(6) 0.5446(3) 0.5121(2) 0.0614(11) Uani 1 1 d . . . . .
H14A H 0.0218 0.5932 0.5392 0.092 Uiso 1 1 calc R U . . .
H14B H 0.0415 0.4931 0.5311 0.092 Uiso 1 1 calc R U . . .
H14C H -0.1465 0.5394 0.5097 0.092 Uiso 1 1 calc R U . . .
C15 C 0.2881(5) 0.32180(18) 0.43988(15) 0.0339(7) Uani 1 1 d . . . . .
C16 C 0.2177(5) 0.2633(2) 0.48360(17) 0.0405(8) Uani 1 1 d . . . . .
H16 H 0.1670 0.2815 0.5238 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2223(5) 0.1789(2) 0.46812(18) 0.0483(9) Uani 1 1 d . . . . .
H17 H 0.1744 0.1385 0.4978 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2955(5) 0.15226(19) 0.40994(18) 0.0462(9) Uani 1 1 d . . . . .
H18 H 0.2994 0.0937 0.3998 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3632(5) 0.2106(2) 0.36647(18) 0.0428(8) Uani 1 1 d . . . . .
H19 H 0.4124 0.1921 0.3262 0.051 Uiso 1 1 calc R U . . .
C20 C 0.3601(5) 0.29596(19) 0.38098(15) 0.0371(8) Uani 1 1 d . . . . .
H20 H 0.4067 0.3362 0.3509 0.045 Uiso 1 1 calc R U . . .
S1 S 1.20714(13) 0.49052(5) 0.21549(4) 0.0417(2) Uani 1 1 d . . . . .
O7 O 1.3909(4) 0.5099(2) 0.19341(14) 0.0776(9) Uani 1 1 d . . . . .
O8 O 1.1853(4) 0.41154(15) 0.24736(12) 0.0587(7) Uani 1 1 d . . . . .
O9 O 1.1138(5) 0.55812(16) 0.24722(14) 0.0718(9) Uani 1 1 d . . . . .
C21 C 1.0800(6) 0.4781(2) 0.14015(19) 0.0523(9) Uani 1 1 d . . . . .
F1 F 1.1380(5) 0.41126(16) 0.10745(11) 0.0864(9) Uani 1 1 d . . . . .
F2 F 1.1012(3) 0.54551(15) 0.10245(11) 0.0698(7) Uani 1 1 d . . . . .
F3 F 0.8991(4) 0.46806(19) 0.15095(13) 0.0918(9) 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
N1 0.0270(15) 0.0346(13) 0.0414(15) -0.0003(11) 0.0032(13) -0.0010(11)
O1 0.0293(13) 0.0312(10) 0.0353(11) 0.0052(9) 0.0002(10) 0.0010(8)
O2 0.0453(15) 0.0312(10) 0.0352(12) 0.0029(9) 0.0058(11) -0.0019(10)
O3 0.0417(16) 0.0344(11) 0.0736(17) 0.0165(12) -0.0040(13) -0.0116(11)
O4 0.0543(18) 0.0375(12) 0.0790(19) -0.0246(12) -0.0187(15) 0.0103(12)
O5 0.0305(14) 0.0530(13) 0.0463(14) -0.0023(11) 0.0044(11) 0.0038(11)
C1 0.0318(18) 0.0279(14) 0.0339(16) 0.0035(12) -0.0013(14) -0.0048(12)
C2 0.036(2) 0.0307(15) 0.047(2) -0.0019(14) -0.0112(16) -0.0034(14)
C3 0.035(2) 0.0272(14) 0.0442(19) -0.0066(14) -0.0070(16) 0.0004(13)
C4 0.027(2) 0.0396(16) 0.0335(17) -0.0048(13) -0.0039(14) 0.0008(14)
C5 0.031(2) 0.0326(15) 0.0323(16) 0.0018(13) -0.0002(14) -0.0012(13)
C6 0.032(2) 0.0328(15) 0.0495(18) 0.0003(14) 0.0013(15) -0.0034(13)
C7 0.0295(19) 0.050(2) 0.047(2) 0.0020(16) -0.0010(16) 0.0039(15)
C8 0.039(2) 0.048(2) 0.064(3) 0.0100(19) 0.004(2) 0.0042(16)
C9 0.046(2) 0.0399(19) 0.086(3) -0.008(2) 0.023(3) 0.0022(18)
C10 0.047(2) 0.056(2) 0.054(2) -0.0173(18) 0.004(2) 0.0015(19)
C11 0.035(2) 0.051(2) 0.0404(19) -0.0009(15) 0.0030(17) 0.0005(17)
C12 0.072(3) 0.065(3) 0.144(5) 0.038(3) -0.020(4) -0.041(3)
C13 0.060(3) 0.042(2) 0.085(3) -0.012(2) 0.003(2) 0.0137(19)
C14 0.051(3) 0.071(3) 0.062(3) 0.001(2) 0.020(2) 0.001(2)
C15 0.0289(18) 0.0330(15) 0.0398(18) 0.0061(13) -0.0026(16) -0.0020(14)
C16 0.0314(19) 0.0463(18) 0.0439(19) 0.0104(15) 0.0000(17) -0.0001(16)
C17 0.044(2) 0.0422(18) 0.059(2) 0.0221(17) -0.003(2) -0.0036(17)
C18 0.039(2) 0.0338(16) 0.066(2) 0.0051(16) -0.008(2) 0.0013(15)
C19 0.034(2) 0.0396(17) 0.055(2) -0.0027(16) -0.0018(18) -0.0014(15)
C20 0.037(2) 0.0350(16) 0.0393(18) 0.0048(14) 0.0023(16) -0.0031(14)
S1 0.0437(5) 0.0465(5) 0.0349(4) 0.0028(4) -0.0009(4) -0.0010(4)
O7 0.0388(17) 0.131(3) 0.0626(17) 0.025(2) -0.0042(14) -0.0061(17)
O8 0.084(2) 0.0495(14) 0.0428(14) 0.0144(12) 0.0002(15) 0.0106(14)
O9 0.103(3) 0.0466(15) 0.0656(18) -0.0133(13) 0.0243(18) -0.0015(15)
C21 0.043(2) 0.063(2) 0.051(2) 0.016(2) 0.0039(19) -0.0013(19)
F1 0.142(3) 0.0722(15) 0.0451(14) -0.0114(12) -0.0029(16) -0.0031(16)
F2 0.0650(16) 0.0827(15) 0.0618(15) 0.0423(12) 0.0002(12) 0.0092(13)
F3 0.0534(17) 0.137(2) 0.0848(18) 0.0473(18) -0.0183(14) -0.0247(16)
#==============================================================================
# MOLECULAR GEOMETRY
_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
N1 C11 1.345(4) . ?
N1 C7 1.348(4) . ?
N1 C6 1.481(4) . ?
O1 C1 1.420(3) . ?
O1 C5 1.426(4) . ?
O2 C5 1.389(3) . ?
O2 C15 1.397(4) . ?
O3 C12 1.413(5) . ?
O3 C2 1.415(4) . ?
O4 C13 1.400(5) . ?
O4 C3 1.428(3) . ?
O5 C14 1.417(4) . ?
O5 C4 1.427(4) . ?
C1 C6 1.517(5) . ?
C1 C2 1.525(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.523(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.520(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.527(4) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.361(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.383(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.375(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
S1 O8 1.422(2) . ?
S1 O9 1.423(3) . ?
S1 O7 1.431(3) . ?
S1 C21 1.815(4) . ?
C21 F1 1.322(4) . ?
C21 F3 1.329(5) . ?
C21 F2 1.330(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
C11 N1 C7 121.0(3) . . ?
C11 N1 C6 119.3(3) . . ?
C7 N1 C6 119.6(3) . . ?
C1 O1 C5 109.4(2) . . ?
C5 O2 C15 118.0(2) . . ?
C12 O3 C2 115.0(3) . . ?
C13 O4 C3 116.5(3) . . ?
C14 O5 C4 115.3(3) . . ?
O1 C1 C6 107.1(2) . . ?
O1 C1 C2 108.7(2) . . ?
C6 C1 C2 112.7(2) . . ?
O1 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O3 C2 C3 109.2(3) . . ?
O3 C2 C1 109.5(3) . . ?
C3 C2 C1 109.6(2) . . ?
O3 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
O4 C3 C4 111.1(3) . . ?
O4 C3 C2 105.7(2) . . ?
C4 C3 C2 113.4(3) . . ?
O4 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
O5 C4 C3 108.9(3) . . ?
O5 C4 C5 109.0(2) . . ?
C3 C4 C5 111.3(2) . . ?
O5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
O2 C5 O1 108.2(2) . . ?
O2 C5 C4 108.4(2) . . ?
O1 C5 C4 108.6(2) . . ?
O2 C5 H5 110.5 . . ?
O1 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
N1 C6 C1 109.3(2) . . ?
N1 C6 H6A 109.8 . . ?
C1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N1 C7 C8 120.5(3) . . ?
N1 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 119.8(3) . . ?
N1 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.7(3) . . ?
C20 C15 O2 124.5(3) . . ?
C16 C15 O2 114.8(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.0(3) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O8 S1 O9 113.34(16) . . ?
O8 S1 O7 115.98(19) . . ?
O9 S1 O7 114.9(2) . . ?
O8 S1 C21 104.20(17) . . ?
O9 S1 C21 103.8(2) . . ?
O7 S1 C21 102.46(17) . . ?
F1 C21 F3 107.4(4) . . ?
F1 C21 F2 107.9(3) . . ?
F3 C21 F2 107.8(3) . . ?
F1 C21 S1 111.4(3) . . ?
F3 C21 S1 111.2(3) . . ?
F2 C21 S1 110.9(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C6 -167.0(2) . . . . ?
C5 O1 C1 C2 71.0(3) . . . . ?
C12 O3 C2 C3 125.7(4) . . . . ?
C12 O3 C2 C1 -114.2(4) . . . . ?
O1 C1 C2 O3 -177.2(2) . . . . ?
C6 C1 C2 O3 64.2(3) . . . . ?
O1 C1 C2 C3 -57.5(3) . . . . ?
C6 C1 C2 C3 -176.1(3) . . . . ?
C13 O4 C3 C4 -90.1(4) . . . . ?
C13 O4 C3 C2 146.6(3) . . . . ?
O3 C2 C3 O4 -72.8(3) . . . . ?
C1 C2 C3 O4 167.3(2) . . . . ?
O3 C2 C3 C4 165.4(2) . . . . ?
C1 C2 C3 C4 45.4(4) . . . . ?
C14 O5 C4 C3 -134.4(3) . . . . ?
C14 O5 C4 C5 104.0(3) . . . . ?
O4 C3 C4 O5 76.8(3) . . . . ?
C2 C3 C4 O5 -164.4(3) . . . . ?
O4 C3 C4 C5 -163.0(3) . . . . ?
C2 C3 C4 C5 -44.2(4) . . . . ?
C15 O2 C5 O1 -74.3(3) . . . . ?
C15 O2 C5 C4 168.0(3) . . . . ?
C1 O1 C5 O2 174.0(2) . . . . ?
C1 O1 C5 C4 -68.5(3) . . . . ?
O5 C4 C5 O2 -68.5(3) . . . . ?
C3 C4 C5 O2 171.3(3) . . . . ?
O5 C4 C5 O1 174.1(2) . . . . ?
C3 C4 C5 O1 54.0(3) . . . . ?
C11 N1 C6 C1 71.6(4) . . . . ?
C7 N1 C6 C1 -104.9(3) . . . . ?
O1 C1 C6 N1 55.1(3) . . . . ?
C2 C1 C6 N1 174.7(2) . . . . ?
C11 N1 C7 C8 1.5(5) . . . . ?
C6 N1 C7 C8 177.9(3) . . . . ?
N1 C7 C8 C9 -2.0(5) . . . . ?
C7 C8 C9 C10 1.8(6) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C7 N1 C11 C10 -0.7(5) . . . . ?
C6 N1 C11 C10 -177.1(3) . . . . ?
C9 C10 C11 N1 0.4(6) . . . . ?
C5 O2 C15 C20 10.2(5) . . . . ?
C5 O2 C15 C16 -169.7(3) . . . . ?
C20 C15 C16 C17 0.8(5) . . . . ?
O2 C15 C16 C17 -179.2(3) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C16 C15 C20 C19 -0.8(5) . . . . ?
O2 C15 C20 C19 179.2(3) . . . . ?
C18 C19 C20 C15 0.1(5) . . . . ?
O8 S1 C21 F1 -54.7(3) . . . . ?
O9 S1 C21 F1 -173.5(3) . . . . ?
O7 S1 C21 F1 66.6(3) . . . . ?
O8 S1 C21 F3 65.2(3) . . . . ?
O9 S1 C21 F3 -53.7(3) . . . . ?
O7 S1 C21 F3 -173.6(3) . . . . ?
O8 S1 C21 F2 -174.9(3) . . . . ?
O9 S1 C21 F2 66.3(3) . . . . ?
O7 S1 C21 F2 -53.6(3) . . . . ?
_refine_diff_density_max 0.222
_refine_diff_density_min -0.285
_refine_diff_density_rms 0.046
_shelxl_version_number 2013-4
_shelx_res_file
;
TITL mha60 in P2(1)2(1)2(1)
CELL 0.71073 7.1908 15.8291 20.6394 90.000 90.000 90.000
ZERR 4.00 0.0004 0.0008 0.0011 0.000 0.000 0.000
LATT -1
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM - X, 1/2 + Y, 1/2 - Z
SYMM 1/2 + X, 1/2 - Y, - Z
SFAC C H N O F S
UNIT 84 104 4 32 12 4
MERG 2
OMIT -3.00 60.00
OMIT 0 6 3
FMAP 2
PLAN 20
SIZE 0.100 0.120 0.600
ACTA
BOND $H
CONF
L.S. 8
TEMP -99.96
WGHT 0.047000 0.063800
FVAR 0.10562
MOLE 1
N1 3 0.779464 0.421327 0.317223 11.00000 0.02703 0.03463 =
0.04137 -0.00034 0.00316 -0.00098
O1 4 0.514542 0.469866 0.405072 11.00000 0.02934 0.03116 =
0.03532 0.00519 0.00017 0.00098
O2 4 0.279250 0.405753 0.460489 11.00000 0.04533 0.03122 =
0.03519 0.00288 0.00577 -0.00194
O3 4 0.558704 0.675408 0.328514 11.00000 0.04174 0.03441 =
0.07361 0.01654 -0.00403 -0.01162
O4 4 0.320491 0.704369 0.437609 11.00000 0.05425 0.03751 =
0.07900 -0.02461 -0.01874 0.01032
O5 4 0.062358 0.556168 0.448994 11.00000 0.03047 0.05300 =
0.04625 -0.00230 0.00436 0.00381
C1 1 0.556894 0.527560 0.354508 11.00000 0.03185 0.02790 =
0.03393 0.00345 -0.00132 -0.00476
AFIX 13
H1 2 0.473027 0.516672 0.316772 11.00000 -1.20000
AFIX 0
C2 1 0.525647 0.617223 0.379241 11.00000 0.03632 0.03066 =
0.04655 -0.00193 -0.01124 -0.00340
AFIX 13
H2 2 0.612765 0.628961 0.415918 11.00000 -1.20000
AFIX 0
C3 1 0.325776 0.626678 0.402530 11.00000 0.03546 0.02719 =
0.04417 -0.00660 -0.00703 0.00041
AFIX 13
H3 2 0.242208 0.631395 0.363972 11.00000 -1.20000
AFIX 0
C4 1 0.260286 0.553505 0.444413 11.00000 0.02724 0.03961 =
0.03349 -0.00478 -0.00385 0.00084
AFIX 13
H4 2 0.314946 0.559296 0.488743 11.00000 -1.20000
AFIX 0
C5 1 0.318609 0.468698 0.415626 11.00000 0.03102 0.03264 =
0.03230 0.00178 -0.00022 -0.00117
AFIX 13
H5 2 0.251153 0.457923 0.374070 11.00000 -1.20000
AFIX 0
C6 1 0.756905 0.511492 0.334635 11.00000 0.03221 0.03284 =
0.04949 0.00025 0.00127 -0.00343
AFIX 23
H6A 2 0.789390 0.547489 0.297078 11.00000 -1.20000
H6B 2 0.841392 0.525955 0.370847 11.00000 -1.20000
AFIX 0
C7 1 0.866712 0.368615 0.358523 11.00000 0.02947 0.04956 =
0.04675 0.00197 -0.00098 0.00388
AFIX 43
H7 2 0.916839 0.389994 0.397827 11.00000 -1.20000
AFIX 0
C8 1 0.883559 0.284981 0.344352 11.00000 0.03908 0.04768 =
0.06406 0.01003 0.00375 0.00424
AFIX 43
H8 2 0.948541 0.248198 0.372817 11.00000 -1.20000
AFIX 0
C9 1 0.804848 0.254335 0.288002 11.00000 0.04598 0.03993 =
0.08575 -0.00755 0.02263 0.00225
AFIX 43
H9 2 0.812342 0.195848 0.278012 11.00000 -1.20000
AFIX 0
C10 1 0.716231 0.308396 0.246706 11.00000 0.04683 0.05627 =
0.05410 -0.01727 0.00440 0.00153
AFIX 43
H10 2 0.663539 0.287798 0.207564 11.00000 -1.20000
AFIX 0
C11 1 0.703585 0.392477 0.261934 11.00000 0.03533 0.05124 =
0.04045 -0.00093 0.00305 0.00049
AFIX 43
H11 2 0.641376 0.430281 0.233504 11.00000 -1.20000
AFIX 0
C12 1 0.713137 0.729261 0.337958 11.00000 0.07205 0.06540 =
0.14447 0.03788 -0.01971 -0.04066
AFIX 137
H12A 2 0.828056 0.696091 0.335878 11.00000 -1.50000
H12B 2 0.703612 0.756436 0.380492 11.00000 -1.50000
H12C 2 0.714817 0.772595 0.304051 11.00000 -1.50000
AFIX 0
C13 1 0.154590 0.750449 0.434230 11.00000 0.05985 0.04233 =
0.08531 -0.01176 0.00285 0.01367
AFIX 137
H13A 2 0.058472 0.721826 0.459749 11.00000 -1.50000
H13B 2 0.114255 0.754449 0.388979 11.00000 -1.50000
H13C 2 0.174915 0.807326 0.451596 11.00000 -1.50000
AFIX 0
C14 1 -0.010832 0.544574 0.512096 11.00000 0.05103 0.07104 =
0.06220 0.00065 0.02015 0.00101
AFIX 137
H14A 2 0.021800 0.593231 0.539165 11.00000 -1.50000
H14B 2 0.041531 0.493077 0.531119 11.00000 -1.50000
H14C 2 -0.146459 0.539393 0.509657 11.00000 -1.50000
AFIX 0
C15 1 0.288125 0.321802 0.439884 11.00000 0.02889 0.03303 =
0.03983 0.00613 -0.00261 -0.00200
C16 1 0.217717 0.263328 0.483601 11.00000 0.03138 0.04632 =
0.04390 0.01043 -0.00003 -0.00007
AFIX 43
H16 2 0.166970 0.281465 0.523757 11.00000 -1.20000
AFIX 0
C17 1 0.222258 0.178866 0.468124 11.00000 0.04383 0.04224 =
0.05875 0.02211 -0.00279 -0.00361
AFIX 43
H17 2 0.174419 0.138497 0.497827 11.00000 -1.20000
AFIX 0
C18 1 0.295544 0.152260 0.409941 11.00000 0.03936 0.03381 =
0.06553 0.00509 -0.00811 0.00129
AFIX 43
H18 2 0.299407 0.093734 0.399836 11.00000 -1.20000
AFIX 0
C19 1 0.363155 0.210579 0.366475 11.00000 0.03387 0.03963 =
0.05504 -0.00273 -0.00176 -0.00144
AFIX 43
H19 2 0.412357 0.192100 0.326177 11.00000 -1.20000
AFIX 0
C20 1 0.360077 0.295965 0.380978 11.00000 0.03696 0.03495 =
0.03935 0.00484 0.00234 -0.00309
AFIX 43
H20 2 0.406676 0.336196 0.350927 11.00000 -1.20000
AFIX 0
MOLE 2
S1 6 1.207141 0.490524 0.215485 11.00000 0.04366 0.04653 =
0.03489 0.00282 -0.00086 -0.00104
O7 4 1.390899 0.509902 0.193411 11.00000 0.03883 0.13148 =
0.06259 0.02513 -0.00422 -0.00606
O8 4 1.185274 0.411535 0.247358 11.00000 0.08376 0.04953 =
0.04278 0.01437 0.00016 0.01062
O9 4 1.113795 0.558118 0.247219 11.00000 0.10330 0.04660 =
0.06565 -0.01335 0.02426 -0.00153
C21 1 1.079995 0.478076 0.140146 11.00000 0.04306 0.06291 =
0.05081 0.01636 0.00394 -0.00131
F1 5 1.137999 0.411258 0.107446 11.00000 0.14188 0.07221 =
0.04507 -0.01140 -0.00291 -0.00312
F2 5 1.101158 0.545508 0.102447 11.00000 0.06502 0.08268 =
0.06184 0.04231 0.00018 0.00923
F3 5 0.899070 0.468059 0.150955 11.00000 0.05338 0.13732 =
0.08485 0.04727 -0.01833 -0.02467
HKLF 4
REM mha60 in P2(1)2(1)2(1)
REM R1 = 0.0499 for 4103 Fo > 4sig(Fo) and 0.1011 for all 6841 data
REM 310 parameters refined using 0 restraints
END
WGHT 0.0471 0.0638
REM Highest difference peak 0.222, deepest hole -0.285, 1-sigma level 0.046
Q1 1 0.2731 0.5145 0.4264 11.00000 0.05 0.20
Q2 1 0.8982 0.5289 0.1716 11.00000 0.05 0.18
Q3 1 0.5366 0.5851 0.3629 11.00000 0.05 0.18
Q4 1 0.6275 0.7609 0.3655 11.00000 0.05 0.17
Q5 1 1.0283 0.5187 0.1530 11.00000 0.05 0.17
Q6 1 1.3722 0.4236 0.1355 11.00000 0.05 0.17
Q7 1 0.7761 0.4600 0.2298 11.00000 0.05 0.16
Q8 1 1.3385 0.5450 0.2054 11.00000 0.05 0.16
Q9 1 1.3223 0.5386 0.1700 11.00000 0.05 0.16
Q10 1 0.1447 0.3212 0.5318 11.00000 0.05 0.16
Q11 1 0.6625 0.3798 0.3404 11.00000 0.05 0.16
Q12 1 1.0443 0.5877 0.1299 11.00000 0.05 0.16
Q13 1 0.2992 0.2548 0.4876 11.00000 0.05 0.16
Q14 1 0.2191 0.4850 0.3490 11.00000 0.05 0.16
Q15 1 0.9525 0.5553 0.1741 11.00000 0.05 0.16
Q16 1 1.4568 0.4758 0.1377 11.00000 0.05 0.16
Q17 1 0.2051 0.2789 0.4993 11.00000 0.05 0.16
Q18 1 0.4999 0.7844 0.3530 11.00000 0.05 0.15
Q19 1 1.3173 0.4368 0.1878 11.00000 0.05 0.15
Q20 1 0.8801 0.5140 0.2114 11.00000 0.05 0.15
;
_shelx_res_checksum 87133
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
#######################################################################
#
# 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_is_mhB61
_database_code_depnum_ccdc_archive 'CCDC 1916778'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;
_audit_update_record
;
2019-05-17 deposited with the CCDC. 2020-03-18 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
#==============================================================================
_chemical_name_systematic
'N-(1,4-anhydro-5-deoxy-2,3-O-isopropyliden-D-ribitol-5-yl)-pyridinium mesylate'
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H18 N O3 +, C H3 O3 S -, 0.5 (H2 O)'
_chemical_formula_sum 'C14 H22 N O6.50 S'
_chemical_formula_weight 340.38
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system monoclinic
_space_group_IT_number 5
_space_group_name_H-M_alt 'C 2'
_space_group_name_Hall 'C 2y'
_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.
;
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'
_cell_length_a 16.0965(11)
_cell_length_b 8.7488(6)
_cell_length_c 13.4481(9)
_cell_angle_alpha 90
_cell_angle_beta 121.558(3)
_cell_angle_gamma 90
_cell_volume 1613.8(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 7182
_cell_measurement_theta_min 2.54
_cell_measurement_theta_max 31.93
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_density_diffrn 1.401
_exptl_crystal_F_000 724
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.360
_exptl_crystal_size_mid 0.080
_exptl_crystal_size_min 0.070
_exptl_absorpt_coefficient_mu 0.232
_shelx_estimated_absorpt_T_min 0.921
_shelx_estimated_absorpt_T_max 0.984
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6126
_exptl_absorpt_correction_T_max 0.7463
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa Apex II CCD diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 13005
_diffrn_reflns_av_unetI/netI 0.0577
_diffrn_reflns_av_R_equivalents 0.0484
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.540
_diffrn_reflns_theta_max 31.975
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total 4965
_reflns_number_gt 4616
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.689
_reflns_Friedel_fraction_max 0.771
_reflns_Friedel_fraction_full 0.931
_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.
;
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material SHELXL-2013
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.3986P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens mixed
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack -0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns 4965
_refine_ls_number_parameters 211
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0432
_refine_ls_R_factor_gt 0.0397
_refine_ls_wR_factor_ref 0.0954
_refine_ls_wR_factor_gt 0.0929
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_restrained_S_all 1.052
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
C1 C 0.18670(14) 0.5459(2) 0.25760(17) 0.0148(4) Uani 1 1 d . . . . .
H1 H 0.1717 0.4501 0.2857 0.018 Uiso 1 1 calc R U . . .
C2 C 0.29411(15) 0.7478(3) 0.33461(19) 0.0224(4) Uani 1 1 d . . . . .
H2A H 0.2961 0.7841 0.2661 0.027 Uiso 1 1 calc R U . . .
H2B H 0.3536 0.7834 0.4065 0.027 Uiso 1 1 calc R U . . .
C3 C 0.20368(16) 0.8056(3) 0.32999(18) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.1821 0.9081 0.2920 0.022 Uiso 1 1 calc R U . . .
C4 C 0.12726(15) 0.6790(2) 0.26431(19) 0.0155(4) Uani 1 1 d . . . . .
H4 H 0.0742 0.7132 0.1852 0.019 Uiso 1 1 calc R U . . .
C5 C 0.13115(14) 0.7483(3) 0.43392(16) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.06098(17) 0.8790(3) 0.40802(19) 0.0212(4) Uani 1 1 d . . . . .
H6A H 0.0481 0.9319 0.3371 0.032 Uiso 1 1 calc R U . . .
H6B H 0.0897 0.9508 0.4736 0.032 Uiso 1 1 calc R U . . .
H6C H -0.0003 0.8388 0.3966 0.032 Uiso 1 1 calc R U . . .
C7 C 0.15737(19) 0.6622(3) 0.5438(2) 0.0280(5) Uani 1 1 d . . . . .
H7A H 0.1877 0.7323 0.6105 0.042 Uiso 1 1 calc R U . . .
H7B H 0.2032 0.5799 0.5562 0.042 Uiso 1 1 calc R U . . .
H7C H 0.0982 0.6184 0.5361 0.042 Uiso 1 1 calc R U . . .
C8 C 0.16394(15) 0.5217(2) 0.13295(18) 0.0158(4) Uani 1 1 d . . . . .
H8A H 0.0929 0.5079 0.0794 0.019 Uiso 1 1 calc R U . . .
H8B H 0.1844 0.6127 0.1073 0.019 Uiso 1 1 calc R U . . .
C9 C 0.17805(14) 0.2454(3) 0.12278(17) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.1173 0.2365 0.1181 0.021 Uiso 1 1 calc R U . . .
C10 C 0.22719(19) 0.1160(2) 0.1236(2) 0.0218(5) Uani 1 1 d . . . . .
H10 H 0.2006 0.0177 0.1200 0.026 Uiso 1 1 calc R U . . .
C11 C 0.31580(19) 0.1300(3) 0.1298(2) 0.0244(5) Uani 1 1 d . . . . .
H11 H 0.3509 0.0418 0.1314 0.029 Uiso 1 1 calc R U . . .
C12 C 0.35190(16) 0.2749(3) 0.1337(2) 0.0243(5) Uani 1 1 d . . . . .
H12 H 0.4118 0.2868 0.1365 0.029 Uiso 1 1 calc R U . . .
C13 C 0.30114(16) 0.4019(3) 0.1334(2) 0.0189(4) Uani 1 1 d . . . . .
H13 H 0.3262 0.5013 0.1367 0.023 Uiso 1 1 calc R U . . .
N1 N 0.21623(13) 0.3848(2) 0.12854(15) 0.0139(3) Uani 1 1 d . . . . .
O1 O 0.28719(11) 0.58393(19) 0.33377(13) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.09103(11) 0.64224(19) 0.33810(13) 0.0208(3) Uani 1 1 d . . . . .
O3 O 0.21894(11) 0.80144(19) 0.44457(13) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.02201(16) 0.2828(3) 0.33006(18) 0.0216(4) Uani 1 1 d . . . . .
H14A H -0.0005 0.2095 0.3661 0.032 Uiso 1 1 calc R U . . .
H14B H 0.0092 0.3870 0.3453 0.032 Uiso 1 1 calc R U . . .
H14C H 0.0922 0.2696 0.3632 0.032 Uiso 1 1 calc R U . . .
S1 S -0.04099(3) 0.25100(6) 0.17756(4) 0.01507(11) Uani 1 1 d . . . . .
O4 O -0.14432(10) 0.2557(2) 0.13776(12) 0.0194(3) Uani 1 1 d . . . . .
O5 O -0.00969(13) 0.10059(18) 0.16213(14) 0.0249(4) Uani 1 1 d . . . . .
O6 O -0.01286(12) 0.37415(19) 0.12790(14) 0.0225(3) Uani 1 1 d . . . . .
O7 O 0.0000 -0.0920(3) 0.0000 0.0408(7) Uani 1 2 d S T P . .
H7 H -0.010(3) -0.032(5) 0.043(3) 0.057(11) Uiso 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
C1 0.0140(9) 0.0151(9) 0.0145(9) -0.0004(7) 0.0068(8) 0.0002(7)
C2 0.0222(10) 0.0261(10) 0.0227(10) -0.0079(10) 0.0144(9) -0.0084(11)
C3 0.0233(10) 0.0158(8) 0.0186(10) -0.0022(8) 0.0133(9) -0.0038(8)
C4 0.0170(10) 0.0141(9) 0.0172(9) -0.0013(7) 0.0101(8) 0.0004(7)
C5 0.0193(8) 0.0145(8) 0.0167(8) 0.0001(8) 0.0108(7) 0.0002(9)
C6 0.0259(11) 0.0185(10) 0.0191(10) -0.0009(8) 0.0118(9) 0.0058(8)
C7 0.0343(13) 0.0279(12) 0.0263(12) 0.0115(9) 0.0191(11) 0.0068(10)
C8 0.0181(9) 0.0132(8) 0.0168(9) -0.0004(7) 0.0096(8) 0.0026(7)
C9 0.0212(9) 0.0153(8) 0.0155(8) -0.0008(8) 0.0101(8) -0.0033(9)
C10 0.0349(13) 0.0124(10) 0.0182(10) -0.0003(8) 0.0140(10) 0.0006(8)
C11 0.0267(12) 0.0231(11) 0.0191(10) 0.0003(9) 0.0091(9) 0.0107(9)
C12 0.0169(9) 0.0296(14) 0.0247(11) -0.0038(9) 0.0097(9) 0.0024(8)
C13 0.0166(10) 0.0199(10) 0.0202(10) -0.0029(8) 0.0096(9) -0.0025(8)
N1 0.0146(8) 0.0133(8) 0.0136(8) -0.0016(6) 0.0072(7) -0.0006(6)
O1 0.0137(7) 0.0248(8) 0.0177(7) -0.0019(6) 0.0053(6) 0.0023(6)
O2 0.0260(8) 0.0186(7) 0.0270(8) -0.0095(6) 0.0204(7) -0.0075(6)
O3 0.0197(7) 0.0242(7) 0.0151(7) -0.0048(6) 0.0096(6) -0.0057(6)
C14 0.0237(10) 0.0220(12) 0.0159(10) -0.0007(8) 0.0081(9) -0.0035(8)
S1 0.0166(2) 0.0152(2) 0.0151(2) 0.00054(18) 0.00943(18) -0.00056(19)
O4 0.0169(6) 0.0220(7) 0.0205(7) -0.0007(7) 0.0105(6) -0.0024(7)
O5 0.0341(9) 0.0218(8) 0.0228(8) 0.0018(7) 0.0177(8) 0.0095(7)
O6 0.0212(8) 0.0262(8) 0.0210(8) 0.0050(7) 0.0117(7) -0.0049(7)
O7 0.082(2) 0.0186(12) 0.0404(16) 0.000 0.0449(17) 0.000
#==============================================================================
# MOLECULAR GEOMETRY
_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
C1 O1 1.429(3) . ?
C1 C8 1.532(3) . ?
C1 C4 1.539(3) . ?
C1 H1 1.0000 . ?
C2 O1 1.438(3) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.428(2) . ?
C3 C4 1.544(3) . ?
C3 H3 1.0000 . ?
C4 O2 1.426(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.422(2) . ?
C5 O2 1.438(3) . ?
C5 C7 1.509(3) . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.482(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.350(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.342(3) . ?
C13 H13 0.9500 . ?
C14 S1 1.771(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O4 1.4570(14) . ?
S1 O6 1.4588(16) . ?
S1 O5 1.4621(16) . ?
O7 H7 0.85(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
O1 C1 C8 110.45(16) . . ?
O1 C1 C4 106.68(16) . . ?
C8 C1 C4 111.65(16) . . ?
O1 C1 H1 109.3 . . ?
C8 C1 H1 109.3 . . ?
C4 C1 H1 109.3 . . ?
O1 C2 C3 105.33(16) . . ?
O1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
O1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O3 C3 C2 109.21(18) . . ?
O3 C3 C4 103.58(16) . . ?
C2 C3 C4 104.20(17) . . ?
O3 C3 H3 113.0 . . ?
C2 C3 H3 113.0 . . ?
C4 C3 H3 113.0 . . ?
O2 C4 C1 111.31(16) . . ?
O2 C4 C3 104.89(16) . . ?
C1 C4 C3 104.05(16) . . ?
O2 C4 H4 112.0 . . ?
C1 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
O3 C5 O2 104.94(14) . . ?
O3 C5 C7 108.11(17) . . ?
O2 C5 C7 108.62(19) . . ?
O3 C5 C6 111.05(19) . . ?
O2 C5 C6 110.49(17) . . ?
C7 C5 C6 113.27(17) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C1 109.88(16) . . ?
N1 C8 H8A 109.7 . . ?
C1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C1 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C10 119.99(17) . . ?
N1 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N1 C13 C12 119.8(2) . . ?
N1 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 N1 C9 121.67(18) . . ?
C13 N1 C8 119.55(17) . . ?
C9 N1 C8 118.76(16) . . ?
C1 O1 C2 106.96(15) . . ?
C4 O2 C5 108.82(15) . . ?
C5 O3 C3 107.39(15) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 S1 O6 112.28(10) . . ?
O4 S1 O5 112.65(11) . . ?
O6 S1 O5 112.78(10) . . ?
O4 S1 C14 105.83(10) . . ?
O6 S1 C14 106.69(10) . . ?
O5 S1 C14 105.96(10) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O3 81.48(19) . . . . ?
O1 C2 C3 C4 -28.7(2) . . . . ?
O1 C1 C4 O2 -101.05(18) . . . . ?
C8 C1 C4 O2 138.20(17) . . . . ?
O1 C1 C4 C3 11.4(2) . . . . ?
C8 C1 C4 C3 -109.34(18) . . . . ?
O3 C3 C4 O2 13.2(2) . . . . ?
C2 C3 C4 O2 127.39(17) . . . . ?
O3 C3 C4 C1 -103.86(18) . . . . ?
C2 C3 C4 C1 10.4(2) . . . . ?
O1 C1 C8 N1 66.2(2) . . . . ?
C4 C1 C8 N1 -175.26(16) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 N1 -0.5(3) . . . . ?
C12 C13 N1 C9 -0.6(3) . . . . ?
C12 C13 N1 C8 177.62(19) . . . . ?
C10 C9 N1 C13 1.0(3) . . . . ?
C10 C9 N1 C8 -177.2(2) . . . . ?
C1 C8 N1 C13 -97.7(2) . . . . ?
C1 C8 N1 C9 80.6(2) . . . . ?
C8 C1 O1 C2 91.15(18) . . . . ?
C4 C1 O1 C2 -30.4(2) . . . . ?
C3 C2 O1 C1 37.4(2) . . . . ?
C1 C4 O2 C5 118.60(18) . . . . ?
C3 C4 O2 C5 6.7(2) . . . . ?
O3 C5 O2 C4 -24.3(2) . . . . ?
C7 C5 O2 C4 -139.72(18) . . . . ?
C6 C5 O2 C4 95.47(19) . . . . ?
O2 C5 O3 C3 33.3(2) . . . . ?
C7 C5 O3 C3 149.10(19) . . . . ?
C6 C5 O3 C3 -86.1(2) . . . . ?
C2 C3 O3 C5 -139.16(19) . . . . ?
C4 C3 O3 C5 -28.6(2) . . . . ?
_refine_diff_density_max 0.383
_refine_diff_density_min -0.366
_refine_diff_density_rms 0.060
#==============================================================================
# SHELX FILES
_shelxl_version_number 2013-4
_shelx_res_file
;
TITL mhb61 in C2
CELL 0.71073 16.0965 8.7488 13.4481 90.000 121.558 90.000
ZERR 4.00 0.0011 0.0006 0.0009 0.000 0.003 0.000
LATT -7
SYMM - X, Y, - Z
SFAC C H N O S
UNIT 56 88 4 26 4
MERG 2
OMIT -3.00 64.00
OMIT 0 0 1
FMAP 2
PLAN 20
SIZE 0.070 0.080 0.360
ACTA
BOND $H
CONF
LIST 4
L.S. 8
TEMP -150.17
WGHT 0.040900 0.398600
FVAR 0.15703
MOLE 1
C1 1 0.186702 0.545902 0.257598 11.00000 0.01395 0.01511 =
0.01452 -0.00038 0.00681 0.00019
AFIX 13
H1 2 0.171678 0.450084 0.285722 11.00000 -1.20000
AFIX 0
C2 1 0.294106 0.747800 0.334605 11.00000 0.02225 0.02613 =
0.02275 -0.00792 0.01441 -0.00843
AFIX 23
H2A 2 0.296061 0.784149 0.266144 11.00000 -1.20000
H2B 2 0.353592 0.783444 0.406520 11.00000 -1.20000
AFIX 0
C3 1 0.203676 0.805585 0.329991 11.00000 0.02331 0.01585 =
0.01860 -0.00223 0.01325 -0.00385
AFIX 13
H3 2 0.182059 0.908081 0.292014 11.00000 -1.20000
AFIX 0
C4 1 0.127265 0.678969 0.264306 11.00000 0.01702 0.01406 =
0.01720 -0.00129 0.01011 0.00040
AFIX 13
H4 2 0.074198 0.713188 0.185189 11.00000 -1.20000
AFIX 0
C5 1 0.131149 0.748347 0.433921 11.00000 0.01927 0.01450 =
0.01666 0.00012 0.01076 0.00017
C6 1 0.060977 0.878962 0.408017 11.00000 0.02592 0.01849 =
0.01910 -0.00095 0.01182 0.00575
AFIX 137
H6A 2 0.048061 0.931893 0.337068 11.00000 -1.50000
H6B 2 0.089704 0.950799 0.473635 11.00000 -1.50000
H6C 2 -0.000265 0.838760 0.396577 11.00000 -1.50000
AFIX 0
C7 1 0.157366 0.662163 0.543823 11.00000 0.03434 0.02788 =
0.02632 0.01151 0.01908 0.00682
AFIX 137
H7A 2 0.187740 0.732262 0.610506 11.00000 -1.50000
H7B 2 0.203156 0.579903 0.556215 11.00000 -1.50000
H7C 2 0.098225 0.618368 0.536106 11.00000 -1.50000
AFIX 0
C8 1 0.163942 0.521652 0.132953 11.00000 0.01806 0.01322 =
0.01684 -0.00041 0.00964 0.00257
AFIX 23
H8A 2 0.092851 0.507917 0.079353 11.00000 -1.20000
H8B 2 0.184365 0.612697 0.107310 11.00000 -1.20000
AFIX 0
C9 1 0.178046 0.245389 0.122778 11.00000 0.02124 0.01530 =
0.01549 -0.00081 0.01006 -0.00328
AFIX 43
H9 2 0.117287 0.236481 0.118131 11.00000 -1.20000
AFIX 0
C10 1 0.227192 0.116021 0.123635 11.00000 0.03492 0.01239 =
0.01819 -0.00026 0.01403 0.00063
AFIX 43
H10 2 0.200647 0.017737 0.120010 11.00000 -1.20000
AFIX 0
C11 1 0.315804 0.129960 0.129830 11.00000 0.02668 0.02312 =
0.01913 0.00026 0.00908 0.01067
AFIX 43
H11 2 0.350905 0.041772 0.131395 11.00000 -1.20000
AFIX 0
C12 1 0.351898 0.274856 0.133674 11.00000 0.01693 0.02962 =
0.02470 -0.00375 0.00971 0.00243
AFIX 43
H12 2 0.411762 0.286771 0.136500 11.00000 -1.20000
AFIX 0
C13 1 0.301139 0.401881 0.133407 11.00000 0.01660 0.01990 =
0.02021 -0.00287 0.00961 -0.00250
AFIX 43
H13 2 0.326198 0.501288 0.136661 11.00000 -1.20000
AFIX 0
N1 3 0.216226 0.384801 0.128539 11.00000 0.01459 0.01330 =
0.01358 -0.00156 0.00724 -0.00063
O1 4 0.287193 0.583929 0.333771 11.00000 0.01374 0.02478 =
0.01767 -0.00189 0.00534 0.00226
O2 4 0.091029 0.642237 0.338102 11.00000 0.02605 0.01861 =
0.02702 -0.00955 0.02042 -0.00750
O3 4 0.218940 0.801445 0.444575 11.00000 0.01965 0.02421 =
0.01514 -0.00476 0.00960 -0.00569
MOLE 2
C14 1 0.022013 0.282832 0.330065 11.00000 0.02366 0.02197 =
0.01593 -0.00074 0.00814 -0.00353
AFIX 137
H14A 2 -0.000455 0.209455 0.366055 11.00000 -1.50000
H14B 2 0.009198 0.387046 0.345340 11.00000 -1.50000
H14C 2 0.092168 0.269612 0.363206 11.00000 -1.50000
AFIX 0
S1 5 -0.040991 0.251000 0.177556 11.00000 0.01658 0.01522 =
0.01506 0.00054 0.00943 -0.00056
O4 4 -0.144325 0.255708 0.137755 11.00000 0.01690 0.02197 =
0.02047 -0.00069 0.01047 -0.00244
O5 4 -0.009695 0.100590 0.162126 11.00000 0.03405 0.02181 =
0.02281 0.00185 0.01768 0.00946
O6 4 -0.012863 0.374151 0.127903 11.00000 0.02125 0.02622 =
0.02102 0.00498 0.01175 -0.00488
MOLE 3
O7 4 0.000000 -0.092004 0.000000 10.50000 0.08200 0.01863 =
0.04041 0.00000 0.04488 0.00000
H7 2 -0.009553 -0.032249 0.042751 11.00000 0.05655
HKLF 4
REM mhb61 in C2
REM R1 = 0.0397 for 4616 Fo > 4sig(Fo) and 0.0432 for all 4965 data
REM 211 parameters refined using 1 restraints
END
WGHT 0.0409 0.3986
REM Highest difference peak 0.383, deepest hole -0.366, 1-sigma level 0.060
Q1 1 0.1584 0.7513 0.2850 11.00000 0.05 0.38
Q2 1 -0.0230 0.1680 0.1794 11.00000 0.05 0.33
Q3 1 -0.0125 0.2538 0.2635 11.00000 0.05 0.32
Q4 1 0.2481 0.7627 0.3454 11.00000 0.05 0.29
Q5 1 -0.0273 0.3438 0.1676 11.00000 0.05 0.27
Q6 1 0.2592 0.3799 0.1264 11.00000 0.05 0.26
Q7 1 0.0305 -0.0373 0.0321 11.00000 0.05 0.24
Q8 1 0.1639 0.6155 0.2622 11.00000 0.05 0.24
Q9 1 0.1376 0.6985 0.4897 11.00000 0.05 0.23
Q10 1 0.1903 0.1823 0.1017 11.00000 0.05 0.23
Q11 1 0.1652 0.5094 0.1976 11.00000 0.05 0.22
Q12 1 0.1911 0.3232 0.1151 11.00000 0.05 0.22
Q13 1 0.0405 0.1376 0.1889 11.00000 0.05 0.21
Q14 1 0.0255 0.4421 0.0458 11.00000 0.05 0.20
Q15 1 0.2615 0.5022 -0.0043 11.00000 0.05 0.19
Q16 1 0.4257 0.3129 0.2538 11.00000 0.05 0.19
Q17 1 0.4279 0.3391 0.0439 11.00000 0.05 0.18
Q18 1 0.1921 0.4485 0.1310 11.00000 0.05 0.18
Q19 1 0.0491 0.4968 0.5142 11.00000 0.05 0.18
Q20 1 0.2668 0.1145 0.1093 11.00000 0.05 0.18
;
_shelx_res_checksum 94426
#######################################################################
#
# 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_is_mha131
_database_code_depnum_ccdc_archive 'CCDC 1916780'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;
_audit_update_record
;
2019-05-17 deposited with the CCDC. 2020-03-18 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2013
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
'N-(Methyl-6-deoxy-2,3,4-tri-O-ethyl-\b-D-glucopyranosid-6-yl)-pyridinium trifluoromethanesulfonate'
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H30 N O5 +, C F3 O3 S -'
_chemical_formula_sum 'C19 H30 F3 N O8 S'
_chemical_formula_weight 489.50
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system monoclinic
_space_group_IT_number 5
_space_group_name_H-M_alt 'C 2'
_space_group_name_Hall 'C 2y'
_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.
;
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'
_cell_length_a 15.5061(9)
_cell_length_b 6.3564(4)
_cell_length_c 24.1497(13)
_cell_angle_alpha 90
_cell_angle_beta 100.865(3)
_cell_angle_gamma 90
_cell_volume 2337.6(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 9648
_cell_measurement_theta_min 2.58
_cell_measurement_theta_max 32.37
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.391
_exptl_crystal_F_000 1032
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.990
_exptl_crystal_size_mid 0.170
_exptl_crystal_size_min 0.110
_exptl_absorpt_coefficient_mu 0.206
_shelx_estimated_absorpt_T_min 0.822
_shelx_estimated_absorpt_T_max 0.978
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6828
_exptl_absorpt_correction_T_max 0.7464
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details ?
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 23163
_diffrn_reflns_av_unetI/netI 0.0341
_diffrn_reflns_av_R_equivalents 0.0287
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_h_max 23
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -36
_diffrn_reflns_limit_l_max 36
_diffrn_reflns_theta_min 2.576
_diffrn_reflns_theta_max 32.499
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total 7523
_reflns_number_gt 6827
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.648
_reflns_Friedel_fraction_max 0.754
_reflns_Friedel_fraction_full 0.956
_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.
;
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material SHELXL-2013
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model, with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+1.0577P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 2418 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack 0.04(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns 7523
_refine_ls_number_parameters 293
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0526
_refine_ls_R_factor_gt 0.0460
_refine_ls_wR_factor_ref 0.1121
_refine_ls_wR_factor_gt 0.1067
_refine_ls_goodness_of_fit_ref 1.077
_refine_ls_restrained_S_all 1.077
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
N1 N 0.51371(12) 0.9683(3) 0.14883(7) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.49049(10) 0.6489(3) 0.23078(6) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.40588(11) 0.3728(3) 0.24832(7) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.44654(11) 0.4668(3) 0.36658(7) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.61325(11) 0.6817(3) 0.39602(6) 0.0259(3) Uani 1 1 d . . . . .
O5 O 0.62244(10) 1.0349(2) 0.31999(7) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.43955(14) 0.5651(3) 0.26917(9) 0.0201(4) Uani 1 1 d . . . . .
H1 H 0.3907 0.6637 0.2729 0.024 Uiso 1 1 calc R U . . .
C2 C 0.49834(14) 0.5286(3) 0.32652(9) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.5418 0.4153 0.3231 0.024 Uiso 1 1 calc R U . . .
C3 C 0.54688(15) 0.7281(3) 0.34820(9) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.5043 0.8301 0.3595 0.024 Uiso 1 1 calc R U . . .
C4 C 0.59110(13) 0.8298(3) 0.30367(8) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.6414 0.7400 0.2976 0.023 Uiso 1 1 calc R U . . .
C5 C 0.52529(12) 0.8506(4) 0.24800(8) 0.0189(3) Uani 1 1 d . . . . .
H5 H 0.4769 0.9492 0.2526 0.023 Uiso 1 1 calc R U . . .
C6 C 0.32847(17) 0.3918(5) 0.20578(12) 0.0366(6) Uani 1 1 d . . . . .
H6A H 0.2829 0.4655 0.2213 0.055 Uiso 1 1 calc R U . . .
H6B H 0.3074 0.2513 0.1931 0.055 Uiso 1 1 calc R U . . .
H6C H 0.3421 0.4715 0.1738 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4491(2) 0.2474(4) 0.37808(14) 0.0440(8) Uani 1 1 d . . . . .
H7A H 0.5109 0.1999 0.3879 0.053 Uiso 1 1 calc R U . . .
H7B H 0.4203 0.1695 0.3441 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4036(2) 0.2026(5) 0.42544(14) 0.0433(7) Uani 1 1 d . . . . .
H8A H 0.4273 0.2937 0.4575 0.065 Uiso 1 1 calc R U . . .
H8B H 0.4127 0.0550 0.4367 0.065 Uiso 1 1 calc R U . . .
H8C H 0.3406 0.2296 0.4135 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5945(3) 0.7433(7) 0.44836(11) 0.0612(11) Uani 1 1 d . . . . .
H9A H 0.5392 0.6764 0.4541 0.073 Uiso 1 1 calc R U . . .
H9B H 0.5867 0.8978 0.4490 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6669(2) 0.6803(7) 0.49396(12) 0.0509(8) Uani 1 1 d . . . . .
H10A H 0.6731 0.5268 0.4941 0.076 Uiso 1 1 calc R U . . .
H10B H 0.6542 0.7268 0.5303 0.076 Uiso 1 1 calc R U . . .
H10C H 0.7217 0.7452 0.4879 0.076 Uiso 1 1 calc R U . . .
C11 C 0.71410(16) 1.0499(4) 0.34271(11) 0.0305(5) Uani 1 1 d . . . . .
H11A H 0.7478 0.9624 0.3203 0.037 Uiso 1 1 calc R U . . .
H11B H 0.7262 0.9985 0.3821 0.037 Uiso 1 1 calc R U . . .
C12 C 0.74108(19) 1.2761(5) 0.34080(14) 0.0392(6) Uani 1 1 d . . . . .
H12A H 0.7275 1.3267 0.3018 0.059 Uiso 1 1 calc R U . . .
H12B H 0.8043 1.2886 0.3552 0.059 Uiso 1 1 calc R U . . .
H12C H 0.7091 1.3606 0.3642 0.059 Uiso 1 1 calc R U . . .
C13 C 0.57324(15) 0.9319(4) 0.20323(9) 0.0246(4) Uani 1 1 d . . . . .
H13A H 0.6032 1.0653 0.2164 0.030 Uiso 1 1 calc R U . . .
H13B H 0.6188 0.8288 0.1978 0.030 Uiso 1 1 calc R U . . .
C14 C 0.47706(16) 1.1586(4) 0.13718(10) 0.0268(4) Uani 1 1 d . . . . .
H14 H 0.4872 1.2674 0.1646 0.032 Uiso 1 1 calc R U . . .
C15 C 0.42478(18) 1.1954(4) 0.08530(11) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.3987 1.3297 0.0769 0.038 Uiso 1 1 calc R U . . .
C16 C 0.41049(16) 1.0380(5) 0.04580(10) 0.0311(5) Uani 1 1 d . . . . .
H16 H 0.3757 1.0630 0.0096 0.037 Uiso 1 1 calc R U . . .
C17 C 0.44739(17) 0.8423(5) 0.05937(10) 0.0322(5) Uani 1 1 d . . . . .
H17 H 0.4372 0.7304 0.0329 0.039 Uiso 1 1 calc R U . . .
C18 C 0.49909(16) 0.8113(4) 0.11163(9) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.5245 0.6771 0.1213 0.032 Uiso 1 1 calc R U . . .
S1 S 0.20519(4) 0.84340(9) 0.13100(2) 0.02572(12) Uani 1 1 d . . . . .
O6 O 0.17897(14) 0.6311(3) 0.11431(10) 0.0413(5) Uani 1 1 d . . . . .
O7 O 0.15054(14) 0.9453(4) 0.16500(8) 0.0395(5) Uani 1 1 d . . . . .
O8 O 0.29783(12) 0.8799(3) 0.14789(8) 0.0365(4) Uani 1 1 d . . . . .
F1 F 0.09039(11) 0.9649(3) 0.04310(7) 0.0398(4) Uani 1 1 d . . . . .
F2 F 0.19532(15) 1.1876(3) 0.06966(8) 0.0517(5) Uani 1 1 d . . . . .
F3 F 0.21924(12) 0.9073(3) 0.02538(7) 0.0467(5) Uani 1 1 d . . . . .
C19 C 0.17696(18) 0.9829(4) 0.06423(11) 0.0294(5) 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
N1 0.0180(8) 0.0256(8) 0.0181(8) 0.0015(7) 0.0042(6) -0.0033(7)
O1 0.0208(7) 0.0237(7) 0.0195(7) -0.0031(6) 0.0044(5) -0.0017(6)
O2 0.0274(8) 0.0205(8) 0.0313(8) -0.0027(6) -0.0015(6) -0.0036(6)
O3 0.0309(9) 0.0165(7) 0.0288(8) 0.0030(6) 0.0125(7) 0.0046(6)
O4 0.0306(9) 0.0277(8) 0.0176(7) 0.0005(6) 0.0005(6) 0.0054(7)
O5 0.0192(7) 0.0194(7) 0.0269(8) -0.0018(6) 0.0006(6) 0.0004(6)
C1 0.0187(9) 0.0172(9) 0.0245(9) -0.0016(7) 0.0045(8) 0.0003(7)
C2 0.0221(10) 0.0168(8) 0.0220(9) 0.0012(7) 0.0060(7) 0.0042(7)
C3 0.0236(10) 0.0179(9) 0.0186(9) -0.0005(7) 0.0024(7) 0.0036(7)
C4 0.0203(9) 0.0175(8) 0.0192(8) -0.0014(7) 0.0018(7) 0.0009(8)
C5 0.0175(8) 0.0210(8) 0.0179(8) 0.0004(7) 0.0025(6) 0.0001(8)
C6 0.0267(12) 0.0377(14) 0.0413(14) -0.0089(11) -0.0040(10) -0.0030(10)
C7 0.063(2) 0.0222(12) 0.0546(18) 0.0103(11) 0.0311(16) 0.0076(12)
C8 0.0513(18) 0.0349(14) 0.0463(16) 0.0164(12) 0.0161(14) 0.0026(13)
C9 0.074(2) 0.087(3) 0.0190(12) -0.0053(15) 0.0005(13) 0.037(2)
C10 0.063(2) 0.062(2) 0.0228(12) 0.0050(13) -0.0044(12) 0.0053(17)
C11 0.0212(11) 0.0305(12) 0.0363(13) -0.0040(10) -0.0036(9) -0.0017(9)
C12 0.0295(13) 0.0333(13) 0.0538(17) -0.0121(12) 0.0055(12) -0.0065(10)
C13 0.0191(9) 0.0350(12) 0.0186(9) 0.0048(8) 0.0007(7) -0.0030(8)
C14 0.0300(12) 0.0236(10) 0.0271(10) 0.0011(8) 0.0058(9) -0.0014(9)
C15 0.0306(12) 0.0300(12) 0.0332(12) 0.0099(10) 0.0023(10) 0.0014(10)
C16 0.0249(11) 0.0441(14) 0.0228(10) 0.0084(10) 0.0009(9) -0.0023(10)
C17 0.0353(12) 0.0375(12) 0.0227(10) -0.0062(10) 0.0024(8) -0.0024(12)
C18 0.0301(11) 0.0286(12) 0.0217(9) -0.0010(8) 0.0048(8) 0.0045(9)
S1 0.0239(2) 0.0220(2) 0.0316(3) 0.0041(2) 0.00630(19) 0.0000(2)
O6 0.0371(11) 0.0217(9) 0.0646(14) 0.0040(9) 0.0079(10) -0.0053(8)
O7 0.0400(11) 0.0475(12) 0.0336(10) 0.0019(9) 0.0140(8) 0.0071(9)
O8 0.0261(8) 0.0362(11) 0.0454(10) 0.0050(8) 0.0025(7) -0.0038(8)
F1 0.0334(8) 0.0471(10) 0.0360(8) 0.0043(7) -0.0006(6) 0.0048(7)
F2 0.0801(14) 0.0238(8) 0.0474(10) 0.0103(7) 0.0023(10) -0.0107(8)
F3 0.0451(10) 0.0659(13) 0.0327(8) -0.0095(8) 0.0163(7) -0.0107(9)
C19 0.0346(13) 0.0261(11) 0.0276(11) 0.0005(9) 0.0059(9) -0.0044(9)
#==============================================================================
# MOLECULAR GEOMETRY
_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
N1 C18 1.333(3) . ?
N1 C14 1.344(3) . ?
N1 C13 1.475(3) . ?
O1 C5 1.422(3) . ?
O1 C1 1.429(3) . ?
O2 C1 1.386(3) . ?
O2 C6 1.430(3) . ?
O3 C7 1.421(3) . ?
O3 C2 1.424(3) . ?
O4 C9 1.405(3) . ?
O4 C3 1.425(3) . ?
O5 C4 1.421(3) . ?
O5 C11 1.427(3) . ?
C1 C2 1.525(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.517(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.533(3) . ?
C4 H4 1.0000 . ?
C5 C13 1.514(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.481(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.472(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.500(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
S1 O8 1.4362(19) . ?
S1 O7 1.440(2) . ?
S1 O6 1.445(2) . ?
S1 C19 1.820(3) . ?
F1 C19 1.348(3) . ?
F2 C19 1.333(3) . ?
F3 C19 1.332(3) . ?
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
C18 N1 C14 121.4(2) . . ?
C18 N1 C13 118.8(2) . . ?
C14 N1 C13 119.8(2) . . ?
C5 O1 C1 111.84(15) . . ?
C1 O2 C6 113.22(19) . . ?
C7 O3 C2 113.88(18) . . ?
C9 O4 C3 115.5(2) . . ?
C4 O5 C11 115.56(17) . . ?
O2 C1 O1 108.02(16) . . ?
O2 C1 C2 108.38(17) . . ?
O1 C1 C2 109.68(17) . . ?
O2 C1 H1 110.2 . . ?
O1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
O3 C2 C3 107.63(16) . . ?
O3 C2 C1 109.98(17) . . ?
C3 C2 C1 111.04(17) . . ?
O3 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
O4 C3 C2 110.01(17) . . ?
O4 C3 C4 107.90(17) . . ?
C2 C3 C4 111.77(17) . . ?
O4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
O5 C4 C3 111.66(16) . . ?
O5 C4 C5 107.48(17) . . ?
C3 C4 C5 109.99(16) . . ?
O5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
O1 C5 C13 108.01(17) . . ?
O1 C5 C4 109.38(17) . . ?
C13 C5 C4 108.69(16) . . ?
O1 C5 H5 110.2 . . ?
C13 C5 H5 110.2 . . ?
C4 C5 H5 110.2 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C8 109.9(2) . . ?
O3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C10 109.8(3) . . ?
O4 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O4 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 C12 108.4(2) . . ?
O5 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O5 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C5 112.37(17) . . ?
N1 C13 H13A 109.1 . . ?
C5 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C5 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N1 C14 C15 119.8(2) . . ?
N1 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N1 C18 C17 120.4(2) . . ?
N1 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
O8 S1 O7 115.46(13) . . ?
O8 S1 O6 116.35(13) . . ?
O7 S1 O6 114.47(13) . . ?
O8 S1 C19 103.51(12) . . ?
O7 S1 C19 102.52(12) . . ?
O6 S1 C19 101.55(13) . . ?
F3 C19 F2 107.3(2) . . ?
F3 C19 F1 106.9(2) . . ?
F2 C19 F1 107.4(2) . . ?
F3 C19 S1 112.34(19) . . ?
F2 C19 S1 112.17(18) . . ?
F1 C19 S1 110.49(17) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O2 C1 O1 -81.6(2) . . . . ?
C6 O2 C1 C2 159.63(19) . . . . ?
C5 O1 C1 O2 178.01(16) . . . . ?
C5 O1 C1 C2 -64.1(2) . . . . ?
C7 O3 C2 C3 -136.9(2) . . . . ?
C7 O3 C2 C1 102.0(3) . . . . ?
O2 C1 C2 O3 -68.5(2) . . . . ?
O1 C1 C2 O3 173.74(16) . . . . ?
O2 C1 C2 C3 172.44(17) . . . . ?
O1 C1 C2 C3 54.7(2) . . . . ?
C9 O4 C3 C2 -105.3(3) . . . . ?
C9 O4 C3 C4 132.6(3) . . . . ?
O3 C2 C3 O4 70.6(2) . . . . ?
C1 C2 C3 O4 -168.99(16) . . . . ?
O3 C2 C3 C4 -169.56(16) . . . . ?
C1 C2 C3 C4 -49.1(2) . . . . ?
C11 O5 C4 C3 100.0(2) . . . . ?
C11 O5 C4 C5 -139.28(19) . . . . ?
O4 C3 C4 O5 -69.8(2) . . . . ?
C2 C3 C4 O5 169.11(16) . . . . ?
O4 C3 C4 C5 170.94(17) . . . . ?
C2 C3 C4 C5 49.9(2) . . . . ?
C1 O1 C5 C13 -176.61(17) . . . . ?
C1 O1 C5 C4 65.3(2) . . . . ?
O5 C4 C5 O1 -178.53(15) . . . . ?
C3 C4 C5 O1 -56.8(2) . . . . ?
O5 C4 C5 C13 63.7(2) . . . . ?
C3 C4 C5 C13 -174.48(18) . . . . ?
C2 O3 C7 C8 172.4(2) . . . . ?
C3 O4 C9 C10 178.2(3) . . . . ?
C4 O5 C11 C12 162.7(2) . . . . ?
C18 N1 C13 C5 -89.9(2) . . . . ?
C14 N1 C13 C5 91.6(2) . . . . ?
O1 C5 C13 N1 64.7(2) . . . . ?
C4 C5 C13 N1 -176.73(19) . . . . ?
C18 N1 C14 C15 -1.5(3) . . . . ?
C13 N1 C14 C15 176.9(2) . . . . ?
N1 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C14 N1 C18 C17 1.7(3) . . . . ?
C13 N1 C18 C17 -176.8(2) . . . . ?
C16 C17 C18 N1 -0.2(4) . . . . ?
O8 S1 C19 F3 61.5(2) . . . . ?
O7 S1 C19 F3 -178.09(19) . . . . ?
O6 S1 C19 F3 -59.5(2) . . . . ?
O8 S1 C19 F2 -59.5(2) . . . . ?
O7 S1 C19 F2 60.9(2) . . . . ?
O6 S1 C19 F2 179.5(2) . . . . ?
O8 S1 C19 F1 -179.28(17) . . . . ?
O7 S1 C19 F1 -58.9(2) . . . . ?
O6 S1 C19 F1 59.7(2) . . . . ?
_refine_diff_density_max 0.617
_refine_diff_density_min -0.297
_refine_diff_density_rms 0.055
_shelxl_version_number 2013-4
_shelx_res_file
;
TITL a1 in C2
CELL 0.71073 15.5061 6.3564 24.1497 90.000 100.865 90.000
ZERR 4.00 0.0009 0.0004 0.0013 0.000 0.003 0.000
LATT -7
SYMM - X, Y, - Z
SFAC C H N O F S
UNIT 76 120 4 32 12 4
MERG 2
OMIT -3.00 65.00
OMIT 0 0 1
OMIT 0 0 2
FMAP 2
PLAN 20
SIZE 0.110 0.170 0.990
ACTA
BOND $H
CONF
L.S. 12
TEMP -100.00
WGHT 0.053100 1.057700
FVAR 0.10925
MOLE 1
N1 3 0.513714 0.968282 0.148830 11.00000 0.01796 0.02557 =
0.01805 0.00153 0.00425 -0.00328
O1 4 0.490485 0.648924 0.230783 11.00000 0.02080 0.02369 =
0.01952 -0.00314 0.00438 -0.00171
O2 4 0.405884 0.372823 0.248322 11.00000 0.02742 0.02054 =
0.03126 -0.00266 -0.00152 -0.00359
O3 4 0.446545 0.466780 0.366578 11.00000 0.03090 0.01652 =
0.02885 0.00303 0.01247 0.00462
O4 4 0.613252 0.681705 0.396023 11.00000 0.03062 0.02772 =
0.01764 0.00048 0.00047 0.00539
O5 4 0.622436 1.034939 0.319989 11.00000 0.01917 0.01936 =
0.02695 -0.00181 0.00058 0.00037
C1 1 0.439547 0.565120 0.269170 11.00000 0.01874 0.01723 =
0.02451 -0.00165 0.00454 0.00034
AFIX 13
H1 2 0.390722 0.663693 0.272938 11.00000 -1.20000
AFIX 0
C2 1 0.498341 0.528596 0.326518 11.00000 0.02208 0.01676 =
0.02196 0.00124 0.00605 0.00416
AFIX 13
H2 2 0.541806 0.415335 0.323132 11.00000 -1.20000
AFIX 0
C3 1 0.546879 0.728118 0.348203 11.00000 0.02359 0.01794 =
0.01861 -0.00054 0.00237 0.00363
AFIX 13
H3 2 0.504265 0.830149 0.359519 11.00000 -1.20000
AFIX 0
C4 1 0.591098 0.829791 0.303667 11.00000 0.02032 0.01755 =
0.01919 -0.00137 0.00176 0.00088
AFIX 13
H4 2 0.641428 0.739969 0.297572 11.00000 -1.20000
AFIX 0
C5 1 0.525292 0.850589 0.247997 11.00000 0.01748 0.02104 =
0.01787 0.00040 0.00249 0.00011
AFIX 13
H5 2 0.476884 0.949161 0.252615 11.00000 -1.20000
AFIX 0
C6 1 0.328473 0.391765 0.205785 11.00000 0.02673 0.03775 =
0.04127 -0.00886 -0.00400 -0.00300
AFIX 137
H6A 2 0.282892 0.465528 0.221332 11.00000 -1.50000
H6B 2 0.307376 0.251290 0.193098 11.00000 -1.50000
H6C 2 0.342112 0.471456 0.173778 11.00000 -1.50000
AFIX 0
C7 1 0.449136 0.247417 0.378080 11.00000 0.06309 0.02220 =
0.05459 0.01026 0.03106 0.00765
AFIX 23
H7A 2 0.510930 0.199858 0.387915 11.00000 -1.20000
H7B 2 0.420270 0.169538 0.344106 11.00000 -1.20000
AFIX 0
C8 1 0.403579 0.202619 0.425444 11.00000 0.05127 0.03492 =
0.04628 0.01645 0.01609 0.00263
AFIX 137
H8A 2 0.427268 0.293659 0.457456 11.00000 -1.50000
H8B 2 0.412736 0.054973 0.436710 11.00000 -1.50000
H8C 2 0.340586 0.229581 0.413509 11.00000 -1.50000
AFIX 0
C9 1 0.594539 0.743341 0.448363 11.00000 0.07449 0.08688 =
0.01899 -0.00527 0.00049 0.03706
AFIX 23
H9A 2 0.539230 0.676445 0.454084 11.00000 -1.20000
H9B 2 0.586720 0.897843 0.448991 11.00000 -1.20000
AFIX 0
C10 1 0.666929 0.680255 0.493960 11.00000 0.06311 0.06190 =
0.02282 0.00500 -0.00437 0.00530
AFIX 137
H10A 2 0.673052 0.526796 0.494094 11.00000 -1.50000
H10B 2 0.654215 0.726815 0.530267 11.00000 -1.50000
H10C 2 0.721708 0.745158 0.487871 11.00000 -1.50000
AFIX 0
C11 1 0.714103 1.049893 0.342714 11.00000 0.02123 0.03047 =
0.03634 -0.00397 -0.00363 -0.00173
AFIX 23
H11A 2 0.747783 0.962437 0.320340 11.00000 -1.20000
H11B 2 0.726211 0.998500 0.382117 11.00000 -1.20000
AFIX 0
C12 1 0.741080 1.276062 0.340797 11.00000 0.02952 0.03327 =
0.05378 -0.01214 0.00554 -0.00648
AFIX 137
H12A 2 0.727457 1.326669 0.301791 11.00000 -1.50000
H12B 2 0.804335 1.288608 0.355152 11.00000 -1.50000
H12C 2 0.709069 1.360632 0.364196 11.00000 -1.50000
AFIX 0
C13 1 0.573241 0.931865 0.203231 11.00000 0.01905 0.03499 =
0.01862 0.00481 0.00066 -0.00296
AFIX 23
H13A 2 0.603179 1.065323 0.216352 11.00000 -1.20000
H13B 2 0.618766 0.828777 0.197777 11.00000 -1.20000
AFIX 0
C14 1 0.477057 1.158595 0.137175 11.00000 0.03001 0.02360 =
0.02709 0.00113 0.00578 -0.00140
AFIX 43
H14 2 0.487150 1.267386 0.164608 11.00000 -1.20000
AFIX 0
C15 1 0.424780 1.195433 0.085303 11.00000 0.03058 0.03004 =
0.03316 0.00987 0.00231 0.00142
AFIX 43
H15 2 0.398671 1.329705 0.076908 11.00000 -1.20000
AFIX 0
C16 1 0.410488 1.037951 0.045802 11.00000 0.02493 0.04413 =
0.02280 0.00840 0.00090 -0.00225
AFIX 43
H16 2 0.375700 1.063003 0.009610 11.00000 -1.20000
AFIX 0
C17 1 0.447386 0.842328 0.059369 11.00000 0.03527 0.03750 =
0.02267 -0.00622 0.00242 -0.00238
AFIX 43
H17 2 0.437153 0.730399 0.032873 11.00000 -1.20000
AFIX 0
C18 1 0.499086 0.811312 0.111630 11.00000 0.03014 0.02861 =
0.02171 -0.00101 0.00484 0.00451
AFIX 43
H18 2 0.524529 0.677147 0.121271 11.00000 -1.20000
AFIX 0
MOLE 2
S1 6 0.205191 0.843398 0.130998 11.00000 0.02392 0.02205 =
0.03161 0.00412 0.00630 0.00003
O6 4 0.178969 0.631075 0.114314 11.00000 0.03706 0.02171 =
0.06460 0.00400 0.00788 -0.00535
O7 4 0.150542 0.945299 0.165000 11.00000 0.04001 0.04750 =
0.03362 0.00192 0.01404 0.00710
O8 4 0.297831 0.879877 0.147892 11.00000 0.02612 0.03623 =
0.04542 0.00503 0.00251 -0.00381
F1 5 0.090388 0.964919 0.043105 11.00000 0.03344 0.04708 =
0.03596 0.00425 -0.00058 0.00478
F2 5 0.195316 1.187646 0.069661 11.00000 0.08012 0.02384 =
0.04743 0.01034 0.00235 -0.01073
F3 5 0.219244 0.907267 0.025378 11.00000 0.04512 0.06586 =
0.03266 -0.00946 0.01625 -0.01067
C19 1 0.176960 0.982931 0.064234 11.00000 0.03460 0.02605 =
0.02764 0.00047 0.00594 -0.00444
HKLF 4
REM a1 in C2
REM R1 = 0.0460 for 6827 Fo > 4sig(Fo) and 0.0526 for all 7523 data
REM 293 parameters refined using 1 restraints
END
WGHT 0.0531 1.0577
REM Highest difference peak 0.617, deepest hole -0.297, 1-sigma level 0.055
Q1 1 0.1416 0.8518 0.0980 11.00000 0.05 0.62
Q2 1 0.5602 0.8440 0.2719 11.00000 0.05 0.36
Q3 1 0.4754 0.5509 0.2979 11.00000 0.05 0.35
Q4 1 0.1978 0.8986 0.0918 11.00000 0.05 0.35
Q5 1 0.1505 0.8559 0.1413 11.00000 0.05 0.34
Q6 1 0.5964 0.6302 0.4484 11.00000 0.05 0.32
Q7 1 0.2551 0.8251 0.1569 11.00000 0.05 0.30
Q8 1 0.2587 0.8308 0.1304 11.00000 0.05 0.30
Q9 1 0.5717 0.7736 0.3285 11.00000 0.05 0.30
Q10 1 0.6245 0.6772 0.4703 11.00000 0.05 0.29
Q11 1 0.5414 0.9001 0.2221 11.00000 0.05 0.28
Q12 1 0.5455 0.9459 0.1778 11.00000 0.05 0.27
Q13 1 0.1955 0.8772 0.1681 11.00000 0.05 0.27
Q14 1 0.3142 0.9264 0.1189 11.00000 0.05 0.25
Q15 1 0.4900 0.4953 0.3643 11.00000 0.05 0.24
Q16 1 0.5780 0.7154 0.3699 11.00000 0.05 0.24
Q17 1 0.4525 0.5020 0.3378 11.00000 0.05 0.24
Q18 1 0.1941 0.9100 0.1971 11.00000 0.05 0.24
Q19 1 0.4507 0.2262 0.4169 11.00000 0.05 0.23
Q20 1 0.4646 0.6594 0.2012 11.00000 0.05 0.23
;
_shelx_res_checksum 23758