# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018
#######################################################################
#
# 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_3ab
_database_code_depnum_ccdc_archive 'CCDC 1491616'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C22 H21 N O3 S'
_chemical_formula_sum 'C22 H21 N O3 S'
_chemical_formula_weight 379.46
_chemical_absolute_configuration ad
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
_cell_length_a 7.9842(9)
_cell_length_b 6.081(2)
_cell_length_c 20.127(2)
_cell_angle_alpha 90.00
_cell_angle_beta 100.170(11)
_cell_angle_gamma 90.00
_cell_volume 961.9(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 835
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 69.1040
_cell_measurement_theta_min 4.4550
_exptl_absorpt_coefficient_mu 1.673
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.29642
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.310
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 400
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0458
_diffrn_reflns_av_unetI/netI 0.0554
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -3
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 3110
_diffrn_reflns_theta_full 67.03
_diffrn_reflns_theta_max 67.03
_diffrn_reflns_theta_min 4.46
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -111.00 -12.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -40.2955 -57.0000 -60.0000 99
#__ type_ start__ end____ width___ exp.time_
2 omega -110.00 -25.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -40.2955 -38.0000 30.0000 85
#__ type_ start__ end____ width___ exp.time_
3 omega 40.00 80.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 40.2955 -125.0000 -150.0000 40
#__ type_ start__ end____ width___ exp.time_
4 omega 59.00 86.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 90.0000 27
#__ type_ start__ end____ width___ exp.time_
5 omega 130.00 172.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 125.0000 -30.0000 42
#__ type_ start__ end____ width___ exp.time_
6 omega 46.00 90.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -120.0000 44
#__ type_ start__ end____ width___ exp.time_
7 omega 94.00 129.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 125.0000 -30.0000 35
#__ type_ start__ end____ width___ exp.time_
8 omega 31.00 67.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -30.0000 36
#__ type_ start__ end____ width___ exp.time_
9 omega 48.00 80.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -150.0000 32
#__ type_ start__ end____ width___ exp.time_
10 omega 43.00 70.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -60.0000 27
#__ type_ start__ end____ width___ exp.time_
11 omega 81.00 177.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 30.0000 90.0000 96
#__ type_ start__ end____ width___ exp.time_
12 omega 50.00 99.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 90.0000 49
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.1673978000
_diffrn_orient_matrix_UB_12 -0.1011666000
_diffrn_orient_matrix_UB_13 0.0372329000
_diffrn_orient_matrix_UB_21 0.0471578000
_diffrn_orient_matrix_UB_22 -0.0665619000
_diffrn_orient_matrix_UB_23 -0.0682209000
_diffrn_orient_matrix_UB_31 0.0902011000
_diffrn_orient_matrix_UB_32 0.2226096000
_diffrn_orient_matrix_UB_33 -0.0035301000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 1654
_reflns_number_total 2346
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.196
_refine_diff_density_min -0.216
_refine_diff_density_rms 0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.03(5)
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.990
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 246
_refine_ls_number_reflns 2346
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0813
_refine_ls_R_factor_gt 0.0621
_refine_ls_restrained_S_all 0.990
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1625
_refine_ls_wR_factor_ref 0.1849
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.1138(8) 0.3500(14) 0.7325(3) 0.091(2) Uani 1 d . . .
H1A H -0.0055 0.3279 0.7345 0.109 Uiso 1 calc . . R
H1B H 0.1815 0.2451 0.7622 0.109 Uiso 1 calc . . R
C2 C 0.1465(7) 0.3305(10) 0.6609(3) 0.0737(16) Uani 1 d . . .
C3 C 0.2405(8) 0.5066(11) 0.6463(3) 0.0739(15) Uani 1 d . . .
C4 C 0.2828(9) 0.6593(12) 0.7061(3) 0.0870(17) Uani 1 d . . .
H4A H 0.4010 0.6461 0.7276 0.104 Uiso 1 calc . . R
H4B H 0.2583 0.8112 0.6933 0.104 Uiso 1 calc . . R
C5 C 0.0967(8) 0.1721(14) 0.6141(3) 0.096(2) Uani 1 d . . .
H5 H 0.0343 0.0518 0.6245 0.115 Uiso 1 calc . . R
C6 C 0.1402(8) 0.1913(12) 0.5498(3) 0.0862(18) Uani 1 d . . .
H6 H 0.1055 0.0837 0.5175 0.103 Uiso 1 calc . . R
C7 C 0.2336(6) 0.3677(9) 0.5342(3) 0.0675(14) Uani 1 d . . .
C8 C 0.2839(7) 0.5279(9) 0.5828(3) 0.0674(14) Uani 1 d . . .
H8 H 0.3464 0.6488 0.5728 0.081 Uiso 1 calc . . R
C9 C 0.2738(6) 0.3899(9) 0.4640(3) 0.0671(13) Uani 1 d . . .
C10 C 0.2277(9) 0.2330(10) 0.4148(4) 0.0879(19) Uani 1 d . . .
H10 H 0.1791 0.1027 0.4264 0.106 Uiso 1 calc . . R
C11 C 0.2510(10) 0.2618(11) 0.3489(4) 0.0884(18) Uani 1 d . . .
H11 H 0.2137 0.1540 0.3169 0.106 Uiso 1 calc . . R
C12 C 0.3277(8) 0.4461(10) 0.3303(3) 0.0729(15) Uani 1 d . . .
C13 C 0.3810(9) 0.6057(13) 0.3782(3) 0.094(2) Uani 1 d . . .
H13 H 0.4349 0.7323 0.3669 0.113 Uiso 1 calc . . R
C14 C 0.3521(9) 0.5730(12) 0.4443(3) 0.090(2) Uani 1 d . . .
H14 H 0.3879 0.6812 0.4763 0.108 Uiso 1 calc . . R
C15 C 0.3993(13) 0.6683(16) 0.2420(4) 0.118(3) Uani 1 d . . .
H15A H 0.3292 0.7833 0.2549 0.177 Uiso 1 calc . . GR
H15B H 0.3897 0.6669 0.1938 0.177 Uiso 1 calc . . GR
H15C H 0.5157 0.6938 0.2625 0.177 Uiso 1 calc . . GR
C16 C 0.3753(8) 0.5340(11) 0.8734(3) 0.0757(15) Uani 1 d . . .
C17 C 0.3678(8) 0.3377(11) 0.9051(3) 0.0765(15) Uani 1 d . . .
H17 H 0.2638 0.2686 0.9048 0.092 Uiso 1 calc . . R
C18 C 0.5172(9) 0.2422(11) 0.9378(3) 0.0776(16) Uani 1 d . . .
H18 H 0.5124 0.1090 0.9601 0.093 Uiso 1 calc . . R
C19 C 0.6734(9) 0.3406(12) 0.9380(3) 0.0822(17) Uani 1 d . . .
C20 C 0.6757(9) 0.5396(13) 0.9062(4) 0.0912(19) Uani 1 d . . .
H20 H 0.7797 0.6089 0.9065 0.109 Uiso 1 calc . . R
C21 C 0.5284(9) 0.6413(13) 0.8735(3) 0.0856(18) Uani 1 d . . .
H21 H 0.5323 0.7767 0.8523 0.103 Uiso 1 calc . . R
C22 C 0.8355(10) 0.2273(19) 0.9709(4) 0.127(4) Uani 1 d . . .
H22A H 0.8079 0.0931 0.9916 0.191 Uiso 1 calc . . GR
H22B H 0.8980 0.3221 1.0046 0.191 Uiso 1 calc . . GR
H22C H 0.9036 0.1946 0.9373 0.191 Uiso 1 calc . . GR
N1 N 0.1664(7) 0.5757(10) 0.7503(3) 0.0854(15) Uani 1 d . . .
O1 O 0.3459(7) 0.4648(9) 0.2638(3) 0.0994(15) Uani 1 d . . .
O2 O 0.0476(6) 0.5672(13) 0.8540(3) 0.122(2) Uani 1 d . . .
O3 O 0.2137(8) 0.8878(9) 0.8273(3) 0.116(2) Uani 1 d . . .
S1 S 0.1886(3) 0.6570(3) 0.82817(9) 0.0934(6) Uani 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 0.073(4) 0.104(5) 0.093(4) 0.034(4) 0.006(3) -0.018(4)
C2 0.060(3) 0.076(4) 0.077(3) 0.016(3) -0.010(3) -0.013(3)
C3 0.069(3) 0.072(3) 0.075(3) 0.016(3) -0.004(3) -0.005(3)
C4 0.112(5) 0.073(3) 0.078(3) 0.016(4) 0.023(3) -0.006(4)
C5 0.087(4) 0.100(5) 0.093(4) 0.021(4) -0.003(3) -0.041(4)
C6 0.083(4) 0.084(4) 0.084(4) 0.006(3) -0.007(3) -0.031(4)
C7 0.053(3) 0.061(3) 0.082(3) 0.014(3) -0.006(2) -0.006(3)
C8 0.070(3) 0.055(3) 0.076(3) 0.013(3) 0.007(3) -0.004(3)
C9 0.055(3) 0.056(3) 0.083(3) 0.009(3) -0.008(2) 0.002(3)
C10 0.096(5) 0.050(3) 0.118(5) -0.004(3) 0.018(4) -0.003(3)
C11 0.109(5) 0.064(3) 0.092(4) -0.020(3) 0.015(4) -0.009(4)
C12 0.069(3) 0.070(3) 0.078(4) -0.011(3) 0.008(3) 0.003(3)
C13 0.105(5) 0.099(5) 0.080(4) -0.009(4) 0.020(3) -0.037(4)
C14 0.104(4) 0.091(4) 0.071(3) -0.012(3) 0.002(3) -0.045(4)
C15 0.159(8) 0.109(6) 0.093(5) -0.008(5) 0.041(5) 0.012(7)
C16 0.092(4) 0.069(3) 0.071(3) 0.013(3) 0.026(3) 0.007(3)
C17 0.087(4) 0.072(3) 0.074(3) 0.006(3) 0.023(3) -0.011(3)
C18 0.102(4) 0.071(3) 0.061(3) 0.013(3) 0.019(3) 0.000(4)
C19 0.091(4) 0.090(4) 0.065(3) 0.010(3) 0.011(3) -0.004(4)
C20 0.089(4) 0.096(5) 0.093(4) 0.006(4) 0.027(3) -0.009(4)
C21 0.108(5) 0.075(4) 0.076(3) 0.010(3) 0.022(3) -0.011(4)
C22 0.098(5) 0.160(10) 0.121(6) 0.038(7) 0.012(4) 0.013(6)
N1 0.082(3) 0.087(4) 0.086(3) 0.026(3) 0.012(2) 0.006(3)
O1 0.116(4) 0.098(4) 0.087(3) -0.023(3) 0.024(3) -0.006(3)
O2 0.090(3) 0.172(6) 0.112(4) 0.025(4) 0.040(3) 0.020(4)
O3 0.164(5) 0.087(3) 0.100(4) 0.013(3) 0.028(4) 0.049(4)
S1 0.1014(12) 0.0949(12) 0.0880(10) 0.0165(10) 0.0281(8) 0.0237(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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(10) . ?
C1 N1 1.461(10) . ?
C2 C3 1.369(9) . ?
C2 C5 1.357(10) . ?
C3 C4 1.510(9) . ?
C3 C8 1.389(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.484(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(8) . ?
C7 C8 1.388(8) . ?
C7 C9 1.509(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(9) . ?
C9 C14 1.370(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(10) . ?
C12 C13 1.381(9) . ?
C12 O1 1.376(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(9) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 O1 1.404(10) . ?
C16 C17 1.360(8) . ?
C16 C21 1.385(9) . ?
C16 S1 1.769(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(9) . ?
C19 C20 1.371(10) . ?
C19 C22 1.512(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(10) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S1 1.624(6) . ?
O2 S1 1.429(6) . ?
O3 S1 1.418(6) . ?
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
H1A C1 H1B 109.2 . . ?
C2 C1 H1A 111.3 . . ?
C2 C1 H1B 111.3 . . ?
N1 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
N1 C1 C2 102.5(5) . . ?
C3 C2 C1 109.6(6) . . ?
C5 C2 C1 129.6(6) . . ?
C5 C2 C3 120.8(6) . . ?
C2 C3 C4 111.4(6) . . ?
C2 C3 C8 120.3(6) . . ?
C8 C3 C4 128.3(6) . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
N1 C4 C3 101.0(6) . . ?
N1 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C2 C5 H5 120.3 . . ?
C2 C5 C6 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(6) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.2(6) . . ?
C6 C7 C9 119.9(5) . . ?
C8 C7 C9 120.9(5) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.6(5) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C7 122.5(5) . . ?
C14 C9 C7 121.8(5) . . ?
C14 C9 C10 115.6(6) . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(6) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.0(6) . . ?
C11 C12 O1 117.7(6) . . ?
O1 C12 C13 123.3(6) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(6) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 123.3(6) . . ?
C9 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
C17 C16 C21 121.7(6) . . ?
C17 C16 S1 120.6(5) . . ?
C21 C16 S1 117.7(5) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(6) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(6) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C22 120.4(7) . . ?
C20 C19 C18 117.9(6) . . ?
C20 C19 C22 121.7(7) . . ?
C19 C20 H20 118.8 . . ?
C19 C20 C21 122.3(7) . . ?
C21 C20 H20 118.8 . . ?
C16 C21 C20 117.7(6) . . ?
C16 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C4 111.0(6) . . ?
C1 N1 S1 120.0(4) . . ?
C4 N1 S1 120.1(5) . . ?
C12 O1 C15 117.8(5) . . ?
N1 S1 C16 107.8(3) . . ?
O2 S1 C16 107.3(3) . . ?
O2 S1 N1 106.0(4) . . ?
O3 S1 C16 108.4(4) . . ?
O3 S1 N1 106.4(3) . . ?
O3 S1 O2 120.3(4) . . ?
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
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C2 C3 C8 -178.7(5) . . . . ?
C1 C2 C5 C6 178.9(7) . . . . ?
C1 N1 S1 C16 72.7(6) . . . . ?
C1 N1 S1 O2 -42.0(6) . . . . ?
C1 N1 S1 O3 -171.1(5) . . . . ?
C2 C1 N1 C4 -20.8(6) . . . . ?
C2 C1 N1 S1 -168.1(4) . . . . ?
C2 C3 C4 N1 -13.0(7) . . . . ?
C2 C3 C8 C7 -1.0(9) . . . . ?
C2 C5 C6 C7 0.6(11) . . . . ?
C3 C2 C5 C6 -1.0(10) . . . . ?
C3 C4 N1 C1 21.1(6) . . . . ?
C3 C4 N1 S1 168.3(4) . . . . ?
C4 C3 C8 C7 179.6(6) . . . . ?
C4 N1 S1 C16 -71.6(6) . . . . ?
C4 N1 S1 O2 173.7(5) . . . . ?
C4 N1 S1 O3 44.5(6) . . . . ?
C5 C2 C3 C4 -179.2(6) . . . . ?
C5 C2 C3 C8 1.2(9) . . . . ?
C5 C6 C7 C8 -0.3(9) . . . . ?
C5 C6 C7 C9 -177.8(6) . . . . ?
C6 C7 C8 C3 0.5(8) . . . . ?
C6 C7 C9 C10 -3.4(8) . . . . ?
C6 C7 C9 C14 173.6(6) . . . . ?
C7 C9 C10 C11 174.1(6) . . . . ?
C7 C9 C14 C13 -175.5(6) . . . . ?
C8 C3 C4 N1 166.5(6) . . . . ?
C8 C7 C9 C10 179.2(6) . . . . ?
C8 C7 C9 C14 -3.8(8) . . . . ?
C9 C7 C8 C3 178.0(5) . . . . ?
C9 C10 C11 C12 2.6(11) . . . . ?
C10 C9 C14 C13 1.7(10) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C10 C11 C12 O1 -179.6(6) . . . . ?
C11 C12 C13 C14 -0.8(10) . . . . ?
C11 C12 O1 C15 169.9(7) . . . . ?
C12 C13 C14 C9 0.2(11) . . . . ?
C13 C12 O1 C15 -9.1(10) . . . . ?
C14 C9 C10 C11 -3.0(10) . . . . ?
C16 C17 C18 C19 -0.9(9) . . . . ?
C17 C16 C21 C20 1.1(10) . . . . ?
C17 C16 S1 N1 -91.6(5) . . . . ?
C17 C16 S1 O2 22.2(6) . . . . ?
C17 C16 S1 O3 153.6(5) . . . . ?
C17 C18 C19 C20 1.6(9) . . . . ?
C17 C18 C19 C22 -176.7(7) . . . . ?
C18 C19 C20 C21 -1.0(10) . . . . ?
C19 C20 C21 C16 -0.3(10) . . . . ?
C21 C16 C17 C18 -0.5(10) . . . . ?
C21 C16 S1 N1 86.4(6) . . . . ?
C21 C16 S1 O2 -159.7(5) . . . . ?
C21 C16 S1 O3 -28.3(6) . . . . ?
C22 C19 C20 C21 177.4(7) . . . . ?
N1 C1 C2 C3 12.0(7) . . . . ?
N1 C1 C2 C5 -167.9(6) . . . . ?
O1 C12 C13 C14 178.3(7) . . . . ?
S1 C16 C17 C18 177.5(5) . . . . ?
S1 C16 C21 C20 -177.0(5) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160527wxn-1_a.res in P2(1)
CELL 1.54184 7.984248 6.081202 20.126825 90 100.1697 90
ZERR 2 0.000863 0.002069 0.001965 0 0.0106 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O S
UNIT 44 42 2 6 2
L.S. 20
PLAN 20
SIZE 0.24 0.2 0.2
BOND $H
LIST 6
htab
conf
fmap 2
acta
SHEL 999 0.837
REM
REM
REM
WGHT 0.092600
FVAR 8.29618
C1 1 0.113832 0.350043 0.732535 11.00000 0.07327 0.10440 =
0.09279 0.03362 0.00592 -0.01786
AFIX 23
H1A 2 -0.005515 0.327870 0.734480 11.00000 -1.20000
H1B 2 0.181519 0.245102 0.762152 11.00000 -1.20000
AFIX 0
C2 1 0.146459 0.330542 0.660861 11.00000 0.05965 0.07615 =
0.07729 0.01610 -0.01013 -0.01344
C3 1 0.240528 0.506650 0.646317 11.00000 0.06886 0.07172 =
0.07477 0.01594 -0.00440 -0.00509
C4 1 0.282779 0.659265 0.706099 11.00000 0.11198 0.07300 =
0.07838 0.01581 0.02324 -0.00563
AFIX 23
H4A 2 0.401047 0.646103 0.727588 11.00000 -1.20000
H4B 2 0.258312 0.811229 0.693284 11.00000 -1.20000
AFIX 0
C5 1 0.096717 0.172069 0.614066 11.00000 0.08705 0.09981 =
0.09286 0.02111 -0.00323 -0.04086
AFIX 43
H5 2 0.034331 0.051753 0.624534 11.00000 -1.20000
AFIX 0
C6 1 0.140155 0.191270 0.549845 11.00000 0.08317 0.08365 =
0.08363 0.00588 -0.00722 -0.03137
AFIX 43
H6 2 0.105454 0.083690 0.517498 11.00000 -1.20000
AFIX 0
C7 1 0.233589 0.367668 0.534220 11.00000 0.05275 0.06081 =
0.08234 0.01383 -0.00607 -0.00645
C8 1 0.283922 0.527906 0.582780 11.00000 0.06963 0.05452 =
0.07587 0.01252 0.00654 -0.00386
AFIX 43
H8 2 0.346365 0.648830 0.572811 11.00000 -1.20000
AFIX 0
C9 1 0.273791 0.389930 0.464010 11.00000 0.05467 0.05583 =
0.08326 0.00886 -0.00849 0.00191
C10 1 0.227737 0.233034 0.414815 11.00000 0.09584 0.04956 =
0.11793 -0.00401 0.01755 -0.00341
AFIX 43
H10 2 0.179134 0.102704 0.426386 11.00000 -1.20000
AFIX 0
C11 1 0.250955 0.261764 0.348894 11.00000 0.10872 0.06361 =
0.09200 -0.01982 0.01500 -0.00864
AFIX 43
H11 2 0.213743 0.153958 0.316912 11.00000 -1.20000
AFIX 0
C12 1 0.327688 0.446126 0.330295 11.00000 0.06927 0.07014 =
0.07760 -0.01090 0.00825 0.00279
C13 1 0.380950 0.605680 0.378185 11.00000 0.10544 0.09883 =
0.08023 -0.00914 0.01988 -0.03726
AFIX 43
H13 2 0.434898 0.732297 0.366870 11.00000 -1.20000
AFIX 0
C14 1 0.352082 0.573047 0.444282 11.00000 0.10354 0.09077 =
0.07060 -0.01177 0.00221 -0.04495
AFIX 43
H14 2 0.387930 0.681239 0.476298 11.00000 -1.20000
AFIX 0
C15 1 0.399342 0.668281 0.242019 11.00000 0.15893 0.10936 =
0.09307 -0.00769 0.04130 0.01221
AFIX 137
H15A 2 0.329152 0.783264 0.254906 11.00000 -1.50000
H15B 2 0.389715 0.666864 0.193797 11.00000 -1.50000
H15C 2 0.515707 0.693826 0.262457 11.00000 -1.50000
AFIX 0
C16 1 0.375335 0.534029 0.873396 11.00000 0.09155 0.06928 =
0.07053 0.01325 0.02587 0.00672
C17 1 0.367817 0.337707 0.905090 11.00000 0.08659 0.07224 =
0.07381 0.00631 0.02276 -0.01078
AFIX 43
H17 2 0.263776 0.268622 0.904806 11.00000 -1.20000
AFIX 0
C18 1 0.517153 0.242187 0.937769 11.00000 0.10238 0.07083 =
0.06140 0.01320 0.01926 -0.00015
AFIX 43
H18 2 0.512355 0.108984 0.960056 11.00000 -1.20000
AFIX 0
C19 1 0.673372 0.340620 0.937985 11.00000 0.09091 0.09010 =
0.06482 0.00996 0.01123 -0.00422
C20 1 0.675713 0.539579 0.906165 11.00000 0.08881 0.09614 =
0.09255 0.00635 0.02691 -0.00882
AFIX 43
H20 2 0.779695 0.608881 0.906507 11.00000 -1.20000
AFIX 0
C21 1 0.528403 0.641254 0.873455 11.00000 0.10777 0.07521 =
0.07591 0.01018 0.02218 -0.01115
AFIX 43
H21 2 0.532322 0.776668 0.852311 11.00000 -1.20000
AFIX 0
C22 1 0.835501 0.227269 0.970864 11.00000 0.09780 0.16007 =
0.12135 0.03755 0.01152 0.01347
AFIX 137
H22A 2 0.807886 0.093119 0.991643 11.00000 -1.50000
H22B 2 0.897988 0.322074 1.004554 11.00000 -1.50000
H22C 2 0.903566 0.194646 0.937271 11.00000 -1.50000
AFIX 0
N1 3 0.166438 0.575687 0.750278 11.00000 0.08237 0.08711 =
0.08581 0.02585 0.01225 0.00604
O1 4 0.345872 0.464765 0.263811 11.00000 0.11583 0.09772 =
0.08697 -0.02286 0.02420 -0.00576
O2 4 0.047623 0.567214 0.853957 11.00000 0.08971 0.17151 =
0.11225 0.02524 0.04001 0.01977
O3 4 0.213749 0.887805 0.827350 11.00000 0.16369 0.08655 =
0.10027 0.01298 0.02835 0.04899
S1 5 0.188612 0.656999 0.828175 11.00000 0.10143 0.09491 =
0.08799 0.01647 0.02809 0.02370
HKLF 4
REM 20160527wxn-1_a.res in P2(1)
REM R1 = 0.0621 for 1654 Fo > 4sig(Fo) and 0.0813 for all 2346 data
REM 246 parameters refined using 1 restraints
END
WGHT 0.0920 0.0000
REM Highest difference peak 0.196, deepest hole -0.216, 1-sigma level 0.044
Q1 1 -0.0417 0.8034 0.8513 11.00000 0.05 0.20
Q2 1 -0.0562 0.7510 0.8600 11.00000 0.05 0.20
Q3 1 0.1025 0.3642 0.6194 11.00000 0.05 0.17
Q4 1 0.4223 0.3739 0.9463 11.00000 0.05 0.16
Q5 1 0.3745 0.3573 0.3702 11.00000 0.05 0.16
Q6 1 0.1402 0.8502 0.7936 11.00000 0.05 0.16
Q7 1 -0.0582 0.4911 0.8520 11.00000 0.05 0.15
Q8 1 0.2140 0.3979 0.4205 11.00000 0.05 0.15
Q9 1 0.2905 0.7773 0.8312 11.00000 0.05 0.15
Q10 1 0.3929 0.7831 0.7195 11.00000 0.05 0.15
Q11 1 0.0583 0.7482 0.8364 11.00000 0.05 0.14
Q12 1 0.9492 0.3283 0.9732 11.00000 0.05 0.14
Q13 1 -0.0031 0.4551 0.7376 11.00000 0.05 0.14
Q14 1 0.3414 0.5824 0.3344 11.00000 0.05 0.13
Q15 1 0.1426 0.6342 0.7836 11.00000 0.05 0.13
Q16 1 0.1656 0.4536 0.8166 11.00000 0.05 0.13
Q17 1 0.8124 0.4324 0.8525 11.00000 0.05 0.13
Q18 1 0.0353 0.5066 0.7456 11.00000 0.05 0.13
Q19 1 0.0816 0.9499 0.8776 11.00000 0.05 0.13
Q20 1 0.6187 0.3344 0.8948 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0621 for 1654 Fo > 4sig(Fo) and 0.0813 for all 3293 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.20, deepest hole -0.22
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0813
REM R1_gt = 0.0621
REM wR_ref = 0.1849
REM GOOF = 0.990
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 3293
REM Reflections_gt = 1654
REM Parameters = n/a
REM Hole = -0.22
REM Peak = 0.20
REM Flack = 0.03(5)
;
_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_3ea
_database_code_depnum_ccdc_archive 'CCDC 1491623'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C21 H17 N O'
_chemical_formula_sum 'C21 H17 N O'
_chemical_formula_weight 299.36
_chemical_absolute_configuration unk
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 7
_space_group_name_H-M_alt 'P 1 c 1'
_space_group_name_Hall 'P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
_cell_length_a 15.5556(11)
_cell_length_b 7.0185(5)
_cell_length_c 7.3310(5)
_cell_angle_alpha 90.00
_cell_angle_beta 94.221(6)
_cell_angle_gamma 90.00
_cell_volume 798.20(10)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 1653
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.5210
_cell_measurement_theta_min 5.7310
_exptl_absorpt_coefficient_mu 0.595
_exptl_absorpt_correction_T_min 0.8702
_exptl_absorpt_correction_T_max 0.8901
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.246
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 316
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0400
_diffrn_reflns_av_unetI/netI 0.0375
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 2470
_diffrn_reflns_theta_full 67.03
_diffrn_reflns_theta_max 67.03
_diffrn_reflns_theta_min 5.70
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega 16.00 115.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 38.0000 120.0000 99
#__ type_ start__ end____ width___ exp.time_
2 omega 87.00 163.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 30.0000 60.0000 76
#__ type_ start__ end____ width___ exp.time_
3 omega 71.00 97.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 30.0000 26
#__ type_ start__ end____ width___ exp.time_
4 omega 34.00 79.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -99.0000 120.0000 45
#__ type_ start__ end____ width___ exp.time_
5 omega 41.00 87.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 120.0000 46
#__ type_ start__ end____ width___ exp.time_
6 omega 55.00 81.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 90.0000 26
#__ type_ start__ end____ width___ exp.time_
7 omega 5.00 32.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -99.0000 120.0000 27
#__ type_ start__ end____ width___ exp.time_
8 omega 36.00 64.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -60.0000 28
#__ type_ start__ end____ width___ exp.time_
9 omega 42.00 73.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -60.0000 31
#__ type_ start__ end____ width___ exp.time_
10 omega 51.00 80.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -120.0000 29
#__ type_ start__ end____ width___ exp.time_
11 omega 40.00 84.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -150.0000 44
#__ type_ start__ end____ width___ exp.time_
12 omega 34.00 121.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -90.0000 87
#__ type_ start__ end____ width___ exp.time_
13 omega -60.00 -2.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 125.0000 -60.0000 58
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0009711000
_diffrn_orient_matrix_UB_12 0.1444963000
_diffrn_orient_matrix_UB_13 0.1582833000
_diffrn_orient_matrix_UB_21 -0.0965038000
_diffrn_orient_matrix_UB_22 -0.0376555000
_diffrn_orient_matrix_UB_23 0.0193610000
_diffrn_orient_matrix_UB_31 0.0235086000
_diffrn_orient_matrix_UB_32 -0.1608611000
_diffrn_orient_matrix_UB_33 0.1376758000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 1508
_reflns_number_total 1658
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max 0.235
_refine_diff_density_min -0.392
_refine_diff_density_rms 0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.3(8)
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.139
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 208
_refine_ls_number_reflns 1658
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0737
_refine_ls_R_factor_gt 0.0712
_refine_ls_restrained_S_all 1.139
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2176
_refine_ls_wR_factor_ref 0.2227
_refine_special_details
;
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^ > 2sigma(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.
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.4874(3) 0.2691(5) 0.3023(7) 0.0437(10) Uani 1 d . . .
H1A H 0.5004 0.3846 0.2370 0.052 Uiso 1 calc . . R
H1B H 0.4998 0.1596 0.2279 0.052 Uiso 1 calc . . R
C2 C 0.5368(4) 0.2608(4) 0.4846(6) 0.0431(10) Uani 1 d . . .
C3 C 0.4810(3) 0.2412(5) 0.6244(7) 0.0432(10) Uani 1 d . . .
C4 C 0.3890(4) 0.2443(6) 0.5482(7) 0.0526(13) Uani 1 d . . .
H4A H 0.3599 0.1261 0.5741 0.063 Uiso 1 calc . . R
H4B H 0.3578 0.3499 0.5976 0.063 Uiso 1 calc . . R
C5 C 0.6257(3) 0.2662(5) 0.5251(7) 0.0468(11) Uani 1 d . . .
H5 H 0.6628 0.2797 0.4320 0.056 Uiso 1 calc . . R
C6 C 0.6587(3) 0.2510(4) 0.7075(7) 0.0465(11) Uani 1 d . . .
C7 C 0.6014(4) 0.2319(5) 0.8438(7) 0.0500(11) Uani 1 d . . .
H7 H 0.6232 0.2212 0.9648 0.060 Uiso 1 calc . . R
C8 C 0.5131(4) 0.2282(6) 0.8050(7) 0.0519(12) Uani 1 d . . .
H8 H 0.4761 0.2173 0.8984 0.062 Uiso 1 calc . . R
C9 C 0.7540(3) 0.2524(5) 0.7557(7) 0.0481(11) Uani 1 d . . .
C10 C 0.8082(3) 0.3712(6) 0.6672(7) 0.0603(11) Uani 1 d . . .
H10 H 0.7855 0.4514 0.5749 0.072 Uiso 1 calc . . R
C11 C 0.8970(3) 0.3721(8) 0.7150(8) 0.0703(14) Uani 1 d . . .
H11 H 0.9333 0.4506 0.6534 0.084 Uiso 1 calc . . R
C12 C 0.9300(4) 0.2553(7) 0.8545(11) 0.0711(16) Uani 1 d . . .
H12 H 0.9887 0.2584 0.8899 0.085 Uiso 1 calc . . R
C13 C 0.8778(4) 0.1366(8) 0.9399(8) 0.0716(14) Uani 1 d . . .
H13 H 0.9011 0.0554 1.0309 0.086 Uiso 1 calc . . R
C14 C 0.7898(4) 0.1343(7) 0.8935(7) 0.0624(12) Uani 1 d . . .
H14 H 0.7545 0.0532 0.9548 0.075 Uiso 1 calc . . R
C15 C 0.2420(4) 0.2543(5) 0.2715(8) 0.0491(11) Uani 1 d . . .
C16 C 0.1866(3) 0.1132(6) 0.1973(7) 0.0588(11) Uani 1 d . . .
H16 H 0.2070 0.0211 0.1202 0.071 Uiso 1 calc . . R
C17 C 0.1008(3) 0.1112(7) 0.2391(7) 0.0671(13) Uani 1 d . . .
H17 H 0.0644 0.0152 0.1920 0.081 Uiso 1 calc . . R
C18 C 0.0692(4) 0.2494(8) 0.3494(9) 0.0740(19) Uani 1 d . . .
H18 H 0.0116 0.2478 0.3754 0.089 Uiso 1 calc . . R
C19 C 0.1235(3) 0.3899(8) 0.4207(7) 0.0673(14) Uani 1 d . . .
H19 H 0.1027 0.4834 0.4958 0.081 Uiso 1 calc . . R
C20 C 0.2098(3) 0.3920(6) 0.3804(7) 0.0581(11) Uani 1 d . . .
H20 H 0.2460 0.4881 0.4280 0.070 Uiso 1 calc . . R
C21 C 0.3336(3) 0.2554(5) 0.2165(7) 0.0472(11) Uani 1 d . . .
N1 N 0.3966(3) 0.2676(4) 0.3506(5) 0.0460(9) Uani 1 d . . .
O1 O 0.3474(3) 0.2481(4) 0.0561(6) 0.0650(11) Uani 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 0.035(2) 0.063(2) 0.034(2) 0.0045(16) 0.0114(18) 0.0005(16)
C2 0.043(2) 0.0541(19) 0.033(2) -0.0001(13) 0.009(2) 0.0007(15)
C3 0.039(3) 0.057(2) 0.036(3) 0.0009(13) 0.0142(19) 0.0013(14)
C4 0.045(3) 0.080(3) 0.034(3) 0.0035(15) 0.009(2) 0.0050(17)
C5 0.041(3) 0.066(2) 0.035(2) 0.0008(16) 0.014(2) 0.0011(17)
C6 0.042(3) 0.057(2) 0.042(3) -0.0006(14) 0.009(2) -0.0010(15)
C7 0.051(3) 0.069(2) 0.030(2) 0.0029(15) 0.007(2) -0.0015(18)
C8 0.044(2) 0.074(3) 0.039(3) 0.0001(17) 0.016(2) -0.0008(19)
C9 0.041(3) 0.062(2) 0.042(3) -0.0017(14) 0.006(2) -0.0040(15)
C10 0.055(3) 0.077(3) 0.050(2) 0.0063(19) 0.008(2) -0.004(2)
C11 0.052(3) 0.094(3) 0.066(3) 0.000(2) 0.013(2) -0.013(2)
C12 0.044(3) 0.093(4) 0.075(4) -0.011(2) -0.001(3) -0.002(2)
C13 0.057(3) 0.085(3) 0.071(3) 0.008(2) -0.010(3) 0.002(2)
C14 0.057(3) 0.069(2) 0.060(3) 0.009(2) 0.001(2) -0.005(2)
C15 0.039(2) 0.070(3) 0.039(2) 0.0017(14) 0.003(2) 0.0034(15)
C16 0.046(2) 0.081(3) 0.050(2) -0.009(2) 0.0037(19) 0.000(2)
C17 0.045(3) 0.097(3) 0.059(3) -0.002(2) 0.007(2) -0.012(2)
C18 0.041(3) 0.133(6) 0.050(3) 0.007(2) 0.013(3) 0.008(2)
C19 0.048(3) 0.104(4) 0.051(3) -0.013(2) 0.009(2) 0.018(2)
C20 0.043(2) 0.081(3) 0.050(2) -0.009(2) 0.0038(19) 0.008(2)
C21 0.039(3) 0.064(2) 0.039(3) 0.0012(13) 0.008(2) 0.0020(15)
N1 0.033(2) 0.072(2) 0.033(2) 0.0020(13) 0.0100(16) 0.0048(14)
O1 0.048(2) 0.110(3) 0.038(2) -0.0028(13) 0.0096(18) 0.0038(13)
_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.493(7) . ?
C1 N1 1.481(5) . ?
C2 C3 1.397(6) . ?
C2 C5 1.394(7) . ?
C3 C4 1.499(7) . ?
C3 C8 1.383(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.471(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(7) . ?
C6 C7 1.393(7) . ?
C6 C9 1.498(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(7) . ?
C9 C14 1.391(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.349(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(7) . ?
C15 C20 1.371(7) . ?
C15 C21 1.510(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(6) . ?
C20 H20 0.9300 . ?
C21 N1 1.339(7) . ?
C21 O1 1.212(6) . ?
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
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
N1 C1 C2 102.8(4) . . ?
C3 C2 C1 110.8(4) . . ?
C5 C2 C1 128.8(4) . . ?
C5 C2 C3 120.4(5) . . ?
C2 C3 C4 110.6(5) . . ?
C8 C3 C2 120.6(5) . . ?
C8 C3 C4 128.7(4) . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C4 C3 103.0(4) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 120.7(5) . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 C9 120.4(5) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(5) . . ?
C8 C7 H7 118.9 . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.6(4) . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C6 121.4(4) . . ?
C10 C9 C14 118.3(5) . . ?
C14 C9 C6 120.3(4) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C21 117.9(4) . . ?
C20 C15 C16 119.1(5) . . ?
C20 C15 C21 122.9(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(5) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.9(5) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N1 C21 C15 117.3(4) . . ?
O1 C21 C15 119.8(5) . . ?
O1 C21 N1 122.9(5) . . ?
C4 N1 C1 112.6(4) . . ?
C21 N1 C1 118.9(4) . . ?
C21 N1 C4 127.5(4) . . ?
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
C1 C2 C3 C4 -2.8(4) . . . . ?
C1 C2 C3 C8 179.2(3) . . . . ?
C1 C2 C5 C6 -178.2(3) . . . . ?
C2 C1 N1 C4 -4.4(4) . . . . ?
C2 C1 N1 C21 -173.6(3) . . . . ?
C2 C3 C4 N1 0.0(4) . . . . ?
C2 C3 C8 C7 -1.1(6) . . . . ?
C2 C5 C6 C7 -0.3(5) . . . . ?
C2 C5 C6 C9 178.8(3) . . . . ?
C3 C2 C5 C6 0.2(5) . . . . ?
C3 C4 N1 C1 2.9(4) . . . . ?
C3 C4 N1 C21 171.0(3) . . . . ?
C4 C3 C8 C7 -178.7(3) . . . . ?
C5 C2 C3 C4 178.5(3) . . . . ?
C5 C2 C3 C8 0.5(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C5 C6 C9 C10 39.4(6) . . . . ?
C5 C6 C9 C14 -141.4(4) . . . . ?
C6 C7 C8 C3 1.0(6) . . . . ?
C6 C9 C10 C11 179.4(4) . . . . ?
C6 C9 C14 C13 -179.3(5) . . . . ?
C7 C6 C9 C10 -141.5(5) . . . . ?
C7 C6 C9 C14 37.7(6) . . . . ?
C8 C3 C4 N1 177.8(4) . . . . ?
C9 C6 C7 C8 -179.4(3) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C9 C14 C13 0.0(7) . . . . ?
C10 C11 C12 C13 2.2(9) . . . . ?
C11 C12 C13 C14 -2.2(9) . . . . ?
C12 C13 C14 C9 1.1(8) . . . . ?
C14 C9 C10 C11 0.1(7) . . . . ?
C15 C16 C17 C18 1.6(8) . . . . ?
C15 C21 N1 C1 180.0(3) . . . . ?
C15 C21 N1 C4 12.5(6) . . . . ?
C16 C15 C20 C19 1.5(8) . . . . ?
C16 C15 C21 N1 -130.9(5) . . . . ?
C16 C15 C21 O1 50.1(6) . . . . ?
C16 C17 C18 C19 -0.8(8) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C18 C19 C20 C15 -0.7(7) . . . . ?
C20 C15 C16 C17 -1.9(8) . . . . ?
C20 C15 C21 N1 53.5(6) . . . . ?
C20 C15 C21 O1 -125.5(5) . . . . ?
C21 C15 C16 C17 -177.7(4) . . . . ?
C21 C15 C20 C19 177.0(5) . . . . ?
N1 C1 C2 C3 4.3(4) . . . . ?
N1 C1 C2 C5 -177.1(3) . . . . ?
O1 C21 N1 C1 -1.1(6) . . . . ?
O1 C21 N1 C4 -168.6(4) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160602wxn-1_a.res in Pc
CELL 1.54184 15.555582 7.018461 7.33104 90 94.2212 90
ZERR 2 0.001112 0.000495 0.000495 0 0.0064 0
LATT -1
SYMM +X,-Y,0.5+Z
SFAC C H N O
UNIT 42 34 2 2
L.S. 10
PLAN 20
SIZE 0.24 0.2 0.2
BOND $H
LIST 6
conf
htab
fmap 2
acta
REM
REM
REM
WGHT 0.159700
FVAR 8.91071
C1 1 0.487378 0.269115 0.302266 11.00000 0.03549 0.06324 =
0.03359 0.00452 0.01144 0.00046
AFIX 23
H1A 2 0.500419 0.384570 0.237011 11.00000 -1.20000
H1B 2 0.499780 0.159563 0.227925 11.00000 -1.20000
AFIX 0
C2 1 0.536772 0.260821 0.484615 11.00000 0.04298 0.05414 =
0.03319 -0.00005 0.00934 0.00068
C3 1 0.481023 0.241193 0.624425 11.00000 0.03894 0.05650 =
0.03598 0.00088 0.01423 0.00131
C4 1 0.388963 0.244275 0.548181 11.00000 0.04473 0.07977 =
0.03435 0.00347 0.00908 0.00499
AFIX 23
H4A 2 0.359882 0.126145 0.574132 11.00000 -1.20000
H4B 2 0.357849 0.349909 0.597584 11.00000 -1.20000
AFIX 0
C5 1 0.625742 0.266206 0.525109 11.00000 0.04104 0.06641 =
0.03458 0.00085 0.01352 0.00106
AFIX 43
H5 2 0.662795 0.279713 0.432014 11.00000 -1.20000
AFIX 0
C6 1 0.658682 0.251048 0.707538 11.00000 0.04152 0.05671 =
0.04201 -0.00064 0.00873 -0.00097
C7 1 0.601356 0.231892 0.843757 11.00000 0.05138 0.06893 =
0.03033 0.00288 0.00750 -0.00152
AFIX 43
H7 2 0.623243 0.221217 0.964833 11.00000 -1.20000
AFIX 0
C8 1 0.513129 0.228224 0.805031 11.00000 0.04446 0.07449 =
0.03859 0.00012 0.01614 -0.00083
AFIX 43
H8 2 0.476081 0.217264 0.898423 11.00000 -1.20000
AFIX 0
C9 1 0.753952 0.252438 0.755676 11.00000 0.04117 0.06185 =
0.04157 -0.00175 0.00585 -0.00402
C10 1 0.808213 0.371181 0.667203 11.00000 0.05470 0.07731 =
0.04961 0.00627 0.00791 -0.00376
AFIX 43
H10 2 0.785500 0.451391 0.574852 11.00000 -1.20000
AFIX 0
C11 1 0.896977 0.372111 0.715005 11.00000 0.05200 0.09371 =
0.06643 0.00020 0.01323 -0.01263
AFIX 43
H11 2 0.933322 0.450636 0.653406 11.00000 -1.20000
AFIX 0
C12 1 0.930047 0.255275 0.854540 11.00000 0.04394 0.09333 =
0.07515 -0.01141 -0.00068 -0.00190
AFIX 43
H12 2 0.988685 0.258415 0.889905 11.00000 -1.20000
AFIX 0
C13 1 0.877841 0.136574 0.939918 11.00000 0.05693 0.08465 =
0.07107 0.00780 -0.00964 0.00247
AFIX 43
H13 2 0.901136 0.055419 1.030886 11.00000 -1.20000
AFIX 0
C14 1 0.789829 0.134319 0.893455 11.00000 0.05725 0.06921 =
0.06011 0.00931 0.00071 -0.00534
AFIX 43
H14 2 0.754498 0.053235 0.954848 11.00000 -1.20000
AFIX 0
C15 1 0.241973 0.254271 0.271464 11.00000 0.03867 0.06970 =
0.03889 0.00170 0.00344 0.00344
C16 1 0.186598 0.113248 0.197258 11.00000 0.04582 0.08051 =
0.05016 -0.00904 0.00369 -0.00026
AFIX 43
H16 2 0.206973 0.021062 0.120161 11.00000 -1.20000
AFIX 0
C17 1 0.100816 0.111157 0.239090 11.00000 0.04530 0.09730 =
0.05922 -0.00231 0.00670 -0.01227
AFIX 43
H17 2 0.064378 0.015237 0.191990 11.00000 -1.20000
AFIX 0
C18 1 0.069233 0.249359 0.349354 11.00000 0.04095 0.13261 =
0.04986 0.00679 0.01260 0.00817
AFIX 43
H18 2 0.011627 0.247800 0.375437 11.00000 -1.20000
AFIX 0
C19 1 0.123490 0.389873 0.420743 11.00000 0.04811 0.10406 =
0.05070 -0.01285 0.00922 0.01758
AFIX 43
H19 2 0.102667 0.483382 0.495830 11.00000 -1.20000
AFIX 0
C20 1 0.209836 0.391984 0.380380 11.00000 0.04301 0.08124 =
0.05004 -0.00895 0.00380 0.00833
AFIX 43
H20 2 0.246029 0.488086 0.428011 11.00000 -1.20000
AFIX 0
C21 1 0.333639 0.255420 0.216477 11.00000 0.03898 0.06411 =
0.03920 0.00117 0.00752 0.00204
N1 3 0.396620 0.267649 0.350631 11.00000 0.03334 0.07235 =
0.03330 0.00203 0.00999 0.00476
O1 4 0.347390 0.248150 0.056054 11.00000 0.04795 0.10966 =
0.03823 -0.00283 0.00961 0.00376
HKLF 4
REM 20160602wxn-1_a.res in Pc
REM R1 = 0.0712 for 1508 Fo > 4sig(Fo) and 0.0737 for all 1658 data
REM 208 parameters refined using 2 restraints
END
WGHT 0.1597 0.0000
REM Highest difference peak 0.235, deepest hole -0.392, 1-sigma level 0.067
Q1 1 0.4806 0.3744 0.6279 11.00000 0.05 0.24
Q2 1 0.4023 0.1204 0.3501 11.00000 0.05 0.22
Q3 1 0.3607 0.4504 0.5768 11.00000 0.05 0.22
Q4 1 0.9213 0.3874 0.8711 11.00000 0.05 0.22
Q5 1 0.1761 0.4835 0.6696 11.00000 0.05 0.21
Q6 1 0.4826 0.1277 0.6365 11.00000 0.05 0.21
Q7 1 0.5285 0.2638 0.5435 11.00000 0.05 0.20
Q8 1 0.3329 0.2600 -0.1835 11.00000 0.05 0.19
Q9 1 0.4429 0.3320 0.5635 11.00000 0.05 0.19
Q10 1 0.5939 0.3616 0.5045 11.00000 0.05 0.18
Q11 1 0.5254 0.1324 0.4545 11.00000 0.05 0.18
Q12 1 0.1833 0.1232 -0.0152 11.00000 0.05 0.18
Q13 1 0.5984 0.1729 0.4727 11.00000 0.05 0.18
Q14 1 0.2906 0.2425 0.6873 11.00000 0.05 0.18
Q15 1 0.2546 0.2517 0.5241 11.00000 0.05 0.18
Q16 1 0.4557 0.1185 0.9194 11.00000 0.05 0.18
Q17 1 0.1465 -0.0166 -0.0389 11.00000 0.05 0.18
Q18 1 0.4015 0.4226 0.3510 11.00000 0.05 0.17
Q19 1 0.4771 0.1280 0.3034 11.00000 0.05 0.17
Q20 1 0.2181 0.1497 0.3689 11.00000 0.05 0.17
REM The information below was added by Olex2.
REM
REM R1 = 0.0712 for 1508 Fo > 4sig(Fo) and 0.0737 for all 2631 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.24, deepest hole -0.39
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0737
REM R1_gt = 0.0712
REM wR_ref = 0.2227
REM GOOF = 1.139
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 2631
REM Reflections_gt = 1508
REM Parameters = n/a
REM Hole = -0.39
REM Peak = 0.24
REM Flack = 0.3(8)
;
_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_3ah
_database_code_depnum_ccdc_archive 'CCDC 1491621'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C21 H18 F N O2 S'
_chemical_formula_sum 'C21 H18 F N O2 S'
_chemical_formula_weight 367.42
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
_cell_length_a 19.4865(5)
_cell_length_b 6.17720(10)
_cell_length_c 15.7523(4)
_cell_angle_alpha 90.00
_cell_angle_beta 109.925(3)
_cell_angle_gamma 90.00
_cell_volume 1782.63(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3672
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.5060
_cell_measurement_theta_min 4.3980
_exptl_absorpt_coefficient_mu 1.828
_exptl_absorpt_correction_T_max 0.7112
_exptl_absorpt_correction_T_min 0.6578
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.369
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 768
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0244
_diffrn_reflns_av_unetI/netI 0.0309
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 6380
_diffrn_reflns_theta_full 73.64
_diffrn_reflns_theta_max 73.64
_diffrn_reflns_theta_min 4.83
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -67.00 33.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 57.0000 -60.0000 100
#__ type_ start__ end____ width___ exp.time_
2 omega -9.00 34.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 -150.0000 43
#__ type_ start__ end____ width___ exp.time_
3 omega -103.00 -76.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -57.0000 150.0000 27
#__ type_ start__ end____ width___ exp.time_
4 omega -55.00 -12.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -57.0000 150.0000 43
#__ type_ start__ end____ width___ exp.time_
5 omega -83.00 -46.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -167.0000 -42.0000 37
#__ type_ start__ end____ width___ exp.time_
6 omega 32.00 84.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 0.0000 52
#__ type_ start__ end____ width___ exp.time_
7 omega 48.00 89.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 90.0000 41
#__ type_ start__ end____ width___ exp.time_
8 omega 55.00 87.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 60.0000 32
#__ type_ start__ end____ width___ exp.time_
9 omega 27.00 102.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 -150.0000 75
#__ type_ start__ end____ width___ exp.time_
10 omega 37.00 88.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -150.0000 51
#__ type_ start__ end____ width___ exp.time_
11 omega 23.00 169.00 1.0000 1.2500
omega____ theta____ kappa____ phi______ frames
- 107.1410 0.0000 -150.0000 146
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0697325000
_diffrn_orient_matrix_UB_12 0.0707715000
_diffrn_orient_matrix_UB_13 -0.0764655000
_diffrn_orient_matrix_UB_21 0.0450434000
_diffrn_orient_matrix_UB_22 0.0391385000
_diffrn_orient_matrix_UB_23 -0.0621796000
_diffrn_orient_matrix_UB_31 -0.0134232000
_diffrn_orient_matrix_UB_32 -0.2359368000
_diffrn_orient_matrix_UB_33 -0.0332125000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 3035
_reflns_number_total 3487
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max 0.200
_refine_diff_density_min -0.432
_refine_diff_density_rms 0.063
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.071
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 3487
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0542
_refine_ls_R_factor_gt 0.0492
_refine_ls_restrained_S_all 1.071
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0841P)^2^+0.1884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1395
_refine_ls_wR_factor_ref 0.1473
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16),
C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.69126(10) 0.2839(3) 0.73439(15) 0.0566(5) Uani 1 d . . .
H1A H 0.6817 0.1373 0.7494 0.068 Uiso 1 calc . . R
H1B H 0.7132 0.2796 0.6876 0.068 Uiso 1 calc . . R
C2 C 0.62325(10) 0.4181(3) 0.70627(12) 0.0482(4) Uani 1 d . . .
C3 C 0.63713(10) 0.6183(3) 0.74900(13) 0.0509(4) Uani 1 d . . .
C4 C 0.71514(11) 0.6319(3) 0.81023(15) 0.0603(5) Uani 1 d . . .
H4A H 0.7438 0.7222 0.7845 0.072 Uiso 1 calc . . R
H4B H 0.7189 0.6874 0.8693 0.072 Uiso 1 calc . . R
C5 C 0.55471(10) 0.3680(3) 0.64621(12) 0.0498(4) Uani 1 d . . .
H5 H 0.5463 0.2333 0.6182 0.060 Uiso 1 calc . . R
C6 C 0.49790(10) 0.5194(3) 0.62736(12) 0.0470(4) Uani 1 d . . .
C7 C 0.51356(11) 0.7203(3) 0.67072(14) 0.0563(5) Uani 1 d . . .
H7 H 0.4767 0.8236 0.6587 0.068 Uiso 1 calc . . R
C8 C 0.58187(11) 0.7700(3) 0.73073(15) 0.0588(5) Uani 1 d . . .
H8 H 0.5907 0.9047 0.7587 0.071 Uiso 1 calc . . R
C9 C 0.42279(10) 0.4670(3) 0.56583(11) 0.0488(4) Uani 1 d . . .
C10 C 0.40856(11) 0.2778(3) 0.51490(14) 0.0571(5) Uani 1 d . . .
H10 H 0.4463 0.1830 0.5175 0.069 Uiso 1 calc . . R
C11 C 0.33838(13) 0.2321(4) 0.46083(15) 0.0645(5) Uani 1 d . . .
C12 C 0.28007(13) 0.3612(4) 0.45363(15) 0.0711(6) Uani 1 d . . .
H12 H 0.2332 0.3245 0.4165 0.085 Uiso 1 calc . . R
C13 C 0.29372(13) 0.5486(5) 0.50384(17) 0.0800(7) Uani 1 d . . .
H13 H 0.2553 0.6413 0.5007 0.096 Uiso 1 calc . . R
C14 C 0.36344(12) 0.6007(4) 0.55866(15) 0.0684(6) Uani 1 d . . .
H14 H 0.3711 0.7285 0.5918 0.082 Uiso 1 calc . . R
C15 C 0.86483(9) 0.4209(3) 0.77824(13) 0.0521(4) Uani 1 d . . .
C16 C 0.86462(11) 0.2809(3) 0.70902(15) 0.0597(5) Uani 1 d . . .
H16 H 0.8449 0.1428 0.7059 0.072 Uiso 1 calc . . R
C17 C 0.89389(11) 0.3485(4) 0.64492(15) 0.0645(5) Uani 1 d . . .
H17 H 0.8939 0.2544 0.5988 0.077 Uiso 1 calc . . R
C18 C 0.92331(10) 0.5542(4) 0.64820(14) 0.0628(5) Uani 1 d . . .
C19 C 0.92314(10) 0.6911(3) 0.71831(15) 0.0608(5) Uani 1 d . . .
H19 H 0.9431 0.8290 0.7217 0.073 Uiso 1 calc . . R
C20 C 0.89409(10) 0.6271(3) 0.78288(14) 0.0567(5) Uani 1 d . . .
H20 H 0.8941 0.7211 0.8290 0.068 Uiso 1 calc . . R
C21 C 0.95537(14) 0.6268(6) 0.57821(18) 0.0931(9) Uani 1 d . . .
H21A H 1.0013 0.5555 0.5886 0.140 Uiso 1 calc . . GR
H21B H 0.9628 0.7806 0.5824 0.140 Uiso 1 calc . . GR
H21C H 0.9225 0.5905 0.5191 0.140 Uiso 1 calc . . GR
F1 F 0.32680(9) 0.0468(3) 0.41163(12) 0.1010(5) Uani 1 d . . .
N1 N 0.73798(9) 0.4024(3) 0.81507(11) 0.0559(4) Uani 1 d . . .
O1 O 0.82662(9) 0.1060(3) 0.86059(12) 0.0795(5) Uani 1 d . . .
O2 O 0.85438(9) 0.4623(3) 0.93748(10) 0.0793(5) Uani 1 d . . .
S1 S 0.82392(3) 0.33787(9) 0.85687(3) 0.06063(19) Uani 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 0.0511(10) 0.0451(9) 0.0667(12) -0.0079(8) 0.0111(9) -0.0059(8)
C2 0.0538(10) 0.0414(8) 0.0516(9) -0.0030(7) 0.0209(8) -0.0040(7)
C3 0.0537(10) 0.0488(9) 0.0551(10) -0.0115(8) 0.0248(9) -0.0098(8)
C4 0.0581(11) 0.0565(11) 0.0676(12) -0.0181(10) 0.0230(10) -0.0096(9)
C5 0.0537(10) 0.0403(8) 0.0538(10) -0.0058(7) 0.0163(8) -0.0035(7)
C6 0.0523(9) 0.0450(8) 0.0474(9) -0.0021(7) 0.0218(8) -0.0025(7)
C7 0.0563(10) 0.0482(9) 0.0713(12) -0.0095(9) 0.0308(10) -0.0001(8)
C8 0.0607(11) 0.0481(9) 0.0749(13) -0.0205(9) 0.0325(10) -0.0071(8)
C9 0.0546(10) 0.0510(9) 0.0416(8) 0.0032(7) 0.0173(8) 0.0019(8)
C10 0.0574(11) 0.0555(10) 0.0561(11) -0.0050(9) 0.0162(9) 0.0006(8)
C11 0.0707(13) 0.0622(12) 0.0542(11) -0.0065(9) 0.0129(10) -0.0076(10)
C12 0.0558(12) 0.0887(16) 0.0561(12) 0.0018(11) 0.0025(10) 0.0012(11)
C13 0.0606(13) 0.0953(18) 0.0700(14) -0.0083(13) 0.0040(11) 0.0206(12)
C14 0.0633(12) 0.0681(12) 0.0635(12) -0.0108(11) 0.0084(10) 0.0125(10)
C15 0.0426(8) 0.0513(9) 0.0524(10) -0.0011(8) 0.0035(7) 0.0005(7)
C16 0.0486(10) 0.0515(10) 0.0680(13) -0.0075(9) 0.0057(9) 0.0041(8)
C17 0.0462(10) 0.0770(14) 0.0609(12) -0.0131(10) 0.0063(9) 0.0113(9)
C18 0.0370(8) 0.0835(14) 0.0602(12) 0.0046(10) 0.0064(8) 0.0093(9)
C19 0.0432(9) 0.0598(11) 0.0710(13) 0.0029(10) 0.0086(9) -0.0030(8)
C20 0.0474(9) 0.0545(10) 0.0601(11) -0.0085(9) 0.0079(8) -0.0046(8)
C21 0.0691(15) 0.137(3) 0.0763(17) 0.0116(17) 0.0281(13) 0.0016(16)
F1 0.0900(10) 0.0835(10) 0.1057(12) -0.0381(9) 0.0026(9) -0.0135(8)
N1 0.0557(9) 0.0531(8) 0.0553(9) -0.0042(7) 0.0141(7) -0.0105(7)
O1 0.0767(11) 0.0609(9) 0.0897(12) 0.0228(8) 0.0137(9) 0.0008(7)
O2 0.0789(10) 0.0986(12) 0.0457(8) -0.0044(8) 0.0020(7) -0.0158(9)
S1 0.0573(3) 0.0614(3) 0.0528(3) 0.0062(2) 0.0054(2) -0.0062(2)
_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.496(3) . ?
C1 N1 1.480(2) . ?
C2 C3 1.390(2) . ?
C2 C5 1.383(2) . ?
C3 C4 1.500(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.480(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(2) . ?
C6 C7 1.399(3) . ?
C6 C9 1.490(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C11 C12 1.361(3) . ?
C11 F1 1.357(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 C20 1.387(3) . ?
C15 S1 1.762(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 C19 1.392(3) . ?
C18 C21 1.509(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6264(17) . ?
O1 S1 1.4340(17) . ?
O2 S1 1.4291(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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
N1 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
N1 C1 C2 101.77(15) . . ?
C3 C2 C1 110.06(16) . . ?
C5 C2 C1 129.03(16) . . ?
C5 C2 C3 120.90(17) . . ?
C2 C3 C4 110.41(16) . . ?
C8 C3 C2 119.56(18) . . ?
C8 C3 C4 130.03(17) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.56(15) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 119.9 . . ?
C2 C5 C6 120.30(16) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C9 121.53(16) . . ?
C7 C6 C5 117.60(17) . . ?
C7 C6 C9 120.84(17) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.07(18) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.57(17) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C6 121.07(17) . . ?
C10 C9 C14 117.02(18) . . ?
C14 C9 C6 121.88(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.45(19) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 123.9(2) . . ?
F1 C11 C10 117.7(2) . . ?
F1 C11 C12 118.4(2) . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.9(2) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.8(2) . . ?
C13 C14 H14 119.1 . . ?
C16 C15 S1 119.27(15) . . ?
C20 C15 C16 120.24(19) . . ?
C20 C15 S1 120.44(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 118.3(2) . . ?
C17 C18 C21 120.9(2) . . ?
C19 C18 C21 120.8(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 H20 120.4 . . ?
C19 C20 C15 119.27(19) . . ?
C19 C20 H20 120.4 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 110.06(16) . . ?
C1 N1 S1 118.27(13) . . ?
C4 N1 S1 120.37(13) . . ?
N1 S1 C15 107.11(8) . . ?
O1 S1 C15 107.49(10) . . ?
O1 S1 N1 106.25(9) . . ?
O2 S1 C15 108.51(10) . . ?
O2 S1 N1 106.65(10) . . ?
O2 S1 O1 120.18(11) . . ?
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
C1 C2 C3 C4 -1.0(2) . . . . ?
C1 C2 C3 C8 178.41(18) . . . . ?
C1 C2 C5 C6 -178.62(18) . . . . ?
C1 N1 S1 C15 68.70(16) . . . . ?
C1 N1 S1 O1 -45.95(17) . . . . ?
C1 N1 S1 O2 -175.28(14) . . . . ?
C2 C1 N1 C4 -24.6(2) . . . . ?
C2 C1 N1 S1 -168.45(12) . . . . ?
C2 C3 C4 N1 -13.8(2) . . . . ?
C2 C3 C8 C7 0.4(3) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -177.54(15) . . . . ?
C3 C2 C5 C6 0.1(3) . . . . ?
C3 C4 N1 C1 24.0(2) . . . . ?
C3 C4 N1 S1 166.96(13) . . . . ?
C4 C3 C8 C7 179.66(19) . . . . ?
C4 N1 S1 C15 -71.35(17) . . . . ?
C4 N1 S1 O1 174.00(16) . . . . ?
C4 N1 S1 O2 44.67(18) . . . . ?
C5 C2 C3 C4 -179.92(16) . . . . ?
C5 C2 C3 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C9 C10 -9.2(3) . . . . ?
C5 C6 C9 C14 168.76(18) . . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C6 C9 C10 C11 178.23(18) . . . . ?
C6 C9 C14 C13 -178.0(2) . . . . ?
C7 C6 C9 C10 172.83(17) . . . . ?
C7 C6 C9 C14 -9.2(3) . . . . ?
C8 C3 C4 N1 166.90(19) . . . . ?
C9 C6 C7 C8 177.41(17) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C9 C10 C11 F1 179.47(19) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C16 C15 S1 N1 -87.51(16) . . . . ?
C16 C15 S1 O1 26.31(18) . . . . ?
C16 C15 S1 O2 157.71(16) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C16 C17 C18 C21 179.8(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C20 C15 S1 N1 89.68(16) . . . . ?
C20 C15 S1 O1 -156.50(16) . . . . ?
C20 C15 S1 O2 -25.10(19) . . . . ?
C21 C18 C19 C20 -180.0(2) . . . . ?
F1 C11 C12 C13 -179.5(2) . . . . ?
N1 C1 C2 C3 15.3(2) . . . . ?
N1 C1 C2 C5 -165.87(17) . . . . ?
S1 C15 C16 C17 177.31(15) . . . . ?
S1 C15 C20 C19 -177.39(14) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160528wxn-1_a.res in P2(1)/c
CELL 1.54184 19.4865 6.1772 15.7523 90 109.925 90
ZERR 4 0.0005 0.0001 0.0004 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S F
UNIT 84 72 4 8 4 4
L.S. 10
PLAN 20
SIZE 0.25 0.2 0.2
BOND $H
LIST 6
CONF
HTAB
fmap 2
acta
REM
REM
REM
WGHT 0.084100 0.188400
FVAR 0.68033
C1 1 0.691260 0.283945 0.734387 11.00000 0.05108 0.04510 =
0.06667 -0.00791 0.01114 -0.00593
AFIX 23
H1A 2 0.681706 0.137324 0.749401 11.00000 -1.20000
H1B 2 0.713165 0.279572 0.687587 11.00000 -1.20000
AFIX 0
C2 1 0.623251 0.418130 0.706268 11.00000 0.05378 0.04144 =
0.05156 -0.00304 0.02094 -0.00400
C3 1 0.637129 0.618313 0.749000 11.00000 0.05374 0.04877 =
0.05508 -0.01155 0.02477 -0.00977
C4 1 0.715140 0.631947 0.810233 11.00000 0.05814 0.05646 =
0.06760 -0.01812 0.02302 -0.00956
AFIX 23
H4A 2 0.743823 0.722150 0.784539 11.00000 -1.20000
H4B 2 0.718933 0.687450 0.869267 11.00000 -1.20000
AFIX 0
C5 1 0.554706 0.368018 0.646207 11.00000 0.05368 0.04029 =
0.05377 -0.00579 0.01627 -0.00349
AFIX 43
H5 2 0.546287 0.233273 0.618210 11.00000 -1.20000
AFIX 0
C6 1 0.497899 0.519382 0.627362 11.00000 0.05234 0.04504 =
0.04736 -0.00211 0.02180 -0.00254
C7 1 0.513556 0.720292 0.670720 11.00000 0.05626 0.04822 =
0.07132 -0.00955 0.03080 -0.00007
AFIX 43
H7 2 0.476741 0.823568 0.658698 11.00000 -1.20000
AFIX 0
C8 1 0.581873 0.769985 0.730729 11.00000 0.06067 0.04812 =
0.07494 -0.02049 0.03254 -0.00707
AFIX 43
H8 2 0.590686 0.904720 0.758712 11.00000 -1.20000
AFIX 0
C9 1 0.422793 0.467029 0.565835 11.00000 0.05456 0.05105 =
0.04157 0.00315 0.01729 0.00193
C10 1 0.408564 0.277772 0.514901 11.00000 0.05740 0.05547 =
0.05615 -0.00501 0.01619 0.00059
AFIX 43
H10 2 0.446321 0.183049 0.517489 11.00000 -1.20000
AFIX 0
C11 1 0.338378 0.232061 0.460832 11.00000 0.07072 0.06223 =
0.05419 -0.00646 0.01285 -0.00757
C12 1 0.280071 0.361226 0.453635 11.00000 0.05578 0.08871 =
0.05614 0.00179 0.00249 0.00124
AFIX 43
H12 2 0.233161 0.324503 0.416487 11.00000 -1.20000
AFIX 0
C13 1 0.293725 0.548575 0.503836 11.00000 0.06065 0.09534 =
0.07004 -0.00829 0.00401 0.02063
AFIX 43
H13 2 0.255336 0.641293 0.500701 11.00000 -1.20000
AFIX 0
C14 1 0.363441 0.600723 0.558660 11.00000 0.06334 0.06813 =
0.06352 -0.01081 0.00837 0.01255
AFIX 43
H14 2 0.371143 0.728544 0.591788 11.00000 -1.20000
AFIX 0
C15 1 0.864827 0.420936 0.778239 11.00000 0.04264 0.05128 =
0.05242 -0.00113 0.00346 0.00048
C16 1 0.864618 0.280939 0.709022 11.00000 0.04861 0.05150 =
0.06795 -0.00754 0.00571 0.00412
AFIX 43
H16 2 0.844920 0.142805 0.705868 11.00000 -1.20000
AFIX 0
C17 1 0.893891 0.348474 0.644921 11.00000 0.04625 0.07704 =
0.06090 -0.01310 0.00627 0.01129
AFIX 43
H17 2 0.893863 0.254422 0.598809 11.00000 -1.20000
AFIX 0
C18 1 0.923311 0.554164 0.648201 11.00000 0.03704 0.08351 =
0.06018 0.00456 0.00643 0.00926
C19 1 0.923145 0.691122 0.718307 11.00000 0.04319 0.05984 =
0.07105 0.00292 0.00861 -0.00297
AFIX 43
H19 2 0.943081 0.828989 0.721705 11.00000 -1.20000
AFIX 0
C20 1 0.894088 0.627094 0.782877 11.00000 0.04743 0.05451 =
0.06011 -0.00853 0.00794 -0.00464
AFIX 43
H20 2 0.894125 0.721135 0.828998 11.00000 -1.20000
AFIX 0
C21 1 0.955373 0.626816 0.578210 11.00000 0.06908 0.13652 =
0.07631 0.01156 0.02806 0.00162
AFIX 137
H21A 2 1.001284 0.555505 0.588564 11.00000 -1.50000
H21B 2 0.962763 0.780647 0.582443 11.00000 -1.50000
H21C 2 0.922468 0.590521 0.519093 11.00000 -1.50000
AFIX 0
F1 6 0.326800 0.046808 0.411629 11.00000 0.09000 0.08353 =
0.10574 -0.03807 0.00258 -0.01350
N1 3 0.737983 0.402382 0.815075 11.00000 0.05566 0.05306 =
0.05525 -0.00417 0.01405 -0.01047
O1 4 0.826623 0.105969 0.860592 11.00000 0.07666 0.06087 =
0.08969 0.02280 0.01365 0.00077
O2 4 0.854383 0.462341 0.937480 11.00000 0.07892 0.09855 =
0.04565 -0.00436 0.00195 -0.01575
S1 5 0.823918 0.337874 0.856866 11.00000 0.05731 0.06141 =
0.05284 0.00616 0.00538 -0.00618
HKLF 4
REM 20160528wxn-1_a.res in P2(1)/c
REM R1 = 0.0492 for 3035 Fo > 4sig(Fo) and 0.0542 for all 3487 data
REM 236 parameters refined using 0 restraints
END
WGHT 0.0841 0.1883
REM Highest difference peak 0.200, deepest hole -0.432, 1-sigma level 0.063
Q1 1 0.9560 0.4471 0.5275 11.00000 0.05 0.20
Q2 1 0.8578 0.2245 0.9485 11.00000 0.05 0.18
Q3 1 0.4386 0.9612 0.5698 11.00000 0.05 0.18
Q4 1 0.4795 1.0394 0.6263 11.00000 0.05 0.17
Q5 1 0.4506 0.1011 0.6226 11.00000 0.05 0.17
Q6 1 0.5880 0.9676 0.7213 11.00000 0.05 0.17
Q7 1 0.4808 0.9969 0.6473 11.00000 0.05 0.16
Q8 1 0.9162 0.4028 0.4612 11.00000 0.05 0.16
Q9 1 0.4902 0.8980 0.6205 11.00000 0.05 0.16
Q10 1 0.5374 0.1019 0.6829 11.00000 0.05 0.16
Q11 1 0.4633 0.4841 0.5966 11.00000 0.05 0.16
Q12 1 0.3113 0.0205 0.4652 11.00000 0.05 0.15
Q13 1 0.8591 -0.0003 0.9412 11.00000 0.05 0.15
Q14 1 0.5404 0.1742 0.6501 11.00000 0.05 0.15
Q15 1 0.5014 0.1785 0.6546 11.00000 0.05 0.14
Q16 1 0.8617 0.0324 0.8792 11.00000 0.05 0.14
Q17 1 0.8711 0.5752 0.4310 11.00000 0.05 0.14
Q18 1 0.4817 0.8303 0.5728 11.00000 0.05 0.14
Q19 1 0.8831 0.5979 0.4231 11.00000 0.05 0.14
Q20 1 0.1725 0.2046 0.3997 11.00000 0.05 0.13
REM The information below was added by Olex2.
REM
REM R1 = 0.0492 for 3035 Fo > 4sig(Fo) and 0.0542 for all 6810 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.20, deepest hole -0.43
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0542
REM R1_gt = 0.0492
REM wR_ref = 0.1473
REM GOOF = 1.071
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 6810
REM Reflections_gt = 3035
REM Parameters = n/a
REM Hole = -0.43
REM Peak = 0.20
REM Flack = n/a
;
_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_3ad
_database_code_depnum_ccdc_archive 'CCDC 1491618'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C22 H21 N O2 S'
_chemical_formula_sum 'C22 H21 N O2 S'
_chemical_formula_weight 363.46
_chemical_absolute_configuration ad
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
_cell_length_a 7.9693(2)
_cell_length_b 6.1218(2)
_cell_length_c 19.3280(5)
_cell_angle_alpha 90.00
_cell_angle_beta 101.204(2)
_cell_angle_gamma 90.00
_cell_volume 924.97(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 7272
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.3580
_cell_measurement_theta_min 4.6670
_exptl_absorpt_coefficient_mu 1.674
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.54914
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.305
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 384
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.18
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0323
_diffrn_reflns_av_unetI/netI 0.0231
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 13752
_diffrn_reflns_theta_full 67.07
_diffrn_reflns_theta_max 67.07
_diffrn_reflns_theta_min 4.66
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -37.00 17.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 -90.0000 54
#__ type_ start__ end____ width___ exp.time_
2 omega -50.00 34.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 30.0000 84
#__ type_ start__ end____ width___ exp.time_
3 omega -95.00 -6.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- -40.5455 125.0000 120.0000 89
#__ type_ start__ end____ width___ exp.time_
4 omega -67.00 31.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- -40.5455 19.0000 150.0000 98
#__ type_ start__ end____ width___ exp.time_
5 omega 23.00 49.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 -60.0000 26
#__ type_ start__ end____ width___ exp.time_
6 omega 53.00 91.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 30.0000 38
#__ type_ start__ end____ width___ exp.time_
7 omega 23.00 50.00 1.0000 12.5000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 -30.0000 27
#__ type_ start__ end____ width___ exp.time_
8 omega 42.00 91.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -90.0000 49
#__ type_ start__ end____ width___ exp.time_
9 omega 49.00 104.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 120.0000 55
#__ type_ start__ end____ width___ exp.time_
10 omega 42.00 90.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 90.0000 48
#__ type_ start__ end____ width___ exp.time_
11 omega 25.00 109.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 30.0000 84
#__ type_ start__ end____ width___ exp.time_
12 omega 44.00 90.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 30.0000 46
#__ type_ start__ end____ width___ exp.time_
13 omega 47.00 139.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -77.0000 -180.0000 92
#__ type_ start__ end____ width___ exp.time_
14 omega 54.00 160.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 15.0000 0.0000 106
#__ type_ start__ end____ width___ exp.time_
15 omega 94.00 121.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -60.0000 27
#__ type_ start__ end____ width___ exp.time_
16 omega 84.00 171.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 30.0000 60.0000 87
#__ type_ start__ end____ width___ exp.time_
17 omega 42.00 70.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -60.0000 28
#__ type_ start__ end____ width___ exp.time_
18 omega 39.00 81.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 90.0000 42
#__ type_ start__ end____ width___ exp.time_
19 omega 31.00 85.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 150.0000 54
#__ type_ start__ end____ width___ exp.time_
20 omega 45.00 88.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 0.0000 43
#__ type_ start__ end____ width___ exp.time_
21 omega 71.00 109.00 1.0000 70.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 30.0000 38
#__ type_ start__ end____ width___ exp.time_
22 omega 8.00 48.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 40.7955 77.0000 -180.0000 40
#__ type_ start__ end____ width___ exp.time_
23 omega 1.00 26.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 38.0000 90.0000 0.7496 25
#__ type_ start__ end____ width___ exp.time_
24 omega -1.00 25.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 38.0000 94.0000 129.9724 26
#__ type_ start__ end____ width___ exp.time_
25 omega -100.00 -47.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -57.0000 -30.0000 53
#__ type_ start__ end____ width___ exp.time_
26 omega -79.00 -53.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -38.0000 90.0000 26
#__ type_ start__ end____ width___ exp.time_
27 omega -42.00 -16.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -38.0000 90.0000 26
#__ type_ start__ end____ width___ exp.time_
28 omega -41.00 -13.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -57.0000 -30.0000 28
#__ type_ start__ end____ width___ exp.time_
29 omega -40.00 -14.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -57.0000 150.0000 26
#__ type_ start__ end____ width___ exp.time_
30 omega -114.00 -88.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -38.0000 90.0000 26
#__ type_ start__ end____ width___ exp.time_
31 omega 18.00 45.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 50.0000 80.0000 38.7730 27
#__ type_ start__ end____ width___ exp.time_
32 omega 19.00 44.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 50.0000 81.0000 -112.1148 25
#__ type_ start__ end____ width___ exp.time_
33 omega 21.00 47.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 54.0000 79.0000 164.2213 26
#__ type_ start__ end____ width___ exp.time_
34 omega 21.00 46.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 54.0000 79.0000 100.8808 25
#__ type_ start__ end____ width___ exp.time_
35 omega 34.00 60.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 58.0000 76.0000 -125.8833 26
#__ type_ start__ end____ width___ exp.time_
36 omega 34.00 68.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 62.0000 75.0000 -26.7581 34
#__ type_ start__ end____ width___ exp.time_
37 omega 31.00 81.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 62.0000 77.0000 -167.1431 50
#__ type_ start__ end____ width___ exp.time_
38 omega 33.00 64.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 25.4504 31
#__ type_ start__ end____ width___ exp.time_
39 omega 33.00 72.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 -86.7803 39
#__ type_ start__ end____ width___ exp.time_
40 omega 88.00 130.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 70.0000 77.0000 69.9721 42
#__ type_ start__ end____ width___ exp.time_
41 omega 37.00 71.00 1.0000 2.5000
omega____ theta____ kappa____ phi______ frames
- 70.0000 77.0000 69.9721 34
#__ type_ start__ end____ width___ exp.time_
42 omega 47.00 94.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 78.0000 72.0000 116.2167 47
#__ type_ start__ end____ width___ exp.time_
43 omega 76.00 153.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -150.0000 77
#__ type_ start__ end____ width___ exp.time_
44 omega 75.00 100.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 0.0000 25
#__ type_ start__ end____ width___ exp.time_
45 omega 125.00 151.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 120.0000 26
#__ type_ start__ end____ width___ exp.time_
46 omega 75.00 114.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 120.0000 39
#__ type_ start__ end____ width___ exp.time_
47 omega 80.00 163.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -180.0000 83
#__ type_ start__ end____ width___ exp.time_
48 omega 83.00 147.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 150.0000 64
#__ type_ start__ end____ width___ exp.time_
49 omega 80.00 105.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 120.0000 25
#__ type_ start__ end____ width___ exp.time_
50 omega 75.00 100.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -90.0000 25
#__ type_ start__ end____ width___ exp.time_
51 omega 76.00 101.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -180.0000 25
#__ type_ start__ end____ width___ exp.time_
52 omega 82.00 108.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -60.0000 26
#__ type_ start__ end____ width___ exp.time_
53 omega 75.00 100.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 30.0000 25
#__ type_ start__ end____ width___ exp.time_
54 omega 75.00 101.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 150.0000 26
#__ type_ start__ end____ width___ exp.time_
55 omega 75.00 101.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -60.0000 26
#__ type_ start__ end____ width___ exp.time_
56 omega 151.00 177.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 60.0000 26
#__ type_ start__ end____ width___ exp.time_
57 omega 78.00 104.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 60.0000 26
#__ type_ start__ end____ width___ exp.time_
58 omega 87.00 113.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
59 omega 80.00 111.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 90.0000 31
#__ type_ start__ end____ width___ exp.time_
60 omega 117.00 173.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 90.0000 56
#__ type_ start__ end____ width___ exp.time_
61 omega 75.00 128.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -120.0000 53
#__ type_ start__ end____ width___ exp.time_
62 omega 78.00 104.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -30.0000 26
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.1632940000
_diffrn_orient_matrix_UB_12 -0.0187297000
_diffrn_orient_matrix_UB_13 -0.0311392000
_diffrn_orient_matrix_UB_21 0.1104180000
_diffrn_orient_matrix_UB_22 0.0245388000
_diffrn_orient_matrix_UB_23 0.0744462000
_diffrn_orient_matrix_UB_31 -0.0014526000
_diffrn_orient_matrix_UB_32 -0.2496345000
_diffrn_orient_matrix_UB_33 0.0096929000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 2969
_reflns_number_total 3178
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max 0.086
_refine_diff_density_min -0.169
_refine_diff_density_rms 0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.002(15)
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 237
_refine_ls_number_reflns 3178
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0345
_refine_ls_R_factor_gt 0.0307
_refine_ls_restrained_S_all 1.040
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0818
_refine_ls_wR_factor_ref 0.0845
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.0737(3) 0.5101(4) 0.30138(10) 0.0683(5) Uani 1 d . . .
H1A H 0.1679 0.5178 0.2764 0.082 Uiso 1 calc . . R
H1B H 0.0538 0.3589 0.3124 0.082 Uiso 1 calc . . R
C2 C 0.1065(2) 0.6502(3) 0.36694(9) 0.0550(4) Uani 1 d . . .
C3 C 0.0124(2) 0.8405(3) 0.35514(9) 0.0569(4) Uani 1 d . . .
C4 C -0.0972(3) 0.8409(4) 0.28272(10) 0.0663(5) Uani 1 d . . .
H4A H -0.2148 0.8783 0.2841 0.080 Uiso 1 calc . . R
H4B H -0.0537 0.9416 0.2517 0.080 Uiso 1 calc . . R
C5 C 0.2152(2) 0.6113(3) 0.43083(9) 0.0565(4) Uani 1 d . . .
H5 H 0.2780 0.4824 0.4377 0.068 Uiso 1 calc . . R
C6 C 0.2309(2) 0.7662(3) 0.48533(9) 0.0519(4) Uani 1 d . . .
C7 C 0.1351(3) 0.9568(4) 0.47160(10) 0.0630(5) Uani 1 d . . .
H7 H 0.1439 1.0620 0.5069 0.076 Uiso 1 calc . . R
C8 C 0.0276(3) 0.9961(4) 0.40782(10) 0.0665(5) Uani 1 d . . .
H8 H -0.0340 1.1259 0.4003 0.080 Uiso 1 calc . . R
C9 C 0.3385(2) 0.7239(3) 0.55600(10) 0.0519(4) Uani 1 d . . .
C10 C 0.4227(3) 0.5273(5) 0.57240(10) 0.0755(6) Uani 1 d . . .
H10 H 0.4204 0.4236 0.5371 0.091 Uiso 1 calc . . R
C11 C 0.5101(3) 0.4807(4) 0.63991(12) 0.0796(7) Uani 1 d . . .
H11 H 0.5646 0.3464 0.6487 0.096 Uiso 1 calc . . R
C12 C 0.5186(2) 0.6274(4) 0.69437(10) 0.0628(5) Uani 1 d . . .
C13 C 0.4380(3) 0.8244(4) 0.67838(12) 0.0770(6) Uani 1 d . . .
H13 H 0.4424 0.9283 0.7138 0.092 Uiso 1 calc . . R
C14 C 0.3508(3) 0.8727(4) 0.61130(12) 0.0747(6) Uani 1 d . . .
H14 H 0.2987 1.0086 0.6027 0.090 Uiso 1 calc . . R
C15 C 0.6055(3) 0.5686(5) 0.76834(12) 0.0867(7) Uani 1 d . . .
H15A H 0.7272 0.5793 0.7725 0.130 Uiso 1 calc . . GR
H15B H 0.5757 0.4217 0.7786 0.130 Uiso 1 calc . . GR
H15C H 0.5690 0.6671 0.8011 0.130 Uiso 1 calc . . GR
C16 C -0.0098(2) 0.6568(3) 0.12930(9) 0.0557(4) Uani 1 d . . .
C17 C 0.1378(2) 0.5432(4) 0.12374(9) 0.0624(4) Uani 1 d . . .
H17 H 0.1565 0.4039 0.1429 0.075 Uiso 1 calc . . R
C18 C 0.2563(3) 0.6372(4) 0.08982(10) 0.0664(5) Uani 1 d . . .
H18 H 0.3553 0.5608 0.0865 0.080 Uiso 1 calc . . R
C19 C 0.2303(3) 0.8439(4) 0.06058(10) 0.0629(5) Uani 1 d . . .
C20 C 0.0800(3) 0.9526(4) 0.06521(10) 0.0618(4) Uani 1 d . . .
H20 H 0.0591 1.0893 0.0443 0.074 Uiso 1 calc . . R
C21 C -0.0392(2) 0.8630(3) 0.10005(9) 0.0576(4) Uani 1 d . . .
H21 H -0.1377 0.9398 0.1038 0.069 Uiso 1 calc . . R
C22 C 0.3624(3) 0.9465(6) 0.02515(14) 0.0955(8) Uani 1 d . . .
H22A H 0.4746 0.9108 0.0509 0.143 Uiso 1 calc . . GR
H22B H 0.3479 1.1022 0.0241 0.143 Uiso 1 calc . . GR
H22C H 0.3492 0.8922 -0.0222 0.143 Uiso 1 calc . . GR
N1 N -0.0822(2) 0.6127(3) 0.26069(8) 0.0629(4) Uani 1 d . . .
O1 O -0.1380(3) 0.3111(3) 0.17618(9) 0.0877(5) Uani 1 d . . .
O2 O -0.31447(18) 0.6476(3) 0.15774(8) 0.0838(5) Uani 1 d . . .
S1 S -0.15209(6) 0.54349(9) 0.17887(2) 0.06553(15) Uani 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 0.0895(13) 0.0566(11) 0.0533(9) 0.0042(9) -0.0001(9) 0.0108(10)
C2 0.0627(9) 0.0528(10) 0.0507(9) 0.0056(8) 0.0138(7) 0.0032(8)
C3 0.0547(9) 0.0658(12) 0.0528(9) 0.0091(8) 0.0171(8) 0.0100(8)
C4 0.0678(11) 0.0740(13) 0.0576(10) 0.0055(10) 0.0133(9) 0.0177(10)
C5 0.0651(9) 0.0505(9) 0.0535(9) 0.0065(7) 0.0106(7) 0.0061(8)
C6 0.0513(9) 0.0564(10) 0.0517(9) 0.0029(7) 0.0189(7) 0.0024(7)
C7 0.0688(10) 0.0668(12) 0.0566(10) -0.0054(8) 0.0200(8) 0.0152(9)
C8 0.0733(11) 0.0681(14) 0.0610(10) 0.0014(9) 0.0205(8) 0.0258(9)
C9 0.0492(8) 0.0570(10) 0.0520(9) -0.0002(7) 0.0157(7) -0.0032(7)
C10 0.0791(12) 0.0873(15) 0.0561(10) -0.0136(11) 0.0030(9) 0.0302(13)
C11 0.0821(13) 0.0822(17) 0.0666(12) -0.0070(10) -0.0049(10) 0.0266(11)
C12 0.0551(9) 0.0758(13) 0.0553(10) 0.0007(9) 0.0049(7) -0.0110(9)
C13 0.0978(16) 0.0648(13) 0.0620(11) -0.0131(10) -0.0001(11) -0.0063(12)
C14 0.0962(15) 0.0535(12) 0.0668(12) -0.0069(9) -0.0027(11) 0.0011(10)
C15 0.0930(15) 0.0966(19) 0.0606(11) 0.0008(13) -0.0095(10) -0.0114(15)
C16 0.0625(10) 0.0574(11) 0.0429(8) -0.0003(7) 0.0000(7) 0.0021(8)
C17 0.0705(10) 0.0544(10) 0.0572(9) 0.0029(9) 0.0000(7) 0.0129(10)
C18 0.0630(10) 0.0771(13) 0.0568(10) -0.0029(9) 0.0060(8) 0.0147(9)
C19 0.0653(11) 0.0747(13) 0.0460(9) -0.0017(8) 0.0038(8) 0.0017(9)
C20 0.0757(11) 0.0573(11) 0.0486(9) 0.0055(8) 0.0026(8) 0.0045(9)
C21 0.0622(10) 0.0578(11) 0.0493(9) 0.0002(7) 0.0025(7) 0.0116(8)
C22 0.0831(15) 0.125(2) 0.0809(15) 0.0177(16) 0.0231(12) -0.0058(15)
N1 0.0671(9) 0.0690(10) 0.0508(8) 0.0069(7) 0.0073(7) 0.0007(7)
O1 0.1141(14) 0.0668(10) 0.0772(10) -0.0005(8) 0.0061(9) -0.0261(9)
O2 0.0559(7) 0.1186(14) 0.0725(9) 0.0057(9) 0.0015(6) -0.0050(8)
S1 0.0658(2) 0.0720(3) 0.0552(2) 0.0036(2) 0.00290(18) -0.0092(2)
_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(3) . ?
C1 N1 1.475(3) . ?
C2 C3 1.380(3) . ?
C2 C5 1.385(3) . ?
C3 C4 1.499(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.472(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(3) . ?
C6 C7 1.392(3) . ?
C6 C9 1.488(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C12 C13 1.373(3) . ?
C12 C15 1.506(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.388(3) . ?
C16 C21 1.384(3) . ?
C16 S1 1.7628(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C19 C20 1.388(3) . ?
C19 C22 1.500(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S1 1.6273(16) . ?
O1 S1 1.429(2) . ?
O2 S1 1.4290(17) . ?
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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.30(17) . . ?
C3 C2 C1 109.94(17) . . ?
C3 C2 C5 121.20(18) . . ?
C5 C2 C1 128.84(17) . . ?
C2 C3 C4 110.79(18) . . ?
C2 C3 C8 119.54(18) . . ?
C8 C3 C4 129.67(18) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.72(16) . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C2 C5 H5 119.9 . . ?
C2 C5 C6 120.13(17) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C9 121.51(16) . . ?
C7 C6 C5 117.24(17) . . ?
C7 C6 C9 121.18(17) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.63(18) . . ?
C8 C7 H7 118.7 . . ?
C3 C8 H8 120.4 . . ?
C7 C8 C3 119.25(18) . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C6 121.91(16) . . ?
C10 C9 C14 115.70(19) . . ?
C14 C9 C6 122.23(18) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C15 121.0(2) . . ?
C13 C12 C11 116.7(2) . . ?
C13 C12 C15 122.2(2) . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.9(2) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 119.28(15) . . ?
C21 C16 C17 120.27(18) . . ?
C21 C16 S1 120.32(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 120.95(19) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 118.32(19) . . ?
C18 C19 C22 120.4(2) . . ?
C20 C19 C22 121.3(2) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.66(19) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 118.92(18) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 S1 120.07(14) . . ?
C4 N1 C1 110.92(16) . . ?
C4 N1 S1 119.76(13) . . ?
N1 S1 C16 106.91(8) . . ?
O1 S1 C16 107.98(11) . . ?
O1 S1 N1 106.27(10) . . ?
O1 S1 O2 120.44(12) . . ?
O2 S1 C16 108.16(9) . . ?
O2 S1 N1 106.36(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
C1 C2 C3 C4 2.7(2) . . . . ?
C1 C2 C3 C8 -177.93(18) . . . . ?
C1 C2 C5 C6 178.38(19) . . . . ?
C1 N1 S1 C16 -72.23(18) . . . . ?
C1 N1 S1 O1 42.90(19) . . . . ?
C1 N1 S1 O2 172.37(16) . . . . ?
C2 C1 N1 C4 23.3(2) . . . . ?
C2 C1 N1 S1 169.99(13) . . . . ?
C2 C3 C4 N1 11.4(2) . . . . ?
C2 C3 C8 C7 -0.8(3) . . . . ?
C2 C5 C6 C7 -0.7(3) . . . . ?
C2 C5 C6 C9 176.31(16) . . . . ?
C3 C2 C5 C6 0.4(3) . . . . ?
C3 C4 N1 C1 -21.9(2) . . . . ?
C3 C4 N1 S1 -168.68(12) . . . . ?
C4 C3 C8 C7 178.4(2) . . . . ?
C4 N1 S1 C16 71.50(17) . . . . ?
C4 N1 S1 O1 -173.36(16) . . . . ?
C4 N1 S1 O2 -43.89(18) . . . . ?
C5 C2 C3 C4 -178.92(17) . . . . ?
C5 C2 C3 C8 0.4(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C9 C10 -2.7(3) . . . . ?
C5 C6 C9 C14 -177.82(19) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
C6 C9 C10 C11 -174.1(2) . . . . ?
C6 C9 C14 C13 174.0(2) . . . . ?
C7 C6 C9 C10 174.26(19) . . . . ?
C7 C6 C9 C14 -0.9(3) . . . . ?
C8 C3 C4 N1 -167.91(19) . . . . ?
C9 C6 C7 C8 -176.72(18) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C10 C11 C12 C15 176.4(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C15 C12 C13 C14 -176.4(2) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C17 C16 S1 N1 85.07(16) . . . . ?
C17 C16 S1 O1 -28.91(18) . . . . ?
C17 C16 S1 O2 -160.75(15) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C17 C18 C19 C22 178.6(2) . . . . ?
C18 C19 C20 C21 2.3(3) . . . . ?
C19 C20 C21 C16 -1.8(3) . . . . ?
C21 C16 C17 C18 0.9(3) . . . . ?
C21 C16 S1 N1 -90.81(16) . . . . ?
C21 C16 S1 O1 155.21(15) . . . . ?
C21 C16 S1 O2 23.37(18) . . . . ?
C22 C19 C20 C21 -177.5(2) . . . . ?
N1 C1 C2 C3 -15.5(2) . . . . ?
N1 C1 C2 C5 166.28(19) . . . . ?
S1 C16 C17 C18 -175.00(15) . . . . ?
S1 C16 C21 C20 176.06(14) . . . . ?
_iucr_refine_instructions_details
;
TITL 1 in P2(1)
CELL 1.54178 7.9693 6.1218 19.328 90 101.204 90
ZERR 2 0.0002 0.0002 0.0005 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O S
UNIT 44 42 2 4 2
L.S. 23
PLAN 20
SIZE 0.22 0.18 0.18
BOND $H
conf
htab
fmap 2
acta
REM
REM
REM
WGHT 0.051400 0.049300
FVAR 0.82846
C1 1 0.073728 0.510115 0.301382 11.00000 0.08948 0.05658 =
0.05328 0.00423 -0.00008 0.01079
AFIX 23
H1A 2 0.167923 0.517796 0.276351 11.00000 -1.20000
H1B 2 0.053844 0.358868 0.312403 11.00000 -1.20000
AFIX 0
C2 1 0.106470 0.650166 0.366936 11.00000 0.06267 0.05279 =
0.05067 0.00561 0.01375 0.00317
C3 1 0.012390 0.840519 0.355141 11.00000 0.05467 0.06578 =
0.05279 0.00911 0.01706 0.00996
C4 1 -0.097213 0.840936 0.282724 11.00000 0.06785 0.07403 =
0.05756 0.00549 0.01330 0.01774
AFIX 23
H4A 2 -0.214789 0.878344 0.284113 11.00000 -1.20000
H4B 2 -0.053736 0.941638 0.251681 11.00000 -1.20000
AFIX 0
C5 1 0.215218 0.611312 0.430833 11.00000 0.06509 0.05049 =
0.05351 0.00650 0.01056 0.00609
AFIX 43
H5 2 0.278033 0.482427 0.437681 11.00000 -1.20000
AFIX 0
C6 1 0.230854 0.766159 0.485326 11.00000 0.05129 0.05636 =
0.05172 0.00293 0.01890 0.00237
C7 1 0.135062 0.956846 0.471598 11.00000 0.06885 0.06679 =
0.05657 -0.00541 0.02001 0.01525
AFIX 43
H7 2 0.143903 1.061962 0.506860 11.00000 -1.20000
AFIX 0
C8 1 0.027592 0.996144 0.407816 11.00000 0.07329 0.06808 =
0.06102 0.00137 0.02048 0.02583
AFIX 43
H8 2 -0.033976 1.125880 0.400315 11.00000 -1.20000
AFIX 0
C9 1 0.338459 0.723950 0.555997 11.00000 0.04917 0.05704 =
0.05199 -0.00020 0.01571 -0.00324
C10 1 0.422666 0.527265 0.572405 11.00000 0.07912 0.08733 =
0.05612 -0.01358 0.00303 0.03021
AFIX 43
H10 2 0.420421 0.423570 0.537072 11.00000 -1.20000
AFIX 0
C11 1 0.510072 0.480690 0.639912 11.00000 0.08213 0.08219 =
0.06662 -0.00702 -0.00493 0.02658
AFIX 43
H11 2 0.564587 0.346384 0.648692 11.00000 -1.20000
AFIX 0
C12 1 0.518588 0.627377 0.694367 11.00000 0.05512 0.07577 =
0.05529 0.00071 0.00486 -0.01101
C13 1 0.438033 0.824419 0.678381 11.00000 0.09775 0.06477 =
0.06201 -0.01306 -0.00011 -0.00626
AFIX 43
H13 2 0.442414 0.928265 0.713806 11.00000 -1.20000
AFIX 0
C14 1 0.350831 0.872691 0.611295 11.00000 0.09622 0.05351 =
0.06680 -0.00693 -0.00271 0.00109
AFIX 43
H14 2 0.298743 1.008561 0.602717 11.00000 -1.20000
AFIX 0
C15 1 0.605511 0.568551 0.768342 11.00000 0.09304 0.09659 =
0.06064 0.00077 -0.00949 -0.01138
AFIX 137
H15A 2 0.727232 0.579308 0.772466 11.00000 -1.50000
H15B 2 0.575741 0.421741 0.778599 11.00000 -1.50000
H15C 2 0.568957 0.667112 0.801105 11.00000 -1.50000
AFIX 0
C16 1 -0.009778 0.656789 0.129303 11.00000 0.06249 0.05743 =
0.04289 -0.00028 0.00000 0.00214
C17 1 0.137804 0.543167 0.123737 11.00000 0.07052 0.05442 =
0.05719 0.00294 -0.00003 0.01292
AFIX 43
H17 2 0.156504 0.403866 0.142880 11.00000 -1.20000
AFIX 0
C18 1 0.256345 0.637182 0.089824 11.00000 0.06296 0.07713 =
0.05682 -0.00289 0.00597 0.01465
AFIX 43
H18 2 0.355348 0.560818 0.086497 11.00000 -1.20000
AFIX 0
C19 1 0.230324 0.843883 0.060580 11.00000 0.06531 0.07465 =
0.04596 -0.00170 0.00383 0.00173
C20 1 0.080011 0.952642 0.065212 11.00000 0.07566 0.05729 =
0.04864 0.00545 0.00262 0.00450
AFIX 43
H20 2 0.059118 1.089339 0.044323 11.00000 -1.20000
AFIX 0
C21 1 -0.039226 0.862956 0.100051 11.00000 0.06216 0.05783 =
0.04935 0.00019 0.00248 0.01157
AFIX 43
H21 2 -0.137723 0.939813 0.103802 11.00000 -1.20000
AFIX 0
C22 1 0.362390 0.946510 0.025151 11.00000 0.08313 0.12532 =
0.08086 0.01769 0.02313 -0.00577
AFIX 137
H22A 2 0.474567 0.910785 0.050884 11.00000 -1.50000
H22B 2 0.347895 1.102230 0.024094 11.00000 -1.50000
H22C 2 0.349203 0.892175 -0.022191 11.00000 -1.50000
AFIX 0
N1 3 -0.082192 0.612683 0.260688 11.00000 0.06710 0.06896 =
0.05084 0.00689 0.00734 0.00068
O1 4 -0.138020 0.311099 0.176178 11.00000 0.11412 0.06683 =
0.07723 -0.00049 0.00613 -0.02608
O2 4 -0.314474 0.647566 0.157741 11.00000 0.05588 0.11864 =
0.07251 0.00574 0.00153 -0.00503
S1 5 -0.152090 0.543488 0.178873 11.00000 0.06583 0.07195 =
0.05523 0.00363 0.00290 -0.00917
HKLF 4
REM 1 in P2(1)
REM R1 = 0.0307 for 2969 Fo > 4sig(Fo) and 0.0345 for all 3178 data
REM 237 parameters refined using 1 restraints
END
WGHT 0.0518 0.0487
REM Highest difference peak 0.086, deepest hole -0.169, 1-sigma level 0.027
Q1 1 -0.0070 0.2845 0.1247 11.00000 0.05 0.09
Q2 1 0.3933 0.8258 0.5850 11.00000 0.05 0.08
Q3 1 0.7051 0.4125 0.7713 11.00000 0.05 0.08
Q4 1 0.5208 0.7813 0.6671 11.00000 0.05 0.08
Q5 1 0.3694 0.9003 0.7287 11.00000 0.05 0.08
Q6 1 0.4988 0.5078 0.5209 11.00000 0.05 0.08
Q7 1 -0.0391 0.6301 0.1522 11.00000 0.05 0.08
Q8 1 0.0804 0.8014 0.3564 11.00000 0.05 0.08
Q9 1 -0.2739 0.2329 0.2377 11.00000 0.05 0.07
Q10 1 -0.2846 0.9806 0.1509 11.00000 0.05 0.07
Q11 1 0.3393 0.3354 0.5392 11.00000 0.05 0.07
Q12 1 0.2187 0.8974 0.4722 11.00000 0.05 0.07
Q13 1 0.4144 0.6558 0.5556 11.00000 0.05 0.07
Q14 1 -0.3650 0.8800 0.2204 11.00000 0.05 0.07
Q15 1 -0.3086 0.8233 0.1480 11.00000 0.05 0.07
Q16 1 0.6425 0.3776 0.6401 11.00000 0.05 0.07
Q17 1 0.0477 0.3165 0.2005 11.00000 0.05 0.07
Q18 1 0.5160 0.5132 0.7967 11.00000 0.05 0.07
Q19 1 -0.0008 1.2365 0.3879 11.00000 0.05 0.07
Q20 1 -0.0280 0.3077 0.3294 11.00000 0.05 0.07
REM The information below was added by Olex2.
REM
REM R1 = 0.0307 for 2969 Fo > 4sig(Fo) and 0.0345 for all 13766 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.09, deepest hole -0.17
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0345
REM R1_gt = 0.0307
REM wR_ref = 0.0845
REM GOOF = 1.040
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 13766
REM Reflections_gt = 2969
REM Parameters = n/a
REM Hole = -0.17
REM Peak = 0.09
REM Flack = -0.002(15)
;
_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_3ac
_database_code_depnum_ccdc_archive 'CCDC 1491617'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C23 H23 N O3 S'
_chemical_formula_sum 'C23 H23 N O3 S'
_chemical_formula_weight 393.48
_chemical_absolute_configuration ad
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
_chemical_oxdiff_usercomment ZYY-2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
_cell_length_a 8.4634(2)
_cell_length_b 9.3587(2)
_cell_length_c 25.6617(7)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2032.57(9)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3141
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.4470
_cell_measurement_theta_min 5.0360
_exptl_absorpt_coefficient_mu 1.601
_exptl_absorpt_correction_T_min 0.87136
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.286
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 832
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.23
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0134
_diffrn_reflns_av_unetI/netI 0.0216
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 5167
_diffrn_reflns_theta_full 73.57
_diffrn_reflns_theta_max 73.57
_diffrn_reflns_theta_min 3.44
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -114.00 -12.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -57.0000 60.0000 102
#__ type_ start__ end____ width___ exp.time_
2 omega -48.00 -12.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 -150.0000 36
#__ type_ start__ end____ width___ exp.time_
3 omega 65.00 91.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
4 omega 70.00 96.00 1.0000 16.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -60.0000 26
#__ type_ start__ end____ width___ exp.time_
5 omega 26.00 95.00 1.0000 16.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 -30.0000 69
#__ type_ start__ end____ width___ exp.time_
6 omega 51.00 78.00 1.0000 16.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 150.0000 27
#__ type_ start__ end____ width___ exp.time_
7 omega 56.00 175.00 1.0000 16.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 15.0000 120.0000 119
#__ type_ start__ end____ width___ exp.time_
8 omega 51.00 76.00 1.0000 16.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -150.0000 25
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0629723000
_diffrn_orient_matrix_UB_12 0.1043621000
_diffrn_orient_matrix_UB_13 0.0415084000
_diffrn_orient_matrix_UB_21 -0.0034959000
_diffrn_orient_matrix_UB_22 0.1206450000
_diffrn_orient_matrix_UB_23 -0.0408545000
_diffrn_orient_matrix_UB_31 -0.1707756000
_diffrn_orient_matrix_UB_32 -0.0407837000
_diffrn_orient_matrix_UB_33 -0.0144732000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 3184
_reflns_number_total 3393
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.098
_refine_diff_density_min -0.318
_refine_diff_density_rms 0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.004(18)
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.028
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 255
_refine_ls_number_reflns 3393
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0349
_refine_ls_R_factor_gt 0.0325
_refine_ls_restrained_S_all 1.028
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.1851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0859
_refine_ls_wR_factor_ref 0.0885
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C18(H18),
C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.0432(2) 0.9084(3) 0.63083(8) 0.0566(5) Uani 1 d . . .
H1A H -0.0142 1.0070 0.6241 0.068 Uiso 1 calc . . R
H1B H -0.0058 0.8487 0.6025 0.068 Uiso 1 calc . . R
C2 C 0.0194(2) 0.85796(19) 0.68279(7) 0.0477(4) Uani 1 d . . .
C3 C -0.0996(2) 0.7899(2) 0.71041(8) 0.0489(4) Uani 1 d . . .
C4 C -0.2526(2) 0.7912(2) 0.68087(8) 0.0572(5) Uani 1 d . . .
H4A H -0.2781 0.6973 0.6673 0.069 Uiso 1 calc . . R
H4B H -0.3391 0.8249 0.7024 0.069 Uiso 1 calc . . R
C5 C 0.1699(2) 0.87195(19) 0.70324(7) 0.0485(4) Uani 1 d . . .
H5 H 0.2491 0.9165 0.6841 0.058 Uiso 1 calc . . R
C6 C 0.2016(2) 0.81805(19) 0.75322(7) 0.0460(4) Uani 1 d . . .
C7 C 0.0808(2) 0.7480(2) 0.77988(8) 0.0546(4) Uani 1 d . . .
H7 H 0.1016 0.7103 0.8127 0.065 Uiso 1 calc . . R
C8 C -0.0697(2) 0.7328(2) 0.75893(8) 0.0556(5) Uani 1 d . . .
H8 H -0.1486 0.6851 0.7772 0.067 Uiso 1 calc . . R
C9 C 0.3571(2) 0.83748(19) 0.77934(7) 0.0457(4) Uani 1 d . . .
C10 C 0.4486(2) 0.9591(2) 0.77213(7) 0.0500(4) Uani 1 d . . .
H10 H 0.4149 1.0281 0.7486 0.060 Uiso 1 calc . . R
C11 C 0.5890(2) 0.9808(2) 0.79909(7) 0.0528(4) Uani 1 d . . .
H11 H 0.6483 1.0630 0.7934 0.063 Uiso 1 calc . . R
C12 C 0.6401(2) 0.8790(2) 0.83456(7) 0.0491(4) Uani 1 d . . .
C13 C 0.5521(2) 0.7550(2) 0.84159(8) 0.0515(4) Uani 1 d . . .
H13 H 0.5871 0.6852 0.8646 0.062 Uiso 1 calc . . R
C14 C 0.4135(2) 0.7354(2) 0.81459(7) 0.0496(4) Uani 1 d . . .
H14 H 0.3557 0.6522 0.8199 0.060 Uiso 1 calc . . R
C15 C 0.8695(3) 1.0131(3) 0.86019(10) 0.0711(6) Uani 1 d . . .
H15A H 0.8089 1.0985 0.8680 0.085 Uiso 1 calc . . R
H15B H 0.9117 1.0213 0.8252 0.085 Uiso 1 calc . . R
C16 C 1.0008(4) 0.9940(3) 0.89905(13) 0.0984(10) Uani 1 d . . .
H16A H 0.9576 0.9922 0.9336 0.148 Uiso 1 calc . . GR
H16B H 1.0740 1.0719 0.8961 0.148 Uiso 1 calc . . GR
H16C H 1.0547 0.9057 0.8923 0.148 Uiso 1 calc . . GR
C17 C -0.3453(2) 0.7471(2) 0.55649(7) 0.0515(4) Uani 1 d . . .
C18 C -0.2521(3) 0.7286(3) 0.51256(8) 0.0650(5) Uani 1 d . . .
H18 H -0.1887 0.8024 0.5003 0.078 Uiso 1 calc . . R
C19 C -0.2554(3) 0.5974(3) 0.48731(8) 0.0731(6) Uani 1 d . . .
H19 H -0.1945 0.5847 0.4575 0.088 Uiso 1 calc . . R
C20 C -0.3458(3) 0.4863(3) 0.50501(8) 0.0682(6) Uani 1 d . . .
C21 C -0.4393(3) 0.5087(2) 0.54902(8) 0.0666(6) Uani 1 d . . .
H21 H -0.5026 0.4349 0.5614 0.080 Uiso 1 calc . . R
C22 C -0.4393(3) 0.6377(2) 0.57423(8) 0.0582(5) Uani 1 d . . .
H22 H -0.5029 0.6512 0.6034 0.070 Uiso 1 calc . . R
C23 C -0.3474(5) 0.3428(3) 0.47779(12) 0.1104(12) Uani 1 d . . .
H23A H -0.4541 0.3177 0.4690 0.166 Uiso 1 calc . . GR
H23B H -0.3039 0.2715 0.5005 0.166 Uiso 1 calc . . GR
H23C H -0.2852 0.3482 0.4466 0.166 Uiso 1 calc . . GR
N1 N -0.2162(2) 0.8930(2) 0.63857(7) 0.0576(4) Uani 1 d . . .
O1 O 0.77253(18) 0.88844(16) 0.86477(6) 0.0632(4) Uani 1 d . . .
O2 O -0.2781(3) 1.01862(18) 0.55750(8) 0.0867(6) Uani 1 d . . .
O3 O -0.49235(19) 0.9277(2) 0.61504(7) 0.0799(5) Uani 1 d . . .
S1 S -0.34033(7) 0.91053(6) 0.59094(2) 0.06198(15) Uani 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 0.0554(10) 0.0586(11) 0.0557(10) 0.0047(9) -0.0020(9) 0.0001(10)
C2 0.0508(9) 0.0425(8) 0.0498(9) -0.0029(7) 0.0031(8) 0.0033(8)
C3 0.0431(9) 0.0502(9) 0.0533(9) -0.0061(8) 0.0036(8) 0.0005(8)
C4 0.0485(10) 0.0682(12) 0.0549(10) -0.0059(9) 0.0005(9) 0.0026(9)
C5 0.0473(9) 0.0447(8) 0.0535(9) 0.0019(7) 0.0063(8) -0.0021(8)
C6 0.0442(9) 0.0416(8) 0.0522(9) -0.0029(7) 0.0033(8) 0.0015(7)
C7 0.0511(9) 0.0604(11) 0.0523(10) 0.0073(9) 0.0019(8) -0.0030(9)
C8 0.0467(9) 0.0632(11) 0.0569(10) 0.0039(9) 0.0079(9) -0.0071(9)
C9 0.0450(8) 0.0420(8) 0.0501(8) -0.0025(7) 0.0048(8) 0.0016(7)
C10 0.0509(9) 0.0453(9) 0.0538(10) 0.0068(8) 0.0026(8) -0.0002(8)
C11 0.0536(10) 0.0463(9) 0.0583(10) 0.0051(8) 0.0045(9) -0.0103(8)
C12 0.0485(9) 0.0507(9) 0.0481(8) -0.0025(7) -0.0012(8) -0.0062(8)
C13 0.0554(10) 0.0452(9) 0.0540(10) 0.0052(8) -0.0038(9) -0.0057(8)
C14 0.0517(9) 0.0407(8) 0.0563(10) 0.0025(8) -0.0014(8) -0.0067(8)
C15 0.0665(13) 0.0630(12) 0.0838(14) 0.0041(11) -0.0125(12) -0.0232(11)
C16 0.0868(18) 0.094(2) 0.114(2) 0.0115(18) -0.0388(18) -0.0379(17)
C17 0.0523(9) 0.0552(9) 0.0471(8) -0.0002(8) -0.0028(9) 0.0084(9)
C18 0.0631(12) 0.0748(14) 0.0571(11) 0.0050(10) 0.0060(10) -0.0046(12)
C19 0.0741(14) 0.0942(17) 0.0511(10) -0.0084(12) 0.0129(11) 0.0085(15)
C20 0.0851(15) 0.0659(12) 0.0536(10) -0.0061(10) -0.0034(12) 0.0133(13)
C21 0.0839(15) 0.0594(12) 0.0567(11) 0.0014(10) 0.0020(12) -0.0049(12)
C22 0.0601(11) 0.0660(12) 0.0486(9) -0.0025(9) 0.0057(9) 0.0006(10)
C23 0.166(4) 0.0748(17) 0.0905(18) -0.0270(15) -0.006(2) 0.024(2)
N1 0.0522(8) 0.0597(10) 0.0609(9) -0.0032(8) -0.0095(8) 0.0044(8)
O1 0.0628(8) 0.0621(8) 0.0646(8) 0.0099(7) -0.0145(7) -0.0222(7)
O2 0.1092(14) 0.0584(8) 0.0925(11) 0.0168(9) -0.0316(12) -0.0025(9)
O3 0.0609(8) 0.0848(12) 0.0940(12) -0.0322(10) -0.0150(8) 0.0277(9)
S1 0.0643(3) 0.0526(2) 0.0690(3) -0.0049(2) -0.0161(3) 0.0117(2)
_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.511(3) . ?
C1 N1 1.484(3) . ?
C2 C3 1.386(3) . ?
C2 C5 1.384(3) . ?
C3 C4 1.501(3) . ?
C3 C8 1.378(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.477(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(3) . ?
C6 C7 1.393(3) . ?
C6 C9 1.488(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 C13 1.391(3) . ?
C12 O1 1.366(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.504(3) . ?
C15 O1 1.431(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.387(3) . ?
C17 C22 1.374(3) . ?
C17 S1 1.767(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 C21 1.395(3) . ?
C20 C23 1.514(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 S1 1.6201(17) . ?
O2 S1 1.4273(19) . ?
O3 S1 1.4366(18) . ?
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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.38(16) . . ?
C3 C2 C1 109.90(17) . . ?
C5 C2 C1 128.91(18) . . ?
C5 C2 C3 121.19(17) . . ?
C2 C3 C4 111.40(16) . . ?
C8 C3 C2 120.48(18) . . ?
C8 C3 C4 128.12(18) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.33(16) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.22(17) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 122.43(17) . . ?
C7 C6 C5 118.52(17) . . ?
C7 C6 C9 119.01(16) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.04(18) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 C7 118.50(19) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C6 122.22(17) . . ?
C10 C9 C14 117.07(17) . . ?
C14 C9 C6 120.63(17) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.00(18) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.53(17) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.43(18) . . ?
O1 C12 C11 125.72(17) . . ?
O1 C12 C13 114.84(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.21(18) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.73(17) . . ?
C13 C14 H14 119.1 . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.6 . . ?
C16 C15 H15B 110.6 . . ?
O1 C15 H15A 110.6 . . ?
O1 C15 H15B 110.6 . . ?
O1 C15 C16 105.8(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 120.08(17) . . ?
C22 C17 C18 120.4(2) . . ?
C22 C17 S1 119.53(15) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.9(2) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 118.2(2) . . ?
C19 C20 C23 121.7(3) . . ?
C21 C20 C23 120.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.00(19) . . ?
C21 C22 H22 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 S1 121.92(15) . . ?
C4 N1 C1 111.54(16) . . ?
C4 N1 S1 119.00(14) . . ?
C12 O1 C15 118.47(16) . . ?
N1 S1 C17 107.75(9) . . ?
O2 S1 C17 108.75(10) . . ?
O2 S1 N1 106.62(11) . . ?
O2 S1 O3 120.67(13) . . ?
O3 S1 C17 106.92(11) . . ?
O3 S1 N1 105.51(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
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C8 179.11(18) . . . . ?
C1 C2 C5 C6 179.11(19) . . . . ?
C1 N1 S1 C17 81.5(2) . . . . ?
C1 N1 S1 O2 -35.2(2) . . . . ?
C1 N1 S1 O3 -164.60(18) . . . . ?
C2 C1 N1 C4 -21.2(2) . . . . ?
C2 C1 N1 S1 -170.55(14) . . . . ?
C2 C3 C4 N1 -11.2(2) . . . . ?
C2 C3 C8 C7 1.5(3) . . . . ?
C2 C5 C6 C7 2.0(3) . . . . ?
C2 C5 C6 C9 -175.80(17) . . . . ?
C3 C2 C5 C6 -1.0(3) . . . . ?
C3 C4 N1 C1 20.4(2) . . . . ?
C3 C4 N1 S1 170.70(13) . . . . ?
C4 C3 C8 C7 -177.8(2) . . . . ?
C4 N1 S1 C17 -65.67(17) . . . . ?
C4 N1 S1 O2 177.73(16) . . . . ?
C4 N1 S1 O3 48.28(18) . . . . ?
C5 C2 C3 C4 178.62(17) . . . . ?
C5 C2 C3 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C5 C6 C9 C10 33.5(3) . . . . ?
C5 C6 C9 C14 -149.78(18) . . . . ?
C6 C7 C8 C3 -0.4(3) . . . . ?
C6 C9 C10 C11 175.91(17) . . . . ?
C6 C9 C14 C13 -175.96(17) . . . . ?
C7 C6 C9 C10 -144.31(19) . . . . ?
C7 C6 C9 C14 32.4(3) . . . . ?
C8 C3 C4 N1 168.1(2) . . . . ?
C9 C6 C7 C8 176.57(19) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C12 O1 -177.86(18) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 O1 C15 -0.1(3) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C13 C12 O1 C15 -179.64(19) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C16 C15 O1 C12 178.2(2) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
C18 C17 S1 N1 -95.49(18) . . . . ?
C18 C17 S1 O2 19.7(2) . . . . ?
C18 C17 S1 O3 151.51(18) . . . . ?
C18 C19 C20 C21 1.6(4) . . . . ?
C18 C19 C20 C23 -179.1(3) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C20 C21 C22 C17 -0.5(4) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C22 C17 S1 N1 83.04(19) . . . . ?
C22 C17 S1 O2 -161.75(17) . . . . ?
C22 C17 S1 O3 -30.0(2) . . . . ?
C23 C20 C21 C22 179.9(3) . . . . ?
N1 C1 C2 C3 13.4(2) . . . . ?
N1 C1 C2 C5 -166.67(19) . . . . ?
O1 C12 C13 C14 177.90(17) . . . . ?
S1 C17 C18 C19 178.17(18) . . . . ?
S1 C17 C22 C21 -177.42(18) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160529tjy-2_a.res in P2(1)2(1)2(1)
CELL 1.54184 8.4634 9.3587 25.6617 90 90 90
ZERR 4 0.0002 0.0002 0.0007 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O S
UNIT 92 92 4 12 4
L.S. 20
PLAN 20
SIZE 0.25 0.23 0.23
conf
htab
BOND $H
LIST 6
fmap 2
acta
REM
REM
REM
WGHT 0.049300 0.185100
FVAR 0.58091
C1 1 -0.043234 0.908439 0.630828 11.00000 0.05545 0.05859 =
0.05571 0.00466 -0.00204 0.00011
AFIX 23
H1A 2 -0.014220 1.006981 0.624067 11.00000 -1.20000
H1B 2 -0.005762 0.848731 0.602510 11.00000 -1.20000
AFIX 0
C2 1 0.019372 0.857962 0.682787 11.00000 0.05077 0.04254 =
0.04977 -0.00290 0.00311 0.00331
C3 1 -0.099556 0.789927 0.710409 11.00000 0.04307 0.05020 =
0.05332 -0.00609 0.00364 0.00055
C4 1 -0.252580 0.791205 0.680874 11.00000 0.04851 0.06824 =
0.05485 -0.00592 0.00048 0.00259
AFIX 23
H4A 2 -0.278114 0.697282 0.667287 11.00000 -1.20000
H4B 2 -0.339114 0.824894 0.702400 11.00000 -1.20000
AFIX 0
C5 1 0.169892 0.871946 0.703244 11.00000 0.04730 0.04472 =
0.05355 0.00190 0.00629 -0.00206
AFIX 43
H5 2 0.249128 0.916525 0.684108 11.00000 -1.20000
AFIX 0
C6 1 0.201557 0.818047 0.753218 11.00000 0.04422 0.04164 =
0.05223 -0.00292 0.00326 0.00151
C7 1 0.080812 0.748030 0.779880 11.00000 0.05106 0.06037 =
0.05226 0.00733 0.00195 -0.00303
AFIX 43
H7 2 0.101579 0.710333 0.812704 11.00000 -1.20000
AFIX 0
C8 1 -0.069749 0.732783 0.758928 11.00000 0.04666 0.06318 =
0.05688 0.00387 0.00791 -0.00707
AFIX 43
H8 2 -0.148570 0.685104 0.777239 11.00000 -1.20000
AFIX 0
C9 1 0.357101 0.837476 0.779335 11.00000 0.04497 0.04200 =
0.05010 -0.00252 0.00484 0.00157
C10 1 0.448597 0.959104 0.772130 11.00000 0.05090 0.04525 =
0.05383 0.00678 0.00256 -0.00021
AFIX 43
H10 2 0.414876 1.028138 0.748554 11.00000 -1.20000
AFIX 0
C11 1 0.589042 0.980776 0.799091 11.00000 0.05363 0.04634 =
0.05829 0.00513 0.00448 -0.01034
AFIX 43
H11 2 0.648333 1.062962 0.793378 11.00000 -1.20000
AFIX 0
C12 1 0.640095 0.878987 0.834561 11.00000 0.04848 0.05067 =
0.04806 -0.00254 -0.00124 -0.00616
C13 1 0.552063 0.755020 0.841589 11.00000 0.05537 0.04519 =
0.05400 0.00516 -0.00383 -0.00572
AFIX 43
H13 2 0.587052 0.685154 0.864632 11.00000 -1.20000
AFIX 0
C14 1 0.413518 0.735424 0.814588 11.00000 0.05172 0.04074 =
0.05629 0.00251 -0.00137 -0.00672
AFIX 43
H14 2 0.355734 0.652156 0.819881 11.00000 -1.20000
AFIX 0
C15 1 0.869464 1.013113 0.860190 11.00000 0.06650 0.06299 =
0.08381 0.00409 -0.01246 -0.02317
AFIX 23
H15A 2 0.808906 1.098465 0.867999 11.00000 -1.20000
H15B 2 0.911660 1.021284 0.825172 11.00000 -1.20000
AFIX 0
C16 1 1.000825 0.994001 0.899053 11.00000 0.08675 0.09407 =
0.11443 0.01153 -0.03883 -0.03791
AFIX 137
H16A 2 0.957604 0.992204 0.933634 11.00000 -1.50000
H16B 2 1.074010 1.071939 0.896051 11.00000 -1.50000
H16C 2 1.054697 0.905664 0.892276 11.00000 -1.50000
AFIX 0
C17 1 -0.345286 0.747083 0.556493 11.00000 0.05234 0.05519 =
0.04710 -0.00018 -0.00275 0.00842
C18 1 -0.252064 0.728574 0.512563 11.00000 0.06307 0.07482 =
0.05709 0.00496 0.00601 -0.00460
AFIX 43
H18 2 -0.188660 0.802425 0.500286 11.00000 -1.20000
AFIX 0
C19 1 -0.255441 0.597403 0.487307 11.00000 0.07406 0.09419 =
0.05111 -0.00841 0.01290 0.00847
AFIX 43
H19 2 -0.194544 0.584691 0.457498 11.00000 -1.20000
AFIX 0
C20 1 -0.345767 0.486330 0.505009 11.00000 0.08514 0.06588 =
0.05364 -0.00612 -0.00335 0.01332
C21 1 -0.439278 0.508686 0.549020 11.00000 0.08387 0.05941 =
0.05666 0.00139 0.00198 -0.00487
AFIX 43
H21 2 -0.502550 0.434907 0.561429 11.00000 -1.20000
AFIX 0
C22 1 -0.439300 0.637683 0.574235 11.00000 0.06008 0.06599 =
0.04856 -0.00254 0.00573 0.00059
AFIX 43
H22 2 -0.502940 0.651237 0.603362 11.00000 -1.20000
AFIX 0
C23 1 -0.347369 0.342796 0.477793 11.00000 0.16601 0.07476 =
0.09051 -0.02701 -0.00572 0.02410
AFIX 137
H23A 2 -0.454098 0.317734 0.469023 11.00000 -1.50000
H23B 2 -0.303874 0.271452 0.500525 11.00000 -1.50000
H23C 2 -0.285152 0.348193 0.446575 11.00000 -1.50000
AFIX 0
N1 3 -0.216184 0.892952 0.638569 11.00000 0.05220 0.05966 =
0.06087 -0.00319 -0.00946 0.00440
O1 4 0.772528 0.888445 0.864774 11.00000 0.06282 0.06208 =
0.06463 0.00992 -0.01454 -0.02222
O2 4 -0.278058 1.018619 0.557505 11.00000 0.10915 0.05843 =
0.09251 0.01682 -0.03157 -0.00248
O3 4 -0.492350 0.927722 0.615044 11.00000 0.06086 0.08485 =
0.09400 -0.03225 -0.01498 0.02772
S1 5 -0.340327 0.910534 0.590943 11.00000 0.06432 0.05263 =
0.06899 -0.00486 -0.01613 0.01171
HKLF 4
REM 20160529tjy-2_a.res in P2(1)2(1)2(1)
REM R1 = 0.0325 for 3184 Fo > 4sig(Fo) and 0.0349 for all 3393 data
REM 255 parameters refined using 0 restraints
END
WGHT 0.0493 0.1852
REM Highest difference peak 0.098, deepest hole -0.318, 1-sigma level 0.030
Q1 1 0.1743 0.8570 0.7311 11.00000 0.05 0.10
Q2 1 -0.1972 0.9881 0.5381 11.00000 0.05 0.10
Q3 1 -0.3357 0.8012 0.5754 11.00000 0.05 0.09
Q4 1 -0.2036 0.9193 0.5002 11.00000 0.05 0.09
Q5 1 0.3769 0.9117 0.7861 11.00000 0.05 0.09
Q6 1 -0.3787 0.2374 0.5038 11.00000 0.05 0.09
Q7 1 -0.3438 0.3974 0.4326 11.00000 0.05 0.09
Q8 1 -0.3476 0.4390 0.4231 11.00000 0.05 0.09
Q9 1 -0.1348 0.6297 0.8297 11.00000 0.05 0.09
Q10 1 -0.3429 0.5474 0.4894 11.00000 0.05 0.08
Q11 1 -0.0814 0.4971 0.4335 11.00000 0.05 0.08
Q12 1 1.0314 1.1045 0.9117 11.00000 0.05 0.08
Q13 1 0.1181 0.8178 0.7696 11.00000 0.05 0.08
Q14 1 -0.3397 0.7579 0.5334 11.00000 0.05 0.08
Q15 1 0.7201 1.0789 0.9332 11.00000 0.05 0.08
Q16 1 -0.0593 0.6149 0.4701 11.00000 0.05 0.08
Q17 1 -0.4044 0.4802 0.5193 11.00000 0.05 0.08
Q18 1 0.7850 1.1482 0.7702 11.00000 0.05 0.08
Q19 1 -0.1834 0.9200 0.5470 11.00000 0.05 0.08
Q20 1 -0.3717 0.7580 0.7123 11.00000 0.05 0.08
REM The information below was added by Olex2.
REM
REM R1 = 0.0325 for 3184 Fo > 4sig(Fo) and 0.0349 for all 5195 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.10, deepest hole -0.32
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0349
REM R1_gt = 0.0325
REM wR_ref = 0.0885
REM GOOF = 1.028
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 5195
REM Reflections_gt = 3184
REM Parameters = n/a
REM Hole = -0.32
REM Peak = 0.10
REM Flack = 0.004(18)
;
_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_3af
_database_code_depnum_ccdc_archive 'CCDC 1491619'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C21 H18 F N O2 S'
_chemical_formula_sum 'C21 H18 F N O2 S'
_chemical_formula_weight 367.42
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
_chemical_oxdiff_usercomment 1-41
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
_cell_length_a 20.5689(8)
_cell_length_b 10.9975(6)
_cell_length_c 7.9534(3)
_cell_angle_alpha 90.00
_cell_angle_beta 91.984(4)
_cell_angle_gamma 90.00
_cell_volume 1798.03(14)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2167
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.3730
_cell_measurement_theta_min 4.5630
_exptl_absorpt_coefficient_mu 1.813
_exptl_absorpt_correction_T_min 0.6702
_exptl_absorpt_correction_T_max 0.7132
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.357
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 768
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0250
_diffrn_reflns_av_unetI/netI 0.0364
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_number 6155
_diffrn_reflns_theta_full 67.07
_diffrn_reflns_theta_max 67.07
_diffrn_reflns_theta_min 4.30
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -30.00 4.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 -90.0000 34
#__ type_ start__ end____ width___ exp.time_
2 omega -42.00 34.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 30.0000 76
#__ type_ start__ end____ width___ exp.time_
3 omega -112.00 -8.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -77.0000 -60.0000 104
#__ type_ start__ end____ width___ exp.time_
4 omega 105.00 175.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 125.0000 -30.0000 70
#__ type_ start__ end____ width___ exp.time_
5 omega 90.00 159.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 45.0000 -180.0000 69
#__ type_ start__ end____ width___ exp.time_
6 omega 43.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
7 omega 37.00 95.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 30.0000 58
#__ type_ start__ end____ width___ exp.time_
8 omega 80.00 109.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -30.0000 29
#__ type_ start__ end____ width___ exp.time_
9 omega 42.00 68.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
10 omega 35.00 138.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -77.0000 -60.0000 103
#__ type_ start__ end____ width___ exp.time_
11 omega 37.00 73.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 90.0000 36
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'multiwire proportional'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_orient_matrix_UB_11 0.0650050000
_diffrn_orient_matrix_UB_12 -0.0691015000
_diffrn_orient_matrix_UB_13 -0.0061775000
_diffrn_orient_matrix_UB_21 0.0336933000
_diffrn_orient_matrix_UB_22 0.1166096000
_diffrn_orient_matrix_UB_23 -0.0593360000
_diffrn_orient_matrix_UB_31 0.0157937000
_diffrn_orient_matrix_UB_32 0.0352840000
_diffrn_orient_matrix_UB_33 0.1845481000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 2454
_reflns_number_total 3201
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max 0.205
_refine_diff_density_min -0.267
_refine_diff_density_rms 0.071
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 3201
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0603
_refine_ls_R_factor_gt 0.0414
_refine_ls_restrained_S_all 1.057
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1070
_refine_ls_wR_factor_ref 0.1312
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.29098(11) 0.7811(2) 0.2929(3) 0.0547(5) Uani 1 d . . .
H1A H 0.3067 0.8187 0.1917 0.066 Uiso 1 calc . . R
H1B H 0.3229 0.7925 0.3842 0.066 Uiso 1 calc . . R
C2 C 0.22561(10) 0.8306(2) 0.3370(3) 0.0470(5) Uani 1 d . . .
C3 C 0.18198(10) 0.7373(2) 0.3626(3) 0.0494(5) Uani 1 d . . .
C4 C 0.21311(11) 0.6162(2) 0.3360(3) 0.0570(6) Uani 1 d . . .
H4A H 0.2193 0.5722 0.4411 0.068 Uiso 1 calc . . R
H4B H 0.1876 0.5668 0.2571 0.068 Uiso 1 calc . . R
C5 C 0.20735(10) 0.9512(2) 0.3527(3) 0.0485(5) Uani 1 d . . .
H5 H 0.2371 1.0131 0.3345 0.058 Uiso 1 calc . . R
C6 C 0.14371(10) 0.9792(2) 0.3961(3) 0.0482(5) Uani 1 d . . .
C7 C 0.10051(11) 0.8838(2) 0.4238(3) 0.0572(6) Uani 1 d . . .
H7 H 0.0582 0.9016 0.4535 0.069 Uiso 1 calc . . R
C8 C 0.11912(11) 0.7633(2) 0.4082(3) 0.0595(6) Uani 1 d . . .
H8 H 0.0899 0.7009 0.4281 0.071 Uiso 1 calc . . R
C9 C 0.12308(10) 1.1078(2) 0.4099(3) 0.0493(5) Uani 1 d . . .
C10 C 0.16485(11) 1.1950(2) 0.4804(3) 0.0556(6) Uani 1 d . . .
H10 H 0.2055 1.1715 0.5238 0.067 Uiso 1 calc . . R
C11 C 0.14686(13) 1.3163(2) 0.4868(4) 0.0659(6) Uani 1 d . . .
H11 H 0.1749 1.3743 0.5338 0.079 Uiso 1 calc . . R
C12 C 0.08702(13) 1.3487(2) 0.4226(4) 0.0671(7) Uani 1 d . . .
C13 C 0.04343(12) 1.2664(3) 0.3557(4) 0.0668(7) Uani 1 d . . .
H13 H 0.0025 1.2912 0.3156 0.080 Uiso 1 calc . . R
C14 C 0.06171(11) 1.1460(2) 0.3493(3) 0.0580(6) Uani 1 d . . .
H14 H 0.0327 1.0889 0.3039 0.070 Uiso 1 calc . . R
C15 C 0.36275(10) 0.5046(2) 0.4407(3) 0.0542(5) Uani 1 d . . .
C16 C 0.41448(12) 0.5651(3) 0.5194(3) 0.0629(6) Uani 1 d . . .
H16 H 0.4322 0.6338 0.4705 0.076 Uiso 1 calc . . R
C17 C 0.43946(12) 0.5216(3) 0.6718(4) 0.0680(7) Uani 1 d . . .
H17 H 0.4742 0.5622 0.7245 0.082 Uiso 1 calc . . R
C18 C 0.41442(12) 0.4202(3) 0.7478(3) 0.0639(6) Uani 1 d . . .
C19 C 0.36137(13) 0.3637(3) 0.6694(4) 0.0688(7) Uani 1 d . . .
H19 H 0.3426 0.2969 0.7205 0.083 Uiso 1 calc . . R
C20 C 0.33559(12) 0.4047(3) 0.5164(4) 0.0650(6) Uani 1 d . . .
H20 H 0.3002 0.3652 0.4650 0.078 Uiso 1 calc . . R
C21 C 0.44499(16) 0.3690(4) 0.9081(4) 0.0866(9) Uani 1 d . . .
H21A H 0.4908 0.3858 0.9118 0.130 Uiso 1 calc . . GR
H21B H 0.4382 0.2827 0.9112 0.130 Uiso 1 calc . . GR
H21C H 0.4254 0.4060 1.0033 0.130 Uiso 1 calc . . GR
F1 F 0.06940(10) 1.46814(16) 0.4270(3) 0.1018(7) Uani 1 d . . .
N1 N 0.27613(9) 0.65179(19) 0.2660(3) 0.0579(5) Uani 1 d . . .
O1 O 0.38394(9) 0.6149(2) 0.1590(2) 0.0743(5) Uani 1 d . . .
O2 O 0.30241(10) 0.44774(18) 0.1641(3) 0.0762(6) Uani 1 d . . .
S1 S 0.33262(3) 0.55225(6) 0.24089(8) 0.0592(2) Uani 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 0.0470(11) 0.0550(14) 0.0624(12) 0.0014(11) 0.0082(9) 0.0028(10)
C2 0.0420(10) 0.0511(13) 0.0480(10) 0.0032(9) 0.0026(8) -0.0006(9)
C3 0.0468(11) 0.0479(12) 0.0535(11) -0.0013(10) 0.0000(9) -0.0004(9)
C4 0.0494(11) 0.0513(13) 0.0702(14) -0.0019(11) 0.0019(10) -0.0004(10)
C5 0.0447(10) 0.0479(12) 0.0531(11) 0.0038(9) 0.0032(9) -0.0029(9)
C6 0.0445(10) 0.0481(12) 0.0518(11) 0.0013(9) 0.0008(9) -0.0011(9)
C7 0.0419(10) 0.0549(14) 0.0753(15) -0.0027(12) 0.0090(10) -0.0014(10)
C8 0.0455(11) 0.0531(14) 0.0804(15) -0.0017(12) 0.0085(10) -0.0066(10)
C9 0.0447(10) 0.0520(13) 0.0515(11) 0.0030(9) 0.0046(9) 0.0024(9)
C10 0.0489(11) 0.0525(14) 0.0655(13) 0.0004(11) 0.0013(10) -0.0001(10)
C11 0.0654(14) 0.0498(14) 0.0827(16) -0.0032(13) 0.0080(12) -0.0057(11)
C12 0.0672(15) 0.0457(14) 0.0896(18) 0.0061(13) 0.0187(13) 0.0088(12)
C13 0.0531(12) 0.0671(17) 0.0803(16) 0.0103(14) 0.0050(11) 0.0127(12)
C14 0.0444(11) 0.0619(15) 0.0676(13) 0.0000(12) 0.0017(10) 0.0014(10)
C15 0.0446(11) 0.0539(13) 0.0644(13) -0.0077(11) 0.0032(10) 0.0083(10)
C16 0.0510(12) 0.0644(16) 0.0735(15) 0.0020(13) 0.0032(11) -0.0059(11)
C17 0.0509(12) 0.0799(19) 0.0729(15) -0.0037(14) -0.0052(11) -0.0050(12)
C18 0.0530(12) 0.0712(17) 0.0678(14) 0.0009(13) 0.0087(11) 0.0093(12)
C19 0.0660(15) 0.0617(16) 0.0793(17) 0.0049(13) 0.0100(13) 0.0002(12)
C20 0.0517(12) 0.0591(16) 0.0840(17) -0.0070(13) 0.0011(12) -0.0035(11)
C21 0.0778(18) 0.107(3) 0.0751(18) 0.0100(17) 0.0025(15) 0.0100(18)
F1 0.0941(13) 0.0512(10) 0.161(2) 0.0066(11) 0.0185(13) 0.0176(9)
N1 0.0460(9) 0.0529(12) 0.0749(12) -0.0026(10) 0.0047(9) 0.0077(8)
O1 0.0622(10) 0.0892(14) 0.0727(11) 0.0031(10) 0.0194(9) 0.0156(10)
O2 0.0787(12) 0.0677(12) 0.0810(12) -0.0245(10) -0.0154(10) 0.0162(9)
S1 0.0538(3) 0.0614(4) 0.0625(3) -0.0088(3) 0.0019(2) 0.0129(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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.503(3) . ?
C1 N1 1.469(3) . ?
C2 C3 1.383(3) . ?
C2 C5 1.385(3) . ?
C3 C4 1.496(3) . ?
C3 C8 1.385(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.481(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C6 C7 1.397(3) . ?
C6 C9 1.483(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(3) . ?
C9 C14 1.400(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(4) . ?
C12 C13 1.368(4) . ?
C12 F1 1.364(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 C20 1.380(4) . ?
C15 S1 1.765(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(4) . ?
C18 C19 1.385(4) . ?
C18 C21 1.511(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6137(19) . ?
O1 S1 1.436(2) . ?
O2 S1 1.433(2) . ?
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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
N1 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
N1 C1 C2 101.63(18) . . ?
C3 C2 C1 110.8(2) . . ?
C3 C2 C5 121.2(2) . . ?
C5 C2 C1 128.0(2) . . ?
C2 C3 C4 110.92(19) . . ?
C2 C3 C8 120.1(2) . . ?
C8 C3 C4 129.0(2) . . ?
C3 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.65(19) . . ?
N1 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C2 C5 H5 120.3 . . ?
C2 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C9 120.0(2) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 C9 121.30(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 118.9(2) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C6 120.86(19) . . ?
C10 C9 C14 118.0(2) . . ?
C14 C9 C6 121.2(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 123.0(2) . . ?
C11 C12 F1 118.6(3) . . ?
F1 C12 C13 118.4(2) . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.3(2) . . ?
C14 C13 H13 120.9 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 S1 120.3(2) . . ?
C20 C15 C16 120.1(2) . . ?
C20 C15 S1 119.61(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C21 121.4(3) . . ?
C19 C18 C21 120.8(3) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 119.6(2) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 112.44(19) . . ?
C1 N1 S1 121.86(15) . . ?
C4 N1 S1 120.68(17) . . ?
N1 S1 C15 108.79(11) . . ?
O1 S1 C15 108.07(12) . . ?
O1 S1 N1 105.92(12) . . ?
O2 S1 C15 106.20(12) . . ?
O2 S1 N1 107.06(11) . . ?
O2 S1 O1 120.42(13) . . ?
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
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C8 178.6(2) . . . . ?
C1 C2 C5 C6 -179.6(2) . . . . ?
C1 N1 S1 C15 84.4(2) . . . . ?
C1 N1 S1 O1 -31.6(2) . . . . ?
C1 N1 S1 O2 -161.2(2) . . . . ?
C2 C1 N1 C4 -16.0(2) . . . . ?
C2 C1 N1 S1 -171.03(16) . . . . ?
C2 C3 C4 N1 -8.7(2) . . . . ?
C2 C3 C8 C7 1.5(4) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -178.77(19) . . . . ?
C3 C2 C5 C6 0.4(3) . . . . ?
C3 C4 N1 C1 15.6(2) . . . . ?
C3 C4 N1 S1 170.96(16) . . . . ?
C4 C3 C8 C7 -179.2(2) . . . . ?
C4 N1 S1 C15 -68.6(2) . . . . ?
C4 N1 S1 O1 175.41(18) . . . . ?
C4 N1 S1 O2 45.7(2) . . . . ?
C5 C2 C3 C4 179.2(2) . . . . ?
C5 C2 C3 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C5 C6 C9 C10 -39.2(3) . . . . ?
C5 C6 C9 C14 139.3(2) . . . . ?
C6 C7 C8 C3 -0.6(4) . . . . ?
C6 C9 C10 C11 177.1(2) . . . . ?
C6 C9 C14 C13 -177.3(2) . . . . ?
C7 C6 C9 C10 141.5(2) . . . . ?
C7 C6 C9 C14 -40.0(3) . . . . ?
C8 C3 C4 N1 172.0(2) . . . . ?
C9 C6 C7 C8 178.9(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
C10 C11 C12 C13 1.5(5) . . . . ?
C10 C11 C12 F1 -179.3(3) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C15 C20 C19 -1.5(4) . . . . ?
C16 C15 S1 N1 -90.1(2) . . . . ?
C16 C15 S1 O1 24.5(2) . . . . ?
C16 C15 S1 O2 155.0(2) . . . . ?
C16 C17 C18 C19 -2.0(4) . . . . ?
C16 C17 C18 C21 175.9(3) . . . . ?
C17 C18 C19 C20 2.4(4) . . . . ?
C18 C19 C20 C15 -0.6(4) . . . . ?
C20 C15 C16 C17 1.9(4) . . . . ?
C20 C15 S1 N1 91.6(2) . . . . ?
C20 C15 S1 O1 -153.8(2) . . . . ?
C20 C15 S1 O2 -23.3(2) . . . . ?
C21 C18 C19 C20 -175.5(3) . . . . ?
F1 C12 C13 C14 179.1(3) . . . . ?
N1 C1 C2 C3 10.0(2) . . . . ?
N1 C1 C2 C5 -170.0(2) . . . . ?
S1 C15 C16 C17 -176.5(2) . . . . ?
S1 C15 C20 C19 176.8(2) . . . . ?
_iucr_refine_instructions_details
;
TITL 1 in P2(1)/c
CELL 1.54178 20.5689 10.9975 7.9534 90 91.984 90
ZERR 4 0.0008 0.0006 0.0003 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S F
UNIT 84 72 4 8 4 4
L.S. 32
PLAN 20
SIZE 0.24 0.2 0.2
BOND $H
CONF
HTAB
fmap 2
acta
REM
REM
REM
WGHT 0.067600
FVAR 0.40925
C1 1 0.290983 0.781133 0.292891 11.00000 0.04703 0.05497 =
0.06241 0.00136 0.00820 0.00283
AFIX 23
H1A 2 0.306694 0.818744 0.191728 11.00000 -1.20000
H1B 2 0.322877 0.792484 0.384248 11.00000 -1.20000
AFIX 0
C2 1 0.225613 0.830639 0.337034 11.00000 0.04197 0.05110 =
0.04804 0.00319 0.00255 -0.00062
C3 1 0.181984 0.737283 0.362594 11.00000 0.04676 0.04788 =
0.05348 -0.00125 0.00005 -0.00040
C4 1 0.213107 0.616154 0.335987 11.00000 0.04939 0.05131 =
0.07020 -0.00189 0.00187 -0.00044
AFIX 23
H4A 2 0.219282 0.572217 0.441080 11.00000 -1.20000
H4B 2 0.187610 0.566776 0.257089 11.00000 -1.20000
AFIX 0
C5 1 0.207354 0.951233 0.352678 11.00000 0.04467 0.04790 =
0.05306 0.00377 0.00316 -0.00291
AFIX 43
H5 2 0.237124 1.013098 0.334487 11.00000 -1.20000
AFIX 0
C6 1 0.143710 0.979150 0.396103 11.00000 0.04450 0.04810 =
0.05183 0.00128 0.00084 -0.00111
C7 1 0.100506 0.883792 0.423818 11.00000 0.04185 0.05492 =
0.07527 -0.00272 0.00901 -0.00145
AFIX 43
H7 2 0.058212 0.901598 0.453457 11.00000 -1.20000
AFIX 0
C8 1 0.119123 0.763268 0.408229 11.00000 0.04551 0.05314 =
0.08039 -0.00170 0.00850 -0.00656
AFIX 43
H8 2 0.089859 0.700862 0.428103 11.00000 -1.20000
AFIX 0
C9 1 0.123075 1.107850 0.409947 11.00000 0.04471 0.05199 =
0.05154 0.00304 0.00465 0.00235
C10 1 0.164854 1.195033 0.480361 11.00000 0.04889 0.05252 =
0.06547 0.00037 0.00130 -0.00008
AFIX 43
H10 2 0.205491 1.171497 0.523775 11.00000 -1.20000
AFIX 0
C11 1 0.146857 1.316314 0.486795 11.00000 0.06543 0.04975 =
0.08274 -0.00321 0.00802 -0.00567
AFIX 43
H11 2 0.174937 1.374289 0.533795 11.00000 -1.20000
AFIX 0
C12 1 0.087022 1.348653 0.422611 11.00000 0.06724 0.04567 =
0.08957 0.00610 0.01866 0.00880
C13 1 0.043426 1.266428 0.355708 11.00000 0.05311 0.06712 =
0.08032 0.01028 0.00500 0.01273
AFIX 43
H13 2 0.002528 1.291158 0.315581 11.00000 -1.20000
AFIX 0
C14 1 0.061707 1.145983 0.349333 11.00000 0.04443 0.06190 =
0.06757 -0.00005 0.00171 0.00136
AFIX 43
H14 2 0.032709 1.088949 0.303885 11.00000 -1.20000
AFIX 0
C15 1 0.362750 0.504574 0.440700 11.00000 0.04456 0.05385 =
0.06436 -0.00770 0.00320 0.00831
C16 1 0.414479 0.565067 0.519369 11.00000 0.05101 0.06436 =
0.07348 0.00202 0.00316 -0.00592
AFIX 43
H16 2 0.432170 0.633835 0.470550 11.00000 -1.20000
AFIX 0
C17 1 0.439459 0.521605 0.671814 11.00000 0.05087 0.07985 =
0.07287 -0.00368 -0.00523 -0.00496
AFIX 43
H17 2 0.474214 0.562188 0.724471 11.00000 -1.20000
AFIX 0
C18 1 0.414418 0.420170 0.747779 11.00000 0.05296 0.07121 =
0.06785 0.00086 0.00870 0.00933
C19 1 0.361368 0.363728 0.669357 11.00000 0.06597 0.06167 =
0.07930 0.00487 0.00998 0.00023
AFIX 43
H19 2 0.342640 0.296882 0.720469 11.00000 -1.20000
AFIX 0
C20 1 0.335590 0.404717 0.516354 11.00000 0.05171 0.05913 =
0.08405 -0.00699 0.00112 -0.00348
AFIX 43
H20 2 0.300212 0.365169 0.465006 11.00000 -1.20000
AFIX 0
C21 1 0.444987 0.368975 0.908130 11.00000 0.07779 0.10694 =
0.07509 0.01002 0.00252 0.01001
AFIX 137
H21A 2 0.490813 0.385790 0.911802 11.00000 -1.50000
H21B 2 0.438194 0.282652 0.911212 11.00000 -1.50000
H21C 2 0.425376 0.405958 1.003250 11.00000 -1.50000
AFIX 0
F1 6 0.069400 1.468138 0.427040 11.00000 0.09409 0.05120 =
0.16096 0.00665 0.01852 0.01761
N1 3 0.276131 0.651790 0.265976 11.00000 0.04596 0.05293 =
0.07488 -0.00265 0.00470 0.00768
O1 4 0.383937 0.614918 0.158993 11.00000 0.06216 0.08923 =
0.07274 0.00312 0.01945 0.01559
O2 4 0.302412 0.447740 0.164094 11.00000 0.07865 0.06774 =
0.08103 -0.02455 -0.01538 0.01623
S1 5 0.332615 0.552250 0.240895 11.00000 0.05383 0.06140 =
0.06246 -0.00879 0.00189 0.01291
HKLF 4
REM 1 in P2(1)/c
REM R1 = 0.0414 for 2454 Fo > 4sig(Fo) and 0.0603 for all 3201 data
REM 236 parameters refined using 0 restraints
END
WGHT 0.0669 0.0000
REM Highest difference peak 0.205, deepest hole -0.267, 1-sigma level 0.071
Q1 1 0.3540 0.5264 0.3762 11.00000 0.05 0.21
Q2 1 0.0379 1.0813 0.2140 11.00000 0.05 0.19
Q3 1 0.0228 1.0381 0.3161 11.00000 0.05 0.18
Q4 1 0.4735 0.2942 0.8556 11.00000 0.05 0.18
Q5 1 0.4654 0.4578 1.0058 11.00000 0.05 0.17
Q6 1 0.4938 0.7478 0.3416 11.00000 0.05 0.17
Q7 1 0.5286 0.5375 0.6065 11.00000 0.05 0.17
Q8 1 0.5039 0.3160 0.8451 11.00000 0.05 0.17
Q9 1 0.4961 0.5906 0.7496 11.00000 0.05 0.17
Q10 1 0.0909 1.1249 0.3995 11.00000 0.05 0.17
Q11 1 0.0004 1.2800 0.2056 11.00000 0.05 0.17
Q12 1 0.4139 0.3329 0.9549 11.00000 0.05 0.17
Q13 1 -0.0026 1.4901 0.4033 11.00000 0.05 0.16
Q14 1 0.4704 0.5609 0.8349 11.00000 0.05 0.15
Q15 1 0.0357 1.3169 0.1038 11.00000 0.05 0.15
Q16 1 -0.0053 1.4383 0.2483 11.00000 0.05 0.15
Q17 1 -0.0022 0.9380 0.3082 11.00000 0.05 0.15
Q18 1 0.5134 0.4254 0.7049 11.00000 0.05 0.15
Q19 1 0.4509 0.5599 0.2425 11.00000 0.05 0.15
Q20 1 -0.0286 1.4132 0.3299 11.00000 0.05 0.15
REM The information below was added by Olex2.
REM
REM R1 = 0.0414 for 2454 Fo > 4sig(Fo) and 0.0603 for all 6402 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.21, deepest hole -0.27
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0603
REM R1_gt = 0.0414
REM wR_ref = 0.1312
REM GOOF = 1.057
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 6402
REM Reflections_gt = 2454
REM Parameters = n/a
REM Hole = -0.27
REM Peak = 0.21
REM Flack = n/a
;
_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_3ba
_database_code_depnum_ccdc_archive 'CCDC 1491622'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C20 H16 Cl N O2 S'
_chemical_formula_sum 'C20 H16 Cl N O2 S'
_chemical_formula_weight 369.85
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
_chemical_oxdiff_usercomment 1-95
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a 7.5142(2)
_cell_length_b 12.7251(4)
_cell_length_c 18.0220(5)
_cell_angle_alpha 88.481(2)
_cell_angle_beta 84.657(2)
_cell_angle_gamma 89.958(2)
_cell_volume 1715.15(9)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6983
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.6600
_cell_measurement_theta_min 4.9200
_exptl_absorpt_coefficient_mu 3.218
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.57132
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.432
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 768
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0330
_diffrn_reflns_av_unetI/netI 0.0429
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 11482
_diffrn_reflns_theta_full 73.78
_diffrn_reflns_theta_max 73.78
_diffrn_reflns_theta_min 3.47
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -35.00 15.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 -60.0000 50
#__ type_ start__ end____ width___ exp.time_
2 omega -48.00 33.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 0.0000 81
#__ type_ start__ end____ width___ exp.time_
3 omega 39.00 81.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -99.0000 -30.0000 42
#__ type_ start__ end____ width___ exp.time_
4 omega 72.00 97.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 0.0000 25
#__ type_ start__ end____ width___ exp.time_
5 omega 42.00 98.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 60.0000 56
#__ type_ start__ end____ width___ exp.time_
6 omega 57.00 90.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -30.0000 33
#__ type_ start__ end____ width___ exp.time_
7 omega 49.00 84.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -30.0000 35
#__ type_ start__ end____ width___ exp.time_
8 omega 52.00 102.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 -30.0000 50
#__ type_ start__ end____ width___ exp.time_
9 omega 90.00 120.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -60.0000 30
#__ type_ start__ end____ width___ exp.time_
10 omega 41.00 108.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 90.0000 67
#__ type_ start__ end____ width___ exp.time_
11 omega 52.00 136.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -77.0000 150.0000 84
#__ type_ start__ end____ width___ exp.time_
12 omega 56.00 160.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 15.0000 150.0000 104
#__ type_ start__ end____ width___ exp.time_
13 omega 94.00 131.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 125.0000 0.0000 37
#__ type_ start__ end____ width___ exp.time_
14 omega 83.00 109.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 45.0000 0.0000 26
#__ type_ start__ end____ width___ exp.time_
15 omega 130.00 162.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 45.0000 0.0000 32
#__ type_ start__ end____ width___ exp.time_
16 omega 39.00 68.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -60.0000 29
#__ type_ start__ end____ width___ exp.time_
17 omega 37.00 88.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -120.0000 51
#__ type_ start__ end____ width___ exp.time_
18 omega 35.00 84.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 -180.0000 49
#__ type_ start__ end____ width___ exp.time_
19 omega 32.00 90.00 1.0000 2.4200
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 120.0000 58
#__ type_ start__ end____ width___ exp.time_
20 omega -68.00 29.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 57.0000 -150.0000 97
#__ type_ start__ end____ width___ exp.time_
21 omega -111.00 -21.00 1.0000 1.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 -57.0000 60.0000 90
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0722086000
_diffrn_orient_matrix_UB_12 0.0554796000
_diffrn_orient_matrix_UB_13 0.0660098000
_diffrn_orient_matrix_UB_21 0.0292259000
_diffrn_orient_matrix_UB_22 -0.1075667000
_diffrn_orient_matrix_UB_23 0.0381914000
_diffrn_orient_matrix_UB_31 0.1906102000
_diffrn_orient_matrix_UB_32 -0.0042970000
_diffrn_orient_matrix_UB_33 -0.0395026000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 5953
_reflns_number_total 6691
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.248
_refine_diff_density_min -0.616
_refine_diff_density_rms 0.098
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 451
_refine_ls_number_reflns 6691
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0506
_refine_ls_R_factor_gt 0.0465
_refine_ls_restrained_S_all 1.045
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+0.2538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1196
_refine_ls_wR_factor_ref 0.1257
_refine_special_details
;
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^ > 2sigma(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.
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B), C21(H21A,H21B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
C16(H16), C17(H17), C18(H18), C19(H19), C25(H25), C27(H27), C28(H28), C30(H30),
C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.6648(3) 0.29632(15) 0.30697(10) 0.0432(4) Uani 1 d . . .
H1A H 0.7626 0.2486 0.2936 0.052 Uiso 1 calc . . R
H1B H 0.5541 0.2567 0.3152 0.052 Uiso 1 calc . . R
C2 C 0.6985(2) 0.35864(15) 0.37418(10) 0.0386(4) Uani 1 d . . .
C3 C 0.7394(3) 0.46172(16) 0.35313(11) 0.0448(4) Uani 1 d . . .
C4 C 0.7368(3) 0.47894(17) 0.27087(12) 0.0526(5) Uani 1 d . . .
H4A H 0.6657 0.5399 0.2593 0.063 Uiso 1 calc . . R
H4B H 0.8566 0.4873 0.2463 0.063 Uiso 1 calc . . R
C5 C 0.6984(3) 0.32422(15) 0.44780(10) 0.0405(4) Uani 1 d . . .
H5 H 0.6702 0.2548 0.4614 0.049 Uiso 1 calc . . R
C6 C 0.7413(3) 0.39533(16) 0.50145(11) 0.0441(4) Uani 1 d . . .
C7 C 0.7815(4) 0.49891(18) 0.47912(13) 0.0585(6) Uani 1 d . . .
H7 H 0.8081 0.5466 0.5147 0.070 Uiso 1 calc . . R
C8 C 0.7828(4) 0.53303(17) 0.40512(13) 0.0597(6) Uani 1 d . . .
H8 H 0.8122 0.6021 0.3910 0.072 Uiso 1 calc . . R
C9 C 0.7546(3) 0.36130(17) 0.58063(11) 0.0455(4) Uani 1 d . . .
C10 C 0.8263(3) 0.26440(18) 0.59843(12) 0.0512(5) Uani 1 d . . .
H10 H 0.8581 0.2175 0.5608 0.061 Uiso 1 calc . . R
C11 C 0.8512(3) 0.2366(2) 0.67201(14) 0.0616(6) Uani 1 d . . .
H11 H 0.8998 0.1714 0.6830 0.074 Uiso 1 calc . . R
C12 C 0.8045(3) 0.3049(2) 0.72874(13) 0.0659(7) Uani 1 d . . .
H12 H 0.8226 0.2863 0.7777 0.079 Uiso 1 calc . . R
C13 C 0.7310(4) 0.4008(2) 0.71211(13) 0.0665(7) Uani 1 d . . .
H13 H 0.6981 0.4470 0.7501 0.080 Uiso 1 calc . . R
C14 C 0.7056(3) 0.4291(2) 0.63875(13) 0.0566(5) Uani 1 d . . .
H14 H 0.6554 0.4940 0.6282 0.068 Uiso 1 calc . . R
C15 C 0.8586(2) 0.31111(14) 0.12560(9) 0.0342(3) Uani 1 d . . .
C16 C 0.8863(3) 0.20349(15) 0.11868(10) 0.0404(4) Uani 1 d . . .
H16 H 0.7937 0.1571 0.1339 0.049 Uiso 1 calc . . R
C17 C 1.0492(3) 0.16442(16) 0.08953(11) 0.0486(5) Uani 1 d . . .
H17 H 1.0657 0.0923 0.0851 0.058 Uiso 1 calc . . R
C18 C 1.1870(3) 0.23299(17) 0.06704(11) 0.0489(5) Uani 1 d . . .
H18 H 1.2971 0.2069 0.0481 0.059 Uiso 1 calc . . R
C19 C 1.1622(3) 0.34019(17) 0.07255(11) 0.0479(4) Uani 1 d . . .
H19 H 1.2556 0.3859 0.0570 0.058 Uiso 1 calc . . R
C20 C 0.9987(3) 0.37996(15) 0.10111(10) 0.0396(4) Uani 1 d . . .
C21 C 0.6619(3) 0.80677(17) 0.29568(11) 0.0504(5) Uani 1 d . . .
H21A H 0.7355 0.7442 0.2916 0.060 Uiso 1 calc . . R
H21B H 0.5370 0.7867 0.2975 0.060 Uiso 1 calc . . R
C22 C 0.6983(2) 0.86856(15) 0.36254(10) 0.0390(4) Uani 1 d . . .
C23 C 0.7555(3) 0.96916(15) 0.34105(11) 0.0409(4) Uani 1 d . . .
C24 C 0.7629(3) 0.98670(15) 0.25844(11) 0.0483(5) Uani 1 d . . .
H24A H 0.6794 1.0407 0.2452 0.058 Uiso 1 calc . . R
H24B H 0.8823 1.0059 0.2374 0.058 Uiso 1 calc . . R
C25 C 0.6890(3) 0.83456(15) 0.43646(11) 0.0414(4) Uani 1 d . . .
H25 H 0.6496 0.7669 0.4501 0.050 Uiso 1 calc . . R
C26 C 0.7392(3) 0.90283(16) 0.49025(11) 0.0419(4) Uani 1 d . . .
C27 C 0.7933(3) 1.00501(16) 0.46796(12) 0.0492(5) Uani 1 d . . .
H27 H 0.8237 1.0515 0.5037 0.059 Uiso 1 calc . . R
C28 C 0.8026(3) 1.03874(15) 0.39384(12) 0.0487(5) Uani 1 d . . .
H28 H 0.8396 1.1067 0.3799 0.058 Uiso 1 calc . . R
C29 C 0.7513(3) 0.86604(18) 0.56874(11) 0.0465(4) Uani 1 d . . .
C30 C 0.8167(3) 0.76640(19) 0.58425(12) 0.0531(5) Uani 1 d . . .
H30 H 0.8453 0.7210 0.5453 0.064 Uiso 1 calc . . R
C31 C 0.8404(4) 0.7331(3) 0.65708(15) 0.0684(7) Uani 1 d . . .
H31 H 0.8830 0.6659 0.6664 0.082 Uiso 1 calc . . R
C32 C 0.8004(4) 0.8000(3) 0.71502(14) 0.0774(9) Uani 1 d . . .
H32 H 0.8170 0.7785 0.7636 0.093 Uiso 1 calc . . R
C33 C 0.7360(4) 0.8988(3) 0.70073(14) 0.0786(9) Uani 1 d . . .
H33 H 0.7092 0.9440 0.7399 0.094 Uiso 1 calc . . R
C34 C 0.7102(3) 0.9321(2) 0.62832(13) 0.0615(6) Uani 1 d . . .
H34 H 0.6652 0.9990 0.6197 0.074 Uiso 1 calc . . R
C35 C 0.5748(2) 0.80430(14) 0.11423(9) 0.0338(3) Uani 1 d . . .
C36 C 0.5487(3) 0.69849(15) 0.10179(10) 0.0406(4) Uani 1 d . . .
H36 H 0.6337 0.6493 0.1138 0.049 Uiso 1 calc . . R
C37 C 0.3950(3) 0.66617(17) 0.07127(11) 0.0477(4) Uani 1 d . . .
H37 H 0.3777 0.5954 0.0625 0.057 Uiso 1 calc . . R
C38 C 0.2687(3) 0.73872(18) 0.05405(11) 0.0492(5) Uani 1 d . . .
H38 H 0.1657 0.7165 0.0341 0.059 Uiso 1 calc . . R
C39 C 0.2932(3) 0.84451(18) 0.06605(11) 0.0472(5) Uani 1 d . . .
H39 H 0.2074 0.8931 0.0539 0.057 Uiso 1 calc . . R
C40 C 0.4463(3) 0.87783(15) 0.09625(10) 0.0382(4) Uani 1 d . . .
Cl1 Cl 0.97818(8) 0.51569(4) 0.10385(3) 0.05965(17) Uani 1 d . . .
Cl2 Cl 0.46957(8) 1.01089(4) 0.11102(3) 0.05428(15) Uani 1 d . . .
N1 N 0.6532(2) 0.38079(13) 0.24965(9) 0.0425(4) Uani 1 d . . .
N2 N 0.7105(3) 0.88243(13) 0.23389(9) 0.0470(4) Uani 1 d . . .
O1 O 0.5326(2) 0.25825(12) 0.16475(8) 0.0501(3) Uani 1 d . . .
O2 O 0.5912(2) 0.44381(12) 0.12460(8) 0.0530(4) Uani 1 d . . .
O3 O 0.8732(2) 0.74469(13) 0.15849(10) 0.0582(4) Uani 1 d . . .
O4 O 0.8576(2) 0.92683(12) 0.10938(9) 0.0527(4) Uani 1 d . . .
S1 S 0.64178(6) 0.35067(4) 0.16317(2) 0.03839(12) Uani 1 d . . .
S2 S 0.77497(6) 0.84016(4) 0.15174(2) 0.04003(13) Uani 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 0.0537(11) 0.0390(10) 0.0375(9) -0.0014(7) -0.0074(8) -0.0039(8)
C2 0.0390(9) 0.0395(9) 0.0374(9) -0.0052(7) -0.0042(7) 0.0016(7)
C3 0.0537(11) 0.0380(10) 0.0431(10) -0.0033(8) -0.0073(8) 0.0004(8)
C4 0.0722(14) 0.0427(11) 0.0432(10) -0.0004(8) -0.0076(10) -0.0068(10)
C5 0.0441(10) 0.0379(9) 0.0397(9) -0.0039(7) -0.0043(7) -0.0002(7)
C6 0.0485(10) 0.0449(10) 0.0400(9) -0.0076(8) -0.0078(8) 0.0042(8)
C7 0.0852(17) 0.0443(11) 0.0492(11) -0.0120(9) -0.0203(11) -0.0014(11)
C8 0.0900(18) 0.0364(10) 0.0547(12) -0.0050(9) -0.0167(12) -0.0038(11)
C9 0.0443(10) 0.0528(11) 0.0404(9) -0.0074(8) -0.0080(8) 0.0009(8)
C10 0.0537(12) 0.0555(12) 0.0451(10) -0.0046(9) -0.0073(9) 0.0054(9)
C11 0.0555(13) 0.0745(16) 0.0550(13) 0.0105(11) -0.0102(10) 0.0089(11)
C12 0.0553(13) 0.103(2) 0.0404(11) 0.0020(12) -0.0127(9) 0.0005(13)
C13 0.0681(15) 0.0906(19) 0.0425(11) -0.0181(12) -0.0086(10) 0.0055(14)
C14 0.0615(13) 0.0625(14) 0.0469(11) -0.0124(10) -0.0078(10) 0.0102(11)
C15 0.0382(9) 0.0357(8) 0.0294(7) 0.0014(6) -0.0074(6) -0.0005(7)
C16 0.0491(10) 0.0354(9) 0.0376(9) 0.0051(7) -0.0095(7) -0.0024(7)
C17 0.0641(13) 0.0364(10) 0.0460(10) 0.0007(8) -0.0100(9) 0.0099(9)
C18 0.0500(11) 0.0549(12) 0.0414(10) 0.0007(8) -0.0030(8) 0.0124(9)
C19 0.0474(11) 0.0504(11) 0.0447(10) 0.0021(8) 0.0014(8) -0.0039(9)
C20 0.0480(10) 0.0353(9) 0.0353(8) -0.0002(7) -0.0039(7) -0.0028(7)
C21 0.0676(13) 0.0456(11) 0.0396(10) -0.0007(8) -0.0138(9) -0.0168(10)
C22 0.0391(9) 0.0389(9) 0.0403(9) -0.0049(7) -0.0095(7) -0.0018(7)
C23 0.0455(10) 0.0350(9) 0.0441(10) -0.0023(7) -0.0134(8) 0.0025(7)
C24 0.0648(13) 0.0366(10) 0.0457(10) 0.0009(8) -0.0174(9) -0.0044(9)
C25 0.0446(10) 0.0400(10) 0.0397(9) -0.0031(7) -0.0044(7) -0.0047(7)
C26 0.0434(10) 0.0432(10) 0.0397(9) -0.0069(7) -0.0060(7) 0.0033(8)
C27 0.0646(13) 0.0383(10) 0.0471(10) -0.0109(8) -0.0155(9) 0.0017(9)
C28 0.0666(13) 0.0318(9) 0.0502(11) -0.0041(8) -0.0176(9) -0.0008(8)
C29 0.0444(10) 0.0581(12) 0.0373(9) -0.0076(8) -0.0024(8) -0.0040(9)
C30 0.0594(13) 0.0570(13) 0.0429(10) 0.0018(9) -0.0061(9) -0.0045(10)
C31 0.0627(15) 0.0871(19) 0.0558(14) 0.0216(13) -0.0137(11) -0.0140(13)
C32 0.0617(15) 0.130(3) 0.0409(12) 0.0115(14) -0.0089(11) -0.0260(17)
C33 0.0685(16) 0.126(3) 0.0406(12) -0.0251(15) 0.0064(11) -0.0151(17)
C34 0.0593(14) 0.0780(16) 0.0469(12) -0.0187(11) 0.0020(10) 0.0003(12)
C35 0.0374(8) 0.0371(9) 0.0271(7) -0.0003(6) -0.0038(6) 0.0025(7)
C36 0.0457(10) 0.0381(9) 0.0377(9) 0.0012(7) -0.0039(7) 0.0022(7)
C37 0.0559(12) 0.0446(11) 0.0430(10) -0.0033(8) -0.0069(9) -0.0107(9)
C38 0.0461(11) 0.0636(13) 0.0395(9) 0.0007(9) -0.0122(8) -0.0106(9)
C39 0.0431(10) 0.0591(12) 0.0410(9) 0.0021(8) -0.0134(8) 0.0056(9)
C40 0.0421(9) 0.0401(9) 0.0326(8) -0.0004(7) -0.0048(7) 0.0043(7)
Cl1 0.0692(4) 0.0342(3) 0.0719(3) -0.0012(2) 0.0127(3) -0.0076(2)
Cl2 0.0644(3) 0.0379(3) 0.0630(3) -0.0055(2) -0.0176(2) 0.0126(2)
N1 0.0538(9) 0.0396(8) 0.0344(7) -0.0005(6) -0.0058(7) -0.0004(7)
N2 0.0661(11) 0.0398(9) 0.0363(8) -0.0012(6) -0.0114(7) -0.0086(8)
O1 0.0450(8) 0.0576(9) 0.0488(8) -0.0045(6) -0.0089(6) -0.0118(6)
O2 0.0555(9) 0.0538(9) 0.0514(8) 0.0067(6) -0.0156(7) 0.0136(7)
O3 0.0490(8) 0.0558(9) 0.0730(10) -0.0104(8) -0.0214(7) 0.0179(7)
O4 0.0469(8) 0.0578(9) 0.0524(8) -0.0004(7) 0.0007(6) -0.0108(7)
S1 0.0384(2) 0.0418(2) 0.0359(2) 0.00045(17) -0.00892(17) 0.00045(17)
S2 0.0365(2) 0.0424(2) 0.0422(2) -0.00321(18) -0.00832(17) 0.00240(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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.506(3) . ?
C1 N1 1.479(2) . ?
C2 C3 1.383(3) . ?
C2 C5 1.386(3) . ?
C3 C4 1.495(3) . ?
C3 C8 1.382(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.474(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(3) . ?
C6 C7 1.393(3) . ?
C6 C9 1.492(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(3) . ?
C15 C20 1.402(3) . ?
C15 S1 1.7827(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C20 Cl1 1.7355(19) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(3) . ?
C21 N2 1.472(3) . ?
C22 C23 1.384(3) . ?
C22 C25 1.385(3) . ?
C23 C24 1.496(3) . ?
C23 C28 1.386(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 N2 1.475(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.397(3) . ?
C26 C27 1.400(3) . ?
C26 C29 1.489(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.391(3) . ?
C29 C34 1.393(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.395(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.373(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.392(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(3) . ?
C35 C40 1.398(2) . ?
C35 S2 1.7705(18) . ?
C36 H36 0.9300 . ?
C36 C37 1.392(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.374(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.384(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.389(3) . ?
C40 Cl2 1.7324(19) . ?
N1 S1 1.6248(16) . ?
N2 S2 1.6200(17) . ?
O1 S1 1.4326(15) . ?
O2 S1 1.4272(15) . ?
O3 S2 1.4295(15) . ?
O4 S2 1.4326(15) . ?
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
H1A C1 H1B 109.3 . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
N1 C1 H1A 111.5 . . ?
N1 C1 H1B 111.5 . . ?
N1 C1 C2 101.45(15) . . ?
C3 C2 C1 110.20(17) . . ?
C3 C2 C5 121.09(17) . . ?
C5 C2 C1 128.67(18) . . ?
C2 C3 C4 111.22(17) . . ?
C8 C3 C2 120.7(2) . . ?
C8 C3 C4 128.1(2) . . ?
C3 C4 H4A 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C4 C3 101.52(16) . . ?
N1 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C2 C5 H5 120.4 . . ?
C2 C5 C6 119.17(18) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 121.58(19) . . ?
C7 C6 C5 118.82(19) . . ?
C7 C6 C9 119.52(18) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 C7 118.4(2) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C6 121.10(18) . . ?
C10 C9 C14 118.0(2) . . ?
C14 C9 C6 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C20 118.60(17) . . ?
C16 C15 S1 116.45(14) . . ?
C20 C15 S1 124.92(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.13(18) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.62(18) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.34(19) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 Cl1 122.92(15) . . ?
C19 C20 C15 119.93(18) . . ?
C19 C20 Cl1 117.14(15) . . ?
H21A C21 H21B 109.2 . . ?
C22 C21 H21A 111.3 . . ?
C22 C21 H21B 111.3 . . ?
N2 C21 H21A 111.3 . . ?
N2 C21 H21B 111.3 . . ?
N2 C21 C22 102.11(16) . . ?
C23 C22 C21 110.53(17) . . ?
C23 C22 C25 121.24(17) . . ?
C25 C22 C21 128.15(18) . . ?
C22 C23 C24 111.88(16) . . ?
C22 C23 C28 120.22(18) . . ?
C28 C23 C24 127.87(18) . . ?
C23 C24 H24A 111.5 . . ?
C23 C24 H24B 111.5 . . ?
H24A C24 H24B 109.3 . . ?
N2 C24 C23 101.58(15) . . ?
N2 C24 H24A 111.5 . . ?
N2 C24 H24B 111.5 . . ?
C22 C25 H25 120.3 . . ?
C22 C25 C26 119.37(18) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 118.76(18) . . ?
C25 C26 C29 121.20(19) . . ?
C27 C26 C29 119.82(18) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.66(18) . . ?
C28 C27 H27 119.2 . . ?
C23 C28 C27 118.72(19) . . ?
C23 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C30 C29 C26 120.46(18) . . ?
C30 C29 C34 117.9(2) . . ?
C34 C29 C26 121.5(2) . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.3(2) . . ?
C31 C30 H30 119.3 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.6(2) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.8(3) . . ?
C34 C33 H33 119.6 . . ?
C29 C34 H34 119.8 . . ?
C33 C34 C29 120.5(3) . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C40 119.83(17) . . ?
C36 C35 S2 117.47(14) . . ?
C40 C35 S2 122.69(14) . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.85(18) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.07(19) . . ?
C38 C37 H37 120.0 . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.67(19) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.1 . . ?
C38 C39 C40 119.82(19) . . ?
C40 C39 H39 120.1 . . ?
C35 C40 Cl2 122.23(15) . . ?
C39 C40 C35 119.76(18) . . ?
C39 C40 Cl2 118.01(15) . . ?
C1 N1 S1 119.75(13) . . ?
C4 N1 C1 111.71(15) . . ?
C4 N1 S1 122.27(13) . . ?
C21 N2 C24 113.77(16) . . ?
C21 N2 S2 119.80(14) . . ?
C24 N2 S2 122.11(14) . . ?
N1 S1 C15 108.19(8) . . ?
O1 S1 C15 105.63(9) . . ?
O1 S1 N1 106.07(9) . . ?
O2 S1 C15 109.20(9) . . ?
O2 S1 N1 107.07(9) . . ?
O2 S1 O1 120.18(10) . . ?
N2 S2 C35 104.58(9) . . ?
O3 S2 C35 105.60(9) . . ?
O3 S2 N2 109.69(10) . . ?
O3 S2 O4 118.97(10) . . ?
O4 S2 C35 109.94(9) . . ?
O4 S2 N2 107.19(9) . . ?
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
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C3 C8 -177.3(2) . . . . ?
C1 C2 C5 C6 177.2(2) . . . . ?
C1 N1 S1 C15 -75.43(17) . . . . ?
C1 N1 S1 O1 37.51(18) . . . . ?
C1 N1 S1 O2 166.99(15) . . . . ?
C2 C1 N1 C4 19.6(2) . . . . ?
C2 C1 N1 S1 172.41(13) . . . . ?
C2 C3 C4 N1 11.4(2) . . . . ?
C2 C3 C8 C7 -1.0(4) . . . . ?
C2 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C9 -176.12(18) . . . . ?
C3 C2 C5 C6 -0.3(3) . . . . ?
C3 C4 N1 C1 -19.5(2) . . . . ?
C3 C4 N1 S1 -171.51(14) . . . . ?
C4 C3 C8 C7 -178.1(2) . . . . ?
C4 N1 S1 C15 74.46(18) . . . . ?
C4 N1 S1 O1 -172.60(17) . . . . ?
C4 N1 S1 O2 -43.1(2) . . . . ?
C5 C2 C3 C4 178.05(19) . . . . ?
C5 C2 C3 C8 0.5(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C5 C6 C9 C10 37.6(3) . . . . ?
C5 C6 C9 C14 -146.6(2) . . . . ?
C6 C7 C8 C3 1.3(4) . . . . ?
C6 C9 C10 C11 174.9(2) . . . . ?
C6 C9 C14 C13 -174.9(2) . . . . ?
C7 C6 C9 C10 -139.0(2) . . . . ?
C7 C6 C9 C14 36.8(3) . . . . ?
C8 C3 C4 N1 -171.3(2) . . . . ?
C9 C6 C7 C8 175.7(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C9 C14 C13 1.1(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C15 C20 C19 -1.7(3) . . . . ?
C16 C15 C20 Cl1 177.76(14) . . . . ?
C16 C15 S1 N1 102.47(14) . . . . ?
C16 C15 S1 O1 -10.77(16) . . . . ?
C16 C15 S1 O2 -141.32(14) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C18 C19 C20 Cl1 -178.49(16) . . . . ?
C20 C15 C16 C17 1.1(3) . . . . ?
C20 C15 S1 N1 -79.38(17) . . . . ?
C20 C15 S1 O1 167.38(15) . . . . ?
C20 C15 S1 O2 36.83(18) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C21 C22 C23 C28 -177.9(2) . . . . ?
C21 C22 C25 C26 176.0(2) . . . . ?
C21 N2 S2 C35 78.56(18) . . . . ?
C21 N2 S2 O3 -34.3(2) . . . . ?
C21 N2 S2 O4 -164.74(17) . . . . ?
C22 C21 N2 C24 -3.5(3) . . . . ?
C22 C21 N2 S2 153.71(15) . . . . ?
C22 C23 C24 N2 -2.4(2) . . . . ?
C22 C23 C28 C27 0.8(3) . . . . ?
C22 C25 C26 C27 1.7(3) . . . . ?
C22 C25 C26 C29 -172.94(18) . . . . ?
C23 C22 C25 C26 -0.4(3) . . . . ?
C23 C24 N2 C21 3.6(2) . . . . ?
C23 C24 N2 S2 -152.93(15) . . . . ?
C24 C23 C28 C27 -177.1(2) . . . . ?
C24 N2 S2 C35 -126.23(17) . . . . ?
C24 N2 S2 O3 120.93(17) . . . . ?
C24 N2 S2 O4 -9.5(2) . . . . ?
C25 C22 C23 C24 177.34(19) . . . . ?
C25 C22 C23 C28 -0.9(3) . . . . ?
C25 C26 C27 C28 -1.8(3) . . . . ?
C25 C26 C29 C30 38.1(3) . . . . ?
C25 C26 C29 C34 -146.6(2) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C26 C29 C30 C31 175.6(2) . . . . ?
C26 C29 C34 C33 -174.9(2) . . . . ?
C27 C26 C29 C30 -136.4(2) . . . . ?
C27 C26 C29 C34 38.9(3) . . . . ?
C28 C23 C24 N2 175.7(2) . . . . ?
C29 C26 C27 C28 172.9(2) . . . . ?
C29 C30 C31 C32 -0.7(4) . . . . ?
C30 C29 C34 C33 0.6(4) . . . . ?
C30 C31 C32 C33 0.6(4) . . . . ?
C31 C32 C33 C34 0.1(4) . . . . ?
C32 C33 C34 C29 -0.7(4) . . . . ?
C34 C29 C30 C31 0.1(3) . . . . ?
C35 C36 C37 C38 -0.5(3) . . . . ?
C36 C35 C40 C39 0.0(3) . . . . ?
C36 C35 C40 Cl2 179.45(14) . . . . ?
C36 C35 S2 N2 -113.58(15) . . . . ?
C36 C35 S2 O3 2.14(17) . . . . ?
C36 C35 S2 O4 131.64(14) . . . . ?
C36 C37 C38 C39 0.7(3) . . . . ?
C37 C38 C39 C40 -0.4(3) . . . . ?
C38 C39 C40 C35 0.1(3) . . . . ?
C38 C39 C40 Cl2 -179.36(16) . . . . ?
C40 C35 C36 C37 0.2(3) . . . . ?
C40 C35 S2 N2 67.28(16) . . . . ?
C40 C35 S2 O3 -177.00(15) . . . . ?
C40 C35 S2 O4 -47.49(17) . . . . ?
N1 C1 C2 C3 -11.7(2) . . . . ?
N1 C1 C2 C5 170.65(19) . . . . ?
N2 C21 C22 C23 1.8(2) . . . . ?
N2 C21 C22 C25 -174.9(2) . . . . ?
S1 C15 C16 C17 179.40(15) . . . . ?
S1 C15 C20 C19 -179.79(15) . . . . ?
S1 C15 C20 Cl1 -0.4(2) . . . . ?
S2 C35 C36 C37 -178.97(14) . . . . ?
S2 C35 C40 C39 179.14(14) . . . . ?
S2 C35 C40 Cl2 -1.4(2) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160608wxn-1_a.res in P-1
CELL 1.54184 7.5142 12.7251 18.022 88.481 84.657 89.958
ZERR 4 0.0002 0.0004 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H N O S Cl
UNIT 80 64 4 8 4 4
L.S. 20
PLAN 20
SIZE 0.35 0.22 0.2
BOND $H
LIST 6
HTAB
CONF
fmap 2
acta
REM
REM
REM
WGHT 0.071600 0.253800
FVAR 0.62859
C1 1 0.664799 0.296323 0.306975 11.00000 0.05366 0.03903 =
0.03748 -0.00140 -0.00742 -0.00388
AFIX 23
H1A 2 0.762580 0.248607 0.293578 11.00000 -1.20000
H1B 2 0.554119 0.256747 0.315171 11.00000 -1.20000
AFIX 0
C2 1 0.698494 0.358641 0.374179 11.00000 0.03903 0.03954 =
0.03741 -0.00518 -0.00415 0.00160
C3 1 0.739413 0.461725 0.353129 11.00000 0.05372 0.03804 =
0.04315 -0.00329 -0.00728 0.00039
C4 1 0.736795 0.478935 0.270869 11.00000 0.07220 0.04274 =
0.04321 -0.00043 -0.00765 -0.00675
AFIX 23
H4A 2 0.665720 0.539857 0.259341 11.00000 -1.20000
H4B 2 0.856622 0.487315 0.246350 11.00000 -1.20000
AFIX 0
C5 1 0.698400 0.324219 0.447797 11.00000 0.04408 0.03789 =
0.03974 -0.00394 -0.00430 -0.00019
AFIX 43
H5 2 0.670181 0.254786 0.461409 11.00000 -1.20000
AFIX 0
C6 1 0.741348 0.395331 0.501446 11.00000 0.04851 0.04492 =
0.03999 -0.00761 -0.00778 0.00424
C7 1 0.781461 0.498906 0.479120 11.00000 0.08525 0.04426 =
0.04923 -0.01199 -0.02031 -0.00139
AFIX 43
H7 2 0.808095 0.546613 0.514718 11.00000 -1.20000
AFIX 0
C8 1 0.782826 0.533031 0.405122 11.00000 0.09003 0.03645 =
0.05467 -0.00498 -0.01667 -0.00383
AFIX 43
H8 2 0.812227 0.602129 0.390971 11.00000 -1.20000
AFIX 0
C9 1 0.754588 0.361304 0.580629 11.00000 0.04433 0.05284 =
0.04040 -0.00742 -0.00802 0.00087
C10 1 0.826303 0.264402 0.598433 11.00000 0.05372 0.05546 =
0.04514 -0.00462 -0.00727 0.00537
AFIX 43
H10 2 0.858091 0.217450 0.560808 11.00000 -1.20000
AFIX 0
C11 1 0.851250 0.236613 0.672011 11.00000 0.05549 0.07452 =
0.05499 0.01046 -0.01017 0.00892
AFIX 43
H11 2 0.899847 0.171429 0.682998 11.00000 -1.20000
AFIX 0
C12 1 0.804544 0.304881 0.728737 11.00000 0.05532 0.10333 =
0.04036 0.00197 -0.01268 0.00052
AFIX 43
H12 2 0.822559 0.286297 0.777727 11.00000 -1.20000
AFIX 0
C13 1 0.730970 0.400831 0.712107 11.00000 0.06809 0.09058 =
0.04246 -0.01806 -0.00857 0.00545
AFIX 43
H13 2 0.698070 0.446971 0.750127 11.00000 -1.20000
AFIX 0
C14 1 0.705594 0.429115 0.638749 11.00000 0.06148 0.06254 =
0.04692 -0.01244 -0.00776 0.01019
AFIX 43
H14 2 0.655356 0.494014 0.628248 11.00000 -1.20000
AFIX 0
C15 1 0.858615 0.311112 0.125600 11.00000 0.03817 0.03571 =
0.02938 0.00139 -0.00739 -0.00053
C16 1 0.886304 0.203489 0.118677 11.00000 0.04906 0.03542 =
0.03755 0.00514 -0.00947 -0.00240
AFIX 43
H16 2 0.793719 0.157054 0.133903 11.00000 -1.20000
AFIX 0
C17 1 1.049218 0.164419 0.089529 11.00000 0.06414 0.03641 =
0.04604 0.00066 -0.01000 0.00988
AFIX 43
H17 2 1.065704 0.092334 0.085134 11.00000 -1.20000
AFIX 0
C18 1 1.186987 0.232989 0.067036 11.00000 0.05000 0.05492 =
0.04140 0.00070 -0.00299 0.01239
AFIX 43
H18 2 1.297142 0.206937 0.048058 11.00000 -1.20000
AFIX 0
C19 1 1.162205 0.340189 0.072549 11.00000 0.04743 0.05043 =
0.04470 0.00212 0.00141 -0.00388
AFIX 43
H19 2 1.255591 0.385936 0.057035 11.00000 -1.20000
AFIX 0
C20 1 0.998722 0.379960 0.101111 11.00000 0.04800 0.03534 =
0.03532 -0.00018 -0.00386 -0.00284
C21 1 0.661853 0.806773 0.295677 11.00000 0.06759 0.04563 =
0.03957 -0.00065 -0.01376 -0.01684
AFIX 23
H21A 2 0.735520 0.744194 0.291556 11.00000 -1.20000
H21B 2 0.536988 0.786680 0.297530 11.00000 -1.20000
AFIX 0
C22 1 0.698336 0.868565 0.362539 11.00000 0.03907 0.03891 =
0.04026 -0.00487 -0.00952 -0.00178
C23 1 0.755547 0.969157 0.341053 11.00000 0.04546 0.03505 =
0.04410 -0.00233 -0.01343 0.00245
C24 1 0.762887 0.986703 0.258442 11.00000 0.06476 0.03661 =
0.04569 0.00089 -0.01738 -0.00440
AFIX 23
H24A 2 0.679369 1.040679 0.245222 11.00000 -1.20000
H24B 2 0.882317 1.005898 0.237396 11.00000 -1.20000
AFIX 0
C25 1 0.688985 0.834558 0.436460 11.00000 0.04462 0.03996 =
0.03974 -0.00311 -0.00443 -0.00467
AFIX 43
H25 2 0.649622 0.766906 0.450136 11.00000 -1.20000
AFIX 0
C26 1 0.739229 0.902828 0.490252 11.00000 0.04341 0.04325 =
0.03968 -0.00694 -0.00602 0.00327
C27 1 0.793280 1.005012 0.467958 11.00000 0.06462 0.03830 =
0.04714 -0.01091 -0.01554 0.00174
AFIX 43
H27 2 0.823736 1.051457 0.503719 11.00000 -1.20000
AFIX 0
C28 1 0.802555 1.038741 0.393842 11.00000 0.06663 0.03181 =
0.05024 -0.00410 -0.01760 -0.00079
AFIX 43
H28 2 0.839591 1.106715 0.379855 11.00000 -1.20000
AFIX 0
C29 1 0.751268 0.866044 0.568737 11.00000 0.04438 0.05805 =
0.03726 -0.00758 -0.00243 -0.00404
C30 1 0.816721 0.766405 0.584254 11.00000 0.05943 0.05703 =
0.04290 0.00181 -0.00614 -0.00452
AFIX 43
H30 2 0.845304 0.721036 0.545324 11.00000 -1.20000
AFIX 0
C31 1 0.840366 0.733143 0.657080 11.00000 0.06272 0.08708 =
0.05580 0.02160 -0.01368 -0.01401
AFIX 43
H31 2 0.883020 0.665919 0.666431 11.00000 -1.20000
AFIX 0
C32 1 0.800435 0.800023 0.715023 11.00000 0.06165 0.12976 =
0.04085 0.01147 -0.00893 -0.02604
AFIX 43
H32 2 0.817010 0.778456 0.763604 11.00000 -1.20000
AFIX 0
C33 1 0.735993 0.898763 0.700731 11.00000 0.06845 0.12592 =
0.04062 -0.02509 0.00637 -0.01509
AFIX 43
H33 2 0.709245 0.943956 0.739922 11.00000 -1.20000
AFIX 0
C34 1 0.710168 0.932114 0.628317 11.00000 0.05928 0.07796 =
0.04692 -0.01875 0.00204 0.00032
AFIX 43
H34 2 0.665162 0.998971 0.619659 11.00000 -1.20000
AFIX 0
C35 1 0.574791 0.804296 0.114230 11.00000 0.03736 0.03715 =
0.02709 -0.00034 -0.00378 0.00250
C36 1 0.548658 0.698491 0.101791 11.00000 0.04572 0.03814 =
0.03768 0.00119 -0.00390 0.00220
AFIX 43
H36 2 0.633668 0.649303 0.113828 11.00000 -1.20000
AFIX 0
C37 1 0.394966 0.666168 0.071265 11.00000 0.05595 0.04461 =
0.04300 -0.00326 -0.00692 -0.01067
AFIX 43
H37 2 0.377712 0.595369 0.062507 11.00000 -1.20000
AFIX 0
C38 1 0.268708 0.738725 0.054054 11.00000 0.04607 0.06355 =
0.03946 0.00069 -0.01216 -0.01056
AFIX 43
H38 2 0.165704 0.716547 0.034143 11.00000 -1.20000
AFIX 0
C39 1 0.293244 0.844507 0.066047 11.00000 0.04312 0.05914 =
0.04101 0.00208 -0.01337 0.00562
AFIX 43
H39 2 0.207445 0.893138 0.053917 11.00000 -1.20000
AFIX 0
C40 1 0.446341 0.877827 0.096245 11.00000 0.04210 0.04012 =
0.03262 -0.00044 -0.00477 0.00432
CL1 6 0.978183 0.515686 0.103851 11.00000 0.06923 0.03418 =
0.07193 -0.00116 0.01269 -0.00759
CL2 6 0.469572 1.010887 0.111021 11.00000 0.06437 0.03789 =
0.06298 -0.00548 -0.01761 0.01259
N1 3 0.653233 0.380788 0.249651 11.00000 0.05384 0.03963 =
0.03436 -0.00053 -0.00576 -0.00036
N2 3 0.710454 0.882425 0.233890 11.00000 0.06606 0.03984 =
0.03631 -0.00123 -0.01140 -0.00859
O1 4 0.532607 0.258247 0.164751 11.00000 0.04500 0.05764 =
0.04882 -0.00451 -0.00888 -0.01175
O2 4 0.591235 0.443805 0.124598 11.00000 0.05549 0.05381 =
0.05138 0.00671 -0.01560 0.01365
O3 4 0.873223 0.744689 0.158492 11.00000 0.04903 0.05584 =
0.07297 -0.01042 -0.02136 0.01792
O4 4 0.857551 0.926828 0.109381 11.00000 0.04687 0.05784 =
0.05243 -0.00044 0.00072 -0.01080
S1 5 0.641783 0.350674 0.163172 11.00000 0.03845 0.04179 =
0.03589 0.00045 -0.00892 0.00045
S2 5 0.774966 0.840163 0.151740 11.00000 0.03651 0.04237 =
0.04220 -0.00321 -0.00832 0.00240
HKLF 4
REM 20160608wxn-1_a.res in P-1
REM R1 = 0.0465 for 5953 Fo > 4sig(Fo) and 0.0506 for all 6691 data
REM 451 parameters refined using 0 restraints
END
WGHT 0.0715 0.2538
REM Highest difference peak 0.248, deepest hole -0.616, 1-sigma level 0.098
Q1 1 0.4535 0.8258 0.3031 11.00000 0.05 0.25
Q2 1 0.2342 0.9967 -0.0177 11.00000 0.05 0.24
Q3 1 1.1667 0.4316 -0.0091 11.00000 0.05 0.24
Q4 1 0.2368 0.9243 -0.0245 11.00000 0.05 0.23
Q5 1 0.9225 0.6650 0.2611 11.00000 0.05 0.23
Q6 1 0.9065 0.6453 0.2269 11.00000 0.05 0.23
Q7 1 0.6234 0.7173 0.7390 11.00000 0.05 0.22
Q8 1 0.2241 0.9419 0.0604 11.00000 0.05 0.22
Q9 1 0.8623 0.5638 0.2290 11.00000 0.05 0.22
Q10 1 1.2123 0.4647 -0.0191 11.00000 0.05 0.22
Q11 1 0.8536 0.5823 0.2174 11.00000 0.05 0.21
Q12 1 0.7721 1.0648 0.2389 11.00000 0.05 0.21
Q13 1 0.8323 0.5759 0.0828 11.00000 0.05 0.21
Q14 1 0.7727 0.3164 0.1378 11.00000 0.05 0.21
Q15 1 0.2155 0.5216 0.0078 11.00000 0.05 0.21
Q16 1 0.9217 0.7158 0.2573 11.00000 0.05 0.21
Q17 1 0.3814 0.3599 0.2454 11.00000 0.05 0.21
Q18 1 0.8085 0.1252 0.2031 11.00000 0.05 0.21
Q19 1 0.8056 0.5624 0.0970 11.00000 0.05 0.20
Q20 1 0.8119 0.6134 0.2012 11.00000 0.05 0.20
REM The information below was added by Olex2.
REM
REM R1 = 0.0465 for 5953 Fo > 4sig(Fo) and 0.0506 for all 11482 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.25, deepest hole -0.62
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0506
REM R1_gt = 0.0465
REM wR_ref = 0.1257
REM GOOF = 1.045
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 11482
REM Reflections_gt = 5953
REM Parameters = n/a
REM Hole = -0.62
REM Peak = 0.25
REM Flack = n/a
;
_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_3ag
_database_code_depnum_ccdc_archive 'CCDC 1491620'
_audit_update_record
;
2017-12-29 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;
_audit_creation_date 2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C21 H18 Cl N O2 S'
_chemical_formula_sum 'C21 H18 Cl N O2 S'
_chemical_formula_weight 383.87
_chemical_absolute_configuration ad
_chemical_melting_point ?
_chemical_oxdiff_formula 'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
_cell_length_a 7.08143(9)
_cell_length_b 9.08409(11)
_cell_length_c 29.0369(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1867.89(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 18135
_cell_measurement_temperature 294(2)
_cell_measurement_theta_max 73.6170
_cell_measurement_theta_min 4.8540
_exptl_absorpt_coefficient_mu 2.975
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.37839
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.365
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 800
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0701
_diffrn_reflns_av_unetI/netI 0.0232
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 30484
_diffrn_reflns_theta_full 66.99
_diffrn_reflns_theta_max 66.99
_diffrn_reflns_theta_min 5.10
_diffrn_ambient_temperature 294(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega 2.00 27.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -99.0000 -90.0000 25
#__ type_ start__ end____ width___ exp.time_
2 omega 34.00 98.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -180.0000 64
#__ type_ start__ end____ width___ exp.time_
3 omega 25.00 96.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 -150.0000 71
#__ type_ start__ end____ width___ exp.time_
4 omega 36.00 78.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -30.0000 42
#__ type_ start__ end____ width___ exp.time_
5 omega 55.00 85.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -30.0000 90.0000 30
#__ type_ start__ end____ width___ exp.time_
6 omega 34.00 77.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 -125.0000 150.0000 43
#__ type_ start__ end____ width___ exp.time_
7 omega -43.00 14.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -40.5455 38.0000 150.0000 57
#__ type_ start__ end____ width___ exp.time_
8 omega 50.00 88.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 40.5455 77.0000 150.0000 38
#__ type_ start__ end____ width___ exp.time_
9 omega 106.00 177.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.1410 125.0000 -150.0000 71
#__ type_ start__ end____ width___ exp.time_
10 omega -104.00 -19.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -38.0000 60.0000 85
#__ type_ start__ end____ width___ exp.time_
11 omega -33.00 -8.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -77.0000 -30.0000 25
#__ type_ start__ end____ width___ exp.time_
12 omega -120.00 -2.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -19.0000 150.0000 118
#__ type_ start__ end____ width___ exp.time_
13 omega -107.00 -60.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 -77.0000 -30.0000 47
#__ type_ start__ end____ width___ exp.time_
14 omega -49.00 33.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -40.7955 38.0000 -120.0000 82
#__ type_ start__ end____ width___ exp.time_
15 omega 5.00 30.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7955 88.0000 112.0905 25
#__ type_ start__ end____ width___ exp.time_
16 omega 24.00 95.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 40.7955 -125.0000 0.0000 71
#__ type_ start__ end____ width___ exp.time_
17 omega 8.00 33.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 42.0000 82.0000 -40.8064 25
#__ type_ start__ end____ width___ exp.time_
18 omega 18.00 43.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 50.0000 80.0000 36.1259 25
#__ type_ start__ end____ width___ exp.time_
19 omega 16.00 41.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 50.0000 82.0000 91.7644 25
#__ type_ start__ end____ width___ exp.time_
20 omega 21.00 47.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 54.0000 79.0000 -116.3879 26
#__ type_ start__ end____ width___ exp.time_
21 omega 21.00 46.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 54.0000 79.0000 156.8730 25
#__ type_ start__ end____ width___ exp.time_
22 omega 31.00 57.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 58.0000 77.0000 -59.9348 26
#__ type_ start__ end____ width___ exp.time_
23 omega 29.00 64.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 58.0000 75.0000 -146.2639 35
#__ type_ start__ end____ width___ exp.time_
24 omega 109.00 134.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 58.0000 77.0000 -59.9348 25
#__ type_ start__ end____ width___ exp.time_
25 omega 30.00 70.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 62.0000 75.0000 -89.0240 40
#__ type_ start__ end____ width___ exp.time_
26 omega 33.00 77.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 174.3629 44
#__ type_ start__ end____ width___ exp.time_
27 omega 100.00 126.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 102.2897 26
#__ type_ start__ end____ width___ exp.time_
28 omega 34.00 82.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 76.0000 -26.5652 48
#__ type_ start__ end____ width___ exp.time_
29 omega 33.00 59.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 102.2897 26
#__ type_ start__ end____ width___ exp.time_
30 omega 110.00 140.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 66.0000 77.0000 174.3629 30
#__ type_ start__ end____ width___ exp.time_
31 omega 38.00 79.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 70.0000 77.0000 115.5086 41
#__ type_ start__ end____ width___ exp.time_
32 omega 118.00 144.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 70.0000 75.0000 49.9610 26
#__ type_ start__ end____ width___ exp.time_
33 omega 38.00 67.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 70.0000 75.0000 49.9610 29
#__ type_ start__ end____ width___ exp.time_
34 omega 42.00 80.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 74.0000 76.0000 18.5036 38
#__ type_ start__ end____ width___ exp.time_
35 omega 75.00 106.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -180.0000 31
#__ type_ start__ end____ width___ exp.time_
36 omega 75.00 163.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 150.0000 88
#__ type_ start__ end____ width___ exp.time_
37 omega 75.00 170.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 90.0000 95
#__ type_ start__ end____ width___ exp.time_
38 omega 58.00 95.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -45.0000 -90.0000 37
#__ type_ start__ end____ width___ exp.time_
39 omega 75.00 101.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -30.0000 26
#__ type_ start__ end____ width___ exp.time_
40 omega 72.00 98.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 90.0000 26
#__ type_ start__ end____ width___ exp.time_
41 omega 76.00 143.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 0.0000 67
#__ type_ start__ end____ width___ exp.time_
42 omega 34.00 67.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 90.0000 33
#__ type_ start__ end____ width___ exp.time_
43 omega 75.00 178.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -60.0000 103
#__ type_ start__ end____ width___ exp.time_
44 omega 79.00 122.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -120.0000 43
#__ type_ start__ end____ width___ exp.time_
45 omega 31.00 111.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -101.0000 -52.0000 80
#__ type_ start__ end____ width___ exp.time_
46 omega 79.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 60.0000 25
#__ type_ start__ end____ width___ exp.time_
47 omega 78.00 117.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 0.0000 39
#__ type_ start__ end____ width___ exp.time_
48 omega 75.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -150.0000 29
#__ type_ start__ end____ width___ exp.time_
49 omega 78.00 156.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -150.0000 78
#__ type_ start__ end____ width___ exp.time_
50 omega 42.00 121.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -125.0000 -180.0000 79
#__ type_ start__ end____ width___ exp.time_
51 omega 75.00 146.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -90.0000 71
#__ type_ start__ end____ width___ exp.time_
52 omega 148.00 175.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -120.0000 27
#__ type_ start__ end____ width___ exp.time_
53 omega 75.00 152.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 30.0000 77
#__ type_ start__ end____ width___ exp.time_
54 omega 78.00 104.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 -180.0000 26
#__ type_ start__ end____ width___ exp.time_
55 omega 79.00 124.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 61.0000 150.0000 45
#__ type_ start__ end____ width___ exp.time_
56 omega 122.00 149.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 120.0000 27
#__ type_ start__ end____ width___ exp.time_
57 omega 75.00 130.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -120.0000 55
#__ type_ start__ end____ width___ exp.time_
58 omega 75.00 101.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 120.0000 26
#__ type_ start__ end____ width___ exp.time_
59 omega 75.00 143.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 60.0000 68
#__ type_ start__ end____ width___ exp.time_
60 omega 118.00 143.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 77.0000 -30.0000 25
#__ type_ start__ end____ width___ exp.time_
61 omega 84.00 109.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 -150.0000 25
#__ type_ start__ end____ width___ exp.time_
62 omega 84.00 109.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 107.1410 -95.0000 120.0000 25
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0598143000
_diffrn_orient_matrix_UB_12 -0.0179338000
_diffrn_orient_matrix_UB_13 -0.0507045000
_diffrn_orient_matrix_UB_21 0.0662621000
_diffrn_orient_matrix_UB_22 0.1615083000
_diffrn_orient_matrix_UB_23 -0.0009226000
_diffrn_orient_matrix_UB_31 0.1983507000
_diffrn_orient_matrix_UB_32 -0.0485259000
_diffrn_orient_matrix_UB_33 0.0156195000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 3241
_reflns_number_total 3334
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max 0.143
_refine_diff_density_min -0.246
_refine_diff_density_rms 0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.005(14)
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.030
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 3334
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0345
_refine_ls_R_factor_gt 0.0337
_refine_ls_restrained_S_all 1.030
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.2179P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0923
_refine_ls_wR_factor_ref 0.0935
_refine_special_details
;
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^ > 2sigma(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.
;
_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.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.2633(3) 0.7806(2) 0.32233(7) 0.0542(4) Uani 1 d . . .
H1A H 0.1457 0.8072 0.3074 0.065 Uiso 1 calc . . R
H1B H 0.2505 0.6841 0.3363 0.065 Uiso 1 calc . . R
C2 C 0.4258(3) 0.78581(19) 0.28948(6) 0.0454(4) Uani 1 d . . .
C3 C 0.5780(3) 0.86058(18) 0.30854(6) 0.0431(4) Uani 1 d . . .
C4 C 0.5299(3) 0.9084(2) 0.35688(6) 0.0515(4) Uani 1 d . . .
H4A H 0.5878 0.8447 0.3797 0.062 Uiso 1 calc . . R
H4B H 0.5676 1.0094 0.3626 0.062 Uiso 1 calc . . R
C5 C 0.4372(3) 0.7295(2) 0.24529(7) 0.0546(5) Uani 1 d . . .
H5 H 0.3358 0.6789 0.2325 0.066 Uiso 1 calc . . R
C6 C 0.6008(3) 0.7496(2) 0.22049(7) 0.0515(4) Uani 1 d . . .
H6 H 0.6085 0.7114 0.1908 0.062 Uiso 1 calc . . R
C7 C 0.7561(3) 0.82582(18) 0.23860(6) 0.0421(4) Uani 1 d . . .
C8 C 0.7433(2) 0.88048(18) 0.28394(6) 0.0426(4) Uani 1 d . . .
H8 H 0.8451 0.9294 0.2972 0.051 Uiso 1 calc . . R
C9 C 0.9258(3) 0.84983(18) 0.20977(6) 0.0434(4) Uani 1 d . . .
C10 C 0.9721(3) 0.7522(2) 0.17423(7) 0.0497(4) Uani 1 d . . .
H10 H 0.8986 0.6684 0.1699 0.060 Uiso 1 calc . . R
C11 C 1.1244(3) 0.7768(2) 0.14531(7) 0.0557(5) Uani 1 d . . .
H11 H 1.1533 0.7102 0.1220 0.067 Uiso 1 calc . . R
C12 C 1.2322(3) 0.9011(2) 0.15148(7) 0.0565(5) Uani 1 d . . .
C13 C 1.1929(3) 0.9979(2) 0.18686(8) 0.0600(5) Uani 1 d . . .
H13 H 1.2691 1.0801 0.1914 0.072 Uiso 1 calc . . R
C14 C 1.0410(3) 0.9728(2) 0.21541(7) 0.0524(4) Uani 1 d . . .
H14 H 1.0148 1.0393 0.2389 0.063 Uiso 1 calc . . R
C15 C 0.2090(3) 0.7445(2) 0.43384(6) 0.0490(4) Uani 1 d . . .
C16 C 0.0730(3) 0.6377(3) 0.42745(8) 0.0646(6) Uani 1 d . . .
H16 H -0.0252 0.6535 0.4068 0.078 Uiso 1 calc . . R
C17 C 0.0830(4) 0.5077(3) 0.45169(8) 0.0680(6) Uani 1 d . . .
H17 H -0.0093 0.4363 0.4472 0.082 Uiso 1 calc . . R
C18 C 0.2274(4) 0.4811(2) 0.48266(7) 0.0605(5) Uani 1 d . . .
C19 C 0.3642(4) 0.5869(3) 0.48777(8) 0.0718(6) Uani 1 d . . .
H19 H 0.4646 0.5697 0.5077 0.086 Uiso 1 calc . . R
C20 C 0.3561(4) 0.7192(3) 0.46381(8) 0.0675(6) Uani 1 d . . .
H20 H 0.4492 0.7901 0.4680 0.081 Uiso 1 calc . . R
C21 C 0.2328(6) 0.3402(3) 0.51024(10) 0.0910(9) Uani 1 d . . .
H21A H 0.1204 0.3327 0.5286 0.137 Uiso 1 calc . . GR
H21B H 0.3415 0.3406 0.5300 0.137 Uiso 1 calc . . GR
H21C H 0.2399 0.2577 0.4897 0.137 Uiso 1 calc . . GR
Cl1 Cl 1.42119(11) 0.93557(9) 0.11493(2) 0.0897(2) Uani 1 d . . .
N1 N 0.3214(2) 0.89235(18) 0.35640(5) 0.0504(4) Uani 1 d . . .
O1 O 0.0051(2) 0.92894(19) 0.38830(6) 0.0708(5) Uani 1 d . . .
O2 O 0.2854(3) 1.02390(17) 0.42954(6) 0.0753(5) Uani 1 d . . .
S1 S 0.19644(7) 0.91133(5) 0.403115(17) 0.05525(15) Uani 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 0.0442(10) 0.0643(11) 0.0541(10) -0.0025(9) -0.0015(8) -0.0009(9)
C2 0.0411(9) 0.0469(9) 0.0483(9) 0.0025(7) -0.0046(8) 0.0030(8)
C3 0.0453(9) 0.0387(8) 0.0452(9) 0.0007(7) -0.0033(8) 0.0034(7)
C4 0.0492(10) 0.0577(10) 0.0475(10) -0.0059(9) 0.0001(8) 0.0001(9)
C5 0.0466(10) 0.0637(11) 0.0535(10) -0.0083(9) -0.0067(8) -0.0074(9)
C6 0.0507(10) 0.0582(10) 0.0457(9) -0.0077(8) -0.0040(8) -0.0038(9)
C7 0.0432(9) 0.0384(8) 0.0447(8) 0.0006(6) -0.0034(7) 0.0034(7)
C8 0.0426(9) 0.0387(8) 0.0466(8) -0.0034(7) -0.0048(7) -0.0019(7)
C9 0.0480(9) 0.0397(8) 0.0425(8) 0.0015(7) -0.0027(8) 0.0016(7)
C10 0.0571(11) 0.0440(9) 0.0479(9) -0.0051(8) 0.0003(8) -0.0055(9)
C11 0.0653(12) 0.0577(11) 0.0439(9) -0.0054(8) 0.0049(9) 0.0015(10)
C12 0.0580(12) 0.0624(11) 0.0491(9) 0.0074(9) 0.0083(9) -0.0023(10)
C13 0.0633(12) 0.0471(10) 0.0697(12) -0.0009(9) 0.0098(11) -0.0112(10)
C14 0.0572(11) 0.0434(9) 0.0565(11) -0.0066(8) 0.0049(9) -0.0036(8)
C15 0.0521(10) 0.0532(10) 0.0416(8) 0.0002(7) 0.0013(8) 0.0057(9)
C16 0.0625(13) 0.0720(13) 0.0594(12) 0.0124(10) -0.0146(10) -0.0041(11)
C17 0.0762(15) 0.0604(12) 0.0676(13) 0.0075(10) -0.0146(12) -0.0125(12)
C18 0.0756(14) 0.0579(11) 0.0479(9) 0.0040(8) -0.0032(10) 0.0078(11)
C19 0.0773(15) 0.0780(14) 0.0602(12) 0.0091(12) -0.0273(12) 0.0022(13)
C20 0.0721(14) 0.0696(13) 0.0609(12) -0.0012(11) -0.0172(11) -0.0122(12)
C21 0.121(2) 0.0715(15) 0.0807(16) 0.0233(13) -0.0133(17) 0.0059(16)
Cl1 0.0881(5) 0.1058(5) 0.0751(4) 0.0008(3) 0.0348(3) -0.0228(4)
N1 0.0478(8) 0.0558(9) 0.0475(8) -0.0007(7) 0.0061(7) 0.0020(7)
O1 0.0581(9) 0.0770(10) 0.0773(10) 0.0219(9) 0.0176(8) 0.0253(8)
O2 0.1042(13) 0.0548(8) 0.0668(9) -0.0108(7) 0.0221(10) -0.0048(9)
S1 0.0611(3) 0.0514(2) 0.0533(3) 0.00363(19) 0.0125(2) 0.0087(2)
_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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.495(3) . ?
C1 N1 1.476(3) . ?
C2 C3 1.389(3) . ?
C2 C5 1.383(3) . ?
C3 C4 1.508(2) . ?
C3 C8 1.383(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.484(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.402(3) . ?
C7 C8 1.410(2) . ?
C7 C9 1.481(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C12 C13 1.381(3) . ?
C12 Cl1 1.737(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 C20 1.376(3) . ?
C15 S1 1.7613(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 C19 1.373(3) . ?
C18 C21 1.510(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 S1 1.6287(16) . ?
O1 S1 1.4309(17) . ?
O2 S1 1.4251(17) . ?
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
H1A C1 H1B 109.4 . . ?
C2 C1 H1A 111.6 . . ?
C2 C1 H1B 111.6 . . ?
N1 C1 H1A 111.6 . . ?
N1 C1 H1B 111.6 . . ?
N1 C1 C2 101.03(15) . . ?
C3 C2 C1 111.01(16) . . ?
C5 C2 C1 128.68(17) . . ?
C5 C2 C3 120.31(18) . . ?
C2 C3 C4 109.66(16) . . ?
C8 C3 C2 120.99(16) . . ?
C8 C3 C4 129.35(16) . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
N1 C4 C3 100.81(15) . . ?
N1 C4 H4A 111.6 . . ?
N1 C4 H4B 111.6 . . ?
C2 C5 H5 120.5 . . ?
C6 C5 C2 119.07(18) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 121.97(17) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 118.28(17) . . ?
C6 C7 C9 119.84(16) . . ?
C8 C7 C9 121.87(16) . . ?
C3 C8 C7 119.36(16) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C7 120.91(16) . . ?
C14 C9 C7 121.81(16) . . ?
C14 C9 C10 117.23(18) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.81(18) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.07(18) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.58(19) . . ?
C11 C12 Cl1 119.76(17) . . ?
C13 C12 Cl1 119.65(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.31(19) . . ?
C13 C14 H14 119.3 . . ?
C16 C15 S1 120.12(15) . . ?
C20 C15 C16 119.76(19) . . ?
C20 C15 S1 120.11(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C21 120.7(2) . . ?
C19 C18 C17 118.03(19) . . ?
C19 C18 C21 121.2(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 119.5(2) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 110.55(15) . . ?
C1 N1 S1 118.67(13) . . ?
C4 N1 S1 121.49(13) . . ?
N1 S1 C15 107.66(9) . . ?
O1 S1 C15 107.23(10) . . ?
O1 S1 N1 106.02(9) . . ?
O2 S1 C15 108.82(10) . . ?
O2 S1 N1 106.52(10) . . ?
O2 S1 O1 120.02(12) . . ?
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
C1 C2 C3 C4 1.5(2) . . . . ?
C1 C2 C3 C8 -179.19(16) . . . . ?
C1 C2 C5 C6 178.7(2) . . . . ?
C1 N1 S1 C15 62.65(17) . . . . ?
C1 N1 S1 O1 -51.87(17) . . . . ?
C1 N1 S1 O2 179.23(15) . . . . ?
C2 C1 N1 C4 -25.4(2) . . . . ?
C2 C1 N1 S1 -172.66(13) . . . . ?
C2 C3 C4 N1 -16.5(2) . . . . ?
C2 C3 C8 C7 1.0(3) . . . . ?
C2 C5 C6 C7 -0.2(3) . . . . ?
C3 C2 C5 C6 -0.4(3) . . . . ?
C3 C4 N1 C1 26.3(2) . . . . ?
C3 C4 N1 S1 172.41(12) . . . . ?
C4 C3 C8 C7 -179.88(17) . . . . ?
C4 N1 S1 C15 -80.87(18) . . . . ?
C4 N1 S1 O1 164.62(16) . . . . ?
C4 N1 S1 O2 35.71(19) . . . . ?
C5 C2 C3 C4 -179.26(18) . . . . ?
C5 C2 C3 C8 0.1(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C9 -177.41(18) . . . . ?
C6 C7 C8 C3 -1.6(2) . . . . ?
C6 C7 C9 C10 -27.3(3) . . . . ?
C6 C7 C9 C14 149.86(19) . . . . ?
C7 C9 C10 C11 176.50(18) . . . . ?
C7 C9 C14 C13 -176.62(19) . . . . ?
C8 C3 C4 N1 164.30(17) . . . . ?
C8 C7 C9 C10 154.07(17) . . . . ?
C8 C7 C9 C14 -28.7(3) . . . . ?
C9 C7 C8 C3 177.04(15) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C10 C11 C12 Cl1 -178.87(16) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C12 C13 C14 C9 0.7(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C16 C15 S1 N1 -92.81(19) . . . . ?
C16 C15 S1 O1 20.9(2) . . . . ?
C16 C15 S1 O2 152.12(18) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C16 C17 C18 C21 177.9(3) . . . . ?
C17 C18 C19 C20 2.0(4) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C20 C15 C16 C17 1.2(4) . . . . ?
C20 C15 S1 N1 86.21(18) . . . . ?
C20 C15 S1 O1 -160.08(18) . . . . ?
C20 C15 S1 O2 -28.9(2) . . . . ?
C21 C18 C19 C20 -177.5(3) . . . . ?
Cl1 C12 C13 C14 178.71(17) . . . . ?
N1 C1 C2 C3 14.2(2) . . . . ?
N1 C1 C2 C5 -164.91(19) . . . . ?
S1 C15 C16 C17 -179.72(19) . . . . ?
S1 C15 C20 C19 -179.90(19) . . . . ?
_iucr_refine_instructions_details
;
TITL 20160525tjy-1_a.res in P2(1)2(1)2(1)
CELL 1.54184 7.081425 9.08409 29.036883 90 90 90
ZERR 4 0.00009 0.000106 0.000318 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O Cl S
UNIT 84 72 4 8 4 4
L.S. 32
PLAN 20
SIZE 0.22 0.2 0.2
BOND $H
LIST 6
htab
conf
fmap 2
acta
SHEL 999 0.83
REM
REM
REM
WGHT 0.061100 0.217900
FVAR 0.57079
C1 1 0.263347 0.780552 0.322327 11.00000 0.04424 0.06433 =
0.05409 -0.00254 -0.00151 -0.00086
AFIX 23
H1A 2 0.145686 0.807153 0.307384 11.00000 -1.20000
H1B 2 0.250525 0.684064 0.336291 11.00000 -1.20000
AFIX 0
C2 1 0.425786 0.785810 0.289479 11.00000 0.04108 0.04692 =
0.04830 0.00248 -0.00457 0.00303
C3 1 0.577999 0.860585 0.308539 11.00000 0.04527 0.03875 =
0.04520 0.00068 -0.00327 0.00341
C4 1 0.529916 0.908385 0.356881 11.00000 0.04922 0.05770 =
0.04752 -0.00587 0.00012 0.00007
AFIX 23
H4A 2 0.587781 0.844715 0.379685 11.00000 -1.20000
H4B 2 0.567602 1.009432 0.362550 11.00000 -1.20000
AFIX 0
C5 1 0.437241 0.729537 0.245293 11.00000 0.04659 0.06374 =
0.05347 -0.00828 -0.00672 -0.00741
AFIX 43
H5 2 0.335820 0.678871 0.232534 11.00000 -1.20000
AFIX 0
C6 1 0.600767 0.749579 0.220494 11.00000 0.05068 0.05822 =
0.04567 -0.00765 -0.00398 -0.00376
AFIX 43
H6 2 0.608518 0.711409 0.190836 11.00000 -1.20000
AFIX 0
C7 1 0.756078 0.825821 0.238595 11.00000 0.04318 0.03836 =
0.04468 0.00056 -0.00336 0.00340
C8 1 0.743327 0.880476 0.283941 11.00000 0.04261 0.03868 =
0.04665 -0.00337 -0.00475 -0.00186
AFIX 43
H8 2 0.845092 0.929426 0.297183 11.00000 -1.20000
AFIX 0
C9 1 0.925760 0.849827 0.209771 11.00000 0.04804 0.03969 =
0.04249 0.00147 -0.00270 0.00162
C10 1 0.972122 0.752154 0.174226 11.00000 0.05715 0.04399 =
0.04791 -0.00514 0.00032 -0.00553
AFIX 43
H10 2 0.898632 0.668433 0.169916 11.00000 -1.20000
AFIX 0
C11 1 1.124399 0.776778 0.145309 11.00000 0.06535 0.05774 =
0.04394 -0.00538 0.00494 0.00146
AFIX 43
H11 2 1.153343 0.710151 0.122039 11.00000 -1.20000
AFIX 0
C12 1 1.232164 0.901075 0.151484 11.00000 0.05803 0.06240 =
0.04905 0.00742 0.00830 -0.00229
C13 1 1.192932 0.997944 0.186864 11.00000 0.06330 0.04711 =
0.06972 -0.00086 0.00977 -0.01122
AFIX 43
H13 2 1.269062 1.080090 0.191410 11.00000 -1.20000
AFIX 0
C14 1 1.041020 0.972840 0.215412 11.00000 0.05724 0.04344 =
0.05650 -0.00659 0.00492 -0.00358
AFIX 43
H14 2 1.014833 1.039302 0.238922 11.00000 -1.20000
AFIX 0
C15 1 0.208982 0.744451 0.433845 11.00000 0.05206 0.05320 =
0.04164 0.00021 0.00132 0.00575
C16 1 0.073032 0.637704 0.427452 11.00000 0.06253 0.07200 =
0.05942 0.01244 -0.01463 -0.00406
AFIX 43
H16 2 -0.025242 0.653528 0.406791 11.00000 -1.20000
AFIX 0
C17 1 0.082952 0.507672 0.451692 11.00000 0.07619 0.06037 =
0.06756 0.00750 -0.01463 -0.01247
AFIX 43
H17 2 -0.009306 0.436271 0.447151 11.00000 -1.20000
AFIX 0
C18 1 0.227398 0.481116 0.482663 11.00000 0.07562 0.05790 =
0.04790 0.00404 -0.00321 0.00780
C19 1 0.364241 0.586945 0.487768 11.00000 0.07726 0.07805 =
0.06016 0.00905 -0.02728 0.00225
AFIX 43
H19 2 0.464631 0.569720 0.507702 11.00000 -1.20000
AFIX 0
C20 1 0.356066 0.719225 0.463811 11.00000 0.07208 0.06957 =
0.06092 -0.00124 -0.01715 -0.01216
AFIX 43
H20 2 0.449229 0.790134 0.467991 11.00000 -1.20000
AFIX 0
C21 1 0.232799 0.340190 0.510236 11.00000 0.12087 0.07154 =
0.08069 0.02325 -0.01334 0.00588
AFIX 137
H21A 2 0.120439 0.332692 0.528585 11.00000 -1.50000
H21B 2 0.341507 0.340648 0.529989 11.00000 -1.50000
H21C 2 0.239885 0.257658 0.489659 11.00000 -1.50000
AFIX 0
CL1 5 1.421191 0.935568 0.114932 11.00000 0.08811 0.10583 =
0.07512 0.00085 0.03479 -0.02280
N1 3 0.321390 0.892349 0.356398 11.00000 0.04781 0.05580 =
0.04751 -0.00074 0.00614 0.00202
O1 4 0.005052 0.928936 0.388301 11.00000 0.05813 0.07702 =
0.07735 0.02192 0.01760 0.02528
O2 4 0.285382 1.023898 0.429539 11.00000 0.10418 0.05485 =
0.06683 -0.01084 0.02212 -0.00483
S1 6 0.196441 0.911330 0.403115 11.00000 0.06111 0.05138 =
0.05326 0.00363 0.01251 0.00868
HKLF 4
REM 20160525tjy-1_a.res in P2(1)2(1)2(1)
REM R1 = 0.0337 for 3241 Fo > 4sig(Fo) and 0.0345 for all 3334 data
REM 236 parameters refined using 0 restraints
END
WGHT 0.0611 0.2184
REM Highest difference peak 0.143, deepest hole -0.246, 1-sigma level 0.039
Q1 1 0.6355 0.5740 0.5042 11.00000 0.05 0.14
Q2 1 0.5603 0.5305 0.4926 11.00000 0.05 0.12
Q3 1 -0.1631 1.0386 0.4098 11.00000 0.05 0.12
Q4 1 0.3089 0.7523 0.2226 11.00000 0.05 0.12
Q5 1 0.4501 1.0144 0.4296 11.00000 0.05 0.11
Q6 1 0.3726 0.5994 0.3870 11.00000 0.05 0.11
Q7 1 0.2865 0.3433 0.4173 11.00000 0.05 0.10
Q8 1 1.3116 1.0902 0.2139 11.00000 0.05 0.10
Q9 1 -0.1248 0.6963 0.4129 11.00000 0.05 0.10
Q10 1 0.6086 0.7844 0.4233 11.00000 0.05 0.10
Q11 1 0.7872 0.8546 0.3769 11.00000 0.05 0.10
Q12 1 0.9821 0.9061 0.2129 11.00000 0.05 0.10
Q13 1 0.6537 0.4803 0.4837 11.00000 0.05 0.10
Q14 1 0.5186 0.7837 0.1788 11.00000 0.05 0.10
Q15 1 0.7978 0.7765 0.3891 11.00000 0.05 0.10
Q16 1 0.4921 0.9411 0.2066 11.00000 0.05 0.10
Q17 1 0.9773 0.8216 0.1153 11.00000 0.05 0.10
Q18 1 1.3309 0.9243 0.2199 11.00000 0.05 0.10
Q19 1 1.3209 0.8882 0.2176 11.00000 0.05 0.09
Q20 1 0.6355 1.0246 0.3805 11.00000 0.05 0.09
REM The information below was added by Olex2.
REM
REM R1 = 0.0337 for 3241 Fo > 4sig(Fo) and 0.0345 for all 30624 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.14, deepest hole -0.25
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0345
REM R1_gt = 0.0337
REM wR_ref = 0.0935
REM GOOF = 1.030
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 30624
REM Reflections_gt = 3241
REM Parameters = n/a
REM Hole = -0.25
REM Peak = 0.14
REM Flack = -0.005(15)
;
_olex2_submission_special_instructions 'No special instructions were received'