# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_w
_audit_block_doi                 10.5517/ccdc.csd.cc2m74rs
_database_code_depnum_ccdc_archive 'CCDC 2419945'
loop_
_audit_author_name
_audit_author_address
'Victoria Gontcharenko'
;MSU
Russia
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 S'
_chemical_formula_sum            'C13 H10 N2 S'
_chemical_formula_weight         226.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7446(7)
_cell_length_b                   14.6012(9)
_cell_length_c                   7.0569(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.194(3)
_cell_angle_gamma                90
_cell_volume                     1051.76(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.6471
_exptl_absorpt_correction_T_min  0.3683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.5692.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11353
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             3202
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+0.1359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
S1 \\sim C1: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C3(H3), C6(H6), C5(H5), C10(H10), C9(H9)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.08431(4) 0.40738(3) 0.17995(6) 0.02713(14) Uani 1 1 d . U . . .
N1 N 0.15493(11) 0.34504(8) 0.38105(18) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.43551(12) 0.38266(9) 0.5505(2) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.38889(13) 0.29532(10) 0.5398(2) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.25039(13) 0.27662(10) 0.4458(2) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.21057(14) 0.18480(10) 0.4147(2) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.47547(15) 0.22027(11) 0.6100(2) 0.0219(3) Uani 1 1 d . . . . .
C2 C -0.00652(15) 0.23171(10) 0.2242(2) 0.0223(3) Uani 1 1 d . . . . .
H2 H -0.091700 0.216723 0.139242 0.027 Uiso 1 1 calc R U . . .
C8 C 0.60887(16) 0.23939(12) 0.7047(2) 0.0269(3) Uani 1 1 d . . . . .
H8 H 0.668728 0.190759 0.755529 0.032 Uiso 1 1 calc R U . . .
C3 C 0.07862(14) 0.16393(10) 0.3035(2) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.050542 0.101942 0.285245 0.027 Uiso 1 1 calc R U . . .
C1 C 0.02843(14) 0.32581(10) 0.2651(2) 0.0202(3) Uani 1 1 d . U . . .
C6 C 0.42920(16) 0.12852(11) 0.5827(2) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.487945 0.079097 0.631775 0.031 Uiso 1 1 calc R U . . .
C5 C 0.30128(16) 0.11187(11) 0.4867(2) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.271199 0.050358 0.466739 0.030 Uiso 1 1 calc R U . . .
C13 C 0.17999(15) 0.44133(10) 0.4473(3) 0.0250(3) Uani 1 1 d . . . . .
H13A H 0.257078 0.444179 0.566570 0.038 Uiso 1 1 calc R U . . .
H13B H 0.103690 0.465670 0.478656 0.038 Uiso 1 1 calc R U . . .
H13C H 0.195817 0.477921 0.340720 0.038 Uiso 1 1 calc R U . . .
C10 C 0.56138(15) 0.39716(12) 0.6394(3) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.592460 0.458396 0.647197 0.033 Uiso 1 1 calc R U . . .
C9 C 0.65226(15) 0.32789(12) 0.7233(2) 0.0289(4) Uani 1 1 d . . . . .
H9 H 0.741370 0.342086 0.791090 0.035 Uiso 1 1 calc R U . . .


_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
S1 C1 1.6710(16) . ?
N1 C12 1.4022(18) . ?
N1 C1 1.3788(18) . ?
N1 C13 1.4797(19) . ?
N2 C11 1.3635(19) . ?
N2 C10 1.318(2) . ?
C11 C12 1.454(2) . ?
C11 C7 1.423(2) . ?
C12 C4 1.403(2) . ?
C4 C3 1.423(2) . ?
C4 C5 1.426(2) . ?
C7 C8 1.407(2) . ?
C7 C6 1.421(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.345(2) . ?
C2 C1 1.430(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(2) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.351(2) . ?
C5 H5 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C9 1.402(2) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C13 122.10(12) . . ?
C1 N1 C12 122.25(12) . . ?
C1 N1 C13 115.43(12) . . ?
C10 N2 C11 118.76(14) . . ?
N2 C11 C12 120.47(13) . . ?
N2 C11 C7 120.80(13) . . ?
C7 C11 C12 118.64(13) . . ?
N1 C12 C11 123.74(13) . . ?
N1 C12 C4 118.25(13) . . ?
C4 C12 C11 118.00(13) . . ?
C12 C4 C3 119.57(14) . . ?
C12 C4 C5 121.11(14) . . ?
C3 C4 C5 119.28(14) . . ?
C8 C7 C11 118.09(14) . . ?
C8 C7 C6 120.85(14) . . ?
C6 C7 C11 121.05(14) . . ?
C3 C2 H2 119.3 . . ?
C3 C2 C1 121.43(14) . . ?
C1 C2 H2 119.3 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.98(15) . . ?
C9 C8 H8 120.0 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.20(14) . . ?
C2 C3 H3 119.9 . . ?
N1 C1 S1 122.54(11) . . ?
N1 C1 C2 117.61(13) . . ?
C2 C1 S1 119.81(11) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.72(14) . . ?
C5 C6 H6 120.1 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.29(15) . . ?
C6 C5 H5 119.4 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C10 H10 117.9 . . ?
N2 C10 C9 124.11(15) . . ?
C9 C10 H10 117.9 . . ?
C8 C9 C10 118.03(15) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?

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
N1 C12 C4 C3 5.72(19) . . . . ?
N1 C12 C4 C5 -176.50(13) . . . . ?
N2 C11 C12 N1 -7.1(2) . . . . ?
N2 C11 C12 C4 171.52(13) . . . . ?
N2 C11 C7 C8 4.8(2) . . . . ?
N2 C11 C7 C6 -174.15(13) . . . . ?
N2 C10 C9 C8 2.8(2) . . . . ?
C11 N2 C10 C9 0.7(2) . . . . ?
C11 C12 C4 C3 -173.02(12) . . . . ?
C11 C12 C4 C5 4.8(2) . . . . ?
C11 C7 C8 C9 -1.3(2) . . . . ?
C11 C7 C6 C5 0.7(2) . . . . ?
C12 N1 C1 S1 -177.57(10) . . . . ?
C12 N1 C1 C2 4.7(2) . . . . ?
C12 C11 C7 C8 -178.64(12) . . . . ?
C12 C11 C7 C6 2.4(2) . . . . ?
C12 C4 C3 C2 1.8(2) . . . . ?
C12 C4 C5 C6 -1.7(2) . . . . ?
C7 C11 C12 N1 176.32(12) . . . . ?
C7 C11 C12 C4 -5.01(19) . . . . ?
C7 C8 C9 C10 -2.3(2) . . . . ?
C7 C6 C5 C4 -1.1(2) . . . . ?
C8 C7 C6 C5 -178.23(14) . . . . ?
C3 C4 C5 C6 176.07(14) . . . . ?
C3 C2 C1 S1 -174.62(12) . . . . ?
C3 C2 C1 N1 3.1(2) . . . . ?
C1 N1 C12 C11 169.60(12) . . . . ?
C1 N1 C12 C4 -9.06(19) . . . . ?
C1 C2 C3 C4 -6.3(2) . . . . ?
C6 C7 C8 C9 177.71(15) . . . . ?
C5 C4 C3 C2 -176.04(14) . . . . ?
C13 N1 C12 C11 -16.0(2) . . . . ?
C13 N1 C12 C4 165.38(13) . . . . ?
C13 N1 C1 S1 7.63(18) . . . . ?
C13 N1 C1 C2 -170.06(12) . . . . ?
C10 N2 C11 C12 179.01(13) . . . . ?
C10 N2 C11 C7 -4.5(2) . . . . ?

_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_q
_audit_block_doi                 10.5517/ccdc.csd.cc2m74vw
_database_code_depnum_ccdc_archive 'CCDC 2419948'
loop_
_audit_author_name
_audit_author_address
'Victoria Gontcharenko'
;MSU
Russia
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_q                   
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.58 Report
RESPONSE: Presence of high peak of residual electron density (1.5e) near heaviest atom of the structure (sulphur) may be caused by twinning with small fraction not detected during data collection
;
_vrf_PLAT340_q                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01589 Ang.
RESPONSE: This is due to bad sample quality, leading to low I/sigma at 2theta>40
;
# Added during the CSD deposition process: Tuesday 28 January 2025 10:25 AM
# end Validation Reply Form

_audit_creation_date             2023-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 N S'
_chemical_formula_sum            'C10 H9 N S'
_chemical_formula_weight         175.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.077(3)
_cell_length_b                   7.584(2)
_cell_length_c                   28.746(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3287.0(14)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.6471
_exptl_absorpt_correction_T_min  0.4691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1733 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.7249.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_av_unetI/netI     0.1502
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            21752
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      110.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III Detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3470
_reflns_number_total             5748
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.519
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0867
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1223P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2392
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(3)
 0.4(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C6(H6), C7(H7), C22(H22), C32(H32), C21(H21), C8(H8), C31(H31),
 C27(H27), C2(H2), C25(H25), C36(H36), C1(H1), C28(H28), C12(H12), C17(H17),
 C5(H5), C35(H35), C11(H11), C18(H18), C37(H37), C38(H38), C16(H16), C15(H15)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C40(H40A,H40B,
 H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S4 S 0.75508(18) 0.4596(4) 0.26081(13) 0.0269(7) Uani 1 1 d . . . . .
S1 S 0.50825(18) 0.9393(4) 0.73927(13) 0.0299(7) Uani 1 1 d . . . . .
S3 S 0.5585(2) 0.4681(4) 0.52618(12) 0.0346(8) Uani 1 1 d . . . . .
S2 S 0.8192(2) 0.9332(4) 0.47317(13) 0.0371(8) Uani 1 1 d . . . . .
N1 N 0.5345(6) 0.9583(12) 0.5828(3) 0.024(2) Uani 1 1 d . . . . .
N2 N 0.7586(6) 0.9533(13) 0.3192(3) 0.026(2) Uani 1 1 d . . . . .
N3 N 0.5091(6) 0.4472(12) 0.6815(4) 0.024(2) Uani 1 1 d . . . . .
N4 N 0.7908(6) 0.4414(13) 0.4170(3) 0.025(2) Uani 1 1 d . . . . .
C26 C 0.3149(7) 0.2415(14) 0.5926(4) 0.020(2) Uani 1 1 d . . . . .
H26 H 0.270073 0.196767 0.572587 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3066(6) 0.7359(13) 0.6383(4) 0.021(3) Uani 1 1 d . . . . .
H6 H 0.253400 0.688558 0.650828 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3182(8) 0.7437(14) 0.5898(4) 0.022(2) Uani 1 1 d . . . . .
H7 H 0.273488 0.699013 0.569735 0.026 Uiso 1 1 calc R U . . .
C22 C 0.5989(7) 0.5198(15) 0.6167(5) 0.022(3) Uani 1 1 d . . . . .
H22 H 0.653289 0.569403 0.606294 0.026 Uiso 1 1 calc R U . . .
C32 C 0.8408(8) 0.5197(15) 0.3421(5) 0.025(3) Uani 1 1 d . . . . .
H32 H 0.886998 0.572311 0.324413 0.030 Uiso 1 1 calc R U . . .
C21 C 0.5829(7) 0.5130(13) 0.6638(4) 0.016(3) Uani 1 1 d . . . . .
H21 H 0.626692 0.557378 0.684489 0.020 Uiso 1 1 calc R U . . .
C33 C 0.7667(6) 0.4526(14) 0.3182(4) 0.019(2) Uani 1 1 d . . . . .
C8 C 0.3916(7) 0.8136(15) 0.5720(4) 0.025(3) Uani 1 1 d . . . . .
H8 H 0.399497 0.817574 0.539195 0.030 Uiso 1 1 calc R U . . .
C31 C 0.8500(8) 0.5133(14) 0.3886(5) 0.024(3) Uani 1 1 d . . . . .
H31 H 0.901910 0.563242 0.401870 0.029 Uiso 1 1 calc R U . . .
C27 C 0.3046(7) 0.2384(14) 0.6410(4) 0.025(3) Uani 1 1 d . . . . .
H27 H 0.251797 0.190361 0.653821 0.030 Uiso 1 1 calc R U . . .
C2 C 0.5892(7) 1.0183(14) 0.6584(4) 0.022(3) Uani 1 1 d . . . . .
H2 H 0.635175 1.067508 0.676935 0.026 Uiso 1 1 calc R U . . .
C25 C 0.3908(7) 0.3102(15) 0.5751(4) 0.028(3) Uani 1 1 d . . . . .
H25 H 0.398690 0.311092 0.542350 0.034 Uiso 1 1 calc R U . . .
C36 C 0.5585(7) 0.2325(14) 0.3602(4) 0.023(3) Uani 1 1 d . . . . .
H36 H 0.505581 0.184547 0.347441 0.028 Uiso 1 1 calc R U . . .
C1 C 0.5967(7) 1.0219(15) 0.6108(5) 0.025(3) Uani 1 1 d . . . . .
H1 H 0.648460 1.071884 0.597436 0.030 Uiso 1 1 calc R U . . .
C29 C 0.4448(7) 0.3768(14) 0.6516(4) 0.022(2) Uani 1 1 d . . . . .
C4 C 0.4490(7) 0.8735(14) 0.6501(4) 0.020(2) Uani 1 1 d . . . . .
C28 C 0.3687(6) 0.3028(14) 0.6704(4) 0.022(3) Uani 1 1 d . . . . .
H28 H 0.361070 0.296812 0.703187 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8540(8) 1.0102(14) 0.3834(5) 0.024(3) Uani 1 1 d . . . . .
H12 H 0.908719 1.057137 0.394092 0.028 Uiso 1 1 calc R U . . .
C39 C 0.7136(6) 0.3688(13) 0.3981(4) 0.018(2) Uani 1 1 d . . . . .
C17 C 0.5561(7) 0.7379(14) 0.3585(4) 0.026(3) Uani 1 1 d . . . . .
H17 H 0.502237 0.694481 0.345686 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3711(6) 0.7957(14) 0.6674(4) 0.022(3) Uani 1 1 d . . . . .
H5 H 0.363281 0.784656 0.700059 0.026 Uiso 1 1 calc R U . . .
C24 C 0.4589(6) 0.3810(14) 0.6035(4) 0.022(2) Uani 1 1 d . . . . .
C9 C 0.4579(7) 0.8818(13) 0.6016(4) 0.022(2) Uani 1 1 d . . . . .
C34 C 0.6999(7) 0.3731(14) 0.3498(4) 0.023(2) Uani 1 1 d . . . . .
C35 C 0.6211(7) 0.3018(15) 0.3318(4) 0.024(3) Uani 1 1 d . . . . .
H35 H 0.611556 0.302163 0.299114 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6965(6) 0.8763(14) 0.3488(4) 0.021(2) Uani 1 1 d . . . . .
C11 C 0.8352(8) 1.0139(15) 0.3383(5) 0.030(3) Uani 1 1 d . . . . .
H11 H 0.878427 1.062396 0.317964 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5471(8) 0.9618(16) 0.5316(6) 0.035(4) Uani 1 1 d . . . . .
H10A H 0.606012 1.008808 0.524370 0.053 Uiso 1 1 calc R U . . .
H10B H 0.501655 1.037134 0.517472 0.053 Uiso 1 1 calc R U . . .
H10C H 0.541802 0.841919 0.519239 0.053 Uiso 1 1 calc R U . . .
C20 C 0.7442(9) 0.9563(16) 0.2686(6) 0.039(4) Uani 1 1 d . . . . .
H20A H 0.688078 1.016198 0.261737 0.059 Uiso 1 1 calc R U . . .
H20B H 0.741788 0.835166 0.256798 0.059 Uiso 1 1 calc R U . . .
H20C H 0.793052 1.019519 0.253542 0.059 Uiso 1 1 calc R U . . .
C23 C 0.5389(7) 0.4571(15) 0.5834(4) 0.025(3) Uani 1 1 d . . . . .
C18 C 0.6173(7) 0.8075(15) 0.3304(4) 0.028(3) Uani 1 1 d . . . . .
H18 H 0.607302 0.810675 0.297758 0.033 Uiso 1 1 calc R U . . .
C37 C 0.5717(7) 0.2317(14) 0.4077(4) 0.025(3) Uani 1 1 d . . . . .
H37 H 0.526373 0.187619 0.427470 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7126(7) 0.8663(14) 0.3969(4) 0.022(2) Uani 1 1 d . . . . .
C3 C 0.5155(7) 0.9442(15) 0.6802(4) 0.022(3) Uani 1 1 d . . . . .
C38 C 0.6489(7) 0.2932(15) 0.4269(4) 0.026(3) Uani 1 1 d . . . . .
H38 H 0.658538 0.284659 0.459446 0.032 Uiso 1 1 calc R U . . .
C30 C 0.4983(7) 0.4370(15) 0.7314(4) 0.027(3) Uani 1 1 d . . . . .
H30A H 0.547843 0.497621 0.746636 0.040 Uiso 1 1 calc R U . . .
H30B H 0.497453 0.313125 0.741038 0.040 Uiso 1 1 calc R U . . .
H30C H 0.442400 0.493512 0.740340 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7936(8) 0.9372(16) 0.4157(5) 0.032(3) Uani 1 1 d . . . . .
C16 C 0.5704(7) 0.7278(15) 0.4071(4) 0.028(3) Uani 1 1 d . . . . .
H16 H 0.526009 0.680880 0.427026 0.034 Uiso 1 1 calc R U . . .
C15 C 0.6488(7) 0.7864(15) 0.4250(4) 0.029(3) Uani 1 1 d . . . . .
H15 H 0.660287 0.772440 0.457279 0.035 Uiso 1 1 calc R U . . .
C40 C 0.8080(7) 0.4313(15) 0.4672(5) 0.026(3) Uani 1 1 d . . . . .
H40A H 0.864499 0.489307 0.474291 0.039 Uiso 1 1 calc R U . . .
H40B H 0.810892 0.307437 0.476801 0.039 Uiso 1 1 calc R U . . .
H40C H 0.760035 0.490538 0.484153 0.039 Uiso 1 1 calc R U . . .


_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
S4 C33 1.660(13) . ?
S1 C3 1.703(13) . ?
S3 C23 1.673(13) . ?
S2 C13 1.697(14) . ?
N1 C1 1.326(15) . ?
N1 C9 1.402(13) . ?
N1 C10 1.483(18) . ?
N2 C19 1.393(14) . ?
N2 C11 1.360(14) . ?
N2 C20 1.47(2) . ?
N3 C21 1.321(14) . ?
N3 C29 1.401(14) . ?
N3 C30 1.447(16) . ?
N4 C31 1.327(16) . ?
N4 C39 1.397(13) . ?
N4 C40 1.470(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.400(15) . ?
C26 C25 1.353(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.406(15) . ?
C6 C5 1.360(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.330(16) . ?
C22 H22 0.9500 . ?
C22 C21 1.377(16) . ?
C22 C23 1.402(16) . ?
C32 H32 0.9500 . ?
C32 C33 1.407(15) . ?
C32 C31 1.343(18) . ?
C21 H21 0.9500 . ?
C33 C34 1.484(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(14) . ?
C31 H31 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.375(15) . ?
C2 H2 0.9500 . ?
C2 C1 1.374(18) . ?
C2 C3 1.392(16) . ?
C25 H25 0.9500 . ?
C25 C24 1.418(14) . ?
C36 H36 0.9500 . ?
C36 C35 1.354(15) . ?
C36 C37 1.380(15) . ?
C1 H1 0.9500 . ?
C29 C28 1.387(13) . ?
C29 C24 1.398(15) . ?
C4 C5 1.405(14) . ?
C4 C9 1.403(14) . ?
C4 C3 1.428(15) . ?
C28 H28 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.326(18) . ?
C12 C13 1.413(18) . ?
C39 C34 1.405(14) . ?
C39 C38 1.401(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.335(15) . ?
C17 C16 1.417(15) . ?
C5 H5 0.9500 . ?
C24 C23 1.456(15) . ?
C34 C35 1.403(14) . ?
C35 H35 0.9500 . ?
C19 C18 1.406(14) . ?
C19 C14 1.405(14) . ?
C11 H11 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C18 H18 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.370(15) . ?
C14 C13 1.440(15) . ?
C14 C15 1.395(15) . ?
C38 H38 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C15 1.363(16) . ?
C15 H15 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 119.9(10) . . ?
C1 N1 C10 120.4(10) . . ?
C9 N1 C10 119.7(9) . . ?
C19 N2 C20 120.7(10) . . ?
C11 N2 C19 117.8(11) . . ?
C11 N2 C20 121.3(11) . . ?
C21 N3 C29 119.4(10) . . ?
C21 N3 C30 119.7(10) . . ?
C29 N3 C30 120.7(9) . . ?
C31 N4 C39 118.9(10) . . ?
C31 N4 C40 120.5(10) . . ?
C39 N4 C40 120.6(9) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 118.0(10) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(11) . . ?
C8 C7 H7 119.9 . . ?
C21 C22 H22 118.4 . . ?
C21 C22 C23 123.1(10) . . ?
C23 C22 H22 118.4 . . ?
C33 C32 H32 118.2 . . ?
C31 C32 H32 118.2 . . ?
C31 C32 C33 123.6(12) . . ?
N3 C21 C22 122.7(10) . . ?
N3 C21 H21 118.7 . . ?
C22 C21 H21 118.7 . . ?
C32 C33 S4 123.9(9) . . ?
C32 C33 C34 112.8(10) . . ?
C34 C33 S4 123.3(8) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(11) . . ?
C9 C8 H8 119.9 . . ?
N4 C31 C32 123.9(12) . . ?
N4 C31 H31 118.1 . . ?
C32 C31 H31 118.1 . . ?
C26 C27 H27 119.1 . . ?
C28 C27 C26 121.8(11) . . ?
C28 C27 H27 119.1 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.3(11) . . ?
C3 C2 H2 119.3 . . ?
C26 C25 H25 118.5 . . ?
C26 C25 C24 123.1(11) . . ?
C24 C25 H25 118.5 . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.8(11) . . ?
C37 C36 H36 120.1 . . ?
N1 C1 C2 122.7(11) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C28 C29 N3 119.1(10) . . ?
C28 C29 C24 121.4(10) . . ?
C24 C29 N3 119.5(9) . . ?
C5 C4 C3 122.1(10) . . ?
C9 C4 C5 116.7(9) . . ?
C9 C4 C3 121.1(10) . . ?
C27 C28 C29 119.0(11) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(11) . . ?
C13 C12 H12 119.6 . . ?
N4 C39 C34 119.9(9) . . ?
N4 C39 C38 120.8(10) . . ?
C38 C39 C34 119.4(10) . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C16 120.8(11) . . ?
C16 C17 H17 119.6 . . ?
C6 C5 C4 121.3(10) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C25 C24 C23 121.5(10) . . ?
C29 C24 C25 116.7(10) . . ?
C29 C24 C23 121.9(9) . . ?
N1 C9 C8 120.2(10) . . ?
N1 C9 C4 118.7(9) . . ?
C4 C9 C8 121.1(10) . . ?
C39 C34 C33 120.9(9) . . ?
C35 C34 C33 120.4(10) . . ?
C35 C34 C39 118.7(10) . . ?
C36 C35 C34 121.1(11) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
N2 C19 C18 119.7(10) . . ?
N2 C19 C14 120.5(10) . . ?
C14 C19 C18 119.8(10) . . ?
N2 C11 H11 117.7 . . ?
C12 C11 N2 124.7(12) . . ?
C12 C11 H11 117.7 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C23 S3 122.7(9) . . ?
C22 C23 C24 113.4(10) . . ?
C24 C23 S3 123.8(9) . . ?
C17 C18 C19 120.4(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C36 C37 H37 119.3 . . ?
C38 C37 C36 121.3(10) . . ?
C38 C37 H37 119.3 . . ?
C19 C14 C13 119.7(10) . . ?
C15 C14 C19 118.3(10) . . ?
C15 C14 C13 121.9(11) . . ?
C2 C3 S1 120.5(9) . . ?
C2 C3 C4 116.1(11) . . ?
C4 C3 S1 123.3(9) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 C39 119.6(11) . . ?
C37 C38 H38 120.2 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C12 C13 S2 120.0(10) . . ?
C12 C13 C14 116.5(11) . . ?
C14 C13 S2 123.5(10) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 C17 119.1(11) . . ?
C15 C16 H16 120.4 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(12) . . ?
C16 C15 H15 119.3 . . ?
N4 C40 H40A 109.5 . . ?
N4 C40 H40B 109.5 . . ?
N4 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
S4 C33 C34 C39 179.2(8) . . . . ?
S4 C33 C34 C35 -1.3(14) . . . . ?
N2 C19 C18 C17 -178.1(10) . . . . ?
N2 C19 C14 C13 0.3(15) . . . . ?
N2 C19 C14 C15 -179.4(10) . . . . ?
N3 C29 C28 C27 178.2(10) . . . . ?
N3 C29 C24 C25 -179.0(9) . . . . ?
N3 C29 C24 C23 -0.1(15) . . . . ?
N4 C39 C34 C33 0.5(15) . . . . ?
N4 C39 C34 C35 -179.0(9) . . . . ?
N4 C39 C38 C37 176.4(10) . . . . ?
C26 C27 C28 C29 1.6(16) . . . . ?
C26 C25 C24 C29 0.2(15) . . . . ?
C26 C25 C24 C23 -178.7(10) . . . . ?
C6 C7 C8 C9 -0.6(16) . . . . ?
C7 C6 C5 C4 2.8(15) . . . . ?
C7 C8 C9 N1 -178.9(10) . . . . ?
C7 C8 C9 C4 1.7(16) . . . . ?
C32 C33 C34 C39 -0.3(14) . . . . ?
C32 C33 C34 C35 179.2(10) . . . . ?
C21 N3 C29 C28 177.9(10) . . . . ?
C21 N3 C29 C24 -1.5(14) . . . . ?
C21 C22 C23 S3 179.3(8) . . . . ?
C21 C22 C23 C24 -1.2(15) . . . . ?
C33 C32 C31 N4 0.8(17) . . . . ?
C33 C34 C35 C36 -178.4(10) . . . . ?
C31 N4 C39 C34 -0.1(15) . . . . ?
C31 N4 C39 C38 -179.3(10) . . . . ?
C31 C32 C33 S4 -179.8(9) . . . . ?
C31 C32 C33 C34 -0.4(15) . . . . ?
C27 C26 C25 C24 -1.0(16) . . . . ?
C25 C26 C27 C28 0.1(16) . . . . ?
C25 C24 C23 S3 -0.2(15) . . . . ?
C25 C24 C23 C22 -179.8(10) . . . . ?
C36 C37 C38 C39 4.1(16) . . . . ?
C1 N1 C9 C8 -179.8(10) . . . . ?
C1 N1 C9 C4 -0.4(15) . . . . ?
C1 C2 C3 S1 179.3(8) . . . . ?
C1 C2 C3 C4 -0.3(15) . . . . ?
C29 N3 C21 C22 1.7(15) . . . . ?
C29 C24 C23 S3 -179.1(8) . . . . ?
C29 C24 C23 C22 1.4(14) . . . . ?
C28 C29 C24 C25 1.6(15) . . . . ?
C28 C29 C24 C23 -179.5(10) . . . . ?
C39 N4 C31 C32 -0.6(16) . . . . ?
C39 C34 C35 C36 1.1(16) . . . . ?
C17 C16 C15 C14 4.3(17) . . . . ?
C5 C6 C7 C8 -1.6(16) . . . . ?
C5 C4 C9 N1 -180.0(9) . . . . ?
C5 C4 C9 C8 -0.5(15) . . . . ?
C5 C4 C3 S1 0.8(15) . . . . ?
C5 C4 C3 C2 -179.7(10) . . . . ?
C24 C29 C28 C27 -2.5(16) . . . . ?
C9 N1 C1 C2 -0.8(16) . . . . ?
C9 C4 C5 C6 -1.7(15) . . . . ?
C9 C4 C3 S1 179.6(8) . . . . ?
C9 C4 C3 C2 -0.8(15) . . . . ?
C34 C39 C38 C37 -2.8(15) . . . . ?
C35 C36 C37 C38 -2.8(16) . . . . ?
C19 N2 C11 C12 -2.3(16) . . . . ?
C19 C14 C13 S2 179.6(8) . . . . ?
C19 C14 C13 C12 -1.5(15) . . . . ?
C19 C14 C15 C16 -3.7(16) . . . . ?
C11 N2 C19 C18 -178.3(10) . . . . ?
C11 N2 C19 C14 1.5(14) . . . . ?
C11 C12 C13 S2 179.8(9) . . . . ?
C11 C12 C13 C14 0.8(16) . . . . ?
C10 N1 C1 C2 -178.6(10) . . . . ?
C10 N1 C9 C8 -2.0(15) . . . . ?
C10 N1 C9 C4 177.5(10) . . . . ?
C20 N2 C19 C18 -2.9(15) . . . . ?
C20 N2 C19 C14 176.9(10) . . . . ?
C20 N2 C11 C12 -177.7(11) . . . . ?
C23 C22 C21 N3 -0.3(16) . . . . ?
C18 C17 C16 C15 -1.6(16) . . . . ?
C18 C19 C14 C13 -179.8(10) . . . . ?
C18 C19 C14 C15 0.5(15) . . . . ?
C37 C36 C35 C34 0.1(16) . . . . ?
C14 C19 C18 C17 2.1(16) . . . . ?
C3 C2 C1 N1 1.1(17) . . . . ?
C3 C4 C5 C6 177.2(10) . . . . ?
C3 C4 C9 N1 1.1(15) . . . . ?
C3 C4 C9 C8 -179.4(10) . . . . ?
C38 C39 C34 C33 179.8(10) . . . . ?
C38 C39 C34 C35 0.3(15) . . . . ?
C30 N3 C21 C22 177.3(10) . . . . ?
C30 N3 C29 C28 2.4(15) . . . . ?
C30 N3 C29 C24 -177.0(10) . . . . ?
C13 C12 C11 N2 1.1(17) . . . . ?
C13 C14 C15 C16 176.6(11) . . . . ?
C16 C17 C18 C19 -1.5(16) . . . . ?
C15 C14 C13 S2 -0.7(16) . . . . ?
C15 C14 C13 C12 178.2(10) . . . . ?
C40 N4 C31 C32 176.7(10) . . . . ?
C40 N4 C39 C34 -177.4(9) . . . . ?
C40 N4 C39 C38 3.4(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(3)
2 0.4(3)

####################################################################### 
# 
# 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_w_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2m74wx
_database_code_depnum_ccdc_archive 'CCDC 2419949'
loop_
_audit_author_name
_audit_author_address
'Victoria Gontcharenko'
;MSU
Russia
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O S'
_chemical_formula_sum            'C19 H15 N O S'
_chemical_formula_weight         305.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8568(3)
_cell_length_b                   10.5889(4)
_cell_length_c                   8.5261(3)
_cell_angle_alpha                77.1900(10)
_cell_angle_beta                 78.4590(10)
_cell_angle_gamma                82.103(2)
_cell_volume                     760.31(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.6471
_exptl_absorpt_correction_T_min  0.3683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.5692.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.982
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3469
_reflns_number_total             4037
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.4321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06512(5) 0.62039(4) 0.19355(5) 0.02202(12) Uani 1 1 d . . . . .
O1 O 0.18693(15) -0.02609(12) 0.38773(16) 0.0311(3) Uani 1 1 d . . . . .
N1 N 0.18121(14) 0.41624(12) 0.39548(14) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.09504(16) 0.46167(14) 0.27150(17) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.03453(18) 0.36349(16) 0.21753(19) 0.0209(3) Uani 1 1 d . . . . .
H3 H -0.023(2) 0.3921(19) 0.129(2) 0.029(5) Uiso 1 1 d . . . . .
C4 C 0.06155(18) 0.23484(15) 0.28150(19) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.020(2) 0.1721(19) 0.243(2) 0.026(5) Uiso 1 1 d . . . . .
C5 C 0.14930(17) 0.19392(14) 0.40886(18) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.20516(17) 0.28777(14) 0.46263(18) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.264(2) 0.2661(18) 0.544(2) 0.023(5) Uiso 1 1 d . . . . .
C7 C 0.25056(18) 0.51013(15) 0.45748(17) 0.0174(3) Uani 1 1 d . . . . .
H7A H 0.172(2) 0.5808(18) 0.477(2) 0.016(4) Uiso 1 1 d . . . . .
H7B H 0.278(2) 0.4634(18) 0.562(2) 0.022(5) Uiso 1 1 d . . . . .
C8 C 0.38815(16) 0.56531(14) 0.34019(17) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.41186(18) 0.69391(15) 0.33251(19) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.333(2) 0.7460(18) 0.395(2) 0.021(5) Uiso 1 1 d . . . . .
C10 C 0.54010(19) 0.74721(17) 0.2305(2) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.555(3) 0.834(2) 0.224(3) 0.046(6) Uiso 1 1 d . . . . .
C11 C 0.64384(19) 0.67341(18) 0.1340(2) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.730(3) 0.710(2) 0.066(3) 0.043(6) Uiso 1 1 d . . . . .
C12 C 0.61971(19) 0.54571(19) 0.1401(2) 0.0267(4) Uani 1 1 d . . . . .
H12 H 0.692(3) 0.497(2) 0.075(3) 0.038(6) Uiso 1 1 d . . . . .
C13 C 0.49313(18) 0.49157(16) 0.24357(19) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.478(2) 0.4000(18) 0.250(2) 0.019(4) Uiso 1 1 d . . . . .
C14 C 0.18939(18) 0.05299(15) 0.4719(2) 0.0220(3) Uani 1 1 d . . . . .
C15 C 0.23189(19) 0.01147(15) 0.6373(2) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.3535(2) -0.08557(18) 0.6630(3) 0.0339(4) Uani 1 1 d . . . . .
H16 H 0.407(3) -0.119(2) 0.572(3) 0.043(6) Uiso 1 1 d . . . . .
C17 C 0.3906(3) -0.12809(19) 0.8179(3) 0.0431(5) Uani 1 1 d . . . . .
H17 H 0.475(3) -0.193(2) 0.837(3) 0.049(7) Uiso 1 1 d . . . . .
C18 C 0.3058(3) -0.07650(18) 0.9478(3) 0.0378(5) Uani 1 1 d . . . . .
H18 H 0.323(3) -0.106(3) 1.056(3) 0.058(7) Uiso 1 1 d . . . . .
C19 C 0.1848(2) 0.01923(17) 0.9231(2) 0.0286(4) Uani 1 1 d . . . . .
H19 H 0.129(2) 0.0549(18) 1.015(2) 0.024(5) Uiso 1 1 d . . . . .
C20 C 0.14853(19) 0.06390(16) 0.7679(2) 0.0227(3) Uani 1 1 d . . . . .
H20 H 0.064(2) 0.1273(19) 0.752(2) 0.027(5) Uiso 1 1 d . . . . .


_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
S1 C2 1.6701(15) . ?
O1 C14 1.2222(19) . ?
N1 C2 1.3884(18) . ?
N1 C6 1.3592(18) . ?
N1 C7 1.4751(18) . ?
C2 C3 1.430(2) . ?
C3 H3 0.96(2) . ?
C3 C4 1.358(2) . ?
C4 H4 0.95(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.368(2) . ?
C5 C14 1.489(2) . ?
C6 H6 0.92(2) . ?
C7 H7A 0.969(18) . ?
C7 H7B 0.976(19) . ?
C7 C8 1.508(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.390(2) . ?
C9 H9 0.977(19) . ?
C9 C10 1.388(2) . ?
C10 H10 0.94(2) . ?
C10 C11 1.385(3) . ?
C11 H11 0.93(2) . ?
C11 C12 1.386(3) . ?
C12 H12 0.94(2) . ?
C12 C13 1.386(2) . ?
C13 H13 0.985(18) . ?
C14 C15 1.489(2) . ?
C15 C16 1.398(2) . ?
C15 C20 1.388(2) . ?
C16 H16 0.94(2) . ?
C16 C17 1.387(3) . ?
C17 H17 0.96(2) . ?
C17 C18 1.383(3) . ?
C18 H18 0.94(3) . ?
C18 C19 1.385(3) . ?
C19 H19 0.961(19) . ?
C19 C20 1.389(2) . ?
C20 H20 0.94(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
C2 N1 C7 119.23(12) . . ?
C6 N1 C2 122.62(12) . . ?
C6 N1 C7 118.15(12) . . ?
N1 C2 S1 121.52(11) . . ?
N1 C2 C3 115.26(13) . . ?
C3 C2 S1 123.22(12) . . ?
C2 C3 H3 117.1(12) . . ?
C4 C3 C2 122.25(14) . . ?
C4 C3 H3 120.6(12) . . ?
C3 C4 H4 120.3(12) . . ?
C3 C4 C5 120.11(14) . . ?
C5 C4 H4 119.6(12) . . ?
C4 C5 C14 120.64(13) . . ?
C6 C5 C4 117.76(14) . . ?
C6 C5 C14 121.42(14) . . ?
N1 C6 C5 121.96(14) . . ?
N1 C6 H6 116.9(12) . . ?
C5 C6 H6 121.1(12) . . ?
N1 C7 H7A 108.1(11) . . ?
N1 C7 H7B 105.8(11) . . ?
N1 C7 C8 113.03(11) . . ?
H7A C7 H7B 108.9(15) . . ?
C8 C7 H7A 108.9(11) . . ?
C8 C7 H7B 111.9(11) . . ?
C9 C8 C7 118.25(13) . . ?
C13 C8 C7 122.42(13) . . ?
C13 C8 C9 119.31(14) . . ?
C8 C9 H9 118.1(11) . . ?
C10 C9 C8 120.16(15) . . ?
C10 C9 H9 121.6(11) . . ?
C9 C10 H10 120.2(15) . . ?
C11 C10 C9 120.23(16) . . ?
C11 C10 H10 119.6(15) . . ?
C10 C11 H11 119.7(14) . . ?
C10 C11 C12 119.76(15) . . ?
C12 C11 H11 120.5(14) . . ?
C11 C12 H12 118.4(14) . . ?
C13 C12 C11 120.18(16) . . ?
C13 C12 H12 121.4(14) . . ?
C8 C13 H13 119.7(11) . . ?
C12 C13 C8 120.36(15) . . ?
C12 C13 H13 119.9(11) . . ?
O1 C14 C5 119.80(15) . . ?
O1 C14 C15 121.32(15) . . ?
C15 C14 C5 118.87(13) . . ?
C16 C15 C14 119.54(15) . . ?
C20 C15 C14 120.96(14) . . ?
C20 C15 C16 119.45(16) . . ?
C15 C16 H16 117.3(14) . . ?
C17 C16 C15 120.00(19) . . ?
C17 C16 H16 122.7(14) . . ?
C16 C17 H17 120.8(15) . . ?
C18 C17 C16 120.18(19) . . ?
C18 C17 H17 119.1(15) . . ?
C17 C18 H18 123.3(16) . . ?
C17 C18 C19 120.05(18) . . ?
C19 C18 H18 116.6(16) . . ?
C18 C19 H19 118.6(12) . . ?
C18 C19 C20 120.12(18) . . ?
C20 C19 H19 121.2(12) . . ?
C15 C20 C19 120.18(16) . . ?
C15 C20 H20 119.6(12) . . ?
C19 C20 H20 120.2(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
S1 C2 C3 C4 179.34(12) . . . . ?
O1 C14 C15 C16 40.6(2) . . . . ?
O1 C14 C15 C20 -136.73(17) . . . . ?
N1 C2 C3 C4 -1.0(2) . . . . ?
N1 C7 C8 C9 145.48(13) . . . . ?
N1 C7 C8 C13 -36.19(19) . . . . ?
C2 N1 C6 C5 1.9(2) . . . . ?
C2 N1 C7 C8 -73.45(17) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C14 -175.57(14) . . . . ?
C4 C5 C6 N1 -1.3(2) . . . . ?
C4 C5 C14 O1 20.8(2) . . . . ?
C4 C5 C14 C15 -159.23(14) . . . . ?
C5 C14 C15 C16 -139.38(16) . . . . ?
C5 C14 C15 C20 43.3(2) . . . . ?
C6 N1 C2 S1 178.96(11) . . . . ?
C6 N1 C2 C3 -0.8(2) . . . . ?
C6 N1 C7 C8 106.35(15) . . . . ?
C6 C5 C14 O1 -154.24(16) . . . . ?
C6 C5 C14 C15 25.8(2) . . . . ?
C7 N1 C2 S1 -1.26(18) . . . . ?
C7 N1 C2 C3 179.03(12) . . . . ?
C7 N1 C6 C5 -177.86(13) . . . . ?
C7 C8 C9 C10 177.70(14) . . . . ?
C7 C8 C13 C12 -178.60(14) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C8 1.0(2) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
C14 C5 C6 N1 173.84(13) . . . . ?
C14 C15 C16 C17 -177.81(17) . . . . ?
C14 C15 C20 C19 176.68(15) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C15 C20 C19 -0.7(2) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C15 1.0(2) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?

_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_q_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2m74st
_database_code_depnum_ccdc_archive 'CCDC 2419946'
loop_
_audit_author_name
_audit_author_address
'Victoria Gontcharenko'
;MSU
Russia
;
_audit_update_record             
;
2025-01-28 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-01-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H10 Cl N O S)'
_chemical_formula_sum            'C22 H20 Cl2 N2 O2 S2'
_chemical_formula_weight         479.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.8909(5)
_cell_length_b                   3.98570(10)
_cell_length_c                   29.2748(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.3060(10)
_cell_angle_gamma                90
_cell_volume                     2039.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.6471
_exptl_absorpt_correction_T_min  0.3683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.5692.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21097
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.510
_diffrn_reflns_theta_min         2.204
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.9
_diffrn_source_power             0.045
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5079
_reflns_number_total             6206
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.9775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C17(H17), C2(H2), C13(H13), C7(H7), C18(H18), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.34949(2) 0.14452(11) 0.25189(2) 0.01976(10) Uani 1 1 d . . . . .
Cl1 Cl 0.14932(2) 0.25203(11) 0.75221(2) 0.02163(10) Uani 1 1 d . . . . .
S1 S -0.13777(2) 1.12437(11) 0.60106(2) 0.01892(10) Uani 1 1 d . . . . .
S2 S 0.63910(2) 0.97839(12) 0.40532(2) 0.02197(11) Uani 1 1 d . . . . .
O2 O 0.37827(7) 0.5529(3) 0.44829(4) 0.0197(3) Uani 1 1 d . . . . .
O1 O 0.11653(7) 0.7030(3) 0.55737(4) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.49751(7) 0.7333(3) 0.40080(4) 0.0133(3) Uani 1 1 d . . . . .
N1 N -0.00796(7) 0.7861(3) 0.60205(4) 0.0136(3) Uani 1 1 d . . . . .
C15 C 0.42409(9) 0.4492(4) 0.33227(5) 0.0135(3) Uani 1 1 d . . . . .
C9 C 0.06095(9) 0.6327(4) 0.62422(5) 0.0135(3) Uani 1 1 d . . . . .
C16 C 0.35758(9) 0.2798(4) 0.30932(5) 0.0153(3) Uani 1 1 d . . . . .
C20 C 0.43098(9) 0.5573(4) 0.37917(5) 0.0137(3) Uani 1 1 d . . . . .
C14 C 0.48626(9) 0.5115(4) 0.30988(5) 0.0165(3) Uani 1 1 d . . . . .
H14 H 0.482399 0.442297 0.278405 0.020 Uiso 1 1 calc R U . . .
C5 C 0.13787(9) 0.3732(4) 0.69389(5) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.01284(9) 0.6388(4) 0.69624(5) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.017367 0.573257 0.727907 0.020 Uiso 1 1 calc R U . . .
C19 C 0.37010(9) 0.4765(4) 0.40184(5) 0.0151(3) Uani 1 1 d . . . . .
C8 C 0.12258(9) 0.5764(4) 0.60151(5) 0.0154(3) Uani 1 1 d . . . . .
C17 C 0.29863(9) 0.2147(4) 0.33106(6) 0.0178(3) Uani 1 1 d . . . . .
H17 H 0.253709 0.104219 0.314843 0.021 Uiso 1 1 calc R U . . .
C4 C 0.07064(9) 0.5424(4) 0.67186(5) 0.0146(3) Uani 1 1 d . . . . .
C2 C -0.04780(9) 0.8209(4) 0.67498(6) 0.0170(3) Uani 1 1 d . . . . .
H2 H -0.083330 0.896732 0.692632 0.020 Uiso 1 1 calc R U . . .
C1 C -0.06023(9) 0.9037(4) 0.62628(5) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.55002(9) 0.6661(4) 0.33257(6) 0.0182(3) Uani 1 1 d . . . . .
H13 H 0.590917 0.698650 0.316981 0.022 Uiso 1 1 calc R U . . .
C7 C 0.18726(9) 0.4092(4) 0.62473(6) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.227408 0.365937 0.608897 0.022 Uiso 1 1 calc R U . . .
C12 C 0.55823(9) 0.7836(4) 0.37960(5) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.30572(9) 0.3134(4) 0.37744(6) 0.0177(3) Uani 1 1 d . . . . .
H18 H 0.265067 0.267230 0.392750 0.021 Uiso 1 1 calc R U . . .
C6 C 0.19495(9) 0.3025(4) 0.67083(6) 0.0186(3) Uani 1 1 d . . . . .
H6 H 0.239166 0.182511 0.686023 0.022 Uiso 1 1 calc R U . . .
C10 C -0.03228(9) 0.7875(5) 0.55082(5) 0.0189(3) Uani 1 1 d . . . . .
H10A H -0.016874 0.999294 0.538508 0.028 Uiso 1 1 calc R U . . .
H10B H -0.088032 0.764507 0.541939 0.028 Uiso 1 1 calc R U . . .
H10C H -0.008144 0.599823 0.537843 0.028 Uiso 1 1 calc R U . . .
C11 C 0.17909(10) 0.6421(5) 0.53507(6) 0.0213(4) Uani 1 1 d . . . . .
H11A H 0.167212 0.736281 0.503419 0.032 Uiso 1 1 calc R U . . .
H11B H 0.187461 0.399903 0.533348 0.032 Uiso 1 1 calc R U . . .
H11C H 0.225410 0.748588 0.553166 0.032 Uiso 1 1 calc R U . . .
C21 C 0.50443(10) 0.8847(5) 0.44741(5) 0.0196(3) Uani 1 1 d . . . . .
H21A H 0.454784 0.976039 0.450300 0.029 Uiso 1 1 calc R U . . .
H21B H 0.542373 1.065614 0.451488 0.029 Uiso 1 1 calc R U . . .
H21C H 0.520722 0.713249 0.471466 0.029 Uiso 1 1 calc R U . . .
C22 C 0.31838(10) 0.4544(5) 0.47093(6) 0.0223(4) Uani 1 1 d . . . . .
H22A H 0.270450 0.562374 0.455442 0.033 Uiso 1 1 calc R U . . .
H22B H 0.331427 0.523188 0.503811 0.033 Uiso 1 1 calc R U . . .
H22C H 0.312210 0.210138 0.469056 0.033 Uiso 1 1 calc R U . . .


_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
Cl2 C16 1.7418(16) . ?
Cl1 C5 1.7438(16) . ?
S1 C1 1.6754(16) . ?
S2 C12 1.6729(17) . ?
O2 C19 1.3706(18) . ?
O2 C22 1.430(2) . ?
O1 C8 1.3698(18) . ?
O1 C11 1.4316(19) . ?
N2 C20 1.410(2) . ?
N2 C12 1.376(2) . ?
N2 C21 1.4729(19) . ?
N1 C9 1.405(2) . ?
N1 C1 1.371(2) . ?
N1 C10 1.4700(19) . ?
C15 C16 1.408(2) . ?
C15 C20 1.419(2) . ?
C15 C14 1.428(2) . ?
C9 C8 1.421(2) . ?
C9 C4 1.415(2) . ?
C16 C17 1.368(2) . ?
C20 C19 1.428(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.341(2) . ?
C5 C4 1.409(2) . ?
C5 C6 1.368(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.428(2) . ?
C3 C2 1.343(2) . ?
C19 C18 1.382(2) . ?
C8 C7 1.382(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.434(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.432(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.394(2) . ?
C18 H18 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O2 C22 117.85(13) . . ?
C8 O1 C11 117.10(13) . . ?
C20 N2 C21 121.06(13) . . ?
C12 N2 C20 122.82(13) . . ?
C12 N2 C21 116.09(13) . . ?
C9 N1 C10 120.85(13) . . ?
C1 N1 C9 122.54(13) . . ?
C1 N1 C10 116.13(13) . . ?
C16 C15 C20 119.83(14) . . ?
C16 C15 C14 121.74(14) . . ?
C20 C15 C14 118.41(14) . . ?
N1 C9 C8 122.99(14) . . ?
N1 C9 C4 118.50(14) . . ?
C4 C9 C8 118.46(14) . . ?
C15 C16 Cl2 119.79(12) . . ?
C17 C16 Cl2 118.47(13) . . ?
C17 C16 C15 121.73(15) . . ?
N2 C20 C15 118.45(14) . . ?
N2 C20 C19 123.91(14) . . ?
C15 C20 C19 117.63(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 C15 121.06(15) . . ?
C13 C14 H14 119.5 . . ?
C4 C5 Cl1 119.41(13) . . ?
C6 C5 Cl1 118.80(13) . . ?
C6 C5 C4 121.78(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.89(15) . . ?
O2 C19 C20 118.73(14) . . ?
O2 C19 C18 121.21(14) . . ?
C18 C19 C20 120.02(14) . . ?
O1 C8 C9 118.02(14) . . ?
O1 C8 C7 122.08(15) . . ?
C7 C8 C9 119.85(15) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.75(15) . . ?
C18 C17 H17 120.6 . . ?
C9 C4 C3 118.31(14) . . ?
C5 C4 C9 119.08(14) . . ?
C5 C4 C3 122.57(14) . . ?
C3 C2 H2 119.2 . . ?
C3 C2 C1 121.59(15) . . ?
C1 C2 H2 119.2 . . ?
N1 C1 S1 122.92(12) . . ?
N1 C1 C2 117.22(14) . . ?
C2 C1 S1 119.82(12) . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C12 121.90(15) . . ?
C12 C13 H13 119.1 . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C6 121.53(15) . . ?
C6 C7 H7 119.2 . . ?
N2 C12 S2 123.71(12) . . ?
N2 C12 C13 117.21(14) . . ?
C13 C12 S2 119.07(12) . . ?
C19 C18 C17 121.96(15) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C5 C6 C7 119.02(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
Cl2 C16 C17 C18 178.13(13) . . . . ?
Cl1 C5 C4 C9 -178.50(12) . . . . ?
Cl1 C5 C4 C3 4.1(2) . . . . ?
Cl1 C5 C6 C7 -177.77(13) . . . . ?
O2 C19 C18 C17 -175.78(15) . . . . ?
O1 C8 C7 C6 175.36(16) . . . . ?
N2 C20 C19 O2 -4.6(2) . . . . ?
N2 C20 C19 C18 177.72(15) . . . . ?
N1 C9 C8 O1 5.6(2) . . . . ?
N1 C9 C8 C7 -176.81(15) . . . . ?
N1 C9 C4 C5 176.84(14) . . . . ?
N1 C9 C4 C3 -5.6(2) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C15 C20 C19 O2 174.53(14) . . . . ?
C15 C20 C19 C18 -3.1(2) . . . . ?
C15 C14 C13 C12 -1.6(3) . . . . ?
C9 N1 C1 S1 173.01(12) . . . . ?
C9 N1 C1 C2 -9.1(2) . . . . ?
C9 C8 C7 C6 -2.1(3) . . . . ?
C16 C15 C20 N2 -178.51(14) . . . . ?
C16 C15 C20 C19 2.3(2) . . . . ?
C16 C15 C14 C13 -178.38(16) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C20 N2 C12 S2 -177.53(12) . . . . ?
C20 N2 C12 C13 3.7(2) . . . . ?
C20 C15 C16 Cl2 -179.53(12) . . . . ?
C20 C15 C16 C17 -0.1(2) . . . . ?
C20 C15 C14 C13 0.5(2) . . . . ?
C20 C19 C18 C17 1.8(3) . . . . ?
C14 C15 C16 Cl2 -0.7(2) . . . . ?
C14 C15 C16 C17 178.77(16) . . . . ?
C14 C15 C20 N2 2.6(2) . . . . ?
C14 C15 C20 C19 -176.61(15) . . . . ?
C14 C13 C12 S2 -179.25(14) . . . . ?
C14 C13 C12 N2 -0.4(2) . . . . ?
C3 C2 C1 S1 178.67(13) . . . . ?
C3 C2 C1 N1 0.7(2) . . . . ?
C8 C9 C4 C5 -5.6(2) . . . . ?
C8 C9 C4 C3 171.93(15) . . . . ?
C8 C7 C6 C5 -1.7(3) . . . . ?
C4 C9 C8 O1 -171.82(14) . . . . ?
C4 C9 C8 C7 5.8(2) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C4 C3 C2 C1 4.9(3) . . . . ?
C2 C3 C4 C9 -2.3(2) . . . . ?
C2 C3 C4 C5 175.13(16) . . . . ?
C1 N1 C9 C8 -165.84(15) . . . . ?
C1 N1 C9 C4 11.6(2) . . . . ?
C12 N2 C20 C15 -4.8(2) . . . . ?
C12 N2 C20 C19 174.36(15) . . . . ?
C6 C5 C4 C9 1.9(2) . . . . ?
C6 C5 C4 C3 -175.56(16) . . . . ?
C10 N1 C9 C8 22.5(2) . . . . ?
C10 N1 C9 C4 -160.13(15) . . . . ?
C10 N1 C1 S1 -14.9(2) . . . . ?
C10 N1 C1 C2 163.01(15) . . . . ?
C11 O1 C8 C9 -179.74(15) . . . . ?
C11 O1 C8 C7 2.7(2) . . . . ?
C21 N2 C20 C15 173.13(14) . . . . ?
C21 N2 C20 C19 -7.7(2) . . . . ?
C21 N2 C12 S2 4.5(2) . . . . ?
C21 N2 C12 C13 -174.35(15) . . . . ?
C22 O2 C19 C20 -176.84(15) . . . . ?
C22 O2 C19 C18 0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
