# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_g230613b_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2hjlc0
_database_code_depnum_ccdc_archive 'CCDC 2309852'
loop_
_audit_author_name
_audit_author_address
'Xu Shuilian'
;Soochow University
China
;
_audit_update_record             
;
2023-11-23 deposited with the CCDC.	2024-05-19 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 Br N O3 S2'
_chemical_formula_sum            'C19 H24 Br N O3 S2'
_chemical_formula_weight         458.42
_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'
Br Br -0.2901 2.4595 '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                   7.9637(6)
_cell_length_b                   8.4266(5)
_cell_length_c                   16.2353(10)
_cell_angle_alpha                78.595(5)
_cell_angle_beta                 76.521(6)
_cell_angle_gamma                84.394(5)
_cell_volume                     1037.05(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3655
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      28.0760
_cell_measurement_theta_min      2.4430
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.558
_exptl_absorpt_coefficient_mu    2.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.129
_diffrn_reflns_theta_min         2.469
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  41.00   1.00    2.00    --   12.72 -57.00 -90.00  100
  2  ω    -62.00  37.00   1.00    2.00    --   12.72 -37.00-150.00   99
  3  ω     16.00  87.00   1.00    2.00    --   12.72  37.00  30.00   71
  4  ω    -41.00  14.00   1.00    2.00    --  -13.50  77.00 150.00   55
  5  ω    -38.00  19.00   1.00    2.00    --  -13.50 -77.00  30.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0750082000
_diffrn_orient_matrix_UB_12      -0.0108822000
_diffrn_orient_matrix_UB_13      -0.0143166000
_diffrn_orient_matrix_UB_21      -0.0335715000
_diffrn_orient_matrix_UB_22      -0.0483015000
_diffrn_orient_matrix_UB_23      0.0405089000
_diffrn_orient_matrix_UB_31      -0.0407429000
_diffrn_orient_matrix_UB_32      0.0703120000
_diffrn_orient_matrix_UB_33      0.0155118000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3375
_reflns_number_total             5275
_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       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.541
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.037
_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)+(0.0289P)²+0.2473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C5(H5), C2(H2), C14(H14), C18(H18), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C)
;
_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
Br1 Br 1.25036(5) 0.20338(4) 0.42858(2) 0.05944(15) Uani 1 1 d . . . . .
S1 S 0.48996(10) 0.39963(8) 0.62757(5) 0.03095(18) Uani 1 1 d . . . . .
O3 O 0.3613(3) 0.7049(2) 0.68254(13) 0.0398(5) Uani 1 1 d . . . . .
O1 O 0.3799(3) 0.2433(2) 0.64164(13) 0.0392(5) Uani 1 1 d . . . . .
O2 O 0.4799(3) 0.6257(3) 0.81268(14) 0.0470(6) Uani 1 1 d . . . . .
N1 N 0.5155(3) 0.4282(3) 0.71779(15) 0.0325(6) Uani 1 1 d . . . . .
C6 C 0.7013(4) 0.3249(3) 0.58153(18) 0.0291(6) Uani 1 1 d . . . . .
C3 C 1.0246(4) 0.2444(3) 0.4937(2) 0.0378(8) Uani 1 1 d . . . . .
C4 C 0.8846(4) 0.2177(3) 0.46397(19) 0.0391(8) Uani 1 1 d . . . . .
H4 H 0.899750 0.171522 0.414395 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8431(4) 0.3494(4) 0.61173(19) 0.0359(7) Uani 1 1 d . . . . .
H1 H 0.828358 0.393084 0.662090 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7201(4) 0.2595(3) 0.50767(18) 0.0362(7) Uani 1 1 d . . . . .
H5 H 0.622507 0.243814 0.487560 0.043 Uiso 1 1 calc R U . . .
C2 C 1.0079(4) 0.3090(4) 0.56718(19) 0.0398(8) Uani 1 1 d . . . . .
H2 H 1.106027 0.325300 0.586669 0.048 Uiso 1 1 calc R U . . .
C14 C 0.0507(4) 0.5404(4) 0.7765(2) 0.0425(8) Uani 1 1 d . . . . .
H14 H 0.058476 0.604329 0.721380 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1846(4) 0.4092(4) 0.8905(2) 0.0446(8) Uani 1 1 d . . . . .
H18 H 0.283399 0.383178 0.913897 0.054 Uiso 1 1 calc R U . . .
C9 C 0.1145(4) 0.0425(4) 0.7607(2) 0.0445(8) Uani 1 1 d . . . . .
H9A H 0.120405 -0.015844 0.713483 0.053 Uiso 1 1 calc R U . . .
H9B H 0.070110 0.153712 0.743164 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4304(4) 0.0890(3) 0.6928(2) 0.0467(9) Uani 1 1 d . . . . .
H7A H 0.541763 0.098114 0.706950 0.056 Uiso 1 1 calc R U . . .
H7B H 0.443667 0.002382 0.659086 0.056 Uiso 1 1 calc R U . . .
C15 C -0.1065(4) 0.4835(4) 0.8233(2) 0.0483(9) Uani 1 1 d . . . . .
H15 H -0.205045 0.509939 0.799839 0.058 Uiso 1 1 calc R U . . .
C16 C -0.1215(4) 0.3888(4) 0.9040(2) 0.0435(8) Uani 1 1 d . . . . .
C8 C 0.2949(4) 0.0475(4) 0.7747(2) 0.0442(8) Uani 1 1 d . . . . .
H8A H 0.293618 0.127636 0.811109 0.053 Uiso 1 1 calc R U . . .
H8B H 0.327574 -0.058608 0.805886 0.053 Uiso 1 1 calc R U . . .
C10 C -0.0119(4) -0.0386(4) 0.8401(2) 0.0445(8) Uani 1 1 d . . . . .
H10A H 0.028834 -0.151688 0.855703 0.053 Uiso 1 1 calc R U . . .
H10B H -0.012859 0.015824 0.888324 0.053 Uiso 1 1 calc R U . . .
C11 C -0.1942(5) -0.0347(5) 0.8275(2) 0.0553(10) Uani 1 1 d . . . . .
H11A H -0.192694 -0.085745 0.778034 0.066 Uiso 1 1 calc R U . . .
H11B H -0.236434 0.078451 0.813930 0.066 Uiso 1 1 calc R U . . .
C17 C 0.0266(5) 0.3531(4) 0.9363(2) 0.0511(9) Uani 1 1 d . . . . .
H17 H 0.019333 0.288561 0.991180 0.061 Uiso 1 1 calc R U . . .
C19 C -0.2942(5) 0.3302(5) 0.9556(2) 0.0653(11) Uani 1 1 d . . . . .
H19A H -0.356325 0.413996 0.985877 0.098 Uiso 1 1 calc R U . . .
H19B H -0.276648 0.233320 0.996939 0.098 Uiso 1 1 calc R U . . .
H19C H -0.360893 0.305467 0.917213 0.098 Uiso 1 1 calc R U . . .
C12 C -0.3196(5) -0.1212(5) 0.9061(2) 0.0677(12) Uani 1 1 d . . . . .
H12A H -0.434472 -0.112707 0.894433 0.102 Uiso 1 1 calc R U . . .
H12B H -0.322346 -0.071152 0.955380 0.102 Uiso 1 1 calc R U . . .
H12C H -0.281559 -0.234590 0.918492 0.102 Uiso 1 1 calc R U . . .
C13 C 0.1960(4) 0.5038(3) 0.81011(18) 0.0305(7) Uani 1 1 d . . . . .
S2 S 0.39594(10) 0.58131(9) 0.75238(5) 0.03311(19) Uani 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
Br1 C3 1.899(3) . ?
S1 O1 1.602(2) . ?
S1 N1 1.591(2) . ?
S1 C6 1.784(3) . ?
O3 S2 1.438(2) . ?
O1 C7 1.473(4) . ?
O2 S2 1.430(2) . ?
N1 S2 1.638(2) . ?
C6 C1 1.379(4) . ?
C6 C5 1.388(4) . ?
C3 C4 1.367(5) . ?
C3 C2 1.381(4) . ?
C4 H4 0.9400 . ?
C4 C5 1.385(4) . ?
C1 H1 0.9400 . ?
C1 C2 1.389(4) . ?
C5 H5 0.9400 . ?
C2 H2 0.9400 . ?
C14 H14 0.9400 . ?
C14 C15 1.380(4) . ?
C14 C13 1.375(4) . ?
C18 H18 0.9400 . ?
C18 C17 1.379(4) . ?
C18 C13 1.377(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C8 1.511(5) . ?
C9 C10 1.525(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C8 1.508(4) . ?
C15 H15 0.9400 . ?
C15 C16 1.378(5) . ?
C16 C17 1.383(5) . ?
C16 C19 1.507(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C11 1.509(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.529(5) . ?
C17 H17 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 S2 1.763(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C6 101.52(12) . . ?
N1 S1 O1 109.85(12) . . ?
N1 S1 C6 101.29(14) . . ?
C7 O1 S1 120.2(2) . . ?
S1 N1 S2 113.63(15) . . ?
C1 C6 S1 121.2(2) . . ?
C1 C6 C5 121.2(3) . . ?
C5 C6 S1 117.1(2) . . ?
C4 C3 Br1 119.2(2) . . ?
C4 C3 C2 122.2(3) . . ?
C2 C3 Br1 118.5(3) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C6 C1 H1 120.3 . . ?
C6 C1 C2 119.5(3) . . ?
C2 C1 H1 120.3 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(3) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C13 C18 C17 119.2(3) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C8 C9 C10 113.6(3) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
O1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
O1 C7 C8 110.2(2) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 117.5(3) . . ?
C15 C16 C19 120.9(3) . . ?
C17 C16 C19 121.5(3) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 C9 114.2(3) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.5(3) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.4(3) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.9(3) . . ?
C14 C13 S2 120.6(2) . . ?
C18 C13 S2 119.6(3) . . ?
O3 S2 N1 111.92(12) . . ?
O3 S2 C13 107.15(14) . . ?
O2 S2 O3 118.11(13) . . ?
O2 S2 N1 105.03(13) . . ?
O2 S2 C13 107.73(14) . . ?
N1 S2 C13 106.28(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
Br1 C3 C4 C5 -175.0(2) . . . . ?
Br1 C3 C2 C1 175.7(2) . . . . ?
S1 O1 C7 C8 113.1(3) . . . . ?
S1 N1 S2 O3 -29.39(19) . . . . ?
S1 N1 S2 O2 -158.72(15) . . . . ?
S1 N1 S2 C13 87.27(17) . . . . ?
S1 C6 C1 C2 -171.4(2) . . . . ?
S1 C6 C5 C4 172.4(2) . . . . ?
O1 S1 N1 S2 -105.94(15) . . . . ?
O1 S1 C6 C1 -132.1(2) . . . . ?
O1 S1 C6 C5 55.7(2) . . . . ?
O1 C7 C8 C9 55.0(4) . . . . ?
N1 S1 O1 C7 -50.6(2) . . . . ?
N1 S1 C6 C1 -18.9(3) . . . . ?
N1 S1 C6 C5 168.9(2) . . . . ?
C6 S1 O1 C7 56.0(2) . . . . ?
C6 S1 N1 S2 147.29(15) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C3 C2 C1 -0.6(5) . . . . ?
C1 C6 C5 C4 0.3(4) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C14 C15 C16 C19 178.7(3) . . . . ?
C14 C13 S2 O3 12.3(3) . . . . ?
C14 C13 S2 O2 140.3(2) . . . . ?
C14 C13 S2 N1 -107.6(2) . . . . ?
C18 C13 S2 O3 -166.1(2) . . . . ?
C18 C13 S2 O2 -38.0(3) . . . . ?
C18 C13 S2 N1 74.1(3) . . . . ?
C9 C10 C11 C12 178.0(3) . . . . ?
C15 C14 C13 C18 0.5(4) . . . . ?
C15 C14 C13 S2 -177.9(2) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C8 C9 C10 C11 176.7(3) . . . . ?
C10 C9 C8 C7 165.9(3) . . . . ?
C17 C18 C13 C14 -0.3(5) . . . . ?
C17 C18 C13 S2 178.1(2) . . . . ?
C19 C16 C17 C18 -178.5(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C13 C18 C17 C16 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.875
####################################################################### 
# 
# 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_mo_b240105e_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2j03h5
_database_code_depnum_ccdc_archive 'CCDC 2323806'
loop_
_audit_author_name
_audit_author_address
'Xu Shuilian'
;Soochow University
China
;
_audit_update_record             
;
2024-01-06 deposited with the CCDC.	2024-05-19 downloaded from the CCDC.
;
_audit_creation_date             2024-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Br Cl2 N O3 S3'
_chemical_formula_sum            'C16 H18 Br Cl2 N O3 S3'
_chemical_formula_weight         519.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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      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                   6.6878(2)
_cell_length_b                   7.1027(3)
_cell_length_c                   22.8301(8)
_cell_angle_alpha                89.7990(10)
_cell_angle_beta                 87.8530(10)
_cell_angle_gamma                75.2420(10)
_cell_volume                     1047.93(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8993
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.517
_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.6727.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14523
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         1.785
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3480
_reflns_number_total             3953
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.967
_refine_diff_density_min         -2.006
_refine_diff_density_rms         0.165
_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     229
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.050
_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)+(0.1065P)²+6.2733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.1946
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C14A
 1.385 with sigma of 0.01
 C14A-C15A
 1.372 with sigma of 0.01
 C13A-C15A
 2.4 with sigma of 0.01
 C14B-C16B
 2.38 with sigma of 0.01
3. Others
 Fixed Sof: Cl2B(0.5) Cl1B(0.5) C13B(0.5) C16B(0.5) C15B(0.5) C14B(0.5)
 H14B(0.5) S3A(0.5) Cl1A(0.5) Cl2A(0.5) C13A(0.5) C15A(0.5) C16A(0.5) C14A(0.5)
 H14A(0.5) S3B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C10(H10A,H10B), C8(H8A,H8B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C14B(H14B), C14A(H14A)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl2B Cl 0.6094(9) 0.3827(9) 0.0677(2) 0.0516(16) Uiso 0.5 1 d . . P A 2
Cl1B Cl 0.9119(7) 0.6423(8) 0.1150(2) 0.0465(12) Uiso 0.5 1 d . . P A 2
S1 S 0.2462(2) 0.5069(2) 0.33519(6) 0.0235(3) Uani 1 1 d . . . . .
S2 S 0.6443(2) 0.3061(2) 0.31718(6) 0.0270(3) Uani 1 1 d . . . . .
O1 O 0.1756(6) 0.6734(6) 0.28650(18) 0.0285(9) Uani 1 1 d . . . . .
O3 O 0.8372(7) 0.2896(7) 0.34403(19) 0.0381(11) Uani 1 1 d . . . . .
O2 O 0.5648(7) 0.1370(6) 0.3128(2) 0.0383(10) Uani 1 1 d . . . . .
N1 N 0.4831(7) 0.4885(7) 0.3492(2) 0.0274(10) Uani 1 1 d . . . . .
C6 C 0.2204(9) 0.6257(8) 0.4517(2) 0.0246(11) Uani 1 1 d . . . . .
H6 H 0.365300 0.569826 0.452747 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1091(9) 0.7053(8) 0.5023(3) 0.0260(12) Uani 1 1 d . . . . .
H5 H 0.176222 0.705609 0.538204 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1015(9) 0.7838(8) 0.4989(3) 0.0268(12) Uani 1 1 d . . . . .
C1 C 0.1187(9) 0.6283(8) 0.3994(2) 0.0237(11) Uani 1 1 d . . . . .
C13B C 0.6814(16) 0.3865(15) 0.2443(4) 0.000(2) Uiso 0.5 1 d . . P A 2
C2 C -0.0925(10) 0.7067(10) 0.3970(3) 0.0344(14) Uani 1 1 d . . . . .
H2 H -0.160321 0.705916 0.361209 0.041 Uiso 1 1 calc R U . . .
C3 C -0.2037(10) 0.7860(10) 0.4471(3) 0.0351(14) Uani 1 1 d . . . . .
H3 H -0.348598 0.841498 0.446007 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2588(10) 0.9159(9) 0.1847(3) 0.0312(13) Uani 1 1 d . . . . .
H9A H 0.250166 0.781540 0.176474 0.037 Uiso 1 1 calc R U . . .
H9B H 0.406670 0.913093 0.188169 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2231(11) 0.8642(9) 0.2947(3) 0.0353(14) Uani 1 1 d . . . . .
H7A H 0.374131 0.846918 0.297368 0.042 Uiso 1 1 calc R U . . .
H7B H 0.153585 0.928347 0.331107 0.042 Uiso 1 1 calc R U . . .
C16B C 0.644(4) 0.425(4) 0.1322(9) 0.059(8) Uiso 0.5 1 d D . P A 2
C10 C 0.1717(11) 1.0466(10) 0.1336(3) 0.0365(14) Uani 1 1 d . . . . .
H10A H 0.023157 1.051072 0.130990 0.044 Uiso 1 1 calc R U . . .
H10B H 0.181828 1.180393 0.142022 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1444(11) 0.9843(9) 0.2422(3) 0.0350(14) Uani 1 1 d . . . . .
H8A H 0.151248 1.119824 0.249568 0.042 Uiso 1 1 calc R U . . .
H8B H -0.003047 0.986435 0.238302 0.042 Uiso 1 1 calc R U . . .
C15B C 0.781(3) 0.511(3) 0.1591(10) 0.032(7) Uiso 0.5 1 d . . P A 2
C11 C 0.2780(12) 0.9835(14) 0.0750(3) 0.053(2) Uani 1 1 d . . . . .
H11A H 0.257862 0.854433 0.064762 0.064 Uiso 1 1 calc R U . . .
H11B H 0.428404 0.968942 0.078197 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1997(15) 1.1242(16) 0.0263(4) 0.066(3) Uani 1 1 d . . . . .
H12A H 0.221290 1.251886 0.035694 0.099 Uiso 1 1 calc R U . . .
H12B H 0.051692 1.136358 0.021941 0.099 Uiso 1 1 calc R U . . .
H12C H 0.275246 1.075626 -0.010515 0.099 Uiso 1 1 calc R U . . .
Br1 Br -0.26106(9) 0.87808(8) 0.56780(2) 0.0316(2) Uani 1 1 d . . . . .
C14B C 0.777(3) 0.493(3) 0.2218(7) 0.046(5) Uiso 0.5 1 d D . P A 2
H14B H 0.847910 0.562878 0.245204 0.055 Uiso 0.5 1 calc R U P A 2
S3A S 0.8174(11) 0.5276(10) 0.2299(3) 0.0728(17) Uiso 0.5 1 d . . P A 1
Cl1A Cl 0.5658(9) 0.4252(8) 0.0690(2) 0.0482(14) Uiso 0.5 1 d . . P A 1
Cl2A Cl 0.8657(7) 0.6950(7) 0.12140(19) 0.0441(11) Uiso 0.5 1 d . . P A 1
C13A C 0.654(3) 0.357(3) 0.2444(5) 0.051(7) Uiso 0.5 1 d D . P A 1
C15A C 0.645(2) 0.418(2) 0.1431(5) 0.015(3) Uiso 0.5 1 d D . P A 1
C16A C 0.760(3) 0.542(3) 0.1624(9) 0.028(6) Uiso 0.5 1 d . . P A 1
C14A C 0.566(2) 0.323(2) 0.1900(5) 0.027(5) Uiso 0.5 1 d D . P A 1
H14A H 0.468742 0.247726 0.186022 0.033 Uiso 0.5 1 calc R U P A 1
S3B S 0.5487(5) 0.2878(6) 0.19101(13) 0.0159(8) Uiso 0.5 1 d . . P A 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
Cl2B C16B 1.541(19) . ?
Cl1B C15B 1.73(2) . ?
S1 O1 1.613(4) . ?
S1 N1 1.600(5) . ?
S1 C1 1.778(6) . ?
S2 O3 1.426(4) . ?
S2 O2 1.438(5) . ?
S2 N1 1.616(5) . ?
S2 C13B 1.787(9) . ?
S2 C13A 1.701(13) . ?
O1 C7 1.482(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(8) . ?
C6 C1 1.393(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(8) . ?
C4 C3 1.388(9) . ?
C4 Br1 1.891(6) . ?
C1 C2 1.383(8) . ?
C13B C14B 1.21(2) . ?
C13B S3B 1.778(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(9) . ?
C3 H3 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(9) . ?
C9 C8 1.512(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.500(9) . ?
C16B C15B 1.38(3) . ?
C16B S3B 1.85(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C15B C14B 1.44(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14B H14B 0.9500 . ?
S3A C13A 1.85(2) . ?
S3A C16A 1.60(2) . ?
Cl1A C15A 1.790(14) . ?
Cl2A C16A 1.70(2) . ?
C13A C14A 1.441(9) . ?
C15A C16A 1.39(2) . ?
C15A C14A 1.417(9) . ?
C14A H14A 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
O1 S1 C1 101.2(2) . . ?
N1 S1 O1 108.9(2) . . ?
N1 S1 C1 101.0(3) . . ?
O3 S2 O2 119.4(3) . . ?
O3 S2 N1 105.7(3) . . ?
O3 S2 C13B 105.0(4) . . ?
O3 S2 C13A 112.7(7) . . ?
O2 S2 N1 113.2(3) . . ?
O2 S2 C13B 107.3(4) . . ?
O2 S2 C13A 97.7(7) . . ?
N1 S2 C13B 105.1(4) . . ?
N1 S2 C13A 107.8(8) . . ?
C7 O1 S1 118.9(4) . . ?
S1 N1 S2 114.0(3) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C1 119.7(5) . . ?
C1 C6 H6 120.1 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.8 . . ?
C5 C4 C3 122.2(5) . . ?
C5 C4 Br1 119.6(4) . . ?
C3 C4 Br1 118.2(4) . . ?
C6 C1 S1 121.9(4) . . ?
C2 C1 S1 116.6(4) . . ?
C2 C1 C6 121.1(5) . . ?
C14B C13B S2 135.3(10) . . ?
C14B C13B S3B 111.0(10) . . ?
S3B C13B S2 113.7(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 H3 120.4 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.5(5) . . ?
O1 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
O1 C7 C8 106.4(5) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
Cl2B C16B S3B 119.4(15) . . ?
C15B C16B Cl2B 133(2) . . ?
C15B C16B S3B 104.7(15) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.7(6) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 C9 115.5(5) . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C16B C15B Cl1B 117.1(18) . . ?
C16B C15B C14B 113.4(19) . . ?
C14B C15B Cl1B 129.2(16) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.4(7) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13B C14B C15B 118.9(16) . . ?
C13B C14B H14B 120.6 . . ?
C15B C14B H14B 120.6 . . ?
C16A S3A C13A 91.1(9) . . ?
S2 C13A S3A 110.5(9) . . ?
C14A C13A S2 141.4(14) . . ?
C14A C13A S3A 107.8(9) . . ?
C16A C15A Cl1A 120.9(12) . . ?
C16A C15A C14A 112.5(13) . . ?
C14A C15A Cl1A 125.3(9) . . ?
S3A C16A Cl2A 115.2(12) . . ?
C15A C16A S3A 116.9(15) . . ?
C15A C16A Cl2A 127.6(15) . . ?
C13A C14A H14A 124.7 . . ?
C15A C14A C13A 110.7(9) . . ?
C15A C14A H14A 124.7 . . ?
C13B S3B C16B 91.1(7) . . ?

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
Cl2B C16B C15B Cl1B 15(4) . . . . ?
Cl2B C16B C15B C14B -171(2) . . . . ?
Cl2B C16B S3B C13B 170.8(18) . . . . ?
Cl1B C15B C14B C13B -176.8(16) . . . . ?
S1 O1 C7 C8 178.5(4) . . . . ?
S1 C1 C2 C3 173.8(5) . . . . ?
S2 C13B C14B C15B 175.5(13) . . . . ?
S2 C13B S3B C16B 178.9(10) . . . . ?
S2 C13A C14A C15A 178(2) . . . . ?
O1 S1 N1 S2 -101.1(3) . . . . ?
O1 S1 C1 C6 -133.0(5) . . . . ?
O1 S1 C1 C2 54.2(5) . . . . ?
O1 C7 C8 C9 -68.0(7) . . . . ?
O3 S2 N1 S1 -168.2(3) . . . . ?
O3 S2 C13B C14B -35.1(16) . . . . ?
O3 S2 C13B S3B 144.6(5) . . . . ?
O3 S2 C13A S3A -38.0(13) . . . . ?
O3 S2 C13A C14A 148(2) . . . . ?
O2 S2 N1 S1 -35.8(4) . . . . ?
O2 S2 C13B C14B -163.1(15) . . . . ?
O2 S2 C13B S3B 16.6(6) . . . . ?
O2 S2 C13A S3A -164.4(10) . . . . ?
O2 S2 C13A C14A 22(3) . . . . ?
N1 S1 O1 C7 -48.2(5) . . . . ?
N1 S1 C1 C6 -21.0(5) . . . . ?
N1 S1 C1 C2 166.2(5) . . . . ?
N1 S2 C13B C14B 76.1(16) . . . . ?
N1 S2 C13B S3B -104.2(5) . . . . ?
N1 S2 C13A S3A 78.2(11) . . . . ?
N1 S2 C13A C14A -95(3) . . . . ?
C6 C5 C4 C3 -0.2(9) . . . . ?
C6 C5 C4 Br1 175.9(4) . . . . ?
C6 C1 C2 C3 0.9(10) . . . . ?
C5 C6 C1 S1 -173.3(4) . . . . ?
C5 C6 C1 C2 -0.8(9) . . . . ?
C5 C4 C3 C2 0.3(10) . . . . ?
C1 S1 O1 C7 57.6(5) . . . . ?
C1 S1 N1 S2 153.0(3) . . . . ?
C1 C6 C5 C4 0.5(8) . . . . ?
C1 C2 C3 C4 -0.6(10) . . . . ?
C13B S2 N1 S1 81.0(5) . . . . ?
C9 C10 C11 C12 -175.4(7) . . . . ?
C16B C15B C14B C13B 10(3) . . . . ?
C10 C9 C8 C7 -179.3(6) . . . . ?
C8 C9 C10 C11 -179.2(6) . . . . ?
C15B C16B S3B C13B 6.2(18) . . . . ?
Br1 C4 C3 C2 -175.9(5) . . . . ?
C14B C13B S3B C16B -1.3(15) . . . . ?
S3A C13A C14A C15A 4.7(19) . . . . ?
Cl1A C15A C16A S3A 178.3(11) . . . . ?
Cl1A C15A C16A Cl2A -8(3) . . . . ?
Cl1A C15A C14A C13A -176.1(13) . . . . ?
C13A S2 N1 S1 71.1(8) . . . . ?
C13A S3A C16A Cl2A 178.6(14) . . . . ?
C13A S3A C16A C15A -6.8(18) . . . . ?
C16A S3A C13A S2 -174.8(13) . . . . ?
C16A S3A C13A C14A 1.0(16) . . . . ?
C16A C15A C14A C13A -10(2) . . . . ?
C14A C15A C16A S3A 11(2) . . . . ?
C14A C15A C16A Cl2A -175.1(15) . . . . ?
S3B C13B C14B C15B -4(2) . . . . ?
S3B C16B C15B Cl1B 176.4(13) . . . . ?
S3B C16B C15B C14B -9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
