# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20200728_whm3pbr
_database_code_depnum_ccdc_archive 'CCDC 2074630'
loop_
_audit_author_name
_audit_author_address
'Hui-Min Wu'
;Wuhan University
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Br N O2 S'
_chemical_formula_sum            'C20 H18 Br N O2 S'
_chemical_formula_weight         416.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.68190(10)
_cell_length_b                   5.89500(10)
_cell_length_c                   20.17430(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.4160(10)
_cell_angle_gamma                90
_cell_volume                     913.31(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15912
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5700
_cell_measurement_theta_min      2.1960
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.363
_exptl_absorpt_coefficient_mu    4.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18153
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.736
_diffrn_reflns_theta_min         2.191
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  14.00   0.50    0.50    --    0.00 -82.00-180.00   56
  2  ω      8.00  47.00   0.50    0.50    --   32.00  71.00  -9.25   78
  3  ω     15.00  52.00   0.50    0.50    --   40.00  67.00 -96.21   74
  4  ω     15.00  86.00   0.50    0.50    --   40.00  71.00 159.26  142
  5  ω      6.00  68.00   0.50    0.50    --   44.00 -68.00 158.21  124
  6  ω     31.00  59.00   0.50    0.50    --   52.00  63.00  85.67   56
  7  ω    116.00 145.00   0.50    0.50    --   56.00  72.00  22.07   58
  8  ω     29.00  60.00   0.50    0.50    --   56.00  72.00  22.07   62
  9  ω     32.00  73.00   0.50    0.50    --   60.00  75.00 -69.13   82
 10  ω     33.00  78.00   0.50    0.50    --   60.00  72.00-143.00   90
 11  ω    121.00 149.00   0.50    0.50    --   60.00  72.00-143.00   56
 12  ω     38.00 104.00   0.50    0.50    --   64.00  72.00   5.36  132
 13  ω     36.00  70.00   0.50    0.50    --   64.00  75.00  60.64   68
 14  ω     37.00  66.00   0.50    0.50    --   64.00  75.00 128.80   58
 15  ω     36.00  72.00   0.50    0.50    --   64.00  75.00-110.49   72
 16  ω     44.00  94.00   0.50    0.50    --   72.00  74.00 -44.00  100
 17  ω    117.00 161.00   0.50    0.50    --   72.00  75.00 136.90   88
 18  ω     46.00 107.00   0.50    0.50    --   72.00  75.00 136.90  122
 19  ω     48.00  74.00   0.50    0.50    --   76.00  75.00  66.40   52
 20  ω    114.00 167.00   0.50    0.50    --   80.00  63.00 101.00  106
 21  ω     56.00  84.00   0.50    0.50    --   80.00  63.00 101.00   56
 22  ω     56.00  86.00   0.50    0.50    --   84.00  75.00 -65.33   60
 23  ω    122.00 173.00   0.50    0.50    --   84.00  57.00-143.99  102
 24  ω     63.00 108.00   0.50    0.50    --   84.00  57.00-143.99   90
 25  ω    106.00 132.00   0.50    0.50    --   88.00  68.00 160.81   52
 26  ω     63.00  94.00   0.50    0.50    --   88.00  68.00 160.81   62
 27  ω    119.00 183.00   0.50    0.50    --   94.60  68.00  47.72  128
 28  ω     69.00 113.00   0.50    0.50    --   94.60  68.00  47.72   88
 29  ω      8.00 115.00   0.50    0.50    --   94.60 -61.00  30.00  214
 30  ω     36.00  62.00   0.50    0.50    --   94.60 -82.00-180.00   52
 31  ω     67.00 100.00   0.50    0.50    --   94.60  72.00-129.15   66
 32  ω     77.00 135.00   0.50    0.50    --   94.60  45.00 -60.00  116
 33  ω     32.00 103.00   0.50    0.50    --   94.60 -61.00 120.00  142
 34  ω    150.00 175.00   0.50    0.50    --   94.60  77.00  90.00   50
 35  ω     81.00 119.00   0.50    0.50    --   94.60  77.00  90.00   76
 36  ω    159.00 184.00   0.50    0.50    --   94.60  45.00-120.00   50
 37  ω     79.00 184.00   0.50    0.50    --   94.60  61.00 120.00  210
 38  ω     83.00 110.00   0.50    0.50    --   94.60  77.00  60.00   54
 39  ω    152.00 179.00   0.50    0.50    --   94.60  61.00  30.00   54
 40  ω    115.00 184.00   0.50    0.50    --   94.60  61.00 -90.00  138
 41  ω     71.00 146.00   0.50    0.50    --   94.60  61.00  30.00  150
 42  ω     72.00  98.00   0.50    0.50    --   94.60  61.00 -90.00   52
 43  ω    136.00 162.00   0.50    0.50    --   94.60  61.00-180.00   52
 44  ω      5.00 125.00   0.50    0.50    --   94.60 -82.00  30.00  240
 45  ω    144.00 169.00   0.50    0.50    --   94.60  77.00  60.00   50
 46  ω     83.00 141.00   0.50    0.50    --   94.60  45.00-120.00  116
 47  ω     80.00 108.00   0.50    0.50    --   94.60  61.00-180.00   56
 48  ω     58.00 120.00   0.50    0.50    --   94.60 -82.00-120.00  124
 49  ω     86.00 174.00   0.50    0.50    --   94.60  61.00 -42.22  176
 50  ω     10.00  49.00   0.50    0.50    --   94.60 -82.00-120.00   78
 51  ω     73.00 120.00   0.50    0.50    --   94.60 -82.00-180.00   94
 52  ω     79.00 182.00   0.50    0.50    --   94.60  77.00 -30.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1388343000
_diffrn_orient_matrix_UB_12      -0.1012099000
_diffrn_orient_matrix_UB_13      0.0478317000
_diffrn_orient_matrix_UB_21      -0.1220848000
_diffrn_orient_matrix_UB_22      0.0369282000
_diffrn_orient_matrix_UB_23      0.0584668000
_diffrn_orient_matrix_UB_31      -0.0778671000
_diffrn_orient_matrix_UB_32      -0.2381290000
_diffrn_orient_matrix_UB_33      -0.0112738000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3567
_reflns_number_total             3585
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0213
_refine_ls_restrained_S_all      1.080
_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)+(0.0324P)²+0.4277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0579
_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:
 C13(H13A,H13B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C9(H9), C11(H11), C15(H15), C16(H16), C21(H21),
 C22(H22), C14(H14), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.09975(3) 1.03039(6) 0.65457(2) 0.02652(10) Uani 1 1 d . . . . .
S2 S 0.66994(9) 0.46566(11) 0.16948(3) 0.02036(16) Uani 1 1 d . . . . .
C1 C 0.6571(3) 0.9769(5) 0.03141(14) 0.0181(6) Uani 1 1 d . . . . .
H1 H 0.593611 1.087354 0.053162 0.022 Uiso 1 1 calc R U . . .
O2 O 0.1982(2) 1.0092(4) 0.21563(9) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.1850(3) 1.0245(6) 0.56678(12) 0.0205(5) Uani 1 1 d . . . . .
C4 C 0.3712(3) 1.0263(6) 0.36963(12) 0.0180(5) Uani 1 1 d . . . . .
H4 H 0.342413 1.155404 0.345246 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3067(3) 1.0178(6) 0.43769(12) 0.0171(5) Uani 1 1 d . . . . .
C6 C 0.7218(3) 1.0204(7) -0.03099(12) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.702082 1.160603 -0.050949 0.025 Uiso 1 1 calc R U . . .
N8 N 0.4942(3) 0.8430(4) 0.15122(11) 0.0153(5) Uani 1 1 d . . . . .
C9 C 0.2798(4) 0.8404(5) 0.54554(15) 0.0206(6) Uani 1 1 d . . . . .
H9 H 0.303153 0.719810 0.574113 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6097(3) 0.7155(5) 0.12603(13) 0.0165(5) Uani 1 1 d . . . . .
C11 C 0.3400(4) 0.8367(5) 0.48114(14) 0.0198(6) Uani 1 1 d . . . . .
H11 H 0.403275 0.712391 0.466709 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0141(3) 1.0584(6) 0.21853(14) 0.0249(6) Uani 1 1 d . . . . .
H12A H -0.046391 0.984156 0.182422 0.037 Uiso 1 1 calc R U . . .
H12B H -0.003673 1.219281 0.215283 0.037 Uiso 1 1 calc R U . . .
H12C H -0.029772 1.004570 0.259796 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4855(3) 0.5049(5) 0.22263(12) 0.0180(5) Uani 1 1 d . . . . .
H13A H 0.388496 0.410133 0.208190 0.022 Uiso 1 1 calc R U . . .
H13B H 0.516487 0.467566 0.268230 0.022 Uiso 1 1 calc R U . . .
C15 C 0.8496(4) 0.6481(6) -0.03379(15) 0.0232(6) Uani 1 1 d . . . . .
H15 H 0.913992 0.538632 -0.055560 0.028 Uiso 1 1 calc R U . . .
C16 C 0.2109(4) 1.2014(5) 0.46123(14) 0.0195(6) Uani 1 1 d . . . . .
H16 H 0.187550 1.323308 0.433114 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2403(3) 0.7891(5) 0.21891(13) 0.0160(5) Uani 1 1 d . . . . .
C18 C 0.4383(3) 0.7585(5) 0.21592(13) 0.0145(5) Uani 1 1 d . . . . .
C19 C 0.6876(3) 0.7663(5) 0.06140(13) 0.0163(5) Uani 1 1 d . . . . .
C20 C 0.5310(3) 0.9053(5) 0.26999(14) 0.0174(6) Uani 1 1 d . . . . .
H20A H 0.654496 0.871215 0.270158 0.021 Uiso 1 1 calc R U . . .
H20B H 0.517154 1.063889 0.258127 0.021 Uiso 1 1 calc R U . . .
C21 C 0.8159(4) 0.8556(6) -0.06366(14) 0.0224(6) Uani 1 1 d . . . . .
H21 H 0.856551 0.884504 -0.105866 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4656(3) 0.8716(5) 0.33884(14) 0.0175(6) Uani 1 1 d . . . . .
H22 H 0.492277 0.736896 0.360829 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1496(4) 1.2069(6) 0.52538(14) 0.0210(6) Uani 1 1 d . . . . .
H14 H 0.086170 1.330493 0.540217 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7865(3) 0.6046(5) 0.02911(14) 0.0207(6) Uani 1 1 d . . . . .
H7 H 0.810648 0.466490 0.049640 0.025 Uiso 1 1 calc R U . . .
O1 O 0.1374(3) 0.6383(4) 0.22355(11) 0.0259(5) 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 1.904(2) . ?
S2 C10 1.769(3) . ?
S2 C13 1.813(3) . ?
C1 H1 0.9300 . ?
C1 C6 1.389(4) . ?
C1 C19 1.398(4) . ?
O2 C12 1.446(3) . ?
O2 C17 1.338(4) . ?
C3 C9 1.381(5) . ?
C3 C14 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.472(3) . ?
C4 C22 1.329(4) . ?
C5 C11 1.401(4) . ?
C5 C16 1.399(4) . ?
C6 H6 0.9300 . ?
C6 C21 1.387(5) . ?
N8 C10 1.278(4) . ?
N8 C18 1.471(3) . ?
C9 H9 0.9300 . ?
C9 C11 1.390(4) . ?
C10 C19 1.479(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C18 1.543(4) . ?
C15 H15 0.9300 . ?
C15 C21 1.385(5) . ?
C15 C7 1.393(4) . ?
C16 H16 0.9300 . ?
C16 C14 1.388(4) . ?
C17 C18 1.534(3) . ?
C17 O1 1.195(4) . ?
C18 C20 1.552(4) . ?
C19 C7 1.391(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C22 1.502(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C14 H14 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S2 C13 89.32(13) . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C19 119.8(3) . . ?
C19 C1 H1 120.1 . . ?
C17 O2 C12 115.3(2) . . ?
C9 C3 Br1 119.9(2) . . ?
C9 C3 C14 121.4(2) . . ?
C14 C3 Br1 118.7(2) . . ?
C5 C4 H4 116.1 . . ?
C22 C4 H4 116.1 . . ?
C22 C4 C5 127.8(3) . . ?
C11 C5 C4 123.3(3) . . ?
C16 C5 C4 118.9(3) . . ?
C16 C5 C11 117.8(2) . . ?
C1 C6 H6 119.9 . . ?
C21 C6 C1 120.2(3) . . ?
C21 C6 H6 119.9 . . ?
C10 N8 C18 112.0(2) . . ?
C3 C9 H9 120.2 . . ?
C3 C9 C11 119.5(3) . . ?
C11 C9 H9 120.2 . . ?
N8 C10 S2 117.9(2) . . ?
N8 C10 C19 122.1(3) . . ?
C19 C10 S2 119.9(2) . . ?
C5 C11 H11 119.6 . . ?
C9 C11 C5 120.9(3) . . ?
C9 C11 H11 119.6 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C13 H13A 110.8 . . ?
S2 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C18 C13 S2 104.90(18) . . ?
C18 C13 H13A 110.8 . . ?
C18 C13 H13B 110.8 . . ?
C21 C15 H15 120.2 . . ?
C21 C15 C7 119.6(3) . . ?
C7 C15 H15 120.2 . . ?
C5 C16 H16 119.1 . . ?
C14 C16 C5 121.9(3) . . ?
C14 C16 H16 119.1 . . ?
O2 C17 C18 110.5(2) . . ?
O1 C17 O2 124.5(2) . . ?
O1 C17 C18 125.0(3) . . ?
N8 C18 C13 109.4(2) . . ?
N8 C18 C17 107.9(2) . . ?
N8 C18 C20 107.2(2) . . ?
C13 C18 C20 112.1(2) . . ?
C17 C18 C13 110.0(2) . . ?
C17 C18 C20 110.2(2) . . ?
C1 C19 C10 119.6(2) . . ?
C7 C19 C1 119.6(3) . . ?
C7 C19 C10 120.8(3) . . ?
C18 C20 H20A 108.6 . . ?
C18 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C22 C20 C18 114.7(2) . . ?
C22 C20 H20A 108.6 . . ?
C22 C20 H20B 108.6 . . ?
C6 C21 H21 119.8 . . ?
C15 C21 C6 120.4(3) . . ?
C15 C21 H21 119.8 . . ?
C4 C22 C20 122.7(3) . . ?
C4 C22 H22 118.6 . . ?
C20 C22 H22 118.6 . . ?
C3 C14 C16 118.6(3) . . ?
C3 C14 H14 120.7 . . ?
C16 C14 H14 120.7 . . ?
C15 C7 H7 119.8 . . ?
C19 C7 C15 120.4(3) . . ?
C19 C7 H7 119.8 . . ?

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 C9 C11 179.4(2) . . . . ?
Br1 C3 C14 C16 -179.5(2) . . . . ?
S2 C10 C19 C1 -171.8(2) . . . . ?
S2 C10 C19 C7 10.2(3) . . . . ?
S2 C13 C18 N8 26.3(2) . . . . ?
S2 C13 C18 C17 144.63(18) . . . . ?
S2 C13 C18 C20 -92.5(2) . . . . ?
C1 C6 C21 C15 -1.5(4) . . . . ?
C1 C19 C7 C15 -2.4(4) . . . . ?
O2 C17 C18 N8 -63.0(3) . . . . ?
O2 C17 C18 C13 177.7(2) . . . . ?
O2 C17 C18 C20 53.7(3) . . . . ?
C3 C9 C11 C5 0.4(4) . . . . ?
C4 C5 C11 C9 178.3(3) . . . . ?
C4 C5 C16 C14 -178.5(3) . . . . ?
C5 C4 C22 C20 -177.0(2) . . . . ?
C5 C16 C14 C3 -0.1(4) . . . . ?
C6 C1 C19 C10 -176.4(2) . . . . ?
C6 C1 C19 C7 1.6(4) . . . . ?
N8 C10 C19 C1 10.7(4) . . . . ?
N8 C10 C19 C7 -167.3(3) . . . . ?
N8 C18 C20 C22 169.6(2) . . . . ?
C9 C3 C14 C16 0.3(4) . . . . ?
C10 S2 C13 C18 -20.61(18) . . . . ?
C10 N8 C18 C13 -19.7(3) . . . . ?
C10 N8 C18 C17 -139.3(2) . . . . ?
C10 N8 C18 C20 102.1(3) . . . . ?
C10 C19 C7 C15 175.7(3) . . . . ?
C11 C5 C16 C14 -0.1(4) . . . . ?
C12 O2 C17 C18 -179.6(2) . . . . ?
C12 O2 C17 O1 0.4(4) . . . . ?
C13 S2 C10 N8 11.6(2) . . . . ?
C13 S2 C10 C19 -166.0(2) . . . . ?
C13 C18 C20 C22 -70.3(3) . . . . ?
C16 C5 C11 C9 -0.1(4) . . . . ?
C17 C18 C20 C22 52.5(3) . . . . ?
C18 N8 C10 S2 3.0(3) . . . . ?
C18 N8 C10 C19 -179.4(2) . . . . ?
C18 C20 C22 C4 -108.2(3) . . . . ?
C19 C1 C6 C21 0.3(4) . . . . ?
C21 C15 C7 C19 1.1(4) . . . . ?
C22 C4 C5 C11 0.7(4) . . . . ?
C22 C4 C5 C16 179.0(3) . . . . ?
C14 C3 C9 C11 -0.5(4) . . . . ?
C7 C15 C21 C6 0.8(4) . . . . ?
O1 C17 C18 N8 117.0(3) . . . . ?
O1 C17 C18 C13 -2.3(4) . . . . ?
O1 C17 C18 C20 -126.3(3) . . . . ?


_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.703
_oxdiff_exptl_absorpt_empirical_full_min 0.513
