# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_20200109
_database_code_depnum_ccdc_archive 'CCDC 2048940'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2020-12-08 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Br N O3 S'
_chemical_formula_sum            'C22 H18 Br N O3 S'
_chemical_formula_weight         456.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N1S1Br1
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      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                   9.6907(12)
_cell_length_b                   10.3979(10)
_cell_length_c                   11.4082(13)
_cell_angle_alpha                88.986(9)
_cell_angle_beta                 65.263(11)
_cell_angle_gamma                80.064(9)
_cell_volume                     1026.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6980
_cell_measurement_theta_min      4.2490
_shelx_estimated_absorpt_T_max   0.698
_shelx_estimated_absorpt_T_min   0.497
_exptl_absorpt_coefficient_mu    3.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7270
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.099
_diffrn_reflns_theta_max         67.099
_diffrn_reflns_theta_min         4.275
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00  90.00   93
  2  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -90.00   93
  3  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 -60.00   76
  4  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   53
  5  ω     57.00 110.00   1.00    1.00    --   36.47 178.00   0.00   53
  6  ω    -33.00  65.00   1.00    1.00    --   36.47 -77.00-150.00   98
  7  ω     18.00 105.00   1.00    1.00    --   36.47  57.00   0.00   87
  8  ω    -36.00  74.00   1.00    1.00    --   36.47 -19.00  30.00  110
  9  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -30.00   81
 10  ω     46.00  77.00   1.00    1.00    --   36.47 -99.00  30.00   31
 11  ω     51.00  93.00   1.00    1.00    --   36.47  77.00 150.00   42
 12  ω      9.00  45.00   1.00    1.00    --   36.47  77.00 150.00   36
 13  ω    100.00 137.00   1.00    1.50    --  108.00  45.00-120.00   37
 14  ω     39.00  94.00   1.00    1.50    --  108.00 -94.00 150.00   55
 15  ω     46.00 122.00   1.00    1.50    --  108.00 -30.00  90.00   76
 16  ω    112.00 137.00   1.00    1.50    --  108.00 -77.00 -90.00   25
 17  ω     41.00 124.00   1.00    1.50    --  108.00 -61.00 150.00   83
 18  ω     46.00 122.00   1.00    1.50    --  108.00 -61.00   0.00   76
 19  ω    117.00 146.00   1.00    1.50    --  108.00 111.00-150.00   29
 20  ω     40.00 122.00   1.00    1.50    --  108.00 -61.00 -90.00   82
 21  ω     71.00 112.00   1.00    1.50    --  108.00-111.00 -90.00   41
 22  ω     40.00  66.00   1.00    1.50    --  108.00 -77.00 -90.00   26
 23  ω     79.00 106.00   1.00    1.50    --  108.00-111.00   0.00   27
 24  ω     98.00 178.00   1.00    1.50    --  108.00  45.00  60.00   80
 25  ω    110.00 170.00   1.00    1.50    --  108.00  61.00 -90.00   60
 26  ω     36.00 153.00   1.00    1.50    --  108.00 -15.00-120.00  117
 27  ω     75.00 111.00   1.00    1.50    --  108.00-111.00  90.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0376332000
_diffrn_orient_matrix_UB_12      0.1369714000
_diffrn_orient_matrix_UB_13      0.0669332000
_diffrn_orient_matrix_UB_21      0.1067284000
_diffrn_orient_matrix_UB_22      -0.0484901000
_diffrn_orient_matrix_UB_23      0.0669189000
_diffrn_orient_matrix_UB_31      0.1374066000
_diffrn_orient_matrix_UB_32      0.0397779000
_diffrn_orient_matrix_UB_33      -0.1150195000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3068
_reflns_number_total             3682
_reflns_odcompleteness_completeness 99.84
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.1797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1104
_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:
 C1(H1), C3(H3), C4(H4), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
Br1 Br 0.67648(5) 0.30170(4) -0.47488(4) 0.07402(17) Uani 1 1 d . . . . .
S1 S 0.16782(8) -0.01709(7) 0.16873(6) 0.04336(18) Uani 1 1 d . . . . .
O1 O -0.0251(3) -0.2050(3) 0.1724(2) 0.0753(8) Uani 1 1 d . . . . .
O2 O 0.3874(3) 0.3333(2) 0.2046(2) 0.0599(6) Uani 1 1 d . . . . .
O3 O 0.2623(2) 0.16632(19) 0.29507(19) 0.0511(5) Uani 1 1 d . . . . .
N1 N 0.3574(3) 0.1785(2) 0.0827(2) 0.0406(5) Uani 1 1 d . . . . .
C1 C 0.4984(3) 0.1644(3) -0.2642(3) 0.0459(6) Uani 1 1 d . . . . .
H1 H 0.4906 0.1135 -0.3266 0.055 Uiso 1 1 calc R . . . .
C2 C 0.5815(3) 0.2648(3) -0.2980(3) 0.0521(7) Uani 1 1 d . . . . .
C3 C 0.5959(4) 0.3417(3) -0.2075(3) 0.0547(8) Uani 1 1 d . . . . .
H3 H 0.6534 0.4082 -0.2344 0.066 Uiso 1 1 calc R . . . .
C4 C 0.5258(3) 0.3207(3) -0.0781(3) 0.0500(7) Uani 1 1 d . . . . .
H4 H 0.5347 0.3723 -0.0167 0.060 Uiso 1 1 calc R . . . .
C5 C 0.4414(3) 0.2202(2) -0.0415(3) 0.0408(6) Uani 1 1 d . . . . .
C6 C 0.4267(3) 0.1420(2) -0.1334(3) 0.0391(6) Uani 1 1 d . . . . .
C7 C 0.3313(3) 0.0484(2) -0.0622(3) 0.0382(6) Uani 1 1 d . . . . .
C8 C 0.2915(3) 0.0749(2) 0.0663(3) 0.0383(6) Uani 1 1 d . . . . .
C9 C 0.2600(3) -0.0528(3) -0.0803(3) 0.0413(6) Uani 1 1 d . . . . .
H9 H 0.2727 -0.0843 -0.1606 0.050 Uiso 1 1 calc R . . . .
C10 C 0.1700(3) -0.0987(3) 0.0348(3) 0.0411(6) Uani 1 1 d . . . . .
C11 C 0.0721(3) -0.1986(3) 0.0631(3) 0.0467(7) Uani 1 1 d . . . . .
C12 C 0.0919(3) -0.2916(2) -0.0433(3) 0.0401(6) Uani 1 1 d . . . . .
C13 C -0.0387(4) -0.3321(3) -0.0406(3) 0.0482(7) Uani 1 1 d . . . . .
H13 H -0.1354 -0.2986 0.0245 0.058 Uiso 1 1 calc R . . . .
C14 C -0.0259(4) -0.4216(3) -0.1336(4) 0.0622(9) Uani 1 1 d . . . . .
H14 H -0.1139 -0.4463 -0.1329 0.075 Uiso 1 1 calc R . . . .
C15 C 0.1175(5) -0.4745(3) -0.2276(3) 0.0655(10) Uani 1 1 d . . . . .
H15 H 0.1263 -0.5356 -0.2900 0.079 Uiso 1 1 calc R . . . .
C16 C 0.2476(4) -0.4371(3) -0.2295(3) 0.0616(9) Uani 1 1 d . . . . .
H16 H 0.3442 -0.4738 -0.2928 0.074 Uiso 1 1 calc R . . . .
C17 C 0.2362(4) -0.3453(3) -0.1382(3) 0.0496(7) Uani 1 1 d . . . . .
H17 H 0.3246 -0.3198 -0.1403 0.060 Uiso 1 1 calc R . . . .
C18 C 0.3383(3) 0.2357(3) 0.1996(3) 0.0443(6) Uani 1 1 d . . . . .
C19 C 0.2146(4) 0.2111(3) 0.4322(3) 0.0549(8) Uani 1 1 d . . . . .
C20 C 0.1104(4) 0.3443(4) 0.4597(4) 0.0758(11) Uani 1 1 d . . . . .
H20A H 0.0354 0.3433 0.4255 0.114 Uiso 1 1 calc GR . . . .
H20B H 0.1715 0.4096 0.4196 0.114 Uiso 1 1 calc GR . . . .
H20C H 0.0585 0.3642 0.5514 0.114 Uiso 1 1 calc GR . . . .
C21 C 0.3569(5) 0.2140(4) 0.4553(4) 0.0822(12) Uani 1 1 d . . . . .
H21A H 0.3273 0.2289 0.5462 0.123 Uiso 1 1 calc GR . . . .
H21B H 0.4071 0.2832 0.4096 0.123 Uiso 1 1 calc GR . . . .
H21C H 0.4266 0.1319 0.4249 0.123 Uiso 1 1 calc GR . . . .
C22 C 0.1270(6) 0.1073(4) 0.5042(3) 0.0910(14) Uani 1 1 d . . . . .
H22A H 0.1926 0.0230 0.4767 0.136 Uiso 1 1 calc GR . . . .
H22B H 0.0381 0.1092 0.4866 0.136 Uiso 1 1 calc GR . . . .
H22C H 0.0943 0.1233 0.5954 0.136 Uiso 1 1 calc GR . . . .


_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 C2 1.899(3) . ?
S1 C8 1.703(3) . ?
S1 C10 1.752(3) . ?
O1 C11 1.217(3) . ?
O2 C18 1.204(3) . ?
O3 C18 1.317(3) . ?
O3 C19 1.492(3) . ?
N1 C5 1.412(3) . ?
N1 C8 1.396(3) . ?
N1 C18 1.396(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 C6 1.405(4) . ?
C6 C7 1.455(3) . ?
C7 C8 1.371(4) . ?
C7 C9 1.416(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(4) . ?
C10 C11 1.468(4) . ?
C11 C12 1.492(4) . ?
C12 C13 1.390(4) . ?
C12 C17 1.387(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9300 . ?
C19 C20 1.518(5) . ?
C19 C21 1.513(5) . ?
C19 C22 1.504(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C8 S1 C10 89.20(12) . . ?
C18 O3 C19 120.7(2) . . ?
C8 N1 C5 107.1(2) . . ?
C8 N1 C18 127.0(2) . . ?
C18 N1 C5 125.8(2) . . ?
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.7(3) . . ?
C6 C1 H1 121.2 . . ?
C1 C2 Br1 119.0(2) . . ?
C1 C2 C3 122.4(3) . . ?
C3 C2 Br1 118.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(3) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 N1 130.0(3) . . ?
C4 C5 C6 121.4(3) . . ?
C6 C5 N1 108.6(2) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C7 133.4(2) . . ?
C5 C6 C7 106.8(2) . . ?
C8 C7 C6 106.9(2) . . ?
C8 C7 C9 111.4(2) . . ?
C9 C7 C6 141.6(2) . . ?
N1 C8 S1 134.6(2) . . ?
C7 C8 S1 114.70(19) . . ?
C7 C8 N1 110.6(2) . . ?
C7 C9 H9 124.0 . . ?
C10 C9 C7 111.9(2) . . ?
C10 C9 H9 124.0 . . ?
C9 C10 S1 112.81(19) . . ?
C9 C10 C11 130.9(2) . . ?
C11 C10 S1 116.2(2) . . ?
O1 C11 C10 120.2(3) . . ?
O1 C11 C12 120.3(2) . . ?
C10 C11 C12 119.5(2) . . ?
C13 C12 C11 118.1(3) . . ?
C17 C12 C11 122.2(2) . . ?
C17 C12 C13 119.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 120.3 . . ?
C16 C17 C12 119.5(3) . . ?
C16 C17 H17 120.3 . . ?
O2 C18 O3 128.7(3) . . ?
O2 C18 N1 122.1(3) . . ?
O3 C18 N1 109.2(2) . . ?
O3 C19 C20 108.8(3) . . ?
O3 C19 C21 109.5(3) . . ?
O3 C19 C22 101.7(2) . . ?
C21 C19 C20 112.2(3) . . ?
C22 C19 C20 111.6(3) . . ?
C22 C19 C21 112.6(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 C2 C3 C4 178.4(2) . . . . ?
S1 C10 C11 O1 13.4(4) . . . . ?
S1 C10 C11 C12 -167.1(2) . . . . ?
O1 C11 C12 C13 34.5(4) . . . . ?
O1 C11 C12 C17 -140.8(3) . . . . ?
N1 C5 C6 C1 179.4(2) . . . . ?
N1 C5 C6 C7 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C7 C8 -179.0(3) . . . . ?
C1 C6 C7 C9 -4.4(6) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 N1 -179.2(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C5 N1 C8 S1 -175.2(2) . . . . ?
C5 N1 C8 C7 0.7(3) . . . . ?
C5 N1 C18 O2 4.0(4) . . . . ?
C5 N1 C18 O3 -175.8(2) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C9 175.6(3) . . . . ?
C6 C1 C2 Br1 -178.3(2) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C6 C7 C8 S1 175.75(18) . . . . ?
C6 C7 C8 N1 -1.1(3) . . . . ?
C6 C7 C9 C10 -174.7(3) . . . . ?
C7 C9 C10 S1 1.0(3) . . . . ?
C7 C9 C10 C11 177.8(3) . . . . ?
C8 S1 C10 C9 -1.1(2) . . . . ?
C8 S1 C10 C11 -178.5(2) . . . . ?
C8 N1 C5 C4 179.0(3) . . . . ?
C8 N1 C5 C6 0.0(3) . . . . ?
C8 N1 C18 O2 -172.4(3) . . . . ?
C8 N1 C18 O3 7.8(4) . . . . ?
C8 C7 C9 C10 -0.2(3) . . . . ?
C9 C7 C8 S1 -0.7(3) . . . . ?
C9 C7 C8 N1 -177.5(2) . . . . ?
C9 C10 C11 O1 -163.4(3) . . . . ?
C9 C10 C11 C12 16.1(5) . . . . ?
C10 S1 C8 N1 176.8(3) . . . . ?
C10 S1 C8 C7 1.0(2) . . . . ?
C10 C11 C12 C13 -145.1(3) . . . . ?
C10 C11 C12 C17 39.6(4) . . . . ?
C11 C12 C13 C14 -177.5(3) . . . . ?
C11 C12 C17 C16 176.0(3) . . . . ?
C12 C13 C14 C15 2.0(5) . . . . ?
C13 C12 C17 C16 0.8(4) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C17 C12 C13 C14 -2.1(4) . . . . ?
C18 O3 C19 C20 59.4(4) . . . . ?
C18 O3 C19 C21 -63.5(4) . . . . ?
C18 O3 C19 C22 177.2(3) . . . . ?
C18 N1 C5 C4 2.0(5) . . . . ?
C18 N1 C5 C6 -177.0(2) . . . . ?
C18 N1 C8 S1 1.7(5) . . . . ?
C18 N1 C8 C7 177.6(3) . . . . ?
C19 O3 C18 O2 5.1(5) . . . . ?
C19 O3 C18 N1 -175.1(2) . . . . ?

_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.827
