# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a201116b
_database_code_depnum_ccdc_archive 'CCDC 2075413'
loop_
_audit_author_name
_audit_author_address
'Dawei Tian'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 B Br N S'
_chemical_formula_sum            'C14 H9 B Br N S'
_chemical_formula_weight         314.00
_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 0.0181 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'
B B 0.0090 0.0039 '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'
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           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                   9.64453(12)
_cell_length_b                   27.2283(3)
_cell_length_c                   9.74695(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.1159(13)
_cell_angle_gamma                90
_cell_volume                     2519.80(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12299
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8870
_cell_measurement_theta_min      4.8350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.246
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  26.00   1.00    1.00    --  -41.42  57.00-120.00   88
  2  ω   -114.00 -15.00   1.00    1.00    --  -41.42 -57.00  90.00   99
  3  ω     56.00  86.00   1.00    1.00    --   41.42-125.00  30.00   30
  4  ω    -32.00  66.00   1.00    1.00    --   41.42 -38.00 -60.00   98
  5  ω    106.00 138.00   1.00    4.00    --  105.20  77.00-120.00   32
  6  ω    115.00 141.00   1.00    4.00    --  105.20 121.00 -70.00   26
  7  ω    118.00 177.00   1.00    4.00    --  105.20  61.00   0.00   59
  8  ω    119.00 177.00   1.00    4.00    --  105.20  61.00-150.00   58
  9  ω     25.00  51.00   1.00    4.00    --  105.20 -94.00 -60.00   26
 10  ω     35.00 109.00   1.00    4.00    --  105.20 -45.00-150.00   74
 11  ω     74.00 112.00   1.00    4.00    --  105.20-125.00-180.00   38
 12  ω     39.00 101.00   1.00    4.00    --  105.20 -94.00   0.00   62
 13  ω     34.00  59.00   1.00    4.00    --  105.20-125.00 -30.00   25
 14  ω     77.00 110.00   1.00    4.00    --  105.20-125.00 -30.00   33
 15  ω     30.00 106.00   1.00    4.00    --  105.20 -94.00-150.00   76
 16  ω     34.00 125.00   1.00    4.00    --  105.20 -45.00  60.00   91
 17  ω     24.00  95.00   1.00    4.00    --  105.20 -94.00  60.00   71
 18  ω    111.00 169.00   1.00    4.00    --  105.20  77.00 150.00   58
 19  ω    105.00 178.00   1.00    4.00    --  105.20  45.00 120.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0769835000
_diffrn_orient_matrix_UB_12      -0.0205050000
_diffrn_orient_matrix_UB_13      0.1401695000
_diffrn_orient_matrix_UB_21      -0.0456119000
_diffrn_orient_matrix_UB_22      -0.0523970000
_diffrn_orient_matrix_UB_23      -0.0476257000
_diffrn_orient_matrix_UB_31      0.1352403000
_diffrn_orient_matrix_UB_32      -0.0059947000
_diffrn_orient_matrix_UB_33      -0.0622515000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4376
_reflns_number_total             4508
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.122
_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)+(0.0638P)²+2.8373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 N2(H2), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C25(H25), C26(H26),
 C28(H28)
;
_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
Br1 Br 0.74976(4) 0.48715(2) 0.65741(4) 0.04781(15) Uani 1 1 d . . . . .
S1 S 0.87004(7) 0.19336(3) 0.69973(7) 0.02889(18) Uani 1 1 d . . . . .
N1 N 0.5374(2) 0.27826(9) 0.5502(2) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.4511 0.2738 0.5115 0.028 Uiso 1 1 calc R . . . .
C1 C 0.7268(3) 0.15549(12) 0.6258(3) 0.0268(6) Uani 1 1 d . . . . .
C2 C 0.6005(3) 0.18051(11) 0.5711(3) 0.0249(6) Uani 1 1 d . . . . .
C3 C 0.4855(3) 0.15167(12) 0.5124(3) 0.0275(6) Uani 1 1 d . . . . .
H3 H 0.4004 0.1668 0.4763 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4960(3) 0.10093(13) 0.5069(3) 0.0337(7) Uani 1 1 d . . . . .
H4 H 0.4180 0.0823 0.4682 0.040 Uiso 1 1 calc R . . . .
C5 C 0.6230(4) 0.07773(13) 0.5593(3) 0.0361(7) Uani 1 1 d . . . . .
H5 H 0.6297 0.0437 0.5538 0.043 Uiso 1 1 calc R . . . .
C6 C 0.7398(3) 0.10493(13) 0.6199(3) 0.0330(7) Uani 1 1 d . . . . .
H6 H 0.8245 0.0895 0.6555 0.040 Uiso 1 1 calc R . . . .
C7 C 0.7749(3) 0.24756(12) 0.6595(3) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.8223(3) 0.29407(12) 0.6814(3) 0.0267(6) Uani 1 1 d . . . . .
H8 H 0.9150 0.3000 0.7233 0.032 Uiso 1 1 calc R . . . .
C9 C 0.7272(3) 0.33454(12) 0.6389(3) 0.0252(6) Uani 1 1 d . . . . .
C10 C 0.5860(3) 0.32602(11) 0.5738(3) 0.0229(6) Uani 1 1 d . . . . .
C11 C 0.4970(3) 0.36647(12) 0.5340(3) 0.0268(6) Uani 1 1 d . . . . .
H11 H 0.4042 0.3611 0.4913 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5450(3) 0.41392(12) 0.5570(3) 0.0311(6) Uani 1 1 d . . . . .
H12 H 0.4857 0.4404 0.5300 0.037 Uiso 1 1 calc R . . . .
C13 C 0.6843(3) 0.42153(12) 0.6218(3) 0.0319(7) Uani 1 1 d . . . . .
C14 C 0.7753(3) 0.38323(12) 0.6603(3) 0.0294(6) Uani 1 1 d . . . . .
H14 H 0.8684 0.3894 0.7005 0.035 Uiso 1 1 calc R . . . .
B1 B 0.6232(3) 0.23669(13) 0.5871(3) 0.0234(6) Uani 1 1 d . . . . .
Br2 Br 0.68322(6) 0.50195(2) 0.22404(5) 0.06130(17) Uani 1 1 d . . . . .
S2 S 0.77767(7) 0.20877(3) 0.30996(7) 0.02893(18) Uani 1 1 d . . . . .
N2 N 0.6259(2) 0.29595(9) -0.0144(2) 0.0242(5) Uani 1 1 d . . . . .
H2 H 0.5920 0.2921 -0.1014 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7008(3) 0.17215(12) 0.1658(3) 0.0267(6) Uani 1 1 d . . . . .
C16 C 0.6499(3) 0.19808(12) 0.0417(3) 0.0261(6) Uani 1 1 d . . . . .
C17 C 0.5902(3) 0.17054(12) -0.0742(3) 0.0297(6) Uani 1 1 d . . . . .
H17 H 0.5569 0.1865 -0.1579 0.036 Uiso 1 1 calc R . . . .
C18 C 0.5796(3) 0.12009(13) -0.0673(3) 0.0339(7) Uani 1 1 d . . . . .
H18 H 0.5406 0.1024 -0.1462 0.041 Uiso 1 1 calc R . . . .
C19 C 0.6271(3) 0.09570(13) 0.0574(4) 0.0365(7) Uani 1 1 d . . . . .
H19 H 0.6182 0.0618 0.0617 0.044 Uiso 1 1 calc R . . . .
C20 C 0.6882(3) 0.12173(13) 0.1763(3) 0.0327(7) Uani 1 1 d . . . . .
H20 H 0.7195 0.1056 0.2602 0.039 Uiso 1 1 calc R . . . .
C21 C 0.7342(3) 0.26366(12) 0.2196(3) 0.0256(6) Uani 1 1 d . . . . .
C22 C 0.7484(3) 0.30967(12) 0.2714(3) 0.0261(6) Uani 1 1 d . . . . .
H22 H 0.7891 0.3150 0.3640 0.031 Uiso 1 1 calc R . . . .
C23 C 0.7000(3) 0.35052(12) 0.1818(3) 0.0261(6) Uani 1 1 d . . . . .
C24 C 0.6390(3) 0.34317(11) 0.0395(3) 0.0247(6) Uani 1 1 d . . . . .
C25 C 0.5938(3) 0.38376(12) -0.0447(3) 0.0303(6) Uani 1 1 d . . . . .
H25 H 0.5536 0.3789 -0.1377 0.036 Uiso 1 1 calc R . . . .
C26 C 0.6081(3) 0.43074(13) 0.0081(4) 0.0372(7) Uani 1 1 d . . . . .
H26 H 0.5801 0.4577 -0.0487 0.045 Uiso 1 1 calc R . . . .
C27 C 0.6656(3) 0.43698(13) 0.1489(4) 0.0365(7) Uani 1 1 d . . . . .
C28 C 0.7105(3) 0.39853(13) 0.2343(3) 0.0323(7) Uani 1 1 d . . . . .
H28 H 0.7482 0.4041 0.3275 0.039 Uiso 1 1 calc R . . . .
B2 B 0.6660(3) 0.25412(13) 0.0680(3) 0.0238(6) 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 C13 1.906(3) . ?
S1 C1 1.772(3) . ?
S1 C7 1.745(3) . ?
N1 H1 0.8600 . ?
N1 C10 1.388(4) . ?
N1 B1 1.411(4) . ?
C1 C2 1.416(4) . ?
C1 C6 1.385(5) . ?
C2 C3 1.397(4) . ?
C2 B1 1.549(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.351(5) . ?
C7 B1 1.538(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.447(4) . ?
C9 C10 1.417(4) . ?
C9 C14 1.408(5) . ?
C10 C11 1.408(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(5) . ?
C13 C14 1.372(5) . ?
C14 H14 0.9300 . ?
Br2 C27 1.911(3) . ?
S2 C15 1.776(3) . ?
S2 C21 1.748(3) . ?
N2 H2 0.8600 . ?
N2 C24 1.386(4) . ?
N2 B2 1.408(4) . ?
C15 C16 1.411(4) . ?
C15 C20 1.384(5) . ?
C16 C17 1.393(4) . ?
C16 B2 1.551(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.348(5) . ?
C21 B2 1.530(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.440(4) . ?
C23 C24 1.423(4) . ?
C23 C28 1.401(5) . ?
C24 C25 1.400(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(5) . ?
C27 C28 1.360(5) . ?
C28 H28 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
C7 S1 C1 93.39(14) . . ?
C10 N1 H1 118.5 . . ?
C10 N1 B1 122.9(2) . . ?
B1 N1 H1 118.5 . . ?
C2 C1 S1 115.5(2) . . ?
C6 C1 S1 121.7(2) . . ?
C6 C1 C2 122.7(3) . . ?
C1 C2 B1 109.9(3) . . ?
C3 C2 C1 116.9(3) . . ?
C3 C2 B1 133.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 S1 127.4(2) . . ?
C8 C7 B1 121.4(3) . . ?
B1 C7 S1 111.1(2) . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 121.0(3) . . ?
C14 C9 C8 119.9(3) . . ?
C14 C9 C10 119.1(3) . . ?
N1 C10 C9 119.8(3) . . ?
N1 C10 C11 121.0(2) . . ?
C11 C10 C9 119.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Br1 118.9(3) . . ?
C14 C13 Br1 119.2(2) . . ?
C14 C13 C12 122.0(3) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
N1 B1 C2 134.5(3) . . ?
N1 B1 C7 115.5(3) . . ?
C7 B1 C2 110.0(2) . . ?
C21 S2 C15 92.95(14) . . ?
C24 N2 H2 118.8 . . ?
C24 N2 B2 122.4(2) . . ?
B2 N2 H2 118.8 . . ?
C16 C15 S2 115.5(2) . . ?
C20 C15 S2 121.9(2) . . ?
C20 C15 C16 122.5(3) . . ?
C15 C16 B2 109.9(3) . . ?
C17 C16 C15 117.2(3) . . ?
C17 C16 B2 132.7(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.1(3) . . ?
C15 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C22 C21 S2 127.3(2) . . ?
C22 C21 B2 121.1(3) . . ?
B2 C21 S2 111.5(2) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.1(3) . . ?
C28 C23 C22 120.3(3) . . ?
C28 C23 C24 118.6(3) . . ?
N2 C24 C23 119.6(3) . . ?
N2 C24 C25 120.8(3) . . ?
C25 C24 C23 119.6(3) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 120.8 . . ?
C25 C26 C27 118.5(3) . . ?
C27 C26 H26 120.8 . . ?
C26 C27 Br2 118.8(3) . . ?
C28 C27 Br2 118.7(3) . . ?
C28 C27 C26 122.4(3) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 C23 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
N2 B2 C16 133.8(3) . . ?
N2 B2 C21 116.2(3) . . ?
C21 B2 C16 109.9(3) . . ?

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 C13 C14 C9 177.9(2) . . . . ?
S1 C1 C2 C3 -179.87(19) . . . . ?
S1 C1 C2 B1 1.8(3) . . . . ?
S1 C1 C6 C5 -179.5(2) . . . . ?
S1 C7 C8 C9 179.2(2) . . . . ?
S1 C7 B1 N1 179.97(19) . . . . ?
S1 C7 B1 C2 -0.2(3) . . . . ?
N1 C10 C11 C12 -179.9(2) . . . . ?
C1 S1 C7 C8 -176.9(3) . . . . ?
C1 S1 C7 B1 1.0(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 B1 N1 178.8(3) . . . . ?
C1 C2 B1 C7 -1.0(3) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C2 B1 N1 0.8(5) . . . . ?
C3 C2 B1 C7 -178.9(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C6 C1 C2 B1 -176.9(3) . . . . ?
C7 S1 C1 C2 -1.7(2) . . . . ?
C7 S1 C1 C6 177.0(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 C14 -179.6(2) . . . . ?
C8 C7 B1 N1 -2.0(4) . . . . ?
C8 C7 B1 C2 177.8(2) . . . . ?
C8 C9 C10 N1 0.1(4) . . . . ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C8 C9 C14 C13 -179.1(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 N1 B1 C2 -178.2(3) . . . . ?
C10 N1 B1 C7 1.6(4) . . . . ?
C10 C9 C14 C13 1.9(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 Br1 -178.7(2) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C12 C13 C14 C9 -2.2(4) . . . . ?
C14 C9 C10 N1 179.2(2) . . . . ?
C14 C9 C10 C11 -0.9(4) . . . . ?
B1 N1 C10 C9 -0.7(4) . . . . ?
B1 N1 C10 C11 179.3(2) . . . . ?
B1 C2 C3 C4 177.2(3) . . . . ?
B1 C7 C8 C9 1.5(4) . . . . ?
Br2 C27 C28 C23 -179.5(2) . . . . ?
S2 C15 C16 C17 179.3(2) . . . . ?
S2 C15 C16 B2 -4.0(3) . . . . ?
S2 C15 C20 C19 -179.6(2) . . . . ?
S2 C21 C22 C23 -176.9(2) . . . . ?
S2 C21 B2 N2 179.63(19) . . . . ?
S2 C21 B2 C16 2.6(3) . . . . ?
N2 C24 C25 C26 -179.3(3) . . . . ?
C15 S2 C21 C22 172.5(3) . . . . ?
C15 S2 C21 B2 -4.0(2) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C15 C16 B2 N2 -175.5(3) . . . . ?
C15 C16 B2 C21 0.9(3) . . . . ?
C16 C15 C20 C19 2.4(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C16 B2 N2 0.5(5) . . . . ?
C17 C16 B2 C21 176.9(3) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C20 C15 C16 C17 -2.6(4) . . . . ?
C20 C15 C16 B2 174.2(3) . . . . ?
C21 S2 C15 C16 4.8(2) . . . . ?
C21 S2 C15 C20 -173.3(2) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C21 C22 C23 C28 178.4(3) . . . . ?
C22 C21 B2 N2 2.9(4) . . . . ?
C22 C21 B2 C16 -174.2(2) . . . . ?
C22 C23 C24 N2 0.0(4) . . . . ?
C22 C23 C24 C25 -179.6(2) . . . . ?
C22 C23 C28 C27 179.5(3) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 N2 B2 C16 172.5(3) . . . . ?
C24 N2 B2 C21 -3.7(4) . . . . ?
C24 C23 C28 C27 -1.3(4) . . . . ?
C24 C25 C26 C27 -1.6(5) . . . . ?
C25 C26 C27 Br2 -179.0(2) . . . . ?
C25 C26 C27 C28 1.4(5) . . . . ?
C26 C27 C28 C23 0.0(5) . . . . ?
C28 C23 C24 N2 -179.2(2) . . . . ?
C28 C23 C24 C25 1.2(4) . . . . ?
B2 N2 C24 C23 2.5(4) . . . . ?
B2 N2 C24 C25 -178.0(3) . . . . ?
B2 C16 C17 C18 -174.9(3) . . . . ?
B2 C21 C22 C23 -0.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-16
_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.627

