# 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_a201009a_pl
_database_code_depnum_ccdc_archive 'CCDC 2075411'
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             2020-10-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_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_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   28.1429(16)
_cell_length_b                   35.0042(16)
_cell_length_c                   4.9701(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4896.1(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4708
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2880
_cell_measurement_theta_min      2.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.505
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8248
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                1771
_reflns_number_total             1992
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.282
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.024
_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)+(0.0141P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0508
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.985(14)
 0.015(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Riding coordinates:
 N1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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 0.29344(2) 0.18966(2) 0.70756(16) 0.05902(19) Uani 1 1 d . . . . .
S1 S 0.26918(4) 0.11115(3) 1.0808(3) 0.0441(3) Uani 1 1 d . . . . .
N1 N 0.15088(11) 0.11972(9) 0.6409(8) 0.0356(10) Uani 1 1 d . . . . .
H1 H 0.124167 0.107892 0.627640 0.043 Uiso 1 1 d R . . . .
C1 C 0.15789(13) 0.15101(11) 0.4738(11) 0.0344(11) Uani 1 1 d . . . . .
C2 C 0.12362(14) 0.16177(12) 0.2878(10) 0.0427(13) Uani 1 1 d . . . . .
H2 H 0.095520 0.147879 0.277168 0.051 Uiso 1 1 calc R . . . .
C3 C 0.13005(16) 0.19202(12) 0.1212(11) 0.0495(15) Uani 1 1 d . . . . .
H3 H 0.106830 0.198392 -0.004103 0.059 Uiso 1 1 calc R . . . .
C4 C 0.17122(16) 0.21329(12) 0.1385(12) 0.0515(15) Uani 1 1 d . . . . .
H4 H 0.175563 0.234194 0.025681 0.062 Uiso 1 1 calc R . . . .
C5 C 0.20557(14) 0.20384(12) 0.3201(11) 0.0445(13) Uani 1 1 d . . . . .
H5 H 0.233047 0.218535 0.329257 0.053 Uiso 1 1 calc R . . . .
C6 C 0.20047(13) 0.17249(11) 0.4934(10) 0.0355(11) Uani 1 1 d . . . . .
C7 C 0.23630(12) 0.16061(11) 0.6857(11) 0.0357(11) Uani 1 1 d . . . . .
C8 C 0.23070(13) 0.13010(11) 0.8412(10) 0.0352(11) Uani 1 1 d . . . . .
C9 C 0.22825(14) 0.07484(11) 1.1784(11) 0.0379(11) Uani 1 1 d . . . . .
C10 C 0.23769(15) 0.04924(12) 1.3812(10) 0.0448(14) Uani 1 1 d . . . . .
H10 H 0.266081 0.050531 1.476513 0.054 Uiso 1 1 calc R . . . .
C11 C 0.20447(15) 0.02169(13) 1.4408(12) 0.0525(14) Uani 1 1 d . . . . .
H11 H 0.210438 0.004246 1.577816 0.063 Uiso 1 1 calc R . . . .
C12 C 0.16211(17) 0.01968(12) 1.2982(12) 0.0525(14) Uani 1 1 d . . . . .
H12 H 0.140009 0.000738 1.337516 0.063 Uiso 1 1 calc R . . . .
C13 C 0.15306(15) 0.04591(12) 1.0984(11) 0.0417(12) Uani 1 1 d . . . . .
H13 H 0.124488 0.044621 1.004813 0.050 Uiso 1 1 calc R . . . .
C14 C 0.18558(14) 0.07422(11) 1.0335(10) 0.0335(11) Uani 1 1 d . . . . .
B1 B 0.18422(16) 0.10693(13) 0.8278(12) 0.0338(12) 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 C7 1.906(3) . ?
S1 C8 1.741(4) . ?
S1 C9 1.783(4) . ?
N1 H1 0.8607 . ?
N1 C1 1.388(5) . ?
N1 B1 1.394(6) . ?
C1 C2 1.388(6) . ?
C1 C6 1.418(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(6) . ?
C6 C7 1.450(6) . ?
C7 C8 1.327(6) . ?
C8 B1 1.540(6) . ?
C9 C10 1.374(6) . ?
C9 C14 1.401(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(5) . ?
C14 B1 1.535(7) . ?

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 C9 93.2(2) . . ?
C1 N1 H1 117.3 . . ?
C1 N1 B1 123.8(3) . . ?
B1 N1 H1 119.0 . . ?
N1 C1 C6 119.8(4) . . ?
C2 C1 N1 120.9(4) . . ?
C2 C1 C6 119.3(4) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 118.7(4) . . ?
C5 C6 C1 117.3(4) . . ?
C5 C6 C7 123.9(4) . . ?
C6 C7 Br1 118.1(3) . . ?
C8 C7 Br1 119.8(3) . . ?
C8 C7 C6 122.1(3) . . ?
C7 C8 S1 129.1(3) . . ?
C7 C8 B1 119.9(4) . . ?
B1 C8 S1 110.9(3) . . ?
C10 C9 S1 122.6(3) . . ?
C10 C9 C14 122.2(4) . . ?
C14 C9 S1 115.2(4) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.9(4) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.5(4) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 B1 110.6(4) . . ?
C13 C14 C9 117.2(4) . . ?
C13 C14 B1 132.2(4) . . ?
N1 B1 C8 115.5(4) . . ?
N1 B1 C14 134.4(4) . . ?
C14 B1 C8 110.0(4) . . ?

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 C7 C8 S1 0.8(6) . . . . ?
Br1 C7 C8 B1 178.9(3) . . . . ?
S1 C8 B1 N1 -179.8(3) . . . . ?
S1 C8 B1 C14 0.7(5) . . . . ?
S1 C9 C10 C11 -178.9(4) . . . . ?
S1 C9 C14 C13 178.6(3) . . . . ?
S1 C9 C14 B1 -2.1(5) . . . . ?
N1 C1 C2 C3 -179.3(4) . . . . ?
N1 C1 C6 C5 -179.9(4) . . . . ?
N1 C1 C6 C7 1.2(6) . . . . ?
C1 N1 B1 C8 0.2(6) . . . . ?
C1 N1 B1 C14 179.5(5) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C6 C7 Br1 179.6(3) . . . . ?
C1 C6 C7 C8 0.8(7) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C2 C1 C6 C7 -179.1(4) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C4 C5 C6 C7 178.5(5) . . . . ?
C5 C6 C7 Br1 0.8(6) . . . . ?
C5 C6 C7 C8 -178.1(4) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C6 C7 C8 S1 179.6(4) . . . . ?
C6 C7 C8 B1 -2.2(7) . . . . ?
C7 C8 B1 N1 1.7(7) . . . . ?
C7 C8 B1 C14 -177.7(4) . . . . ?
C8 S1 C9 C10 -177.8(4) . . . . ?
C8 S1 C9 C14 2.2(4) . . . . ?
C9 S1 C8 C7 176.7(5) . . . . ?
C9 S1 C8 B1 -1.6(4) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C9 C14 B1 N1 -178.5(5) . . . . ?
C9 C14 B1 C8 0.8(5) . . . . ?
C10 C9 C14 C13 -1.4(7) . . . . ?
C10 C9 C14 B1 177.9(4) . . . . ?
C10 C11 C12 C13 -1.0(8) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C9 0.5(7) . . . . ?
C12 C13 C14 B1 -178.6(5) . . . . ?
C13 C14 B1 N1 0.7(9) . . . . ?
C13 C14 B1 C8 -180.0(4) . . . . ?
C14 C9 C10 C11 1.1(7) . . . . ?
B1 N1 C1 C2 178.6(4) . . . . ?
B1 N1 C1 C6 -1.7(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.985(14)
2 0.015(14)

