# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_9
_database_code_depnum_ccdc_archive 'CCDC 2415031'
loop_
_audit_author_name
_audit_author_address
'Guangping Sun'
;Nantong University
China
;
_audit_update_record             
;
2025-01-07 deposited with the CCDC.	2025-03-21 downloaded from the CCDC.
;
_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br N S'
_chemical_formula_sum            'C15 H12 Br N S'
_chemical_formula_weight         318.23
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.968(5)
_cell_length_b                   5.187(3)
_cell_length_c                   33.210(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.005(10)
_cell_angle_gamma                90
_cell_volume                     1369.2(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2828
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.041
_cell_measurement_theta_min      2.562
_shelx_estimated_absorpt_T_max   0.292
_shelx_estimated_absorpt_T_min   0.255
_exptl_absorpt_coefficient_mu    3.135
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0841 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.7594.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.52
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            7258
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         1.844
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2350
_reflns_number_total             3073
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.137
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.091
_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)+(0.1698P)²+6.0833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2768
_refine_ls_wR_factor_ref         0.2986
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.780(3)
 0.220(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C01C(H01A,H01B), C01J(H01C,H01D)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C00C(H00C), C00G(H00G), C013(H013), C01L(H01L), C00S(H00S), C18(H18),
 C24(H24)
;
_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 0.31310(16) -2.1892(3) 1.62377(3) 0.0598(5) Uani 1 1 d . . . . .
S008 S 0.1886(4) -2.5914(5) 1.80198(8) 0.0435(6) Uani 1 1 d . . . . .
N00R N 0.2725(16) -1.490(3) 2.0239(4) 0.074(3) Uani 1 1 d . . . . .
C1 C 0.3494(12) -2.1620(19) 1.7094(3) 0.038(2) Uani 1 1 d . . . . .
H1 H 0.411673 -2.013892 1.705236 0.046 Uiso 1 1 calc R U . . .
C00C C 0.0827(14) -1.919(2) 1.9542(3) 0.046(2) Uani 1 1 d . . . . .
H00C H -0.013524 -1.850021 1.964304 0.055 Uiso 1 1 calc R U . . .
C00G C 0.0701(15) -2.110(2) 1.9250(3) 0.049(2) Uani 1 1 d . . . . .
H00G H -0.035694 -2.166880 1.915110 0.059 Uiso 1 1 calc R U . . .
C01G C 0.2132(14) -2.2196(19) 1.9101(3) 0.041(2) Uani 1 1 d . . . . .
C011 C 0.2392(14) -1.833(2) 1.9680(3) 0.044(2) Uani 1 1 d . . . . .
C00P C 0.2821(13) -2.305(2) 1.6769(3) 0.040(2) Uani 1 1 d . . . . .
C013 C 0.1913(13) -2.521(2) 1.6829(3) 0.047(2) Uani 1 1 d . . . . .
H013 H 0.145642 -2.613721 1.660784 0.057 Uiso 1 1 calc R U . . .
C01L C 0.1660(13) -2.6043(18) 1.7213(3) 0.038(2) Uani 1 1 d . . . . .
H01L H 0.105397 -2.754579 1.725097 0.046 Uiso 1 1 calc R U . . .
C019 C 0.2320(11) -2.4615(16) 1.7550(3) 0.0324(18) Uani 1 1 d . . . . .
C00S C 0.3218(13) -2.2453(17) 1.7487(3) 0.039(2) Uani 1 1 d . . . . .
H00S H 0.365881 -2.150340 1.770722 0.047 Uiso 1 1 calc R U . . .
C00W C 0.2560(15) -1.637(2) 1.9993(3) 0.052(3) Uani 1 1 d . . . . .
C01C C 0.1941(15) -2.4311(19) 1.8787(3) 0.045(2) Uani 1 1 d . . . . .
H01A H 0.267131 -2.574188 1.886893 0.054 Uiso 1 1 calc R U . . .
H01B H 0.079019 -2.493095 1.876857 0.054 Uiso 1 1 calc R U . . .
C01J C 0.2385(14) -2.3338(19) 1.8379(3) 0.041(2) Uani 1 1 d . . . . .
H01C H 0.357236 -2.291326 1.838463 0.049 Uiso 1 1 calc R U . . .
H01D H 0.173844 -2.180528 1.830491 0.049 Uiso 1 1 calc R U . . .
C18 C 0.3793(13) -1.937(2) 1.9528(3) 0.045(2) Uani 1 1 d . . . . .
H18 H 0.484739 -1.874464 1.961880 0.054 Uiso 1 1 calc R U . . .
C24 C 0.3688(14) -2.130(2) 1.9247(3) 0.046(2) Uani 1 1 d . . . . .
H24 H 0.466276 -2.200606 1.915487 0.056 Uiso 1 1 calc R U . . .


_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 C00P 1.898(10) . ?
S008 C019 1.757(10) . ?
S008 C01J 1.817(11) . ?
N00R C00W 1.117(16) . ?
C1 H1 0.9300 . ?
C1 C00P 1.385(14) . ?
C1 C00S 1.408(14) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.388(16) . ?
C00C C011 1.373(17) . ?
C00G H00G 0.9300 . ?
C00G C01G 1.394(16) . ?
C01G C01C 1.512(14) . ?
C01G C24 1.381(16) . ?
C011 C00W 1.452(15) . ?
C011 C18 1.368(15) . ?
C00P C013 1.355(16) . ?
C013 H013 0.9300 . ?
C013 C01L 1.375(15) . ?
C01L H01L 0.9300 . ?
C01L C019 1.412(13) . ?
C019 C00S 1.354(14) . ?
C00S H00S 0.9300 . ?
C01C H01A 0.9700 . ?
C01C H01B 0.9700 . ?
C01C C01J 1.511(13) . ?
C01J H01C 0.9700 . ?
C01J H01D 0.9700 . ?
C18 H18 0.9300 . ?
C18 C24 1.368(16) . ?
C24 H24 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
C019 S008 C01J 104.7(5) . . ?
C00P C1 H1 120.7 . . ?
C00P C1 C00S 118.7(9) . . ?
C00S C1 H1 120.7 . . ?
C00G C00C H00C 120.4 . . ?
C011 C00C H00C 120.4 . . ?
C011 C00C C00G 119.2(10) . . ?
C00C C00G H00G 119.4 . . ?
C00C C00G C01G 121.2(11) . . ?
C01G C00G H00G 119.4 . . ?
C00G C01G C01C 119.6(10) . . ?
C24 C01G C00G 118.3(10) . . ?
C24 C01G C01C 122.1(9) . . ?
C00C C011 C00W 120.2(10) . . ?
C18 C011 C00C 119.6(10) . . ?
C18 C011 C00W 120.2(11) . . ?
C1 C00P Br1 119.0(8) . . ?
C013 C00P Br1 120.2(8) . . ?
C013 C00P C1 120.8(10) . . ?
C00P C013 H013 119.7 . . ?
C00P C013 C01L 120.6(10) . . ?
C01L C013 H013 119.7 . . ?
C013 C01L H01L 120.0 . . ?
C013 C01L C019 120.0(9) . . ?
C019 C01L H01L 120.0 . . ?
C01L C019 S008 114.7(7) . . ?
C00S C019 S008 126.4(7) . . ?
C00S C019 C01L 119.0(9) . . ?
C1 C00S H00S 119.5 . . ?
C019 C00S C1 121.0(9) . . ?
C019 C00S H00S 119.5 . . ?
N00R C00W C011 178.1(14) . . ?
C01G C01C H01A 109.5 . . ?
C01G C01C H01B 109.5 . . ?
H01A C01C H01B 108.0 . . ?
C01J C01C C01G 110.9(8) . . ?
C01J C01C H01A 109.5 . . ?
C01J C01C H01B 109.5 . . ?
S008 C01J H01C 110.4 . . ?
S008 C01J H01D 110.4 . . ?
C01C C01J S008 106.8(7) . . ?
C01C C01J H01C 110.4 . . ?
C01C C01J H01D 110.4 . . ?
H01C C01J H01D 108.6 . . ?
C011 C18 H18 119.1 . . ?
C011 C18 C24 121.9(10) . . ?
C24 C18 H18 119.1 . . ?
C01G C24 H24 120.1 . . ?
C18 C24 C01G 119.9(10) . . ?
C18 C24 H24 120.1 . . ?

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 C00P C013 C01L -179.0(9) . . . . ?
S008 C019 C00S C1 179.3(8) . . . . ?
C1 C00P C013 C01L -0.8(16) . . . . ?
C00C C00G C01G C01C 178.9(9) . . . . ?
C00C C00G C01G C24 -0.9(16) . . . . ?
C00C C011 C18 C24 -1.5(17) . . . . ?
C00G C00C C011 C00W -178.5(10) . . . . ?
C00G C00C C011 C18 -0.1(16) . . . . ?
C00G C01G C01C C01J 108.3(11) . . . . ?
C00G C01G C24 C18 -0.6(15) . . . . ?
C01G C01C C01J S008 -173.7(7) . . . . ?
C011 C00C C00G C01G 1.3(17) . . . . ?
C011 C18 C24 C01G 1.9(17) . . . . ?
C00P C1 C00S C019 0.3(15) . . . . ?
C00P C013 C01L C019 1.3(17) . . . . ?
C013 C01L C019 S008 179.8(8) . . . . ?
C013 C01L C019 C00S -0.9(15) . . . . ?
C01L C019 C00S C1 0.1(14) . . . . ?
C019 S008 C01J C01C 176.9(7) . . . . ?
C00S C1 C00P Br1 178.2(7) . . . . ?
C00S C1 C00P C013 0.0(15) . . . . ?
C00W C011 C18 C24 176.9(10) . . . . ?
C01C C01G C24 C18 179.5(9) . . . . ?
C01J S008 C019 C01L -165.8(7) . . . . ?
C01J S008 C019 C00S 14.9(10) . . . . ?
C24 C01G C01C C01J -71.9(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.780(3)
2 0.220(3)

