# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_z20250925a
_database_code_depnum_ccdc_archive 'CCDC 2548904'
loop_
_audit_author_name
_audit_author_address
'Jing Xiao'
;Hunan University of Science and Technology
China
;
_audit_update_record             
;
2026-04-24 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V154 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H18 Br N S'
_chemical_formula_moiety         'C20 H18 Br N S'
_chemical_formula_weight         384.32
_chemical_melting_point          ?
_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'
_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.
;

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                   9.1192(13)
_cell_length_b                   6.3388(8)
_cell_length_c                   30.887(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.367(5)
_cell_angle_gamma                90
_cell_volume                     1780.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.15
_cell_measurement_reflns_used    9767
_cell_measurement_theta_min      2.287
_cell_measurement_theta_max      23.910
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4899
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.6571.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.550
_shelx_estimated_absorpt_T_max   0.760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      296.15
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 QUEST Mo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            37507
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3124
_reflns_number_gt                2492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+1.3313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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.
;
_audit_creation_date             2025-09-25
_exptl_crystal_colour_primary    colourless
_diffrn_source_power             0.07
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
;

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 1.17390(4) 1.30699(6) 0.57210(2) 0.08765(17) Uani 1 1 d . . . . .
S1 S 0.61648(8) 0.70360(12) 0.52828(2) 0.0572(2) Uani 1 1 d . . . . .
N1 N 0.6117(2) 0.5036(3) 0.62019(7) 0.0504(5) Uani 1 1 d D . . . .
C1 C 0.4961(3) 0.7640(4) 0.57089(8) 0.0531(6) Uani 1 1 d . . . . .
H1A H 0.469786 0.912103 0.568761 0.064 Uiso 1 1 calc R U . . .
H1B H 0.406312 0.682970 0.565586 0.064 Uiso 1 1 calc R U . . .
C2 C 0.5594(3) 0.7198(4) 0.61718(8) 0.0453(6) Uani 1 1 d . . . . .
H2 H 0.642784 0.814731 0.623988 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4416(3) 0.7663(4) 0.64816(8) 0.0454(6) Uani 1 1 d . . . . .
C4 C 0.3484(3) 0.6091(5) 0.66044(9) 0.0574(7) Uani 1 1 d . . . . .
H4 H 0.360172 0.471878 0.650629 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2375(3) 0.6542(5) 0.68724(10) 0.0690(8) Uani 1 1 d . . . . .
H5 H 0.174682 0.547574 0.695091 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2201(3) 0.8545(5) 0.70216(10) 0.0686(8) Uani 1 1 d . . . . .
H6 H 0.146054 0.884101 0.720340 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3114(4) 1.0112(5) 0.69040(10) 0.0704(8) Uani 1 1 d . . . . .
H7 H 0.299360 1.147759 0.700523 0.084 Uiso 1 1 calc R U . . .
C8 C 0.4220(3) 0.9675(4) 0.66345(9) 0.0601(7) Uani 1 1 d . . . . .
H8 H 0.483833 1.075367 0.655583 0.072 Uiso 1 1 calc R U . . .
C9 C 0.7164(2) 0.4418(4) 0.65320(7) 0.0444(6) Uani 1 1 d . . . . .
C10 C 0.7904(3) 0.2536(4) 0.64865(9) 0.0543(6) Uani 1 1 d . . . . .
H10 H 0.771994 0.173863 0.623549 0.065 Uiso 1 1 calc R U . . .
C11 C 0.8909(3) 0.1831(5) 0.68082(10) 0.0656(8) Uani 1 1 d . . . . .
H11 H 0.939420 0.055924 0.677272 0.079 Uiso 1 1 calc R U . . .
C12 C 0.9207(3) 0.2984(5) 0.71826(10) 0.0653(8) Uani 1 1 d . . . . .
H12 H 0.988671 0.250138 0.739990 0.078 Uiso 1 1 calc R U . . .
C13 C 0.8485(3) 0.4856(5) 0.72289(9) 0.0651(8) Uani 1 1 d . . . . .
H13 H 0.868126 0.565118 0.747968 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7468(3) 0.5580(5) 0.69086(8) 0.0566(7) Uani 1 1 d . . . . .
H14 H 0.698460 0.685191 0.694575 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7689(3) 0.8723(4) 0.54224(8) 0.0485(6) Uani 1 1 d . . . . .
C16 C 0.7718(3) 1.0732(5) 0.52502(8) 0.0569(7) Uani 1 1 d . . . . .
H16 H 0.691608 1.122267 0.507456 0.068 Uiso 1 1 calc R U . . .
C17 C 0.8925(3) 1.2018(4) 0.53362(9) 0.0614(7) Uani 1 1 d . . . . .
H17 H 0.894262 1.336735 0.521844 0.074 Uiso 1 1 calc R U . . .
C18 C 1.0097(3) 1.1287(5) 0.55967(8) 0.0547(7) Uani 1 1 d . . . . .
C19 C 1.0097(3) 0.9306(5) 0.57763(9) 0.0572(7) Uani 1 1 d . . . . .
H19 H 1.089636 0.883695 0.595571 0.069 Uiso 1 1 calc R U . . .
C20 C 0.8886(3) 0.8020(4) 0.56855(8) 0.0531(6) Uani 1 1 d . . . . .
H20 H 0.887640 0.666862 0.580248 0.064 Uiso 1 1 calc R U . . .
H1 H 0.624(3) 0.452(4) 0.5953(6) 0.059(8) Uiso 1 1 d D . . . .


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 C18 1.892(3) . ?
S1 C1 1.818(3) . ?
S1 C15 1.780(3) . ?
N1 C2 1.452(3) . ?
N1 C9 1.399(3) . ?
N1 H1 0.851(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.520(3) . ?
C3 C4 1.382(4) . ?
C3 C8 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(4) . ?
C9 C14 1.387(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 C20 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(4) . ?
C18 C19 1.373(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(4) . ?
C20 H20 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
C15 S1 C1 101.61(12) . . ?
C2 N1 H1 112.0(19) . . ?
C9 N1 C2 120.9(2) . . ?
C9 N1 H1 114.7(19) . . ?
S1 C1 H1A 108.4 . . ?
S1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C2 C1 S1 115.70(18) . . ?
C2 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C2 C1 109.4(2) . . ?
N1 C2 H2 108.7 . . ?
N1 C2 C3 112.8(2) . . ?
C1 C2 H2 108.7 . . ?
C3 C2 C1 108.6(2) . . ?
C3 C2 H2 108.7 . . ?
C4 C3 C2 120.8(2) . . ?
C8 C3 C2 120.8(2) . . ?
C8 C3 C4 118.4(2) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.7(3) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 N1 118.6(2) . . ?
C10 C9 C14 118.4(2) . . ?
C14 C9 N1 122.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C16 C15 S1 119.9(2) . . ?
C16 C15 C20 119.0(2) . . ?
C20 C15 S1 121.0(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 Br1 119.2(2) . . ?
C17 C18 C19 121.6(3) . . ?
C19 C18 Br1 119.2(2) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.7(3) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?

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 C18 C19 C20 179.59(19) . . . . ?
S1 C1 C2 N1 -53.1(3) . . . . ?
S1 C1 C2 C3 -176.59(17) . . . . ?
S1 C15 C16 C17 -176.5(2) . . . . ?
S1 C15 C20 C19 177.0(2) . . . . ?
N1 C2 C3 C4 -29.4(3) . . . . ?
N1 C2 C3 C8 152.9(2) . . . . ?
N1 C9 C10 C11 -178.0(2) . . . . ?
N1 C9 C14 C13 178.1(3) . . . . ?
C1 S1 C15 C16 -91.0(2) . . . . ?
C1 S1 C15 C20 92.2(2) . . . . ?
C1 C2 C3 C4 92.1(3) . . . . ?
C1 C2 C3 C8 -85.7(3) . . . . ?
C2 N1 C9 C10 -163.5(2) . . . . ?
C2 N1 C9 C14 18.2(4) . . . . ?
C2 C3 C4 C5 -177.3(2) . . . . ?
C2 C3 C8 C7 177.7(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 C7 C8 C3 0.0(5) . . . . ?
C8 C3 C4 C5 0.4(4) . . . . ?
C9 N1 C2 C1 158.3(2) . . . . ?
C9 N1 C2 C3 -80.7(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C15 S1 C1 C2 -60.4(2) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
C16 C17 C18 Br1 -179.1(2) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C15 -0.7(4) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
