# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_230406_sja20230401_0m
_database_code_depnum_ccdc_archive 'CCDC 2428942'
loop_
_audit_author_name
_audit_author_address
'Zheng Wang'
;Hangzhou City University
China
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 Br N2 S'
_chemical_formula_sum            'C13 H13 Br N2 S'
_chemical_formula_weight         309.22
_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                   12.2575(10)
_cell_length_b                   7.9358(6)
_cell_length_c                   13.1764(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.726(3)
_cell_angle_gamma                90
_cell_volume                     1275.31(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7228
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.412
_exptl_absorpt_coefficient_mu    3.365
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.7776.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.000
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2425
_reflns_number_total             2913
_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       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.056
_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)+(0.0250P)²+0.6092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0721
_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. Restrained distances
 S1-C2 \\sim S1A-C2
 with sigma of 0.02
 S1-C12 \\sim S1A-C12A
 with sigma of 0.02
 C2-C12 \\sim C2-C12A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C2 \\sim S1 \\sim C12 \\sim S1A \\sim C12A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(S1A)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(S1)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C12A(H12D,H12E,
 H12F)
;
_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 0.13209(2) 0.39872(4) 0.02902(2) 0.04826(10) Uani 1 1 d . . . . .
N1 N 0.64263(14) 0.3333(2) 0.47241(14) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.55624(13) 0.3303(2) 0.40147(13) 0.0318(4) Uani 1 1 d . . . . .
C1 C 0.74076(17) 0.3810(3) 0.44685(19) 0.0368(5) Uani 1 1 d . . . . .
C2 C 0.75670(16) 0.4315(3) 0.34767(19) 0.0355(5) Uani 1 1 d D U . . .
C3 C 0.66771(16) 0.4363(2) 0.27400(17) 0.0300(4) Uani 1 1 d . . . . .
C4 C 0.56726(16) 0.3798(2) 0.30658(15) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.46299(16) 0.3791(2) 0.23794(15) 0.0272(4) Uani 1 1 d . . . . .
C6 C 0.45555(17) 0.3129(2) 0.13943(15) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.518785 0.265112 0.114581 0.037 Uiso 1 1 calc R U . . .
C7 C 0.35768(17) 0.3157(3) 0.07726(16) 0.0338(4) Uani 1 1 d . . . . .
H7 H 0.353108 0.269754 0.010394 0.041 Uiso 1 1 calc R U . . .
C8 C 0.26671(17) 0.3867(3) 0.11447(17) 0.0337(4) Uani 1 1 d . . . . .
C9 C 0.27108(17) 0.4520(3) 0.21209(17) 0.0354(5) Uani 1 1 d . . . . .
H9 H 0.207487 0.499745 0.236285 0.042 Uiso 1 1 calc R U . . .
C10 C 0.36886(16) 0.4471(3) 0.27415(16) 0.0309(4) Uani 1 1 d . . . . .
H10 H 0.372189 0.489987 0.341694 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8295(2) 0.3829(3) 0.5342(2) 0.0534(7) Uani 1 1 d . . . . .
H11A H 0.858282 0.497638 0.543890 0.080 Uiso 1 1 calc R U . . .
H11B H 0.888855 0.306992 0.519043 0.080 Uiso 1 1 calc R U . . .
H11C H 0.799353 0.345417 0.596481 0.080 Uiso 1 1 calc R U . . .
C13 C 0.6741(2) 0.5064(3) 0.16921(18) 0.0415(5) Uani 1 1 d . . . . .
H13A H 0.685468 0.414234 0.121894 0.062 Uiso 1 1 calc R U . . .
H13B H 0.735377 0.585854 0.170494 0.062 Uiso 1 1 calc R U . . .
H13C H 0.605493 0.564896 0.146681 0.062 Uiso 1 1 calc R U . . .
S1 S 0.8832(4) 0.5018(9) 0.3021(9) 0.0475(12) Uani 0.467(19) 1 d D U P A 1
C12 C 0.9581(9) 0.3077(13) 0.3048(10) 0.049(2) Uani 0.467(19) 1 d D U P A 1
H12A H 0.921071 0.228831 0.255592 0.074 Uiso 0.467(19) 1 calc R U P A 1
H12B H 0.961734 0.258988 0.373404 0.074 Uiso 0.467(19) 1 calc R U P A 1
H12C H 1.032594 0.329214 0.286920 0.074 Uiso 0.467(19) 1 calc R U P A 1
S1A S 0.8931(4) 0.5022(7) 0.3371(5) 0.0408(9) Uani 0.533(19) 1 d D U P A 2
C12A C 0.9432(9) 0.3380(14) 0.2630(12) 0.062(3) Uani 0.533(19) 1 d D U P A 2
H12D H 0.898949 0.331982 0.196947 0.094 Uiso 0.533(19) 1 calc R U P A 2
H12E H 0.938539 0.230543 0.298987 0.094 Uiso 0.533(19) 1 calc R U P A 2
H12F H 1.019762 0.360797 0.252259 0.094 Uiso 0.533(19) 1 calc R U P A 2


_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 C8 1.905(2) . ?
N1 N2 1.341(2) . ?
N1 C1 1.336(3) . ?
N2 C4 1.330(3) . ?
C1 C2 1.399(3) . ?
C1 C11 1.503(3) . ?
C2 C3 1.386(3) . ?
C2 S1 1.806(5) . ?
C2 S1A 1.782(4) . ?
C3 C4 1.417(3) . ?
C3 C13 1.498(3) . ?
C4 C5 1.490(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.400(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(3) . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
S1 C12 1.792(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S1A C12A 1.774(8) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

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
C1 N1 N2 119.84(19) . . ?
C4 N2 N1 120.19(17) . . ?
N1 C1 C2 122.0(2) . . ?
N1 C1 C11 114.3(2) . . ?
C2 C1 C11 123.7(2) . . ?
C1 C2 S1 127.1(4) . . ?
C1 C2 S1A 112.5(3) . . ?
C3 C2 C1 119.24(18) . . ?
C3 C2 S1 113.6(4) . . ?
C3 C2 S1A 128.0(3) . . ?
C2 C3 C4 115.22(19) . . ?
C2 C3 C13 123.10(19) . . ?
C4 C3 C13 121.6(2) . . ?
N2 C4 C3 123.44(19) . . ?
N2 C4 C5 114.08(16) . . ?
C3 C4 C5 122.41(18) . . ?
C6 C5 C4 122.59(17) . . ?
C6 C5 C10 118.86(19) . . ?
C10 C5 C4 118.55(18) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.15(19) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 Br1 119.51(17) . . ?
C7 C8 C9 121.7(2) . . ?
C9 C8 Br1 118.81(16) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.3(2) . . ?
C9 C10 H10 119.8 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 S1 C2 100.5(5) . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12A S1A C2 101.0(4) . . ?
S1A C12A H12D 109.5 . . ?
S1A C12A H12E 109.5 . . ?
S1A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 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 C8 C9 C10 -178.72(16) . . . . ?
N1 N2 C4 C3 0.5(3) . . . . ?
N1 N2 C4 C5 -176.57(17) . . . . ?
N1 C1 C2 C3 1.5(3) . . . . ?
N1 C1 C2 S1 179.0(4) . . . . ?
N1 C1 C2 S1A 175.9(2) . . . . ?
N2 N1 C1 C2 1.2(3) . . . . ?
N2 N1 C1 C11 178.46(19) . . . . ?
N2 C4 C5 C6 -134.6(2) . . . . ?
N2 C4 C5 C10 45.1(2) . . . . ?
C1 N1 N2 C4 -2.2(3) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
C1 C2 C3 C13 173.08(19) . . . . ?
C1 C2 S1 C12 70.9(10) . . . . ?
C1 C2 S1A C12A 110.5(8) . . . . ?
C2 C3 C4 N2 2.1(3) . . . . ?
C2 C3 C4 C5 178.94(17) . . . . ?
C3 C2 S1 C12 -111.5(7) . . . . ?
C3 C2 S1A C12A -75.7(9) . . . . ?
C3 C4 C5 C6 48.3(3) . . . . ?
C3 C4 C5 C10 -132.0(2) . . . . ?
C4 C5 C6 C7 -179.37(18) . . . . ?
C4 C5 C10 C9 178.65(18) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C5 C10 C9 -1.6(3) . . . . ?
C6 C7 C8 Br1 178.01(15) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
C11 C1 C2 C3 -175.5(2) . . . . ?
C11 C1 C2 S1 2.0(5) . . . . ?
C11 C1 C2 S1A -1.1(3) . . . . ?
C13 C3 C4 N2 -174.04(19) . . . . ?
C13 C3 C4 C5 2.8(3) . . . . ?
S1 C2 C3 C4 179.2(3) . . . . ?
S1 C2 C3 C13 -4.7(4) . . . . ?
S1A C2 C3 C4 -176.4(2) . . . . ?
S1A C2 C3 C13 -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
