# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_240625_hj_3_150_0m
_database_code_depnum_ccdc_archive 'CCDC 2368233'
loop_
_audit_author_name
_audit_author_address
'Yu Zhu'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2024-07-05 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_audit_creation_date             2024-07-01
_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         'C17 H16 Br N S'
_chemical_formula_sum            'C17 H16 Br N S'
_chemical_formula_weight         346.28
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   9.4027(4)
_cell_length_b                   12.8347(5)
_cell_length_c                   13.5644(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.2640(10)
_cell_angle_gamma                90
_cell_volume                     1554.50(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7654
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.697
_cell_measurement_theta_min      4.231
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    3.146
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1601 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.8972.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14153
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.798
_diffrn_reflns_theta_min         4.230
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3253
_reflns_number_total             3532
_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         0.593
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.104
_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)+(0.0339P)²+0.7755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_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 0.68954(2) 0.55499(2) 0.24982(2) 0.03541(9) Uani 1 1 d . . . . .
S1 S 0.05688(4) 0.67060(3) 0.29969(3) 0.02224(11) Uani 1 1 d . . . . .
N1 N 0.03885(19) 0.43651(12) 0.17647(14) 0.0330(4) Uani 1 1 d . . . . .
H1A H 0.036083 0.371250 0.195726 0.040 Uiso 1 1 d R U . . .
H1B H 0.001725 0.477018 0.214684 0.040 Uiso 1 1 d R U . . .
C1 C 0.37924(19) 0.59537(12) 0.21292(12) 0.0221(3) Uani 1 1 d . . . . .
H1 H 0.409956 0.666234 0.219780 0.027 Uiso 1 1 calc R U . . .
C2 C 0.48430(19) 0.51724(13) 0.22085(13) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.4425(2) 0.41353(14) 0.20974(13) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.514281 0.360667 0.212323 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2943(2) 0.38816(13) 0.19481(14) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.264974 0.317026 0.187518 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1865(2) 0.46490(13) 0.19019(12) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.22924(19) 0.57053(12) 0.19498(12) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.11636(18) 0.65658(12) 0.18239(12) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.15212(19) 0.76427(13) 0.14274(13) 0.0246(3) Uani 1 1 d . . . . .
H8A H 0.177941 0.819172 0.196714 0.030 Uiso 1 1 calc R U . . .
H8B H 0.226953 0.761059 0.105227 0.030 Uiso 1 1 calc R U . . .
C9 C -0.0084(2) 0.76860(14) 0.07228(13) 0.0291(4) Uani 1 1 d . . . . .
C10 C -0.0315(2) 0.65382(14) 0.08733(13) 0.0277(4) Uani 1 1 d . . . . .
H10A H -0.025147 0.609347 0.029229 0.033 Uiso 1 1 calc R U . . .
H10B H -0.122719 0.638042 0.106246 0.033 Uiso 1 1 calc R U . . .
C11 C 0.23229(19) 0.69253(13) 0.39608(12) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.3108(2) 0.60905(14) 0.45345(13) 0.0316(4) Uani 1 1 d . . . . .
H12 H 0.270233 0.540721 0.441355 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4483(3) 0.62564(17) 0.52825(15) 0.0396(5) Uani 1 1 d . . . . .
H13 H 0.500968 0.568686 0.567984 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5092(2) 0.72467(18) 0.54531(14) 0.0387(5) Uani 1 1 d . . . . .
H14 H 0.604417 0.735305 0.595630 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4317(2) 0.80822(17) 0.48915(14) 0.0348(4) Uani 1 1 d . . . . .
H15 H 0.473423 0.876235 0.500999 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2924(2) 0.79253(14) 0.41532(13) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.238211 0.850154 0.377900 0.034 Uiso 1 1 calc R U . . .
C17 C -0.0967(3) 0.84471(18) 0.02379(18) 0.0455(5) Uani 1 1 d . . . . .
H17A H -0.199407 0.831280 -0.011630 0.055 Uiso 1 1 calc R U . . .
H17B H -0.057672 0.913041 0.024216 0.055 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 C2 1.9074(17) . ?
S1 C7 1.8532(16) . ?
S1 C11 1.7768(17) . ?
N1 H1A 0.8802 . ?
N1 H1B 0.8799 . ?
N1 C5 1.390(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(3) . ?
C5 C6 1.410(2) . ?
C6 C7 1.504(2) . ?
C7 C8 1.558(2) . ?
C7 C10 1.573(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.513(2) . ?
C9 C10 1.512(3) . ?
C9 C17 1.317(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.392(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?

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
C11 S1 C7 100.77(7) . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1A 109.3 . . ?
C5 N1 H1B 109.3 . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.40(15) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 Br1 118.82(13) . . ?
C3 C2 Br1 120.12(13) . . ?
C3 C2 C1 121.06(16) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.80(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.54(16) . . ?
C5 C4 H4 119.2 . . ?
N1 C5 C4 120.01(15) . . ?
N1 C5 C6 121.11(15) . . ?
C4 C5 C6 118.82(16) . . ?
C1 C6 C5 119.16(15) . . ?
C1 C6 C7 119.50(14) . . ?
C5 C6 C7 121.33(15) . . ?
C6 C7 S1 111.46(11) . . ?
C6 C7 C8 118.02(14) . . ?
C6 C7 C10 119.19(13) . . ?
C8 C7 S1 111.48(11) . . ?
C8 C7 C10 88.16(12) . . ?
C10 C7 S1 106.20(11) . . ?
C7 C8 H8A 113.9 . . ?
C7 C8 H8B 113.9 . . ?
H8A C8 H8B 111.1 . . ?
C9 C8 C7 88.29(13) . . ?
C9 C8 H8A 113.9 . . ?
C9 C8 H8B 113.9 . . ?
C10 C9 C8 92.07(13) . . ?
C17 C9 C8 133.68(19) . . ?
C17 C9 C10 134.0(2) . . ?
C7 C10 H10A 114.0 . . ?
C7 C10 H10B 114.0 . . ?
C9 C10 C7 87.77(13) . . ?
C9 C10 H10A 114.0 . . ?
C9 C10 H10B 114.0 . . ?
H10A C10 H10B 111.2 . . ?
C12 C11 S1 119.78(14) . . ?
C12 C11 C16 119.40(16) . . ?
C16 C11 S1 120.82(13) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.02(18) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.36(18) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.06(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.93(19) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.21(17) . . ?
C15 C16 H16 119.9 . . ?
C9 C17 H17A 120.0 . . ?
C9 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

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 C2 C3 C4 176.27(13) . . . . ?
S1 C7 C8 C9 -92.46(12) . . . . ?
S1 C7 C10 C9 97.60(12) . . . . ?
S1 C11 C12 C13 179.52(15) . . . . ?
S1 C11 C16 C15 -178.35(14) . . . . ?
N1 C5 C6 C1 177.47(15) . . . . ?
N1 C5 C6 C7 -1.8(2) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
C1 C6 C7 S1 -105.00(15) . . . . ?
C1 C6 C7 C8 25.9(2) . . . . ?
C1 C6 C7 C10 130.74(16) . . . . ?
C2 C1 C6 C5 3.2(2) . . . . ?
C2 C1 C6 C7 -177.56(14) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 N1 -179.14(17) . . . . ?
C3 C4 C5 C6 3.7(3) . . . . ?
C4 C5 C6 C1 -5.4(2) . . . . ?
C4 C5 C6 C7 175.36(15) . . . . ?
C5 C6 C7 S1 74.24(17) . . . . ?
C5 C6 C7 C8 -154.84(15) . . . . ?
C5 C6 C7 C10 -50.0(2) . . . . ?
C6 C1 C2 Br1 -178.06(12) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C7 C8 C9 136.62(14) . . . . ?
C6 C7 C10 C9 -135.61(15) . . . . ?
C7 S1 C11 C12 -94.20(15) . . . . ?
C7 S1 C11 C16 85.96(15) . . . . ?
C7 C8 C9 C10 -14.82(13) . . . . ?
C7 C8 C9 C17 160.4(2) . . . . ?
C8 C7 C10 C9 -14.25(13) . . . . ?
C8 C9 C10 C7 14.68(13) . . . . ?
C10 C7 C8 C9 14.24(12) . . . . ?
C11 S1 C7 C6 57.23(12) . . . . ?
C11 S1 C7 C8 -76.98(12) . . . . ?
C11 S1 C7 C10 -171.48(11) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C11 C16 C15 1.8(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 -1.4(3) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
C17 C9 C10 C7 -160.5(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
