# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2182405'
loop_
_audit_author_name
_audit_author_address
'Kai-kai Wang'
;xinxiang University
China
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Br N3 S'
_chemical_formula_weight         450.39

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.0251(10)
_cell_length_b                   11.4612(13)
_cell_length_c                   11.5392(13)
_cell_angle_alpha                64.078(2)
_cell_angle_beta                 82.620(2)
_cell_angle_gamma                83.522(2)
_cell_volume                     1062.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1763
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      24.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.046
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.662
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5465
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3717
_reflns_number_gt                2504
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0448P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3717
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.22317(5) 0.60164(5) 1.06520(3) 0.1109(2) Uani 1 1 d . . . . .
S1 S 0.11853(9) 0.38676(7) 0.65179(7) 0.0605(2) Uani 1 1 d . . . . .
N2 N 0.2863(2) 0.5753(2) 0.47055(19) 0.0488(5) Uani 1 1 d . . . . .
N3 N 0.3206(2) 0.7694(2) 0.2951(2) 0.0541(6) Uani 1 1 d . . . . .
N1 N 0.3083(3) 0.3724(2) 0.4673(2) 0.0613(6) Uani 1 1 d . . . . .
C11 C 0.2095(3) 0.6516(2) 0.6444(2) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.2034(3) 0.6758(2) 0.5054(2) 0.0458(6) Uani 1 1 d . . . . .
H10 H 0.0987 0.6839 0.4871 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2487(3) 0.4519(3) 0.5161(2) 0.0472(6) Uani 1 1 d . . . . .
C16 C 0.3428(3) 0.6186(3) 0.7012(2) 0.0509(7) Uani 1 1 d . . . . .
H16 H 0.4308 0.6076 0.6544 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0806(3) 0.6679(3) 0.7155(3) 0.0558(7) Uani 1 1 d . . . . .
H12 H -0.0102 0.6896 0.6786 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2816(3) 0.7963(3) 0.4081(2) 0.0544(7) Uani 1 1 d . . . . .
H9A H 0.2151 0.8740 0.3877 0.065 Uiso 1 1 calc R U . . .
H9B H 0.3704 0.8071 0.4408 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3470(3) 0.6018(3) 0.8263(3) 0.0595(8) Uani 1 1 d . . . . .
H15 H 0.4367 0.5775 0.8650 0.071 Uiso 1 1 calc R U . . .
C14 C 0.2172(4) 0.6215(3) 0.8932(3) 0.0594(8) Uani 1 1 d . . . . .
C8 C 0.3767(3) 0.6347(3) 0.3478(2) 0.0555(7) Uani 1 1 d . . . . .
H8A H 0.4821 0.6265 0.3609 0.067 Uiso 1 1 calc R U . . .
H8B H 0.3630 0.5952 0.2911 0.067 Uiso 1 1 calc R U . . .
C13 C 0.0842(4) 0.6525(3) 0.8403(3) 0.0651(8) Uani 1 1 d . . . . .
H13 H -0.0033 0.6631 0.8878 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1466(4) 0.2391(3) 0.6411(3) 0.0632(8) Uani 1 1 d . . . . .
C6 C 0.2513(4) 0.2509(3) 0.5377(3) 0.0653(8) Uani 1 1 d . . . . .
C18 C 0.3714(3) 0.9917(3) 0.1364(3) 0.0619(8) Uani 1 1 d . . . . .
C23 C 0.2604(4) 1.0256(3) 0.0557(3) 0.0695(9) Uani 1 1 d . . . . .
H23 H 0.2217 0.9609 0.0425 0.083 Uiso 1 1 calc R U . . .
C17 C 0.4326(3) 0.8537(3) 0.2012(3) 0.0711(9) Uani 1 1 d . . . . .
H17A H 0.4657 0.8219 0.1362 0.085 Uiso 1 1 calc R U . . .
H17B H 0.5189 0.8502 0.2451 0.085 Uiso 1 1 calc R U . . .
C4 C 0.0788(4) 0.1236(3) 0.7174(4) 0.0893(11) Uani 1 1 d . . . . .
H4 H 0.0073 0.1174 0.7851 0.107 Uiso 1 1 calc R U . . .
C22 C 0.2032(5) 1.1517(4) -0.0070(4) 0.0898(11) Uani 1 1 d . . . . .
H22 H 0.1266 1.1705 -0.0604 0.108 Uiso 1 1 calc R U . . .
C1 C 0.2916(5) 0.1431(4) 0.5116(5) 0.0983(12) Uani 1 1 d . . . . .
H1 H 0.3613 0.1482 0.4431 0.118 Uiso 1 1 calc R U . . .
C3 C 0.1199(7) 0.0195(4) 0.6901(6) 0.1198(17) Uani 1 1 d . . . . .
H3 H 0.0760 -0.0589 0.7400 0.144 Uiso 1 1 calc R U . . .
C21 C 0.2567(6) 1.2457(5) 0.0083(5) 0.1079(15) Uani 1 1 d . . . . .
H21 H 0.2188 1.3310 -0.0358 0.129 Uiso 1 1 calc R U . . .
C19 C 0.4250(5) 1.0893(5) 0.1525(4) 0.1043(13) Uani 1 1 d . . . . .
H19 H 0.5008 1.0709 0.2066 0.125 Uiso 1 1 calc R U . . .
C2 C 0.2249(6) 0.0287(5) 0.5903(7) 0.1217(18) Uani 1 1 d . . . . .
H2 H 0.2522 -0.0444 0.5751 0.146 Uiso 1 1 calc R U . . .
C20 C 0.3657(7) 1.2195(6) 0.0871(6) 0.1258(19) Uani 1 1 d . . . . .
H20 H 0.4020 1.2860 0.0987 0.151 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 C14 1.904(3) . ?
S1 C5 1.738(3) . ?
S1 C7 1.759(3) . ?
N2 C7 1.344(3) . ?
N2 C8 1.456(3) . ?
N2 C10 1.476(3) . ?
N3 C8 1.446(3) . ?
N3 C9 1.458(3) . ?
N3 C17 1.467(3) . ?
N1 C7 1.302(3) . ?
N1 C6 1.389(4) . ?
C11 C16 1.380(3) . ?
C11 C12 1.379(4) . ?
C11 C10 1.510(3) . ?
C10 C9 1.526(4) . ?
C10 H10 0.9800 . ?
C16 C15 1.376(4) . ?
C16 H16 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 C14 1.371(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.357(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9300 . ?
C5 C4 1.388(4) . ?
C5 C6 1.390(4) . ?
C6 C1 1.395(5) . ?
C18 C19 1.360(5) . ?
C18 C23 1.363(4) . ?
C18 C17 1.496(4) . ?
C23 C22 1.375(5) . ?
C23 H23 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 C3 1.363(6) . ?
C4 H4 0.9300 . ?
C22 C21 1.315(6) . ?
C22 H22 0.9300 . ?
C1 C2 1.379(7) . ?
C1 H1 0.9300 . ?
C3 C2 1.368(7) . ?
C3 H3 0.9300 . ?
C21 C20 1.345(7) . ?
C21 H21 0.9300 . ?
C19 C20 1.421(7) . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?
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
C5 S1 C7 88.61(15) . . ?
C7 N2 C8 120.4(2) . . ?
C7 N2 C10 125.1(2) . . ?
C8 N2 C10 110.8(2) . . ?
C8 N3 C9 104.4(2) . . ?
C8 N3 C17 111.1(2) . . ?
C9 N3 C17 113.4(2) . . ?
C7 N1 C6 109.9(3) . . ?
C16 C11 C12 118.6(2) . . ?
C16 C11 C10 121.5(2) . . ?
C12 C11 C10 119.8(2) . . ?
N2 C10 C11 114.5(2) . . ?
N2 C10 C9 100.4(2) . . ?
C11 C10 C9 113.4(2) . . ?
N2 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
N1 C7 N2 123.3(2) . . ?
N1 C7 S1 116.0(2) . . ?
N2 C7 S1 120.7(2) . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N3 C9 C10 103.3(2) . . ?
N3 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
N3 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 Br1 119.3(2) . . ?
C15 C14 Br1 119.2(2) . . ?
N3 C8 N2 103.6(2) . . ?
N3 C8 H8A 111.0 . . ?
N2 C8 H8A 111.0 . . ?
N3 C8 H8B 111.0 . . ?
N2 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 S1 128.9(3) . . ?
C6 C5 S1 109.4(2) . . ?
N1 C6 C5 116.1(3) . . ?
N1 C6 C1 124.8(4) . . ?
C5 C6 C1 119.1(3) . . ?
C19 C18 C23 116.7(4) . . ?
C19 C18 C17 122.2(3) . . ?
C23 C18 C17 121.1(3) . . ?
C18 C23 C22 122.6(4) . . ?
C18 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
N3 C17 C18 111.8(2) . . ?
N3 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N3 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C2 C1 C6 118.1(4) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C22 C21 C20 120.5(5) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C3 C2 C1 122.0(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C21 C20 C19 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?

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
C7 N2 C10 C11 67.5(3) . . . . ?
C8 N2 C10 C11 -134.3(2) . . . . ?
C7 N2 C10 C9 -170.6(2) . . . . ?
C8 N2 C10 C9 -12.4(3) . . . . ?
C16 C11 C10 N2 47.8(3) . . . . ?
C12 C11 C10 N2 -134.9(3) . . . . ?
C16 C11 C10 C9 -66.7(3) . . . . ?
C12 C11 C10 C9 110.6(3) . . . . ?
C6 N1 C7 N2 177.7(2) . . . . ?
C6 N1 C7 S1 0.2(3) . . . . ?
C8 N2 C7 N1 11.6(4) . . . . ?
C10 N2 C7 N1 167.9(2) . . . . ?
C8 N2 C7 S1 -170.95(19) . . . . ?
C10 N2 C7 S1 -14.7(3) . . . . ?
C5 S1 C7 N1 -0.3(2) . . . . ?
C5 S1 C7 N2 -177.9(2) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C10 C11 C16 C15 177.5(2) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C13 -176.9(3) . . . . ?
C8 N3 C9 C10 -43.0(3) . . . . ?
C17 N3 C9 C10 -164.0(2) . . . . ?
N2 C10 C9 N3 33.1(2) . . . . ?
C11 C10 C9 N3 155.6(2) . . . . ?
C11 C16 C15 C14 -1.6(4) . . . . ?
C16 C15 C14 C13 2.4(5) . . . . ?
C16 C15 C14 Br1 -178.8(2) . . . . ?
C9 N3 C8 N2 34.5(3) . . . . ?
C17 N3 C8 N2 157.1(2) . . . . ?
C7 N2 C8 N3 146.4(2) . . . . ?
C10 N2 C8 N3 -13.0(3) . . . . ?
C15 C14 C13 C12 -1.8(5) . . . . ?
Br1 C14 C13 C12 179.4(2) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C7 S1 C5 C4 -178.5(3) . . . . ?
C7 S1 C5 C6 0.3(2) . . . . ?
C7 N1 C6 C5 0.1(4) . . . . ?
C7 N1 C6 C1 -179.9(3) . . . . ?
C4 C5 C6 N1 178.6(3) . . . . ?
S1 C5 C6 N1 -0.4(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
S1 C5 C6 C1 179.7(3) . . . . ?
C19 C18 C23 C22 -0.2(5) . . . . ?
C17 C18 C23 C22 -178.9(3) . . . . ?
C8 N3 C17 C18 174.5(3) . . . . ?
C9 N3 C17 C18 -68.3(3) . . . . ?
C19 C18 C17 N3 114.9(3) . . . . ?
C23 C18 C17 N3 -66.4(4) . . . . ?
C6 C5 C4 C3 1.4(5) . . . . ?
S1 C5 C4 C3 -179.9(3) . . . . ?
C18 C23 C22 C21 0.8(5) . . . . ?
N1 C6 C1 C2 -179.9(4) . . . . ?
C5 C6 C1 C2 0.0(5) . . . . ?
C5 C4 C3 C2 -0.1(7) . . . . ?
C23 C22 C21 C20 -1.2(6) . . . . ?
C23 C18 C19 C20 0.0(5) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C4 C3 C2 C1 -1.3(8) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
C22 C21 C20 C19 1.0(7) . . . . ?
C18 C19 C20 C21 -0.4(7) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.044

