# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ldy221215_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2g6jhq
_database_code_depnum_ccdc_archive 'CCDC 2270393'
loop_
_audit_author_name
_audit_author_address
'Weiguang Yang'
;Guangdong Medical University
China
;
_audit_update_record             
;
2023-06-16 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H12 Br N3 O2 S2'
_chemical_formula_sum            'C17 H12 Br N3 O2 S2'
_chemical_formula_weight         434.33
_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'
O O 0.0106 0.0060 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.614(4)
_cell_length_b                   9.373(3)
_cell_length_c                   14.491(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.835(4)
_cell_angle_gamma                90
_cell_volume                     1709.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2904
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.723
_exptl_absorpt_coefficient_mu    2.665
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1149 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.6512.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10172
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.073
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2848
_reflns_number_total             3883
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.026
_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)+(0.0384P)²+1.2431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1019
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C15(H15), C6(H6), C2(H2), C16(H16), C8(H8), C14(H14), C5(H5)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.104
;
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 -0.03338(3) 0.20824(5) 0.54466(3) 0.07045(17) Uani 1 1 d . . . . .
S1 S 0.14551(5) 0.42275(8) 0.16646(4) 0.03160(17) Uani 1 1 d . . . . .
N1 N 0.07156(17) 0.3372(3) 0.09029(15) 0.0346(5) Uani 1 1 d . . . . .
N11 N 0.14031(19) 0.2913(3) -0.18326(16) 0.0471(7) Uani 1 1 d . . . . .
C12 C 0.0625(2) 0.2286(3) -0.14543(18) 0.0373(7) Uani 1 1 d . . . . .
S2 S -0.01995(6) 0.11075(10) -0.20691(5) 0.0442(2) Uani 1 1 d . . . . .
C3 C 0.1406(2) 0.2460(3) 0.3153(2) 0.0403(7) Uani 1 1 d . . . . .
H3 H 0.198489 0.200455 0.291787 0.048 Uiso 1 1 calc R U . . .
C17 C -0.1093(2) 0.1636(3) 0.04517(19) 0.0403(7) Uani 1 1 d . . . . .
H17 H -0.085868 0.218446 0.095983 0.048 Uiso 1 1 calc R U . . .
C15 C -0.2325(3) -0.0062(4) -0.0269(2) 0.0497(8) Uani 1 1 d . . . . .
H15 H -0.291159 -0.065302 -0.022564 0.060 Uiso 1 1 calc R U . . .
C6 C -0.0270(3) 0.3849(5) 0.3870(3) 0.0738(13) Uani 1 1 d . . . . .
H6 H -0.082623 0.433074 0.412340 0.089 Uiso 1 1 calc R U . . .
O1 O 0.12580(17) 0.5730(2) 0.16112(14) 0.0464(5) Uani 1 1 d . . . . .
O2 O 0.25443(15) 0.3787(3) 0.16767(13) 0.0458(5) Uani 1 1 d . . . . .
C2 C 0.1024(3) 0.1999(3) 0.3963(2) 0.0436(7) Uani 1 1 d . . . . .
H2 H 0.133488 0.122179 0.427479 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0967(2) 0.3342(3) 0.00381(18) 0.0324(6) Uani 1 1 d . . . . .
N2 N 0.03475(16) 0.2461(3) -0.05594(14) 0.0315(5) Uani 1 1 d . . . . .
C16 C -0.1973(3) 0.0774(4) 0.0484(2) 0.0506(8) Uani 1 1 d . . . . .
H16 H -0.233994 0.075026 0.101992 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1781(2) 0.4062(4) -0.0382(2) 0.0479(8) Uani 1 1 d . . . . .
H8 H 0.219961 0.470826 -0.003327 0.057 Uiso 1 1 calc R U . . .
C14 C -0.1817(2) -0.0021(3) -0.1069(2) 0.0431(7) Uani 1 1 d . . . . .
H14 H -0.205431 -0.057512 -0.157312 0.052 Uiso 1 1 calc R U . . .
C1 C 0.0182(2) 0.2685(4) 0.4313(2) 0.0435(7) Uani 1 1 d . . . . .
C4 C 0.0937(2) 0.3596(3) 0.26882(18) 0.0310(6) Uani 1 1 d . . . . .
C18 C -0.0565(2) 0.1667(3) -0.03572(17) 0.0307(6) Uani 1 1 d . . . . .
C5 C 0.0105(3) 0.4303(4) 0.3048(2) 0.0585(10) Uani 1 1 d . . . . .
H5 H -0.020357 0.508325 0.273814 0.070 Uiso 1 1 calc R U . . .
C9 C 0.1979(2) 0.3849(4) -0.1282(2) 0.0503(9) Uani 1 1 d . . . . .
C13 C -0.0942(2) 0.0858(3) -0.11186(19) 0.0346(6) Uani 1 1 d . . . . .
C10 C 0.2849(3) 0.4616(6) -0.1728(3) 0.0840(15) Uani 1 1 d . . . . .
H10A H 0.322731 0.395497 -0.209128 0.126 Uiso 1 1 calc R U . . .
H10B H 0.332918 0.502617 -0.125927 0.126 Uiso 1 1 calc R U . . .
H10C H 0.254943 0.535795 -0.212052 0.126 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 C1 1.893(3) . ?
S1 N1 1.610(2) . ?
S1 O1 1.432(2) . ?
S1 O2 1.434(2) . ?
S1 C4 1.763(3) . ?
N1 C7 1.313(3) . ?
N11 C12 1.296(4) . ?
N11 C9 1.363(4) . ?
C12 S2 1.724(3) . ?
C12 N2 1.376(3) . ?
S2 C13 1.732(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.369(4) . ?
C3 C4 1.373(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.376(4) . ?
C17 C18 1.387(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(5) . ?
C15 C14 1.362(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.371(5) . ?
C6 C5 1.379(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.367(4) . ?
C7 N2 1.397(3) . ?
C7 C8 1.401(4) . ?
N2 C18 1.418(3) . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.359(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(4) . ?
C4 C5 1.372(4) . ?
C18 C13 1.396(4) . ?
C5 H5 0.9300 . ?
C9 C10 1.495(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N1 S1 C4 100.31(13) . . ?
O1 S1 N1 111.23(13) . . ?
O1 S1 O2 116.54(14) . . ?
O1 S1 C4 107.64(13) . . ?
O2 S1 N1 112.08(13) . . ?
O2 S1 C4 107.59(13) . . ?
C7 N1 S1 119.9(2) . . ?
C12 N11 C9 115.7(2) . . ?
N11 C12 S2 121.3(2) . . ?
N11 C12 N2 126.3(3) . . ?
N2 C12 S2 112.4(2) . . ?
C12 S2 C13 90.86(14) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.4(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C1 C6 H6 120.2 . . ?
C1 C6 C5 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C3 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
N1 C7 N2 116.3(2) . . ?
N1 C7 C8 129.4(3) . . ?
N2 C7 C8 114.3(2) . . ?
C12 N2 C7 119.2(2) . . ?
C12 N2 C18 113.2(2) . . ?
C7 N2 C18 127.6(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 118.9(3) . . ?
C13 C14 H14 120.5 . . ?
C6 C1 Br1 119.2(2) . . ?
C2 C1 Br1 120.1(2) . . ?
C2 C1 C6 120.7(3) . . ?
C3 C4 S1 120.1(2) . . ?
C5 C4 S1 119.6(2) . . ?
C5 C4 C3 120.2(3) . . ?
C17 C18 N2 128.9(3) . . ?
C17 C18 C13 120.0(3) . . ?
C13 C18 N2 111.1(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
N11 C9 C10 115.7(3) . . ?
C8 C9 N11 122.1(3) . . ?
C8 C9 C10 122.1(3) . . ?
C14 C13 S2 126.7(2) . . ?
C14 C13 C18 120.9(3) . . ?
C18 C13 S2 112.5(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
S1 N1 C7 N2 173.76(19) . . . . ?
S1 N1 C7 C8 -5.8(5) . . . . ?
S1 C4 C5 C6 -177.1(3) . . . . ?
N1 S1 C4 C3 94.9(3) . . . . ?
N1 S1 C4 C5 -89.3(3) . . . . ?
N1 C7 N2 C12 -174.5(3) . . . . ?
N1 C7 N2 C18 4.5(4) . . . . ?
N1 C7 C8 C9 175.9(3) . . . . ?
N11 C12 S2 C13 -178.8(3) . . . . ?
N11 C12 N2 C7 -3.0(4) . . . . ?
N11 C12 N2 C18 177.9(3) . . . . ?
C12 N11 C9 C8 2.9(5) . . . . ?
C12 N11 C9 C10 -177.7(3) . . . . ?
C12 S2 C13 C14 -179.7(3) . . . . ?
C12 S2 C13 C18 0.4(2) . . . . ?
C12 N2 C18 C17 -176.8(3) . . . . ?
C12 N2 C18 C13 1.9(3) . . . . ?
S2 C12 N2 C7 177.5(2) . . . . ?
S2 C12 N2 C18 -1.6(3) . . . . ?
C3 C2 C1 Br1 -178.6(2) . . . . ?
C3 C2 C1 C6 -1.3(5) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C17 C18 C13 S2 177.5(2) . . . . ?
C17 C18 C13 C14 -2.4(4) . . . . ?
C15 C14 C13 S2 -178.3(2) . . . . ?
C15 C14 C13 C18 1.5(4) . . . . ?
O1 S1 N1 C7 78.7(3) . . . . ?
O1 S1 C4 C3 -148.8(2) . . . . ?
O1 S1 C4 C5 27.1(3) . . . . ?
O2 S1 N1 C7 -53.8(3) . . . . ?
O2 S1 C4 C3 -22.4(3) . . . . ?
O2 S1 C4 C5 153.4(3) . . . . ?
C2 C3 C4 S1 178.0(2) . . . . ?
C2 C3 C4 C5 2.2(5) . . . . ?
C7 N2 C18 C17 4.2(5) . . . . ?
C7 N2 C18 C13 -177.1(3) . . . . ?
C7 C8 C9 N11 -0.4(6) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
N2 C12 S2 C13 0.7(2) . . . . ?
N2 C7 C8 C9 -3.6(5) . . . . ?
N2 C18 C13 S2 -1.3(3) . . . . ?
N2 C18 C13 C14 178.8(3) . . . . ?
C16 C17 C18 N2 179.9(3) . . . . ?
C16 C17 C18 C13 1.3(4) . . . . ?
C16 C15 C14 C13 0.4(5) . . . . ?
C8 C7 N2 C12 5.1(4) . . . . ?
C8 C7 N2 C18 -175.9(3) . . . . ?
C14 C15 C16 C17 -1.5(5) . . . . ?
C1 C6 C5 C4 -0.9(7) . . . . ?
C4 S1 N1 C7 -167.7(2) . . . . ?
C4 C3 C2 C1 -0.9(5) . . . . ?
C18 C17 C16 C15 0.7(5) . . . . ?
C5 C6 C1 Br1 179.5(3) . . . . ?
C5 C6 C1 C2 2.2(6) . . . . ?
C9 N11 C12 S2 178.3(2) . . . . ?
C9 N11 C12 N2 -1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
