# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_22aprb_0m
_database_code_depnum_ccdc_archive 'CCDC 2178469'
loop_
_audit_author_name
_audit_author_address
'RAMESH METRE'
;IIT Jodhpur
India
;
_audit_update_record             
;
2022-06-11 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br N O3 S2'
_chemical_formula_sum            'C20 H16 Br N O3 S2'
_chemical_formula_weight         462.37
_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/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                   14.0219(3)
_cell_length_b                   7.5128(2)
_cell_length_c                   19.5632(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.9260(10)
_cell_angle_gamma                90
_cell_volume                     1924.93(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      2.22
_cell_measurement_theta_min      28.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0872 before and 0.0611 after correction. The Ratio of minimum to maximum transmission is 0.7400. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30510
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         2.932
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4269
_reflns_number_total             4772
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.087
_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)+(0.0346P)²+1.0592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.83593(2) -0.01408(3) 0.79265(2) 0.02404(7) Uani 1 1 d . . . . .
S1 S 0.81291(3) 0.39409(5) 0.47566(2) 0.01069(9) Uani 1 1 d . . . . .
O1 O 0.56824(9) 0.11702(16) 0.41210(7) 0.0145(2) Uani 1 1 d . . . . .
N1 N 0.72943(10) 0.10081(18) 0.40609(8) 0.0112(3) Uani 1 1 d . . . . .
C1 C 0.77557(13) 0.3812(2) 0.63532(9) 0.0142(3) Uani 1 1 d . . . . .
H1 H 0.807268 0.484594 0.628206 0.017 Uiso 1 1 calc R . . . .
S2 S 0.64472(3) 0.66709(5) 0.51866(2) 0.01371(9) Uani 1 1 d . . . . .
O2 O 0.51843(9) 0.48852(15) 0.35770(7) 0.0124(2) Uani 1 1 d . . . . .
C2 C 0.81997(13) 0.2821(2) 0.69876(10) 0.0162(3) Uani 1 1 d . . . . .
H2 H 0.881236 0.318078 0.734100 0.019 Uiso 1 1 calc R . . . .
O3 O 0.53882(11) 0.3357(2) 0.26455(8) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.77139(14) 0.1285(2) 0.70850(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.67905(14) 0.0738(3) 0.65780(10) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.646731 -0.027927 0.665812 0.021 Uiso 1 1 calc R . . . .
C5 C 0.63560(13) 0.1743(2) 0.59453(10) 0.0148(3) Uani 1 1 d . . . . .
H5 H 0.573457 0.139298 0.559968 0.018 Uiso 1 1 calc R . . . .
C6 C 0.68371(12) 0.3268(2) 0.58214(9) 0.0115(3) Uani 1 1 d . . . . .
C7 C 0.63459(12) 0.4239(2) 0.51052(9) 0.0101(3) Uani 1 1 d . . . . .
H7 H 0.561738 0.394222 0.492403 0.012 Uiso 1 1 calc R . . . .
C8 C 0.67529(12) 0.3780(2) 0.44950(9) 0.0092(3) Uani 1 1 d . . . . .
C9 C 0.62652(13) 0.5180(2) 0.38866(10) 0.0119(3) Uani 1 1 d . . . . .
H9 H 0.657286 0.512778 0.350913 0.014 Uiso 1 1 calc R . . . .
C10 C 0.64302(13) 0.6992(2) 0.42541(10) 0.0156(3) Uani 1 1 d . . . . .
H10A H 0.588315 0.779643 0.398663 0.019 Uiso 1 1 calc R . . . .
H10B H 0.707250 0.749764 0.426610 0.019 Uiso 1 1 calc R . . . .
C11 C 0.48340(14) 0.4000(2) 0.29268(9) 0.0164(3) Uani 1 1 d . . . . .
C12 C 0.36996(14) 0.3980(3) 0.26342(11) 0.0236(4) Uani 1 1 d . . . . .
H12A H 0.345513 0.366252 0.301785 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.346149 0.312591 0.224511 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.344927 0.514046 0.245067 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.64979(12) 0.1857(2) 0.42106(9) 0.0099(3) Uani 1 1 d . . . . .
C14 C 0.81326(12) 0.1915(2) 0.43042(9) 0.0101(3) Uani 1 1 d . . . . .
C15 C 0.90768(12) 0.1324(2) 0.42084(9) 0.0112(3) Uani 1 1 d . . . . .
C16 C 0.90664(14) -0.0219(2) 0.38091(10) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.847100 -0.088575 0.361751 0.020 Uiso 1 1 calc R . . . .
C17 C 0.99460(14) -0.0755(3) 0.36988(11) 0.0209(4) Uani 1 1 d . . . . .
H17 H 0.993979 -0.178563 0.343376 0.025 Uiso 1 1 calc R . . . .
C18 C 1.08386(14) 0.0239(2) 0.39824(10) 0.0169(4) Uani 1 1 d . . . . .
H18 H 1.142725 -0.012661 0.390740 0.020 Uiso 1 1 calc R . . . .
C19 C 1.08482(13) 0.1771(2) 0.43758(11) 0.0183(4) Uani 1 1 d . . . . .
H19 H 1.144359 0.243908 0.456413 0.022 Uiso 1 1 calc R . . . .
C20 C 0.99705(13) 0.2315(2) 0.44905(10) 0.0163(3) Uani 1 1 d . . . . .
H20 H 0.998033 0.334471 0.475675 0.020 Uiso 1 1 calc R . . . .


_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 C3 1.9007(18) . ?
S1 C8 1.8152(16) . ?
S1 C14 1.7617(16) . ?
O1 C13 1.209(2) . ?
N1 C13 1.405(2) . ?
N1 C14 1.293(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
S2 C7 1.8348(17) . ?
S2 C10 1.8317(19) . ?
O2 C9 1.434(2) . ?
O2 C11 1.362(2) . ?
C2 C3 1.387(3) . ?
O3 C11 1.202(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.391(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.510(2) . ?
C7 C8 1.535(2) . ?
C8 C9 1.552(2) . ?
C8 C13 1.543(2) . ?
C9 C10 1.518(2) . ?
C11 C12 1.486(3) . ?
C14 C15 1.470(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.391(2) . ?
C16 C17 1.386(2) . ?
C17 C18 1.391(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.389(2) . ?

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
C14 S1 C8 89.67(7) . . ?
C14 N1 C13 111.71(14) . . ?
C2 C1 C6 120.55(16) . . ?
C10 S2 C7 94.11(8) . . ?
C11 O2 C9 116.35(13) . . ?
C3 C2 C1 118.89(16) . . ?
C2 C3 Br1 118.85(14) . . ?
C4 C3 Br1 119.20(14) . . ?
C4 C3 C2 121.92(17) . . ?
C3 C4 C5 118.51(17) . . ?
C4 C5 C6 121.03(17) . . ?
C1 C6 C7 122.90(15) . . ?
C5 C6 C1 119.06(16) . . ?
C5 C6 C7 118.03(15) . . ?
C6 C7 S2 113.91(11) . . ?
C6 C7 C8 116.08(13) . . ?
C8 C7 S2 104.64(11) . . ?
C7 C8 S1 114.76(11) . . ?
C7 C8 C9 105.05(13) . . ?
C7 C8 C13 112.85(13) . . ?
C9 C8 S1 107.68(11) . . ?
C13 C8 S1 104.48(10) . . ?
C13 C8 C9 112.08(13) . . ?
O2 C9 C8 109.20(13) . . ?
O2 C9 C10 107.32(13) . . ?
C10 C9 C8 107.07(14) . . ?
C9 C10 S2 107.41(12) . . ?
O2 C11 C12 110.11(15) . . ?
O3 C11 O2 123.18(17) . . ?
O3 C11 C12 126.70(17) . . ?
O1 C13 N1 123.87(15) . . ?
O1 C13 C8 122.48(14) . . ?
N1 C13 C8 113.65(13) . . ?
N1 C14 S1 118.34(12) . . ?
N1 C14 C15 122.39(15) . . ?
C15 C14 S1 119.27(12) . . ?
C16 C15 C14 119.49(15) . . ?
C20 C15 C14 120.84(15) . . ?
C20 C15 C16 119.64(15) . . ?
C17 C16 C15 119.80(17) . . ?
C16 C17 C18 120.38(17) . . ?
C19 C18 C17 119.85(16) . . ?
C18 C19 C20 120.13(16) . . ?
C19 C20 C15 120.21(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
