# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_4A-R1
_database_code_depnum_ccdc_archive 'CCDC 2119472'
loop_
_audit_author_name
_audit_author_address
'Ravi Singh K'
;DoS in Chemistry, University of Mysore
India
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Br2 N4 O2 S4'
_chemical_formula_weight         658.46

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'

_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                   10.6549(6)
_cell_length_b                   11.8312(6)
_cell_length_c                   12.7053(7)
_cell_angle_alpha                62.656(2)
_cell_angle_beta                 78.805(2)
_cell_angle_gamma                65.198(2)
_cell_volume                     1291.45(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6367
_cell_measurement_theta_min      3.295
_cell_measurement_theta_max      28.273

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear whitish'
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.490
_shelx_estimated_absorpt_T_min   0.542
_shelx_estimated_absorpt_T_max   0.623
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_T_max  0.592
_exptl_absorpt_process_details   'Crys Alis RED'
_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  Bruker
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         46752
_diffrn_detector_area_resol_mean ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46752
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.295
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6367
_reflns_number_gt                4665
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0504P)²+1.1271P] 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         6367
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_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
Br2 Br 0.56457(4) 0.38055(4) 0.81392(4) 0.06463(13) Uani 1 1 d . . . . .
Br1 Br 0.81300(4) 0.16825(5) 0.04653(3) 0.06853(13) Uani 1 1 d . . . . .
S3 S 0.13238(8) -0.11604(7) 0.62022(7) 0.04739(18) Uani 1 1 d . . . . .
S2 S 0.00372(10) 0.48567(9) 0.23309(9) 0.0588(2) Uani 1 1 d . . . . .
S4 S -0.11053(10) -0.09421(10) 0.77525(9) 0.0630(2) Uani 1 1 d . . . . .
S1 S -0.20686(14) 0.65121(13) 0.02982(10) 0.0786(3) Uani 1 1 d . . . . .
O2 O 0.3652(2) -0.1108(2) 0.4573(2) 0.0589(6) Uani 1 1 d . . . . .
O1 O 0.2022(3) 0.3754(2) 0.4203(2) 0.0613(6) Uani 1 1 d . . . . .
N2 N 0.1710(3) 0.5755(2) 0.4237(2) 0.0459(6) Uani 1 1 d . . . . .
H2 H 0.125097 0.662850 0.392464 0.055 Uiso 1 1 calc R U . . .
N4 N -0.0099(3) 0.1098(3) 0.6413(2) 0.0477(6) Uani 1 1 d . . . . .
N3 N 0.3425(3) 0.1102(2) 0.3982(2) 0.0463(6) Uani 1 1 d . . . . .
H3A H 0.295298 0.182483 0.410444 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2631(3) 0.5243(3) 0.5158(3) 0.0417(6) Uani 1 1 d . . . . .
N1 N -0.1048(3) 0.7501(3) 0.1278(3) 0.0626(8) Uani 1 1 d . . . . .
C7 C 0.3098(3) 0.6154(3) 0.5198(3) 0.0455(7) Uani 1 1 d . . . . .
H7 H 0.280411 0.705882 0.462567 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1834(3) 0.0214(3) 0.5399(3) 0.0404(6) Uani 1 1 d . . . . .
C13 C -0.0030(3) -0.0164(3) 0.6781(3) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.1472(3) 0.5020(3) 0.3796(3) 0.0459(7) Uani 1 1 d . . . . .
C16 C 0.3053(3) 0.0001(3) 0.4622(3) 0.0430(6) Uani 1 1 d . . . . .
C14 C 0.0953(3) 0.1293(3) 0.5632(3) 0.0484(7) Uani 1 1 d . . . . .
H14 H 0.105898 0.213184 0.527590 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4402(3) 0.4402(3) 0.6930(3) 0.0473(7) Uani 1 1 d . . . . .
C17 C 0.4496(3) 0.1190(3) 0.3141(3) 0.0436(6) Uani 1 1 d . . . . .
C4 C 0.0498(3) 0.5795(3) 0.2797(3) 0.0483(7) Uani 1 1 d . . . . .
C20 C 0.6609(3) 0.1505(4) 0.1510(3) 0.0499(7) Uani 1 1 d . . . . .
C8 C 0.3990(3) 0.5741(3) 0.6073(3) 0.0476(7) Uani 1 1 d . . . . .
H8 H 0.430933 0.635542 0.608576 0.057 Uiso 1 1 calc R U . . .
C3 C -0.0174(4) 0.7151(3) 0.2132(3) 0.0533(8) Uani 1 1 d . . . . .
H3 H -0.004818 0.781666 0.224959 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3935(3) 0.3484(3) 0.6911(3) 0.0532(8) Uani 1 1 d . . . . .
H10 H 0.421737 0.258540 0.749456 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4668(4) 0.2435(3) 0.2557(3) 0.0585(9) Uani 1 1 d . . . . .
H18 H 0.406187 0.317887 0.271304 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3062(3) 0.3893(3) 0.6040(3) 0.0510(7) Uani 1 1 d . . . . .
H11 H 0.275085 0.327137 0.603095 0.061 Uiso 1 1 calc R U . . .
C21 C 0.6453(4) 0.0274(4) 0.2053(4) 0.0638(9) Uani 1 1 d . . . . .
H21 H 0.705022 -0.045293 0.187118 0.077 Uiso 1 1 calc R U . . .
C2 C -0.1046(4) 0.6392(4) 0.1288(3) 0.0552(8) Uani 1 1 d . . . . .
C19 C 0.5717(4) 0.2590(4) 0.1752(3) 0.0648(9) Uani 1 1 d . . . . .
H19 H 0.582023 0.343128 0.137188 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5404(4) 0.0106(4) 0.2875(4) 0.0628(9) Uani 1 1 d . . . . .
H22 H 0.530830 -0.073805 0.324968 0.075 Uiso 1 1 calc R U . . .
C12 C -0.2239(5) 0.0367(4) 0.8188(4) 0.0807(12) Uani 1 1 d . . . . .
H12A H -0.272683 0.116463 0.750768 0.121 Uiso 1 1 calc R U . . .
H12B H -0.171664 0.060218 0.853693 0.121 Uiso 1 1 calc R U . . .
H12C H -0.288996 0.004662 0.875753 0.121 Uiso 1 1 calc R U . . .
C1 C -0.1860(5) 0.4768(5) 0.0802(4) 0.0841(13) Uani 1 1 d . . . . .
H1A H -0.238709 0.471126 0.030811 0.126 Uiso 1 1 calc R U . . .
H1B H -0.218029 0.443404 0.160565 0.126 Uiso 1 1 calc R U . . .
H1C H -0.090059 0.421935 0.076502 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
Br2 C9 1.904(3) . ?
Br1 C20 1.904(3) . ?
S3 C13 1.723(3) . ?
S3 C15 1.727(3) . ?
S2 C4 1.731(3) . ?
S2 C2 1.736(4) . ?
S4 C13 1.725(3) . ?
S4 C12 1.768(4) . ?
S1 C2 1.740(4) . ?
S1 C1 1.781(4) . ?
O2 C16 1.220(3) . ?
O1 C5 1.235(4) . ?
N2 C5 1.351(4) . ?
N2 C6 1.412(4) . ?
N2 H2 0.8600 . ?
N4 C13 1.317(4) . ?
N4 C14 1.366(4) . ?
N3 C16 1.361(4) . ?
N3 C17 1.407(4) . ?
N3 H3A 0.8600 . ?
C6 C7 1.387(4) . ?
C6 C11 1.399(4) . ?
N1 C2 1.305(4) . ?
N1 C3 1.368(5) . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C15 C14 1.354(4) . ?
C15 C16 1.477(4) . ?
C5 C4 1.474(5) . ?
C14 H14 0.9300 . ?
C9 C8 1.380(4) . ?
C9 C10 1.382(4) . ?
C17 C22 1.387(4) . ?
C17 C18 1.387(4) . ?
C4 C3 1.351(5) . ?
C20 C21 1.364(5) . ?
C20 C19 1.368(5) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C21 C22 1.386(5) . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C22 H22 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C13 S3 C15 89.47(14) . . ?
C4 S2 C2 88.83(16) . . ?
C13 S4 C12 101.26(18) . . ?
C2 S1 C1 102.3(2) . . ?
C5 N2 C6 127.0(2) . . ?
C5 N2 H2 116.5 . . ?
C6 N2 H2 116.5 . . ?
C13 N4 C14 109.5(2) . . ?
C16 N3 C17 127.2(2) . . ?
C16 N3 H3A 116.4 . . ?
C17 N3 H3A 116.4 . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 N2 117.4(3) . . ?
C11 C6 N2 124.0(3) . . ?
C2 N1 C3 109.9(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C14 C15 C16 134.4(3) . . ?
C14 C15 S3 108.8(2) . . ?
C16 C15 S3 116.8(2) . . ?
N4 C13 S3 114.9(2) . . ?
N4 C13 S4 128.9(2) . . ?
S3 C13 S4 116.24(16) . . ?
O1 C5 N2 122.6(3) . . ?
O1 C5 C4 120.4(3) . . ?
N2 C5 C4 117.0(3) . . ?
O2 C16 N3 124.0(3) . . ?
O2 C16 C15 120.1(3) . . ?
N3 C16 C15 115.9(2) . . ?
C15 C14 N4 117.3(3) . . ?
C15 C14 H14 121.3 . . ?
N4 C14 H14 121.3 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 Br2 119.7(2) . . ?
C10 C9 Br2 119.6(2) . . ?
C22 C17 C18 118.0(3) . . ?
C22 C17 N3 124.2(3) . . ?
C18 C17 N3 117.7(3) . . ?
C3 C4 C5 133.4(3) . . ?
C3 C4 S2 109.2(3) . . ?
C5 C4 S2 117.4(2) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 Br1 119.5(2) . . ?
C19 C20 Br1 120.0(3) . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C4 C3 N1 117.0(3) . . ?
C4 C3 H3 121.5 . . ?
N1 C3 H3 121.5 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N1 C2 S2 115.0(3) . . ?
N1 C2 S1 120.5(3) . . ?
S2 C2 S1 124.5(2) . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C22 C17 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
S4 C12 H12A 109.5 . . ?
S4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C5 N2 C6 C7 157.3(3) . . . . ?
C5 N2 C6 C11 -24.6(5) . . . . ?
C11 C6 C7 C8 1.3(4) . . . . ?
N2 C6 C7 C8 179.5(3) . . . . ?
C13 S3 C15 C14 0.0(2) . . . . ?
C13 S3 C15 C16 -178.8(2) . . . . ?
C14 N4 C13 S3 0.6(3) . . . . ?
C14 N4 C13 S4 -179.3(2) . . . . ?
C15 S3 C13 N4 -0.4(2) . . . . ?
C15 S3 C13 S4 179.51(18) . . . . ?
C12 S4 C13 N4 -3.7(4) . . . . ?
C12 S4 C13 S3 176.4(2) . . . . ?
C6 N2 C5 O1 3.1(5) . . . . ?
C6 N2 C5 C4 -177.6(3) . . . . ?
C17 N3 C16 O2 2.4(5) . . . . ?
C17 N3 C16 C15 -176.7(3) . . . . ?
C14 C15 C16 O2 -178.7(3) . . . . ?
S3 C15 C16 O2 -0.3(4) . . . . ?
C14 C15 C16 N3 0.5(5) . . . . ?
S3 C15 C16 N3 178.9(2) . . . . ?
C16 C15 C14 N4 178.9(3) . . . . ?
S3 C15 C14 N4 0.3(4) . . . . ?
C13 N4 C14 C15 -0.6(4) . . . . ?
C16 N3 C17 C22 -3.4(5) . . . . ?
C16 N3 C17 C18 177.8(3) . . . . ?
O1 C5 C4 C3 -174.9(3) . . . . ?
N2 C5 C4 C3 5.8(5) . . . . ?
O1 C5 C4 S2 6.3(4) . . . . ?
N2 C5 C4 S2 -173.0(2) . . . . ?
C2 S2 C4 C3 -0.8(2) . . . . ?
C2 S2 C4 C5 178.3(2) . . . . ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C10 C9 C8 C7 0.3(4) . . . . ?
Br2 C9 C8 C7 179.5(2) . . . . ?
C5 C4 C3 N1 -178.2(3) . . . . ?
S2 C4 C3 N1 0.6(4) . . . . ?
C2 N1 C3 C4 0.0(4) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
Br2 C9 C10 C11 -179.0(2) . . . . ?
C22 C17 C18 C19 -1.0(6) . . . . ?
N3 C17 C18 C19 177.9(3) . . . . ?
C9 C10 C11 C6 0.0(5) . . . . ?
C7 C6 C11 C10 -0.7(4) . . . . ?
N2 C6 C11 C10 -178.8(3) . . . . ?
C19 C20 C21 C22 -1.5(6) . . . . ?
Br1 C20 C21 C22 175.7(3) . . . . ?
C3 N1 C2 S2 -0.7(4) . . . . ?
C3 N1 C2 S1 179.8(2) . . . . ?
C4 S2 C2 N1 0.9(3) . . . . ?
C4 S2 C2 S1 -179.6(2) . . . . ?
C1 S1 C2 N1 -172.9(3) . . . . ?
C1 S1 C2 S2 7.6(3) . . . . ?
C21 C20 C19 C18 0.9(6) . . . . ?
Br1 C20 C19 C18 -176.3(3) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C20 C21 C22 C17 0.8(6) . . . . ?
C18 C17 C22 C21 0.4(6) . . . . ?
N3 C17 C22 C21 -178.4(3) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2119473'
loop_
_audit_author_name
_audit_author_address
'Ravi Singh K'
;DoS in Chemistry, University of Mysore
India
;
_audit_update_record             
;
2021-11-01 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-09-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c4697 for OlexSys, GUI svn.r6394)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 Br N2 O3 S'
_chemical_formula_sum            'C13 H11 Br N2 O3 S'
_chemical_formula_weight         355.21
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.5681(4)
_cell_length_b                   14.0924(9)
_cell_length_c                   15.4674(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.190(4)
_cell_angle_gamma                90
_cell_volume                     1427.84(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.25
_shelx_estimated_absorpt_T_max   0.499
_shelx_estimated_absorpt_T_min   0.413
_exptl_absorpt_coefficient_mu    5.380
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.2288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.3458.
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    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23502
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.436
_diffrn_reflns_theta_min         4.249
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2295
_reflns_number_total             2689
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0686
_refine_ls_restrained_S_all      1.330
_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)+5.7894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1507
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C7(H7), C4(H4), C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.12946(10) 0.41802(6) 0.90936(5) 0.0692(3) Uani 1 1 d . . . . .
S12 S -0.1053(2) 0.63900(12) 0.60033(11) 0.0576(4) Uani 1 1 d . . . . .
O18 O -0.2409(6) 0.3084(3) 0.5728(3) 0.0504(10) Uani 1 1 d . . . . .
O17 O 0.0740(6) 0.3185(3) 0.6376(3) 0.0595(11) Uani 1 1 d . . . . .
N8 N 0.3189(7) 0.4653(3) 0.6990(3) 0.0471(11) Uani 1 1 d . . . . .
H8 H 0.266002 0.412640 0.680426 0.056 Uiso 1 1 calc R U . . .
N14 N -0.2935(7) 0.4880(4) 0.5522(3) 0.0520(12) Uani 1 1 d . . . . .
O10 O 0.2689(8) 0.6251(3) 0.6959(4) 0.0865(18) Uani 1 1 d . . . . .
C5 C 0.5066(8) 0.4588(4) 0.7486(4) 0.0405(12) Uani 1 1 d . . . . .
C6 C 0.6202(9) 0.5372(4) 0.7793(4) 0.0516(14) Uani 1 1 d . . . . .
H6 H 0.572455 0.598281 0.767394 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8040(9) 0.5238(5) 0.8274(4) 0.0534(15) Uani 1 1 d . . . . .
H7 H 0.878559 0.575944 0.848695 0.064 Uiso 1 1 calc R U . . .
C2 C 0.8763(8) 0.4337(5) 0.8437(4) 0.0494(14) Uani 1 1 d . . . . .
C16 C -0.0798(8) 0.3562(4) 0.6051(4) 0.0435(12) Uani 1 1 d . . . . .
C15 C -0.1134(8) 0.4597(4) 0.5962(4) 0.0438(12) Uani 1 1 d . . . . .
C4 C 0.5845(9) 0.3688(4) 0.7660(4) 0.0523(15) Uani 1 1 d . . . . .
H4 H 0.511465 0.316125 0.744951 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7671(9) 0.3558(5) 0.8136(4) 0.0527(15) Uani 1 1 d . . . . .
H3 H 0.816344 0.294965 0.825258 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0112(8) 0.5329(4) 0.6268(4) 0.0462(13) Uani 1 1 d . . . . .
C9 C 0.2132(9) 0.5442(4) 0.6773(4) 0.0506(14) Uani 1 1 d . . . . .
C13 C -0.3059(9) 0.5802(5) 0.5500(4) 0.0561(16) Uani 1 1 d . . . . .
H13 H -0.417104 0.611722 0.522578 0.067 Uiso 1 1 calc R U . . .
C19 C -0.2310(10) 0.2046(4) 0.5783(4) 0.0563(16) Uani 1 1 d . . . . .
H19A H -0.215333 0.184255 0.638350 0.068 Uiso 1 1 calc R U . . .
H19B H -0.116671 0.180698 0.548495 0.068 Uiso 1 1 calc R U . . .
C20 C -0.4295(12) 0.1691(5) 0.5355(5) 0.076(2) Uani 1 1 d . . . . .
H20A H -0.443122 0.190306 0.476358 0.115 Uiso 1 1 calc R U . . .
H20B H -0.540894 0.193346 0.565792 0.115 Uiso 1 1 calc R U . . .
H20C H -0.431276 0.101006 0.536955 0.115 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 1.897(5) . ?
S12 C11 1.715(6) . ?
S12 C13 1.697(6) . ?
O18 C16 1.321(6) . ?
O18 C19 1.466(7) . ?
O17 C16 1.217(6) . ?
N8 H8 0.8600 . ?
N8 C5 1.406(6) . ?
N8 C9 1.341(7) . ?
N14 C15 1.380(7) . ?
N14 C13 1.303(8) . ?
O10 C9 1.225(7) . ?
C5 C6 1.397(8) . ?
C5 C4 1.386(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(8) . ?
C7 H7 0.9300 . ?
C7 C2 1.372(9) . ?
C2 C3 1.374(9) . ?
C16 C15 1.481(8) . ?
C15 C11 1.378(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(8) . ?
C3 H3 0.9300 . ?
C11 C9 1.499(8) . ?
C13 H13 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.504(9) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C13 S12 C11 90.1(3) . . ?
C16 O18 C19 117.1(4) . . ?
C5 N8 H8 116.3 . . ?
C9 N8 H8 116.3 . . ?
C9 N8 C5 127.4(5) . . ?
C13 N14 C15 110.5(5) . . ?
C6 C5 N8 124.0(5) . . ?
C4 C5 N8 117.5(5) . . ?
C4 C5 C6 118.5(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.9(6) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.9 . . ?
C2 C7 C6 120.1(6) . . ?
C2 C7 H7 119.9 . . ?
C7 C2 Br1 119.0(5) . . ?
C7 C2 C3 120.7(5) . . ?
C3 C2 Br1 120.3(5) . . ?
O18 C16 C15 111.0(4) . . ?
O17 C16 O18 123.4(5) . . ?
O17 C16 C15 125.6(5) . . ?
N14 C15 C16 116.5(5) . . ?
C11 C15 N14 114.8(5) . . ?
C11 C15 C16 128.7(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.3 . . ?
C15 C11 S12 109.1(4) . . ?
C15 C11 C9 137.7(5) . . ?
C9 C11 S12 113.2(4) . . ?
N8 C9 C11 117.7(5) . . ?
O10 C9 N8 125.0(5) . . ?
O10 C9 C11 117.3(5) . . ?
S12 C13 H13 122.3 . . ?
N14 C13 S12 115.5(4) . . ?
N14 C13 H13 122.3 . . ?
O18 C19 H19A 110.6 . . ?
O18 C19 H19B 110.6 . . ?
O18 C19 C20 105.8(5) . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 H19A 110.6 . . ?
C20 C19 H19B 110.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C2 C3 C4 -179.8(5) . . . . ?
S12 C11 C9 N8 -178.2(5) . . . . ?
S12 C11 C9 O10 2.0(8) . . . . ?
O18 C16 C15 N14 -4.2(7) . . . . ?
O18 C16 C15 C11 175.1(6) . . . . ?
O17 C16 C15 N14 175.9(6) . . . . ?
O17 C16 C15 C11 -4.7(10) . . . . ?
N8 C5 C6 C7 -179.7(6) . . . . ?
N8 C5 C4 C3 179.7(6) . . . . ?
N14 C15 C11 S12 0.9(7) . . . . ?
N14 C15 C11 C9 179.1(7) . . . . ?
C5 N8 C9 O10 2.4(11) . . . . ?
C5 N8 C9 C11 -177.4(5) . . . . ?
C5 C6 C7 C2 1.1(9) . . . . ?
C5 C4 C3 C2 -0.8(10) . . . . ?
C6 C5 C4 C3 1.2(9) . . . . ?
C6 C7 C2 Br1 179.7(5) . . . . ?
C6 C7 C2 C3 -0.7(9) . . . . ?
C7 C2 C3 C4 0.6(10) . . . . ?
C16 O18 C19 C20 -178.7(5) . . . . ?
C16 C15 C11 S12 -178.5(5) . . . . ?
C16 C15 C11 C9 -0.3(12) . . . . ?
C15 N14 C13 S12 -0.3(7) . . . . ?
C15 C11 C9 N8 3.6(11) . . . . ?
C15 C11 C9 O10 -176.2(7) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C11 S12 C13 N14 0.7(6) . . . . ?
C9 N8 C5 C6 -4.2(9) . . . . ?
C9 N8 C5 C4 177.5(6) . . . . ?
C13 S12 C11 C15 -0.9(5) . . . . ?
C13 S12 C11 C9 -179.6(5) . . . . ?
C13 N14 C15 C16 179.1(5) . . . . ?
C13 N14 C15 C11 -0.4(8) . . . . ?
C19 O18 C16 O17 0.8(9) . . . . ?
C19 O18 C16 C15 -179.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
