# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2056356'
loop_
_audit_author_name
_audit_author_address
'PRINCE KUMAR GUPTA'
;Banaras Hindu University
India
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2021-03-19 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         'C24 H17 Cl N2 S'
_chemical_formula_sum            'C24 H17 Cl N2 S'
_chemical_formula_weight         400.91

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2203(3)
_cell_length_b                   15.9604(5)
_cell_length_c                   13.5514(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.9210(10)
_cell_angle_gamma                90
_cell_volume                     1975.19(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3370
_cell_measurement_theta_min      2.552
_cell_measurement_theta_max      26.731

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18278
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4184
_reflns_number_gt                3307
_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 2014/5 (Sheldrick, 2014)'
_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)+2.7515P] 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         4184
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
S1 S 1.58839(6) 0.39669(4) -0.30279(4) 0.01643(14) Uani 1 1 d . . . . .
Cl1 Cl 2.52474(7) 0.36343(4) 0.05102(5) 0.02564(16) Uani 1 1 d . . . . .
N1 N 1.8130(2) 0.18836(12) -0.24505(14) 0.0201(4) Uani 1 1 d . . . . .
H1 H 1.887969 0.156735 -0.247345 0.024 Uiso 1 1 calc R U . . .
C13 C 1.4641(3) 0.23148(16) -0.17052(18) 0.0229(6) Uani 1 1 d . . . . .
H13 H 1.399073 0.276311 -0.176308 0.028 Uiso 1 1 calc R U . . .
C1 C 2.3405(3) 0.38085(15) 0.00725(17) 0.0182(5) Uani 1 1 d . . . . .
C19 C 1.9087(3) 0.30701(14) -0.33671(17) 0.0171(5) Uani 1 1 d . . . . .
N2 N 1.9310(2) 0.56794(14) -0.27648(16) 0.0260(5) Uani 1 1 d . . . . .
C10 C 1.6490(3) 0.45748(15) -0.18950(17) 0.0175(5) Uani 1 1 d . . . . .
H10A H 1.609115 0.513699 -0.197546 0.021 Uiso 1 1 calc R U . . .
H10B H 1.610746 0.431741 -0.133584 0.021 Uiso 1 1 calc R U . . .
C12 C 1.5952(3) 0.23599(14) -0.21166(17) 0.0176(5) Uani 1 1 d . . . . .
C18 C 1.7950(3) 0.26763(14) -0.28559(17) 0.0168(5) Uani 1 1 d . . . . .
C7 C 1.8876(3) 0.41474(14) -0.09650(17) 0.0172(5) Uani 1 1 d . . . . .
H7 H 1.829502 0.380825 -0.062196 0.021 Uiso 1 1 calc R U . . .
C8 C 1.8120(3) 0.46254(14) -0.16710(17) 0.0154(5) Uani 1 1 d . . . . .
C9 C 1.8807(3) 0.52015(15) -0.22827(18) 0.0182(5) Uani 1 1 d . . . . .
C4 C 2.0453(3) 0.40625(14) -0.06359(17) 0.0158(5) Uani 1 1 d . . . . .
C24 C 1.8703(3) 0.34524(15) -0.42924(18) 0.0211(5) Uani 1 1 d . . . . .
H24 H 1.773437 0.344433 -0.459439 0.025 Uiso 1 1 calc R U . . .
C3 C 2.1548(3) 0.44871(15) -0.10534(18) 0.0204(5) Uani 1 1 d . . . . .
H3 H 2.128773 0.486380 -0.157104 0.025 Uiso 1 1 calc R U . . .
C22 C 2.1199(3) 0.38669(16) -0.43160(19) 0.0249(6) Uani 1 1 d . . . . .
H22 H 2.190188 0.413773 -0.463025 0.030 Uiso 1 1 calc R U . . .
C5 C 2.0895(3) 0.35158(15) 0.01548(18) 0.0232(6) Uani 1 1 d . . . . .
H5 H 2.018769 0.322777 0.044710 0.028 Uiso 1 1 calc R U . . .
C2 C 2.3013(3) 0.43552(15) -0.07079(18) 0.0202(5) Uani 1 1 d . . . . .
H2 H 2.373084 0.463371 -0.100035 0.024 Uiso 1 1 calc R U . . .
C23 C 1.9762(3) 0.38443(16) -0.47628(19) 0.0265(6) Uani 1 1 d . . . . .
H23 H 1.950184 0.409309 -0.538253 0.032 Uiso 1 1 calc R U . . .
C11 C 1.6618(3) 0.29854(14) -0.26719(17) 0.0160(5) Uani 1 1 d . . . . .
C15 C 1.5304(3) 0.09156(17) -0.11277(19) 0.0309(7) Uani 1 1 d . . . . .
H15 H 1.507035 0.043689 -0.079162 0.037 Uiso 1 1 calc R U . . .
C16 C 1.6594(3) 0.09380(16) -0.15266(18) 0.0265(6) Uani 1 1 d . . . . .
H16 H 1.722392 0.048015 -0.148166 0.032 Uiso 1 1 calc R U . . .
C17 C 1.6922(3) 0.16764(15) -0.20025(17) 0.0192(5) Uani 1 1 d . . . . .
C14 C 1.4332(3) 0.15940(17) -0.12129(19) 0.0292(6) Uani 1 1 d . . . . .
H14 H 1.346658 0.155802 -0.093424 0.035 Uiso 1 1 calc R U . . .
C6 C 2.2358(3) 0.33924(16) 0.05134(19) 0.0242(6) Uani 1 1 d . . . . .
H6 H 2.262942 0.303222 0.104631 0.029 Uiso 1 1 calc R U . . .
C20 C 2.0547(3) 0.30816(15) -0.29312(18) 0.0202(5) Uani 1 1 d . . . . .
H20 H 2.082211 0.281649 -0.232303 0.024 Uiso 1 1 calc R U . . .
C21 C 2.1594(3) 0.34882(16) -0.34029(19) 0.0232(6) Uani 1 1 d . . . . .
H21 H 2.256342 0.350510 -0.310267 0.028 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
S1 C11 1.748(2) . ?
S1 C10 1.837(2) . ?
Cl1 C1 1.742(2) . ?
N1 C18 1.380(3) . ?
N1 C17 1.380(3) . ?
N1 H1 0.8600 . ?
C13 C14 1.379(4) . ?
C13 C12 1.401(3) . ?
C13 H13 0.9300 . ?
C1 C6 1.375(3) . ?
C1 C2 1.380(3) . ?
C19 C20 1.394(3) . ?
C19 C24 1.396(3) . ?
C19 C18 1.474(3) . ?
N2 C9 1.144(3) . ?
C10 C8 1.494(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C17 1.406(3) . ?
C12 C11 1.438(3) . ?
C18 C11 1.378(3) . ?
C7 C8 1.341(3) . ?
C7 C4 1.467(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.441(3) . ?
C4 C5 1.398(3) . ?
C4 C3 1.399(3) . ?
C24 C23 1.386(3) . ?
C24 H24 0.9300 . ?
C3 C2 1.383(3) . ?
C3 H3 0.9300 . ?
C22 C23 1.379(4) . ?
C22 C21 1.380(4) . ?
C22 H22 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C23 H23 0.9300 . ?
C15 C16 1.373(4) . ?
C15 C14 1.401(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C11 S1 C10 100.44(11) . . ?
C18 N1 C17 109.6(2) . . ?
C18 N1 H1 125.2 . . ?
C17 N1 H1 125.2 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C6 C1 C2 120.8(2) . . ?
C6 C1 Cl1 119.03(19) . . ?
C2 C1 Cl1 120.13(19) . . ?
C20 C19 C24 119.0(2) . . ?
C20 C19 C18 121.0(2) . . ?
C24 C19 C18 120.0(2) . . ?
C8 C10 S1 112.33(16) . . ?
C8 C10 H10A 109.1 . . ?
S1 C10 H10A 109.1 . . ?
C8 C10 H10B 109.1 . . ?
S1 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 C11 134.3(2) . . ?
C17 C12 C11 106.6(2) . . ?
C11 C18 N1 108.5(2) . . ?
C11 C18 C19 129.9(2) . . ?
N1 C18 C19 121.6(2) . . ?
C8 C7 C4 131.7(2) . . ?
C8 C7 H7 114.2 . . ?
C4 C7 H7 114.2 . . ?
C7 C8 C9 123.2(2) . . ?
C7 C8 C10 121.6(2) . . ?
C9 C8 C10 115.3(2) . . ?
N2 C9 C8 177.4(3) . . ?
C5 C4 C3 117.5(2) . . ?
C5 C4 C7 117.6(2) . . ?
C3 C4 C7 124.9(2) . . ?
C23 C24 C19 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.1 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C18 C11 C12 107.6(2) . . ?
C18 C11 S1 126.28(19) . . ?
C12 C11 S1 126.15(18) . . ?
C16 C15 C14 121.8(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 117.3(2) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
N1 C17 C16 130.1(2) . . ?
N1 C17 C12 107.8(2) . . ?
C16 C17 C12 122.1(2) . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?

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
C11 S1 C10 C8 62.73(19) . . . . ?
C14 C13 C12 C17 -1.0(3) . . . . ?
C14 C13 C12 C11 179.3(2) . . . . ?
C17 N1 C18 C11 -0.1(3) . . . . ?
C17 N1 C18 C19 178.8(2) . . . . ?
C20 C19 C18 C11 129.9(3) . . . . ?
C24 C19 C18 C11 -48.9(4) . . . . ?
C20 C19 C18 N1 -48.7(3) . . . . ?
C24 C19 C18 N1 132.5(2) . . . . ?
C4 C7 C8 C9 -0.6(4) . . . . ?
C4 C7 C8 C10 177.6(2) . . . . ?
S1 C10 C8 C7 -102.1(2) . . . . ?
S1 C10 C8 C9 76.3(2) . . . . ?
C8 C7 C4 C5 178.2(2) . . . . ?
C8 C7 C4 C3 -1.9(4) . . . . ?
C20 C19 C24 C23 -0.6(4) . . . . ?
C18 C19 C24 C23 178.2(2) . . . . ?
C5 C4 C3 C2 1.3(4) . . . . ?
C7 C4 C3 C2 -178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C4 C5 C6 179.7(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
Cl1 C1 C2 C3 179.73(19) . . . . ?
C4 C3 C2 C1 -1.2(4) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C19 C24 C23 C22 -0.7(4) . . . . ?
N1 C18 C11 C12 0.8(3) . . . . ?
C19 C18 C11 C12 -178.0(2) . . . . ?
N1 C18 C11 S1 179.66(17) . . . . ?
C19 C18 C11 S1 0.9(4) . . . . ?
C13 C12 C11 C18 178.6(3) . . . . ?
C17 C12 C11 C18 -1.1(3) . . . . ?
C13 C12 C11 S1 -0.3(4) . . . . ?
C17 C12 C11 S1 179.96(17) . . . . ?
C10 S1 C11 C18 -94.1(2) . . . . ?
C10 S1 C11 C12 84.6(2) . . . . ?
C14 C15 C16 C17 1.6(4) . . . . ?
C18 N1 C17 C16 177.8(2) . . . . ?
C18 N1 C17 C12 -0.6(3) . . . . ?
C15 C16 C17 N1 178.8(2) . . . . ?
C15 C16 C17 C12 -3.0(4) . . . . ?
C13 C12 C17 N1 -178.7(2) . . . . ?
C11 C12 C17 N1 1.1(3) . . . . ?
C13 C12 C17 C16 2.7(3) . . . . ?
C11 C12 C17 C16 -177.6(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
Cl1 C1 C6 C5 -178.68(19) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C24 C19 C20 C21 1.7(4) . . . . ?
C18 C19 C20 C21 -177.1(2) . . . . ?
C23 C22 C21 C20 0.1(4) . . . . ?
C19 C20 C21 C22 -1.4(4) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.066

