# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2166274'
loop_
_audit_author_name
_audit_author_address
'MALLI M.BHANUCHANDRA'
;Central University of Rajasthan 
India
;
_audit_update_record             
;
2022-04-13 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         'C17 H13 N O S2'
_chemical_formula_sum            'C17 H13 N O S2'
_chemical_formula_weight         311.40

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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.973(2)
_cell_length_b                   7.1655(9)
_cell_length_c                   14.941(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.041(5)
_cell_angle_gamma                90
_cell_volume                     1487.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)

_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      30.54
_exptl_crystal_description       block
_exptl_crystal_colour            brown

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.355
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40383
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.199
_diffrn_reflns_theta_max         30.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4577
_reflns_number_gt                4013
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0384P)²+0.6864P] 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         4577
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.86880(11) 0.62264(19) 0.71381(9) 0.0342(3) Uani 1 1 d . . . . .
H1 H 0.809231 0.647262 0.736817 0.041 Uiso 1 1 calc R U . . .
C2 C 0.94996(13) 0.7226(2) 0.74568(10) 0.0424(3) Uani 1 1 d . . . . .
H2 H 0.945845 0.815794 0.790331 0.051 Uiso 1 1 calc R U . . .
C3 C 1.03744(13) 0.6873(2) 0.71271(12) 0.0480(4) Uani 1 1 d . . . . .
H3 H 1.093182 0.756210 0.734398 0.058 Uiso 1 1 calc R U . . .
C4 C 1.04264(11) 0.5502(2) 0.64770(12) 0.0435(3) Uani 1 1 d . . . . .
H4 H 1.102593 0.524324 0.625665 0.052 Uiso 1 1 calc R U . . .
C5 C 0.96128(9) 0.45016(19) 0.61443(9) 0.0328(3) Uani 1 1 d . . . . .
H5 H 0.965314 0.358271 0.569151 0.039 Uiso 1 1 calc R U . . .
C6 C 0.87392(9) 0.48582(17) 0.64803(8) 0.0262(2) Uani 1 1 d . . . . .
C7 C 0.79292(8) 0.20065(16) 0.53675(8) 0.0246(2) Uani 1 1 d . . . . .
C8 C 0.85071(9) 0.04874(19) 0.56482(9) 0.0329(3) Uani 1 1 d . . . . .
H8 H 0.877177 0.039444 0.625881 0.040 Uiso 1 1 calc R U . . .
C9 C 0.86966(11) -0.08864(19) 0.50401(11) 0.0397(3) Uani 1 1 d . . . . .
H9 H 0.910058 -0.190663 0.523386 0.048 Uiso 1 1 calc R U . . .
C10 C 0.83013(12) -0.0786(2) 0.41493(11) 0.0408(3) Uani 1 1 d . . . . .
H10 H 0.843170 -0.174034 0.373765 0.049 Uiso 1 1 calc R U . . .
C11 C 0.77168(10) 0.0704(2) 0.38597(9) 0.0341(3) Uani 1 1 d . . . . .
H11 H 0.744139 0.077517 0.325162 0.041 Uiso 1 1 calc R U . . .
C12 C 0.75382(8) 0.20936(16) 0.44700(8) 0.0248(2) Uani 1 1 d . . . . .
C13 C 0.56781(9) 0.31618(17) 0.42170(8) 0.0272(2) Uani 1 1 d . . . . .
C14 C 0.50128(11) 0.2982(2) 0.34722(9) 0.0394(3) Uani 1 1 d . . . . .
H14 H 0.517139 0.326019 0.288387 0.047 Uiso 1 1 calc R U . . .
C15 C 0.40993(11) 0.2375(2) 0.36236(12) 0.0464(4) Uani 1 1 d . . . . .
H15 H 0.361103 0.223483 0.313563 0.056 Uiso 1 1 calc R U . . .
C16 C 0.39111(10) 0.1981(2) 0.44867(12) 0.0425(3) Uani 1 1 d . . . . .
H16 H 0.329035 0.157009 0.460463 0.051 Uiso 1 1 calc R U . . .
C17 C 0.46390(10) 0.2192(2) 0.51835(10) 0.0362(3) Uani 1 1 d . . . . .
H17 H 0.450479 0.189431 0.577713 0.043 Uiso 1 1 calc R U . . .
N1 N 0.55232(8) 0.27957(15) 0.50609(7) 0.0298(2) Uani 1 1 d . . . . .
O1 O 0.68925(9) 0.4170(2) 0.30673(8) 0.0557(3) Uani 1 1 d . . . . .
S1 S 0.76286(2) 0.37493(5) 0.61323(2) 0.03204(9) Uani 1 1 d . . . . .
S2 S 0.68534(2) 0.41013(5) 0.40610(2) 0.03316(9) Uani 1 1 d . . . . .


_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
C1 C2 1.383(2) . ?
C1 C6 1.3953(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3907(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3915(18) . ?
C5 H5 0.9500 . ?
C6 S1 1.7720(13) . ?
C7 C8 1.3934(17) . ?
C7 C12 1.3951(16) . ?
C7 S1 1.7728(12) . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3904(17) . ?
C11 H11 0.9500 . ?
C12 S2 1.7988(12) . ?
C13 N1 1.3279(16) . ?
C13 C14 1.3790(18) . ?
C13 S2 1.8123(13) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 N1 1.3395(17) . ?
C17 H17 0.9500 . ?
O1 S2 1.4923(12) . ?

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
C2 C1 C6 120.37(14) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.27(14) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.33(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.90(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.45(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.67(12) . . ?
C5 C6 S1 125.89(10) . . ?
C1 C6 S1 114.42(10) . . ?
C8 C7 C12 118.70(11) . . ?
C8 C7 S1 121.69(9) . . ?
C12 C7 S1 119.52(9) . . ?
C9 C8 C7 120.19(13) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.56(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.08(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.18(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 121.28(11) . . ?
C11 C12 S2 118.41(9) . . ?
C7 C12 S2 120.19(9) . . ?
N1 C13 C14 125.76(13) . . ?
N1 C13 S2 115.85(9) . . ?
C14 C13 S2 118.29(11) . . ?
C13 C14 C15 116.79(14) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 H14 121.6 . . ?
C16 C15 C14 119.18(13) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 119.06(14) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N1 C17 C16 123.18(14) . . ?
N1 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C13 N1 C17 116.01(12) . . ?
C6 S1 C7 104.21(6) . . ?
O1 S2 C12 106.88(6) . . ?
O1 S2 C13 105.59(7) . . ?
C12 S2 C13 96.67(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
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C5 C6 S1 179.26(11) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 S1 -178.73(11) . . . . ?
C12 C7 C8 C9 0.94(19) . . . . ?
S1 C7 C8 C9 177.45(11) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
C10 C11 C12 S2 175.35(11) . . . . ?
C8 C7 C12 C11 -0.10(18) . . . . ?
S1 C7 C12 C11 -176.69(10) . . . . ?
C8 C7 C12 S2 -175.94(9) . . . . ?
S1 C7 C12 S2 7.48(14) . . . . ?
N1 C13 C14 C15 0.4(2) . . . . ?
S2 C13 C14 C15 -175.84(11) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 N1 1.1(2) . . . . ?
C14 C13 N1 C17 0.33(19) . . . . ?
S2 C13 N1 C17 176.68(10) . . . . ?
C16 C17 N1 C13 -1.1(2) . . . . ?
C5 C6 S1 C7 5.24(13) . . . . ?
C1 C6 S1 C7 -176.15(9) . . . . ?
C8 C7 S1 C6 66.50(11) . . . . ?
C12 C7 S1 C6 -117.02(10) . . . . ?
C11 C12 S2 O1 -19.17(12) . . . . ?
C7 C12 S2 O1 156.78(10) . . . . ?
C11 C12 S2 C13 89.39(11) . . . . ?
C7 C12 S2 C13 -94.66(10) . . . . ?
N1 C13 S2 O1 173.27(10) . . . . ?
C14 C13 S2 O1 -10.10(12) . . . . ?
N1 C13 S2 C12 63.62(10) . . . . ?
C14 C13 S2 C12 -119.74(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 S1 0.95 3.03 3.7858(14) 137.7 2_656 yes
C11 H11 O1 0.95 2.54 3.1823(17) 124.9 2_645 yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.058

