# 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_AP_a
_database_code_depnum_ccdc_archive 'CCDC 2165367'
loop_
_audit_author_name
_audit_author_address
Samiran
;UNIVERSITY OF CALCUTTA
India
;
_audit_update_record             
;
2022-04-08 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O S'
_chemical_formula_weight         241.30

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/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                   9.6609(7)
_cell_length_b                   6.3361(5)
_cell_length_c                   19.6298(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.172(3)
_cell_angle_gamma                90
_cell_volume                     1194.62(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.087
_cell_measurement_theta_max      24.995

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   SADABS
_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 Apex II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9949
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.087
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2109
_reflns_number_gt                1906
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1000P)²+0.9269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2109
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1767
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
S001 S 0.57110(7) 0.61097(12) 0.58140(4) 0.0590(4) Uani 1 1 d . . . . .
O002 O 0.9271(2) 0.6416(4) 0.68292(11) 0.0592(6) Uani 1 1 d . . . . .
N1 N 0.7323(2) 0.7055(4) 0.60819(11) 0.0481(6) Uani 1 1 d . . . . .
C2 C 0.7282(2) 0.4081(4) 0.67560(12) 0.0392(6) Uani 1 1 d . . . . .
C9 C 0.8074(3) 0.8806(4) 0.50471(13) 0.0441(6) Uani 1 1 d . . . . .
C1 C 0.8095(3) 0.5909(4) 0.65829(12) 0.0413(6) Uani 1 1 d . . . . .
C3 C 0.5961(3) 0.4006(4) 0.63820(14) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.7683(3) 0.2496(5) 0.72256(13) 0.0502(7) Uani 1 1 d . . . . .
C4 C 0.5032(3) 0.2392(5) 0.64809(16) 0.0569(8) Uani 1 1 d . . . . .
C8 C 0.7808(4) 0.8999(4) 0.57884(15) 0.0543(7) Uani 1 1 d . . . . .
C10 C 0.8552(3) 0.6958(5) 0.47820(16) 0.0580(8) Uani 1 1 d . . . . .
C14 C 0.7901(3) 1.0562(5) 0.46335(16) 0.0586(8) Uani 1 1 d . . . . .
C5 C 0.5432(4) 0.0877(5) 0.69578(18) 0.0630(9) Uani 1 1 d . . . . .
C6 C 0.6757(4) 0.0908(5) 0.73274(16) 0.0617(8) Uani 1 1 d . . . . .
C11 C 0.8871(3) 0.6890(7) 0.41054(19) 0.0710(10) Uani 1 1 d . . . . .
C12 C 0.8714(4) 0.8666(8) 0.37015(18) 0.0776(12) Uani 1 1 d . . . . .
C13 C 0.8228(4) 1.0480(7) 0.39639(18) 0.0765(11) Uani 1 1 d . . . . .
H1 H 0.413(5) 0.249(7) 0.625(2) 0.103(14) Uiso 1 1 d . . . . .
H2 H 0.488(4) -0.023(7) 0.7048(19) 0.076(11) Uiso 1 1 d . . . . .
H3 H 0.696(3) -0.020(6) 0.7629(18) 0.066(9) Uiso 1 1 d . . . . .
H4 H 0.856(4) 0.257(6) 0.743(2) 0.077(11) Uiso 1 1 d . . . . .
H5 H 0.705(4) 1.007(7) 0.5856(19) 0.078(10) Uiso 1 1 d . . . . .
H6 H 0.872(5) 0.937(6) 0.607(2) 0.085(12) Uiso 1 1 d . . . . .
H7 H 0.871(4) 0.568(6) 0.505(2) 0.085(12) Uiso 1 1 d . . . . .
H8 H 0.916(4) 0.557(6) 0.396(2) 0.076(11) Uiso 1 1 d . . . . .
H9 H 0.903(5) 0.863(7) 0.324(3) 0.119(17) Uiso 1 1 d . . . . .
H10 H 0.817(5) 1.177(8) 0.371(3) 0.109(15) Uiso 1 1 d . . . . .
H11 H 0.753(4) 1.183(6) 0.4817(17) 0.065(9) Uiso 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
S001 N1 1.698(2) . ?
S001 C3 1.738(3) . ?
O002 C1 1.229(3) . ?
N1 C1 1.376(3) . ?
N1 C8 1.458(4) . ?
C2 C7 1.390(4) . ?
C2 C3 1.403(3) . ?
C2 C1 1.460(4) . ?
C9 C14 1.377(4) . ?
C9 C10 1.381(4) . ?
C9 C8 1.510(4) . ?
C3 C4 1.388(4) . ?
C7 C6 1.375(5) . ?
C7 H4 0.90(4) . ?
C4 C5 1.367(5) . ?
C4 H1 0.93(5) . ?
C8 H5 1.02(4) . ?
C8 H6 1.01(4) . ?
C10 C11 1.396(5) . ?
C10 H7 0.96(4) . ?
C14 C13 1.385(5) . ?
C14 H11 0.97(3) . ?
C5 C6 1.402(5) . ?
C5 H2 0.91(4) . ?
C6 H3 0.93(4) . ?
C11 C12 1.376(6) . ?
C11 H8 0.94(4) . ?
C12 C13 1.363(6) . ?
C12 H9 0.99(6) . ?
C13 H10 0.96(5) . ?

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 S001 C3 90.71(11) . . ?
C1 N1 C8 123.7(2) . . ?
C1 N1 S001 116.34(18) . . ?
C8 N1 S001 119.9(2) . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 C1 127.6(2) . . ?
C3 C2 C1 112.8(2) . . ?
C14 C9 C10 119.2(3) . . ?
C14 C9 C8 118.7(3) . . ?
C10 C9 C8 122.0(2) . . ?
O002 C1 N1 123.4(2) . . ?
O002 C1 C2 127.8(2) . . ?
N1 C1 C2 108.8(2) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 S001 127.4(2) . . ?
C2 C3 S001 111.43(19) . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H4 125(2) . . ?
C2 C7 H4 116(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H1 123(3) . . ?
C3 C4 H1 118(3) . . ?
N1 C8 C9 114.1(2) . . ?
N1 C8 H5 104(2) . . ?
C9 C8 H5 112(2) . . ?
N1 C8 H6 107(2) . . ?
C9 C8 H6 108(2) . . ?
H5 C8 H6 112(3) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H7 123(2) . . ?
C11 C10 H7 117(2) . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H11 119(2) . . ?
C13 C14 H11 121(2) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H2 123(3) . . ?
C6 C5 H2 116(2) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H3 123(2) . . ?
C5 C6 H3 116(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H8 125(2) . . ?
C10 C11 H8 115(2) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H9 121(3) . . ?
C11 C12 H9 119(3) . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H10 122(3) . . ?
C14 C13 H10 117(3) . . ?

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.074

