# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1029634'
loop_
_audit_author_name
_audit_author_address
'Hadi Amiri Rudbari'
;university of Isfahan
Iran
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N S2'
_chemical_formula_weight         323.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.837(3)
_cell_length_b                   8.8654(18)
_cell_length_c                   15.322(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.87(3)
_cell_angle_gamma                90
_cell_volume                     1677.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1615
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      31.59

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3709
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             1435
_reflns_number_gt                825
_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       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0147P)²+5.5482P] 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         1435
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.1168
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.000
_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 0.64837(16) 0.2349(2) 0.16799(16) 0.0509(6) Uani 1 1 d . . . . .
N1 N 0.500000 0.1922(8) 0.250000 0.035(2) Uani 1 2 d S T P . .
C4 C 0.7097(5) 0.1131(8) 0.1029(5) 0.0365(18) Uani 1 1 d . . . . .
C2 C 0.5683(5) -0.0416(8) 0.2098(5) 0.0423(18) Uani 1 1 d . . . . .
H2 H 0.614723 -0.092636 0.182864 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5648(5) 0.1134(8) 0.2112(5) 0.0338(17) Uani 1 1 d . . . . .
C9 C 0.6646(6) 0.0951(8) 0.0126(5) 0.049(2) Uani 1 1 d . . . . .
H9 H 0.598521 0.140523 -0.015144 0.059 Uiso 1 1 calc R U . . .
C6 C 0.8578(5) -0.0408(8) 0.0914(6) 0.046(2) Uani 1 1 d . . . . .
H6 H 0.923412 -0.087668 0.118924 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8138(6) -0.0585(8) 0.0000(5) 0.0428(19) Uani 1 1 d . . . . .
C10 C 0.8704(6) -0.1499(9) -0.0562(6) 0.068(3) Uani 1 1 d . . . . .
H10A H 0.946494 -0.128050 -0.037697 0.103 Uiso 1 1 calc R U . . .
H10B H 0.841369 -0.124638 -0.119120 0.103 Uiso 1 1 calc R U . . .
H10C H 0.859269 -0.255369 -0.047649 0.103 Uiso 1 1 calc R U . . .
C5 C 0.8078(5) 0.0453(8) 0.1452(5) 0.0464(19) Uani 1 1 d . . . . .
H5 H 0.839296 0.056590 0.207122 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7159(6) 0.0100(9) -0.0384(5) 0.049(2) Uani 1 1 d . . . . .
H8 H 0.683632 -0.001407 -0.100222 0.059 Uiso 1 1 calc R U . . .
C1 C 0.500000 -0.1184(11) 0.250000 0.044(3) Uani 1 2 d S T P . .
H1 H 0.500000 -0.223336 0.250000 0.053 Uiso 1 2 calc R U P . .


_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 C3 1.771(7) . ?
S1 C4 1.792(6) . ?
N1 C3 1.343(7) . ?
N1 C3 1.344(7) 2_655 ?
C4 C9 1.355(10) . ?
C4 C5 1.385(9) . ?
C2 C3 1.376(9) . ?
C2 C1 1.381(8) . ?
C2 H2 0.9300 . ?
C9 C8 1.376(9) . ?
C9 H9 0.9300 . ?
C6 C7 1.369(11) . ?
C6 C5 1.401(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(9) . ?
C7 C10 1.505(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C1 H1 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
C3 S1 C4 104.1(3) . . ?
C3 N1 C3 117.4(8) . 2_655 ?
C9 C4 C5 120.4(6) . . ?
C9 C4 S1 120.6(6) . . ?
C5 C4 S1 118.8(6) . . ?
C3 C2 C1 117.3(7) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
N1 C3 C2 123.5(7) . . ?
N1 C3 S1 111.2(5) . . ?
C2 C3 S1 125.2(5) . . ?
C4 C9 C8 120.4(7) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C7 C6 C5 122.5(7) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C8 117.4(7) . . ?
C6 C7 C10 121.2(7) . . ?
C8 C7 C10 121.4(8) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 117.8(7) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C8 C9 121.5(8) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C2 C1 C2 120.9(10) . 2_655 ?
C2 C1 H1 119.6 . . ?
C2 C1 H1 119.6 2_655 . ?

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
C3 S1 C4 C9 93.6(7) . . . . ?
C3 S1 C4 C5 -90.6(6) . . . . ?
C3 N1 C3 C2 -0.4(6) 2_655 . . . ?
C3 N1 C3 S1 -177.5(5) 2_655 . . . ?
C1 C2 C3 N1 0.7(11) . . . . ?
C1 C2 C3 S1 177.4(4) . . . . ?
C4 S1 C3 N1 -170.3(4) . . . . ?
C4 S1 C3 C2 12.7(8) . . . . ?
C5 C4 C9 C8 -0.4(11) . . . . ?
S1 C4 C9 C8 175.3(6) . . . . ?
C5 C6 C7 C8 -1.1(11) . . . . ?
C5 C6 C7 C10 179.1(7) . . . . ?
C9 C4 C5 C6 0.2(11) . . . . ?
S1 C4 C5 C6 -175.6(5) . . . . ?
C7 C6 C5 C4 0.5(11) . . . . ?
C6 C7 C8 C9 1.0(11) . . . . ?
C10 C7 C8 C9 -179.2(7) . . . . ?
C4 C9 C8 C7 -0.2(12) . . . . ?
C3 C2 C1 C2 -0.3(5) . . . 2_655 ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.063

