# 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 2023

####################################################################### 
# 
# 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_mr-24_auto
_database_code_depnum_ccdc_archive 'CCDC 2208821'
loop_
_audit_author_name
_audit_author_address
'MAHESH KUMAR'
;Banaras Hindu University 
India
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2022-12-22 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            'C19 H21 N O2 S2'
_chemical_formula_weight         359.49

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'
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'

_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                   15.3229(3)
_cell_length_b                   8.7687(2)
_cell_length_c                   13.8326(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.502(2)
_cell_angle_gamma                90
_cell_volume                     1799.36(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11346
_cell_measurement_theta_min      2.9640
_cell_measurement_theta_max      67.9430

_exptl_crystal_description       rod-shape
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.766
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17240
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         68.125
_diffrn_reflns_theta_full        68.125
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3262
_reflns_number_gt                2985
_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)+(0.0661P)²+1.6195P] 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         3262
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
S001 S 0.24645(4) 0.30159(8) 0.70419(5) 0.0541(2) Uani 1 1 d . . . . .
S002 S 0.08120(4) 0.30342(8) 0.52921(5) 0.0549(2) Uani 1 1 d . . . . .
O003 O 0.23427(13) 0.6887(2) 0.55752(14) 0.0549(5) Uani 1 1 d . . . . .
N004 N 0.10581(12) 0.1331(2) 0.69135(14) 0.0413(4) Uani 1 1 d . . . . .
O005 O 0.20067(18) 0.6388(3) 0.70230(18) 0.0855(7) Uani 1 1 d . . . . .
C006 C 0.42228(15) 0.3730(2) 0.58637(16) 0.0377(5) Uani 1 1 d . . . . .
C007 C 0.37424(15) 0.4561(2) 0.64510(16) 0.0381(5) Uani 1 1 d . . . . .
C008 C 0.51795(15) 0.3826(3) 0.61101(18) 0.0427(5) Uani 1 1 d . . . . .
C009 C 0.13744(15) 0.2389(3) 0.64032(17) 0.0399(5) Uani 1 1 d . . . . .
C00A C 0.27224(15) 0.4464(3) 0.62249(18) 0.0428(5) Uani 1 1 d . . . . .
H00A H 0.249217 0.412807 0.553215 0.051 Uiso 1 1 calc R U . . .
C00B C 0.37977(18) 0.2776(3) 0.50523(18) 0.0471(6) Uani 1 1 d . . . . .
H00B H 0.317353 0.267711 0.488093 0.057 Uiso 1 1 calc R U . . .
C00C C 0.23061(17) 0.6003(3) 0.6348(2) 0.0510(6) Uani 1 1 d . . . . .
C00D C 0.42122(17) 0.5412(3) 0.72405(19) 0.0494(6) Uani 1 1 d . . . . .
H00D H 0.389617 0.595385 0.762112 0.059 Uiso 1 1 calc R U . . .
C00E C 0.15185(17) 0.0760(3) 0.79149(19) 0.0512(6) Uani 1 1 d . . . . .
H00C H 0.155761 0.154896 0.841524 0.061 Uiso 1 1 calc R U . . .
H00E H 0.212163 0.040656 0.792954 0.061 Uiso 1 1 calc R U . . .
C00F C 0.01586(16) 0.0643(3) 0.6560(2) 0.0524(6) Uani 1 1 d . . . . .
H00F H 0.013995 -0.005543 0.601088 0.063 Uiso 1 1 calc R U . . .
H00G H -0.030036 0.141859 0.634596 0.063 Uiso 1 1 calc R U . . .
C00G C 0.56235(17) 0.4723(3) 0.6936(2) 0.0557(7) Uani 1 1 d . . . . .
H00H H 0.624918 0.478787 0.710075 0.067 Uiso 1 1 calc R U . . .
C00H C 0.56607(19) 0.3018(3) 0.5528(2) 0.0575(7) Uani 1 1 d . . . . .
H00I H 0.628529 0.310123 0.567836 0.069 Uiso 1 1 calc R U . . .
C00I C 0.51539(19) 0.5491(3) 0.7491(2) 0.0589(7) Uani 1 1 d . . . . .
H00J H 0.545673 0.606763 0.803664 0.071 Uiso 1 1 calc R U . . .
C00J C 0.4296(2) 0.2002(3) 0.4521(2) 0.0622(8) Uani 1 1 d . . . . .
H00K H 0.400589 0.138086 0.399355 0.075 Uiso 1 1 calc R U . . .
C00K C 0.5235(2) 0.2127(3) 0.4757(2) 0.0644(8) Uani 1 1 d . . . . .
H00L H 0.556516 0.160015 0.438440 0.077 Uiso 1 1 calc R U . . .
C00L C 0.1979(2) 0.8422(4) 0.5566(3) 0.0705(9) Uani 1 1 d . . . . .
H00M H 0.223445 0.892242 0.619865 0.085 Uiso 1 1 calc R U . . .
H00N H 0.132940 0.837968 0.546419 0.085 Uiso 1 1 calc R U . . .
C00M C 0.0936(2) -0.0536(4) 0.8091(2) 0.0709(9) Uani 1 1 d . . . . .
H00O H 0.115295 -0.149889 0.789603 0.085 Uiso 1 1 calc R U . . .
H00P H 0.093008 -0.059212 0.878983 0.085 Uiso 1 1 calc R U . . .
C00N C 0.2211(2) 0.9280(3) 0.4742(3) 0.0759(10) Uani 1 1 d . . . . .
H00Q H 0.200619 0.872492 0.412894 0.114 Uiso 1 1 calc R U . . .
H00R H 0.285306 0.940931 0.488475 0.114 Uiso 1 1 calc R U . . .
H00S H 0.192542 1.026176 0.467906 0.114 Uiso 1 1 calc R U . . .
C00O C 0.0033(2) -0.0192(5) 0.7467(3) 0.0924(12) Uani 1 1 d . . . . .
H00T H -0.029548 0.043861 0.783188 0.111 Uiso 1 1 calc R U . . .
H00U H -0.030320 -0.112686 0.727137 0.111 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
S001 C009 1.770(2) . ?
S001 C00A 1.808(2) . ?
S002 C009 1.662(2) . ?
O003 C00C 1.333(3) . ?
O003 C00L 1.455(3) . ?
N004 C009 1.329(3) . ?
N004 C00F 1.472(3) . ?
N004 C00E 1.476(3) . ?
O005 C00C 1.187(3) . ?
C006 C00B 1.420(3) . ?
C006 C008 1.422(3) . ?
C006 C007 1.426(3) . ?
C007 C00D 1.369(3) . ?
C007 C00A 1.518(3) . ?
C008 C00H 1.411(4) . ?
C008 C00G 1.413(4) . ?
C00A C00C 1.520(3) . ?
C00A H00A 0.9800 . ?
C00B C00J 1.365(4) . ?
C00B H00B 0.9300 . ?
C00D C00I 1.399(4) . ?
C00D H00D 0.9300 . ?
C00E C00M 1.502(4) . ?
C00E H00C 0.9700 . ?
C00E H00E 0.9700 . ?
C00F C00O 1.507(4) . ?
C00F H00F 0.9700 . ?
C00F H00G 0.9700 . ?
C00G C00I 1.356(4) . ?
C00G H00H 0.9300 . ?
C00H C00K 1.351(4) . ?
C00H H00I 0.9300 . ?
C00I H00J 0.9300 . ?
C00J C00K 1.398(4) . ?
C00J H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00L C00N 1.482(5) . ?
C00L H00M 0.9700 . ?
C00L H00N 0.9700 . ?
C00M C00O 1.467(5) . ?
C00M H00O 0.9700 . ?
C00M H00P 0.9700 . ?
C00N H00Q 0.9600 . ?
C00N H00R 0.9600 . ?
C00N H00S 0.9600 . ?
C00O H00T 0.9700 . ?
C00O H00U 0.9700 . ?

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
C009 S001 C00A 103.45(11) . . ?
C00C O003 C00L 116.8(2) . . ?
C009 N004 C00F 123.1(2) . . ?
C009 N004 C00E 125.7(2) . . ?
C00F N004 C00E 111.14(19) . . ?
C00B C006 C008 117.7(2) . . ?
C00B C006 C007 123.5(2) . . ?
C008 C006 C007 118.8(2) . . ?
C00D C007 C006 119.3(2) . . ?
C00D C007 C00A 120.2(2) . . ?
C006 C007 C00A 120.4(2) . . ?
C00H C008 C00G 121.7(2) . . ?
C00H C008 C006 119.2(2) . . ?
C00G C008 C006 119.1(2) . . ?
N004 C009 S002 123.74(18) . . ?
N004 C009 S001 112.07(17) . . ?
S002 C009 S001 124.19(14) . . ?
C007 C00A C00C 111.49(19) . . ?
C007 C00A S001 106.59(16) . . ?
C00C C00A S001 112.95(16) . . ?
C007 C00A H00A 108.6 . . ?
C00C C00A H00A 108.6 . . ?
S001 C00A H00A 108.6 . . ?
C00J C00B C006 120.7(3) . . ?
C00J C00B H00B 119.7 . . ?
C006 C00B H00B 119.7 . . ?
O005 C00C O003 124.6(3) . . ?
O005 C00C C00A 126.5(3) . . ?
O003 C00C C00A 108.8(2) . . ?
C007 C00D C00I 121.9(2) . . ?
C007 C00D H00D 119.0 . . ?
C00I C00D H00D 119.0 . . ?
N004 C00E C00M 104.2(2) . . ?
N004 C00E H00C 110.9 . . ?
C00M C00E H00C 110.9 . . ?
N004 C00E H00E 110.9 . . ?
C00M C00E H00E 110.9 . . ?
H00C C00E H00E 108.9 . . ?
N004 C00F C00O 103.1(2) . . ?
N004 C00F H00F 111.1 . . ?
C00O C00F H00F 111.1 . . ?
N004 C00F H00G 111.1 . . ?
C00O C00F H00G 111.1 . . ?
H00F C00F H00G 109.1 . . ?
C00I C00G C008 121.2(2) . . ?
C00I C00G H00H 119.4 . . ?
C008 C00G H00H 119.4 . . ?
C00K C00H C008 121.5(3) . . ?
C00K C00H H00I 119.2 . . ?
C008 C00H H00I 119.2 . . ?
C00G C00I C00D 119.7(2) . . ?
C00G C00I H00J 120.1 . . ?
C00D C00I H00J 120.1 . . ?
C00B C00J C00K 121.2(3) . . ?
C00B C00J H00K 119.4 . . ?
C00K C00J H00K 119.4 . . ?
C00H C00K C00J 119.6(3) . . ?
C00H C00K H00L 120.2 . . ?
C00J C00K H00L 120.2 . . ?
O003 C00L C00N 108.1(3) . . ?
O003 C00L H00M 110.1 . . ?
C00N C00L H00M 110.1 . . ?
O003 C00L H00N 110.1 . . ?
C00N C00L H00N 110.1 . . ?
H00M C00L H00N 108.4 . . ?
C00O C00M C00E 105.1(3) . . ?
C00O C00M H00O 110.7 . . ?
C00E C00M H00O 110.7 . . ?
C00O C00M H00P 110.7 . . ?
C00E C00M H00P 110.7 . . ?
H00O C00M H00P 108.8 . . ?
C00L C00N H00Q 109.5 . . ?
C00L C00N H00R 109.5 . . ?
H00Q C00N H00R 109.5 . . ?
C00L C00N H00S 109.5 . . ?
H00Q C00N H00S 109.5 . . ?
H00R C00N H00S 109.5 . . ?
C00M C00O C00F 107.0(2) . . ?
C00M C00O H00T 110.3 . . ?
C00F C00O H00T 110.3 . . ?
C00M C00O H00U 110.3 . . ?
C00F C00O H00U 110.3 . . ?
H00T C00O H00U 108.6 . . ?

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
C00B C006 C007 C00D 177.8(2) . . . . ?
C008 C006 C007 C00D -0.8(3) . . . . ?
C00B C006 C007 C00A -0.2(3) . . . . ?
C008 C006 C007 C00A -178.8(2) . . . . ?
C00B C006 C008 C00H 1.9(3) . . . . ?
C007 C006 C008 C00H -179.4(2) . . . . ?
C00B C006 C008 C00G -177.8(2) . . . . ?
C007 C006 C008 C00G 0.9(3) . . . . ?
C00F N004 C009 S002 -1.8(3) . . . . ?
C00E N004 C009 S002 -177.87(19) . . . . ?
C00F N004 C009 S001 178.64(18) . . . . ?
C00E N004 C009 S001 2.6(3) . . . . ?
C00A S001 C009 N004 -178.35(17) . . . . ?
C00A S001 C009 S002 2.07(19) . . . . ?
C00D C007 C00A C00C 41.0(3) . . . . ?
C006 C007 C00A C00C -141.0(2) . . . . ?
C00D C007 C00A S001 -82.6(2) . . . . ?
C006 C007 C00A S001 95.4(2) . . . . ?
C009 S001 C00A C007 -155.51(16) . . . . ?
C009 S001 C00A C00C 81.71(19) . . . . ?
C008 C006 C00B C00J -1.1(4) . . . . ?
C007 C006 C00B C00J -179.7(2) . . . . ?
C00L O003 C00C O005 -0.6(4) . . . . ?
C00L O003 C00C C00A -179.6(2) . . . . ?
C007 C00A C00C O005 -104.3(3) . . . . ?
S001 C00A C00C O005 15.7(4) . . . . ?
C007 C00A C00C O003 74.6(3) . . . . ?
S001 C00A C00C O003 -165.39(18) . . . . ?
C006 C007 C00D C00I -0.1(4) . . . . ?
C00A C007 C00D C00I 178.0(2) . . . . ?
C009 N004 C00E C00M -173.3(2) . . . . ?
C00F N004 C00E C00M 10.2(3) . . . . ?
C009 N004 C00F C00O -167.9(3) . . . . ?
C00E N004 C00F C00O 8.7(3) . . . . ?
C00H C008 C00G C00I -179.8(3) . . . . ?
C006 C008 C00G C00I -0.1(4) . . . . ?
C00G C008 C00H C00K 178.1(3) . . . . ?
C006 C008 C00H C00K -1.6(4) . . . . ?
C008 C00G C00I C00D -0.7(4) . . . . ?
C007 C00D C00I C00G 0.8(4) . . . . ?
C006 C00B C00J C00K -0.2(4) . . . . ?
C008 C00H C00K C00J 0.4(4) . . . . ?
C00B C00J C00K C00H 0.6(5) . . . . ?
C00C O003 C00L C00N 171.3(3) . . . . ?
N004 C00E C00M C00O -25.5(3) . . . . ?
C00E C00M C00O C00F 31.9(4) . . . . ?
N004 C00F C00O C00M -25.0(4) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.053

