# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_gn_st_312_b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2259851'
loop_
_audit_author_name
_audit_author_address
'Guddeangadi Gururaja'
;Central University of Gujarat, Gandhinagar
India
;
_audit_update_record             
;
2023-04-29 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O2 S2'
_chemical_formula_sum            'C10 H11 N O2 S2'
_chemical_formula_weight         241.32
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.8649(7)
_cell_length_b                   8.9005(5)
_cell_length_c                   11.3860(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.427(4)
_cell_angle_gamma                90
_cell_volume                     1100.72(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      34.20
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.8771. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.41
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66766
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.451
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4038
_reflns_number_total             5360
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         5360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.70509(4) 0.26417(4) 0.77406(3) 0.04686(10) Uani 1 1 d . . . . .
S2 S 0.64226(3) 0.59931(4) 0.42692(3) 0.04122(9) Uani 1 1 d . . . . .
O2 O 0.84316(10) 0.35776(11) 0.55984(9) 0.0461(2) Uani 1 1 d . . . . .
O1 O 0.93522(11) 0.96763(11) 0.65714(9) 0.0484(2) Uani 1 1 d . . . . .
N1 N 0.83617(9) 0.70637(10) 0.55161(8) 0.02942(17) Uani 1 1 d . . . . .
C1 C 0.92708(14) 0.83161(16) 0.72230(11) 0.0414(3) Uani 1 1 d . . . . .
H1A H 0.850116 0.829966 0.763664 0.050 Uiso 1 1 calc R . . . .
H1B H 0.993924 0.827536 0.780290 0.050 Uiso 1 1 calc R . . . .
C2 C 0.93354(11) 0.69600(14) 0.64318(11) 0.0345(2) Uani 1 1 d . . . . .
H2A H 1.013462 0.691689 0.607211 0.041 Uiso 1 1 calc R . . . .
H2B H 0.922884 0.605120 0.688836 0.041 Uiso 1 1 calc R . . . .
C5 C 0.75588(10) 0.59870(11) 0.52690(8) 0.02645(17) Uani 1 1 d . . . . .
C6 C 0.77067(10) 0.45224(11) 0.59399(9) 0.02934(19) Uani 1 1 d . . . . .
C7 C 0.69432(10) 0.42971(12) 0.69575(9) 0.02955(19) Uani 1 1 d . . . . .
C10 C 0.59840(15) 0.32495(18) 0.86995(12) 0.0475(3) Uani 1 1 d . . . . .
H10 H 0.571772 0.268522 0.933201 0.057 Uiso 1 1 calc R . . . .
C9 C 0.55633(14) 0.46527(19) 0.84386(12) 0.0459(3) Uani 1 1 d . . . . .
H9 H 0.497679 0.515305 0.887314 0.055 Uiso 1 1 calc R . . . .
C8 C 0.61148(12) 0.52675(15) 0.74349(11) 0.0368(2) Uani 1 1 d . . . . .
H8 H 0.593655 0.621682 0.713487 0.044 Uiso 1 1 calc R . . . .
C4 C 0.83492(16) 0.97720(14) 0.57551(14) 0.0466(3) Uani 1 1 d . . . . .
H4A H 0.838639 1.072121 0.533893 0.056 Uiso 1 1 calc R . . . .
H4B H 0.758262 0.974383 0.617347 0.056 Uiso 1 1 calc R . . . .
C3 C 0.83718(13) 0.84995(13) 0.48848(10) 0.0375(2) Uani 1 1 d . . . . .
H3A H 0.765919 0.856252 0.435677 0.045 Uiso 1 1 calc R . . . .
H3B H 0.910608 0.856826 0.442027 0.045 Uiso 1 1 calc R . . . .


_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 C7 1.7246(11) . ?
S1 C10 1.7004(16) . ?
S2 C5 1.6583(11) . ?
O2 C6 1.2222(14) . ?
O1 C1 1.4238(17) . ?
O1 C4 1.4171(19) . ?
N1 C2 1.4696(14) . ?
N1 C5 1.3215(13) . ?
N1 C3 1.4664(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5088(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.5174(14) . ?
C6 C7 1.4556(15) . ?
C7 C8 1.3696(17) . ?
C10 H10 0.9300 . ?
C10 C9 1.360(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.4137(18) . ?
C8 H8 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.5055(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 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
C10 S1 C7 91.24(7) . . ?
C4 O1 C1 109.64(10) . . ?
C5 N1 C2 124.42(9) . . ?
C5 N1 C3 122.72(10) . . ?
C3 N1 C2 112.86(9) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.39(10) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 109.27(10) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C5 S2 128.31(8) . . ?
N1 C5 C6 117.05(9) . . ?
C6 C5 S2 114.59(7) . . ?
O2 C6 C5 119.46(10) . . ?
O2 C6 C7 122.89(10) . . ?
C7 C6 C5 117.63(9) . . ?
C6 C7 S1 119.77(8) . . ?
C8 C7 S1 111.74(8) . . ?
C8 C7 C6 128.48(10) . . ?
S1 C10 H10 123.8 . . ?
C9 C10 S1 112.49(10) . . ?
C9 C10 H10 123.8 . . ?
C10 C9 H9 123.7 . . ?
C10 C9 C8 112.65(13) . . ?
C8 C9 H9 123.7 . . ?
C7 C8 C9 111.88(12) . . ?
C7 C8 H8 124.1 . . ?
C9 C8 H8 124.1 . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
O1 C4 C3 111.19(12) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
N1 C3 C4 109.42(10) . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?

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
S1 C7 C8 C9 -0.31(14) . . . . ?
S1 C10 C9 C8 -0.06(17) . . . . ?
S2 C5 C6 O2 93.90(12) . . . . ?
S2 C5 C6 C7 -84.63(11) . . . . ?
O2 C6 C7 S1 0.43(16) . . . . ?
O2 C6 C7 C8 179.01(13) . . . . ?
O1 C1 C2 N1 -56.09(14) . . . . ?
O1 C4 C3 N1 56.99(15) . . . . ?
N1 C5 C6 O2 -83.77(14) . . . . ?
N1 C5 C6 C7 97.71(12) . . . . ?
C1 O1 C4 C3 -61.73(15) . . . . ?
C2 N1 C5 S2 179.37(9) . . . . ?
C2 N1 C5 C6 -3.34(15) . . . . ?
C2 N1 C3 C4 -52.79(15) . . . . ?
C5 N1 C2 C1 -128.10(11) . . . . ?
C5 N1 C3 C4 127.63(12) . . . . ?
C5 C6 C7 S1 178.90(8) . . . . ?
C5 C6 C7 C8 -2.51(18) . . . . ?
C6 C7 C8 C9 -178.99(12) . . . . ?
C7 S1 C10 C9 -0.10(12) . . . . ?
C10 S1 C7 C6 179.04(10) . . . . ?
C10 S1 C7 C8 0.23(10) . . . . ?
C10 C9 C8 C7 0.24(18) . . . . ?
C4 O1 C1 C2 61.42(15) . . . . ?
C3 N1 C2 C1 52.33(13) . . . . ?
C3 N1 C5 S2 -1.10(16) . . . . ?
C3 N1 C5 C6 176.19(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
