# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_exp192_a
_database_code_depnum_ccdc_archive 'CCDC 2470371'
loop_
_audit_author_name
_audit_author_address
'Mohammad Fadzlee Bin Ngatiman'
;Makmal i CRIM, ALAF UKM
Malaysia
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2026-05-22 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            'C10 H15 N2 S3'
_chemical_formula_weight         259.42

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           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                   17.644(6)
_cell_length_b                   5.6480(18)
_cell_length_c                   12.488(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.834(12)
_cell_angle_gamma                90
_cell_volume                     1241.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9564
_cell_measurement_theta_min      3.395
_cell_measurement_theta_max      26.976

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.567
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker D8 Quest Photon III HPAD diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35642
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.270
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2867
_reflns_number_gt                2398
_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       'BRUKER APEX5'
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0370P)²+0.5170P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0085(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2867
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S1_1 S 0.79650(3) 0.61225(9) 0.42003(5) 0.06386(18) Uani 1 1 d . . . . .
S2_1 S 0.71300(3) 0.73405(7) 0.61515(4) 0.05403(16) Uani 1 1 d . . . . .
S3_1 S 0.62381(3) 0.54620(8) 0.79505(4) 0.05371(15) Uani 1 1 d . . . . .
N1_1 N 0.68874(9) 0.2936(2) 0.64313(12) 0.0492(4) Uani 1 1 d . . . . .
N2_1 N 0.73075(9) 0.3083(3) 0.55315(12) 0.0510(4) Uani 1 1 d . . . . .
C1_1 C 0.83467(10) 0.3334(3) 0.37755(14) 0.0470(4) Uani 1 1 d . . . . .
H1_1 H 0.793491 0.216965 0.369428 0.056 Uiso 1 1 calc R U . . .
C2_1 C 0.89867(12) 0.2323(5) 0.45061(16) 0.0673(6) Uani 1 1 d . . . . .
H2A_1 H 0.925908 0.357748 0.489755 0.081 Uiso 1 1 calc R U . . .
H2B_1 H 0.879029 0.122603 0.501736 0.081 Uiso 1 1 calc R U . . .
C3_1 C 0.95032(13) 0.1055(5) 0.37721(18) 0.0756(7) Uani 1 1 d . . . . .
H3A_1 H 0.951180 -0.062945 0.392381 0.091 Uiso 1 1 calc R U . . .
H3B_1 H 1.001722 0.166202 0.387537 0.091 Uiso 1 1 calc R U . . .
C4_1 C 0.91875(13) 0.1504(5) 0.26318(16) 0.0698(6) Uani 1 1 d . . . . .
H4A_1 H 0.959520 0.178824 0.216389 0.084 Uiso 1 1 calc R U . . .
H4B_1 H 0.889194 0.015831 0.236008 0.084 Uiso 1 1 calc R U . . .
C5_1 C 0.86939(11) 0.3659(4) 0.26945(14) 0.0571(5) Uani 1 1 d . . . . .
H5A_1 H 0.830430 0.369718 0.210869 0.069 Uiso 1 1 calc R U . . .
H5B_1 H 0.899199 0.510090 0.268360 0.069 Uiso 1 1 calc R U . . .
C6_1 C 0.74706(9) 0.5239(3) 0.52988(14) 0.0440(4) Uani 1 1 d . . . . .
C7_1 C 0.67577(9) 0.4989(3) 0.68333(14) 0.0416(4) Uani 1 1 d . . . . .
C8_1 C 0.59579(10) 0.2460(3) 0.82384(14) 0.0450(4) Uani 1 1 d . . . . .
H8A_1 H 0.568198 0.177853 0.761468 0.054 Uiso 1 1 calc R U . . .
H8B_1 H 0.640450 0.149716 0.841281 0.054 Uiso 1 1 calc R U . . .
C9_1 C 0.54543(10) 0.2502(3) 0.91848(14) 0.0472(4) Uani 1 1 d . . . . .
H9A_1 H 0.571826 0.331219 0.978468 0.057 Uiso 1 1 calc R U . . .
H9B_1 H 0.499323 0.337712 0.898567 0.057 Uiso 1 1 calc R U . . .
C10_1 C 0.52491(9) 0.0021(3) 0.95250(13) 0.0448(4) Uani 1 1 d . . . . .
H10A_1 H 0.571253 -0.085148 0.971292 0.054 Uiso 1 1 calc R U . . .
H10B_1 H 0.498485 -0.077832 0.892228 0.054 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
S1_1 C6_1 1.7470(17) . ?
S1_1 C1_1 1.8066(19) . ?
S2_1 C6_1 1.7289(17) . ?
S2_1 C7_1 1.7307(17) . ?
S3_1 C7_1 1.7406(17) . ?
S3_1 C8_1 1.8091(18) . ?
N1_1 C7_1 1.290(2) . ?
N1_1 N2_1 1.389(2) . ?
N2_1 C6_1 1.289(2) . ?
C1_1 C2_1 1.515(3) . ?
C1_1 C5_1 1.530(2) . ?
C1_1 H1_1 0.9800 . ?
C2_1 C3_1 1.515(3) . ?
C2_1 H2A_1 0.9700 . ?
C2_1 H2B_1 0.9700 . ?
C3_1 C4_1 1.515(3) . ?
C3_1 H3A_1 0.9700 . ?
C3_1 H3B_1 0.9700 . ?
C4_1 C5_1 1.502(3) . ?
C4_1 H4A_1 0.9700 . ?
C4_1 H4B_1 0.9700 . ?
C5_1 H5A_1 0.9700 . ?
C5_1 H5B_1 0.9700 . ?
C8_1 C9_1 1.526(2) . ?
C8_1 H8A_1 0.9700 . ?
C8_1 H8B_1 0.9700 . ?
C9_1 C10_1 1.515(2) . ?
C9_1 H9A_1 0.9700 . ?
C9_1 H9B_1 0.9700 . ?
C10_1 C10_1 1.523(3) 3_657 ?
C10_1 H10A_1 0.9700 . ?
C10_1 H10B_1 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
C6_1 S1_1 C1_1 101.37(8) . . ?
C6_1 S2_1 C7_1 86.28(8) . . ?
C7_1 S3_1 C8_1 100.43(8) . . ?
C7_1 N1_1 N2_1 112.27(13) . . ?
C6_1 N2_1 N1_1 112.23(14) . . ?
C2_1 C1_1 C5_1 104.49(15) . . ?
C2_1 C1_1 S1_1 115.41(14) . . ?
C5_1 C1_1 S1_1 109.47(13) . . ?
C2_1 C1_1 H1_1 109.1 . . ?
C5_1 C1_1 H1_1 109.1 . . ?
S1_1 C1_1 H1_1 109.1 . . ?
C3_1 C2_1 C1_1 105.55(16) . . ?
C3_1 C2_1 H2A_1 110.6 . . ?
C1_1 C2_1 H2A_1 110.6 . . ?
C3_1 C2_1 H2B_1 110.6 . . ?
C1_1 C2_1 H2B_1 110.6 . . ?
H2A_1 C2_1 H2B_1 108.8 . . ?
C2_1 C3_1 C4_1 106.94(17) . . ?
C2_1 C3_1 H3A_1 110.3 . . ?
C4_1 C3_1 H3A_1 110.3 . . ?
C2_1 C3_1 H3B_1 110.3 . . ?
C4_1 C3_1 H3B_1 110.3 . . ?
H3A_1 C3_1 H3B_1 108.6 . . ?
C5_1 C4_1 C3_1 105.34(18) . . ?
C5_1 C4_1 H4A_1 110.7 . . ?
C3_1 C4_1 H4A_1 110.7 . . ?
C5_1 C4_1 H4B_1 110.7 . . ?
C3_1 C4_1 H4B_1 110.7 . . ?
H4A_1 C4_1 H4B_1 108.8 . . ?
C4_1 C5_1 C1_1 102.49(16) . . ?
C4_1 C5_1 H5A_1 111.3 . . ?
C1_1 C5_1 H5A_1 111.3 . . ?
C4_1 C5_1 H5B_1 111.3 . . ?
C1_1 C5_1 H5B_1 111.3 . . ?
H5A_1 C5_1 H5B_1 109.2 . . ?
N2_1 C6_1 S2_1 114.68(13) . . ?
N2_1 C6_1 S1_1 125.28(13) . . ?
S2_1 C6_1 S1_1 120.00(10) . . ?
N1_1 C7_1 S2_1 114.54(12) . . ?
N1_1 C7_1 S3_1 124.51(12) . . ?
S2_1 C7_1 S3_1 120.94(9) . . ?
C9_1 C8_1 S3_1 108.68(12) . . ?
C9_1 C8_1 H8A_1 110.0 . . ?
S3_1 C8_1 H8A_1 110.0 . . ?
C9_1 C8_1 H8B_1 110.0 . . ?
S3_1 C8_1 H8B_1 110.0 . . ?
H8A_1 C8_1 H8B_1 108.3 . . ?
C10_1 C9_1 C8_1 111.42(14) . . ?
C10_1 C9_1 H9A_1 109.3 . . ?
C8_1 C9_1 H9A_1 109.3 . . ?
C10_1 C9_1 H9B_1 109.3 . . ?
C8_1 C9_1 H9B_1 109.3 . . ?
H9A_1 C9_1 H9B_1 108.0 . . ?
C9_1 C10_1 C10_1 113.21(17) . 3_657 ?
C9_1 C10_1 H10A_1 108.9 . . ?
C10_1 C10_1 H10A_1 108.9 3_657 . ?
C9_1 C10_1 H10B_1 108.9 . . ?
C10_1 C10_1 H10B_1 108.9 3_657 . ?
H10A_1 C10_1 H10B_1 107.7 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
