# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_25pm_L_173K
_database_code_depnum_ccdc_archive 'CCDC 2451965'
loop_
_audit_author_name
_audit_author_address
'Dr Banele Vatsha'
;University of Johannesburg
South Africa
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
S-benzyl-(N,N-dimethyl-carbonyl)carbamothioate
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 N2 O2 S'
_chemical_formula_sum            'C11 H14 N2 O2 S'
_chemical_formula_weight         238.30

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.8421(3)
_cell_length_b                   9.9787(5)
_cell_length_c                   10.4247(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.544(2)
_cell_angle_gamma                90
_cell_volume                     595.43(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6242
_cell_measurement_theta_min      2.8538
_cell_measurement_theta_max      28.7322

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?

# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - -
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Fixed-Chi three-circle diffractometer'
_diffrn_radiation_source         'I\mS micro-focus sealed tube'
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_radiation_monochromator  'Incoatec I\mS multilayer optics'
_diffrn_detector                 CPAD
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_detector_area_resol_mean 7.4
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            10468
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2678
_reflns_number_gt                2471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
# - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 
_computing_data_collection       'APEX4 v2022.1.1 (Bruker-AXS, 2023)'
_computing_cell_refinement       'SAINT 8.40B (Bruker-AXS, 2022)'
_computing_data_reduction        'SAINT 8.40B (Bruker-AXS, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019 (Sheldrick, 2015)'
_computing_molecular_graphics    (Olex2)
_computing_publication_material  encifer
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2678
_refine_ls_number_parameters     149
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.007
_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 0.60642(12) 0.32238(7) 0.86034(6) 0.02836(19) Uani 1 1 d . U . . .
O2 O 0.8399(4) 0.7531(2) 0.9394(2) 0.0308(5) Uani 1 1 d . U . . .
O1 O 0.9184(5) 0.4934(3) 0.9734(3) 0.0454(6) Uani 1 1 d . U . . .
H1 H 0.956390 0.573728 0.990057 0.068 Uiso 1 1 calc R U . . .
N1 N 0.5685(4) 0.5873(2) 0.8504(2) 0.0229(5) Uani 1 1 d . U . . .
N2 N 0.4963(4) 0.8095(3) 0.8090(2) 0.0267(5) Uani 1 1 d . U . . .
C8 C 0.7059(5) 0.4886(3) 0.8982(2) 0.0211(5) Uani 1 1 d . U . . .
C2 C 0.2580(5) 0.2458(3) 0.6561(3) 0.0243(6) Uani 1 1 d . U . . .
C10 C 0.2579(5) 0.7780(3) 0.7433(3) 0.0325(7) Uani 1 1 d . U . . .
H10A H 0.225851 0.683130 0.756748 0.049 Uiso 1 1 calc R U . . .
H10B H 0.239417 0.795933 0.649403 0.049 Uiso 1 1 calc R U . . .
H10C H 0.148137 0.833586 0.779720 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3903(5) 0.2300(4) 0.5599(3) 0.0308(6) Uani 1 1 d . U . . .
H3 H 0.520644 0.286840 0.559639 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6477(5) 0.7172(3) 0.8722(3) 0.0219(5) Uani 1 1 d . U . . .
C5 C 0.1415(6) 0.0509(4) 0.4627(3) 0.0381(8) Uani 1 1 d . U . . .
H5 H 0.102989 -0.016206 0.397284 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0065(6) 0.0671(3) 0.5552(3) 0.0363(7) Uani 1 1 d . U . . .
H6 H -0.126462 0.011742 0.553234 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3335(7) 0.1323(4) 0.4646(3) 0.0394(8) Uani 1 1 d . U . . .
H4 H 0.426802 0.121083 0.400475 0.047 Uiso 1 1 calc R U . . .
C7 C 0.0643(5) 0.1646(3) 0.6521(3) 0.0286(6) Uani 1 1 d . U . . .
H7 H -0.029794 0.175345 0.715946 0.034 Uiso 1 1 calc R U . . .
C1 C 0.3182(5) 0.3516(3) 0.7595(3) 0.0348(7) Uani 1 1 d . U . . .
H1A H 0.199955 0.351466 0.815565 0.042 Uiso 1 1 calc R U . . .
H1B H 0.315006 0.440708 0.717418 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5653(6) 0.9498(3) 0.8161(4) 0.0378(7) Uani 1 1 d . U . . .
H11A H 0.458407 1.000846 0.749370 0.057 Uiso 1 1 calc R U . . .
H11B H 0.724858 0.957792 0.800792 0.057 Uiso 1 1 calc R U . . .
H11C H 0.559219 0.985185 0.903076 0.057 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 C8 1.775(3) . ?
S1 C1 1.821(3) . ?
O2 C9 1.251(4) . ?
O1 C8 1.330(4) . ?
O1 H1 0.8400 . ?
N1 C8 1.305(4) . ?
N1 C9 1.380(4) . ?
N2 C9 1.354(4) . ?
N2 C11 1.454(4) . ?
N2 C10 1.458(4) . ?
C2 C7 1.386(4) . ?
C2 C3 1.392(4) . ?
C2 C1 1.499(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C5 C6 1.372(5) . ?
C5 C4 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C8 S1 C1 101.69(14) . . ?
C8 O1 H1 109.5 . . ?
C8 N1 C9 119.1(2) . . ?
C9 N2 C11 118.9(3) . . ?
C9 N2 C10 123.4(3) . . ?
C11 N2 C10 117.5(2) . . ?
N1 C8 O1 128.9(3) . . ?
N1 C8 S1 118.1(2) . . ?
O1 C8 S1 113.0(2) . . ?
C7 C2 C3 118.7(3) . . ?
C7 C2 C1 120.4(3) . . ?
C3 C2 C1 120.9(3) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C9 N2 120.2(3) . . ?
O2 C9 N1 126.5(3) . . ?
N2 C9 N1 113.2(3) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C7 C6 120.5(3) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C2 C1 S1 111.0(2) . . ?
C2 C1 H1A 109.4 . . ?
S1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
S1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C9 N1 C8 O1 3.2(4) . . . . ?
C9 N1 C8 S1 -176.24(19) . . . . ?
C1 S1 C8 N1 -0.6(2) . . . . ?
C1 S1 C8 O1 179.8(2) . . . . ?
C7 C2 C3 C4 -2.0(5) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C11 N2 C9 O2 2.7(4) . . . . ?
C10 N2 C9 O2 -171.6(3) . . . . ?
C11 N2 C9 N1 -175.7(3) . . . . ?
C10 N2 C9 N1 10.0(4) . . . . ?
C8 N1 C9 O2 -3.2(4) . . . . ?
C8 N1 C9 N2 175.1(2) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C6 C5 C4 C3 0.1(5) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
C1 C2 C7 C6 179.3(3) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C7 C2 C1 S1 119.5(3) . . . . ?
C3 C2 C1 S1 -62.5(4) . . . . ?
C8 S1 C1 C2 146.7(2) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and n-hexane'
