# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_SM_37_a
_audit_block_doi                 10.5517/ccdc.csd.cc2l6050
_database_code_depnum_ccdc_archive 'CCDC 2389051'
loop_
_audit_author_name
_audit_author_address
'Sudip Mondal'
;Visva Bharati (A central university)
India
;
_audit_update_record             
;
2024-10-07 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N O S'
_chemical_formula_sum            'C13 H17 N O S'
_chemical_formula_weight         235.33

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           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                   9.1512(8)
_cell_length_b                   13.1236(12)
_cell_length_c                   10.5647(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.670(2)
_cell_angle_gamma                90
_cell_volume                     1262.58(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    191(2)
_cell_measurement_reflns_used    4381
_cell_measurement_theta_min      2.294
_cell_measurement_theta_max      30.600

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.236
_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      191(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17609
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         34.191
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4672
_reflns_number_gt                3410
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] 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         4672
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1883
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_restrained_S_all      1.266
_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 0.46258(4) 0.61785(3) 0.18549(3) 0.02994(14) Uani 1 1 d . . . . .
O002 O 0.82550(12) 0.70319(8) 0.21118(10) 0.0309(3) Uani 1 1 d . . . . .
N003 N 0.56053(13) 0.78377(9) 0.31461(10) 0.0233(2) Uani 1 1 d . . . . .
C004 C 0.78616(14) 0.55694(10) 0.33768(12) 0.0195(2) Uani 1 1 d . . . . .
C005 C 0.73503(14) 0.52996(10) 0.45533(12) 0.0210(3) Uani 1 1 d . . . . .
C006 C 0.74287(14) 0.65434(10) 0.27264(12) 0.0214(3) Uani 1 1 d . . . . .
C007 C 0.78198(15) 0.43836(11) 0.51233(13) 0.0235(3) Uani 1 1 d . . . . .
H007 H 0.7492 0.4205 0.5920 0.028 Uiso 1 1 calc R U . . .
C008 C 0.88449(14) 0.49168(10) 0.28098(12) 0.0226(3) Uani 1 1 d . . . . .
C009 C 0.58529(15) 0.69278(10) 0.26773(12) 0.0218(3) Uani 1 1 d . . . . .
C00A C 0.92631(15) 0.40044(10) 0.34124(13) 0.0234(3) Uani 1 1 d . . . . .
H00A H 0.9914 0.3562 0.3029 0.028 Uiso 1 1 calc R U . . .
C00B C 0.87545(15) 0.37212(10) 0.45615(13) 0.0231(3) Uani 1 1 d . . . . .
C00C C 0.63736(17) 0.59776(12) 0.52665(13) 0.0283(3) Uani 1 1 d . . . . .
H00B H 0.6149 0.5635 0.6049 0.043 Uiso 1 1 calc R U . . .
H00C H 0.5459 0.6115 0.4731 0.043 Uiso 1 1 calc R U . . .
H00D H 0.6880 0.6622 0.5482 0.043 Uiso 1 1 calc R U . . .
C00D C 0.41347(16) 0.82908(12) 0.29936(17) 0.0324(3) Uani 1 1 d . . . . .
H00E H 0.3807 0.8359 0.2086 0.049 Uiso 1 1 calc R U . . .
H00F H 0.4164 0.8965 0.3394 0.049 Uiso 1 1 calc R U . . .
H00G H 0.3450 0.7852 0.3398 0.049 Uiso 1 1 calc R U . . .
C00E C 0.67409(17) 0.84545(12) 0.38630(14) 0.0293(3) Uani 1 1 d . . . . .
H00H H 0.7567 0.8017 0.4175 0.044 Uiso 1 1 calc R U . . .
H00I H 0.6330 0.8776 0.4586 0.044 Uiso 1 1 calc R U . . .
H00J H 0.7084 0.8982 0.3307 0.044 Uiso 1 1 calc R U . . .
C00F C 0.91788(18) 0.27074(12) 0.51565(16) 0.0329(3) Uani 1 1 d . . . . .
H00K H 0.9305 0.2778 0.6084 0.049 Uiso 1 1 calc R U . . .
H00L H 1.0103 0.2476 0.4856 0.049 Uiso 1 1 calc R U . . .
H00M H 0.8405 0.2208 0.4916 0.049 Uiso 1 1 calc R U . . .
C00G C 0.9438(2) 0.51357(14) 0.15590(16) 0.0365(4) Uani 1 1 d . . . . .
H00N H 1.0197 0.5663 0.1679 0.055 Uiso 1 1 calc R U . . .
H00O H 0.8639 0.5374 0.0944 0.055 Uiso 1 1 calc R U . . .
H00P H 0.9864 0.4513 0.1240 0.055 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 1.6704(14) . ?
O002 C006 1.2253(17) . ?
N003 C009 1.3209(17) . ?
N003 C00D 1.4656(18) . ?
N003 C00E 1.4674(18) . ?
C004 C005 1.4156(18) . ?
C004 C008 1.4172(17) . ?
C004 C006 1.4864(18) . ?
C005 C007 1.3933(18) . ?
C005 C00C 1.5138(18) . ?
C006 C009 1.5239(19) . ?
C007 C00B 1.3928(19) . ?
C007 H007 0.9500 . ?
C008 C00A 1.3919(18) . ?
C008 C00G 1.505(2) . ?
C00A C00B 1.3929(19) . ?
C00A H00A 0.9500 . ?
C00B C00F 1.506(2) . ?
C00C H00B 0.9800 . ?
C00C H00C 0.9800 . ?
C00C H00D 0.9800 . ?
C00D H00E 0.9800 . ?
C00D H00F 0.9800 . ?
C00D H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E H00I 0.9800 . ?
C00E H00J 0.9800 . ?
C00F H00K 0.9800 . ?
C00F H00L 0.9800 . ?
C00F H00M 0.9800 . ?
C00G H00N 0.9800 . ?
C00G H00O 0.9800 . ?
C00G H00P 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
C009 N003 C00D 121.01(12) . . ?
C009 N003 C00E 123.59(12) . . ?
C00D N003 C00E 115.39(12) . . ?
C005 C004 C008 119.91(12) . . ?
C005 C004 C006 121.66(11) . . ?
C008 C004 C006 118.40(11) . . ?
C007 C005 C004 118.73(12) . . ?
C007 C005 C00C 117.65(12) . . ?
C004 C005 C00C 123.55(12) . . ?
O002 C006 C004 123.00(12) . . ?
O002 C006 C009 116.12(12) . . ?
C004 C006 C009 120.57(11) . . ?
C00B C007 C005 122.03(12) . . ?
C00B C007 H007 119.0 . . ?
C005 C007 H007 119.0 . . ?
C00A C008 C004 118.94(12) . . ?
C00A C008 C00G 117.33(12) . . ?
C004 C008 C00G 123.70(12) . . ?
N003 C009 C006 118.90(12) . . ?
N003 C009 S001 126.58(11) . . ?
C006 C009 S001 114.08(9) . . ?
C008 C00A C00B 121.85(12) . . ?
C008 C00A H00A 119.1 . . ?
C00B C00A H00A 119.1 . . ?
C007 C00B C00A 118.49(12) . . ?
C007 C00B C00F 121.16(12) . . ?
C00A C00B C00F 120.32(13) . . ?
C005 C00C H00B 109.5 . . ?
C005 C00C H00C 109.5 . . ?
H00B C00C H00C 109.5 . . ?
C005 C00C H00D 109.5 . . ?
H00B C00C H00D 109.5 . . ?
H00C C00C H00D 109.5 . . ?
N003 C00D H00E 109.5 . . ?
N003 C00D H00F 109.5 . . ?
H00E C00D H00F 109.5 . . ?
N003 C00D H00G 109.5 . . ?
H00E C00D H00G 109.5 . . ?
H00F C00D H00G 109.5 . . ?
N003 C00E H00H 109.5 . . ?
N003 C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
N003 C00E H00J 109.5 . . ?
H00H C00E H00J 109.5 . . ?
H00I C00E H00J 109.5 . . ?
C00B C00F H00K 109.5 . . ?
C00B C00F H00L 109.5 . . ?
H00K C00F H00L 109.5 . . ?
C00B C00F H00M 109.5 . . ?
H00K C00F H00M 109.5 . . ?
H00L C00F H00M 109.5 . . ?
C008 C00G H00N 109.5 . . ?
C008 C00G H00O 109.5 . . ?
H00N C00G H00O 109.5 . . ?
C008 C00G H00P 109.5 . . ?
H00N C00G H00P 109.5 . . ?
H00O C00G H00P 109.5 . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.064

