# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
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data_aks013a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2377839'
loop_
_audit_author_name
_audit_author_address
'Laxmidhar Rout'
;Berhampur University
India
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6374)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O3 S'
_chemical_formula_sum            'C18 H19 N O3 S'
_chemical_formula_weight         329.40
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9365(5)
_cell_length_b                   7.9877(3)
_cell_length_c                   19.0534(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.804(2)
_cell_angle_gamma                90
_cell_volume                     1664.29(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9714
_cell_measurement_temperature    299.0
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1263 before and 0.0776 after correction.
The Ratio of minimum to maximum transmission is 0.8908.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            60807
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.134
_diffrn_ambient_temperature      299.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3154
_reflns_number_total             3838
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.124
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0739
_refine_ls_restrained_S_all      1.251
_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)+(0.1047P)²+0.1988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C16(H16), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_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 0.65545(4) 0.40604(6) 0.33948(2) 0.0493(2) Uani 1 1 d . . . . .
O1 O 0.66761(13) 0.41269(16) 0.51320(7) 0.0502(4) Uani 1 1 d . . . . .
O2 O 0.89133(14) 0.5136(2) 0.59537(8) 0.0659(4) Uani 1 1 d . . . . .
O3 O 1.00564(15) 0.7469(2) 0.56681(9) 0.0731(5) Uani 1 1 d . . . . .
N1 N 0.55501(15) 0.7300(2) 0.35399(8) 0.0487(4) Uani 1 1 d . . . . .
C10 C 0.71198(15) 0.6429(2) 0.43823(8) 0.0394(4) Uani 1 1 d . . . . .
C9 C 0.77964(17) 0.7860(2) 0.42253(9) 0.0448(4) Uani 1 1 d . . . . .
C11 C 0.60285(16) 0.5933(2) 0.39396(9) 0.0396(4) Uani 1 1 d . . . . .
H11 H 0.538701 0.554536 0.425471 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6485(2) 0.8189(3) 0.31443(11) 0.0564(5) Uani 1 1 d . . . . .
H7A H 0.610160 0.903067 0.284779 0.068 Uiso 1 1 calc R U . . .
H7B H 0.691248 0.740695 0.284494 0.068 Uiso 1 1 calc R U . . .
C15 C 0.91305(18) 0.7257(3) 0.51813(11) 0.0516(5) Uani 1 1 d . . . . .
C6 C 0.51843(17) 0.2880(2) 0.33155(10) 0.0469(4) Uani 1 1 d . . . . .
C13 C 0.74404(16) 0.5416(2) 0.49617(9) 0.0413(4) Uani 1 1 d . . . . .
C2 C 0.3473(2) 0.1470(3) 0.38306(14) 0.0639(6) Uani 1 1 d . . . . .
H2 H 0.304949 0.114501 0.422805 0.077 Uiso 1 1 calc R U . . .
C1 C 0.45546(19) 0.2358(2) 0.39016(11) 0.0533(5) Uani 1 1 d . . . . .
H1 H 0.486120 0.260669 0.434729 0.064 Uiso 1 1 calc R U . . .
C16 C 0.88318(18) 0.8284(3) 0.46280(11) 0.0525(5) Uani 1 1 d . . . . .
H16 H 0.929795 0.922325 0.452447 0.063 Uiso 1 1 calc R U . . .
C14 C 0.84559(18) 0.5864(2) 0.53483(9) 0.0469(4) Uani 1 1 d . . . . .
C8 C 0.7380(2) 0.9010(3) 0.36411(11) 0.0559(5) Uani 1 1 d . . . . .
H8A H 0.700173 0.999340 0.384319 0.067 Uiso 1 1 calc R U . . .
H8B H 0.808701 0.937629 0.338076 0.067 Uiso 1 1 calc R U . . .
C12 C 0.4500(2) 0.6849(3) 0.31055(13) 0.0624(6) Uani 1 1 d . . . . .
H12A H 0.476580 0.620387 0.271102 0.094 Uiso 1 1 calc R U . . .
H12B H 0.409900 0.784756 0.294160 0.094 Uiso 1 1 calc R U . . .
H12C H 0.393948 0.619815 0.337671 0.094 Uiso 1 1 calc R U . . .
C18 C 0.7224(2) 0.2533(3) 0.52650(14) 0.0665(6) Uani 1 1 d . . . . .
H18A H 0.766710 0.218162 0.485943 0.100 Uiso 1 1 calc R U . . .
H18B H 0.659781 0.172886 0.536493 0.100 Uiso 1 1 calc R U . . .
H18C H 0.777481 0.261829 0.566007 0.100 Uiso 1 1 calc R U . . .
C5 C 0.4723(2) 0.2455(3) 0.26553(12) 0.0615(6) Uani 1 1 d . . . . .
H5 H 0.513853 0.277940 0.225497 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3025(2) 0.1070(3) 0.31808(17) 0.0729(7) Uani 1 1 d . . . . .
H3 H 0.229792 0.047262 0.313504 0.087 Uiso 1 1 calc R U . . .
C17 C 0.9959(2) 0.6099(3) 0.61377(12) 0.0689(7) Uani 1 1 d . . . . .
H17A H 0.988843 0.650797 0.661479 0.083 Uiso 1 1 calc R U . . .
H17B H 1.068729 0.540893 0.611298 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3651(2) 0.1551(3) 0.25924(15) 0.0741(7) Uani 1 1 d . . . . .
H4 H 0.334933 0.126589 0.214950 0.089 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 C11 1.9137(17) . ?
S1 C6 1.775(2) . ?
O1 C13 1.368(2) . ?
O1 C18 1.428(3) . ?
O2 C14 1.379(2) . ?
O2 C17 1.419(3) . ?
O3 C15 1.374(2) . ?
O3 C17 1.418(3) . ?
N1 C11 1.426(2) . ?
N1 C7 1.463(3) . ?
N1 C12 1.452(3) . ?
C10 C9 1.397(3) . ?
C10 C11 1.505(2) . ?
C10 C13 1.409(2) . ?
C9 C16 1.400(3) . ?
C9 C8 1.509(3) . ?
C11 H11 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(3) . ?
C15 C16 1.372(3) . ?
C15 C14 1.375(3) . ?
C6 C1 1.384(3) . ?
C6 C5 1.391(3) . ?
C13 C14 1.371(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.385(3) . ?
C2 C3 1.363(4) . ?
C1 H1 0.9300 . ?
C16 H16 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 H4 0.9300 . ?

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 S1 C11 101.61(8) . . ?
C13 O1 C18 117.18(16) . . ?
C14 O2 C17 105.06(17) . . ?
C15 O3 C17 105.64(17) . . ?
C11 N1 C7 113.12(15) . . ?
C11 N1 C12 113.32(16) . . ?
C12 N1 C7 112.33(16) . . ?
C9 C10 C11 120.91(15) . . ?
C9 C10 C13 120.73(16) . . ?
C13 C10 C11 118.36(15) . . ?
C10 C9 C16 120.49(17) . . ?
C10 C9 C8 120.06(17) . . ?
C16 C9 C8 119.38(17) . . ?
S1 C11 H11 108.0 . . ?
N1 C11 S1 114.81(12) . . ?
N1 C11 C10 112.33(15) . . ?
N1 C11 H11 108.0 . . ?
C10 C11 S1 105.52(11) . . ?
C10 C11 H11 108.0 . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.93(16) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O3 C15 C14 109.67(18) . . ?
C16 C15 O3 127.61(19) . . ?
C16 C15 C14 122.62(18) . . ?
C1 C6 S1 121.35(15) . . ?
C1 C6 C5 118.54(19) . . ?
C5 C6 S1 120.11(17) . . ?
O1 C13 C10 118.14(16) . . ?
O1 C13 C14 124.18(16) . . ?
C14 C13 C10 117.51(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C6 C1 C2 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C9 C16 H16 121.4 . . ?
C15 C16 C9 117.30(18) . . ?
C15 C16 H16 121.4 . . ?
C15 C14 O2 110.19(17) . . ?
C13 C14 O2 128.36(18) . . ?
C13 C14 C15 121.33(17) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 C9 112.73(16) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
O2 C17 H17A 109.8 . . ?
O2 C17 H17B 109.8 . . ?
O3 C17 O2 109.25(17) . . ?
O3 C17 H17A 109.8 . . ?
O3 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?

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 C6 C1 C2 178.58(16) . . . . ?
S1 C6 C5 C4 -179.35(18) . . . . ?
O1 C13 C14 O2 1.0(3) . . . . ?
O1 C13 C14 C15 -174.59(17) . . . . ?
O3 C15 C16 C9 -176.14(19) . . . . ?
O3 C15 C14 O2 0.7(2) . . . . ?
O3 C15 C14 C13 177.02(18) . . . . ?
N1 C7 C8 C9 46.1(2) . . . . ?
C10 C9 C16 C15 -1.0(3) . . . . ?
C10 C9 C8 C7 -18.2(3) . . . . ?
C10 C13 C14 O2 176.21(18) . . . . ?
C10 C13 C14 C15 0.6(3) . . . . ?
C9 C10 C11 S1 105.58(16) . . . . ?
C9 C10 C11 N1 -20.2(2) . . . . ?
C9 C10 C13 O1 173.60(15) . . . . ?
C9 C10 C13 C14 -1.9(3) . . . . ?
C11 S1 C6 C1 -56.36(17) . . . . ?
C11 S1 C6 C5 123.91(17) . . . . ?
C11 N1 C7 C8 -64.9(2) . . . . ?
C11 C10 C9 C16 -178.11(16) . . . . ?
C11 C10 C9 C8 4.9(3) . . . . ?
C11 C10 C13 O1 -6.2(2) . . . . ?
C11 C10 C13 C14 178.37(16) . . . . ?
C7 N1 C11 S1 -70.20(18) . . . . ?
C7 N1 C11 C10 50.4(2) . . . . ?
C15 O3 C17 O2 -4.1(3) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C13 C10 C9 C16 2.1(3) . . . . ?
C13 C10 C9 C8 -174.83(17) . . . . ?
C13 C10 C11 S1 -74.67(16) . . . . ?
C13 C10 C11 N1 159.54(15) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C1 C6 C5 C4 0.9(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C16 C9 C8 C7 164.78(18) . . . . ?
C16 C15 C14 O2 -175.86(19) . . . . ?
C16 C15 C14 C13 0.5(3) . . . . ?
C14 O2 C17 O3 4.5(2) . . . . ?
C14 C15 C16 C9 -0.3(3) . . . . ?
C8 C9 C16 C15 175.94(18) . . . . ?
C12 N1 C11 S1 59.13(19) . . . . ?
C12 N1 C11 C10 179.70(16) . . . . ?
C12 N1 C7 C8 165.25(18) . . . . ?
C18 O1 C13 C10 132.96(19) . . . . ?
C18 O1 C13 C14 -51.9(3) . . . . ?
C5 C6 C1 C2 -1.7(3) . . . . ?
C3 C2 C1 C6 1.3(3) . . . . ?
C17 O2 C14 C15 -3.2(2) . . . . ?
C17 O2 C14 C13 -179.2(2) . . . . ?
C17 O3 C15 C16 178.4(2) . . . . ?
C17 O3 C15 C14 2.1(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
