# 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_257_200924_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2l68bf
_database_code_depnum_ccdc_archive 'CCDC 2389304'
loop_
_audit_author_name
_audit_author_address
'BALLANKI TRINADH'
;NATIONAL Institute of TECHNOLOGY, TRICHY
India
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 O3 S'
_chemical_formula_sum            'C19 H20 O3 S'
_chemical_formula_weight         328.41

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'
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                   5.2763(4)
_cell_length_b                   22.1253(17)
_cell_length_c                   14.7638(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.053(2)
_cell_angle_gamma                90
_cell_volume                     1716.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'i-mu-s microfocus source'
_diffrn_measurement_device_type  
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40667
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4259
_reflns_number_gt                2778
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0498P)²+0.8540P] 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         4259
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.62052(11) 0.51575(3) 0.37753(4) 0.05323(18) Uani 1 1 d . . . . .
O1 O 0.8633(4) 0.43340(9) 0.22654(14) 0.0840(6) Uani 1 1 d . . . . .
O2 O 0.3426(3) 0.52748(8) 0.37935(11) 0.0657(5) Uani 1 1 d . . . . .
O3 O 0.5646(4) 0.41517(10) 0.11492(15) 0.1065(8) Uani 1 1 d . . . . .
C1 C 0.6699(4) 0.63279(10) 0.44667(15) 0.0549(5) Uani 1 1 d . . . . .
C2 C 0.4669(5) 0.64532(12) 0.49679(18) 0.0669(7) Uani 1 1 d . . . . .
H2 H 0.406678 0.615070 0.533025 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3514(6) 0.70087(15) 0.4949(3) 0.0908(10) Uani 1 1 d . . . . .
H3 H 0.216148 0.707968 0.529790 0.109 Uiso 1 1 calc R U . . .
C4 C 0.4336(8) 0.74478(16) 0.4426(3) 0.1061(13) Uani 1 1 d . . . . .
H4 H 0.355206 0.782444 0.441818 0.127 Uiso 1 1 calc R U . . .
C5 C 0.6319(9) 0.73515(16) 0.3903(3) 0.1083(14) Uani 1 1 d . . . . .
H5 H 0.686185 0.765832 0.353511 0.130 Uiso 1 1 calc R U . . .
C6 C 0.7533(6) 0.67789(14) 0.39278(19) 0.0828(9) Uani 1 1 d . . . . .
H6 H 0.888962 0.670924 0.358002 0.099 Uiso 1 1 calc R U . . .
C7 C 0.7901(4) 0.57138(11) 0.45163(15) 0.0580(6) Uani 1 1 d . . . . .
H7A H 0.797192 0.557060 0.513898 0.070 Uiso 1 1 calc R U . . .
H7B H 0.963447 0.574704 0.435120 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7133(4) 0.54371(10) 0.26928(14) 0.0529(5) Uani 1 1 d . . . . .
H8A H 0.677704 0.586652 0.264232 0.064 Uiso 1 1 calc R U . . .
H8B H 0.894717 0.537944 0.266507 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5711(4) 0.51099(11) 0.19212(15) 0.0564(5) Uani 1 1 d . . . . .
C10 C 0.6611(5) 0.44886(12) 0.17208(17) 0.0680(7) Uani 1 1 d . . . . .
C11 C 0.9702(7) 0.37382(15) 0.2161(2) 0.1021(11) Uani 1 1 d . . . . .
H11A H 1.055913 0.371916 0.160666 0.122 Uiso 1 1 calc R U . . .
H11B H 0.836390 0.343621 0.212595 0.122 Uiso 1 1 calc R U . . .
C12 C 1.1501(8) 0.36249(16) 0.2946(3) 0.1122(12) Uani 1 1 d . . . . .
H12A H 1.235663 0.324819 0.286654 0.168 Uiso 1 1 calc R U . . .
H12B H 1.060695 0.360578 0.348404 0.168 Uiso 1 1 calc R U . . .
H12C H 1.272812 0.394606 0.300562 0.168 Uiso 1 1 calc R U . . .
C13 C 0.3699(5) 0.53067(12) 0.13927(16) 0.0635(6) Uani 1 1 d . . . . .
H13 H 0.309426 0.502511 0.095858 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2238(4) 0.58696(11) 0.13479(16) 0.0595(6) Uani 1 1 d . . . . .
C15 C 0.2538(6) 0.63560(14) 0.1942(2) 0.0861(9) Uani 1 1 d . . . . .
H15 H 0.377043 0.633791 0.243250 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1043(6) 0.68645(14) 0.1818(2) 0.0870(9) Uani 1 1 d . . . . .
H16 H 0.132468 0.719064 0.221184 0.104 Uiso 1 1 calc R U . . .
C17 C -0.0842(6) 0.68968(14) 0.1129(2) 0.0811(8) Uani 1 1 d . . . . .
H17 H -0.183398 0.724314 0.104589 0.097 Uiso 1 1 calc R U . . .
C18 C -0.1254(7) 0.64148(15) 0.0562(2) 0.0942(10) Uani 1 1 d . . . . .
H18 H -0.257405 0.642559 0.010120 0.113 Uiso 1 1 calc R U . . .
C19 C 0.0273(6) 0.59131(13) 0.06675(18) 0.0773(8) Uani 1 1 d . . . . .
H19 H -0.002562 0.559112 0.026742 0.093 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 O2 1.4918(16) . ?
S1 C8 1.821(2) . ?
S1 C7 1.827(2) . ?
O1 C10 1.323(3) . ?
O1 C11 1.447(3) . ?
O3 C10 1.205(3) . ?
C1 C6 1.372(4) . ?
C1 C2 1.383(3) . ?
C1 C7 1.498(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.336(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.495(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.334(3) . ?
C9 C10 1.492(4) . ?
C11 C12 1.454(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.463(3) . ?
C13 H13 0.9300 . ?
C14 C19 1.382(3) . ?
C14 C15 1.389(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(4) . ?
C18 H18 0.9300 . ?
C19 H19 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
O2 S1 C8 107.31(10) . . ?
O2 S1 C7 107.59(10) . . ?
C8 S1 C7 98.12(11) . . ?
C10 O1 C11 118.1(2) . . ?
C6 C1 C2 117.9(3) . . ?
C6 C1 C7 122.1(2) . . ?
C2 C1 C7 120.0(2) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C1 C7 S1 113.50(15) . . ?
C1 C7 H7A 108.9 . . ?
S1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
S1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 S1 110.40(15) . . ?
C9 C8 H8A 109.6 . . ?
S1 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
S1 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C13 C9 C10 115.8(2) . . ?
C13 C9 C8 127.4(2) . . ?
C10 C9 C8 116.7(2) . . ?
O3 C10 O1 122.3(3) . . ?
O3 C10 C9 125.9(3) . . ?
O1 C10 C9 111.8(2) . . ?
O1 C11 C12 107.8(3) . . ?
O1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 133.9(2) . . ?
C9 C13 H13 113.1 . . ?
C14 C13 H13 113.1 . . ?
C19 C14 C15 116.2(2) . . ?
C19 C14 C13 116.8(2) . . ?
C15 C14 C13 126.9(2) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 122.3(3) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?

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
C6 C1 C2 C3 -0.8(4) . . . . ?
C7 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C7 C1 C6 C5 179.7(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C6 C1 C7 S1 -97.1(2) . . . . ?
C2 C1 C7 S1 82.4(2) . . . . ?
O2 S1 C7 C1 -37.9(2) . . . . ?
C8 S1 C7 C1 73.23(18) . . . . ?
O2 S1 C8 C9 -60.98(19) . . . . ?
C7 S1 C8 C9 -172.35(17) . . . . ?
S1 C8 C9 C13 101.7(3) . . . . ?
S1 C8 C9 C10 -77.5(2) . . . . ?
C11 O1 C10 O3 0.1(4) . . . . ?
C11 O1 C10 C9 179.1(3) . . . . ?
C13 C9 C10 O3 -2.1(4) . . . . ?
C8 C9 C10 O3 177.2(3) . . . . ?
C13 C9 C10 O1 179.0(2) . . . . ?
C8 C9 C10 O1 -1.8(3) . . . . ?
C10 O1 C11 C12 -167.6(3) . . . . ?
C10 C9 C13 C14 -179.7(3) . . . . ?
C8 C9 C13 C14 1.1(5) . . . . ?
C9 C13 C14 C19 177.9(3) . . . . ?
C9 C13 C14 C15 -5.3(5) . . . . ?
C19 C14 C15 C16 -3.7(4) . . . . ?
C13 C14 C15 C16 179.4(3) . . . . ?
C14 C15 C16 C17 2.5(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -2.3(5) . . . . ?
C17 C18 C19 C14 0.9(5) . . . . ?
C15 C14 C19 C18 2.0(4) . . . . ?
C13 C14 C19 C18 179.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7A O2 0.97 2.59 3.436(3) 145.0 3_666 yes
C7 H7B O2 0.97 2.46 3.336(3) 150.0 1_655 yes

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045

