# 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_p3149
_database_code_depnum_ccdc_archive 'CCDC 2370262'
loop_
_audit_author_name
_audit_author_address
'SURAJIT DUARI'
;Calcutta University
India
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.4993(14)
_cell_length_b                   15.165(4)
_cell_length_c                   19.844(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.395(10)
_cell_angle_gamma                90
_cell_volume                     1345.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6115
_cell_measurement_temperature    189.68
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15607
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.073
_diffrn_reflns_theta_min         2.464
_diffrn_ambient_temperature      189.68
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_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_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2428
_reflns_number_total             2926
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.012(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.058
_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)+(0.0300P)²+0.5124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1009
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.39379(12) 0.44995(3) 0.32569(2) 0.05279(19) Uani 1 1 d . . . . .
O1 O 0.5669(3) 0.28861(8) 0.29965(7) 0.0632(4) Uani 1 1 d . . . . .
O2 O 1.1454(3) 0.29226(10) 0.60614(7) 0.0680(4) Uani 1 1 d . . . . .
O3 O 0.3096(3) 0.60876(8) 0.21581(6) 0.0560(3) Uani 1 1 d . . . . .
H3 H 0.347404 0.660619 0.204556 0.084 Uiso 1 1 calc R U . . .
C1 C 0.5725(4) 0.34754(10) 0.34314(8) 0.0452(4) Uani 1 1 d . . . . .
C2 C 0.7265(4) 0.33831(10) 0.41257(8) 0.0431(4) Uani 1 1 d . . . . .
C3 C 0.9243(4) 0.26877(12) 0.42716(9) 0.0526(4) Uani 1 1 d . . . . .
H3A H 0.964738 0.229647 0.391914 0.063 Uiso 1 1 calc R U . . .
C4 C 1.0621(4) 0.25564(13) 0.49145(10) 0.0590(5) Uani 1 1 d . . . . .
H4 H 1.197863 0.207959 0.500234 0.071 Uiso 1 1 calc R U . . .
C5 C 1.0047(4) 0.31160(11) 0.54395(9) 0.0490(4) Uani 1 1 d . . . . .
C6 C 0.8084(5) 0.38074(13) 0.53032(10) 0.0677(6) Uani 1 1 d . . . . .
H6 H 0.765967 0.419398 0.565689 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6741(5) 0.39358(13) 0.46536(10) 0.0685(6) Uani 1 1 d . . . . .
H7 H 0.541161 0.441923 0.456493 0.082 Uiso 1 1 calc R U . . .
C8 C 1.0529(6) 0.33679(16) 0.66342(10) 0.0728(6) Uani 1 1 d . . . . .
H8A H 0.835586 0.331525 0.662914 0.109 Uiso 1 1 calc R U . . .
H8B H 1.107801 0.399220 0.661705 0.109 Uiso 1 1 calc R U . . .
H8C H 1.151659 0.310274 0.705070 0.109 Uiso 1 1 calc R U . . .
C9 C 0.2065(4) 0.43297(11) 0.24053(9) 0.0507(4) Uani 1 1 d . . . . .
H9A H 0.157416 0.369607 0.234561 0.061 Uiso 1 1 calc R U . . .
H9B H 0.015883 0.466200 0.235811 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3884(4) 0.46125(10) 0.18530(8) 0.0422(4) Uani 1 1 d . . . . .
C11 C 0.4312(4) 0.55087(11) 0.17389(8) 0.0432(4) Uani 1 1 d . . . . .
C12 C 0.5901(4) 0.57855(13) 0.12168(9) 0.0546(5) Uani 1 1 d . . . . .
H12 H 0.617084 0.639698 0.113944 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7083(5) 0.51714(16) 0.08119(10) 0.0656(5) Uani 1 1 d . . . . .
H13 H 0.818392 0.536148 0.045693 0.079 Uiso 1 1 calc R U . . .
C14 C 0.6684(5) 0.42803(16) 0.09167(10) 0.0672(6) Uani 1 1 d . . . . .
H14 H 0.749786 0.385833 0.063465 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5091(4) 0.40097(12) 0.14355(10) 0.0550(5) Uani 1 1 d . . . . .
H15 H 0.481800 0.339707 0.150750 0.066 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 C1 1.7654(17) . ?
S1 C9 1.8208(19) . ?
O1 C1 1.241(2) . ?
O2 C5 1.355(2) . ?
O2 C8 1.424(2) . ?
O3 H3 0.8400 . ?
O3 C11 1.365(2) . ?
C1 C2 1.478(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.382(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.378(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.502(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.385(2) . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?

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
C1 S1 C9 102.20(8) . . ?
C5 O2 C8 118.43(15) . . ?
C11 O3 H3 109.5 . . ?
O1 C1 S1 121.58(13) . . ?
O1 C1 C2 123.46(15) . . ?
C2 C1 S1 114.96(12) . . ?
C3 C2 C1 119.27(15) . . ?
C7 C2 C1 123.17(15) . . ?
C7 C2 C3 117.50(16) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 C2 121.16(16) . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.45(16) . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C4 116.33(15) . . ?
O2 C5 C6 124.58(16) . . ?
C6 C5 C4 119.08(17) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.78(17) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.0 . . ?
C6 C7 C2 122.02(17) . . ?
C6 C7 H7 119.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S1 C9 H9A 108.8 . . ?
S1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 S1 113.79(12) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 119.56(15) . . ?
C15 C10 C9 122.02(16) . . ?
C15 C10 C11 118.39(16) . . ?
O3 C11 C10 117.11(15) . . ?
O3 C11 C12 122.35(15) . . ?
C12 C11 C10 120.54(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(18) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.61(19) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.32(19) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.38(18) . . ?
C14 C15 H15 119.3 . . ?

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 C1 C2 C3 -166.63(14) . . . . ?
S1 C1 C2 C7 16.3(2) . . . . ?
S1 C9 C10 C11 -72.14(18) . . . . ?
S1 C9 C10 C15 109.81(16) . . . . ?
O1 C1 C2 C3 13.3(3) . . . . ?
O1 C1 C2 C7 -163.7(2) . . . . ?
O2 C5 C6 C7 -179.0(2) . . . . ?
O3 C11 C12 C13 179.79(17) . . . . ?
C1 S1 C9 C10 -92.30(14) . . . . ?
C1 C2 C3 C4 -177.24(18) . . . . ?
C1 C2 C7 C6 176.5(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 O2 178.42(18) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C8 O2 C5 C4 -168.41(19) . . . . ?
C8 O2 C5 C6 10.2(3) . . . . ?
C9 S1 C1 O1 4.91(17) . . . . ?
C9 S1 C1 C2 -175.15(13) . . . . ?
C9 C10 C11 O3 1.9(2) . . . . ?
C9 C10 C11 C12 -177.85(15) . . . . ?
C9 C10 C15 C14 178.04(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C15 C10 C11 O3 179.99(14) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
