# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_5S_PhCl
_database_code_depnum_ccdc_archive 'CCDC 2375469'
loop_
_audit_author_name
_audit_author_address
'Dr. Indrajit Karmakar'
;National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2025-08-29 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H13 Cl O3 S2'
_chemical_formula_sum            'C15 H13 Cl O3 S2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         340.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.2579(12)
_cell_length_b                   12.7858(7)
_cell_length_c                   11.3836(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.9390(16)
_cell_angle_gamma                90
_cell_volume                     3115.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.807
_cell_measurement_theta_max      27.856
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.519
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68816
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         27.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3722
_reflns_number_gt                3217
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0413P)²+4.1947P] 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         3722
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_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
Cl Cl 0.05372(2) 0.45236(3) 0.63384(4) 0.04248(13) Uani 1 1 d . . . . .
S1 S 0.17605(2) -0.21901(3) 0.89045(4) 0.03134(11) Uani 1 1 d . . . . .
S2 S 0.19380(2) 0.02895(3) 0.78479(3) 0.02472(10) Uani 1 1 d . . . . .
O1 O 0.05404(5) 0.12364(9) 1.01418(12) 0.0351(3) Uani 1 1 d . . . . .
O2 O 0.14583(5) 0.19840(9) 1.02022(10) 0.0290(2) Uani 1 1 d . . . . .
O3 O 0.25921(6) 0.04611(10) 0.77846(12) 0.0381(3) Uani 1 1 d . . . . .
C1 C 0.14491(9) -0.34136(13) 0.86005(15) 0.0342(4) Uani 1 1 d . . . . .
H1A H 0.167389 -0.400222 0.843701 0.041 Uiso 1 1 calc R U . . .
C2 C 0.08438(8) -0.34453(13) 0.86202(15) 0.0340(4) Uani 1 1 d . . . . .
H2A H 0.059464 -0.405995 0.846847 0.041 Uiso 1 1 calc R U . . .
C3 C 0.06247(8) -0.24654(13) 0.88907(14) 0.0296(3) Uani 1 1 d . . . . .
H3B H 0.021046 -0.235322 0.894041 0.036 Uiso 1 1 calc R U . . .
C4 C 0.10665(7) -0.16876(12) 0.90757(13) 0.0241(3) Uani 1 1 d . . . . .
C5 C 0.09607(7) -0.06363(12) 0.94280(12) 0.0229(3) Uani 1 1 d . . . . .
H5A H 0.055373 -0.051763 0.951494 0.028 Uiso 1 1 calc R U . . .
C6 C 0.13368(7) 0.02088(11) 0.96561(12) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.10620(7) 0.11749(12) 1.00232(13) 0.0240(3) Uani 1 1 d . . . . .
C8 C 0.12075(8) 0.29774(14) 1.04485(17) 0.0367(4) Uani 1 1 d . . . . .
H8A H 0.153228 0.351536 1.056534 0.055 Uiso 1 1 calc R U . . .
H8B H 0.085337 0.316996 0.975742 0.055 Uiso 1 1 calc R U . . .
H8C H 0.106698 0.292045 1.118989 0.055 Uiso 1 1 calc R U . . .
C9 C 0.19800(7) 0.02528(12) 0.94877(13) 0.0244(3) Uani 1 1 d . . . . .
H9A H 0.222099 -0.036883 0.986938 0.029 Uiso 1 1 calc R U . . .
H9B H 0.219895 0.088406 0.989547 0.029 Uiso 1 1 calc R U . . .
C10 C 0.15428(7) 0.15093(11) 0.74892(13) 0.0225(3) Uani 1 1 d . . . . .
C11 C 0.08960(7) 0.15147(12) 0.70874(13) 0.0246(3) Uani 1 1 d . . . . .
H11A H 0.066790 0.088046 0.703634 0.030 Uiso 1 1 calc R U . . .
C12 C 0.05866(7) 0.24512(13) 0.67621(13) 0.0279(3) Uani 1 1 d . . . . .
H12A H 0.014304 0.247127 0.649885 0.033 Uiso 1 1 calc R U . . .
C13 C 0.09308(8) 0.33597(12) 0.68246(13) 0.0270(3) Uani 1 1 d . . . . .
C14 C 0.15765(8) 0.33643(12) 0.72121(15) 0.0308(3) Uani 1 1 d . . . . .
H14A H 0.180383 0.399768 0.724634 0.037 Uiso 1 1 calc R U . . .
C15 C 0.18845(7) 0.24219(12) 0.75496(15) 0.0285(3) Uani 1 1 d . . . . .
H15A H 0.232789 0.240303 0.782090 0.034 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
Cl C13 1.7384(16) . ?
S1 C1 1.7074(18) . ?
S1 C4 1.7327(15) . ?
S2 O3 1.4935(12) . ?
S2 C10 1.7820(15) . ?
S2 C9 1.8438(15) . ?
O1 C7 1.2077(18) . ?
O2 C7 1.3384(19) . ?
O2 C8 1.4455(19) . ?
C1 C2 1.354(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.409(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.373(2) . ?
C3 H3B 0.9500 . ?
C4 C5 1.441(2) . ?
C5 C6 1.348(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.488(2) . ?
C6 C9 1.4969(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.384(2) . ?
C10 C11 1.386(2) . ?
C11 C12 1.380(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(2) . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 H15A 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 C4 92.16(8) . . ?
O3 S2 C10 106.67(7) . . ?
O3 S2 C9 105.87(7) . . ?
C10 S2 C9 97.98(7) . . ?
C7 O2 C8 115.80(12) . . ?
C2 C1 S1 111.99(13) . . ?
C2 C1 H1A 124.0 . . ?
S1 C1 H1A 124.0 . . ?
C1 C2 C3 112.50(15) . . ?
C1 C2 H2A 123.7 . . ?
C3 C2 H2A 123.7 . . ?
C4 C3 C2 113.65(14) . . ?
C4 C3 H3B 123.2 . . ?
C2 C3 H3B 123.2 . . ?
C3 C4 C5 123.60(14) . . ?
C3 C4 S1 109.70(12) . . ?
C5 C4 S1 126.60(11) . . ?
C6 C5 C4 131.41(13) . . ?
C6 C5 H5A 114.3 . . ?
C4 C5 H5A 114.3 . . ?
C5 C6 C7 115.98(13) . . ?
C5 C6 C9 124.81(13) . . ?
C7 C6 C9 119.08(13) . . ?
O1 C7 O2 123.12(14) . . ?
O1 C7 C6 124.56(14) . . ?
O2 C7 C6 112.32(12) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 S2 110.26(10) . . ?
C6 C9 H9A 109.6 . . ?
S2 C9 H9A 109.6 . . ?
C6 C9 H9B 109.6 . . ?
S2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C15 C10 C11 121.27(14) . . ?
C15 C10 S2 119.76(11) . . ?
C11 C10 S2 118.87(11) . . ?
C12 C11 C10 119.31(14) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C13 119.10(14) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C14 C13 C12 122.20(14) . . ?
C14 C13 Cl 119.12(12) . . ?
C12 C13 Cl 118.63(12) . . ?
C13 C14 C15 118.42(14) . . ?
C13 C14 H14A 120.8 . . ?
C15 C14 H14A 120.8 . . ?
C10 C15 C14 119.70(14) . . ?
C10 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?

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
C4 S1 C1 C2 0.30(13) . . . . ?
S1 C1 C2 C3 -0.25(19) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -176.54(14) . . . . ?
C2 C3 C4 S1 0.16(17) . . . . ?
C1 S1 C4 C3 -0.26(12) . . . . ?
C1 S1 C4 C5 176.32(13) . . . . ?
C3 C4 C5 C6 179.30(15) . . . . ?
S1 C4 C5 C6 3.2(2) . . . . ?
C4 C5 C6 C7 -179.02(14) . . . . ?
C4 C5 C6 C9 5.1(2) . . . . ?
C8 O2 C7 O1 -5.1(2) . . . . ?
C8 O2 C7 C6 174.37(12) . . . . ?
C5 C6 C7 O1 1.1(2) . . . . ?
C9 C6 C7 O1 177.25(14) . . . . ?
C5 C6 C7 O2 -178.38(12) . . . . ?
C9 C6 C7 O2 -2.27(18) . . . . ?
C5 C6 C9 S2 72.75(16) . . . . ?
C7 C6 C9 S2 -103.00(13) . . . . ?
O3 S2 C9 C6 173.39(10) . . . . ?
C10 S2 C9 C6 63.46(11) . . . . ?
O3 S2 C10 C15 -17.43(14) . . . . ?
C9 S2 C10 C15 91.86(13) . . . . ?
O3 S2 C10 C11 158.96(12) . . . . ?
C9 S2 C10 C11 -91.75(12) . . . . ?
C15 C10 C11 C12 -1.2(2) . . . . ?
S2 C10 C11 C12 -177.51(11) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C11 C12 C13 Cl 176.76(11) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
Cl C13 C14 C15 -177.40(12) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
S2 C10 C15 C14 176.82(12) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.049

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   C2/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

