# 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_AS1
_database_code_depnum_ccdc_archive 'CCDC 2302174'
loop_
_audit_author_name
_audit_author_address
'Debabrata Patra'
;Jadavpur University
India
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 N O2 S'
_chemical_formula_weight         331.37

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.8169(5)
_cell_length_b                   8.3525(6)
_cell_length_c                   12.4587(8)
_cell_angle_alpha                81.958(2)
_cell_angle_beta                 82.535(2)
_cell_angle_gamma                78.805(2)
_cell_volume                     785.68(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24491
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.503
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3566
_reflns_number_gt                2737
_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       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0854P)²+0.2124P] 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         3566
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.003
_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 0.67945(8) 0.71725(9) 0.65765(5) 0.0468(2) Uani 1 1 d . . . . .
O1 O 0.4370(2) 0.8077(2) 0.34082(14) 0.0465(5) Uani 1 1 d . . . . .
O2 O 0.4357(3) 0.8867(3) 0.16419(16) 0.0614(6) Uani 1 1 d . . . . .
N1 N 0.6549(3) 0.8420(3) 0.44310(17) 0.0448(5) Uani 1 1 d . . . . .
C1 C 0.7860(4) 0.4514(4) 0.9925(2) 0.0583(8) Uani 1 1 d . . . . .
H1 H 0.813916 0.398383 1.060399 0.070 Uiso 1 1 calc R U . . .
C2 C 0.7176(4) 0.6152(4) 0.9808(2) 0.0628(8) Uani 1 1 d . . . . .
H2 H 0.695964 0.672871 1.041230 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6803(4) 0.6954(4) 0.8804(2) 0.0536(7) Uani 1 1 d . . . . .
H3 H 0.634593 0.807301 0.873192 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7103(3) 0.6109(3) 0.7899(2) 0.0404(6) Uani 1 1 d . . . . .
C16 C 0.4782(3) 0.6680(3) 0.6320(2) 0.0385(6) Uani 1 1 d . . . . .
C11 C 0.4157(3) 0.7091(3) 0.5284(2) 0.0382(5) Uani 1 1 d . . . . .
C7 C 0.5139(3) 0.7920(3) 0.4360(2) 0.0399(6) Uani 1 1 d . . . . .
C8 C 0.7433(3) 0.9102(3) 0.3493(2) 0.0444(6) Uani 1 1 d . . . . .
C9 C 0.6770(4) 0.9289(3) 0.2483(2) 0.0441(6) Uani 1 1 d . . . . .
C20 C 0.7698(4) 0.9976(4) 0.1549(2) 0.0561(7) Uani 1 1 d . . . . .
H20 H 0.725495 1.011336 0.087826 0.067 Uiso 1 1 calc R U . . .
C19 C 0.9252(4) 1.0445(4) 0.1626(3) 0.0612(8) Uani 1 1 d . . . . .
H19 H 0.987021 1.089326 0.100490 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2576(3) 0.6644(3) 0.5132(2) 0.0482(7) Uani 1 1 d . . . . .
H12 H 0.216273 0.690213 0.445032 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1624(3) 0.5838(4) 0.5959(2) 0.0527(7) Uani 1 1 d . . . . .
H13 H 0.057555 0.555789 0.583871 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2225(4) 0.5442(4) 0.6973(2) 0.0530(7) Uani 1 1 d . . . . .
H14 H 0.158243 0.489459 0.753850 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3776(3) 0.5859(3) 0.7143(2) 0.0487(7) Uani 1 1 d . . . . .
H15 H 0.416753 0.558425 0.783042 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5125(4) 0.8768(3) 0.2432(2) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.9912(4) 1.0255(4) 0.2625(3) 0.0615(8) Uani 1 1 d . . . . .
H18 H 1.096972 1.058223 0.266863 0.074 Uiso 1 1 calc R U . . .
C17 C 0.9023(4) 0.9589(4) 0.3550(3) 0.0555(7) Uani 1 1 d . . . . .
H17 H 0.948178 0.946298 0.421588 0.067 Uiso 1 1 calc R U . . .
C5 C 0.7782(4) 0.4448(3) 0.8031(2) 0.0521(7) Uani 1 1 d . . . . .
H5 H 0.800232 0.386401 0.742950 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8137(4) 0.3650(4) 0.9041(3) 0.0589(8) Uani 1 1 d . . . . .
H6 H 0.856471 0.252497 0.912460 0.071 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 C16 1.779(2) . ?
S1 C4 1.781(3) . ?
O1 C7 1.376(3) . ?
O1 C10 1.381(3) . ?
O2 C10 1.203(3) . ?
N1 C7 1.269(3) . ?
N1 C8 1.388(3) . ?
C1 C2 1.363(4) . ?
C1 C6 1.372(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C16 C15 1.395(4) . ?
C16 C11 1.413(4) . ?
C11 C12 1.401(3) . ?
C11 C7 1.466(4) . ?
C8 C17 1.394(4) . ?
C8 C9 1.399(4) . ?
C9 C20 1.402(4) . ?
C9 C10 1.447(4) . ?
C20 C19 1.365(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.386(4) . ?
C19 H19 0.9300 . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C18 C17 1.373(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 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
C16 S1 C4 102.59(11) . . ?
C7 O1 C10 121.6(2) . . ?
C7 N1 C8 119.0(2) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 S1 120.6(2) . . ?
C3 C4 S1 120.7(2) . . ?
C15 C16 C11 117.9(2) . . ?
C15 C16 S1 120.46(19) . . ?
C11 C16 S1 121.60(19) . . ?
C12 C11 C16 118.7(2) . . ?
C12 C11 C7 119.3(2) . . ?
C16 C11 C7 122.0(2) . . ?
N1 C7 O1 124.0(2) . . ?
N1 C7 C11 123.6(2) . . ?
O1 C7 C11 112.4(2) . . ?
N1 C8 C17 119.6(3) . . ?
N1 C8 C9 121.1(2) . . ?
C17 C8 C9 119.2(3) . . ?
C8 C9 C20 119.8(3) . . ?
C8 C9 C10 118.7(2) . . ?
C20 C9 C10 121.5(3) . . ?
C19 C20 C9 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C9 C20 H20 120.0 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 122.1(3) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
O2 C10 O1 117.2(3) . . ?
O2 C10 C9 127.4(3) . . ?
O1 C10 C9 115.4(2) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C17 C8 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C8 C17 H17 120.0 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?

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 -1.7(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 S1 -174.8(2) . . . . ?
C16 S1 C4 C5 80.7(2) . . . . ?
C16 S1 C4 C3 -104.7(2) . . . . ?
C4 S1 C16 C15 8.5(2) . . . . ?
C4 S1 C16 C11 -171.1(2) . . . . ?
C15 C16 C11 C12 -0.6(4) . . . . ?
S1 C16 C11 C12 179.00(18) . . . . ?
C15 C16 C11 C7 -178.6(2) . . . . ?
S1 C16 C11 C7 1.0(3) . . . . ?
C8 N1 C7 O1 -3.1(4) . . . . ?
C8 N1 C7 C11 176.2(2) . . . . ?
C10 O1 C7 N1 1.9(4) . . . . ?
C10 O1 C7 C11 -177.5(2) . . . . ?
C12 C11 C7 N1 177.5(2) . . . . ?
C16 C11 C7 N1 -4.6(4) . . . . ?
C12 C11 C7 O1 -3.2(3) . . . . ?
C16 C11 C7 O1 174.8(2) . . . . ?
C7 N1 C8 C17 -177.2(2) . . . . ?
C7 N1 C8 C9 1.9(4) . . . . ?
N1 C8 C9 C20 -179.8(2) . . . . ?
C17 C8 C9 C20 -0.7(4) . . . . ?
N1 C8 C9 C10 0.5(4) . . . . ?
C17 C8 C9 C10 179.6(2) . . . . ?
C8 C9 C20 C19 0.7(4) . . . . ?
C10 C9 C20 C19 -179.6(3) . . . . ?
C9 C20 C19 C18 -0.5(5) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C7 C11 C12 C13 178.6(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C11 C16 C15 C14 0.3(4) . . . . ?
S1 C16 C15 C14 -179.3(2) . . . . ?
C7 O1 C10 O2 -179.5(2) . . . . ?
C7 O1 C10 C9 0.6(3) . . . . ?
C8 C9 C10 O2 178.5(3) . . . . ?
C20 C9 C10 O2 -1.2(4) . . . . ?
C8 C9 C10 O1 -1.7(3) . . . . ?
C20 C9 C10 O1 178.6(2) . . . . ?
C20 C19 C18 C17 0.3(5) . . . . ?
C19 C18 C17 C8 -0.3(5) . . . . ?
N1 C8 C17 C18 179.6(3) . . . . ?
C9 C8 C17 C18 0.5(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
S1 C4 C5 C6 175.4(2) . . . . ?
C2 C1 C6 C5 2.3(5) . . . . ?
C4 C5 C6 C1 -1.8(5) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.053

