# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_SA84
_database_code_depnum_ccdc_archive 'CCDC 2152756'
loop_
_audit_author_name
_audit_author_address
'Prof. Dilip K. Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2023-02-14 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         'C13 H11 N O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.107(4)
_cell_length_b                   24.81(2)
_cell_length_c                   9.865(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.955(17)
_cell_angle_gamma                90
_cell_volume                     1248.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    18299
_cell_measurement_theta_min      1.642
_cell_measurement_theta_max      24.995

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18299
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_av_R_equivalents  0.1588
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.642
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4346
_reflns_number_gt                2053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1052P)²+0.1091P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(14)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4346
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2395
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.2595(8) 0.39328(18) 0.0795(4) 0.0748(14) Uani 1 1 d . . . . .
S2 S -0.2192(9) 0.6094(2) 0.1567(4) 0.0796(15) Uani 1 1 d . . . . .
O1 O 0.9758(19) 0.4068(4) 0.7081(9) 0.061(3) Uani 1 1 d . . . . .
O2 O 0.6034(18) 0.4766(4) 0.6302(9) 0.057(3) Uani 1 1 d . . . . .
H2 H 0.759610 0.484075 0.640729 0.085 Uiso 1 1 calc R U . . .
O3 O 0.1865(17) 0.4048(5) 0.3796(9) 0.069(3) Uani 1 1 d . . . . .
O4 O 0.103(2) 0.5277(4) 0.7007(11) 0.066(3) Uani 1 1 d . . . . .
H4 H 0.254559 0.517088 0.710026 0.099 Uiso 1 1 calc R U . . .
O5 O 0.5017(19) 0.5914(4) 0.7918(9) 0.064(3) Uani 1 1 d . . . . .
O6 O -0.2964(18) 0.6032(4) 0.4604(9) 0.065(3) Uani 1 1 d . . . . .
C1 C 0.431(3) 0.4184(7) -0.0457(15) 0.073(5) Uani 1 1 d . . . . .
H1 H 0.383882 0.413404 -0.137117 0.088 Uiso 1 1 calc R U . . .
C2 C 0.469(3) 0.4201(5) 0.1972(12) 0.044(3) Uani 1 1 d . . . . .
N3 N 0.616(2) 0.4200(5) 0.4358(9) 0.050(3) Uani 1 1 d . . . . .
H3 H 0.773120 0.422108 0.408585 0.060 Uiso 1 1 calc R U . . .
N4 N 0.136(2) 0.5876(5) 0.5168(10) 0.050(3) Uani 1 1 d . . . . .
H4A H 0.292218 0.587570 0.487961 0.060 Uiso 1 1 calc R U . . .
C5 C 0.200(3) 0.5523(5) 0.2317(11) 0.042(3) Uani 1 1 d . . . . .
H5 H 0.330103 0.533532 0.281594 0.050 Uiso 1 1 calc R U . . .
C1AA C 0.414(3) 0.4148(6) 0.3423(14) 0.049(4) Uani 1 1 d . . . . .
C0AA C 0.576(3) 0.4222(6) 0.5842(13) 0.050(4) Uani 1 1 d . . . . .
H0AA H 0.399093 0.409227 0.601382 0.060 Uiso 1 1 calc R U . . .
C3 C 0.778(3) 0.3861(6) 0.6570(12) 0.048(4) Uani 1 1 d . . . . .
C4 C 0.727(3) 0.3284(6) 0.6628(14) 0.057(4) Uani 1 1 d . . . . .
C2AA C 0.537(4) 0.3020(8) 0.586(2) 0.099(6) Uani 1 1 d . . . . .
H2AA H 0.428135 0.320936 0.524545 0.119 Uiso 1 1 calc R U . . .
C6 C 0.508(5) 0.2472(10) 0.601(3) 0.128(8) Uani 1 1 d . . . . .
H6 H 0.381765 0.229563 0.546017 0.154 Uiso 1 1 calc R U . . .
C7 C 0.660(6) 0.2172(10) 0.695(3) 0.127(10) Uani 1 1 d . . . . .
H7 H 0.628865 0.180812 0.709275 0.153 Uiso 1 1 calc R U . . .
C8 C 0.847(6) 0.2427(10) 0.760(3) 0.148(12) Uani 1 1 d . . . . .
H8 H 0.964184 0.223533 0.816786 0.177 Uiso 1 1 calc R U . . .
C9 C 0.878(4) 0.2969(9) 0.747(2) 0.113(8) Uani 1 1 d . . . . .
H9 H 1.011453 0.313400 0.800260 0.135 Uiso 1 1 calc R U . . .
C10 C 0.677(3) 0.4513(6) 0.1468(13) 0.053(4) Uani 1 1 d . . . . .
H10 H 0.804641 0.470342 0.197551 0.063 Uiso 1 1 calc R U . . .
C11 C 0.648(3) 0.4473(7) -0.0004(14) 0.074(5) Uani 1 1 d . . . . .
H11 H 0.765421 0.462661 -0.058190 0.088 Uiso 1 1 calc R U . . .
C12 C -0.041(3) 0.5823(7) 0.0358(14) 0.072(5) Uani 1 1 d . . . . .
H12 H -0.083925 0.585861 -0.056547 0.086 Uiso 1 1 calc R U . . .
C13 C -0.013(3) 0.5846(6) 0.2871(13) 0.055(4) Uani 1 1 d . . . . .
C14 C -0.070(3) 0.5934(6) 0.4271(13) 0.055(4) Uani 1 1 d . . . . .
C15 C 0.100(2) 0.5815(6) 0.6612(12) 0.044(3) Uani 1 1 d . . . . .
H15 H -0.071275 0.596605 0.680303 0.053 Uiso 1 1 calc R U . . .
C16 C 0.308(3) 0.6142(6) 0.7389(12) 0.048(3) Uani 1 1 d . . . . .
C17 C 0.271(3) 0.6743(7) 0.7568(14) 0.057(4) Uani 1 1 d . . . . .
C18 C 0.083(4) 0.7025(7) 0.689(2) 0.096(7) Uani 1 1 d . . . . .
H18 H -0.027485 0.684428 0.626434 0.115 Uiso 1 1 calc R U . . .
C19 C 0.046(5) 0.7571(9) 0.706(3) 0.126(8) Uani 1 1 d . . . . .
H19 H -0.091919 0.774834 0.660099 0.152 Uiso 1 1 calc R U . . .
C20 C 0.211(5) 0.7840(10) 0.791(3) 0.117(8) Uani 1 1 d . . . . .
H20 H 0.196406 0.821287 0.797989 0.141 Uiso 1 1 calc R U . . .
C21 C 0.168(3) 0.5553(6) 0.0847(14) 0.060(4) Uani 1 1 d . . . . .
H21 H 0.286294 0.539304 0.028317 0.072 Uiso 1 1 calc R U . . .
C22 C 0.403(5) 0.7574(9) 0.870(3) 0.130(9) Uani 1 1 d . . . . .
H22 H 0.511288 0.776385 0.932265 0.156 Uiso 1 1 calc R U . . .
C23 C 0.434(4) 0.7011(8) 0.8550(19) 0.103(7) Uani 1 1 d . . . . .
H23 H 0.558165 0.682216 0.908392 0.124 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 1.671(17) . ?
S1 C2 1.675(13) . ?
S2 C12 1.679(17) . ?
S2 C13 1.734(13) . ?
O1 C3 1.218(14) . ?
O2 C0AA 1.429(16) . ?
O2 H2 0.8200 . ?
O3 C1AA 1.262(15) . ?
O4 C15 1.391(15) . ?
O4 H4 0.8200 . ?
O5 C16 1.232(14) . ?
O6 C14 1.240(16) . ?
C1 C11 1.38(2) . ?
C1 H1 0.9300 . ?
C2 C10 1.42(2) . ?
C2 C1AA 1.479(18) . ?
N3 C1AA 1.353(15) . ?
N3 C0AA 1.490(16) . ?
N3 H3 0.8600 . ?
N4 C14 1.348(16) . ?
N4 C15 1.453(15) . ?
N4 H4A 0.8600 . ?
C5 C21 1.454(17) . ?
C5 C13 1.48(2) . ?
C5 H5 0.9300 . ?
C0AA C3 1.520(17) . ?
C0AA H0AA 0.9800 . ?
C3 C4 1.46(2) . ?
C4 C9 1.36(2) . ?
C4 C2AA 1.36(2) . ?
C2AA C6 1.37(3) . ?
C2AA H2AA 0.9300 . ?
C6 C7 1.39(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.29(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.36(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.456(18) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C21 1.33(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.44(2) . ?
C15 C16 1.511(18) . ?
C15 H15 0.9800 . ?
C16 C17 1.51(2) . ?
C17 C18 1.34(2) . ?
C17 C23 1.41(2) . ?
C18 C19 1.38(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.34(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.39(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.41(3) . ?
C22 H22 0.9300 . ?
C23 H23 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
C1 S1 C2 91.4(8) . . ?
C12 S2 C13 93.1(9) . . ?
C0AA O2 H2 109.5 . . ?
C15 O4 H4 109.5 . . ?
C11 C1 S1 113.5(12) . . ?
C11 C1 H1 123.2 . . ?
S1 C1 H1 123.2 . . ?
C10 C2 C1AA 124.6(12) . . ?
C10 C2 S1 115.8(10) . . ?
C1AA C2 S1 119.3(11) . . ?
C1AA N3 C0AA 122.2(12) . . ?
C1AA N3 H3 118.9 . . ?
C0AA N3 H3 118.9 . . ?
C14 N4 C15 121.3(11) . . ?
C14 N4 H4A 119.3 . . ?
C15 N4 H4A 119.3 . . ?
C21 C5 C13 107.1(12) . . ?
C21 C5 H5 126.5 . . ?
C13 C5 H5 126.5 . . ?
O3 C1AA N3 120.1(12) . . ?
O3 C1AA C2 121.5(11) . . ?
N3 C1AA C2 118.4(13) . . ?
O2 C0AA N3 109.3(11) . . ?
O2 C0AA C3 110.6(11) . . ?
N3 C0AA C3 108.5(11) . . ?
O2 C0AA H0AA 109.5 . . ?
N3 C0AA H0AA 109.5 . . ?
C3 C0AA H0AA 109.5 . . ?
O1 C3 C4 123.0(13) . . ?
O1 C3 C0AA 118.5(13) . . ?
C4 C3 C0AA 118.5(12) . . ?
C9 C4 C2AA 115.6(16) . . ?
C9 C4 C3 119.4(14) . . ?
C2AA C4 C3 125.0(15) . . ?
C4 C2AA C6 120(2) . . ?
C4 C2AA H2AA 120.2 . . ?
C6 C2AA H2AA 120.2 . . ?
C2AA C6 C7 123(2) . . ?
C2AA C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C8 C7 C6 116(2) . . ?
C8 C7 H7 121.9 . . ?
C6 C7 H7 121.9 . . ?
C7 C8 C9 122(2) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C8 124(2) . . ?
C4 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C2 C10 C11 105.8(13) . . ?
C2 C10 H10 127.1 . . ?
C11 C10 H10 127.1 . . ?
C1 C11 C10 113.5(15) . . ?
C1 C11 H11 123.3 . . ?
C10 C11 H11 123.3 . . ?
C21 C12 S2 113.5(11) . . ?
C21 C12 H12 123.2 . . ?
S2 C12 H12 123.2 . . ?
C14 C13 C5 128.7(12) . . ?
C14 C13 S2 120.7(13) . . ?
C5 C13 S2 110.4(10) . . ?
O6 C14 N4 123.7(13) . . ?
O6 C14 C13 121.4(12) . . ?
N4 C14 C13 114.9(14) . . ?
O4 C15 N4 112.1(11) . . ?
O4 C15 C16 112.1(11) . . ?
N4 C15 C16 108.7(10) . . ?
O4 C15 H15 107.9 . . ?
N4 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
O5 C16 C15 119.7(13) . . ?
O5 C16 C17 120.2(13) . . ?
C15 C16 C17 120.0(12) . . ?
C18 C17 C23 118.6(16) . . ?
C18 C17 C16 123.1(14) . . ?
C23 C17 C16 118.2(15) . . ?
C17 C18 C19 123.4(19) . . ?
C17 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C20 C19 C18 119(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C22 121(2) . . ?
C19 C20 H20 119.4 . . ?
C22 C20 H20 119.4 . . ?
C12 C21 C5 115.8(14) . . ?
C12 C21 H21 122.1 . . ?
C5 C21 H21 122.1 . . ?
C20 C22 C23 119.3(19) . . ?
C20 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C17 C23 C22 118.3(18) . . ?
C17 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.098

