# 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_AV-SGD866
_database_code_depnum_ccdc_archive 'CCDC 2254798'
loop_
_audit_author_name
_audit_author_address
'Sudam Dawande'
;Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-04-07 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;

_audit_creation_date             2020-01-24T13:38:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23  H18  N2  O3  S1'
_chemical_formula_sum            'C23 H18 N2 O3 S'
_chemical_formula_weight         402.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0778(5)
_cell_length_b                   20.7672(14)
_cell_length_c                   11.4161(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.705(5)
_cell_angle_gamma                90
_cell_volume                     1893.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      1.961
_cell_measurement_theta_max      28.794
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.2
_exptl_absorpt_correction_type   NONE

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_number            19287
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.961
_diffrn_reflns_theta_max         28.794
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             4892
_reflns_number_gt                3397
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.1269P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4892
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.08317(6) 0.28763(2) 0.65401(5) 0.02115(14) Uani 1 1 d . . . . .
O3 O 0.33615(16) 0.41208(6) 0.85128(12) 0.0260(3) Uani 1 1 d . . . . .
O1 O -0.00576(17) 0.26971(6) 0.54087(13) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.01538(18) 0.27222(6) 0.75941(13) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.11051(18) 0.36638(7) 0.65735(14) 0.0171(4) Uani 1 1 d . . . . .
N1 N 0.17897(18) 0.46389(7) 0.58606(14) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.2453(2) 0.50242(9) 0.50741(17) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.1731(2) 0.40170(9) 0.56670(17) 0.0162(4) Uani 1 1 d . . . . .
C18 C 0.1685(2) 0.50212(8) 0.88012(17) 0.0165(4) Uani 1 1 d . . . . .
C4 C 0.3121(2) 0.47670(9) 0.40962(17) 0.0181(4) Uani 1 1 d . . . . .
C17 C 0.2001(2) 0.43871(9) 0.82752(17) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.2855(2) 0.25373(9) 0.66650(18) 0.0199(4) Uani 1 1 d . . . . .
C20 C 0.2389(2) 0.57861(9) 1.03815(18) 0.0221(4) Uani 1 1 d . . . . .
H20 H 0.301475 0.589706 1.110525 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2268(2) 0.37165(9) 0.46731(17) 0.0176(4) Uani 1 1 d . . . . .
H2 H 0.213547 0.327615 0.45429 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0561(2) 0.40456(9) 0.75211(17) 0.0182(4) Uani 1 1 d . . . . .
H16A H 0.001094 0.376519 0.802229 0.022 Uiso 1 1 calc R U . . .
H16B H -0.025005 0.436268 0.717494 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2982(2) 0.40959(9) 0.39189(17) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.338594 0.39104 0.327644 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2491(2) 0.56950(9) 0.52691(18) 0.0209(4) Uani 1 1 d . . . . .
H8 H 0.202771 0.58683 0.589722 0.025 Uiso 1 1 calc R U . . .
C21 C 0.1223(2) 0.62098(9) 0.98142(17) 0.0206(4) Uani 1 1 d . . . . .
H21 H 0.106497 0.660795 1.015349 0.025 Uiso 1 1 calc R U . . .
C23 C 0.0505(2) 0.54514(9) 0.82323(18) 0.0212(4) Uani 1 1 d . . . . .
H23 H -0.013322 0.534064 0.7513 0.025 Uiso 1 1 calc R U . . .
C22 C 0.0286(2) 0.60442(9) 0.87417(19) 0.0237(5) Uani 1 1 d . . . . .
H22 H -0.049635 0.63327 0.835985 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3929(2) 0.58381(10) 0.35828(18) 0.0240(5) Uani 1 1 d . . . . .
H6 H 0.443924 0.611232 0.310149 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3879(2) 0.51905(9) 0.33639(17) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.434606 0.502735 0.27293 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3214(2) 0.60906(9) 0.45288(18) 0.0229(5) Uani 1 1 d . . . . .
H7 H 0.322977 0.653297 0.465637 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2630(2) 0.51933(9) 0.98716(17) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.342905 0.491009 1.025021 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3210(3) 0.20993(9) 0.58181(19) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.24136 0.200201 0.516551 0.031 Uiso 1 1 calc R U . . .
C15 C 0.4036(3) 0.26842(9) 0.76498(19) 0.0258(5) Uani 1 1 d . . . . .
H15 H 0.378036 0.297355 0.821787 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5591(3) 0.23944(10) 0.7771(2) 0.0306(5) Uani 1 1 d . . . . .
H14 H 0.639657 0.249274 0.841775 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4772(3) 0.18102(10) 0.5963(2) 0.0337(6) Uani 1 1 d . . . . .
H12 H 0.502604 0.151452 0.540475 0.04 Uiso 1 1 calc R U . . .
C13 C 0.5952(3) 0.19573(10) 0.6928(2) 0.0334(5) Uani 1 1 d . . . . .
H13 H 0.699945 0.176161 0.701486 0.04 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.4290(15) . ?
S1 O2 1.4317(14) . ?
S1 N2 1.6499(15) . ?
S1 C10 1.766(2) . ?
O3 C17 1.223(2) . ?
N2 C1 1.422(2) . ?
N2 C16 1.461(2) . ?
N1 C1 1.310(2) . ?
N1 C9 1.371(2) . ?
C9 C8 1.410(3) . ?
C9 C4 1.416(3) . ?
C1 C2 1.419(2) . ?
C18 C19 1.386(3) . ?
C18 C23 1.393(3) . ?
C18 C17 1.485(3) . ?
C4 C3 1.410(3) . ?
C4 C5 1.415(3) . ?
C17 C16 1.515(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.394(3) . ?
C20 C21 1.377(3) . ?
C20 C19 1.388(3) . ?
C20 H20 0.93 . ?
C2 C3 1.359(2) . ?
C2 H2 0.93 . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C3 H3 0.93 . ?
C8 C7 1.371(3) . ?
C8 H8 0.93 . ?
C21 C22 1.382(3) . ?
C21 H21 0.93 . ?
C23 C22 1.384(3) . ?
C23 H23 0.93 . ?
C22 H22 0.93 . ?
C6 C5 1.367(3) . ?
C6 C7 1.401(3) . ?
C6 H6 0.93 . ?
C5 H5 0.93 . ?
C7 H7 0.93 . ?
C19 H19 0.93 . ?
C11 C12 1.384(3) . ?
C11 H11 0.93 . ?
C15 C14 1.381(3) . ?
C15 H15 0.93 . ?
C14 C13 1.385(3) . ?
C14 H14 0.93 . ?
C12 C13 1.378(3) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?

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
O1 S1 O2 119.83(9) . . ?
O1 S1 N2 109.05(8) . . ?
O2 S1 N2 105.61(8) . . ?
O1 S1 C10 107.56(9) . . ?
O2 S1 C10 108.07(9) . . ?
N2 S1 C10 105.92(8) . . ?
C1 N2 C16 116.02(14) . . ?
C1 N2 S1 123.74(12) . . ?
C16 N2 S1 120.04(12) . . ?
C1 N1 C9 118.22(16) . . ?
N1 C9 C8 118.33(17) . . ?
N1 C9 C4 121.98(16) . . ?
C8 C9 C4 119.67(17) . . ?
N1 C1 C2 124.10(17) . . ?
N1 C1 N2 113.18(15) . . ?
C2 C1 N2 122.70(16) . . ?
C19 C18 C23 119.48(17) . . ?
C19 C18 C17 118.67(16) . . ?
C23 C18 C17 121.82(18) . . ?
C3 C4 C5 124.16(17) . . ?
C3 C4 C9 117.03(17) . . ?
C5 C4 C9 118.81(17) . . ?
O3 C17 C18 120.98(17) . . ?
O3 C17 C16 120.06(17) . . ?
C18 C17 C16 118.74(15) . . ?
C11 C10 C15 121.11(19) . . ?
C11 C10 S1 119.42(17) . . ?
C15 C10 S1 119.35(15) . . ?
C21 C20 C19 119.92(19) . . ?
C21 C20 H20 120 . . ?
C19 C20 H20 120 . . ?
C3 C2 C1 117.53(17) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
N2 C16 C17 112.56(14) . . ?
N2 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C2 C3 C4 120.95(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C7 C8 C9 119.72(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C20 C21 C22 120.10(18) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C22 C23 C18 119.76(19) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C21 C22 C23 120.39(19) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C5 C6 C7 120.31(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C5 C4 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C8 C7 C6 120.97(18) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C18 C19 C20 120.34(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C14 C15 C10 119.1(2) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

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
O1 S1 N2 C1 -48.66(16) . . . . ?
O2 S1 N2 C1 -178.66(14) . . . . ?
C10 S1 N2 C1 66.84(16) . . . . ?
O1 S1 N2 C16 125.97(14) . . . . ?
O2 S1 N2 C16 -4.03(16) . . . . ?
C10 S1 N2 C16 -118.53(15) . . . . ?
C1 N1 C9 C8 178.91(17) . . . . ?
C1 N1 C9 C4 -2.3(3) . . . . ?
C9 N1 C1 C2 -1.9(3) . . . . ?
C9 N1 C1 N2 176.74(15) . . . . ?
C16 N2 C1 N1 3.0(2) . . . . ?
S1 N2 C1 N1 177.80(13) . . . . ?
C16 N2 C1 C2 -178.41(16) . . . . ?
S1 N2 C1 C2 -3.6(2) . . . . ?
N1 C9 C4 C3 3.9(3) . . . . ?
C8 C9 C4 C3 -177.38(17) . . . . ?
N1 C9 C4 C5 -176.10(17) . . . . ?
C8 C9 C4 C5 2.6(3) . . . . ?
C19 C18 C17 O3 -25.0(3) . . . . ?
C23 C18 C17 O3 153.18(18) . . . . ?
C19 C18 C17 C16 149.68(17) . . . . ?
C23 C18 C17 C16 -32.2(3) . . . . ?
O1 S1 C10 C11 -9.26(18) . . . . ?
O2 S1 C10 C11 121.44(16) . . . . ?
N2 S1 C10 C11 -125.77(15) . . . . ?
O1 S1 C10 C15 174.60(14) . . . . ?
O2 S1 C10 C15 -54.70(17) . . . . ?
N2 S1 C10 C15 58.09(17) . . . . ?
N1 C1 C2 C3 4.3(3) . . . . ?
N2 C1 C2 C3 -174.18(16) . . . . ?
C1 N2 C16 C17 -67.1(2) . . . . ?
S1 N2 C16 C17 117.88(15) . . . . ?
O3 C17 C16 N2 -37.5(2) . . . . ?
C18 C17 C16 N2 147.78(16) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C5 C4 C3 C2 178.66(18) . . . . ?
C9 C4 C3 C2 -1.3(3) . . . . ?
N1 C9 C8 C7 177.09(17) . . . . ?
C4 C9 C8 C7 -1.7(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C17 C18 C23 C22 -178.26(17) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C18 C23 C22 C21 -0.4(3) . . . . ?
C7 C6 C5 C4 -0.7(3) . . . . ?
C3 C4 C5 C6 178.54(18) . . . . ?
C9 C4 C5 C6 -1.5(3) . . . . ?
C9 C8 C7 C6 -0.5(3) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C23 C18 C19 C20 0.8(3) . . . . ?
C17 C18 C19 C20 178.98(17) . . . . ?
C21 C20 C19 C18 -0.9(3) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
S1 C10 C11 C12 -176.42(15) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
S1 C10 C15 C14 177.01(15) . . . . ?
C10 C15 C14 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?

