# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_w1
_database_code_depnum_ccdc_archive 'CCDC 2263782'
loop_
_audit_author_name
_audit_author_address
'Karthik V'
;University of mysore
India
;
_audit_update_record             
;
2023-05-18 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O2 S'
_chemical_formula_sum            'C17 H13 N O2 S'
_chemical_formula_weight         295.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   14.0054(11)
_cell_length_b                   13.9608(11)
_cell_length_c                   7.3675(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.698(2)
_cell_angle_gamma                90.00
_cell_volume                     1427.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9533
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33795
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3296
_reflns_number_gt                2843
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  PLATON

_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0413P)²+1.9667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3296
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S10 S 0.95361(5) 0.18762(5) 0.09308(10) 0.03182(19) Uani 1 1 d . . .
O13 O 0.97492(13) -0.06522(12) 0.3308(3) 0.0315(4) Uani 1 1 d . . .
O14 O 0.85870(13) 0.04812(13) 0.2891(2) 0.0303(4) Uani 1 1 d . . .
N8 N 1.09234(15) 0.06800(14) 0.1607(3) 0.0245(4) Uani 1 1 d . . .
C7 C 1.12783(19) 0.14471(17) 0.0729(3) 0.0247(5) Uani 1 1 d . . .
C11 C 1.0621(2) 0.21639(18) 0.0304(4) 0.0314(6) Uani 1 1 d . . .
H11 H 1.0753 0.2737 -0.0257 0.038 Uiso 1 1 calc R . .
C9 C 1.00242(18) 0.08101(17) 0.1787(3) 0.0244(5) Uani 1 1 d . . .
C6 C 1.22893(18) 0.14369(16) 0.0375(3) 0.0241(5) Uani 1 1 d . . .
C5 C 1.2896(2) 0.06762(18) 0.0991(4) 0.0299(6) Uani 1 1 d . . .
H5 H 1.2661 0.0172 0.1627 0.036 Uiso 1 1 calc R . .
C16 C 0.73254(19) 0.06140(17) 0.4759(3) 0.0262(5) Uani 1 1 d . . .
C12 C 0.94533(18) 0.01172(17) 0.2743(3) 0.0256(5) Uani 1 1 d . . .
C4 C 1.3847(2) 0.0668(2) 0.0661(4) 0.0349(6) Uani 1 1 d . . .
H4 H 1.4247 0.0163 0.1096 0.042 Uiso 1 1 calc R . .
C15 C 0.79704(19) -0.00745(18) 0.3943(4) 0.0300(6) Uani 1 1 d . . .
H15A H 0.8360 -0.0430 0.4904 0.036 Uiso 1 1 calc R . .
H15B H 0.7588 -0.0527 0.3152 0.036 Uiso 1 1 calc R . .
C2 C 1.3607(2) 0.2156(2) -0.0937(4) 0.0341(6) Uani 1 1 d . . .
H2 H 1.3844 0.2652 -0.1593 0.041 Uiso 1 1 calc R . .
C19 C 0.6146(2) 0.1860(2) 0.6381(4) 0.0438(7) Uani 1 1 d . . .
H19 H 0.5752 0.2280 0.6920 0.053 Uiso 1 1 calc R . .
C1 C 1.2663(2) 0.21763(18) -0.0596(3) 0.0300(6) Uani 1 1 d . . .
H1 H 1.2271 0.2688 -0.1019 0.036 Uiso 1 1 calc R . .
C3 C 1.4207(2) 0.1402(2) -0.0309(4) 0.0343(6) Uani 1 1 d . . .
H3 H 1.4844 0.1391 -0.0538 0.041 Uiso 1 1 calc R . .
C21 C 0.7722(2) 0.12733(18) 0.6055(4) 0.0305(6) Uani 1 1 d . . .
H21 H 0.8386 0.1295 0.6390 0.037 Uiso 1 1 calc R . .
C20 C 0.7133(2) 0.1900(2) 0.6850(4) 0.0401(7) Uani 1 1 d . . .
H20 H 0.7403 0.2348 0.7702 0.048 Uiso 1 1 calc R . .
C17 C 0.6339(2) 0.0588(2) 0.4291(4) 0.0347(6) Uani 1 1 d . . .
H17 H 0.6066 0.0155 0.3412 0.042 Uiso 1 1 calc R . .
C18 C 0.5748(2) 0.1202(2) 0.5119(5) 0.0443(7) Uani 1 1 d . . .
H18 H 0.5082 0.1167 0.4819 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S10 0.0343(4) 0.0264(3) 0.0347(4) 0.0028(3) 0.0044(3) 0.0076(3)
O13 0.0369(10) 0.0198(9) 0.0381(11) -0.0011(8) 0.0067(8) 0.0017(7)
O14 0.0320(10) 0.0305(10) 0.0299(10) 0.0053(8) 0.0089(8) 0.0036(8)
N8 0.0312(11) 0.0212(10) 0.0209(10) 0.0002(8) 0.0028(8) 0.0008(8)
C7 0.0369(14) 0.0189(11) 0.0178(11) -0.0010(9) 0.0016(9) 0.0015(10)
C11 0.0411(15) 0.0224(12) 0.0304(14) 0.0029(10) 0.0042(11) 0.0031(11)
C9 0.0335(13) 0.0182(11) 0.0209(11) -0.0027(9) 0.0015(9) 0.0018(9)
C6 0.0374(14) 0.0171(11) 0.0178(11) -0.0006(9) 0.0033(10) -0.0003(10)
C5 0.0400(15) 0.0228(12) 0.0288(13) 0.0036(10) 0.0115(11) 0.0008(11)
C16 0.0371(14) 0.0210(11) 0.0215(12) 0.0036(9) 0.0074(10) 0.0001(10)
C12 0.0311(13) 0.0234(12) 0.0219(12) -0.0050(9) 0.0019(10) -0.0011(10)
C4 0.0388(15) 0.0315(14) 0.0360(15) 0.0012(11) 0.0106(12) 0.0064(12)
C15 0.0351(14) 0.0255(12) 0.0301(13) 0.0012(10) 0.0070(11) -0.0011(10)
C2 0.0450(16) 0.0311(14) 0.0273(14) 0.0039(11) 0.0086(12) -0.0077(12)
C19 0.0582(19) 0.0356(15) 0.0430(17) 0.0044(13) 0.0264(15) 0.0125(14)
C1 0.0419(15) 0.0248(12) 0.0232(13) 0.0028(10) 0.0040(11) -0.0003(11)
C3 0.0345(14) 0.0395(15) 0.0304(14) -0.0022(12) 0.0099(11) -0.0018(12)
C21 0.0375(14) 0.0239(12) 0.0301(13) 0.0029(10) 0.0049(11) -0.0037(11)
C20 0.062(2) 0.0262(13) 0.0332(15) -0.0017(12) 0.0106(13) 0.0003(13)
C17 0.0365(15) 0.0349(15) 0.0326(15) -0.0007(12) 0.0042(11) -0.0022(12)
C18 0.0342(15) 0.0476(18) 0.0523(19) 0.0053(15) 0.0106(14) 0.0062(13)

_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
S10 C11 1.694(3) . ?
S10 C9 1.722(2) . ?
O13 C12 1.205(3) . ?
O14 C12 1.333(3) . ?
O14 C15 1.459(3) . ?
N8 C9 1.297(3) . ?
N8 C7 1.378(3) . ?
C7 C11 1.367(3) . ?
C7 C6 1.474(4) . ?
C9 C12 1.491(3) . ?
C6 C5 1.398(3) . ?
C6 C1 1.397(3) . ?
C5 C4 1.384(4) . ?
C16 C17 1.379(4) . ?
C16 C21 1.387(4) . ?
C16 C15 1.499(4) . ?
C4 C3 1.383(4) . ?
C2 C1 1.378(4) . ?
C2 C3 1.386(4) . ?
C19 C18 1.372(5) . ?
C19 C20 1.379(5) . ?
C21 C20 1.385(4) . ?
C17 C18 1.388(4) . ?

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
C11 S10 C9 88.75(12) . . ?
C12 O14 C15 116.80(19) . . ?
C9 N8 C7 110.8(2) . . ?
C11 C7 N8 113.7(2) . . ?
C11 C7 C6 126.9(2) . . ?
N8 C7 C6 119.4(2) . . ?
C7 C11 S10 111.4(2) . . ?
N8 C9 C12 123.2(2) . . ?
N8 C9 S10 115.27(19) . . ?
C12 C9 S10 121.48(19) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 121.2(2) . . ?
C4 C5 C6 120.5(2) . . ?
C17 C16 C21 119.0(2) . . ?
C17 C16 C15 121.4(2) . . ?
C21 C16 C15 119.6(2) . . ?
O13 C12 O14 125.9(2) . . ?
O13 C12 C9 124.1(2) . . ?
O14 C12 C9 110.1(2) . . ?
C3 C4 C5 120.7(3) . . ?
O14 C15 C16 107.7(2) . . ?
C1 C2 C3 120.5(2) . . ?
C18 C19 C20 120.0(3) . . ?
C2 C1 C6 120.8(2) . . ?
C4 C3 C2 119.2(3) . . ?
C20 C21 C16 120.3(3) . . ?
C19 C20 C21 120.1(3) . . ?
C16 C17 C18 120.7(3) . . ?
C19 C18 C17 119.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.068
_exptl_crystal_recrystallization_method 'Vapour deposition'
