# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1897439'
loop_
_audit_author_name
_audit_author_address
'Satbir Mor'
;Guru Jambheshwar University of Science and Technology Hisar Haryana India 
India
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2019-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N O2 S'
_chemical_formula_sum            'C23 H17 N O2 S'
_chemical_formula_weight         371.44

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0068(7)
_cell_length_b                   9.5362(10)
_cell_length_c                   12.2550(9)
_cell_angle_alpha                95.494(3)
_cell_angle_beta                 98.424(3)
_cell_angle_gamma                97.562(4)
_cell_volume                     911.24(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3150
_cell_measurement_theta_min      5.180
_cell_measurement_theta_max      55.195

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9436
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7513
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4092
_reflns_number_gt                3077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0811P)²+0.1615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0383(3) 0.3234(2) -0.08159(17) 0.0483(5) Uani 1 1 d . . .
H1 H -0.0023 0.3934 -0.1244 0.058 Uiso 1 1 calc R . .
C2 C 0.0659(3) 0.3063(2) 0.01492(16) 0.0442(5) Uani 1 1 d . . .
H2 H 0.1702 0.3645 0.0379 0.053 Uiso 1 1 calc R . .
C3 C 0.0104(2) 0.19930(19) 0.07718(14) 0.0344(4) Uani 1 1 d . . .
C4 C 0.0883(2) 0.14715(19) 0.17750(14) 0.0344(4) Uani 1 1 d . . .
C5 C 0.2440(2) 0.1887(2) 0.23804(15) 0.0388(4) Uani 1 1 d . . .
C6 C 0.1518(2) -0.0219(2) 0.36323(15) 0.0373(4) Uani 1 1 d . . .
C7 C 0.1797(2) -0.1008(2) 0.45227(15) 0.0412(4) Uani 1 1 d . . .
H7 H 0.2845 -0.0841 0.4990 0.049 Uiso 1 1 calc R . .
C8 C 0.0531(2) -0.2034(2) 0.47157(16) 0.0441(5) Uani 1 1 d . . .
C9 C 0.2226(3) -0.2705(3) 0.62877(19) 0.0630(6) Uani 1 1 d . . .
H9A H 0.2124 -0.3324 0.6855 0.094 Uiso 1 1 calc R . .
H9B H 0.2521 -0.1735 0.6624 0.094 Uiso 1 1 calc R . .
H9C H 0.3100 -0.2950 0.5877 0.094 Uiso 1 1 calc R . .
C10 C 0.3674(2) 0.30954(19) 0.21521(14) 0.0372(4) Uani 1 1 d . . .
C11 C 0.4713(2) 0.2866(2) 0.13569(16) 0.0440(5) Uani 1 1 d . . .
H11 H 0.4644 0.1958 0.0984 0.053 Uiso 1 1 calc R . .
C12 C 0.5845(3) 0.3968(2) 0.11154(17) 0.0485(5) Uani 1 1 d . . .
H12 H 0.6527 0.3808 0.0577 0.058 Uiso 1 1 calc R . .
C13 C 0.5958(2) 0.5307(2) 0.16743(17) 0.0472(5) Uani 1 1 d . . .
H13 H 0.6711 0.6056 0.1509 0.057 Uiso 1 1 calc R . .
C14 C 0.4963(2) 0.5535(2) 0.24746(16) 0.0439(5) Uani 1 1 d . . .
H14 H 0.5066 0.6442 0.2856 0.053 Uiso 1 1 calc R . .
C15 C 0.3802(2) 0.4446(2) 0.27318(15) 0.0411(4) Uani 1 1 d . . .
C16 C 0.2692(4) 0.4761(3) 0.3591(2) 0.0749(8) Uani 1 1 d . . .
H16A H 0.3065 0.4344 0.4249 0.112 Uiso 1 1 calc R . .
H16B H 0.1527 0.4367 0.3302 0.112 Uiso 1 1 calc R . .
H16C H 0.2777 0.5773 0.3768 0.112 Uiso 1 1 calc R . .
C17 C -0.1801(2) 0.0134(2) 0.11979(15) 0.0379(4) Uani 1 1 d . . .
C18 C -0.1486(2) 0.11707(19) 0.04186(14) 0.0362(4) Uani 1 1 d . . .
C19 C -0.2540(2) 0.1351(2) -0.05488(16) 0.0440(5) Uani 1 1 d . . .
H19 H -0.3600 0.0792 -0.0771 0.053 Uiso 1 1 calc R . .
C20 C -0.1959(3) 0.2383(2) -0.11636(17) 0.0489(5) Uani 1 1 d . . .
H20 H -0.2626 0.2517 -0.1822 0.059 Uiso 1 1 calc R . .
C21 C -0.0048(2) -0.04455(18) 0.29229(13) 0.0336(4) Uani 1 1 d . . .
C22 C -0.1317(2) -0.1471(2) 0.31483(16) 0.0433(5) Uani 1 1 d . . .
H22 H -0.2381 -0.1626 0.2700 0.052 Uiso 1 1 calc R . .
C23 C -0.1028(3) -0.2258(2) 0.40190(17) 0.0507(5) Uani 1 1 d . . .
H23 H -0.1890 -0.2951 0.4143 0.061 Uiso 1 1 calc R . .
N1 N -0.03309(17) 0.03336(16) 0.19998(12) 0.0348(3) Uani 1 1 d . . .
O1 O 0.06626(19) -0.28588(19) 0.55646(13) 0.0663(5) Uani 1 1 d . . .
O2 O -0.30853(17) -0.07244(17) 0.11693(12) 0.0556(4) Uani 1 1 d . . .
S1 S 0.32490(6) 0.10462(7) 0.34973(5) 0.0587(2) Uani 1 1 d . . .


_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
C1 C2 1.380(3) . ?
C1 C20 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(2) . ?
C2 H2 0.9300 . ?
C3 C18 1.391(2) . ?
C3 C4 1.457(2) . ?
C4 C5 1.343(2) . ?
C4 N1 1.434(2) . ?
C5 C10 1.492(2) . ?
C5 S1 1.7387(19) . ?
C6 C7 1.392(3) . ?
C6 C21 1.396(2) . ?
C6 S1 1.7521(17) . ?
C7 C8 1.376(2) . ?
C7 H7 0.9300 . ?
C8 O1 1.363(2) . ?
C8 C23 1.384(3) . ?
C9 O1 1.405(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.391(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.507(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O2 1.221(2) . ?
C17 N1 1.398(2) . ?
C17 C18 1.462(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.392(2) . ?
C21 N1 1.419(2) . ?
C22 C23 1.372(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
C2 C1 C20 121.57(19) . . ?
C2 C1 H1 119.2 . . ?
C20 C1 H1 119.2 . . ?
C1 C2 C3 118.25(18) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C18 C3 C2 119.21(17) . . ?
C18 C3 C4 107.67(15) . . ?
C2 C3 C4 133.10(16) . . ?
C5 C4 N1 124.34(16) . . ?
C5 C4 C3 129.25(16) . . ?
N1 C4 C3 106.36(14) . . ?
C4 C5 C10 123.73(16) . . ?
C4 C5 S1 123.46(14) . . ?
C10 C5 S1 112.79(12) . . ?
C7 C6 C21 120.82(16) . . ?
C7 C6 S1 115.03(13) . . ?
C21 C6 S1 124.16(14) . . ?
C8 C7 C6 120.42(17) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O1 C8 C7 125.28(17) . . ?
O1 C8 C23 115.66(16) . . ?
C7 C8 C23 119.06(17) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 119.83(16) . . ?
C11 C10 C5 119.49(17) . . ?
C15 C10 C5 120.68(16) . . ?
C12 C11 C10 120.73(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.63(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.98(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.72(19) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 118.09(17) . . ?
C14 C15 C16 119.78(19) . . ?
C10 C15 C16 122.10(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 N1 126.53(17) . . ?
O2 C17 C18 127.55(17) . . ?
N1 C17 C18 105.91(14) . . ?
C19 C18 C3 122.46(18) . . ?
C19 C18 C17 127.88(17) . . ?
C3 C18 C17 109.65(15) . . ?
C20 C19 C18 117.57(18) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
C19 C20 C1 120.91(19) . . ?
C19 C20 H20 119.5 . . ?
C1 C20 H20 119.5 . . ?
C22 C21 C6 117.60(16) . . ?
C22 C21 N1 121.23(15) . . ?
C6 C21 N1 121.17(15) . . ?
C23 C22 C21 121.34(17) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C8 120.75(17) . . ?
C22 C23 H23 119.6 . . ?
C8 C23 H23 119.6 . . ?
C17 N1 C21 126.08(14) . . ?
C17 N1 C4 110.37(14) . . ?
C21 N1 C4 123.55(14) . . ?
C8 O1 C9 118.47(16) . . ?
C5 S1 C6 103.01(9) . . ?

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
C20 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C18 -1.8(3) . . . . ?
C1 C2 C3 C4 176.35(19) . . . . ?
C18 C3 C4 C5 176.54(19) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C18 C3 C4 N1 -1.05(19) . . . . ?
C2 C3 C4 N1 -179.38(19) . . . . ?
N1 C4 C5 C10 -178.51(17) . . . . ?
C3 C4 C5 C10 4.3(3) . . . . ?
N1 C4 C5 S1 2.9(3) . . . . ?
C3 C4 C5 S1 -174.27(15) . . . . ?
C21 C6 C7 C8 0.3(3) . . . . ?
S1 C6 C7 C8 179.93(16) . . . . ?
C6 C7 C8 O1 -179.53(19) . . . . ?
C6 C7 C8 C23 -0.7(3) . . . . ?
C4 C5 C10 C11 -83.6(3) . . . . ?
S1 C5 C10 C11 95.10(19) . . . . ?
C4 C5 C10 C15 96.8(2) . . . . ?
S1 C5 C10 C15 -84.5(2) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
C5 C10 C11 C12 178.88(17) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C10 0.2(3) . . . . ?
C13 C14 C15 C16 -177.9(2) . . . . ?
C11 C10 C15 C14 1.1(3) . . . . ?
C5 C10 C15 C14 -179.33(17) . . . . ?
C11 C10 C15 C16 179.1(2) . . . . ?
C5 C10 C15 C16 -1.2(3) . . . . ?
C2 C3 C18 C19 1.4(3) . . . . ?
C4 C3 C18 C19 -177.21(17) . . . . ?
C2 C3 C18 C17 -179.53(17) . . . . ?
C4 C3 C18 C17 1.9(2) . . . . ?
O2 C17 C18 C19 -3.6(3) . . . . ?
N1 C17 C18 C19 177.04(18) . . . . ?
O2 C17 C18 C3 177.35(19) . . . . ?
N1 C17 C18 C3 -2.0(2) . . . . ?
C3 C18 C19 C20 0.1(3) . . . . ?
C17 C18 C19 C20 -178.76(18) . . . . ?
C18 C19 C20 C1 -1.2(3) . . . . ?
C2 C1 C20 C19 0.7(3) . . . . ?
C7 C6 C21 C22 0.8(3) . . . . ?
S1 C6 C21 C22 -178.76(15) . . . . ?
C7 C6 C21 N1 -178.67(17) . . . . ?
S1 C6 C21 N1 1.8(3) . . . . ?
C6 C21 C22 C23 -1.6(3) . . . . ?
N1 C21 C22 C23 177.85(18) . . . . ?
C21 C22 C23 C8 1.3(3) . . . . ?
O1 C8 C23 C22 178.8(2) . . . . ?
C7 C8 C23 C22 -0.1(3) . . . . ?
O2 C17 N1 C21 1.1(3) . . . . ?
C18 C17 N1 C21 -179.55(16) . . . . ?
O2 C17 N1 C4 -178.04(19) . . . . ?
C18 C17 N1 C4 1.3(2) . . . . ?
C22 C21 N1 C17 -3.8(3) . . . . ?
C6 C21 N1 C17 175.68(17) . . . . ?
C22 C21 N1 C4 175.30(17) . . . . ?
C6 C21 N1 C4 -5.3(3) . . . . ?
C5 C4 N1 C17 -177.93(18) . . . . ?
C3 C4 N1 C17 -0.19(19) . . . . ?
C5 C4 N1 C21 2.9(3) . . . . ?
C3 C4 N1 C21 -179.38(15) . . . . ?
C7 C8 O1 C9 -2.5(3) . . . . ?
C23 C8 O1 C9 178.6(2) . . . . ?
C4 C5 S1 C6 -5.1(2) . . . . ?
C10 C5 S1 C6 176.18(14) . . . . ?
C7 C6 S1 C5 -176.75(15) . . . . ?
C21 C6 S1 C5 2.82(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.899
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.899
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.067
