# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_ups3310_kns_bhu_0m
_database_code_depnum_ccdc_archive 'CCDC 1843990'
loop_
_audit_author_name
_audit_author_address
'Preeti Wadhwa'
;Department Of Chemistry, Institute Of Science, B.H.U, Varanasi-221005
India
;
_audit_update_record             
;
2018-05-18 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O5 S2'
_chemical_formula_sum            'C19 H17 N3 O5 S2'
_chemical_formula_weight         431.48

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                   9.050(5)
_cell_length_b                   10.325(5)
_cell_length_c                   11.792(5)
_cell_angle_alpha                97.739(5)
_cell_angle_beta                 103.231(5)
_cell_angle_gamma                109.788(5)
_cell_volume                     981.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4085
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.89

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   (SADABS;Bruker,2000)

_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15992
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4805
_reflns_number_gt                3772
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0891P)²+0.2032P] 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         4805
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_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
S1 S 0.29171(6) 0.02799(5) 0.41272(4) 0.03889(16) Uani 1 1 d . . .
S2 S 0.29487(7) 0.01907(5) 0.74816(5) 0.04365(17) Uani 1 1 d . . .
C17 C 0.1913(2) 0.2232(2) 0.33027(17) 0.0381(4) Uani 1 1 d . . .
C19 C 0.1846(3) -0.1066(2) 0.13436(17) 0.0425(5) Uani 1 1 d . . .
O1 O 0.3740(3) -0.06896(18) 0.79555(16) 0.0634(5) Uani 1 1 d . . .
N1 N 0.4083(2) 0.09844(19) 0.66635(14) 0.0398(4) Uani 1 1 d . . .
O4 O 0.2377(2) -0.17108(18) 0.20012(13) 0.0531(4) Uani 1 1 d . . .
O3 O 0.1374(2) 0.28739(18) 0.26512(14) 0.0532(4) Uani 1 1 d . . .
O5 O 0.1295(2) -0.14977(19) 0.01589(13) 0.0541(4) Uani 1 1 d . . .
N2 N 0.3603(2) 0.20821(18) 0.62642(14) 0.0388(4) Uani 1 1 d . . .
N3 N 0.2425(2) 0.26399(17) 0.45399(14) 0.0360(4) Uani 1 1 d . . .
C18 C 0.2127(2) 0.0886(2) 0.29141(17) 0.0372(4) Uani 1 1 d . . .
O2 O 0.1300(2) -0.03965(18) 0.67081(16) 0.0622(5) Uani 1 1 d . . .
C16 C 0.3542(3) 0.3722(2) 1.05063(19) 0.0476(5) Uani 1 1 d . . .
C1 C 0.3018(2) 0.17638(19) 0.51259(16) 0.0326(4) Uani 1 1 d . . .
C2 C 0.0781(3) 0.4604(3) 0.6432(2) 0.0583(6) Uani 1 1 d . . .
H2 H 0.0006 0.4415 0.6851 0.070 Uiso 1 1 calc R . .
C3 C 0.2429(3) 0.3436(3) 0.9394(2) 0.0503(5) Uani 1 1 d . . .
H3 H 0.1827 0.4003 0.9261 0.060 Uiso 1 1 calc R . .
C4 C 0.2177(2) 0.3798(2) 0.51859(18) 0.0383(4) Uani 1 1 d . . .
C5 C 0.1689(4) 0.5972(3) 0.6450(2) 0.0621(7) Uani 1 1 d . . .
H5 H 0.1531 0.6710 0.6884 0.074 Uiso 1 1 calc R . .
C6 C 0.1709(3) 0.0276(2) 0.17494(18) 0.0435(5) Uani 1 1 d . . .
C7 C 0.3098(3) 0.1502(2) 0.86706(17) 0.0384(4) Uani 1 1 d . . .
C8 C 0.3088(3) 0.5171(2) 0.5186(2) 0.0517(6) Uani 1 1 d . . .
H8 H 0.3858 0.5365 0.4764 0.062 Uiso 1 1 calc R . .
C9 C 0.1014(3) 0.3497(3) 0.57915(18) 0.0465(5) Uani 1 1 d . . .
H9 H 0.0393 0.2564 0.5771 0.056 Uiso 1 1 calc R . .
C10 C 0.4407(3) 0.2845(3) 1.0689(2) 0.0528(6) Uani 1 1 d . . .
H10 H 0.5138 0.3001 1.1438 0.063 Uiso 1 1 calc R . .
C11 C 0.2187(3) 0.2335(2) 0.84759(19) 0.0455(5) Uani 1 1 d . . .
H11 H 0.1424 0.2155 0.7737 0.055 Uiso 1 1 calc R . .
C12 C 0.3818(4) 0.4952(3) 1.1485(2) 0.0656(7) Uani 1 1 d . . .
H12A H 0.4627 0.4987 1.2189 0.098 Uiso 1 1 calc R . .
H12B H 0.2806 0.4837 1.1665 0.098 Uiso 1 1 calc R . .
H12C H 0.4199 0.5815 1.1225 0.098 Uiso 1 1 calc R . .
C13 C 0.2826(3) 0.6265(3) 0.5835(3) 0.0648(8) Uani 1 1 d . . .
H13 H 0.3430 0.7199 0.5849 0.078 Uiso 1 1 calc R . .
C14 C 0.1301(4) -0.2848(3) -0.0353(2) 0.0628(7) Uani 1 1 d . . .
H14A H 0.0880 -0.3052 -0.1209 0.094 Uiso 1 1 calc R . .
H14B H 0.0622 -0.3575 -0.0055 0.094 Uiso 1 1 calc R . .
H14C H 0.2405 -0.2815 -0.0134 0.094 Uiso 1 1 calc R . .
C15 C 0.4201(3) 0.1747(2) 0.97805(19) 0.0470(5) Uani 1 1 d . . .
H15 H 0.4799 0.1177 0.9913 0.056 Uiso 1 1 calc R . .
H6 H 0.128(3) 0.071(3) 0.121(2) 0.054(7) Uiso 1 1 d . . .
H21 H 0.518(3) 0.134(3) 0.710(2) 0.060(8) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C18 1.739(2) . ?
S1 C1 1.7642(19) . ?
S2 O2 1.4287(18) . ?
S2 O1 1.4300(18) . ?
S2 N1 1.659(2) . ?
S2 C7 1.759(2) . ?
C17 O3 1.205(2) . ?
C17 N3 1.383(2) . ?
C17 C18 1.493(3) . ?
C19 O4 1.208(3) . ?
C19 O5 1.327(2) . ?
C19 C6 1.459(3) . ?
N1 N2 1.442(2) . ?
N1 H21 0.92(3) . ?
O5 C14 1.445(3) . ?
N2 C1 1.276(2) . ?
N3 C1 1.383(2) . ?
N3 C4 1.440(2) . ?
C18 C6 1.339(3) . ?
C16 C3 1.383(3) . ?
C16 C10 1.391(4) . ?
C16 C12 1.505(3) . ?
C2 C5 1.367(4) . ?
C2 C9 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C11 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.377(3) . ?
C4 C8 1.378(3) . ?
C5 C13 1.366(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.92(3) . ?
C7 C15 1.384(3) . ?
C7 C11 1.385(3) . ?
C8 C13 1.395(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.381(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 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
C18 S1 C1 90.40(9) . . ?
O2 S2 O1 121.41(12) . . ?
O2 S2 N1 105.10(11) . . ?
O1 S2 N1 104.26(11) . . ?
O2 S2 C7 108.61(11) . . ?
O1 S2 C7 108.88(11) . . ?
N1 S2 C7 107.77(10) . . ?
O3 C17 N3 124.48(19) . . ?
O3 C17 C18 125.96(19) . . ?
N3 C17 C18 109.56(16) . . ?
O4 C19 O5 124.3(2) . . ?
O4 C19 C6 124.41(19) . . ?
O5 C19 C6 111.32(19) . . ?
N2 N1 S2 111.49(13) . . ?
N2 N1 H21 111.0(17) . . ?
S2 N1 H21 109.6(17) . . ?
C19 O5 C14 116.66(19) . . ?
C1 N2 N1 110.27(16) . . ?
C1 N3 C17 115.61(16) . . ?
C1 N3 C4 121.42(16) . . ?
C17 N3 C4 122.55(16) . . ?
C6 C18 C17 120.68(19) . . ?
C6 C18 S1 127.37(18) . . ?
C17 C18 S1 111.94(14) . . ?
C3 C16 C10 118.0(2) . . ?
C3 C16 C12 120.9(2) . . ?
C10 C16 C12 121.1(2) . . ?
N2 C1 N3 120.70(17) . . ?
N2 C1 S1 126.81(15) . . ?
N3 C1 S1 112.46(13) . . ?
C5 C2 C9 120.1(2) . . ?
C5 C2 H2 120.0 . . ?
C9 C2 H2 120.0 . . ?
C11 C3 C16 121.8(2) . . ?
C11 C3 H3 119.1 . . ?
C16 C3 H3 119.1 . . ?
C9 C4 C8 121.3(2) . . ?
C9 C4 N3 118.57(19) . . ?
C8 C4 N3 120.1(2) . . ?
C13 C5 C2 120.6(2) . . ?
C13 C5 H5 119.7 . . ?
C2 C5 H5 119.7 . . ?
C18 C6 C19 121.9(2) . . ?
C18 C6 H6 117.4(17) . . ?
C19 C6 H6 120.7(17) . . ?
C15 C7 C11 120.4(2) . . ?
C15 C7 S2 119.41(17) . . ?
C11 C7 S2 120.06(16) . . ?
C4 C8 C13 118.4(2) . . ?
C4 C8 H8 120.8 . . ?
C13 C8 H8 120.8 . . ?
C4 C9 C2 119.1(2) . . ?
C4 C9 H9 120.4 . . ?
C2 C9 H9 120.4 . . ?
C15 C10 C16 121.2(2) . . ?
C15 C10 H10 119.4 . . ?
C16 C10 H10 119.4 . . ?
C3 C11 C7 119.1(2) . . ?
C3 C11 H11 120.5 . . ?
C7 C11 H11 120.5 . . ?
C16 C12 H12A 109.5 . . ?
C16 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C16 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 C8 120.5(2) . . ?
C5 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 C7 119.4(2) . . ?
C10 C15 H15 120.3 . . ?
C7 C15 H15 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.082
