# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_vbchem348A_a
_database_code_depnum_ccdc_archive 'CCDC 1976157'
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N2 O3 S'
_chemical_formula_sum            'C20 H18 N2 O3 S'
_chemical_formula_weight         366.42

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.0148(14)
_cell_length_b                   17.582(4)
_cell_length_c                   14.402(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1776.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    68068
_cell_measurement_theta_min      2.317
_cell_measurement_theta_max      28.298

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68068
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4404
_reflns_number_gt                3413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.6064P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4404
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_restrained_S_all      0.855
_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 0.60645(13) 0.44608(6) 0.70116(6) 0.0501(3) Uani 1 1 d . . . . .
O3 O 0.4289(4) 0.22238(17) 0.3533(2) 0.0575(8) Uani 1 1 d . . . . .
O1 O 0.6395(4) 0.68300(18) 0.4839(2) 0.0543(7) Uani 1 1 d . . . . .
O2 O 0.4566(5) 0.34038(19) 0.2985(2) 0.0610(8) Uani 1 1 d . . . . .
N1 N 0.6311(4) 0.37329(18) 0.5456(2) 0.0386(6) Uani 1 1 d . . . . .
N2 N 0.6403(5) 0.2907(2) 0.6633(2) 0.0491(8) Uani 1 1 d . . . . .
C3 C 0.6190(4) 0.5758(2) 0.5903(2) 0.0417(8) Uani 1 1 d . . . . .
H3 H 0.6123 0.6065 0.6427 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6162(4) 0.4976(2) 0.5972(2) 0.0382(7) Uani 1 1 d . . . . .
C9 C 0.6613(5) 0.2518(2) 0.5799(3) 0.0474(8) Uani 1 1 d . . . . .
C2 C 0.6322(4) 0.6068(2) 0.5019(2) 0.0411(7) Uani 1 1 d . . . . .
C18 C 0.5137(5) 0.2896(2) 0.3458(3) 0.0455(8) Uani 1 1 d . . . . .
C8 C 0.6237(5) 0.3611(2) 0.6396(3) 0.0446(8) Uani 1 1 d . . . . .
C10 C 0.6584(5) 0.3017(2) 0.5056(3) 0.0424(8) Uani 1 1 d . . . . .
C6 C 0.6331(4) 0.4826(2) 0.4309(2) 0.0394(7) Uani 1 1 d . . . . .
H6 H 0.6340 0.4521 0.3782 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6268(4) 0.4501(2) 0.5196(2) 0.0350(7) Uani 1 1 d . . . . .
C11 C 0.6979(5) 0.1695(3) 0.5818(3) 0.0546(10) Uani 1 1 d . . . . .
C19 C 0.2514(8) 0.2120(3) 0.3032(4) 0.0684(12) Uani 1 1 d . . . . .
H19A H 0.2730 0.2165 0.2369 0.082 Uiso 1 1 calc R U . . .
H19B H 0.1597 0.2504 0.3217 0.082 Uiso 1 1 calc R U . . .
C17 C 0.6949(5) 0.2923(2) 0.4044(3) 0.0463(8) Uani 1 1 d . . . . .
H17A H 0.7660 0.2456 0.3947 0.056 Uiso 1 1 calc R U . . .
H17B H 0.7736 0.3342 0.3831 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6378(5) 0.5602(2) 0.4233(2) 0.0422(8) Uani 1 1 d . . . . .
H7 H 0.6449 0.5823 0.3648 0.051 Uiso 1 1 calc R U . . .
C1 C 0.6566(6) 0.7326(3) 0.5613(3) 0.0569(11) Uani 1 1 d . . . . .
H1A H 0.5463 0.7275 0.6003 0.085 Uiso 1 1 calc R U . . .
H1B H 0.6663 0.7841 0.5399 0.085 Uiso 1 1 calc R U . . .
H1C H 0.7688 0.7197 0.5961 0.085 Uiso 1 1 calc R U . . .
C12 C 0.7718(7) 0.1377(3) 0.6628(4) 0.0705(13) Uani 1 1 d . . . . .
H12 H 0.7952 0.1687 0.7139 0.085 Uiso 1 1 calc R U . . .
C16 C 0.6674(8) 0.1221(3) 0.5075(4) 0.0721(13) Uani 1 1 d . . . . .
H16 H 0.6171 0.1418 0.4528 0.087 Uiso 1 1 calc R U . . .
C13 C 0.8106(9) 0.0612(3) 0.6683(6) 0.092(2) Uani 1 1 d . . . . .
H13 H 0.8555 0.0406 0.7236 0.110 Uiso 1 1 calc R U . . .
C14 C 0.7835(9) 0.0152(3) 0.5927(7) 0.094(2) Uani 1 1 d . . . . .
H14 H 0.8146 -0.0362 0.5958 0.112 Uiso 1 1 calc R U . . .
C15 C 0.7107(11) 0.0451(3) 0.5129(6) 0.095(2) Uani 1 1 d . . . . .
H15 H 0.6899 0.0138 0.4618 0.114 Uiso 1 1 calc R U . . .
C20 C 0.1782(11) 0.1350(4) 0.3258(7) 0.115(3) Uani 1 1 d . . . . .
H20A H 0.2703 0.0975 0.3074 0.173 Uiso 1 1 calc R U . . .
H20B H 0.0609 0.1264 0.2932 0.173 Uiso 1 1 calc R U . . .
H20C H 0.1562 0.1314 0.3915 0.173 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 C8 1.741(4) . ?
S1 C4 1.751(4) . ?
O3 C18 1.327(5) . ?
O3 C19 1.451(5) . ?
O1 C2 1.366(5) . ?
O1 C1 1.420(5) . ?
O2 C18 1.192(5) . ?
N1 C8 1.372(5) . ?
N1 C10 1.397(5) . ?
N1 C5 1.402(5) . ?
N2 C8 1.290(5) . ?
N2 C9 1.390(5) . ?
C3 C4 1.379(6) . ?
C3 C2 1.388(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C9 C10 1.384(6) . ?
C9 C11 1.470(6) . ?
C2 C7 1.397(5) . ?
C18 C17 1.526(6) . ?
C10 C17 1.490(5) . ?
C6 C7 1.369(5) . ?
C6 C5 1.401(5) . ?
C6 H6 0.9300 . ?
C11 C16 1.374(8) . ?
C11 C12 1.394(7) . ?
C19 C20 1.483(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C12 C13 1.375(7) . ?
C12 H12 0.9300 . ?
C16 C15 1.390(8) . ?
C16 H16 0.9300 . ?
C13 C14 1.370(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C8 S1 C4 90.31(18) . . ?
C18 O3 C19 117.1(3) . . ?
C2 O1 C1 117.2(3) . . ?
C8 N1 C10 105.7(3) . . ?
C8 N1 C5 114.4(3) . . ?
C10 N1 C5 139.6(3) . . ?
C8 N2 C9 104.7(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 S1 125.3(3) . . ?
C5 C4 S1 112.2(3) . . ?
C10 C9 N2 110.8(4) . . ?
C10 C9 C11 129.9(4) . . ?
N2 C9 C11 119.1(4) . . ?
O1 C2 C3 124.2(3) . . ?
O1 C2 C7 114.9(3) . . ?
C3 C2 C7 121.0(4) . . ?
O2 C18 O3 124.3(4) . . ?
O2 C18 C17 124.9(4) . . ?
O3 C18 C17 110.8(3) . . ?
N2 C8 N1 114.0(4) . . ?
N2 C8 S1 134.1(3) . . ?
N1 C8 S1 111.8(3) . . ?
C9 C10 N1 104.8(3) . . ?
C9 C10 C17 133.1(4) . . ?
N1 C10 C17 121.8(4) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 N1 111.3(3) . . ?
C6 C5 N1 129.5(3) . . ?
C16 C11 C12 117.8(4) . . ?
C16 C11 C9 123.8(4) . . ?
C12 C11 C9 118.4(4) . . ?
O3 C19 C20 107.6(4) . . ?
O3 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C10 C17 C18 113.7(3) . . ?
C10 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C10 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C11 C16 C15 120.9(6) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.3(7) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051

