# 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 2022

####################################################################### 
# 
# 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_AKS_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2130146'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2021-12-21 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O4 S'
_chemical_formula_weight         384.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.2570(8)
_cell_length_b                   13.741(2)
_cell_length_c                   13.614(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.765(4)
_cell_angle_gamma                90
_cell_volume                     980.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      23.35

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.193
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17997
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.501
_diffrn_reflns_theta_max         23.362
_diffrn_reflns_theta_full        23.362
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2731
_reflns_number_gt                2332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.935

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0535P)²+1.5625P] 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 813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2731
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2045
_refine_ls_wR_factor_gt          0.1953
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_restrained_S_all      1.318
_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 0.4807(6) 0.1407(2) 0.2079(2) 0.0737(10) Uani 1 1 d . . . . .
N1 N 0.3026(17) 0.5667(6) 0.1700(6) 0.047(2) Uani 1 1 d . . . . .
N2 N 0.0955(17) 0.5921(6) 0.1070(7) 0.052(2) Uani 1 1 d . . . . .
O3 O 0.9791(19) 0.5268(7) 0.4190(6) 0.090(3) Uani 1 1 d . . . . .
O2 O 0.3399(18) 0.7220(8) 0.4802(8) 0.096(3) Uani 1 1 d . . . . .
C5 C 0.356(2) 0.4664(7) 0.1809(8) 0.045(3) Uani 1 1 d . . . . .
O4 O 0.8132(17) 0.5942(7) 0.5446(6) 0.087(3) Uani 1 1 d . . . . .
O1 O 0.666(2) 0.7948(8) 0.4160(8) 0.102(3) Uani 1 1 d . . . . .
C14 C 0.4345(17) 0.6434(9) 0.2100(7) 0.047(2) Uani 1 1 d . . . . .
C19 C 0.822(2) 0.5762(8) 0.4518(8) 0.056(3) Uani 1 1 d . . . . .
C8 C 0.100(2) 0.6907(8) 0.1096(8) 0.050(3) Uani 1 1 d . . . . .
C9 C -0.065(2) 0.7549(9) 0.0567(9) 0.062(3) Uani 1 1 d . . . . .
H8 H -0.200327 0.731567 0.014855 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6023(19) 0.6247(8) 0.3886(8) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.449889 0.584126 0.391555 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6634(18) 0.6309(9) 0.2816(7) 0.058(3) Uani 1 1 d . . . . .
H12 H 0.778178 0.685252 0.274489 0.070 Uiso 1 1 calc R U . . .
H13 H 0.752264 0.572052 0.264963 0.070 Uiso 1 1 calc R U . . .
C3 C 0.261(2) 0.3117(9) 0.2465(9) 0.067(3) Uani 1 1 d . . . . .
H4 H 0.165280 0.273969 0.286452 0.080 Uiso 1 1 calc R U . . .
C4 C 0.218(2) 0.4094(8) 0.2392(9) 0.063(3) Uani 1 1 d . . . . .
H5 H 0.092382 0.437611 0.274346 0.076 Uiso 1 1 calc R U . . .
C2 C 0.448(2) 0.2679(8) 0.1944(7) 0.050(3) Uani 1 1 d . . . . .
C6 C 0.542(2) 0.4227(8) 0.1302(8) 0.058(3) Uani 1 1 d . . . . .
H6 H 0.639097 0.460641 0.090913 0.070 Uiso 1 1 calc R U . . .
C17 C 0.546(3) 0.7233(10) 0.4295(10) 0.070(3) Uani 1 1 d . . . . .
C11 C 0.182(3) 0.8885(9) 0.1298(10) 0.077(4) Uani 1 1 d . . . . .
H10 H 0.206532 0.955400 0.134688 0.093 Uiso 1 1 calc R U . . .
C7 C 0.586(2) 0.3254(8) 0.1363(9) 0.060(3) Uani 1 1 d . . . . .
H7 H 0.710180 0.297546 0.100526 0.073 Uiso 1 1 calc R U . . .
C10 C -0.025(3) 0.8512(10) 0.0674(10) 0.072(4) Uani 1 1 d . . . . .
H9 H -0.135275 0.894373 0.033006 0.087 Uiso 1 1 calc R U . . .
C13 C 0.308(2) 0.7250(8) 0.1725(8) 0.053(3) Uani 1 1 d . . . . .
C12 C 0.343(2) 0.8277(8) 0.1823(10) 0.065(4) Uani 1 1 d . . . . .
H11 H 0.475169 0.852517 0.224436 0.078 Uiso 1 1 calc R U . . .
C1 C 0.681(3) 0.1072(10) 0.1172(11) 0.099(5) Uani 1 1 d . . . . .
H3 H 0.614147 0.132277 0.054497 0.149 Uiso 1 1 calc R U . . .
H2 H 0.691320 0.037543 0.113855 0.149 Uiso 1 1 calc R U . . .
H1 H 0.848939 0.133453 0.133410 0.149 Uiso 1 1 calc R U . . .
C20 C 1.007(4) 0.5471(15) 0.6107(11) 0.123(6) Uani 1 1 d . . . . .
H19 H 1.009041 0.478594 0.596945 0.185 Uiso 1 1 calc R U . . .
H18 H 0.968980 0.557161 0.677723 0.185 Uiso 1 1 calc R U . . .
H20 H 1.171225 0.574469 0.601157 0.185 Uiso 1 1 calc R U . . .
C18 C 0.275(4) 0.8130(15) 0.5245(14) 0.140(8) Uani 1 1 d . . . . .
H15 H 0.407565 0.831045 0.573818 0.211 Uiso 1 1 calc R U . . .
H16 H 0.116877 0.805882 0.554387 0.211 Uiso 1 1 calc R U . . .
H17 H 0.256931 0.862530 0.474698 0.211 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 C1 1.752(14) . ?
S1 C2 1.764(11) . ?
N1 C14 1.350(13) . ?
N1 N2 1.374(12) . ?
N1 C5 1.413(13) . ?
N2 C8 1.355(12) . ?
O3 C19 1.185(13) . ?
O2 C17 1.332(15) . ?
O2 C18 1.440(18) . ?
C5 C4 1.368(15) . ?
C5 C6 1.379(15) . ?
O4 C19 1.291(13) . ?
O4 C20 1.454(16) . ?
O1 C17 1.190(16) . ?
C14 C13 1.381(15) . ?
C14 C15 1.494(13) . ?
C19 C16 1.534(15) . ?
C8 C9 1.396(15) . ?
C8 C13 1.411(16) . ?
C9 C10 1.346(16) . ?
C16 C17 1.503(17) . ?
C16 C15 1.520(14) . ?
C3 C4 1.364(17) . ?
C3 C2 1.394(15) . ?
C2 C7 1.367(15) . ?
C6 C7 1.358(16) . ?
C11 C12 1.350(17) . ?
C11 C10 1.417(19) . ?
C13 C12 1.427(16) . ?

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
C1 S1 C2 104.3(6) . . ?
C14 N1 N2 114.1(8) . . ?
C14 N1 C5 128.8(9) . . ?
N2 N1 C5 117.0(8) . . ?
C8 N2 N1 103.0(9) . . ?
C17 O2 C18 115.9(13) . . ?
C4 C5 C6 118.3(10) . . ?
C4 C5 N1 120.5(9) . . ?
C6 C5 N1 121.1(10) . . ?
C19 O4 C20 116.1(10) . . ?
N1 C14 C13 105.6(8) . . ?
N1 C14 C15 122.2(10) . . ?
C13 C14 C15 132.2(11) . . ?
O3 C19 O4 124.1(11) . . ?
O3 C19 C16 123.6(10) . . ?
O4 C19 C16 112.3(10) . . ?
N2 C8 C9 127.5(12) . . ?
N2 C8 C13 111.2(11) . . ?
C9 C8 C13 121.3(11) . . ?
C10 C9 C8 118.6(12) . . ?
C17 C16 C15 111.6(11) . . ?
C17 C16 C19 110.3(9) . . ?
C15 C16 C19 110.7(9) . . ?
C14 C15 C16 114.1(8) . . ?
C4 C3 C2 120.6(11) . . ?
C3 C4 C5 120.7(10) . . ?
C7 C2 C3 118.3(10) . . ?
C7 C2 S1 125.5(8) . . ?
C3 C2 S1 116.2(9) . . ?
C7 C6 C5 121.5(11) . . ?
O1 C17 O2 123.7(13) . . ?
O1 C17 C16 124.3(13) . . ?
O2 C17 C16 112.0(12) . . ?
C12 C11 C10 120.5(12) . . ?
C6 C7 C2 120.6(10) . . ?
C9 C10 C11 121.8(12) . . ?
C14 C13 C8 106.1(10) . . ?
C14 C13 C12 135.6(12) . . ?
C8 C13 C12 118.3(11) . . ?
C11 C12 C13 119.5(12) . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.061

