# 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. 
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data_pb_15_nu1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2269889'
loop_
_audit_author_name
_audit_author_address
'Kamlesh Satpute'
;IIT Ropar
India
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2023-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N2 O7 S2'
_chemical_formula_sum            'C24 H20 N2 O7 S2'
_chemical_formula_weight         512.54
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   15.700(2)
_cell_length_b                   11.2137(13)
_cell_length_c                   13.4533(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2368.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.2073 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.7416.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'plate shape'
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   0.7453
_exptl_transmission_factor_min   0.5527
_diffrn_reflns_av_R_equivalents  0.1737
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36961
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.695
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1263
_reflns_number_total             2258
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
1.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.28895(5) 0.62112(6) 0.53476(5) 0.0568(6) Uani 1 1 d . . . . .
O1 O 0.33691(13) 0.72793(16) 0.54289(13) 0.0681(8) Uani 1 1 d . . . . .
O4 O 0.24004(13) 0.60083(19) 0.44742(13) 0.0741(8) Uani 1 1 d . . . . .
O3 O 0.41206(14) 0.6369(2) 0.71996(15) 0.0809(9) Uani 1 1 d . . . . .
N1 N 0.35723(13) 0.50477(19) 0.53741(13) 0.0527(8) Uani 1 1 d . . . . .
O2 O 0.500000 0.4823(3) 0.750000 0.0870(11) Uani 1 2 d S T P . .
C13 C 0.06384(19) 0.5455(3) 0.8930(2) 0.0830(11) Uani 1 1 d . . . . .
H13A H 0.088761 0.583502 0.949904 0.124 Uiso 1 1 calc R U . . .
H13B H 0.057779 0.461642 0.905699 0.124 Uiso 1 1 calc R U . . .
H13C H 0.008860 0.579580 0.880096 0.124 Uiso 1 1 calc R U . . .
C2 C 0.12082(17) 0.5638(3) 0.80344(19) 0.0623(10) Uani 1 1 d . . . . .
C3 C 0.13166(18) 0.4748(3) 0.7330(2) 0.0652(10) Uani 1 1 d . . . . .
H3 H 0.103829 0.402214 0.741019 0.078 Uiso 1 1 calc R U . . .
C4 C 0.18288(17) 0.4923(3) 0.6516(2) 0.0609(9) Uani 1 1 d . . . . .
H4 H 0.188794 0.432372 0.604274 0.073 Uiso 1 1 calc R U . . .
C5 C 0.22573(16) 0.5994(2) 0.64019(18) 0.0503(9) Uani 1 1 d . . . . .
C6 C 0.41967(16) 0.4741(2) 0.60679(19) 0.0536(8) Uani 1 1 d . . . . .
C7 C 0.44083(18) 0.5446(3) 0.6936(2) 0.0617(9) Uani 1 1 d . . . . .
C8 C 0.21682(18) 0.6881(3) 0.7100(2) 0.0629(9) Uani 1 1 d . . . . .
H8 H 0.246238 0.759574 0.703202 0.075 Uiso 1 1 calc R U . . .
C9 C 0.16400(19) 0.6699(3) 0.7900(2) 0.0677(10) Uani 1 1 d . . . . .
H9 H 0.157142 0.730617 0.836399 0.081 Uiso 1 1 calc R U . . .
C10 C 0.45492(19) 0.3693(3) 0.5752(2) 0.0702(10) Uani 1 1 d . . . . .
H10 H 0.498544 0.328118 0.606944 0.084 Uiso 1 1 calc R U . . .
C11 C 0.4149(2) 0.3346(3) 0.4880(2) 0.0797(11) Uani 1 1 d . . . . .
H11 H 0.427133 0.266545 0.451228 0.096 Uiso 1 1 calc R U . . .
C12 C 0.3554(2) 0.4161(3) 0.4660(2) 0.0659(10) Uani 1 1 d . . . . .
H12 H 0.318826 0.413511 0.411677 0.079 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 O1 1.4190(19) . ?
S1 O4 1.4220(19) . ?
S1 N1 1.689(2) . ?
S1 C5 1.748(3) . ?
O3 C7 1.184(3) . ?
N1 C6 1.396(3) . ?
N1 C12 1.382(3) . ?
O2 C7 1.387(3) . ?
O2 C7 1.387(3) 3_656 ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C2 1.515(4) . ?
C2 C3 1.387(4) . ?
C2 C9 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 C8 1.376(3) . ?
C6 C7 1.449(4) . ?
C6 C10 1.367(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.340(4) . ?
C12 H12 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
O1 S1 O4 119.03(12) . . ?
O1 S1 N1 108.27(11) . . ?
O1 S1 C5 110.89(12) . . ?
O4 S1 N1 103.69(11) . . ?
O4 S1 C5 109.97(13) . . ?
N1 S1 C5 103.61(11) . . ?
C6 N1 S1 130.52(17) . . ?
C12 N1 S1 121.8(2) . . ?
C12 N1 C6 107.6(2) . . ?
C7 O2 C7 119.6(3) . 3_656 ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
C3 C2 C13 121.2(3) . . ?
C9 C2 C13 120.7(3) . . ?
C9 C2 C3 118.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 S1 119.1(2) . . ?
C8 C5 S1 120.7(2) . . ?
C8 C5 C4 120.1(3) . . ?
N1 C6 C7 124.5(2) . . ?
C10 C6 N1 106.7(2) . . ?
C10 C6 C7 128.8(3) . . ?
O3 C7 O2 122.1(3) . . ?
O3 C7 C6 129.1(3) . . ?
O2 C7 C6 108.7(3) . . ?
C5 C8 H8 120.4 . . ?
C9 C8 C5 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C2 C9 H9 119.1 . . ?
C8 C9 C2 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C6 C10 H10 125.6 . . ?
C6 C10 C11 108.7(3) . . ?
C11 C10 H10 125.6 . . ?
C10 C11 H11 125.9 . . ?
C12 C11 C10 108.1(3) . . ?
C12 C11 H11 125.9 . . ?
N1 C12 H12 125.6 . . ?
C11 C12 N1 108.8(3) . . ?
C11 C12 H12 125.6 . . ?

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
S1 N1 C6 C7 -2.7(4) . . . . ?
S1 N1 C6 C10 178.0(2) . . . . ?
S1 N1 C12 C11 -178.5(2) . . . . ?
S1 C5 C8 C9 177.4(2) . . . . ?
O1 S1 N1 C6 54.4(2) . . . . ?
O1 S1 N1 C12 -128.9(2) . . . . ?
O1 S1 C5 C4 -171.66(19) . . . . ?
O1 S1 C5 C8 9.8(3) . . . . ?
O4 S1 N1 C6 -178.3(2) . . . . ?
O4 S1 N1 C12 -1.5(2) . . . . ?
O4 S1 C5 C4 54.6(2) . . . . ?
O4 S1 C5 C8 -123.9(2) . . . . ?
N1 S1 C5 C4 -55.7(2) . . . . ?
N1 S1 C5 C8 125.8(2) . . . . ?
N1 C6 C7 O3 -1.3(5) . . . . ?
N1 C6 C7 O2 174.8(2) . . . . ?
N1 C6 C10 C11 -0.4(3) . . . . ?
C13 C2 C3 C4 179.5(2) . . . . ?
C13 C2 C9 C8 179.2(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C2 C9 C8 -0.4(4) . . . . ?
C3 C4 C5 S1 -178.70(19) . . . . ?
C3 C4 C5 C8 -0.2(4) . . . . ?
C4 C5 C8 C9 -1.1(4) . . . . ?
C5 S1 N1 C6 -63.4(2) . . . . ?
C5 S1 N1 C12 113.3(2) . . . . ?
C5 C8 C9 C2 1.4(4) . . . . ?
C6 N1 C12 C11 -1.2(3) . . . . ?
C6 C10 C11 C12 -0.3(4) . . . . ?
C7 O2 C7 O3 -34.0(2) 3_656 . . . ?
C7 O2 C7 C6 149.6(2) 3_656 . . . ?
C7 C6 C10 C11 -179.7(3) . . . . ?
C9 C2 C3 C4 -0.9(4) . . . . ?
C10 C6 C7 O3 177.8(3) . . . . ?
C10 C6 C7 O2 -6.0(4) . . . . ?
C10 C11 C12 N1 0.9(4) . . . . ?
C12 N1 C6 C7 -179.7(3) . . . . ?
C12 N1 C6 C10 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
