# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_PRR_EN_17_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2335021'
loop_
_audit_author_name
_audit_author_address
'PARBIN RAHMAN'
;GAUHATI UNIVERSITY
India
;
_audit_update_record             
;
2024-02-24 deposited with the CCDC.	2025-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O5 S'
_chemical_formula_weight         332.33

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.7745(7)
_cell_length_b                   8.9918(9)
_cell_length_c                   11.1848(11)
_cell_angle_alpha                84.052(2)
_cell_angle_beta                 77.840(2)
_cell_angle_gamma                78.812(2)
_cell_volume                     748.22(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.244
_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      297(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            15816
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2618
_reflns_number_gt                2273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2019/1 (Sheldrick, 2019)'
_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)+(0.0538P)²+0.6626P] 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_number_reflns         2618
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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 0.68462(7) 0.16583(6) 0.47162(5) 0.03663(18) Uani 1 1 d . . . . .
O4 O 0.6139(2) 0.31235(17) 0.69418(14) 0.0461(4) Uani 1 1 d . . . . .
O5 O 0.5005(2) 0.22369(19) 0.46606(16) 0.0500(4) Uani 1 1 d . . . . .
N2 N 0.7298(2) 0.0888(2) 0.59739(16) 0.0411(4) Uani 1 1 d . . . . .
O2 O 0.3879(3) 0.0971(3) 0.85242(18) 0.0699(6) Uani 1 1 d . . . . .
O3 O 0.8306(3) -0.0237(2) 0.81295(18) 0.0760(6) Uani 1 1 d . . . . .
C9 C 0.8142(3) 0.3086(2) 0.41589(18) 0.0332(4) Uani 1 1 d . . . . .
N1 N 0.3487(3) 0.2031(3) 0.91869(19) 0.0545(5) Uani 1 1 d . . . . .
C8 C 0.6819(3) 0.1785(2) 0.69325(19) 0.0358(5) Uani 1 1 d . . . . .
C10 C 0.7269(3) 0.4526(2) 0.3871(2) 0.0406(5) Uani 1 1 d . . . . .
H10 H 0.602876 0.474521 0.398497 0.049 Uiso 1 1 calc R U . . .
C1 C 0.6658(3) 0.1820(2) 0.92586(19) 0.0398(5) Uani 1 1 d . . . . .
O1 O 0.2004(3) 0.2817(3) 0.9402(2) 0.0882(7) Uani 1 1 d . . . . .
C14 C 0.9983(3) 0.2724(3) 0.4013(2) 0.0438(5) Uani 1 1 d . . . . .
H14 H 1.054459 0.174543 0.420972 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4881(3) 0.2388(3) 0.9741(2) 0.0432(5) Uani 1 1 d . . . . .
C7 C 0.7301(3) 0.0956(3) 0.8128(2) 0.0428(5) Uani 1 1 d . . . . .
C15 C 0.7702(4) 0.0186(3) 0.3732(2) 0.0519(6) Uani 1 1 d . . . . .
H15A H 0.714727 -0.067785 0.404204 0.078 Uiso 1 1 calc R U . . .
H15B H 0.897050 -0.008949 0.368250 0.078 Uiso 1 1 calc R U . . .
H15C H 0.745930 0.051830 0.293082 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8282(4) 0.5633(3) 0.3409(2) 0.0529(6) Uani 1 1 d . . . . .
H11 H 0.772549 0.660993 0.320092 0.063 Uiso 1 1 calc R U . . .
C13 C 1.0965(3) 0.3863(3) 0.3566(2) 0.0570(7) Uani 1 1 d . . . . .
H13 H 1.220331 0.365920 0.347524 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4370(4) 0.3231(3) 1.0754(2) 0.0609(7) Uani 1 1 d . . . . .
H5 H 0.316749 0.358501 1.106098 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7926(3) 0.2136(3) 0.9850(2) 0.0559(6) Uani 1 1 d . . . . .
H2A H 0.912823 0.175866 0.956287 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0113(4) 0.5292(3) 0.3256(2) 0.0596(7) Uani 1 1 d . . . . .
H12 H 1.078627 0.604211 0.293769 0.071 Uiso 1 1 calc R U . . .
C3 C 0.7444(4) 0.2996(4) 1.0852(3) 0.0679(8) Uani 1 1 d . . . . .
H3 H 0.832011 0.321138 1.122606 0.082 Uiso 1 1 calc R U . . .
C4 C 0.5675(5) 0.3539(4) 1.1304(3) 0.0695(8) Uani 1 1 d . . . . .
H4 H 0.535760 0.411777 1.198546 0.083 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 O5 1.4375(16) . ?
S1 N2 1.5792(19) . ?
S1 C15 1.749(2) . ?
S1 C9 1.767(2) . ?
O4 C8 1.217(2) . ?
N2 C8 1.354(3) . ?
O2 N1 1.220(3) . ?
O3 C7 1.198(3) . ?
C9 C14 1.383(3) . ?
C9 C10 1.381(3) . ?
N1 O1 1.220(3) . ?
N1 C6 1.456(3) . ?
C8 C7 1.543(3) . ?
C10 C11 1.380(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.496(3) . ?
C14 C13 1.385(4) . ?
C6 C5 1.374(4) . ?
C11 C12 1.374(4) . ?
C13 C12 1.372(4) . ?
C5 C4 1.376(4) . ?
C2 C3 1.373(4) . ?
C3 C4 1.372(4) . ?

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
O5 S1 N2 118.16(10) . . ?
O5 S1 C15 110.15(12) . . ?
N2 S1 C15 102.03(11) . . ?
O5 S1 C9 109.73(10) . . ?
N2 S1 C9 110.48(10) . . ?
C15 S1 C9 105.34(11) . . ?
C8 N2 S1 115.88(15) . . ?
C14 C9 C10 122.3(2) . . ?
C14 C9 S1 119.29(16) . . ?
C10 C9 S1 118.36(16) . . ?
O2 N1 O1 124.0(2) . . ?
O2 N1 C6 117.9(2) . . ?
O1 N1 C6 118.1(2) . . ?
O4 C8 N2 128.4(2) . . ?
O4 C8 C7 118.62(19) . . ?
N2 C8 C7 112.93(18) . . ?
C11 C10 C9 118.4(2) . . ?
C2 C1 C6 116.9(2) . . ?
C2 C1 C7 117.9(2) . . ?
C6 C1 C7 125.2(2) . . ?
C9 C14 C13 118.0(2) . . ?
C5 C6 C1 122.7(2) . . ?
C5 C6 N1 118.1(2) . . ?
C1 C6 N1 119.1(2) . . ?
O3 C7 C1 121.4(2) . . ?
O3 C7 C8 121.8(2) . . ?
C1 C7 C8 116.26(18) . . ?
C10 C11 C12 120.0(2) . . ?
C12 C13 C14 120.1(2) . . ?
C6 C5 C4 118.6(3) . . ?
C3 C2 C1 121.3(3) . . ?
C13 C12 C11 121.2(2) . . ?
C2 C3 C4 120.3(3) . . ?
C3 C4 C5 120.2(3) . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.045

