# Supplementary Information (SI) 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. 
# 
#######################################################################

data_rajat_nts_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2370283'
loop_
_audit_author_name
_audit_author_address
RAJAT
;IIT DELHI
India
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;
_audit_creation_date             2023-06-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.453(4)
_cell_length_b                   10.846(5)
_cell_length_c                   11.701(6)
_cell_angle_alpha                84.04(3)
_cell_angle_beta                 75.55(3)
_cell_angle_gamma                76.36(3)
_cell_volume                     889.1(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4809
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1255 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.7468.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21802
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.799
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_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                2500
_reflns_number_total             3112
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.277
_refine_ls_extinction_coef       0.49(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0972
_refine_ls_restrained_S_all      1.316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2816
_refine_ls_wR_factor_ref         0.3037
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.22479(12) 0.10630(8) 0.12379(8) 0.0425(5) Uani 1 1 d . . . . .
O002 O 0.2562(4) -0.0014(3) 0.0534(3) 0.0525(8) Uani 1 1 d . . . . .
O003 O 0.5423(4) 0.6140(2) 0.1946(3) 0.0519(8) Uani 1 1 d . . . . .
H003 H 0.656486 0.606868 0.187426 0.078 Uiso 1 1 calc R U . . .
O004 O 0.0495(4) 0.1978(3) 0.1390(3) 0.0556(8) Uani 1 1 d . . . . .
N1 N 0.3963(4) 0.1771(3) 0.0596(3) 0.0448(8) Uani 1 1 d . . . . .
H1 H 0.472865 0.146946 -0.004137 0.054 Uiso 1 1 calc R U . . .
N006 N 0.2012(4) 0.6270(3) 0.1644(3) 0.0453(9) Uani 1 1 d . . . . .
H006 H 0.247(7) 0.688(4) 0.167(4) 0.054 Uiso 1 1 d . U . . .
O007 O -0.0789(4) 0.5779(3) 0.1704(4) 0.0751(11) Uani 1 1 d . . . . .
C2 C 0.2867(5) 0.3988(3) 0.1181(3) 0.0417(9) Uani 1 1 d . . . . .
H2 H 0.167490 0.400930 0.105655 0.050 Uiso 1 1 calc R U . . .
C3 C 0.4265(5) 0.2882(3) 0.1045(3) 0.0367(8) Uani 1 1 d . . . . .
C4 C 0.3283(5) 0.5074(3) 0.1510(3) 0.0376(9) Uani 1 1 d . . . . .
C5 C 0.2548(5) 0.0476(3) 0.2639(4) 0.0444(9) Uani 1 1 d . . . . .
C6 C 0.5101(5) 0.5040(3) 0.1672(3) 0.0417(9) Uani 1 1 d . . . . .
C7 C 0.6022(5) 0.2828(3) 0.1230(3) 0.0418(9) Uani 1 1 d . . . . .
H7 H 0.692874 0.206874 0.114868 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6454(5) 0.3913(3) 0.1540(4) 0.0461(10) Uani 1 1 d . . . . .
H8 H 0.765335 0.387816 0.165950 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0777(6) 0.7945(4) 0.1823(5) 0.0640(13) Uani 1 1 d . . . . .
H9A H -0.145258 0.810095 0.262586 0.096 Uiso 1 1 calc R U . . .
H9B H -0.164673 0.818575 0.131496 0.096 Uiso 1 1 calc R U . . .
H9C H 0.018453 0.843412 0.159488 0.096 Uiso 1 1 calc R U . . .
C10 C 0.0124(5) 0.6573(3) 0.1720(3) 0.0447(9) Uani 1 1 d . . . . .
C11 C 0.3561(6) -0.0748(4) 0.2810(4) 0.0558(11) Uani 1 1 d . . . . .
H11 H 0.413109 -0.125795 0.216910 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1764(6) 0.1245(4) 0.3610(4) 0.0574(11) Uani 1 1 d . . . . .
H12 H 0.112174 0.208022 0.350678 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1949(7) 0.0762(5) 0.4701(4) 0.0675(13) Uani 1 1 d . . . . .
H13 H 0.140199 0.128029 0.533816 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2914(7) -0.0469(5) 0.4914(4) 0.0616(12) Uani 1 1 d . . . . .
C15 C 0.3720(7) -0.1201(5) 0.3915(5) 0.0694(13) Uani 1 1 d . . . . .
H15 H 0.438907 -0.202959 0.401491 0.083 Uiso 1 1 calc R U . . .
C16 C 0.3085(9) -0.0997(6) 0.6126(5) 0.0845(17) Uani 1 1 d . . . . .
H16A H 0.285878 -0.031164 0.663716 0.127 Uiso 1 1 calc R U . . .
H16B H 0.433876 -0.150753 0.608714 0.127 Uiso 1 1 calc R U . . .
H16C H 0.216759 -0.151035 0.643053 0.127 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 O002 1.440(3) . ?
S1 O004 1.426(3) . ?
S1 N1 1.628(3) . ?
S1 C5 1.744(4) . ?
O003 H003 0.8200 . ?
O003 C6 1.355(4) . ?
N1 H1 0.8600 . ?
N1 C3 1.448(4) . ?
N006 H006 0.82(5) . ?
N006 C4 1.412(5) . ?
N006 C10 1.350(5) . ?
O007 C10 1.221(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(5) . ?
C2 C4 1.399(5) . ?
C3 C7 1.367(5) . ?
C4 C6 1.406(5) . ?
C5 C11 1.386(5) . ?
C5 C12 1.402(6) . ?
C6 C8 1.384(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C10 1.484(5) . ?
C11 H11 0.9300 . ?
C11 C15 1.359(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(7) . ?
C14 C15 1.406(7) . ?
C14 C16 1.497(6) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O002 S1 N1 104.08(17) . . ?
O002 S1 C5 107.31(18) . . ?
O004 S1 O002 119.91(18) . . ?
O004 S1 N1 108.64(17) . . ?
O004 S1 C5 107.56(18) . . ?
N1 S1 C5 108.98(17) . . ?
C6 O003 H003 109.5 . . ?
S1 N1 H1 118.3 . . ?
C3 N1 S1 123.4(2) . . ?
C3 N1 H1 118.3 . . ?
C4 N006 H006 116(3) . . ?
C10 N006 H006 114(3) . . ?
C10 N006 C4 129.4(3) . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C4 118.6(3) . . ?
C4 C2 H2 120.7 . . ?
C2 C3 N1 120.6(3) . . ?
C7 C3 N1 117.5(3) . . ?
C7 C3 C2 121.7(3) . . ?
C2 C4 N006 124.5(3) . . ?
C2 C4 C6 120.2(3) . . ?
C6 C4 N006 115.2(3) . . ?
C11 C5 S1 120.8(3) . . ?
C11 C5 C12 119.1(4) . . ?
C12 C5 S1 120.1(3) . . ?
O003 C6 C4 116.9(3) . . ?
O003 C6 C8 123.7(3) . . ?
C8 C6 C4 119.4(3) . . ?
C3 C7 H7 120.0 . . ?
C3 C7 C8 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C8 C7 120.1(3) . . ?
C6 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
N006 C10 C9 115.4(3) . . ?
O007 C10 N006 122.6(3) . . ?
O007 C10 C9 122.0(4) . . ?
C5 C11 H11 120.1 . . ?
C15 C11 C5 119.9(4) . . ?
C15 C11 H11 120.1 . . ?
C5 C12 H12 120.3 . . ?
C13 C12 C5 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(4) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 115.7(4) . . ?
C13 C14 C16 122.7(5) . . ?
C15 C14 C16 121.6(5) . . ?
C11 C15 C14 122.6(4) . . ?
C11 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C3 C2 -59.5(4) . . . . ?
S1 N1 C3 C7 125.9(3) . . . . ?
S1 C5 C11 C15 -177.7(3) . . . . ?
S1 C5 C12 C13 177.6(3) . . . . ?
O002 S1 N1 C3 -176.9(3) . . . . ?
O002 S1 C5 C11 20.6(4) . . . . ?
O002 S1 C5 C12 -159.6(3) . . . . ?
O003 C6 C8 C7 -178.5(3) . . . . ?
O004 S1 N1 C3 54.3(3) . . . . ?
O004 S1 C5 C11 150.8(3) . . . . ?
O004 S1 C5 C12 -29.3(4) . . . . ?
N1 S1 C5 C11 -91.6(4) . . . . ?
N1 S1 C5 C12 88.3(4) . . . . ?
N1 C3 C7 C8 173.2(3) . . . . ?
N006 C4 C6 O003 0.6(5) . . . . ?
N006 C4 C6 C8 -179.0(3) . . . . ?
C2 C3 C7 C8 -1.4(5) . . . . ?
C2 C4 C6 O003 177.5(3) . . . . ?
C2 C4 C6 C8 -2.1(5) . . . . ?
C3 C2 C4 N006 178.0(3) . . . . ?
C3 C2 C4 C6 1.3(5) . . . . ?
C3 C7 C8 C6 0.6(6) . . . . ?
C4 N006 C10 O007 1.7(7) . . . . ?
C4 N006 C10 C9 -178.3(4) . . . . ?
C4 C2 C3 N1 -174.0(3) . . . . ?
C4 C2 C3 C7 0.4(5) . . . . ?
C4 C6 C8 C7 1.1(6) . . . . ?
C5 S1 N1 C3 -62.6(3) . . . . ?
C5 C11 C15 C14 -1.0(7) . . . . ?
C5 C12 C13 C14 1.1(7) . . . . ?
C10 N006 C4 C2 14.1(6) . . . . ?
C10 N006 C4 C6 -169.1(4) . . . . ?
C11 C5 C12 C13 -2.5(6) . . . . ?
C12 C5 C11 C15 2.5(6) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C12 C13 C14 C16 -179.1(4) . . . . ?
C13 C14 C15 C11 -0.5(7) . . . . ?
C16 C14 C15 C11 179.1(4) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 58 electrons were 
found in a volume of 182Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CHCl3] per Asymmetric Unit 
which account for 58 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.062 0.500 0.500 182.2 57.8 '1 CHCl3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
