# 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. 
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data_rajat_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2n4dbk
_database_code_depnum_ccdc_archive 'CCDC 2447088'
loop_
_audit_author_name
_audit_author_address
RAJAT
;IIT DELHI
India
;
_audit_update_record             
;
2025-04-28 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_audit_creation_date             2024-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.21
_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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.146(4)
_cell_length_b                   17.380(8)
_cell_length_c                   7.782(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.193(19)
_cell_angle_gamma                90
_cell_volume                     1100.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3348
_cell_measurement_temperature    152(2)
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1570 before and 0.1116 after correction.
The Ratio of minimum to maximum transmission is 0.6861.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8670
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.418
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_temperature      152.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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                1159
_reflns_number_total             2019
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    ?
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      0.996
_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)+(0.1661P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1_1 O 0.6769(4) 0.54237(16) 0.5593(3) 0.0884(10) Uani 1 1 d . . . . .
O2_1 O 0.9540(3) 0.64743(16) 0.3781(4) 0.0742(9) Uani 1 1 d . . . . .
O3_1 O 0.9465(4) 0.73658(17) 0.1883(5) 0.0937(11) Uani 1 1 d . . . . .
N1_1 N 0.8804(4) 0.69598(17) 0.2942(4) 0.0605(8) Uani 1 1 d . . . . .
C1_1 C 0.7407(4) 0.51873(18) 0.2706(5) 0.0535(9) Uani 1 1 d . . . . .
C2_1 C 0.8415(5) 0.4569(2) 0.3083(6) 0.0668(11) Uani 1 1 d . . . . .
H2_1 H 0.874302 0.445853 0.424125 0.080 Uiso 1 1 calc R U . . .
C3_1 C 0.8949(5) 0.4108(2) 0.1764(8) 0.0793(13) Uani 1 1 d . . . . .
H3_1 H 0.964761 0.368198 0.201906 0.095 Uiso 1 1 calc R U . . .
C4_1 C 0.8479(5) 0.4263(3) 0.0106(8) 0.0835(14) Uani 1 1 d . . . . .
H4_1 H 0.885494 0.394542 -0.079077 0.100 Uiso 1 1 calc R U . . .
C5_1 C 0.7471(5) 0.4871(3) -0.0283(5) 0.0761(12) Uani 1 1 d . . . . .
H5_1 H 0.713800 0.497022 -0.144469 0.091 Uiso 1 1 calc R U . . .
C6_1 C 0.6936(5) 0.5341(2) 0.1007(5) 0.0600(10) Uani 1 1 d . . . . .
H6_1 H 0.624816 0.576868 0.073464 0.072 Uiso 1 1 calc R U . . .
C7_1 C 0.6796(5) 0.5664(2) 0.4119(5) 0.0602(10) Uani 1 1 d . . . . .
C8_1 C 0.6125(4) 0.64510(19) 0.3744(4) 0.0553(9) Uani 1 1 d . . . . .
C9_1 C 0.4481(5) 0.6590(3) 0.3967(5) 0.0712(11) Uani 1 1 d . . . . .
H9_1 H 0.379459 0.618013 0.430772 0.085 Uiso 1 1 calc R U . . .
C10_1 C 0.3810(5) 0.7311(3) 0.3708(6) 0.0787(12) Uani 1 1 d . . . . .
H10_1 H 0.267298 0.739221 0.387108 0.094 Uiso 1 1 calc R U . . .
C11_1 C 0.4780(5) 0.7913(2) 0.3216(5) 0.0733(12) Uani 1 1 d . . . . .
H11_1 H 0.431459 0.841046 0.306450 0.088 Uiso 1 1 calc R U . . .
C12_1 C 0.6412(5) 0.7799(2) 0.2943(5) 0.0634(10) Uani 1 1 d . . . . .
H12_1 H 0.708550 0.821073 0.258331 0.076 Uiso 1 1 calc R U . . .
C13_1 C 0.7059(4) 0.70696(19) 0.3204(4) 0.0521(9) Uani 1 1 d . . . . .


_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
O1_1 C7_1 1.221(4) . ?
O2_1 N1_1 1.212(4) . ?
O3_1 N1_1 1.225(4) . ?
N1_1 C13_1 1.457(4) . ?
C1_1 C2_1 1.378(5) . ?
C1_1 C6_1 1.389(5) . ?
C1_1 C7_1 1.478(5) . ?
C2_1 H2_1 0.9500 . ?
C2_1 C3_1 1.385(6) . ?
C3_1 H3_1 0.9500 . ?
C3_1 C4_1 1.359(7) . ?
C4_1 H4_1 0.9500 . ?
C4_1 C5_1 1.365(7) . ?
C5_1 H5_1 0.9500 . ?
C5_1 C6_1 1.378(5) . ?
C6_1 H6_1 0.9500 . ?
C7_1 C8_1 1.498(5) . ?
C8_1 C9_1 1.378(5) . ?
C8_1 C13_1 1.391(5) . ?
C9_1 H9_1 0.9500 . ?
C9_1 C10_1 1.379(6) . ?
C10_1 H10_1 0.9500 . ?
C10_1 C11_1 1.373(6) . ?
C11_1 H11_1 0.9500 . ?
C11_1 C12_1 1.369(5) . ?
C12_1 H12_1 0.9500 . ?
C12_1 C13_1 1.385(5) . ?

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
O2_1 N1_1 O3_1 122.9(3) . . ?
O2_1 N1_1 C13_1 118.8(3) . . ?
O3_1 N1_1 C13_1 118.4(3) . . ?
C2_1 C1_1 C6_1 119.5(4) . . ?
C2_1 C1_1 C7_1 119.6(3) . . ?
C6_1 C1_1 C7_1 120.8(3) . . ?
C1_1 C2_1 H2_1 120.2 . . ?
C1_1 C2_1 C3_1 119.7(4) . . ?
C3_1 C2_1 H2_1 120.2 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C4_1 C3_1 C2_1 120.2(4) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 H4_1 119.7 . . ?
C3_1 C4_1 C5_1 120.6(4) . . ?
C5_1 C4_1 H4_1 119.7 . . ?
C4_1 C5_1 H5_1 119.9 . . ?
C4_1 C5_1 C6_1 120.1(4) . . ?
C6_1 C5_1 H5_1 119.9 . . ?
C1_1 C6_1 H6_1 120.1 . . ?
C5_1 C6_1 C1_1 119.8(4) . . ?
C5_1 C6_1 H6_1 120.1 . . ?
O1_1 C7_1 C1_1 121.7(3) . . ?
O1_1 C7_1 C8_1 118.4(3) . . ?
C1_1 C7_1 C8_1 119.8(3) . . ?
C9_1 C8_1 C7_1 119.0(3) . . ?
C9_1 C8_1 C13_1 116.6(3) . . ?
C13_1 C8_1 C7_1 124.4(3) . . ?
C8_1 C9_1 H9_1 119.2 . . ?
C8_1 C9_1 C10_1 121.5(4) . . ?
C10_1 C9_1 H9_1 119.2 . . ?
C9_1 C10_1 H10_1 119.9 . . ?
C11_1 C10_1 C9_1 120.2(4) . . ?
C11_1 C10_1 H10_1 119.9 . . ?
C10_1 C11_1 H11_1 119.8 . . ?
C12_1 C11_1 C10_1 120.4(4) . . ?
C12_1 C11_1 H11_1 119.8 . . ?
C11_1 C12_1 H12_1 120.8 . . ?
C11_1 C12_1 C13_1 118.4(4) . . ?
C13_1 C12_1 H12_1 120.8 . . ?
C8_1 C13_1 N1_1 119.3(3) . . ?
C12_1 C13_1 N1_1 117.8(3) . . ?
C12_1 C13_1 C8_1 122.9(3) . . ?

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
O1_1 C7_1 C8_1 C9_1 -63.7(5) . . . . ?
O1_1 C7_1 C8_1 C13_1 115.1(4) . . . . ?
O2_1 N1_1 C13_1 C8_1 -28.6(5) . . . . ?
O2_1 N1_1 C13_1 C12_1 149.7(3) . . . . ?
O3_1 N1_1 C13_1 C8_1 151.6(4) . . . . ?
O3_1 N1_1 C13_1 C12_1 -30.0(5) . . . . ?
C1_1 C2_1 C3_1 C4_1 -0.2(6) . . . . ?
C1_1 C7_1 C8_1 C9_1 113.9(4) . . . . ?
C1_1 C7_1 C8_1 C13_1 -67.3(5) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.5(5) . . . . ?
C2_1 C1_1 C7_1 O1_1 -20.2(5) . . . . ?
C2_1 C1_1 C7_1 C8_1 162.3(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.3(6) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.8(6) . . . . ?
C4_1 C5_1 C6_1 C1_1 -0.9(6) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.1(5) . . . . ?
C6_1 C1_1 C7_1 O1_1 157.8(4) . . . . ?
C6_1 C1_1 C7_1 C8_1 -19.7(5) . . . . ?
C7_1 C1_1 C2_1 C3_1 178.1(3) . . . . ?
C7_1 C1_1 C6_1 C5_1 -177.5(3) . . . . ?
C7_1 C8_1 C9_1 C10_1 177.4(4) . . . . ?
C7_1 C8_1 C13_1 N1_1 1.3(5) . . . . ?
C7_1 C8_1 C13_1 C12_1 -177.0(3) . . . . ?
C8_1 C9_1 C10_1 C11_1 0.0(7) . . . . ?
C9_1 C8_1 C13_1 N1_1 -179.9(3) . . . . ?
C9_1 C8_1 C13_1 C12_1 1.8(5) . . . . ?
C9_1 C10_1 C11_1 C12_1 1.4(6) . . . . ?
C10_1 C11_1 C12_1 C13_1 -1.1(6) . . . . ?
C11_1 C12_1 C13_1 N1_1 -178.8(3) . . . . ?
C11_1 C12_1 C13_1 C8_1 -0.5(6) . . . . ?
C13_1 C8_1 C9_1 C10_1 -1.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
