# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_tpkv111_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2516536'
loop_
_audit_author_name
_audit_author_address
'kshitiz verma'
;IIT guwahati
India
;
_audit_update_record             
;
2025-12-16 deposited with the CCDC.	2026-05-01 downloaded from the CCDC.
;
_audit_creation_date             2025-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O5'
_chemical_formula_sum            'C14 H13 N3 O5'
_chemical_formula_weight         303.27
_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                   8.740(3)
_cell_length_b                   21.397(7)
_cell_length_c                   7.686(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.897(9)
_cell_angle_gamma                90
_cell_volume                     1411.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            34323
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.903
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2093
_reflns_number_total             2459
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.059
_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)+(0.0371P)²+0.5174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00C,H00D), C00L(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00H(H00H), C00I(H00I)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C00M(H00G,H00J,H00K)
;
_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
O001 O 0.90517(15) 0.37341(7) 1.05016(18) 0.0728(4) Uani 1 1 d . . . . .
O002 O 0.35632(15) 0.32286(7) 0.7829(2) 0.0722(4) Uani 1 1 d . . . . .
N003 N 0.82817(16) 0.34972(7) 0.75836(18) 0.0505(4) Uani 1 1 d . . . . .
O004 O 0.19259(18) 0.45918(8) 0.3215(2) 0.0813(5) Uani 1 1 d . . . . .
O2 O 0.30054(19) 0.50310(7) 0.12406(19) 0.0817(5) Uani 1 1 d . . . . .
O1 O 0.37124(17) 0.22078(6) 0.7336(2) 0.0755(4) Uani 1 1 d . . . . .
N1 N 0.86836(17) 0.36819(7) 0.5917(2) 0.0574(4) Uani 1 1 d . . . . .
N2 N 0.3068(2) 0.46980(7) 0.2556(2) 0.0593(4) Uani 1 1 d . . . . .
C009 C 0.60785(18) 0.38677(7) 0.5736(2) 0.0410(4) Uani 1 1 d . . . . .
C00A C 0.46486(19) 0.41002(7) 0.4953(2) 0.0438(4) Uani 1 1 d . . . . .
H00A H 0.377296 0.403852 0.545611 0.053 Uiso 1 1 calc R U . . .
C00B C 0.65778(18) 0.34829(7) 0.7411(2) 0.0425(4) Uani 1 1 d . . . . .
H00B H 0.627275 0.369606 0.842167 0.051 Uiso 1 1 calc R U . . .
C00C C 0.7378(2) 0.39697(8) 0.4959(2) 0.0471(4) Uani 1 1 d . . . . .
C00D C 0.5928(2) 0.28238(7) 0.7255(2) 0.0462(4) Uani 1 1 d . . . . .
C00E C 0.9247(2) 0.37734(9) 0.8990(3) 0.0560(5) Uani 1 1 d . . . . .
C00F C 0.4559(2) 0.44315(7) 0.3377(2) 0.0479(4) Uani 1 1 d . . . . .
C00G C 0.4296(2) 0.27838(8) 0.7501(2) 0.0510(4) Uani 1 1 d . . . . .
C00H C 0.7271(2) 0.42983(9) 0.3379(2) 0.0573(5) Uani 1 1 d . . . . .
H00H H 0.814257 0.435929 0.286768 0.069 Uiso 1 1 calc R U . . .
C00I C 0.5841(2) 0.45298(8) 0.2597(2) 0.0567(5) Uani 1 1 d . . . . .
H00I H 0.573437 0.475291 0.154265 0.068 Uiso 1 1 calc R U . . .
C1 C 0.6724(3) 0.23289(9) 0.6926(3) 0.0695(6) Uani 1 1 d . . . . .
H1A H 0.625883 0.193636 0.684164 0.083 Uiso 1 1 calc R U . . .
H1B H 0.775030 0.237209 0.677886 0.083 Uiso 1 1 calc R U . . .
C00K C 1.0531(2) 0.40987(11) 0.8293(3) 0.0746(6) Uani 1 1 d . . . . .
H00C H 1.052418 0.454282 0.854483 0.090 Uiso 1 1 calc R U . . .
H00D H 1.153679 0.392894 0.883720 0.090 Uiso 1 1 calc R U . . .
C00L C 1.0222(2) 0.39872(12) 0.6338(3) 0.0808(7) Uani 1 1 d . . . . .
H00E H 1.021150 0.437929 0.570194 0.097 Uiso 1 1 calc R U . . .
H00F H 1.101878 0.371935 0.601304 0.097 Uiso 1 1 calc R U . . .
C00M C 0.2120(3) 0.21372(13) 0.7565(4) 0.0928(8) Uani 1 1 d . . . . .
H00G H 0.202755 0.227818 0.872691 0.139 Uiso 1 1 calc R U . . .
H00J H 0.182514 0.170513 0.743278 0.139 Uiso 1 1 calc R U . . .
H00K H 0.144793 0.238137 0.668951 0.139 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
O001 C00E 1.208(2) . ?
O002 C00G 1.200(2) . ?
N003 N1 1.446(2) . ?
N003 C00B 1.470(2) . ?
N003 C00E 1.373(2) . ?
O004 N2 1.223(2) . ?
O2 N2 1.229(2) . ?
O1 C00G 1.331(2) . ?
O1 C00M 1.444(3) . ?
N1 C00C 1.381(2) . ?
N1 C00L 1.475(3) . ?
N2 C00F 1.453(2) . ?
C009 C00A 1.374(2) . ?
C009 C00B 1.521(2) . ?
C009 C00C 1.397(2) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.392(2) . ?
C00B H00B 0.9800 . ?
C00B C00D 1.517(2) . ?
C00C C00H 1.391(2) . ?
C00D C00G 1.477(3) . ?
C00D C1 1.317(2) . ?
C00E C00K 1.502(3) . ?
C00F C00I 1.384(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.373(3) . ?
C00I H00I 0.9300 . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C00K H00C 0.9700 . ?
C00K H00D 0.9700 . ?
C00K C00L 1.495(3) . ?
C00L H00E 0.9700 . ?
C00L H00F 0.9700 . ?
C00M H00G 0.9600 . ?
C00M H00J 0.9600 . ?
C00M H00K 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
N1 N003 C00B 109.72(12) . . ?
C00E N003 N1 111.34(14) . . ?
C00E N003 C00B 122.77(14) . . ?
C00G O1 C00M 116.50(17) . . ?
N003 N1 C00L 106.91(15) . . ?
C00C N1 N003 106.24(12) . . ?
C00C N1 C00L 123.16(16) . . ?
O004 N2 O2 122.40(17) . . ?
O004 N2 C00F 118.81(15) . . ?
O2 N2 C00F 118.78(18) . . ?
C00A C009 C00B 131.18(14) . . ?
C00A C009 C00C 120.13(15) . . ?
C00C C009 C00B 108.68(14) . . ?
C009 C00A H00A 121.2 . . ?
C009 C00A C00F 117.55(15) . . ?
C00F C00A H00A 121.2 . . ?
N003 C00B C009 100.87(12) . . ?
N003 C00B H00B 110.0 . . ?
N003 C00B C00D 112.60(13) . . ?
C009 C00B H00B 110.0 . . ?
C00D C00B C009 113.14(13) . . ?
C00D C00B H00B 110.0 . . ?
N1 C00C C009 111.05(14) . . ?
N1 C00C C00H 127.11(16) . . ?
C00H C00C C009 121.78(17) . . ?
C00G C00D C00B 113.59(14) . . ?
C1 C00D C00B 124.01(17) . . ?
C1 C00D C00G 122.40(17) . . ?
O001 C00E N003 123.32(17) . . ?
O001 C00E C00K 128.74(19) . . ?
N003 C00E C00K 107.92(17) . . ?
C00A C00F N2 118.45(16) . . ?
C00I C00F N2 119.05(16) . . ?
C00I C00F C00A 122.48(16) . . ?
O002 C00G O1 123.00(17) . . ?
O002 C00G C00D 123.20(16) . . ?
O1 C00G C00D 113.80(16) . . ?
C00C C00H H00H 121.0 . . ?
C00I C00H C00C 118.02(17) . . ?
C00I C00H H00H 121.0 . . ?
C00F C00I H00I 120.0 . . ?
C00H C00I C00F 120.04(16) . . ?
C00H C00I H00I 120.0 . . ?
C00D C1 H1A 120.0 . . ?
C00D C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C00E C00K H00C 110.5 . . ?
C00E C00K H00D 110.5 . . ?
H00C C00K H00D 108.7 . . ?
C00L C00K C00E 106.24(17) . . ?
C00L C00K H00C 110.5 . . ?
C00L C00K H00D 110.5 . . ?
N1 C00L C00K 105.94(16) . . ?
N1 C00L H00E 110.5 . . ?
N1 C00L H00F 110.5 . . ?
C00K C00L H00E 110.5 . . ?
C00K C00L H00F 110.5 . . ?
H00E C00L H00F 108.7 . . ?
O1 C00M H00G 109.5 . . ?
O1 C00M H00J 109.5 . . ?
O1 C00M H00K 109.5 . . ?
H00G C00M H00J 109.5 . . ?
H00G C00M H00K 109.5 . . ?
H00J C00M H00K 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
O001 C00E C00K C00L 178.7(2) . . . . ?
N003 N1 C00C C009 -12.31(19) . . . . ?
N003 N1 C00C C00H 170.61(17) . . . . ?
N003 N1 C00L C00K -12.2(2) . . . . ?
N003 C00B C00D C00G 166.47(13) . . . . ?
N003 C00B C00D C1 -13.7(2) . . . . ?
N003 C00E C00K C00L 0.1(2) . . . . ?
O004 N2 C00F C00A -4.2(2) . . . . ?
O004 N2 C00F C00I 177.49(17) . . . . ?
O2 N2 C00F C00A 174.50(15) . . . . ?
O2 N2 C00F C00I -3.8(2) . . . . ?
N1 N003 C00B C009 -17.29(16) . . . . ?
N1 N003 C00B C00D 103.60(15) . . . . ?
N1 N003 C00E O001 173.18(16) . . . . ?
N1 N003 C00E C00K -8.09(19) . . . . ?
N1 C00C C00H C00I 177.50(17) . . . . ?
N2 C00F C00I C00H 178.05(16) . . . . ?
C009 C00A C00F N2 -178.13(14) . . . . ?
C009 C00A C00F C00I 0.1(2) . . . . ?
C009 C00B C00D C00G -79.96(17) . . . . ?
C009 C00B C00D C1 99.8(2) . . . . ?
C009 C00C C00H C00I 0.7(3) . . . . ?
C00A C009 C00B N003 -170.92(16) . . . . ?
C00A C009 C00B C00D 68.6(2) . . . . ?
C00A C009 C00C N1 -178.04(14) . . . . ?
C00A C009 C00C C00H -0.8(2) . . . . ?
C00A C00F C00I C00H -0.1(3) . . . . ?
C00B N003 N1 C00C 19.07(18) . . . . ?
C00B N003 N1 C00L 152.22(15) . . . . ?
C00B N003 C00E O001 40.1(3) . . . . ?
C00B N003 C00E C00K -141.12(16) . . . . ?
C00B C009 C00A C00F -178.86(15) . . . . ?
C00B C009 C00C N1 1.35(19) . . . . ?
C00B C009 C00C C00H 178.61(15) . . . . ?
C00B C00D C00G O002 -1.4(2) . . . . ?
C00B C00D C00G O1 178.95(14) . . . . ?
C00C N1 C00L C00K 111.0(2) . . . . ?
C00C C009 C00A C00F 0.4(2) . . . . ?
C00C C009 C00B N003 9.78(16) . . . . ?
C00C C009 C00B C00D -110.72(15) . . . . ?
C00C C00H C00I C00F -0.3(3) . . . . ?
C00E N003 N1 C00C -120.17(15) . . . . ?
C00E N003 N1 C00L 13.0(2) . . . . ?
C00E N003 C00B C009 116.38(17) . . . . ?
C00E N003 C00B C00D -122.73(17) . . . . ?
C00E C00K C00L N1 7.6(2) . . . . ?
C1 C00D C00G O002 178.78(19) . . . . ?
C1 C00D C00G O1 -0.9(2) . . . . ?
C00L N1 C00C C009 -135.84(18) . . . . ?
C00L N1 C00C C00H 47.1(3) . . . . ?
C00M O1 C00G O002 0.2(3) . . . . ?
C00M O1 C00G C00D 179.87(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
