# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2168144'
loop_
_audit_author_name
_audit_author_address
'Sasidhar B. S.'
;CSIR National Institute for Interdisciplinary Science and Technology
India
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O3, H2 O '

_chemical_formula_sum            'C15 H13 N O4'
_chemical_formula_weight         271.26

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'

_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                   7.2227(3)
_cell_length_b                   9.2625(4)
_cell_length_c                   11.1958(4)
_cell_angle_alpha                68.4130(10)
_cell_angle_beta                 86.8380(10)
_cell_angle_gamma                67.7030(10)
_cell_volume                     641.28(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9134
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      31.45
_exptl_crystal_description       block
_exptl_crystal_colour            colourless


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27762
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.338
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3099
_reflns_number_gt                2658
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0622P)²+0.2108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3099
_refine_ls_number_parameters     199
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.62132(18) 0.25041(15) 0.48168(12) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.8239(2) 0.19200(17) 0.52731(14) 0.0367(3) Uani 1 1 d . . . . .
H2 H 0.924892 0.151629 0.478870 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8737(2) 0.19421(18) 0.64359(14) 0.0401(3) Uani 1 1 d . . . . .
H3 H 1.008013 0.155718 0.673281 0.048 Uiso 1 1 calc R U . . .
C4 C 0.7225(2) 0.25418(18) 0.71666(13) 0.0397(3) Uani 1 1 d . . . . .
H4 H 0.757147 0.253937 0.795543 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5232(2) 0.31364(17) 0.67362(12) 0.0358(3) Uani 1 1 d . . . . .
H5 H 0.423461 0.353775 0.722884 0.043 Uiso 1 1 calc R U . . .
C6 C 0.47111(18) 0.31336(15) 0.55474(11) 0.0291(3) Uani 1 1 d . . . . .
C7 C 0.20970(18) 0.38803(15) 0.39184(11) 0.0288(2) Uani 1 1 d . . . . .
C8 C 0.35954(18) 0.31491(15) 0.31772(11) 0.0292(3) Uani 1 1 d . . . . .
C9 C 0.55856(19) 0.24888(16) 0.36186(12) 0.0321(3) Uani 1 1 d . . . . .
C10 C 0.29189(18) 0.31043(15) 0.19622(11) 0.0295(3) Uani 1 1 d . . . . .
C11 C 0.29889(19) 0.42487(16) 0.07546(12) 0.0324(3) Uani 1 1 d . . . . .
H11 H 0.344512 0.508329 0.069747 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2387(2) 0.41661(17) -0.03713(12) 0.0344(3) Uani 1 1 d . . . . .
H12 H 0.245571 0.493154 -0.117349 0.041 Uiso 1 1 calc R U . . .
C13 C 0.16862(19) 0.29364(16) -0.02876(12) 0.0330(3) Uani 1 1 d . . . . .
C14 C 0.1590(3) 0.17971(19) 0.09086(14) 0.0432(3) Uani 1 1 d . . . . .
H14 H 0.111656 0.097258 0.096478 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2201(2) 0.18868(18) 0.20218(13) 0.0415(3) Uani 1 1 d . . . . .
H15 H 0.212965 0.111932 0.282207 0.050 Uiso 1 1 calc R U . . .
N1 N 0.27209(16) 0.37781(14) 0.50778(10) 0.0314(2) Uani 1 1 d . . . . .
O1 O 0.10665(17) 0.27720(14) -0.13494(10) 0.0444(3) Uani 1 1 d . . . . .
O2 O 0.71002(15) 0.17957(16) 0.30032(11) 0.0505(3) Uani 1 1 d . . . . .
O3 O 0.02451(13) 0.46071(13) 0.35386(8) 0.0361(2) Uani 1 1 d . . . . .
H1 H 0.177(3) 0.427(2) 0.5489(17) 0.040(4) Uiso 1 1 d . . . . .
H1A H 0.071(3) 0.372(3) -0.201(2) 0.066(6) Uiso 1 1 d . . . . .
H2A H 0.665(4) 0.160(3) 0.235(2) 0.077(7) Uiso 1 1 d . . . . .
O4 O 0.6915(3) 0.0718(2) 0.10648(18) 0.0887(6) Uani 1 1 d D . . . .
H4B H 0.761(4) -0.034(2) 0.120(3) 0.106 Uiso 1 1 d D U . . .
H4A H 0.571(3) 0.092(3) 0.081(3) 0.106 Uiso 1 1 d D 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
C1 C6 1.3996(17) . ?
C1 C2 1.4044(17) . ?
C1 C9 1.4460(17) . ?
C2 C3 1.3790(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3743(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4042(16) . ?
C5 H5 0.9300 . ?
C6 N1 1.3786(15) . ?
C7 O3 1.2617(15) . ?
C7 N1 1.3560(15) . ?
C7 C8 1.4411(16) . ?
C8 C9 1.3687(17) . ?
C8 C10 1.4904(15) . ?
C9 O2 1.3390(15) . ?
C10 C15 1.3889(18) . ?
C10 C11 1.3902(17) . ?
C11 C12 1.3930(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.3842(19) . ?
C12 H12 0.9300 . ?
C13 O1 1.3713(15) . ?
C13 C14 1.3846(19) . ?
C14 C15 1.3855(19) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 H1 0.878(19) . ?
O1 H1A 0.87(2) . ?
O2 H2A 0.92(3) . ?
O4 H4B 0.874(17) . ?
O4 H4A 0.860(16) . ?

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
C6 C1 C2 119.10(11) . . ?
C6 C1 C9 117.69(11) . . ?
C2 C1 C9 123.21(12) . . ?
C3 C2 C1 120.32(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.98(12) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.87(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.52(12) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C1 119.40(11) . . ?
N1 C6 C5 120.40(11) . . ?
C1 C6 C5 120.18(11) . . ?
O3 C7 N1 118.84(11) . . ?
O3 C7 C8 123.16(11) . . ?
N1 C7 C8 118.01(11) . . ?
C9 C8 C7 119.35(11) . . ?
C9 C8 C10 122.00(11) . . ?
C7 C8 C10 118.64(10) . . ?
O2 C9 C8 124.35(11) . . ?
O2 C9 C1 114.36(11) . . ?
C8 C9 C1 121.28(11) . . ?
C15 C10 C11 118.32(11) . . ?
C15 C10 C8 119.74(11) . . ?
C11 C10 C8 121.94(11) . . ?
C10 C11 C12 121.10(12) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.52(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O1 C13 C12 123.04(12) . . ?
O1 C13 C14 116.91(12) . . ?
C12 C13 C14 120.05(12) . . ?
C13 C14 C15 119.92(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.08(12) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C7 N1 C6 124.01(10) . . ?
C7 N1 H1 115.3(11) . . ?
C6 N1 H1 120.3(11) . . ?
C13 O1 H1A 110.7(15) . . ?
C9 O2 H2A 111.8(15) . . ?
H4B O4 H4A 106(2) . . ?

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
C6 C1 C2 C3 1.06(19) . . . . ?
C9 C1 C2 C3 -178.86(12) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C2 C1 C6 N1 177.13(11) . . . . ?
C9 C1 C6 N1 -2.95(18) . . . . ?
C2 C1 C6 C5 -1.67(19) . . . . ?
C9 C1 C6 C5 178.25(11) . . . . ?
C4 C5 C6 N1 -177.75(12) . . . . ?
C4 C5 C6 C1 1.03(19) . . . . ?
O3 C7 C8 C9 175.42(12) . . . . ?
N1 C7 C8 C9 -4.50(18) . . . . ?
O3 C7 C8 C10 -5.86(18) . . . . ?
N1 C7 C8 C10 174.21(11) . . . . ?
C7 C8 C9 O2 -179.31(12) . . . . ?
C10 C8 C9 O2 2.0(2) . . . . ?
C7 C8 C9 C1 0.28(19) . . . . ?
C10 C8 C9 C1 -178.39(11) . . . . ?
C6 C1 C9 O2 -176.93(12) . . . . ?
C2 C1 C9 O2 2.99(19) . . . . ?
C6 C1 C9 C8 3.44(19) . . . . ?
C2 C1 C9 C8 -176.63(12) . . . . ?
C9 C8 C10 C15 100.14(16) . . . . ?
C7 C8 C10 C15 -78.54(16) . . . . ?
C9 C8 C10 C11 -79.60(16) . . . . ?
C7 C8 C10 C11 101.72(14) . . . . ?
C15 C10 C11 C12 -1.02(19) . . . . ?
C8 C10 C11 C12 178.72(11) . . . . ?
C10 C11 C12 C13 0.73(19) . . . . ?
C11 C12 C13 O1 180.00(12) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
O1 C13 C14 C15 179.73(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C11 C10 C15 C14 0.7(2) . . . . ?
C8 C10 C15 C14 -179.01(13) . . . . ?
O3 C7 N1 C6 -174.74(11) . . . . ?
C8 C7 N1 C6 5.19(18) . . . . ?
C1 C6 N1 C7 -1.41(19) . . . . ?
C5 C6 N1 C7 177.39(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.878(19) 1.975(19) 2.8519(14) 176.4(16) 2_566 yes
O1 H1A O3 0.87(2) 1.78(2) 2.6326(15) 166(2) 2_565 yes
O2 H2A O4 0.92(3) 1.87(3) 2.7295(18) 156(2) . yes
O4 H4B O1 0.874(17) 2.029(18) 2.8976(19) 172(3) 2_655 yes

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.044

# start Validation Reply Form
_vrf_PLAT420_shelx               
;
PROBLEM: D-H Bond Without Acceptor  O4       --H4A      .     Please Check 
RESPONSE: There is no acceptor in the vicinity. 
;
# end Validation Reply Form

