# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2268025'
loop_
_audit_author_name
_audit_author_address
'zhan-yong wang'
;Xinxiang University
China
;
_audit_update_record             
;
2023-06-07 deposited with the CCDC.	2026-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_weight         321.32

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.3469(11)
_cell_length_b                   13.9960(14)
_cell_length_c                   9.8736(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.705(2)
_cell_angle_gamma                90
_cell_volume                     1501.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.42

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.978
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3771
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.909
_reflns_number_total             2409
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_max     0.821
_reflns_Friedel_fraction_full    0.821

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0399P)²+0.1448P] 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_abs_structure_details 
; 
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2409
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O1 O 0.46150(16) 0.31982(12) 0.84212(17) 0.0438(4) Uani 1 1 d . . . . .
O4 O 0.54275(17) 0.05540(11) 0.4054(2) 0.0485(5) Uani 1 1 d . . . . .
O3 O 0.27022(16) 0.29741(13) 0.55037(19) 0.0480(5) Uani 1 1 d . . . . .
N1 N 0.47724(17) 0.20732(12) 0.3735(2) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.32671(18) 0.21417(15) 0.8687(2) 0.0588(5) Uani 1 1 d . . . . .
C11 C 0.33749(19) 0.28253(16) 0.4758(2) 0.0319(5) Uani 1 1 d . . . . .
C17 C 0.43629(19) 0.29367(15) 0.3004(2) 0.0297(5) Uani 1 1 d . . . . .
C12 C 0.35335(19) 0.33980(15) 0.3594(2) 0.0297(5) Uani 1 1 d . . . . .
C18 C 0.5278(2) 0.12629(16) 0.3310(2) 0.0356(5) Uani 1 1 d . . . . .
C6 C 0.5544(2) 0.34681(17) 0.7825(2) 0.0348(5) Uani 1 1 d . . . . .
C5 C 0.58513(19) 0.29247(16) 0.6799(2) 0.0308(5) Uani 1 1 d . . . . .
C13 C 0.2980(2) 0.42632(16) 0.3065(2) 0.0351(5) Uani 1 1 d . . . . .
H13 H 0.2443 0.4567 0.3481 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4118(2) 0.23098(18) 0.8225(2) 0.0402(6) Uani 1 1 d . . . . .
C10 C 0.4248(2) 0.19753(15) 0.4932(2) 0.0310(5) Uani 1 1 d . . . . .
H10 H 0.3771 0.1382 0.4824 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5249(2) 0.19659(15) 0.6381(2) 0.0326(5) Uani 1 1 d . . . . .
H9 H 0.5894 0.1523 0.6298 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3252(2) 0.46557(17) 0.1908(3) 0.0424(6) Uani 1 1 d . . . . .
H14 H 0.2880 0.5223 0.1516 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4662(2) 0.33544(17) 0.1864(3) 0.0398(6) Uani 1 1 d . . . . .
H16 H 0.5233 0.3074 0.1474 0.048 Uiso 1 1 calc R U . . .
C1 C 0.6106(2) 0.43282(18) 0.8289(3) 0.0463(7) Uani 1 1 d . . . . .
H1 H 0.5900 0.4666 0.9000 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6740(2) 0.3297(2) 0.6215(3) 0.0390(6) Uani 1 1 d . . . . .
H4 H 0.6970 0.2950 0.5529 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7279(2) 0.4170(2) 0.6640(3) 0.0488(7) Uani 1 1 d . . . . .
H3 H 0.7849 0.4415 0.6217 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6980(2) 0.4686(2) 0.7689(3) 0.0514(7) Uani 1 1 d . . . . .
H2 H 0.7362 0.5267 0.7990 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4753(3) 0.15909(17) 0.7572(3) 0.0426(6) Uani 1 1 d . . . . .
H8A H 0.4184 0.1074 0.7199 0.051 Uiso 1 1 calc R U . . .
H8B H 0.5435 0.1326 0.8308 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4079(3) 0.42008(18) 0.1334(3) 0.0458(6) Uani 1 1 d . . . . .
H15 H 0.4251 0.4477 0.0555 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5597(3) 0.1287(2) 0.1949(3) 0.0515(7) Uani 1 1 d . . . . .
H19A H 0.6305 0.1685 0.2049 0.077 Uiso 1 1 calc R U . . .
H19B H 0.4915 0.1539 0.1219 0.077 Uiso 1 1 calc R U . . .
H19C H 0.5775 0.0651 0.1701 0.077 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
O1 C7 1.356(3) . ?
O1 C6 1.400(3) . ?
O4 C18 1.217(3) . ?
O3 C11 1.221(3) . ?
N1 C18 1.389(3) . ?
N1 C17 1.416(3) . ?
N1 C10 1.475(3) . ?
O2 C7 1.203(3) . ?
C11 C12 1.454(3) . ?
C11 C10 1.526(3) . ?
C17 C16 1.394(3) . ?
C17 C12 1.399(3) . ?
C12 C13 1.395(3) . ?
C18 C19 1.489(3) . ?
C6 C1 1.378(3) . ?
C6 C5 1.389(3) . ?
C5 C4 1.398(3) . ?
C5 C9 1.509(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C7 C8 1.489(4) . ?
C10 C9 1.550(3) . ?
C10 H10 0.9800 . ?
C9 C8 1.535(3) . ?
C9 H9 0.9800 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C16 C15 1.384(4) . ?
C16 H16 0.9300 . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C4 C3 1.376(4) . ?
C4 H4 0.9300 . ?
C3 C2 1.383(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C7 O1 C6 121.35(18) . . ?
C18 N1 C17 130.27(19) . . ?
C18 N1 C10 117.58(18) . . ?
C17 N1 C10 109.83(17) . . ?
O3 C11 C12 128.6(2) . . ?
O3 C11 C10 124.3(2) . . ?
C12 C11 C10 107.16(18) . . ?
C16 C17 C12 119.5(2) . . ?
C16 C17 N1 130.5(2) . . ?
C12 C17 N1 110.03(19) . . ?
C13 C12 C17 121.9(2) . . ?
C13 C12 C11 129.1(2) . . ?
C17 C12 C11 109.02(18) . . ?
O4 C18 N1 118.8(2) . . ?
O4 C18 C19 122.3(2) . . ?
N1 C18 C19 118.9(2) . . ?
C1 C6 C5 122.2(2) . . ?
C1 C6 O1 115.3(2) . . ?
C5 C6 O1 122.4(2) . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 C9 119.9(2) . . ?
C4 C5 C9 122.9(2) . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
O2 C7 O1 118.1(2) . . ?
O2 C7 C8 125.0(2) . . ?
O1 C7 C8 116.6(2) . . ?
N1 C10 C11 103.64(17) . . ?
N1 C10 C9 112.49(18) . . ?
C11 C10 C9 112.99(17) . . ?
N1 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C5 C9 C8 109.37(18) . . ?
C5 C9 C10 113.51(17) . . ?
C8 C9 C10 112.15(19) . . ?
C5 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C15 C16 C17 117.6(2) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C7 C8 C9 115.5(2) . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C14 C15 C16 123.1(2) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C18 N1 C17 C16 -21.9(4) . . . . ?
C10 N1 C17 C16 176.2(2) . . . . ?
C18 N1 C17 C12 158.4(2) . . . . ?
C10 N1 C17 C12 -3.5(2) . . . . ?
C16 C17 C12 C13 0.8(3) . . . . ?
N1 C17 C12 C13 -179.47(19) . . . . ?
C16 C17 C12 C11 -180.0(2) . . . . ?
N1 C17 C12 C11 -0.2(2) . . . . ?
O3 C11 C12 C13 1.5(4) . . . . ?
C10 C11 C12 C13 -177.2(2) . . . . ?
O3 C11 C12 C17 -177.6(2) . . . . ?
C10 C11 C12 C17 3.6(2) . . . . ?
C17 N1 C18 O4 -171.1(2) . . . . ?
C10 N1 C18 O4 -10.4(3) . . . . ?
C17 N1 C18 C19 7.8(3) . . . . ?
C10 N1 C18 C19 168.5(2) . . . . ?
C7 O1 C6 C1 -169.9(2) . . . . ?
C7 O1 C6 C5 12.3(3) . . . . ?
C1 C6 C5 C4 -1.7(3) . . . . ?
O1 C6 C5 C4 175.9(2) . . . . ?
C1 C6 C5 C9 177.1(2) . . . . ?
O1 C6 C5 C9 -5.3(3) . . . . ?
C17 C12 C13 C14 1.3(3) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C6 O1 C7 O2 -175.2(2) . . . . ?
C6 O1 C7 C8 10.6(3) . . . . ?
C18 N1 C10 C11 -159.05(18) . . . . ?
C17 N1 C10 C11 5.4(2) . . . . ?
C18 N1 C10 C9 78.6(2) . . . . ?
C17 N1 C10 C9 -116.97(19) . . . . ?
O3 C11 C10 N1 175.8(2) . . . . ?
C12 C11 C10 N1 -5.4(2) . . . . ?
O3 C11 C10 C9 -62.2(3) . . . . ?
C12 C11 C10 C9 116.6(2) . . . . ?
C6 C5 C9 C8 -21.6(3) . . . . ?
C4 C5 C9 C8 157.1(2) . . . . ?
C6 C5 C9 C10 104.5(2) . . . . ?
C4 C5 C9 C10 -76.8(3) . . . . ?
N1 C10 C9 C5 71.3(2) . . . . ?
C11 C10 C9 C5 -45.6(3) . . . . ?
N1 C10 C9 C8 -164.11(18) . . . . ?
C11 C10 C9 C8 79.0(2) . . . . ?
C12 C13 C14 C15 -1.7(3) . . . . ?
C12 C17 C16 C15 -2.3(3) . . . . ?
N1 C17 C16 C15 178.0(2) . . . . ?
C5 C6 C1 C2 2.1(4) . . . . ?
O1 C6 C1 C2 -175.7(2) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C9 C5 C4 C3 -179.1(2) . . . . ?
C5 C4 C3 C2 2.0(4) . . . . ?
C4 C3 C2 C1 -1.6(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
O2 C7 C8 C9 147.1(3) . . . . ?
O1 C7 C8 C9 -39.1(3) . . . . ?
C5 C9 C8 C7 42.8(3) . . . . ?
C10 C9 C8 C7 -84.1(3) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C17 C16 C15 C14 2.0(4) . . . . ?

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
C19 H19A O3 0.96 2.54 3.282(3) 134.1 4_554
C9 H9 O4 0.98 2.52 3.081(3) 116.1 .

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034

