# Supplementary Information (SI) for Chemical Science.
# 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. 
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data_xzc-1
_database_code_depnum_ccdc_archive 'CCDC 2467629'
loop_
_audit_author_name
_audit_author_address
'Zeyuan Dong'
;Jilin University
China
;
_audit_update_record             
;
2025-06-26 deposited with the CCDC.	2026-02-17 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V138 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_smtbx_masks_special_details     ?
_audit_creation_date             2025-05-10
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C4(H4), C3(H3), C2(H2), C16(H16), C19(H19),
 C1(H1), C18(H18), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C19 H11 N7 O2'
_chemical_formula_moiety         'C19 H11 N7 O2'
_chemical_formula_weight         369.35
_chemical_melting_point          ?
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.3394(5)
_cell_length_b                   36.940(5)
_cell_length_c                   11.2673(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.790(5)
_cell_angle_gamma                90
_cell_volume                     1804.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298.00
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      24.46
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.990
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.00
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            45194
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_theta_min         2.853
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3087
_reflns_number_gt                2084
_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.
 
 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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_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)+(0.1690P)²+0.2439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2657
_refine_ls_wR_factor_gt          0.2090
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.8733(5) 0.40598(5) 0.67268(18) 0.0649(6) Uani 1 1 d . . . . .
O2 O 0.0183(4) 0.34848(6) 0.47381(18) 0.0628(6) Uani 1 1 d . . . . .
N4 N 0.4390(5) 0.40346(6) 0.4851(2) 0.0608(7) Uani 1 1 d . . . . .
N5 N -0.1165(6) 0.35911(8) 0.2861(2) 0.0739(8) Uani 1 1 d . . . . .
N6 N -0.2831(6) 0.32891(8) 0.3237(2) 0.0732(8) Uani 1 1 d . . . . .
N3 N 0.9924(7) 0.46271(8) 0.6345(3) 0.0792(8) Uani 1 1 d . . . . .
N2 N 1.1690(7) 0.45123(8) 0.7363(3) 0.0818(9) Uani 1 1 d . . . . .
C12 C 0.2579(7) 0.40104(8) 0.3866(3) 0.0621(8) Uani 1 1 d . . . . .
C7 C 0.8253(7) 0.43537(8) 0.6012(3) 0.0621(7) Uani 1 1 d . . . . .
C13 C 0.0546(7) 0.36938(8) 0.3762(3) 0.0615(8) Uani 1 1 d . . . . .
C8 C 0.6163(7) 0.43309(8) 0.4967(3) 0.0616(8) Uani 1 1 d . . . . .
C14 C -0.1975(6) 0.32421(8) 0.4341(3) 0.0626(8) Uani 1 1 d . . . . .
C6 C 1.0906(7) 0.41814(10) 0.7542(3) 0.0692(8) Uani 1 1 d . . . . .
C15 C -0.3055(8) 0.29734(9) 0.5183(3) 0.0721(9) Uani 1 1 d . . . . .
N7 N -0.4891(9) 0.27109(10) 0.4745(3) 0.1039(11) Uani 1 1 d . . . . .
C5 C 1.2111(8) 0.39345(10) 0.8473(3) 0.0734(9) Uani 1 1 d . . . . .
C9 C 0.6129(8) 0.46110(9) 0.4131(3) 0.0739(9) Uani 1 1 d . . . . .
H9 H 0.734665 0.481589 0.425640 0.089 Uiso 1 1 calc R U . . .
C11 C 0.2467(8) 0.42693(10) 0.2973(3) 0.0739(9) Uani 1 1 d . . . . .
H11 H 0.121348 0.423698 0.228802 0.089 Uiso 1 1 calc R U . . .
C10 C 0.4259(8) 0.45758(10) 0.3125(3) 0.0802(10) Uani 1 1 d . . . . .
H10 H 0.419619 0.475651 0.254978 0.096 Uiso 1 1 calc R U . . .
N1 N 1.1328(10) 0.35895(11) 0.8402(4) 0.1118(13) Uani 1 1 d . . . . .
C4 C 1.3909(9) 0.40761(12) 0.9385(3) 0.0921(12) Uani 1 1 d . . . . .
H4 H 1.440422 0.432100 0.940798 0.111 Uiso 1 1 calc R U . . .
C3 C 1.4967(12) 0.38440(19) 1.0269(4) 0.1149(17) Uani 1 1 d . . . . .
H3 H 1.621984 0.393236 1.089688 0.138 Uiso 1 1 calc R U . . .
C2 C 1.4209(12) 0.34911(18) 1.0237(4) 0.1139(15) Uani 1 1 d . . . . .
H2 H 1.486985 0.333622 1.084794 0.137 Uiso 1 1 calc R U . . .
C16 C -0.2229(13) 0.30035(14) 0.6344(4) 0.1195(17) Uani 1 1 d . . . . .
H16 H -0.099821 0.319479 0.662007 0.143 Uiso 1 1 calc R U . . .
C19 C -0.5900(14) 0.24716(14) 0.5530(6) 0.1215(17) Uani 1 1 d . . . . .
H19 H -0.726325 0.229313 0.525178 0.146 Uiso 1 1 calc R U . . .
C1 C 1.2450(14) 0.33647(16) 0.9287(5) 0.1312(19) Uani 1 1 d . . . . .
H1 H 1.200180 0.311877 0.924014 0.157 Uiso 1 1 calc R U . . .
C18 C -0.5082(16) 0.24731(16) 0.6670(6) 0.142(2) Uani 1 1 d . . . . .
H18 H -0.573806 0.229228 0.717319 0.170 Uiso 1 1 calc R U . . .
C17 C -0.321(2) 0.2753(2) 0.7095(5) 0.178(3) Uani 1 1 d . . . . .
H17 H -0.264232 0.276679 0.790052 0.213 Uiso 1 1 calc R U . . .


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 1.362(4) . ?
O1 C6 1.360(4) . ?
O2 C13 1.359(4) . ?
O2 C14 1.357(3) . ?
N4 C12 1.331(4) . ?
N4 C8 1.341(4) . ?
N5 N6 1.406(4) . ?
N5 C13 1.286(4) . ?
N6 C14 1.292(4) . ?
N3 N2 1.413(4) . ?
N3 C7 1.289(4) . ?
N2 C6 1.287(4) . ?
C12 C13 1.466(4) . ?
C12 C11 1.387(4) . ?
C7 C8 1.453(5) . ?
C8 C9 1.398(5) . ?
C14 C15 1.466(5) . ?
C6 C5 1.467(5) . ?
C15 N7 1.334(4) . ?
C15 C16 1.344(5) . ?
N7 C19 1.339(6) . ?
C5 N1 1.321(5) . ?
C5 C4 1.363(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(5) . ?
C10 H10 0.9300 . ?
N1 C1 1.369(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.344(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.366(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.338(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.316(8) . ?
C1 H1 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.386(9) . ?
C17 H17 0.9300 . ?

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 O1 C7 102.5(2) . . ?
C14 O2 C13 102.3(2) . . ?
C12 N4 C8 116.7(3) . . ?
C13 N5 N6 106.4(3) . . ?
C14 N6 N5 105.6(2) . . ?
C7 N3 N2 106.0(3) . . ?
C6 N2 N3 105.9(3) . . ?
N4 C12 C13 116.7(3) . . ?
N4 C12 C11 123.8(3) . . ?
C11 C12 C13 119.5(3) . . ?
O1 C7 C8 120.3(3) . . ?
N3 C7 O1 112.6(3) . . ?
N3 C7 C8 127.0(3) . . ?
O2 C13 C12 118.8(3) . . ?
N5 C13 O2 112.7(3) . . ?
N5 C13 C12 128.4(3) . . ?
N4 C8 C7 117.3(3) . . ?
N4 C8 C9 123.4(3) . . ?
C9 C8 C7 119.3(3) . . ?
O2 C14 C15 118.1(3) . . ?
N6 C14 O2 113.0(3) . . ?
N6 C14 C15 128.9(3) . . ?
O1 C6 C5 119.3(3) . . ?
N2 C6 O1 112.8(3) . . ?
N2 C6 C5 127.9(3) . . ?
N7 C15 C14 117.1(3) . . ?
N7 C15 C16 123.1(4) . . ?
C16 C15 C14 119.7(3) . . ?
C15 N7 C19 116.4(4) . . ?
N1 C5 C6 118.3(3) . . ?
N1 C5 C4 123.5(4) . . ?
C4 C5 C6 118.1(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C12 C11 H11 120.8 . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H11 120.8 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C5 N1 C1 117.4(4) . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C3 117.7(4) . . ?
C3 C4 H4 121.1 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.6(5) . . ?
C1 C2 H2 120.7 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(5) . . ?
C17 C16 H16 120.6 . . ?
N7 C19 H19 118.0 . . ?
C18 C19 N7 124.1(5) . . ?
C18 C19 H19 118.0 . . ?
N1 C1 H1 119.0 . . ?
C2 C1 N1 121.9(5) . . ?
C2 C1 H1 119.0 . . ?
C19 C18 H18 121.1 . . ?
C19 C18 C17 117.8(5) . . ?
C17 C18 H18 121.1 . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?

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 C7 C8 N4 10.6(4) . . . . ?
O1 C7 C8 C9 -168.3(3) . . . . ?
O1 C6 C5 N1 8.3(5) . . . . ?
O1 C6 C5 C4 -169.8(3) . . . . ?
O2 C14 C15 N7 -172.1(3) . . . . ?
O2 C14 C15 C16 9.1(5) . . . . ?
N4 C12 C13 O2 12.3(4) . . . . ?
N4 C12 C13 N5 -172.4(3) . . . . ?
N4 C12 C11 C10 -2.1(5) . . . . ?
N4 C8 C9 C10 -2.1(5) . . . . ?
N5 N6 C14 O2 -1.1(3) . . . . ?
N5 N6 C14 C15 177.7(3) . . . . ?
N6 N5 C13 O2 -0.1(3) . . . . ?
N6 N5 C13 C12 -175.6(3) . . . . ?
N6 C14 C15 N7 9.1(5) . . . . ?
N6 C14 C15 C16 -169.6(4) . . . . ?
N3 N2 C6 O1 -0.1(4) . . . . ?
N3 N2 C6 C5 178.6(3) . . . . ?
N3 C7 C8 N4 -173.0(3) . . . . ?
N3 C7 C8 C9 8.1(5) . . . . ?
N2 N3 C7 O1 0.1(3) . . . . ?
N2 N3 C7 C8 -176.5(3) . . . . ?
N2 C6 C5 N1 -170.3(4) . . . . ?
N2 C6 C5 C4 11.5(5) . . . . ?
C12 N4 C8 C7 -177.4(2) . . . . ?
C12 N4 C8 C9 1.5(4) . . . . ?
C12 C11 C10 C9 1.5(5) . . . . ?
C7 O1 C6 N2 0.2(3) . . . . ?
C7 O1 C6 C5 -178.6(3) . . . . ?
C7 N3 N2 C6 0.0(4) . . . . ?
C7 C8 C9 C10 176.8(3) . . . . ?
C13 O2 C14 N6 1.0(3) . . . . ?
C13 O2 C14 C15 -177.9(3) . . . . ?
C13 N5 N6 C14 0.7(3) . . . . ?
C13 C12 C11 C10 176.0(3) . . . . ?
C8 N4 C12 C13 -177.5(2) . . . . ?
C8 N4 C12 C11 0.6(4) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C14 O2 C13 N5 -0.5(3) . . . . ?
C14 O2 C13 C12 175.5(2) . . . . ?
C14 C15 N7 C19 -178.9(4) . . . . ?
C14 C15 C16 C17 -179.3(6) . . . . ?
C6 O1 C7 N3 -0.2(3) . . . . ?
C6 O1 C7 C8 176.7(3) . . . . ?
C6 C5 N1 C1 -179.3(4) . . . . ?
C6 C5 C4 C3 178.4(4) . . . . ?
C15 N7 C19 C18 -3.1(9) . . . . ?
C15 C16 C17 C18 -1.0(12) . . . . ?
N7 C15 C16 C17 2.1(9) . . . . ?
N7 C19 C18 C17 4.1(11) . . . . ?
C5 N1 C1 C2 2.6(9) . . . . ?
C5 C4 C3 C2 -0.8(7) . . . . ?
C11 C12 C13 O2 -166.0(3) . . . . ?
C11 C12 C13 N5 9.4(5) . . . . ?
N1 C5 C4 C3 0.4(6) . . . . ?
C4 C5 N1 C1 -1.3(7) . . . . ?
C4 C3 C2 C1 2.1(9) . . . . ?
C3 C2 C1 N1 -3.1(9) . . . . ?
C16 C15 N7 C19 -0.2(7) . . . . ?
C19 C18 C17 C16 -2.0(13) . . . . ?

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 -0.979 0.000 0.500 75.6 17.3 ?
2 -0.645 0.500 0.000 75.6 17.3 ?

