# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2440035'
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C6 H8 N'
_chemical_formula_sum            'C12 H10 N4 O7'
_chemical_formula_weight         322.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.0531(2)
_cell_length_b                   7.09940(10)
_cell_length_c                   14.8649(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0100(10)
_cell_angle_gamma                90
_cell_volume                     1375.62(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7620
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      76.77

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    1.136
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_T_min  0.21056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      298(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Rotating-anode
_diffrn_measurement_device_type  'Rigaku FR-X diffractometer'
_diffrn_detector                 'Hybrid Pixel Array'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8491
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.390
_diffrn_reflns_theta_max         76.509
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2659
_reflns_number_gt                2576
_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       'CrysAlisPro (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0638P)²+0.4410P] 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         2659
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.88640(7) 0.13326(15) 0.46758(6) 0.0393(3) Uani 1 1 d . . . . .
O2 O 0.78996(10) 0.1264(2) 0.62370(7) 0.0596(3) Uani 1 1 d . . . . .
O3 O 0.65442(11) 0.2981(2) 0.60693(9) 0.0713(4) Uani 1 1 d . . . . .
O4 O 0.41853(8) 0.1201(2) 0.36332(9) 0.0702(4) Uani 1 1 d . . . . .
O5 O 0.47675(10) 0.0119(3) 0.24018(9) 0.0813(5) Uani 1 1 d . . . . .
O6 O 0.83179(9) -0.06155(18) 0.20978(7) 0.0531(3) Uani 1 1 d . . . . .
O7 O 0.93855(9) 0.0887(3) 0.29604(8) 0.0727(5) Uani 1 1 d . . . . .
N1 N 0.71855(10) 0.1932(2) 0.57727(8) 0.0446(3) Uani 1 1 d . . . . .
N2 N 0.48896(9) 0.0703(2) 0.31731(9) 0.0510(4) Uani 1 1 d . . . . .
N3 N 0.85298(8) 0.02802(18) 0.27873(7) 0.0368(3) Uani 1 1 d . . . . .
C1 C 0.79785(9) 0.11536(17) 0.43239(8) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.70706(10) 0.14342(19) 0.48221(8) 0.0327(3) Uani 1 1 d . . . . .
C3 C 0.60879(10) 0.1350(2) 0.44611(9) 0.0358(3) Uani 1 1 d . . . . .
H3 H 0.553665 0.163844 0.480807 0.043 Uiso 1 1 calc R U . . .
C4 C 0.59290(10) 0.0823(2) 0.35646(9) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.67386(10) 0.04324(19) 0.30373(8) 0.0329(3) Uani 1 1 d . . . . .
H5 H 0.661974 0.003390 0.244502 0.040 Uiso 1 1 calc R U . . .
C6 C 0.77250(9) 0.06380(17) 0.33957(8) 0.0294(3) Uani 1 1 d . . . . .
N4 N 0.91839(9) -0.2107(2) 0.57240(8) 0.0389(3) Uani 1 1 d . . . . .
H2N H 0.9085(15) -0.273(3) 0.6255(14) 0.058 Uiso 1 1 d . U . . .
H3N H 0.8962(16) -0.095(3) 0.5805(14) 0.058 Uiso 1 1 d . U . . .
H1N H 0.9910(17) -0.196(3) 0.5654(13) 0.058 Uiso 1 1 d . U . . .
C7 C 0.86544(10) -0.30182(19) 0.49463(9) 0.0335(3) Uani 1 1 d . . . . .
C8 C 0.76045(10) -0.3281(2) 0.49602(10) 0.0381(3) Uani 1 1 d . . . . .
H8 H 0.725249 -0.297016 0.546750 0.046 Uiso 1 1 calc R U . . .
C9 C 0.70899(11) -0.4018(2) 0.41993(11) 0.0431(3) Uani 1 1 d . . . . .
H9 H 0.638293 -0.418687 0.419229 0.052 Uiso 1 1 calc R U . . .
C10 C 0.76174(12) -0.4504(2) 0.34529(10) 0.0446(4) Uani 1 1 d . . . . .
H10 H 0.726554 -0.498569 0.294342 0.054 Uiso 1 1 calc R U . . .
C11 C 0.86674(12) -0.4274(2) 0.34634(10) 0.0444(3) Uani 1 1 d . . . . .
H11 H 0.902386 -0.463491 0.296610 0.053 Uiso 1 1 calc R U . . .
C12 C 0.91964(11) -0.3506(2) 0.42122(10) 0.0398(3) Uani 1 1 d . . . . .
H12 H 0.990235 -0.332487 0.421670 0.048 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 C1 1.2499(15) . ?
O2 N1 1.2260(18) . ?
O3 N1 1.2200(19) . ?
O4 N2 1.2263(18) . ?
O5 N2 1.2218(19) . ?
O6 N3 1.2254(15) . ?
O7 N3 1.2122(16) . ?
N1 C2 1.4566(16) . ?
N2 C4 1.4504(17) . ?
N3 C6 1.4441(15) . ?
C1 C2 1.4438(17) . ?
C1 C6 1.4490(16) . ?
C2 C3 1.3656(18) . ?
C3 C4 1.3891(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3767(19) . ?
C5 C6 1.3750(17) . ?
C5 H5 0.9300 . ?
N4 C7 1.4659(17) . ?
N4 H2N 0.92(2) . ?
N4 H3N 0.88(2) . ?
N4 H1N 0.96(2) . ?
C7 C12 1.376(2) . ?
C7 C8 1.3842(18) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 H12 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
O3 N1 O2 123.28(13) . . ?
O3 N1 C2 117.46(13) . . ?
O2 N1 C2 119.25(12) . . ?
O5 N2 O4 123.81(13) . . ?
O5 N2 C4 118.02(13) . . ?
O4 N2 C4 118.17(13) . . ?
O7 N3 O6 121.80(11) . . ?
O7 N3 C6 119.80(11) . . ?
O6 N3 C6 118.39(11) . . ?
O1 C1 C2 122.49(11) . . ?
O1 C1 C6 125.74(11) . . ?
C2 C1 C6 111.77(10) . . ?
C3 C2 C1 124.87(11) . . ?
C3 C2 N1 116.02(11) . . ?
C1 C2 N1 119.05(11) . . ?
C2 C3 C4 118.61(12) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.33(12) . . ?
C5 C4 N2 119.31(12) . . ?
C3 C4 N2 119.35(12) . . ?
C6 C5 C4 119.29(12) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 N3 115.84(11) . . ?
C5 C6 C1 123.92(11) . . ?
N3 C6 C1 120.23(11) . . ?
C7 N4 H2N 112.5(13) . . ?
C7 N4 H3N 112.0(14) . . ?
H2N N4 H3N 105.6(18) . . ?
C7 N4 H1N 112.8(12) . . ?
H2N N4 H1N 109.1(17) . . ?
H3N N4 H1N 104.3(18) . . ?
C12 C7 C8 121.92(13) . . ?
C12 C7 N4 119.72(12) . . ?
C8 C7 N4 118.29(12) . . ?
C7 C8 C9 118.43(13) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.60(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.91(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.47(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.64(13) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2440041'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          240
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H10 N O'
_chemical_formula_sum            'C13 H12 N4 O8'
_chemical_formula_weight         352.27

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           14
_space_group_name_H-M_alt        'P 21/n'
_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                   17.3160(11)
_cell_length_b                   4.0020(4)
_cell_length_c                   21.9731(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.198(6)
_cell_angle_gamma                90
_cell_volume                     1513.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4698
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      23.69

_exptl_crystal_description       block
_exptl_crystal_colour            'Deep brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7546
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.850
_diffrn_reflns_theta_max         24.696
_diffrn_reflns_theta_full        24.696
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             2477
_reflns_number_gt                1716
_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       'APEX4 2021.4-0'
_computing_cell_refinement       'SAINT (Bruker, 2020)'
_computing_data_reduction        'SAINT (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1424P)²] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2387
_refine_ls_wR_factor_gt          0.2014
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.54991(14) 0.3646(6) 0.39179(10) 0.0373(7) Uani 1 1 d . . . . .
O2 O 0.61614(17) -0.0074(8) 0.31143(12) 0.0600(9) Uani 1 1 d . . . . .
O3 O 0.5957(2) 0.1478(12) 0.21915(13) 0.0985(16) Uani 1 1 d . . . . .
O4 O 0.34794(18) 0.5400(9) 0.14173(12) 0.0702(11) Uani 1 1 d . . . . .
O5 O 0.27827(16) 0.8219(9) 0.19889(12) 0.0612(9) Uani 1 1 d . . . . .
O6 O 0.3621(2) 0.9384(11) 0.41132(14) 0.0906(14) Uani 1 1 d . . . . .
O7 O 0.4467(2) 0.6485(14) 0.45537(13) 0.124(2) Uani 1 1 d . . . . .
N1 N 0.57897(17) 0.1477(8) 0.27127(13) 0.0402(8) Uani 1 1 d . . . . .
N2 N 0.33532(18) 0.6518(9) 0.19122(14) 0.0450(9) Uani 1 1 d . . . . .
N3 N 0.41275(16) 0.7411(8) 0.40955(12) 0.0360(8) Uani 1 1 d . . . . .
C1 C 0.50134(17) 0.4294(8) 0.34668(14) 0.0269(8) Uani 1 1 d . . . . .
C2 C 0.51005(18) 0.3315(9) 0.28422(14) 0.0297(8) Uani 1 1 d . . . . .
C3 C 0.45786(19) 0.4052(9) 0.23493(14) 0.0319(8) Uani 1 1 d . . . . .
H3 H 0.467188 0.336525 0.194987 0.038 Uiso 1 1 calc R U . . .
C4 C 0.39121(19) 0.5812(9) 0.24390(14) 0.0333(8) Uani 1 1 d . . . . .
C5 C 0.37778(18) 0.6905(9) 0.30132(14) 0.0309(8) Uani 1 1 d . . . . .
H5 H 0.332272 0.814168 0.306975 0.037 Uiso 1 1 calc R U . . .
C6 C 0.43151(18) 0.6172(8) 0.35029(13) 0.0275(8) Uani 1 1 d . . . . .
O8 O 0.92897(14) 0.2400(8) 0.46962(11) 0.0475(8) Uani 1 1 d . . . . .
N4 N 0.63732(16) 0.8513(7) 0.45272(12) 0.0344(8) Uani 1 1 d . . . . .
H4A H 0.634151 1.014932 0.423812 0.041 Uiso 1 1 calc R U . . .
H4B H 0.630607 0.941969 0.489763 0.041 Uiso 1 1 calc R U . . .
H4C H 0.599696 0.696077 0.442617 0.041 Uiso 1 1 calc R U . . .
C7 C 0.71433(18) 0.6904(9) 0.45593(14) 0.0309(8) Uani 1 1 d . . . . .
C8 C 0.7553(2) 0.6314(10) 0.51213(16) 0.0397(9) Uani 1 1 d . . . . .
H8 H 0.734638 0.696376 0.548663 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8264(2) 0.4777(10) 0.51476(15) 0.0404(10) Uani 1 1 d . . . . .
H9 H 0.854669 0.433312 0.553411 0.049 Uiso 1 1 calc R U . . .
C10 C 0.85753(19) 0.3860(9) 0.46137(15) 0.0341(9) Uani 1 1 d . . . . .
C11 C 0.8161(2) 0.4439(9) 0.40555(16) 0.0384(9) Uani 1 1 d . . . . .
H11 H 0.836914 0.380195 0.369012 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7429(2) 0.5970(9) 0.40246(15) 0.0370(9) Uani 1 1 d . . . . .
H12 H 0.713571 0.635623 0.364027 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9659(2) 0.1577(12) 0.41710(18) 0.0512(11) Uani 1 1 d . . . . .
H13A H 0.933212 0.001701 0.391403 0.077 Uiso 1 1 calc R U . . .
H13B H 1.016276 0.053139 0.429803 0.077 Uiso 1 1 calc R U . . .
H13C H 0.973862 0.361280 0.393783 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 C1 1.256(4) . ?
O2 N1 1.207(4) . ?
O3 N1 1.211(4) . ?
O4 N2 1.217(4) . ?
O5 N2 1.226(4) . ?
O6 N3 1.184(4) . ?
O7 N3 1.170(4) . ?
N1 C2 1.456(4) . ?
N2 C4 1.454(4) . ?
N3 C6 1.462(4) . ?
C1 C6 1.433(4) . ?
C1 C2 1.451(4) . ?
C2 C3 1.366(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9500 . ?
O8 C10 1.362(4) . ?
O8 C13 1.418(4) . ?
N4 C7 1.476(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
C7 C12 1.375(5) . ?
C7 C8 1.377(5) . ?
C8 C9 1.371(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(5) . ?
C11 C12 1.402(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 N1 O3 121.9(3) . . ?
O2 N1 C2 120.1(3) . . ?
O3 N1 C2 118.0(3) . . ?
O4 N2 O5 123.5(3) . . ?
O4 N2 C4 118.1(3) . . ?
O5 N2 C4 118.4(3) . . ?
O7 N3 O6 119.2(3) . . ?
O7 N3 C6 121.3(3) . . ?
O6 N3 C6 119.5(3) . . ?
O1 C1 C6 124.2(3) . . ?
O1 C1 C2 124.2(3) . . ?
C6 C1 C2 111.6(3) . . ?
C3 C2 C1 124.4(3) . . ?
C3 C2 N1 116.1(3) . . ?
C1 C2 N1 119.5(3) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 N2 120.2(3) . . ?
C3 C4 N2 118.6(3) . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 124.9(3) . . ?
C5 C6 N3 115.3(3) . . ?
C1 C6 N3 119.8(3) . . ?
C10 O8 C13 118.3(3) . . ?
C7 N4 H4A 109.5 . . ?
C7 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C7 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C12 C7 C8 121.4(3) . . ?
C12 C7 N4 119.0(3) . . ?
C8 C7 N4 119.6(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O8 C10 C11 124.8(3) . . ?
O8 C10 C9 115.4(3) . . ?
C11 C10 C9 119.7(3) . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.0(3) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O8 C13 H13A 109.5 . . ?
O8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C1 C2 C3 -179.1(3) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
O1 C1 C2 N1 -0.4(5) . . . . ?
C6 C1 C2 N1 178.0(3) . . . . ?
O2 N1 C2 C3 -159.0(3) . . . . ?
O3 N1 C2 C3 18.6(5) . . . . ?
O2 N1 C2 C1 22.1(5) . . . . ?
O3 N1 C2 C1 -160.2(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
N1 C2 C3 C4 -179.6(3) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C2 C3 C4 N2 -178.7(3) . . . . ?
O4 N2 C4 C5 -177.3(3) . . . . ?
O5 N2 C4 C5 3.1(5) . . . . ?
O4 N2 C4 C3 3.2(5) . . . . ?
O5 N2 C4 C3 -176.5(3) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
N2 C4 C5 C6 179.5(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 N3 -179.8(3) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 1.6(5) . . . . ?
O1 C1 C6 N3 -1.1(5) . . . . ?
C2 C1 C6 N3 -179.5(3) . . . . ?
O7 N3 C6 C5 167.1(4) . . . . ?
O6 N3 C6 C5 -12.7(5) . . . . ?
O7 N3 C6 C1 -12.0(6) . . . . ?
O6 N3 C6 C1 168.2(4) . . . . ?
C12 C7 C8 C9 0.3(6) . . . . ?
N4 C7 C8 C9 179.1(3) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C13 O8 C10 C11 3.8(6) . . . . ?
C13 O8 C10 C9 -176.5(3) . . . . ?
C8 C9 C10 O8 179.0(4) . . . . ?
C8 C9 C10 C11 -1.3(6) . . . . ?
O8 C10 C11 C12 -179.8(3) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C8 C7 C12 C11 -1.2(6) . . . . ?
N4 C7 C12 C11 -179.9(3) . . . . ?
C10 C11 C12 C7 0.7(6) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.088


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2440044'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H3 N3 O7), C6 H6 N2 O2'
_chemical_formula_sum            'C18 H12 N8 O16'
_chemical_formula_weight         596.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.40790(10)
_cell_length_b                   9.24020(10)
_cell_length_c                   23.1207(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2223.54(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    6746
_cell_measurement_theta_min      4.22
_cell_measurement_theta_max      76.24

_exptl_crystal_description       block
_exptl_crystal_colour            'orange yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    1.416
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      118(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   Rotating-anode
_diffrn_measurement_device_type  'Rigaku FR-X diffractometer'
_diffrn_detector                 'Hybrid Pixel Array'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7441
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.155
_diffrn_reflns_theta_max         75.788
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_point_group_measured_fraction_full 0.770
_reflns_number_total             3295
_reflns_number_gt                3293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.490
_reflns_Friedel_fraction_max     0.480
_reflns_Friedel_fraction_full    0.539

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.5681P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.65(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3295
_refine_ls_number_parameters     403
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.2433(2) 0.2770(2) 0.54984(11) 0.0298(4) Uani 1 1 d . . . . .
H2N H 0.178(3) 0.226(4) 0.5658(16) 0.036 Uiso 1 1 d . U . . .
H1N H 0.304(3) 0.216(3) 0.5314(15) 0.036 Uiso 1 1 d . U . . .
N2 N 0.23137(18) 0.8810(2) 0.53592(9) 0.0255(4) Uani 1 1 d . . . . .
O1 O 0.14464(17) 0.94638(19) 0.56090(9) 0.0351(4) Uani 1 1 d . . . . .
O2 O 0.31697(18) 0.94393(19) 0.50916(10) 0.0391(5) Uani 1 1 d . . . . .
C1 C 0.2386(2) 0.4240(2) 0.54531(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.3419(2) 0.5006(2) 0.52046(10) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.414386 0.449310 0.506229 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3385(2) 0.6493(2) 0.51666(10) 0.0208(4) Uani 1 1 d . . . . .
H3 H 0.407656 0.700435 0.499317 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2329(2) 0.7242(2) 0.53842(10) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.1299(2) 0.6513(2) 0.56353(10) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.058711 0.703758 0.578436 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1323(2) 0.5023(2) 0.56654(10) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.061707 0.451899 0.583056 0.025 Uiso 1 1 calc R U . . .
N3 N 0.44786(18) 0.4186(2) 0.31765(9) 0.0258(4) Uani 1 1 d . . . . .
N4 N 0.15563(18) 0.7861(2) 0.38968(10) 0.0277(4) Uani 1 1 d . . . . .
N5 N 0.06777(18) 0.2792(2) 0.43663(9) 0.0249(4) Uani 1 1 d . . . . .
O4 O 0.49348(18) 0.2975(2) 0.31951(10) 0.0377(5) Uani 1 1 d . . . . .
O5 O 0.4957(2) 0.5155(2) 0.29025(12) 0.0529(6) Uani 1 1 d . . . . .
O6 O 0.2278(2) 0.8738(2) 0.36665(10) 0.0425(5) Uani 1 1 d . . . . .
O7 O 0.05692(18) 0.8173(2) 0.41607(9) 0.0394(5) Uani 1 1 d . . . . .
O8 O -0.02356(17) 0.32243(19) 0.46480(9) 0.0327(4) Uani 1 1 d . . . . .
O9 O 0.09724(18) 0.15005(18) 0.43298(8) 0.0341(4) Uani 1 1 d . . . . .
C7 C 0.2556(2) 0.3394(2) 0.37494(10) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.276289 0.239951 0.370265 0.027 Uiso 0.172(4) 1 calc R U P A 1
O3 O 0.28905(18) 0.1999(2) 0.36581(10) 0.0258(5) Uani 0.828(4) 1 d D . P A 2
H3A H 0.233(3) 0.152(4) 0.3842(17) 0.039 Uiso 0.828(4) 1 d D U P A 2
C8 C 0.33020(19) 0.4511(2) 0.35060(10) 0.0203(4) Uani 1 1 d . . . . .
C9 C 0.2982(2) 0.5949(2) 0.35491(10) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.349901 0.667155 0.337235 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1890(2) 0.6323(2) 0.38553(10) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.1116(2) 0.5301(2) 0.41196(10) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.036747 0.557444 0.432796 0.026 Uiso 0.828(4) 1 calc R U P A 1
O3B O -0.0026(9) 0.6039(10) 0.4348(4) 0.026(2) Uiso 0.172(4) 1 d . . P A 2
H3B H -0.042969 0.547340 0.456702 0.039 Uiso 0.172(4) 1 calc R U P A 2
C12 C 0.1474(2) 0.3865(2) 0.40685(10) 0.0221(4) Uani 1 1 d . . . . .
N6 N 0.42461(17) 0.3050(2) 0.65838(8) 0.0234(4) Uani 1 1 d . . . . .
N7 N 0.2974(2) 0.8114(2) 0.68184(10) 0.0287(4) Uani 1 1 d . . . . .
N8 N 0.02883(18) 0.4386(2) 0.76755(9) 0.0234(4) Uani 1 1 d . . . . .
O11 O 0.40571(17) 0.17536(17) 0.66792(9) 0.0327(4) Uani 1 1 d . . . . .
O12 O 0.51365(16) 0.34896(18) 0.62915(9) 0.0336(4) Uani 1 1 d . . . . .
O13 O 0.3910(2) 0.8447(2) 0.65260(9) 0.0430(5) Uani 1 1 d . . . . .
O14 O 0.22005(18) 0.8977(2) 0.70206(10) 0.0389(4) Uani 1 1 d . . . . .
O15 O -0.05432(16) 0.53132(18) 0.77066(8) 0.0299(4) Uani 1 1 d . . . . .
O16 O 0.01947(19) 0.3201(2) 0.79004(11) 0.0472(6) Uani 1 1 d . . . . .
C13 C 0.2281(2) 0.3636(3) 0.71419(9) 0.0217(4) Uani 1 1 d . . . . .
H13 H 0.212037 0.264000 0.721343 0.026 Uiso 0.172(4) 1 calc R U P A 1
O10 O 0.19916(19) 0.2234(2) 0.72433(9) 0.0263(5) Uani 0.828(4) 1 d D . P A 2
H10A H 0.254(3) 0.167(4) 0.7084(17) 0.039 Uiso 0.828(4) 1 d D U P A 2
C14 C 0.3359(2) 0.4111(2) 0.68262(10) 0.0208(4) Uani 1 1 d . . . . .
C15 C 0.3625(2) 0.5564(2) 0.67257(10) 0.0217(4) Uani 1 1 d . . . . .
H15 H 0.437249 0.585221 0.652020 0.026 Uiso 0.828(4) 1 calc R U P A 1
O10B O 0.4695(9) 0.6241(9) 0.6500(4) 0.022(2) Uiso 0.172(4) 1 d . . P A 2
H10B H 0.502586 0.571233 0.624500 0.034 Uiso 0.172(4) 1 calc R U P A 2
C16 C 0.2766(2) 0.6572(3) 0.69342(10) 0.0224(5) Uani 1 1 d . . . . .
C17 C 0.1677(2) 0.6178(3) 0.72406(10) 0.0226(5) Uani 1 1 d . . . . .
H17 H 0.109264 0.689137 0.737615 0.027 Uiso 1 1 calc R U . . .
C18 C 0.14578(19) 0.4734(2) 0.73445(10) 0.0214(4) 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
N1 C1 1.364(3) . ?
N1 H2N 0.90(4) . ?
N1 H1N 0.95(3) . ?
N2 O1 1.230(3) . ?
N2 O2 1.231(3) . ?
N2 C4 1.450(3) . ?
C1 C2 1.410(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N3 O5 1.205(3) . ?
N3 O4 1.216(3) . ?
N3 C8 1.473(3) . ?
N4 O6 1.227(3) . ?
N4 O7 1.229(3) . ?
N4 C10 1.466(3) . ?
N5 O8 1.220(3) . ?
N5 O9 1.235(3) . ?
N5 C12 1.464(3) . ?
C7 O3 1.352(3) . ?
C7 C8 1.409(3) . ?
C7 C12 1.414(3) . ?
C7 H7 0.9500 . ?
O3 H3A 0.84(2) . ?
C8 C9 1.374(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C11 C12 1.384(3) . ?
C11 O3B 1.468(9) . ?
C11 H11 0.9500 . ?
O3B H3B 0.8400 . ?
N6 O12 1.217(3) . ?
N6 O11 1.234(2) . ?
N6 C14 1.458(3) . ?
N7 O14 1.225(3) . ?
N7 O13 1.226(3) . ?
N7 C16 1.466(3) . ?
N8 O16 1.216(3) . ?
N8 O15 1.220(2) . ?
N8 C18 1.473(3) . ?
C13 O10 1.351(3) . ?
C13 C14 1.408(3) . ?
C13 C18 1.409(3) . ?
C13 H13 0.9500 . ?
O10 H10A 0.86(2) . ?
C14 C15 1.391(3) . ?
C15 C16 1.378(3) . ?
C15 O10B 1.379(9) . ?
C15 H15 0.9500 . ?
O10B H10B 0.8400 . ?
C16 C17 1.385(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?

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
C1 N1 H2N 122(2) . . ?
C1 N1 H1N 125.4(19) . . ?
H2N N1 H1N 112(3) . . ?
O1 N2 O2 122.38(19) . . ?
O1 N2 C4 118.70(19) . . ?
O2 N2 C4 118.93(19) . . ?
N1 C1 C2 120.3(2) . . ?
N1 C1 C6 120.8(2) . . ?
C2 C1 C6 118.86(18) . . ?
C3 C2 C1 120.48(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 121.17(19) . . ?
C3 C4 N2 119.42(19) . . ?
C5 C4 N2 119.40(19) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.59(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O5 N3 O4 122.7(2) . . ?
O5 N3 C8 117.7(2) . . ?
O4 N3 C8 119.6(2) . . ?
O6 N4 O7 124.9(2) . . ?
O6 N4 C10 117.88(19) . . ?
O7 N4 C10 117.2(2) . . ?
O8 N5 O9 123.14(19) . . ?
O8 N5 C12 118.08(19) . . ?
O9 N5 C12 118.77(19) . . ?
O3 C7 C8 119.6(2) . . ?
O3 C7 C12 125.5(2) . . ?
C8 C7 C12 115.0(2) . . ?
C8 C7 H7 122.5 . . ?
C12 C7 H7 122.5 . . ?
C7 O3 H3A 104(3) . . ?
C9 C8 C7 123.1(2) . . ?
C9 C8 N3 115.9(2) . . ?
C7 C8 N3 121.06(19) . . ?
C8 C9 C10 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 122.3(2) . . ?
C9 C10 N4 118.0(2) . . ?
C11 C10 N4 119.67(19) . . ?
C10 C11 C12 117.4(2) . . ?
C10 C11 O3B 108.3(4) . . ?
C12 C11 O3B 134.0(4) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 O3B H3B 109.5 . . ?
C11 C12 C7 123.7(2) . . ?
C11 C12 N5 117.15(19) . . ?
C7 C12 N5 119.2(2) . . ?
O12 N6 O11 123.03(19) . . ?
O12 N6 C14 118.09(18) . . ?
O11 N6 C14 118.88(18) . . ?
O14 N7 O13 124.7(2) . . ?
O14 N7 C16 117.8(2) . . ?
O13 N7 C16 117.5(2) . . ?
O16 N8 O15 123.4(2) . . ?
O16 N8 C18 118.99(19) . . ?
O15 N8 C18 117.63(19) . . ?
O10 C13 C14 124.5(2) . . ?
O10 C13 C18 119.8(2) . . ?
C14 C13 C18 115.7(2) . . ?
C14 C13 H13 122.2 . . ?
C18 C13 H13 122.2 . . ?
C13 O10 H10A 111(3) . . ?
C15 C14 C13 123.1(2) . . ?
C15 C14 N6 117.34(19) . . ?
C13 C14 N6 119.6(2) . . ?
C16 C15 O10B 110.5(4) . . ?
C16 C15 C14 117.8(2) . . ?
O10B C15 C14 131.4(4) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 O10B H10B 109.5 . . ?
C15 C16 C17 122.1(2) . . ?
C15 C16 N7 119.8(2) . . ?
C17 C16 N7 118.0(2) . . ?
C18 C17 C16 118.7(2) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C13 122.7(2) . . ?
C17 C18 N8 116.07(19) . . ?
C13 C18 N8 121.2(2) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2440042'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H8 Cl N2 O'
_chemical_formula_sum            'C13 H10 Cl N5 O8'
_chemical_formula_weight         399.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.2420(2)
_cell_length_b                   14.9824(6)
_cell_length_c                   24.6205(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.692(4)
_cell_angle_gamma                90
_cell_volume                     1564.08(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5190
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.54

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.305
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9781
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         29.207
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3395
_reflns_number_gt                2203
_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       'APEX4 2021.4-0'
_computing_cell_refinement       'SAINT (Bruker, 2020)'
_computing_data_reduction        'SAINT (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0781P)²+0.8840P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.2161
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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 0.6283(6) 0.49448(17) 0.34822(10) 0.0361(6) Uani 1 1 d . . . . .
O2 O 0.8928(10) 0.3603(2) 0.29720(16) 0.0789(13) Uani 1 1 d . . . . .
O3 O 1.1950(8) 0.3943(2) 0.23274(14) 0.0634(10) Uani 1 1 d . . . . .
O4 O 1.0196(8) 0.6555(2) 0.12622(12) 0.0588(9) Uani 1 1 d . . . . .
O5 O 0.6511(8) 0.7480(2) 0.14828(12) 0.0550(9) Uani 1 1 d . . . . .
O6 O 0.2333(7) 0.74278(19) 0.32099(12) 0.0512(8) Uani 1 1 d . . . . .
O7 O 0.2059(7) 0.62150(18) 0.36672(12) 0.0460(8) Uani 1 1 d . . . . .
N1 N 0.9909(7) 0.4133(2) 0.26428(14) 0.0398(8) Uani 1 1 d . . . . .
N2 N 0.8157(8) 0.6818(2) 0.15680(13) 0.0423(9) Uani 1 1 d . . . . .
N3 N 0.3108(7) 0.6648(2) 0.32949(13) 0.0331(7) Uani 1 1 d . . . . .
C1 C 0.6592(8) 0.5360(2) 0.30361(14) 0.0292(8) Uani 1 1 d . . . . .
C2 C 0.8474(8) 0.5021(2) 0.26027(15) 0.0313(8) Uani 1 1 d . . . . .
C3 C 0.9013(8) 0.5489(3) 0.21329(15) 0.0346(9) Uani 1 1 d . . . . .
H3 H 1.029185 0.524307 0.186016 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7659(9) 0.6323(3) 0.20650(15) 0.0347(9) Uani 1 1 d . . . . .
C5 C 0.5747(8) 0.6692(2) 0.24465(15) 0.0324(8) Uani 1 1 d . . . . .
H5 H 0.480686 0.726013 0.238703 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5216(8) 0.6223(2) 0.29161(14) 0.0290(8) Uani 1 1 d . . . . .
Cl1 Cl 0.7159(3) 0.01659(7) 0.57948(5) 0.0591(4) Uani 1 1 d . . . . .
O8 O 0.2240(7) 0.42987(18) 0.51990(11) 0.0458(8) Uani 1 1 d . . . . .
N4 N 0.2543(7) 0.37716(19) 0.43543(12) 0.0338(7) Uani 1 1 d . . . . .
H4 H 0.294298 0.332562 0.413413 0.041 Uiso 1 1 calc R U . . .
N5 N 0.1573(7) 0.46103(19) 0.41499(12) 0.0311(7) Uani 1 1 d . . . . .
H5A H 0.112258 0.497804 0.443139 0.047 Uiso 1 1 calc R U . . .
H5B H -0.017732 0.454091 0.393140 0.047 Uiso 1 1 calc R U . . .
H5C H 0.314880 0.485324 0.395511 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2837(8) 0.3675(2) 0.48975(13) 0.0283(8) Uani 1 1 d . . . . .
C8 C 0.3918(8) 0.2790(2) 0.50987(14) 0.0276(8) Uani 1 1 d . . . . .
C9 C 0.3012(9) 0.2533(3) 0.56164(15) 0.0356(9) Uani 1 1 d . . . . .
H9 H 0.174269 0.292028 0.582348 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3948(9) 0.1723(2) 0.58281(16) 0.0375(9) Uani 1 1 d . . . . .
H10 H 0.329639 0.153949 0.617670 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5858(9) 0.1179(2) 0.55237(17) 0.0398(9) Uani 1 1 d . . . . .
C12 C 0.6804(9) 0.1422(3) 0.50137(17) 0.0392(9) Uani 1 1 d . . . . .
H12 H 0.810452 0.103567 0.481158 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5839(8) 0.2232(2) 0.48000(15) 0.0324(8) Uani 1 1 d . . . . .
H13 H 0.648412 0.240845 0.444981 0.039 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 C1 1.272(4) . ?
O2 N1 1.217(4) . ?
O3 N1 1.214(4) . ?
O4 N2 1.228(5) . ?
O5 N2 1.227(5) . ?
O6 N3 1.229(4) . ?
O7 N3 1.218(4) . ?
N1 C2 1.465(5) . ?
N2 C4 1.452(5) . ?
N3 C6 1.457(5) . ?
C1 C2 1.443(5) . ?
C1 C6 1.446(5) . ?
C2 C3 1.377(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9500 . ?
Cl1 C11 1.742(4) . ?
O8 C7 1.224(4) . ?
N4 C7 1.347(4) . ?
N4 N5 1.410(4) . ?
N4 H4 0.8800 . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
C7 C8 1.484(5) . ?
C8 C13 1.392(5) . ?
C8 C9 1.396(5) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(6) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O3 N1 O2 122.5(4) . . ?
O3 N1 C2 118.2(3) . . ?
O2 N1 C2 119.2(3) . . ?
O5 N2 O4 124.2(4) . . ?
O5 N2 C4 117.4(3) . . ?
O4 N2 C4 118.4(4) . . ?
O7 N3 O6 122.2(3) . . ?
O7 N3 C6 119.6(3) . . ?
O6 N3 C6 118.2(3) . . ?
O1 C1 C2 122.7(3) . . ?
O1 C1 C6 124.2(3) . . ?
C2 C1 C6 113.1(3) . . ?
C3 C2 C1 123.5(3) . . ?
C3 C2 N1 116.1(3) . . ?
C1 C2 N1 120.5(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 122.1(3) . . ?
C5 C4 N2 118.3(4) . . ?
C3 C4 N2 119.5(4) . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 123.5(3) . . ?
C5 C6 N3 115.7(3) . . ?
C1 C6 N3 120.8(3) . . ?
C7 N4 N5 117.8(3) . . ?
C7 N4 H4 121.1 . . ?
N5 N4 H4 121.1 . . ?
N4 N5 H5A 109.5 . . ?
N4 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
N4 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
O8 C7 N4 120.4(3) . . ?
O8 C7 C8 123.2(3) . . ?
N4 C7 C8 116.5(3) . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 C7 122.7(3) . . ?
C9 C8 C7 117.4(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 118.8(4) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 Cl1 118.8(3) . . ?
C10 C11 Cl1 119.3(3) . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2440043'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2025-04-01 deposited with the CCDC.	2026-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C6 H8 N O'
_chemical_formula_sum            'C12 H10 N4 O8'
_chemical_formula_weight         338.24

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                   8.0915(4)
_cell_length_b                   8.4379(4)
_cell_length_c                   10.3328(5)
_cell_angle_alpha                79.285(4)
_cell_angle_beta                 82.174(4)
_cell_angle_gamma                88.062(4)
_cell_volume                     686.69(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4698
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      23.69

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            23067
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         33.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4535
_reflns_number_gt                4113
_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       'APEX4 2021.4-0'
_computing_cell_refinement       'SAINT (Bruker, 2020)'
_computing_data_reduction        'SAINT (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0741P)²+0.1948P] 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         4535
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.05040(10) 0.13602(10) 0.81523(7) 0.02697(18) Uani 1 1 d . . . . .
O2 O -0.07831(15) 0.42119(16) 0.86765(14) 0.0581(4) Uani 1 1 d . . . . .
O3 O 0.09550(15) 0.61497(11) 0.79434(10) 0.0418(2) Uani 1 1 d . . . . .
O4 O 0.38102(19) 0.65891(12) 0.35263(12) 0.0589(4) Uani 1 1 d . . . . .
O5 O 0.44087(15) 0.44402(12) 0.27077(10) 0.0453(3) Uani 1 1 d . . . . .
O6 O 0.27414(14) -0.07783(11) 0.52992(10) 0.0417(2) Uani 1 1 d . . . . .
O7 O 0.02878(12) -0.07493(10) 0.64379(9) 0.0338(2) Uani 1 1 d . . . . .
N1 N 0.03848(13) 0.48293(12) 0.78946(10) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.37063(14) 0.51373(12) 0.35784(10) 0.0313(2) Uani 1 1 d . . . . .
N3 N 0.16042(13) -0.00917(11) 0.58875(9) 0.02609(19) Uani 1 1 d . . . . .
C1 C 0.10615(12) 0.22439(12) 0.70655(9) 0.02066(19) Uani 1 1 d . . . . .
C2 C 0.11699(13) 0.39825(12) 0.68649(10) 0.02240(19) Uani 1 1 d . . . . .
C3 C 0.20139(14) 0.49245(12) 0.57514(10) 0.0245(2) Uani 1 1 d . . . . .
H3 H 0.208370 0.605874 0.568684 0.029 Uiso 1 1 calc R U . . .
C4 C 0.27580(14) 0.41784(12) 0.47285(10) 0.0242(2) Uani 1 1 d . . . . .
C5 C 0.26426(13) 0.25255(12) 0.47862(10) 0.0236(2) Uani 1 1 d . . . . .
H5 H 0.315113 0.203361 0.407418 0.028 Uiso 1 1 calc R U . . .
C6 C 0.17732(13) 0.16208(11) 0.59006(9) 0.02145(19) Uani 1 1 d . . . . .
O8 O 0.32482(11) 0.36512(11) 0.91536(9) 0.0331(2) Uani 1 1 d . . . . .
H8A H 0.398(3) 0.413(3) 0.864(2) 0.055(6) Uiso 1 1 d . . . . .
N4 N 0.10977(10) 0.15534(10) 1.07355(8) 0.02104(17) Uani 1 1 d . . . . .
H4A H 0.102119 0.162011 0.985648 0.025 Uiso 1 1 calc R U . . .
H4B H 0.060258 0.243535 1.101777 0.025 Uiso 1 1 calc R U . . .
H4C H 0.057596 0.064655 1.120680 0.025 Uiso 1 1 calc R U . . .
C7 C 0.28541(12) 0.14860(11) 1.09373(9) 0.02025(18) Uani 1 1 d . . . . .
C8 C 0.34137(14) 0.03272(13) 1.19179(11) 0.0267(2) Uani 1 1 d . . . . .
H8 H 0.266293 -0.043563 1.246749 0.032 Uiso 1 1 calc R U . . .
C9 C 0.50837(16) 0.02954(16) 1.20866(14) 0.0353(3) Uani 1 1 d . . . . .
H9 H 0.548897 -0.048991 1.275666 0.042 Uiso 1 1 calc R U . . .
C10 C 0.61624(15) 0.14167(17) 1.12714(15) 0.0362(3) Uani 1 1 d . . . . .
H10 H 0.730492 0.139806 1.139664 0.043 Uiso 1 1 calc R U . . .
C11 C 0.56033(14) 0.25653(15) 1.02766(12) 0.0311(2) Uani 1 1 d . . . . .
H11 H 0.635731 0.332135 0.972232 0.037 Uiso 1 1 calc R U . . .
C12 C 0.39325(13) 0.25978(12) 1.00998(10) 0.0234(2) 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 C1 1.2626(11) . ?
O2 N1 1.2190(14) . ?
O3 N1 1.2324(14) . ?
O4 N2 1.2215(13) . ?
O5 N2 1.2302(14) . ?
O6 N3 1.2226(14) . ?
O7 N3 1.2343(13) . ?
N1 C2 1.4540(13) . ?
N2 C4 1.4463(13) . ?
N3 C6 1.4587(13) . ?
C1 C6 1.4432(14) . ?
C1 C2 1.4469(14) . ?
C2 C3 1.3800(13) . ?
C3 C4 1.3872(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3907(14) . ?
C5 C6 1.3756(13) . ?
C5 H5 0.9500 . ?
O8 C12 1.3578(13) . ?
O8 H8A 0.81(2) . ?
N4 C7 1.4620(13) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
C7 C8 1.3836(14) . ?
C7 C12 1.3922(13) . ?
C8 C9 1.3846(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3877(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3882(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3874(15) . ?
C11 H11 0.9500 . ?

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 N1 O3 122.75(11) . . ?
O2 N1 C2 119.53(10) . . ?
O3 N1 C2 117.71(9) . . ?
O4 N2 O5 122.89(10) . . ?
O4 N2 C4 118.97(10) . . ?
O5 N2 C4 118.11(9) . . ?
O6 N3 O7 123.82(10) . . ?
O6 N3 C6 118.52(9) . . ?
O7 N3 C6 117.61(9) . . ?
O1 C1 C6 123.54(9) . . ?
O1 C1 C2 124.31(9) . . ?
C6 C1 C2 112.02(8) . . ?
C3 C2 C1 124.23(9) . . ?
C3 C2 N1 116.26(9) . . ?
C1 C2 N1 119.50(9) . . ?
C2 C3 C4 118.53(9) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 121.84(9) . . ?
C3 C4 N2 119.27(9) . . ?
C5 C4 N2 118.88(9) . . ?
C6 C5 C4 118.31(9) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 124.63(9) . . ?
C5 C6 N3 116.46(9) . . ?
C1 C6 N3 118.91(8) . . ?
C12 O8 H8A 109.2(16) . . ?
C7 N4 H4A 109.5 . . ?
C7 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C7 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C8 C7 C12 121.71(9) . . ?
C8 C7 N4 120.38(9) . . ?
C12 C7 N4 117.90(9) . . ?
C7 C8 C9 119.05(10) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 119.64(11) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 121.25(11) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.34(10) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
O8 C12 C11 124.58(10) . . ?
O8 C12 C7 116.42(9) . . ?
C11 C12 C7 119.00(10) . . ?

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 C1 C2 C3 169.27(10) . . . . ?
C6 C1 C2 C3 -6.73(15) . . . . ?
O1 C1 C2 N1 -9.32(16) . . . . ?
C6 C1 C2 N1 174.68(9) . . . . ?
O2 N1 C2 C3 156.68(13) . . . . ?
O3 N1 C2 C3 -24.13(15) . . . . ?
O2 N1 C2 C1 -24.62(17) . . . . ?
O3 N1 C2 C1 154.57(11) . . . . ?
C1 C2 C3 C4 2.60(17) . . . . ?
N1 C2 C3 C4 -178.78(10) . . . . ?
C2 C3 C4 C5 1.44(17) . . . . ?
C2 C3 C4 N2 -177.44(10) . . . . ?
O4 N2 C4 C3 -1.03(19) . . . . ?
O5 N2 C4 C3 177.23(12) . . . . ?
O4 N2 C4 C5 -179.95(13) . . . . ?
O5 N2 C4 C5 -1.69(18) . . . . ?
C3 C4 C5 C6 -0.54(17) . . . . ?
N2 C4 C5 C6 178.35(10) . . . . ?
C4 C5 C6 C1 -4.52(16) . . . . ?
C4 C5 C6 N3 176.68(10) . . . . ?
O1 C1 C6 C5 -168.29(10) . . . . ?
C2 C1 C6 C5 7.74(15) . . . . ?
O1 C1 C6 N3 10.49(15) . . . . ?
C2 C1 C6 N3 -173.48(9) . . . . ?
O6 N3 C6 C5 33.11(15) . . . . ?
O7 N3 C6 C5 -144.51(10) . . . . ?
O6 N3 C6 C1 -145.77(11) . . . . ?
O7 N3 C6 C1 36.61(14) . . . . ?
C12 C7 C8 C9 1.34(16) . . . . ?
N4 C7 C8 C9 -179.90(10) . . . . ?
C7 C8 C9 C10 -0.19(19) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 O8 -179.27(11) . . . . ?
C10 C11 C12 C7 0.73(17) . . . . ?
C8 C7 C12 O8 178.39(10) . . . . ?
N4 C7 C12 O8 -0.41(14) . . . . ?
C8 C7 C12 C11 -1.61(16) . . . . ?
N4 C7 C12 C11 179.60(9) . . . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.051

