# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2308065'
loop_
_audit_author_name
_audit_author_address
'Yuteng Cao'
;CAEP
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H N9 O3, H2 O'
_chemical_formula_sum            'C4 H3 N9 O4'
_chemical_formula_weight         241.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4697(4)
_cell_length_b                   11.6283(6)
_cell_length_c                   9.2837(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.7430(10)
_cell_angle_gamma                90
_cell_volume                     896.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1155 before and 0.0671 after correction. The Ratio of minimum to maximum transmission is 0.9027. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9210
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.346
_diffrn_reflns_theta_min         2.453
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1268
_reflns_number_total             1829
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0352P)²+0.3649P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43863(19) 0.28138(15) 0.40582(19) 0.0286(4) Uani 1 1 d . . . . .
O4 O 0.0726(2) 0.58722(18) 0.3184(2) 0.0347(5) Uani 1 1 d . . . . .
O3 O 0.0951(2) 0.38028(16) 0.4982(2) 0.0357(5) Uani 1 1 d . . . . .
O2 O 0.0929(2) 0.20944(16) 0.5919(2) 0.0358(5) Uani 1 1 d . . . . .
N5 N 0.2916(2) 0.42759(18) 0.3901(2) 0.0259(5) Uani 1 1 d . . . . .
N4 N 0.3888(2) 0.46305(18) 0.3247(2) 0.0271(5) Uani 1 1 d . . . . .
N9 N 0.1464(2) 0.2795(2) 0.5303(2) 0.0293(5) Uani 1 1 d . . . . .
N2 N 0.7682(2) 0.28171(19) 0.2307(2) 0.0297(5) Uani 1 1 d . . . . .
N8 N 0.2648(2) 0.24101(18) 0.5008(2) 0.0304(5) Uani 1 1 d . . . . .
N6 N 0.7876(2) 0.43312(18) 0.0740(3) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.6140(2) 0.44248(19) 0.1922(2) 0.0303(5) Uani 1 1 d . . . . .
N3 N 0.6796(2) 0.26433(19) 0.3077(2) 0.0310(5) Uani 1 1 d . . . . .
N7 N 0.8423(3) 0.4659(2) 0.0012(3) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.4734(3) 0.3739(2) 0.3364(3) 0.0247(6) Uani 1 1 d . . . . .
C1 C 0.7228(3) 0.3866(2) 0.1671(3) 0.0279(6) Uani 1 1 d . . . . .
C4 C 0.3203(3) 0.3192(2) 0.4364(3) 0.0260(6) Uani 1 1 d . . . . .
C2 C 0.5916(3) 0.3612(2) 0.2813(3) 0.0257(6) Uani 1 1 d . . . . .
H5 H 0.209(3) 0.481(3) 0.377(3) 0.051(9) Uiso 1 1 d . . . . .
H4A H 0.113(4) 0.651(3) 0.303(4) 0.068(12) Uiso 1 1 d . . . . .
H4B H 0.029(4) 0.609(3) 0.385(4) 0.076(12) Uiso 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 C3 1.372(3) . ?
O1 C4 1.355(3) . ?
O4 H4A 0.88(4) . ?
O4 H4B 0.93(4) . ?
O3 N9 1.249(3) . ?
O2 N9 1.235(3) . ?
N5 N4 1.387(3) . ?
N5 C4 1.317(3) . ?
N5 H5 0.96(3) . ?
N4 C3 1.283(3) . ?
N9 N8 1.351(3) . ?
N2 N3 1.353(3) . ?
N2 C1 1.333(3) . ?
N8 C4 1.328(3) . ?
N6 N7 1.098(3) . ?
N6 C1 1.389(3) . ?
N1 C1 1.330(3) . ?
N1 C2 1.338(3) . ?
N3 C2 1.352(3) . ?
C3 C2 1.445(3) . ?
C1 C2 2.005(3) . ?

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
C4 O1 C3 104.65(19) . . ?
H4A O4 H4B 105(3) . . ?
N4 N5 H5 115.1(17) . . ?
C4 N5 N4 110.6(2) . . ?
C4 N5 H5 133.5(17) . . ?
C3 N4 N5 104.0(2) . . ?
O3 N9 N8 121.8(2) . . ?
O2 N9 O3 122.0(2) . . ?
O2 N9 N8 116.1(2) . . ?
C1 N2 N3 102.8(2) . . ?
C4 N8 N9 114.3(2) . . ?
N7 N6 C1 177.1(3) . . ?
C1 N1 C2 97.4(2) . . ?
C2 N3 N2 105.3(2) . . ?
O1 C3 C2 119.2(2) . . ?
N4 C3 O1 113.1(2) . . ?
N4 C3 C2 127.6(2) . . ?
N2 C1 N6 119.2(2) . . ?
N2 C1 C2 77.35(16) . . ?
N6 C1 C2 163.4(2) . . ?
N1 C1 N2 118.8(2) . . ?
N1 C1 N6 122.0(2) . . ?
N1 C1 C2 41.44(13) . . ?
N5 C4 O1 107.7(2) . . ?
N5 C4 N8 137.6(2) . . ?
N8 C4 O1 114.7(2) . . ?
N1 C2 N3 115.7(2) . . ?
N1 C2 C3 121.8(2) . . ?
N1 C2 C1 41.12(13) . . ?
N3 C2 C3 122.4(2) . . ?
N3 C2 C1 74.55(16) . . ?
C3 C2 C1 162.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C2 N1 170.4(2) . . . . ?
O1 C3 C2 N3 -5.6(3) . . . . ?
O1 C3 C2 C1 162.0(5) . . . . ?
O3 N9 N8 C4 0.2(3) . . . . ?
O2 N9 N8 C4 -179.2(2) . . . . ?
N5 N4 C3 O1 -0.1(2) . . . . ?
N5 N4 C3 C2 177.7(2) . . . . ?
N4 N5 C4 O1 1.1(3) . . . . ?
N4 N5 C4 N8 -178.1(3) . . . . ?
N4 C3 C2 N1 -7.4(4) . . . . ?
N4 C3 C2 N3 176.6(2) . . . . ?
N4 C3 C2 C1 -15.8(8) . . . . ?
N9 N8 C4 O1 -179.76(18) . . . . ?
N9 N8 C4 N5 -0.5(4) . . . . ?
N2 N3 C2 N1 0.1(3) . . . . ?
N2 N3 C2 C3 176.3(2) . . . . ?
N2 N3 C2 C1 0.09(16) . . . . ?
N3 N2 C1 N6 -178.5(2) . . . . ?
N3 N2 C1 N1 0.2(3) . . . . ?
N3 N2 C1 C2 0.09(16) . . . . ?
C3 O1 C4 N5 -1.2(2) . . . . ?
C3 O1 C4 N8 178.29(19) . . . . ?
C1 N2 N3 C2 -0.1(2) . . . . ?
C1 N1 C2 N3 0.0(3) . . . . ?
C1 N1 C2 C3 -176.2(2) . . . . ?
C4 O1 C3 N4 0.8(3) . . . . ?
C4 O1 C3 C2 -177.3(2) . . . . ?
C4 N5 N4 C3 -0.6(2) . . . . ?
C2 N1 C1 N2 -0.1(3) . . . . ?
C2 N1 C1 N6 178.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2308066'
loop_
_audit_author_name
_audit_author_address
'Yuteng Cao'
;CAEP
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H3 N9 O5, H3 N O'
_chemical_formula_sum            'C4 H6 N10 O6'
_chemical_formula_weight         290.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.0641(4)
_cell_length_b                   18.1481(18)
_cell_length_c                   6.2142(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.131(3)
_cell_angle_gamma                90
_cell_volume                     525.20(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.736
_cell_measurement_theta_min      2.244
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0983 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.7654.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4042
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         2.244
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                849
_reflns_number_total             1071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.6175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Shared sites
{N1, O1}
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(O1)
4. Others
 Fixed Sof: N1(0.5) H1(0.5) H4(0.5) H2(0.5) O4(0.5) H4A(0.5) N6(0.5) H6A(0.5)
 H6B(0.5) O1(0.5)
5.a Riding coordinates:
 N6(H6A,H6B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), N2(H2)
5.c Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.5184(5) 0.25647(12) 0.5459(4) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.6403(5) 0.45945(13) 0.7963(4) 0.0250(6) Uani 0.5 1 d . . P A 1
H1 H 0.737682 0.493990 0.760053 0.030 Uiso 0.5 1 calc R U P A 1
O2 O 0.7578(6) 0.28563(13) 0.3333(4) 0.0323(6) Uani 1 1 d . . . . .
N5 N 0.6566(6) 0.30073(14) 0.4821(4) 0.0226(6) Uani 1 1 d . . . . .
N4 N 0.7115(6) 0.37000(14) 0.5657(4) 0.0237(6) Uani 1 1 d . . . . .
H4 H 0.815753 0.400744 0.522319 0.028 Uiso 0.5 1 calc R U P B 2
N2 N 0.4430(6) 0.35650(14) 0.8203(4) 0.0232(6) Uani 1 1 d . . . . .
H2 H 0.388369 0.310094 0.799736 0.028 Uiso 0.5 1 calc R U P C 1
N3 N 0.3788(6) 0.40505(15) 0.9632(4) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.5983(7) 0.38898(16) 0.7175(5) 0.0219(7) Uani 1 1 d . . . . .
C2 C 0.5011(7) 0.46571(18) 0.9426(5) 0.0259(7) Uani 1 1 d . . . . .
O4 O 1.0598(9) 0.4120(2) 0.2839(8) 0.0264(10) Uani 0.5 1 d . . P D -1
H4A H 0.977025 0.374858 0.308885 0.040 Uiso 0.5 1 calc R U P D -1
N6 N 1.0408(12) 0.4765(3) 0.4398(9) 0.0261(12) Uani 0.5 1 d . . P D -1
H6A H 0.967979 0.469131 0.545394 0.031 Uiso 0.5 1 d R U P D -1
H6B H 1.102319 0.520531 0.422624 0.031 Uiso 0.5 1 d R U P D -1
O1 O 0.6403(5) 0.45945(13) 0.7963(4) 0.0250(6) Uani 0.5 1 d . . P A 2


_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
O3 N5 1.229(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.356(4) . ?
N1 C2 1.357(4) . ?
O2 N5 1.251(3) . ?
N5 N4 1.347(4) . ?
N4 H4 0.8800 . ?
N4 C1 1.327(4) . ?
N2 H2 0.8800 . ?
N2 N3 1.378(3) . ?
N2 C1 1.330(4) . ?
N3 C2 1.294(4) . ?
C1 O1 1.356(4) . ?
C2 C2 1.436(6) 3_667 ?
C2 O1 1.357(4) . ?
O4 H4A 0.8400 . ?
O4 N6 1.545(7) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8799 . ?

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 H1 127.1 . . ?
C1 N1 C2 105.8(3) . . ?
C2 N1 H1 127.1 . . ?
O3 N5 O2 123.1(3) . . ?
O3 N5 N4 122.9(2) . . ?
O2 N5 N4 114.0(3) . . ?
N5 N4 H4 122.1 . . ?
C1 N4 N5 115.8(3) . . ?
C1 N4 H4 122.1 . . ?
N3 N2 H2 124.4 . . ?
C1 N2 H2 124.4 . . ?
C1 N2 N3 111.1(3) . . ?
C2 N3 N2 103.7(2) . . ?
N4 C1 N1 116.8(3) . . ?
N4 C1 N2 136.8(3) . . ?
N4 C1 O1 116.8(3) . . ?
N2 C1 N1 106.4(3) . . ?
N2 C1 O1 106.4(3) . . ?
N1 C2 C2 120.8(4) . 3_667 ?
N3 C2 N1 113.0(3) . . ?
N3 C2 C2 126.2(4) . 3_667 ?
N3 C2 O1 113.0(3) . . ?
O1 C2 C2 120.8(4) . 3_667 ?
N6 O4 H4A 109.5 . . ?
O4 N6 H6A 120.0 . . ?
O4 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C1 O1 C2 105.8(3) . . ?

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
O3 N5 N4 C1 -2.2(4) . . . . ?
O2 N5 N4 C1 177.6(3) . . . . ?
N5 N4 C1 N1 -177.2(2) . . . . ?
N5 N4 C1 N2 2.1(5) . . . . ?
N5 N4 C1 O1 -177.2(2) . . . . ?
N4 C1 O1 C2 178.7(3) . . . . ?
N2 N3 C2 N1 -0.1(3) . . . . ?
N2 N3 C2 C2 180.0(4) . . . 3_667 ?
N2 N3 C2 O1 -0.1(3) . . . . ?
N2 C1 O1 C2 -0.9(3) . . . . ?
N3 N2 C1 N1 0.9(3) . . . . ?
N3 N2 C1 N4 -178.5(4) . . . . ?
N3 N2 C1 O1 0.9(3) . . . . ?
N3 C2 O1 C1 0.6(4) . . . . ?
C1 N1 C2 N3 0.6(4) . . . . ?
C1 N1 C2 C2 -179.5(4) . . . 3_667 ?
C1 N2 N3 C2 -0.5(3) . . . . ?
C2 N1 C1 N4 178.7(3) . . . . ?
C2 N1 C1 N2 -0.9(3) . . . . ?
C2 C2 O1 C1 -179.5(4) 3_667 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_2                   
;
PROBLEM: Short Inter D...A Contact  O2       ..O3       .       2.71 Ang.
RESPONSE: Checked, it's okay.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2308067'
loop_
_audit_author_name
_audit_author_address
'Yuteng Cao'
;CAEP
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N10 O3, 2(H2 O)'
_chemical_formula_sum            'C4 H6 N10 O5'
_chemical_formula_weight         274.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   20.5383(13)
_cell_length_b                   13.8050(13)
_cell_length_c                   8.0494(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.633(4)
_cell_angle_gamma                90
_cell_volume                     2106.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      2.15
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5677
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0958 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.7616. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8836
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1512
_reflns_number_total             2123
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+1.2713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1338
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H4B(0.5) H4C(0.5)
3.a Riding coordinates:
 O4(H4A,H4B,H4C)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66929(8) 0.22051(12) 0.5193(2) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.59917(9) -0.08061(13) 0.3462(3) 0.0299(5) Uani 1 1 d . . . . .
O3 O 0.54891(9) 0.03701(13) 0.1613(2) 0.0305(5) Uani 1 1 d . . . . .
N2 N 0.76314(10) 0.47719(15) 0.7504(3) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.798233 0.496673 0.848113 0.027 Uiso 1 1 calc R U . . .
N5 N 0.58743(10) 0.21417(15) 0.2531(3) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.555731 0.191146 0.152558 0.026 Uiso 1 1 calc R U . . .
N10 N 0.59083(11) 0.00628(16) 0.3068(3) 0.0237(5) Uani 1 1 d . . . . .
N9 N 0.63292(10) 0.06719(15) 0.4375(3) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.74410(10) 0.38328(15) 0.7077(3) 0.0228(5) Uani 1 1 d . . . . .
N1 N 0.67320(10) 0.48554(15) 0.4900(3) 0.0227(5) Uani 1 1 d . . . . .
N7 N 0.68261(12) 0.67997(16) 0.5144(3) 0.0277(5) Uani 1 1 d . . . . .
N4 N 0.60392(10) 0.31156(15) 0.2872(3) 0.0233(5) Uani 1 1 d . . . . .
N6 N 0.73036(11) 0.63499(16) 0.6382(3) 0.0277(5) Uani 1 1 d . . . . .
C3 C 0.65266(12) 0.31103(18) 0.4465(3) 0.0212(6) Uani 1 1 d . . . . .
C1 C 0.72074(12) 0.53536(19) 0.6222(3) 0.0221(6) Uani 1 1 d . . . . .
C4 C 0.62601(12) 0.16072(18) 0.3929(3) 0.0212(6) Uani 1 1 d . . . . .
C2 C 0.69041(12) 0.39337(18) 0.5500(3) 0.0213(5) Uani 1 1 d . . . . .
N8 N 0.64362(13) 0.72776(18) 0.4131(4) 0.0391(6) Uani 1 1 d . . . . .
O5 O 0.47503(10) 0.22027(18) -0.0548(3) 0.0298(5) Uani 1 1 d . . . . .
O4 O 0.54102(11) 0.56488(16) 0.1493(3) 0.0443(6) Uani 1 1 d . . . . .
H4A H 0.576413 0.526682 0.205291 0.066 Uiso 1 1 d R U . . .
H4B H 0.515583 0.533002 0.054741 0.066 Uiso 0.5 1 d R U P . .
H4C H 0.515423 0.568302 0.212111 0.08(3) Uiso 0.5 1 d R . P . .
H5A H 0.4709(17) 0.276(3) -0.088(5) 0.051(11) Uiso 1 1 d . . . . .
H5B H 0.4600(17) 0.180(3) -0.136(5) 0.049(11) Uiso 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 C3 1.367(3) . ?
O1 C4 1.346(3) . ?
O2 N10 1.236(3) . ?
O3 N10 1.232(3) . ?
N2 H2 0.8800 . ?
N2 N3 1.359(3) . ?
N2 C1 1.333(3) . ?
N5 H5 0.8800 . ?
N5 N4 1.388(3) . ?
N5 C4 1.324(3) . ?
N10 N9 1.364(3) . ?
N9 C4 1.333(3) . ?
N3 C2 1.330(3) . ?
N1 C1 1.326(3) . ?
N1 C2 1.359(3) . ?
N7 N6 1.260(3) . ?
N7 N8 1.113(3) . ?
N4 C3 1.288(3) . ?
N6 C1 1.388(3) . ?
C3 C2 1.446(3) . ?
O5 H5A 0.80(4) . ?
O5 H5B 0.82(4) . ?
O4 H4A 0.8704 . ?
O4 H4B 0.8599 . ?
O4 H4C 0.8599 . ?

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
C4 O1 C3 104.68(18) . . ?
N3 N2 H2 125.1 . . ?
C1 N2 H2 125.1 . . ?
C1 N2 N3 109.9(2) . . ?
N4 N5 H5 124.7 . . ?
C4 N5 H5 124.7 . . ?
C4 N5 N4 110.6(2) . . ?
O2 N10 N9 114.6(2) . . ?
O3 N10 O2 123.7(2) . . ?
O3 N10 N9 121.6(2) . . ?
C4 N9 N10 114.8(2) . . ?
C2 N3 N2 101.16(19) . . ?
C1 N1 C2 101.0(2) . . ?
N8 N7 N6 173.2(3) . . ?
C3 N4 N5 103.2(2) . . ?
N7 N6 C1 112.0(2) . . ?
O1 C3 C2 118.8(2) . . ?
N4 C3 O1 113.7(2) . . ?
N4 C3 C2 127.5(2) . . ?
N2 C1 N6 119.8(2) . . ?
N1 C1 N2 111.6(2) . . ?
N1 C1 N6 128.5(2) . . ?
N5 C4 O1 107.8(2) . . ?
N5 C4 N9 137.4(2) . . ?
N9 C4 O1 114.8(2) . . ?
N3 C2 N1 116.4(2) . . ?
N3 C2 C3 122.1(2) . . ?
N1 C2 C3 121.6(2) . . ?
H5A O5 H5B 114(3) . . ?
H4A O4 H4B 104.5 . . ?
H4A O4 H4C 107.8 . . ?
H4B O4 H4C 104.3 . . ?

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 C3 C2 N3 4.9(3) . . . . ?
O1 C3 C2 N1 -175.6(2) . . . . ?
O2 N10 N9 C4 177.5(2) . . . . ?
O3 N10 N9 C4 -1.6(3) . . . . ?
N2 N3 C2 N1 -0.8(3) . . . . ?
N2 N3 C2 C3 178.6(2) . . . . ?
N5 N4 C3 O1 0.0(2) . . . . ?
N5 N4 C3 C2 179.1(2) . . . . ?
N10 N9 C4 O1 -177.74(19) . . . . ?
N10 N9 C4 N5 1.6(4) . . . . ?
N3 N2 C1 N1 -0.8(3) . . . . ?
N3 N2 C1 N6 179.7(2) . . . . ?
N7 N6 C1 N2 -174.4(2) . . . . ?
N7 N6 C1 N1 6.2(4) . . . . ?
N4 N5 C4 O1 -1.2(3) . . . . ?
N4 N5 C4 N9 179.4(3) . . . . ?
N4 C3 C2 N3 -174.1(2) . . . . ?
N4 C3 C2 N1 5.3(4) . . . . ?
C3 O1 C4 N5 1.2(2) . . . . ?
C3 O1 C4 N9 -179.33(19) . . . . ?
C1 N2 N3 C2 0.9(2) . . . . ?
C1 N1 C2 N3 0.4(3) . . . . ?
C1 N1 C2 C3 -179.1(2) . . . . ?
C4 O1 C3 N4 -0.7(2) . . . . ?
C4 O1 C3 C2 -179.9(2) . . . . ?
C4 N5 N4 C3 0.8(3) . . . . ?
C2 N1 C1 N2 0.3(2) . . . . ?
C2 N1 C1 N6 179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2308068'
loop_
_audit_author_name
_audit_author_address
'Yuteng Cao'
;CAEP
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N7 O4, 2(H2 O)'
_chemical_formula_sum            'C5 H9 N7 O6'
_chemical_formula_weight         263.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   20.3703(16)
_cell_length_b                   13.3273(11)
_cell_length_c                   8.3036(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.407(3)
_cell_angle_gamma                90
_cell_volume                     2068.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.168
_cell_measurement_theta_min      2.890
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0840 before and 0.0647 after correction. The Ratio of minimum to maximum transmission is 0.9300. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11672
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             2125
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+2.7542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1188
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H5E(0.5) H5F(0.5)
3.a Riding coordinates:
 O5(H5D,H5E,H5F)
3.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33031(8) 0.77239(12) 0.6700(2) 0.0226(4) Uani 1 1 d . . . . .
O6 O 0.53024(10) 0.77592(17) 0.5016(2) 0.0285(4) Uani 1 1 d . . . . .
O5 O 0.53915(10) 0.56822(13) 0.4303(2) 0.0305(4) Uani 1 1 d . . . . .
H5D H 0.577071 0.538072 0.436029 0.053(10) Uiso 1 1 d R . . . .
H5E H 0.501171 0.547413 0.345289 0.17(5) Uiso 0.5 1 d R . P . .
H5F H 0.523081 0.529732 0.489449 0.044(18) Uiso 0.5 1 d R . P . .
O4 O 0.27941(9) 0.34665(13) 0.6848(2) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.39982(10) 1.08656(13) 0.6521(2) 0.0333(4) Uani 1 1 d . . . . .
O3 O 0.45132(10) 0.96793(13) 0.5664(2) 0.0347(5) Uani 1 1 d . . . . .
N1 N 0.33281(10) 0.49734(15) 0.6404(3) 0.0232(5) Uani 1 1 d . . . . .
N5 N 0.41654(10) 0.78280(15) 0.5824(2) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.449326 0.808207 0.550217 0.028 Uiso 1 1 calc R U . . .
N4 N 0.40171(10) 0.68098(14) 0.5827(2) 0.0237(5) Uani 1 1 d . . . . .
N2 N 0.24159(10) 0.50375(15) 0.7189(3) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.206590 0.482704 0.747039 0.029 Uiso 1 1 calc R U . . .
N6 N 0.36583(10) 0.93189(15) 0.6669(3) 0.0250(5) Uani 1 1 d . . . . .
N3 N 0.25864(10) 0.60132(15) 0.7090(3) 0.0248(5) Uani 1 1 d . . . . .
N7 N 0.40849(11) 0.99742(16) 0.6260(3) 0.0271(5) Uani 1 1 d . . . . .
C4 C 0.37470(12) 0.83630(18) 0.6372(3) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.35040(12) 0.67916(18) 0.6361(3) 0.0226(5) Uani 1 1 d . . . . .
C2 C 0.31330(12) 0.59282(18) 0.6623(3) 0.0225(5) Uani 1 1 d . . . . .
C1 C 0.28585(12) 0.44459(17) 0.6795(3) 0.0225(5) Uani 1 1 d . . . . .
C5 C 0.33106(14) 0.28890(19) 0.6467(3) 0.0331(6) Uani 1 1 d . . . . .
H5A H 0.323345 0.298395 0.523422 0.050 Uiso 1 1 calc R U . . .
H5B H 0.325693 0.217698 0.668331 0.050 Uiso 1 1 calc R U . . .
H5C H 0.379382 0.311222 0.722272 0.050 Uiso 1 1 calc R U . . .
H6A H 0.5454(17) 0.817(3) 0.444(4) 0.052(10) Uiso 1 1 d . . . . .
H6B H 0.5312(18) 0.721(3) 0.478(4) 0.058(12) Uiso 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 C4 1.347(3) . ?
O1 C3 1.372(3) . ?
O6 H6A 0.86(3) . ?
O6 H6B 0.76(4) . ?
O5 H5D 0.8550 . ?
O5 H5E 0.8600 . ?
O5 H5F 0.8600 . ?
O4 C1 1.314(3) . ?
O4 C5 1.437(3) . ?
O2 N7 1.233(3) . ?
O3 N7 1.226(3) . ?
N1 C2 1.367(3) . ?
N1 C1 1.327(3) . ?
N5 H5 0.8800 . ?
N5 N4 1.390(3) . ?
N5 C4 1.322(3) . ?
N4 C3 1.288(3) . ?
N2 H2 0.8800 . ?
N2 N3 1.357(3) . ?
N2 C1 1.333(3) . ?
N6 N7 1.367(3) . ?
N6 C4 1.324(3) . ?
N3 C2 1.322(3) . ?
C3 C2 1.440(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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
C4 O1 C3 104.62(17) . . ?
H6A O6 H6B 114(3) . . ?
H5D O5 H5E 113.1 . . ?
H5D O5 H5F 103.2 . . ?
H5E O5 H5F 81.6 . . ?
C1 O4 C5 115.64(19) . . ?
C1 N1 C2 100.65(19) . . ?
N4 N5 H5 124.6 . . ?
C4 N5 H5 124.6 . . ?
C4 N5 N4 110.83(18) . . ?
C3 N4 N5 103.03(18) . . ?
N3 N2 H2 125.1 . . ?
C1 N2 H2 125.1 . . ?
C1 N2 N3 109.76(19) . . ?
C4 N6 N7 114.91(19) . . ?
C2 N3 N2 101.61(19) . . ?
O2 N7 N6 115.01(19) . . ?
O3 N7 O2 123.7(2) . . ?
O3 N7 N6 121.3(2) . . ?
N5 C4 O1 107.7(2) . . ?
N5 C4 N6 137.5(2) . . ?
N6 C4 O1 114.7(2) . . ?
O1 C3 C2 118.4(2) . . ?
N4 C3 O1 113.7(2) . . ?
N4 C3 C2 127.8(2) . . ?
N1 C2 C3 121.8(2) . . ?
N3 C2 N1 116.2(2) . . ?
N3 C2 C3 122.0(2) . . ?
O4 C1 N1 128.7(2) . . ?
O4 C1 N2 119.5(2) . . ?
N1 C1 N2 111.7(2) . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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 C3 C2 N1 -176.4(2) . . . . ?
O1 C3 C2 N3 3.4(3) . . . . ?
N5 N4 C3 O1 0.3(2) . . . . ?
N5 N4 C3 C2 -179.9(2) . . . . ?
N4 N5 C4 O1 -1.7(2) . . . . ?
N4 N5 C4 N6 178.1(3) . . . . ?
N4 C3 C2 N1 3.8(4) . . . . ?
N4 C3 C2 N3 -176.3(2) . . . . ?
N2 N3 C2 N1 0.3(3) . . . . ?
N2 N3 C2 C3 -179.6(2) . . . . ?
N3 N2 C1 O4 178.6(2) . . . . ?
N3 N2 C1 N1 -0.7(3) . . . . ?
N7 N6 C4 O1 -177.10(18) . . . . ?
N7 N6 C4 N5 3.2(4) . . . . ?
C4 O1 C3 N4 -1.3(2) . . . . ?
C4 O1 C3 C2 178.92(19) . . . . ?
C4 N5 N4 C3 0.8(2) . . . . ?
C4 N6 N7 O2 179.3(2) . . . . ?
C4 N6 N7 O3 0.0(3) . . . . ?
C3 O1 C4 N5 1.7(2) . . . . ?
C3 O1 C4 N6 -178.1(2) . . . . ?
C2 N1 C1 O4 -178.4(2) . . . . ?
C2 N1 C1 N2 0.8(2) . . . . ?
C1 N1 C2 N3 -0.7(3) . . . . ?
C1 N1 C2 C3 179.2(2) . . . . ?
C1 N2 N3 C2 0.3(2) . . . . ?
C5 O4 C1 N1 1.4(4) . . . . ?
C5 O4 C1 N2 -177.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
