# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_comp_2
_database_code_depnum_ccdc_archive 'CCDC 2300028'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_comp_2              
;
PROBLEM: Short Inter D...A Contact  O1       ..O1       .       2.81 Ang.
RESPONSE: The dense accumulation of the title compound molecules
 in the crystal structure triggers this alert.
;
# end Validation Reply Form
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N6 O'
_chemical_formula_sum            'C6 H4 N6 O'
_chemical_formula_weight         176.15
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7290(4)
_cell_length_b                   7.4768(8)
_cell_length_c                   14.4819(16)
_cell_angle_alpha                100.016(3)
_cell_angle_beta                 93.884(4)
_cell_angle_gamma                104.266(4)
_cell_volume                     382.76(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      26.014
_cell_measurement_theta_min      2.868
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0784 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8990.
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    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4289
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.867
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1013
_reflns_number_total             1563
_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       'Bruker D8 Venture diffractometer'
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.041
_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)+(0.0251P)²+0.3744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.2880(5) 0.1637(3) 0.03575(13) 0.0326(5) Uani 1 1 d . . . . .
N2 N 0.7877(7) 0.5281(3) 0.31339(19) 0.0281(6) Uani 1 1 d . . . . .
N6 N 0.2491(7) 0.6106(3) 0.14667(18) 0.0271(6) Uani 1 1 d . . . . .
N4 N 0.4197(7) 0.1570(3) 0.12508(16) 0.0296(6) Uani 1 1 d . . . . .
N5 N 0.2149(6) 0.3374(3) 0.03239(16) 0.0294(6) Uani 1 1 d . . . . .
N3 N -0.0673(7) -0.0839(3) 0.26993(17) 0.0327(6) Uani 1 1 d . . . . .
N1 N 0.7050(8) 0.3002(4) 0.50735(19) 0.0417(7) Uani 1 1 d . . . . .
C5 C 0.4302(7) 0.3203(4) 0.17704(19) 0.0235(6) Uani 1 1 d . . . . .
C3 C 0.4239(8) 0.2290(4) 0.33398(19) 0.0249(7) Uani 1 1 d . . . . .
C4 C 0.5530(7) 0.3607(4) 0.27906(19) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.1547(8) 0.0555(4) 0.29701(19) 0.0248(6) Uani 1 1 d . . . . .
C1 C 0.5705(8) 0.2639(4) 0.4302(2) 0.0275(7) Uani 1 1 d . . . . .
C6 C 0.3061(7) 0.4346(4) 0.11886(19) 0.0241(6) Uani 1 1 d . . . . .
H6A H 0.439(8) 0.693(4) 0.1857(19) 0.018(7) Uiso 1 1 d . . . . .
H2A H 0.879(8) 0.565(4) 0.376(2) 0.040(9) Uiso 1 1 d . . . . .
H6B H 0.152(8) 0.651(4) 0.100(2) 0.036(9) Uiso 1 1 d . . . . .
H2B H 0.889(9) 0.613(5) 0.271(2) 0.057(10) 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 N4 1.366(3) . ?
O1 N5 1.399(3) . ?
N2 C4 1.328(3) . ?
N2 H2A 0.92(3) . ?
N2 H2B 0.98(4) . ?
N6 C6 1.379(3) . ?
N6 H6A 0.90(3) . ?
N6 H6B 0.88(3) . ?
N4 C5 1.309(3) . ?
N5 C6 1.310(3) . ?
N3 C2 1.146(3) . ?
N1 C1 1.152(4) . ?
C5 C4 1.473(4) . ?
C5 C6 1.431(4) . ?
C3 C4 1.387(3) . ?
C3 C2 1.422(4) . ?
C3 C1 1.417(4) . ?

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
N4 O1 N5 111.17(19) . . ?
C4 N2 H2A 121.8(19) . . ?
C4 N2 H2B 120.9(19) . . ?
H2A N2 H2B 117(3) . . ?
C6 N6 H6A 114.2(17) . . ?
C6 N6 H6B 112.6(19) . . ?
H6A N6 H6B 117(2) . . ?
C5 N4 O1 105.8(2) . . ?
C6 N5 O1 105.1(2) . . ?
N4 C5 C4 120.5(2) . . ?
N4 C5 C6 109.2(2) . . ?
C6 C5 C4 130.3(2) . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 C1 119.6(2) . . ?
C1 C3 C2 117.8(2) . . ?
N2 C4 C5 116.0(2) . . ?
N2 C4 C3 123.5(3) . . ?
C3 C4 C5 120.6(2) . . ?
N3 C2 C3 177.8(3) . . ?
N1 C1 C3 176.2(3) . . ?
N6 C6 C5 127.9(2) . . ?
N5 C6 N6 123.1(3) . . ?
N5 C6 C5 108.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6A N3 0.90(3) 2.27(3) 3.162(4) 174(2) 1_665 yes
N2 H2A N1 0.92(3) 2.14(3) 2.991(4) 155(3) 2_766 yes
N6 H6B N5 0.88(3) 2.30(3) 3.154(4) 162(3) 2_565 yes
N2 H2B N6 0.98(4) 2.32(4) 3.119(3) 138(3) 1_655 yes
N2 H2B N3 0.98(4) 2.24(3) 3.003(3) 134(3) 1_665 yes

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 N4 C5 C4 178.7(2) . . . . ?
O1 N4 C5 C6 -0.7(3) . . . . ?
O1 N5 C6 N6 -175.1(2) . . . . ?
O1 N5 C6 C5 -1.1(3) . . . . ?
N4 O1 N5 C6 0.7(3) . . . . ?
N4 C5 C4 N2 135.5(3) . . . . ?
N4 C5 C4 C3 -44.9(4) . . . . ?
N4 C5 C6 N6 174.9(3) . . . . ?
N4 C5 C6 N5 1.2(3) . . . . ?
N5 O1 N4 C5 0.1(3) . . . . ?
C4 C5 C6 N6 -4.5(4) . . . . ?
C4 C5 C6 N5 -178.2(3) . . . . ?
C2 C3 C4 N2 175.9(3) . . . . ?
C2 C3 C4 C5 -3.7(4) . . . . ?
C1 C3 C4 N2 -5.9(4) . . . . ?
C1 C3 C4 C5 174.5(3) . . . . ?
C6 C5 C4 N2 -45.2(4) . . . . ?
C6 C5 C4 C3 134.4(3) . . . . ?

_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_comp_12
_database_code_depnum_ccdc_archive 'CCDC 2300040'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 N8 O4'
_chemical_formula_sum            'C5 H4 N8 O4'
_chemical_formula_weight         240.16

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6738(4)
_cell_length_b                   9.0828(6)
_cell_length_c                   13.7480(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     958.23(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5960
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6524
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            9472
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2165
_reflns_number_gt                1869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.0798P] 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       0.051(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 677 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2165
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2931(3) -0.1427(2) 0.44632(15) 0.0322(5) Uani 1 1 d . . . . .
C2 C 0.3897(3) 0.0184(2) 0.32326(16) 0.0347(5) Uani 1 1 d . . . . .
C3 C 0.1367(3) 0.0554(2) 0.40252(16) 0.0346(5) Uani 1 1 d . . . . .
C4 C -0.0245(3) 0.1420(3) 0.40928(17) 0.0388(5) Uani 1 1 d . . . . .
C5 C -0.0660(3) 0.2757(3) 0.36158(19) 0.0451(6) Uani 1 1 d . . . . .
N1 N 0.4126(2) -0.10561(19) 0.37708(13) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.2476(2) 0.1034(2) 0.33620(14) 0.0390(5) Uani 1 1 d . . . . .
N3 N 0.1495(2) -0.0607(2) 0.45973(13) 0.0356(4) Uani 1 1 d . . . . .
N4 N 0.5074(3) 0.0516(2) 0.25809(16) 0.0452(5) Uani 1 1 d . . . . .
H4A H 0.494829 0.128861 0.222573 0.054 Uiso 1 1 calc R U . . .
H4B H 0.597306 -0.003735 0.250740 0.054 Uiso 1 1 calc R U . . .
N5 N 0.3200(3) -0.2611(2) 0.49800(16) 0.0433(5) Uani 1 1 d . . . . .
H5A H 0.245269 -0.287387 0.541277 0.052 Uiso 1 1 calc R U . . .
H5B H 0.412386 -0.312793 0.488777 0.052 Uiso 1 1 calc R U . . .
N6 N -0.1605(3) 0.1030(3) 0.45841(19) 0.0582(6) Uani 1 1 d . . . . .
N7 N -0.2237(3) 0.3165(3) 0.38044(19) 0.0622(7) Uani 1 1 d . . . . .
N8 N 0.0409(4) 0.3635(4) 0.2977(2) 0.0736(8) Uani 1 1 d . . . . .
O1 O 0.5519(2) -0.19122(18) 0.36092(12) 0.0414(4) Uani 1 1 d . . . . .
O2 O -0.2843(3) 0.2093(2) 0.44116(17) 0.0688(6) Uani 1 1 d . . . . .
O3 O 0.0367(4) 0.3341(4) 0.2126(2) 0.1231(13) Uani 1 1 d . . . . .
O4 O 0.1272(5) 0.4564(4) 0.3338(3) 0.1266(13) 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
C1 N5 1.305(3) . ?
C1 N3 1.343(3) . ?
C1 N1 1.364(3) . ?
C2 N4 1.307(3) . ?
C2 N2 1.348(3) . ?
C2 N1 1.359(3) . ?
C3 N3 1.319(3) . ?
C3 N2 1.321(3) . ?
C3 C4 1.469(3) . ?
C4 N6 1.293(3) . ?
C4 C5 1.416(3) . ?
C5 N7 1.291(3) . ?
C5 N8 1.442(4) . ?
N1 O1 1.341(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O2 1.375(3) . ?
N7 O2 1.364(3) . ?
N8 O4 1.182(5) . ?
N8 O3 1.200(4) . ?

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
N5 C1 N3 120.8(2) . . ?
N5 C1 N1 118.50(19) . . ?
N3 C1 N1 120.67(18) . . ?
N4 C2 N2 121.2(2) . . ?
N4 C2 N1 118.36(19) . . ?
N2 C2 N1 120.48(19) . . ?
N3 C3 N2 128.87(19) . . ?
N3 C3 C4 116.95(19) . . ?
N2 C3 C4 114.14(18) . . ?
N6 C4 C5 107.2(2) . . ?
N6 C4 C3 124.5(2) . . ?
C5 C4 C3 128.3(2) . . ?
N7 C5 C4 111.4(3) . . ?
N7 C5 N8 119.8(2) . . ?
C4 C5 N8 128.9(2) . . ?
O1 N1 C2 119.57(17) . . ?
O1 N1 C1 120.56(17) . . ?
C2 N1 C1 119.86(17) . . ?
C3 N2 C2 115.03(18) . . ?
C3 N3 C1 115.01(18) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N6 O2 105.9(2) . . ?
C5 N7 O2 103.7(2) . . ?
O4 N8 O3 125.7(4) . . ?
O4 N8 C5 117.3(3) . . ?
O3 N8 C5 117.1(4) . . ?
N7 O2 N6 111.79(19) . . ?

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
N3 C3 C4 N6 -8.4(4) . . . . ?
N2 C3 C4 N6 169.4(2) . . . . ?
N3 C3 C4 C5 175.2(2) . . . . ?
N2 C3 C4 C5 -7.0(3) . . . . ?
N6 C4 C5 N7 -0.5(3) . . . . ?
C3 C4 C5 N7 176.4(2) . . . . ?
N6 C4 C5 N8 -179.6(3) . . . . ?
C3 C4 C5 N8 -2.8(5) . . . . ?
N4 C2 N1 O1 -1.2(3) . . . . ?
N2 C2 N1 O1 177.84(18) . . . . ?
N4 C2 N1 C1 179.4(2) . . . . ?
N2 C2 N1 C1 -1.6(3) . . . . ?
N5 C1 N1 O1 1.7(3) . . . . ?
N3 C1 N1 O1 -177.07(18) . . . . ?
N5 C1 N1 C2 -178.9(2) . . . . ?
N3 C1 N1 C2 2.3(3) . . . . ?
N3 C3 N2 C2 2.7(3) . . . . ?
C4 C3 N2 C2 -174.76(19) . . . . ?
N4 C2 N2 C3 178.3(2) . . . . ?
N1 C2 N2 C3 -0.8(3) . . . . ?
N2 C3 N3 C1 -2.0(3) . . . . ?
C4 C3 N3 C1 175.41(18) . . . . ?
N5 C1 N3 C3 -179.5(2) . . . . ?
N1 C1 N3 C3 -0.7(3) . . . . ?
C5 C4 N6 O2 0.4(3) . . . . ?
C3 C4 N6 O2 -176.6(2) . . . . ?
C4 C5 N7 O2 0.4(3) . . . . ?
N8 C5 N7 O2 179.6(3) . . . . ?
N7 C5 N8 O4 90.6(4) . . . . ?
C4 C5 N8 O4 -90.3(4) . . . . ?
N7 C5 N8 O3 -90.6(4) . . . . ?
C4 C5 N8 O3 88.4(4) . . . . ?
C5 N7 O2 N6 -0.1(3) . . . . ?
C4 N6 O2 N7 -0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5B N3 0.86 2.27 3.058(3) 153.3 2_546 yes
N5 H5A O1 0.86 2.01 2.860(2) 168.8 2_446 yes
N4 H4B O4 0.86 2.44 3.195(4) 147.0 3_645 yes
N4 H4A O1 0.86 2.03 2.888(3) 176.2 3_655 yes

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032



####################################################################### 
# 
# 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_comp_6
_database_code_depnum_ccdc_archive 'CCDC 2300035'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N9 O'
_chemical_formula_sum            'C6 H5 N9 O'
_chemical_formula_weight         219.19

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/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                   6.8621(15)
_cell_length_b                   20.664(4)
_cell_length_c                   6.9785(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.407(6)
_cell_angle_gamma                90
_cell_volume                     886.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3574
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5679
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            7858
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2023
_reflns_number_gt                1391
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0958P)²+0.1234P] 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         2023
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2633(3) 0.49209(10) 0.5228(3) 0.0284(5) Uani 1 1 d . . . . .
C2 C 0.2285(3) 0.55966(10) 0.4636(3) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.1195(4) 0.57301(10) 0.2411(4) 0.0345(5) Uani 1 1 d . . . . .
C4 C 0.2999(3) 0.60858(10) 0.6151(3) 0.0290(5) Uani 1 1 d . . . . .
C5 C 0.2646(3) 0.67726(10) 0.5489(3) 0.0294(5) Uani 1 1 d . . . . .
C6 C 0.4150(3) 0.73036(10) 0.6274(4) 0.0320(5) Uani 1 1 d . . . . .
N1 N 0.3632(3) 0.46783(9) 0.7183(3) 0.0363(5) Uani 1 1 d . . . . .
N2 N 0.3598(3) 0.40241(9) 0.6935(3) 0.0407(5) Uani 1 1 d . . . . .
N3 N 0.2644(3) 0.38705(9) 0.4948(3) 0.0392(5) Uani 1 1 d . . . . .
N4 N 0.2024(3) 0.44273(8) 0.3844(3) 0.0334(5) Uani 1 1 d . . . . .
H4 H 0.134713 0.446069 0.247428 0.040 Uiso 1 1 calc R U . . .
N5 N 0.0302(4) 0.57770(10) 0.0606(3) 0.0525(6) Uani 1 1 d . . . . .
N6 N 0.4074(3) 0.59810(9) 0.8235(3) 0.0407(5) Uani 1 1 d . . . . .
H6A H 0.436467 0.559172 0.871462 0.049 Uiso 1 1 calc R U . . .
H6B H 0.448143 0.630229 0.910977 0.049 Uiso 1 1 calc R U . . .
N7 N 0.3143(3) 0.78262(9) 0.5291(3) 0.0405(5) Uani 1 1 d . . . . .
N8 N 0.0790(3) 0.69810(9) 0.4067(3) 0.0384(5) Uani 1 1 d . . . . .
N9 N 0.6225(3) 0.72976(11) 0.7811(4) 0.0452(6) Uani 1 1 d . . . . .
H9A H 0.708(4) 0.7688(13) 0.807(4) 0.054 Uiso 1 1 d . U . . .
H9B H 0.696(4) 0.6938(14) 0.803(4) 0.054 Uiso 1 1 d . U . . .
O1 O 0.1036(3) 0.76330(7) 0.3909(3) 0.0444(5) 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
C1 N1 1.323(3) . ?
C1 N4 1.337(3) . ?
C1 C2 1.445(3) . ?
C2 C4 1.385(3) . ?
C2 C3 1.419(3) . ?
C3 N5 1.133(3) . ?
C4 N6 1.324(3) . ?
C4 C5 1.479(3) . ?
C5 N8 1.292(3) . ?
C5 C6 1.438(3) . ?
C6 N7 1.301(3) . ?
C6 N9 1.349(3) . ?
N1 N2 1.362(3) . ?
N2 N3 1.283(3) . ?
N3 N4 1.344(3) . ?
N4 H4 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O1 1.393(3) . ?
N8 O1 1.368(2) . ?
N9 H9A 0.97(3) . ?
N9 H9B 0.87(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
N1 C1 N4 107.91(19) . . ?
N1 C1 C2 127.20(19) . . ?
N4 C1 C2 124.87(19) . . ?
C4 C2 C3 121.91(19) . . ?
C4 C2 C1 121.99(19) . . ?
C3 C2 C1 116.10(18) . . ?
N5 C3 C2 173.7(2) . . ?
N6 C4 C2 123.65(19) . . ?
N6 C4 C5 115.72(18) . . ?
C2 C4 C5 120.60(19) . . ?
N8 C5 C6 109.50(19) . . ?
N8 C5 C4 121.91(19) . . ?
C6 C5 C4 128.57(19) . . ?
N7 C6 N9 123.5(2) . . ?
N7 C6 C5 108.0(2) . . ?
N9 C6 C5 128.4(2) . . ?
C1 N1 N2 105.89(17) . . ?
N3 N2 N1 110.75(17) . . ?
N2 N3 N4 106.68(17) . . ?
C1 N4 N3 108.77(18) . . ?
C1 N4 H4 125.6 . . ?
N3 N4 H4 125.6 . . ?
C4 N6 H6A 120.0 . . ?
C4 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C6 N7 O1 105.77(17) . . ?
C5 N8 O1 105.99(16) . . ?
C6 N9 H9A 118.7(16) . . ?
C6 N9 H9B 117.9(18) . . ?
H9A N9 H9B 115(3) . . ?
N8 O1 N7 110.70(15) . . ?

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
N1 C1 C2 C4 -0.3(3) . . . . ?
N4 C1 C2 C4 -178.60(19) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
N4 C1 C2 C3 0.6(3) . . . . ?
C3 C2 C4 N6 -178.1(2) . . . . ?
C1 C2 C4 N6 1.1(3) . . . . ?
C3 C2 C4 C5 -0.1(3) . . . . ?
C1 C2 C4 C5 179.06(18) . . . . ?
N6 C4 C5 N8 -135.6(2) . . . . ?
C2 C4 C5 N8 46.2(3) . . . . ?
N6 C4 C5 C6 42.5(3) . . . . ?
C2 C4 C5 C6 -135.6(2) . . . . ?
N8 C5 C6 N7 0.1(3) . . . . ?
C4 C5 C6 N7 -178.2(2) . . . . ?
N8 C5 C6 N9 177.7(2) . . . . ?
C4 C5 C6 N9 -0.7(4) . . . . ?
N4 C1 N1 N2 -0.3(2) . . . . ?
C2 C1 N1 N2 -178.79(19) . . . . ?
C1 N1 N2 N3 0.3(2) . . . . ?
N1 N2 N3 N4 -0.2(2) . . . . ?
N1 C1 N4 N3 0.2(2) . . . . ?
C2 C1 N4 N3 178.75(18) . . . . ?
N2 N3 N4 C1 0.0(2) . . . . ?
N9 C6 N7 O1 -177.6(2) . . . . ?
C5 C6 N7 O1 0.1(2) . . . . ?
C6 C5 N8 O1 -0.3(2) . . . . ?
C4 C5 N8 O1 178.15(18) . . . . ?
C5 N8 O1 N7 0.4(2) . . . . ?
C6 N7 O1 N8 -0.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 N5 0.86 1.99 2.822(3) 161.0 3_565 yes
N6 H6A N1 0.86 2.12 2.771(3) 132.5 . yes
N6 H6A N1 0.86 2.63 3.175(3) 122.8 3_667 yes
N6 H6B N2 0.86 2.56 3.020(3) 114.2 3_667 yes
N6 H6B N7 0.86 2.33 3.059(3) 142.4 4_576 yes
N9 H9A N8 0.97(3) 2.42(3) 3.219(3) 140(2) 4_676 yes

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_comp_19
_database_code_depnum_ccdc_archive 'CCDC 2300052'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C6 H2 N10 O2, H2 O'
_chemical_formula_sum            'C6 H4 N10 O3'
_chemical_formula_weight         264.19

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.5756(4)
_cell_length_b                   11.2579(7)
_cell_length_c                   12.2596(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1045.56(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6455
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            11695
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.456
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2401
_reflns_number_gt                1998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.0832P] 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     '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_abs_structure_details 
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2401
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5025(3) 0.43380(19) 0.53125(17) 0.0435(5) Uani 1 1 d . . . . .
C2 C 0.3720(3) 0.50604(19) 0.48129(17) 0.0405(5) Uani 1 1 d . . . . .
C3 C 0.3915(3) 0.61918(18) 0.42148(16) 0.0359(4) Uani 1 1 d . . . . .
C4 C 0.2437(3) 0.76939(18) 0.33016(15) 0.0365(5) Uani 1 1 d . . . . .
C5 C 0.4160(2) 0.82277(18) 0.31527(15) 0.0355(5) Uani 1 1 d . . . . .
C6 C 0.5634(2) 0.76312(17) 0.35918(16) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.4288(3) 0.34261(18) 0.57803(17) 0.0585(5) Uani 1 1 d . . . . .
N2 N 0.2182(3) 0.45760(18) 0.49830(17) 0.0553(5) Uani 1 1 d . . . . .
N3 N 0.6839(3) 0.45461(18) 0.53057(18) 0.0537(5) Uani 1 1 d . . . . .
N4 N 0.7717(3) 0.37887(18) 0.58241(16) 0.0520(5) Uani 1 1 d . . . . .
N5 N 0.8677(3) 0.3207(2) 0.62500(19) 0.0702(7) Uani 1 1 d . . . . .
N6 N 0.5546(2) 0.65847(15) 0.41510(14) 0.0391(4) Uani 1 1 d . . . . .
N7 N 0.2378(2) 0.66617(15) 0.38326(14) 0.0392(4) Uani 1 1 d . . . . .
N8 N 0.7069(2) 0.82226(17) 0.33463(16) 0.0448(5) Uani 1 1 d . . . . .
N9 N 0.4662(2) 0.91845(17) 0.26387(16) 0.0476(5) Uani 1 1 d . . . . .
N10 N 0.1007(2) 0.82061(18) 0.29276(14) 0.0471(5) Uani 1 1 d . . . . .
H10A H -0.000554 0.787617 0.302224 0.057 Uiso 1 1 calc R U . . .
H10B H 0.108045 0.887243 0.258752 0.057 Uiso 1 1 calc R U . . .
O1 O 0.2501(3) 0.35660(16) 0.55803(15) 0.0661(5) Uani 1 1 d . . . . .
O2 O 0.6472(2) 0.91860(15) 0.27558(14) 0.0513(4) Uani 1 1 d . . . . .
O3 O 0.1009(2) 0.04568(17) 0.18282(15) 0.0584(5) Uani 1 1 d . . . . .
H3A H 0.179(5) 0.044(3) 0.133(3) 0.088 Uiso 1 1 d . U . . .
H3B H 0.010(5) 0.068(3) 0.142(3) 0.088 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.302(3) . ?
C1 N3 1.394(3) . ?
C1 C2 1.419(3) . ?
C2 N2 1.303(3) . ?
C2 C3 1.477(3) . ?
C3 N6 1.314(2) . ?
C3 N7 1.362(3) . ?
C4 N10 1.310(3) . ?
C4 N7 1.333(3) . ?
C4 C5 1.449(3) . ?
C5 N9 1.305(3) . ?
C5 C6 1.410(3) . ?
C6 N8 1.310(2) . ?
C6 N6 1.365(3) . ?
N1 O1 1.384(3) . ?
N2 O1 1.374(3) . ?
N3 N4 1.254(3) . ?
N4 N5 1.109(3) . ?
N8 O2 1.380(2) . ?
N9 O2 1.379(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
O3 H3A 0.85(3) . ?
O3 H3B 0.89(4) . ?

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
N1 C1 N3 123.9(2) . . ?
N1 C1 C2 110.0(2) . . ?
N3 C1 C2 126.0(2) . . ?
N2 C2 C1 108.31(19) . . ?
N2 C2 C3 122.0(2) . . ?
C1 C2 C3 129.67(19) . . ?
N6 C3 N7 130.72(19) . . ?
N6 C3 C2 114.45(17) . . ?
N7 C3 C2 114.83(17) . . ?
N10 C4 N7 121.81(19) . . ?
N10 C4 C5 121.22(19) . . ?
N7 C4 C5 116.97(17) . . ?
N9 C5 C6 110.30(17) . . ?
N9 C5 C4 131.76(18) . . ?
C6 C5 C4 117.90(18) . . ?
N8 C6 N6 126.50(17) . . ?
N8 C6 C5 109.12(17) . . ?
N6 C6 C5 124.35(17) . . ?
C1 N1 O1 104.60(19) . . ?
C2 N2 O1 105.92(19) . . ?
N4 N3 C1 113.9(2) . . ?
N5 N4 N3 170.9(3) . . ?
C3 N6 C6 111.49(16) . . ?
C4 N7 C3 118.55(18) . . ?
C6 N8 O2 104.35(15) . . ?
C5 N9 O2 103.91(17) . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N2 O1 N1 111.14(16) . . ?
N9 O2 N8 112.32(16) . . ?
H3A O3 H3B 98(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
N1 C1 C2 N2 0.0(3) . . . . ?
N3 C1 C2 N2 179.3(2) . . . . ?
N1 C1 C2 C3 178.4(2) . . . . ?
N3 C1 C2 C3 -2.3(4) . . . . ?
N2 C2 C3 N6 177.4(2) . . . . ?
C1 C2 C3 N6 -0.8(3) . . . . ?
N2 C2 C3 N7 -1.9(3) . . . . ?
C1 C2 C3 N7 180.0(2) . . . . ?
N10 C4 C5 N9 -3.3(3) . . . . ?
N7 C4 C5 N9 176.6(2) . . . . ?
N10 C4 C5 C6 179.12(19) . . . . ?
N7 C4 C5 C6 -1.0(3) . . . . ?
N9 C5 C6 N8 -0.1(2) . . . . ?
C4 C5 C6 N8 177.93(17) . . . . ?
N9 C5 C6 N6 -178.23(17) . . . . ?
C4 C5 C6 N6 -0.2(3) . . . . ?
N3 C1 N1 O1 -179.4(2) . . . . ?
C2 C1 N1 O1 -0.1(2) . . . . ?
C1 C2 N2 O1 0.1(2) . . . . ?
C3 C2 N2 O1 -178.43(18) . . . . ?
N1 C1 N3 N4 -2.1(4) . . . . ?
C2 C1 N3 N4 178.7(2) . . . . ?
N7 C3 N6 C6 -0.8(3) . . . . ?
C2 C3 N6 C6 -179.88(17) . . . . ?
N8 C6 N6 C3 -176.8(2) . . . . ?
C5 C6 N6 C3 1.0(3) . . . . ?
N10 C4 N7 C3 -178.87(18) . . . . ?
C5 C4 N7 C3 1.2(3) . . . . ?
N6 C3 N7 C4 -0.4(3) . . . . ?
C2 C3 N7 C4 178.75(16) . . . . ?
N6 C6 N8 O2 178.14(18) . . . . ?
C5 C6 N8 O2 0.1(2) . . . . ?
C6 C5 N9 O2 0.1(2) . . . . ?
C4 C5 N9 O2 -177.6(2) . . . . ?
C2 N2 O1 N1 -0.1(3) . . . . ?
C1 N1 O1 N2 0.1(2) . . . . ?
C5 N9 O2 N8 -0.1(2) . . . . ?
C6 N8 O2 N9 0.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3B N7 0.89(4) 2.20(4) 3.013(3) 152(3) 3_545 yes
O3 H3A N6 0.85(3) 2.47(4) 3.141(3) 136(3) 3_645 yes
O3 H3A N3 0.85(3) 2.47(3) 3.248(3) 152(3) 3_645 yes
N10 H10B O3 0.86 2.01 2.870(3) 174.5 1_565 yes
N10 H10A N8 0.86 2.29 3.027(2) 144.5 1_455 yes

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030



####################################################################### 
# 
# 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_comp_10
_database_code_depnum_ccdc_archive 'CCDC 2300038'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H6 N9 O3, 2(N O3), H N O3, H5 O2'
_chemical_formula_sum            'C5 H12 N12 O14'
_chemical_formula_weight         464.27
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3729(4)
_cell_length_b                   10.7694(6)
_cell_length_c                   10.9412(7)
_cell_angle_alpha                75.967(3)
_cell_angle_beta                 70.563(2)
_cell_angle_gamma                69.452(2)
_cell_volume                     862.29(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      26.325
_cell_measurement_theta_min      2.701
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1081 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9351.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10033
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         1.994
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2831
_reflns_number_total             3513
_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       'Bruker D8 Venture diffractometer'
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.025
_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)+(0.0418P)²+0.2702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
O16A \\sim O16: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
2. Same fragment restrains
{N12, O1A, O3A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{N12, O1, O3}
3. Others
 Sof(O1A)=Sof(O3A)=1-FVAR(1)
 Sof(O1)=Sof(O3)=FVAR(1)
 Sof(O14)=1-FVAR(2)
 Sof(O15)=FVAR(2)
 Sof(O16A)=1-FVAR(3)
 Sof(O16)=FVAR(3)
 Sof(O9)=1-FVAR(4)
 Sof(O8)=FVAR(4)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.01474(19) 0.22916(14) 0.87537(14) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.22162(18) 0.09793(14) 0.99523(14) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.30872(19) 0.19969(14) 0.78914(14) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.45219(19) 0.23093(15) 0.67694(14) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.4441(2) 0.31415(16) 0.55369(14) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.25175(19) 0.02070(14) 1.10287(13) 0.0241(3) Uani 1 1 d . . . . .
H1A H 0.360(3) -0.0170(18) 1.1049(17) 0.029(5) Uiso 1 1 d . . . . .
H1B H 0.164(3) 0.005(2) 1.169(2) 0.044(6) Uiso 1 1 d . . . . .
N2 N 0.05058(16) 0.15452(12) 0.98811(12) 0.0192(3) Uani 1 1 d . . . . .
H2 H -0.035(3) 0.141(2) 1.055(2) 0.041(5) Uiso 1 1 d . . . . .
N3 N -0.14836(17) 0.27644(14) 0.86712(14) 0.0246(3) Uani 1 1 d . . . . .
H3A H -0.237(3) 0.2673(19) 0.931(2) 0.037(5) Uiso 1 1 d . . . . .
H3B H -0.167(3) 0.328(2) 0.796(2) 0.037(5) Uiso 1 1 d . . . . .
N4 N 0.14766(15) 0.25308(12) 0.77107(11) 0.0192(3) Uani 1 1 d . . . . .
N5 N 0.35683(16) 0.12174(12) 0.89384(12) 0.0202(3) Uani 1 1 d . . . . .
N6 N 0.61732(18) 0.18249(15) 0.67889(13) 0.0332(4) Uani 1 1 d . . . . .
N7 N 0.60376(18) 0.31429(16) 0.48261(14) 0.0374(4) Uani 1 1 d . . . . .
N8 N 0.29046(18) 0.38251(14) 0.51664(13) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.198(3) 0.381(2) 0.568(2) 0.046(6) Uiso 1 1 d . . . . .
N9 N 0.28636(19) 0.46784(15) 0.40253(13) 0.0335(3) Uani 1 1 d . . . . .
O7 O 0.71257(15) 0.23162(14) 0.56142(12) 0.0437(4) Uani 1 1 d . . . . .
O10 O 0.14114(16) 0.53024(14) 0.38626(12) 0.0442(3) Uani 1 1 d . . . . .
H4 H 0.312(4) 0.518(3) 0.893(3) 0.106(10) Uiso 1 1 d . . . . .
O8 O 0.4240(12) 0.4904(19) 0.3330(15) 0.048(2) Uani 0.66(7) 1 d . . P A 1
O9 O 0.424(2) 0.441(7) 0.3138(17) 0.062(9) Uani 0.34(7) 1 d . . P A 2
N11 N 0.15289(17) 0.62268(13) 0.78988(12) 0.0250(3) Uani 1 1 d . . . . .
N12 N 0.40732(18) 0.33006(15) 1.03563(13) 0.0308(3) Uani 1 1 d D . . . .
O1 O 0.2506(11) 0.346(2) 1.0942(17) 0.042(2) Uani 0.50(8) 1 d D . P B 1
O3 O 0.452(3) 0.386(2) 0.9184(11) 0.033(2) Uani 0.50(8) 1 d D . P B 1
O2 O 0.52910(14) 0.23485(12) 1.07266(11) 0.0334(3) Uani 1 1 d . . . . .
O4 O 0.22699(18) 0.61756(13) 0.88263(12) 0.0401(3) Uani 1 1 d . . . . .
O5 O 0.06578(15) 0.73454(11) 0.75371(11) 0.0301(3) Uani 1 1 d . . . . .
O6 O 0.17658(17) 0.52071(12) 0.75080(13) 0.0391(3) Uani 1 1 d . . . . .
O1A O 0.260(2) 0.365(3) 1.113(3) 0.051(4) Uani 0.50(8) 1 d D . P B 2
O3A O 0.451(3) 0.409(3) 0.932(2) 0.039(4) Uani 0.50(8) 1 d D . P B 2
N10 N 0.81764(16) 0.01036(13) 0.31704(12) 0.0238(3) Uani 1 1 d . . . . .
O11 O 0.80405(14) 0.05600(11) 0.20325(10) 0.0264(3) Uani 1 1 d . . . . .
O12 O 0.68062(14) 0.00541(13) 0.40904(11) 0.0347(3) Uani 1 1 d . . . . .
O13 O 0.96534(14) -0.03294(12) 0.33997(11) 0.0331(3) Uani 1 1 d . . . . .
O16 O 0.1111(2) 0.2145(3) 0.43303(16) 0.0323(6) Uani 0.968(8) 1 d . U P C 1
O15 O 0.4125(3) 0.1097(6) 0.3032(3) 0.0290(11) Uani 0.663(17) 1 d . . P D 1
O14 O 0.4183(6) 0.1747(16) 0.3248(6) 0.040(3) Uani 0.337(17) 1 d . . P D 2
H16A H 0.077(3) 0.154(2) 0.500(2) 0.056(7) Uiso 1 1 d . . . . .
H15A H 0.501(4) 0.090(3) 0.346(3) 0.074(8) Uiso 1 1 d . . . . .
H16B H 0.049(3) 0.237(2) 0.385(2) 0.054(7) Uiso 1 1 d . . . . .
H15B H 0.455(4) 0.174(3) 0.220(3) 0.087(9) Uiso 1 1 d . . . . .
O16A O 0.128(6) 0.152(8) 0.407(5) 0.036(7) Uani 0.032(8) 1 d . U P C 2
H16C H 0.283(4) 0.160(3) 0.368(3) 0.089(9) 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
C1 N2 1.3616(18) . ?
C1 N3 1.3053(19) . ?
C1 N4 1.3493(18) . ?
C2 N1 1.3106(19) . ?
C2 N2 1.3664(18) . ?
C2 N5 1.3446(18) . ?
C3 C4 1.4715(19) . ?
C3 N4 1.3290(18) . ?
C3 N5 1.3351(19) . ?
C4 C5 1.435(2) . ?
C4 N6 1.301(2) . ?
C5 N7 1.304(2) . ?
C5 N8 1.378(2) . ?
N1 H1A 0.86(2) . ?
N1 H1B 0.87(2) . ?
N2 H2 0.86(2) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.87(2) . ?
N6 O7 1.3610(17) . ?
N7 O7 1.3954(18) . ?
N8 H8 0.79(2) . ?
N8 N9 1.3617(18) . ?
N9 O10 1.2141(18) . ?
N9 O8 1.220(7) . ?
N9 O9 1.229(15) . ?
N11 O4 1.3363(17) . ?
N11 O5 1.2182(17) . ?
N11 O6 1.2027(17) . ?
N12 O1 1.223(6) . ?
N12 O3 1.268(6) . ?
N12 O2 1.2629(17) . ?
N12 O1A 1.227(7) . ?
N12 O3A 1.268(6) . ?
O4 H4 1.06(3) . ?
N10 O11 1.2501(16) . ?
N10 O12 1.2572(16) . ?
N10 O13 1.2469(16) . ?
O16 H16A 0.90(3) . ?
O16 H16B 0.80(2) . ?
O16 H16C 1.36(3) . ?
O15 H15A 0.94(3) . ?
O15 H15B 1.04(3) . ?
O15 H16C 1.11(3) . ?
O14 H15A 0.96(3) . ?
O14 H15B 1.08(3) . ?
O14 H16C 1.12(3) . ?
O16A H16A 0.97(6) . ?
O16A H16B 0.96(6) . ?
O16A H16C 1.26(6) . ?

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
N3 C1 N2 120.10(14) . . ?
N3 C1 N4 119.66(13) . . ?
N4 C1 N2 120.24(13) . . ?
N1 C2 N2 118.92(13) . . ?
N1 C2 N5 120.50(13) . . ?
N5 C2 N2 120.58(13) . . ?
N4 C3 C4 114.66(12) . . ?
N4 C3 N5 128.90(13) . . ?
N5 C3 C4 116.43(13) . . ?
C5 C4 C3 130.01(13) . . ?
N6 C4 C3 121.61(13) . . ?
N6 C4 C5 108.38(13) . . ?
N7 C5 C4 109.61(13) . . ?
N7 C5 N8 125.55(14) . . ?
N8 C5 C4 124.84(14) . . ?
C2 N1 H1A 118.1(12) . . ?
C2 N1 H1B 120.9(13) . . ?
H1A N1 H1B 121.0(18) . . ?
C1 N2 C2 120.55(12) . . ?
C1 N2 H2 120.1(13) . . ?
C2 N2 H2 119.4(13) . . ?
C1 N3 H3A 123.4(13) . . ?
C1 N3 H3B 117.7(13) . . ?
H3A N3 H3B 118.5(18) . . ?
C3 N4 C1 114.97(12) . . ?
C3 N5 C2 114.60(12) . . ?
C4 N6 O7 106.06(12) . . ?
C5 N7 O7 104.15(12) . . ?
C5 N8 H8 118.8(15) . . ?
N9 N8 C5 123.26(13) . . ?
N9 N8 H8 117.3(16) . . ?
O10 N9 N8 116.80(13) . . ?
O10 N9 O8 124.0(4) . . ?
O10 N9 O9 124.7(8) . . ?
O8 N9 N8 118.4(3) . . ?
O9 N9 N8 114.1(13) . . ?
N6 O7 N7 111.81(11) . . ?
O5 N11 O4 114.32(13) . . ?
O6 N11 O4 119.00(13) . . ?
O6 N11 O5 126.68(14) . . ?
O1 N12 O3 120.2(10) . . ?
O1 N12 O2 122.3(10) . . ?
O2 N12 O3 115.1(10) . . ?
O2 N12 O3A 117.9(9) . . ?
O1A N12 O2 120.0(10) . . ?
O1A N12 O3A 119.7(11) . . ?
N11 O4 H4 105.2(16) . . ?
N12 O3A H4 117.3(17) . . ?
O11 N10 O12 119.39(12) . . ?
O13 N10 O11 120.95(12) . . ?
O13 N10 O12 119.64(12) . . ?
H16A O16 H16B 111(2) . . ?
H16A O16 H16C 109.0(19) . . ?
H16B O16 H16C 110(2) . . ?
H15A O15 H15B 101(2) . . ?
H15A O15 H16C 109(2) . . ?
H15B O15 H16C 112(2) . . ?
H15A O14 H15B 98(2) . . ?
H15A O14 H16C 106(2) . . ?
H15B O14 H16C 108(2) . . ?
H16A O16A H16B 93(7) . . ?
H16A O16A H16C 113(7) . . ?
H16B O16A H16C 108(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O11 0.86(2) 1.99(2) 2.8319(16) 163.4(19) 1_456 yes
N8 H8 N4 0.79(2) 2.30(2) 2.8628(18) 128.1(19) . yes
O4 H4 O3 1.06(3) 1.53(4) 2.58(2) 170(3) . yes
O4 H4 O3A 1.06(3) 1.43(4) 2.451(18) 158(3) . yes
O16 H16A O13 0.90(3) 1.92(3) 2.805(2) 168(2) 2_656 yes
O16A H16A O13 0.97(6) 1.92(3) 2.73(4) 139(6) 2_656 yes
O15 H15A O12 0.94(3) 1.73(3) 2.640(3) 162(3) . yes
O14 H15A O12 0.96(3) 1.73(3) 2.592(5) 148(3) . yes
O16 H16B O5 0.80(2) 1.96(3) 2.751(2) 168(2) 2_566 yes
O16A H16B O5 0.96(6) 1.96(3) 2.58(5) 121(6) 2_566 yes
O15 H15B O2 1.04(3) 1.59(3) 2.602(3) 162(3) 1_554 yes
O14 H15B O2 1.08(3) 1.59(3) 2.596(5) 153(3) 1_554 yes
O15 H16C O16 1.11(3) 1.36(3) 2.461(4) 169(3) . yes
O14 H16C O16A 1.12(3) 1.26(6) 2.38(5) 175(3) . yes

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
C3 C4 C5 N7 179.70(15) . . . . ?
C3 C4 C5 N8 -0.6(3) . . . . ?
C3 C4 N6 O7 -179.69(14) . . . . ?
C4 C3 N4 C1 -177.54(12) . . . . ?
C4 C3 N5 C2 178.62(12) . . . . ?
C4 C5 N7 O7 -0.30(19) . . . . ?
C4 C5 N8 N9 175.39(15) . . . . ?
C4 N6 O7 N7 0.2(2) . . . . ?
C5 C4 N6 O7 -0.33(19) . . . . ?
C5 N7 O7 N6 0.1(2) . . . . ?
C5 N8 N9 O10 -174.12(16) . . . . ?
C5 N8 N9 O8 -4.1(14) . . . . ?
C5 N8 N9 O9 28(4) . . . . ?
N1 C2 N2 C1 -176.30(14) . . . . ?
N1 C2 N5 C3 178.68(14) . . . . ?
N2 C1 N4 C3 -0.4(2) . . . . ?
N2 C2 N5 C3 -1.8(2) . . . . ?
N3 C1 N2 C2 176.10(14) . . . . ?
N3 C1 N4 C3 -179.46(14) . . . . ?
N4 C1 N2 C2 -3.0(2) . . . . ?
N4 C3 C4 C5 2.8(2) . . . . ?
N4 C3 C4 N6 -177.98(15) . . . . ?
N4 C3 N5 C2 -1.9(2) . . . . ?
N5 C2 N2 C1 4.1(2) . . . . ?
N5 C3 C4 C5 -177.67(15) . . . . ?
N5 C3 C4 N6 1.5(2) . . . . ?
N5 C3 N4 C1 3.0(2) . . . . ?
N6 C4 C5 N7 0.4(2) . . . . ?
N6 C4 C5 N8 -179.92(16) . . . . ?
N7 C5 N8 N9 -5.0(3) . . . . ?
N8 C5 N7 O7 -179.95(16) . . . . ?

_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_comp_5
_database_code_depnum_ccdc_archive 'CCDC 2300034'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N9 O, C4 H8 O2'
_chemical_formula_sum            'C10 H13 N9 O3'
_chemical_formula_weight         307.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1990(4)
_cell_length_b                   9.2561(5)
_cell_length_c                   11.4281(5)
_cell_angle_alpha                97.933(2)
_cell_angle_beta                 98.9200(10)
_cell_angle_gamma                106.848(2)
_cell_volume                     706.40(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5755
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.43

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            11062
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3241
_reflns_number_gt                2516
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.0993P] 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       0.066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6260(3) 0.5375(2) 0.11223(14) 0.0641(4) Uani 1 1 d . . . . .
H1A H 0.600924 0.438294 0.136419 0.077 Uiso 1 1 calc R U . . .
H1B H 0.726854 0.613286 0.175222 0.077 Uiso 1 1 calc R U . . .
C2 C 0.6986(2) 0.5302(2) -0.00374(16) 0.0676(5) Uani 1 1 d . . . . .
H2A H 0.731547 0.631012 -0.025243 0.081 Uiso 1 1 calc R U . . .
H2B H 0.817761 0.500326 0.006544 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3242(2) 0.88612(19) 0.94937(15) 0.0632(4) Uani 1 1 d . . . . .
H3A H 0.309872 0.822637 1.010302 0.076 Uiso 1 1 calc R U . . .
H3B H 0.208540 0.841942 0.884208 0.076 Uiso 1 1 calc R U . . .
C4 C 0.3332(2) 1.0447(2) 1.00296(15) 0.0650(4) Uani 1 1 d . . . . .
H4A H 0.335523 1.106051 0.940559 0.078 Uiso 1 1 calc R U . . .
H4B H 0.215654 1.040521 1.035728 0.078 Uiso 1 1 calc R U . . .
C5 C 1.0341(2) 0.07061(16) 0.67851(12) 0.0455(3) Uani 1 1 d . . . . .
C6 C 0.88024(18) 0.14088(15) 0.67465(11) 0.0380(3) Uani 1 1 d . . . . .
C7 C 0.64898(17) 0.22199(14) 0.61126(10) 0.0347(3) Uani 1 1 d . . . . .
C8 C 0.46523(17) 0.24213(13) 0.43309(11) 0.0346(3) Uani 1 1 d . . . . .
C9 C 0.30853(17) 0.30166(14) 0.38031(11) 0.0363(3) Uani 1 1 d . . . . .
C10 C 0.19694(17) 0.38070(14) 0.44275(12) 0.0382(3) Uani 1 1 d . . . . .
N1 N 0.84347(17) 0.20404(14) 0.77559(10) 0.0488(3) Uani 1 1 d . . . . .
N2 N 0.69367(17) 0.25434(14) 0.73238(10) 0.0464(3) Uani 1 1 d . . . . .
H2 H 0.634347 0.301116 0.776652 0.056 Uiso 1 1 calc R U . . .
N3 N 0.76654(15) 0.14800(12) 0.57098(9) 0.0380(3) Uani 1 1 d . . . . .
N4 N 0.50401(14) 0.26789(12) 0.55091(9) 0.0372(3) Uani 1 1 d . . . . .
N5 N 0.54806(15) 0.17115(13) 0.35779(9) 0.0425(3) Uani 1 1 d . . . . .
H5A H 0.639936 0.135327 0.385628 0.051 Uiso 1 1 calc R U . . .
H5B H 0.509914 0.160936 0.281121 0.051 Uiso 1 1 calc R U . . .
N6 N 0.21598(17) 0.41700(14) 0.56264(10) 0.0520(3) Uani 1 1 d . . . . .
H6A H 0.143720 0.466131 0.592057 0.062 Uiso 1 1 calc R U . . .
H6B H 0.300463 0.391156 0.610149 0.062 Uiso 1 1 calc R U . . .
N7 N 1.1577(2) 0.01708(18) 0.68442(12) 0.0673(4) Uani 1 1 d . . . . .
N8 N 0.25257(17) 0.28997(15) 0.26538(11) 0.0516(3) Uani 1 1 d . . . . .
N9 N 0.07348(17) 0.41458(14) 0.36326(10) 0.0490(3) Uani 1 1 d . . . . .
O1 O 0.55102(17) 0.42229(13) -0.09759(10) 0.0620(3) Uani 1 1 d . . . . .
O2 O 0.49591(17) 0.88517(13) 0.90441(9) 0.0620(3) Uani 1 1 d . . . . .
O3 O 0.10776(15) 0.35835(13) 0.25082(9) 0.0584(3) 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
C1 O1 1.4204(19) 2_665 ?
C1 C2 1.498(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.419(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.412(2) . ?
C3 C4 1.490(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.4138(19) 2_677 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N7 1.1349(17) . ?
C5 C6 1.4360(17) . ?
C6 N1 1.3193(16) . ?
C6 N3 1.3528(16) . ?
C7 N3 1.3292(15) . ?
C7 N2 1.3420(16) . ?
C7 N4 1.3638(15) . ?
C8 N4 1.3054(16) . ?
C8 N5 1.3258(15) . ?
C8 C9 1.4769(16) . ?
C9 N8 1.2925(17) . ?
C9 C10 1.4367(16) . ?
C10 N9 1.3051(17) . ?
C10 N6 1.3406(17) . ?
N1 N2 1.3464(14) . ?
N2 H2 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N8 O3 1.3685(14) . ?
N9 O3 1.4040(15) . ?

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
O1 C1 C2 110.13(14) 2_665 . ?
O1 C1 H1A 109.6 2_665 . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 2_665 . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C1 110.37(14) . . ?
O1 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C4 111.78(14) . . ?
O2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C3 110.82(13) 2_677 . ?
O2 C4 H4A 109.5 2_677 . ?
C3 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 2_677 . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N7 C5 C6 178.28(15) . . ?
N1 C6 N3 116.09(11) . . ?
N1 C6 C5 120.32(11) . . ?
N3 C6 C5 123.59(11) . . ?
N3 C7 N2 109.25(10) . . ?
N3 C7 N4 131.05(11) . . ?
N2 C7 N4 119.69(10) . . ?
N4 C8 N5 128.35(11) . . ?
N4 C8 C9 113.97(10) . . ?
N5 C8 C9 117.68(11) . . ?
N8 C9 C10 109.12(11) . . ?
N8 C9 C8 122.99(11) . . ?
C10 C9 C8 127.88(11) . . ?
N9 C10 N6 124.70(11) . . ?
N9 C10 C9 108.75(11) . . ?
N6 C10 C9 126.54(11) . . ?
C6 N1 N2 101.19(10) . . ?
C7 N2 N1 111.20(10) . . ?
C7 N2 H2 124.4 . . ?
N1 N2 H2 124.4 . . ?
C7 N3 C6 102.26(10) . . ?
C8 N4 C7 119.97(10) . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 N6 H6A 120.0 . . ?
C10 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C9 N8 O3 106.44(10) . . ?
C10 N9 O3 105.06(10) . . ?
C2 O1 C1 110.33(11) . 2_665 ?
C3 O2 C4 110.05(12) . 2_677 ?
N8 O3 N9 110.62(9) . . ?

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 O1 -57.93(19) 2_665 . . . ?
O2 C3 C4 O2 -56.85(19) . . . 2_677 ?
N4 C8 C9 N8 178.55(12) . . . . ?
N5 C8 C9 N8 -1.34(18) . . . . ?
N4 C8 C9 C10 -0.67(18) . . . . ?
N5 C8 C9 C10 179.45(12) . . . . ?
N8 C9 C10 N9 0.43(15) . . . . ?
C8 C9 C10 N9 179.73(12) . . . . ?
N8 C9 C10 N6 -178.61(13) . . . . ?
C8 C9 C10 N6 0.7(2) . . . . ?
N3 C6 N1 N2 0.39(16) . . . . ?
C5 C6 N1 N2 -179.95(12) . . . . ?
N3 C7 N2 N1 0.64(15) . . . . ?
N4 C7 N2 N1 -178.25(11) . . . . ?
C6 N1 N2 C7 -0.61(15) . . . . ?
N2 C7 N3 C6 -0.36(14) . . . . ?
N4 C7 N3 C6 178.36(13) . . . . ?
N1 C6 N3 C7 -0.03(15) . . . . ?
C5 C6 N3 C7 -179.67(12) . . . . ?
N5 C8 N4 C7 1.4(2) . . . . ?
C9 C8 N4 C7 -178.49(10) . . . . ?
N3 C7 N4 C8 -1.3(2) . . . . ?
N2 C7 N4 C8 177.29(12) . . . . ?
C10 C9 N8 O3 -0.18(15) . . . . ?
C8 C9 N8 O3 -179.53(11) . . . . ?
N6 C10 N9 O3 178.60(12) . . . . ?
C9 C10 N9 O3 -0.46(14) . . . . ?
C1 C2 O1 C1 58.1(2) . . . 2_665 ?
C4 C3 O2 C4 56.42(19) . . . 2_677 ?
C9 N8 O3 N9 -0.11(15) . . . . ?
C10 N9 O3 N8 0.37(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6B N4 0.86 2.23 2.8136(14) 125.1 . yes
N6 H6A N9 0.86 2.24 3.0912(15) 170.4 2_566 yes
N5 H5B O2 0.86 2.10 2.9206(14) 160.5 2_666 yes
N5 H5A N7 0.86 2.45 3.1590(16) 140.4 2_756 yes
N5 H5A N3 0.86 2.15 2.7580(15) 127.9 . yes
N2 H2 O1 0.86 1.97 2.8210(14) 168.1 1_556 yes
C3 H3B O3 0.97 2.58 3.5084(19) 159.4 2_566 yes

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_comp_9
_database_code_depnum_ccdc_archive 'CCDC 2300037'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N10 O2'
_chemical_formula_sum            'C6 H2 N10 O2'
_chemical_formula_weight         246.18

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/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                   6.8409(5)
_cell_length_b                   6.1690(5)
_cell_length_c                   20.9286(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.363(3)
_cell_angle_gamma                90
_cell_volume                     882.97(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            7586
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         27.443
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1985
_reflns_number_gt                1398
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+0.0196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1985
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3904(3) -0.1003(3) 0.43901(8) 0.0274(4) Uani 1 1 d . . . . .
C2 C 0.5283(2) -0.0032(3) 0.39846(8) 0.0271(4) Uani 1 1 d . . . . .
C3 C 0.4796(2) 0.1993(3) 0.36818(8) 0.0243(4) Uani 1 1 d . . . . .
C4 C 0.2938(2) 0.2808(3) 0.38101(8) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.1675(3) 0.1705(3) 0.42750(8) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.2501(2) 0.4711(3) 0.34702(8) 0.0243(4) Uani 1 1 d . . . . .
N1 N 0.4605(3) -0.2847(3) 0.46051(8) 0.0371(4) Uani 1 1 d . . . . .
N2 N 0.6835(2) -0.1256(3) 0.39470(8) 0.0363(4) Uani 1 1 d . . . . .
N3 N 0.2142(2) -0.0173(2) 0.45418(7) 0.0305(4) Uani 1 1 d . . . . .
N4 N 0.0019(2) 0.2616(3) 0.44472(7) 0.0381(4) Uani 1 1 d . . . . .
H4A H -0.070340 0.198695 0.472213 0.046 Uiso 1 1 calc R U . . .
H4B H -0.033534 0.383846 0.428425 0.046 Uiso 1 1 calc R U . . .
N5 N 0.6108(2) 0.2920(2) 0.33033(7) 0.0285(4) Uani 1 1 d . . . . .
N6 N 0.5515(2) 0.4738(2) 0.30228(7) 0.0278(4) Uani 1 1 d . . . . .
N7 N 0.3746(2) 0.5673(2) 0.30799(7) 0.0285(4) Uani 1 1 d . . . . .
N8 N 0.0690(2) 0.5681(2) 0.35351(7) 0.0315(4) Uani 1 1 d . . . . .
N9 N 0.0436(2) 0.7363(3) 0.31913(8) 0.0331(4) Uani 1 1 d . . . . .
N10 N -0.0017(3) 0.8841(3) 0.29282(9) 0.0512(5) Uani 1 1 d . . . . .
O1 O 0.6438(2) -0.3017(2) 0.43288(6) 0.0404(4) Uani 1 1 d . . . . .
O2 O 0.66682(18) 0.5697(2) 0.26744(6) 0.0403(4) Uani 1 1 d 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
C1 N1 1.310(2) . ?
C1 N3 1.355(2) . ?
C1 C2 1.417(2) . ?
C2 N2 1.307(2) . ?
C2 C3 1.436(2) . ?
C3 N5 1.340(2) . ?
C3 C4 1.399(2) . ?
C4 C6 1.402(2) . ?
C4 C5 1.482(2) . ?
C5 N3 1.321(2) . ?
C5 N4 1.323(2) . ?
C6 N7 1.333(2) . ?
C6 N8 1.385(2) . ?
N1 O1 1.397(2) . ?
N2 O1 1.379(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 N6 1.3252(19) . ?
N6 O2 1.2376(18) . ?
N6 N7 1.3483(19) . ?
N8 N9 1.272(2) . ?
N9 N10 1.105(2) . ?

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
N1 C1 N3 124.65(17) . . ?
N1 C1 C2 109.22(17) . . ?
N3 C1 C2 126.13(16) . . ?
N2 C2 C1 110.19(17) . . ?
N2 C2 C3 131.04(17) . . ?
C1 C2 C3 118.76(16) . . ?
N5 C3 C4 125.82(17) . . ?
N5 C3 C2 118.70(15) . . ?
C4 C3 C2 115.48(15) . . ?
C3 C4 C6 112.80(15) . . ?
C3 C4 C5 120.51(16) . . ?
C6 C4 C5 126.68(15) . . ?
N3 C5 N4 117.22(16) . . ?
N3 C5 C4 122.77(16) . . ?
N4 C5 C4 120.01(16) . . ?
N7 C6 N8 116.98(15) . . ?
N7 C6 C4 123.50(16) . . ?
N8 C6 C4 119.52(15) . . ?
C1 N1 O1 104.36(14) . . ?
C2 N2 O1 104.43(15) . . ?
C5 N3 C1 116.08(15) . . ?
C5 N4 H4A 120.0 . . ?
C5 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N6 N5 C3 114.86(14) . . ?
O2 N6 N5 118.20(14) . . ?
O2 N6 N7 115.72(14) . . ?
N5 N6 N7 126.08(14) . . ?
C6 N7 N6 116.87(15) . . ?
N9 N8 C6 114.03(14) . . ?
N10 N9 N8 170.80(18) . . ?
N2 O1 N1 111.81(13) . . ?

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
N1 C1 C2 N2 -0.1(2) . . . . ?
N3 C1 C2 N2 179.35(15) . . . . ?
N1 C1 C2 C3 178.56(15) . . . . ?
N3 C1 C2 C3 -2.0(3) . . . . ?
N2 C2 C3 N5 -2.3(3) . . . . ?
C1 C2 C3 N5 179.36(15) . . . . ?
N2 C2 C3 C4 177.00(17) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
N5 C3 C4 C6 3.0(3) . . . . ?
C2 C3 C4 C6 -176.21(14) . . . . ?
N5 C3 C4 C5 -175.59(15) . . . . ?
C2 C3 C4 C5 5.2(2) . . . . ?
C3 C4 C5 N3 -6.5(3) . . . . ?
C6 C4 C5 N3 175.09(16) . . . . ?
C3 C4 C5 N4 172.35(15) . . . . ?
C6 C4 C5 N4 -6.1(3) . . . . ?
C3 C4 C6 N7 -1.7(2) . . . . ?
C5 C4 C6 N7 176.80(16) . . . . ?
C3 C4 C6 N8 178.37(14) . . . . ?
C5 C4 C6 N8 -3.1(3) . . . . ?
N3 C1 N1 O1 -179.50(15) . . . . ?
C2 C1 N1 O1 -0.03(19) . . . . ?
C1 C2 N2 O1 0.19(19) . . . . ?
C3 C2 N2 O1 -178.26(17) . . . . ?
N4 C5 N3 C1 -175.77(15) . . . . ?
C4 C5 N3 C1 3.1(3) . . . . ?
N1 C1 N3 C5 -179.58(17) . . . . ?
C2 C1 N3 C5 1.1(3) . . . . ?
C4 C3 N5 N6 -1.8(3) . . . . ?
C2 C3 N5 N6 177.44(14) . . . . ?
C3 N5 N6 O2 178.88(15) . . . . ?
C3 N5 N6 N7 -1.0(2) . . . . ?
N8 C6 N7 N6 179.31(13) . . . . ?
C4 C6 N7 N6 -0.6(3) . . . . ?
O2 N6 N7 C6 -177.74(14) . . . . ?
N5 N6 N7 C6 2.2(2) . . . . ?
N7 C6 N8 N9 1.9(2) . . . . ?
C4 C6 N8 N9 -178.15(15) . . . . ?
C2 N2 O1 N1 -0.22(18) . . . . ?
C1 N1 O1 N2 0.16(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4B N8 0.86 2.07 2.733(2) 133.1 . yes
N4 H4A N3 0.86 2.16 3.014(2) 171.8 3_556 yes

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_comp_4
_database_code_depnum_ccdc_archive 'CCDC 2300032'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-19
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N8 O2'
_chemical_formula_sum            'C6 H4 N8 O2'
_chemical_formula_weight         220.17
_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                   9.522(3)
_cell_length_b                   4.7197(17)
_cell_length_c                   18.552(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.397(11)
_cell_angle_gamma                90
_cell_volume                     820.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1543
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.741
_cell_measurement_theta_min      2.258
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1689 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.8861.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5777
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1045
_reflns_number_total             1648
_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       APEX-III
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.068
_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)+(0.0290P)²+0.7014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N5-H5B = N5-H5A = N8-H8A = N8-H8B
 0.87 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.2682(2) 0.1584(4) 0.34493(11) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.3273(2) 0.8715(4) 0.73081(11) 0.0319(6) Uani 1 1 d . . . . .
N4 N 0.1544(2) 0.7296(5) 0.51553(12) 0.0208(6) Uani 1 1 d . . . . .
N3 N 0.3472(2) 0.3779(5) 0.52699(12) 0.0241(6) Uani 1 1 d . . . . .
N5 N 0.0041(3) 0.8298(5) 0.40639(14) 0.0251(6) Uani 1 1 d D . . . .
N1 N 0.1657(3) 0.3691(5) 0.34258(13) 0.0266(6) Uani 1 1 d . . . . .
N2 N 0.3521(3) 0.1307(5) 0.41486(13) 0.0274(6) Uani 1 1 d . . . . .
N7 N 0.4385(3) 0.6737(5) 0.74362(13) 0.0274(6) Uani 1 1 d . . . . .
N6 N 0.2554(3) 0.8540(5) 0.65989(13) 0.0294(6) Uani 1 1 d . . . . .
N8 N 0.5232(3) 0.3282(6) 0.67150(15) 0.0303(6) Uani 1 1 d D . . . .
C2 C 0.1864(3) 0.4688(6) 0.40965(16) 0.0216(7) Uani 1 1 d . . . . .
C1 C 0.1114(3) 0.6847(6) 0.44380(15) 0.0202(6) Uani 1 1 d . . . . .
C6 C 0.4322(3) 0.5357(6) 0.68196(16) 0.0227(7) Uani 1 1 d . . . . .
C4 C 0.2699(3) 0.5794(6) 0.55127(15) 0.0229(7) Uani 1 1 d . . . . .
C3 C 0.3001(3) 0.3236(6) 0.45416(16) 0.0229(7) Uani 1 1 d . . . . .
C5 C 0.3168(3) 0.6525(6) 0.62895(15) 0.0231(7) Uani 1 1 d . . . . .
H5A H -0.042(3) 0.955(6) 0.4300(15) 0.038(10) Uiso 1 1 d D . . . .
H5B H -0.016(3) 0.803(7) 0.3601(10) 0.042(10) Uiso 1 1 d D . . . .
H8A H 0.506(4) 0.244(7) 0.6274(12) 0.054(12) Uiso 1 1 d D . . . .
H8B H 0.580(3) 0.245(7) 0.7098(15) 0.064(13) Uiso 1 1 d 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 N1 1.388(3) . ?
O1 N2 1.401(3) . ?
O2 N7 1.399(3) . ?
O2 N6 1.372(3) . ?
N4 C1 1.337(3) . ?
N4 C4 1.374(3) . ?
N3 C4 1.330(4) . ?
N3 C3 1.369(4) . ?
N5 C1 1.319(4) . ?
N5 H5A 0.896(18) . ?
N5 H5B 0.855(18) . ?
N1 C2 1.311(4) . ?
N2 C3 1.317(4) . ?
N7 C6 1.308(4) . ?
N6 C5 1.303(4) . ?
N8 C6 1.345(4) . ?
N8 H8A 0.898(18) . ?
N8 H8B 0.902(18) . ?
C2 C1 1.454(4) . ?
C2 C3 1.415(4) . ?
C6 C5 1.445(4) . ?
C4 C5 1.471(4) . ?

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
N1 O1 N2 112.07(19) . . ?
N6 O2 N7 110.8(2) . . ?
C1 N4 C4 118.2(2) . . ?
C4 N3 C3 111.5(2) . . ?
C1 N5 H5A 119(2) . . ?
C1 N5 H5B 117(2) . . ?
H5A N5 H5B 123(3) . . ?
C2 N1 O1 104.1(2) . . ?
C3 N2 O1 103.9(2) . . ?
C6 N7 O2 105.6(2) . . ?
C5 N6 O2 106.3(2) . . ?
C6 N8 H8A 116(2) . . ?
C6 N8 H8B 121(2) . . ?
H8A N8 H8B 120(3) . . ?
N1 C2 C1 131.6(3) . . ?
N1 C2 C3 110.4(3) . . ?
C3 C2 C1 118.0(2) . . ?
N4 C1 C2 117.3(2) . . ?
N5 C1 N4 120.7(3) . . ?
N5 C1 C2 122.0(3) . . ?
N7 C6 N8 124.0(3) . . ?
N7 C6 C5 108.3(3) . . ?
N8 C6 C5 127.6(3) . . ?
N4 C4 C5 115.3(3) . . ?
N3 C4 N4 130.5(3) . . ?
N3 C4 C5 114.3(2) . . ?
N3 C3 C2 124.4(3) . . ?
N2 C3 N3 126.0(3) . . ?
N2 C3 C2 109.6(3) . . ?
N6 C5 C6 109.0(3) . . ?
N6 C5 C4 121.5(3) . . ?
C6 C5 C4 129.5(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 N1 C2 C1 -177.5(3) . . . . ?
O1 N1 C2 C3 -0.1(3) . . . . ?
O1 N2 C3 N3 179.8(3) . . . . ?
O1 N2 C3 C2 -0.1(3) . . . . ?
O2 N7 C6 N8 179.1(3) . . . . ?
O2 N7 C6 C5 1.2(3) . . . . ?
O2 N6 C5 C6 0.2(3) . . . . ?
O2 N6 C5 C4 -178.2(2) . . . . ?
N4 C4 C5 N6 -2.6(4) . . . . ?
N4 C4 C5 C6 179.4(3) . . . . ?
N3 C4 C5 N6 177.2(3) . . . . ?
N3 C4 C5 C6 -0.8(4) . . . . ?
N1 O1 N2 C3 0.0(3) . . . . ?
N1 C2 C1 N4 176.6(3) . . . . ?
N1 C2 C1 N5 -2.7(5) . . . . ?
N1 C2 C3 N3 -179.7(3) . . . . ?
N1 C2 C3 N2 0.1(3) . . . . ?
N2 O1 N1 C2 0.1(3) . . . . ?
N7 O2 N6 C5 0.6(3) . . . . ?
N7 C6 C5 N6 -0.9(3) . . . . ?
N7 C6 C5 C4 177.3(3) . . . . ?
N6 O2 N7 C6 -1.1(3) . . . . ?
N8 C6 C5 N6 -178.7(3) . . . . ?
N8 C6 C5 C4 -0.5(5) . . . . ?
C1 N4 C4 N3 -3.5(4) . . . . ?
C1 N4 C4 C5 176.3(3) . . . . ?
C1 C2 C3 N3 -1.9(4) . . . . ?
C1 C2 C3 N2 177.9(2) . . . . ?
C4 N4 C1 N5 -177.8(3) . . . . ?
C4 N4 C1 C2 3.0(4) . . . . ?
C4 N3 C3 N2 -178.1(3) . . . . ?
C4 N3 C3 C2 1.7(4) . . . . ?
C3 N3 C4 N4 1.0(4) . . . . ?
C3 N3 C4 C5 -178.8(2) . . . . ?
C3 C2 C1 N4 -0.6(4) . . . . ?
C3 C2 C1 N5 -179.9(3) . . . . ?


_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_comp_11
_database_code_depnum_ccdc_archive 'CCDC 2300039'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 N8 O3'
_chemical_formula_sum            'C5 H4 N8 O3'
_chemical_formula_weight         224.16

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/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                   9.437(2)
_cell_length_b                   7.6269(18)
_cell_length_c                   12.404(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.116(8)
_cell_angle_gamma                90
_cell_volume                     889.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4628
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            8562
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2024
_reflns_number_gt                1569
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.1950P] 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       0.057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2024
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06838(14) 0.25884(17) 0.44150(11) 0.0333(3) Uani 1 1 d . . . . .
C2 C 0.20214(16) 0.29784(18) 0.60050(11) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.19646(13) 0.50226(17) 0.47143(10) 0.0298(3) Uani 1 1 d . . . . .
C4 C 0.24609(14) 0.67518(17) 0.43645(11) 0.0330(3) Uani 1 1 d . . . . .
C5 C 0.34782(15) 0.78864(19) 0.49126(11) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.11278(13) 0.19488(14) 0.53946(9) 0.0375(3) Uani 1 1 d . . . . .
N2 N 0.10908(12) 0.41485(14) 0.40147(9) 0.0339(3) Uani 1 1 d . . . . .
N3 N 0.24645(12) 0.45788(14) 0.57042(9) 0.0351(3) Uani 1 1 d . . . . .
N4 N -0.02341(14) 0.16294(16) 0.37921(11) 0.0487(4) Uani 1 1 d . . . . .
H4A H -0.052151 0.063854 0.402171 0.058 Uiso 1 1 calc R U . . .
H4B H -0.054132 0.199921 0.315904 0.058 Uiso 1 1 calc R U . . .
N5 N 0.25270(18) 0.24139(18) 0.69722(11) 0.0620(5) Uani 1 1 d . . . . .
H5A H 0.227957 0.140205 0.719729 0.074 Uiso 1 1 calc R U . . .
H5B H 0.310298 0.305877 0.737590 0.074 Uiso 1 1 calc R U . . .
N6 N 0.19897(14) 0.75247(17) 0.34734(11) 0.0472(4) Uani 1 1 d . . . . .
N7 N 0.36215(16) 0.93027(18) 0.43712(12) 0.0551(4) Uani 1 1 d . . . . .
N8 N 0.43263(14) 0.76453(17) 0.59409(11) 0.0427(3) Uani 1 1 d . . . . .
O1 O 0.27008(14) 0.90993(16) 0.34585(10) 0.0617(4) Uani 1 1 d . . . . .
O2 O 0.53361(13) 0.66791(18) 0.59445(12) 0.0680(4) Uani 1 1 d . . . . .
O3 O 0.39682(16) 0.84525(18) 0.67078(10) 0.0678(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
C1 N4 1.3278(18) . ?
C1 N1 1.3413(18) . ?
C1 N2 1.3579(17) . ?
C2 N5 1.3230(19) . ?
C2 N1 1.3369(18) . ?
C2 N3 1.3535(17) . ?
C3 N3 1.3196(17) . ?
C3 N2 1.3229(17) . ?
C3 C4 1.4776(18) . ?
C4 N6 1.2959(19) . ?
C4 C5 1.420(2) . ?
C5 N7 1.285(2) . ?
C5 N8 1.456(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O1 1.3766(17) . ?
N7 O1 1.3730(19) . ?
N8 O2 1.2043(18) . ?
N8 O3 1.2065(17) . ?

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
N4 C1 N1 117.50(12) . . ?
N4 C1 N2 117.45(12) . . ?
N1 C1 N2 125.05(12) . . ?
N5 C2 N1 118.73(13) . . ?
N5 C2 N3 116.63(13) . . ?
N1 C2 N3 124.64(12) . . ?
N3 C3 N2 129.15(12) . . ?
N3 C3 C4 113.94(11) . . ?
N2 C3 C4 116.91(11) . . ?
N6 C4 C5 107.28(12) . . ?
N6 C4 C3 124.25(12) . . ?
C5 C4 C3 128.45(12) . . ?
N7 C5 C4 111.11(13) . . ?
N7 C5 N8 119.26(13) . . ?
C4 C5 N8 129.64(12) . . ?
C2 N1 C1 115.45(12) . . ?
C3 N2 C1 112.45(11) . . ?
C3 N3 C2 113.22(11) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N6 O1 106.12(12) . . ?
C5 N7 O1 104.33(12) . . ?
O2 N8 O3 125.91(15) . . ?
O2 N8 C5 116.97(13) . . ?
O3 N8 C5 117.11(14) . . ?
N7 O1 N6 111.16(11) . . ?

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
N3 C3 C4 N6 -172.46(13) . . . . ?
N2 C3 C4 N6 7.1(2) . . . . ?
N3 C3 C4 C5 6.0(2) . . . . ?
N2 C3 C4 C5 -174.46(13) . . . . ?
N6 C4 C5 N7 -0.07(18) . . . . ?
C3 C4 C5 N7 -178.73(14) . . . . ?
N6 C4 C5 N8 -179.61(14) . . . . ?
C3 C4 C5 N8 1.7(2) . . . . ?
N5 C2 N1 C1 -178.55(14) . . . . ?
N3 C2 N1 C1 1.1(2) . . . . ?
N4 C1 N1 C2 -178.29(13) . . . . ?
N2 C1 N1 C2 1.1(2) . . . . ?
N3 C3 N2 C1 0.15(19) . . . . ?
C4 C3 N2 C1 -179.32(11) . . . . ?
N4 C1 N2 C3 177.73(12) . . . . ?
N1 C1 N2 C3 -1.64(19) . . . . ?
N2 C3 N3 C2 1.7(2) . . . . ?
C4 C3 N3 C2 -178.85(11) . . . . ?
N5 C2 N3 C3 177.33(14) . . . . ?
N1 C2 N3 C3 -2.3(2) . . . . ?
C5 C4 N6 O1 0.42(16) . . . . ?
C3 C4 N6 O1 179.16(12) . . . . ?
C4 C5 N7 O1 -0.32(17) . . . . ?
N8 C5 N7 O1 179.28(13) . . . . ?
N7 C5 N8 O2 -102.96(18) . . . . ?
C4 C5 N8 O2 76.6(2) . . . . ?
N7 C5 N8 O3 75.88(19) . . . . ?
C4 C5 N8 O3 -104.61(18) . . . . ?
C5 N7 O1 N6 0.59(18) . . . . ?
C4 N6 O1 N7 -0.65(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5B O2 0.86 2.66 3.183(2) 120.5 2_646 yes
N5 H5B O1 0.86 2.60 3.2317(19) 131.7 4_576 yes
N5 H5A N2 0.86 2.64 3.2075(19) 124.6 4_566 yes
N4 H4B N6 0.86 2.37 3.2059(19) 162.9 2_545 yes
N4 H4A N1 0.86 2.20 3.0543(18) 176.7 3_556 yes

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_comp_13
_database_code_depnum_ccdc_archive 'CCDC 2300041'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 H5 N10 O), O4 S, H2 O'
_chemical_formula_sum            'C10 H12 N20 O7 S'
_chemical_formula_weight         556.46

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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

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

_cell_length_a                   30.8441(18)
_cell_length_b                   7.2786(4)
_cell_length_c                   9.4707(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2126.19(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4921
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.91

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            9423
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.641
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             2310
_reflns_number_gt                1946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.888

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+1.5268P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0047(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62738(11) 0.7136(5) 0.4746(4) 0.0337(7) Uani 1 1 d . . . . .
C2 C 0.57941(11) 0.7092(5) 0.6527(4) 0.0398(9) Uani 1 1 d . . . . .
C3 C 0.60172(10) 0.9852(5) 0.5475(4) 0.0389(8) Uani 1 1 d . . . . .
C4 C 0.65572(12) 0.6099(5) 0.3771(4) 0.0417(9) Uani 1 1 d . . . . .
C5 C 0.68317(13) 0.6726(7) 0.2642(4) 0.0544(11) Uani 1 1 d . . . . .
N1 N 0.60434(10) 0.6114(4) 0.5644(3) 0.0372(7) Uani 1 1 d . . . . .
N2 N 0.57862(10) 0.8936(5) 0.6460(4) 0.0434(8) Uani 1 1 d . . . . .
H2 H 0.5604(13) 0.937(6) 0.685(5) 0.052 Uiso 1 1 d . U . . .
N3 N 0.62818(9) 0.8929(4) 0.4592(3) 0.0400(7) Uani 1 1 d . . . . .
N4 N 0.55624(12) 0.6277(6) 0.7495(3) 0.0620(11) Uani 1 1 d . . . . .
H4A H 0.556852 0.509945 0.757113 0.074 Uiso 1 1 calc R U . . .
H4B H 0.540358 0.691609 0.805686 0.074 Uiso 1 1 calc R U . . .
N5 N 0.59814(13) 1.1634(5) 0.5386(5) 0.0659(12) Uani 1 1 d . . . . .
H5A H 0.612715 1.222755 0.476107 0.079 Uiso 1 1 calc R U . . .
H5B H 0.581196 1.221443 0.595266 0.079 Uiso 1 1 calc R U . . .
N6 N 0.65889(13) 0.4321(5) 0.3834(4) 0.0645(11) Uani 1 1 d . . . . .
N7 N 0.70210(13) 0.5314(8) 0.2075(4) 0.0806(15) Uani 1 1 d . . . . .
N8 N 0.68861(13) 0.8527(6) 0.2193(4) 0.0674(11) Uani 1 1 d . . . . .
N9 N 0.71012(12) 0.8637(7) 0.1070(4) 0.0793(14) Uani 1 1 d . . . . .
N10 N 0.72823(17) 0.8969(9) 0.0089(5) 0.117(2) Uani 1 1 d . . . . .
O1 O 0.68739(15) 0.3800(6) 0.2808(4) 0.0899(13) Uani 1 1 d . . . . .
S1 S 0.500000 0.16999(14) 0.83479(11) 0.0267(3) Uani 1 2 d S T P . .
O2 O 0.53789(11) 0.2382(6) 0.7618(4) 0.0867(13) Uani 1 1 d . . . . .
O3 O 0.500000 -0.0279(5) 0.8221(5) 0.0854(16) Uani 1 2 d S T P . .
O4 O 0.500000 0.2305(5) 0.9799(4) 0.0478(10) Uani 1 2 d S T P . .
O5 O 0.500000 0.6100(6) -0.0119(4) 0.0648(13) Uani 1 2 d GS T P . .
H5C H 0.490603 0.662172 0.062319 0.097 Uiso 0.5 1 d G U P . .
H5D H 0.500082 0.495574 0.001644 0.097 Uiso 1 2 d G U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.314(4) . ?
C1 N1 1.334(4) . ?
C1 C4 1.478(5) . ?
C2 N4 1.305(5) . ?
C2 N1 1.341(5) . ?
C2 N2 1.344(5) . ?
C3 N5 1.304(5) . ?
C3 N3 1.348(5) . ?
C3 N2 1.350(5) . ?
C4 N6 1.299(5) . ?
C4 C5 1.438(5) . ?
C5 N7 1.298(6) . ?
C5 N8 1.388(6) . ?
N2 H2 0.74(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O1 1.364(5) . ?
N7 O1 1.379(6) . ?
N8 N9 1.256(5) . ?
N9 N10 1.111(5) . ?
S1 O4 1.443(4) . ?
S1 O3 1.446(4) . ?
S1 O2 1.446(3) . ?
S1 O2 1.446(3) 3_655 ?
O5 H5C 0.8500 . ?
O5 H5D 0.8428 . ?
O5 H5C 0.85(7) 3_655 ?

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
N3 C1 N1 129.4(3) . . ?
N3 C1 C4 115.3(3) . . ?
N1 C1 C4 115.4(3) . . ?
N4 C2 N1 120.7(4) . . ?
N4 C2 N2 118.5(4) . . ?
N1 C2 N2 120.7(3) . . ?
N5 C3 N3 120.4(4) . . ?
N5 C3 N2 119.4(4) . . ?
N3 C3 N2 120.2(3) . . ?
N6 C4 C5 107.8(3) . . ?
N6 C4 C1 121.6(4) . . ?
C5 C4 C1 130.6(4) . . ?
N7 C5 N8 124.5(4) . . ?
N7 C5 C4 108.8(5) . . ?
N8 C5 C4 126.8(4) . . ?
C1 N1 C2 114.0(3) . . ?
C2 N2 C3 121.1(3) . . ?
C2 N2 H2 114(3) . . ?
C3 N2 H2 122(4) . . ?
C1 N3 C3 114.5(3) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N6 O1 107.0(4) . . ?
C5 N7 O1 106.0(4) . . ?
N9 N8 C5 112.6(4) . . ?
N10 N9 N8 171.0(7) . . ?
N6 O1 N7 110.4(3) . . ?
O4 S1 O3 112.6(3) . . ?
O4 S1 O2 110.52(17) . . ?
O3 S1 O2 107.6(2) . . ?
O4 S1 O2 110.52(17) . 3_655 ?
O3 S1 O2 107.6(2) . 3_655 ?
O2 S1 O2 107.9(4) . 3_655 ?
H5C O5 H5D 108.4 . . ?
H5C O5 H5C 39.9 . 3_655 ?
H5D O5 H5C 108.3 . 3_655 ?

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
N3 C1 C4 N6 178.2(4) . . . . ?
N1 C1 C4 N6 -2.6(5) . . . . ?
N3 C1 C4 C5 -2.3(6) . . . . ?
N1 C1 C4 C5 176.9(4) . . . . ?
N6 C4 C5 N7 -0.5(5) . . . . ?
C1 C4 C5 N7 179.9(4) . . . . ?
N6 C4 C5 N8 178.4(4) . . . . ?
C1 C4 C5 N8 -1.1(7) . . . . ?
N3 C1 N1 C2 -1.7(5) . . . . ?
C4 C1 N1 C2 179.1(3) . . . . ?
N4 C2 N1 C1 -177.6(3) . . . . ?
N2 C2 N1 C1 0.6(5) . . . . ?
N4 C2 N2 C3 -179.6(3) . . . . ?
N1 C2 N2 C3 2.1(5) . . . . ?
N5 C3 N2 C2 175.9(3) . . . . ?
N3 C3 N2 C2 -4.1(5) . . . . ?
N1 C1 N3 C3 0.0(5) . . . . ?
C4 C1 N3 C3 179.1(3) . . . . ?
N5 C3 N3 C1 -177.0(3) . . . . ?
N2 C3 N3 C1 2.9(5) . . . . ?
C5 C4 N6 O1 0.6(5) . . . . ?
C1 C4 N6 O1 -179.8(3) . . . . ?
N8 C5 N7 O1 -178.8(4) . . . . ?
C4 C5 N7 O1 0.2(5) . . . . ?
N7 C5 N8 N9 7.6(6) . . . . ?
C4 C5 N8 N9 -171.2(4) . . . . ?
C4 N6 O1 N7 -0.5(5) . . . . ?
C5 N7 O1 N6 0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A O2 0.86 2.06 2.893(6) 161.9 . yes
N4 H4B O3 0.86 2.40 3.125(5) 142.9 1_565 yes
N4 H4B O5 0.86 2.21 2.851(5) 131.2 1_556 yes
N5 H5A N6 0.86 2.26 3.082(6) 159.2 1_565 yes
N5 H5B O2 0.86 2.07 2.867(6) 153.7 1_565 yes
N2 H2 S1 0.74(4) 2.89(4) 3.623(3) 168(4) 1_565 yes
N2 H2 O2 0.74(4) 2.42(4) 3.012(5) 139(4) 1_565 yes
N2 H2 O3 0.74(4) 2.29(4) 2.998(4) 162(4) 1_565 yes

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_comp_14
_database_code_depnum_ccdc_archive 'CCDC 2300042'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N8 O, Cl O4'
_chemical_formula_sum            'C5 H7 Cl N8 O5'
_chemical_formula_weight         294.64

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4349(6)
_cell_length_b                   8.3262(8)
_cell_length_c                   9.1790(8)
_cell_angle_alpha                68.801(3)
_cell_angle_beta                 84.893(3)
_cell_angle_gamma                87.370(3)
_cell_volume                     527.61(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4628
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            8048
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2398
_reflns_number_gt                2077
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.2956P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2398
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5372(2) 0.7457(2) 0.81441(19) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.8124(2) 0.8872(2) 0.70500(19) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.6277(2) 0.8140(2) 0.55825(18) 0.0221(3) Uani 1 1 d . . . . .
C4 C 0.5824(2) 0.8165(2) 0.40430(18) 0.0231(3) Uani 1 1 d . . . . .
C5 C 0.4365(2) 0.7340(2) 0.3676(2) 0.0272(4) Uani 1 1 d . . . . .
N1 N 0.6910(2) 0.8171(2) 0.83091(16) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.720(3) 0.813(3) 0.921(3) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.7789(2) 0.8909(2) 0.56239(16) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.50583(19) 0.73890(19) 0.67468(16) 0.0253(3) Uani 1 1 d . . . . .
N4 N 0.4178(2) 0.6857(2) 0.93289(17) 0.0305(4) Uani 1 1 d . . . . .
H4A H 0.319687 0.642252 0.921485 0.037 Uiso 1 1 calc R U . . .
H4B H 0.437076 0.689683 1.022540 0.037 Uiso 1 1 calc R U . . .
N5 N 0.9591(2) 0.9540(3) 0.72383(19) 0.0413(5) Uani 1 1 d . . . . .
H5A H 1.035171 1.000720 0.644879 0.050 Uiso 1 1 calc R U . . .
H5B H 0.980194 0.951484 0.815256 0.050 Uiso 1 1 calc R U . . .
N6 N 0.3140(2) 0.6296(3) 0.46798(19) 0.0444(5) Uani 1 1 d . . . . .
H6A H 0.232260 0.585789 0.433656 0.053 Uiso 1 1 calc R U . . .
H6B H 0.316845 0.606043 0.567029 0.053 Uiso 1 1 calc R U . . .
N7 N 0.4437(2) 0.7779(2) 0.21454(18) 0.0336(4) Uani 1 1 d . . . . .
N8 N 0.6738(2) 0.9082(2) 0.27568(16) 0.0271(3) Uani 1 1 d . . . . .
O1 O 0.59276(18) 0.88767(17) 0.15674(13) 0.0318(3) Uani 1 1 d . . . . .
Cl1 Cl 0.97328(6) 0.61402(6) 0.18040(5) 0.03111(17) Uani 1 1 d . . . . .
O2 O 0.8046(2) 0.5478(3) 0.1645(2) 0.0621(5) Uani 1 1 d . . . . .
O3 O 1.1212(2) 0.5086(2) 0.1615(2) 0.0621(5) Uani 1 1 d . . . . .
O4 O 0.9936(3) 0.7829(2) 0.06244(19) 0.0602(5) Uani 1 1 d . . . . .
O5 O 0.9667(2) 0.6278(2) 0.33086(16) 0.0438(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
C1 N4 1.302(2) . ?
C1 N3 1.345(2) . ?
C1 N1 1.357(2) . ?
C2 N5 1.299(2) . ?
C2 N2 1.344(2) . ?
C2 N1 1.366(2) . ?
C3 N3 1.323(2) . ?
C3 N2 1.329(2) . ?
C3 C4 1.474(2) . ?
C4 N8 1.300(2) . ?
C4 C5 1.436(2) . ?
C5 N7 1.315(2) . ?
C5 N6 1.333(2) . ?
N1 H1 0.86(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 O1 1.408(2) . ?
N8 O1 1.3585(18) . ?
Cl1 O3 1.4133(17) . ?
Cl1 O5 1.4232(14) . ?
Cl1 O2 1.4329(16) . ?
Cl1 O4 1.4357(17) . ?

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
N4 C1 N3 119.55(16) . . ?
N4 C1 N1 120.31(15) . . ?
N3 C1 N1 120.14(15) . . ?
N5 C2 N2 120.21(16) . . ?
N5 C2 N1 119.27(15) . . ?
N2 C2 N1 120.50(15) . . ?
N3 C3 N2 128.49(15) . . ?
N3 C3 C4 114.22(14) . . ?
N2 C3 C4 117.24(14) . . ?
N8 C4 C5 109.70(14) . . ?
N8 C4 C3 121.28(15) . . ?
C5 C4 C3 128.94(15) . . ?
N7 C5 N6 124.66(16) . . ?
N7 C5 C4 107.96(15) . . ?
N6 C5 C4 127.37(16) . . ?
C1 N1 C2 120.38(14) . . ?
C1 N1 H1 121.9(15) . . ?
C2 N1 H1 117.5(15) . . ?
C3 N2 C2 114.85(14) . . ?
C3 N3 C1 115.48(14) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C5 N7 O1 105.17(13) . . ?
C4 N8 O1 106.16(14) . . ?
N8 O1 N7 111.01(12) . . ?
O3 Cl1 O5 110.26(11) . . ?
O3 Cl1 O2 112.07(12) . . ?
O5 Cl1 O2 108.42(10) . . ?
O3 Cl1 O4 109.23(11) . . ?
O5 Cl1 O4 108.93(11) . . ?
O2 Cl1 O4 107.85(12) . . ?

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
N3 C3 C4 N8 169.24(16) . . . . ?
N2 C3 C4 N8 -8.5(2) . . . . ?
N3 C3 C4 C5 -7.2(3) . . . . ?
N2 C3 C4 C5 175.08(17) . . . . ?
N8 C4 C5 N7 0.4(2) . . . . ?
C3 C4 C5 N7 177.17(17) . . . . ?
N8 C4 C5 N6 179.80(19) . . . . ?
C3 C4 C5 N6 -3.4(3) . . . . ?
N4 C1 N1 C2 -176.95(17) . . . . ?
N3 C1 N1 C2 1.9(3) . . . . ?
N5 C2 N1 C1 -179.60(17) . . . . ?
N2 C2 N1 C1 1.9(3) . . . . ?
N3 C3 N2 C2 1.7(3) . . . . ?
C4 C3 N2 C2 179.00(15) . . . . ?
N5 C2 N2 C3 177.99(18) . . . . ?
N1 C2 N2 C3 -3.6(2) . . . . ?
N2 C3 N3 C1 2.0(3) . . . . ?
C4 C3 N3 C1 -175.43(14) . . . . ?
N4 C1 N3 C3 175.19(16) . . . . ?
N1 C1 N3 C3 -3.7(2) . . . . ?
N6 C5 N7 O1 -179.75(19) . . . . ?
C4 C5 N7 O1 -0.3(2) . . . . ?
C5 C4 N8 O1 -0.27(19) . . . . ?
C3 C4 N8 O1 -177.34(15) . . . . ?
C4 N8 O1 N7 0.07(19) . . . . ?
C5 N7 O1 N8 0.16(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6B O2 0.86 2.44 3.214(3) 149.9 2_666 yes
N6 H6B N3 0.86 2.31 2.883(2) 123.8 . yes
N6 H6A O5 0.86 2.63 3.037(2) 110.3 2_666 yes
N6 H6A O5 0.86 2.22 2.975(2) 146.0 1_455 yes
N5 H5B O4 0.86 2.20 2.943(2) 144.1 1_556 yes
N5 H5A N8 0.86 2.57 3.010(2) 112.6 2_776 yes
N5 H5A N2 0.86 2.18 3.038(2) 176.4 2_776 yes
N4 H4B N7 0.86 2.15 2.974(2) 161.7 1_556 yes
N4 H4A O3 0.86 2.46 2.946(2) 116.2 1_456 yes
N4 H4A O2 0.86 2.27 3.021(2) 146.2 2_666 yes
N1 H1 O4 0.86(2) 2.46(2) 3.165(2) 138.8(19) 1_556 yes
N1 H1 O1 0.86(2) 2.55(2) 3.2659(18) 140.7(19) 1_556 yes

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_comp_3
_database_code_depnum_ccdc_archive 'CCDC 2300033'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;

_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-19
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H6 N8 O'
_chemical_formula_sum            'C5 H6 N8 O'
_chemical_formula_weight         194.18
_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                   3.6810(3)
_cell_length_b                   15.3434(13)
_cell_length_c                   13.3774(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.609(2)
_cell_angle_gamma                90
_cell_volume                     755.24(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1795
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.863
_cell_measurement_theta_min      2.655
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1098 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8379
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.020
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1040
_reflns_number_total             1550
_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       APEX-III
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1550
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.073
_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)+(0.0429P)²+0.3940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N7-H7B = N7-H7A = N3-H3A = N3-H3B = N8-H8A = N8-H8B
 0.87 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.4697(5) 0.19823(10) 0.51762(13) 0.0276(5) Uani 1 1 d . . . . .
N4 N 0.7356(5) 0.43828(12) 0.40050(14) 0.0199(5) Uani 1 1 d . . . . .
N6 N 0.6624(5) 0.52585(12) 0.25308(15) 0.0210(5) Uani 1 1 d . . . . .
N5 N 0.4421(5) 0.37914(12) 0.25423(14) 0.0210(5) Uani 1 1 d . . . . .
N8 N 0.9530(6) 0.57829(14) 0.39407(17) 0.0229(5) Uani 1 1 d D . . . .
N2 N 0.5876(6) 0.28055(13) 0.49499(16) 0.0255(5) Uani 1 1 d . . . . .
N3 N 0.1785(6) 0.20355(14) 0.26881(17) 0.0268(5) Uani 1 1 d D . . . .
N7 N 0.3878(6) 0.46492(14) 0.11392(16) 0.0257(5) Uani 1 1 d D . . . .
N1 N 0.2976(6) 0.15868(13) 0.43384(16) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.5631(6) 0.37597(15) 0.34910(17) 0.0185(5) Uani 1 1 d . . . . .
C4 C 0.4908(6) 0.29349(15) 0.40134(18) 0.0200(5) Uani 1 1 d . . . . .
C1 C 0.5001(6) 0.45734(15) 0.20942(18) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.7815(6) 0.51346(15) 0.34762(18) 0.0193(6) Uani 1 1 d . . . . .
C5 C 0.3102(6) 0.21720(15) 0.36289(18) 0.0216(6) Uani 1 1 d . . . . .
H8A H 1.006(7) 0.6238(13) 0.3584(17) 0.025(7) Uiso 1 1 d D . . . .
H3A H 0.159(8) 0.2513(14) 0.2318(19) 0.037(8) Uiso 1 1 d D . . . .
H7A H 0.363(8) 0.5165(13) 0.088(2) 0.036(8) Uiso 1 1 d D . . . .
H7B H 0.263(8) 0.4217(16) 0.086(2) 0.047(9) Uiso 1 1 d D . . . .
H8B H 1.046(8) 0.5727(19) 0.4570(15) 0.045(9) Uiso 1 1 d D . . . .
H3B H 0.044(8) 0.1564(15) 0.261(2) 0.052(10) Uiso 1 1 d 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 N2 1.372(3) . ?
O1 N1 1.409(3) . ?
N4 C3 1.329(3) . ?
N4 C2 1.366(3) . ?
N6 C1 1.335(3) . ?
N6 C2 1.340(3) . ?
N5 C3 1.334(3) . ?
N5 C1 1.361(3) . ?
N8 C2 1.324(3) . ?
N8 H8A 0.870(17) . ?
N8 H8B 0.904(18) . ?
N2 C4 1.308(3) . ?
N3 C5 1.352(3) . ?
N3 H3A 0.886(17) . ?
N3 H3B 0.881(18) . ?
N7 C1 1.337(3) . ?
N7 H7A 0.867(17) . ?
N7 H7B 0.882(18) . ?
N1 C5 1.308(3) . ?
C3 C4 1.473(3) . ?
C4 C5 1.434(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
N2 O1 N1 111.03(17) . . ?
C3 N4 C2 113.8(2) . . ?
C1 N6 C2 115.6(2) . . ?
C3 N5 C1 113.5(2) . . ?
C2 N8 H8A 117.2(16) . . ?
C2 N8 H8B 121.9(19) . . ?
H8A N8 H8B 120(3) . . ?
C4 N2 O1 105.76(19) . . ?
C5 N3 H3A 114.4(19) . . ?
C5 N3 H3B 115(2) . . ?
H3A N3 H3B 125(3) . . ?
C1 N7 H7A 119.1(19) . . ?
C1 N7 H7B 119(2) . . ?
H7A N7 H7B 118(3) . . ?
C5 N1 O1 104.91(18) . . ?
N4 C3 N5 127.4(2) . . ?
N4 C3 C4 117.6(2) . . ?
N5 C3 C4 115.0(2) . . ?
N2 C4 C3 122.5(2) . . ?
N2 C4 C5 109.3(2) . . ?
C5 C4 C3 128.2(2) . . ?
N6 C1 N5 125.1(2) . . ?
N6 C1 N7 118.2(2) . . ?
N7 C1 N5 116.7(2) . . ?
N6 C2 N4 124.5(2) . . ?
N8 C2 N4 117.1(2) . . ?
N8 C2 N6 118.4(2) . . ?
N3 C5 C4 127.6(2) . . ?
N1 C5 N3 123.4(2) . . ?
N1 C5 C4 109.0(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 N2 C4 C3 178.8(2) . . . . ?
O1 N2 C4 C5 -0.7(3) . . . . ?
O1 N1 C5 N3 178.6(2) . . . . ?
O1 N1 C5 C4 0.2(3) . . . . ?
N4 C3 C4 N2 0.4(3) . . . . ?
N4 C3 C4 C5 179.8(2) . . . . ?
N5 C3 C4 N2 -179.0(2) . . . . ?
N5 C3 C4 C5 0.3(4) . . . . ?
N2 O1 N1 C5 -0.6(3) . . . . ?
N2 C4 C5 N3 -178.0(2) . . . . ?
N2 C4 C5 N1 0.3(3) . . . . ?
N1 O1 N2 C4 0.8(3) . . . . ?
C3 N4 C2 N6 0.9(3) . . . . ?
C3 N4 C2 N8 -179.7(2) . . . . ?
C3 N5 C1 N6 0.3(3) . . . . ?
C3 N5 C1 N7 179.5(2) . . . . ?
C3 C4 C5 N3 2.6(4) . . . . ?
C3 C4 C5 N1 -179.1(2) . . . . ?
C1 N6 C2 N4 -2.3(3) . . . . ?
C1 N6 C2 N8 178.3(2) . . . . ?
C1 N5 C3 N4 -1.9(4) . . . . ?
C1 N5 C3 C4 177.5(2) . . . . ?
C2 N4 C3 N5 1.4(4) . . . . ?
C2 N4 C3 C4 -178.0(2) . . . . ?
C2 N6 C1 N5 1.7(3) . . . . ?
C2 N6 C1 N7 -177.6(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_comp_17
_database_code_depnum_ccdc_archive 'CCDC 2300047'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N10 O5'
_chemical_formula_sum            'C6 H6 N10 O5'
_chemical_formula_weight         298.21
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.851(2)
_cell_length_b                   6.1775(8)
_cell_length_c                   11.9579(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1097.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    710
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.980
_cell_measurement_theta_min      3.408
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.6896.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3710
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.187
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_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
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                707
_reflns_number_total             1219
_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       APEX-III
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1219
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0813
_refine_ls_restrained_S_all      1.138
_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)+(0.0529P)²+1.4263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 O5-H5
 0.87 with sigma of 0.02
 N5-H5A = N5-H5B
 0.87 with sigma of 0.02
 N6-H6
 0.87 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
O5 O 0.5123(3) 0.250000 0.7444(4) 0.0295(11) Uani 1 2 d DS T P . .
H5 H 0.467(3) 0.250000 0.697(5) 0.044 Uiso 1 2 d DS U P . .
O3 O 0.4766(3) 0.250000 0.1531(4) 0.0327(12) Uani 1 2 d S T P . .
O1 O 0.3703(3) 0.250000 0.5893(4) 0.0303(11) Uani 1 2 d S T P . .
O2 O 0.3141(3) 0.250000 0.4223(4) 0.0315(12) Uani 1 2 d S T P . .
O4 O 0.8696(3) 0.250000 0.5747(4) 0.0353(12) Uani 1 2 d S T P . .
N7 N 0.4650(3) 0.250000 0.4484(4) 0.0231(13) Uani 1 2 d S T P . .
N2 N 0.5841(3) 0.250000 0.6678(4) 0.0250(13) Uani 1 2 d S T P . .
N5 N 0.7270(4) 0.250000 0.2858(5) 0.0290(15) Uani 1 2 d DS T P . .
N8 N 0.3819(3) 0.250000 0.4837(4) 0.0232(13) Uani 1 2 d S T P . .
N6 N 0.6548(4) 0.250000 0.4578(5) 0.0256(14) Uani 1 2 d DS T P . .
N9 N 0.4210(3) 0.250000 0.2486(5) 0.0281(13) Uani 1 2 d S T P . .
N4 N 0.8137(3) 0.250000 0.4815(5) 0.0294(14) Uani 1 2 d S T P . .
N1 N 0.6739(4) 0.250000 0.8313(5) 0.0308(15) Uani 1 2 d DS T P . .
N10 N 0.5656(3) 0.250000 0.1817(5) 0.0310(14) Uani 1 2 d S T P . .
C4 C 0.6548(4) 0.250000 0.3469(5) 0.0216(15) Uani 1 2 d S T P . .
N3 N 0.8210(3) 0.250000 0.6727(5) 0.0345(15) Uani 1 2 d S T P . .
C2 C 0.7363(4) 0.250000 0.6424(5) 0.0224(15) Uani 1 2 d S T P . .
C5 C 0.5671(4) 0.250000 0.2898(6) 0.0231(15) Uani 1 2 d S T P . .
C6 C 0.4771(4) 0.250000 0.3329(5) 0.0212(15) Uani 1 2 d S T P . .
C3 C 0.7324(4) 0.250000 0.5232(5) 0.0236(15) Uani 1 2 d S T P . .
C1 C 0.6602(4) 0.250000 0.7199(6) 0.0251(16) Uani 1 2 d S T P . .
H1A H 0.628(2) 0.250000 0.876(4) 0.003(14) Uiso 1 2 d DS . P . .
H1B H 0.729(2) 0.250000 0.853(6) 0.05(3) Uiso 1 2 d DS . P . .
H5A H 0.780(2) 0.250000 0.316(6) 0.04(2) Uiso 1 2 d DS . P . .
H5B H 0.719(5) 0.250000 0.213(2) 0.05(3) Uiso 1 2 d DS . P . .
H6 H 0.608(3) 0.250000 0.502(4) 0.031(19) Uiso 1 2 d DS . P . .


_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
O5 H5 0.88(2) . ?
O5 N2 1.406(6) . ?
O3 N9 1.409(6) . ?
O3 N10 1.364(6) . ?
O1 N8 1.275(7) . ?
O2 N8 1.245(6) . ?
O4 N4 1.389(7) . ?
O4 N3 1.376(7) . ?
N7 N8 1.305(7) . ?
N7 C6 1.392(8) . ?
N2 C1 1.291(8) . ?
N5 C4 1.297(8) . ?
N5 H5A 0.87(2) . ?
N5 H5B 0.88(2) . ?
N6 C4 1.326(8) . ?
N6 C3 1.393(8) . ?
N6 H6 0.87(2) . ?
N9 C6 1.308(7) . ?
N4 C3 1.306(8) . ?
N1 C1 1.347(9) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.86(2) . ?
N10 C5 1.293(8) . ?
C4 C5 1.471(8) . ?
N3 C2 1.308(7) . ?
C2 C3 1.427(8) . ?
C2 C1 1.461(9) . ?
C5 C6 1.432(8) . ?

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
N2 O5 H5 99(5) . . ?
N10 O3 N9 111.3(4) . . ?
N3 O4 N4 111.7(4) . . ?
N8 N7 C6 116.3(5) . . ?
C1 N2 O5 110.5(5) . . ?
C4 N5 H5A 121(5) . . ?
C4 N5 H5B 116(5) . . ?
H5A N5 H5B 123(7) . . ?
O1 N8 N7 116.6(5) . . ?
O2 N8 O1 118.3(5) . . ?
O2 N8 N7 125.0(5) . . ?
C4 N6 C3 124.2(5) . . ?
C4 N6 H6 128(4) . . ?
C3 N6 H6 108(4) . . ?
C6 N9 O3 104.6(5) . . ?
C3 N4 O4 104.3(5) . . ?
C1 N1 H1A 119(3) . . ?
C1 N1 H1B 116(5) . . ?
H1A N1 H1B 125(6) . . ?
C5 N10 O3 105.5(5) . . ?
N5 C4 N6 124.2(6) . . ?
N5 C4 C5 118.0(6) . . ?
N6 C4 C5 117.7(6) . . ?
C2 N3 O4 105.6(5) . . ?
N3 C2 C3 108.4(6) . . ?
N3 C2 C1 124.6(6) . . ?
C3 C2 C1 127.0(6) . . ?
N10 C5 C4 118.7(6) . . ?
N10 C5 C6 110.1(5) . . ?
C6 C5 C4 131.2(6) . . ?
N7 C6 C5 118.6(5) . . ?
N9 C6 N7 133.0(6) . . ?
N9 C6 C5 108.4(5) . . ?
N6 C3 C2 126.5(6) . . ?
N4 C3 N6 123.4(6) . . ?
N4 C3 C2 110.1(5) . . ?
N2 C1 N1 127.5(6) . . ?
N2 C1 C2 111.8(6) . . ?
N1 C1 C2 120.7(6) . . ?

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
O5 N2 C1 N1 0.000(1) . . . . ?
O5 N2 C1 C2 180.000(1) . . . . ?
O3 N9 C6 N7 180.000(1) . . . . ?
O3 N9 C6 C5 0.000(0) . . . . ?
O3 N10 C5 C4 180.000(0) . . . . ?
O3 N10 C5 C6 0.000(0) . . . . ?
O4 N4 C3 N6 180.000(1) . . . . ?
O4 N4 C3 C2 0.000(1) . . . . ?
O4 N3 C2 C3 0.000(1) . . . . ?
O4 N3 C2 C1 180.000(1) . . . . ?
N5 C4 C5 N10 0.000(1) . . . . ?
N5 C4 C5 C6 180.000(1) . . . . ?
N8 N7 C6 N9 0.000(1) . . . . ?
N8 N7 C6 C5 180.000(1) . . . . ?
N6 C4 C5 N10 180.000(1) . . . . ?
N6 C4 C5 C6 0.000(1) . . . . ?
N9 O3 N10 C5 0.000(0) . . . . ?
N4 O4 N3 C2 0.000(1) . . . . ?
N10 O3 N9 C6 0.000(0) . . . . ?
N10 C5 C6 N7 180.000(1) . . . . ?
N10 C5 C6 N9 0.000(0) . . . . ?
C4 N6 C3 N4 0.000(1) . . . . ?
C4 N6 C3 C2 180.000(1) . . . . ?
C4 C5 C6 N7 0.000(1) . . . . ?
C4 C5 C6 N9 180.000(1) . . . . ?
N3 O4 N4 C3 0.000(1) . . . . ?
N3 C2 C3 N6 180.000(1) . . . . ?
N3 C2 C3 N4 0.000(1) . . . . ?
N3 C2 C1 N2 180.000(1) . . . . ?
N3 C2 C1 N1 0.000(2) . . . . ?
C6 N7 N8 O1 180.000(1) . . . . ?
C6 N7 N8 O2 0.000(1) . . . . ?
C3 N6 C4 N5 0.000(1) . . . . ?
C3 N6 C4 C5 180.000(1) . . . . ?
C3 C2 C1 N2 0.000(1) . . . . ?
C3 C2 C1 N1 180.000(1) . . . . ?
C1 C2 C3 N6 0.000(1) . . . . ?
C1 C2 C3 N4 180.000(1) . . . . ?


_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_comp_18
_database_code_depnum_ccdc_archive 'CCDC 2300049'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-04
_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         'C6 H2 N8 O4, 3(C2 H4 O)'
_chemical_formula_sum            'C12 H14 N8 O7'
_chemical_formula_weight         382.31
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0395(4)
_cell_length_b                   11.1075(8)
_cell_length_c                   11.9166(9)
_cell_angle_alpha                110.120(3)
_cell_angle_beta                 99.467(2)
_cell_angle_gamma                98.084(2)
_cell_volume                     843.21(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.9573.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23612
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         3.003
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2998
_reflns_number_total             3796
_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 V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 V2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.060
_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)+(0.0511P)²+0.1858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B), C8(H8C,H8D),
 C7(H7A,H7B)
2.b X=CH2 refined with riding coordinates:
 N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.36102(15) 0.40637(11) 0.16795(9) 0.0358(3) Uani 1 1 d . . . . .
O6 O 0.05230(17) 0.09505(10) 0.44964(10) 0.0400(3) Uani 1 1 d . . . . .
O7 O -0.01136(17) 0.46594(11) 0.87383(9) 0.0402(3) Uani 1 1 d . . . . .
O4 O 0.46512(17) 0.25447(12) 0.76652(10) 0.0429(3) Uani 1 1 d . . . . .
N5 N 0.21161(16) 0.40315(11) 0.48806(10) 0.0251(2) Uani 1 1 d . . . . .
N8 N 0.03214(18) 0.44408(12) 0.63759(10) 0.0307(3) Uani 1 1 d . . . . .
H8A H -0.042136 0.481612 0.598871 0.037 Uiso 1 1 calc R U . . .
H8B H 0.010299 0.438674 0.706496 0.037 Uiso 1 1 calc R U . . .
O5 O 0.1105(2) 0.12575(12) 0.07760(12) 0.0549(4) Uani 1 1 d . . . . .
N2 N 0.29260(17) 0.42116(12) 0.27273(11) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.5529(2) 0.08936(12) 0.23167(13) 0.0597(4) Uani 1 1 d . . . . .
N4 N 0.47570(17) 0.28289(12) 0.48620(10) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.49437(18) 0.32567(13) 0.15488(11) 0.0360(3) Uani 1 1 d . . . . .
N6 N 0.5497(2) 0.23097(14) 0.66597(12) 0.0392(3) Uani 1 1 d . . . . .
N3 N 0.63087(19) 0.20388(14) 0.26353(12) 0.0384(3) Uani 1 1 d . . . . .
N7 N 0.31204(19) 0.31873(13) 0.75837(11) 0.0357(3) Uani 1 1 d . . . . .
C6 C 0.17504(19) 0.39630(12) 0.59270(12) 0.0251(3) Uani 1 1 d . . . . .
O3 O 0.80398(19) 0.25128(16) 0.30672(17) 0.0723(5) Uani 1 1 d . . . . .
C2 C 0.37971(19) 0.35123(13) 0.32440(12) 0.0260(3) Uani 1 1 d . . . . .
C4 C 0.4486(2) 0.28100(13) 0.59643(13) 0.0286(3) Uani 1 1 d . . . . .
C3 C 0.35375(18) 0.34400(12) 0.44267(12) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.5044(2) 0.29273(14) 0.24900(12) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.3028(2) 0.33458(13) 0.65431(12) 0.0273(3) Uani 1 1 d . . . . .
C9 C 0.1258(3) -0.02291(16) 0.41986(16) 0.0430(4) Uani 1 1 d . . . . .
H9A H 0.258711 -0.006047 0.403913 0.052 Uiso 1 1 calc R U . . .
H9B H 0.038120 -0.090867 0.344307 0.052 Uiso 1 1 calc R U . . .
C10 C -0.1366(2) 0.07188(16) 0.47655(17) 0.0427(4) Uani 1 1 d . . . . .
H10A H -0.230856 0.006180 0.402449 0.051 Uiso 1 1 calc R U . . .
H10B H -0.185694 0.154315 0.499371 0.051 Uiso 1 1 calc R U . . .
C12 C -0.0240(3) 0.36800(17) 0.92573(14) 0.0404(4) Uani 1 1 d . . . . .
H12A H 0.108767 0.351277 0.948191 0.049 Uiso 1 1 calc R U . . .
H12B H -0.109598 0.285124 0.864531 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1072(3) 0.58769(18) 0.96205(16) 0.0442(4) Uani 1 1 d . . . . .
H11A H 0.111872 0.655204 0.925237 0.053 Uiso 1 1 calc R U . . .
H11B H 0.243426 0.576921 0.985613 0.053 Uiso 1 1 calc R U . . .
C8 C 0.0356(3) 0.03285(19) 0.12581(17) 0.0515(4) Uani 1 1 d . . . . .
H8C H 0.006955 0.079457 0.206309 0.062 Uiso 1 1 calc R U . . .
H8D H 0.135868 -0.018269 0.138465 0.062 Uiso 1 1 calc R U . . .
C7 C 0.1485(3) 0.05809(19) -0.03943(17) 0.0524(5) Uani 1 1 d . . . . .
H7A H 0.250785 0.007393 -0.029841 0.063 Uiso 1 1 calc R U . . .
H7B H 0.198708 0.122475 -0.073674 0.063 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 N2 1.3773(15) . ?
O1 N1 1.3775(16) . ?
O6 C9 1.4289(19) . ?
O6 C10 1.428(2) . ?
O7 C12 1.4240(19) . ?
O7 C11 1.430(2) . ?
O4 N6 1.3861(17) . ?
O4 N7 1.3819(16) . ?
N5 C6 1.3388(17) . ?
N5 C3 1.3579(17) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C6 1.3082(17) . ?
O5 C8 1.424(2) . ?
O5 C7 1.428(2) . ?
N2 C2 1.3027(18) . ?
O2 N3 1.2109(18) . ?
N4 C4 1.3648(18) . ?
N4 C3 1.3139(17) . ?
N1 C1 1.2886(19) . ?
N6 C4 1.3177(18) . ?
N3 O3 1.2058(19) . ?
N3 C1 1.4528(19) . ?
N7 C5 1.3038(18) . ?
C6 C5 1.4560(18) . ?
C2 C3 1.4781(19) . ?
C2 C1 1.4205(18) . ?
C4 C5 1.4162(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.506(2) 2_556 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.503(2) 2_567 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8C 0.9900 . ?
C8 H8D 0.9900 . ?
C8 C7 1.496(3) 2 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
N2 O1 N1 111.25(10) . . ?
C10 O6 C9 109.56(12) . . ?
C12 O7 C11 110.53(12) . . ?
N7 O4 N6 112.34(10) . . ?
C6 N5 C3 118.07(11) . . ?
H8A N8 H8B 120.0 . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
C8 O5 C7 109.43(13) . . ?
C2 N2 O1 106.20(11) . . ?
C3 N4 C4 111.50(11) . . ?
C1 N1 O1 104.07(11) . . ?
C4 N6 O4 104.16(11) . . ?
O2 N3 C1 117.14(13) . . ?
O3 N3 O2 126.02(15) . . ?
O3 N3 C1 116.84(14) . . ?
C5 N7 O4 104.11(11) . . ?
N5 C6 C5 116.87(12) . . ?
N8 C6 N5 121.28(12) . . ?
N8 C6 C5 121.85(12) . . ?
N2 C2 C3 123.94(12) . . ?
N2 C2 C1 107.00(12) . . ?
C1 C2 C3 129.00(12) . . ?
N4 C4 C5 124.04(12) . . ?
N6 C4 N4 126.94(13) . . ?
N6 C4 C5 109.02(13) . . ?
N5 C3 C2 114.82(11) . . ?
N4 C3 N5 131.45(13) . . ?
N4 C3 C2 113.72(12) . . ?
N1 C1 N3 119.08(13) . . ?
N1 C1 C2 111.48(13) . . ?
C2 C1 N3 129.43(13) . . ?
N7 C5 C6 131.75(13) . . ?
N7 C5 C4 110.36(12) . . ?
C4 C5 C6 117.89(12) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
O6 C9 C10 110.60(13) . 2_556 ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 2_556 . ?
C10 C9 H9B 109.5 2_556 . ?
O6 C10 C9 111.01(13) . 2_556 ?
O6 C10 H10A 109.4 . . ?
O6 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 2_556 . ?
C9 C10 H10B 109.4 2_556 . ?
H10A C10 H10B 108.0 . . ?
O7 C12 H12A 109.6 . . ?
O7 C12 H12B 109.6 . . ?
O7 C12 C11 110.09(13) . 2_567 ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.6 2_567 . ?
C11 C12 H12B 109.6 2_567 . ?
O7 C11 C12 110.54(13) . 2_567 ?
O7 C11 H11A 109.5 . . ?
O7 C11 H11B 109.5 . . ?
C12 C11 H11A 109.5 2_567 . ?
C12 C11 H11B 109.5 2_567 . ?
H11A C11 H11B 108.1 . . ?
O5 C8 H8C 109.6 . . ?
O5 C8 H8D 109.6 . . ?
O5 C8 C7 110.29(16) . 2 ?
H8C C8 H8D 108.1 . . ?
C7 C8 H8C 109.6 2 . ?
C7 C8 H8D 109.6 2 . ?
O5 C7 C8 110.46(15) . 2 ?
O5 C7 H7A 109.6 . . ?
O5 C7 H7B 109.6 . . ?
C8 C7 H7A 109.6 2 . ?
C8 C7 H7B 109.6 2 . ?
H7A C7 H7B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C2 C3 177.44(11) . . . . ?
O1 N2 C2 C1 0.09(14) . . . . ?
O1 N1 C1 N3 178.68(12) . . . . ?
O1 N1 C1 C2 -0.24(15) . . . . ?
O4 N6 C4 N4 179.83(13) . . . . ?
O4 N6 C4 C5 -0.09(16) . . . . ?
O4 N7 C5 C6 -179.28(14) . . . . ?
O4 N7 C5 C4 -0.01(16) . . . . ?
N5 C6 C5 N7 176.16(14) . . . . ?
N5 C6 C5 C4 -3.06(18) . . . . ?
N8 C6 C5 N7 -3.2(2) . . . . ?
N8 C6 C5 C4 177.54(13) . . . . ?
N2 O1 N1 C1 0.31(15) . . . . ?
N2 C2 C3 N5 7.94(19) . . . . ?
N2 C2 C3 N4 -170.97(13) . . . . ?
N2 C2 C1 N1 0.10(16) . . . . ?
N2 C2 C1 N3 -178.68(14) . . . . ?
O2 N3 C1 N1 -98.91(17) . . . . ?
O2 N3 C1 C2 79.8(2) . . . . ?
N4 C4 C5 N7 -179.86(13) . . . . ?
N4 C4 C5 C6 -0.5(2) . . . . ?
N1 O1 N2 C2 -0.25(14) . . . . ?
N6 O4 N7 C5 -0.05(16) . . . . ?
N6 C4 C5 N7 0.07(17) . . . . ?
N6 C4 C5 C6 179.45(12) . . . . ?
N7 O4 N6 C4 0.09(16) . . . . ?
C6 N5 C3 N4 -3.7(2) . . . . ?
C6 N5 C3 C2 177.61(11) . . . . ?
O3 N3 C1 N1 81.35(19) . . . . ?
O3 N3 C1 C2 -99.94(19) . . . . ?
C4 N4 C3 N5 0.1(2) . . . . ?
C4 N4 C3 C2 178.82(11) . . . . ?
C3 N5 C6 N8 -175.77(12) . . . . ?
C3 N5 C6 C5 4.83(17) . . . . ?
C3 N4 C4 N6 -178.00(14) . . . . ?
C3 N4 C4 C5 1.91(19) . . . . ?
C3 C2 C1 N1 -177.07(13) . . . . ?
C3 C2 C1 N3 4.1(2) . . . . ?
C1 C2 C3 N5 -175.32(13) . . . . ?
C1 C2 C3 N4 5.8(2) . . . . ?
C9 O6 C10 C9 57.56(19) . . . 2_556 ?
C10 O6 C9 C10 -57.32(19) . . . 2_556 ?
C12 O7 C11 C12 -57.87(18) . . . 2_567 ?
C11 O7 C12 C11 57.60(19) . . . 2_567 ?
C8 O5 C7 C8 58.4(2) . . . 2 ?
C7 O5 C8 C7 -58.3(2) . . . 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_comp_14a
_database_code_depnum_ccdc_archive 'CCDC 2300045'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 N8 O, 2(Cl O4), H2 O'
_chemical_formula_sum            'C5 H10 Cl2 N8 O10'
_chemical_formula_weight         413.11

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/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                   9.3759(13)
_cell_length_b                   11.1406(13)
_cell_length_c                   14.6936(19)
_cell_angle_alpha                90
_cell_angle_beta                 107.926(4)
_cell_angle_gamma                90
_cell_volume                     1460.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6582
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            12616
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3330
_reflns_number_gt                2569
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+1.2194P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0087(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3330
_refine_ls_number_parameters     233
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7110(2) 0.2665(2) 0.39911(16) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.5567(2) 0.29444(19) 0.49607(15) 0.0231(5) Uani 1 1 d . . . . .
C3 C 0.4903(2) 0.3806(2) 0.34997(16) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.5299(2) 0.2719(2) 0.58644(16) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.4077(3) 0.3137(2) 0.61799(18) 0.0314(5) Uani 1 1 d . . . . .
N1 N 0.6160(2) 0.33718(17) 0.33457(13) 0.0266(4) Uani 1 1 d . . . . .
H1 H 0.634991 0.355309 0.282584 0.032 Uiso 1 1 calc R U . . .
N2 N 0.6780(2) 0.24218(17) 0.47998(13) 0.0264(4) Uani 1 1 d . . . . .
H2 H 0.733485 0.193662 0.521513 0.032 Uiso 1 1 calc R U . . .
N3 N 0.4630(2) 0.36252(17) 0.43449(13) 0.0266(4) Uani 1 1 d . . . . .
N4 N 0.3948(2) 0.4420(2) 0.28417(15) 0.0375(5) Uani 1 1 d . . . . .
H4A H 0.411031 0.455333 0.230554 0.045 Uiso 1 1 calc R U . . .
H4B H 0.315137 0.469433 0.294020 0.045 Uiso 1 1 calc R U . . .
N5 N 0.8308(2) 0.22272(19) 0.38396(15) 0.0339(5) Uani 1 1 d . . . . .
H5A H 0.849954 0.239092 0.331718 0.041 Uiso 1 1 calc R U . . .
H5B H 0.890598 0.177477 0.426220 0.041 Uiso 1 1 calc R U . . .
N6 N 0.4267(3) 0.2698(2) 0.70330(17) 0.0431(6) Uani 1 1 d . . . . .
N7 N 0.6179(2) 0.2047(2) 0.65216(15) 0.0375(5) Uani 1 1 d . . . . .
N8 N 0.2981(2) 0.3889(2) 0.57167(18) 0.0439(6) Uani 1 1 d . . . . .
H8A H 0.232856 0.412157 0.598186 0.053 Uiso 1 1 calc R U . . .
H8B H 0.292931 0.414083 0.515409 0.053 Uiso 1 1 calc R U . . .
O1 O 0.5584(2) 0.20107(19) 0.72471(13) 0.0461(5) Uani 1 1 d . . . . .
Cl1 Cl 0.03909(7) 0.58106(6) 0.33797(5) 0.0400(2) Uani 1 1 d . . . . .
O2 O 0.1903(2) 0.5455(2) 0.37681(18) 0.0624(7) Uani 1 1 d . . . . .
O3 O -0.0024(5) 0.5817(3) 0.23742(19) 0.1118(13) Uani 1 1 d . . . . .
O4 O 0.0171(3) 0.6966(2) 0.37331(19) 0.0708(7) Uani 1 1 d . . . . .
O5 O -0.0531(3) 0.4950(3) 0.3641(3) 0.1002(11) Uani 1 1 d . . . . .
Cl2 Cl 0.78359(7) 0.93818(5) 0.53970(4) 0.03320(18) Uani 1 1 d . . . . .
O6 O 0.6530(2) 0.9644(2) 0.46239(17) 0.0643(7) Uani 1 1 d . . . . .
O7 O 0.85507(19) 1.05095(15) 0.57755(13) 0.0376(4) Uani 1 1 d . . . . .
O8 O 0.8842(2) 0.8709(2) 0.50312(15) 0.0564(6) Uani 1 1 d . . . . .
O9 O 0.7515(4) 0.8753(2) 0.6133(2) 0.0910(10) Uani 1 1 d . . . . .
O10 O 0.6783(2) 0.4395(2) 0.19377(14) 0.0456(5) Uani 1 1 d D . . . .
H10A H 0.764(2) 0.465(3) 0.207(2) 0.068 Uiso 1 1 d D U . . .
H10B H 0.648(3) 0.407(3) 0.1406(17) 0.068 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N5 1.305(3) . ?
C1 N1 1.339(3) . ?
C1 N2 1.344(3) . ?
C2 N3 1.295(3) . ?
C2 N2 1.362(3) . ?
C2 C4 1.447(3) . ?
C3 N4 1.293(3) . ?
C3 N1 1.356(3) . ?
C3 N3 1.358(3) . ?
C4 N7 1.297(3) . ?
C4 C5 1.439(3) . ?
C5 N6 1.306(3) . ?
C5 N8 1.339(3) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O1 1.403(3) . ?
N7 O1 1.347(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
Cl1 O3 1.407(3) . ?
Cl1 O2 1.412(2) . ?
Cl1 O5 1.420(3) . ?
Cl1 O4 1.427(2) . ?
Cl2 O9 1.397(2) . ?
Cl2 O6 1.421(2) . ?
Cl2 O8 1.4324(19) . ?
Cl2 O7 1.4517(18) . ?
O10 H10A 0.817(17) . ?
O10 H10B 0.830(17) . ?

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
N5 C1 N1 121.3(2) . . ?
N5 C1 N2 121.3(2) . . ?
N1 C1 N2 117.44(19) . . ?
N3 C2 N2 123.5(2) . . ?
N3 C2 C4 118.10(19) . . ?
N2 C2 C4 118.4(2) . . ?
N4 C3 N1 120.1(2) . . ?
N4 C3 N3 118.7(2) . . ?
N1 C3 N3 121.2(2) . . ?
N7 C4 C5 109.5(2) . . ?
N7 C4 C2 122.2(2) . . ?
C5 C4 C2 128.3(2) . . ?
N6 C5 N8 125.4(2) . . ?
N6 C5 C4 107.5(2) . . ?
N8 C5 C4 127.0(2) . . ?
C1 N1 C3 120.96(19) . . ?
C1 N1 H1 119.5 . . ?
C3 N1 H1 119.5 . . ?
C1 N2 C2 119.93(19) . . ?
C1 N2 H2 120.0 . . ?
C2 N2 H2 120.0 . . ?
C2 N3 C3 116.60(18) . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C5 N6 O1 105.68(18) . . ?
C4 N7 O1 106.44(19) . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N7 O1 N6 110.87(18) . . ?
O3 Cl1 O2 110.14(19) . . ?
O3 Cl1 O5 107.0(2) . . ?
O2 Cl1 O5 108.66(18) . . ?
O3 Cl1 O4 110.69(17) . . ?
O2 Cl1 O4 110.23(14) . . ?
O5 Cl1 O4 110.02(16) . . ?
O9 Cl2 O6 112.60(19) . . ?
O9 Cl2 O8 110.60(17) . . ?
O6 Cl2 O8 108.21(13) . . ?
O9 Cl2 O7 108.75(15) . . ?
O6 Cl2 O7 108.12(13) . . ?
O8 Cl2 O7 108.47(13) . . ?
H10A O10 H10B 114(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
N3 C2 C4 N7 179.9(2) . . . . ?
N2 C2 C4 N7 0.5(3) . . . . ?
N3 C2 C4 C5 1.5(4) . . . . ?
N2 C2 C4 C5 -177.8(2) . . . . ?
N7 C4 C5 N6 0.2(3) . . . . ?
C2 C4 C5 N6 178.7(2) . . . . ?
N7 C4 C5 N8 176.9(2) . . . . ?
C2 C4 C5 N8 -4.6(4) . . . . ?
N5 C1 N1 C3 178.8(2) . . . . ?
N2 C1 N1 C3 -1.1(3) . . . . ?
N4 C3 N1 C1 -175.4(2) . . . . ?
N3 C3 N1 C1 5.7(3) . . . . ?
N5 C1 N2 C2 176.4(2) . . . . ?
N1 C1 N2 C2 -3.8(3) . . . . ?
N3 C2 N2 C1 4.3(3) . . . . ?
C4 C2 N2 C1 -176.3(2) . . . . ?
N2 C2 N3 C3 0.2(3) . . . . ?
C4 C2 N3 C3 -179.14(19) . . . . ?
N4 C3 N3 C2 175.9(2) . . . . ?
N1 C3 N3 C2 -5.2(3) . . . . ?
N8 C5 N6 O1 -177.0(2) . . . . ?
C4 C5 N6 O1 -0.3(3) . . . . ?
C5 C4 N7 O1 0.0(3) . . . . ?
C2 C4 N7 O1 -178.6(2) . . . . ?
C4 N7 O1 N6 -0.2(3) . . . . ?
C5 N6 O1 N7 0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 Cl2 0.86 2.88 3.562(2) 137.0 1_545 yes
N2 H2 O7 0.86 1.98 2.808(3) 160.7 1_545 yes
N4 H4B O2 0.86 2.11 2.910(3) 154.9 . yes
N4 H4A Cl2 0.86 2.94 3.670(2) 144.1 4_575 yes
N4 H4A O7 0.86 2.15 2.944(3) 154.0 4_575 yes
N5 H5A N6 0.86 2.22 3.055(3) 163.9 4_665 yes
N5 H5B O8 0.86 2.12 2.873(3) 146.5 3_766 yes
N8 H8A Cl1 0.86 2.98 3.802(2) 161.5 3_566 yes
N8 H8A O5 0.86 2.19 3.028(3) 165.3 3_566 yes
N8 H8B N3 0.86 2.34 2.909(3) 124.3 . yes
N8 H8B O2 0.86 2.45 3.237(4) 152.2 . yes

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_comp_16
_database_code_depnum_ccdc_archive 'CCDC 2300046'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 N9 O4'
_chemical_formula_sum            'C6 H3 N9 O4'
_chemical_formula_weight         265.17
_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                   5.4102(3)
_cell_length_b                   10.9235(5)
_cell_length_c                   16.6422(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.878(2)
_cell_angle_gamma                90
_cell_volume                     971.74(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1857
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.683
_cell_measurement_theta_min      2.239
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0954 before and 0.0647 after correction. The Ratio of minimum to maximum transmission is 0.8744. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10308
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.658
_diffrn_reflns_theta_min         2.477
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1223
_reflns_number_total             1846
_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       APEX-III
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0490
_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)+(0.0394P)²+0.4892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 N2, N1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
2. Uiso/Uaniso restraints and constraints
N2 \\sim N1: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.0910(3) 0.25382(19) 0.38326(11) 0.0368(5) Uani 1 1 d . . . . .
O2 O 1.2738(4) 0.30136(18) 0.71753(12) 0.0383(5) Uani 1 1 d . . . . .
O3 O 0.8457(4) 0.58765(18) 0.77890(12) 0.0426(6) Uani 1 1 d . . . . .
O4 O 0.4932(4) 0.62106(19) 0.69888(13) 0.0437(6) Uani 1 1 d . . . . .
N5 N 0.8205(4) 0.1432(2) 0.52317(13) 0.0290(6) Uani 1 1 d . . . . .
N9 N 0.7160(5) 0.0055(2) 0.41863(16) 0.0331(6) Uani 1 1 d . . . . .
N6 N 0.5642(4) 0.3213(2) 0.54310(13) 0.0312(6) Uani 1 1 d . . . . .
N4 N 1.1612(4) 0.2374(2) 0.65123(13) 0.0347(6) Uani 1 1 d . . . . .
N3 N 1.1227(4) 0.3957(2) 0.73852(14) 0.0353(6) Uani 1 1 d . . . . .
N8 N 0.1841(4) 0.3311(2) 0.44736(14) 0.0361(6) Uani 1 1 d . . . . .
N2 N 0.7109(5) 0.4593(2) 0.67779(16) 0.0374(6) Uani 1 1 d . U . . .
N1 N 0.6834(5) 0.5623(2) 0.72215(15) 0.0363(6) Uani 1 1 d . U . . .
N7 N 0.2489(4) 0.1565(2) 0.37525(14) 0.0350(6) Uani 1 1 d . . . . .
C6 C 0.6655(5) 0.1043(2) 0.45759(16) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.4382(5) 0.1745(2) 0.43307(16) 0.0295(7) Uani 1 1 d . . . . .
C1 C 0.9213(5) 0.3875(3) 0.68452(17) 0.0300(7) Uani 1 1 d . . . . .
C4 C 0.3994(5) 0.2800(3) 0.47763(16) 0.0304(7) Uani 1 1 d . . . . .
C3 C 0.7605(5) 0.2484(3) 0.56017(16) 0.0291(7) Uani 1 1 d . . . . .
C2 C 0.9433(5) 0.2890(3) 0.62992(16) 0.0294(7) Uani 1 1 d . . . . .
H2 H 0.588(6) 0.453(3) 0.6346(19) 0.049(10) Uiso 1 1 d . . . . .
H9A H 0.852(6) -0.037(3) 0.4345(19) 0.047(10) Uiso 1 1 d . . . . .
H9B H 0.625(6) -0.013(3) 0.3774(19) 0.039(9) 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 N8 1.393(3) . ?
O1 N7 1.383(3) . ?
O2 N4 1.367(3) . ?
O2 N3 1.393(3) . ?
O3 N1 1.218(3) . ?
O4 N1 1.224(3) . ?
N5 C6 1.339(3) . ?
N5 C3 1.366(3) . ?
N9 C6 1.309(4) . ?
N9 H9A 0.87(3) . ?
N9 H9B 0.81(3) . ?
N6 C4 1.373(3) . ?
N6 C3 1.323(3) . ?
N4 C2 1.305(3) . ?
N3 C1 1.304(3) . ?
N8 C4 1.320(3) . ?
N2 N1 1.366(3) . ?
N2 C1 1.373(4) . ?
N2 H2 0.90(3) . ?
N7 C5 1.308(3) . ?
C6 C5 1.453(4) . ?
C5 C4 1.404(4) . ?
C1 C2 1.425(4) . ?
C3 C2 1.472(4) . ?

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
N7 O1 N8 112.58(19) . . ?
N4 O2 N3 112.01(19) . . ?
C6 N5 C3 118.2(2) . . ?
C6 N9 H9A 121(2) . . ?
C6 N9 H9B 119(2) . . ?
H9A N9 H9B 120(3) . . ?
C3 N6 C4 112.0(2) . . ?
C2 N4 O2 105.7(2) . . ?
C1 N3 O2 103.7(2) . . ?
C4 N8 O1 103.3(2) . . ?
N1 N2 C1 125.8(3) . . ?
N1 N2 H2 112(2) . . ?
C1 N2 H2 121(2) . . ?
O3 N1 O4 126.6(2) . . ?
O3 N1 N2 118.7(2) . . ?
O4 N1 N2 114.7(2) . . ?
C5 N7 O1 103.8(2) . . ?
N5 C6 C5 117.2(2) . . ?
N9 C6 N5 120.9(3) . . ?
N9 C6 C5 121.9(2) . . ?
N7 C5 C6 131.3(3) . . ?
N7 C5 C4 110.4(2) . . ?
C4 C5 C6 118.3(2) . . ?
N3 C1 N2 127.6(3) . . ?
N3 C1 C2 110.4(2) . . ?
N2 C1 C2 122.0(2) . . ?
N6 C4 C5 123.9(3) . . ?
N8 C4 N6 126.2(3) . . ?
N8 C4 C5 109.9(2) . . ?
N5 C3 C2 115.5(2) . . ?
N6 C3 N5 130.4(2) . . ?
N6 C3 C2 114.0(2) . . ?
N4 C2 C1 108.3(2) . . ?
N4 C2 C3 123.6(3) . . ?
C1 C2 C3 128.2(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
