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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_YF_097_a
_database_code_depnum_ccdc_archive 'CCDC 2217234'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-11-03 deposited with the CCDC.	2025-03-13 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         'C3 H2 N7 O2, H5 N2'
_chemical_formula_sum            'C3 H7 N9 O2'
_chemical_formula_weight         201.18

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                   25.649(5)
_cell_length_b                   9.0726(16)
_cell_length_c                   6.7690(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.424(6)
_cell_angle_gamma                90
_cell_volume                     1573.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5991
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5393
_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            11860
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2712
_reflns_number_gt                2279
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1701P)²+2.4625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2572
_refine_ls_wR_factor_gt          0.2414
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.39689(19) 0.6176(6) 0.8998(8) 0.0227(11) Uani 1 1 d . . . . .
C2 C 0.39652(19) 0.4596(6) 0.8941(8) 0.0231(11) Uani 1 1 d . . . . .
C3 C 0.42714(18) 0.2462(6) 0.8560(8) 0.0213(11) Uani 1 1 d . . . . .
C4 C 0.1062(2) 0.5584(6) 0.1480(8) 0.0280(12) Uani 1 1 d . . . . .
C5 C 0.1069(2) 0.3996(6) 0.1353(8) 0.0256(12) Uani 1 1 d . . . . .
C6 C 0.0758(2) 0.1841(6) 0.1519(9) 0.0271(12) Uani 1 1 d . . . . .
N1 N 0.35631(16) 0.7022(5) 0.9490(7) 0.0238(10) Uani 1 1 d . . . . .
N2 N 0.37075(19) 0.8442(5) 0.9382(7) 0.0293(11) Uani 1 1 d . . . . .
N3 N 0.41917(19) 0.8440(5) 0.8819(8) 0.0327(12) Uani 1 1 d . . . . .
N4 N 0.43658(18) 0.7065(5) 0.8571(7) 0.0272(11) Uani 1 1 d . . . . .
N5 N 0.35992(17) 0.3711(5) 0.9407(7) 0.0263(10) Uani 1 1 d . . . . .
N6 N 0.38004(17) 0.2295(5) 0.9175(7) 0.0260(10) Uani 1 1 d . . . . .
N7 N 0.46194(18) 0.1450(5) 0.8153(8) 0.0337(12) Uani 1 1 d . . . . .
H7A H 0.454599 0.053107 0.828656 0.040 Uiso 1 1 calc R U . . .
H7B H 0.491992 0.170789 0.775444 0.040 Uiso 1 1 calc R U . . .
N8 N 0.14783(16) 0.6441(5) 0.1312(7) 0.0266(11) Uani 1 1 d . . . . .
N9 N 0.13275(19) 0.7849(5) 0.1474(9) 0.0389(13) Uani 1 1 d . . . . .
N10 N 0.0827(2) 0.7812(5) 0.1735(10) 0.0433(14) Uani 1 1 d . . . . .
N11 N 0.06477(18) 0.6430(5) 0.1756(9) 0.0370(13) Uani 1 1 d . . . . .
N12 N 0.14377(17) 0.3128(5) 0.0901(8) 0.0299(11) Uani 1 1 d . . . . .
N13 N 0.12381(18) 0.1698(5) 0.1003(8) 0.0305(11) Uani 1 1 d . . . . .
N14 N 0.04082(18) 0.0818(6) 0.1867(9) 0.0423(14) Uani 1 1 d . . . . .
H14A H 0.048791 -0.009894 0.176013 0.051 Uiso 1 1 calc R U . . .
H14B H 0.010066 0.106668 0.220050 0.051 Uiso 1 1 calc R U . . .
N15 N 0.29354(17) 0.4515(5) 0.2888(7) 0.0261(10) Uani 1 1 d . . . . .
H15A H 0.277211 0.491742 0.388907 0.039 Uiso 1 1 calc R U . . .
H15B H 0.298059 0.519320 0.196024 0.039 Uiso 1 1 calc R U . . .
H15C H 0.324458 0.417253 0.332151 0.039 Uiso 1 1 calc R U . . .
N16 N 0.26247(18) 0.3316(5) 0.2062(9) 0.0362(13) Uani 1 1 d . . . . .
H16A H 0.274953 0.304826 0.090867 0.054 Uiso 1 1 d R U . . .
H16B H 0.229642 0.361989 0.187544 0.054 Uiso 1 1 d R U . . .
N17 N 0.2462(2) 0.5752(7) 0.6359(10) 0.0516(16) Uani 1 1 d . . . . .
H17A H 0.228986 0.658796 0.610872 0.077 Uiso 1 1 d R U . . .
H17B H 0.276107 0.595138 0.702063 0.077 Uiso 1 1 d R U . . .
N18 N 0.2154(2) 0.4827(6) 0.7513(10) 0.0461(15) Uani 1 1 d . . . . .
H18A H 0.230847 0.395223 0.765354 0.069 Uiso 1 1 calc R U . . .
H18B H 0.184106 0.471245 0.691492 0.069 Uiso 1 1 calc R U . . .
H18C H 0.211890 0.523193 0.869693 0.069 Uiso 1 1 calc R U . . .
O1 O 0.30941(14) 0.6649(4) 0.9982(6) 0.0338(10) Uani 1 1 d . . . . .
O2 O 0.44054(13) 0.3903(4) 0.8378(6) 0.0247(9) Uani 1 1 d . . . . .
O3 O 0.19666(15) 0.6100(5) 0.1069(7) 0.0375(11) Uani 1 1 d . . . . .
O4 O 0.06160(14) 0.3274(4) 0.1742(6) 0.0276(9) 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 1.339(7) . ?
C1 N1 1.346(7) . ?
C1 C2 1.434(7) . ?
C2 N5 1.285(7) . ?
C2 O2 1.361(6) . ?
C3 N6 1.303(7) . ?
C3 N7 1.318(7) . ?
C3 O2 1.359(6) . ?
C4 N8 1.329(7) . ?
C4 N11 1.331(7) . ?
C4 C5 1.444(8) . ?
C5 N12 1.278(7) . ?
C5 O4 1.368(6) . ?
C6 N13 1.301(7) . ?
C6 N14 1.319(7) . ?
C6 O4 1.360(6) . ?
N1 O1 1.307(6) . ?
N1 N2 1.343(6) . ?
N2 N3 1.314(7) . ?
N3 N4 1.339(7) . ?
N5 N6 1.396(7) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 O3 1.307(6) . ?
N8 N9 1.341(7) . ?
N9 N10 1.303(7) . ?
N10 N11 1.336(7) . ?
N12 N13 1.397(7) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
N15 N16 1.447(6) . ?
N15 H15A 0.8900 . ?
N15 H15B 0.8900 . ?
N15 H15C 0.8900 . ?
N16 H16A 0.8900 . ?
N16 H16B 0.8900 . ?
N17 N18 1.411(8) . ?
N17 H17A 0.8900 . ?
N17 H17B 0.8900 . ?
N18 H18A 0.8900 . ?
N18 H18B 0.8900 . ?
N18 H18C 0.8900 . ?

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 108.2(4) . . ?
N4 C1 C2 126.9(5) . . ?
N1 C1 C2 124.9(5) . . ?
N5 C2 O2 113.8(4) . . ?
N5 C2 C1 128.5(5) . . ?
O2 C2 C1 117.7(4) . . ?
N6 C3 N7 129.2(5) . . ?
N6 C3 O2 112.5(4) . . ?
N7 C3 O2 118.4(4) . . ?
N8 C4 N11 108.9(5) . . ?
N8 C4 C5 124.5(5) . . ?
N11 C4 C5 126.5(5) . . ?
N12 C5 O4 113.2(5) . . ?
N12 C5 C4 129.8(5) . . ?
O4 C5 C4 117.0(4) . . ?
N13 C6 N14 129.5(5) . . ?
N13 C6 O4 112.7(5) . . ?
N14 C6 O4 117.8(5) . . ?
O1 N1 N2 121.4(4) . . ?
O1 N1 C1 130.2(4) . . ?
N2 N1 C1 108.4(4) . . ?
N3 N2 N1 106.3(4) . . ?
N2 N3 N4 111.2(4) . . ?
N3 N4 C1 105.9(4) . . ?
C2 N5 N6 105.7(4) . . ?
C3 N6 N5 106.3(4) . . ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O3 N8 C4 130.5(5) . . ?
O3 N8 N9 121.1(4) . . ?
C4 N8 N9 108.3(4) . . ?
N10 N9 N8 106.0(4) . . ?
N9 N10 N11 111.6(5) . . ?
C4 N11 N10 105.2(4) . . ?
C5 N12 N13 106.5(4) . . ?
C6 N13 N12 105.9(4) . . ?
C6 N14 H14A 120.0 . . ?
C6 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N16 N15 H15A 109.5 . . ?
N16 N15 H15B 109.5 . . ?
H15A N15 H15B 109.5 . . ?
N16 N15 H15C 109.5 . . ?
H15A N15 H15C 109.5 . . ?
H15B N15 H15C 109.5 . . ?
N15 N16 H16A 109.4 . . ?
N15 N16 H16B 108.9 . . ?
H16A N16 H16B 109.5 . . ?
N18 N17 H17A 109.1 . . ?
N18 N17 H17B 109.4 . . ?
H17A N17 H17B 109.5 . . ?
N17 N18 H18A 109.5 . . ?
N17 N18 H18B 109.5 . . ?
H18A N18 H18B 109.5 . . ?
N17 N18 H18C 109.5 . . ?
H18A N18 H18C 109.5 . . ?
H18B N18 H18C 109.5 . . ?
C3 O2 C2 101.7(4) . . ?
C6 O4 C5 101.7(4) . . ?

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
N4 C1 C2 N5 177.3(6) . . . . ?
N1 C1 C2 N5 -3.1(10) . . . . ?
N4 C1 C2 O2 -0.8(8) . . . . ?
N1 C1 C2 O2 178.8(5) . . . . ?
N8 C4 C5 N12 -6.8(10) . . . . ?
N11 C4 C5 N12 172.3(6) . . . . ?
N8 C4 C5 O4 174.1(5) . . . . ?
N11 C4 C5 O4 -6.8(9) . . . . ?
N4 C1 N1 O1 178.8(5) . . . . ?
C2 C1 N1 O1 -0.9(9) . . . . ?
N4 C1 N1 N2 -0.4(6) . . . . ?
C2 C1 N1 N2 180.0(5) . . . . ?
O1 N1 N2 N3 -178.8(5) . . . . ?
C1 N1 N2 N3 0.4(6) . . . . ?
N1 N2 N3 N4 -0.4(6) . . . . ?
N2 N3 N4 C1 0.1(6) . . . . ?
N1 C1 N4 N3 0.1(6) . . . . ?
C2 C1 N4 N3 179.8(5) . . . . ?
O2 C2 N5 N6 0.8(6) . . . . ?
C1 C2 N5 N6 -177.4(5) . . . . ?
N7 C3 N6 N5 179.2(6) . . . . ?
O2 C3 N6 N5 0.6(6) . . . . ?
C2 N5 N6 C3 -0.8(6) . . . . ?
N11 C4 N8 O3 178.4(6) . . . . ?
C5 C4 N8 O3 -2.3(10) . . . . ?
N11 C4 N8 N9 -0.3(7) . . . . ?
C5 C4 N8 N9 179.0(5) . . . . ?
O3 N8 N9 N10 -178.8(6) . . . . ?
C4 N8 N9 N10 0.0(7) . . . . ?
N8 N9 N10 N11 0.2(8) . . . . ?
N8 C4 N11 N10 0.4(7) . . . . ?
C5 C4 N11 N10 -178.9(6) . . . . ?
N9 N10 N11 C4 -0.4(8) . . . . ?
O4 C5 N12 N13 -0.9(6) . . . . ?
C4 C5 N12 N13 180.0(6) . . . . ?
N14 C6 N13 N12 -177.9(6) . . . . ?
O4 C6 N13 N12 1.0(7) . . . . ?
C5 N12 N13 C6 0.0(6) . . . . ?
N6 C3 O2 C2 -0.2(5) . . . . ?
N7 C3 O2 C2 -178.9(5) . . . . ?
N5 C2 O2 C3 -0.4(6) . . . . ?
C1 C2 O2 C3 177.9(5) . . . . ?
N13 C6 O4 C5 -1.4(6) . . . . ?
N14 C6 O4 C5 177.6(5) . . . . ?
N12 C5 O4 C6 1.4(6) . . . . ?
C4 C5 O4 C6 -179.3(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
N7 H7A N3 0.86 2.14 2.984(7) 166.6 1_545 yes
N7 H7B N4 0.86 2.10 2.951(6) 170.5 2_646 yes
N14 H14A N10 0.86 2.09 2.934(7) 168.5 1_545 yes
N14 H14B N11 0.86 2.10 2.954(7) 172.6 2_545 yes
N18 H18A N16 0.89 2.25 3.116(7) 163.1 4_566 yes
N18 H18B N9 0.89 2.59 3.051(7) 113.5 4_576 yes
N18 H18B N13 0.89 2.08 2.877(7) 148.4 4_566 yes
N18 H18C O3 0.89 1.84 2.731(8) 173.5 1_556 yes
N17 H17A O3 0.89 2.26 3.129(7) 166.8 4_576 yes
N17 H17A N9 0.89 2.54 3.179(7) 128.9 4_576 yes
N17 H17B O1 0.89 2.24 2.995(8) 142.8 . yes
N16 H16A N5 0.89 2.52 3.160(7) 129.7 1_554 yes
N16 H16B O3 0.89 2.46 3.096(6) 129.1 . yes
N16 H16B N12 0.89 2.32 3.117(6) 149.7 . yes
N15 H15A N17 0.89 2.03 2.915(8) 174.0 . yes
N15 H15B O1 0.89 1.91 2.802(6) 178.7 1_554 yes
N15 H15C N6 0.89 2.02 2.866(6) 159.1 4_565 yes

_refine_diff_density_max         0.794
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_YF_113_a
_database_code_depnum_ccdc_archive 'CCDC 2277160'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-06-27 deposited with the CCDC.	2025-03-13 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         'C3 H3 N7 O2, H2 O'
_chemical_formula_sum            'C3 H5 N7 O3'
_chemical_formula_weight         187.14

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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   7.2861(5)
_cell_length_b                   5.9922(4)
_cell_length_c                   8.2491(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.669(2)
_cell_angle_gamma                90
_cell_volume                     356.93(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2080
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6874
_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            3318
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.821
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             892
_reflns_number_gt                744
_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'
_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+0.1735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         892
_refine_ls_number_parameters     89
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.088
_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 0.3766(3) 0.750000 0.3599(2) 0.0239(5) Uani 1 2 d S T P . .
C2 C 0.3147(3) 0.750000 0.5183(2) 0.0234(5) Uani 1 2 d S T P . .
C3 C 0.1034(3) 0.750000 0.6764(2) 0.0261(5) Uani 1 2 d S T P . .
N1 N 0.5538(2) 0.750000 0.3300(2) 0.0253(4) Uani 1 2 d S T P . .
N2 N 0.5522(3) 0.750000 0.1677(2) 0.0307(5) Uani 1 2 d S T P . .
N3 N 0.3774(3) 0.750000 0.1033(2) 0.0330(5) Uani 1 2 d S T P . .
N4 N 0.2657(3) 0.750000 0.2183(2) 0.0305(5) Uani 1 2 d S T P . .
N5 N 0.4069(3) 0.750000 0.6622(2) 0.0271(4) Uani 1 2 d S T P . .
N6 N 0.2688(3) 0.750000 0.7636(2) 0.0279(4) Uani 1 2 d S T P . .
H6 H 0.292(4) 0.750000 0.876(4) 0.033 Uiso 1 2 d S U P . .
N7 N -0.0602(3) 0.750000 0.7206(2) 0.0353(5) Uani 1 2 d DS T P . .
H7A H -0.153(3) 0.750000 0.651(3) 0.042 Uiso 1 2 d DS U P . .
H7B H -0.077(4) 0.750000 0.821(2) 0.042 Uiso 1 2 d DS U P . .
O1 O 0.1258(2) 0.750000 0.51699(17) 0.0262(4) Uani 1 2 d S T P . .
O2 O 0.7064(2) 0.750000 0.4289(2) 0.0396(5) Uani 1 2 d S T P . .
O3 O 0.9002(3) 0.750000 0.0431(3) 0.1053(15) Uani 1 2 d S T P . .
H3A H 0.988(8) 0.750000 0.111(6) 0.126 Uiso 1 2 d S U P . .
H3B H 0.806(8) 0.750000 0.072(6) 0.126 Uiso 1 2 d S 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 N4 1.329(3) . ?
C1 N1 1.346(3) . ?
C1 C2 1.438(3) . ?
C2 N5 1.283(3) . ?
C2 O1 1.375(2) . ?
C3 N7 1.292(3) . ?
C3 N6 1.319(3) . ?
C3 O1 1.346(2) . ?
N1 O2 1.289(2) . ?
N1 N2 1.337(3) . ?
N2 N3 1.313(3) . ?
N3 N4 1.330(3) . ?
N5 N6 1.392(3) . ?
N6 H6 0.92(3) . ?
N7 H7A 0.828(16) . ?
N7 H7B 0.857(16) . ?
O3 H3A 0.79(5) . ?
O3 H3B 0.76(5) . ?

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 108.90(18) . . ?
N4 C1 C2 124.8(2) . . ?
N1 C1 C2 126.27(19) . . ?
N5 C2 O1 114.00(18) . . ?
N5 C2 C1 130.6(2) . . ?
O1 C2 C1 115.35(18) . . ?
N7 C3 N6 131.0(2) . . ?
N7 C3 O1 120.8(2) . . ?
N6 C3 O1 108.18(19) . . ?
O2 N1 N2 121.70(18) . . ?
O2 N1 C1 130.65(18) . . ?
N2 N1 C1 107.66(17) . . ?
N3 N2 N1 106.47(17) . . ?
N2 N3 N4 111.36(17) . . ?
C1 N4 N3 105.61(18) . . ?
C2 N5 N6 103.02(17) . . ?
C3 N6 N5 110.65(17) . . ?
C3 N6 H6 125.6(17) . . ?
N5 N6 H6 123.7(17) . . ?
C3 N7 H7A 120.0(18) . . ?
C3 N7 H7B 122.2(19) . . ?
H7A N7 H7B 118(2) . . ?
C3 O1 C2 104.14(16) . . ?
H3A O3 H3B 117(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 C2 N5 180.000(1) . . . . ?
N1 C1 C2 N5 0.000(1) . . . . ?
N4 C1 C2 O1 0.000(0) . . . . ?
N1 C1 C2 O1 180.000(0) . . . . ?
N4 C1 N1 O2 180.000(0) . . . . ?
C2 C1 N1 O2 0.000(0) . . . . ?
N4 C1 N1 N2 0.000(0) . . . . ?
C2 C1 N1 N2 180.000(0) . . . . ?
O2 N1 N2 N3 180.000(0) . . . . ?
C1 N1 N2 N3 0.000(0) . . . . ?
N1 N2 N3 N4 0.0 . . . . ?
N1 C1 N4 N3 0.000(0) . . . . ?
C2 C1 N4 N3 180.000(0) . . . . ?
N2 N3 N4 C1 0.000(0) . . . . ?
O1 C2 N5 N6 0.000(1) . . . . ?
C1 C2 N5 N6 180.000(1) . . . . ?
N7 C3 N6 N5 180.000(1) . . . . ?
O1 C3 N6 N5 0.000(1) . . . . ?
C2 N5 N6 C3 0.000(1) . . . . ?
N7 C3 O1 C2 180.000(1) . . . . ?
N6 C3 O1 C2 0.000(1) . . . . ?
N5 C2 O1 C3 0.000(1) . . . . ?
C1 C2 O1 C3 180.000(0) . . . . ?

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 H3A N4 0.79(5) 2.10(6) 2.855(3) 160(5) 1_655 yes
O3 H3B N2 0.76(5) 2.10(5) 2.861(3) 177(5) . yes
N7 H7B O3 0.857(16) 1.858(17) 2.713(3) 177(3) 1_456 yes
N7 H7A O2 0.828(16) 1.974(17) 2.755(3) 157(3) 1_455 yes
N6 H6 N3 0.92(3) 1.90(3) 2.808(3) 172(2) 1_556 yes

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_YF_111_a
_database_code_depnum_ccdc_archive 'CCDC 2268512'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H3 N8 O, H4 N O'
_chemical_formula_sum            'C3 H7 N9 O2'
_chemical_formula_weight         201.18

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                   7.7908(10)
_cell_length_b                   15.457(2)
_cell_length_c                   7.2605(11)
_cell_angle_alpha                90
_cell_angle_beta                 114.635(4)
_cell_angle_gamma                90
_cell_volume                     794.75(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2712
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5872
_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            6393
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.635
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1803
_reflns_number_gt                1335
_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-2018/1 (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)+(0.0551P)²+0.2919P] 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         1803
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.7891(3) 0.19113(12) 0.7681(3) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.8189(3) 0.28360(12) 0.7684(3) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.7707(3) 0.41770(13) 0.7639(3) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.9161(2) 0.13009(10) 0.7825(3) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.8374(2) 0.05239(11) 0.7724(3) 0.0315(4) Uani 1 1 d . . . . .
N3 N 0.6649(2) 0.06635(11) 0.7514(3) 0.0340(5) Uani 1 1 d . . . . .
N4 N 0.6307(2) 0.15175(11) 0.7493(3) 0.0295(4) Uani 1 1 d . . . . .
N5 N 0.6912(2) 0.34230(10) 0.7728(3) 0.0275(4) Uani 1 1 d . . . . .
N6 N 0.9370(2) 0.40254(10) 0.7565(3) 0.0299(4) Uani 1 1 d . . . . .
H6 H 1.012352 0.442110 0.751068 0.036 Uiso 1 1 calc R U . . .
N7 N 0.9706(2) 0.31587(10) 0.7586(3) 0.0296(4) Uani 1 1 d . . . . .
N8 N 0.7020(3) 0.49614(12) 0.7650(3) 0.0461(6) Uani 1 1 d . . . . .
H8A H 0.595071 0.502021 0.771973 0.055 Uiso 1 1 calc R U . . .
H8B H 0.764322 0.541108 0.758715 0.055 Uiso 1 1 calc R U . . .
O1 O 1.09302(19) 0.13903(9) 0.8068(2) 0.0332(4) Uani 1 1 d . . . . .
N9 N 0.2803(3) 0.25620(13) 0.6516(3) 0.0288(4) Uani 1 1 d . . . . .
H9A H 0.362(3) 0.2207(14) 0.634(3) 0.035 Uiso 1 1 d . U . . .
H9B H 0.184(3) 0.2285(14) 0.679(3) 0.035 Uiso 1 1 d . U . . .
H9C H 0.221(3) 0.2950(14) 0.534(4) 0.035 Uiso 1 1 d . U . . .
O2 O 0.3776(2) 0.30862(12) 0.8216(2) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.474(5) 0.3227(19) 0.809(4) 0.066 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 N4 1.331(2) . ?
C1 N1 1.339(2) . ?
C1 C2 1.448(3) . ?
C2 N7 1.312(2) . ?
C2 N5 1.357(2) . ?
C3 N8 1.327(3) . ?
C3 N5 1.334(3) . ?
C3 N6 1.340(3) . ?
N1 O1 1.322(2) . ?
N1 N2 1.336(2) . ?
N2 N3 1.306(2) . ?
N3 N4 1.345(2) . ?
N6 N7 1.364(2) . ?
N6 H6 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 O2 1.405(2) . ?
N9 H9A 0.89(2) . ?
N9 H9B 0.95(2) . ?
N9 H9C 0.99(2) . ?
O2 H2 0.82(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
N4 C1 N1 108.00(16) . . ?
N4 C1 C2 126.35(17) . . ?
N1 C1 C2 125.64(17) . . ?
N7 C2 N5 115.66(17) . . ?
N7 C2 C1 121.52(17) . . ?
N5 C2 C1 122.79(17) . . ?
N8 C3 N5 126.97(19) . . ?
N8 C3 N6 124.02(19) . . ?
N5 C3 N6 109.00(17) . . ?
O1 N1 N2 122.01(15) . . ?
O1 N1 C1 129.19(16) . . ?
N2 N1 C1 108.78(16) . . ?
N3 N2 N1 106.50(16) . . ?
N2 N3 N4 110.65(15) . . ?
C1 N4 N3 106.06(16) . . ?
C3 N5 C2 102.90(16) . . ?
C3 N6 N7 110.82(15) . . ?
C3 N6 H6 124.6 . . ?
N7 N6 H6 124.6 . . ?
C2 N7 N6 101.61(15) . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
O2 N9 H9A 109.0(15) . . ?
O2 N9 H9B 104.9(13) . . ?
H9A N9 H9B 115(2) . . ?
O2 N9 H9C 107.2(13) . . ?
H9A N9 H9C 111(2) . . ?
H9B N9 H9C 109.0(19) . . ?
N9 O2 H2 104(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
N4 C1 C2 N7 -170.1(2) . . . . ?
N1 C1 C2 N7 8.4(3) . . . . ?
N4 C1 C2 N5 8.0(3) . . . . ?
N1 C1 C2 N5 -173.56(19) . . . . ?
N4 C1 N1 O1 -178.61(18) . . . . ?
C2 C1 N1 O1 2.7(3) . . . . ?
N4 C1 N1 N2 0.1(2) . . . . ?
C2 C1 N1 N2 -178.58(17) . . . . ?
O1 N1 N2 N3 179.04(17) . . . . ?
C1 N1 N2 N3 0.2(2) . . . . ?
N1 N2 N3 N4 -0.5(2) . . . . ?
N1 C1 N4 N3 -0.4(2) . . . . ?
C2 C1 N4 N3 178.30(18) . . . . ?
N2 N3 N4 C1 0.5(2) . . . . ?
N8 C3 N5 C2 -179.6(2) . . . . ?
N6 C3 N5 C2 -0.5(2) . . . . ?
N7 C2 N5 C3 0.3(2) . . . . ?
C1 C2 N5 C3 -177.86(18) . . . . ?
N8 C3 N6 N7 179.6(2) . . . . ?
N5 C3 N6 N7 0.5(2) . . . . ?
N5 C2 N7 N6 0.0(2) . . . . ?
C1 C2 N7 N6 178.17(17) . . . . ?
C3 N6 N7 C2 -0.3(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 H6 N2 0.86 2.11 2.967(2) 171.3 2_756 yes
N8 H8B O1 0.86 2.05 2.898(2) 169.4 2_756 yes
N8 H8A N3 0.86 2.20 3.013(2) 157.9 2_656 yes
N9 H9A N4 0.89(2) 2.18(2) 2.991(3) 151(2) . yes
N9 H9A O2 0.89(2) 2.36(2) 2.972(3) 125.7(18) 4_565 yes
N9 H9B N7 0.95(2) 2.39(2) 2.973(3) 118.9(16) 1_455 yes
N9 H9B O1 0.95(2) 1.95(2) 2.837(2) 152.7(19) 1_455 yes
N9 H9C N1 0.99(2) 2.59(2) 3.462(3) 147.8(17) 4_465 yes
N9 H9C O1 0.99(2) 1.84(2) 2.824(2) 175.2(19) 4_465 yes
O2 H2 N5 0.82(3) 1.85(3) 2.662(2) 174(3) . yes

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_NLG_YF_099_a
_database_code_depnum_ccdc_archive 'CCDC 2217973'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-11-07 deposited with the CCDC.	2025-03-13 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         'C3 H2 N7 O2, H4 N'
_chemical_formula_sum            'C3 H6 N8 O2'
_chemical_formula_weight         186.16

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.8698(2)
_cell_length_b                   8.3310(5)
_cell_length_c                   11.6487(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.015(2)
_cell_angle_gamma                90
_cell_volume                     374.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2551
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.19

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6926
_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            3742
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             1548
_reflns_number_gt                1417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.825
_reflns_Friedel_fraction_full    0.866

_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)+(0.0430P)²+0.0194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1548
_refine_ls_number_parameters     130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.108
_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 0.8468(6) 0.1643(3) 0.83504(18) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.6771(6) 0.3915(3) 0.77024(17) 0.0243(5) Uani 1 1 d . . . . .
C3 C 0.5230(6) 0.5487(3) 0.77403(17) 0.0239(5) Uani 1 1 d . . . . .
N1 N 0.9315(5) 0.1718(3) 0.72895(15) 0.0317(5) Uani 1 1 d . . . . .
N2 N 0.8163(5) 0.3226(2) 0.68737(15) 0.0304(5) Uani 1 1 d . . . . .
N3 N 0.5202(4) 0.6568(2) 0.68857(14) 0.0239(4) Uani 1 1 d . . . . .
N4 N 0.3618(6) 0.7898(2) 0.72140(17) 0.0336(5) Uani 1 1 d . . . . .
N5 N 0.2693(6) 0.7603(3) 0.82482(17) 0.0344(5) Uani 1 1 d . . . . .
N6 N 0.3645(5) 0.6116(3) 0.85964(17) 0.0300(5) Uani 1 1 d . . . . .
N7 N 0.9001(6) 0.0491(3) 0.91155(18) 0.0422(6) Uani 1 1 d . . . . .
H7A H 1.005410 -0.037242 0.894046 0.051 Uiso 1 1 calc R U . . .
H7B H 0.829781 0.060041 0.979127 0.051 Uiso 1 1 calc R U . . .
O1 O 0.6847(4) 0.30024(19) 0.86756(12) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.6450(4) 0.6441(2) 0.58744(12) 0.0320(4) Uani 1 1 d . . . . .
N8 N 0.8705(6) 0.9521(3) 0.52978(19) 0.0308(5) Uani 1 1 d . . . . .
H8A H 0.695(8) 1.012(4) 0.497(2) 0.037 Uiso 1 1 d . U . . .
H8B H 0.789(7) 0.844(4) 0.547(2) 0.037 Uiso 1 1 d . U . . .
H8C H 1.021(8) 0.943(4) 0.479(3) 0.037 Uiso 1 1 d . U . . .
H8D H 0.941(7) 1.002(4) 0.600(2) 0.037 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 1.307(3) . ?
C1 N7 1.314(3) . ?
C1 O1 1.364(3) . ?
C2 N2 1.282(3) . ?
C2 O1 1.363(3) . ?
C2 C3 1.441(3) . ?
C3 N6 1.323(3) . ?
C3 N3 1.342(3) . ?
N1 N2 1.405(3) . ?
N3 O2 1.316(2) . ?
N3 N4 1.338(3) . ?
N4 N5 1.310(3) . ?
N5 N6 1.345(3) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 H8A 0.90(3) . ?
N8 H8B 0.98(3) . ?
N8 H8C 0.87(3) . ?
N8 H8D 0.93(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 N7 129.7(2) . . ?
N1 C1 O1 112.5(2) . . ?
N7 C1 O1 117.84(19) . . ?
N2 C2 O1 113.4(2) . . ?
N2 C2 C3 129.2(2) . . ?
O1 C2 C3 117.40(17) . . ?
N6 C3 N3 108.6(2) . . ?
N6 C3 C2 127.1(2) . . ?
N3 C3 C2 124.30(18) . . ?
C1 N1 N2 105.69(19) . . ?
C2 N2 N1 106.41(17) . . ?
O2 N3 N4 122.35(18) . . ?
O2 N3 C3 129.12(18) . . ?
N4 N3 C3 108.53(17) . . ?
N5 N4 N3 106.04(19) . . ?
N4 N5 N6 111.12(19) . . ?
C3 N6 N5 105.7(2) . . ?
C1 N7 H7A 120.0 . . ?
C1 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C2 O1 C1 102.07(16) . . ?
H8A N8 H8B 110(2) . . ?
H8A N8 H8C 106(3) . . ?
H8B N8 H8C 108(3) . . ?
H8A N8 H8D 106(2) . . ?
H8B N8 H8D 108(2) . . ?
H8C N8 H8D 118(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
N2 C2 C3 N6 175.9(3) . . . . ?
O1 C2 C3 N6 -5.1(3) . . . . ?
N2 C2 C3 N3 -4.4(3) . . . . ?
O1 C2 C3 N3 174.7(2) . . . . ?
N7 C1 N1 N2 -179.2(3) . . . . ?
O1 C1 N1 N2 -0.4(3) . . . . ?
O1 C2 N2 N1 -0.1(3) . . . . ?
C3 C2 N2 N1 179.0(2) . . . . ?
C1 N1 N2 C2 0.3(2) . . . . ?
N6 C3 N3 O2 -179.2(2) . . . . ?
C2 C3 N3 O2 1.0(3) . . . . ?
N6 C3 N3 N4 0.7(2) . . . . ?
C2 C3 N3 N4 -179.0(2) . . . . ?
O2 N3 N4 N5 179.45(19) . . . . ?
C3 N3 N4 N5 -0.5(2) . . . . ?
N3 N4 N5 N6 0.1(3) . . . . ?
N3 C3 N6 N5 -0.7(2) . . . . ?
C2 C3 N6 N5 179.1(2) . . . . ?
N4 N5 N6 C3 0.3(3) . . . . ?
N2 C2 O1 C1 -0.1(3) . . . . ?
C3 C2 O1 C1 -179.31(19) . . . . ?
N1 C1 O1 C2 0.3(3) . . . . ?
N7 C1 O1 C2 179.3(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
N7 H7A N5 0.86 2.16 3.017(3) 171.6 1_645 yes
N7 H7B N6 0.86 2.13 2.984(3) 173.9 2_647 yes
N8 H8A N3 0.90(3) 2.55(3) 3.315(3) 143(2) 2_656 yes
N8 H8A O2 0.90(3) 1.92(3) 2.816(3) 173(2) 2_656 yes
N8 H8B N3 0.98(3) 2.56(3) 3.428(3) 148(2) . yes
N8 H8B O2 0.98(3) 1.83(3) 2.810(3) 177(2) . yes
N8 H8C N2 0.87(3) 2.32(3) 3.093(3) 148(3) 2_756 yes
N8 H8C O2 0.87(3) 2.29(3) 2.896(3) 127(3) 2_756 yes
N8 H8D N1 0.93(3) 2.07(3) 2.949(3) 156(2) 1_565 yes

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_YF_110
_database_code_depnum_ccdc_archive 'CCDC 2267698'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2025-03-13 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         'C3 H4 N8 O, H4 N2'
_chemical_formula_sum            'C3 H8 N10 O'
_chemical_formula_weight         200.19

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           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 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'
'-x+1/2, y, -z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x+1, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, z'
'x-1/2, -y, z-1/2'
'x-1/2, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z-1/2'
'x, y+1/2, -z-1/2'

_cell_length_a                   6.5314(4)
_cell_length_b                   25.0039(17)
_cell_length_c                   9.2895(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1517.07(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4665
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.38

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6828
_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            724
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.732
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_full        24.983
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             724
_reflns_number_gt                664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       '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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+20.9846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         724
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.500000 0.3644(2) 0.6761(6) 0.0211(14) Uani 1 2 d S T P . .
C2 C 0.500000 0.3363(2) 0.5394(6) 0.0222(14) Uani 1 2 d S T P . .
C3 C 0.500000 0.3189(2) 0.3188(7) 0.0324(17) Uani 1 2 d S T P . .
N1 N 0.500000 0.41776(19) 0.6949(5) 0.0206(12) Uani 1 2 d S T P . .
N2 N 0.500000 0.4286(2) 0.8363(5) 0.0274(13) Uani 1 2 d S T P . .
N3 N 0.500000 0.3820(2) 0.9029(5) 0.0269(13) Uani 1 2 d S T P . .
N4 N 0.500000 0.3417(2) 0.8064(5) 0.0223(12) Uani 1 2 d S T P . .
N5 N 0.500000 0.36073(19) 0.4081(6) 0.0350(16) Uani 1 2 d S T P . .
N6 N 0.500000 0.28376(19) 0.5363(5) 0.0272(13) Uani 1 2 d S T P . .
N7 N 0.500000 0.27314(19) 0.3908(5) 0.0281(14) Uani 1 2 d S T P . .
H7 H 0.500000 0.241787 0.352753 0.034 Uiso 1 2 calc R U P . .
N8 N 0.500000 0.3208(2) 0.1747(6) 0.062(3) Uani 1 2 d S T P . .
H8A H 0.500000 0.291582 0.125656 0.075 Uiso 1 2 calc R U P . .
H8B H 0.500000 0.351120 0.131163 0.075 Uiso 1 2 calc R U P . .
N9 N 0.7289(7) 0.54432(14) 0.8269(4) 0.0364(11) Uani 1 1 d . . . . .
H9A H 0.784625 0.515350 0.866437 0.055 Uiso 1 1 d R U . . .
H9B H 0.783488 0.573475 0.866287 0.055 Uiso 1 1 d R U . . .
O1 O 0.500000 0.45605(16) 0.5974(5) 0.0282(12) Uani 1 2 d S T P . .
H1 H 0.582786 0.479175 0.620383 0.042 Uiso 0.5 1 calc R 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 N4 1.337(7) . ?
C1 N1 1.346(7) . ?
C1 C2 1.450(8) . ?
C2 N6 1.315(8) . ?
C2 N5 1.364(8) . ?
C3 N7 1.326(8) . ?
C3 N5 1.334(8) . ?
C3 N8 1.340(8) . ?
N1 O1 1.318(6) . ?
N1 N2 1.341(7) . ?
N2 N3 1.321(7) . ?
N3 N4 1.348(7) . ?
N6 N7 1.377(7) . ?
N7 H7 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 N9 1.455(7) 3_656 ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
O1 H1 0.8200 . ?
O1 H1 0.82(9) 10_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
N4 C1 N1 107.7(5) . . ?
N4 C1 C2 126.0(5) . . ?
N1 C1 C2 126.4(5) . . ?
N6 C2 N5 115.3(5) . . ?
N6 C2 C1 120.2(5) . . ?
N5 C2 C1 124.5(5) . . ?
N7 C3 N5 111.3(5) . . ?
N7 C3 N8 122.3(6) . . ?
N5 C3 N8 126.4(6) . . ?
O1 N1 N2 121.7(5) . . ?
O1 N1 C1 129.1(5) . . ?
N2 N1 C1 109.2(5) . . ?
N3 N2 N1 106.2(5) . . ?
N2 N3 N4 110.4(5) . . ?
C1 N4 N3 106.5(5) . . ?
C3 N5 C2 101.8(5) . . ?
C2 N6 N7 102.4(5) . . ?
C3 N7 N6 109.2(5) . . ?
C3 N7 H7 125.4 . . ?
N6 N7 H7 125.4 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N9 N9 H9A 109.1 3_656 . ?
N9 N9 H9B 109.1 3_656 . ?
H9A N9 H9B 109.5 . . ?
N1 O1 H1 109.5 . . ?
N1 O1 H1 109(2) . 10_655 ?
H1 O1 H1 82.5 . 10_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
N4 C1 C2 N6 0.000(3) . . . . ?
N1 C1 C2 N6 180.000(2) . . . . ?
N4 C1 C2 N5 180.000(2) . . . . ?
N1 C1 C2 N5 0.000(3) . . . . ?
N4 C1 N1 O1 180.000(2) . . . . ?
C2 C1 N1 O1 0.000(3) . . . . ?
N4 C1 N1 N2 0.000(2) . . . . ?
C2 C1 N1 N2 180.000(2) . . . . ?
O1 N1 N2 N3 180.000(2) . . . . ?
C1 N1 N2 N3 0.000(2) . . . . ?
N1 N2 N3 N4 0.000(2) . . . . ?
N1 C1 N4 N3 0.000(2) . . . . ?
C2 C1 N4 N3 180.000(2) . . . . ?
N2 N3 N4 C1 0.000(2) . . . . ?
N7 C3 N5 C2 0.000(2) . . . . ?
N8 C3 N5 C2 180.000(2) . . . . ?
N6 C2 N5 C3 0.000(2) . . . . ?
C1 C2 N5 C3 180.000(2) . . . . ?
N5 C2 N6 N7 0.000(2) . . . . ?
C1 C2 N6 N7 180.000(2) . . . . ?
N5 C3 N7 N6 0.000(2) . . . . ?
N8 C3 N7 N6 180.000(2) . . . . ?
C2 N6 N7 C3 0.000(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
N7 H7 N4 0.86 2.13 2.976(7) 167.4 15 yes
N8 H8A N6 0.86 2.06 2.912(8) 171.8 15 yes
N8 H8B N3 0.86 2.26 2.952(8) 138.0 1_554 yes
N9 H9A O1 0.89 2.07 2.916(5) 158.0 3_656 yes
N9 H9B N5 0.89 2.20 3.056(5) 160.2 11_666 yes
O1 H1 N9 0.82 2.69 3.414(5) 147.8 . yes
O1 H1 N9 0.82 2.10 2.916(5) 173.9 3_656 yes

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_YF_109_a
_database_code_depnum_ccdc_archive 'CCDC 2265664'
loop_
_audit_author_name
_audit_author_address
'feng yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-05-26 deposited with the CCDC.	2025-03-13 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         ' C3 H3 N8 O, H2 O, H4 N'
_chemical_formula_sum            'C3 H9 N9 O2'
_chemical_formula_weight         203.19

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                   9.2271(12)
_cell_length_b                   14.2917(17)
_cell_length_c                   6.4999(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.078(4)
_cell_angle_gamma                90
_cell_volume                     841.18(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3973
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.43

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6704
_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            8363
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1940
_reflns_number_gt                1472
_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)+(0.0945P)²+0.2133P] 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         1940
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.58579(19) 0.52027(12) 0.2689(3) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.45580(19) 0.58047(12) 0.2384(3) 0.0234(4) Uani 1 1 d . . . . .
C3 C 0.2341(2) 0.61771(13) 0.1885(3) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.72729(17) 0.54603(11) 0.2915(2) 0.0256(4) Uani 1 1 d . . . . .
N2 N 0.81223(19) 0.46959(11) 0.3139(3) 0.0333(4) Uani 1 1 d . . . . .
N3 N 0.72131(18) 0.39832(12) 0.3040(3) 0.0332(4) Uani 1 1 d . . . . .
N4 N 0.57996(17) 0.42729(11) 0.2754(2) 0.0288(4) Uani 1 1 d . . . . .
N5 N 0.46258(17) 0.67224(12) 0.2348(3) 0.0314(4) Uani 1 1 d . . . . .
N6 N 0.31533(19) 0.69526(13) 0.2021(3) 0.0335(4) Uani 1 1 d . . . . .
H6 H 0.290(2) 0.752(2) 0.196(3) 0.035(6) Uiso 1 1 d . . . . .
N7 N 0.31877(17) 0.54224(11) 0.2107(2) 0.0282(4) Uani 1 1 d . . . . .
N8 N 0.08369(19) 0.61785(13) 0.1498(3) 0.0445(5) Uani 1 1 d . . . . .
H8A H 0.036087 0.565778 0.137818 0.053 Uiso 1 1 calc R U . . .
H8B H 0.036319 0.670004 0.137269 0.053 Uiso 1 1 calc R U . . .
O1 O 0.78348(16) 0.63087(9) 0.2890(2) 0.0361(4) Uani 1 1 d . . . . .
N9 N 0.6975(2) 0.82254(15) 0.3597(3) 0.0385(5) Uani 1 1 d . . . . .
H9A H 0.778(3) 0.8273(19) 0.305(4) 0.049(7) Uiso 1 1 d . . . . .
H9B H 0.727(3) 0.8332(19) 0.514(5) 0.057(7) Uiso 1 1 d . . . . .
H9C H 0.649(5) 0.863(3) 0.289(6) 0.104(15) Uiso 1 1 d . . . . .
H9D H 0.647(4) 0.766(3) 0.333(6) 0.091(11) Uiso 1 1 d . . . . .
O2 O 0.9504(2) 0.68535(13) 0.6597(3) 0.0473(5) Uani 1 1 d . . . . .
H2A H 0.919(3) 0.666(2) 0.524(5) 0.064(8) Uiso 1 1 d . . . . .
H2B H 1.017(4) 0.644(3) 0.693(6) 0.095(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.331(2) . ?
C1 N1 1.337(2) . ?
C1 C2 1.458(2) . ?
C2 N5 1.313(3) . ?
C2 N7 1.357(2) . ?
C3 N7 1.323(2) . ?
C3 N6 1.332(3) . ?
C3 N8 1.362(3) . ?
N1 O1 1.320(2) . ?
N1 N2 1.336(2) . ?
N2 N3 1.313(2) . ?
N3 N4 1.347(2) . ?
N5 N6 1.374(2) . ?
N6 H6 0.84(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 H9A 0.89(3) . ?
N9 H9B 1.00(3) . ?
N9 H9C 0.81(4) . ?
N9 H9D 0.93(4) . ?
O2 H2A 0.92(3) . ?
O2 H2B 0.85(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 C1 N1 108.42(15) . . ?
N4 C1 C2 123.79(16) . . ?
N1 C1 C2 127.79(16) . . ?
N5 C2 N7 116.48(15) . . ?
N5 C2 C1 123.42(16) . . ?
N7 C2 C1 120.10(16) . . ?
N7 C3 N6 110.97(17) . . ?
N7 C3 N8 125.50(17) . . ?
N6 C3 N8 123.50(18) . . ?
O1 N1 N2 121.92(15) . . ?
O1 N1 C1 128.98(15) . . ?
N2 N1 C1 109.08(15) . . ?
N3 N2 N1 105.84(16) . . ?
N2 N3 N4 111.16(15) . . ?
C1 N4 N3 105.50(15) . . ?
C2 N5 N6 101.12(14) . . ?
C3 N6 N5 109.78(17) . . ?
C3 N6 H6 130.3(16) . . ?
N5 N6 H6 119.9(15) . . ?
C3 N7 C2 101.65(15) . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
H9A N9 H9B 108(2) . . ?
H9A N9 H9C 97(3) . . ?
H9B N9 H9C 118(3) . . ?
H9A N9 H9D 115(3) . . ?
H9B N9 H9D 111(3) . . ?
H9C N9 H9D 108(4) . . ?
H2A O2 H2B 96(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
N4 C1 C2 N5 179.15(17) . . . . ?
N1 C1 C2 N5 -2.0(3) . . . . ?
N4 C1 C2 N7 -1.2(3) . . . . ?
N1 C1 C2 N7 177.66(17) . . . . ?
N4 C1 N1 O1 178.02(16) . . . . ?
C2 C1 N1 O1 -1.0(3) . . . . ?
N4 C1 N1 N2 -0.4(2) . . . . ?
C2 C1 N1 N2 -179.45(17) . . . . ?
O1 N1 N2 N3 -178.40(15) . . . . ?
C1 N1 N2 N3 0.2(2) . . . . ?
N1 N2 N3 N4 0.1(2) . . . . ?
N1 C1 N4 N3 0.48(19) . . . . ?
C2 C1 N4 N3 179.56(16) . . . . ?
N2 N3 N4 C1 -0.4(2) . . . . ?
N7 C2 N5 N6 0.2(2) . . . . ?
C1 C2 N5 N6 179.82(17) . . . . ?
N7 C3 N6 N5 0.1(2) . . . . ?
N8 C3 N6 N5 -177.87(19) . . . . ?
C2 N5 N6 C3 -0.2(2) . . . . ?
N6 C3 N7 C2 0.0(2) . . . . ?
N8 C3 N7 C2 177.95(19) . . . . ?
N5 C2 N7 C3 -0.1(2) . . . . ?
C1 C2 N7 C3 -179.77(16) . . . . ?

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 H6 N3 0.84(3) 2.10(3) 2.921(3) 167(2) 2_655 yes
N8 H8B O2 0.86 2.23 3.075(3) 168.1 4_475 yes
N9 H9A O2 0.89(3) 2.00(3) 2.884(3) 170(2) 4_575 yes
N9 H9B N1 1.00(3) 2.50(3) 3.344(3) 142(2) 4_576 yes
N9 H9B O1 1.00(3) 1.84(3) 2.830(3) 172(2) 4_576 yes
N9 H9C N4 0.81(4) 2.27(4) 2.950(3) 141(4) 2_655 yes
N9 H9C N7 0.81(4) 2.58(4) 3.172(3) 130(3) 2_655 yes
N9 H9D N5 0.93(4) 2.17(4) 3.049(3) 158(3) . yes
N9 H9D O1 0.93(4) 2.35(4) 2.913(3) 119(3) . yes
O2 H2A N1 0.92(3) 2.70(3) 3.470(2) 141(2) . yes
O2 H2A O1 0.92(3) 1.85(3) 2.713(2) 156(3) . yes
O2 H2B N2 0.85(4) 2.27(4) 3.096(2) 164(4) 3_766 yes
O2 H2B N3 0.85(4) 2.48(4) 3.222(2) 146(4) 3_766 yes

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.064

