# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_RT
_database_code_depnum_ccdc_archive 'CCDC 1961357'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0700(12)
_cell_length_b                   9.7833(16)
_cell_length_c                   15.443(2)
_cell_angle_alpha                101.117(3)
_cell_angle_beta                 100.009(2)
_cell_angle_gamma                96.887(2)
_cell_volume                     1019.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6356
_cell_measurement_theta_min      1.37
_cell_measurement_theta_max      25.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            6356
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3495
_reflns_number_gt                3030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3495
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2674(2) 0.27080(14) 1.00424(8) 0.0185(3) Uani 1 1 d . . .
N2 N 0.1846(2) 0.51590(14) 0.94699(9) 0.0184(3) Uani 1 1 d . . .
N3 N 0.1060(2) 1.04158(14) 0.62300(9) 0.0178(3) Uani 1 1 d . . .
H3A H 0.0571 1.0802 0.5806 0.021 Uiso 1 1 calc R . .
H3B H 0.1280 1.0871 0.6782 0.021 Uiso 1 1 calc R . .
N4 N 0.2262(2) 0.85604(13) 0.67333(8) 0.0150(3) Uani 1 1 d . . .
H4 H 0.2495 0.9047 0.7278 0.018 Uiso 1 1 calc R . .
N5 N 0.3433(2) 0.67187(14) 0.72544(9) 0.0204(3) Uani 1 1 d . . .
H5A H 0.3726 0.5881 0.7172 0.025 Uiso 1 1 calc R . .
H5B H 0.3633 0.7232 0.7790 0.025 Uiso 1 1 calc R . .
N6 N 0.2350(2) 0.64530(13) 0.57249(8) 0.0154(3) Uani 1 1 d . . .
N7 N 0.1324(2) 0.63561(14) 0.42243(8) 0.0194(3) Uani 1 1 d . . .
H7A H 0.0865 0.6720 0.3784 0.023 Uiso 1 1 calc R . .
H7B H 0.1600 0.5515 0.4120 0.023 Uiso 1 1 calc R . .
N8 N 0.1141(2) 0.84075(13) 0.51860(8) 0.0153(3) Uani 1 1 d . . .
N9 N 0.3584(2) 0.36686(14) 0.53571(9) 0.0205(3) Uani 1 1 d . . .
H9A H 0.3243 0.4487 0.5379 0.025 Uiso 1 1 calc R . .
H9B H 0.4117 0.3443 0.5843 0.025 Uiso 1 1 calc R . .
N10 N 0.3864(2) 0.14839(13) 0.45913(8) 0.0155(3) Uani 1 1 d . . .
N11 N 0.2440(2) 0.31878(13) 0.38383(8) 0.0161(3) Uani 1 1 d . . .
N12 N 0.1276(2) 0.25087(14) 0.23015(8) 0.0185(3) Uani 1 1 d . . .
H12A H 0.0922 0.3318 0.2294 0.022 Uiso 1 1 calc R . .
H12B H 0.1081 0.1878 0.1810 0.022 Uiso 1 1 calc R . .
N13 N 0.2646(2) 0.09294(13) 0.30309(8) 0.0154(3) Uani 1 1 d . . .
H13 H 0.2431 0.0330 0.2524 0.019 Uiso 1 1 calc R . .
N14 N 0.4020(2) -0.06882(13) 0.37365(9) 0.0182(3) Uani 1 1 d . . .
H14A H 0.4583 -0.0933 0.4210 0.022 Uiso 1 1 calc R . .
H14B H 0.3787 -0.1268 0.3221 0.022 Uiso 1 1 calc R . .
C1 C 0.0072(3) 0.37913(16) 0.79840(10) 0.0186(4) Uani 1 1 d . . .
C2 C 0.0853(2) 0.11828(16) 0.86513(9) 0.0145(3) Uani 1 1 d . . .
C3 C 0.1639(2) 0.26548(16) 0.92155(10) 0.0148(3) Uani 1 1 d . . .
C4 C 0.1238(2) 0.38755(16) 0.89243(10) 0.0150(3) Uani 1 1 d . . .
C5 C 0.2858(3) 0.52013(17) 1.02924(11) 0.0209(4) Uani 1 1 d . . .
H5 H 0.3299 0.6071 1.0689 0.025 Uiso 1 1 calc R . .
C6 C 0.3271(3) 0.39902(18) 1.05709(11) 0.0207(4) Uani 1 1 d . . .
H6 H 0.3991 0.4073 1.1148 0.025 Uiso 1 1 calc R . .
C7 C 0.2116(2) 0.22367(16) 0.30653(10) 0.0145(3) Uani 1 1 d . . .
C8 C 0.3290(2) 0.27602(16) 0.45791(10) 0.0147(3) Uani 1 1 d . . .
C9 C 0.3514(2) 0.05765(16) 0.38006(10) 0.0140(3) Uani 1 1 d . . .
C10 C 0.1602(2) 0.70875(16) 0.50605(10) 0.0144(3) Uani 1 1 d . . .
C11 C 0.1471(2) 0.91266(16) 0.60345(10) 0.0146(3) Uani 1 1 d . . .
C12 C 0.2677(2) 0.72152(16) 0.65588(10) 0.0140(3) Uani 1 1 d . . .
O1 O 0.5600(2) 0.17688(13) 0.81644(8) 0.0254(3) Uani 1 1 d . . .
H1A H 0.454(4) 0.133(2) 0.8295(14) 0.038 Uiso 1 1 d . . .
H1B H 0.663(4) 0.142(2) 0.8456(14) 0.038 Uiso 1 1 d . . .
O2 O 0.19659(11) 0.05335(8) 0.82414(5) 0.0188(3) Uani 1 1 d G . .
O3 O -0.08747(11) 0.07150(7) 0.86738(6) 0.0230(3) Uani 1 1 d G . .
O4 O 0.01006(10) 0.27215(7) 0.74025(4) 0.0382(4) Uani 1 1 d G . .
O5 O -0.08482(12) 0.47727(6) 0.78695(6) 0.0261(3) Uani 1 1 d G . .
O6 O -0.48184(11) 0.40432(9) 0.72476(7) 0.0275(3) Uani 1 1 d G . .
H6A H -0.5106 0.3432 0.7546 0.041 Uiso 1 1 d G . .
H6B H -0.3597 0.4319 0.7375 0.041 Uiso 1 1 d G . .
O7 O 0.1577(2) 0.81694(13) 0.94786(8) 0.0290(3) Uani 1 1 d G . .
H7C H 0.1463 0.8538 1.0010 0.043 Uiso 1 1 d G . .
H7D H 0.1478 0.7279 0.9417 0.043 Uiso 1 1 d G . .
O8 O 0.4976(2) 0.88422(14) 0.88487(8) 0.0272(3) Uani 1 1 d G . .
H8A H 0.5883 0.8585 0.9190 0.041 Uiso 1 1 d G . .
H8B H 0.3976 0.8842 0.9085 0.041 Uiso 1 1 d G . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.333(2) . ?
N1 C3 1.345(2) . ?
N2 C5 1.336(2) . ?
N2 C4 1.345(2) . ?
N3 C11 1.318(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C12 1.369(2) . ?
N4 C11 1.371(2) . ?
N4 H4 0.8600 . ?
N5 C12 1.319(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C12 1.324(2) . ?
N6 C10 1.361(2) . ?
N7 C10 1.319(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C11 1.329(2) . ?
N8 C10 1.356(2) . ?
N9 C8 1.317(2) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C9 1.328(2) . ?
N10 C8 1.361(2) . ?
N11 C7 1.330(2) . ?
N11 C8 1.360(2) . ?
N12 C7 1.315(2) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C9 1.366(2) . ?
N13 C7 1.369(2) . ?
N13 H13 0.8600 . ?
N14 C9 1.319(2) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
C1 O4 1.2455(17) . ?
C1 O5 1.2458(17) . ?
C1 C4 1.522(2) . ?
C2 O2 1.2496(18) . ?
C2 O3 1.2606(19) . ?
C2 C3 1.516(2) . ?
C3 C4 1.398(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O1 H1A 0.89(2) . ?
O1 H1B 0.92(2) . ?
O6 H6A 0.8488 . ?
O6 H6B 0.8499 . ?
O7 H7C 0.8518 . ?
O7 H7D 0.8503 . ?
O8 H8A 0.8509 . ?
O8 H8B 0.8503 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 116.12(14) . . ?
C5 N2 C4 116.67(14) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C12 N4 C11 119.57(13) . . ?
C12 N4 H4 120.2 . . ?
C11 N4 H4 120.2 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C12 N6 C10 116.27(13) . . ?
C10 N7 H7A 120.0 . . ?
C10 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C11 N8 C10 116.07(13) . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C9 N10 C8 115.83(13) . . ?
C7 N11 C8 115.51(13) . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C9 N13 C7 120.04(13) . . ?
C9 N13 H13 120.0 . . ?
C7 N13 H13 120.0 . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
O4 C1 O5 126.07(14) . . ?
O4 C1 C4 116.30(13) . . ?
O5 C1 C4 117.61(13) . . ?
O2 C2 O3 126.32(14) . . ?
O2 C2 C3 118.29(14) . . ?
O3 C2 C3 115.33(13) . . ?
N1 C3 C4 121.86(14) . . ?
N1 C3 C2 115.17(13) . . ?
C4 C3 C2 122.88(13) . . ?
N2 C4 C3 121.07(14) . . ?
N2 C4 C1 117.94(14) . . ?
C3 C4 C1 120.99(14) . . ?
N2 C5 C6 121.89(15) . . ?
N2 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
N1 C6 C5 122.39(15) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N12 C7 N11 121.60(14) . . ?
N12 C7 N13 117.09(13) . . ?
N11 C7 N13 121.31(14) . . ?
N9 C8 N11 116.83(14) . . ?
N9 C8 N10 117.02(14) . . ?
N11 C8 N10 126.15(13) . . ?
N14 C9 N10 120.75(14) . . ?
N14 C9 N13 118.11(13) . . ?
N10 C9 N13 121.14(14) . . ?
N7 C10 N8 117.51(14) . . ?
N7 C10 N6 116.94(14) . . ?
N8 C10 N6 125.56(14) . . ?
N3 C11 N8 120.87(14) . . ?
N3 C11 N4 117.85(14) . . ?
N8 C11 N4 121.28(14) . . ?
N5 C12 N6 121.56(14) . . ?
N5 C12 N4 117.21(14) . . ?
N6 C12 N4 121.22(13) . . ?
H1A O1 H1B 105.5(19) . . ?
H6A O6 H6B 109.5 . . ?
H7C O7 H7D 109.3 . . ?
H8A O8 H8B 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_H-110
_database_code_depnum_ccdc_archive 'CCDC 1961359'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1004(10)
_cell_length_b                   9.7553(13)
_cell_length_c                   15.4226(18)
_cell_angle_alpha                101.355(10)
_cell_angle_beta                 100.201(11)
_cell_angle_gamma                96.398(11)
_cell_volume                     1018.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13211
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            13211
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.1736
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         29.47
_reflns_number_total             4686
_reflns_number_gt                2027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0817P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4686
_refine_ls_number_parameters     320
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1929
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.643
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.2644(8) 0.2699(6) 1.0027(4) 0.0328(14) Uani 1 1 d . . .
N2 N 1.1835(8) 0.5150(6) 0.9457(4) 0.0342(15) Uani 1 1 d . . .
N3 N 0.4002(8) -0.0681(6) 0.3739(4) 0.0323(14) Uani 1 1 d . . .
H3A H 0.4579 -0.0927 0.4211 0.039 Uiso 1 1 calc R . .
H3B H 0.3752 -0.1264 0.3222 0.039 Uiso 1 1 calc R . .
N4 N 0.2637(7) 0.0950(6) 0.3047(3) 0.0266(13) Uani 1 1 d . . .
H4 H 0.2408 0.0348 0.2538 0.032 Uiso 1 1 calc R . .
N5 N 0.1284(8) 0.2536(6) 0.2322(4) 0.0340(15) Uani 1 1 d . . .
H5A H 0.0923 0.3348 0.2318 0.041 Uiso 1 1 calc R . .
H5B H 0.1090 0.1904 0.1828 0.041 Uiso 1 1 calc R . .
N6 N 0.2443(8) 0.3203(6) 0.3847(3) 0.0262(13) Uani 1 1 d . . .
N7 N 0.3604(8) 0.3674(6) 0.5361(4) 0.0351(15) Uani 1 1 d . . .
H7A H 0.4132 0.3445 0.5848 0.042 Uiso 1 1 calc R . .
H7B H 0.3267 0.4499 0.5385 0.042 Uiso 1 1 calc R . .
N8 N 0.3870(7) 0.1494(6) 0.4592(3) 0.0264(13) Uani 1 1 d . . .
N9 N 0.8946(8) -0.0418(6) 0.3773(4) 0.0317(14) Uani 1 1 d . . .
H9A H 0.9438 -0.0797 0.4201 0.038 Uiso 1 1 calc R . .
H9B H 0.8726 -0.0883 0.3221 0.038 Uiso 1 1 calc R . .
N10 N 0.7756(8) 0.1440(6) 0.3266(4) 0.0268(13) Uani 1 1 d . . .
H10 H 0.7540 0.0955 0.2719 0.032 Uiso 1 1 calc R . .
N11 N 0.8862(7) 0.1596(6) 0.4806(3) 0.0259(13) Uani 1 1 d . . .
N12 N 0.8689(8) 0.3657(6) 0.5763(4) 0.0338(15) Uani 1 1 d . . .
H12A H 0.8409 0.4502 0.5868 0.041 Uiso 1 1 calc R . .
H12B H 0.9167 0.3298 0.6204 0.041 Uiso 1 1 calc R . .
N13 N 0.7633(7) 0.3539(6) 0.4266(3) 0.0244(13) Uani 1 1 d . . .
N14 N 0.6574(8) 0.3268(6) 0.2751(4) 0.0349(15) Uani 1 1 d . . .
H14A H 0.6270 0.4107 0.2834 0.042 Uiso 1 1 calc R . .
H14B H 0.6382 0.2752 0.2214 0.042 Uiso 1 1 calc R . .
C1 C 1.0101(11) 0.3802(8) 0.7969(5) 0.0335(17) Uani 1 1 d . . .
C2 C 1.0866(11) 0.1182(7) 0.8635(4) 0.0289(16) Uani 1 1 d . . .
C3 C 1.1632(9) 0.2648(7) 0.9202(4) 0.0272(16) Uani 1 1 d . . .
C4 C 1.1231(9) 0.3871(7) 0.8909(4) 0.0268(16) Uani 1 1 d . . .
C5 C 1.3236(11) 0.3982(8) 1.0549(5) 0.0380(19) Uani 1 1 d . . .
H5 H 1.3959 0.4069 1.1128 0.046 Uiso 1 1 calc R . .
C6 C 1.2826(10) 0.5178(8) 1.0272(5) 0.0378(19) Uani 1 1 d . . .
H6 H 1.3261 0.6049 1.0672 0.045 Uiso 1 1 calc R . .
C7 C 0.8388(9) 0.2918(7) 0.4931(4) 0.0244(15) Uani 1 1 d . . .
C8 C 0.8530(9) 0.0874(7) 0.3961(4) 0.0239(15) Uani 1 1 d . . .
C9 C 0.7325(9) 0.2779(7) 0.3442(4) 0.0256(15) Uani 1 1 d . . .
C10 C 0.3314(9) 0.2774(7) 0.4589(4) 0.0249(15) Uani 1 1 d . . .
C11 C 0.3501(9) 0.0590(7) 0.3809(4) 0.0235(15) Uani 1 1 d . . .
C12 C 0.2132(9) 0.2261(7) 0.3086(4) 0.0241(15) Uani 1 1 d . . .
O1 O 0.5180(11) 0.4047(7) 0.7247(4) 0.0522(17) Uani 1 1 d . . .
H1A H 0.497(17) 0.389(13) 0.758(8) 0.078 Uiso 1 1 d . . .
H1B H 0.653(14) 0.441(10) 0.732(6) 0.078 Uiso 1 1 d . . .
O2 O 0.9172(7) 0.0704(5) 0.8641(3) 0.0438(14) Uani 1 1 d . . .
O3 O 1.1989(7) 0.0539(5) 0.8233(3) 0.0341(12) Uani 1 1 d . . .
O4 O 0.9163(8) 0.4764(5) 0.7860(3) 0.0470(14) Uani 1 1 d . . .
O5 O 1.0166(10) 0.2763(6) 0.7390(3) 0.069(2) Uani 1 1 d . . .
O6 O 0.4385(9) -0.1772(6) 0.1831(4) 0.0460(15) Uani 1 1 d . . .
H6A H 0.546(13) -0.131(10) 0.172(6) 0.069 Uiso 1 1 d . . .
H6B H 0.342(13) -0.163(10) 0.147(6) 0.069 Uiso 1 1 d . . .
O7 O 0.8503(9) 0.1859(7) 0.0506(4) 0.0655(18) Uani 1 1 d D . .
H7C H 0.8174 0.2329 0.0989 0.079 Uiso 1 1 d RD . .
H7D H 0.7340 0.1101 0.0099 0.079 Uiso 1 1 d RD . .
O8 O 0.4947(8) 0.1148(6) 0.1157(4) 0.0574(17) Uani 1 1 d D . .
H8A H 0.3927 0.1292 0.0602 0.069 Uiso 1 1 d RD . .
H8B H 0.5351 0.0926 0.0665 0.04(2) Uiso 1 1 d RD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.326(9) . ?
N1 C3 1.334(8) . ?
N2 C6 1.320(9) . ?
N2 C4 1.339(9) . ?
N3 C11 1.317(8) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C11 1.354(8) . ?
N4 C12 1.360(8) . ?
N4 H4 0.8600 . ?
N5 C12 1.316(8) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C12 1.307(8) . ?
N6 C10 1.365(8) . ?
N7 C10 1.301(8) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C11 1.313(8) . ?
N8 C10 1.351(8) . ?
N9 C8 1.315(8) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C9 1.362(8) . ?
N10 C8 1.360(8) . ?
N10 H10 0.8600 . ?
N11 C8 1.320(8) . ?
N11 C7 1.355(8) . ?
N12 C7 1.310(8) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C9 1.307(8) . ?
N13 C7 1.353(8) . ?
N14 C9 1.304(8) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
C1 O5 1.223(8) . ?
C1 O4 1.231(8) . ?
C1 C4 1.512(9) . ?
C2 O3 1.244(8) . ?
C2 O2 1.244(8) . ?
C2 C3 1.508(10) . ?
C3 C4 1.397(9) . ?
C5 C6 1.363(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O1 H1A 0.60(10) . ?
O1 H1B 0.96(10) . ?
O6 H6A 0.90(9) . ?
O6 H6B 0.84(9) . ?
O7 H7C 0.8787 . ?
O7 H7D 1.0587 . ?
O8 H8A 1.0611 . ?
O8 H8B 0.8551 . ?

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
C5 N1 C3 115.7(6) . . ?
C6 N2 C4 116.4(6) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 C12 120.1(5) . . ?
C11 N4 H4 119.9 . . ?
C12 N4 H4 119.9 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C12 N6 C10 115.2(6) . . ?
C10 N7 H7A 120.0 . . ?
C10 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C11 N8 C10 116.2(6) . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C9 N10 C8 119.5(6) . . ?
C9 N10 H10 120.3 . . ?
C8 N10 H10 120.3 . . ?
C8 N11 C7 116.0(5) . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C9 N13 C7 116.3(6) . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
O5 C1 O4 126.0(7) . . ?
O5 C1 C4 116.3(6) . . ?
O4 C1 C4 117.7(6) . . ?
O3 C2 O2 125.8(7) . . ?
O3 C2 C3 117.9(6) . . ?
O2 C2 C3 116.2(6) . . ?
N1 C3 C4 122.0(6) . . ?
N1 C3 C2 115.2(6) . . ?
C4 C3 C2 122.7(6) . . ?
N2 C4 C3 120.7(6) . . ?
N2 C4 C1 117.7(6) . . ?
C3 C4 C1 121.6(6) . . ?
N1 C5 C6 122.6(7) . . ?
N1 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
N2 C6 C5 122.6(7) . . ?
N2 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
N12 C7 N13 117.3(6) . . ?
N12 C7 N11 117.4(6) . . ?
N13 C7 N11 125.3(6) . . ?
N9 C8 N11 120.4(6) . . ?
N9 C8 N10 118.3(6) . . ?
N11 C8 N10 121.3(6) . . ?
N14 C9 N13 121.3(6) . . ?
N14 C9 N10 117.1(6) . . ?
N13 C9 N10 121.6(6) . . ?
N7 C10 N8 117.5(6) . . ?
N7 C10 N6 116.8(6) . . ?
N8 C10 N6 125.7(6) . . ?
N8 C11 N3 120.8(6) . . ?
N8 C11 N4 120.9(6) . . ?
N3 C11 N4 118.2(6) . . ?
N6 C12 N5 121.3(6) . . ?
N6 C12 N4 121.8(6) . . ?
N5 C12 N4 116.9(6) . . ?
H1A O1 H1B 114(10) . . ?
H6A O6 H6B 108(8) . . ?
H7C O7 H7D 111.6 . . ?
H8A O8 H8B 69.4 . . ?

_diffrn_measured_fraction_theta_max 2.15
_diffrn_reflns_theta_full        29.47
_diffrn_measured_fraction_theta_full 0.828
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_p-1h
_database_code_depnum_ccdc_archive 'CCDC 1961361'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1231(13)
_cell_length_b                   9.7927(16)
_cell_length_c                   15.574(3)
_cell_angle_alpha                101.404(14)
_cell_angle_beta                 100.300(15)
_cell_angle_gamma                96.379(15)
_cell_volume                     1035.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14087
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      24.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            14087
_diffrn_reflns_av_R_equivalents  0.1633
_diffrn_reflns_av_sigmaI/netI    0.2080
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3656
_reflns_number_gt                1318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1482P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2524
_refine_ls_R_factor_gt           0.0940
_refine_ls_wR_factor_ref         0.2904
_refine_ls_wR_factor_gt          0.2230
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2356(9) 0.2302(6) -0.5023(4) 0.0568(17) Uani 1 1 d . . .
N2 N 0.3166(9) -0.0153(6) -0.4452(4) 0.0536(16) Uani 1 1 d . . .
N3 N 0.0984(8) 0.5671(5) 0.1253(4) 0.0440(15) Uani 1 1 d . . .
H3A H 0.0438 0.5916 0.0780 0.053 Uiso 1 1 calc R . .
H3B H 0.1209 0.6254 0.1764 0.053 Uiso 1 1 calc R . .
N4 N 0.2363(8) 0.4049(5) 0.1952(4) 0.0436(15) Uani 1 1 d . . .
H4 H 0.2607 0.4651 0.2457 0.052 Uiso 1 1 calc R . .
N5 N 0.3683(8) 0.2447(6) 0.2664(4) 0.0495(16) Uani 1 1 d . . .
H5A H 0.4023 0.1634 0.2675 0.059 Uiso 1 1 calc R . .
H5B H 0.3878 0.3084 0.3151 0.059 Uiso 1 1 calc R . .
N6 N 0.2537(8) 0.1800(5) 0.1151(4) 0.0409(14) Uani 1 1 d . . .
N7 N 0.1379(8) 0.1317(5) -0.0364(4) 0.0479(16) Uani 1 1 d . . .
H7A H 0.1713 0.0493 -0.0396 0.058 Uiso 1 1 calc R . .
H7B H 0.0843 0.1555 -0.0842 0.058 Uiso 1 1 calc R . .
N8 N 0.1131(7) 0.3500(5) 0.0407(3) 0.0395(14) Uani 1 1 d . . .
N9 N 0.6304(8) 0.1353(6) -0.0753(4) 0.0488(16) Uani 1 1 d . . .
H9A H 0.6591 0.0514 -0.0865 0.059 Uiso 1 1 calc R . .
H9B H 0.5812 0.1716 -0.1184 0.059 Uiso 1 1 calc R . .
N10 N 0.6133(7) 0.3405(5) 0.0199(3) 0.0357(13) Uani 1 1 d . . .
N11 N 0.7384(7) 0.1478(5) 0.0730(3) 0.0338(13) Uani 1 1 d . . .
N12 N 0.8391(8) 0.1727(6) 0.2246(4) 0.0475(15) Uani 1 1 d . . .
H12A H 0.8719 0.0899 0.2173 0.057 Uiso 1 1 calc R . .
H12B H 0.8545 0.2243 0.2776 0.057 Uiso 1 1 calc R . .
N13 N 0.7213(8) 0.3560(5) 0.1717(4) 0.0395(14) Uani 1 1 d . . .
H13 H 0.7424 0.4041 0.2260 0.047 Uiso 1 1 calc R . .
N14 N 0.6054(8) 0.5415(5) 0.1235(4) 0.0473(15) Uani 1 1 d . . .
H14A H 0.5571 0.5799 0.0812 0.057 Uiso 1 1 calc R . .
H14B H 0.6271 0.5875 0.1783 0.057 Uiso 1 1 calc R . .
O1 O -0.0618(8) 0.3218(5) -0.3162(4) 0.0740(17) Uani 1 1 d . . .
H1A H 0.0533 0.3694 -0.3431 0.111 Uiso 1 1 d R . .
H1B H -0.1384 0.3646 -0.3543 0.111 Uiso 1 1 d R . .
O2 O 0.5844(8) 0.4300(5) -0.3625(4) 0.0707(16) Uani 1 1 d . . .
O3 O 0.2988(8) 0.4456(5) -0.3236(3) 0.0579(14) Uani 1 1 d . . .
O4 O 0.4821(10) 0.2235(6) -0.2389(4) 0.092(2) Uani 1 1 d . . .
O5 O 0.5831(8) 0.0243(5) -0.2861(3) 0.0678(16) Uani 1 1 d . . .
O6 O -0.0140(8) 0.0994(6) -0.2248(4) 0.0735(17) Uani 1 1 d . . .
H6A H -0.1152 0.0778 -0.2264 0.110 Uiso 1 1 d R . .
H6B H -0.0603 0.0311 -0.2677 0.18(6) Uiso 1 1 d R . .
O7 O 0.3444(10) -0.3136(7) -0.4464(5) 0.113(3) Uani 1 1 d . . .
H7C H 0.2913 -0.2782 -0.4043 0.169 Uiso 1 1 d R . .
H7D H 0.2593 -0.3668 -0.4885 0.169 Uiso 1 1 d R . .
O8 O 0.9992(10) 0.3816(7) 0.3863(4) 0.096(2) Uani 1 1 d . . .
H8A H 0.9149 0.3490 0.4123 0.143 Uiso 1 1 d R . .
H8B H 1.0783 0.4411 0.4277 0.143 Uiso 1 1 d R . .
C1 C 0.4899(11) 0.1208(7) -0.2982(5) 0.050(2) Uani 1 1 d . . .
C2 C 0.4121(12) 0.3830(8) -0.3626(5) 0.052(2) Uani 1 1 d . . .
C3 C 0.3361(10) 0.2353(7) -0.4192(5) 0.0454(18) Uani 1 1 d . . .
C4 C 0.3779(10) 0.1132(7) -0.3907(4) 0.0411(17) Uani 1 1 d . . .
C5 C 0.2170(11) -0.0187(8) -0.5274(5) 0.058(2) Uani 1 1 d . . .
H5 H 0.1722 -0.1052 -0.5672 0.070 Uiso 1 1 calc R . .
C6 C 0.1791(12) 0.1048(8) -0.5546(5) 0.060(2) Uani 1 1 d . . .
H6 H 0.1106 0.0975 -0.6125 0.072 Uiso 1 1 calc R . .
C7 C 0.7651(9) 0.2204(7) 0.1545(5) 0.0383(17) Uani 1 1 d . . .
C8 C 0.6617(9) 0.2077(7) 0.0076(4) 0.0374(17) Uani 1 1 d . . .
C9 C 0.6463(9) 0.4123(7) 0.1044(5) 0.0397(17) Uani 1 1 d . . .
C10 C 0.1689(9) 0.2208(7) 0.0411(5) 0.0382(17) Uani 1 1 d . . .
C11 C 0.1478(9) 0.4399(7) 0.1195(4) 0.0358(16) Uani 1 1 d . . .
C12 C 0.2866(9) 0.2716(7) 0.1903(5) 0.0372(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.309(9) . ?
N1 C3 1.351(9) . ?
N2 C5 1.340(9) . ?
N2 C4 1.348(8) . ?
N3 C11 1.323(8) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C11 1.359(8) . ?
N4 C12 1.384(8) . ?
N4 H4 0.8600 . ?
N5 C12 1.313(8) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C12 1.293(8) . ?
N6 C10 1.356(8) . ?
N7 C10 1.309(8) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C11 1.326(8) . ?
N8 C10 1.369(8) . ?
N9 C8 1.311(8) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C9 1.330(8) . ?
N10 C8 1.369(8) . ?
N11 C7 1.296(8) . ?
N11 C8 1.337(8) . ?
N12 C7 1.319(8) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C9 1.336(8) . ?
N13 C7 1.383(8) . ?
N13 H13 0.8600 . ?
N14 C9 1.318(8) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
O1 H1A 1.0871 . ?
O1 H1B 0.9267 . ?
O2 C2 1.261(9) . ?
O3 C2 1.239(9) . ?
O4 C1 1.238(8) . ?
O5 C1 1.239(8) . ?
O6 H6A 0.7228 . ?
O6 H6B 0.8353 . ?
O7 H7C 0.8502 . ?
O7 H7D 0.8491 . ?
O8 H8A 0.8498 . ?
O8 H8B 0.8491 . ?
C1 C4 1.499(10) . ?
C2 C3 1.521(10) . ?
C3 C4 1.399(9) . ?
C5 C6 1.396(11) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 116.3(6) . . ?
C5 N2 C4 116.5(6) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 C12 119.3(5) . . ?
C11 N4 H4 120.4 . . ?
C12 N4 H4 120.4 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C12 N6 C10 117.0(5) . . ?
C10 N7 H7A 120.0 . . ?
C10 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C11 N8 C10 115.9(5) . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C9 N10 C8 115.6(5) . . ?
C7 N11 C8 117.3(5) . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C9 N13 C7 120.2(6) . . ?
C9 N13 H13 119.9 . . ?
C7 N13 H13 119.9 . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
H1A O1 H1B 83.0 . . ?
H6A O6 H6B 69.1 . . ?
H7C O7 H7D 109.5 . . ?
H8A O8 H8B 104.6 . . ?
O4 C1 O5 124.4(7) . . ?
O4 C1 C4 117.4(6) . . ?
O5 C1 C4 118.2(6) . . ?
O3 C2 O2 126.9(7) . . ?
O3 C2 C3 117.3(7) . . ?
O2 C2 C3 115.8(7) . . ?
N1 C3 C4 121.9(6) . . ?
N1 C3 C2 114.9(6) . . ?
C4 C3 C2 123.1(6) . . ?
N2 C4 C3 121.0(6) . . ?
N2 C4 C1 117.9(6) . . ?
C3 C4 C1 121.1(6) . . ?
N2 C5 C6 121.4(7) . . ?
N2 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 122.9(7) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
N11 C7 N12 122.9(6) . . ?
N11 C7 N13 120.6(6) . . ?
N12 C7 N13 116.4(6) . . ?
N9 C8 N11 118.3(6) . . ?
N9 C8 N10 116.5(6) . . ?
N11 C8 N10 125.2(6) . . ?
N14 C9 N10 120.4(6) . . ?
N14 C9 N13 118.5(6) . . ?
N10 C9 N13 121.1(6) . . ?
N7 C10 N6 118.5(6) . . ?
N7 C10 N8 116.5(6) . . ?
N6 C10 N8 124.9(6) . . ?
N3 C11 N8 120.0(6) . . ?
N3 C11 N4 118.6(6) . . ?
N8 C11 N4 121.4(6) . . ?
N6 C12 N5 122.7(6) . . ?
N6 C12 N4 121.5(6) . . ?
N5 C12 N4 115.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_P-90min
_database_code_depnum_ccdc_archive 'CCDC 1961362'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1186(7)
_cell_length_b                   9.7784(6)
_cell_length_c                   15.4920(12)
_cell_angle_alpha                101.367(6)
_cell_angle_beta                 100.201(7)
_cell_angle_gamma                96.332(6)
_cell_volume                     1028.67(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13950
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      29.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            13950
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.1312
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         29.49
_reflns_number_total             4786
_reflns_number_gt                2125
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1569P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4786
_refine_ls_number_parameters     319
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1950
_refine_ls_R_factor_gt           0.0917
_refine_ls_wR_factor_ref         0.3152
_refine_ls_wR_factor_gt          0.2622
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7641(7) 1.2690(5) 0.5024(3) 0.0438(13) Uani 1 1 d . . .
N2 N 0.6839(7) 1.5136(5) 0.4456(4) 0.0449(13) Uani 1 1 d . . .
N3 N 0.6040(7) 1.0417(5) 0.1222(3) 0.0406(12) Uani 1 1 d . . .
H3A H 0.5543 1.0789 0.0792 0.049 Uiso 1 1 calc R . .
H3B H 0.6257 1.0887 0.1770 0.049 Uiso 1 1 calc R . .
N6 N 0.7370(6) 0.6476(4) 0.0742(3) 0.0336(11) Uani 1 1 d . . .
N8 N 0.6135(6) 0.8408(4) 0.0199(3) 0.0336(11) Uani 1 1 d . . .
N4 N 0.7236(7) 0.8566(4) 0.1727(3) 0.0343(11) Uani 1 1 d . . .
H4 H 0.7441 0.9049 0.2272 0.041 Uiso 1 1 calc R . .
N5 N 0.8424(8) 0.6743(5) 0.2250(3) 0.0471(13) Uani 1 1 d . . .
H5A H 0.8713 0.5903 0.2171 0.056 Uiso 1 1 calc R . .
H5B H 0.8620 0.7263 0.2784 0.056 Uiso 1 1 calc R . .
N7 N 0.6316(7) 0.6351(5) -0.0759(3) 0.0435(13) Uani 1 1 d . . .
H7A H 0.6612 0.5514 -0.0866 0.052 Uiso 1 1 calc R . .
H7B H 0.5832 0.6710 -0.1197 0.052 Uiso 1 1 calc R . .
N9 N 0.8621(7) 0.3673(5) 0.0364(3) 0.0454(13) Uani 1 1 d . . .
H9A H 0.8288 0.4497 0.0393 0.054 Uiso 1 1 calc R . .
H9B H 0.9159 0.3439 0.0845 0.054 Uiso 1 1 calc R . .
N10 N 0.8869(6) 0.1486(4) -0.0409(3) 0.0334(11) Uani 1 1 d . . .
N11 N 0.7460(7) 0.3195(4) -0.1144(3) 0.0363(11) Uani 1 1 d . . .
N12 N 0.6302(7) 0.2538(5) -0.2671(3) 0.0448(13) Uani 1 1 d . . .
H12A H 0.5968 0.3356 -0.2676 0.054 Uiso 1 1 calc R . .
H12B H 0.6098 0.1906 -0.3163 0.054 Uiso 1 1 calc R . .
N13 N 0.7644(7) 0.0953(5) -0.1951(3) 0.0370(12) Uani 1 1 d . . .
H13 H 0.7423 0.0355 -0.2458 0.044 Uiso 1 1 calc R . .
N14 N 0.8999(7) -0.0678(4) -0.1258(3) 0.0410(12) Uani 1 1 d . . .
H14A H 0.9553 -0.0927 -0.0786 0.049 Uiso 1 1 calc R . .
H14B H 0.8763 -0.1259 -0.1773 0.049 Uiso 1 1 calc R . .
O1 O 1.0616(7) 1.1775(5) 0.3164(3) 0.0627(13) Uani 1 1 d D . .
H1A H 1.1501 1.1413 0.3613 0.094 Uiso 1 1 d RD . .
H1B H 0.9375 1.1257 0.3336 0.094 Uiso 1 1 d RD . .
O2 O 0.7003(6) 1.0533(4) 0.3239(3) 0.0487(11) Uani 1 1 d . . .
O3 O 0.4155(7) 1.0705(4) 0.3638(3) 0.0576(13) Uani 1 1 d . . .
O4 O 0.5158(9) 1.2751(5) 0.2388(3) 0.0816(19) Uani 1 1 d . . .
O5 O 0.4143(7) 1.4749(4) 0.2860(3) 0.0596(13) Uani 1 1 d . . .
O6 O 0.0174(9) 1.4049(5) 0.2246(4) 0.0635(15) Uani 1 1 d . . .
H6A H -0.004(14) 1.352(10) 0.248(7) 0.095 Uiso 1 1 d . . .
H6B H 0.134(13) 1.437(9) 0.232(6) 0.095 Uiso 1 1 d . . .
O7 O 0.6557(9) 1.8148(7) 0.4478(4) 0.0909(19) Uani 1 1 d G . .
H7C H 0.7237 1.7801 0.4116 0.136 Uiso 1 1 d G . .
H7D H 0.7321 1.8822 0.4849 0.136 Uiso 1 1 d G . .
O8 O 0.9989(8) 0.8835(5) 0.3868(3) 0.0750(15) Uani 1 1 d GD . .
H8A H 1.0863 0.9364 0.4282 0.112 Uiso 1 1 d RD . .
H8B H 0.9109 0.8592 0.4138 0.112 Uiso 1 1 d RD . .
C1 C 0.5093(9) 1.3802(6) 0.2972(4) 0.0458(16) Uani 1 1 d . . .
C2 C 0.5863(10) 1.1174(6) 0.3639(4) 0.0402(15) Uani 1 1 d . . .
C3 C 0.6631(8) 1.2650(6) 0.4200(4) 0.0374(14) Uani 1 1 d . . .
C4 C 0.6219(8) 1.3863(6) 0.3903(4) 0.0377(14) Uani 1 1 d . . .
C5 C 0.7823(9) 1.5164(6) 0.5270(4) 0.0472(16) Uani 1 1 d . . .
H5 H 0.8264 1.6033 0.5666 0.057 Uiso 1 1 calc R . .
C6 C 0.8220(10) 1.3962(7) 0.5555(4) 0.0512(17) Uani 1 1 d . . .
H6 H 0.8912 1.4043 0.6136 0.061 Uiso 1 1 calc R . .
C7 C 0.7127(8) 0.2254(5) -0.1909(4) 0.0330(13) Uani 1 1 d . . .
C8 C 0.8308(8) 0.2773(5) -0.0412(4) 0.0319(13) Uani 1 1 d . . .
C9 C 0.8509(8) 0.0600(5) -0.1193(4) 0.0314(12) Uani 1 1 d . . .
C11 C 0.6468(7) 0.9131(5) 0.1040(4) 0.0311(13) Uani 1 1 d . . .
C10 C 0.6603(8) 0.7082(6) 0.0072(4) 0.0344(13) Uani 1 1 d . . .
C12 C 0.7685(8) 0.7232(6) 0.1558(4) 0.0333(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
N1 C6 1.326(7) . ?
N1 C3 1.340(7) . ?
N2 C5 1.323(8) . ?
N2 C4 1.343(7) . ?
N3 C11 1.315(6) . ?
N6 C12 1.299(7) . ?
N6 C10 1.356(7) . ?
N8 C11 1.321(7) . ?
N8 C10 1.360(7) . ?
N4 C11 1.352(7) . ?
N4 C12 1.364(7) . ?
N5 C12 1.309(7) . ?
N7 C10 1.312(7) . ?
N9 C8 1.309(7) . ?
N10 C9 1.311(7) . ?
N10 C8 1.362(6) . ?
N11 C7 1.315(7) . ?
N11 C8 1.349(7) . ?
N12 C7 1.318(7) . ?
N13 C9 1.352(7) . ?
N13 C7 1.355(7) . ?
N14 C9 1.323(7) . ?
O2 C2 1.254(7) . ?
O3 C2 1.251(8) . ?
O4 C1 1.239(7) . ?
O5 C1 1.227(7) . ?
C1 C4 1.507(8) . ?
C2 C3 1.517(8) . ?
C3 C4 1.396(8) . ?
C5 C6 1.375(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 116.0(5) . . ?
C5 N2 C4 117.0(5) . . ?
C12 N6 C10 117.0(5) . . ?
C11 N8 C10 116.3(5) . . ?
C11 N4 C12 120.0(5) . . ?
C9 N10 C8 115.6(5) . . ?
C7 N11 C8 115.8(4) . . ?
C9 N13 C7 119.8(4) . . ?
O5 C1 O4 125.5(6) . . ?
O5 C1 C4 118.4(5) . . ?
O4 C1 C4 116.0(5) . . ?
O3 C2 O2 126.4(5) . . ?
O3 C2 C3 116.3(5) . . ?
O2 C2 C3 117.3(6) . . ?
N1 C3 C4 122.8(5) . . ?
N1 C3 C2 114.4(5) . . ?
C4 C3 C2 122.7(5) . . ?
N2 C4 C3 119.6(5) . . ?
N2 C4 C1 118.1(5) . . ?
C3 C4 C1 122.3(5) . . ?
N2 C5 C6 122.8(5) . . ?
N1 C6 C5 121.7(6) . . ?
N11 C7 N12 121.6(5) . . ?
N11 C7 N13 121.5(5) . . ?
N12 C7 N13 116.9(5) . . ?
N9 C8 N11 117.5(5) . . ?
N9 C8 N10 117.0(5) . . ?
N11 C8 N10 125.6(5) . . ?
N10 C9 N14 120.0(5) . . ?
N10 C9 N13 121.7(5) . . ?
N14 C9 N13 118.3(5) . . ?
N3 C11 N8 120.1(5) . . ?
N3 C11 N4 118.9(5) . . ?
N8 C11 N4 121.0(5) . . ?
N7 C10 N6 118.1(5) . . ?
N7 C10 N8 117.4(5) . . ?
N6 C10 N8 124.5(5) . . ?
N6 C12 N5 121.6(5) . . ?
N6 C12 N4 121.2(5) . . ?
N5 C12 N4 117.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        29.49
_diffrn_measured_fraction_theta_full 0.836
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_H-107
_database_code_depnum_ccdc_archive 'CCDC 1961358'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1278(15)
_cell_length_b                   9.7918(11)
_cell_length_c                   15.501(2)
_cell_angle_alpha                101.310(11)
_cell_angle_beta                 100.178(15)
_cell_angle_gamma                96.415(13)
_cell_volume                     1032.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7142
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      29.51

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            17142
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_sigmaI/netI    0.2030
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         29.51
_reflns_number_total             4802
_reflns_number_gt                1873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4802
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2386
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.3116
_refine_ls_wR_factor_gt          0.2241
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      1.113
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2360(8) 0.2302(6) -0.0025(4) 0.0365(14) Uani 1 1 d . . .
N2 N 0.3170(8) -0.0136(6) 0.0548(4) 0.0370(14) Uani 1 1 d . . .
N3 N 0.3948(8) 0.4583(5) 0.3774(4) 0.0356(14) Uani 1 1 d . . .
H3A H 0.4436 0.4206 0.4202 0.043 Uiso 1 1 calc R . .
H3B H 0.3729 0.4117 0.3226 0.043 Uiso 1 1 calc R . .
N4 N 0.2763(7) 0.6432(5) 0.3269(3) 0.0290(13) Uani 1 1 d . . .
H4 H 0.2542 0.5946 0.2725 0.035 Uiso 1 1 calc R . .
N5 N 0.1624(8) 0.8294(6) 0.2774(4) 0.0405(15) Uani 1 1 d . . .
H5A H 0.1339 0.9133 0.2867 0.05(2) Uiso 1 1 calc R . .
H5B H 0.1435 0.7797 0.2234 0.014(15) Uiso 1 1 calc RD . .
N6 N 0.2629(6) 0.8526(4) 0.4263(2) 0.0280(12) Uani 1 1 d G . .
N7 N 0.3689(6) 0.8646(4) 0.5760(2) 0.0389(15) Uani 1 1 d G . .
H7A H 0.4167 0.8287 0.6199 0.047 Uiso 1 1 calc R . .
H7B H 0.3404 0.9485 0.5865 0.047 Uiso 1 1 calc R . .
N8 N 0.3875(4) 0.6594(3) 0.4806(2) 0.0293(13) Uani 1 1 d R . .
N9 N 0.9028(6) 0.4327(5) 0.3744(3) 0.0338(14) Uani 1 1 d R . .
H9A H 0.8816 0.4086 0.4231 0.041 Uiso 1 1 d R . .
H9B H 0.8456 0.3666 0.3287 0.041 Uiso 1 1 d R . .
N10 N 0.7636(7) 0.5943(5) 0.3042(3) 0.0299(13) Uani 1 1 d . . .
H10 H 0.7405 0.5338 0.2538 0.036 Uiso 1 1 calc R . .
N11 N 0.8874(7) 0.6491(5) 0.4594(3) 0.0283(13) Uani 1 1 d . . .
N12 N 0.8608(8) 0.8672(5) 0.5366(4) 0.0384(15) Uani 1 1 d . . .
H12A H 0.9125 0.8436 0.5849 0.046 Uiso 1 1 calc R . .
H12B H 0.8279 0.9495 0.5392 0.046 Uiso 1 1 calc R . .
N13 N 0.7444(8) 0.8191(5) 0.3841(4) 0.0320(13) Uani 1 1 d . . .
N14 N 0.6292(8) 0.7535(6) 0.2325(4) 0.0371(14) Uani 1 1 d . . .
H14A H 0.5946 0.8347 0.2317 0.045 Uiso 1 1 calc R . .
H14B H 0.6095 0.6903 0.1835 0.045 Uiso 1 1 calc R . .
O1 O 0.9398(3) 0.3250(3) 0.1834(2) 0.0540(15) Uani 1 1 d G . .
H1A H 0.8455 0.3353 0.1447 0.065 Uiso 1 1 d G . .
H1B H 0.9592 0.2419 0.1673 0.065 Uiso 1 1 d G . .
O2 O 0.3004(4) 0.4466(3) 0.1763(2) 0.0394(12) Uani 1 1 d G . .
O3 O 0.5834(4) 0.4298(3) 0.13617(19) 0.0503(14) Uani 1 1 d G . .
O4 O 0.4850(4) 0.2246(3) 0.26124(18) 0.073(2) Uani 1 1 d G . .
O5 O 0.5843(4) 0.0246(2) 0.2142(2) 0.0520(15) Uani 1 1 d G . .
O6 O 0.9807(4) 0.0956(3) 0.2756(2) 0.0564(15) Uani 1 1 d G . .
H6A H 1.0211 0.1017 0.2416 0.085 Uiso 1 1 d G . .
H6B H 0.8475 0.0543 0.2787 0.085 Uiso 1 1 d G . .
O7 O 0.3478(7) -0.3138(3) 0.0533(3) 0.079(2) Uani 1 1 d G . .
H7C H 0.2535 -0.3652 0.0151 0.118 Uiso 1 1 d G . .
H7D H 0.2965 -0.2705 0.0940 0.118 Uiso 1 1 d G . .
O8 O 0.0003(6) 0.6138(3) 0.1107(3) 0.0660(17) Uani 1 1 d G . .
H8A H -0.0338 0.6952 0.1174 0.099 Uiso 1 1 d GD . .
H8B H -0.0879 0.5546 0.0735 0.099 Uiso 1 1 d G . .
C1 C 0.4897(6) 0.1211(3) 0.20342(19) 0.0372(17) Uani 1 1 d R . .
C2 C 0.4112(4) 0.3823(2) 0.1360(2) 0.0332(16) Uani 1 1 d R . .
C3 C 0.3375(3) 0.2347(2) 0.07991(16) 0.0282(15) Uani 1 1 d R . .
C4 C 0.3767(4) 0.1131(2) 0.10978(16) 0.0310(16) Uani 1 1 d R . .
C5 C 0.2192(5) -0.0183(3) -0.02787(19) 0.0423(19) Uani 1 1 d R . .
H5 H 0.1793 -0.1050 -0.0680 0.051 Uiso 1 1 calc R . .
C6 C 0.1757(6) 0.1032(3) -0.05530(16) 0.0425(19) Uani 1 1 d R . .
H6 H 0.1021 0.0953 -0.1124 0.051 Uiso 1 1 calc R . .
C7 C 0.8320(9) 0.7774(6) 0.4587(4) 0.0273(15) Uani 1 1 d . . .
C8 C 0.8509(9) 0.5603(6) 0.3798(4) 0.0290(15) Uani 1 1 d . . .
C9 C 0.7117(9) 0.7264(6) 0.3081(4) 0.0288(15) Uani 1 1 d . . .
C10 C 0.3397(9) 0.7915(6) 0.4934(4) 0.0283(15) Uani 1 1 d . . .
C11 C 0.3538(9) 0.5869(6) 0.3959(4) 0.0282(15) Uani 1 1 d . . .
C12 C 0.2333(9) 0.7782(6) 0.3439(4) 0.0269(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.326(6) . ?
N1 C3 1.342(6) . ?
N2 C4 1.336(6) . ?
N2 C5 1.336(6) . ?
N3 C11 1.313(8) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C11 1.358(8) . ?
N4 C12 1.376(7) . ?
N4 H4 0.8600 . ?
N5 C12 1.283(8) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C12 1.308(7) . ?
N6 C10 1.362(7) . ?
N7 C10 1.307(7) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C11 1.331(7) . ?
N8 C10 1.360(7) . ?
N9 C8 1.334(7) . ?
N9 H9A 0.8654 . ?
N9 H9B 0.8636 . ?
N10 C8 1.346(8) . ?
N10 C9 1.378(8) . ?
N10 H10 0.8600 . ?
N11 C8 1.327(8) . ?
N11 C7 1.360(8) . ?
N12 C7 1.315(8) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C9 1.305(8) . ?
N13 C7 1.371(8) . ?
N14 C9 1.306(8) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
O1 H1A 0.8477 . ?
O1 H1B 0.8370 . ?
O2 C2 1.242(4) . ?
O3 C2 1.262(4) . ?
O4 C1 1.222(4) . ?
O5 C1 1.241(3) . ?
O6 H6A 0.6525 . ?
O6 H6B 1.0027 . ?
O7 H7C 0.8495 . ?
O7 H7D 0.8503 . ?
O8 H8A 0.8510 . ?
O8 H8B 0.8502 . ?
C1 C4 1.5132 . ?
C2 C3 1.5156 . ?
C3 C4 1.3981 . ?
C5 C6 1.3880 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 116.3(4) . . ?
C4 N2 C5 117.6(5) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 C12 119.9(5) . . ?
C11 N4 H4 120.0 . . ?
C12 N4 H4 120.0 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C12 N6 C10 117.2(4) . . ?
C10 N7 H7A 120.0 . . ?
C10 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C11 N8 C10 116.2(5) . . ?
C8 N9 H9A 104.7 . . ?
C8 N9 H9B 118.1 . . ?
H9A N9 H9B 109.0 . . ?
C8 N10 C9 119.6(5) . . ?
C8 N10 H10 120.2 . . ?
C9 N10 H10 120.2 . . ?
C8 N11 C7 115.0(5) . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C9 N13 C7 116.3(5) . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
H1A O1 H1B 105.9 . . ?
H6A O6 H6B 131.9 . . ?
H7C O7 H7D 104.5 . . ?
H8A O8 H8B 109.4 . . ?
O4 C1 O5 125.6(3) . . ?
O4 C1 C4 117.06(17) . . ?
O5 C1 C4 117.3(2) . . ?
O2 C2 O3 125.6(3) . . ?
O2 C2 C3 118.8(2) . . ?
O3 C2 C3 115.5(2) . . ?
N1 C3 C4 122.5(3) . . ?
N1 C3 C2 114.3(3) . . ?
C4 C3 C2 123.2 . . ?
N2 C4 C3 120.1(3) . . ?
N2 C4 C1 118.5(3) . . ?
C3 C4 C1 121.4 . . ?
N2 C5 C6 121.5(3) . . ?
N2 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
N1 C6 C5 122.0(3) . . ?
N1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N12 C7 N11 116.9(6) . . ?
N12 C7 N13 117.6(6) . . ?
N11 C7 N13 125.5(5) . . ?
N11 C8 N9 118.8(6) . . ?
N11 C8 N10 122.5(6) . . ?
N9 C8 N10 118.7(6) . . ?
N13 C9 N14 122.1(6) . . ?
N13 C9 N10 121.1(6) . . ?
N14 C9 N10 116.8(6) . . ?
N7 C10 N8 117.5(5) . . ?
N7 C10 N6 117.8(5) . . ?
N8 C10 N6 124.7(5) . . ?
N3 C11 N8 120.2(6) . . ?
N3 C11 N4 118.5(6) . . ?
N8 C11 N4 121.2(5) . . ?
N5 C12 N6 120.6(5) . . ?
N5 C12 N4 118.6(6) . . ?
N6 C12 N4 120.8(5) . . ?

_diffrn_measured_fraction_theta_max 2.15
_diffrn_reflns_theta_full        29.51
_diffrn_measured_fraction_theta_full 0.835
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.130
####################################################################### 
# 
# 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_P-30min
_database_code_depnum_ccdc_archive 'CCDC 1961360'
loop_
_audit_author_name
_audit_author_address
'H.H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2019-10-25 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N2 O4, 2(C3 H7 N6), 4(H2 O)'
_chemical_formula_sum            'C12 H24 N14 O8'
_chemical_formula_weight         492.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1340(6)
_cell_length_b                   9.8000(7)
_cell_length_c                   15.5172(12)
_cell_angle_alpha                101.331(6)
_cell_angle_beta                 100.248(7)
_cell_angle_gamma                96.380(7)
_cell_volume                     1034.68(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13573
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      29.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            13573
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.1262
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         29.43
_reflns_number_total             4746
_reflns_number_gt                2250
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius CAD4 software'
_computing_cell_refinement       'Nonius CAD4 software'
_computing_data_reduction        'XCAD (P.McArdle, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0844P)²+0.0054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4746
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      2.090
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.006

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2353(9) 0.7297(6) -0.5024(4) 0.0347(15) Uani 1 1 d . . .
N2 N 0.3170(9) 0.4858(6) -0.4457(4) 0.0339(15) Uani 1 1 d . . .
N3 N 0.6058(8) 1.0418(6) 0.1228(4) 0.0328(15) Uani 1 1 d . . .
H3A H 0.5563 1.0795 0.0802 0.039 Uiso 1 1 calc R . .
H3B H 0.6282 1.0882 0.1776 0.039 Uiso 1 1 calc R . .
N4 N 0.7248(8) 0.8563(6) 0.1729(4) 0.0277(14) Uani 1 1 d . . .
H4 H 0.7467 0.9048 0.2272 0.033 Uiso 1 1 calc R . .
N5 N 0.8428(9) 0.6738(6) 0.2249(4) 0.0381(16) Uani 1 1 d . . .
H5A H 0.8730 0.5903 0.2170 0.046 Uiso 1 1 calc R . .
H5B H 0.8617 0.7254 0.2782 0.046 Uiso 1 1 calc R . .
N6 N 0.7368(8) 0.6470(5) 0.0733(4) 0.0264(14) Uani 1 1 d . . .
N7 N 0.6316(9) 0.6346(6) -0.0762(4) 0.0356(16) Uani 1 1 d . . .
H7A H 0.6608 0.5509 -0.0866 0.043 Uiso 1 1 calc R . .
H7B H 0.5833 0.6702 -0.1200 0.043 Uiso 1 1 calc R . .
N8 N 0.6130(8) 0.8402(5) 0.0191(4) 0.0269(14) Uani 1 1 d . . .
N9 N 0.8609(9) 0.3695(6) 0.0344(4) 0.0376(16) Uani 1 1 d . . .
H9A H 0.8261 0.4510 0.0357 0.045 Uiso 1 1 calc R . .
H9B H 0.9152 0.3487 0.0832 0.045 Uiso 1 1 calc RD . .
N10 N 0.8873(8) 0.1495(5) -0.0409(4) 0.0276(14) Uani 1 1 d . . .
N11 N 0.7449(8) 0.3199(6) -0.1150(4) 0.0279(14) Uani 1 1 d . . .
N12 N 0.6294(9) 0.2539(6) -0.2674(4) 0.0356(15) Uani 1 1 d . . .
H12A H 0.5954 0.3352 -0.2678 0.043 Uiso 1 1 calc R . .
H12B H 0.6093 0.1910 -0.3165 0.043 Uiso 1 1 calc R . .
N13 N 0.7628(8) 0.0941(5) -0.1956(4) 0.0290(14) Uani 1 1 d . . .
H13 H 0.7392 0.0338 -0.2460 0.035 Uiso 1 1 calc R . .
N14 N 0.8996(9) -0.0680(6) -0.1262(4) 0.0329(15) Uani 1 1 d . . .
H14A H 0.9559 -0.0927 -0.0792 0.039 Uiso 1 1 calc R . .
H14B H 0.8753 -0.1261 -0.1776 0.039 Uiso 1 1 calc R . .
O1 O -0.0607(10) 0.8229(6) -0.3169(4) 0.0501(16) Uani 1 1 d . . .
H1A H 0.060(14) 0.881(10) -0.334(6) 0.075 Uiso 1 1 d . . .
H1B H -0.156(15) 0.856(10) -0.345(7) 0.075 Uiso 1 1 d . . .
O2 O 0.3013(5) 0.9460(3) -0.3235(2) 0.0367(13) Uani 1 1 d G . .
O3 O 0.5844(5) 0.9292(3) -0.3640(3) 0.0447(14) Uani 1 1 d G . .
O4 O 0.4821(5) 0.7234(3) -0.23895(19) 0.071(2) Uani 1 1 d G . .
O5 O 0.5832(5) 0.5231(3) -0.2861(2) 0.0485(15) Uani 1 1 d G . .
O6 O 0.9819(5) 0.5954(4) -0.2253(3) 0.0534(16) Uani 1 1 d G . .
H6A H 0.9798 0.6206 -0.1699 0.080 Uiso 1 1 d GD . .
H6B H 0.8729 0.5494 -0.2536 0.080 Uiso 1 1 d G . .
O7 O 0.3424(11) 0.1840(7) -0.4468(4) 0.069(2) Uani 1 1 d G . .
H7C H 0.3409 0.2722 -0.4379 0.104 Uiso 1 1 d G . .
H7D H 0.3549 0.1530 -0.5003 0.104 Uiso 1 1 d G . .
O8 O 0.9991(9) 0.8848(7) 0.3866(4) 0.0583(17) Uani 1 1 d G . .
H8A H 0.8953 0.8675 0.4049 0.087 Uiso 1 1 d G . .
H8B H 1.0855 0.8633 0.4247 0.087 Uiso 1 1 d G . .
C1 C 0.4898(9) 0.6201(5) -0.2972(3) 0.0350(18) Uani 1 1 d G . .
C2 C 0.4135(9) 0.8826(3) -0.3632(3) 0.0299(17) Uani 1 1 d G . .
C3 C 0.3370(6) 0.7351(3) -0.4201(2) 0.0259(16) Uani 1 1 d G . .
C4 C 0.3769(5) 0.6128(3) -0.3908(2) 0.0269(16) Uani 1 1 d G . .
C5 C 0.2180(9) 0.4823(5) -0.5275(3) 0.039(2) Uani 1 1 d G . .
H5 H 0.1751 0.3957 -0.5673 0.047 Uiso 1 1 calc R . .
C6 C 0.1770(11) 0.6026(8) -0.5552(5) 0.039(2) Uani 1 1 d . . .
H6 H 0.1061 0.5945 -0.6128 0.047 Uiso 1 1 calc R . .
C7 C 0.7119(7) 0.2258(4) -0.1917(2) 0.0257(16) Uani 1 1 d G . .
C8 C 0.8313(5) 0.2775(3) -0.0416(2) 0.0262(16) Uani 1 1 d G . .
C9 C 0.8503(7) 0.0597(3) -0.1196(3) 0.0250(16) Uani 1 1 d G . .
C10 C 0.6606(6) 0.7082(3) 0.0070(2) 0.0263(16) Uani 1 1 d G . .
C11 C 0.6473(7) 0.9128(3) 0.1039(3) 0.0244(16) Uani 1 1 d G . .
C12 C 0.7681(7) 0.7221(4) 0.1558(2) 0.0253(16) Uani 1 1 d G . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.326(9) . ?
N1 C3 1.340(7) . ?
N2 C5 1.331(7) . ?
N2 C4 1.339(6) . ?
N3 C11 1.319(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C11 1.359(7) . ?
N4 C12 1.370(6) . ?
N4 H4 0.8600 . ?
N5 C12 1.308(6) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C12 1.313(6) . ?
N6 C10 1.353(6) . ?
N7 C10 1.317(6) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C11 1.334(6) . ?
N8 C10 1.359(6) . ?
N9 C8 1.304(6) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C9 1.321(6) . ?
N10 C8 1.359(6) . ?
N11 C7 1.321(6) . ?
N11 C8 1.357(6) . ?
N12 C7 1.310(7) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C9 1.355(7) . ?
N13 C7 1.372(6) . ?
N13 H13 0.8600 . ?
N14 C9 1.327(6) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
O1 H1A 1.08(10) . ?
O1 H1B 0.87(10) . ?
O2 C2 1.241(6) . ?
O3 C2 1.257(7) . ?
O4 C1 1.231(6) . ?
O5 C1 1.241(5) . ?
O6 H6A 0.8497 . ?
O6 H6B 0.8501 . ?
O7 H7C 0.8497 . ?
O7 H7D 0.8502 . ?
O8 H8A 0.8504 . ?
O8 H8B 0.8497 . ?
C1 C4 1.5146 . ?
C2 C3 1.5235 . ?
C3 C4 1.4028 . ?
C5 C6 1.374(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C3 116.4(6) . . ?
C5 N2 C4 116.9(5) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 C12 120.0(5) . . ?
C11 N4 H4 120.0 . . ?
C12 N4 H4 120.0 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C12 N6 C10 116.9(4) . . ?
C10 N7 H7A 120.0 . . ?
C10 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C11 N8 C10 115.7(5) . . ?
C8 N9 H9A 120.0 . . ?
C8 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C9 N10 C8 115.6(5) . . ?
C7 N11 C8 115.7(4) . . ?
C7 N12 H12A 120.0 . . ?
C7 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C9 N13 C7 119.7(4) . . ?
C9 N13 H13 120.2 . . ?
C7 N13 H13 120.2 . . ?
C9 N14 H14A 120.0 . . ?
C9 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
H1A O1 H1B 100(8) . . ?
H6A O6 H6B 109.5 . . ?
H7C O7 H7D 109.5 . . ?
H8A O8 H8B 104.5 . . ?
O4 C1 O5 125.9(4) . . ?
O4 C1 C4 116.6(3) . . ?
O5 C1 C4 117.6(3) . . ?
O2 C2 O3 126.7(4) . . ?
O2 C2 C3 117.8(4) . . ?
O3 C2 C3 115.5(3) . . ?
N1 C3 C4 121.9(3) . . ?
N1 C3 C2 115.3(3) . . ?
C4 C3 C2 122.8 . . ?
N2 C4 C3 120.5(3) . . ?
N2 C4 C1 118.1(3) . . ?
C3 C4 C1 121.4 . . ?
N2 C5 C6 122.2(5) . . ?
N2 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
N1 C6 C5 122.2(6) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N12 C7 N11 121.6(4) . . ?
N12 C7 N13 117.1(4) . . ?
N11 C7 N13 121.3(4) . . ?
N9 C8 N11 115.7(4) . . ?
N9 C8 N10 118.3(4) . . ?
N11 C8 N10 126.0(4) . . ?
N10 C9 N14 120.4(5) . . ?
N10 C9 N13 121.7(4) . . ?
N14 C9 N13 117.9(4) . . ?
N7 C10 N6 117.4(4) . . ?
N7 C10 N8 117.2(4) . . ?
N6 C10 N8 125.4(4) . . ?
N3 C11 N8 120.4(5) . . ?
N3 C11 N4 118.4(4) . . ?
N8 C11 N4 121.2(4) . . ?
N5 C12 N6 122.1(4) . . ?
N5 C12 N4 117.1(4) . . ?
N6 C12 N4 120.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        29.43
_diffrn_measured_fraction_theta_full 0.828
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.074
