# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1500614'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N4 O6'
_chemical_formula_weight         232.16

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.125(2)
_cell_length_b                   8.3450(17)
_cell_length_c                   10.583(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.10(3)
_cell_angle_gamma                90.00
_cell_volume                     859.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            1669
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.38
_reflns_number_total             1577
_reflns_number_gt                1176
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0900P)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         1577
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
O1 O 0.06440(18) 0.1554(2) 0.56135(18) 0.0321(5) Uani 1 1 d . . .
N1 N 0.3091(2) 0.1282(3) 0.5991(2) 0.0274(5) Uani 1 1 d . . .
H1A H 0.3141 0.1737 0.5277 0.033 Uiso 1 1 calc R . .
C1 C 0.0568(3) 0.3109(4) 0.6166(3) 0.0361(7) Uani 1 1 d . . .
H1B H -0.0313 0.3595 0.5741 0.043 Uiso 1 1 calc R . .
H1C H 0.1284 0.3791 0.6013 0.043 Uiso 1 1 calc R . .
O2 O 0.20609(19) 0.2305(3) 0.82383(17) 0.0401(6) Uani 1 1 d . . .
N2 N 0.3681(2) 0.0466(3) 0.8022(2) 0.0298(6) Uani 1 1 d . . .
H2A H 0.4180 0.0017 0.8723 0.036 Uiso 1 1 calc R . .
C2 C 0.1812(3) 0.0699(3) 0.6242(3) 0.0289(6) Uani 1 1 d . . .
H2B H 0.1676 -0.0423 0.5964 0.035 Uiso 1 1 calc R . .
N3 N 0.6590(2) 0.0998(3) 0.8310(2) 0.0295(5) Uani 1 1 d . . .
O3 O 0.7698(2) 0.1679(3) 0.8502(2) 0.0431(6) Uani 1 1 d . . .
C3 C 0.2233(3) 0.0756(4) 0.7744(3) 0.0315(6) Uani 1 1 d . . .
H3A H 0.1771 -0.0075 0.8119 0.038 Uiso 1 1 calc R . .
N4 N 0.5998(2) 0.1586(3) 0.5981(2) 0.0303(6) Uani 1 1 d . . .
O4 O 0.6311(2) 0.0113(3) 0.91439(19) 0.0419(6) Uani 1 1 d . . .
C4 C 0.0738(3) 0.2974(4) 0.7615(3) 0.0413(8) Uani 1 1 d . . .
H4A H 0.0659 0.4025 0.7979 0.050 Uiso 1 1 calc R . .
H4B H 0.0023 0.2293 0.7772 0.050 Uiso 1 1 calc R . .
O5 O 0.7216(2) 0.1524(3) 0.6010(2) 0.0496(6) Uani 1 1 d . . .
C5 C 0.4145(3) 0.1003(3) 0.7020(2) 0.0250(6) Uani 1 1 d . . .
O6 O 0.5093(2) 0.1892(3) 0.49440(19) 0.0396(5) Uani 1 1 d . . .
C6 C 0.5561(3) 0.1224(3) 0.7098(2) 0.0276(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.383(3) . ?
O1 C1 1.434(3) . ?
N1 C5 1.317(3) . ?
N1 C2 1.475(3) . ?
N1 H1A 0.8600 . ?
C1 C4 1.499(4) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
O2 C3 1.424(4) . ?
O2 C4 1.432(3) . ?
N2 C5 1.350(3) . ?
N2 C3 1.433(3) . ?
N2 H2A 0.8600 . ?
C2 C3 1.527(4) . ?
C2 H2B 0.9800 . ?
N3 O3 1.223(3) . ?
N3 O4 1.243(3) . ?
N3 C6 1.423(3) . ?
C3 H3A 0.9800 . ?
N4 O5 1.226(3) . ?
N4 O6 1.246(3) . ?
N4 C6 1.405(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.425(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
C2 O1 C1 113.9(2) . . ?
C5 N1 C2 110.1(2) . . ?
C5 N1 H1A 124.9 . . ?
C2 N1 H1A 124.9 . . ?
O1 C1 C4 110.2(2) . . ?
O1 C1 H1B 109.6 . . ?
C4 C1 H1B 109.6 . . ?
O1 C1 H1C 109.6 . . ?
C4 C1 H1C 109.6 . . ?
H1B C1 H1C 108.1 . . ?
C3 O2 C4 112.3(2) . . ?
C5 N2 C3 110.0(2) . . ?
C5 N2 H2A 125.0 . . ?
C3 N2 H2A 125.0 . . ?
O1 C2 N1 114.8(2) . . ?
O1 C2 C3 116.0(2) . . ?
N1 C2 C3 99.9(2) . . ?
O1 C2 H2B 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
O3 N3 O4 122.5(2) . . ?
O3 N3 C6 119.8(2) . . ?
O4 N3 C6 117.7(2) . . ?
O2 C3 N2 107.4(2) . . ?
O2 C3 C2 112.5(2) . . ?
N2 C3 C2 100.5(2) . . ?
O2 C3 H3A 111.9 . . ?
N2 C3 H3A 111.9 . . ?
C2 C3 H3A 111.9 . . ?
O5 N4 O6 121.3(2) . . ?
O5 N4 C6 121.3(2) . . ?
O6 N4 C6 117.3(2) . . ?
O2 C4 C1 109.1(2) . . ?
O2 C4 H4A 109.9 . . ?
C1 C4 H4A 109.9 . . ?
O2 C4 H4B 109.9 . . ?
C1 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 N2 109.2(2) . . ?
N1 C5 C6 126.7(2) . . ?
N2 C5 C6 124.2(2) . . ?
N4 C6 N3 117.6(2) . . ?
N4 C6 C5 121.7(2) . . ?
N3 C6 C5 120.6(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
C2 O1 C1 C4 -53.4(3) . . . . ?
C1 O1 C2 N1 -72.7(3) . . . . ?
C1 O1 C2 C3 43.1(3) . . . . ?
C5 N1 C2 O1 149.3(2) . . . . ?
C5 N1 C2 C3 24.5(3) . . . . ?
C4 O2 C3 N2 158.1(2) . . . . ?
C4 O2 C3 C2 48.4(3) . . . . ?
C5 N2 C3 O2 -89.3(3) . . . . ?
C5 N2 C3 C2 28.5(3) . . . . ?
O1 C2 C3 O2 -40.1(3) . . . . ?
N1 C2 C3 O2 83.9(2) . . . . ?
O1 C2 C3 N2 -154.1(2) . . . . ?
N1 C2 C3 N2 -30.1(3) . . . . ?
C3 O2 C4 C1 -59.7(3) . . . . ?
O1 C1 C4 O2 61.2(3) . . . . ?
C2 N1 C5 N2 -7.9(3) . . . . ?
C2 N1 C5 C6 172.3(2) . . . . ?
C3 N2 C5 N1 -14.2(3) . . . . ?
C3 N2 C5 C6 165.7(3) . . . . ?
O5 N4 C6 N3 8.5(4) . . . . ?
O6 N4 C6 N3 -175.1(2) . . . . ?
O5 N4 C6 C5 -168.3(3) . . . . ?
O6 N4 C6 C5 8.1(4) . . . . ?
O3 N3 C6 N4 27.9(4) . . . . ?
O4 N3 C6 N4 -152.7(2) . . . . ?
O3 N3 C6 C5 -155.2(2) . . . . ?
O4 N3 C6 C5 24.1(4) . . . . ?
N1 C5 C6 N4 -8.5(4) . . . . ?
N2 C5 C6 N4 171.7(3) . . . . ?
N1 C5 C6 N3 174.8(2) . . . . ?
N2 C5 C6 N3 -5.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1500623'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N6 O10'
_chemical_formula_weight         322.17

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           Monoclinic
_symmetry_space_group_name_H-M   P21/N

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.437(4)
_cell_length_b                   6.2410(12)
_cell_length_c                   20.588(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.82(3)
_cell_angle_gamma                90.00
_cell_volume                     2402.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4527
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         25.46
_reflns_number_total             4399
_reflns_number_gt                1894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0580P)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         4399
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.1322(3) 0.2791(8) 0.4696(2) 0.0439(12) Uani 1 1 d . . .
O1 O 0.1107(4) -0.0553(8) 0.4177(3) 0.123(2) Uani 1 1 d . . .
O2 O 0.0251(3) 0.0962(9) 0.4365(2) 0.1068(17) Uani 1 1 d . . .
O3 O 0.1743(2) 0.3169(10) 0.3799(2) 0.114(2) Uani 1 1 d . . .
O4 O 0.2476(2) 0.2142(9) 0.4819(2) 0.1071(19) Uani 1 1 d . . .
O5 O 0.0576(2) 0.5010(7) 0.37863(19) 0.0789(13) Uani 1 1 d . . .
O6 O 0.0691(2) 0.5671(7) 0.4866(2) 0.0786(13) Uani 1 1 d . . .
O7 O 0.2755(2) 0.7063(8) 0.6275(2) 0.0850(13) Uani 1 1 d . . .
O8 O 0.2178(2) 0.6295(7) 0.5142(2) 0.0772(12) Uani 1 1 d . . .
O9 O 0.1494(2) 0.0778(7) 0.69440(16) 0.0731(12) Uani 1 1 d . . .
O10 O 0.18627(19) 0.4965(7) 0.69585(18) 0.0738(12) Uani 1 1 d . . .
N1 N 0.0848(3) 0.0789(10) 0.4365(2) 0.0682(15) Uani 1 1 d . . .
N2 N 0.1917(3) 0.2760(8) 0.4404(2) 0.0649(14) Uani 1 1 d . . .
N3 N 0.0823(2) 0.4672(8) 0.4441(2) 0.0582(12) Uani 1 1 d . . .
N4 N 0.2356(2) 0.5950(9) 0.5780(3) 0.0631(13) Uani 1 1 d . . .
N5 N 0.2107(2) 0.4075(8) 0.5949(2) 0.0558(12) Uani 1 1 d . . .
N6 N 0.1492(2) 0.1026(7) 0.57817(19) 0.0540(11) Uani 1 1 d . . .
C2 C 0.1650(3) 0.2618(8) 0.5494(2) 0.0409(12) Uani 1 1 d . . .
C3 C 0.1917(3) 0.1283(11) 0.6566(2) 0.0660(17) Uani 1 1 d . . .
H3A H 0.2324 0.0292 0.6714 0.079 Uiso 1 1 calc R . .
C4 C 0.0996(3) 0.2362(11) 0.6940(3) 0.078(2) Uani 1 1 d . . .
H4A H 0.1014 0.2499 0.7416 0.093 Uiso 1 1 calc R . .
H4B H 0.0518 0.1884 0.6634 0.093 Uiso 1 1 calc R . .
C5 C 0.1121(3) 0.4543(11) 0.6691(3) 0.0709(18) Uani 1 1 d . . .
H5A H 0.0919 0.4583 0.6176 0.085 Uiso 1 1 calc R . .
H5B H 0.0886 0.5633 0.6856 0.085 Uiso 1 1 calc R . .
C6 C 0.2207(3) 0.3587(9) 0.6701(2) 0.0556(15) Uani 1 1 d . . .
H6B H 0.2718 0.3570 0.7012 0.067 Uiso 1 1 calc R . .
O11 O 0.3757(2) 0.1796(9) 0.6732(2) 0.0958(16) Uani 1 1 d . . .
O12 O 0.4776(2) 0.3020(7) 0.7438(2) 0.0780(13) Uani 1 1 d . . .
O13 O 0.3770(2) -0.0120(7) 0.5584(2) 0.0762(12) Uani 1 1 d . . .
O14 O 0.4845(2) -0.0734(7) 0.57083(17) 0.0706(12) Uani 1 1 d . . .
O15 O 0.4372(2) 0.3946(9) 0.5249(2) 0.0982(16) Uani 1 1 d . . .
O16 O 0.4130(2) 0.5482(8) 0.6066(3) 0.1005(16) Uani 1 1 d . . .
O17 O 0.5096(2) -0.1325(7) 0.71701(19) 0.0668(11) Uani 1 1 d . . .
O18 O 0.6224(2) -0.2135(7) 0.7719(2) 0.0762(12) Uani 1 1 d . . .
O19 O 0.69579(18) 0.4033(8) 0.6510(2) 0.0784(12) Uani 1 1 d . . .
O20 O 0.69434(19) -0.0110(7) 0.68691(18) 0.0746(12) Uani 1 1 d . . .
N7 N 0.4361(3) 0.2330(8) 0.6878(2) 0.0600(13) Uani 1 1 d . . .
N8 N 0.4406(3) 0.0233(8) 0.5832(2) 0.0528(12) Uani 1 1 d . . .
N9 N 0.4353(2) 0.4041(8) 0.5810(3) 0.0596(12) Uani 1 1 d . . .
N10 N 0.5725(3) -0.1052(9) 0.7344(2) 0.0608(13) Uani 1 1 d . . .
N11 N 0.5933(2) 0.0800(8) 0.7110(2) 0.0523(11) Uani 1 1 d . . .
N12 N 0.5781(2) 0.3874(7) 0.64929(19) 0.0447(10) Uani 1 1 d . . .
C7 C 0.4679(2) 0.2191(8) 0.6323(2) 0.0425(12) Uani 1 1 d . . .
C8 C 0.5482(2) 0.2335(9) 0.6644(2) 0.0425(13) Uani 1 1 d . . .
C9 C 0.6670(3) 0.1321(10) 0.7214(3) 0.0575(15) Uani 1 1 d . . .
H9A H 0.6979 0.1354 0.7722 0.069 Uiso 1 1 calc R . .
C10 C 0.6668(3) 0.0333(11) 0.6117(3) 0.0677(17) Uani 1 1 d . . .
H10A H 0.6150 0.0301 0.5919 0.081 Uiso 1 1 calc R . .
H10B H 0.6830 -0.0768 0.5883 0.081 Uiso 1 1 calc R . .
C11 C 0.6909(4) 0.2426(11) 0.5985(3) 0.078(2) Uani 1 1 d . . .
H11A H 0.7376 0.2265 0.5971 0.094 Uiso 1 1 calc R . .
H11B H 0.6581 0.2930 0.5522 0.094 Uiso 1 1 calc R . .
C12 C 0.6554(3) 0.3605(10) 0.6912(3) 0.0566(15) Uani 1 1 d . . .
H12B H 0.6702 0.4614 0.7311 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.503(6) . ?
C1 C2 1.506(6) . ?
C1 N2 1.559(6) . ?
C1 N1 1.559(7) . ?
O1 N1 1.138(6) . ?
O2 N1 1.225(6) . ?
O3 N2 1.178(5) . ?
O4 N2 1.180(5) . ?
O5 N3 1.251(5) . ?
O6 N3 1.193(5) . ?
O7 N4 1.230(5) . ?
O8 N4 1.232(5) . ?
O9 C3 1.414(6) . ?
O9 C4 1.417(6) . ?
O10 C6 1.348(6) . ?
O10 C5 1.413(6) . ?
N4 N5 1.377(6) . ?
N5 C2 1.367(6) . ?
N5 C6 1.508(6) . ?
N6 C2 1.264(6) . ?
N6 C3 1.501(6) . ?
C3 C6 1.538(8) . ?
C3 H3A 0.9800 . ?
C4 C5 1.512(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6B 0.9800 . ?
O11 N7 1.193(5) . ?
O12 N7 1.201(5) . ?
O13 N8 1.211(5) . ?
O14 N8 1.190(5) . ?
O15 N9 1.173(6) . ?
O16 N9 1.220(6) . ?
O17 N10 1.199(5) . ?
O18 N10 1.206(5) . ?
O19 C12 1.410(5) . ?
O19 C11 1.449(7) . ?
O20 C9 1.391(5) . ?
O20 C10 1.445(6) . ?
N7 C7 1.530(6) . ?
N8 C7 1.539(6) . ?
N9 C7 1.524(6) . ?
N10 N11 1.384(6) . ?
N11 C8 1.404(6) . ?
N11 C9 1.469(6) . ?
N12 C8 1.243(6) . ?
N12 C12 1.472(6) . ?
C7 C8 1.504(6) . ?
C9 C12 1.534(8) . ?
C9 H9A 0.9800 . ?
C10 C11 1.460(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 112.2(4) . . ?
N3 C1 N2 113.5(4) . . ?
C2 C1 N2 110.3(4) . . ?
N3 C1 N1 105.0(4) . . ?
C2 C1 N1 110.1(4) . . ?
N2 C1 N1 105.3(4) . . ?
C3 O9 C4 116.1(5) . . ?
C6 O10 C5 112.1(4) . . ?
O1 N1 O2 131.7(7) . . ?
O1 N1 C1 116.5(6) . . ?
O2 N1 C1 111.8(6) . . ?
O3 N2 O4 128.7(5) . . ?
O3 N2 C1 117.2(5) . . ?
O4 N2 C1 113.7(4) . . ?
O6 N3 O5 126.1(5) . . ?
O6 N3 C1 118.3(4) . . ?
O5 N3 C1 115.5(5) . . ?
O7 N4 O8 126.6(6) . . ?
O7 N4 N5 117.4(5) . . ?
O8 N4 N5 116.0(5) . . ?
C2 N5 N4 127.7(4) . . ?
C2 N5 C6 110.0(4) . . ?
N4 N5 C6 121.3(4) . . ?
C2 N6 C3 105.9(4) . . ?
N6 C2 N5 115.7(4) . . ?
N6 C2 C1 118.8(5) . . ?
N5 C2 C1 125.5(4) . . ?
O9 C3 N6 110.6(4) . . ?
O9 C3 C6 112.7(4) . . ?
N6 C3 C6 108.0(4) . . ?
O9 C3 H3A 108.5 . . ?
N6 C3 H3A 108.5 . . ?
C6 C3 H3A 108.5 . . ?
O9 C4 C5 114.3(5) . . ?
O9 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
O9 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O10 C5 C4 109.7(5) . . ?
O10 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
O10 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O10 C6 N5 113.5(4) . . ?
O10 C6 C3 116.3(5) . . ?
N5 C6 C3 96.9(4) . . ?
O10 C6 H6B 109.8 . . ?
N5 C6 H6B 109.8 . . ?
C3 C6 H6B 109.8 . . ?
C12 O19 C11 115.3(5) . . ?
C9 O20 C10 111.2(4) . . ?
O11 N7 O12 126.8(5) . . ?
O11 N7 C7 120.3(5) . . ?
O12 N7 C7 112.8(4) . . ?
O14 N8 O13 126.2(5) . . ?
O14 N8 C7 116.0(4) . . ?
O13 N8 C7 117.7(4) . . ?
O15 N9 O16 129.0(5) . . ?
O15 N9 C7 117.7(5) . . ?
O16 N9 C7 113.2(5) . . ?
O17 N10 O18 129.6(6) . . ?
O17 N10 N11 117.2(5) . . ?
O18 N10 N11 113.1(5) . . ?
N10 N11 C8 126.8(4) . . ?
N10 N11 C9 125.1(5) . . ?
C8 N11 C9 107.4(4) . . ?
C8 N12 C12 106.5(4) . . ?
C8 C7 N9 110.7(4) . . ?
C8 C7 N7 112.7(4) . . ?
N9 C7 N7 106.0(4) . . ?
C8 C7 N8 112.2(4) . . ?
N9 C7 N8 101.9(4) . . ?
N7 C7 N8 112.6(4) . . ?
N12 C8 N11 116.4(4) . . ?
N12 C8 C7 119.7(5) . . ?
N11 C8 C7 123.9(5) . . ?
O20 C9 N11 112.5(4) . . ?
O20 C9 C12 114.7(4) . . ?
N11 C9 C12 99.5(4) . . ?
O20 C9 H9A 109.9 . . ?
N11 C9 H9A 109.9 . . ?
C12 C9 H9A 109.9 . . ?
O20 C10 C11 110.9(5) . . ?
O20 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
O20 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
O19 C11 C10 114.0(5) . . ?
O19 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
O19 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
O19 C12 N12 112.2(4) . . ?
O19 C12 C9 112.5(4) . . ?
N12 C12 C9 107.3(4) . . ?
O19 C12 H12B 108.2 . . ?
N12 C12 H12B 108.2 . . ?
C9 C12 H12B 108.2 . . ?

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
N3 C1 N1 O1 142.2(5) . . . . ?
C2 C1 N1 O1 -96.8(5) . . . . ?
N2 C1 N1 O1 22.0(6) . . . . ?
N3 C1 N1 O2 -38.7(5) . . . . ?
C2 C1 N1 O2 82.3(5) . . . . ?
N2 C1 N1 O2 -158.9(4) . . . . ?
N3 C1 N2 O3 -43.3(7) . . . . ?
C2 C1 N2 O3 -170.2(5) . . . . ?
N1 C1 N2 O3 71.1(6) . . . . ?
N3 C1 N2 O4 142.8(5) . . . . ?
C2 C1 N2 O4 15.9(7) . . . . ?
N1 C1 N2 O4 -102.9(6) . . . . ?
C2 C1 N3 O6 -6.6(6) . . . . ?
N2 C1 N3 O6 -132.4(5) . . . . ?
N1 C1 N3 O6 113.0(5) . . . . ?
C2 C1 N3 O5 174.6(4) . . . . ?
N2 C1 N3 O5 48.7(6) . . . . ?
N1 C1 N3 O5 -65.8(5) . . . . ?
O7 N4 N5 C2 178.6(5) . . . . ?
O8 N4 N5 C2 -4.4(7) . . . . ?
O7 N4 N5 C6 10.6(7) . . . . ?
O8 N4 N5 C6 -172.4(5) . . . . ?
C3 N6 C2 N5 -2.8(6) . . . . ?
C3 N6 C2 C1 178.3(4) . . . . ?
N4 N5 C2 N6 -179.0(4) . . . . ?
C6 N5 C2 N6 -10.0(6) . . . . ?
N4 N5 C2 C1 -0.1(8) . . . . ?
C6 N5 C2 C1 169.0(4) . . . . ?
N3 C1 C2 N6 114.0(5) . . . . ?
N2 C1 C2 N6 -118.4(5) . . . . ?
N1 C1 C2 N6 -2.6(6) . . . . ?
N3 C1 C2 N5 -64.9(6) . . . . ?
N2 C1 C2 N5 62.7(6) . . . . ?
N1 C1 C2 N5 178.6(5) . . . . ?
C4 O9 C3 N6 -77.0(6) . . . . ?
C4 O9 C3 C6 43.9(6) . . . . ?
C2 N6 C3 O9 137.7(5) . . . . ?
C2 N6 C3 C6 14.1(6) . . . . ?
C3 O9 C4 C5 -14.6(7) . . . . ?
C6 O10 C5 C4 64.1(5) . . . . ?
O9 C4 C5 O10 -39.1(6) . . . . ?
C5 O10 C6 N5 76.9(6) . . . . ?
C5 O10 C6 C3 -34.2(6) . . . . ?
C2 N5 C6 O10 -106.0(5) . . . . ?
N4 N5 C6 O10 63.9(6) . . . . ?
C2 N5 C6 C3 16.6(5) . . . . ?
N4 N5 C6 C3 -173.5(4) . . . . ?
O9 C3 C6 O10 -19.8(6) . . . . ?
N6 C3 C6 O10 102.7(5) . . . . ?
O9 C3 C6 N5 -140.2(4) . . . . ?
N6 C3 C6 N5 -17.8(5) . . . . ?
O17 N10 N11 C8 -5.1(7) . . . . ?
O18 N10 N11 C8 177.0(4) . . . . ?
O17 N10 N11 C9 -174.3(4) . . . . ?
O18 N10 N11 C9 7.8(6) . . . . ?
O15 N9 C7 C8 76.5(6) . . . . ?
O16 N9 C7 C8 -100.6(5) . . . . ?
O15 N9 C7 N7 -160.9(5) . . . . ?
O16 N9 C7 N7 21.9(6) . . . . ?
O15 N9 C7 N8 -42.9(6) . . . . ?
O16 N9 C7 N8 139.9(4) . . . . ?
O11 N7 C7 C8 -164.2(5) . . . . ?
O12 N7 C7 C8 16.4(7) . . . . ?
O11 N7 C7 N9 74.6(6) . . . . ?
O12 N7 C7 N9 -104.9(5) . . . . ?
O11 N7 C7 N8 -36.0(7) . . . . ?
O12 N7 C7 N8 144.5(5) . . . . ?
O14 N8 C7 C8 -8.3(6) . . . . ?
O13 N8 C7 C8 175.1(4) . . . . ?
O14 N8 C7 N9 110.1(4) . . . . ?
O13 N8 C7 N9 -66.5(5) . . . . ?
O14 N8 C7 N7 -136.8(4) . . . . ?
O13 N8 C7 N7 46.6(6) . . . . ?
C12 N12 C8 N11 -3.2(5) . . . . ?
C12 N12 C8 C7 177.4(4) . . . . ?
N10 N11 C8 N12 -178.9(4) . . . . ?
C9 N11 C8 N12 -8.2(5) . . . . ?
N10 N11 C8 C7 0.4(6) . . . . ?
C9 N11 C8 C7 171.1(4) . . . . ?
N9 C7 C8 N12 2.5(6) . . . . ?
N7 C7 C8 N12 -116.0(5) . . . . ?
N8 C7 C8 N12 115.5(5) . . . . ?
N9 C7 C8 N11 -176.8(4) . . . . ?
N7 C7 C8 N11 64.7(6) . . . . ?
N8 C7 C8 N11 -63.8(5) . . . . ?
C10 O20 C9 N11 77.6(6) . . . . ?
C10 O20 C9 C12 -35.1(6) . . . . ?
N10 N11 C9 O20 63.6(6) . . . . ?
C8 N11 C9 O20 -107.3(5) . . . . ?
N10 N11 C9 C12 -174.5(4) . . . . ?
C8 N11 C9 C12 14.6(4) . . . . ?
C9 O20 C10 C11 64.6(6) . . . . ?
C12 O19 C11 C10 -20.5(8) . . . . ?
O20 C10 C11 O19 -35.7(7) . . . . ?
C11 O19 C12 N12 -72.3(6) . . . . ?
C11 O19 C12 C9 48.8(6) . . . . ?
C8 N12 C12 O19 136.9(5) . . . . ?
C8 N12 C12 C9 12.9(5) . . . . ?
O20 C9 C12 O19 -20.1(6) . . . . ?
N11 C9 C12 O19 -140.3(4) . . . . ?
O20 C9 C12 N12 103.8(4) . . . . ?
N11 C9 C12 N12 -16.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1500624'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 N6 O8'
_chemical_formula_weight         278.16

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4150(17)
_cell_length_b                   10.916(2)
_cell_length_c                   12.774(3)
_cell_angle_alpha                72.30(3)
_cell_angle_beta                 83.98(3)
_cell_angle_gamma                83.60(3)
_cell_volume                     1107.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4371
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.39
_reflns_number_total             4072
_reflns_number_gt                2012
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0850P)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         4072
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O1 O 0.0468(4) 1.0001(3) 0.1226(2) 0.0846(9) Uani 1 1 d . . .
O2 O 0.1948(4) 0.9240(3) 0.2602(3) 0.0821(8) Uani 1 1 d . . .
O3 O 0.5020(5) 0.7524(4) 0.3551(3) 0.1347(15) Uani 1 1 d . . .
O4 O 0.4408(4) 0.7388(3) 0.2014(3) 0.1023(11) Uani 1 1 d . . .
O5 O 0.4306(5) 0.4779(3) 0.3616(3) 0.1118(12) Uani 1 1 d . . .
O6 O 0.2248(5) 0.4654(3) 0.4779(3) 0.1019(11) Uani 1 1 d . . .
O7 O 0.2702(5) 0.7114(4) 0.5159(3) 0.1264(14) Uani 1 1 d . . .
O8 O 0.0452(5) 0.7401(4) 0.4468(3) 0.1072(11) Uani 1 1 d . . .
N1 N 0.1034(4) 0.5765(3) 0.2520(2) 0.0634(8) Uani 1 1 d . . .
N2 N 0.0733(4) 0.7924(3) 0.2018(2) 0.0684(9) Uani 1 1 d . . .
N3 N 0.1074(4) 0.9121(3) 0.1936(3) 0.0623(8) Uani 1 1 d . . .
N4 N 0.4167(4) 0.7269(4) 0.2973(4) 0.0820(10) Uani 1 1 d . . .
N5 N 0.3129(5) 0.5222(3) 0.4025(3) 0.0744(10) Uani 1 1 d . . .
N6 N 0.1849(6) 0.7126(3) 0.4464(3) 0.0800(10) Uani 1 1 d . . .
C1 C -0.0207(5) 0.6164(4) 0.1703(3) 0.0688(11) Uani 1 1 d . . .
H1B H 0.0126 0.5804 0.1091 0.083 Uiso 1 1 calc R . .
C2 C -0.0285(5) 0.7635(4) 0.1277(3) 0.0714(11) Uani 1 1 d . . .
H2A H 0.0142 0.7931 0.0516 0.086 Uiso 1 1 calc R . .
H2B H -0.1373 0.8019 0.1343 0.086 Uiso 1 1 calc R . .
C3 C 0.1453(4) 0.6752(4) 0.2668(3) 0.0526(9) Uani 1 1 d . . .
C4 C -0.1759(6) 0.5656(6) 0.2260(4) 0.1108(18) Uani 1 1 d . . .
H4A H -0.1634 0.4730 0.2506 0.166 Uiso 1 1 calc R . .
H4B H -0.2580 0.5937 0.1750 0.166 Uiso 1 1 calc R . .
H4C H -0.2058 0.5975 0.2882 0.166 Uiso 1 1 calc R . .
C5 C 0.2614(4) 0.6657(3) 0.3510(3) 0.0591(9) Uani 1 1 d . . .
O9 O 0.3323(4) 0.2926(3) 0.0328(2) 0.0944(10) Uani 1 1 d . . .
O10 O 0.0893(4) 0.3202(3) 0.1030(2) 0.0925(10) Uani 1 1 d . . .
O11 O 0.4738(6) 0.0390(4) 0.1166(4) 0.1505(19) Uani 1 1 d . . .
O12 O 0.6837(4) 0.1107(4) 0.0210(3) 0.1226(13) Uani 1 1 d . . .
O13 O 0.7898(5) 0.2167(7) 0.2575(4) 0.172(3) Uani 1 1 d . . .
O14 O 0.7526(5) 0.0271(6) 0.2535(3) 0.152(2) Uani 1 1 d . . .
O15 O 0.7116(5) 0.3510(4) 0.0188(3) 0.1407(16) Uani 1 1 d . . .
O16 O 0.5367(5) 0.4196(4) 0.1273(3) 0.1225(14) Uani 1 1 d . . .
N7 N 0.4470(4) 0.1513(4) 0.3427(2) 0.0788(11) Uani 1 1 d . . .
N8 N 0.2819(3) 0.2431(3) 0.2125(2) 0.0679(9) Uani 1 1 d . . .
N9 N 0.2305(5) 0.2881(3) 0.1095(3) 0.0730(9) Uani 1 1 d . . .
N10 N 0.5784(5) 0.1096(4) 0.0913(3) 0.0896(12) Uani 1 1 d . . .
N11 N 0.7266(6) 0.1446(7) 0.2304(3) 0.1108(18) Uani 1 1 d . . .
N12 N 0.6127(5) 0.3362(5) 0.0953(3) 0.0895(12) Uani 1 1 d . . .
C6 C 0.2880(4) 0.1638(4) 0.4004(3) 0.0721(11) Uani 1 1 d . . .
H6A H 0.2920 0.2242 0.4431 0.087 Uiso 1 1 calc R . .
C7 C 0.1732(4) 0.2255(4) 0.3105(3) 0.0641(10) Uani 1 1 d . . .
H7B H 0.0917 0.1687 0.3117 0.077 Uiso 1 1 calc R . .
H7C H 0.1218 0.3072 0.3170 0.077 Uiso 1 1 calc R . .
C8 C 0.4343(4) 0.1961(4) 0.2411(3) 0.0583(9) Uani 1 1 d . . .
C9 C 0.2471(6) 0.0418(5) 0.4760(4) 0.1016(16) Uani 1 1 d . . .
H9A H 0.3256 0.0111 0.5295 0.152 Uiso 1 1 calc R . .
H9B H 0.2450 -0.0196 0.4362 0.152 Uiso 1 1 calc R . .
H9C H 0.1434 0.0527 0.5129 0.152 Uiso 1 1 calc R . .
C10 C 0.5784(4) 0.1996(4) 0.1620(3) 0.0689(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.209(4) . ?
O2 N3 1.225(4) . ?
O3 N4 1.191(4) . ?
O4 N4 1.191(4) . ?
O5 N5 1.195(4) . ?
O6 N5 1.205(5) . ?
O7 N6 1.195(4) . ?
O8 N6 1.181(4) . ?
N1 C3 1.242(4) . ?
N1 C1 1.490(4) . ?
N2 N3 1.339(4) . ?
N2 C3 1.408(4) . ?
N2 C2 1.463(5) . ?
N4 C5 1.534(5) . ?
N5 C5 1.535(5) . ?
N6 C5 1.517(5) . ?
C1 C4 1.499(6) . ?
C1 C2 1.527(5) . ?
C1 H1B 0.9800 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C5 1.501(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O9 N9 1.225(4) . ?
O10 N9 1.205(4) . ?
O11 N10 1.188(5) . ?
O12 N10 1.192(4) . ?
O13 N11 1.148(7) . ?
O14 N11 1.225(7) . ?
O15 N12 1.198(5) . ?
O16 N12 1.203(5) . ?
N7 C8 1.251(4) . ?
N7 C6 1.472(5) . ?
N8 N9 1.356(4) . ?
N8 C8 1.371(4) . ?
N8 C7 1.447(4) . ?
N10 C10 1.523(6) . ?
N11 C10 1.556(6) . ?
N12 C10 1.519(6) . ?
C6 C9 1.441(6) . ?
C6 C7 1.524(5) . ?
C6 H6A 0.9800 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C10 1.491(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C3 N1 C1 108.3(3) . . ?
N3 N2 C3 127.6(3) . . ?
N3 N2 C2 123.4(3) . . ?
C3 N2 C2 108.3(3) . . ?
O1 N3 O2 125.1(4) . . ?
O1 N3 N2 117.5(3) . . ?
O2 N3 N2 117.3(3) . . ?
O4 N4 O3 127.2(4) . . ?
O4 N4 C5 114.9(4) . . ?
O3 N4 C5 117.8(4) . . ?
O5 N5 O6 127.1(4) . . ?
O5 N5 C5 117.4(4) . . ?
O6 N5 C5 115.4(4) . . ?
O8 N6 O7 126.8(4) . . ?
O8 N6 C5 116.1(4) . . ?
O7 N6 C5 116.9(4) . . ?
N1 C1 C4 108.7(3) . . ?
N1 C1 C2 106.1(3) . . ?
C4 C1 C2 113.5(4) . . ?
N1 C1 H1B 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N2 C2 C1 101.4(3) . . ?
N2 C2 H2A 111.5 . . ?
C1 C2 H2A 111.5 . . ?
N2 C2 H2B 111.5 . . ?
C1 C2 H2B 111.5 . . ?
H2A C2 H2B 109.3 . . ?
N1 C3 N2 115.2(3) . . ?
N1 C3 C5 120.9(3) . . ?
N2 C3 C5 123.9(3) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 N6 112.6(3) . . ?
C3 C5 N4 111.6(3) . . ?
N6 C5 N4 114.2(3) . . ?
C3 C5 N5 107.7(3) . . ?
N6 C5 N5 105.1(3) . . ?
N4 C5 N5 104.9(3) . . ?
C8 N7 C6 108.7(3) . . ?
N9 N8 C8 127.3(3) . . ?
N9 N8 C7 122.5(3) . . ?
C8 N8 C7 109.9(3) . . ?
O10 N9 O9 126.8(3) . . ?
O10 N9 N8 116.5(3) . . ?
O9 N9 N8 116.7(3) . . ?
O11 N10 O12 125.9(5) . . ?
O11 N10 C10 114.9(4) . . ?
O12 N10 C10 119.1(4) . . ?
O13 N11 O14 129.1(6) . . ?
O13 N11 C10 116.9(7) . . ?
O14 N11 C10 113.9(6) . . ?
O15 N12 O16 126.6(5) . . ?
O15 N12 C10 118.5(5) . . ?
O16 N12 C10 114.8(4) . . ?
C9 C6 N7 111.1(4) . . ?
C9 C6 C7 115.6(4) . . ?
N7 C6 C7 105.9(3) . . ?
C9 C6 H6A 108.0 . . ?
N7 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
N8 C7 C6 101.1(3) . . ?
N8 C7 H7B 111.6 . . ?
C6 C7 H7B 111.6 . . ?
N8 C7 H7C 111.6 . . ?
C6 C7 H7C 111.6 . . ?
H7B C7 H7C 109.4 . . ?
N7 C8 N8 114.4(3) . . ?
N7 C8 C10 120.5(3) . . ?
N8 C8 C10 125.1(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 N12 112.4(4) . . ?
C8 C10 N10 113.8(3) . . ?
N12 C10 N10 113.1(3) . . ?
C8 C10 N11 107.7(3) . . ?
N12 C10 N11 105.3(4) . . ?
N10 C10 N11 103.4(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
C3 N2 N3 O1 170.7(3) . . . . ?
C2 N2 N3 O1 1.9(5) . . . . ?
C3 N2 N3 O2 -10.9(5) . . . . ?
C2 N2 N3 O2 -179.6(3) . . . . ?
C3 N1 C1 C4 -115.2(4) . . . . ?
C3 N1 C1 C2 7.2(4) . . . . ?
N3 N2 C2 C1 177.7(3) . . . . ?
C3 N2 C2 C1 7.1(4) . . . . ?
N1 C1 C2 N2 -8.4(4) . . . . ?
C4 C1 C2 N2 110.9(4) . . . . ?
C1 N1 C3 N2 -2.7(4) . . . . ?
C1 N1 C3 C5 175.7(3) . . . . ?
N3 N2 C3 N1 -173.2(3) . . . . ?
C2 N2 C3 N1 -3.1(4) . . . . ?
N3 N2 C3 C5 8.4(6) . . . . ?
C2 N2 C3 C5 178.5(3) . . . . ?
N1 C3 C5 N6 -113.2(4) . . . . ?
N2 C3 C5 N6 65.2(4) . . . . ?
N1 C3 C5 N4 116.9(4) . . . . ?
N2 C3 C5 N4 -64.8(4) . . . . ?
N1 C3 C5 N5 2.3(5) . . . . ?
N2 C3 C5 N5 -179.4(3) . . . . ?
O8 N6 C5 C3 5.6(5) . . . . ?
O7 N6 C5 C3 -178.1(4) . . . . ?
O8 N6 C5 N4 134.2(4) . . . . ?
O7 N6 C5 N4 -49.6(5) . . . . ?
O8 N6 C5 N5 -111.4(4) . . . . ?
O7 N6 C5 N5 64.9(4) . . . . ?
O4 N4 C5 C3 -19.7(5) . . . . ?
O3 N4 C5 C3 163.1(4) . . . . ?
O4 N4 C5 N6 -148.8(4) . . . . ?
O3 N4 C5 N6 34.0(5) . . . . ?
O4 N4 C5 N5 96.6(4) . . . . ?
O3 N4 C5 N5 -80.6(5) . . . . ?
O5 N5 C5 C3 92.1(4) . . . . ?
O6 N5 C5 C3 -84.9(4) . . . . ?
O5 N5 C5 N6 -147.7(4) . . . . ?
O6 N5 C5 N6 35.4(4) . . . . ?
O5 N5 C5 N4 -26.9(5) . . . . ?
O6 N5 C5 N4 156.1(3) . . . . ?
C8 N8 N9 O10 177.1(4) . . . . ?
C7 N8 N9 O10 4.2(6) . . . . ?
C8 N8 N9 O9 -3.3(6) . . . . ?
C7 N8 N9 O9 -176.2(4) . . . . ?
C8 N7 C6 C9 127.0(4) . . . . ?
C8 N7 C6 C7 0.7(5) . . . . ?
N9 N8 C7 C6 175.4(4) . . . . ?
C8 N8 C7 C6 1.3(4) . . . . ?
C9 C6 C7 N8 -124.7(4) . . . . ?
N7 C6 C7 N8 -1.2(4) . . . . ?
C6 N7 C8 N8 0.2(5) . . . . ?
C6 N7 C8 C10 178.2(4) . . . . ?
N9 N8 C8 N7 -174.7(4) . . . . ?
C7 N8 C8 N7 -1.0(5) . . . . ?
N9 N8 C8 C10 7.4(6) . . . . ?
C7 N8 C8 C10 -179.0(4) . . . . ?
N7 C8 C10 N12 -117.1(4) . . . . ?
N8 C8 C10 N12 60.7(5) . . . . ?
N7 C8 C10 N10 112.5(4) . . . . ?
N8 C8 C10 N10 -69.7(5) . . . . ?
N7 C8 C10 N11 -1.6(6) . . . . ?
N8 C8 C10 N11 176.3(5) . . . . ?
O15 N12 C10 C8 -169.9(4) . . . . ?
O16 N12 C10 C8 11.2(5) . . . . ?
O15 N12 C10 N10 -39.2(5) . . . . ?
O16 N12 C10 N10 141.9(4) . . . . ?
O15 N12 C10 N11 73.1(5) . . . . ?
O16 N12 C10 N11 -105.8(5) . . . . ?
O11 N10 C10 C8 -7.9(5) . . . . ?
O12 N10 C10 C8 175.7(4) . . . . ?
O11 N10 C10 N12 -137.9(4) . . . . ?
O12 N10 C10 N12 45.7(5) . . . . ?
O11 N10 C10 N11 108.7(5) . . . . ?
O12 N10 C10 N11 -67.8(5) . . . . ?
O13 N11 C10 C8 -88.0(5) . . . . ?
O14 N11 C10 C8 87.6(5) . . . . ?
O13 N11 C10 N12 32.2(6) . . . . ?
O14 N11 C10 N12 -152.3(4) . . . . ?
O13 N11 C10 N10 151.2(5) . . . . ?
O14 N11 C10 N10 -33.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1500625'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N6 O12'
_chemical_formula_weight         380.20

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

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

_cell_length_a                   8.6990(17)
_cell_length_b                   8.7890(18)
_cell_length_c                   10.723(2)
_cell_angle_alpha                86.59(3)
_cell_angle_beta                 89.54(3)
_cell_angle_gamma                72.16(3)
_cell_volume                     779.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3069
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2867
_reflns_number_gt                1833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.3300P] 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         2867
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1889
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
O1 O 0.1125(3) 0.6464(3) 0.1801(2) 0.0509(6) Uani 1 1 d . . .
N1 N -0.1653(3) 0.9646(3) 0.2098(3) 0.0486(7) Uani 1 1 d . . .
C1 C 0.0156(4) 0.7255(4) 0.2779(3) 0.0449(8) Uani 1 1 d . . .
H1A H 0.0207 0.6526 0.3516 0.054 Uiso 1 1 calc R . .
N2 N 0.0741(3) 0.8594(3) 0.3065(2) 0.0448(7) Uani 1 1 d . . .
C2 C -0.1582(4) 0.7981(4) 0.2283(3) 0.0437(8) Uani 1 1 d . . .
H2B H -0.1768 0.7524 0.1508 0.052 Uiso 1 1 calc R . .
O2 O 0.2615(4) 0.4651(4) 0.3212(3) 0.0891(10) Uani 1 1 d . . .
O3 O -0.2681(3) 0.7850(3) 0.3228(2) 0.0525(6) Uani 1 1 d . . .
C3 C -0.0274(4) 0.9853(4) 0.2624(3) 0.0381(7) Uani 1 1 d . . .
N3 N -0.2825(4) 1.0749(4) 0.1387(3) 0.0578(8) Uani 1 1 d . . .
N4 N -0.1159(4) 1.2648(4) 0.3425(3) 0.0631(9) Uani 1 1 d . . .
C4 C 0.2415(4) 0.5158(4) 0.2156(4) 0.0595(10) Uani 1 1 d . . .
O4 O -0.3787(5) 0.6492(5) 0.2021(3) 0.1016(13) Uani 1 1 d . . .
O5 O -0.2671(3) 1.2077(3) 0.1217(3) 0.0747(9) Uani 1 1 d . . .
N5 N 0.1680(4) 1.1111(3) 0.3367(3) 0.0551(8) Uani 1 1 d . . .
C5 C 0.3403(5) 0.4567(5) 0.1066(5) 0.0812(14) Uani 1 1 d . . .
H5A H 0.4302 0.3657 0.1324 0.122 Uiso 1 1 calc R . .
H5B H 0.3793 0.5397 0.0695 0.122 Uiso 1 1 calc R . .
H5C H 0.2758 0.4258 0.0465 0.122 Uiso 1 1 calc R . .
N6 N 0.0284(4) 1.2125(4) 0.1372(3) 0.0564(8) Uani 1 1 d . . .
O6 O -0.3890(3) 1.0280(4) 0.1006(3) 0.0808(9) Uani 1 1 d . . .
C6 C -0.3761(5) 0.7060(5) 0.2985(4) 0.0579(9) Uani 1 1 d . . .
O7 O -0.2287(4) 1.2253(4) 0.3808(3) 0.0960(11) Uani 1 1 d . . .
C7 C -0.4819(5) 0.7065(6) 0.4068(4) 0.0805(13) Uani 1 1 d . . .
H7A H -0.5573 0.6506 0.3885 0.121 Uiso 1 1 calc R . .
H7B H -0.5398 0.8150 0.4240 0.121 Uiso 1 1 calc R . .
H7C H -0.4175 0.6543 0.4784 0.121 Uiso 1 1 calc R . .
C8 C 0.0054(4) 1.1434(4) 0.2676(3) 0.0443(8) Uani 1 1 d . . .
O8 O -0.0854(5) 1.3850(4) 0.3616(4) 0.1043(13) Uani 1 1 d . . .
O9 O 0.1608(4) 1.0996(4) 0.4484(3) 0.0877(10) Uani 1 1 d . . .
O10 O 0.2843(4) 1.0969(4) 0.2736(3) 0.0820(9) Uani 1 1 d . . .
O11 O 0.0048(4) 1.3544(4) 0.1210(3) 0.0835(10) Uani 1 1 d . . .
O12 O 0.0759(4) 1.1111(4) 0.0626(3) 0.0755(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
O1 C4 1.374(4) . ?
O1 C1 1.417(4) . ?
N1 N3 1.370(4) . ?
N1 C3 1.396(4) . ?
N1 C2 1.447(4) . ?
C1 N2 1.467(4) . ?
C1 C2 1.535(5) . ?
C1 H1A 0.9800 . ?
N2 C3 1.254(4) . ?
C2 O3 1.411(4) . ?
C2 H2B 0.9800 . ?
O2 C4 1.186(5) . ?
O3 C6 1.363(4) . ?
C3 C8 1.506(4) . ?
N3 O6 1.206(4) . ?
N3 O5 1.218(4) . ?
N4 O8 1.195(4) . ?
N4 O7 1.198(4) . ?
N4 C8 1.515(4) . ?
C4 C5 1.469(6) . ?
O4 C6 1.177(5) . ?
N5 O10 1.191(4) . ?
N5 O9 1.199(4) . ?
N5 C8 1.541(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
N6 O11 1.202(4) . ?
N6 O12 1.208(4) . ?
N6 C8 1.528(4) . ?
C6 C7 1.475(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 116.1(3) . . ?
N3 N1 C3 127.5(3) . . ?
N3 N1 C2 123.1(3) . . ?
C3 N1 C2 109.0(3) . . ?
O1 C1 N2 106.9(3) . . ?
O1 C1 C2 108.3(3) . . ?
N2 C1 C2 107.0(3) . . ?
O1 C1 H1A 111.5 . . ?
N2 C1 H1A 111.5 . . ?
C2 C1 H1A 111.5 . . ?
C3 N2 C1 107.2(3) . . ?
O3 C2 N1 108.5(3) . . ?
O3 C2 C1 109.8(3) . . ?
N1 C2 C1 100.2(2) . . ?
O3 C2 H2B 112.6 . . ?
N1 C2 H2B 112.6 . . ?
C1 C2 H2B 112.6 . . ?
C6 O3 C2 118.1(3) . . ?
N2 C3 N1 115.1(3) . . ?
N2 C3 C8 120.0(3) . . ?
N1 C3 C8 124.9(3) . . ?
O6 N3 O5 127.8(3) . . ?
O6 N3 N1 115.6(3) . . ?
O5 N3 N1 116.6(3) . . ?
O8 N4 O7 127.3(4) . . ?
O8 N4 C8 116.9(3) . . ?
O7 N4 C8 115.7(3) . . ?
O2 C4 O1 121.3(4) . . ?
O2 C4 C5 128.6(4) . . ?
O1 C4 C5 110.1(4) . . ?
O10 N5 O9 128.3(4) . . ?
O10 N5 C8 116.8(3) . . ?
O9 N5 C8 114.9(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O11 N6 O12 128.0(3) . . ?
O11 N6 C8 119.0(3) . . ?
O12 N6 C8 113.0(3) . . ?
O4 C6 O3 121.7(4) . . ?
O4 C6 C7 128.0(4) . . ?
O3 C6 C7 110.3(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 N4 114.4(3) . . ?
C3 C8 N6 111.5(3) . . ?
N4 C8 N6 111.9(3) . . ?
C3 C8 N5 107.3(2) . . ?
N4 C8 N5 105.2(3) . . ?
N6 C8 N5 105.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 N2 95.6(3) . . . . ?
C4 O1 C1 C2 -149.4(3) . . . . ?
O1 C1 N2 C3 105.6(3) . . . . ?
C2 C1 N2 C3 -10.2(3) . . . . ?
N3 N1 C2 O3 -81.1(4) . . . . ?
C3 N1 C2 O3 105.7(3) . . . . ?
N3 N1 C2 C1 163.9(3) . . . . ?
C3 N1 C2 C1 -9.3(3) . . . . ?
O1 C1 C2 O3 142.7(2) . . . . ?
N2 C1 C2 O3 -102.4(3) . . . . ?
O1 C1 C2 N1 -103.3(3) . . . . ?
N2 C1 C2 N1 11.6(3) . . . . ?
N1 C2 O3 C6 128.7(3) . . . . ?
C1 C2 O3 C6 -122.7(3) . . . . ?
C1 N2 C3 N1 4.3(4) . . . . ?
C1 N2 C3 C8 -175.1(3) . . . . ?
N3 N1 C3 N2 -169.1(3) . . . . ?
C2 N1 C3 N2 3.8(4) . . . . ?
N3 N1 C3 C8 10.3(5) . . . . ?
C2 N1 C3 C8 -176.8(3) . . . . ?
C3 N1 N3 O6 178.2(3) . . . . ?
C2 N1 N3 O6 6.2(5) . . . . ?
C3 N1 N3 O5 -1.9(5) . . . . ?
C2 N1 N3 O5 -173.9(3) . . . . ?
C1 O1 C4 O2 6.2(5) . . . . ?
C1 O1 C4 C5 -174.0(3) . . . . ?
C2 O3 C6 O4 0.3(6) . . . . ?
C2 O3 C6 C7 -179.2(3) . . . . ?
N2 C3 C8 N4 -118.5(3) . . . . ?
N1 C3 C8 N4 62.1(4) . . . . ?
N2 C3 C8 N6 113.2(3) . . . . ?
N1 C3 C8 N6 -66.1(4) . . . . ?
N2 C3 C8 N5 -2.3(4) . . . . ?
N1 C3 C8 N5 178.4(3) . . . . ?
O8 N4 C8 C3 171.7(4) . . . . ?
O7 N4 C8 C3 -5.1(5) . . . . ?
O8 N4 C8 N6 -60.3(4) . . . . ?
O7 N4 C8 N6 123.0(4) . . . . ?
O8 N4 C8 N5 54.2(4) . . . . ?
O7 N4 C8 N5 -122.5(4) . . . . ?
O11 N6 C8 C3 156.7(3) . . . . ?
O12 N6 C8 C3 -26.0(4) . . . . ?
O11 N6 C8 N4 27.1(4) . . . . ?
O12 N6 C8 N4 -155.6(3) . . . . ?
O11 N6 C8 N5 -86.9(4) . . . . ?
O12 N6 C8 N5 90.4(3) . . . . ?
O10 N5 C8 C3 97.5(3) . . . . ?
O9 N5 C8 C3 -80.8(3) . . . . ?
O10 N5 C8 N4 -140.4(3) . . . . ?
O9 N5 C8 N4 41.4(4) . . . . ?
O10 N5 C8 N6 -21.7(4) . . . . ?
O9 N5 C8 N6 160.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1500626'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H6 N6 O8'
_chemical_formula_weight         278.16

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.821(2)
_cell_length_b                   8.8200(18)
_cell_length_c                   11.286(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.44(3)
_cell_angle_gamma                90.00
_cell_volume                     1075.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       rod
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2223
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.36
_reflns_number_total             2108
_reflns_number_gt                1154
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0290P)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         2108
_refine_ls_number_parameters     337
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.005
_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 0.8264(7) 0.2997(6) 0.1425(5) 0.097(2) Uani 1 1 d . . .
O1 O 0.8848(9) -0.0184(7) 0.3816(6) 0.189(4) Uani 1 1 d . . .
C1 C 0.8145(9) 0.4555(8) 0.1826(7) 0.112(3) Uani 1 1 d . . .
H1B H 0.8392 0.5232 0.1206 0.134 Uiso 1 1 calc R . .
H1C H 0.7283 0.4757 0.1956 0.134 Uiso 1 1 calc R . .
N2 N 0.8729(5) 0.2223(6) 0.3356(5) 0.0639(15) Uani 1 1 d . . .
O2 O 0.8959(5) 0.1460(7) 0.5206(4) 0.1026(18) Uani 1 1 d . . .
C2 C 0.8850(9) 0.4865(8) 0.2857(6) 0.116(3) Uani 1 1 d . . .
H2A H 0.8610 0.5856 0.3137 0.139 Uiso 1 1 calc R . .
H2B H 0.9709 0.4934 0.2661 0.139 Uiso 1 1 calc R . .
C3 C 0.8778(7) 0.3803(8) 0.3830(5) 0.071(2) Uani 1 1 d . . .
H3A H 0.8044 0.4006 0.4256 0.086 Uiso 1 1 calc R . .
H3B H 0.9497 0.3920 0.4379 0.086 Uiso 1 1 calc R . .
N3 N 0.8804(7) 0.1123(8) 0.4195(5) 0.091(2) Uani 1 1 d . . .
O3 O 0.7276(10) 0.0486(11) -0.0084(7) 0.187(4) Uani 1 1 d . . .
C4 C 0.8516(5) 0.1981(7) 0.2178(5) 0.0574(16) Uani 1 1 d . . .
N4 N 0.8415(13) 0.0580(11) 0.0217(9) 0.147(5) Uani 1 1 d . . .
O4 O 0.9258(12) 0.0755(14) -0.0222(10) 0.272(10) Uani 1 1 d . . .
N5 N 0.9756(5) -0.0441(7) 0.1821(7) 0.104(3) Uani 1 1 d . . .
C5 C 0.8612(6) 0.0414(6) 0.1606(5) 0.0587(17) Uani 1 1 d . . .
O5 O 1.0564(6) 0.0310(8) 0.2224(6) 0.150 Uani 1 1 d . . .
C6 C 0.3278(6) -0.1848(7) 0.3196(5) 0.0645(18) Uani 1 1 d . . .
H6A H 0.3613 -0.2447 0.3862 0.077 Uiso 1 1 calc R . .
H6B H 0.2436 -0.2187 0.3011 0.077 Uiso 1 1 calc R . .
N6 N 0.7538(5) -0.0599(7) 0.1907(7) 0.101(3) Uani 1 1 d . . .
O6 O 0.9890(5) -0.1702(6) 0.1557(6) 0.136(2) Uani 1 1 d . . .
N7 N 0.3250(5) -0.0245(5) 0.3559(4) 0.0533(13) Uani 1 1 d . . .
O7 O 0.6698(6) 0.0017(8) 0.2349(7) 0.174(3) Uani 1 1 d . . .
C7 C 0.4003(6) -0.2140(7) 0.2181(5) 0.0705(19) Uani 1 1 d . . .
H7B H 0.3817 -0.3149 0.1877 0.085 Uiso 1 1 calc R . .
H7C H 0.4877 -0.2105 0.2427 0.085 Uiso 1 1 calc R . .
N8 N 0.3875(4) 0.0534(5) 0.1738(4) 0.0498(12) Uani 1 1 d . . .
C8 C 0.3732(6) -0.0996(8) 0.1213(6) 0.0693(19) Uani 1 1 d . . .
H8A H 0.4301 -0.1127 0.0589 0.083 Uiso 1 1 calc R . .
H8B H 0.2895 -0.1131 0.0873 0.083 Uiso 1 1 calc R . .
O8 O 0.7499(5) -0.1893(6) 0.1709(6) 0.116(2) Uani 1 1 d . . .
N9 N 0.4308(5) 0.1641(7) 0.1018(5) 0.0706(16) Uani 1 1 d . . .
O9 O 0.4403(5) 0.1313(6) -0.0002(4) 0.0947(17) Uani 1 1 d . . .
C9 C 0.3555(4) 0.0778(6) 0.2898(5) 0.0423(13) Uani 1 1 d . . .
C10 C 0.3477(6) 0.2348(6) 0.3394(5) 0.0589(17) Uani 1 1 d U . .
O10 O 0.4538(5) 0.2861(6) 0.1488(4) 0.0864(15) Uani 1 1 d . . .
N10 N 0.2608(5) 0.3448(6) 0.2692(5) 0.0657(16) Uani 1 1 d U . .
N11 N 0.4733(6) 0.3063(8) 0.3681(5) 0.0819(18) Uani 1 1 d U . .
O11 O 0.2491(5) 0.4685(5) 0.3085(5) 0.1004(18) Uani 1 1 d . . .
N12 N 0.2890(6) 0.2228(6) 0.4591(5) 0.0697(15) Uani 1 1 d . . .
O12 O 0.2081(4) 0.2901(6) 0.1860(5) 0.0919(16) Uani 1 1 d U . .
O13 O 0.5555(4) 0.2139(7) 0.3857(5) 0.0972(17) Uani 1 1 d . . .
O14 O 0.4835(5) 0.4404(7) 0.3792(6) 0.126(2) Uani 1 1 d . . .
O15 O 0.1746(4) 0.2121(6) 0.4521(4) 0.0891(15) Uani 1 1 d . . .
O16 O 0.3555(5) 0.2204(7) 0.5475(4) 0.1020(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 C4 1.254(7) . ?
N1 C1 1.455(8) . ?
O1 N3 1.231(8) . ?
C1 C2 1.380(9) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
N2 C4 1.353(7) . ?
N2 N3 1.355(7) . ?
N2 C3 1.492(7) . ?
O2 N3 1.182(6) . ?
C2 C3 1.449(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O3 N4 1.262(13) . ?
C4 C5 1.531(8) . ?
N4 O4 1.075(16) . ?
N4 C5 1.576(11) . ?
N5 O6 1.162(6) . ?
N5 O5 1.167(7) . ?
N5 C5 1.457(8) . ?
C5 N6 1.521(8) . ?
C6 C7 1.450(8) . ?
C6 N7 1.473(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N6 O8 1.163(7) . ?
N6 O7 1.194(7) . ?
N7 C9 1.229(6) . ?
C7 C8 1.502(8) . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
N8 N9 1.371(6) . ?
N8 C9 1.391(6) . ?
N8 C8 1.479(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N9 O9 1.197(6) . ?
N9 O10 1.219(7) . ?
C9 C10 1.498(7) . ?
C10 N11 1.515(8) . ?
C10 N12 1.530(7) . ?
C10 N10 1.538(7) . ?
N10 O12 1.173(6) . ?
N10 O11 1.187(6) . ?
N11 O14 1.194(7) . ?
N11 O13 1.214(7) . ?
N12 O16 1.196(6) . ?
N12 O15 1.239(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 118.9(6) . . ?
C2 C1 N1 113.3(7) . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1C 108.9 . . ?
N1 C1 H1C 108.9 . . ?
H1B C1 H1C 107.7 . . ?
C4 N2 N3 125.0(5) . . ?
C4 N2 C3 120.0(5) . . ?
N3 N2 C3 114.8(5) . . ?
C1 C2 C3 117.3(8) . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2B 108.0 . . ?
C3 C2 H2B 108.0 . . ?
H2A C2 H2B 107.2 . . ?
C2 C3 N2 109.6(5) . . ?
C2 C3 H3A 109.8 . . ?
N2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
N2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O2 N3 O1 124.4(7) . . ?
O2 N3 N2 119.6(7) . . ?
O1 N3 N2 115.5(6) . . ?
N1 C4 N2 124.8(6) . . ?
N1 C4 C5 112.1(5) . . ?
N2 C4 C5 123.0(5) . . ?
O4 N4 O3 136.7(15) . . ?
O4 N4 C5 113.9(14) . . ?
O3 N4 C5 109.5(11) . . ?
O6 N5 O5 122.7(8) . . ?
O6 N5 C5 124.8(7) . . ?
O5 N5 C5 112.3(6) . . ?
N5 C5 N6 108.1(5) . . ?
N5 C5 C4 118.4(5) . . ?
N6 C5 C4 111.4(5) . . ?
N5 C5 N4 106.0(7) . . ?
N6 C5 N4 102.5(7) . . ?
C4 C5 N4 109.1(5) . . ?
C7 C6 N7 114.3(5) . . ?
C7 C6 H6A 108.7 . . ?
N7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
N7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O8 N6 O7 120.5(8) . . ?
O8 N6 C5 123.6(7) . . ?
O7 N6 C5 115.9(6) . . ?
C9 N7 C6 121.7(5) . . ?
C6 C7 C8 111.3(6) . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7C 109.4 . . ?
C8 C7 H7C 109.4 . . ?
H7B C7 H7C 108.0 . . ?
N9 N8 C9 124.2(5) . . ?
N9 N8 C8 116.4(5) . . ?
C9 N8 C8 119.5(5) . . ?
N8 C8 C7 108.1(5) . . ?
N8 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N8 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
O9 N9 O10 127.2(6) . . ?
O9 N9 N8 116.8(6) . . ?
O10 N9 N8 116.0(6) . . ?
N7 C9 N8 123.3(5) . . ?
N7 C9 C10 115.4(5) . . ?
N8 C9 C10 121.2(5) . . ?
C9 C10 N11 113.3(5) . . ?
C9 C10 N12 107.6(5) . . ?
N11 C10 N12 104.8(5) . . ?
C9 C10 N10 115.9(5) . . ?
N11 C10 N10 111.1(5) . . ?
N12 C10 N10 103.0(5) . . ?
O12 N10 O11 128.2(6) . . ?
O12 N10 C10 114.0(6) . . ?
O11 N10 C10 117.6(6) . . ?
O14 N11 O13 125.8(7) . . ?
O14 N11 C10 120.7(7) . . ?
O13 N11 C10 113.2(6) . . ?
O16 N12 O15 126.9(6) . . ?
O16 N12 C10 118.5(6) . . ?
O15 N12 C10 114.6(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
C4 N1 C1 C2 28.2(14) . . . . ?
N1 C1 C2 C3 -47.9(13) . . . . ?
C1 C2 C3 N2 39.4(11) . . . . ?
C4 N2 C3 C2 -12.7(9) . . . . ?
N3 N2 C3 C2 172.8(7) . . . . ?
C4 N2 N3 O2 -177.9(6) . . . . ?
C3 N2 N3 O2 -3.6(10) . . . . ?
C4 N2 N3 O1 10.4(11) . . . . ?
C3 N2 N3 O1 -175.3(8) . . . . ?
C1 N1 C4 N2 -2.1(12) . . . . ?
C1 N1 C4 C5 -179.7(8) . . . . ?
N3 N2 C4 N1 168.7(7) . . . . ?
C3 N2 C4 N1 -5.2(10) . . . . ?
N3 N2 C4 C5 -13.9(10) . . . . ?
C3 N2 C4 C5 172.1(6) . . . . ?
O6 N5 C5 N6 42.6(11) . . . . ?
O5 N5 C5 N6 -142.0(7) . . . . ?
O6 N5 C5 C4 170.4(8) . . . . ?
O5 N5 C5 C4 -14.2(10) . . . . ?
O6 N5 C5 N4 -66.8(10) . . . . ?
O5 N5 C5 N4 108.6(8) . . . . ?
N1 C4 C5 N5 123.7(7) . . . . ?
N2 C4 C5 N5 -54.0(9) . . . . ?
N1 C4 C5 N6 -110.0(7) . . . . ?
N2 C4 C5 N6 72.3(8) . . . . ?
N1 C4 C5 N4 2.4(10) . . . . ?
N2 C4 C5 N4 -175.3(7) . . . . ?
O4 N4 C5 N5 -37.6(13) . . . . ?
O3 N4 C5 N5 143.1(9) . . . . ?
O4 N4 C5 N6 -151.0(12) . . . . ?
O3 N4 C5 N6 29.8(10) . . . . ?
O4 N4 C5 C4 90.9(13) . . . . ?
O3 N4 C5 C4 -88.4(10) . . . . ?
N5 C5 N6 O8 -37.5(11) . . . . ?
C4 C5 N6 O8 -169.3(8) . . . . ?
N4 C5 N6 O8 74.2(10) . . . . ?
N5 C5 N6 O7 143.9(8) . . . . ?
C4 C5 N6 O7 12.1(10) . . . . ?
N4 C5 N6 O7 -104.4(9) . . . . ?
C7 C6 N7 C9 16.5(9) . . . . ?
N7 C6 C7 C8 -45.2(8) . . . . ?
N9 N8 C8 C7 146.8(5) . . . . ?
C9 N8 C8 C7 -34.2(7) . . . . ?
C6 C7 C8 N8 52.2(7) . . . . ?
C9 N8 N9 O9 -171.1(5) . . . . ?
C8 N8 N9 O9 7.8(8) . . . . ?
C9 N8 N9 O10 7.9(8) . . . . ?
C8 N8 N9 O10 -173.1(6) . . . . ?
C6 N7 C9 N8 4.1(9) . . . . ?
C6 N7 C9 C10 -179.9(6) . . . . ?
N9 N8 C9 N7 -174.8(5) . . . . ?
C8 N8 C9 N7 6.3(8) . . . . ?
N9 N8 C9 C10 9.5(8) . . . . ?
C8 N8 C9 C10 -169.4(5) . . . . ?
N7 C9 C10 N11 109.5(6) . . . . ?
N8 C9 C10 N11 -74.5(7) . . . . ?
N7 C9 C10 N12 -5.8(7) . . . . ?
N8 C9 C10 N12 170.2(5) . . . . ?
N7 C9 C10 N10 -120.4(5) . . . . ?
N8 C9 C10 N10 55.6(7) . . . . ?
C9 C10 N10 O12 2.0(8) . . . . ?
N11 C10 N10 O12 133.1(6) . . . . ?
N12 C10 N10 O12 -115.2(6) . . . . ?
C9 C10 N10 O11 177.3(6) . . . . ?
N11 C10 N10 O11 -51.5(7) . . . . ?
N12 C10 N10 O11 60.2(7) . . . . ?
C9 C10 N11 O14 161.0(7) . . . . ?
N12 C10 N11 O14 -82.1(8) . . . . ?
N10 C10 N11 O14 28.5(9) . . . . ?
C9 C10 N11 O13 -23.9(8) . . . . ?
N12 C10 N11 O13 93.1(7) . . . . ?
N10 C10 N11 O13 -156.4(6) . . . . ?
C9 C10 N12 O16 97.4(7) . . . . ?
N11 C10 N12 O16 -23.4(8) . . . . ?
N10 C10 N12 O16 -139.7(6) . . . . ?
C9 C10 N12 O15 -80.6(6) . . . . ?
N11 C10 N12 O15 158.6(5) . . . . ?
N10 C10 N12 O15 42.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1502271'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 N6 O8'
_chemical_formula_weight         318.22

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           Monoclinic
_symmetry_space_group_name_H-M   C2/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.390(4)
_cell_length_b                   12.501(3)
_cell_length_c                   9.957(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.08(3)
_cell_angle_gamma                90.00
_cell_volume                     2652.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2490
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2424
_reflns_number_gt                1565
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)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         2424
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.118
_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
O1 O 0.30626(12) 0.9508(2) 0.0678(3) 0.0684(8) Uani 1 1 d . . .
C1 C 0.34816(16) 0.7366(3) 0.2978(3) 0.0478(8) Uani 1 1 d . . .
H1A H 0.3139 0.6900 0.2613 0.057 Uiso 1 1 calc R . .
N2 N 0.41975(13) 0.6996(2) 0.1351(3) 0.0488(7) Uani 1 1 d . . .
N1 N 0.35148(12) 0.8235(2) 0.1987(3) 0.0471(7) Uani 1 1 d . . .
O2 O 0.26933(12) 0.9106(2) 0.2564(3) 0.0762(8) Uani 1 1 d . . .
C2 C 0.3382(2) 0.7515(3) 0.4432(4) 0.0699(11) Uani 1 1 d . . .
H2B H 0.2977 0.7843 0.4523 0.084 Uiso 1 1 calc R . .
H2C H 0.3707 0.7973 0.4866 0.084 Uiso 1 1 calc R . .
N3 N 0.30557(12) 0.8989(2) 0.1723(3) 0.0513(7) Uani 1 1 d . . .
O3 O 0.29811(13) 0.7618(3) -0.0910(3) 0.1015(12) Uani 1 1 d D . .
C3 C 0.3411(2) 0.6415(3) 0.5069(4) 0.0712(11) Uani 1 1 d . . .
H3A H 0.3417 0.6503 0.6038 0.085 Uiso 1 1 calc R . .
H3B H 0.3028 0.6038 0.4770 0.085 Uiso 1 1 calc R . .
N4 N 0.33618(14) 0.8187(3) -0.1312(3) 0.0571(8) Uani 1 1 d . . .
O4 O 0.33416(15) 0.8595(3) -0.2397(3) 0.0890(10) Uani 1 1 d . . .
C4 C 0.3958(2) 0.5720(3) 0.4784(4) 0.0750(12) Uani 1 1 d . . .
H4A H 0.3875 0.4995 0.5069 0.090 Uiso 1 1 calc R . .
H4B H 0.4329 0.5971 0.5324 0.090 Uiso 1 1 calc R . .
N5 N 0.41849(13) 0.9464(2) -0.0247(3) 0.0501(7) Uani 1 1 d . . .
O5 O 0.44391(14) 0.9684(2) 0.0854(3) 0.0784(9) Uani 1 1 d . . .
C5 C 0.4098(3) 0.5694(3) 0.3318(4) 0.0805(13) Uani 1 1 d . . .
H5A H 0.4513 0.5399 0.3247 0.097 Uiso 1 1 calc R . .
H5B H 0.3795 0.5241 0.2807 0.097 Uiso 1 1 calc R . .
N6 N 0.44581(14) 0.7684(2) -0.1034(3) 0.0479(7) Uani 1 1 d . . .
O6 O 0.41347(13) 1.0018(2) -0.1226(3) 0.0781(9) Uani 1 1 d . . .
C6 C 0.40653(18) 0.6785(3) 0.2768(3) 0.0565(9) Uani 1 1 d . . .
H6A H 0.4394 0.7177 0.3313 0.068 Uiso 1 1 calc R . .
C7 C 0.38843(14) 0.7818(2) 0.0998(3) 0.0385(7) Uani 1 1 d . . .
O7 O 0.49854(12) 0.8016(2) -0.0833(3) 0.0695(8) Uani 1 1 d . . .
O8 O 0.42797(14) 0.6916(2) -0.1678(3) 0.0734(8) Uani 1 1 d . . .
C8 C 0.39517(14) 0.8309(2) -0.0352(3) 0.0396(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.228(4) . ?
C1 N1 1.473(4) . ?
C1 C6 1.476(5) . ?
C1 C2 1.493(5) . ?
C1 H1A 0.9800 . ?
N2 C7 1.259(4) . ?
N2 C6 1.487(4) . ?
N1 N3 1.370(4) . ?
N1 C7 1.416(4) . ?
O2 N3 1.199(3) . ?
C2 C3 1.513(5) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
O3 N4 1.178(4) . ?
C3 C4 1.504(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 O4 1.191(4) . ?
N4 C8 1.522(4) . ?
C4 C5 1.516(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N5 O6 1.194(3) . ?
N5 O5 1.211(4) . ?
N5 C8 1.528(4) . ?
C5 C6 1.469(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N6 O8 1.198(4) . ?
N6 O7 1.202(3) . ?
N6 C8 1.541(4) . ?
C6 H6A 0.9800 . ?
C7 C8 1.497(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 100.2(2) . . ?
N1 C1 C2 125.2(3) . . ?
C6 C1 C2 113.2(3) . . ?
N1 C1 H1A 105.6 . . ?
C6 C1 H1A 105.6 . . ?
C2 C1 H1A 105.6 . . ?
C7 N2 C6 105.6(2) . . ?
N3 N1 C7 123.7(3) . . ?
N3 N1 C1 124.0(2) . . ?
C7 N1 C1 104.9(2) . . ?
C1 C2 C3 106.8(3) . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C1 C2 H2C 110.4 . . ?
C3 C2 H2C 110.4 . . ?
H2B C2 H2C 108.6 . . ?
O2 N3 O1 125.8(3) . . ?
O2 N3 N1 116.5(3) . . ?
O1 N3 N1 117.7(3) . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
O3 N4 O4 126.6(3) . . ?
O3 N4 C8 114.0(3) . . ?
O4 N4 C8 119.2(3) . . ?
C3 C4 C5 114.6(3) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
O6 N5 O5 127.4(3) . . ?
O6 N5 C8 119.2(3) . . ?
O5 N5 C8 113.3(3) . . ?
C6 C5 C4 109.4(3) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O8 N6 O7 128.0(3) . . ?
O8 N6 C8 116.1(3) . . ?
O7 N6 C8 116.0(3) . . ?
C5 C6 C1 114.6(3) . . ?
C5 C6 N2 120.8(3) . . ?
C1 C6 N2 106.4(3) . . ?
C5 C6 H6A 104.4 . . ?
C1 C6 H6A 104.4 . . ?
N2 C6 H6A 104.4 . . ?
N2 C7 N1 115.0(3) . . ?
N2 C7 C8 119.6(3) . . ?
N1 C7 C8 125.3(3) . . ?
C7 C8 N4 112.5(2) . . ?
C7 C8 N5 112.5(2) . . ?
N4 C8 N5 112.7(3) . . ?
C7 C8 N6 108.4(2) . . ?
N4 C8 N6 104.4(2) . . ?
N5 C8 N6 105.8(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
C6 C1 N1 N3 176.5(3) . . . . ?
C2 C1 N1 N3 -55.5(5) . . . . ?
C6 C1 N1 C7 25.7(3) . . . . ?
C2 C1 N1 C7 153.7(3) . . . . ?
N1 C1 C2 C3 -177.4(3) . . . . ?
C6 C1 C2 C3 -54.9(4) . . . . ?
C7 N1 N3 O2 164.7(3) . . . . ?
C1 N1 N3 O2 19.2(4) . . . . ?
C7 N1 N3 O1 -17.7(4) . . . . ?
C1 N1 N3 O1 -163.2(3) . . . . ?
C1 C2 C3 C4 48.7(5) . . . . ?
C2 C3 C4 C5 -45.6(6) . . . . ?
C3 C4 C5 C6 44.0(6) . . . . ?
C4 C5 C6 C1 -52.1(5) . . . . ?
C4 C5 C6 N2 178.6(4) . . . . ?
N1 C1 C6 C5 -163.3(3) . . . . ?
C2 C1 C6 C5 61.1(5) . . . . ?
N1 C1 C6 N2 -27.1(3) . . . . ?
C2 C1 C6 N2 -162.7(3) . . . . ?
C7 N2 C6 C5 151.9(4) . . . . ?
C7 N2 C6 C1 19.1(4) . . . . ?
C6 N2 C7 N1 -1.7(4) . . . . ?
C6 N2 C7 C8 174.9(3) . . . . ?
N3 N1 C7 N2 -167.2(3) . . . . ?
C1 N1 C7 N2 -16.2(4) . . . . ?
N3 N1 C7 C8 16.4(5) . . . . ?
C1 N1 C7 C8 167.4(3) . . . . ?
N2 C7 C8 N4 111.6(3) . . . . ?
N1 C7 C8 N4 -72.2(4) . . . . ?
N2 C7 C8 N5 -119.9(3) . . . . ?
N1 C7 C8 N5 56.3(4) . . . . ?
N2 C7 C8 N6 -3.3(4) . . . . ?
N1 C7 C8 N6 172.9(3) . . . . ?
O3 N4 C8 C7 -9.1(4) . . . . ?
O4 N4 C8 C7 175.9(3) . . . . ?
O3 N4 C8 N5 -137.5(3) . . . . ?
O4 N4 C8 N5 47.5(4) . . . . ?
O3 N4 C8 N6 108.2(3) . . . . ?
O4 N4 C8 N6 -66.8(4) . . . . ?
O6 N5 C8 C7 -164.4(3) . . . . ?
O5 N5 C8 C7 19.7(4) . . . . ?
O6 N5 C8 N4 -35.9(4) . . . . ?
O5 N5 C8 N4 148.1(3) . . . . ?
O6 N5 C8 N6 77.5(3) . . . . ?
O5 N5 C8 N6 -98.4(3) . . . . ?
O8 N6 C8 C7 87.5(3) . . . . ?
O7 N6 C8 C7 -91.2(3) . . . . ?
O8 N6 C8 N4 -32.6(3) . . . . ?
O7 N6 C8 N4 148.7(3) . . . . ?
O8 N6 C8 N5 -151.7(3) . . . . ?
O7 N6 C8 N5 29.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1502272'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 N6 O8'
_chemical_formula_weight         318.22

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           Monoclinic
_symmetry_space_group_name_H-M   P21/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.267(2)
_cell_length_b                   10.248(2)
_cell_length_c                   11.444(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1321.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2561
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2432
_reflns_number_gt                1193
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0560P)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         2432
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.8562(3) 0.1226(3) 0.3739(3) 0.0533(9) Uani 1 1 d . . .
O1 O 0.5540(3) 0.3103(3) 0.2911(3) 0.0691(9) Uani 1 1 d . . .
C1 C 0.8253(3) -0.0064(4) 0.3191(4) 0.0487(10) Uani 1 1 d . . .
H1B H 0.8543 -0.0057 0.2391 0.058 Uiso 1 1 calc R . .
N2 N 0.6704(3) 0.1358(3) 0.2965(3) 0.0485(9) Uani 1 1 d . . .
O2 O 0.4808(3) 0.1182(3) 0.2537(3) 0.0746(10) Uani 1 1 d . . .
C2 C 0.8797(4) -0.1236(4) 0.3814(4) 0.0618(13) Uani 1 1 d . . .
H2A H 0.8789 -0.1971 0.3280 0.074 Uiso 1 1 calc R . .
H2B H 0.9619 -0.1041 0.4015 0.074 Uiso 1 1 calc R . .
N3 N 0.5600(3) 0.1899(4) 0.2809(3) 0.0548(9) Uani 1 1 d . . .
O3 O 0.7792(4) 0.3782(3) 0.1915(3) 0.0911(12) Uani 1 1 d . . .
C3 C 0.8174(4) -0.1624(4) 0.4904(4) 0.0692(13) Uani 1 1 d . . .
H3A H 0.8290 -0.0953 0.5494 0.083 Uiso 1 1 calc R . .
H3B H 0.8515 -0.2429 0.5206 0.083 Uiso 1 1 calc R . .
O4 O 0.7731(3) 0.5451(3) 0.3056(3) 0.0814(11) Uani 1 1 d . . .
N4 N 0.7733(3) 0.4303(3) 0.2853(4) 0.0543(10) Uani 1 1 d . . .
C4 C 0.6865(4) -0.1813(4) 0.4663(4) 0.0662(13) Uani 1 1 d . . .
H4A H 0.6487 -0.2095 0.5373 0.079 Uiso 1 1 calc R . .
H4B H 0.6749 -0.2490 0.4079 0.079 Uiso 1 1 calc R . .
C5 C 0.6294(4) -0.0556(4) 0.4232(4) 0.0574(12) Uani 1 1 d . . .
H5A H 0.6369 0.0107 0.4834 0.069 Uiso 1 1 calc R . .
H5B H 0.5455 -0.0702 0.4070 0.069 Uiso 1 1 calc R . .
O5 O 0.6746(3) 0.4871(3) 0.5083(3) 0.0985(13) Uani 1 1 d . . .
N5 N 0.6828(3) 0.3727(3) 0.4821(3) 0.0550(9) Uani 1 1 d . . .
N6 N 0.8966(3) 0.3599(3) 0.4513(4) 0.0573(10) Uani 1 1 d . . .
O6 O 0.6318(3) 0.2824(3) 0.5246(3) 0.0668(9) Uani 1 1 d . . .
C6 C 0.6889(3) -0.0082(4) 0.3120(4) 0.0497(10) Uani 1 1 d . . .
H6A H 0.6600 -0.0567 0.2432 0.060 Uiso 1 1 calc R . .
C7 C 0.7687(3) 0.1964(4) 0.3551(3) 0.0452(10) Uani 1 1 d . . .
O7 O 0.9002(3) 0.3437(3) 0.5564(3) 0.0797(10) Uani 1 1 d . . .
O8 O 0.9755(3) 0.3908(3) 0.3894(3) 0.0774(11) Uani 1 1 d . . .
C8 C 0.7753(3) 0.3377(3) 0.3903(3) 0.0431(10) 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 C7 1.256(4) . ?
N1 C1 1.500(5) . ?
O1 N3 1.241(4) . ?
C1 C2 1.518(5) . ?
C1 C6 1.537(5) . ?
C1 H1B 0.9800 . ?
N2 N3 1.370(4) . ?
N2 C7 1.424(5) . ?
N2 C6 1.500(4) . ?
O2 N3 1.191(4) . ?
C2 C3 1.500(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 N4 1.202(4) . ?
C3 C4 1.506(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 N4 1.199(4) . ?
N4 C8 1.531(5) . ?
C4 C5 1.517(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.532(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O5 N5 1.214(4) . ?
N5 O6 1.199(4) . ?
N5 C8 1.540(5) . ?
N6 O8 1.193(4) . ?
N6 O7 1.214(5) . ?
N6 C8 1.536(5) . ?
C6 H6A 0.9800 . ?
C7 C8 1.504(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
C7 N1 C1 106.7(3) . . ?
N1 C1 C2 114.5(3) . . ?
N1 C1 C6 104.7(3) . . ?
C2 C1 C6 114.0(3) . . ?
N1 C1 H1B 107.8 . . ?
C2 C1 H1B 107.8 . . ?
C6 C1 H1B 107.8 . . ?
N3 N2 C7 125.3(3) . . ?
N3 N2 C6 122.5(3) . . ?
C7 N2 C6 105.6(3) . . ?
C3 C2 C1 114.1(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
O2 N3 O1 126.6(4) . . ?
O2 N3 N2 117.1(3) . . ?
O1 N3 N2 116.2(4) . . ?
C2 C3 C4 111.0(4) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O4 N4 O3 127.5(4) . . ?
O4 N4 C8 117.2(4) . . ?
O3 N4 C8 115.1(3) . . ?
C3 C4 C5 110.9(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.4(3) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O6 N5 O5 127.2(4) . . ?
O6 N5 C8 115.9(3) . . ?
O5 N5 C8 116.8(3) . . ?
O8 N6 O7 128.1(4) . . ?
O8 N6 C8 115.9(4) . . ?
O7 N6 C8 116.0(4) . . ?
N2 C6 C5 110.3(3) . . ?
N2 C6 C1 97.5(3) . . ?
C5 C6 C1 114.7(4) . . ?
N2 C6 H6A 111.2 . . ?
C5 C6 H6A 111.2 . . ?
C1 C6 H6A 111.2 . . ?
N1 C7 N2 114.5(3) . . ?
N1 C7 C8 120.1(4) . . ?
N2 C7 C8 125.4(3) . . ?
C7 C8 N4 112.8(3) . . ?
C7 C8 N6 107.5(3) . . ?
N4 C8 N6 105.1(3) . . ?
C7 C8 N5 112.2(3) . . ?
N4 C8 N5 113.2(3) . . ?
N6 C8 N5 105.3(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
C7 N1 C1 C2 -148.5(4) . . . . ?
C7 N1 C1 C6 -22.9(4) . . . . ?
N1 C1 C2 C3 77.8(4) . . . . ?
C6 C1 C2 C3 -42.7(5) . . . . ?
C7 N2 N3 O2 -163.9(4) . . . . ?
C6 N2 N3 O2 -16.4(6) . . . . ?
C7 N2 N3 O1 19.4(6) . . . . ?
C6 N2 N3 O1 166.9(4) . . . . ?
C1 C2 C3 C4 53.0(5) . . . . ?
C2 C3 C4 C5 -61.2(5) . . . . ?
C3 C4 C5 C6 58.3(5) . . . . ?
N3 N2 C6 C5 -62.6(5) . . . . ?
C7 N2 C6 C5 90.3(4) . . . . ?
N3 N2 C6 C1 177.6(3) . . . . ?
C7 N2 C6 C1 -29.5(4) . . . . ?
C4 C5 C6 N2 -157.0(3) . . . . ?
C4 C5 C6 C1 -48.2(5) . . . . ?
N1 C1 C6 N2 31.2(4) . . . . ?
C2 C1 C6 N2 157.0(3) . . . . ?
N1 C1 C6 C5 -85.3(4) . . . . ?
C2 C1 C6 C5 40.6(5) . . . . ?
C1 N1 C7 N2 3.1(5) . . . . ?
C1 N1 C7 C8 -174.8(3) . . . . ?
N3 N2 C7 N1 170.4(4) . . . . ?
C6 N2 C7 N1 18.5(5) . . . . ?
N3 N2 C7 C8 -11.8(6) . . . . ?
C6 N2 C7 C8 -163.7(4) . . . . ?
N1 C7 C8 N4 112.8(4) . . . . ?
N2 C7 C8 N4 -64.9(5) . . . . ?
N1 C7 C8 N6 -2.6(5) . . . . ?
N2 C7 C8 N6 179.7(4) . . . . ?
N1 C7 C8 N5 -117.9(4) . . . . ?
N2 C7 C8 N5 64.4(5) . . . . ?
O4 N4 C8 C7 176.9(4) . . . . ?
O3 N4 C8 C7 -7.2(5) . . . . ?
O4 N4 C8 N6 -66.3(4) . . . . ?
O3 N4 C8 N6 109.6(4) . . . . ?
O4 N4 C8 N5 48.2(5) . . . . ?
O3 N4 C8 N5 -136.0(4) . . . . ?
O8 N6 C8 C7 89.8(4) . . . . ?
O7 N6 C8 C7 -90.1(4) . . . . ?
O8 N6 C8 N4 -30.5(4) . . . . ?
O7 N6 C8 N4 149.5(4) . . . . ?
O8 N6 C8 N5 -150.4(3) . . . . ?
O7 N6 C8 N5 29.7(4) . . . . ?
O6 N5 C8 C7 10.3(5) . . . . ?
O5 N5 C8 C7 -173.9(4) . . . . ?
O6 N5 C8 N4 139.3(4) . . . . ?
O5 N5 C8 N4 -44.8(5) . . . . ?
O6 N5 C8 N6 -106.4(4) . . . . ?
O5 N5 C8 N6 69.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1502273'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2016-10-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H6 N4 O6'
_chemical_formula_sum            'C4 H6 N4 O6'
_chemical_formula_weight         206.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.531(2)
_cell_length_b                   7.5300(15)
_cell_length_c                   17.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.46(3)
_cell_angle_gamma                90
_cell_volume                     1474.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            2702
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.365
_diffrn_reflns_theta_min         1.785
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2043
_reflns_number_total             2702
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+0.4315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1644
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 N2-H2
 0.84 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C1(H1b), C2(H2b), C5(H5a), C6(H6a)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1a), N5(H5), N6(H6)
4.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2a), O7(H7), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1190(2) 0.1456(3) 0.68872(13) 0.0451(6) Uani 1 1 d . . . . .
H1 H 0.0504 0.1618 0.6695 0.068 Uiso 1 1 calc R . . . .
N1 N 0.1112(2) 0.3085(4) 0.80464(14) 0.0384(7) Uani 1 1 d . . . . .
H1A H 0.0435 0.3532 0.8082 0.046 Uiso 1 1 calc R . . . .
C1 C 0.1616(3) 0.2961(4) 0.73186(16) 0.0329(7) Uani 1 1 d . . . . .
H1B H 0.1489 0.4049 0.7004 0.040 Uiso 1 1 calc R . . . .
N2 N 0.2859(2) 0.2047(4) 0.84262(14) 0.0331(6) Uani 1 1 d D . . . .
O2 O 0.35508(19) 0.4243(3) 0.76455(14) 0.0469(6) Uani 1 1 d . . . . .
H2A H 0.4059 0.4143 0.7361 0.070 Uiso 1 1 calc R . . . .
C2 C 0.2904(2) 0.2665(4) 0.76269(17) 0.0310(7) Uani 1 1 d . . . . .
H2B H 0.3238 0.1754 0.7318 0.037 Uiso 1 1 calc R . . . .
N3 N 0.0422(2) 0.2540(4) 0.95948(14) 0.0413(7) Uani 1 1 d . . . . .
C3 C 0.1841(2) 0.2410(4) 0.86527(16) 0.0284(6) Uani 1 1 d . . . . .
O3 O 0.0198(2) 0.2423(6) 1.02242(16) 0.1002(14) Uani 1 1 d . U . . .
N4 N 0.2351(2) 0.1363(3) 1.00247(14) 0.0323(6) Uani 1 1 d . . . . .
C4 C 0.1546(2) 0.2109(4) 0.94210(16) 0.0309(6) Uani 1 1 d . . . . .
O4 O -0.0305(2) 0.3138(5) 0.90732(15) 0.0830(11) Uani 1 1 d . U . . .
N5 N 0.4293(2) 0.6975(3) 0.98644(14) 0.0320(6) Uani 1 1 d . . . . .
H5 H 0.4935 0.6816 0.9673 0.038 Uiso 1 1 calc R . . . .
C5 C 0.4215(2) 0.6999(4) 1.06974(16) 0.0317(7) Uani 1 1 d . . . . .
H5A H 0.4672 0.6009 1.0955 0.038 Uiso 1 1 calc R . . . .
O5 O 0.33829(17) 0.1184(3) 0.98993(12) 0.0398(6) Uani 1 1 d . . . . .
N6 N 0.24187(19) 0.7108(3) 0.98897(13) 0.0312(6) Uani 1 1 d . . . . .
H6 H 0.1685 0.7290 0.9733 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2904(2) 0.6631(4) 1.06929(16) 0.0316(7) Uani 1 1 d . . . . .
H6A H 0.2580 0.7373 1.1077 0.038 Uiso 1 1 calc R . . . .
O6 O 0.2068(2) 0.0856(4) 1.06446(12) 0.0523(7) Uani 1 1 d . . . . .
O7 O 0.46150(17) 0.8590(3) 1.10622(12) 0.0361(5) Uani 1 1 d . . . . .
H7 H 0.4876 0.9230 1.0743 0.054 Uiso 1 1 calc R . . . .
N7 N 0.1920(2) 0.7705(4) 0.81785(14) 0.0339(6) Uani 1 1 d . . . . .
C7 C 0.3246(2) 0.7229(4) 0.94270(16) 0.0255(6) Uani 1 1 d . . . . .
N8 N 0.4003(2) 0.7868(3) 0.81838(14) 0.0323(6) Uani 1 1 d . . . . .
O8 O 0.27278(19) 0.4828(3) 1.08258(13) 0.0429(6) Uani 1 1 d . . . . .
H8 H 0.2265 0.4715 1.1142 0.064 Uiso 1 1 calc R . . . .
C8 C 0.3062(2) 0.7581(4) 0.86000(15) 0.0273(6) Uani 1 1 d . . . . .
O9 O 0.1132(2) 0.7996(5) 0.85575(14) 0.0632(8) Uani 1 1 d . . . . .
O10 O 0.1724(2) 0.7548(4) 0.74668(12) 0.0518(7) Uani 1 1 d . . . . .
O11 O 0.50033(18) 0.7425(3) 0.85091(13) 0.0450(6) Uani 1 1 d . . . . .
O12 O 0.3855(2) 0.8577(3) 0.75359(13) 0.0473(6) Uani 1 1 d . . . . .
H2 H 0.343(4) 0.176(9) 0.876(3) 0.13(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.403(4) . ?
N1 H1A 0.8600 . ?
N1 C1 1.456(4) . ?
N1 C3 1.338(4) . ?
C1 H1B 0.9800 . ?
C1 C2 1.518(4) . ?
N2 C2 1.457(4) . ?
N2 C3 1.319(4) . ?
N2 H2 0.83(2) . ?
O2 H2A 0.8200 . ?
O2 C2 1.400(4) . ?
C2 H2B 0.9800 . ?
N3 O3 1.151(4) . ?
N3 C4 1.410(4) . ?
N3 O4 1.219(3) . ?
C3 C4 1.428(4) . ?
N4 C4 1.403(4) . ?
N4 O5 1.248(3) . ?
N4 O6 1.219(3) . ?
N5 H5 0.8600 . ?
N5 C5 1.446(3) . ?
N5 C7 1.339(3) . ?
C5 H5A 0.9800 . ?
C5 C6 1.535(4) . ?
C5 O7 1.399(4) . ?
N6 H6 0.8600 . ?
N6 C6 1.455(4) . ?
N6 C7 1.331(3) . ?
C6 H6A 0.9800 . ?
C6 O8 1.396(4) . ?
O7 H7 0.8200 . ?
N7 C8 1.409(4) . ?
N7 O9 1.213(3) . ?
N7 O10 1.215(3) . ?
C7 C8 1.429(4) . ?
N8 C8 1.401(3) . ?
N8 O11 1.250(3) . ?
N8 O12 1.223(3) . ?
O8 H8 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C1 N1 H1A 124.5 . . ?
C3 N1 H1A 124.5 . . ?
C3 N1 C1 111.0(2) . . ?
O1 C1 N1 110.6(3) . . ?
O1 C1 H1B 111.9 . . ?
O1 C1 C2 108.3(2) . . ?
N1 C1 H1B 111.9 . . ?
N1 C1 C2 101.8(2) . . ?
C2 C1 H1B 111.9 . . ?
C2 N2 H2 126(4) . . ?
C3 N2 C2 111.6(2) . . ?
C3 N2 H2 120(4) . . ?
C2 O2 H2A 109.5 . . ?
C1 C2 H2B 110.9 . . ?
N2 C2 C1 101.9(2) . . ?
N2 C2 H2B 110.9 . . ?
O2 C2 C1 112.0(3) . . ?
O2 C2 N2 110.0(2) . . ?
O2 C2 H2B 110.9 . . ?
O3 N3 C4 121.4(3) . . ?
O3 N3 O4 119.5(3) . . ?
O4 N3 C4 118.9(2) . . ?
N1 C3 C4 124.8(3) . . ?
N2 C3 N1 109.5(3) . . ?
N2 C3 C4 125.7(3) . . ?
O5 N4 C4 117.4(2) . . ?
O6 N4 C4 122.5(3) . . ?
O6 N4 O5 120.1(2) . . ?
N3 C4 C3 120.7(2) . . ?
N4 C4 N3 117.7(2) . . ?
N4 C4 C3 121.6(2) . . ?
C5 N5 H5 124.1 . . ?
C7 N5 H5 124.1 . . ?
C7 N5 C5 111.7(2) . . ?
N5 C5 H5A 109.2 . . ?
N5 C5 C6 101.4(2) . . ?
C6 C5 H5A 109.2 . . ?
O7 C5 N5 112.9(2) . . ?
O7 C5 H5A 109.2 . . ?
O7 C5 C6 114.6(2) . . ?
C6 N6 H6 124.1 . . ?
C7 N6 H6 124.1 . . ?
C7 N6 C6 111.9(2) . . ?
C5 C6 H6A 111.5 . . ?
N6 C6 C5 101.6(2) . . ?
N6 C6 H6A 111.5 . . ?
O8 C6 C5 110.0(2) . . ?
O8 C6 N6 110.5(2) . . ?
O8 C6 H6A 111.5 . . ?
C5 O7 H7 109.5 . . ?
O9 N7 C8 117.0(2) . . ?
O9 N7 O10 120.9(2) . . ?
O10 N7 C8 122.1(2) . . ?
N5 C7 C8 125.0(2) . . ?
N6 C7 N5 108.8(2) . . ?
N6 C7 C8 126.2(2) . . ?
O11 N8 C8 117.6(2) . . ?
O12 N8 C8 121.1(2) . . ?
O12 N8 O11 121.3(2) . . ?
C6 O8 H8 109.5 . . ?
N7 C8 C7 120.9(2) . . ?
N8 C8 N7 117.6(2) . . ?
N8 C8 C7 121.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 -97.2(3) . . . . ?
O1 C1 C2 O2 145.3(2) . . . . ?
N1 C1 C2 N2 19.4(3) . . . . ?
N1 C1 C2 O2 -98.1(3) . . . . ?
N1 C3 C4 N3 -0.6(5) . . . . ?
N1 C3 C4 N4 178.7(3) . . . . ?
C1 N1 C3 N2 8.1(4) . . . . ?
C1 N1 C3 C4 -171.0(3) . . . . ?
N2 C3 C4 N3 -179.5(3) . . . . ?
N2 C3 C4 N4 -0.2(5) . . . . ?
C2 N2 C3 N1 6.1(4) . . . . ?
C2 N2 C3 C4 -174.8(3) . . . . ?
C3 N1 C1 O1 97.1(3) . . . . ?
C3 N1 C1 C2 -17.7(3) . . . . ?
C3 N2 C2 C1 -16.6(3) . . . . ?
C3 N2 C2 O2 102.3(3) . . . . ?
O3 N3 C4 C3 -174.4(4) . . . . ?
O3 N3 C4 N4 6.3(5) . . . . ?
O4 N3 C4 C3 1.6(5) . . . . ?
O4 N3 C4 N4 -177.7(3) . . . . ?
N5 C5 C6 N6 -20.0(3) . . . . ?
N5 C5 C6 O8 97.1(3) . . . . ?
N5 C7 C8 N7 175.4(3) . . . . ?
N5 C7 C8 N8 -6.5(4) . . . . ?
C5 N5 C7 N6 -11.1(3) . . . . ?
C5 N5 C7 C8 168.6(3) . . . . ?
O5 N4 C4 N3 -171.5(3) . . . . ?
O5 N4 C4 C3 9.1(4) . . . . ?
N6 C7 C8 N7 -5.0(4) . . . . ?
N6 C7 C8 N8 173.1(3) . . . . ?
C6 N6 C7 N5 -3.8(3) . . . . ?
C6 N6 C7 C8 176.6(3) . . . . ?
O6 N4 C4 N3 10.4(4) . . . . ?
O6 N4 C4 C3 -168.9(3) . . . . ?
O7 C5 C6 N6 101.9(3) . . . . ?
O7 C5 C6 O8 -141.0(2) . . . . ?
C7 N5 C5 C6 19.9(3) . . . . ?
C7 N5 C5 O7 -103.2(3) . . . . ?
C7 N6 C6 C5 15.6(3) . . . . ?
C7 N6 C6 O8 -101.1(3) . . . . ?
O9 N7 C8 C7 20.0(4) . . . . ?
O9 N7 C8 N8 -158.2(3) . . . . ?
O10 N7 C8 C7 -160.8(3) . . . . ?
O10 N7 C8 N8 21.0(4) . . . . ?
O11 N8 C8 N7 -166.3(3) . . . . ?
O11 N8 C8 C7 15.5(4) . . . . ?
O12 N8 C8 N7 15.9(4) . . . . ?
O12 N8 C8 C7 -162.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
