# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_aks244
_database_code_depnum_ccdc_archive 'CCDC 1515419'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H6 N6 O4'
_chemical_formula_weight         250.19

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.790(3)
_cell_length_b                   13.286(7)
_cell_length_c                   13.788(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1060.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4472
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      26.24

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9588
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.55
_reflns_number_total             2149
_reflns_number_gt                1647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(15)
_refine_ls_number_reflns         2149
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 -0.0435(2) 0.80392(11) 0.19297(9) 0.0462(4) Uani 1 1 d . . .
N5 N 0.6001(3) 1.02067(13) 0.41884(13) 0.0574(4) Uani 1 1 d . . .
C4 C 0.1252(3) 0.84998(13) 0.35107(12) 0.0427(4) Uani 1 1 d . . .
C1 C 0.4206(3) 0.98555(14) 0.25580(12) 0.0491(5) Uani 1 1 d . . .
C3 C 0.2785(3) 0.90620(14) 0.40437(12) 0.0460(5) Uani 1 1 d . . .
H3 H 0.2821 0.9010 0.4716 0.055 Uiso 1 1 calc R . .
N6 N -0.0215(3) 0.77742(13) 0.40322(10) 0.0513(4) Uani 1 1 d . . .
O3 O -0.1153(3) 0.80701(11) 0.47710(10) 0.0780(5) Uani 1 1 d . . .
C6 C 0.2568(3) 0.92978(15) 0.20568(12) 0.0489(5) Uani 1 1 d . . .
H6 H 0.2425 0.9394 0.1391 0.059 Uiso 1 1 calc R . .
C5 C 0.1138(3) 0.86060(13) 0.25050(11) 0.0426(4) Uani 1 1 d . . .
O4 O -0.0361(3) 0.69192(11) 0.37124(9) 0.0660(4) Uani 1 1 d . . .
C2 C 0.4270(3) 0.97040(13) 0.35663(11) 0.0441(4) Uani 1 1 d . . .
N4 N -0.2032(3) 0.71517(15) 0.08076(12) 0.0718(5) Uani 1 1 d . . .
O2 O 0.7851(3) 1.04192(13) 0.38251(12) 0.0836(5) Uani 1 1 d . . .
O1 O 0.5529(3) 1.03462(11) 0.50403(10) 0.0768(5) Uani 1 1 d . . .
N2 N -0.2699(3) 0.79725(15) 0.21583(13) 0.0675(5) Uani 1 1 d . . .
C7 C -0.0093(4) 0.75382(15) 0.11061(12) 0.0590(6) Uani 1 1 d . . .
H7 H 0.1320 0.7474 0.0791 0.071 Uiso 1 1 calc R . .
N3 N -0.3627(3) 0.74407(15) 0.14714(13) 0.0739(6) Uani 1 1 d . . .
C8 C 0.5742(4) 1.05634(17) 0.19926(15) 0.0693(6) Uani 1 1 d . . .
H8A H 0.5186 1.0617 0.1339 0.104 Uiso 1 1 calc R . .
H8B H 0.7293 1.0307 0.1988 0.104 Uiso 1 1 calc R . .
H8C H 0.5725 1.1216 0.2292 0.104 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
N1 C7 1.331(2) . ?
N1 N2 1.351(2) . ?
N1 C5 1.424(2) . ?
N5 O2 1.215(2) . ?
N5 O1 1.220(2) . ?
N5 C2 1.479(2) . ?
C4 C3 1.373(2) . ?
C4 C5 1.395(2) . ?
C4 N6 1.472(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.405(2) . ?
C1 C8 1.511(3) . ?
C3 C2 1.379(2) . ?
N6 O3 1.2196(19) . ?
N6 O4 1.221(2) . ?
C6 C5 1.383(3) . ?
N4 C7 1.302(3) . ?
N4 N3 1.356(3) . ?
N2 N3 1.298(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 108.12(16) . . ?
C7 N1 C5 130.12(16) . . ?
N2 N1 C5 121.71(15) . . ?
O2 N5 O1 123.98(18) . . ?
O2 N5 C2 117.58(17) . . ?
O1 N5 C2 118.37(17) . . ?
C3 C4 C5 120.49(17) . . ?
C3 C4 N6 117.88(15) . . ?
C5 C4 N6 121.62(17) . . ?
C6 C1 C2 115.74(17) . . ?
C6 C1 C8 118.53(16) . . ?
C2 C1 C8 125.73(18) . . ?
C4 C3 C2 118.97(15) . . ?
O3 N6 O4 124.78(16) . . ?
O3 N6 C4 116.98(16) . . ?
O4 N6 C4 118.21(15) . . ?
C5 C6 C1 122.78(15) . . ?
C6 C5 C4 118.89(17) . . ?
C6 C5 N1 119.06(15) . . ?
C4 C5 N1 122.04(17) . . ?
C3 C2 C1 122.99(17) . . ?
C3 C2 N5 115.17(15) . . ?
C1 C2 N5 121.82(17) . . ?
C7 N4 N3 105.22(17) . . ?
N3 N2 N1 105.49(17) . . ?
N4 C7 N1 109.78(19) . . ?
N2 N3 N4 111.39(18) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.55
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_nag208
_database_code_depnum_ccdc_archive 'CCDC 1515415'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 N7 O4'
_chemical_formula_weight         251.18

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.780(2)
_cell_length_b                   7.1353(12)
_cell_length_c                   11.0435(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.625(3)
_cell_angle_gamma                90.00
_cell_volume                     948.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      25.73

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10566
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.27
_reflns_number_total             2289
_reflns_number_gt                1702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2289
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N6 N 0.17813(11) 0.87456(19) 0.66407(13) 0.0353(3) Uani 1 1 d . . .
C2 C 0.20723(12) 0.6859(2) 0.63816(14) 0.0287(4) Uani 1 1 d . . .
N5 N 0.13439(12) 0.2886(2) 0.40233(12) 0.0380(4) Uani 1 1 d . . .
N1 N 0.43007(10) 0.36065(18) 0.81236(12) 0.0307(3) Uani 1 1 d . . .
C3 C 0.29683(12) 0.6085(2) 0.73172(14) 0.0298(4) Uani 1 1 d . . .
H3 H 0.3330 0.6754 0.8064 0.036 Uiso 1 1 calc R . .
C5 C 0.27908(13) 0.3307(2) 0.60580(14) 0.0306(4) Uani 1 1 d . . .
H5 H 0.3042 0.2119 0.5943 0.037 Uiso 1 1 calc R . .
O2 O 0.04194(11) 0.3315(2) 0.32886(12) 0.0546(4) Uani 1 1 d . . .
C1 C 0.14689(12) 0.5910(2) 0.52160(14) 0.0297(4) Uani 1 1 d . . .
N9 N 0.06190(13) 0.6687(3) 0.42971(15) 0.0434(4) Uani 1 1 d . . .
O3 O 0.10248(12) 0.95739(19) 0.58459(13) 0.0594(4) Uani 1 1 d . . .
N4 N 0.59441(12) 0.3694(2) 0.94192(14) 0.0446(4) Uani 1 1 d . . .
O1 O 0.18329(13) 0.1507(2) 0.38591(13) 0.0605(4) Uani 1 1 d . . .
C6 C 0.18740(13) 0.4073(2) 0.51362(14) 0.0305(4) Uani 1 1 d . . .
C4 C 0.33288(12) 0.4324(2) 0.71492(14) 0.0290(4) Uani 1 1 d . . .
N8 N 0.52424(11) 0.4630(2) 0.85159(14) 0.0404(4) Uani 1 1 d . . .
O4 O 0.23142(11) 0.94716(18) 0.76622(13) 0.0537(4) Uani 1 1 d . . .
N3 N 0.54909(12) 0.2068(2) 0.96477(13) 0.0436(4) Uani 1 1 d . . .
C9 C 0.44794(14) 0.2062(2) 0.88353(15) 0.0366(4) Uani 1 1 d . . .
H9 H 0.3960 0.1117 0.8764 0.044 Uiso 1 1 calc R . .
H2 H 0.0296(17) 0.599(3) 0.361(2) 0.064(7) Uiso 1 1 d . . .
H1 H 0.0424(18) 0.793(3) 0.434(2) 0.065(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N6 O3 1.2184(17) . ?
N6 O4 1.2202(17) . ?
N6 C2 1.450(2) . ?
C2 C3 1.375(2) . ?
C2 C1 1.430(2) . ?
N5 O1 1.2113(19) . ?
N5 O2 1.2264(17) . ?
N5 C6 1.459(2) . ?
N1 C9 1.328(2) . ?
N1 N8 1.3489(19) . ?
N1 C4 1.4371(18) . ?
C3 C4 1.372(2) . ?
C5 C4 1.377(2) . ?
C5 C6 1.381(2) . ?
C1 N9 1.333(2) . ?
C1 C6 1.423(2) . ?
N4 N8 1.2823(19) . ?
N4 N3 1.358(2) . ?
N3 C9 1.303(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N6 O4 121.44(15) . . ?
O3 N6 C2 120.13(14) . . ?
O4 N6 C2 118.42(13) . . ?
C3 C2 C1 123.20(15) . . ?
C3 C2 N6 115.40(13) . . ?
C1 C2 N6 121.39(13) . . ?
O1 N5 O2 122.32(14) . . ?
O1 N5 C6 118.73(14) . . ?
O2 N5 C6 118.95(15) . . ?
C9 N1 N8 107.56(13) . . ?
C9 N1 C4 132.26(14) . . ?
N8 N1 C4 120.07(13) . . ?
C4 C3 C2 119.96(14) . . ?
C4 C5 C6 119.15(15) . . ?
N9 C1 C6 123.81(15) . . ?
N9 C1 C2 122.94(16) . . ?
C6 C1 C2 113.25(13) . . ?
N8 N4 N3 111.04(14) . . ?
C5 C6 C1 123.73(14) . . ?
C5 C6 N5 115.49(15) . . ?
C1 C6 N5 120.76(13) . . ?
C3 C4 C5 120.64(14) . . ?
C3 C4 N1 118.05(13) . . ?
C5 C4 N1 121.28(14) . . ?
N4 N8 N1 106.46(14) . . ?
C9 N3 N4 105.15(14) . . ?
N3 C9 N1 109.78(16) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.255
_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_kommu
_database_code_depnum_ccdc_archive 'CCDC 1515413'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H6 N6 O5'
_chemical_formula_weight         266.19

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.1410(7)
_cell_length_b                   8.3150(7)
_cell_length_c                   10.2670(12)
_cell_angle_alpha                84.165(8)
_cell_angle_beta                 73.123(10)
_cell_angle_gamma                66.337(9)
_cell_volume                     534.25(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1796
_cell_measurement_theta_min      3.2319
_cell_measurement_theta_max      26.3137

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73167
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3590
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_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         3.24
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2191
_reflns_number_gt                1845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0896P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2191
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.008

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 0.10972(16) 0.12637(13) 0.92101(10) 0.0396(3) Uani 1 1 d . . .
N2 N 0.0340(2) 0.33650(15) 0.69797(13) 0.0377(3) Uani 1 1 d . . .
C2 C 0.1931(2) 0.07595(19) 0.55637(15) 0.0374(3) Uani 1 1 d . . .
H2 H 0.1700 0.1452 0.4810 0.045 Uiso 1 1 calc R . .
C11 C 0.2695(2) -0.13225(18) 0.77871(15) 0.0340(3) Uani 1 1 d . . .
C4 C 0.1757(2) 0.05000(17) 0.79782(14) 0.0321(3) Uani 1 1 d . . .
C12 C 0.1372(2) 0.15035(17) 0.68360(15) 0.0339(3) Uani 1 1 d . . .
C13 C 0.3218(2) -0.21195(19) 0.65409(15) 0.0372(3) Uani 1 1 d . . .
H6 H 0.3801 -0.3336 0.6441 0.045 Uiso 1 1 calc R . .
O2 O 0.3601(2) -0.19908(16) 0.98200(12) 0.0539(3) Uani 1 1 d . . .
N8 N 0.3150(2) -0.24932(16) 0.89278(13) 0.0403(3) Uani 1 1 d . . .
N5 N 0.3344(2) -0.18543(19) 0.41238(14) 0.0475(4) Uani 1 1 d . . .
O3 O 0.3066(2) -0.39208(14) 0.89015(13) 0.0590(4) Uani 1 1 d . . .
C1 C 0.2843(2) -0.10468(19) 0.54556(15) 0.0369(3) Uani 1 1 d . . .
O4 O 0.3838(3) -0.34192(18) 0.40651(15) 0.0725(5) Uani 1 1 d . . .
N9 N -0.1919(3) 0.60188(17) 0.74706(15) 0.0545(4) Uani 1 1 d . . .
N4 N -0.0113(3) 0.59972(18) 0.65472(18) 0.0613(4) Uani 1 1 d . . .
C14 C -0.1590(3) 0.4370(2) 0.77217(17) 0.0463(4) Uani 1 1 d . . .
H14 H -0.2551 0.3963 0.8323 0.056 Uiso 1 1 calc R . .
N7 N 0.1257(3) 0.44202(18) 0.62302(17) 0.0574(4) Uani 1 1 d . . .
O5 O 0.3168(3) -0.0897(2) 0.31581(14) 0.0848(5) Uani 1 1 d . . .
C8 C 0.2386(3) 0.2061(3) 0.9498(2) 0.0647(5) Uani 1 1 d . . .
H8A H 0.2166 0.3152 0.9028 0.097 Uiso 1 1 calc R . .
H8B H 0.3857 0.1287 0.9199 0.097 Uiso 1 1 calc R . .
H8C H 0.1997 0.2276 1.0460 0.097 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
O1 C4 1.3424(17) . ?
O1 C8 1.436(2) . ?
N2 C14 1.332(2) . ?
N2 N7 1.3497(19) . ?
N2 C12 1.4242(17) . ?
C2 C1 1.378(2) . ?
C2 C12 1.383(2) . ?
C11 C13 1.383(2) . ?
C11 C4 1.3975(19) . ?
C11 N8 1.4698(19) . ?
C4 C12 1.397(2) . ?
C13 C1 1.374(2) . ?
O2 N8 1.2142(17) . ?
N8 O3 1.2159(17) . ?
N5 O4 1.2068(19) . ?
N5 O5 1.210(2) . ?
N5 C1 1.4692(19) . ?
N9 C14 1.306(2) . ?
N9 N4 1.355(2) . ?
N4 N7 1.286(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C8 116.91(12) . . ?
C14 N2 N7 108.35(13) . . ?
C14 N2 C12 130.37(13) . . ?
N7 N2 C12 121.13(12) . . ?
C1 C2 C12 117.45(14) . . ?
C13 C11 C4 122.57(14) . . ?
C13 C11 N8 116.62(12) . . ?
C4 C11 N8 120.80(13) . . ?
O1 C4 C11 122.34(13) . . ?
O1 C4 C12 120.82(12) . . ?
C11 C4 C12 116.64(12) . . ?
C2 C12 C4 122.55(13) . . ?
C2 C12 N2 118.24(13) . . ?
C4 C12 N2 119.20(12) . . ?
C1 C13 C11 117.50(13) . . ?
O2 N8 O3 124.39(14) . . ?
O2 N8 C11 118.62(12) . . ?
O3 N8 C11 116.99(13) . . ?
O4 N5 O5 123.93(15) . . ?
O4 N5 C1 118.25(15) . . ?
O5 N5 C1 117.77(14) . . ?
C13 C1 C2 123.23(13) . . ?
C13 C1 N5 118.78(13) . . ?
C2 C1 N5 117.93(14) . . ?
C14 N9 N4 105.22(14) . . ?
N7 N4 N9 111.67(14) . . ?
N9 C14 N2 109.17(16) . . ?
N4 N7 N2 105.59(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_azidebala
_database_code_depnum_ccdc_archive 'CCDC 1515418'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 N9 O4'
_chemical_formula_weight         277.18

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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                   13.9435(18)
_cell_length_b                   6.9570(6)
_cell_length_c                   12.8193(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.363(4)
_cell_angle_gamma                90.00
_cell_volume                     1104.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      29.68

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9292
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28338
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         29.73
_reflns_number_total             3088
_reflns_number_gt                2556
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0980P)²+0.4743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.1960
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.010

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
C4 C 0.16180(14) -0.0003(3) 0.12716(15) 0.0425(4) Uani 1 1 d . . .
H4 H 0.0951 -0.0332 0.1219 0.051 Uiso 1 1 calc R . .
N6 N 0.16781(13) 0.2844(2) 0.23991(14) 0.0450(4) Uani 1 1 d . . .
C5 C 0.21317(14) 0.1661(3) 0.18344(15) 0.0411(4) Uani 1 1 d . . .
C2 C 0.30968(15) -0.0707(3) 0.08071(16) 0.0466(4) Uani 1 1 d . . .
C3 C 0.21082(16) -0.1179(3) 0.07860(15) 0.0433(4) Uani 1 1 d . . .
C1 C 0.35434(15) 0.1037(3) 0.13591(19) 0.0501(5) Uani 1 1 d . . .
N2 N 0.15192(17) -0.2937(3) 0.02218(15) 0.0543(5) Uani 1 1 d . . .
C6 C 0.31054(15) 0.2207(3) 0.18803(19) 0.0488(5) Uani 1 1 d . . .
H6 H 0.3449 0.3336 0.2254 0.059 Uiso 1 1 calc R . .
O3 O 0.05451(16) -0.2924(3) -0.01655(18) 0.0750(5) Uani 1 1 d . . .
N3 N 0.37346(17) -0.1635(4) 0.0385(2) 0.0700(6) Uani 1 1 d . . .
N10 N 0.18717(17) 0.4750(3) 0.25310(18) 0.0615(5) Uani 1 1 d . . .
O4 O 0.20466(19) -0.4321(2) 0.01949(19) 0.0788(6) Uani 1 1 d . . .
N8 N 0.08126(17) 0.3973(3) 0.32872(19) 0.0654(6) Uani 1 1 d . . .
N4 N 0.33844(17) -0.2859(3) -0.03846(18) 0.0639(5) Uani 1 1 d . . .
N9 N 0.13513(18) 0.5390(3) 0.3068(2) 0.0676(6) Uani 1 1 d . . .
C8 C 0.10332(19) 0.2410(4) 0.2880(2) 0.0590(5) Uani 1 1 d . . .
H8 H 0.0782 0.1186 0.2917 0.071 Uiso 1 1 calc R . .
N1 N 0.45444(18) 0.1691(4) 0.1344(3) 0.0758(7) Uani 1 1 d . . .
O2 O 0.4429(3) 0.2690(7) 0.0529(5) 0.194(2) Uani 1 1 d . . .
O1 O 0.53822(17) 0.1193(5) 0.2104(3) 0.1193(10) Uani 1 1 d . . .
N5 N 0.3223(3) -0.3926(5) -0.1093(3) 0.0968(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
C4 C5 1.378(3) . ?
C4 C3 1.384(3) . ?
N6 C8 1.337(3) . ?
N6 N10 1.348(3) . ?
N6 C5 1.422(2) . ?
C5 C6 1.385(3) . ?
C2 N3 1.394(3) . ?
C2 C1 1.398(3) . ?
C2 C3 1.405(3) . ?
C3 N2 1.465(3) . ?
C1 C6 1.363(3) . ?
C1 N1 1.477(3) . ?
N2 O3 1.213(3) . ?
N2 O4 1.222(3) . ?
N3 N4 1.222(3) . ?
N10 N9 1.288(3) . ?
N8 C8 1.303(3) . ?
N8 N9 1.345(3) . ?
N4 N5 1.113(3) . ?
N1 O1 1.178(4) . ?
N1 O2 1.203(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
C5 C4 C3 119.12(17) . . ?
C8 N6 N10 107.62(17) . . ?
C8 N6 C5 130.86(18) . . ?
N10 N6 C5 121.52(16) . . ?
C4 C5 C6 121.09(17) . . ?
C4 C5 N6 120.46(16) . . ?
C6 C5 N6 118.44(17) . . ?
N3 C2 C1 112.51(19) . . ?
N3 C2 C3 132.8(2) . . ?
C1 C2 C3 114.65(17) . . ?
C4 C3 C2 122.44(17) . . ?
C4 C3 N2 115.76(17) . . ?
C2 C3 N2 121.78(17) . . ?
C6 C1 C2 124.81(19) . . ?
C6 C1 N1 117.5(2) . . ?
C2 C1 N1 117.68(18) . . ?
O3 N2 O4 124.7(2) . . ?
O3 N2 C3 117.64(18) . . ?
O4 N2 C3 117.6(2) . . ?
C1 C6 C5 117.81(19) . . ?
N4 N3 C2 123.1(2) . . ?
N9 N10 N6 106.13(18) . . ?
C8 N8 N9 105.69(19) . . ?
N5 N4 N3 168.3(3) . . ?
N10 N9 N8 111.36(19) . . ?
N8 C8 N6 109.2(2) . . ?
O1 N1 O2 125.0(3) . . ?
O1 N1 C1 118.8(3) . . ?
O2 N1 C1 116.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        29.73
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.419
_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_aks241
_database_code_depnum_ccdc_archive 'CCDC 1515416'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H7 N5 O2'
_chemical_formula_weight         205.19

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.162(7)
_cell_length_b                   12.424(11)
_cell_length_c                   9.201(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.868(14)
_cell_angle_gamma                90.00
_cell_volume                     901.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3056
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8069
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         26.09
_reflns_number_total             1770
_reflns_number_gt                1197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1770
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.03949(19) 0.27031(12) 0.51428(18) 0.0451(4) Uani 1 1 d . . .
O1 O 0.03951(19) 0.24190(10) 0.64234(16) 0.0619(4) Uani 1 1 d . . .
N2 N 0.22033(18) 0.52771(11) 0.18998(15) 0.0374(4) Uani 1 1 d . . .
C5 C 0.2923(2) 0.56108(14) 0.46250(19) 0.0362(4) Uani 1 1 d . . .
C6 C 0.2180(2) 0.49515(13) 0.33976(18) 0.0335(4) Uani 1 1 d . . .
O2 O -0.03414(19) 0.22153(12) 0.40115(17) 0.0672(5) Uani 1 1 d . . .
C1 C 0.1369(2) 0.40036(13) 0.35505(19) 0.0362(4) Uani 1 1 d . . .
H1 H 0.0873 0.3586 0.2715 0.043 Uiso 1 1 calc R . .
C2 C 0.1312(2) 0.36896(13) 0.49709(19) 0.0360(4) Uani 1 1 d . . .
C4 C 0.2806(2) 0.52544(14) 0.60332(19) 0.0408(4) Uani 1 1 d . . .
H4 H 0.3277 0.5674 0.6873 0.049 Uiso 1 1 calc R . .
C3 C 0.2021(2) 0.43060(14) 0.6225(2) 0.0403(5) Uani 1 1 d . . .
H3 H 0.1969 0.4084 0.7177 0.048 Uiso 1 1 calc R . .
C8 C 0.3790(2) 0.66484(15) 0.4453(2) 0.0502(5) Uani 1 1 d . . .
H8A H 0.4615 0.6523 0.3892 0.075 Uiso 1 1 calc R . .
H8B H 0.4345 0.6927 0.5428 0.075 Uiso 1 1 calc R . .
H8C H 0.2967 0.7159 0.3928 0.075 Uiso 1 1 calc R . .
N3 N 0.1299(2) 0.61309(13) 0.12234(18) 0.0548(5) Uani 1 1 d . . .
N4 N 0.1502(2) 0.61693(14) -0.01226(18) 0.0586(5) Uani 1 1 d . . .
N5 N 0.2530(2) 0.53622(14) -0.03546(18) 0.0582(5) Uani 1 1 d . . .
C7 C 0.2936(3) 0.48275(15) 0.0911(2) 0.0485(5) Uani 1 1 d . . .
H7 H 0.3632 0.4224 0.1094 0.058 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
N1 O2 1.221(2) . ?
N1 O1 1.230(2) . ?
N1 C2 1.466(2) . ?
N2 C7 1.333(2) . ?
N2 N3 1.350(2) . ?
N2 C6 1.441(2) . ?
C5 C4 1.395(3) . ?
C5 C6 1.401(2) . ?
C5 C8 1.499(3) . ?
C6 C1 1.376(2) . ?
C1 C2 1.376(2) . ?
C2 C3 1.382(3) . ?
C4 C3 1.374(3) . ?
N3 N4 1.292(2) . ?
N4 N5 1.359(2) . ?
N5 C7 1.307(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 123.59(17) . . ?
O2 N1 C2 118.45(16) . . ?
O1 N1 C2 117.95(16) . . ?
C7 N2 N3 107.62(15) . . ?
C7 N2 C6 130.80(16) . . ?
N3 N2 C6 121.44(13) . . ?
C4 C5 C6 116.39(17) . . ?
C4 C5 C8 121.19(16) . . ?
C6 C5 C8 122.41(16) . . ?
C1 C6 C5 122.55(16) . . ?
C1 C6 N2 117.57(15) . . ?
C5 C6 N2 119.85(16) . . ?
C6 C1 C2 118.31(16) . . ?
C1 C2 C3 121.77(17) . . ?
C1 C2 N1 118.84(16) . . ?
C3 C2 N1 119.31(16) . . ?
C3 C4 C5 122.43(17) . . ?
C4 C3 C2 118.52(17) . . ?
N4 N3 N2 106.34(15) . . ?
N3 N4 N5 111.08(15) . . ?
C7 N5 N4 105.10(16) . . ?
N5 C7 N2 109.84(18) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.09
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.194
_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_nag
_database_code_depnum_ccdc_archive 'CCDC 1515420'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H6 N6 O4'
_chemical_formula_weight         250.19

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   13.869(9)
_cell_length_b                   5.589(2)
_cell_length_c                   14.800(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.46(9)
_cell_angle_gamma                90.00
_cell_volume                     1018.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    881
_cell_measurement_theta_min      4.5060
_cell_measurement_theta_max      28.3440

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3945
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1758
_reflns_number_gt                1065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1758
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1992
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.002

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 -0.00988(19) -0.2804(4) 0.8658(2) 0.0415(8) Uani 1 1 d . . .
C2 C 0.1646(2) 0.1656(5) 0.8342(3) 0.0370(9) Uani 1 1 d . . .
C3 C 0.0762(2) 0.0239(5) 0.8136(3) 0.0418(10) Uani 1 1 d . . .
H3 H 0.0138 0.0359 0.7514 0.050 Uiso 1 1 calc R . .
N4 N 0.1519(2) 0.3393(5) 0.7559(2) 0.0434(8) Uani 1 1 d . . .
O5 O 0.1890(2) 0.5381(4) 0.7826(2) 0.0618(9) Uani 1 1 d . . .
O6 O 0.1032(2) 0.2761(4) 0.6682(2) 0.0586(8) Uani 1 1 d . . .
N7 N 0.0036(2) -0.5133(5) 0.8926(2) 0.0503(9) Uani 1 1 d . . .
C8 C 0.0809(2) -0.1341(5) 0.8851(3) 0.0372(9) Uani 1 1 d . . .
C9 C 0.2605(2) 0.1581(5) 0.9237(3) 0.0378(9) Uani 1 1 d . . .
C10 C 0.3604(2) 0.2992(6) 0.9447(3) 0.0515(11) Uani 1 1 d . . .
H10A H 0.3568 0.4524 0.9724 0.077 Uiso 1 1 calc R . .
H10B H 0.3650 0.3214 0.8825 0.077 Uiso 1 1 calc R . .
H10C H 0.4234 0.2144 0.9928 0.077 Uiso 1 1 calc R . .
C11 C 0.1731(2) -0.1551(6) 0.9751(3) 0.0487(10) Uani 1 1 d . . .
H11 H 0.1778 -0.2642 1.0245 0.058 Uiso 1 1 calc R . .
C12 C 0.2586(2) -0.0090(5) 0.9901(3) 0.0434(10) Uani 1 1 d . . .
N13 N -0.0922(3) -0.5959(5) 0.8637(3) 0.0614(10) Uani 1 1 d . . .
O14 O 0.3837(2) 0.1383(6) 1.1425(2) 0.0866(12) Uani 1 1 d . . .
N15 N 0.3536(2) -0.0350(7) 1.0903(3) 0.0589(10) Uani 1 1 d . . .
N16 N -0.1685(2) -0.4254(6) 0.8204(3) 0.0675(12) Uani 1 1 d . . .
C17 C -0.1153(2) -0.2360(6) 0.8212(3) 0.0516(11) Uani 1 1 d . . .
H17 H -0.1466 -0.0888 0.7941 0.062 Uiso 1 1 calc R . .
O18 O 0.3946(3) -0.2260(7) 1.1135(3) 0.1072(15) 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 C17 1.320(4) . ?
N1 N7 1.348(4) . ?
N1 C8 1.416(4) . ?
C2 C3 1.370(4) . ?
C2 C9 1.379(5) . ?
C2 N4 1.459(5) . ?
C3 C8 1.356(5) . ?
N4 O6 1.207(4) . ?
N4 O5 1.212(3) . ?
N7 N13 1.280(4) . ?
C8 C11 1.361(5) . ?
C9 C12 1.365(5) . ?
C9 C10 1.497(4) . ?
C11 C12 1.371(5) . ?
C12 N15 1.468(5) . ?
N13 N16 1.347(4) . ?
O14 N15 1.188(4) . ?
N15 O18 1.184(4) . ?
N16 C17 1.288(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
C17 N1 N7 107.5(3) . . ?
C17 N1 C8 132.0(3) . . ?
N7 N1 C8 120.5(2) . . ?
C3 C2 C9 124.4(3) . . ?
C3 C2 N4 116.1(3) . . ?
C9 C2 N4 119.5(3) . . ?
C8 C3 C2 119.0(3) . . ?
O6 N4 O5 124.2(3) . . ?
O6 N4 C2 117.5(3) . . ?
O5 N4 C2 118.2(3) . . ?
N13 N7 N1 105.5(3) . . ?
C3 C8 C11 120.4(3) . . ?
C3 C8 N1 120.0(3) . . ?
C11 C8 N1 119.5(3) . . ?
C12 C9 C2 112.4(3) . . ?
C12 C9 C10 122.3(3) . . ?
C2 C9 C10 125.1(3) . . ?
C8 C11 C12 117.3(4) . . ?
C9 C12 C11 126.4(3) . . ?
C9 C12 N15 119.2(3) . . ?
C11 C12 N15 114.3(3) . . ?
N7 N13 N16 111.8(3) . . ?
O18 N15 O14 124.7(4) . . ?
O18 N15 C12 118.0(3) . . ?
O14 N15 C12 117.3(3) . . ?
C17 N16 N13 104.8(3) . . ?
N16 C17 N1 110.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.848
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.279
_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_aks92
_database_code_depnum_ccdc_archive 'CCDC 1515422'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H6 N6 O5'
_chemical_formula_weight         266.19

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.9081(8)
_cell_length_b                   10.2255(7)
_cell_length_c                   21.181(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2146.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    931
_cell_measurement_theta_min      4.1050
_cell_measurement_theta_max      26.9230

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'

_exptl_special_details           
; 
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4067
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         28.93
_reflns_number_total             2258
_reflns_number_gt                1475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.3448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2258
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_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 1.08600(17) 0.08171(15) 0.05924(9) 0.0518(5) Uani 1 1 d . . .
N2 N 0.83590(18) 0.35802(18) 0.19693(10) 0.0406(5) Uani 1 1 d . . .
C3 C 0.9613(2) 0.2215(2) 0.12834(12) 0.0364(6) Uani 1 1 d . . .
H3 H 0.9182 0.1508 0.1472 0.044 Uiso 1 1 calc R . .
O4 O 0.9222(2) 0.60456(18) 0.19235(12) 0.0799(7) Uani 1 1 d . . .
C5 C 1.1123(2) 0.3082(2) 0.05232(11) 0.0362(5) Uani 1 1 d . . .
C6 C 0.9322(2) 0.3450(2) 0.14799(12) 0.0352(5) Uani 1 1 d . . .
N7 N 1.2083(2) 0.2957(2) 0.00079(11) 0.0469(6) Uani 1 1 d . . .
C8 C 1.0833(2) 0.4326(2) 0.07216(12) 0.0416(6) Uani 1 1 d . . .
H8 H 1.1236 0.5039 0.0525 0.050 Uiso 1 1 calc R . .
N9 N 0.9805(3) 0.5846(2) 0.14415(13) 0.0573(7) Uani 1 1 d . . .
C10 C 1.0538(2) 0.1995(2) 0.08082(12) 0.0364(6) Uani 1 1 d . . .
C11 C 0.9954(2) 0.4517(2) 0.12081(13) 0.0389(6) Uani 1 1 d . . .
N12 N 0.7185(2) 0.4205(2) 0.18898(14) 0.0666(8) Uani 1 1 d . . .
N13 N 0.6581(2) 0.4159(3) 0.24200(16) 0.0792(9) Uani 1 1 d . . .
O14 O 1.2206(2) 0.3879(2) -0.03402(11) 0.0856(8) Uani 1 1 d . . .
O15 O 1.2740(2) 0.1983(2) -0.00426(12) 0.0877(8) Uani 1 1 d . . .
N16 N 0.7331(3) 0.3530(3) 0.28541(14) 0.0770(8) Uani 1 1 d . . .
O17 O 1.0323(3) 0.67046(19) 0.11449(14) 0.1157(11) Uani 1 1 d . . .
C18 C 1.0259(3) -0.0302(2) 0.08842(15) 0.0616(8) Uani 1 1 d . . .
H18A H 1.0576 -0.1082 0.0680 0.092 Uiso 1 1 calc R . .
H18B H 0.9295 -0.0250 0.0846 0.092 Uiso 1 1 calc R . .
H18C H 1.0502 -0.0326 0.1323 0.092 Uiso 1 1 calc R . .
C19 C 0.8412(3) 0.3186(3) 0.25586(14) 0.0589(8) Uani 1 1 d . . .
H19 H 0.9126 0.2726 0.2737 0.071 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
O1 C10 1.328(3) . ?
O1 C18 1.431(3) . ?
N2 C19 1.313(3) . ?
N2 N12 1.338(3) . ?
N2 C6 1.415(3) . ?
C3 C6 1.360(3) . ?
C3 C10 1.379(3) . ?
O4 N9 1.191(3) . ?
C5 C8 1.370(3) . ?
C5 C10 1.391(3) . ?
C5 N7 1.453(3) . ?
C6 C11 1.384(3) . ?
N7 O15 1.195(3) . ?
N7 O14 1.203(2) . ?
C8 C11 1.364(3) . ?
N9 O17 1.195(3) . ?
N9 C11 1.453(3) . ?
N12 N13 1.273(3) . ?
N13 N16 1.346(4) . ?
N16 C19 1.289(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C18 118.49(19) . . ?
C19 N2 N12 107.5(2) . . ?
C19 N2 C6 129.8(2) . . ?
N12 N2 C6 122.6(2) . . ?
C6 C3 C10 121.0(2) . . ?
C8 C5 C10 121.4(2) . . ?
C8 C5 N7 116.7(2) . . ?
C10 C5 N7 121.9(2) . . ?
C3 C6 C11 120.6(2) . . ?
C3 C6 N2 117.0(2) . . ?
C11 C6 N2 122.4(2) . . ?
O15 N7 O14 122.9(2) . . ?
O15 N7 C5 119.8(2) . . ?
O14 N7 C5 117.3(2) . . ?
C11 C8 C5 119.9(2) . . ?
O4 N9 O17 122.2(2) . . ?
O4 N9 C11 120.1(2) . . ?
O17 N9 C11 117.7(3) . . ?
O1 C10 C3 124.0(2) . . ?
O1 C10 C5 118.4(2) . . ?
C3 C10 C5 117.6(2) . . ?
C8 C11 C6 119.4(2) . . ?
C8 C11 N9 117.1(2) . . ?
C6 C11 N9 123.4(2) . . ?
N13 N12 N2 106.3(2) . . ?
N12 N13 N16 111.1(2) . . ?
C19 N16 N13 104.9(3) . . ?
N16 C19 N2 110.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.797
_diffrn_reflns_theta_full        28.93
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.260
_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_exp_8701
_database_code_depnum_ccdc_archive 'CCDC 1515421'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 N7 O6'
_chemical_formula_weight         281.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.2628(3)
_cell_length_b                   10.5375(4)
_cell_length_c                   13.5924(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1040.25(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1538
_cell_measurement_theta_min      3.2420
_cell_measurement_theta_max      71.5190

_exptl_crystal_description       round
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2410
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         71.43
_reflns_number_total             1604
_reflns_number_gt                1582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1062P)²+0.5524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(5)
_refine_ls_number_reflns         1604
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1584
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8169(4) 0.8178(3) 0.2369(2) 0.0282(6) Uani 1 1 d . . .
N2 N 0.9613(4) 0.7590(2) 0.18398(18) 0.0308(6) Uani 1 1 d . . .
C3 C 0.6887(5) 0.8803(3) 0.3909(2) 0.0323(7) Uani 1 1 d . . .
C4 C 0.5236(4) 0.9175(3) 0.2415(2) 0.0317(7) Uani 1 1 d . . .
N5 N 0.3655(4) 0.9665(3) 0.1869(2) 0.0436(7) Uani 1 1 d . . .
C6 C 0.5321(4) 0.9264(3) 0.3447(2) 0.0328(7) Uani 1 1 d . . .
C7 C 0.8310(5) 0.8261(3) 0.3388(2) 0.0323(7) Uani 1 1 d . . .
H7 H 0.9348 0.7956 0.3711 0.039 Uiso 1 1 calc R . .
C8 C 0.6634(5) 0.8636(3) 0.1883(2) 0.0321(7) Uani 1 1 d . . .
H8 H 0.6551 0.8579 0.1202 0.038 Uiso 1 1 calc R . .
N9 N 0.7123(5) 0.8898(3) 0.4988(2) 0.0438(7) Uani 1 1 d . . .
C10 C 1.1114(4) 0.7144(3) 0.2300(2) 0.0348(7) Uani 1 1 d . . .
H10 H 1.1355 0.7197 0.2971 0.042 Uiso 1 1 calc R . .
N11 N 0.3791(4) 0.9842(3) 0.3992(2) 0.0440(7) Uani 1 1 d . . .
O12 O 0.3461(5) 0.9312(4) 0.1038(2) 0.0673(9) Uani 1 1 d . . .
N1 N 1.1334(4) 0.6722(3) 0.0744(2) 0.0461(7) Uani 1 1 d . . .
N3 N 1.2144(5) 0.6639(3) 0.1660(3) 0.0522(8) Uani 1 1 d . . .
N4 N 0.9787(5) 0.7317(3) 0.0869(3) 0.0531(9) Uani 1 1 d . . .
O1 O 0.5834(5) 0.9264(4) 0.5467(2) 0.0774(11) Uani 1 1 d . . .
O2 O 0.8621(5) 0.8649(4) 0.5323(2) 0.0701(10) Uani 1 1 d . . .
O3 O 0.3938(4) 1.0957(3) 0.4207(2) 0.0561(8) Uani 1 1 d . . .
O4 O 0.2492(5) 0.9172(4) 0.4166(3) 0.0854(13) Uani 1 1 d . . .
O5 O 0.2571(6) 1.0353(5) 0.2285(3) 0.1094(18) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.383(4) . ?
C1 C7 1.390(4) . ?
C1 N2 1.415(4) . ?
N2 C10 1.343(4) . ?
N2 N4 1.356(4) . ?
C3 C7 1.377(5) . ?
C3 C6 1.387(5) . ?
C3 N9 1.480(4) . ?
C4 C8 1.369(5) . ?
C4 C6 1.406(5) . ?
C4 N5 1.462(4) . ?
N5 O12 1.196(4) . ?
N5 O5 1.210(5) . ?
C6 N11 1.467(4) . ?
N9 O1 1.204(4) . ?
N9 O2 1.209(5) . ?
C10 N3 1.264(4) . ?
N11 O4 1.202(4) . ?
N11 O3 1.216(4) . ?
N1 N4 1.298(5) . ?
N1 N3 1.380(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
C8 C1 C7 120.9(3) . . ?
C8 C1 N2 120.5(3) . . ?
C7 C1 N2 118.7(3) . . ?
C10 N2 N4 107.7(3) . . ?
C10 N2 C1 121.2(2) . . ?
N4 N2 C1 131.1(3) . . ?
C7 C3 C6 121.8(3) . . ?
C7 C3 N9 116.8(3) . . ?
C6 C3 N9 121.3(3) . . ?
C8 C4 C6 121.5(3) . . ?
C8 C4 N5 117.4(3) . . ?
C6 C4 N5 121.2(3) . . ?
O12 N5 O5 123.4(3) . . ?
O12 N5 C4 117.5(3) . . ?
O5 N5 C4 119.0(3) . . ?
C3 C6 C4 117.6(3) . . ?
C3 C6 N11 122.5(3) . . ?
C4 C6 N11 119.9(3) . . ?
C3 C7 C1 118.9(3) . . ?
C4 C8 C1 119.3(3) . . ?
O1 N9 O2 124.5(3) . . ?
O1 N9 C3 117.9(3) . . ?
O2 N9 C3 117.6(3) . . ?
N3 C10 N2 107.9(3) . . ?
O4 N11 O3 126.1(3) . . ?
O4 N11 C6 116.7(3) . . ?
O3 N11 C6 117.1(3) . . ?
N4 N1 N3 106.3(3) . . ?
C10 N3 N1 110.0(3) . . ?
N1 N4 N2 108.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        71.43
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_naga138
_database_code_depnum_ccdc_archive 'CCDC 1515414'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 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 H6 N6 O5'
_chemical_formula_weight         266.19

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   71.027(5)
_cell_length_b                   9.0269(7)
_cell_length_c                   13.8125(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.138(2)
_cell_angle_gamma                90.00
_cell_volume                     8717.7(11)
_cell_formula_units_Z            32
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5832
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      21.86

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4352
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45293
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -88
_diffrn_reflns_limit_h_max       88
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.16
_diffrn_reflns_theta_max         26.41
_reflns_number_total             8940
_reflns_number_gt                5947
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1298P)²+20.0085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8940
_refine_ls_number_parameters     689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0863
_refine_ls_wR_factor_ref         0.2568
_refine_ls_wR_factor_gt          0.2279
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N21 N 0.16402(4) 0.9924(3) 1.0302(2) 0.0425(7) Uani 1 1 d . . .
O20 O 0.22636(4) 0.7587(3) 0.8867(2) 0.0574(7) Uani 1 1 d . . .
C3 C 0.17663(5) 0.8376(4) 0.9117(3) 0.0418(8) Uani 1 1 d . . .
H3 H 0.1643 0.8119 0.8820 0.050 Uiso 1 1 calc R . .
C1 C 0.19808(5) 0.9631(4) 1.0391(3) 0.0450(9) Uani 1 1 d . . .
H1 H 0.2001 1.0213 1.0956 0.054 Uiso 1 1 calc R . .
C4 C 0.19233(5) 0.7848(4) 0.8757(3) 0.0427(8) Uani 1 1 d . . .
C2 C 0.17977(5) 0.9296(4) 0.9930(3) 0.0412(8) Uani 1 1 d . . .
N19 N 0.18849(5) 0.6853(4) 0.7910(3) 0.0560(9) Uani 1 1 d . . .
N22 N 0.16681(5) 1.1094(4) 1.0925(3) 0.0567(9) Uani 1 1 d . . .
C5 C 0.21116(5) 0.8200(4) 0.9172(3) 0.0437(9) Uani 1 1 d . . .
C6 C 0.21318(5) 0.9096(4) 1.0008(3) 0.0455(9) Uani 1 1 d . . .
N20 N 0.23233(5) 0.9503(4) 1.0513(3) 0.0612(10) Uani 1 1 d . . .
N23 N 0.15039(5) 1.1450(4) 1.1114(3) 0.0587(9) Uani 1 1 d . . .
N24 N 0.13662(5) 1.0545(5) 1.0628(3) 0.0624(10) Uani 1 1 d . . .
O16 O 0.17454(6) 0.6071(4) 0.7827(3) 0.0886(12) Uani 1 1 d . . .
O19 O 0.24385(5) 0.9931(5) 1.0022(3) 0.0911(12) Uani 1 1 d . . .
O18 O 0.23540(5) 0.9421(5) 1.1401(2) 0.0873(12) Uani 1 1 d . . .
O17 O 0.19903(5) 0.6908(6) 0.7307(3) 0.1112(17) Uani 1 1 d . . .
C7 C 0.14549(6) 0.9626(5) 1.0141(3) 0.0558(11) Uani 1 1 d . . .
H7 H 0.1397 0.8870 0.9738 0.067 Uiso 1 1 calc R . .
C8 C 0.23415(7) 0.8374(7) 0.8122(3) 0.0771(15) Uani 1 1 d . . .
H8A H 0.2261 0.9208 0.7902 0.116 Uiso 1 1 calc R . .
H8B H 0.2347 0.7725 0.7577 0.116 Uiso 1 1 calc R . .
H8C H 0.2468 0.8714 0.8391 0.116 Uiso 1 1 calc R . .
O13 O 0.20729(4) 0.7730(3) 0.3788(2) 0.0542(7) Uani 1 1 d . . .
C25 C 0.18033(5) 0.5421(4) 0.5269(3) 0.0424(8) Uani 1 1 d . . .
H25 H 0.1825 0.4789 0.5809 0.051 Uiso 1 1 calc R . .
N13 N 0.14636(4) 0.5132(4) 0.5197(2) 0.0456(7) Uani 1 1 d . . .
C30 C 0.19545(5) 0.6082(4) 0.4934(2) 0.0400(8) Uani 1 1 d . . .
C29 C 0.19310(5) 0.6989(4) 0.4101(3) 0.0407(8) Uani 1 1 d . . .
N17 N 0.21439(5) 0.5840(5) 0.5539(2) 0.0529(9) Uani 1 1 d . . .
C27 C 0.15881(5) 0.6609(4) 0.3975(3) 0.0433(8) Uani 1 1 d . . .
H27 H 0.1464 0.6809 0.3655 0.052 Uiso 1 1 calc R . .
C28 C 0.17424(5) 0.7203(4) 0.3642(3) 0.0421(8) Uani 1 1 d . . .
C26 C 0.16198(5) 0.5709(4) 0.4794(3) 0.0388(8) Uani 1 1 d . . .
N18 N 0.17031(6) 0.8117(4) 0.2754(3) 0.0608(10) Uani 1 1 d . . .
O11 O 0.22482(4) 0.6910(4) 0.5711(2) 0.0699(9) Uani 1 1 d . . .
O12 O 0.21807(4) 0.4599(4) 0.5864(3) 0.0771(10) Uani 1 1 d . . .
O15 O 0.15704(5) 0.8996(4) 0.2692(3) 0.0881(11) Uani 1 1 d . . .
C32 C 0.12878(5) 0.5642(5) 0.5192(3) 0.0541(10) Uani 1 1 d . . .
H32 H 0.1235 0.6481 0.4858 0.065 Uiso 1 1 calc R . .
O14 O 0.18043(5) 0.7944(5) 0.2125(3) 0.0904(12) Uani 1 1 d . . .
N16 N 0.12013(5) 0.4784(5) 0.5727(3) 0.0713(11) Uani 1 1 d . . .
N14 N 0.14857(6) 0.3912(5) 0.5759(4) 0.0837(14) Uani 1 1 d . . .
C31 C 0.22166(7) 0.6884(6) 0.3417(4) 0.0782(15) Uani 1 1 d . . .
H31A H 0.2220 0.5897 0.3679 0.117 Uiso 1 1 calc R . .
H31B H 0.2339 0.7346 0.3613 0.117 Uiso 1 1 calc R . .
H31C H 0.2186 0.6844 0.2713 0.117 Uiso 1 1 calc R . .
N15 N 0.13276(7) 0.3717(6) 0.6072(4) 0.0964(16) Uani 1 1 d . . .
N1 N 0.08381(4) 0.7430(3) 0.2284(2) 0.0380(7) Uani 1 1 d . . .
N9 N 0.10329(4) 0.7755(4) 0.7203(2) 0.0470(8) Uani 1 1 d . . .
C14 C 0.07404(5) 0.5940(4) 0.0829(3) 0.0406(8) Uani 1 1 d . . .
H14 H 0.0867 0.5689 0.0823 0.049 Uiso 1 1 calc R . .
C18 C 0.08723(5) 0.8363(4) 0.6559(3) 0.0407(8) Uani 1 1 d . . .
C9 C 0.06922(5) 0.6822(4) 0.1566(2) 0.0365(8) Uani 1 1 d . . .
C21 C 0.05549(5) 0.9637(4) 0.5368(3) 0.0431(9) Uani 1 1 d . . .
O8 O 0.04015(4) 1.0318(4) 0.4839(2) 0.0618(8) Uani 1 1 d . . .
C19 C 0.06915(5) 0.7957(4) 0.6683(3) 0.0440(9) Uani 1 1 d . . .
H19 H 0.0674 0.7252 0.7151 0.053 Uiso 1 1 calc R . .
C23 C 0.09006(5) 0.9381(4) 0.5852(3) 0.0435(9) Uani 1 1 d . . .
H23 H 0.1023 0.9649 0.5772 0.052 Uiso 1 1 calc R . .
C22 C 0.07413(5) 0.9994(4) 0.5266(3) 0.0425(8) Uani 1 1 d . . .
C20 C 0.05376(5) 0.8614(4) 0.6104(3) 0.0433(8) Uani 1 1 d . . .
C10 C 0.05028(5) 0.7152(4) 0.1592(3) 0.0457(9) Uani 1 1 d . . .
H10 H 0.0471 0.7717 0.2101 0.055 Uiso 1 1 calc R . .
C13 C 0.05960(6) 0.5445(4) 0.0105(3) 0.0442(9) Uani 1 1 d . . .
N7 N 0.03495(5) 0.8263(5) 0.6337(3) 0.0571(9) Uani 1 1 d . . .
C15 C 0.08024(5) 0.8527(4) 0.2878(3) 0.0408(8) Uani 1 1 d . . .
H15 H 0.0685 0.8973 0.2885 0.049 Uiso 1 1 calc R . .
N3 N 0.11029(5) 0.7993(4) 0.3228(3) 0.0607(9) Uani 1 1 d . . .
N8 N 0.07817(6) 1.1101(4) 0.4547(3) 0.0566(9) Uani 1 1 d . . .
N4 N 0.09597(6) 0.8844(4) 0.3431(3) 0.0625(10) Uani 1 1 d . . .
O1 O 0.02656(5) 0.5137(4) -0.0589(2) 0.0733(9) Uani 1 1 d . . .
O9 O 0.06583(6) 1.1305(4) 0.3822(3) 0.0825(10) Uani 1 1 d . . .
C11 C 0.03638(5) 0.6633(5) 0.0854(3) 0.0482(9) Uani 1 1 d . . .
O7 O 0.03115(5) 0.6958(5) 0.6422(3) 0.0832(11) Uani 1 1 d . . .
O10 O 0.09339(5) 1.1744(4) 0.4717(3) 0.0772(10) Uani 1 1 d . . .
N6 N 0.06548(7) 0.4553(5) -0.0665(3) 0.0699(11) Uani 1 1 d . . .
C17 C 0.10307(5) 0.6403(4) 0.7579(3) 0.0453(9) Uani 1 1 d . . .
H17 H 0.0932 0.5721 0.7434 0.054 Uiso 1 1 calc R . .
N11 N 0.12993(5) 0.7432(5) 0.8199(3) 0.0654(10) Uani 1 1 d . . .
N5 N 0.01668(5) 0.7049(5) 0.0901(3) 0.0696(11) Uani 1 1 d . . .
N10 N 0.12012(6) 0.8389(6) 0.7600(3) 0.0802(12) Uani 1 1 d . . .
N12 N 0.11865(6) 0.6200(5) 0.8168(3) 0.0711(11) Uani 1 1 d . . .
C12 C 0.04043(6) 0.5763(5) 0.0079(3) 0.0490(9) Uani 1 1 d . . .
O3 O 0.00595(5) 0.7371(5) 0.0149(3) 0.1021(14) Uani 1 1 d . . .
O6 O 0.02457(5) 0.9291(5) 0.6467(3) 0.0904(12) Uani 1 1 d . . .
N2 N 0.10242(6) 0.7112(5) 0.2511(3) 0.0789(12) Uani 1 1 d . . .
O2 O 0.01227(5) 0.7103(6) 0.1712(3) 0.1063(15) Uani 1 1 d . . .
O5 O 0.05987(9) 0.4812(8) -0.1488(4) 0.171(3) Uani 1 1 d . . .
O4 O 0.07914(9) 0.3749(7) -0.0457(4) 0.151(2) Uani 1 1 d . . .
C24 C 0.02868(8) 0.9474(7) 0.4074(4) 0.0926(18) Uani 1 1 d . . .
H24A H 0.0353 0.9372 0.3530 0.139 Uiso 1 1 calc R . .
H24B H 0.0167 0.9974 0.3860 0.139 Uiso 1 1 calc R . .
H24C H 0.0263 0.8510 0.4321 0.139 Uiso 1 1 calc R . .
C16 C 0.02085(8) 0.5917(8) -0.1500(4) 0.0955(19) Uani 1 1 d . . .
H16A H 0.0088 0.6396 -0.1499 0.143 Uiso 1 1 calc R . .
H16B H 0.0196 0.5229 -0.2038 0.143 Uiso 1 1 calc R . .
H16C H 0.0303 0.6648 -0.1573 0.143 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
N21 C7 1.324(5) . ?
N21 N22 1.354(5) . ?
N21 C2 1.428(5) . ?
O20 C5 1.345(4) . ?
O20 C8 1.438(6) . ?
C3 C2 1.383(5) . ?
C3 C4 1.384(5) . ?
C1 C6 1.365(5) . ?
C1 C2 1.378(5) . ?
C4 C5 1.395(5) . ?
C4 N19 1.462(5) . ?
N19 O16 1.205(5) . ?
N19 O17 1.215(5) . ?
N22 N23 1.280(5) . ?
C5 C6 1.397(5) . ?
C6 N20 1.463(5) . ?
N20 O18 1.210(5) . ?
N20 O19 1.213(5) . ?
N23 N24 1.357(5) . ?
N24 C7 1.299(5) . ?
O13 C29 1.344(4) . ?
O13 C31 1.439(5) . ?
C25 C26 1.377(5) . ?
C25 C30 1.377(5) . ?
N13 C32 1.330(5) . ?
N13 N14 1.341(5) . ?
N13 C26 1.424(5) . ?
C30 C29 1.398(5) . ?
C30 N17 1.470(5) . ?
C29 C28 1.392(5) . ?
N17 O11 1.215(5) . ?
N17 O12 1.218(5) . ?
C27 C28 1.371(5) . ?
C27 C26 1.379(5) . ?
C28 N18 1.464(5) . ?
N18 O15 1.223(5) . ?
N18 O14 1.231(5) . ?
C32 N16 1.297(6) . ?
N16 N15 1.345(6) . ?
N14 N15 1.285(6) . ?
N1 N2 1.335(5) . ?
N1 C15 1.338(4) . ?
N1 C9 1.414(4) . ?
N9 C17 1.327(5) . ?
N9 N10 1.351(5) . ?
N9 C18 1.428(5) . ?
C14 C13 1.376(5) . ?
C14 C9 1.381(5) . ?
C18 C19 1.374(5) . ?
C18 C23 1.381(5) . ?
C9 C10 1.384(5) . ?
C21 O8 1.349(4) . ?
C21 C22 1.394(5) . ?
C21 C20 1.395(5) . ?
O8 C24 1.434(6) . ?
C19 C20 1.371(5) . ?
C23 C22 1.386(5) . ?
C22 N8 1.472(5) . ?
C20 N7 1.463(5) . ?
C10 C11 1.371(5) . ?
C13 C12 1.386(6) . ?
C13 N6 1.452(5) . ?
N7 O6 1.218(5) . ?
N7 O7 1.220(5) . ?
C15 N4 1.271(5) . ?
N3 N2 1.316(5) . ?
N3 N4 1.343(5) . ?
N8 O10 1.213(5) . ?
N8 O9 1.223(5) . ?
O1 C12 1.350(5) . ?
O1 C16 1.436(6) . ?
C11 C12 1.398(6) . ?
C11 N5 1.461(5) . ?
N6 O5 1.160(6) . ?
N6 O4 1.206(6) . ?
C17 N12 1.266(5) . ?
N11 N10 1.310(6) . ?
N11 N12 1.367(6) . ?
N5 O3 1.211(5) . ?
N5 O2 1.216(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 N21 N22 107.2(3) . . ?
C7 N21 C2 132.6(3) . . ?
N22 N21 C2 120.2(3) . . ?
C5 O20 C8 116.9(3) . . ?
C2 C3 C4 118.3(3) . . ?
C6 C1 C2 119.0(4) . . ?
C3 C4 C5 123.3(3) . . ?
C3 C4 N19 116.8(3) . . ?
C5 C4 N19 119.9(3) . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 N21 118.8(3) . . ?
C3 C2 N21 120.4(3) . . ?
O16 N19 O17 123.6(4) . . ?
O16 N19 C4 118.1(4) . . ?
O17 N19 C4 118.2(4) . . ?
N23 N22 N21 106.8(3) . . ?
O20 C5 C4 122.9(3) . . ?
O20 C5 C6 121.7(3) . . ?
C4 C5 C6 115.0(3) . . ?
C1 C6 C5 123.5(3) . . ?
C1 C6 N20 117.0(3) . . ?
C5 C6 N20 119.4(3) . . ?
O18 N20 O19 124.5(4) . . ?
O18 N20 C6 117.0(4) . . ?
O19 N20 C6 118.4(4) . . ?
N22 N23 N24 110.6(3) . . ?
C7 N24 N23 105.5(3) . . ?
N24 C7 N21 110.0(4) . . ?
C29 O13 C31 118.0(3) . . ?
C26 C25 C30 119.1(3) . . ?
C32 N13 N14 107.5(3) . . ?
C32 N13 C26 131.8(3) . . ?
N14 N13 C26 120.4(3) . . ?
C25 C30 C29 122.9(3) . . ?
C25 C30 N17 115.8(3) . . ?
C29 C30 N17 121.3(3) . . ?
O13 C29 C28 120.0(3) . . ?
O13 C29 C30 124.7(3) . . ?
C28 C29 C30 115.0(3) . . ?
O11 N17 O12 125.1(4) . . ?
O11 N17 C30 117.3(4) . . ?
O12 N17 C30 117.5(4) . . ?
C28 C27 C26 118.8(3) . . ?
C27 C28 C29 123.7(3) . . ?
C27 C28 N18 117.2(3) . . ?
C29 C28 N18 119.1(3) . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 N13 118.8(3) . . ?
C27 C26 N13 120.6(3) . . ?
O15 N18 O14 124.9(4) . . ?
O15 N18 C28 117.0(4) . . ?
O14 N18 C28 118.1(4) . . ?
N16 C32 N13 109.2(4) . . ?
C32 N16 N15 106.1(4) . . ?
N15 N14 N13 106.7(4) . . ?
N14 N15 N16 110.5(4) . . ?
N2 N1 C15 107.6(3) . . ?
N2 N1 C9 130.9(3) . . ?
C15 N1 C9 121.5(3) . . ?
C17 N9 N10 107.6(3) . . ?
C17 N9 C18 122.3(3) . . ?
N10 N9 C18 130.0(4) . . ?
C13 C14 C9 118.2(3) . . ?
C19 C18 C23 121.4(3) . . ?
C19 C18 N9 118.8(3) . . ?
C23 C18 N9 119.8(3) . . ?
C14 C9 C10 120.8(3) . . ?
C14 C9 N1 119.6(3) . . ?
C10 C9 N1 119.6(3) . . ?
O8 C21 C22 122.1(4) . . ?
O8 C21 C20 122.0(3) . . ?
C22 C21 C20 115.8(3) . . ?
C21 O8 C24 117.2(4) . . ?
C20 C19 C18 118.6(4) . . ?
C18 C23 C22 118.3(3) . . ?
C23 C22 C21 122.7(3) . . ?
C23 C22 N8 115.4(3) . . ?
C21 C22 N8 121.8(3) . . ?
C19 C20 C21 123.2(3) . . ?
C19 C20 N7 116.3(3) . . ?
C21 C20 N7 120.3(3) . . ?
C11 C10 C9 118.9(3) . . ?
C14 C13 C12 123.7(3) . . ?
C14 C13 N6 116.0(4) . . ?
C12 C13 N6 120.3(3) . . ?
O6 N7 O7 124.9(4) . . ?
O6 N7 C20 117.9(4) . . ?
O7 N7 C20 117.1(4) . . ?
N4 C15 N1 107.1(3) . . ?
N2 N3 N4 105.4(3) . . ?
O10 N8 O9 124.9(4) . . ?
O10 N8 C22 117.8(4) . . ?
O9 N8 C22 117.3(4) . . ?
C15 N4 N3 111.3(3) . . ?
C12 O1 C16 117.0(4) . . ?
C10 C11 C12 122.8(4) . . ?
C10 C11 N5 116.7(4) . . ?
C12 C11 N5 120.4(4) . . ?
O5 N6 O4 118.5(5) . . ?
O5 N6 C13 120.8(5) . . ?
O4 N6 C13 118.9(4) . . ?
N12 C17 N9 108.4(4) . . ?
N10 N11 N12 105.9(4) . . ?
O3 N5 O2 123.7(4) . . ?
O3 N5 C11 119.1(4) . . ?
O2 N5 C11 117.1(4) . . ?
N11 N10 N9 108.1(4) . . ?
C17 N12 N11 110.1(4) . . ?
O1 C12 C13 121.7(4) . . ?
O1 C12 C11 122.4(4) . . ?
C13 C12 C11 115.5(3) . . ?
N3 N2 N1 108.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.600
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_aks8vr_a
_database_code_depnum_ccdc_archive 'CCDC 1515417'
_audit_update_record             
;
2016-11-07 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 N8 O6'
_chemical_formula_weight         296.18

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   7.9223(5)
_cell_length_b                   18.5920(11)
_cell_length_c                   7.5610(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.730(2)
_cell_angle_gamma                90.00
_cell_volume                     1100.77(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2530
_cell_measurement_theta_min      0.990
_cell_measurement_theta_max      27.52

_exptl_crystal_description       round
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   Sadabs

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8239
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2505
_reflns_number_gt                2029
_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)+(0.0508P)²+0.6561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O001 O 0.8044(2) 0.76708(8) 0.7882(2) 0.0531(5) Uani 1 1 d . . .
N002 N 0.90462(19) 0.65581(8) 0.8009(2) 0.0308(5) Uani 0.987(6) 1 d P . .
H002 H 0.9770 0.6249 0.8518 0.037 Uiso 0.987(6) 1 calc PR . .
O003 O 0.4156(2) 0.71802(9) 0.7938(2) 0.0549(5) Uani 1 1 d . . .
N004 N 0.39728(18) 0.57986(8) 0.2270(2) 0.0275(3) Uani 1 1 d . . .
O005 O 0.6130(2) 0.66174(10) 0.96854(19) 0.0541(5) Uani 1 1 d . . .
O006 O 1.0354(2) 0.74124(9) 0.9686(2) 0.0603(5) Uani 1 1 d . . .
N007 N 0.9144(2) 0.72549(9) 0.8543(2) 0.0380(4) Uani 1 1 d . . .
N008 N 0.5408(2) 0.67930(9) 0.8210(2) 0.0357(4) Uani 1 1 d . . .
N009 N 0.1943(2) 0.58621(9) 0.0050(2) 0.0396(4) Uani 1 1 d . . .
N00A N 0.9927(2) 0.58463(9) 0.4884(2) 0.0339(4) Uani 1 1 d . . .
O00B O 1.09926(19) 0.57799(11) 0.6177(2) 0.0647(6) Uani 1 1 d . . .
C00C C 0.7766(2) 0.63417(9) 0.6630(2) 0.0241(4) Uani 1 1 d . . .
C00D C 0.5253(2) 0.59631(9) 0.3761(2) 0.0253(4) Uani 1 1 d . . .
C00E C 0.8146(2) 0.59854(9) 0.5115(2) 0.0248(4) Uani 1 1 d . . .
C00F C 0.6031(2) 0.64854(9) 0.6633(2) 0.0259(4) Uani 1 1 d . . .
C00G C 0.6927(2) 0.57882(9) 0.3688(2) 0.0261(4) Uani 1 1 d . . .
H00G H 0.7231 0.5545 0.2709 0.031 Uiso 1 1 calc R . .
C00H C 0.4788(2) 0.63160(9) 0.5217(2) 0.0283(4) Uani 1 1 d . . .
H00H H 0.3653 0.6437 0.5243 0.034 Uiso 1 1 calc R . .
O00I O 1.0243(2) 0.57847(13) 0.3392(2) 0.0745(6) Uani 1 1 d . . .
N00J N 0.3760(2) 0.51334(10) 0.1576(3) 0.0483(5) Uani 1 1 d . . .
N00K N 0.2532(3) 0.51813(10) 0.0244(3) 0.0526(5) Uani 1 1 d . . .
C00L C 0.2850(2) 0.62303(11) 0.1309(3) 0.0363(4) Uani 1 1 d . . .
H00L H 0.2732 0.6720 0.1509 0.044 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
O001 N007 1.215(2) . ?
N002 N007 1.356(2) . ?
N002 C00C 1.399(2) . ?
N002 H002 0.8600 . ?
O003 N008 1.217(2) . ?
N004 C00L 1.329(2) . ?
N004 N00J 1.344(2) . ?
N004 C00D 1.430(2) . ?
O005 N008 1.219(2) . ?
O006 N007 1.225(2) . ?
N008 C00F 1.473(2) . ?
N009 C00L 1.298(2) . ?
N009 N00K 1.349(2) . ?
N00A O00B 1.197(2) . ?
N00A O00I 1.198(2) . ?
N00A C00E 1.471(2) . ?
C00C C00E 1.395(2) . ?
C00C C00F 1.401(2) . ?
C00D C00G 1.375(2) . ?
C00D C00H 1.379(2) . ?
C00E C00G 1.384(2) . ?
C00F C00H 1.376(2) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
N00J N00K 1.292(2) . ?
C00L H00L 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N007 N002 C00C 119.96(14) . . ?
N007 N002 H002 120.0 . . ?
C00C N002 H002 120.0 . . ?
C00L N004 N00J 107.94(15) . . ?
C00L N004 C00D 129.59(15) . . ?
N00J N004 C00D 122.46(15) . . ?
O001 N007 O006 125.05(17) . . ?
O001 N007 N002 118.72(15) . . ?
O006 N007 N002 116.23(16) . . ?
O003 N008 O005 124.75(17) . . ?
O003 N008 C00F 117.21(16) . . ?
O005 N008 C00F 117.95(16) . . ?
C00L N009 N00K 105.74(16) . . ?
O00B N00A O00I 122.51(18) . . ?
O00B N00A C00E 119.44(16) . . ?
O00I N00A C00E 118.02(16) . . ?
C00E C00C N002 121.77(15) . . ?
C00E C00C C00F 115.21(15) . . ?
N002 C00C C00F 122.98(15) . . ?
C00G C00D C00H 121.38(15) . . ?
C00G C00D N004 119.40(16) . . ?
C00H C00D N004 119.18(15) . . ?
C00G C00E C00C 123.64(15) . . ?
C00G C00E N00A 115.44(15) . . ?
C00C C00E N00A 120.75(15) . . ?
C00H C00F C00C 122.79(16) . . ?
C00H C00F N008 115.49(15) . . ?
C00C C00F N008 121.63(15) . . ?
C00D C00G C00E 118.00(16) . . ?
C00D C00G H00G 121.0 . . ?
C00E C00G H00G 121.0 . . ?
C00F C00H C00D 118.92(16) . . ?
C00F C00H H00H 120.5 . . ?
C00D C00H H00H 120.5 . . ?
N00K N00J N004 106.02(16) . . ?
N00J N00K N009 110.88(16) . . ?
N009 C00L N004 109.43(18) . . ?
N009 C00L H00L 125.3 . . ?
N004 C00L H00L 125.3 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.049
