# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1477784'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N8 O8'
_chemical_formula_sum            'C7 H6 N8 O8'
_chemical_formula_weight         330.20

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   5.9313(6)
_cell_length_b                   25.036(3)
_cell_length_c                   8.5659(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.723(4)
_cell_angle_gamma                90.00
_cell_volume                     1269.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1164
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      23.96

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5179
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2267
_reflns_number_gt                1448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0363P)²+0.1747P] 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         2267
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1970(4) 0.20806(9) 0.2616(3) 0.0231(6) Uani 1 1 d . . .
C2 C -0.1484(4) 0.26287(9) 0.2952(3) 0.0223(6) Uani 1 1 d . . .
C3 C -0.1497(4) 0.12103(9) 0.1419(3) 0.0221(6) Uani 1 1 d . . .
H3A H -0.1175 0.1145 0.0315 0.027 Uiso 1 1 calc R . .
H3B H -0.3157 0.1208 0.1484 0.027 Uiso 1 1 calc R . .
C4 C -0.0458(4) 0.07616(9) 0.2436(3) 0.0216(6) Uani 1 1 d . . .
C5 C 0.0434(4) 0.29436(9) 0.2497(3) 0.0229(6) Uani 1 1 d . . .
C6 C 0.2862(4) 0.35349(9) 0.2408(3) 0.0230(6) Uani 1 1 d . . .
C7 C 0.4412(4) 0.39973(9) 0.2581(3) 0.0303(6) Uani 1 1 d . . .
H7A H 0.3939 0.4272 0.1814 0.045 Uiso 1 1 calc R . .
H7B H 0.5954 0.3882 0.2405 0.045 Uiso 1 1 calc R . .
H7C H 0.4370 0.4144 0.3639 0.045 Uiso 1 1 calc R . .
N1 N -0.3892(3) 0.19514(8) 0.3186(3) 0.0313(6) Uani 1 1 d . . .
N2 N -0.3086(3) 0.28293(8) 0.3740(3) 0.0300(5) Uani 1 1 d . . .
N3 N -0.0633(3) 0.17258(8) 0.1889(3) 0.0243(5) Uani 1 1 d D . .
H3 H 0.044(3) 0.1847(9) 0.142(3) 0.029 Uiso 1 1 d D . .
N4 N -0.1282(3) 0.07373(9) 0.4082(3) 0.0286(5) Uani 1 1 d . . .
N5 N 0.2102(3) 0.08043(8) 0.2595(3) 0.0281(5) Uani 1 1 d . . .
N6 N -0.1018(4) 0.02227(8) 0.1692(3) 0.0289(5) Uani 1 1 d . . .
N7 N 0.1543(3) 0.27913(8) 0.1313(3) 0.0298(5) Uani 1 1 d . . .
N8 N 0.1186(3) 0.34039(8) 0.3230(2) 0.0249(5) Uani 1 1 d . . .
O1 O -0.4594(3) 0.24207(7) 0.3904(2) 0.0360(5) Uani 1 1 d . . .
O2 O -0.2158(3) 0.03236(7) 0.4477(2) 0.0419(5) Uani 1 1 d . . .
O3 O -0.1010(3) 0.11409(8) 0.4851(2) 0.0441(5) Uani 1 1 d . . .
O4 O 0.3072(3) 0.07241(8) 0.3858(2) 0.0452(5) Uani 1 1 d . . .
O5 O 0.2941(3) 0.09099(7) 0.1378(2) 0.0383(5) Uani 1 1 d . . .
O6 O -0.2893(3) 0.01856(7) 0.1041(2) 0.0414(5) Uani 1 1 d . . .
O7 O 0.0420(3) -0.01254(7) 0.1826(2) 0.0419(5) Uani 1 1 d . . .
O8 O 0.3195(3) 0.31912(7) 0.1242(2) 0.0315(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0213(13) 0.0261(15) 0.0219(14) 0.0054(12) 0.0008(11) 0.0022(11)
C2 0.0233(13) 0.0239(14) 0.0196(14) 0.0012(11) 0.0011(12) 0.0042(11)
C3 0.0209(13) 0.0240(14) 0.0212(14) 0.0009(11) -0.0006(11) -0.0015(11)
C4 0.0207(13) 0.0226(13) 0.0219(14) -0.0032(11) 0.0031(11) -0.0022(11)
C5 0.0254(13) 0.0209(13) 0.0224(14) 0.0015(12) 0.0010(12) 0.0053(11)
C6 0.0277(13) 0.0238(14) 0.0174(14) 0.0016(11) -0.0002(12) 0.0055(11)
C7 0.0366(15) 0.0266(14) 0.0283(16) -0.0017(13) 0.0056(13) -0.0026(12)
N1 0.0284(12) 0.0290(13) 0.0378(14) -0.0005(11) 0.0111(11) 0.0028(10)
N2 0.0274(11) 0.0294(12) 0.0338(14) 0.0014(10) 0.0066(11) 0.0007(10)
N3 0.0229(11) 0.0220(12) 0.0289(13) 0.0009(10) 0.0085(10) -0.0031(9)
N4 0.0297(12) 0.0319(13) 0.0240(13) 0.0032(11) 0.0016(10) 0.0063(11)
N5 0.0246(11) 0.0269(13) 0.0325(15) -0.0004(11) -0.0004(11) 0.0024(10)
N6 0.0320(13) 0.0237(13) 0.0316(14) 0.0008(10) 0.0060(11) -0.0009(11)
N7 0.0298(12) 0.0284(12) 0.0320(13) -0.0065(10) 0.0075(11) -0.0065(10)
N8 0.0292(11) 0.0216(11) 0.0244(12) -0.0013(10) 0.0044(10) 0.0006(9)
O1 0.0315(10) 0.0343(11) 0.0441(12) -0.0014(9) 0.0164(9) 0.0020(9)
O2 0.0461(12) 0.0384(11) 0.0426(13) 0.0131(10) 0.0128(10) -0.0041(10)
O3 0.0656(14) 0.0391(12) 0.0279(12) -0.0069(10) 0.0062(10) 0.0016(11)
O4 0.0340(11) 0.0599(14) 0.0399(13) 0.0097(11) -0.0126(10) 0.0039(10)
O5 0.0252(10) 0.0509(12) 0.0401(12) 0.0022(10) 0.0113(9) -0.0006(9)
O6 0.0345(11) 0.0352(11) 0.0529(15) -0.0057(10) -0.0098(10) -0.0094(9)
O7 0.0445(11) 0.0275(10) 0.0540(14) -0.0026(9) 0.0046(10) 0.0095(10)
O8 0.0327(10) 0.0301(10) 0.0331(11) -0.0083(9) 0.0113(8) -0.0075(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.310(3) . ?
C1 N3 1.367(3) . ?
C1 C2 1.428(3) . ?
C2 N2 1.302(3) . ?
C2 C5 1.458(3) . ?
C3 N3 1.437(3) . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N6 1.520(3) . ?
C4 N5 1.520(3) . ?
C4 N4 1.523(3) . ?
C5 N7 1.301(3) . ?
C5 N8 1.373(3) . ?
C6 N8 1.297(3) . ?
C6 O8 1.342(3) . ?
C6 C7 1.480(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 O1 1.402(2) . ?
N2 O1 1.372(2) . ?
N3 H3 0.832(15) . ?
N4 O3 1.212(3) . ?
N4 O2 1.217(2) . ?
N5 O4 1.209(3) . ?
N5 O5 1.213(3) . ?
N6 O6 1.215(3) . ?
N6 O7 1.220(2) . ?
N7 O8 1.405(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 123.6(2) . . ?
N1 C1 C2 109.4(2) . . ?
N3 C1 C2 126.9(2) . . ?
N2 C2 C1 109.3(2) . . ?
N2 C2 C5 122.6(2) . . ?
C1 C2 C5 128.1(2) . . ?
N3 C3 C4 112.17(19) . . ?
N3 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N3 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N6 C4 N5 106.86(18) . . ?
N6 C4 N4 106.14(18) . . ?
N5 C4 N4 107.38(19) . . ?
N6 C4 C3 110.2(2) . . ?
N5 C4 C3 111.30(18) . . ?
N4 C4 C3 114.58(18) . . ?
N7 C5 N8 115.9(2) . . ?
N7 C5 C2 119.5(2) . . ?
N8 C5 C2 124.6(2) . . ?
N8 C6 O8 113.4(2) . . ?
N8 C6 C7 129.5(2) . . ?
O8 C6 C7 117.12(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 O1 104.30(18) . . ?
C2 N2 O1 105.55(18) . . ?
C1 N3 C3 120.29(19) . . ?
C1 N3 H3 117.8(17) . . ?
C3 N3 H3 117.6(17) . . ?
O3 N4 O2 127.1(2) . . ?
O3 N4 C4 115.5(2) . . ?
O2 N4 C4 117.4(2) . . ?
O4 N5 O5 127.4(2) . . ?
O4 N5 C4 118.9(2) . . ?
O5 N5 C4 113.7(2) . . ?
O6 N6 O7 127.0(2) . . ?
O6 N6 C4 115.4(2) . . ?
O7 N6 C4 117.6(2) . . ?
C5 N7 O8 102.36(18) . . ?
C6 N8 C5 101.6(2) . . ?
N2 O1 N1 111.46(15) . . ?
C6 O8 N7 106.74(16) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1477785'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 N6 Na O5'
_chemical_formula_sum            'C5 H5 N6 Na O5'
_chemical_formula_weight         252.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   7.6336(9)
_cell_length_b                   3.8428(5)
_cell_length_c                   32.115(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.568(5)
_cell_angle_gamma                90.00
_cell_volume                     942.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    662
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.68

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4464
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1677
_reflns_number_gt                1074
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0675P)²+1.5412P] 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         1677
_refine_ls_number_parameters     161
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2104(6) 0.4568(11) 0.14585(12) 0.0119(10) Uani 1 1 d . . .
C2 C 0.2751(5) 0.3500(11) 0.10589(13) 0.0130(10) Uani 1 1 d . . .
C3 C 0.4474(5) 0.4114(11) 0.08739(12) 0.0121(9) Uani 1 1 d . . .
C4 C 0.6524(6) 0.3702(12) 0.04535(13) 0.0166(10) Uani 1 1 d . . .
C5 C 0.7791(6) 0.2899(12) 0.01212(13) 0.0173(11) Uani 1 1 d . . .
H5A H 0.7242 0.1340 -0.0083 0.026 Uiso 1 1 calc R . .
H5B H 0.8824 0.1765 0.0243 0.026 Uiso 1 1 calc R . .
H5C H 0.8144 0.5060 -0.0017 0.026 Uiso 1 1 calc R . .
N1 N 0.0506(5) 0.3375(10) 0.14970(11) 0.0166(9) Uani 1 1 d . . .
N2 N 0.1574(5) 0.1696(10) 0.08636(11) 0.0173(9) Uani 1 1 d . . .
N3 N 0.3142(4) 0.6604(10) 0.17121(11) 0.0156(9) Uani 1 1 d . . .
N4 N 0.2561(4) 0.7346(9) 0.20818(11) 0.0118(8) Uani 1 1 d . . .
N5 N 0.5682(5) 0.5965(10) 0.10529(11) 0.0175(9) Uani 1 1 d . . .
N6 N 0.4930(4) 0.2610(9) 0.04984(11) 0.0125(8) Uani 1 1 d . . .
Na1 Na 0.1633(2) 0.9008(5) 0.29276(5) 0.0182(5) Uani 1 1 d . . .
O1 O 0.0152(4) 0.1562(9) 0.11286(9) 0.0203(8) Uani 1 1 d . . .
O2 O 0.3537(4) 0.9151(9) 0.23133(9) 0.0205(8) Uani 1 1 d . . .
O3 O 0.1106(4) 0.6389(9) 0.22212(9) 0.0233(8) Uani 1 1 d . . .
O4 O 0.7086(4) 0.5731(9) 0.07689(9) 0.0194(8) Uani 1 1 d . . .
O5 O 0.3200(4) 0.4110(9) 0.31278(10) 0.0192(8) Uani 1 1 d D . .
H5D H 0.404(4) 0.466(13) 0.2992(13) 0.023 Uiso 1 1 d D . .
H5E H 0.335(6) 0.324(12) 0.3362(8) 0.023 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.016(2) 0.007(2) 0.013(2) 0.0033(18) 0.0004(17) 0.000(2)
C2 0.013(2) 0.011(2) 0.015(2) 0.0008(19) 0.0032(18) 0.001(2)
C3 0.013(2) 0.009(2) 0.014(2) 0.0013(19) -0.0008(18) 0.002(2)
C4 0.014(2) 0.016(2) 0.019(2) 0.001(2) -0.0003(19) 0.004(2)
C5 0.015(2) 0.021(3) 0.016(2) -0.003(2) 0.0055(19) 0.000(2)
N1 0.015(2) 0.020(2) 0.015(2) -0.0048(17) 0.0009(15) -0.0036(18)
N2 0.0118(19) 0.022(2) 0.018(2) -0.0017(17) 0.0062(16) -0.0025(18)
N3 0.0120(19) 0.022(2) 0.0124(19) -0.0048(17) 0.0059(15) -0.0033(18)
N4 0.0099(19) 0.0108(19) 0.015(2) -0.0006(16) 0.0032(15) 0.0012(16)
N5 0.0137(19) 0.021(2) 0.018(2) -0.0038(18) 0.0081(15) -0.0015(19)
N6 0.0127(19) 0.011(2) 0.0140(19) -0.0028(16) 0.0037(15) -0.0021(17)
Na1 0.0152(9) 0.0207(10) 0.0188(9) 0.0001(8) 0.0045(7) 0.0032(8)
O1 0.0137(16) 0.030(2) 0.0169(17) -0.0055(15) 0.0018(13) -0.0068(15)
O2 0.0178(17) 0.0268(19) 0.0169(17) -0.0067(15) -0.0009(13) -0.0095(16)
O3 0.0127(16) 0.039(2) 0.0187(17) -0.0055(16) 0.0093(13) -0.0091(16)
O4 0.0126(16) 0.0239(18) 0.0218(18) -0.0058(15) 0.0058(13) -0.0011(15)
O5 0.0151(17) 0.025(2) 0.0176(17) 0.0041(15) 0.0030(14) 0.0017(16)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.310(5) . ?
C1 N3 1.375(5) . ?
C1 C2 1.439(6) . ?
C2 N2 1.292(5) . ?
C2 C3 1.468(6) . ?
C3 N5 1.295(5) . ?
C3 N6 1.385(5) . ?
C4 N6 1.297(5) . ?
C4 O4 1.345(5) . ?
C4 C5 1.480(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N1 O1 1.397(4) . ?
N1 Na1 2.490(4) 2_545 ?
N2 O1 1.387(4) . ?
N3 N4 1.303(5) . ?
N4 O3 1.256(4) . ?
N4 O2 1.257(4) . ?
N4 Na1 2.886(4) . ?
N5 O4 1.417(4) . ?
Na1 O5 2.318(4) . ?
Na1 O3 2.328(3) 2 ?
Na1 O5 2.382(4) 1_565 ?
Na1 O2 2.463(3) . ?
Na1 N1 2.490(4) 2 ?
Na1 O3 2.511(3) . ?
Na1 Na1 3.8428(5) 1_565 ?
Na1 Na1 3.8428(5) 1_545 ?
Na1 Na1 4.161(3) 2 ?
Na1 Na1 4.161(3) 2_545 ?
Na1 H5D 2.49(5) . ?
O3 Na1 2.328(3) 2_545 ?
O5 Na1 2.382(4) 1_545 ?
O5 H5D 0.81(2) . ?
O5 H5E 0.831(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 132.4(4) . . ?
N1 C1 C2 108.2(4) . . ?
N3 C1 C2 119.3(4) . . ?
N2 C2 C1 110.0(4) . . ?
N2 C2 C3 120.8(4) . . ?
C1 C2 C3 129.2(4) . . ?
N5 C3 N6 115.6(4) . . ?
N5 C3 C2 123.1(4) . . ?
N6 C3 C2 121.3(4) . . ?
N6 C4 O4 113.4(4) . . ?
N6 C4 C5 129.3(4) . . ?
O4 C4 C5 117.3(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 O1 105.5(3) . . ?
C1 N1 Na1 130.8(3) . 2_545 ?
O1 N1 Na1 123.7(2) . 2_545 ?
C2 N2 O1 105.5(3) . . ?
N4 N3 C1 117.7(3) . . ?
O3 N4 O2 118.1(3) . . ?
O3 N4 N3 124.8(3) . . ?
O2 N4 N3 117.0(3) . . ?
O3 N4 Na1 60.2(2) . . ?
O2 N4 Na1 58.01(19) . . ?
N3 N4 Na1 174.3(3) . . ?
C3 N5 O4 102.7(3) . . ?
C4 N6 C3 101.9(4) . . ?
O5 Na1 O3 146.76(14) . 2 ?
O5 Na1 O5 109.69(14) . 1_565 ?
O3 Na1 O5 100.35(13) 2 1_565 ?
O5 Na1 O2 86.17(12) . . ?
O3 Na1 O2 111.28(12) 2 . ?
O5 Na1 O2 84.20(12) 1_565 . ?
O5 Na1 N1 93.17(13) . 2 ?
O3 Na1 N1 66.20(12) 2 2 ?
O5 Na1 N1 102.20(13) 1_565 2 ?
O2 Na1 N1 173.37(14) . 2 ?
O5 Na1 O3 90.16(13) . . ?
O3 Na1 O3 80.59(9) 2 . ?
O5 Na1 O3 130.50(13) 1_565 . ?
O2 Na1 O3 51.36(10) . . ?
N1 Na1 O3 122.08(13) 2 . ?
O5 Na1 N4 87.16(12) . . ?
O3 Na1 N4 97.01(11) 2 . ?
O5 Na1 N4 108.00(12) 1_565 . ?
O2 Na1 N4 25.65(9) . . ?
N1 Na1 N4 147.77(13) 2 . ?
O3 Na1 N4 25.74(9) . . ?
O5 Na1 Na1 144.30(9) . 1_565 ?
O3 Na1 Na1 66.85(10) 2 1_565 ?
O5 Na1 Na1 34.60(9) 1_565 1_565 ?
O2 Na1 Na1 88.72(9) . 1_565 ?
N1 Na1 Na1 95.60(10) 2 1_565 ?
O3 Na1 Na1 113.63(9) . 1_565 ?
N4 Na1 Na1 102.79(8) . 1_565 ?
O5 Na1 Na1 35.70(9) . 1_545 ?
O3 Na1 Na1 113.15(10) 2 1_545 ?
O5 Na1 Na1 145.39(9) 1_565 1_545 ?
O2 Na1 Na1 91.28(9) . 1_545 ?
N1 Na1 Na1 84.39(10) 2 1_545 ?
O3 Na1 Na1 66.37(9) . 1_545 ?
N4 Na1 Na1 77.21(8) . 1_545 ?
Na1 Na1 Na1 179.998(1) 1_565 1_545 ?
O5 Na1 Na1 149.58(10) . 2 ?
O3 Na1 Na1 31.99(7) 2 2 ?
O5 Na1 Na1 95.40(8) 1_565 2 ?
O2 Na1 Na1 79.36(9) . 2 ?
N1 Na1 Na1 98.16(11) 2 2 ?
O3 Na1 Na1 59.94(9) . 2 ?
N4 Na1 Na1 68.40(8) . 2 ?
Na1 Na1 Na1 62.50(2) 1_565 2 ?
Na1 Na1 Na1 117.50(2) 1_545 2 ?
O5 Na1 Na1 96.45(9) . 2_545 ?
O3 Na1 Na1 60.98(10) 2 2_545 ?
O5 Na1 Na1 148.68(10) 1_565 2_545 ?
O2 Na1 Na1 80.57(9) . 2_545 ?
N1 Na1 Na1 92.97(11) 2 2_545 ?
O3 Na1 Na1 29.42(7) . 2_545 ?
N4 Na1 Na1 55.07(8) . 2_545 ?
Na1 Na1 Na1 117.50(2) 1_565 2_545 ?
Na1 Na1 Na1 62.50(2) 1_545 2_545 ?
Na1 Na1 Na1 55.00(4) 2 2_545 ?
O5 Na1 H5D 18.9(6) . . ?
O3 Na1 H5D 160.3(10) 2 . ?
O5 Na1 H5D 99.2(10) 1_565 . ?
O2 Na1 H5D 68.9(7) . . ?
N1 Na1 H5D 111.2(7) 2 . ?
O3 Na1 H5D 85.3(11) . . ?
N4 Na1 H5D 75.1(9) . . ?
Na1 Na1 H5D 132.1(9) 1_565 . ?
Na1 Na1 H5D 47.9(9) 1_545 . ?
Na1 Na1 H5D 143.3(10) 2 . ?
Na1 Na1 H5D 100.5(11) 2_545 . ?
N2 O1 N1 110.8(3) . . ?
N4 O2 Na1 96.3(2) . . ?
N4 O3 Na1 146.8(3) . 2_545 ?
N4 O3 Na1 94.1(2) . . ?
Na1 O3 Na1 118.60(12) 2_545 . ?
C4 O4 N5 106.5(3) . . ?
Na1 O5 Na1 109.69(14) . 1_545 ?
Na1 O5 H5D 93(4) . . ?
Na1 O5 H5D 118(4) 1_545 . ?
Na1 O5 H5E 130(3) . . ?
Na1 O5 H5E 89(3) 1_545 . ?
H5D O5 H5E 119(5) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1477786'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 N6 O4'
_chemical_formula_sum            'C5 H4 N6 O4'
_chemical_formula_weight         212.14
_chemical_absolute_configuration unk

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   'Pca2(1) '
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   8.3172(10)
_cell_length_b                   7.2260(10)
_cell_length_c                   14.148(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     850.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1639
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      24.26

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5466
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         25.42
_reflns_number_total             812
_reflns_number_gt                693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0307P)²+0.2969P] 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_number_reflns         812
_refine_ls_number_parameters     140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1020(4) 0.7331(4) 0.6780(2) 0.0226(7) Uani 1 1 d . . .
C2 C 0.1657(4) 0.5597(4) 0.6469(2) 0.0218(7) Uani 1 1 d . . .
C3 C 0.1372(3) 0.4607(4) 0.5586(2) 0.0205(7) Uani 1 1 d . . .
C4 C 0.1511(4) 0.2624(5) 0.4519(3) 0.0252(8) Uani 1 1 d . . .
C5 C 0.1849(5) 0.1065(5) 0.3875(3) 0.0385(9) Uani 1 1 d . . .
H5A H 0.2513 0.0145 0.4201 0.058 Uiso 1 1 calc R . .
H5B H 0.2424 0.1522 0.3317 0.058 Uiso 1 1 calc R . .
H5C H 0.0835 0.0493 0.3678 0.058 Uiso 1 1 calc R . .
N1 N 0.1616(3) 0.7745(4) 0.7606(2) 0.0302(7) Uani 1 1 d . . .
N2 N 0.2650(4) 0.4980(4) 0.71071(19) 0.0290(7) Uani 1 1 d . . .
N3 N -0.0058(3) 0.8391(4) 0.6269(2) 0.0280(7) Uani 1 1 d D . .
H3 H -0.082(3) 0.786(4) 0.594(2) 0.034 Uiso 1 1 d D . .
N4 N -0.0230(3) 1.0246(4) 0.6388(2) 0.0268(6) Uani 1 1 d . . .
N5 N 0.0350(4) 0.5226(4) 0.4971(2) 0.0329(7) Uani 1 1 d . . .
N6 N 0.2136(3) 0.3001(3) 0.5339(2) 0.0217(6) Uani 1 1 d . . .
O1 O 0.2647(3) 0.6284(3) 0.78149(17) 0.0331(6) Uani 1 1 d . . .
O2 O 0.0537(3) 1.1025(3) 0.70002(17) 0.0407(7) Uani 1 1 d . . .
O3 O -0.1169(3) 1.0993(3) 0.58301(18) 0.0321(6) Uani 1 1 d . . .
O4 O 0.0431(3) 0.3890(3) 0.42401(17) 0.0343(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0169(16) 0.0229(17) 0.0278(18) -0.0040(14) -0.0011(13) -0.0037(14)
C2 0.0164(16) 0.0210(17) 0.0279(19) 0.0016(14) -0.0014(15) -0.0017(12)
C3 0.0181(15) 0.0183(16) 0.0251(19) -0.0009(14) 0.0000(13) 0.0000(13)
C4 0.0221(18) 0.027(2) 0.027(2) -0.0029(16) 0.0019(15) 0.0027(15)
C5 0.041(2) 0.040(2) 0.035(2) -0.0139(19) -0.0009(17) 0.0091(18)
N1 0.0292(16) 0.0289(16) 0.0326(19) -0.0055(14) -0.0036(13) 0.0032(13)
N2 0.0309(16) 0.0261(16) 0.0300(16) -0.0071(14) -0.0043(13) 0.0026(14)
N3 0.0260(17) 0.0154(13) 0.0428(19) -0.0045(14) -0.0110(13) -0.0009(12)
N4 0.0328(15) 0.0190(13) 0.0285(15) -0.0012(15) 0.0044(14) -0.0017(12)
N5 0.0379(18) 0.0320(17) 0.0287(15) -0.0105(14) -0.0061(13) 0.0121(15)
N6 0.0175(14) 0.0211(13) 0.0265(14) -0.0035(12) -0.0003(12) 0.0018(10)
O1 0.0378(14) 0.0325(13) 0.0291(12) -0.0051(12) -0.0104(12) 0.0064(12)
O2 0.0643(19) 0.0216(14) 0.0363(16) -0.0069(12) -0.0077(14) -0.0040(12)
O3 0.0344(14) 0.0218(11) 0.0401(15) 0.0040(11) -0.0005(12) 0.0052(10)
O4 0.0391(15) 0.0336(14) 0.0302(13) -0.0098(11) -0.0099(11) 0.0117(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.305(5) . ?
C1 N3 1.382(4) . ?
C1 C2 1.430(4) . ?
C2 N2 1.302(4) . ?
C2 C3 1.459(4) . ?
C3 N5 1.296(4) . ?
C3 N6 1.368(4) . ?
C4 N6 1.300(4) . ?
C4 O4 1.342(4) . ?
C4 C5 1.476(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N1 O1 1.391(3) . ?
N2 O1 1.375(3) . ?
N3 N4 1.359(4) . ?
N3 H3 0.874(19) . ?
N4 O2 1.214(4) . ?
N4 O3 1.234(4) . ?
N5 O4 1.417(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 126.0(3) . . ?
N1 C1 C2 109.6(3) . . ?
N3 C1 C2 124.4(3) . . ?
N2 C2 C1 108.8(3) . . ?
N2 C2 C3 121.9(3) . . ?
C1 C2 C3 129.3(3) . . ?
N5 C3 N6 115.2(3) . . ?
N5 C3 C2 120.8(3) . . ?
N6 C3 C2 124.0(3) . . ?
N6 C4 O4 112.8(3) . . ?
N6 C4 C5 129.4(3) . . ?
O4 C4 C5 117.8(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 O1 104.5(3) . . ?
C2 N2 O1 105.6(2) . . ?
N4 N3 C1 123.4(3) . . ?
N4 N3 H3 115(2) . . ?
C1 N3 H3 121(2) . . ?
O2 N4 O3 125.9(3) . . ?
O2 N4 N3 119.3(3) . . ?
O3 N4 N3 114.8(3) . . ?
C3 N5 O4 102.9(2) . . ?
C4 N6 C3 102.7(3) . . ?
N2 O1 N1 111.5(2) . . ?
C4 O4 N5 106.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1477787'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N6 O4, H4 N O'
_chemical_formula_sum            'C5 H7 N7 O5'
_chemical_formula_weight         245.18

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   'C2/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                   32.485(7)
_cell_length_b                   4.0540(8)
_cell_length_c                   14.208(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.098(8)
_cell_angle_gamma                90.00
_cell_volume                     1852.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1586
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      25.59

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4768
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.23
_reflns_number_total             1641
_reflns_number_gt                1113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0417P)²+1.3515P] 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         1641
_refine_ls_number_parameters     168
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35582(8) 0.1536(7) 0.14258(19) 0.0168(6) Uani 1 1 d . . .
C2 C 0.39274(8) 0.2622(7) 0.1082(2) 0.0167(6) Uani 1 1 d . . .
C3 C 0.40902(8) 0.1740(7) 0.0214(2) 0.0193(7) Uani 1 1 d . . .
C4 C 0.44896(9) 0.1587(7) -0.0791(2) 0.0205(7) Uani 1 1 d . . .
C5 C 0.48155(9) 0.1880(8) -0.1401(2) 0.0273(7) Uani 1 1 d . . .
H5A H 0.4699 0.2877 -0.2009 0.041 Uiso 1 1 calc R . .
H5B H 0.4925 -0.0315 -0.1514 0.041 Uiso 1 1 calc R . .
H5C H 0.5041 0.3273 -0.1087 0.041 Uiso 1 1 calc R . .
N1 N 0.35367(7) 0.3021(6) 0.22379(17) 0.0201(6) Uani 1 1 d . . .
N2 N 0.41246(7) 0.4684(6) 0.16680(17) 0.0227(6) Uani 1 1 d . . .
N3 N 0.32966(7) -0.0669(6) 0.09212(16) 0.0182(5) Uani 1 1 d . . .
N4 N 0.29866(7) -0.1759(6) 0.13393(16) 0.0201(6) Uani 1 1 d . . .
N5 N 0.38958(7) -0.0162(6) -0.04226(17) 0.0246(6) Uani 1 1 d . . .
N6 N 0.44645(7) 0.2897(6) 0.00176(17) 0.0221(6) Uani 1 1 d . . .
N7 N 0.19533(7) 0.7671(6) 0.11935(17) 0.0191(6) Uani 1 1 d D . .
H7A H 0.2207(6) 0.675(5) 0.1269(16) 0.023 Uiso 1 1 d D . .
H7B H 0.1760(6) 0.643(5) 0.0849(16) 0.023 Uiso 1 1 d D . .
H7C H 0.1877(7) 0.811(5) 0.1773(13) 0.023 Uiso 1 1 d D . .
O1 O 0.38902(6) 0.5005(5) 0.23924(14) 0.0238(5) Uani 1 1 d . . .
O2 O 0.29110(7) -0.0868(5) 0.21237(14) 0.0287(5) Uani 1 1 d . . .
O3 O 0.27586(6) -0.3895(5) 0.08740(13) 0.0206(5) Uani 1 1 d . . .
O4 O 0.41628(6) -0.0303(5) -0.11138(14) 0.0251(5) Uani 1 1 d . . .
O5 O 0.19730(7) 1.0713(5) 0.07378(14) 0.0247(5) Uani 1 1 d D . .
H5 H 0.2052(10) 1.012(7) 0.0235(17) 0.030 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0184(15) 0.0164(15) 0.0147(14) 0.0027(12) -0.0008(12) 0.0020(12)
C2 0.0164(14) 0.0152(14) 0.0171(15) 0.0035(12) -0.0030(12) 0.0009(12)
C3 0.0171(15) 0.0191(16) 0.0215(16) 0.0014(13) 0.0021(13) -0.0024(12)
C4 0.0169(15) 0.0232(16) 0.0201(16) 0.0038(13) -0.0013(12) -0.0003(12)
C5 0.0210(17) 0.0343(19) 0.0272(17) 0.0023(15) 0.0054(13) 0.0005(14)
N1 0.0216(13) 0.0189(13) 0.0186(13) -0.0001(11) -0.0008(10) -0.0018(10)
N2 0.0228(13) 0.0246(14) 0.0208(13) 0.0018(12) 0.0028(11) -0.0025(11)
N3 0.0182(13) 0.0207(13) 0.0160(12) 0.0014(10) 0.0036(10) -0.0019(10)
N4 0.0188(13) 0.0226(14) 0.0189(14) 0.0003(11) 0.0031(11) 0.0010(11)
N5 0.0224(13) 0.0307(15) 0.0223(13) -0.0022(12) 0.0087(11) -0.0050(12)
N6 0.0198(13) 0.0262(14) 0.0204(14) 0.0012(11) 0.0025(11) -0.0013(11)
N7 0.0184(13) 0.0201(14) 0.0189(13) 0.0026(11) 0.0032(11) -0.0011(10)
O1 0.0286(12) 0.0241(11) 0.0181(10) -0.0036(9) 0.0016(9) -0.0053(9)
O2 0.0325(12) 0.0363(13) 0.0195(12) -0.0105(9) 0.0114(9) -0.0076(10)
O3 0.0186(10) 0.0241(11) 0.0188(11) -0.0034(9) 0.0011(9) -0.0053(9)
O4 0.0240(11) 0.0337(12) 0.0188(11) -0.0048(10) 0.0071(9) -0.0057(10)
O5 0.0379(13) 0.0176(11) 0.0206(11) 0.0023(9) 0.0102(10) 0.0020(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.312(3) . ?
C1 N3 1.365(4) . ?
C1 C2 1.427(4) . ?
C2 N2 1.285(3) . ?
C2 C3 1.454(4) . ?
C3 N5 1.284(4) . ?
C3 N6 1.368(3) . ?
C4 N6 1.279(4) . ?
C4 O4 1.337(3) . ?
C4 C5 1.464(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N1 O1 1.394(3) . ?
N2 O1 1.370(3) . ?
N3 N4 1.316(3) . ?
N4 O2 1.229(3) . ?
N4 O3 1.264(3) . ?
N5 O4 1.400(3) . ?
N7 O5 1.399(3) . ?
N7 H7A 0.898(18) . ?
N7 H7B 0.894(18) . ?
N7 H7C 0.911(18) . ?
O5 H5 0.828(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 131.0(3) . . ?
N1 C1 C2 108.1(2) . . ?
N3 C1 C2 120.9(2) . . ?
N2 C2 C1 110.2(3) . . ?
N2 C2 C3 120.1(3) . . ?
C1 C2 C3 129.7(3) . . ?
N5 C3 N6 115.2(3) . . ?
N5 C3 C2 122.9(2) . . ?
N6 C3 C2 121.9(3) . . ?
N6 C4 O4 113.4(2) . . ?
N6 C4 C5 129.8(3) . . ?
O4 C4 C5 116.7(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 O1 105.0(2) . . ?
C2 N2 O1 105.6(2) . . ?
N4 N3 C1 116.2(2) . . ?
O2 N4 O3 119.9(2) . . ?
O2 N4 N3 125.1(2) . . ?
O3 N4 N3 115.0(2) . . ?
C3 N5 O4 103.1(2) . . ?
C4 N6 C3 102.2(2) . . ?
O5 N7 H7A 108.7(15) . . ?
O5 N7 H7B 108.5(15) . . ?
H7A N7 H7B 113.2(17) . . ?
O5 N7 H7C 106.3(14) . . ?
H7A N7 H7C 109.6(17) . . ?
H7B N7 H7C 110.3(17) . . ?
N2 O1 N1 111.08(19) . . ?
C4 O4 N5 106.1(2) . . ?
N7 O5 H5 101(2) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1477792'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H7 N4, C5 H3 N6 O4'
_chemical_formula_sum            'C6 H10 N10 O4'
_chemical_formula_weight         286.24

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                   8.0321(8)
_cell_length_b                   8.2137(8)
_cell_length_c                   10.1222(9)
_cell_angle_alpha                73.271(3)
_cell_angle_beta                 80.987(3)
_cell_angle_gamma                65.449(3)
_cell_volume                     581.19(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1313
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      24.83

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5545
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2109
_reflns_number_gt                1463
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0479P)²+0.0945P] 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         2109
_refine_ls_number_parameters     203
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5698(3) 0.8090(3) 0.3601(2) 0.0182(5) Uani 1 1 d . . .
C2 C 0.5984(3) 0.6644(3) 0.4861(2) 0.0174(5) Uani 1 1 d . . .
C3 C 0.7459(3) 0.4813(3) 0.5207(2) 0.0183(5) Uani 1 1 d . . .
C4 C 0.8973(3) 0.2148(3) 0.6322(2) 0.0209(5) Uani 1 1 d . . .
C5 C 0.9764(3) 0.0323(3) 0.7305(2) 0.0289(6) Uani 1 1 d . . .
H5A H 0.9432 0.0462 0.8252 0.043 Uiso 1 1 calc R . .
H5B H 1.1101 -0.0183 0.7170 0.043 Uiso 1 1 calc R . .
H5C H 0.9282 -0.0519 0.7146 0.043 Uiso 1 1 calc R . .
C6 C 0.2601(3) 0.5347(3) -0.0146(2) 0.0195(5) Uani 1 1 d . . .
N1 N 0.4184(3) 0.9503(3) 0.37652(18) 0.0229(5) Uani 1 1 d . . .
N2 N 0.4651(3) 0.7186(3) 0.57543(18) 0.0222(5) Uani 1 1 d . . .
N3 N 0.6837(3) 0.7804(3) 0.24415(18) 0.0245(5) Uani 1 1 d . . .
N4 N 0.6740(3) 0.9308(3) 0.14582(18) 0.0242(5) Uani 1 1 d . . .
N5 N 0.8836(3) 0.4238(3) 0.43495(19) 0.0263(5) Uani 1 1 d . . .
N6 N 0.7479(3) 0.3555(3) 0.64510(18) 0.0200(5) Uani 1 1 d . . .
N7 N 0.2713(3) 0.5628(3) -0.1519(2) 0.0283(5) Uani 1 1 d D . .
H7A H 0.332(3) 0.629(3) -0.200(2) 0.034 Uiso 1 1 d D . .
H7B H 0.273(4) 0.474(3) -0.187(2) 0.034 Uiso 1 1 d D . .
N8 N 0.2112(3) 0.4000(3) 0.06123(19) 0.0225(5) Uani 1 1 d D . .
H8 H 0.204(3) 0.317(3) 0.027(2) 0.027 Uiso 1 1 d D . .
N9 N 0.2029(3) 0.3693(3) 0.20588(19) 0.0258(5) Uani 1 1 d D . .
H9A H 0.087(2) 0.391(3) 0.234(2) 0.031 Uiso 1 1 d D . .
H9B H 0.275(3) 0.254(2) 0.239(2) 0.031 Uiso 1 1 d D . .
N10 N 0.2892(3) 0.6434(3) 0.04488(19) 0.0250(5) Uani 1 1 d D . .
H10A H 0.279(3) 0.620(3) 0.1350(16) 0.030 Uiso 1 1 d D . .
H10B H 0.320(3) 0.732(3) -0.009(2) 0.030 Uiso 1 1 d D . .
O1 O 0.3511(2) 0.8943(2) 0.51070(15) 0.0248(4) Uani 1 1 d . . .
O2 O 0.7676(3) 0.9054(2) 0.03637(16) 0.0364(5) Uani 1 1 d . . .
O3 O 0.5837(2) 1.0915(2) 0.15991(16) 0.0312(4) Uani 1 1 d . . .
O4 O 0.9878(2) 0.2432(2) 0.50970(15) 0.0279(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0219(13) 0.0158(13) 0.0196(11) -0.0049(9) -0.0013(10) -0.0096(11)
C2 0.0193(13) 0.0215(14) 0.0157(11) -0.0063(10) 0.0025(10) -0.0123(11)
C3 0.0203(13) 0.0214(14) 0.0167(11) -0.0045(10) -0.0006(9) -0.0118(11)
C4 0.0257(14) 0.0231(14) 0.0172(11) -0.0063(10) 0.0006(10) -0.0123(13)
C5 0.0281(15) 0.0239(15) 0.0292(13) -0.0024(11) -0.0022(11) -0.0075(13)
C6 0.0183(12) 0.0163(13) 0.0187(11) -0.0019(10) -0.0010(9) -0.0034(11)
N1 0.0270(12) 0.0223(12) 0.0186(10) -0.0008(8) -0.0001(8) -0.0119(10)
N2 0.0249(12) 0.0175(11) 0.0229(10) -0.0021(9) -0.0021(9) -0.0086(10)
N3 0.0340(13) 0.0211(12) 0.0171(10) -0.0012(9) 0.0040(9) -0.0137(11)
N4 0.0322(12) 0.0222(13) 0.0203(11) -0.0018(9) -0.0013(9) -0.0149(11)
N5 0.0245(12) 0.0230(12) 0.0216(10) -0.0006(9) 0.0005(9) -0.0037(10)
N6 0.0241(11) 0.0180(11) 0.0170(10) -0.0043(8) 0.0008(8) -0.0080(10)
N7 0.0384(13) 0.0294(14) 0.0179(11) -0.0030(9) 0.0018(9) -0.0170(11)
N8 0.0295(12) 0.0228(12) 0.0180(10) -0.0045(9) -0.0002(9) -0.0135(10)
N9 0.0306(13) 0.0247(13) 0.0179(10) -0.0006(9) 0.0016(9) -0.0109(11)
N10 0.0378(13) 0.0227(12) 0.0158(10) -0.0016(9) 0.0039(9) -0.0169(11)
O1 0.0248(9) 0.0222(10) 0.0230(9) -0.0031(7) 0.0019(7) -0.0077(8)
O2 0.0598(13) 0.0371(12) 0.0190(9) -0.0091(8) 0.0151(9) -0.0299(11)
O3 0.0374(11) 0.0193(10) 0.0316(10) -0.0006(8) 0.0038(8) -0.0116(9)
O4 0.0252(10) 0.0257(10) 0.0234(9) -0.0033(7) 0.0029(7) -0.0039(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.315(3) . ?
C1 N3 1.383(3) . ?
C1 C2 1.443(3) . ?
C2 N2 1.301(3) . ?
C2 C3 1.461(3) . ?
C3 N5 1.304(3) . ?
C3 N6 1.378(3) . ?
C4 N6 1.296(3) . ?
C4 O4 1.346(3) . ?
C4 C5 1.480(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N10 1.320(3) . ?
C6 N8 1.321(3) . ?
C6 N7 1.337(3) . ?
N1 O1 1.402(2) . ?
N2 O1 1.377(2) . ?
N3 N4 1.326(3) . ?
N4 O3 1.253(2) . ?
N4 O2 1.256(2) . ?
N5 O4 1.412(2) . ?
N7 H7A 0.875(15) . ?
N7 H7B 0.889(15) . ?
N8 N9 1.408(3) . ?
N8 H8 0.867(15) . ?
N9 H9A 0.885(15) . ?
N9 H9B 0.872(15) . ?
N10 H10A 0.875(15) . ?
N10 H10B 0.874(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 130.3(2) . . ?
N1 C1 C2 108.5(2) . . ?
N3 C1 C2 121.0(2) . . ?
N2 C2 C1 109.4(2) . . ?
N2 C2 C3 120.69(19) . . ?
C1 C2 C3 129.9(2) . . ?
N5 C3 N6 115.1(2) . . ?
N5 C3 C2 122.42(19) . . ?
N6 C3 C2 122.5(2) . . ?
N6 C4 O4 113.2(2) . . ?
N6 C4 C5 129.2(2) . . ?
O4 C4 C5 117.6(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N10 C6 N8 120.1(2) . . ?
N10 C6 N7 121.2(2) . . ?
N8 C6 N7 118.6(2) . . ?
C1 N1 O1 105.09(17) . . ?
C2 N2 O1 105.89(18) . . ?
N4 N3 C1 116.1(2) . . ?
O3 N4 O2 120.15(19) . . ?
O3 N4 N3 123.37(19) . . ?
O2 N4 N3 116.4(2) . . ?
C3 N5 O4 102.82(17) . . ?
C4 N6 C3 102.35(19) . . ?
C6 N7 H7A 117.7(16) . . ?
C6 N7 H7B 118.1(16) . . ?
H7A N7 H7B 116(2) . . ?
C6 N8 N9 118.25(18) . . ?
C6 N8 H8 122.8(16) . . ?
N9 N8 H8 117.9(16) . . ?
N8 N9 H9A 107.3(16) . . ?
N8 N9 H9B 107.1(17) . . ?
H9A N9 H9B 111(2) . . ?
C6 N10 H10A 117.4(16) . . ?
C6 N10 H10B 117.2(15) . . ?
H10A N10 H10B 125(2) . . ?
N2 O1 N1 111.14(15) . . ?
C4 O4 N5 106.48(17) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
