# 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 2015

####################################################################### 
# 
# 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1004434'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H6 Cl N5 O4'
_chemical_formula_weight         199.57

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.2870(17)
_cell_length_b                   9.1930(18)
_cell_length_c                   9.926(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.89(3)
_cell_angle_gamma                90.00
_cell_volume                     737.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9055
_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  AFC10/Saturn724+
_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            4408
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.10
_reflns_number_total             1303
_reflns_number_gt                1208
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL

_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)+(0.0860P)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         1303
_refine_ls_number_parameters     154
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.128
_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
Cl1 Cl 0.11384(6) 0.22094(6) 0.40156(5) 0.0232(3) Uani 1 1 d D . .
C1 C 0.1350(3) 0.2015(2) 0.9701(2) 0.0172(5) Uani 1 1 d . . .
N1 N 0.1841(2) 0.09113(19) 1.05585(17) 0.0257(5) Uani 1 1 d . B .
H1A H 0.1909 0.1017 1.1430 0.031 Uiso 1 1 calc R . .
H1B H 0.2091 0.0091 1.0242 0.031 Uiso 1 1 calc R . .
O1 O 0.2420(9) 0.2825(8) 0.5079(6) 0.0286(14) Uani 0.765(9) 1 d PDU A 1
O1A O 0.238(2) 0.257(3) 0.5267(16) 0.020(4) Uani 0.235(9) 1 d PDU A 2
N2 N 0.1239(2) 0.19735(17) 0.83266(17) 0.0165(4) Uani 1 1 d . B 1
C2 C 0.0736(2) 0.3334(2) 0.7819(2) 0.0207(5) Uani 1 1 d . B 1
H2A H 0.0577 0.3603 0.6896 0.025 Uiso 1 1 calc R B 1
O2 O 0.1660(9) 0.0885(4) 0.3490(7) 0.0277(11) Uani 0.765(9) 1 d PDU A 1
O2A O 0.142(3) 0.0718(11) 0.370(2) 0.030(4) Uani 0.235(9) 1 d PDU A 2
N3 N 0.1762(3) 0.07530(19) 0.76860(19) 0.0251(5) Uani 1 1 d D . .
H3B H 0.252(3) 0.106(3) 0.728(3) 0.040(8) Uiso 1 1 d D . .
H3A H 0.087(2) 0.057(3) 0.7042(19) 0.031(7) Uiso 1 1 d D . .
O3 O 0.0632(5) 0.3232(3) 0.2910(2) 0.0389(9) Uani 0.765(9) 1 d PDU A 1
O3A O 0.171(2) 0.3076(10) 0.2916(8) 0.049(4) Uani 0.235(9) 1 d PDU A 2
N4 N 0.0516(2) 0.41835(18) 0.87933(17) 0.0218(4) Uani 1 1 d . . .
O4 O -0.0306(3) 0.1890(4) 0.4600(3) 0.0315(8) Uani 0.765(9) 1 d PDU A 1
O4A O -0.0395(10) 0.2604(18) 0.4120(17) 0.069(4) Uani 0.235(9) 1 d PDU A 2
N5 N 0.0913(2) 0.33508(18) 0.99730(18) 0.0199(4) Uani 1 1 d . B .
H5A H 0.0881 0.3659 1.0785 0.024 Uiso 1 1 calc R . .

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
Cl1 0.0302(4) 0.0226(4) 0.0152(4) 0.00078(17) 0.0015(3) 0.00553(19)
C1 0.0159(10) 0.0185(10) 0.0170(10) -0.0018(8) 0.0033(8) -0.0020(8)
N1 0.0412(11) 0.0197(9) 0.0169(9) 0.0021(7) 0.0079(8) 0.0048(8)
O1 0.0351(19) 0.024(3) 0.0247(19) 0.0029(17) 0.0021(16) -0.0093(14)
O1A 0.024(5) 0.020(7) 0.018(5) 0.008(4) 0.004(4) -0.007(4)
N2 0.0179(9) 0.0156(8) 0.0161(9) -0.0019(6) 0.0040(7) 0.0009(6)
C2 0.0224(11) 0.0221(11) 0.0174(10) 0.0027(8) 0.0038(9) 0.0011(8)
O2 0.034(2) 0.0235(17) 0.0289(17) -0.0019(15) 0.0138(14) 0.0017(16)
O2A 0.027(6) 0.013(5) 0.051(9) 0.008(4) 0.009(5) -0.006(4)
N3 0.0358(11) 0.0192(9) 0.0221(10) -0.0053(7) 0.0101(9) 0.0023(8)
O3 0.059(2) 0.0342(13) 0.0214(13) 0.0120(9) 0.0036(13) 0.0166(13)
O3A 0.086(9) 0.029(4) 0.024(4) 0.004(3) -0.004(5) 0.000(5)
N4 0.0266(10) 0.0185(9) 0.0206(9) 0.0031(7) 0.0063(7) 0.0043(7)
O4 0.0219(12) 0.0450(17) 0.0293(14) 0.0002(11) 0.0094(10) 0.0027(11)
O4A 0.034(5) 0.081(8) 0.087(8) -0.021(7) 0.003(5) 0.027(5)
N5 0.0251(10) 0.0205(10) 0.0154(8) -0.0003(7) 0.0070(7) 0.0031(7)

_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
Cl1 O4A 1.347(7) . ?
Cl1 O2 1.429(3) . ?
Cl1 O3 1.435(2) . ?
Cl1 O1 1.436(4) . ?
Cl1 O2A 1.437(9) . ?
Cl1 O1A 1.464(9) . ?
Cl1 O4 1.472(2) . ?
Cl1 O3A 1.509(7) . ?
C1 N5 1.325(2) . ?
C1 N1 1.328(3) . ?
C1 N2 1.347(3) . ?
N2 C2 1.377(3) . ?
N2 N3 1.405(2) . ?
C2 N4 1.287(3) . ?
N4 N5 1.376(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
O4A Cl1 O2 128.7(6) . . ?
O4A Cl1 O3 76.3(8) . . ?
O2 Cl1 O3 109.8(3) . . ?
O4A Cl1 O1 113.1(7) . . ?
O2 Cl1 O1 111.7(4) . . ?
O3 Cl1 O1 110.3(3) . . ?
O4A Cl1 O2A 118.4(10) . . ?
O2 Cl1 O2A 14.3(9) . . ?
O3 Cl1 O2A 119.6(9) . . ?
O1 Cl1 O2A 113.9(11) . . ?
O4A Cl1 O1A 111.9(11) . . ?
O2 Cl1 O1A 106.7(12) . . ?
O3 Cl1 O1A 122.2(9) . . ?
O1 Cl1 O1A 12.1(11) . . ?
O2A Cl1 O1A 106.2(11) . . ?
O4A Cl1 O4 32.8(8) . . ?
O2 Cl1 O4 108.2(3) . . ?
O3 Cl1 O4 107.89(15) . . ?
O1 Cl1 O4 108.8(3) . . ?
O2A Cl1 O4 94.6(8) . . ?
O1A Cl1 O4 101.1(10) . . ?
O4A Cl1 O3A 111.4(6) . . ?
O2 Cl1 O3A 91.0(5) . . ?
O3 Cl1 O3A 35.5(5) . . ?
O1 Cl1 O3A 91.4(5) . . ?
O2A Cl1 O3A 104.8(8) . . ?
O1A Cl1 O3A 102.7(9) . . ?
O4 Cl1 O3A 143.4(6) . . ?
N5 C1 N1 129.50(19) . . ?
N5 C1 N2 105.79(17) . . ?
N1 C1 N2 124.69(17) . . ?
C1 N2 C2 106.94(16) . . ?
C1 N2 N3 121.50(16) . . ?
C2 N2 N3 131.17(17) . . ?
N4 C2 N2 111.01(18) . . ?
C2 N4 N5 104.75(16) . . ?
C1 N5 N4 111.51(16) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.477
_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_bn2919
_database_code_depnum_ccdc_archive 'CCDC 1004435'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N8 O7'
_chemical_formula_weight         328.22

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.797(4)
_cell_length_b                   6.5463(19)
_cell_length_c                   14.572(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.617(4)
_cell_angle_gamma                90.00
_cell_volume                     1279.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3812
_cell_measurement_theta_min      2.877
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12552
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         29.12
_reflns_number_total             3383
_reflns_number_gt                2825
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL

_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)+(0.0689P)²+0.4690P] 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         3383
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45149(9) 0.2485(2) 0.61088(9) 0.0341(3) Uani 1 1 d . . .
O2 O 0.50180(9) 0.0960(2) 0.78270(9) 0.0347(3) Uani 1 1 d . . .
O3 O 0.65640(10) 0.0286(2) 0.84184(8) 0.0378(3) Uani 1 1 d . . .
O4 O 0.90063(10) 0.0247(2) 0.66435(10) 0.0421(4) Uani 1 1 d . . .
O5 O 0.86240(10) 0.1018(2) 0.51551(10) 0.0376(3) Uani 1 1 d . . .
O6 O 0.53531(10) 0.2532(2) 0.35781(9) 0.0388(4) Uani 1 1 d . . .
O7 O 0.42161(9) 0.3386(2) 0.42958(8) 0.0302(3) Uani 1 1 d . . .
N1 N 0.24071(11) 0.0838(3) 0.74073(11) 0.0305(3) Uani 1 1 d . . .
N2 N 0.29274(10) 0.1586(2) 0.67739(10) 0.0240(3) Uani 1 1 d . . .
N3 N 0.14100(9) 0.2437(2) 0.62219(9) 0.0221(3) Uani 1 1 d . . .
N4 N 0.05902(10) 0.3339(3) 0.56036(11) 0.0284(3) Uani 1 1 d . . .
N5 N 0.25581(11) 0.3493(3) 0.53357(10) 0.0277(3) Uani 1 1 d . . .
N6 N 0.58835(10) 0.0830(2) 0.77492(9) 0.0246(3) Uani 1 1 d . . .
N7 N 0.84000(10) 0.0770(2) 0.59227(11) 0.0291(3) Uani 1 1 d . . .
N8 N 0.50568(10) 0.2745(2) 0.43069(9) 0.0239(3) Uani 1 1 d . . .
C1 C 0.14945(13) 0.1369(3) 0.70487(12) 0.0280(4) Uani 1 1 d . . .
H1 H 0.0951 0.1061 0.7322 0.034 Uiso 1 1 calc R . .
C2 C 0.23325(11) 0.2568(2) 0.60619(10) 0.0208(3) Uani 1 1 d . . .
C3 C 0.53720(12) 0.2020(3) 0.60568(11) 0.0223(3) Uani 1 1 d . . .
C4 C 0.61364(11) 0.1252(3) 0.68538(11) 0.0217(3) Uani 1 1 d . . .
C5 C 0.71054(12) 0.0872(3) 0.68135(12) 0.0250(3) Uani 1 1 d . . .
H5 H 0.7582 0.0437 0.7361 0.030 Uiso 1 1 calc R . .
C6 C 0.73768(11) 0.1131(3) 0.59642(12) 0.0245(3) Uani 1 1 d . . .
C7 C 0.66960(12) 0.1733(2) 0.51534(11) 0.0229(3) Uani 1 1 d . . .
H7 H 0.6893 0.1857 0.4574 0.027 Uiso 1 1 calc R . .
C8 C 0.57329(11) 0.2148(2) 0.51958(11) 0.0213(3) Uani 1 1 d . . .
H2 H 0.3577(19) 0.151(4) 0.6875(18) 0.057(8) Uiso 1 1 d . . .
H4A H 0.0337(18) 0.428(4) 0.5930(16) 0.045(6) Uiso 1 1 d . . .
H4B H 0.0143(18) 0.239(4) 0.5362(17) 0.047(7) Uiso 1 1 d . . .
H5A H 0.3142(18) 0.346(4) 0.5284(16) 0.042(6) Uiso 1 1 d . . .
H5B H 0.2079(17) 0.399(3) 0.4888(16) 0.038(6) Uiso 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
O1 0.0166(6) 0.0579(9) 0.0292(6) 0.0116(6) 0.0083(5) 0.0071(6)
O2 0.0207(6) 0.0575(9) 0.0270(6) 0.0056(6) 0.0080(5) 0.0000(6)
O3 0.0289(7) 0.0590(9) 0.0224(6) 0.0036(6) -0.0002(5) 0.0106(6)
O4 0.0186(6) 0.0560(9) 0.0493(8) 0.0063(7) 0.0033(6) 0.0069(6)
O5 0.0222(6) 0.0529(9) 0.0412(7) -0.0128(6) 0.0145(6) -0.0054(6)
O6 0.0355(7) 0.0594(10) 0.0248(6) 0.0068(6) 0.0139(5) 0.0058(6)
O7 0.0213(6) 0.0402(7) 0.0285(6) 0.0037(5) 0.0049(5) 0.0052(5)
N1 0.0259(7) 0.0402(9) 0.0281(7) 0.0087(6) 0.0117(6) 0.0032(6)
N2 0.0170(6) 0.0318(8) 0.0245(6) 0.0055(5) 0.0073(5) 0.0036(5)
N3 0.0145(6) 0.0291(7) 0.0235(6) -0.0004(5) 0.0057(5) 0.0010(5)
N4 0.0149(6) 0.0387(9) 0.0299(7) -0.0008(6) 0.0020(6) 0.0054(6)
N5 0.0173(7) 0.0416(9) 0.0253(7) 0.0085(6) 0.0072(6) 0.0024(6)
N6 0.0207(7) 0.0308(7) 0.0209(6) -0.0005(5) 0.0023(5) 0.0006(5)
N7 0.0177(7) 0.0313(8) 0.0390(8) -0.0072(6) 0.0084(6) -0.0017(6)
N8 0.0227(7) 0.0269(7) 0.0229(6) 0.0018(5) 0.0066(5) -0.0010(5)
C1 0.0230(8) 0.0361(9) 0.0275(8) 0.0016(7) 0.0114(6) -0.0004(7)
C2 0.0174(7) 0.0234(8) 0.0219(7) -0.0015(6) 0.0054(6) 0.0008(6)
C3 0.0165(7) 0.0276(8) 0.0232(7) 0.0015(6) 0.0050(6) -0.0010(6)
C4 0.0168(7) 0.0268(8) 0.0215(7) -0.0015(6) 0.0048(6) -0.0015(6)
C5 0.0173(7) 0.0264(8) 0.0293(8) -0.0018(6) 0.0019(6) -0.0005(6)
C6 0.0144(7) 0.0274(8) 0.0327(8) -0.0039(7) 0.0073(6) -0.0009(6)
C7 0.0208(8) 0.0231(8) 0.0267(8) -0.0037(6) 0.0093(6) -0.0035(6)
C8 0.0177(7) 0.0244(8) 0.0218(7) 0.0004(6) 0.0045(6) -0.0012(6)

_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 C3 1.2406(19) . ?
O2 N6 1.2288(18) . ?
O3 N6 1.2361(18) . ?
O4 N7 1.228(2) . ?
O5 N7 1.239(2) . ?
O6 N8 1.2325(18) . ?
O7 N8 1.2299(18) . ?
N1 C1 1.292(2) . ?
N1 N2 1.385(2) . ?
N2 C2 1.327(2) . ?
N2 H2 0.87(2) . ?
N3 C2 1.3496(19) . ?
N3 C1 1.374(2) . ?
N3 N4 1.4000(19) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.89(3) . ?
N5 C2 1.319(2) . ?
N5 H5A 0.83(2) . ?
N5 H5B 0.87(2) . ?
N6 C4 1.454(2) . ?
N7 C6 1.447(2) . ?
N8 C8 1.460(2) . ?
C1 H1 0.9500 . ?
C3 C8 1.457(2) . ?
C3 C4 1.462(2) . ?
C4 C5 1.375(2) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C7 C8 1.372(2) . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 104.11(14) . . ?
C2 N2 N1 111.71(13) . . ?
C2 N2 H2 125.5(17) . . ?
N1 N2 H2 122.5(17) . . ?
C2 N3 C1 107.16(13) . . ?
C2 N3 N4 120.93(13) . . ?
C1 N3 N4 131.90(14) . . ?
N3 N4 H4A 107.8(15) . . ?
N3 N4 H4B 109.8(16) . . ?
H4A N4 H4B 112(2) . . ?
C2 N5 H5A 118.7(17) . . ?
C2 N5 H5B 119.3(14) . . ?
H5A N5 H5B 122(2) . . ?
O2 N6 O3 121.42(14) . . ?
O2 N6 C4 120.88(13) . . ?
O3 N6 C4 117.67(14) . . ?
O4 N7 O5 122.99(15) . . ?
O4 N7 C6 119.00(15) . . ?
O5 N7 C6 118.01(15) . . ?
O7 N8 O6 122.04(14) . . ?
O7 N8 C8 120.44(13) . . ?
O6 N8 C8 117.50(14) . . ?
N1 C1 N3 111.41(15) . . ?
N1 C1 H1 124.3 . . ?
N3 C1 H1 124.3 . . ?
N5 C2 N2 129.08(15) . . ?
N5 C2 N3 125.32(15) . . ?
N2 C2 N3 105.61(14) . . ?
O1 C3 C8 124.22(15) . . ?
O1 C3 C4 123.75(14) . . ?
C8 C3 C4 112.02(13) . . ?
C5 C4 N6 116.43(14) . . ?
C5 C4 C3 123.73(14) . . ?
N6 C4 C3 119.84(13) . . ?
C4 C5 C6 119.09(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 121.76(15) . . ?
C7 C6 N7 118.96(15) . . ?
C5 C6 N7 119.29(15) . . ?
C8 C7 C6 119.24(15) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 123.94(14) . . ?
C7 C8 N8 115.88(14) . . ?
C3 C8 N8 120.18(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.9(2) . . . . ?
N2 N1 C1 N3 -0.6(2) . . . . ?
C2 N3 C1 N1 0.1(2) . . . . ?
N4 N3 C1 N1 -178.62(17) . . . . ?
N1 N2 C2 N5 179.26(17) . . . . ?
N1 N2 C2 N3 -0.90(19) . . . . ?
C1 N3 C2 N5 -179.64(17) . . . . ?
N4 N3 C2 N5 -0.8(3) . . . . ?
C1 N3 C2 N2 0.51(18) . . . . ?
N4 N3 C2 N2 179.37(14) . . . . ?
O2 N6 C4 C5 -173.82(15) . . . . ?
O3 N6 C4 C5 4.3(2) . . . . ?
O2 N6 C4 C3 5.6(2) . . . . ?
O3 N6 C4 C3 -176.27(15) . . . . ?
O1 C3 C4 C5 -175.29(17) . . . . ?
C8 C3 C4 C5 5.4(2) . . . . ?
O1 C3 C4 N6 5.4(3) . . . . ?
C8 C3 C4 N6 -173.95(14) . . . . ?
N6 C4 C5 C6 176.27(15) . . . . ?
C3 C4 C5 C6 -3.1(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C4 C5 C6 N7 178.82(15) . . . . ?
O4 N7 C6 C7 179.59(16) . . . . ?
O5 N7 C6 C7 0.0(2) . . . . ?
O4 N7 C6 C5 -0.2(2) . . . . ?
O5 N7 C6 C5 -179.81(15) . . . . ?
C5 C6 C7 C8 2.1(3) . . . . ?
N7 C6 C7 C8 -177.69(14) . . . . ?
C6 C7 C8 C3 0.8(2) . . . . ?
C6 C7 C8 N8 -179.16(14) . . . . ?
O1 C3 C8 C7 176.47(17) . . . . ?
C4 C3 C8 C7 -4.2(2) . . . . ?
O1 C3 C8 N8 -3.6(3) . . . . ?
C4 C3 C8 N8 175.71(14) . . . . ?
O7 N8 C8 C7 -171.06(14) . . . . ?
O6 N8 C8 C7 10.7(2) . . . . ?
O7 N8 C8 C3 9.0(2) . . . . ?
O6 N8 C8 C3 -169.21(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1004436'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N8 O9'
_chemical_formula_weight         360.22

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.840(2)
_cell_length_b                   6.6164(13)
_cell_length_c                   18.342(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.26(3)
_cell_angle_gamma                90.00
_cell_volume                     1314.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9675
_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  AFC10/Saturn724+
_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            9293
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2311
_reflns_number_gt                2220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL

_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)+(0.0728P)²+0.2242P] 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         2311
_refine_ls_number_parameters     242
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51916(11) 0.22931(17) -0.02039(6) 0.0237(3) Uani 1 1 d D . .
C1 C 0.37389(13) 0.2138(2) 0.07590(8) 0.0173(3) Uani 1 1 d . . .
N1 N 0.27840(12) 0.15496(19) 0.02772(7) 0.0213(3) Uani 1 1 d . A 1
O2 O 0.65543(9) 0.39555(16) 0.21932(5) 0.0177(3) Uani 1 1 d . A 1
N2 N 0.70959(11) 0.34615(19) 0.07250(7) 0.0181(3) Uani 1 1 d . A 1
C2 C 0.35041(13) 0.2442(2) 0.15193(8) 0.0158(3) Uani 1 1 d . A 1
O3 O 0.23964(10) 0.21658(17) 0.17761(6) 0.0212(3) Uani 1 1 d D A 1
H3WA H 0.1933(18) 0.180(3) 0.1400(9) 0.048(6) Uiso 1 1 d D B 1
N3 N 0.42218(11) 0.33688(18) 0.27460(7) 0.0161(3) Uani 1 1 d . A 1
C3 C 0.44767(13) 0.3000(2) 0.19861(8) 0.0152(3) Uani 1 1 d . A 1
O4 O 0.29701(10) 0.12493(18) -0.03858(6) 0.0283(3) Uani 1 1 d . A 1
C4 C 0.57201(13) 0.3345(2) 0.17648(8) 0.0152(3) Uani 1 1 d . A 1
N4 N 0.23629(11) 0.7082(2) 0.13670(7) 0.0219(3) Uani 1 1 d . C 1
H4A H 0.3059 0.7268 0.1599 0.026 Uiso 1 1 calc R C 1
H4B H 0.2343 0.6844 0.0906 0.026 Uiso 1 1 calc R C 1
O5 O 0.17013(10) 0.13252(19) 0.04943(6) 0.0290(3) Uani 1 1 d . A 1
C5 C 0.58841(13) 0.3060(2) 0.09902(8) 0.0158(3) Uani 1 1 d . A 1
N5 N -0.00436(13) 0.6445(3) 0.06860(7) 0.0286(4) Uani 1 1 d D C 1
H5B H -0.0438(19) 0.748(2) 0.0497(12) 0.050(7) Uiso 1 1 d D D 1
H5A H -0.0530(17) 0.540(2) 0.0685(12) 0.046(6) Uiso 1 1 d D E 1
O6 O 0.32838(9) 0.43121(17) 0.28896(6) 0.0231(3) Uani 1 1 d . A 1
C6 C 0.49483(14) 0.2512(2) 0.04950(8) 0.0171(3) Uani 1 1 d . A 1
N6 N 0.01756(11) 0.6932(2) 0.14229(7) 0.0208(3) Uani 1 1 d . C 1
O7 O 0.49634(10) 0.27476(17) 0.32229(6) 0.0212(3) Uani 1 1 d . A 1
C7 C 0.13263(13) 0.7165(2) 0.17187(8) 0.0179(3) Uani 1 1 d . C 1
N7 N -0.00418(13) 0.7518(3) 0.25959(8) 0.0332(4) Uani 1 1 d . C 1
O8 O 0.80162(10) 0.29583(19) 0.10962(6) 0.0264(3) Uani 1 1 d . A 1
N8 N 0.11870(12) 0.7513(2) 0.24215(7) 0.0257(3) Uani 1 1 d . C 1
H8B H 0.1789 0.7712 0.2733 0.031 Uiso 1 1 calc R C 1
C8 C -0.06237(15) 0.7164(3) 0.19847(9) 0.0285(4) Uani 1 1 d . C 1
H8A H -0.1478 0.7074 0.1928 0.034 Uiso 1 1 calc R C 1
O9 O 0.71805(10) 0.43350(18) 0.01329(6) 0.0259(3) Uani 1 1 d . A 1
H1WA H 0.4510(14) 0.191(3) -0.0435(12) 0.054(7) Uiso 1 1 d D F 1

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
O1 0.0275(6) 0.0319(7) 0.0115(5) -0.0031(4) -0.0021(5) 0.0011(5)
C1 0.0183(8) 0.0170(7) 0.0161(8) -0.0001(5) -0.0049(6) 0.0001(6)
N1 0.0221(7) 0.0211(7) 0.0201(7) -0.0004(5) -0.0069(5) -0.0002(5)
O2 0.0147(5) 0.0229(6) 0.0151(5) -0.0028(4) -0.0030(4) -0.0006(4)
N2 0.0198(7) 0.0202(7) 0.0143(6) -0.0009(5) 0.0016(5) -0.0003(5)
C2 0.0148(7) 0.0130(7) 0.0194(8) 0.0026(5) -0.0010(6) 0.0018(5)
O3 0.0144(5) 0.0276(6) 0.0214(6) 0.0010(4) -0.0015(4) -0.0031(4)
N3 0.0148(6) 0.0174(6) 0.0161(6) 0.0001(5) 0.0004(5) -0.0024(5)
C3 0.0173(7) 0.0156(7) 0.0126(7) -0.0001(5) -0.0009(6) 0.0012(5)
O4 0.0305(6) 0.0368(7) 0.0168(6) -0.0080(5) -0.0083(5) 0.0012(5)
C4 0.0168(8) 0.0124(7) 0.0163(7) 0.0007(5) -0.0011(6) 0.0027(5)
N4 0.0136(7) 0.0347(8) 0.0172(7) -0.0011(5) -0.0010(5) -0.0008(5)
O5 0.0201(6) 0.0387(7) 0.0274(6) 0.0022(5) -0.0079(5) -0.0074(5)
C5 0.0158(7) 0.0164(7) 0.0153(7) 0.0011(5) 0.0006(6) 0.0009(5)
N5 0.0213(7) 0.0457(10) 0.0185(7) -0.0038(6) -0.0060(6) -0.0042(7)
O6 0.0175(6) 0.0273(6) 0.0247(6) -0.0056(4) 0.0041(4) 0.0033(4)
C6 0.0230(8) 0.0151(7) 0.0129(7) 0.0005(5) -0.0026(6) 0.0039(6)
N6 0.0150(7) 0.0296(7) 0.0175(7) -0.0030(5) -0.0022(5) -0.0003(5)
O7 0.0201(6) 0.0298(6) 0.0134(5) 0.0028(4) -0.0037(4) -0.0005(4)
C7 0.0162(7) 0.0193(7) 0.0179(8) -0.0006(6) -0.0011(6) 0.0004(6)
N7 0.0159(7) 0.0582(11) 0.0259(8) -0.0146(7) 0.0047(6) 0.0001(6)
O8 0.0156(6) 0.0444(7) 0.0191(6) 0.0038(5) -0.0011(4) 0.0009(5)
N8 0.0132(6) 0.0437(9) 0.0200(7) -0.0092(6) -0.0014(5) 0.0008(6)
C8 0.0133(8) 0.0454(11) 0.0269(9) -0.0102(7) 0.0015(7) 0.0000(7)
O9 0.0300(6) 0.0323(7) 0.0158(6) 0.0065(4) 0.0062(5) -0.0004(5)

_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 C6 1.3268(19) . ?
C1 N1 1.3898(19) . ?
C1 C6 1.437(2) . ?
C1 C2 1.442(2) . ?
N1 O4 1.2563(17) . ?
N1 O5 1.2629(17) . ?
O2 C4 1.2420(18) . ?
N2 O8 1.2312(17) . ?
N2 O9 1.2368(16) . ?
N2 C5 1.4432(18) . ?
C2 O3 1.3197(18) . ?
C2 C3 1.382(2) . ?
N3 O6 1.2304(16) . ?
N3 O7 1.2348(17) . ?
N3 C3 1.4523(19) . ?
C3 C4 1.441(2) . ?
C4 C5 1.451(2) . ?
N4 C7 1.319(2) . ?
C5 C6 1.383(2) . ?
N5 N6 1.4007(18) . ?
N6 C7 1.349(2) . ?
N6 C8 1.381(2) . ?
C7 N8 1.324(2) . ?
N7 C8 1.286(2) . ?
N7 N8 1.3821(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 C6 120.04(13) . . ?
N1 C1 C2 119.91(13) . . ?
C6 C1 C2 120.01(13) . . ?
O4 N1 O5 118.26(12) . . ?
O4 N1 C1 121.04(13) . . ?
O5 N1 C1 120.70(13) . . ?
O8 N2 O9 121.69(12) . . ?
O8 N2 C5 119.49(12) . . ?
O9 N2 C5 118.81(12) . . ?
O3 C2 C3 119.90(13) . . ?
O3 C2 C1 121.59(13) . . ?
C3 C2 C1 118.50(13) . . ?
O6 N3 O7 122.52(12) . . ?
O6 N3 C3 118.74(12) . . ?
O7 N3 C3 118.73(12) . . ?
C2 C3 C4 124.53(13) . . ?
C2 C3 N3 118.05(13) . . ?
C4 C3 N3 117.34(12) . . ?
O2 C4 C3 122.61(13) . . ?
O2 C4 C5 123.19(13) . . ?
C3 C4 C5 114.05(13) . . ?
C6 C5 N2 118.72(13) . . ?
C6 C5 C4 124.19(13) . . ?
N2 C5 C4 117.04(12) . . ?
O1 C6 C5 119.64(14) . . ?
O1 C6 C1 121.70(13) . . ?
C5 C6 C1 118.63(13) . . ?
C7 N6 C8 106.54(13) . . ?
C7 N6 N5 122.22(13) . . ?
C8 N6 N5 131.16(13) . . ?
N4 C7 N8 128.00(14) . . ?
N4 C7 N6 126.21(14) . . ?
N8 C7 N6 105.79(13) . . ?
C8 N7 N8 103.99(13) . . ?
C7 N8 N7 111.96(13) . . ?
N7 C8 N6 111.73(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1004437'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H6 N6 O3'
_chemical_formula_weight         162.13

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.5269(7)
_cell_length_b                   6.2650(4)
_cell_length_c                   12.7601(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.003(2)
_cell_angle_gamma                90.00
_cell_volume                     632.01(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9413
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            3268
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.2012
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         26.25
_reflns_number_total             1261
_reflns_number_gt                784
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+1.0610P] 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         1261
_refine_ls_number_parameters     158
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.3002
_refine_ls_wR_factor_gt          0.2642
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5525(7) 0.6219(8) 0.3865(5) 0.0453(15) Uani 0.696(6) 1 d P A 1
N1' N 0.5539(15) 0.8787(19) 0.3908(9) 0.041(3) Uani 0.304(6) 1 d PU A 2
O1 O 0.8362(4) 0.2526(4) 0.2093(4) 0.0580(12) Uani 1 1 d . . .
C1 C 0.506(3) 0.270(2) 0.3774(19) 0.026(3) Uani 0.696(6) 1 d P A 1
C1' C 0.495(8) 1.224(7) 0.371(5) 0.026(3) Uani 0.304(6) 1 d PU A 2
N2 N 0.432(3) 0.461(2) 0.3586(16) 0.035(3) Uani 0.696(6) 1 d P A 1
H2 H 0.3245 0.4818 0.3327 0.042 Uiso 0.696(6) 1 calc PR A 1
N2' N 0.427(4) 1.039(5) 0.357(2) 0.021(4) Uani 0.304(6) 1 d PU A 2
H2' H 0.3195 1.0148 0.3318 0.025 Uiso 0.304(6) 1 calc PR A 2
O2 O 1.0732(6) 0.2503(6) 0.3504(4) 0.0822(16) Uani 1 1 d . . .
C2 C 0.6926(8) 0.5192(10) 0.4214(5) 0.0433(16) Uani 0.696(6) 1 d P A 1
H2A H 0.7984 0.5841 0.4469 0.052 Uiso 0.696(6) 1 calc PR A 1
C2' C 0.6881(17) 0.980(2) 0.4234(11) 0.039(3) Uani 0.304(6) 1 d PU A 2
H2'1 H 0.7936 0.9140 0.4498 0.047 Uiso 0.304(6) 1 calc PR A 2
N3 N 0.6685(8) 0.3044(10) 0.4166(5) 0.0345(14) Uani 0.696(6) 1 d P A 1
N3' N 0.668(2) 1.191(3) 0.4175(12) 0.034(4) Uani 0.304(6) 1 d PU A 2
O3 O 1.0733(6) 0.2602(6) 0.1863(4) 0.0797(15) Uani 1 1 d . . .
N4 N 0.430(2) 0.086(2) 0.3591(13) 0.051(4) Uani 0.696(6) 1 d P A 1
H4A H 0.4882 -0.0299 0.3732 0.061 Uiso 0.696(6) 1 calc PR A 1
H4B H 0.3210 0.0796 0.3330 0.061 Uiso 0.696(6) 1 calc PR A 1
N4' N 0.427(7) 1.411(5) 0.350(4) 0.040(8) Uani 0.304(6) 1 d PU A 2
H4'1 H 0.3185 1.4230 0.3222 0.048 Uiso 0.304(6) 1 calc PR A 2
H4'2 H 0.4895 1.5229 0.3637 0.048 Uiso 0.304(6) 1 calc PR A 2
N5 N 0.7876(8) 0.1354(9) 0.4470(5) 0.0474(16) Uani 0.696(6) 1 d P A 1
H5A H 0.7533 0.0051 0.4399 0.057 Uiso 0.696(6) 1 calc PR A 1
H5B H 0.8941 0.1630 0.4725 0.057 Uiso 0.696(6) 1 calc PR A 1
N5' N 0.7883(17) 1.3657(19) 0.4459(10) 0.040(3) Uani 0.304(6) 1 d PU A 2
H5'1 H 0.8951 1.3398 0.4721 0.048 Uiso 0.304(6) 1 calc PR A 2
H5'2 H 0.7527 1.4954 0.4366 0.048 Uiso 0.304(6) 1 calc PR A 2
N6 N 0.9945(5) 0.2539(4) 0.2492(4) 0.0370(10) 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
N1 0.049(3) 0.038(3) 0.049(3) -0.003(2) 0.020(3) -0.005(2)
N1' 0.043(6) 0.044(6) 0.037(6) 0.002(5) 0.016(5) 0.008(5)
O1 0.0304(18) 0.043(2) 0.091(3) 0.0035(15) 0.0115(17) 0.0000(12)
C1 0.028(4) 0.026(8) 0.025(3) -0.003(5) 0.009(3) -0.002(6)
C1' 0.028(4) 0.026(8) 0.025(3) -0.003(5) 0.009(3) -0.002(6)
N2 0.031(4) 0.027(6) 0.045(5) -0.001(4) 0.011(3) 0.005(5)
N2' 0.023(7) 0.014(8) 0.021(6) 0.005(5) 0.004(5) -0.005(6)
O2 0.060(3) 0.124(4) 0.050(2) 0.002(2) 0.007(2) -0.001(2)
C2 0.038(3) 0.046(4) 0.045(3) -0.005(3) 0.014(3) -0.010(3)
C2' 0.026(6) 0.049(7) 0.041(6) 0.008(5) 0.011(5) 0.011(5)
N3 0.027(3) 0.043(3) 0.033(3) 0.000(3) 0.009(2) -0.001(3)
N3' 0.031(7) 0.049(7) 0.025(6) 0.001(6) 0.013(5) 0.001(7)
O3 0.060(3) 0.116(4) 0.074(3) 0.004(2) 0.036(2) 0.0055(19)
N4 0.042(5) 0.030(7) 0.077(6) -0.008(4) 0.018(4) -0.013(5)
N4' 0.034(9) 0.034(13) 0.051(10) -0.002(9) 0.014(7) -0.005(9)
N5 0.029(3) 0.049(4) 0.059(4) 0.006(3) 0.010(2) 0.012(3)
N5' 0.034(6) 0.042(6) 0.046(6) 0.002(5) 0.016(5) 0.000(5)
N6 0.0329(18) 0.0252(18) 0.050(2) 0.0003(14) 0.0124(16) 0.0008(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
N1 C2 1.281(8) . ?
N1 N2 1.387(19) . ?
N1' C2' 1.235(18) . ?
N1' N2' 1.42(3) . ?
O1 N6 1.251(6) . ?
C1 N4 1.30(2) . ?
C1 N3 1.31(3) . ?
C1 N2 1.33(2) . ?
C1' N2' 1.28(6) . ?
C1' N4' 1.29(6) . ?
C1' N3' 1.38(7) . ?
N2 H2 0.8600 . ?
N2' H2' 0.8600 . ?
O2 N6 1.212(6) . ?
C2 N3 1.359(9) . ?
C2 H2A 0.9300 . ?
C2' N3' 1.33(2) . ?
C2' H2'1 0.9300 . ?
N3 N5 1.417(8) . ?
N3' N5' 1.45(2) . ?
O3 N6 1.226(6) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4' H4'1 0.8600 . ?
N4' H4'2 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5' H5'1 0.8600 . ?
N5' H5'2 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 103.3(8) . . ?
C2' N1' N2' 104.3(17) . . ?
N4 C1 N3 126.9(19) . . ?
N4 C1 N2 127(2) . . ?
N3 C1 N2 106.5(14) . . ?
N2' C1' N4' 130(6) . . ?
N2' C1' N3' 106(4) . . ?
N4' C1' N3' 124(5) . . ?
C1 N2 N1 110.7(17) . . ?
C1 N2 H2 124.7 . . ?
N1 N2 H2 124.7 . . ?
C1' N2' N1' 110(4) . . ?
C1' N2' H2' 125.1 . . ?
N1' N2' H2' 125.1 . . ?
N1 C2 N3 112.1(6) . . ?
N1 C2 H2A 124.0 . . ?
N3 C2 H2A 124.0 . . ?
N1' C2' N3' 114.0(13) . . ?
N1' C2' H2'1 123.0 . . ?
N3' C2' H2'1 123.0 . . ?
C1 N3 C2 107.5(9) . . ?
C1 N3 N5 122.2(9) . . ?
C2 N3 N5 130.3(6) . . ?
C2' N3' C1' 106(2) . . ?
C2' N3' N5' 132.3(14) . . ?
C1' N3' N5' 122(2) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C1' N4' H4'1 120.0 . . ?
C1' N4' H4'2 120.0 . . ?
H4'1 N4' H4'2 120.0 . . ?
N3 N5 H5A 120.0 . . ?
N3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N3' N5' H5'1 120.0 . . ?
N3' N5' H5'2 120.0 . . ?
H5'1 N5' H5'2 120.0 . . ?
O2 N6 O3 118.5(5) . . ?
O2 N6 O1 121.1(5) . . ?
O3 N6 O1 120.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N2 N1 -179(2) . . . . ?
N3 C1 N2 N1 0(3) . . . . ?
C2 N1 N2 C1 0(2) . . . . ?
N4' C1' N2' N1' 179(6) . . . . ?
N3' C1' N2' N1' -2(5) . . . . ?
C2' N1' N2' C1' 1(4) . . . . ?
N2 N1 C2 N3 0.4(11) . . . . ?
N2' N1' C2' N3' 0.7(18) . . . . ?
N4 C1 N3 C2 179(2) . . . . ?
N2 C1 N3 C2 0(2) . . . . ?
N4 C1 N3 N5 -1(3) . . . . ?
N2 C1 N3 N5 179.6(14) . . . . ?
N1 C2 N3 C1 -0.3(13) . . . . ?
N1 C2 N3 N5 -179.8(6) . . . . ?
N1' C2' N3' C1' -2(3) . . . . ?
N1' C2' N3' N5' -179.7(14) . . . . ?
N2' C1' N3' C2' 2(5) . . . . ?
N4' C1' N3' C2' -178(6) . . . . ?
N2' C1' N3' N5' -180(3) . . . . ?
N4' C1' N3' N5' 0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.25
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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 1037538'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N8 O4'
_chemical_formula_weight         256.20

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

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                   5.1010(4)
_cell_length_b                   7.9797(6)
_cell_length_c                   24.095(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.788(2)
_cell_angle_gamma                90.00
_cell_volume                     980.30(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    195
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      25.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II Smart 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            6185
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.41
_reflns_number_total             1806
_reflns_number_gt                1580
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0390P)²+0.3639P] 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         1806
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1186(3) 0.92972(19) 0.59578(6) 0.0250(3) Uani 1 1 d . . .
C2 C 0.1001(3) 0.80814(18) 0.59070(6) 0.0229(3) Uani 1 1 d . . .
C3 C 0.1807(3) 0.71149(18) 0.54688(6) 0.0220(3) Uani 1 1 d . . .
C4 C 0.0808(3) 0.68882(18) 0.48837(6) 0.0234(3) Uani 1 1 d . . .
C5 C 0.7646(3) 0.71026(19) 0.33498(6) 0.0241(3) Uani 1 1 d . . .
C6 C 0.9357(3) 0.6104(2) 0.25985(7) 0.0363(4) Uani 1 1 d . . .
H1 H -0.220(4) 0.877(3) 0.5215(9) 0.061(6) Uiso 1 1 d . . .
H2 H 0.488(4) 0.555(2) 0.5516(7) 0.032(5) Uiso 1 1 d . . .
H3 H 0.666(4) 0.787(3) 0.4041(10) 0.056(6) Uiso 1 1 d . . .
H4 H 0.479(4) 0.845(3) 0.3563(9) 0.044(6) Uiso 1 1 d . . .
H5 H 0.436(4) 0.721(3) 0.2300(10) 0.060(7) Uiso 1 1 d . . .
H6 H 0.627(4) 0.863(3) 0.2247(9) 0.048(6) Uiso 1 1 d . . .
H7 H 0.956(4) 0.587(3) 0.2207(9) 0.051(6) Uiso 1 1 d . . .
H8 H 1.054(4) 0.603(2) 0.3789(9) 0.042(5) Uiso 1 1 d . . .
N1 N 0.2626(3) 0.77704(17) 0.63535(5) 0.0287(3) Uani 1 1 d . . .
N2 N 0.4383(3) 0.66628(17) 0.62128(5) 0.0307(3) Uani 1 1 d . . .
N3 N 0.3883(3) 0.62668(17) 0.56785(5) 0.0254(3) Uani 1 1 d . . .
N4 N 0.6092(3) 0.78576(19) 0.36918(6) 0.0341(4) Uani 1 1 d . . .
N5 N 0.5422(3) 0.7991(2) 0.24977(6) 0.0378(4) Uani 1 1 d . . .
N6 N 0.7372(3) 0.70740(17) 0.27903(5) 0.0284(3) Uani 1 1 d . . .
N7 N 1.0855(3) 0.55410(19) 0.29966(6) 0.0365(4) Uani 1 1 d . . .
N8 N 0.9753(3) 0.61728(17) 0.34703(6) 0.0290(3) Uani 1 1 d . . .
O1 O -0.1317(2) 0.76225(15) 0.47556(4) 0.0337(3) Uani 1 1 d . . .
O2 O 0.2084(2) 0.59854(14) 0.45687(4) 0.0297(3) Uani 1 1 d . . .
O3 O -0.2761(2) 0.95266(15) 0.55230(5) 0.0320(3) Uani 1 1 d . . .
O4 O -0.1499(2) 1.00544(15) 0.63882(4) 0.0348(3) 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 0.0255(8) 0.0264(7) 0.0231(8) 0.0006(6) 0.0020(6) -0.0008(6)
C2 0.0245(8) 0.0252(7) 0.0189(7) 0.0006(6) -0.0011(6) -0.0013(6)
C3 0.0214(7) 0.0247(7) 0.0198(7) 0.0012(6) -0.0013(6) -0.0003(6)
C4 0.0256(8) 0.0262(8) 0.0183(7) 0.0005(6) -0.0010(6) -0.0015(7)
C5 0.0249(8) 0.0279(8) 0.0192(7) 0.0018(6) -0.0027(6) -0.0039(6)
C6 0.0384(10) 0.0478(11) 0.0228(9) -0.0053(8) 0.0048(7) -0.0015(8)
N1 0.0318(7) 0.0331(7) 0.0210(6) -0.0024(5) -0.0031(5) 0.0029(6)
N2 0.0329(7) 0.0362(8) 0.0225(7) -0.0027(6) -0.0067(6) 0.0053(6)
N3 0.0260(7) 0.0291(7) 0.0209(6) -0.0034(5) -0.0033(5) 0.0046(6)
N4 0.0336(8) 0.0470(9) 0.0214(7) -0.0011(6) -0.0020(6) 0.0110(7)
N5 0.0318(8) 0.0551(10) 0.0260(7) 0.0130(7) -0.0075(6) -0.0041(8)
N6 0.0287(7) 0.0383(8) 0.0180(6) 0.0032(5) -0.0027(5) -0.0023(6)
N7 0.0370(8) 0.0443(8) 0.0283(7) -0.0052(6) 0.0042(6) 0.0061(7)
N8 0.0315(7) 0.0357(8) 0.0196(7) -0.0012(6) -0.0028(6) 0.0050(6)
O1 0.0318(6) 0.0469(7) 0.0218(6) -0.0037(5) -0.0071(5) 0.0115(5)
O2 0.0330(6) 0.0363(6) 0.0197(5) -0.0044(5) -0.0003(5) 0.0062(5)
O3 0.0322(6) 0.0379(7) 0.0257(6) -0.0026(5) -0.0042(5) 0.0088(5)
O4 0.0389(7) 0.0406(7) 0.0250(6) -0.0088(5) 0.0013(5) 0.0094(5)

_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 O4 1.2149(18) . ?
C1 O3 1.3131(18) . ?
C1 C2 1.486(2) . ?
C2 N1 1.3603(19) . ?
C2 C3 1.381(2) . ?
C3 N3 1.342(2) . ?
C3 C4 1.495(2) . ?
C4 O2 1.2448(18) . ?
C4 O1 1.2618(18) . ?
C5 N4 1.308(2) . ?
C5 N8 1.331(2) . ?
C5 N6 1.3512(19) . ?
C6 N7 1.289(2) . ?
C6 N6 1.366(2) . ?
N1 N2 1.3110(19) . ?
N2 N3 1.3424(18) . ?
N5 N6 1.4063(19) . ?
N7 N8 1.3831(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
O4 C1 O3 121.23(14) . . ?
O4 C1 C2 120.92(14) . . ?
O3 C1 C2 117.85(13) . . ?
N1 C2 C3 108.31(13) . . ?
N1 C2 C1 119.62(13) . . ?
C3 C2 C1 132.07(14) . . ?
N3 C3 C2 104.14(13) . . ?
N3 C3 C4 122.40(13) . . ?
C2 C3 C4 133.45(14) . . ?
O2 C4 O1 125.52(14) . . ?
O2 C4 C3 118.40(13) . . ?
O1 C4 C3 116.07(13) . . ?
N4 C5 N8 128.35(14) . . ?
N4 C5 N6 126.20(15) . . ?
N8 C5 N6 105.42(13) . . ?
N7 C6 N6 111.97(14) . . ?
N2 N1 C2 108.86(12) . . ?
N1 N2 N3 107.20(12) . . ?
C3 N3 N2 111.50(13) . . ?
C5 N6 C6 107.01(13) . . ?
C5 N6 N5 122.74(14) . . ?
C6 N6 N5 130.17(14) . . ?
C6 N7 N8 103.92(14) . . ?
C5 N8 N7 111.68(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1039373'
_audit_update_record             
;
2015-03-17 deposited with the CCDC.
2015-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N8 O6'
_chemical_formula_weight         250.16

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.4007(4)
_cell_length_b                   7.6439(5)
_cell_length_c                   10.1075(8)
_cell_angle_alpha                70.9850(10)
_cell_angle_beta                 87.798(2)
_cell_angle_gamma                85.279(2)
_cell_volume                     465.92(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            1575
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1575
_reflns_number_gt                950
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1800P)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         1575
_refine_ls_number_parameters     156
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.1101
_refine_ls_wR_factor_ref         0.3047
_refine_ls_wR_factor_gt          0.2824
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.109
_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 -0.0951(12) 0.7968(12) 0.4360(8) 0.049(2) Uani 1 1 d . . .
N2 N 0.0627(11) 0.7408(11) 0.5340(7) 0.044(2) Uani 1 1 d U . .
H2 H 0.0406 0.6923 0.6224 0.053 Uiso 1 1 calc R . .
N3 N 0.2180(10) 0.8480(9) 0.3387(6) 0.0278(15) Uani 1 1 d . . .
N4 N 0.4334(13) 0.7347(13) 0.5338(8) 0.058(2) Uani 1 1 d U . .
H4A H 0.4424 0.6840 0.6230 0.069 Uiso 1 1 calc R . .
H4B H 0.5451 0.7612 0.4835 0.069 Uiso 1 1 calc R . .
N5 N 0.3878(11) 0.8947(10) 0.2452(7) 0.0422(19) Uani 1 1 d . . .
H5B H 0.3695 1.0142 0.1946 0.063 Uiso 1 1 d R . .
H5C H 0.3917 0.8260 0.1889 0.063 Uiso 1 1 d R . .
N6 N 0.2374(10) 0.7009(9) 0.9315(6) 0.0317(16) Uani 1 1 d . . .
N7 N 0.2681(9) 0.3844(9) 0.9201(6) 0.0289(16) Uani 1 1 d . . .
N8 N 0.2386(9) 0.4362(9) 1.1454(6) 0.0264(15) Uani 1 1 d . . .
O1 O 0.1517(9) 0.8022(8) 0.9943(6) 0.0412(15) Uani 1 1 d . . .
O2 O 0.3167(10) 0.7588(8) 0.8134(6) 0.0472(17) Uani 1 1 d . . .
O3 O 0.2003(9) 0.4445(8) 0.7998(6) 0.0416(15) Uani 1 1 d . . .
O4 O 0.3480(9) 0.2287(8) 0.9734(6) 0.0401(15) Uani 1 1 d . . .
O5 O 0.1778(8) 0.2802(7) 1.2029(5) 0.0320(14) Uani 1 1 d . . .
O6 O 0.2951(9) 0.5289(8) 1.2159(6) 0.0395(15) Uani 1 1 d . . .
C1 C 0.2542(13) 0.7704(12) 0.4760(7) 0.035(2) Uani 1 1 d . . .
C2 C 0.0070(16) 0.8593(13) 0.3201(9) 0.045(2) Uani 1 1 d . . .
H2A H -0.0564 0.9069 0.2331 0.054 Uiso 1 1 calc R . .
C3 C 0.2475(12) 0.5071(11) 1.0009(7) 0.0272(17) 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
N1 0.033(4) 0.076(6) 0.037(4) -0.017(4) -0.009(4) 0.000(4)
N2 0.033(4) 0.077(5) 0.013(3) -0.001(3) 0.006(3) -0.009(3)
N3 0.037(4) 0.033(4) 0.011(3) -0.003(3) 0.003(3) -0.009(3)
N4 0.048(5) 0.093(6) 0.019(3) -0.001(4) -0.003(3) -0.007(4)
N5 0.045(4) 0.046(4) 0.033(4) -0.009(3) 0.019(3) -0.015(3)
N6 0.029(4) 0.037(4) 0.024(4) 0.000(3) -0.010(3) -0.008(3)
N7 0.020(3) 0.049(5) 0.014(3) -0.003(3) -0.001(3) -0.006(3)
N8 0.023(3) 0.037(4) 0.020(3) -0.009(3) 0.004(3) -0.010(3)
O1 0.048(4) 0.040(3) 0.034(3) -0.011(3) 0.002(3) -0.002(3)
O2 0.056(4) 0.049(4) 0.027(3) 0.004(3) 0.016(3) -0.022(3)
O3 0.040(3) 0.060(4) 0.023(3) -0.013(3) -0.009(3) 0.000(3)
O4 0.053(4) 0.036(3) 0.021(3) 0.003(2) 0.002(3) 0.001(3)
O5 0.036(3) 0.031(3) 0.022(3) 0.002(2) 0.012(2) -0.011(2)
O6 0.046(4) 0.052(4) 0.020(3) -0.009(3) -0.007(2) -0.008(3)
C1 0.036(5) 0.055(6) 0.010(4) -0.003(3) 0.001(3) -0.010(4)
C2 0.054(6) 0.049(5) 0.027(5) -0.004(4) -0.013(4) 0.000(4)
C3 0.029(4) 0.034(4) 0.016(4) -0.003(3) -0.004(3) -0.008(3)

_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 C2 1.287(12) . ?
N1 N2 1.383(10) . ?
N2 C1 1.342(10) . ?
N2 H2 0.8600 . ?
N3 C1 1.340(9) . ?
N3 C2 1.363(12) . ?
N3 N5 1.402(8) . ?
N4 C1 1.275(11) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8899 . ?
N6 O1 1.236(9) . ?
N6 O2 1.234(8) . ?
N6 C3 1.415(10) . ?
N7 O4 1.213(8) . ?
N7 O3 1.233(8) . ?
N7 C3 1.426(10) . ?
N8 O5 1.232(7) . ?
N8 O6 1.238(8) . ?
N8 C3 1.383(9) . ?
C2 H2A 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
C2 N1 N2 102.7(7) . . ?
C1 N2 N1 112.7(6) . . ?
C1 N2 H2 123.7 . . ?
N1 N2 H2 123.7 . . ?
C1 N3 C2 107.7(7) . . ?
C1 N3 N5 119.5(6) . . ?
C2 N3 N5 132.8(7) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N3 N5 H5B 108.8 . . ?
N3 N5 H5C 108.9 . . ?
H5B N5 H5C 109.5 . . ?
O1 N6 O2 124.0(7) . . ?
O1 N6 C3 117.6(6) . . ?
O2 N6 C3 118.5(7) . . ?
O4 N7 O3 124.3(7) . . ?
O4 N7 C3 118.6(6) . . ?
O3 N7 C3 117.1(6) . . ?
O5 N8 O6 120.5(6) . . ?
O5 N8 C3 119.8(7) . . ?
O6 N8 C3 119.7(6) . . ?
N4 C1 N2 129.6(7) . . ?
N4 C1 N3 126.1(7) . . ?
N2 C1 N3 104.3(7) . . ?
N1 C2 N3 112.6(8) . . ?
N1 C2 H2A 123.7 . . ?
N3 C2 H2A 123.7 . . ?
N8 C3 N6 120.8(7) . . ?
N8 C3 N7 120.0(7) . . ?
N6 C3 N7 119.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 C1 0.1(10) . . . . ?
N1 N2 C1 N4 -179.3(10) . . . . ?
N1 N2 C1 N3 0.5(10) . . . . ?
C2 N3 C1 N4 179.0(9) . . . . ?
N5 N3 C1 N4 0.9(13) . . . . ?
C2 N3 C1 N2 -0.8(9) . . . . ?
N5 N3 C1 N2 -178.8(7) . . . . ?
N2 N1 C2 N3 -0.6(10) . . . . ?
C1 N3 C2 N1 1.0(10) . . . . ?
N5 N3 C2 N1 178.6(8) . . . . ?
O5 N8 C3 N6 155.7(7) . . . . ?
O6 N8 C3 N6 -25.5(11) . . . . ?
O5 N8 C3 N7 -24.6(10) . . . . ?
O6 N8 C3 N7 154.3(7) . . . . ?
O1 N6 C3 N8 -24.1(10) . . . . ?
O2 N6 C3 N8 154.9(7) . . . . ?
O1 N6 C3 N7 156.2(7) . . . . ?
O2 N6 C3 N7 -24.9(10) . . . . ?
O4 N7 C3 N8 -25.2(10) . . . . ?
O3 N7 C3 N8 154.0(7) . . . . ?
O4 N7 C3 N6 154.6(6) . . . . ?
O3 N7 C3 N6 -26.2(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.146
