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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1442342'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C1 H6 N3, C3 H N6 O6'

_chemical_formula_sum            'C4 H7 N9 O6'

_chemical_formula_weight         277.19



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   'P2(1)/n  '

_symmetry_space_group_name_Hall  '-P 2yn  '



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   7.0482(7)

_cell_length_b                   15.5415(18)

_cell_length_c                   9.6301(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 94.891(3)

_cell_angle_gamma                90.00

_cell_volume                     1051.04(19)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    2097

_cell_measurement_theta_min      3.18

_cell_measurement_theta_max      23.28



_exptl_crystal_description       block

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.23

_exptl_crystal_size_min          0.18

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.752

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             568

_exptl_absorpt_coefficient_mu    0.161

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6834

_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            5981

_diffrn_reflns_av_R_equivalents  0.0375

_diffrn_reflns_av_sigmaI/netI    0.0534

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -18

_diffrn_reflns_limit_k_max       14

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         3.18

_diffrn_reflns_theta_max         25.41

_reflns_number_total             1887

_reflns_number_gt                1294

_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)+(0.0437P)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         1887

_refine_ls_number_parameters     190

_refine_ls_number_restraints     15

_refine_ls_R_factor_all          0.0786

_refine_ls_R_factor_gt           0.0392

_refine_ls_wR_factor_ref         0.0881

_refine_ls_wR_factor_gt          0.0763

_refine_ls_goodness_of_fit_ref   1.028

_refine_ls_restrained_S_all      1.025

_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 0.5449(3) 0.27689(13) 1.0309(2) 0.0186(5) Uani 1 1 d . . .
C2 C 0.6968(3) 0.37925(15) 1.1169(2) 0.0283(6) Uani 1 1 d . . .
H2 H 0.7483 0.4232 1.1774 0.034 Uiso 1 1 calc R . .
C3 C 0.8792(3) 0.41042(13) 0.9144(2) 0.0206(5) Uani 1 1 d . . .
C4 C 0.3582(3) 0.38788(13) 0.5414(2) 0.0206(5) Uani 1 1 d . . .
N1 N 0.7434(2) 0.36696(11) 0.98508(16) 0.0210(4) Uani 1 1 d . . .
N2 N 0.6421(2) 0.29906(11) 0.92707(16) 0.0206(4) Uani 1 1 d . . .
N3 N 0.5708(2) 0.32233(11) 1.15014(17) 0.0274(5) Uani 1 1 d . . .
N4 N 1.0610(2) 0.37692(11) 0.92227(17) 0.0226(4) Uani 1 1 d . . .
N5 N 0.8142(3) 0.47209(11) 0.81796(17) 0.0242(4) Uani 1 1 d . . .
N6 N 0.4213(2) 0.20216(12) 1.0189(2) 0.0256(5) Uani 1 1 d . . .
N7 N 0.4053(3) 0.33511(12) 0.64657(19) 0.0278(5) Uani 1 1 d D . .
H7A H 0.485(3) 0.2943(12) 0.638(2) 0.033 Uiso 1 1 d D . .
H7B H 0.373(3) 0.3475(14) 0.7284(16) 0.033 Uiso 1 1 d D . .
N8 N 0.2424(3) 0.45322(13) 0.5596(2) 0.0309(5) Uani 1 1 d D . .
H8A H 0.188(3) 0.4578(14) 0.6353(18) 0.037 Uiso 1 1 d D . .
H8B H 0.206(3) 0.4835(13) 0.4875(18) 0.037 Uiso 1 1 d D . .
N9 N 0.4238(3) 0.37511(13) 0.41894(19) 0.0301(5) Uani 1 1 d D . .
H9A H 0.386(3) 0.4085(12) 0.3493(19) 0.036 Uiso 1 1 d D . .
H9B H 0.500(3) 0.3320(12) 0.405(2) 0.036 Uiso 1 1 d D . .
O1 O 1.19169(19) 0.41315(9) 0.86474(14) 0.0289(4) Uani 1 1 d . . .
O2 O 1.09201(19) 0.31012(10) 0.99255(15) 0.0321(4) Uani 1 1 d . . .
O3 O 0.92401(19) 0.50983(9) 0.74262(14) 0.0316(4) Uani 1 1 d . . .
O4 O 0.6407(2) 0.48883(10) 0.80933(15) 0.0347(4) Uani 1 1 d . . .
O5 O 0.3603(2) 0.17471(10) 1.12536(16) 0.0367(4) Uani 1 1 d . . .
O6 O 0.3886(2) 0.17020(11) 0.90325(17) 0.0411(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 0.0160(11) 0.0210(12) 0.0188(12) 0.0035(10) 0.0018(9) 0.0032(10)
C2 0.0361(14) 0.0300(14) 0.0195(13) -0.0065(10) 0.0062(10) 0.0000(11)
C3 0.0211(11) 0.0213(12) 0.0195(12) 0.0052(10) 0.0032(9) 0.0005(10)
C4 0.0188(11) 0.0225(13) 0.0203(13) -0.0009(10) 0.0008(9) -0.0056(10)
N1 0.0251(10) 0.0215(10) 0.0167(10) -0.0009(8) 0.0039(8) -0.0023(8)
N2 0.0215(10) 0.0218(10) 0.0181(10) 0.0009(8) 0.0001(8) 0.0000(8)
N3 0.0294(10) 0.0300(12) 0.0242(11) -0.0012(9) 0.0097(8) -0.0036(9)
N4 0.0254(10) 0.0221(11) 0.0202(10) -0.0002(8) 0.0017(8) -0.0027(9)
N5 0.0272(11) 0.0221(11) 0.0233(10) -0.0005(8) 0.0024(8) 0.0011(9)
N6 0.0191(10) 0.0287(12) 0.0292(13) 0.0047(9) 0.0027(9) 0.0019(9)
N7 0.0338(12) 0.0289(12) 0.0209(11) 0.0007(9) 0.0035(9) 0.0073(9)
N8 0.0356(12) 0.0339(13) 0.0242(12) 0.0037(9) 0.0076(9) 0.0113(10)
N9 0.0357(12) 0.0350(14) 0.0206(12) 0.0049(9) 0.0083(9) 0.0086(10)
O1 0.0239(8) 0.0321(10) 0.0321(9) 0.0042(7) 0.0102(7) -0.0035(7)
O2 0.0291(9) 0.0265(10) 0.0404(10) 0.0144(8) 0.0017(7) 0.0046(7)
O3 0.0350(9) 0.0299(10) 0.0307(9) 0.0127(7) 0.0068(7) -0.0044(8)
O4 0.0270(9) 0.0334(10) 0.0436(10) 0.0087(8) 0.0028(7) 0.0079(8)
O5 0.0335(9) 0.0408(11) 0.0368(10) 0.0169(8) 0.0092(8) -0.0052(8)
O6 0.0414(10) 0.0467(12) 0.0351(11) -0.0092(8) 0.0022(8) -0.0163(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 N2 1.305(2) . ?
C1 N3 1.347(3) . ?
C1 N6 1.451(3) . ?
C2 N3 1.312(3) . ?
C2 N1 1.352(2) . ?
C2 H2 0.9500 . ?
C3 N4 1.379(2) . ?
C3 N5 1.385(3) . ?
C3 N1 1.395(2) . ?
C4 N9 1.318(3) . ?
C4 N7 1.323(3) . ?
C4 N8 1.324(3) . ?
N1 N2 1.366(2) . ?
N4 O2 1.248(2) . ?
N4 O1 1.249(2) . ?
N5 O4 1.246(2) . ?
N5 O3 1.2512(19) . ?
N6 O5 1.222(2) . ?
N6 O6 1.223(2) . ?
N7 H7A 0.854(14) . ?
N7 H7B 0.862(13) . ?
N8 H8A 0.857(14) . ?
N8 H8B 0.859(14) . ?
N9 H9A 0.872(14) . ?
N9 H9B 0.877(14) . ?



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



































N2 C1 N3 118.22(18) . . ?
N2 C1 N6 120.04(18) . . ?
N3 C1 N6 121.65(17) . . ?
N3 C2 N1 110.96(19) . . ?
N3 C2 H2 124.5 . . ?
N1 C2 H2 124.5 . . ?
N4 C3 N5 123.42(17) . . ?
N4 C3 N1 117.59(17) . . ?
N5 C3 N1 117.43(17) . . ?
N9 C4 N7 120.5(2) . . ?
N9 C4 N8 120.1(2) . . ?
N7 C4 N8 119.44(19) . . ?
C2 N1 N2 109.43(16) . . ?
C2 N1 C3 128.44(18) . . ?
N2 N1 C3 122.04(15) . . ?
C1 N2 N1 100.40(15) . . ?
C2 N3 C1 100.99(17) . . ?
O2 N4 O1 120.93(17) . . ?
O2 N4 C3 117.55(17) . . ?
O1 N4 C3 121.49(17) . . ?
O4 N5 O3 121.05(17) . . ?
O4 N5 C3 117.12(17) . . ?
O3 N5 C3 121.83(17) . . ?
O5 N6 O6 124.71(19) . . ?
O5 N6 C1 117.66(17) . . ?
O6 N6 C1 117.61(17) . . ?
C4 N7 H7A 120.5(15) . . ?
C4 N7 H7B 119.5(15) . . ?
H7A N7 H7B 119(2) . . ?
C4 N8 H8A 120.3(15) . . ?
C4 N8 H8B 117.2(15) . . ?
H8A N8 H8B 121(2) . . ?
C4 N9 H9A 119.3(14) . . ?
C4 N9 H9B 121.1(14) . . ?
H9A N9 H9B 119(2) . . ?



_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        25.41

_diffrn_measured_fraction_theta_full 0.971

_refine_diff_density_max         0.175

_refine_diff_density_min         -0.227

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1442343'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'H4 N, C3 H N6 O6, 0.13(H2 O)'

_chemical_formula_sum            'C3 H5.26 N7 O6.13'

_chemical_formula_weight         237.44



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                   6.3136(5)

_cell_length_b                   15.3604(13)

_cell_length_c                   9.3411(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 98.223(2)

_cell_angle_gamma                90.00

_cell_volume                     896.58(13)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    2607

_cell_measurement_theta_min      3.45

_cell_measurement_theta_max      25.25



_exptl_crystal_description       block

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.759

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             485

_exptl_absorpt_coefficient_mu    0.167

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6864

_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            8925

_diffrn_reflns_av_R_equivalents  0.0528

_diffrn_reflns_av_sigmaI/netI    0.0514

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -18

_diffrn_reflns_limit_k_max       18

_diffrn_reflns_limit_l_min       -10

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         3.26

_diffrn_reflns_theta_max         25.21

_reflns_number_total             1589

_reflns_number_gt                1111

_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)+(0.0332P)²+0.5291P] 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         1589

_refine_ls_number_parameters     162

_refine_ls_number_restraints     21

_refine_ls_R_factor_all          0.0763

_refine_ls_R_factor_gt           0.0424

_refine_ls_wR_factor_ref         0.0865

_refine_ls_wR_factor_gt          0.0762

_refine_ls_goodness_of_fit_ref   1.020

_refine_ls_restrained_S_all      1.015

_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 0.8482(3) 0.22015(14) 1.0492(2) 0.0172(5) Uani 1 1 d . . .
C2 C 0.6085(4) 0.22301(15) 0.8750(2) 0.0199(6) Uani 1 1 d . . .
H2 H 0.5107 0.2088 0.7913 0.024 Uiso 1 1 calc R . .
C3 C 0.4845(4) 0.37292(14) 0.9137(2) 0.0174(5) Uani 1 1 d . . .
N1 N 0.6117(3) 0.29926(12) 0.94610(19) 0.0176(5) Uani 1 1 d . . .
N2 N 0.7705(3) 0.29818(12) 1.0627(2) 0.0186(5) Uani 1 1 d . . .
N3 N 0.7596(3) 0.17073(12) 0.9373(2) 0.0216(5) Uani 1 1 d . . .
N4 N 0.3169(3) 0.38548(13) 0.9901(2) 0.0199(5) Uani 1 1 d . . .
N5 N 0.5458(3) 0.43174(13) 0.8154(2) 0.0208(5) Uani 1 1 d . . .
N6 N 1.0267(3) 0.18850(13) 1.1515(2) 0.0224(5) Uani 1 1 d . . .
N7 N 0.9935(3) 0.55925(13) 0.7415(2) 0.0219(5) Uani 1 1 d D . .
H7A H 0.939(3) 0.5988(11) 0.800(2) 0.033 Uiso 1 1 d D . .
H7B H 1.047(3) 0.5868(12) 0.6699(18) 0.033 Uiso 1 1 d D . .
H7C H 0.885(3) 0.5227(12) 0.707(2) 0.033 Uiso 1 1 d D . .
H7D H 1.099(3) 0.5284(12) 0.796(2) 0.033 Uiso 1 1 d D . .
O1 O 0.1953(3) 0.44924(11) 0.96976(17) 0.0265(4) Uani 1 1 d . . .
O2 O 0.2903(2) 0.32920(11) 1.08371(17) 0.0239(4) Uani 1 1 d . . .
O3 O 0.4499(2) 0.50142(11) 0.78732(17) 0.0257(4) Uani 1 1 d . . .
O4 O 0.7036(3) 0.41084(11) 0.75583(18) 0.0282(5) Uani 1 1 d . . .
O5 O 1.0726(2) 0.22827(11) 1.26473(17) 0.0262(4) Uani 1 1 d . . .
O6 O 1.1190(3) 0.12351(11) 1.11663(19) 0.0374(5) Uani 1 1 d . . .
O7 O 0.379(2) 0.0404(8) 0.9652(14) 0.034(5) Uiso 0.128(5) 1 d P . .
H7E H 0.4821 0.0745 0.9571 0.041 Uiso 0.128(5) 1 d PR . .
H7F H 0.2936 0.0660 1.0142 0.041 Uiso 0.128(5) 1 d PR . .



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 0.0160(12) 0.0180(13) 0.0182(13) 0.0027(11) 0.0050(11) 0.0013(11)
C2 0.0227(13) 0.0195(14) 0.0175(13) -0.0053(11) 0.0030(11) -0.0025(11)
C3 0.0156(12) 0.0176(13) 0.0186(13) 0.0006(10) 0.0013(11) 0.0022(10)
N1 0.0153(10) 0.0200(11) 0.0166(11) 0.0000(9) -0.0009(9) 0.0008(9)
N2 0.0171(10) 0.0191(11) 0.0185(11) 0.0001(9) -0.0013(9) 0.0004(9)
N3 0.0247(11) 0.0199(11) 0.0202(11) -0.0017(9) 0.0024(9) 0.0019(10)
N4 0.0177(11) 0.0242(12) 0.0165(11) -0.0002(10) -0.0017(9) 0.0015(10)
N5 0.0178(11) 0.0235(12) 0.0204(12) -0.0016(10) 0.0002(10) -0.0012(10)
N6 0.0216(11) 0.0207(12) 0.0242(12) 0.0041(10) 0.0014(10) 0.0004(10)
N7 0.0226(11) 0.0213(12) 0.0219(12) 0.0013(10) 0.0040(9) -0.0005(10)
O1 0.0243(9) 0.0293(10) 0.0262(10) 0.0051(8) 0.0045(7) 0.0140(8)
O2 0.0235(9) 0.0280(10) 0.0204(9) 0.0072(8) 0.0038(8) 0.0003(8)
O3 0.0259(9) 0.0183(9) 0.0320(10) 0.0061(8) 0.0015(8) 0.0043(8)
O4 0.0250(10) 0.0287(10) 0.0339(11) 0.0009(8) 0.0151(9) 0.0016(8)
O5 0.0267(10) 0.0304(11) 0.0202(10) 0.0026(8) -0.0016(8) 0.0009(8)
O6 0.0374(11) 0.0264(11) 0.0463(12) -0.0010(9) -0.0015(9) 0.0163(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 N2 1.308(3) . ?
C1 N3 1.346(3) . ?
C1 N6 1.453(3) . ?
C2 N3 1.317(3) . ?
C2 N1 1.345(3) . ?
C2 H2 0.9500 . ?
C3 N4 1.372(3) . ?
C3 N5 1.383(3) . ?
C3 N1 1.395(3) . ?
N1 N2 1.371(2) . ?
N4 O1 1.242(2) . ?
N4 O2 1.258(2) . ?
N5 O3 1.239(2) . ?
N5 O4 1.250(2) . ?
N6 O5 1.220(2) . ?
N6 O6 1.224(2) . ?
N7 H7A 0.917(14) . ?
N7 H7B 0.898(14) . ?
N7 H7C 0.907(14) . ?
N7 H7D 0.911(14) . ?
O7 H7E 0.8500 . ?
O7 H7F 0.8500 . ?



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






























N2 C1 N3 118.2(2) . . ?
N2 C1 N6 120.6(2) . . ?
N3 C1 N6 121.2(2) . . ?
N3 C2 N1 110.72(19) . . ?
N3 C2 H2 124.6 . . ?
N1 C2 H2 124.6 . . ?
N4 C3 N5 124.3(2) . . ?
N4 C3 N1 117.7(2) . . ?
N5 C3 N1 117.8(2) . . ?
C2 N1 N2 109.84(17) . . ?
C2 N1 C3 129.15(19) . . ?
N2 N1 C3 120.99(18) . . ?
C1 N2 N1 100.13(17) . . ?
C2 N3 C1 101.15(18) . . ?
O1 N4 O2 120.47(19) . . ?
O1 N4 C3 122.51(19) . . ?
O2 N4 C3 117.01(19) . . ?
O3 N5 O4 121.61(19) . . ?
O3 N5 C3 122.0(2) . . ?
O4 N5 C3 116.37(19) . . ?
O5 N6 O6 125.2(2) . . ?
O5 N6 C1 117.94(19) . . ?
O6 N6 C1 116.9(2) . . ?
H7A N7 H7B 110.3(14) . . ?
H7A N7 H7C 107.0(14) . . ?
H7B N7 H7C 111.8(14) . . ?
H7A N7 H7D 108.6(14) . . ?
H7B N7 H7D 109.9(14) . . ?
H7C N7 H7D 109.2(14) . . ?
H7E O7 H7F 108.3 . . ?



_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        25.21

_diffrn_measured_fraction_theta_full 0.980

_refine_diff_density_max         0.217

_refine_diff_density_min         -0.204

_refine_diff_density_rms         0.053




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

data_exp_3283
_database_code_depnum_ccdc_archive 'CCDC 1442344'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2015-06-03

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C4 H3 N5 O6'

_chemical_formula_sum            'C4 H3 N5 O6'

_chemical_formula_weight         217.11

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   12.7070(8)

_cell_length_b                   11.6741(8)

_cell_length_c                   10.8273(8)

_cell_angle_alpha                90.00

_cell_angle_beta                 99.727(7)

_cell_angle_gamma                90.00

_cell_volume                     1583.06(19)

_cell_formula_units_Z            8

_cell_measurement_reflns_used    2142

_cell_measurement_temperature    101.7

_cell_measurement_theta_max      29.4033

_cell_measurement_theta_min      3.2160

_exptl_absorpt_coefficient_mu    0.172

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.51073

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.822

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             880

_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.45

_exptl_crystal_size_min          0.45

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0446

_diffrn_reflns_av_unetI/netI     0.0556

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_k_max       13

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_l_max       13

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_number            7014

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         3.22

_diffrn_ambient_temperature      101.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.998

_diffrn_measured_fraction_theta_max 0.998

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega  -49.00   35.00   1.0000    3.5000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -52.0000   57.0000 84

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -39.00   46.00   1.0000    3.5000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -78.0000  -52.0000 85

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -32.00   -5.00   1.0000    3.5000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210  -37.0000  -60.0000 27

 

#__ type_ start__ end____ width___ exp.time_

  4 omega  -14.00   24.00   1.0000    3.5000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -37.0000 -180.0000 38

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      0.0472175000

_diffrn_orient_matrix_UB_12      0.0247923000

_diffrn_orient_matrix_UB_13      -0.0150187000

_diffrn_orient_matrix_UB_21      0.0083423000

_diffrn_orient_matrix_UB_22      0.0294418000

_diffrn_orient_matrix_UB_23      0.0581104000

_diffrn_orient_matrix_UB_31      0.0300956000

_diffrn_orient_matrix_UB_32      -0.0470201000

_diffrn_orient_matrix_UB_33      0.0286032000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                2431

_reflns_number_total             3111

_reflns_odcompleteness_completeness 99.74

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.414

_refine_diff_density_min         -0.438

_refine_diff_density_rms         0.098

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.054

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     271

_refine_ls_number_reflns         3111

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0748

_refine_ls_R_factor_gt           0.0587

_refine_ls_restrained_S_all      1.054

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0903P)²+0.3690P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.1484

_refine_ls_wR_factor_ref         0.1637

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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




































O8 O 0.16654(14) 0.02156(15) 0.30487(17) 0.0243(5) Uani 1 1 d . . .
O6 O -0.07069(14) -0.22879(16) 0.86000(17) 0.0238(4) Uani 1 1 d . . .
N3 N 0.33481(17) 0.02101(18) 1.0715(2) 0.0235(5) Uani 1 1 d . . .
O4 O 0.05416(14) -0.33284(15) 0.64391(17) 0.0224(4) Uani 1 1 d . . .
N9 N 0.39479(16) -0.24496(17) 0.7558(2) 0.0192(5) Uani 1 1 d . . .
N1 N 0.13714(15) -0.14560(17) 0.89547(19) 0.0160(5) Uani 1 1 d . . .
N8 N 0.18423(16) 0.07997(18) 0.4005(2) 0.0193(5) Uani 1 1 d . . .
N5 N 0.00222(16) -0.29782(18) 0.87089(19) 0.0178(5) Uani 1 1 d . . .
N4 N 0.09380(16) -0.24829(17) 0.6989(2) 0.0170(5) Uani 1 1 d . . .
O2 O 0.41507(14) -0.03943(16) 1.0919(2) 0.0325(5) Uani 1 1 d . . .
N6 N 0.35245(16) -0.08813(17) 0.61302(19) 0.0177(5) Uani 1 1 d . . .
N7 N 0.28721(15) -0.07316(17) 0.50071(18) 0.0164(5) Uani 1 1 d . . .
O3 O 0.12481(16) -0.16387(16) 0.65141(18) 0.0295(5) Uani 1 1 d . . .
O12 O 0.56166(15) -0.08327(17) 0.6192(2) 0.0355(5) Uani 1 1 d . . .
O7 O 0.14845(16) 0.17543(16) 0.41215(18) 0.0302(5) Uani 1 1 d . . .
N2 N 0.23661(15) -0.13468(18) 0.9651(2) 0.0181(5) Uani 1 1 d . . .
N10 N 0.52843(17) -0.1785(2) 0.6332(2) 0.0215(5) Uani 1 1 d . . .
O11 O 0.57927(15) -0.26668(16) 0.6459(2) 0.0312(5) Uani 1 1 d . . .
O5 O -0.00131(15) -0.39767(15) 0.89859(19) 0.0279(5) Uani 1 1 d . . .
C8 C 0.40819(19) -0.1927(2) 0.6305(2) 0.0171(5) Uani 1 1 d . . .
H8 H 0.3787 -0.2467 0.5615 0.021 Uiso 1 1 calc R . .
O9 O 0.31611(16) -0.30352(18) 0.75345(18) 0.0351(5) Uani 1 1 d . . .
O1 O 0.32789(16) 0.11771(16) 1.1106(2) 0.0351(5) Uani 1 1 d . . .
C5 C 0.25430(18) 0.0325(2) 0.5085(2) 0.0169(6) Uani 1 1 d . . .
C3 C 0.08320(19) -0.0438(2) 0.8811(2) 0.0184(6) Uani 1 1 d . . .
H3 H 0.0137 -0.0313 0.8348 0.022 Uiso 1 1 calc R . .
C2 C 0.14802(19) 0.0360(2) 0.9458(2) 0.0190(6) Uani 1 1 d . . .
H2 H 0.1341 0.1151 0.9559 0.023 Uiso 1 1 calc R . .
C4 C 0.10898(18) -0.2537(2) 0.8431(2) 0.0158(5) Uani 1 1 d . . .
H4 H 0.1665 -0.3101 0.8747 0.019 Uiso 1 1 calc R . .
C7 C 0.3592(2) 0.0079(2) 0.6863(3) 0.0217(6) Uani 1 1 d . . .
H7 H 0.4011 0.0169 0.7671 0.026 Uiso 1 1 calc R . .
C1 C 0.23958(18) -0.0254(2) 0.9938(2) 0.0181(6) Uani 1 1 d . . .
C6 C 0.2945(2) 0.0880(2) 0.6214(3) 0.0217(6) Uani 1 1 d . . .
H6 H 0.2800 0.1635 0.6466 0.026 Uiso 1 1 calc R . .
O10 O 0.45796(18) -0.2213(2) 0.8479(2) 0.0534(7) 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






























O8 0.0215(10) 0.0273(10) 0.0201(10) -0.0017(8) -0.0075(8) -0.0007(8)
O6 0.0132(9) 0.0336(10) 0.0230(10) 0.0032(8) -0.0013(8) 0.0035(8)
N3 0.0154(11) 0.0235(12) 0.0272(13) -0.0009(10) -0.0087(10) -0.0041(9)
O4 0.0187(9) 0.0282(10) 0.0180(10) -0.0048(8) -0.0033(8) -0.0052(8)
N9 0.0102(10) 0.0260(12) 0.0194(12) 0.0018(9) -0.0027(9) -0.0007(9)
N1 0.0092(10) 0.0217(11) 0.0144(11) -0.0001(8) -0.0053(8) -0.0010(8)
N8 0.0140(11) 0.0237(12) 0.0191(12) 0.0008(9) -0.0008(9) -0.0001(9)
N5 0.0140(11) 0.0242(12) 0.0135(11) -0.0006(9) -0.0028(9) -0.0020(9)
N4 0.0091(10) 0.0244(12) 0.0162(11) -0.0003(9) -0.0016(8) -0.0018(9)
O2 0.0141(10) 0.0307(11) 0.0460(13) -0.0043(9) -0.0144(9) 0.0025(8)
N6 0.0128(10) 0.0240(12) 0.0137(11) 0.0004(8) -0.0051(9) -0.0020(8)
N7 0.0101(10) 0.0245(11) 0.0122(11) 0.0026(8) -0.0045(8) -0.0035(8)
O3 0.0344(12) 0.0342(11) 0.0195(10) 0.0042(8) 0.0033(9) -0.0134(9)
O12 0.0216(10) 0.0357(12) 0.0488(14) 0.0130(10) 0.0050(10) -0.0054(9)
O7 0.0359(12) 0.0261(11) 0.0268(11) 0.0009(8) -0.0003(9) 0.0136(9)
N2 0.0097(10) 0.0233(12) 0.0181(11) -0.0001(9) -0.0067(9) -0.0008(8)
N10 0.0148(11) 0.0326(13) 0.0154(11) 0.0021(9) -0.0020(9) -0.0017(10)
O11 0.0175(10) 0.0341(11) 0.0381(12) 0.0015(9) -0.0063(9) 0.0086(9)
O5 0.0262(10) 0.0220(11) 0.0353(12) 0.0015(8) 0.0051(9) -0.0051(8)
C8 0.0105(11) 0.0235(13) 0.0156(12) 0.0022(10) -0.0026(10) 0.0001(10)
O9 0.0247(11) 0.0544(13) 0.0259(11) 0.0017(10) 0.0033(9) -0.0171(10)
O1 0.0283(11) 0.0244(11) 0.0461(13) -0.0111(9) -0.0126(10) -0.0011(9)
C5 0.0106(12) 0.0222(13) 0.0163(13) 0.0021(10) -0.0026(10) -0.0020(10)
C3 0.0122(12) 0.0220(13) 0.0192(13) 0.0014(10) -0.0026(10) 0.0022(10)
C2 0.0150(12) 0.0198(13) 0.0200(13) -0.0002(10) -0.0034(10) 0.0019(10)
C4 0.0110(12) 0.0228(13) 0.0119(12) 0.0014(9) -0.0029(10) -0.0020(10)
C7 0.0187(13) 0.0246(14) 0.0192(14) -0.0053(11) -0.0044(11) -0.0038(11)
C1 0.0123(12) 0.0213(14) 0.0176(13) -0.0006(10) -0.0058(10) -0.0007(10)
C6 0.0195(13) 0.0225(13) 0.0214(14) -0.0035(11) -0.0010(11) -0.0020(11)
O10 0.0325(12) 0.103(2) 0.0187(11) 0.0127(12) -0.0132(10) -0.0326(13)



_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




































O8 N8 1.228(3) . ?
O6 N5 1.219(3) . ?
N3 O2 1.229(3) . ?
N3 O1 1.214(3) . ?
N3 C1 1.457(3) . ?
O4 N4 1.217(3) . ?
N9 C8 1.523(3) . ?
N9 O9 1.208(3) . ?
N9 O10 1.202(3) . ?
N1 N2 1.364(3) . ?
N1 C3 1.368(3) . ?
N1 C4 1.404(3) . ?
N8 O7 1.218(3) . ?
N8 C5 1.455(3) . ?
N5 O5 1.206(3) . ?
N5 C4 1.528(3) . ?
N4 O3 1.208(3) . ?
N4 C4 1.542(3) . ?
N6 N7 1.362(3) . ?
N6 C8 1.408(3) . ?
N6 C7 1.368(3) . ?
N7 C5 1.310(3) . ?
O12 N10 1.208(3) . ?
N2 C1 1.312(3) . ?
N10 O11 1.211(3) . ?
N10 C8 1.532(3) . ?
C8 H8 1.0000 . ?
C5 C6 1.401(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.357(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.390(3) . ?
C4 H4 1.0000 . ?
C7 H7 0.9500 . ?
C7 C6 1.359(4) . ?
C6 H6 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
























































O2 N3 C1 118.2(2) . . ?
O1 N3 O2 125.3(2) . . ?
O1 N3 C1 116.5(2) . . ?
O9 N9 C8 115.1(2) . . ?
O10 N9 C8 119.2(2) . . ?
O10 N9 O9 125.6(2) . . ?
N2 N1 C3 112.4(2) . . ?
N2 N1 C4 117.14(19) . . ?
C3 N1 C4 130.3(2) . . ?
O8 N8 C5 117.8(2) . . ?
O7 N8 O8 125.2(2) . . ?
O7 N8 C5 117.0(2) . . ?
O6 N5 C4 116.34(19) . . ?
O5 N5 O6 127.1(2) . . ?
O5 N5 C4 116.5(2) . . ?
O4 N4 C4 115.7(2) . . ?
O3 N4 O4 126.2(2) . . ?
O3 N4 C4 118.05(19) . . ?
N7 N6 C8 116.6(2) . . ?
N7 N6 C7 112.4(2) . . ?
C7 N6 C8 130.7(2) . . ?
C5 N7 N6 102.48(19) . . ?
C1 N2 N1 102.05(19) . . ?
O12 N10 O11 127.3(2) . . ?
O12 N10 C8 117.8(2) . . ?
O11 N10 C8 114.9(2) . . ?
N9 C8 N10 106.72(18) . . ?
N9 C8 H8 109.2 . . ?
N6 C8 N9 109.7(2) . . ?
N6 C8 N10 112.7(2) . . ?
N6 C8 H8 109.2 . . ?
N10 C8 H8 109.2 . . ?
N7 C5 N8 117.8(2) . . ?
N7 C5 C6 114.7(2) . . ?
C6 C5 N8 127.5(2) . . ?
N1 C3 H3 126.6 . . ?
C2 C3 N1 106.8(2) . . ?
C2 C3 H3 126.6 . . ?
C3 C2 H2 128.2 . . ?
C3 C2 C1 103.6(2) . . ?
C1 C2 H2 128.2 . . ?
N1 C4 N5 113.45(19) . . ?
N1 C4 N4 110.60(19) . . ?
N1 C4 H4 109.4 . . ?
N5 C4 N4 104.45(17) . . ?
N5 C4 H4 109.4 . . ?
N4 C4 H4 109.4 . . ?
N6 C7 H7 126.5 . . ?
C6 C7 N6 106.9(2) . . ?
C6 C7 H7 126.5 . . ?
N2 C1 N3 119.1(2) . . ?
N2 C1 C2 115.1(2) . . ?
C2 C1 N3 125.8(2) . . ?
C5 C6 H6 128.3 . . ?
C7 C6 C5 103.4(2) . . ?
C7 C6 H6 128.3 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


















































O8 N8 C5 N7 -5.5(3) . . . . ?
O8 N8 C5 C6 172.5(2) . . . . ?
O6 N5 C4 N1 43.7(3) . . . . ?
O6 N5 C4 N4 -76.8(2) . . . . ?
O4 N4 C4 N1 -169.57(19) . . . . ?
O4 N4 C4 N5 -47.2(3) . . . . ?
N1 N2 C1 N3 179.0(2) . . . . ?
N1 N2 C1 C2 -0.6(3) . . . . ?
N1 C3 C2 C1 1.0(3) . . . . ?
N8 C5 C6 C7 -176.9(2) . . . . ?
O2 N3 C1 N2 10.8(4) . . . . ?
O2 N3 C1 C2 -169.6(2) . . . . ?
N6 N7 C5 N8 177.92(19) . . . . ?
N6 N7 C5 C6 -0.3(3) . . . . ?
N6 C7 C6 C5 -1.4(3) . . . . ?
N7 N6 C8 N9 -131.0(2) . . . . ?
N7 N6 C8 N10 110.2(2) . . . . ?
N7 N6 C7 C6 1.4(3) . . . . ?
N7 C5 C6 C7 1.1(3) . . . . ?
O3 N4 C4 N1 12.8(3) . . . . ?
O3 N4 C4 N5 135.2(2) . . . . ?
O12 N10 C8 N9 -121.3(2) . . . . ?
O12 N10 C8 N6 -0.8(3) . . . . ?
O7 N8 C5 N7 175.1(2) . . . . ?
O7 N8 C5 C6 -6.9(4) . . . . ?
N2 N1 C3 C2 -1.5(3) . . . . ?
N2 N1 C4 N5 128.8(2) . . . . ?
N2 N1 C4 N4 -114.2(2) . . . . ?
O11 N10 C8 N9 60.7(3) . . . . ?
O11 N10 C8 N6 -178.8(2) . . . . ?
O5 N5 C4 N1 -137.8(2) . . . . ?
O5 N5 C4 N4 101.7(2) . . . . ?
C8 N6 N7 C5 -175.2(2) . . . . ?
C8 N6 C7 C6 174.9(2) . . . . ?
O9 N9 C8 N6 86.6(3) . . . . ?
O9 N9 C8 N10 -151.1(2) . . . . ?
O1 N3 C1 N2 -169.5(2) . . . . ?
O1 N3 C1 C2 10.1(4) . . . . ?
C3 N1 N2 C1 1.3(3) . . . . ?
C3 N1 C4 N5 -56.5(3) . . . . ?
C3 N1 C4 N4 60.5(3) . . . . ?
C3 C2 C1 N3 -179.9(2) . . . . ?
C3 C2 C1 N2 -0.3(3) . . . . ?
C4 N1 N2 C1 176.9(2) . . . . ?
C4 N1 C3 C2 -176.4(2) . . . . ?
C7 N6 N7 C5 -0.7(3) . . . . ?
C7 N6 C8 N9 55.6(3) . . . . ?
C7 N6 C8 N10 -63.1(3) . . . . ?
O10 N9 C8 N6 -89.9(3) . . . . ?
O10 N9 C8 N10 32.5(3) . . . . ?






####################################################################### 
# 
# 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 1442345'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'H5 N2, C3 H N6 O6'

_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           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                   6.4094(9)

_cell_length_b                   16.106(2)

_cell_length_c                   9.1462(11)

_cell_angle_alpha                90.00

_cell_angle_beta                 100.123(4)

_cell_angle_gamma                90.00

_cell_volume                     929.5(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    1477

_cell_measurement_theta_min      3.39

_cell_measurement_theta_max      23.22



_exptl_crystal_description       block

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.19

_exptl_crystal_size_mid          0.17

_exptl_crystal_size_min          0.17

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.788

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.168

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6934

_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            5568

_diffrn_reflns_av_R_equivalents  0.0519

_diffrn_reflns_av_sigmaI/netI    0.0812

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       4

_diffrn_reflns_limit_k_min       -19

_diffrn_reflns_limit_k_max       19

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         3.39

_diffrn_reflns_theta_max         25.39

_reflns_number_total             1676

_reflns_number_gt                1022

_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)+(0.0418P)²+0.5596P] 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         1676

_refine_ls_number_parameters     169

_refine_ls_number_restraints     21

_refine_ls_R_factor_all          0.1081

_refine_ls_R_factor_gt           0.0508

_refine_ls_wR_factor_ref         0.1107

_refine_ls_wR_factor_gt          0.0931

_refine_ls_goodness_of_fit_ref   1.027

_refine_ls_restrained_S_all      1.025

_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 0.8258(4) 0.22733(19) 1.0782(3) 0.0167(7) Uani 1 1 d . . .
C2 C 0.5775(5) 0.2267(2) 0.9027(3) 0.0228(8) Uani 1 1 d . . .
H2 H 0.4764 0.2120 0.8178 0.027 Uiso 1 1 calc R . .
C3 C 0.4594(5) 0.37140(19) 0.9345(3) 0.0183(7) Uani 1 1 d . . .
N1 N 0.5802(4) 0.29958(15) 0.9745(3) 0.0182(6) Uani 1 1 d . . .
N2 N 0.7466(4) 0.30059(16) 1.0913(2) 0.0199(6) Uani 1 1 d . . .
N3 N 0.7336(4) 0.17834(16) 0.9656(3) 0.0225(7) Uani 1 1 d . . .
N4 N 0.2945(4) 0.38896(17) 1.0071(3) 0.0225(7) Uani 1 1 d . . .
N5 N 0.5248(4) 0.42247(16) 0.8298(3) 0.0220(6) Uani 1 1 d . . .
N6 N 1.0111(4) 0.20074(17) 1.1828(3) 0.0250(7) Uani 1 1 d . . .
N7 N 1.0162(5) 0.56570(18) 0.7227(3) 0.0346(8) Uani 1 1 d D . .
H7A H 1.104(3) 0.5991(15) 0.692(3) 0.052 Uiso 1 1 d D . .
H7B H 0.965(4) 0.5942(15) 0.791(2) 0.052 Uiso 1 1 d D . .
H7C H 1.095(4) 0.5283(15) 0.774(3) 0.052 Uiso 1 1 d D . .
N8 N 0.8577(6) 0.5349(3) 0.6121(4) 0.0769(14) Uani 1 1 d D . .
H8A H 0.787(5) 0.4925(18) 0.644(4) 0.092 Uiso 1 1 d D . .
H8B H 0.759(5) 0.5670(18) 0.573(4) 0.092 Uiso 1 1 d D . .
O1 O 0.1775(4) 0.44972(14) 0.9754(2) 0.0319(6) Uani 1 1 d . . .
O2 O 0.2663(3) 0.33884(14) 1.1082(2) 0.0279(6) Uani 1 1 d . . .
O3 O 0.4338(3) 0.48918(14) 0.7915(2) 0.0302(6) Uani 1 1 d . . .
O4 O 0.6811(4) 0.39835(14) 0.7775(3) 0.0352(6) Uani 1 1 d . . .
O5 O 1.0586(3) 0.24009(14) 1.2984(2) 0.0276(6) Uani 1 1 d . . .
O6 O 1.1092(4) 0.14151(15) 1.1474(3) 0.0443(7) 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 0.0158(17) 0.0166(18) 0.0178(16) 0.0022(14) 0.0035(14) 0.0013(14)
C2 0.0231(19) 0.025(2) 0.0198(17) -0.0028(15) 0.0020(15) -0.0019(16)
C3 0.0159(17) 0.0194(19) 0.0187(17) -0.0005(14) 0.0007(14) 0.0030(14)
N1 0.0163(15) 0.0193(16) 0.0183(13) -0.0010(12) 0.0011(11) 0.0020(11)
N2 0.0177(14) 0.0226(16) 0.0187(14) -0.0001(12) 0.0010(11) 0.0013(12)
N3 0.0215(15) 0.0230(16) 0.0224(14) -0.0028(12) 0.0020(12) 0.0043(13)
N4 0.0190(15) 0.0262(17) 0.0212(15) -0.0015(13) 0.0007(12) 0.0023(13)
N5 0.0227(16) 0.0205(16) 0.0222(15) -0.0024(12) 0.0022(12) 0.0013(13)
N6 0.0247(16) 0.0251(17) 0.0248(16) 0.0030(14) 0.0031(13) 0.0051(13)
N7 0.0310(18) 0.0306(19) 0.0425(19) -0.0007(15) 0.0074(15) 0.0005(15)
N8 0.095(3) 0.086(3) 0.044(2) 0.007(2) -0.001(2) -0.060(3)
O1 0.0293(14) 0.0313(14) 0.0363(13) 0.0043(11) 0.0090(11) 0.0172(12)
O2 0.0276(14) 0.0348(15) 0.0230(12) 0.0084(11) 0.0092(10) 0.0024(11)
O3 0.0304(14) 0.0206(14) 0.0391(14) 0.0091(11) 0.0046(11) 0.0051(11)
O4 0.0364(15) 0.0337(15) 0.0423(14) 0.0052(11) 0.0255(12) 0.0083(12)
O5 0.0288(14) 0.0311(14) 0.0217(12) 0.0003(11) 0.0009(10) 0.0031(11)
O6 0.0426(16) 0.0393(17) 0.0456(16) -0.0083(13) -0.0070(13) 0.0236(14)



_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 N2 1.299(4) . ?
C1 N3 1.348(4) . ?
C1 N6 1.453(4) . ?
C2 N3 1.318(4) . ?
C2 N1 1.344(4) . ?
C2 H2 0.9500 . ?
C3 N4 1.373(4) . ?
C3 N5 1.382(4) . ?
C3 N1 1.404(4) . ?
N1 N2 1.370(3) . ?
N4 O1 1.236(3) . ?
N4 O2 1.264(3) . ?
N5 O3 1.243(3) . ?
N5 O4 1.246(3) . ?
N6 O6 1.217(3) . ?
N6 O5 1.224(3) . ?
N7 N8 1.392(5) . ?
N7 H7A 0.863(16) . ?
N7 H7B 0.883(16) . ?
N7 H7C 0.868(16) . ?
N8 H8A 0.898(17) . ?
N8 H8B 0.846(17) . ?



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
































N2 C1 N3 118.4(3) . . ?
N2 C1 N6 119.7(3) . . ?
N3 C1 N6 121.9(3) . . ?
N3 C2 N1 111.0(3) . . ?
N3 C2 H2 124.5 . . ?
N1 C2 H2 124.5 . . ?
N4 C3 N5 124.4(3) . . ?
N4 C3 N1 118.6(3) . . ?
N5 C3 N1 116.8(3) . . ?
C2 N1 N2 109.4(2) . . ?
C2 N1 C3 129.3(2) . . ?
N2 N1 C3 120.8(2) . . ?
C1 N2 N1 100.4(2) . . ?
C2 N3 C1 100.7(2) . . ?
O1 N4 O2 121.2(3) . . ?
O1 N4 C3 122.4(3) . . ?
O2 N4 C3 116.3(3) . . ?
O3 N5 O4 122.0(3) . . ?
O3 N5 C3 121.7(3) . . ?
O4 N5 C3 116.3(3) . . ?
O6 N6 O5 125.0(3) . . ?
O6 N6 C1 117.2(3) . . ?
O5 N6 C1 117.8(3) . . ?
N8 N7 H7A 114.8(18) . . ?
N8 N7 H7B 112.6(18) . . ?
H7A N7 H7B 105(2) . . ?
N8 N7 H7C 115.2(18) . . ?
H7A N7 H7C 105(2) . . ?
H7B N7 H7C 104(2) . . ?
N7 N8 H8A 112.1(19) . . ?
N7 N8 H8B 119(2) . . ?
H8A N8 H8B 103(3) . . ?



_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        25.39

_diffrn_measured_fraction_theta_full 0.980

_refine_diff_density_max         0.498

_refine_diff_density_min         -0.294

_refine_diff_density_rms         0.065




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

data_exp_2304
_database_code_depnum_ccdc_archive 'CCDC 1442346'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2014-06-25

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C2 N7 O6, C H6 N3'

_chemical_formula_sum            'C3 H6 N10 O6'

_chemical_formula_weight         278.18

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   9.1227(5)

_cell_length_b                   7.0640(4)

_cell_length_c                   16.2597(11)

_cell_angle_alpha                90.00

_cell_angle_beta                 103.139(6)

_cell_angle_gamma                90.00

_cell_volume                     1020.39(10)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1560

_cell_measurement_temperature    98.7

_cell_measurement_theta_max      29.4016

_cell_measurement_theta_min      3.0263

_exptl_absorpt_coefficient_mu    0.168

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.92600

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.811

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             568

_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.45

_exptl_crystal_size_min          0.40

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0235

_diffrn_reflns_av_unetI/netI     0.0354

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_k_min       -4

_diffrn_reflns_limit_l_max       20

_diffrn_reflns_limit_l_min       -19

_diffrn_reflns_number            4294

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         3.03

_diffrn_ambient_temperature      98.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.998

_diffrn_measured_fraction_theta_max 0.998

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega   -3.00   24.00   1.0000    1.5400

omega____ theta____ kappa____ phi______ frames

    -      -13.4210  -99.0000  119.0000 27

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -40.00   -5.00   1.0000    1.5400

omega____ theta____ kappa____ phi______ frames

    -      -13.4210   77.0000 -150.0000 35

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -40.00   36.00   1.0000    1.5400

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -37.0000  -60.0000 76

 

#__ type_ start__ end____ width___ exp.time_

  4 omega  -48.00   45.00   1.0000    1.5400

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -77.0000  -90.0000 93

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.0070588000

_diffrn_orient_matrix_UB_12      -0.0130019000

_diffrn_orient_matrix_UB_13      0.0421907000

_diffrn_orient_matrix_UB_21      0.0023519000

_diffrn_orient_matrix_UB_22      -0.0995720000

_diffrn_orient_matrix_UB_23      -0.0052663000

_diffrn_orient_matrix_UB_31      0.0794590000

_diffrn_orient_matrix_UB_32      0.0018191000

_diffrn_orient_matrix_UB_33      0.0141266000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1714

_reflns_number_total             1999

_reflns_odcompleteness_completeness 99.65

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.212

_refine_diff_density_min         -0.350

_refine_diff_density_rms         0.063

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.062

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     172

_refine_ls_number_reflns         1999

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0448

_refine_ls_R_factor_gt           0.0368

_refine_ls_restrained_S_all      1.062

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.3275P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0840

_refine_ls_wR_factor_ref         0.0893

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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 0.96570(13) 0.20072(18) 0.02712(7) 0.0165(3) Uani 1 1 d . . .
O4 O 1.29484(13) 1.08323(18) 0.26706(7) 0.0180(3) Uani 1 1 d . . .
O3 O 1.14476(12) 0.97117(19) 0.15332(7) 0.0169(3) Uani 1 1 d . . .
O5 O 1.43829(13) 0.53778(19) 0.31304(7) 0.0191(3) Uani 1 1 d . . .
N7 N 1.40481(15) 0.7094(2) 0.30747(8) 0.0144(3) Uani 1 1 d . . .
O2 O 0.88401(14) 0.2815(2) 0.13798(8) 0.0250(3) Uani 1 1 d . . .
N1 N 1.11789(14) 0.5255(2) 0.18534(8) 0.0141(3) Uani 1 1 d . . .
N6 N 1.24659(15) 0.9484(2) 0.21923(8) 0.0133(3) Uani 1 1 d . . .
N4 N 1.18973(15) 0.4633(2) 0.06445(8) 0.0146(3) Uani 1 1 d . . .
N5 N 0.97231(15) 0.2931(2) 0.09179(8) 0.0141(3) Uani 1 1 d . . .
N8 N 1.58374(15) 0.7038(2) 0.05618(8) 0.0157(3) Uani 1 1 d . . .
H8A H 1.5905 0.6255 0.0990 0.019 Uiso 1 1 calc R . .
H8B H 1.5018 0.7055 0.0154 0.019 Uiso 1 1 calc R . .
N9 N 1.68564(15) 0.9396(2) -0.01115(9) 0.0165(3) Uani 1 1 d . . .
H9A H 1.6030 0.9424 -0.0515 0.020 Uiso 1 1 calc R . .
H9B H 1.7608 1.0163 -0.0132 0.020 Uiso 1 1 calc R . .
N2 N 1.23772(14) 0.6269(2) 0.17721(8) 0.0127(3) Uani 1 1 d . . .
O6 O 1.45747(13) 0.82423(19) 0.36460(7) 0.0209(3) Uani 1 1 d . . .
N10 N 1.82047(15) 0.8160(2) 0.11490(9) 0.0164(3) Uani 1 1 d . . .
H10A H 1.8270 0.7376 0.1576 0.020 Uiso 1 1 calc R . .
H10B H 1.8958 0.8925 0.1131 0.020 Uiso 1 1 calc R . .
N3 N 1.28180(14) 0.5922(2) 0.10495(8) 0.0148(3) Uani 1 1 d . . .
C1 C 1.09487(17) 0.4276(2) 0.11522(10) 0.0124(4) Uani 1 1 d . . .
C3 C 1.69698(18) 0.8191(3) 0.05321(10) 0.0132(4) Uani 1 1 d . . .
C2 C 1.30432(17) 0.7682(3) 0.23418(10) 0.0132(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



















O1 0.0185(6) 0.0145(7) 0.0153(6) -0.0030(5) 0.0012(4) -0.0011(5)
O4 0.0234(6) 0.0127(7) 0.0172(6) -0.0047(5) 0.0028(5) -0.0013(5)
O3 0.0152(6) 0.0187(7) 0.0147(6) 0.0034(5) -0.0012(4) 0.0028(5)
O5 0.0188(6) 0.0144(7) 0.0233(7) 0.0046(5) 0.0032(5) 0.0034(5)
N7 0.0123(7) 0.0153(9) 0.0155(7) 0.0017(6) 0.0031(5) -0.0009(6)
O2 0.0243(7) 0.0260(8) 0.0296(7) -0.0062(6) 0.0166(6) -0.0097(6)
N1 0.0134(7) 0.0131(8) 0.0156(7) 0.0006(6) 0.0027(5) -0.0011(6)
N6 0.0134(7) 0.0146(8) 0.0125(7) -0.0011(6) 0.0039(5) -0.0013(6)
N4 0.0141(7) 0.0148(8) 0.0152(7) -0.0016(6) 0.0038(5) -0.0013(6)
N5 0.0152(7) 0.0107(8) 0.0158(7) 0.0008(6) 0.0024(5) 0.0000(6)
N8 0.0149(7) 0.0166(8) 0.0148(7) 0.0026(6) 0.0018(5) -0.0029(6)
N9 0.0142(7) 0.0166(8) 0.0175(7) 0.0028(6) 0.0012(5) -0.0050(6)
N2 0.0122(7) 0.0134(8) 0.0127(7) 0.0000(6) 0.0035(5) -0.0012(6)
O6 0.0230(6) 0.0201(8) 0.0159(6) -0.0035(6) -0.0035(5) -0.0019(6)
N10 0.0142(7) 0.0170(8) 0.0167(7) 0.0031(6) 0.0006(5) -0.0033(6)
N3 0.0148(7) 0.0147(8) 0.0157(7) -0.0026(6) 0.0055(5) -0.0006(6)
C1 0.0125(8) 0.0109(9) 0.0140(8) 0.0009(7) 0.0031(6) 0.0010(7)
C3 0.0136(8) 0.0136(9) 0.0135(8) -0.0024(7) 0.0054(6) 0.0012(7)
C2 0.0136(8) 0.0117(9) 0.0132(8) -0.0015(7) 0.0005(6) 0.0000(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
























O1 N5 1.2275(18) . ?
O4 N6 1.2453(18) . ?
O3 N6 1.2588(17) . ?
O5 N7 1.2482(19) . ?
N7 O6 1.2447(19) . ?
N7 C2 1.392(2) . ?
O2 N5 1.2226(17) . ?
N1 N2 1.3385(19) . ?
N1 C1 1.309(2) . ?
N6 C2 1.378(2) . ?
N4 N3 1.310(2) . ?
N4 C1 1.349(2) . ?
N5 C1 1.450(2) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C3 1.325(2) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C3 1.335(2) . ?
N2 N3 1.3480(18) . ?
N2 C2 1.403(2) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C3 1.327(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

































O5 N7 C2 117.06(14) . . ?
O6 N7 O5 122.16(14) . . ?
O6 N7 C2 120.78(15) . . ?
C1 N1 N2 99.77(12) . . ?
O4 N6 O3 121.43(15) . . ?
O4 N6 C2 122.00(14) . . ?
O3 N6 C2 116.55(14) . . ?
N3 N4 C1 104.46(13) . . ?
O1 N5 C1 117.27(13) . . ?
O2 N5 O1 125.41(14) . . ?
O2 N5 C1 117.32(14) . . ?
H8A N8 H8B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
N1 N2 N3 113.64(13) . . ?
N1 N2 C2 123.82(13) . . ?
N3 N2 C2 122.32(13) . . ?
H10A N10 H10B 120.0 . . ?
C3 N10 H10A 120.0 . . ?
C3 N10 H10B 120.0 . . ?
N4 N3 N2 106.27(12) . . ?
N1 C1 N4 115.85(15) . . ?
N1 C1 N5 122.43(14) . . ?
N4 C1 N5 121.69(14) . . ?
N8 C3 N9 119.90(14) . . ?
N8 C3 N10 119.83(15) . . ?
N10 C3 N9 120.26(16) . . ?
N7 C2 N2 117.07(15) . . ?
N6 C2 N7 125.31(15) . . ?
N6 C2 N2 116.74(14) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag

























O1 N5 C1 N1 -175.93(15) . . . . ?
O1 N5 C1 N4 6.1(2) . . . . ?
O4 N6 C2 N7 9.2(2) . . . . ?
O4 N6 C2 N2 178.15(13) . . . . ?
O3 N6 C2 N7 -172.57(13) . . . . ?
O3 N6 C2 N2 -3.6(2) . . . . ?
O5 N7 C2 N6 175.38(14) . . . . ?
O5 N7 C2 N2 6.5(2) . . . . ?
O2 N5 C1 N1 4.2(2) . . . . ?
O2 N5 C1 N4 -173.80(16) . . . . ?
N1 N2 N3 N4 -0.55(19) . . . . ?
N1 N2 C2 N7 81.92(19) . . . . ?
N1 N2 C2 N6 -87.96(19) . . . . ?
N2 N1 C1 N4 -0.94(19) . . . . ?
N2 N1 C1 N5 -179.05(15) . . . . ?
O6 N7 C2 N6 -4.3(2) . . . . ?
O6 N7 C2 N2 -173.18(13) . . . . ?
N3 N4 C1 N1 0.7(2) . . . . ?
N3 N4 C1 N5 178.79(15) . . . . ?
N3 N2 C2 N7 -103.82(18) . . . . ?
N3 N2 C2 N6 86.30(18) . . . . ?
C1 N1 N2 N3 0.88(18) . . . . ?
C1 N1 N2 C2 175.59(15) . . . . ?
C1 N4 N3 N2 -0.05(17) . . . . ?
C2 N2 N3 N4 -175.35(15) . . . . ?






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

data_exp_3285
_database_code_depnum_ccdc_archive 'CCDC 1442347'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2015-06-03

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C4 H2 N5 O6, N H3.5352 O0.5352'

_chemical_formula_sum            'C4 H5.54 N6 O6.54'

_chemical_formula_weight         242.24

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   4.9109(4)

_cell_length_b                   27.172(2)

_cell_length_c                   6.9470(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 106.073(8)

_cell_angle_gamma                90.00

_cell_volume                     890.77(13)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1238

_cell_measurement_temperature    101.7

_cell_measurement_theta_max      29.2632

_cell_measurement_theta_min      3.0454

_exptl_absorpt_coefficient_mu    0.170

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.86850

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.806

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             495

_exptl_crystal_size_max          0.70

_exptl_crystal_size_mid          0.45

_exptl_crystal_size_min          0.30

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0284

_diffrn_reflns_av_unetI/netI     0.0451

_diffrn_reflns_limit_h_max       4

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_k_max       31

_diffrn_reflns_limit_k_min       -33

_diffrn_reflns_limit_l_max       8

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_number            3676

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         3.14

_diffrn_ambient_temperature      101.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.999

_diffrn_measured_fraction_theta_max 0.999

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega  -33.00   30.00   1.0000    1.8000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210   37.0000  -90.0000 63

 

#__ type_ start__ end____ width___ exp.time_

  2 omega   -7.00   51.00   1.0000    1.8000

omega____ theta____ kappa____ phi______ frames

    -       18.7335   77.0000 -180.0000 58

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -45.00   45.00   1.0000    1.8000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -77.0000    0.0000 90

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.1248293000

_diffrn_orient_matrix_UB_12      0.0120034000

_diffrn_orient_matrix_UB_13      0.0076540000

_diffrn_orient_matrix_UB_21      0.0732619000

_diffrn_orient_matrix_UB_22      0.0227865000

_diffrn_orient_matrix_UB_23      0.0154217000

_diffrn_orient_matrix_UB_31      -0.0405003000

_diffrn_orient_matrix_UB_32      0.0042166000

_diffrn_orient_matrix_UB_33      -0.1048828000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1459

_reflns_number_total             1736

_reflns_odcompleteness_completeness 99.79

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.241

_refine_diff_density_min         -0.280

_refine_diff_density_rms         0.059

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.090

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     157

_refine_ls_number_reflns         1736

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0542

_refine_ls_R_factor_gt           0.0436

_refine_ls_restrained_S_all      1.090

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.2661P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0979

_refine_ls_wR_factor_ref         0.1038

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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























O5 O 0.2433(3) 0.55911(5) 0.5133(2) 0.0210(4) Uani 1 1 d . . .
O6 O 0.4698(3) 0.62708(5) 0.6218(2) 0.0214(4) Uani 1 1 d . . .
O4 O -0.1087(3) 0.52844(5) 0.7083(2) 0.0193(4) Uani 1 1 d . . .
N4 N -0.0146(4) 0.56363(6) 0.8262(2) 0.0159(4) Uani 1 1 d . . .
O2 O 0.8766(3) 0.65964(6) 1.3972(2) 0.0245(4) Uani 1 1 d . . .
O3 O -0.0790(3) 0.56816(6) 0.9862(2) 0.0266(4) Uani 1 1 d . . .
N1 N 0.2311(3) 0.63900(6) 0.9141(2) 0.0154(4) Uani 1 1 d . . .
N5 N 0.2948(3) 0.59487(6) 0.6322(2) 0.0156(4) Uani 1 1 d . . .
N3 N 0.6824(4) 0.68931(7) 1.3432(3) 0.0191(4) Uani 1 1 d . . .
N2 N 0.4656(3) 0.63662(6) 1.0723(2) 0.0158(4) Uani 1 1 d . . .
O1 O 0.6658(3) 0.72807(6) 1.4299(2) 0.0281(4) Uani 1 1 d . . .
C2 C 0.2253(5) 0.70842(8) 1.0738(3) 0.0198(5) Uani 1 1 d . . .
H2 H 0.1795 0.7392 1.1141 0.024 Uiso 1 1 calc R . .
C4 C 0.1599(4) 0.59932(8) 0.7826(3) 0.0161(5) Uani 1 1 d . . .
C3 C 0.0825(4) 0.68134(7) 0.9123(3) 0.0171(5) Uani 1 1 d . . .
H3 H -0.0853 0.6902 0.8183 0.021 Uiso 1 1 calc R . .
C1 C 0.4573(4) 0.67863(8) 1.1642(3) 0.0158(5) Uani 1 1 d . . .
N6 N 0.3717(4) 0.45683(7) 0.7264(2) 0.0201(4) Uani 1 1 d . . .
H6A H 0.4655 0.4534 0.6344 0.024 Uiso 1 1 calc R . .
H6B H 0.2022 0.4699 0.6701 0.024 Uiso 1 1 calc R . .
H6C H 0.3503 0.4275 0.7773 0.024 Uiso 1 1 calc R . .
O7 O 0.5160(6) 0.48606(11) 0.8711(4) 0.0255(10) Uani 0.535(5) 1 d P . .
H7 H 0.6439 0.4995 0.8358 0.038 Uiso 0.535(5) 1 calc PR . .



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

















O5 0.0195(8) 0.0257(9) 0.0191(8) -0.0059(7) 0.0074(6) -0.0020(6)
O6 0.0153(8) 0.0263(9) 0.0228(8) 0.0034(7) 0.0056(6) -0.0058(6)
O4 0.0179(8) 0.0178(8) 0.0218(8) -0.0006(6) 0.0048(6) -0.0028(6)
N4 0.0140(9) 0.0183(10) 0.0161(9) 0.0026(7) 0.0056(7) 0.0032(7)
O2 0.0167(8) 0.0331(9) 0.0220(8) 0.0041(7) 0.0024(6) 0.0045(7)
O3 0.0320(10) 0.0316(9) 0.0230(8) -0.0001(7) 0.0186(7) -0.0041(7)
N1 0.0140(9) 0.0169(9) 0.0143(8) 0.0004(7) 0.0020(7) 0.0007(7)
N5 0.0115(9) 0.0203(9) 0.0143(8) 0.0016(7) 0.0025(7) -0.0004(7)
N3 0.0149(9) 0.0222(10) 0.0198(9) 0.0031(8) 0.0042(7) -0.0024(8)
N2 0.0119(9) 0.0182(9) 0.0171(8) 0.0029(7) 0.0034(7) 0.0005(7)
O1 0.0272(9) 0.0246(9) 0.0286(9) -0.0083(7) 0.0013(7) -0.0022(7)
C2 0.0188(12) 0.0164(11) 0.0241(11) -0.0004(9) 0.0060(9) 0.0010(9)
C4 0.0150(11) 0.0160(11) 0.0178(10) -0.0005(8) 0.0053(8) -0.0001(8)
C3 0.0170(11) 0.0162(11) 0.0171(10) 0.0040(8) 0.0028(8) 0.0044(8)
C1 0.0142(10) 0.0186(11) 0.0152(10) 0.0010(8) 0.0049(8) -0.0015(8)
N6 0.0230(10) 0.0227(10) 0.0163(9) 0.0046(7) 0.0082(8) 0.0075(8)
O7 0.0212(18) 0.0296(19) 0.0249(17) -0.0021(13) 0.0052(12) -0.0082(13)



_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






















O5 N5 1.255(2) . ?
O6 N5 1.243(2) . ?
O4 N4 1.261(2) . ?
N4 O3 1.243(2) . ?
N4 C4 1.383(3) . ?
O2 N3 1.226(2) . ?
N1 N2 1.356(2) . ?
N1 C4 1.394(3) . ?
N1 C3 1.361(3) . ?
N5 C4 1.388(3) . ?
N3 O1 1.227(2) . ?
N3 C1 1.446(3) . ?
N2 C1 1.314(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(3) . ?
C2 C1 1.397(3) . ?
C3 H3 0.9300 . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
N6 O7 1.322(3) . ?
O7 H7 0.8200 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag
































O4 N4 C4 121.83(17) . . ?
O3 N4 O4 121.20(17) . . ?
O3 N4 C4 116.96(17) . . ?
N2 N1 C4 119.82(16) . . ?
N2 N1 C3 112.37(16) . . ?
C3 N1 C4 127.71(17) . . ?
O5 N5 C4 120.77(17) . . ?
O6 N5 O5 121.56(17) . . ?
O6 N5 C4 117.67(17) . . ?
O2 N3 O1 124.49(17) . . ?
O2 N3 C1 118.43(18) . . ?
O1 N3 C1 117.08(17) . . ?
C1 N2 N1 102.64(16) . . ?
C3 C2 H2 128.4 . . ?
C3 C2 C1 103.10(18) . . ?
C1 C2 H2 128.4 . . ?
N4 C4 N1 117.20(18) . . ?
N4 C4 N5 123.91(18) . . ?
N5 C4 N1 118.37(18) . . ?
N1 C3 C2 107.27(18) . . ?
N1 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
N2 C1 N3 118.22(18) . . ?
N2 C1 C2 114.60(18) . . ?
C2 C1 N3 127.17(19) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
O7 N6 H6A 109.5 . . ?
O7 N6 H6B 109.5 . . ?
O7 N6 H6C 109.5 . . ?
N6 O7 H7 109.5 . . ?



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

























O5 N5 C4 N4 6.7(3) . . . . ?
O5 N5 C4 N1 178.17(17) . . . . ?
O6 N5 C4 N4 -172.43(17) . . . . ?
O6 N5 C4 N1 -0.9(3) . . . . ?
O4 N4 C4 N1 174.29(16) . . . . ?
O4 N4 C4 N5 -14.1(3) . . . . ?
O2 N3 C1 N2 2.8(3) . . . . ?
O2 N3 C1 C2 -177.1(2) . . . . ?
O3 N4 C4 N1 -4.5(3) . . . . ?
O3 N4 C4 N5 167.05(18) . . . . ?
N1 N2 C1 N3 -179.32(17) . . . . ?
N1 N2 C1 C2 0.6(2) . . . . ?
N2 N1 C4 N4 90.0(2) . . . . ?
N2 N1 C4 N5 -82.1(2) . . . . ?
N2 N1 C3 C2 0.8(2) . . . . ?
O1 N3 C1 N2 -177.84(19) . . . . ?
O1 N3 C1 C2 2.3(3) . . . . ?
C4 N1 N2 C1 -177.50(18) . . . . ?
C4 N1 C3 C2 177.2(2) . . . . ?
C3 N1 N2 C1 -0.8(2) . . . . ?
C3 N1 C4 N4 -86.1(3) . . . . ?
C3 N1 C4 N5 101.8(2) . . . . ?
C3 C2 C1 N3 179.8(2) . . . . ?
C3 C2 C1 N2 -0.1(3) . . . . ?
C1 C2 C3 N1 -0.4(2) . . . . ?






####################################################################### 
# 
# 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_bo1814
_database_code_depnum_ccdc_archive 'CCDC 1442348'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 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 H3 N7 O7'

_chemical_formula_weight         249.12



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                   11.481(3)

_cell_length_b                   6.6275(16)

_cell_length_c                   12.722(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 110.433(3)

_cell_angle_gamma                90.00

_cell_volume                     907.1(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    153(2)

_cell_measurement_reflns_used    3491

_cell_measurement_theta_min      2.060

_cell_measurement_theta_max      31.507



_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.42

_exptl_crystal_size_mid          0.38

_exptl_crystal_size_min          0.28

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.824

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.177

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_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            11121

_diffrn_reflns_av_R_equivalents  0.0260

_diffrn_reflns_av_sigmaI/netI    0.0215

_diffrn_reflns_limit_h_min       -16

_diffrn_reflns_limit_h_max       16

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -18

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         3.28

_diffrn_reflns_theta_max         31.51

_reflns_number_total             3017

_reflns_number_gt                2934

_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    ?

_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)+(0.0256P)²+0.6520P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.011(2)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         3017

_refine_ls_number_parameters     159

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0418

_refine_ls_R_factor_gt           0.0402

_refine_ls_wR_factor_ref         0.0862

_refine_ls_wR_factor_gt          0.0853

_refine_ls_goodness_of_fit_ref   0.999

_refine_ls_restrained_S_all      0.999

_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 0.14622(8) 0.14364(14) 0.64303(7) 0.02391(18) Uani 1 1 d . . .
O2 O 0.24688(9) 0.74944(13) 0.23645(7) 0.02547(19) Uani 1 1 d . . .
O3 O 0.05033(9) 0.78990(17) 0.21131(8) 0.0360(2) Uani 1 1 d . . .
O4 O 0.47030(9) 0.45703(18) 0.67409(9) 0.0410(3) Uani 1 1 d . . .
O5 O 0.49894(9) 0.2415(2) 0.55719(10) 0.0438(3) Uani 1 1 d . . .
O6 O 0.33712(10) -0.07657(14) 0.56641(8) 0.0311(2) Uani 1 1 d . . .
O7 O 0.21520(10) 0.05999(14) 0.41165(7) 0.0315(2) Uani 1 1 d . . .
N1 N 0.08841(8) 0.62828(14) 0.41791(7) 0.01745(17) Uani 1 1 d . . .
N2 N 0.12947(8) 0.50575(14) 0.50293(7) 0.01693(17) Uani 1 1 d . . .
N3 N 0.23171(8) 0.42099(13) 0.49430(7) 0.01507(17) Uani 1 1 d . . .
N4 N 0.26029(8) 0.48324(14) 0.40629(7) 0.01665(17) Uani 1 1 d . . .
N5 N 0.15445(9) 0.72575(14) 0.26139(8) 0.02007(19) Uani 1 1 d . . .
N6 N 0.43759(9) 0.32495(16) 0.60420(8) 0.0233(2) Uani 1 1 d . . .
N7 N 0.28327(9) 0.06453(15) 0.50944(8) 0.02040(19) Uani 1 1 d . . .
C1 C 0.16888(9) 0.61072(15) 0.36232(8) 0.01597(18) Uani 1 1 d . . .
C2 C 0.30008(9) 0.26777(16) 0.57065(8) 0.01596(18) Uani 1 1 d . . .
C3 C 0.26078(10) 0.24335(17) 0.67390(9) 0.0199(2) Uani 1 1 d . . .
H3A H 0.3245 0.1648 0.7324 0.024 Uiso 1 1 calc R . .
H3B H 0.2538 0.3777 0.7052 0.024 Uiso 1 1 calc R . .
H1O H 0.0892(19) 0.228(3) 0.6243(16) 0.043(5) 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 0.0201(4) 0.0240(4) 0.0314(4) 0.0096(3) 0.0136(3) 0.0059(3)
O2 0.0321(4) 0.0239(4) 0.0251(4) 0.0035(3) 0.0160(3) -0.0021(3)
O3 0.0331(5) 0.0448(6) 0.0291(5) 0.0166(4) 0.0098(4) 0.0174(4)
O4 0.0265(5) 0.0449(6) 0.0462(6) -0.0167(5) 0.0058(4) -0.0101(4)
O5 0.0219(4) 0.0632(8) 0.0524(6) -0.0130(6) 0.0205(4) -0.0010(5)
O6 0.0421(5) 0.0221(4) 0.0333(5) 0.0067(4) 0.0183(4) 0.0137(4)
O7 0.0448(6) 0.0234(4) 0.0218(4) -0.0051(3) 0.0058(4) -0.0034(4)
N1 0.0169(4) 0.0172(4) 0.0189(4) 0.0015(3) 0.0070(3) 0.0008(3)
N2 0.0155(4) 0.0175(4) 0.0188(4) 0.0003(3) 0.0074(3) 0.0020(3)
N3 0.0152(4) 0.0162(4) 0.0151(3) 0.0009(3) 0.0069(3) 0.0009(3)
N4 0.0188(4) 0.0173(4) 0.0156(4) 0.0014(3) 0.0082(3) 0.0004(3)
N5 0.0265(4) 0.0169(4) 0.0176(4) 0.0022(3) 0.0087(3) 0.0024(3)
N6 0.0164(4) 0.0287(5) 0.0230(4) 0.0022(4) 0.0046(3) 0.0001(4)
N7 0.0251(4) 0.0177(4) 0.0218(4) 0.0004(3) 0.0124(4) 0.0019(3)
C1 0.0179(4) 0.0147(4) 0.0155(4) -0.0003(3) 0.0061(3) -0.0009(3)
C2 0.0148(4) 0.0176(4) 0.0154(4) 0.0007(3) 0.0051(3) 0.0016(3)
C3 0.0232(5) 0.0227(5) 0.0159(4) 0.0029(4) 0.0095(4) 0.0037(4)



_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 1.4002(14) . ?
O1 H1O 0.83(2) . ?
O2 N5 1.2193(13) . ?
O3 N5 1.2182(13) . ?
O4 N6 1.2102(15) . ?
O5 N6 1.2056(14) . ?
O6 N7 1.2121(13) . ?
O7 N7 1.2168(13) . ?
N1 N2 1.3021(12) . ?
N1 C1 1.3505(13) . ?
N2 N3 1.3400(12) . ?
N3 N4 1.3371(12) . ?
N3 C2 1.4347(13) . ?
N4 C1 1.3108(13) . ?
N5 C1 1.4521(13) . ?
N6 C2 1.5322(14) . ?
N7 C2 1.5340(14) . ?
C2 C3 1.5391(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag































C3 O1 H1O 109.3(13) . . ?
N2 N1 C1 105.41(8) . . ?
N1 N2 N3 105.48(8) . . ?
N4 N3 N2 114.66(8) . . ?
N4 N3 C2 123.30(8) . . ?
N2 N3 C2 121.95(8) . . ?
C1 N4 N3 99.34(8) . . ?
O3 N5 O2 127.11(10) . . ?
O3 N5 C1 115.71(9) . . ?
O2 N5 C1 117.17(9) . . ?
O5 N6 O4 127.65(11) . . ?
O5 N6 C2 118.17(10) . . ?
O4 N6 C2 114.13(10) . . ?
O6 N7 O7 127.14(11) . . ?
O6 N7 C2 115.24(9) . . ?
O7 N7 C2 117.57(9) . . ?
N4 C1 N1 115.11(9) . . ?
N4 C1 N5 122.88(9) . . ?
N1 C1 N5 122.01(9) . . ?
N3 C2 N6 106.29(8) . . ?
N3 C2 N7 109.62(8) . . ?
N6 C2 N7 107.06(8) . . ?
N3 C2 C3 113.46(8) . . ?
N6 C2 C3 111.64(8) . . ?
N7 C2 C3 108.57(8) . . ?
O1 C3 C2 109.68(9) . . ?
O1 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
O1 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


































C1 N1 N2 N3 -0.08(11) . . . . ?
N1 N2 N3 N4 0.07(11) . . . . ?
N1 N2 N3 C2 -176.69(9) . . . . ?
N2 N3 N4 C1 -0.04(11) . . . . ?
C2 N3 N4 C1 176.68(9) . . . . ?
N3 N4 C1 N1 -0.02(11) . . . . ?
N3 N4 C1 N5 179.86(9) . . . . ?
N2 N1 C1 N4 0.06(12) . . . . ?
N2 N1 C1 N5 -179.82(9) . . . . ?
O3 N5 C1 N4 158.90(11) . . . . ?
O2 N5 C1 N4 -21.78(15) . . . . ?
O3 N5 C1 N1 -21.23(15) . . . . ?
O2 N5 C1 N1 158.10(10) . . . . ?
N4 N3 C2 N6 48.91(12) . . . . ?
N2 N3 C2 N6 -134.61(9) . . . . ?
N4 N3 C2 N7 -66.47(12) . . . . ?
N2 N3 C2 N7 110.01(10) . . . . ?
N4 N3 C2 C3 171.98(9) . . . . ?
N2 N3 C2 C3 -11.54(13) . . . . ?
O5 N6 C2 N3 -99.02(12) . . . . ?
O4 N6 C2 N3 78.60(12) . . . . ?
O5 N6 C2 N7 18.07(14) . . . . ?
O4 N6 C2 N7 -164.30(10) . . . . ?
O5 N6 C2 C3 136.77(12) . . . . ?
O4 N6 C2 C3 -45.60(13) . . . . ?
O6 N7 C2 N3 -179.84(9) . . . . ?
O7 N7 C2 N3 -2.26(13) . . . . ?
O6 N7 C2 N6 65.27(11) . . . . ?
O7 N7 C2 N6 -117.15(10) . . . . ?
O6 N7 C2 C3 -55.40(12) . . . . ?
O7 N7 C2 C3 122.18(11) . . . . ?
N3 C2 C3 O1 74.67(11) . . . . ?
N6 C2 C3 O1 -165.25(9) . . . . ?
N7 C2 C3 O1 -47.45(11) . . . . ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        31.51

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.412

_refine_diff_density_min         -0.232

_refine_diff_density_rms         0.059




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

data_exp_3284
_database_code_depnum_ccdc_archive 'CCDC 1442349'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2015-06-03

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C4 H2 N5 O6, H5 N2'

_chemical_formula_sum            'C4 H7 N7 O6'

_chemical_formula_weight         249.17

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   4.8027(2)

_cell_length_b                   27.5834(14)

_cell_length_c                   7.2531(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 104.940(6)

_cell_angle_gamma                90.00

_cell_volume                     928.37(8)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    2234

_cell_measurement_temperature    101.7

_cell_measurement_theta_max      29.5642

_cell_measurement_theta_min      2.9927

_exptl_absorpt_coefficient_mu    0.165

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.91046

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.783

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             512

_exptl_crystal_size_max          0.50

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.15

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0199

_diffrn_reflns_av_unetI/netI     0.0217

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_k_max       33

_diffrn_reflns_limit_k_min       -34

_diffrn_reflns_limit_l_max       8

_diffrn_reflns_limit_l_min       -8

_diffrn_reflns_number            5667

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         3.00

_diffrn_ambient_temperature      101.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.998

_diffrn_measured_fraction_theta_max 0.998

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega    6.00   40.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210   37.0000 -150.0000 34

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -49.00   -1.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210  -37.0000 -150.0000 48

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -32.00   -6.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210  110.0000 -135.0000 26

 

#__ type_ start__ end____ width___ exp.time_

  4 omega  -14.00   19.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210 -110.0000  -44.0000 33

 

#__ type_ start__ end____ width___ exp.time_

  5 omega  -29.00   -3.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.4210   37.0000 -150.0000 26

 

#__ type_ start__ end____ width___ exp.time_

  6 omega    8.00   34.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -       18.7335   37.0000 -180.0000 26

 

#__ type_ start__ end____ width___ exp.time_

  7 omega  -37.00   44.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -77.0000  150.0000 81

 

#__ type_ start__ end____ width___ exp.time_

  8 omega  -50.00   -3.00   1.0000   10.0000

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -37.0000   30.0000 47

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.0331005000

_diffrn_orient_matrix_UB_12      0.0250933000

_diffrn_orient_matrix_UB_13      -0.0041706000

_diffrn_orient_matrix_UB_21      -0.0307810000

_diffrn_orient_matrix_UB_22      -0.0015405000

_diffrn_orient_matrix_UB_23      0.0903443000

_diffrn_orient_matrix_UB_31      0.1459901000

_diffrn_orient_matrix_UB_32      0.0053729000

_diffrn_orient_matrix_UB_33      0.0454631000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1592

_reflns_number_total             1814

_reflns_odcompleteness_completeness 99.69

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.574

_refine_diff_density_min         -0.778

_refine_diff_density_rms         0.084

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.054

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     157

_refine_ls_number_reflns         1814

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0849

_refine_ls_R_factor_gt           0.0771

_refine_ls_restrained_S_all      1.054

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0466P)²+3.2850P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.1669

_refine_ls_wR_factor_ref         0.1726

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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

























C2 C 0.2352(8) 0.21026(14) 0.5799(6) 0.0405(10) Uani 1 1 d . . .
H2 H 0.1894 0.2413 0.6205 0.049 Uiso 1 1 calc R . .
O2 O 0.8775(5) 0.15854(10) 0.8901(3) 0.0347(6) Uani 1 1 d . . .
N2 N 0.4703(5) 0.13855(11) 0.5763(4) 0.0261(6) Uani 1 1 d . . .
N1 N 0.2388(6) 0.14226(11) 0.4231(4) 0.0278(7) Uani 1 1 d . . .
N3 N 0.6874(6) 0.18903(11) 0.8395(4) 0.0323(7) Uani 1 1 d . . .
O1 O 0.6760(7) 0.22727(10) 0.9229(5) 0.0571(10) Uani 1 1 d . . .
O4 O -0.1025(8) 0.07019(12) 0.4372(5) 0.0637(11) Uani 1 1 d . . .
O3 O -0.0655(6) 0.03719(11) 0.1725(4) 0.0475(8) Uani 1 1 d . . .
N4 N 0.0027(7) 0.06987(12) 0.2975(5) 0.0361(8) Uani 1 1 d . . .
O6 O 0.4927(6) 0.1450(2) 0.1493(4) 0.0888(17) Uani 1 1 d . . .
C3 C 0.0952(8) 0.18475(14) 0.4229(6) 0.0384(9) Uani 1 1 d . . .
H3 H -0.0728 0.1948 0.3298 0.046 Uiso 1 1 calc R . .
C1 C 0.4629(7) 0.17962(13) 0.6668(5) 0.0286(8) Uani 1 1 d . . .
O5 O 0.3163(6) 0.07627(18) 0.0224(4) 0.0744(14) Uani 1 1 d . . .
N5 N 0.3381(6) 0.1088(2) 0.1440(4) 0.0577(13) Uani 1 1 d . . .
C4 C 0.1865(7) 0.10624(15) 0.2848(5) 0.0311(8) Uani 1 1 d . . .
N6 N 0.7369(13) 0.05266(13) 0.7713(5) 0.0788(18) Uani 1 1 d . . .
H6A H 0.7171 0.0820 0.7116 0.095 Uiso 1 1 calc R . .
H6B H 0.8962 0.0374 0.7539 0.095 Uiso 1 1 calc R . .
H6C H 0.7559 0.0571 0.8983 0.095 Uiso 1 1 calc R . .
N7 N 0.4882(15) 0.02373(12) 0.6930(5) 0.0829(19) Uani 1 1 d . . .
H7A H 0.4898 0.0139 0.5735 0.099 Uiso 0.71(8) 1 calc PR . .
H7B H 0.3265 0.0415 0.6873 0.099 Uiso 0.29(8) 1 calc PR . .
H7C H 0.4896 -0.0027 0.7683 0.099 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

















C2 0.033(2) 0.0307(19) 0.044(2) 0.0046(17) -0.0143(17) 0.0006(15)
O2 0.0183(12) 0.0578(17) 0.0255(12) 0.0132(12) 0.0008(9) 0.0009(11)
N2 0.0133(12) 0.0387(16) 0.0240(14) 0.0083(12) 0.0008(10) -0.0037(11)
N1 0.0163(13) 0.0360(16) 0.0272(15) 0.0055(12) -0.0011(11) -0.0048(11)
N3 0.0214(14) 0.0377(17) 0.0316(16) 0.0144(14) -0.0045(12) -0.0103(13)
O1 0.066(2) 0.0269(14) 0.0542(19) 0.0006(13) -0.0277(16) -0.0095(14)
O4 0.085(2) 0.062(2) 0.068(2) -0.0451(17) 0.063(2) -0.0498(18)
O3 0.0490(17) 0.0515(18) 0.0363(15) -0.0296(13) 0.0005(12) 0.0125(14)
N4 0.0343(17) 0.0430(18) 0.0354(17) -0.0193(14) 0.0165(14) 0.0003(14)
O6 0.0247(15) 0.205(5) 0.0312(17) 0.038(2) -0.0034(12) -0.041(2)
C3 0.0235(17) 0.041(2) 0.041(2) 0.0084(17) -0.0109(15) 0.0003(15)
C1 0.0195(16) 0.0304(18) 0.0296(18) 0.0081(14) -0.0050(13) -0.0081(13)
O5 0.0329(16) 0.174(4) 0.0174(14) -0.0029(19) 0.0088(11) 0.043(2)
N5 0.0122(15) 0.141(4) 0.0183(16) 0.017(2) 0.0017(12) 0.014(2)
C4 0.0150(15) 0.057(2) 0.0226(16) -0.0019(16) 0.0077(12) 0.0005(15)
N6 0.171(5) 0.0285(19) 0.0216(17) -0.0102(15) -0.002(2) 0.036(3)
N7 0.209(6) 0.0155(16) 0.0229(18) -0.0031(14) 0.028(3) -0.003(2)



_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
























C2 H2 0.9500 . ?
C2 C3 1.360(5) . ?
C2 C1 1.398(5) . ?
O2 N3 1.226(4) . ?
N2 N1 1.358(4) . ?
N2 C1 1.314(5) . ?
N1 C3 1.360(5) . ?
N1 C4 1.388(5) . ?
N3 O1 1.224(4) . ?
N3 C1 1.450(4) . ?
O4 N4 1.243(4) . ?
O3 N4 1.260(4) . ?
N4 C4 1.355(5) . ?
O6 N5 1.239(6) . ?
C3 H3 0.9500 . ?
O5 N5 1.244(6) . ?
N5 C4 1.400(4) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 N7 1.427(7) . ?
N7 H7A 0.9100 . ?
N7 H7B 0.9100 . ?
N7 H7C 0.9100 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag





































C3 C2 H2 128.5 . . ?
C3 C2 C1 103.0(3) . . ?
C1 C2 H2 128.5 . . ?
C1 N2 N1 102.8(3) . . ?
N2 N1 C3 112.0(3) . . ?
N2 N1 C4 119.7(3) . . ?
C3 N1 C4 128.2(3) . . ?
O2 N3 C1 117.8(3) . . ?
O1 N3 O2 124.6(3) . . ?
O1 N3 C1 117.6(3) . . ?
O4 N4 O3 120.4(3) . . ?
O4 N4 C4 117.3(3) . . ?
O3 N4 C4 122.3(3) . . ?
C2 C3 N1 107.7(3) . . ?
C2 C3 H3 126.2 . . ?
N1 C3 H3 126.2 . . ?
C2 C1 N3 127.1(3) . . ?
N2 C1 C2 114.5(3) . . ?
N2 C1 N3 118.4(3) . . ?
O6 N5 O5 123.0(4) . . ?
O6 N5 C4 116.0(4) . . ?
O5 N5 C4 121.0(4) . . ?
N1 C4 N5 117.3(4) . . ?
N4 C4 N1 118.7(3) . . ?
N4 C4 N5 123.9(4) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
N7 N6 H6A 109.5 . . ?
N7 N6 H6B 109.5 . . ?
N7 N6 H6C 109.5 . . ?
N6 N7 H7A 109.5 . . ?
N6 N7 H7B 109.5 . . ?
N6 N7 H7C 109.5 . . ?
H7A N7 H7B 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?



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

























O2 N3 C1 C2 -176.9(4) . . . . ?
O2 N3 C1 N2 1.7(4) . . . . ?
N2 N1 C3 C2 0.3(4) . . . . ?
N2 N1 C4 N4 94.6(4) . . . . ?
N2 N1 C4 N5 -82.8(4) . . . . ?
N1 N2 C1 C2 0.2(4) . . . . ?
N1 N2 C1 N3 -178.6(3) . . . . ?
O1 N3 C1 C2 1.9(5) . . . . ?
O1 N3 C1 N2 -179.4(3) . . . . ?
O4 N4 C4 N1 -2.2(5) . . . . ?
O4 N4 C4 N5 175.1(4) . . . . ?
O3 N4 C4 N1 176.6(3) . . . . ?
O3 N4 C4 N5 -6.1(6) . . . . ?
O6 N5 C4 N1 -4.4(5) . . . . ?
O6 N5 C4 N4 178.4(4) . . . . ?
C3 C2 C1 N2 0.0(5) . . . . ?
C3 C2 C1 N3 178.6(3) . . . . ?
C3 N1 C4 N4 -90.1(5) . . . . ?
C3 N1 C4 N5 92.5(4) . . . . ?
C1 C2 C3 N1 -0.1(4) . . . . ?
C1 N2 N1 C3 -0.3(4) . . . . ?
C1 N2 N1 C4 175.7(3) . . . . ?
O5 N5 C4 N1 175.5(3) . . . . ?
O5 N5 C4 N4 -1.8(6) . . . . ?
C4 N1 C3 C2 -175.3(3) . . . . ?






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

data_exp_2330
_database_code_depnum_ccdc_archive 'CCDC 1442350'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2014-09-02

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C2 N7 O6, H5 N2'

_chemical_formula_sum            'C2 H5 N9 O6'

_chemical_formula_weight         251.15

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      orthorhombic

_space_group_IT_number           61

_space_group_name_H-M_alt        'P b c a'

_space_group_name_Hall           '-P 2ac 2ab'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz








1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'



_cell_length_a                   6.43139(19)

_cell_length_b                   16.4647(4)

_cell_length_c                   16.8638(5)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1785.73(9)

_cell_formula_units_Z            8

_cell_measurement_reflns_used    1989

_cell_measurement_temperature    99.4

_cell_measurement_theta_max      29.3812

_cell_measurement_theta_min      3.1611

_exptl_absorpt_coefficient_mu    0.178

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.89710

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.868

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       orthorhombic

_exptl_crystal_F_000             1024

_exptl_crystal_size_max          0.15

_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.08

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0244

_diffrn_reflns_av_unetI/netI     0.0294

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_k_max       20

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_l_max       14

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_number            4817

_diffrn_reflns_theta_full        25.99

_diffrn_reflns_theta_max         25.99

_diffrn_reflns_theta_min         3.46

_diffrn_ambient_temperature      99.4

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.998

_diffrn_measured_fraction_theta_max 0.998

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega   22.00   58.00   1.0000    4.5600

omega____ theta____ kappa____ phi______ frames

    -       18.5772 -165.0000  -40.0000 36

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -31.00   38.00   1.0000    4.5600

omega____ theta____ kappa____ phi______ frames

    -       18.5772  -77.0000  150.0000 69

 

#__ type_ start__ end____ width___ exp.time_

  3 omega    1.00   49.00   1.0000    4.5600

omega____ theta____ kappa____ phi______ frames

    -       18.5772    0.0000   30.0000 48

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.0500708000

_diffrn_orient_matrix_UB_12      -0.0082999000

_diffrn_orient_matrix_UB_13      0.0365800000

_diffrn_orient_matrix_UB_21      0.0701355000

_diffrn_orient_matrix_UB_22      0.0264404000

_diffrn_orient_matrix_UB_23      0.0196605000

_diffrn_orient_matrix_UB_31      -0.0688540000

_diffrn_orient_matrix_UB_32      0.0329859000

_diffrn_orient_matrix_UB_33      -0.0066150000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1534

_reflns_number_total             1743

_reflns_odcompleteness_completeness 99.67

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.204

_refine_diff_density_min         -0.244

_refine_diff_density_rms         0.052

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.034

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     155

_refine_ls_number_reflns         1743

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0400

_refine_ls_R_factor_gt           0.0333

_refine_ls_restrained_S_all      1.034

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.9539P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0772

_refine_ls_wR_factor_ref         0.0808

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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






















O4 O 0.03189(18) 0.96077(6) 0.39345(7) 0.0164(3) Uani 1 1 d . . .
O6 O 0.31145(17) 0.95736(7) 0.50788(7) 0.0176(3) Uani 1 1 d . . .
O2 O -0.49402(19) 0.82830(7) 0.72934(7) 0.0219(3) Uani 1 1 d . . .
O3 O -0.22713(18) 0.87606(7) 0.40750(7) 0.0189(3) Uani 1 1 d . . .
O5 O 0.23793(18) 0.87520(7) 0.60495(7) 0.0199(3) Uani 1 1 d . . .
O1 O -0.4346(2) 0.69795(7) 0.72883(8) 0.0288(3) Uani 1 1 d . . .
N2 N -0.0710(2) 0.74411(8) 0.54320(8) 0.0157(3) Uani 1 1 d . . .
N6 N -0.0613(2) 0.90736(8) 0.43200(8) 0.0137(3) Uani 1 1 d . . .
N3 N -0.1051(2) 0.82494(8) 0.54670(8) 0.0131(3) Uani 1 1 d . . .
N1 N -0.1833(2) 0.71217(8) 0.59995(8) 0.0161(3) Uani 1 1 d . . .
N5 N -0.4136(2) 0.76702(8) 0.70266(8) 0.0173(3) Uani 1 1 d . . .
N4 N -0.2359(2) 0.84729(8) 0.60414(8) 0.0138(3) Uani 1 1 d . . .
N7 N 0.1966(2) 0.90603(8) 0.53930(8) 0.0142(3) Uani 1 1 d . . .
N8 N 0.4584(2) 0.99020(8) 0.34853(8) 0.0164(3) Uani 1 1 d . . .
H8A H 0.5036 1.0413 0.3468 0.020 Uiso 1 1 calc R . .
H8B H 0.5650 0.9571 0.3578 0.020 Uiso 1 1 calc R . .
H8C H 0.3650 0.9851 0.3872 0.020 Uiso 1 1 calc R . .
C1 C -0.2784(2) 0.77595(9) 0.63434(9) 0.0140(3) Uani 1 1 d . . .
N9 N 0.3637(2) 0.96939(9) 0.27366(8) 0.0195(3) Uani 1 1 d . . .
H9A H 0.4533 0.9790 0.2346 0.023 Uiso 1 1 d R . .
H9B H 0.3296 0.9170 0.2738 0.023 Uiso 1 1 d R . .
C2 C 0.0138(2) 0.88035(9) 0.50332(9) 0.0136(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

















O4 0.0174(6) 0.0170(5) 0.0148(6) 0.0045(5) 0.0022(5) -0.0014(5)
O6 0.0159(6) 0.0214(6) 0.0156(6) 0.0008(5) 0.0021(5) -0.0072(5)
O2 0.0201(7) 0.0290(6) 0.0167(6) 0.0005(5) 0.0028(5) 0.0048(6)
O3 0.0153(6) 0.0219(6) 0.0195(6) 0.0000(5) -0.0047(5) -0.0046(5)
O5 0.0207(6) 0.0252(6) 0.0138(6) 0.0050(5) -0.0041(5) -0.0022(5)
O1 0.0355(8) 0.0236(6) 0.0274(7) 0.0082(6) 0.0086(6) -0.0082(6)
N2 0.0164(7) 0.0143(6) 0.0165(7) 0.0000(6) -0.0011(6) -0.0008(6)
N6 0.0129(7) 0.0141(6) 0.0141(7) -0.0018(6) 0.0005(6) 0.0012(6)
N3 0.0133(7) 0.0133(6) 0.0128(6) -0.0004(6) 0.0007(6) -0.0006(6)
N1 0.0167(7) 0.0168(7) 0.0148(7) 0.0008(6) -0.0015(6) -0.0025(6)
N5 0.0151(7) 0.0224(7) 0.0144(7) 0.0021(6) -0.0009(6) -0.0035(6)
N4 0.0126(7) 0.0170(6) 0.0118(6) -0.0001(6) 0.0009(6) -0.0007(6)
N7 0.0144(7) 0.0156(6) 0.0127(7) -0.0009(6) 0.0009(6) 0.0002(6)
N8 0.0156(7) 0.0186(7) 0.0151(7) -0.0009(6) 0.0006(6) 0.0009(6)
C1 0.0129(8) 0.0169(7) 0.0120(7) 0.0002(7) -0.0023(7) -0.0024(7)
N9 0.0193(8) 0.0264(7) 0.0126(7) -0.0039(6) -0.0012(6) -0.0016(7)
C2 0.0136(8) 0.0151(7) 0.0120(8) 0.0022(7) 0.0016(7) -0.0015(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





















O4 N6 1.2472(16) . ?
O6 N7 1.2413(17) . ?
O2 N5 1.2197(17) . ?
O3 N6 1.2544(17) . ?
O5 N7 1.2466(17) . ?
O1 N5 1.2274(18) . ?
N2 N3 1.3502(17) . ?
N2 N1 1.3093(19) . ?
N6 C2 1.370(2) . ?
N3 N4 1.3347(18) . ?
N3 C2 1.397(2) . ?
N1 C1 1.347(2) . ?
N5 C1 1.451(2) . ?
N4 C1 1.309(2) . ?
N7 C2 1.389(2) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N8 N9 1.4431(19) . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8901 . ?



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 N2 N3 105.91(13) . . ?
O4 N6 O3 121.77(13) . . ?
O4 N6 C2 121.13(13) . . ?
O3 N6 C2 117.09(13) . . ?
N2 N3 C2 122.12(13) . . ?
N4 N3 N2 113.95(13) . . ?
N4 N3 C2 123.03(13) . . ?
N2 N1 C1 104.61(13) . . ?
O2 N5 O1 125.96(14) . . ?
O2 N5 C1 117.59(13) . . ?
O1 N5 C1 116.44(14) . . ?
C1 N4 N3 99.59(13) . . ?
O6 N7 O5 121.96(13) . . ?
O6 N7 C2 121.63(13) . . ?
O5 N7 C2 116.40(13) . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
N9 N8 H8A 109.5 . . ?
N9 N8 H8B 109.5 . . ?
N9 N8 H8C 109.5 . . ?
N1 C1 N5 122.36(14) . . ?
N4 C1 N1 115.93(14) . . ?
N4 C1 N5 121.67(14) . . ?
N8 N9 H9A 109.5 . . ?
N8 N9 H9B 109.4 . . ?
H9A N9 H9B 109.5 . . ?
N6 C2 N3 118.59(14) . . ?
N6 C2 N7 125.67(14) . . ?
N7 C2 N3 115.67(14) . . ?



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

























O4 N6 C2 N3 175.22(13) . . . . ?
O4 N6 C2 N7 -1.6(2) . . . . ?
O6 N7 C2 N6 -0.5(2) . . . . ?
O6 N7 C2 N3 -177.38(13) . . . . ?
O2 N5 C1 N1 -179.49(14) . . . . ?
O2 N5 C1 N4 3.0(2) . . . . ?
O3 N6 C2 N3 -4.7(2) . . . . ?
O3 N6 C2 N7 178.42(14) . . . . ?
O5 N7 C2 N6 179.04(14) . . . . ?
O5 N7 C2 N3 2.1(2) . . . . ?
O1 N5 C1 N1 1.2(2) . . . . ?
O1 N5 C1 N4 -176.30(15) . . . . ?
N2 N3 N4 C1 -0.23(16) . . . . ?
N2 N3 C2 N6 96.51(18) . . . . ?
N2 N3 C2 N7 -86.34(18) . . . . ?
N2 N1 C1 N5 -177.78(13) . . . . ?
N2 N1 C1 N4 -0.10(19) . . . . ?
N3 N2 N1 C1 -0.05(16) . . . . ?
N3 N4 C1 N1 0.20(18) . . . . ?
N3 N4 C1 N5 177.90(13) . . . . ?
N1 N2 N3 N4 0.19(17) . . . . ?
N1 N2 N3 C2 169.61(14) . . . . ?
N4 N3 C2 N6 -95.03(18) . . . . ?
N4 N3 C2 N7 82.13(18) . . . . ?
C2 N3 N4 C1 -169.55(14) . . . . ?






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

data_exp_2303
_database_code_depnum_ccdc_archive 'CCDC 1442351'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2014-06-25

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C2 N7 O6, H4 N'

_chemical_formula_sum            'C2 H4 N8 O6'

_chemical_formula_weight         236.13

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   8.0847(3)

_cell_length_b                   7.5557(3)

_cell_length_c                   14.1232(6)

_cell_angle_alpha                90.00

_cell_angle_beta                 99.661(4)

_cell_angle_gamma                90.00

_cell_volume                     850.49(6)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1480

_cell_measurement_temperature    98.7

_cell_measurement_theta_max      29.4594

_cell_measurement_theta_min      2.9202

_exptl_absorpt_coefficient_mu    0.177

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.99506

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.844

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             480

_exptl_crystal_size_max          0.15

_exptl_crystal_size_mid          0.14

_exptl_crystal_size_min          0.12

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0192

_diffrn_reflns_av_unetI/netI     0.0303

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_number            3503

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         2.93

_diffrn_ambient_temperature      98.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.999

_diffrn_measured_fraction_theta_max 0.999

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega   53.00   80.00   1.0000    3.3100

omega____ theta____ kappa____ phi______ frames

    -       18.7335   37.0000 -120.0000 27

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -49.00   36.00   1.0000    3.3100

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -37.0000 -120.0000 85

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -30.00   13.00   1.0000    3.3100

omega____ theta____ kappa____ phi______ frames

    -       18.7335  -77.0000 -180.0000 43

 

#__ type_ start__ end____ width___ exp.time_

  4 omega   13.00   74.00   1.0000    3.3100

omega____ theta____ kappa____ phi______ frames

    -       18.7335   37.0000   30.0000 61

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.0203227000

_diffrn_orient_matrix_UB_12      -0.0488765000

_diffrn_orient_matrix_UB_13      0.0393466000

_diffrn_orient_matrix_UB_21      0.0521410000

_diffrn_orient_matrix_UB_22      0.0564357000

_diffrn_orient_matrix_UB_23      0.0322964000

_diffrn_orient_matrix_UB_31      -0.0692140000

_diffrn_orient_matrix_UB_32      0.0569020000

_diffrn_orient_matrix_UB_33      0.0018193000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1430

_reflns_number_total             1669

_reflns_odcompleteness_completeness 99.73

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.215

_refine_diff_density_min         -0.327

_refine_diff_density_rms         0.055

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.070

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     145

_refine_ls_number_reflns         1669

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0393

_refine_ls_R_factor_gt           0.0319

_refine_ls_restrained_S_all      1.070

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0333P)²+0.2399P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0744

_refine_ls_wR_factor_ref         0.0786

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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




















O4 O 0.33713(13) 0.22034(14) 0.48717(8) 0.0175(3) Uani 1 1 d . . .
O5 O 0.35914(14) -0.25181(14) 0.62942(8) 0.0205(3) Uani 1 1 d . . .
O6 O 0.46137(13) 0.01573(14) 0.63447(7) 0.0165(3) Uani 1 1 d . . .
O2 O 0.22785(15) -0.58259(14) 0.26472(9) 0.0236(3) Uani 1 1 d . . .
N5 N 0.10070(17) -0.56074(17) 0.30026(9) 0.0163(3) Uani 1 1 d . . .
O1 O -0.03020(14) -0.64330(15) 0.28089(8) 0.0209(3) Uani 1 1 d . . .
N3 N 0.17783(16) -0.21432(16) 0.46005(9) 0.0143(3) Uani 1 1 d . . .
O3 O 0.17609(14) 0.08174(15) 0.37185(8) 0.0217(3) Uani 1 1 d . . .
N6 N 0.26179(16) 0.08578(16) 0.45298(9) 0.0146(3) Uani 1 1 d . . .
N1 N -0.03267(16) -0.37335(16) 0.40633(9) 0.0156(3) Uani 1 1 d . . .
N7 N 0.36605(16) -0.10193(16) 0.59276(9) 0.0146(3) Uani 1 1 d . . .
N2 N 0.01473(16) -0.23918(17) 0.46321(9) 0.0165(3) Uani 1 1 d . . .
N4 N 0.23995(16) -0.32746(16) 0.40177(9) 0.0145(3) Uani 1 1 d . . .
C1 C 0.10516(19) -0.42133(19) 0.37132(11) 0.0129(3) Uani 1 1 d . . .
C2 C 0.26761(19) -0.0712(2) 0.50585(11) 0.0147(3) Uani 1 1 d . . .
N8 N 0.59279(16) -0.38743(16) 0.32676(9) 0.0167(3) Uani 1 1 d . . .
H8A H 0.5623 -0.3953 0.2634 0.020 Uiso 1 1 d R . .
H8B H 0.5701 -0.2796 0.3462 0.020 Uiso 1 1 d R . .
H8C H 0.7024 -0.4082 0.3423 0.020 Uiso 1 1 d R . .
H8D H 0.5366 -0.4672 0.3552 0.020 Uiso 1 1 d 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
















O4 0.0204(6) 0.0128(6) 0.0191(6) -0.0020(5) 0.0031(5) -0.0026(5)
O5 0.0256(6) 0.0140(6) 0.0220(6) 0.0064(5) 0.0042(5) -0.0006(5)
O6 0.0168(6) 0.0162(6) 0.0155(6) -0.0037(5) -0.0002(4) -0.0017(5)
O2 0.0276(7) 0.0206(6) 0.0258(7) -0.0047(5) 0.0138(5) -0.0029(5)
N5 0.0204(7) 0.0137(7) 0.0145(7) 0.0014(5) 0.0018(5) 0.0005(6)
O1 0.0199(6) 0.0191(6) 0.0210(6) -0.0031(5) -0.0045(5) -0.0030(5)
N3 0.0131(7) 0.0131(6) 0.0171(7) -0.0019(5) 0.0035(5) -0.0002(5)
O3 0.0239(6) 0.0228(6) 0.0156(6) 0.0008(5) -0.0051(5) 0.0006(5)
N6 0.0133(7) 0.0152(7) 0.0153(7) -0.0013(5) 0.0027(5) 0.0014(6)
N1 0.0162(7) 0.0140(6) 0.0163(7) -0.0007(5) 0.0019(5) -0.0008(5)
N7 0.0156(7) 0.0143(7) 0.0147(7) -0.0012(5) 0.0044(5) 0.0002(6)
N2 0.0130(7) 0.0165(7) 0.0200(7) -0.0013(6) 0.0025(5) -0.0013(6)
N4 0.0166(7) 0.0120(6) 0.0149(7) -0.0001(5) 0.0029(5) 0.0019(5)
C1 0.0151(8) 0.0105(7) 0.0129(8) 0.0017(6) 0.0017(6) -0.0004(6)
C2 0.0148(8) 0.0133(7) 0.0152(8) -0.0024(6) 0.0008(6) -0.0010(6)
N8 0.0174(7) 0.0150(7) 0.0169(7) -0.0014(5) 0.0005(5) -0.0007(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



















O4 N6 1.2406(16) . ?
O5 N7 1.2503(16) . ?
O6 N7 1.2565(16) . ?
O2 N5 1.2284(17) . ?
N5 O1 1.2193(17) . ?
N5 C1 1.451(2) . ?
N3 N2 1.3400(17) . ?
N3 N4 1.3414(18) . ?
N3 C2 1.3991(19) . ?
O3 N6 1.2359(17) . ?
N6 C2 1.398(2) . ?
N1 N2 1.3101(17) . ?
N1 C1 1.343(2) . ?
N7 C2 1.366(2) . ?
N4 C1 1.3108(19) . ?
N8 H8A 0.8895 . ?
N8 H8B 0.8887 . ?
N8 H8C 0.8902 . ?
N8 H8D 0.8903 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag



























O2 N5 C1 117.05(13) . . ?
O1 N5 O2 126.43(13) . . ?
O1 N5 C1 116.51(13) . . ?
N2 N3 N4 113.76(12) . . ?
N2 N3 C2 122.01(12) . . ?
N4 N3 C2 123.90(13) . . ?
O4 N6 C2 121.13(12) . . ?
O3 N6 O4 122.91(13) . . ?
O3 N6 C2 115.95(12) . . ?
N2 N1 C1 105.03(12) . . ?
O5 N7 O6 120.87(12) . . ?
O5 N7 C2 117.80(12) . . ?
O6 N7 C2 121.32(12) . . ?
N1 N2 N3 106.04(12) . . ?
C1 N4 N3 99.78(12) . . ?
N1 C1 N5 121.66(13) . . ?
N4 C1 N5 122.85(14) . . ?
N4 C1 N1 115.39(13) . . ?
N6 C2 N3 116.14(13) . . ?
N7 C2 N3 117.55(13) . . ?
N7 C2 N6 125.92(13) . . ?
H8A N8 H8B 109.6 . . ?
H8A N8 H8C 109.4 . . ?
H8A N8 H8D 109.4 . . ?
H8B N8 H8C 109.5 . . ?
H8B N8 H8D 109.5 . . ?
H8C N8 H8D 109.4 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag

























O4 N6 C2 N3 179.96(13) . . . . ?
O4 N6 C2 N7 -7.4(2) . . . . ?
O5 N7 C2 N3 -5.7(2) . . . . ?
O5 N7 C2 N6 -178.26(13) . . . . ?
O6 N7 C2 N3 173.84(12) . . . . ?
O6 N7 C2 N6 1.3(2) . . . . ?
O2 N5 C1 N1 172.29(13) . . . . ?
O2 N5 C1 N4 -3.9(2) . . . . ?
O1 N5 C1 N1 -6.8(2) . . . . ?
O1 N5 C1 N4 177.03(13) . . . . ?
N3 N4 C1 N5 176.58(13) . . . . ?
N3 N4 C1 N1 0.21(16) . . . . ?
O3 N6 C2 N3 0.9(2) . . . . ?
O3 N6 C2 N7 173.52(14) . . . . ?
N2 N3 N4 C1 -0.50(16) . . . . ?
N2 N3 C2 N6 -86.84(17) . . . . ?
N2 N3 C2 N7 99.89(17) . . . . ?
N2 N1 C1 N5 -176.28(13) . . . . ?
N2 N1 C1 N4 0.14(17) . . . . ?
N4 N3 N2 N1 0.61(16) . . . . ?
N4 N3 C2 N6 86.13(17) . . . . ?
N4 N3 C2 N7 -87.14(18) . . . . ?
C1 N1 N2 N3 -0.43(15) . . . . ?
C2 N3 N2 N1 174.23(13) . . . . ?
C2 N3 N4 C1 -173.98(13) . . . . ?







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

data_exp_3286
_database_code_depnum_ccdc_archive 'CCDC 1442352'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2015-06-03

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C4 H2 N5 O6, H4 N'

_chemical_formula_sum            'C4 H6 N6 O6'

_chemical_formula_weight         234.15

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   4.9037(3)

_cell_length_b                   25.6452(14)

_cell_length_c                   7.3737(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 106.189(6)

_cell_angle_gamma                90.00

_cell_volume                     890.53(9)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1006

_cell_measurement_temperature    101.7

_cell_measurement_theta_max      29.3693

_cell_measurement_theta_min      2.9784

_exptl_absorpt_coefficient_mu    0.163

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.97918

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.746

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             480

_exptl_crystal_size_max          0.22

_exptl_crystal_size_mid          0.14

_exptl_crystal_size_min          0.05

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0335

_diffrn_reflns_av_unetI/netI     0.0495

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_k_max       31

_diffrn_reflns_limit_k_min       -22

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_limit_l_min       -6

_diffrn_reflns_number            4027

_diffrn_reflns_theta_full        25.99

_diffrn_reflns_theta_max         25.99

_diffrn_reflns_theta_min         2.98

_diffrn_ambient_temperature      101.7

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.999

_diffrn_measured_fraction_theta_max 0.999

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega   -4.00   84.00   1.0000    6.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772   77.0000 -120.0000 88

 

#__ type_ start__ end____ width___ exp.time_

  2 omega    3.00   30.00   1.0000    6.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772   77.0000   30.0000 27

 

#__ type_ start__ end____ width___ exp.time_

  3 omega   -6.00   83.00   1.0000    6.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772   77.0000  120.0000 89

 

#__ type_ start__ end____ width___ exp.time_

  4 omega   -8.00   18.00   1.0000    6.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772   77.0000    0.0000 26

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      -0.0483677000

_diffrn_orient_matrix_UB_12      0.0261735000

_diffrn_orient_matrix_UB_13      -0.0132092000

_diffrn_orient_matrix_UB_21      0.1001348000

_diffrn_orient_matrix_UB_22      0.0053157000

_diffrn_orient_matrix_UB_23      -0.0508943000

_diffrn_orient_matrix_UB_31      -0.1015835000

_diffrn_orient_matrix_UB_32      -0.0072152000

_diffrn_orient_matrix_UB_33      -0.0852349000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1377

_reflns_number_total             1732

_reflns_odcompleteness_completeness 99.73

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.235

_refine_diff_density_min         -0.259

_refine_diff_density_rms         0.055

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.085

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     145

_refine_ls_number_reflns         1732

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0542

_refine_ls_R_factor_gt           0.0397

_refine_ls_restrained_S_all      1.085

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.1607P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0807

_refine_ls_wR_factor_ref         0.0884

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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






















O4 O 0.3515(3) 0.52274(5) 0.71443(17) 0.0164(3) Uani 1 1 d . . .
O5 O 0.7182(3) 0.57275(5) 0.58095(19) 0.0199(3) Uani 1 1 d . . .
O6 O 0.8567(3) 0.64737(6) 0.71534(19) 0.0229(4) Uani 1 1 d . . .
O2 O 1.0369(3) 0.72815(6) 1.47877(19) 0.0235(4) Uani 1 1 d . . .
O3 O 0.2680(3) 0.55634(6) 0.96587(18) 0.0199(3) Uani 1 1 d . . .
N5 N 0.7223(3) 0.60618(7) 0.7033(2) 0.0161(4) Uani 1 1 d . . .
N4 N 0.3948(3) 0.55841(6) 0.8402(2) 0.0144(4) Uani 1 1 d . . .
N3 N 1.0512(3) 0.68692(7) 1.3980(2) 0.0171(4) Uani 1 1 d . . .
N6 N 0.1522(3) 0.53940(6) 0.3116(2) 0.0152(4) Uani 1 1 d . . .
H6A H 0.0999 0.5716 0.2601 0.018 Uiso 1 1 d R . .
H6B H -0.0025 0.5179 0.2842 0.018 Uiso 1 1 d R . .
H6C H 0.2229 0.5425 0.4396 0.018 Uiso 1 1 d R . .
H6D H 0.2883 0.5257 0.2624 0.018 Uiso 1 1 d R . .
O1 O 1.2407(3) 0.65448(6) 1.45133(19) 0.0236(4) Uani 1 1 d . . .
N2 N 0.8441(3) 0.63318(6) 1.1329(2) 0.0157(4) Uani 1 1 d . . .
N1 N 0.6110(3) 0.63650(6) 0.9815(2) 0.0154(4) Uani 1 1 d . . .
C4 C 0.5705(4) 0.59895(8) 0.8393(3) 0.0142(4) Uani 1 1 d . . .
C3 C 0.4596(4) 0.68099(8) 0.9835(3) 0.0177(5) Uani 1 1 d . . .
H3 H 0.2942 0.6910 0.8933 0.021 Uiso 1 1 calc R . .
C1 C 0.8281(4) 0.67656(8) 1.2259(3) 0.0155(4) Uani 1 1 d . . .
C2 C 0.5951(4) 0.70812(8) 1.1418(3) 0.0183(5) Uani 1 1 d . . .
H2 H 0.5446 0.7399 1.1838 0.022 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
















O4 0.0189(7) 0.0149(7) 0.0146(7) -0.0037(6) 0.0033(6) -0.0008(6)
O5 0.0216(8) 0.0227(8) 0.0171(7) -0.0026(6) 0.0081(6) 0.0001(6)
O6 0.0217(8) 0.0238(9) 0.0221(8) 0.0025(6) 0.0041(6) -0.0104(7)
O2 0.0274(8) 0.0185(8) 0.0227(8) -0.0061(6) 0.0039(6) -0.0048(7)
O3 0.0225(8) 0.0237(8) 0.0168(7) 0.0009(6) 0.0110(6) -0.0002(6)
N5 0.0124(8) 0.0196(10) 0.0143(9) 0.0007(7) 0.0005(6) -0.0002(7)
N4 0.0134(8) 0.0163(9) 0.0126(8) 0.0012(7) 0.0023(6) 0.0018(7)
N3 0.0165(9) 0.0184(10) 0.0163(9) 0.0000(7) 0.0045(7) -0.0037(8)
N6 0.0163(8) 0.0157(9) 0.0133(8) 0.0010(7) 0.0037(6) -0.0004(7)
O1 0.0177(8) 0.0274(9) 0.0226(8) 0.0010(7) 0.0004(6) 0.0067(7)
N2 0.0141(8) 0.0185(9) 0.0130(8) 0.0002(7) 0.0014(6) -0.0001(7)
N1 0.0151(8) 0.0148(9) 0.0141(8) -0.0007(7) 0.0006(6) 0.0013(7)
C4 0.0148(9) 0.0133(11) 0.0140(10) -0.0010(8) 0.0032(7) -0.0014(8)
C3 0.0151(10) 0.0163(11) 0.0195(11) 0.0023(9) 0.0015(8) 0.0023(9)
C1 0.0140(10) 0.0171(11) 0.0151(10) -0.0013(8) 0.0037(8) -0.0023(8)
C2 0.0169(10) 0.0154(11) 0.0223(11) -0.0029(9) 0.0050(8) 0.0009(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





















O4 N4 1.2778(19) . ?
O5 N5 1.241(2) . ?
O6 N5 1.235(2) . ?
O2 N3 1.225(2) . ?
O3 N4 1.252(2) . ?
N5 C4 1.418(2) . ?
N4 C4 1.351(2) . ?
N3 O1 1.227(2) . ?
N3 C1 1.450(2) . ?
N6 H6A 0.9139 . ?
N6 H6B 0.9139 . ?
N6 H6C 0.9138 . ?
N6 H6D 0.9135 . ?
N2 N1 1.360(2) . ?
N2 C1 1.320(2) . ?
N1 C4 1.397(2) . ?
N1 C3 1.364(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.363(3) . ?
C1 C2 1.396(3) . ?
C2 H2 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































O5 N5 C4 121.23(16) . . ?
O6 N5 O5 122.90(17) . . ?
O6 N5 C4 115.86(16) . . ?
O4 N4 C4 121.60(16) . . ?
O3 N4 O4 119.36(16) . . ?
O3 N4 C4 119.03(16) . . ?
O2 N3 O1 124.74(16) . . ?
O2 N3 C1 116.87(16) . . ?
O1 N3 C1 118.39(16) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6A N6 H6D 109.5 . . ?
H6B N6 H6C 109.4 . . ?
H6B N6 H6D 109.5 . . ?
H6C N6 H6D 109.5 . . ?
C1 N2 N1 102.44(15) . . ?
N2 N1 C4 118.98(16) . . ?
N2 N1 C3 112.29(15) . . ?
C3 N1 C4 128.40(16) . . ?
N4 C4 N5 124.46(17) . . ?
N4 C4 N1 118.94(17) . . ?
N1 C4 N5 116.60(17) . . ?
N1 C3 H3 126.3 . . ?
C2 C3 N1 107.43(17) . . ?
C2 C3 H3 126.3 . . ?
N2 C1 N3 117.97(17) . . ?
N2 C1 C2 114.69(17) . . ?
C2 C1 N3 127.33(18) . . ?
C3 C2 C1 103.14(17) . . ?
C3 C2 H2 128.4 . . ?
C1 C2 H2 128.4 . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag

























O4 N4 C4 N5 -0.2(3) . . . . ?
O4 N4 C4 N1 -179.48(15) . . . . ?
O5 N5 C4 N4 -5.3(3) . . . . ?
O5 N5 C4 N1 174.03(16) . . . . ?
O6 N5 C4 N4 174.79(16) . . . . ?
O6 N5 C4 N1 -5.9(2) . . . . ?
O2 N3 C1 N2 177.78(17) . . . . ?
O2 N3 C1 C2 -0.7(3) . . . . ?
O3 N4 C4 N5 -178.97(16) . . . . ?
O3 N4 C4 N1 1.7(3) . . . . ?
N3 C1 C2 C3 178.45(18) . . . . ?
O1 N3 C1 N2 -1.6(3) . . . . ?
O1 N3 C1 C2 179.93(18) . . . . ?
N2 N1 C4 N5 -81.5(2) . . . . ?
N2 N1 C4 N4 97.8(2) . . . . ?
N2 N1 C3 C2 -0.3(2) . . . . ?
N2 C1 C2 C3 -0.1(2) . . . . ?
N1 N2 C1 N3 -178.79(16) . . . . ?
N1 N2 C1 C2 -0.1(2) . . . . ?
N1 C3 C2 C1 0.3(2) . . . . ?
C4 N1 C3 C2 -173.48(19) . . . . ?
C3 N1 C4 N5 91.2(2) . . . . ?
C3 N1 C4 N4 -89.4(2) . . . . ?
C1 N2 N1 C4 174.11(17) . . . . ?
C1 N2 N1 C3 0.3(2) . . . . ?






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

data_exp_3195
_database_code_depnum_ccdc_archive 'CCDC 1442353'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_date             2015-05-19

_audit_creation_method           
;

  Olex2 1.1

  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;

_chemical_name_common            ?

_chemical_name_systematic        
;

 ? 

;

_chemical_formula_moiety         'C4 H2 N5 O6, C H6 N3'

_chemical_formula_sum            'C5 H8 N8 O6'

_chemical_formula_weight         276.19

_chemical_melting_point          ?

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source




C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_space_group_crystal_system      monoclinic

_space_group_IT_number           14

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_id

_space_group_symop_operation_xyz




1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'



_cell_length_a                   8.1268(5)

_cell_length_b                   9.3064(4)

_cell_length_c                   14.0786(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 92.296(7)

_cell_angle_gamma                90.00

_cell_volume                     1063.92(10)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1626

_cell_measurement_temperature    101.8

_cell_measurement_theta_max      29.5510

_cell_measurement_theta_min      2.9388

_exptl_absorpt_coefficient_mu    0.156

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_correction_T_min  0.76710

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.

;

_exptl_crystal_colour            ?

_exptl_crystal_density_diffrn    1.724

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_description       monoclinic

_exptl_crystal_F_000             568

_exptl_crystal_size_max          0.34

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.15

_exptl_special_details           
;

 ? 

;

_diffrn_reflns_av_R_equivalents  0.0344

_diffrn_reflns_av_unetI/netI     0.0462

_diffrn_reflns_limit_h_max       9

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_number            4871

_diffrn_reflns_theta_full        26.00

_diffrn_reflns_theta_max         26.00

_diffrn_reflns_theta_min         3.33

_diffrn_ambient_temperature      101.8

_diffrn_detector_area_resol_mean 16.0971

_diffrn_measured_fraction_theta_full 0.999

_diffrn_measured_fraction_theta_max 0.999

_diffrn_measurement_details      
;

#__ type_ start__ end____ width___ exp.time_

  1 omega  -72.00  -45.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.2647  -37.0000 -180.0000 27

 

#__ type_ start__ end____ width___ exp.time_

  2 omega  -27.00    5.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.2647  -37.0000   90.0000 32

 

#__ type_ start__ end____ width___ exp.time_

  3 omega  -76.00  -50.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -      -13.2647  -48.0000  -80.0000 26

 

#__ type_ start__ end____ width___ exp.time_

  4 omega  -49.00   36.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772  -37.0000 -150.0000 85

 

#__ type_ start__ end____ width___ exp.time_

  5 omega   -8.00   66.00   1.0000    5.0000

omega____ theta____ kappa____ phi______ frames

    -       18.5772   77.0000    0.0000 74

;

_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'

_diffrn_measurement_method       'ω scans'

_diffrn_orient_matrix_UB_11      0.0388281000

_diffrn_orient_matrix_UB_12      0.0448982000

_diffrn_orient_matrix_UB_13      0.0348803000

_diffrn_orient_matrix_UB_21      -0.0750045000

_diffrn_orient_matrix_UB_22      0.0051752000

_diffrn_orient_matrix_UB_23      0.0238220000

_diffrn_orient_matrix_UB_31      0.0221487000

_diffrn_orient_matrix_UB_32      -0.0613049000

_diffrn_orient_matrix_UB_33      0.0275780000

_diffrn_radiation_monochromator  graphite

_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.7107

_diffrn_source                   'Enhance (Mo) X-ray Source'

_diffrn_standards_decay_%        ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_number         ?

_reflns_number_gt                1713

_reflns_number_total             2082

_reflns_odcompleteness_completeness 99.74

_reflns_odcompleteness_iscentric 1

_reflns_odcompleteness_theta     26.32

_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)

(compiled May 16 2011,17:55:39)

;

_computing_molecular_graphics    
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_publication_material  
;

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,

OLEX2: a complete structure solution, refinement and analysis program.

J. Appl. Cryst. (2009). 42, 339-341.

;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'

_refine_diff_density_max         0.215

_refine_diff_density_min         -0.287

_refine_diff_density_rms         0.055

_refine_ls_extinction_coef       ?

_refine_ls_extinction_method     none

_refine_ls_goodness_of_fit_ref   1.087

_refine_ls_hydrogen_treatment    mixed

_refine_ls_matrix_type           full

_refine_ls_number_parameters     172

_refine_ls_number_reflns         2082

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0512

_refine_ls_R_factor_gt           0.0403

_refine_ls_restrained_S_all      1.087

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_ls_structure_factor_coef Fsqd

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.3014P] where P=(Fo²+2Fc²)/3'

_refine_ls_weighting_scheme      calc

_refine_ls_wR_factor_gt          0.0943

_refine_ls_wR_factor_ref         0.1023

_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. 

;

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

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



























O3 O 0.75671(17) 0.08075(14) 0.57743(9) 0.0248(3) Uani 1 1 d . . .
O4 O 0.59609(17) 0.12683(14) 0.45390(9) 0.0237(3) Uani 1 1 d . . .
O2 O 0.94612(16) -0.14298(14) 0.56333(9) 0.0231(3) Uani 1 1 d . . .
N4 N 0.70041(18) 0.04955(16) 0.49670(10) 0.0175(4) Uani 1 1 d . . .
N3 N 0.87654(18) -0.16056(16) 0.48301(10) 0.0177(4) Uani 1 1 d . . .
O6 O 0.64013(18) -0.11593(15) 0.04906(9) 0.0285(4) Uani 1 1 d . . .
C3 C 0.5512(2) -0.1973(2) 0.23546(13) 0.0186(4) Uani 1 1 d . . .
H3 H 0.4816 -0.2545 0.1949 0.022 Uiso 1 1 calc R . .
O5 O 0.77399(19) 0.06885(15) 0.10589(10) 0.0351(4) Uani 1 1 d . . .
O1 O 0.92016(16) -0.26190(13) 0.42951(9) 0.0216(3) Uani 1 1 d . . .
N2 N 0.74404(18) -0.02911(16) 0.28309(10) 0.0173(4) Uani 1 1 d . . .
N1 N 0.68366(18) -0.09954(15) 0.35895(10) 0.0157(3) Uani 1 1 d . . .
N5 N 0.69440(19) -0.04184(16) 0.11518(11) 0.0197(4) Uani 1 1 d . . .
C2 C 0.5677(2) -0.19963(19) 0.33280(13) 0.0182(4) Uani 1 1 d . . .
H2 H 0.5092 -0.2597 0.3743 0.022 Uiso 1 1 calc R . .
C1 C 0.7509(2) -0.07374(18) 0.44998(12) 0.0159(4) Uani 1 1 d . . .
C4 C 0.6620(2) -0.09007(19) 0.21063(12) 0.0160(4) Uani 1 1 d . . .
N6 N 0.87496(19) 0.20711(16) 0.75858(11) 0.0197(4) Uani 1 1 d . . .
H6A H 0.8765 0.2059 0.6961 0.024 Uiso 1 1 calc R . .
H6B H 0.8823 0.2893 0.7894 0.024 Uiso 1 1 calc R . .
N8 N 0.85032(19) -0.03928(16) 0.76056(11) 0.0200(4) Uani 1 1 d . . .
H8A H 0.8518 -0.0413 0.6981 0.024 Uiso 1 1 calc R . .
H8B H 0.8414 -0.1198 0.7927 0.024 Uiso 1 1 calc R . .
N7 N 0.8571(2) 0.08673(18) 0.90027(11) 0.0281(4) Uani 1 1 d . . .
H7A H 0.8632 0.1689 0.9312 0.034 Uiso 1 1 calc R . .
H7B H 0.8482 0.0056 0.9318 0.034 Uiso 1 1 calc R . .
C5 C 0.8615(2) 0.08515(19) 0.80623(13) 0.0176(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



















O3 0.0309(8) 0.0270(7) 0.0159(7) -0.0062(6) -0.0067(6) 0.0052(6)
O4 0.0265(7) 0.0228(7) 0.0214(7) 0.0016(6) -0.0044(6) 0.0083(6)
O2 0.0241(7) 0.0298(7) 0.0149(7) -0.0019(6) -0.0063(6) 0.0060(6)
N4 0.0177(8) 0.0186(8) 0.0160(8) 0.0015(6) -0.0001(6) -0.0008(7)
N3 0.0185(8) 0.0198(8) 0.0148(8) 0.0004(6) 0.0013(6) -0.0006(7)
O6 0.0376(8) 0.0324(8) 0.0154(7) -0.0057(6) -0.0017(6) -0.0067(7)
C3 0.0154(9) 0.0213(9) 0.0190(9) -0.0044(8) -0.0012(7) -0.0009(8)
O5 0.0507(10) 0.0343(8) 0.0204(8) 0.0013(6) 0.0031(7) -0.0205(8)
O1 0.0232(7) 0.0210(7) 0.0206(7) -0.0051(6) 0.0015(6) 0.0043(6)
N2 0.0174(8) 0.0199(8) 0.0149(8) 0.0008(6) 0.0020(6) -0.0011(7)
N1 0.0153(7) 0.0183(7) 0.0136(8) 0.0010(6) -0.0005(6) -0.0020(6)
N5 0.0190(8) 0.0243(8) 0.0156(8) -0.0011(7) -0.0001(6) 0.0004(7)
C2 0.0173(9) 0.0173(9) 0.0201(9) 0.0002(8) 0.0016(8) -0.0010(8)
C1 0.0162(9) 0.0169(9) 0.0145(9) -0.0007(7) -0.0004(7) 0.0010(7)
C4 0.0160(9) 0.0185(9) 0.0135(9) -0.0015(7) 0.0003(7) 0.0029(8)
N6 0.0253(9) 0.0167(8) 0.0170(8) -0.0008(6) -0.0010(7) -0.0027(7)
N8 0.0279(9) 0.0159(7) 0.0161(8) 0.0012(6) -0.0002(7) -0.0028(7)
N7 0.0460(11) 0.0223(8) 0.0162(8) -0.0011(7) 0.0022(8) -0.0041(8)
C5 0.0134(9) 0.0216(9) 0.0179(9) -0.0004(8) -0.0006(7) -0.0009(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


























O3 N4 1.2425(18) . ?
O4 N4 1.2482(19) . ?
O2 N3 1.2545(18) . ?
N4 C1 1.392(2) . ?
N3 O1 1.2664(18) . ?
N3 C1 1.369(2) . ?
O6 N5 1.2262(19) . ?
C3 H3 0.9500 . ?
C3 C2 1.372(3) . ?
C3 C4 1.398(3) . ?
O5 N5 1.226(2) . ?
N2 N1 1.361(2) . ?
N2 C4 1.324(2) . ?
N1 C2 1.365(2) . ?
N1 C1 1.394(2) . ?
N5 C4 1.451(2) . ?
C2 H2 0.9500 . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C5 1.325(2) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C5 1.326(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C5 1.326(2) . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag





































O3 N4 O4 121.67(15) . . ?
O3 N4 C1 121.34(15) . . ?
O4 N4 C1 116.99(15) . . ?
O2 N3 O1 120.43(14) . . ?
O2 N3 C1 122.16(15) . . ?
O1 N3 C1 117.41(14) . . ?
C2 C3 H3 128.6 . . ?
C2 C3 C4 102.87(16) . . ?
C4 C3 H3 128.6 . . ?
C4 N2 N1 102.24(14) . . ?
N2 N1 C2 112.56(14) . . ?
N2 N1 C1 119.88(14) . . ?
C2 N1 C1 127.32(15) . . ?
O6 N5 C4 117.13(15) . . ?
O5 N5 O6 124.52(16) . . ?
O5 N5 C4 118.34(15) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 C3 107.31(16) . . ?
N1 C2 H2 126.3 . . ?
N4 C1 N1 117.67(15) . . ?
N3 C1 N4 123.76(15) . . ?
N3 C1 N1 118.05(15) . . ?
C3 C4 N5 126.51(16) . . ?
N2 C4 C3 115.02(16) . . ?
N2 C4 N5 118.47(15) . . ?
H6A N6 H6B 120.0 . . ?
C5 N6 H6A 120.0 . . ?
C5 N6 H6B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C5 N7 H7A 120.0 . . ?
C5 N7 H7B 120.0 . . ?
N6 C5 N8 120.53(16) . . ?
N6 C5 N7 120.14(17) . . ?
N8 C5 N7 119.33(17) . . ?



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

























O3 N4 C1 N3 -7.4(3) . . . . ?
O3 N4 C1 N1 -178.95(15) . . . . ?
O4 N4 C1 N3 172.70(16) . . . . ?
O4 N4 C1 N1 1.2(2) . . . . ?
O2 N3 C1 N4 7.1(3) . . . . ?
O2 N3 C1 N1 178.55(15) . . . . ?
O6 N5 C4 C3 -12.3(3) . . . . ?
O6 N5 C4 N2 167.33(16) . . . . ?
O5 N5 C4 C3 167.97(18) . . . . ?
O5 N5 C4 N2 -12.4(2) . . . . ?
O1 N3 C1 N4 -173.65(15) . . . . ?
O1 N3 C1 N1 -2.2(2) . . . . ?
N2 N1 C2 C3 0.8(2) . . . . ?
N2 N1 C1 N4 79.8(2) . . . . ?
N2 N1 C1 N3 -92.16(19) . . . . ?
N1 N2 C4 C3 -0.2(2) . . . . ?
N1 N2 C4 N5 -179.88(14) . . . . ?
C2 C3 C4 N2 0.6(2) . . . . ?
C2 C3 C4 N5 -179.71(17) . . . . ?
C2 N1 C1 N4 -106.1(2) . . . . ?
C2 N1 C1 N3 81.9(2) . . . . ?
C1 N1 C2 C3 -173.70(16) . . . . ?
C4 C3 C2 N1 -0.78(19) . . . . ?
C4 N2 N1 C2 -0.35(19) . . . . ?
C4 N2 N1 C1 174.57(15) . . . . ?






####################################################################### 
# 
# 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 1442398'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
; 

 ? 

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'H4 N O, C3 H N6 O6'

_chemical_formula_sum            'C3 H5 N7 O7'

_chemical_formula_weight         251.14



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'



_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                   6.4054(9)

_cell_length_b                   15.829(2)

_cell_length_c                   8.9085(10)

_cell_angle_alpha                90.00

_cell_angle_beta                 99.085(4)

_cell_angle_gamma                90.00

_cell_volume                     891.9(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    1430

_cell_measurement_theta_min      3.22

_cell_measurement_theta_max      25.03



_exptl_crystal_description       block

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.22

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.870

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             512

_exptl_absorpt_coefficient_mu    0.180

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7018

_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            5074

_diffrn_reflns_av_R_equivalents  0.0472

_diffrn_reflns_av_sigmaI/netI    0.0731

_diffrn_reflns_limit_h_min       -4

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -19

_diffrn_reflns_limit_k_max       17

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       10

_diffrn_reflns_theta_min         3.22

_diffrn_reflns_theta_max         25.39

_reflns_number_total             1601

_reflns_number_gt                1049

_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)+(0.0212P)²+0.5753P] 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         1601

_refine_ls_number_parameters     166

_refine_ls_number_restraints     10

_refine_ls_R_factor_all          0.0941

_refine_ls_R_factor_gt           0.0458

_refine_ls_wR_factor_ref         0.0787

_refine_ls_wR_factor_gt          0.0680

_refine_ls_goodness_of_fit_ref   1.030

_refine_ls_restrained_S_all      1.030

_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 0.1689(4) 0.77223(17) 0.4172(3) 0.0137(6) Uani 1 1 d . . .
C2 C 0.4202(4) 0.77429(16) 0.5919(3) 0.0150(6) Uani 1 1 d . . .
H2 H 0.5229 0.7902 0.6761 0.018 Uiso 1 1 calc R . .
C3 C 0.5369(4) 0.62716(16) 0.5633(3) 0.0136(6) Uani 1 1 d . . .
N1 N 0.4150(3) 0.69878(13) 0.5215(2) 0.0135(5) Uani 1 1 d . . .
N2 N 0.2465(3) 0.69660(13) 0.4046(2) 0.0153(5) Uani 1 1 d . . .
N3 N 0.2642(3) 0.82306(13) 0.5286(2) 0.0165(6) Uani 1 1 d . . .
N4 N 0.7074(3) 0.61071(14) 0.4899(2) 0.0167(5) Uani 1 1 d . . .
N5 N 0.4711(3) 0.57331(14) 0.6669(2) 0.0168(5) Uani 1 1 d . . .
N6 N -0.0172(3) 0.79976(14) 0.3131(2) 0.0174(5) Uani 1 1 d . . .
N7 N -0.0126(4) 0.44064(14) 0.8002(3) 0.0218(6) Uani 1 1 d D . .
H7A H -0.084(3) 0.4096(12) 0.859(2) 0.033 Uiso 1 1 d D . .
H7B H 0.036(4) 0.4067(12) 0.732(2) 0.033 Uiso 1 1 d D . .
H7C H -0.087(3) 0.4814(12) 0.754(2) 0.033 Uiso 1 1 d D . .
O1 O 0.8283(3) 0.55065(11) 0.5257(2) 0.0248(5) Uani 1 1 d . . .
O2 O 0.7349(3) 0.66047(12) 0.3845(2) 0.0215(5) Uani 1 1 d . . .
O3 O 0.5635(3) 0.50603(11) 0.70675(19) 0.0218(5) Uani 1 1 d . . .
O4 O 0.3068(3) 0.59495(11) 0.7190(2) 0.0238(5) Uani 1 1 d . . .
O5 O -0.0646(3) 0.76077(11) 0.1937(2) 0.0206(5) Uani 1 1 d . . .
O6 O -0.1129(3) 0.85991(12) 0.3537(2) 0.0311(5) Uani 1 1 d . . .
O7 O 0.1652(3) 0.47329(13) 0.8946(2) 0.0354(6) Uani 1 1 d D . .
H7D H 0.218(5) 0.5098(16) 0.842(3) 0.042 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 0.0150(15) 0.0134(15) 0.0132(15) 0.0017(12) 0.0039(12) 0.0013(12)
C2 0.0169(16) 0.0159(16) 0.0117(14) -0.0023(13) 0.0008(12) -0.0022(13)
C3 0.0129(15) 0.0146(16) 0.0137(15) 0.0020(12) 0.0032(12) 0.0024(12)
N1 0.0118(12) 0.0158(13) 0.0119(12) -0.0013(10) -0.0016(10) 0.0020(10)
N2 0.0145(13) 0.0173(13) 0.0132(12) 0.0004(10) -0.0008(10) 0.0014(11)
N3 0.0185(13) 0.0148(13) 0.0158(12) -0.0028(10) 0.0018(11) 0.0021(11)
N4 0.0155(14) 0.0199(13) 0.0137(13) -0.0005(11) -0.0003(10) 0.0006(11)
N5 0.0144(14) 0.0189(13) 0.0161(13) -0.0035(11) -0.0003(10) 0.0009(11)
N6 0.0164(14) 0.0164(13) 0.0195(14) 0.0020(12) 0.0028(11) 0.0018(11)
N7 0.0208(14) 0.0180(14) 0.0262(14) 0.0040(12) 0.0025(12) 0.0006(12)
O1 0.0220(12) 0.0230(12) 0.0295(11) 0.0030(9) 0.0047(9) 0.0129(10)
O2 0.0208(12) 0.0277(12) 0.0168(11) 0.0080(9) 0.0053(9) 0.0009(9)
O3 0.0208(12) 0.0149(11) 0.0282(11) 0.0061(9) -0.0006(9) 0.0036(9)
O4 0.0236(12) 0.0240(12) 0.0267(11) 0.0018(9) 0.0130(9) 0.0019(9)
O5 0.0232(12) 0.0231(11) 0.0141(10) -0.0034(9) -0.0009(9) 0.0004(9)
O6 0.0303(13) 0.0265(12) 0.0340(13) -0.0067(10) -0.0026(10) 0.0163(11)
O7 0.0330(14) 0.0418(15) 0.0299(13) 0.0080(11) 0.0004(10) -0.0176(11)



_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 N2 1.308(3) . ?
C1 N3 1.346(3) . ?
C1 N6 1.457(3) . ?
C2 N3 1.317(3) . ?
C2 N1 1.348(3) . ?
C2 H2 0.9500 . ?
C3 N5 1.371(3) . ?
C3 N4 1.383(3) . ?
C3 N1 1.394(3) . ?
N1 N2 1.377(3) . ?
N4 O1 1.236(3) . ?
N4 O2 1.259(3) . ?
N5 O3 1.243(2) . ?
N5 O4 1.263(3) . ?
N6 O6 1.218(3) . ?
N6 O5 1.225(3) . ?
N7 O7 1.403(3) . ?
N7 H7A 0.892(15) . ?
N7 H7B 0.904(15) . ?
N7 H7C 0.867(15) . ?
O7 H7D 0.845(17) . ?



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






























N2 C1 N3 118.4(2) . . ?
N2 C1 N6 120.2(2) . . ?
N3 C1 N6 121.4(2) . . ?
N3 C2 N1 111.0(2) . . ?
N3 C2 H2 124.5 . . ?
N1 C2 H2 124.5 . . ?
N5 C3 N4 123.4(2) . . ?
N5 C3 N1 117.8(2) . . ?
N4 C3 N1 118.5(2) . . ?
C2 N1 N2 109.5(2) . . ?
C2 N1 C3 128.7(2) . . ?
N2 N1 C3 121.4(2) . . ?
C1 N2 N1 100.1(2) . . ?
C2 N3 C1 101.0(2) . . ?
O1 N4 O2 121.2(2) . . ?
O1 N4 C3 122.2(2) . . ?
O2 N4 C3 116.7(2) . . ?
O3 N5 O4 121.0(2) . . ?
O3 N5 C3 122.8(2) . . ?
O4 N5 C3 116.2(2) . . ?
O6 N6 O5 125.8(2) . . ?
O6 N6 C1 116.3(2) . . ?
O5 N6 C1 117.9(2) . . ?
O7 N7 H7A 107.2(14) . . ?
O7 N7 H7B 106.9(15) . . ?
H7A N7 H7B 109.2(17) . . ?
O7 N7 H7C 110.2(15) . . ?
H7A N7 H7C 112.8(19) . . ?
H7B N7 H7C 110.3(17) . . ?
N7 O7 H7D 106(2) . . ?



_diffrn_measured_fraction_theta_max 0.976

_diffrn_reflns_theta_full        25.39

_diffrn_measured_fraction_theta_full 0.976

_refine_diff_density_max         0.235

_refine_diff_density_min         -0.273

_refine_diff_density_rms         0.063




