# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014


data_xb6888_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N10 O3'
_chemical_formula_weight         272.26

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   5.1633(11)
_cell_length_b                   9.5569(19)
_cell_length_c                   12.229(3)
_cell_angle_alpha                87.326(3)
_cell_angle_beta                 83.816(3)
_cell_angle_gamma                76.459(3)
_cell_volume                     583.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    904
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      24.12

_exptl_crystal_description       colourless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2879
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2014
_reflns_number_gt                1529
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1600P)²+0.3285P] 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         2014
_refine_ls_number_parameters     187
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2373
_refine_ls_wR_factor_gt          0.2099
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4377(6) 0.3196(3) 0.4735(2) 0.0386(7) Uani 1 1 d U . .
N4 N 0.6736(6) 0.2921(4) 0.3175(3) 0.0499(9) Uani 1 1 d . . .
N2 N 0.4719(7) 0.4118(3) 0.3151(3) 0.0536(9) Uani 1 1 d . . .
N3 N 0.6442(8) 0.2363(4) 0.4172(3) 0.0636(10) Uani 1 1 d U . .
N7 N 0.3319(5) 0.3600(3) -0.0198(2) 0.0359(7) Uani 1 1 d . . .
N9 N 0.7154(5) 0.1618(3) -0.0229(2) 0.0347(7) Uani 1 1 d . . .
N6 N 0.3670(5) 0.1812(3) 0.1188(2) 0.0348(7) Uani 1 1 d . . .
H5 H 0.3000 0.1466 0.1786 0.042 Uiso 1 1 calc R . .
C4 C 0.6090(6) 0.1128(4) 0.0707(3) 0.0321(8) Uani 1 1 d . . .
C6 C 0.5699(7) 0.2856(3) -0.0639(3) 0.0326(8) Uani 1 1 d . . .
C5 C 0.2296(6) 0.3048(3) 0.0724(3) 0.0325(8) Uani 1 1 d . . .
C3 C 0.3309(7) 0.4282(3) 0.4078(3) 0.0400(9) Uani 1 1 d U . .
H8 H 0.1817 0.5020 0.4262 0.048 Uiso 1 1 calc R . .
C2 C 0.3216(9) 0.3015(4) 0.5856(3) 0.0464(10) Uani 1 1 d D . .
C1 C 0.1774(7) 0.1797(4) 0.5985(3) 0.0353(8) Uani 1 1 d . . .
O2 O 0.1852(6) 0.1035(3) 0.5196(2) 0.0508(8) Uani 1 1 d . . .
O3 O 0.0640(5) 0.1664(3) 0.69331(19) 0.0468(7) Uani 1 1 d . . .
O1 O 0.2652(6) 0.0256(3) 0.3024(2) 0.0500(8) Uani 1 1 d . . .
N8 N 0.6754(6) 0.3370(3) -0.1566(2) 0.0442(8) Uani 1 1 d . . .
H1 H 0.5911 0.4157 -0.1861 0.053 Uiso 1 1 calc R . .
H2 H 0.8281 0.2918 -0.1870 0.053 Uiso 1 1 calc R . .
N5 N 0.7372(6) -0.0046(3) 0.1196(2) 0.0426(8) Uani 1 1 d . . .
H4 H 0.8914 -0.0505 0.0909 0.051 Uiso 1 1 calc R . .
H3 H 0.6668 -0.0355 0.1801 0.051 Uiso 1 1 calc R . .
N10 N -0.0007(6) 0.3686(3) 0.1217(2) 0.0422(8) Uani 1 1 d . . .
H7 H -0.0900 0.4478 0.0948 0.051 Uiso 1 1 calc R . .
H6 H -0.0639 0.3315 0.1811 0.051 Uiso 1 1 calc R . .
H10 H 0.251(8) 0.055(4) 0.376(4) 0.051 Uiso 1 1 d . . .
H12 H 0.461(8) 0.277(4) 0.628(3) 0.048(11) Uiso 1 1 d . . .
H11 H 0.140(11) -0.026(5) 0.317(4) 0.070(14) Uiso 1 1 d . . .
H9 H 0.191(8) 0.382(4) 0.603(4) 0.073(15) 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
N1 0.0415(16) 0.0382(15) 0.0338(15) 0.0059(12) 0.0063(12) -0.0102(13)
N4 0.0512(19) 0.0535(19) 0.0396(18) 0.0149(15) 0.0076(14) -0.0097(16)
N2 0.060(2) 0.0488(19) 0.0440(19) 0.0197(15) 0.0008(16) -0.0042(16)
N3 0.058(2) 0.070(2) 0.056(2) 0.0130(18) 0.0093(17) -0.0107(18)
N7 0.0357(16) 0.0348(15) 0.0307(15) 0.0046(12) 0.0056(12) -0.0004(12)
N9 0.0371(16) 0.0341(15) 0.0284(14) 0.0065(12) 0.0016(12) -0.0026(12)
N6 0.0370(16) 0.0357(15) 0.0268(14) 0.0089(12) 0.0030(12) -0.0031(12)
C4 0.0316(17) 0.0390(17) 0.0246(16) 0.0007(13) 0.0006(13) -0.0076(14)
C6 0.0343(17) 0.0334(17) 0.0261(16) 0.0030(13) 0.0016(13) -0.0026(13)
C5 0.0337(17) 0.0315(16) 0.0290(16) 0.0012(13) 0.0022(13) -0.0036(13)
C3 0.0417(19) 0.0303(17) 0.0366(19) 0.0127(14) 0.0091(15) 0.0060(14)
C2 0.060(3) 0.048(2) 0.0284(19) 0.0030(17) 0.0094(18) -0.014(2)
C1 0.0348(18) 0.0379(17) 0.0280(17) 0.0057(14) 0.0023(13) -0.0021(14)
O2 0.0645(18) 0.0563(16) 0.0362(14) -0.0036(12) 0.0049(12) -0.0273(14)
O3 0.0522(16) 0.0501(15) 0.0318(13) 0.0080(11) 0.0142(11) -0.0091(12)
O1 0.0559(17) 0.0615(17) 0.0331(14) 0.0070(12) 0.0070(12) -0.0214(14)
N8 0.0445(17) 0.0377(16) 0.0368(16) 0.0122(13) 0.0142(13) 0.0072(13)
N5 0.0413(16) 0.0442(16) 0.0326(15) 0.0132(13) 0.0049(12) 0.0029(13)
N10 0.0384(16) 0.0425(17) 0.0371(16) 0.0081(13) 0.0096(13) 0.0004(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
N1 N3 1.319(5) . ?
N1 C3 1.333(4) . ?
N1 C2 1.455(4) . ?
N4 N3 1.316(5) . ?
N4 N2 1.356(5) . ?
N2 C3 1.274(5) . ?
N7 C5 1.332(4) . ?
N7 C6 1.338(4) . ?
N9 C4 1.330(4) . ?
N9 C6 1.351(4) . ?
N6 C4 1.353(4) . ?
N6 C5 1.362(4) . ?
N6 H5 0.8600 . ?
C4 N5 1.315(4) . ?
C6 N8 1.328(4) . ?
C5 N10 1.300(4) . ?
C3 H8 0.9300 . ?
C2 C1 1.516(5) . ?
C2 H12 0.91(4) . ?
C2 H9 0.914(19) . ?
C1 O2 1.228(4) . ?
C1 O3 1.256(4) . ?
O1 H10 0.95(4) . ?
O1 H11 0.90(5) . ?
N8 H1 0.8600 . ?
N8 H2 0.8600 . ?
N5 H4 0.8600 . ?
N5 H3 0.8600 . ?
N10 H7 0.8600 . ?
N10 H6 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N1 C3 108.4(3) . . ?
N3 N1 C2 129.5(3) . . ?
C3 N1 C2 122.1(3) . . ?
N3 N4 N2 105.2(3) . . ?
C3 N2 N4 110.6(3) . . ?
N4 N3 N1 108.8(3) . . ?
C5 N7 C6 116.3(3) . . ?
C4 N9 C6 115.5(3) . . ?
C4 N6 C5 119.9(3) . . ?
C4 N6 H5 120.1 . . ?
C5 N6 H5 120.1 . . ?
N5 C4 N9 120.6(3) . . ?
N5 C4 N6 117.8(3) . . ?
N9 C4 N6 121.5(3) . . ?
N8 C6 N7 117.7(3) . . ?
N8 C6 N9 116.2(3) . . ?
N7 C6 N9 126.1(3) . . ?
N10 C5 N7 121.2(3) . . ?
N10 C5 N6 118.2(3) . . ?
N7 C5 N6 120.6(3) . . ?
N2 C3 N1 107.1(3) . . ?
N2 C3 H8 126.5 . . ?
N1 C3 H8 126.5 . . ?
N1 C2 C1 113.0(3) . . ?
N1 C2 H12 106(3) . . ?
C1 C2 H12 107(3) . . ?
N1 C2 H9 108(3) . . ?
C1 C2 H9 104(3) . . ?
H12 C2 H9 118(4) . . ?
O2 C1 O3 126.6(3) . . ?
O2 C1 C2 119.2(3) . . ?
O3 C1 C2 114.2(3) . . ?
H10 O1 H11 93(4) . . ?
C6 N8 H1 120.0 . . ?
C6 N8 H2 120.0 . . ?
H1 N8 H2 120.0 . . ?
C4 N5 H4 120.0 . . ?
C4 N5 H3 120.0 . . ?
H4 N5 H3 120.0 . . ?
C5 N10 H7 120.0 . . ?
C5 N10 H6 120.0 . . ?
H7 N10 H6 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 969657'

data_xb6910_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 N10 O4'
_chemical_formula_weight         260.20

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   3.6377(10)
_cell_length_b                   11.723(3)
_cell_length_c                   12.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.696(5)
_cell_angle_gamma                90.00
_cell_volume                     523.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    365
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2832
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         26.64
_reflns_number_total             1085
_reflns_number_gt                690
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.2995P] 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         1085
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1819
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
N2 N 0.1567(8) 0.8707(3) 0.2268(3) 0.0398(8) Uani 1 1 d . . .
N4 N -0.0262(9) 0.8439(3) 0.3809(3) 0.0455(8) Uani 1 1 d . . .
N3 N -0.0392(8) 0.7432(2) 0.3260(2) 0.0377(8) Uani 1 1 d . . .
H1 H -0.1094 0.6789 0.3499 0.045 Uiso 1 1 calc R . .
N5 N 0.0889(9) 0.9209(3) 0.3217(3) 0.0456(8) Uani 1 1 d . . .
N1 N 0.1103(10) 0.6832(3) 0.1535(3) 0.0494(9) Uani 1 1 d . . .
H2 H 0.0578 0.6128 0.1639 0.059 Uiso 1 1 calc R . .
H3 H 0.1864 0.7036 0.0936 0.059 Uiso 1 1 calc R . .
C2 C 0.0738(9) 0.7599(3) 0.2296(3) 0.0335(8) Uani 1 1 d . . .
O2 O 0.7046(7) 0.55597(19) 0.39212(19) 0.0400(7) Uani 1 1 d . . .
O1 O 0.5030(7) 0.64443(19) 0.53212(19) 0.0396(7) Uani 1 1 d . . .
C1 C 0.5573(9) 0.5593(3) 0.4803(3) 0.0299(8) Uani 1 1 d . . .
H4 H 0.184(17) 0.913(5) 0.153(4) 0.113(19) 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
N2 0.0429(18) 0.0388(17) 0.0393(17) 0.0099(13) 0.0117(14) -0.0030(14)
N4 0.057(2) 0.0356(17) 0.0472(19) 0.0059(13) 0.0185(16) -0.0032(14)
N3 0.0440(17) 0.0294(15) 0.0423(17) 0.0085(13) 0.0154(14) -0.0032(13)
N5 0.0501(19) 0.0399(17) 0.0488(19) 0.0065(14) 0.0142(16) -0.0043(14)
N1 0.069(2) 0.0406(19) 0.043(2) 0.0057(14) 0.0220(17) -0.0004(16)
C2 0.0312(17) 0.0354(19) 0.0348(18) 0.0090(14) 0.0072(15) 0.0000(14)
O2 0.0559(16) 0.0319(13) 0.0376(14) -0.0002(10) 0.0262(12) -0.0031(11)
O1 0.0517(16) 0.0311(13) 0.0394(14) -0.0036(10) 0.0191(12) -0.0017(11)
C1 0.0291(17) 0.0296(18) 0.0322(17) 0.0011(14) 0.0081(15) -0.0010(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
N2 C2 1.335(4) . ?
N2 N5 1.366(4) . ?
N2 H4 1.06(6) . ?
N4 N5 1.269(4) . ?
N4 N3 1.360(4) . ?
N3 C2 1.329(4) . ?
N3 H1 0.8600 . ?
N1 C2 1.322(5) . ?
N1 H2 0.8600 . ?
N1 H3 0.8600 . ?
O2 C1 1.280(4) . ?
O1 C1 1.217(4) . ?
C1 C1 1.548(6) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 N5 109.2(3) . . ?
C2 N2 H4 122(3) . . ?
N5 N2 H4 126(3) . . ?
N5 N4 N3 108.7(3) . . ?
C2 N3 N4 109.1(3) . . ?
C2 N3 H1 125.4 . . ?
N4 N3 H1 125.4 . . ?
N4 N5 N2 107.6(3) . . ?
C2 N1 H2 120.0 . . ?
C2 N1 H3 120.0 . . ?
H2 N1 H3 120.0 . . ?
N1 C2 N3 127.8(3) . . ?
N1 C2 N2 126.8(3) . . ?
N3 C2 N2 105.4(3) . . ?
O1 C1 O2 126.2(3) . . ?
O1 C1 C1 120.0(3) . 3_666 ?
O2 C1 C1 113.8(3) . 3_666 ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        26.64
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 969658'

data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H7 N7 O6'
_chemical_formula_weight         225.15

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                   13.559(3)
_cell_length_b                   8.9163(17)
_cell_length_c                   6.7232(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.051(4)
_cell_angle_gamma                90.00
_cell_volume                     811.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1129
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      23.4

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4292
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         26.31
_reflns_number_total             1635
_reflns_number_gt                1129
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)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     SHELXL
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1635
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46489(12) 1.00656(17) 0.7176(3) 0.0493(5) Uani 1 1 d . . .
O2 O 0.32927(11) 0.95625(19) 0.5520(3) 0.0553(5) Uani 1 1 d . . .
O3 O 0.42200(11) 0.77767(17) 0.6727(2) 0.0511(5) Uani 1 1 d . . .
N1 N 0.40600(12) 0.91311(19) 0.6458(3) 0.0350(5) Uani 1 1 d . . .
O4 O 0.02644(12) -0.04432(17) 0.2819(3) 0.0568(6) Uani 1 1 d . . .
O5 O 0.03362(12) 0.19355(17) 0.2648(3) 0.0642(6) Uani 1 1 d . . .
O6 O 0.15582(11) 0.07088(17) 0.3978(3) 0.0491(5) Uani 1 1 d . . .
N2 N 0.07062(12) 0.07520(18) 0.3149(3) 0.0344(5) Uani 1 1 d . . .
N3 N 0.21894(13) 0.3511(2) 0.4456(3) 0.0355(5) Uani 1 1 d . . .
H3 H 0.1967(16) 0.264(3) 0.433(3) 0.049(8) Uiso 1 1 d . . .
N4 N 0.15954(13) 0.47367(19) 0.3958(3) 0.0340(5) Uani 1 1 d . . .
H4 H 0.0968(18) 0.458(3) 0.339(3) 0.057(8) Uiso 1 1 d . . .
N5 N 0.29656(13) 0.5532(2) 0.5361(3) 0.0295(5) Uani 1 1 d . . .
H5 H 0.338(2) 0.614(3) 0.584(4) 0.062(9) Uiso 1 1 d . . .
N6 N 0.37453(14) 0.3206(3) 0.6126(3) 0.0416(5) Uani 1 1 d . . .
H6A H 0.3734(17) 0.230(3) 0.598(3) 0.042(7) Uiso 1 1 d . . .
H6B H 0.431(2) 0.364(3) 0.672(4) 0.080(9) Uiso 1 1 d . . .
N7 N 0.17820(16) 0.7348(2) 0.4245(3) 0.0410(5) Uani 1 1 d . . .
H7A H 0.1112(18) 0.756(3) 0.365(3) 0.052(7) Uiso 1 1 d . . .
H7B H 0.2168(19) 0.805(3) 0.461(4) 0.058(9) Uiso 1 1 d . . .
C1 C 0.30132(14) 0.4015(2) 0.5353(3) 0.0288(5) Uani 1 1 d . . .
C2 C 0.20821(15) 0.5959(2) 0.4496(3) 0.0289(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
O1 0.0414(10) 0.0354(9) 0.0697(12) -0.0079(8) -0.0096(8) -0.0088(7)
O2 0.0341(10) 0.0506(11) 0.0790(13) 0.0085(9) -0.0182(9) 0.0056(8)
O3 0.0473(10) 0.0267(9) 0.0766(13) 0.0015(8) -0.0223(9) -0.0009(7)
N1 0.0261(10) 0.0339(11) 0.0447(11) -0.0020(8) -0.0003(8) 0.0013(8)
O4 0.0372(10) 0.0261(9) 0.1037(15) 0.0023(9) -0.0288(9) -0.0075(7)
O5 0.0474(11) 0.0260(9) 0.1152(16) 0.0094(9) -0.0328(11) 0.0052(8)
O6 0.0288(9) 0.0299(9) 0.0856(13) 0.0016(8) -0.0232(8) -0.0012(6)
N2 0.0271(10) 0.0234(10) 0.0517(12) 0.0014(8) -0.0084(8) -0.0018(7)
N3 0.0287(10) 0.0237(10) 0.0530(12) -0.0026(9) -0.0090(8) -0.0044(8)
N4 0.0248(10) 0.0273(10) 0.0487(12) -0.0013(8) -0.0102(9) 0.0002(7)
N5 0.0259(9) 0.0253(10) 0.0365(10) -0.0004(7) -0.0069(8) -0.0059(7)
N6 0.0316(11) 0.0344(13) 0.0574(13) 0.0049(10) -0.0102(10) 0.0053(9)
N7 0.0384(12) 0.0300(11) 0.0536(13) 0.0028(9) -0.0058(10) 0.0045(9)
C1 0.0249(10) 0.0271(11) 0.0339(11) -0.0001(9) -0.0024(9) -0.0035(8)
C2 0.0268(11) 0.0296(12) 0.0302(11) 0.0014(9) -0.0008(9) 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
O1 N1 1.234(2) . ?
O2 N1 1.248(2) . ?
O3 N1 1.239(2) . ?
O4 N2 1.237(2) . ?
O5 N2 1.209(2) . ?
O6 N2 1.256(2) . ?
N3 C1 1.320(3) . ?
N3 N4 1.388(3) . ?
N3 H3 0.84(2) . ?
N4 C2 1.314(3) . ?
N4 H4 0.92(2) . ?
N5 C1 1.355(3) . ?
N5 C2 1.358(3) . ?
N5 H5 0.83(3) . ?
N6 C1 1.312(3) . ?
N6 H6A 0.82(3) . ?
N6 H6B 0.93(3) . ?
N7 C2 1.312(3) . ?
N7 H7A 0.99(2) . ?
N7 H7B 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O3 119.77(18) . . ?
O1 N1 O2 119.60(18) . . ?
O3 N1 O2 120.60(18) . . ?
O5 N2 O4 120.83(17) . . ?
O5 N2 O6 120.57(17) . . ?
O4 N2 O6 118.58(17) . . ?
C1 N3 N4 107.95(17) . . ?
C1 N3 H3 130.9(15) . . ?
N4 N3 H3 120.3(15) . . ?
C2 N4 N3 108.06(17) . . ?
C2 N4 H4 132.3(15) . . ?
N3 N4 H4 119.6(15) . . ?
C1 N5 C2 108.62(17) . . ?
C1 N5 H5 128.5(19) . . ?
C2 N5 H5 122.8(19) . . ?
C1 N6 H6A 119.3(17) . . ?
C1 N6 H6B 121.8(17) . . ?
H6A N6 H6B 119(2) . . ?
C2 N7 H7A 120.1(14) . . ?
C2 N7 H7B 118.5(18) . . ?
H7A N7 H7B 121(2) . . ?
N6 C1 N3 126.7(2) . . ?
N6 C1 N5 125.66(19) . . ?
N3 C1 N5 107.61(17) . . ?
N7 C2 N4 126.8(2) . . ?
N7 C2 N5 125.4(2) . . ?
N4 C2 N5 107.70(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O6 0.84(2) 1.82(2) 2.655(2) 176(2) .
N3 H3 O5 0.84(2) 2.51(2) 3.072(2) 125.7(19) .
N4 H4 O4 0.92(2) 1.82(2) 2.737(2) 172(2) 2
N4 H4 O5 0.92(2) 2.55(2) 3.126(2) 120.6(18) .
N5 H5 O3 0.83(3) 1.93(3) 2.752(2) 171(3) .
N6 H6A O1 0.82(3) 2.46(3) 3.122(3) 139(2) 1_545
N6 H6A O2 0.82(3) 2.53(3) 3.327(3) 167(2) 1_545
N6 H6B O1 0.93(3) 2.01(3) 2.920(3) 166(2) 2_646
N6 H6B O3 0.93(3) 2.34(3) 3.069(2) 136(2) 2_646
N7 H7A O4 0.99(2) 2.18(2) 2.970(2) 135.9(19) 1_565
N7 H7A O5 0.99(2) 2.18(2) 3.101(3) 154.4(19) 2
N7 H7B O2 0.84(3) 2.10(3) 2.940(3) 172(3) .
N7 H7B O6 0.84(3) 2.54(3) 3.016(3) 117(2) 1_565

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.31
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 976693'
