# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

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

data_bo2940
_database_code_depnum_ccdc_archive 'CCDC 1046183'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H4 N6 O4'
_chemical_formula_weight         176.11

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                   9.2802(15)
_cell_length_b                   9.4120(11)
_cell_length_c                   9.6659(14)
_cell_angle_alpha                61.762(9)
_cell_angle_beta                 77.352(13)
_cell_angle_gamma                64.011(9)
_cell_volume                     668.51(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2635
_cell_measurement_theta_min      2.392
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9198
_exptl_absorpt_correction_T_max  0.9665
_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            9912
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         31.50
_reflns_number_total             4365
_reflns_number_gt                3547
_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)+(0.0468P)²+0.0560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4365
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.66943(10) -0.12549(9) 1.10982(10) 0.03099(19) Uani 1 1 d . . .
O2 O 0.76618(9) 0.06886(10) 0.94741(9) 0.02641(17) Uani 1 1 d . . .
O3 O 0.53658(9) 0.38617(11) 0.74714(9) 0.02751(17) Uani 1 1 d . . .
O4 O 0.36083(9) 0.60287(9) 0.79725(9) 0.02573(17) Uani 1 1 d . . .
O5 O 1.13746(10) 0.09161(11) 0.27574(9) 0.02754(17) Uani 1 1 d . . .
O6 O 0.99350(9) 0.36312(10) 0.23151(9) 0.02813(17) Uani 1 1 d . . .
O7 O 0.74593(10) 0.46300(12) 0.43754(11) 0.0373(2) Uani 1 1 d . . .
O8 O 0.83119(10) 0.50713(10) 0.59953(10) 0.02986(18) Uani 1 1 d . . .
N1 N 0.48445(9) 0.10875(10) 1.23284(10) 0.01853(16) Uani 1 1 d . . .
N2 N 0.37059(10) 0.25400(11) 1.24151(10) 0.02022(17) Uani 1 1 d . . .
N3 N 0.34662(9) 0.39049(10) 1.10085(9) 0.01801(16) Uani 1 1 d . . .
N4 N 0.66525(10) 0.02445(10) 1.04240(10) 0.01903(16) Uani 1 1 d . . .
N5 N 0.44884(9) 0.44781(11) 0.83725(10) 0.01806(16) Uani 1 1 d . . .
N6 N 1.16823(10) 0.00769(11) 0.58035(9) 0.01836(16) Uani 1 1 d . . .
N7 N 1.14355(10) 0.00745(11) 0.72228(10) 0.02033(17) Uani 1 1 d . . .
N8 N 1.02751(9) 0.15792(10) 0.71825(9) 0.01763(16) Uani 1 1 d . . .
N9 N 1.06424(10) 0.20838(11) 0.31967(10) 0.01882(16) Uani 1 1 d . . .
N10 N 0.84260(10) 0.42053(11) 0.53166(10) 0.02037(17) Uani 1 1 d . . .
N11 N 0.92830(11) 0.27195(12) 0.97638(11) 0.01916(16) Uani 1 1 d . . .
N12 N 0.51972(11) 0.21590(12) 0.51999(11) 0.02191(18) Uani 1 1 d . . .
C1 C 0.53544(10) 0.15461(12) 1.08421(11) 0.01562(17) Uani 1 1 d . . .
C2 C 0.44940(10) 0.33182(12) 1.00071(11) 0.01529(17) Uani 1 1 d . . .
C3 C 1.06374(10) 0.16078(12) 0.48451(10) 0.01477(17) Uani 1 1 d . . .
C4 C 0.97611(10) 0.25445(12) 0.57123(11) 0.01548(17) Uani 1 1 d . . .
H11A H 0.9553(16) 0.2387(17) 0.8976(16) 0.028(3) Uiso 1 1 d . . .
H11B H 0.8554(18) 0.380(2) 0.9393(17) 0.036(4) Uiso 1 1 d . . .
H11C H 0.9001(18) 0.197(2) 1.0575(18) 0.035(4) Uiso 1 1 d . . .
H11D H 1.0151(17) 0.2783(18) 0.9967(16) 0.035(4) Uiso 1 1 d . . .
H12A H 0.6135(19) 0.1831(19) 0.4825(18) 0.038(4) Uiso 1 1 d . . .
H12B H 0.5053(17) 0.120(2) 0.6067(18) 0.036(4) Uiso 1 1 d . . .
H12C H 0.448(2) 0.265(2) 0.442(2) 0.049(5) Uiso 1 1 d . . .
H12D H 0.509(2) 0.295(2) 0.5528(19) 0.050(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 0.0343(4) 0.0154(3) 0.0417(5) -0.0123(3) -0.0066(4) -0.0056(3)
O2 0.0220(3) 0.0309(4) 0.0243(4) -0.0164(3) 0.0057(3) -0.0064(3)
O3 0.0276(4) 0.0322(4) 0.0164(4) -0.0106(3) 0.0042(3) -0.0083(3)
O4 0.0297(4) 0.0157(3) 0.0219(4) -0.0017(3) -0.0037(3) -0.0062(3)
O5 0.0316(4) 0.0370(4) 0.0254(4) -0.0236(4) 0.0068(3) -0.0148(3)
O6 0.0280(4) 0.0289(4) 0.0165(4) -0.0039(3) -0.0047(3) -0.0064(3)
O7 0.0271(4) 0.0403(5) 0.0357(5) -0.0235(4) -0.0158(3) 0.0093(4)
O8 0.0302(4) 0.0250(4) 0.0386(5) -0.0228(4) -0.0009(3) -0.0040(3)
N1 0.0183(4) 0.0156(3) 0.0166(4) -0.0046(3) 0.0010(3) -0.0055(3)
N2 0.0196(4) 0.0183(4) 0.0160(4) -0.0053(3) 0.0024(3) -0.0053(3)
N3 0.0176(4) 0.0162(4) 0.0161(4) -0.0063(3) 0.0013(3) -0.0046(3)
N4 0.0193(4) 0.0167(4) 0.0209(4) -0.0102(3) -0.0038(3) -0.0029(3)
N5 0.0184(4) 0.0182(4) 0.0149(4) -0.0042(3) -0.0010(3) -0.0079(3)
N6 0.0184(4) 0.0183(4) 0.0157(4) -0.0081(3) -0.0001(3) -0.0042(3)
N7 0.0205(4) 0.0199(4) 0.0157(4) -0.0079(3) -0.0002(3) -0.0035(3)
N8 0.0175(3) 0.0192(4) 0.0151(4) -0.0084(3) -0.0001(3) -0.0052(3)
N9 0.0182(4) 0.0258(4) 0.0153(4) -0.0105(3) 0.0008(3) -0.0096(3)
N10 0.0189(4) 0.0193(4) 0.0198(4) -0.0106(3) -0.0008(3) -0.0024(3)
N11 0.0205(4) 0.0178(4) 0.0163(4) -0.0082(3) -0.0022(3) -0.0032(3)
N12 0.0244(4) 0.0162(4) 0.0173(4) -0.0056(3) 0.0020(3) -0.0041(3)
C1 0.0151(4) 0.0150(4) 0.0165(4) -0.0071(3) 0.0000(3) -0.0053(3)
C2 0.0161(4) 0.0149(4) 0.0139(4) -0.0055(3) 0.0002(3) -0.0063(3)
C3 0.0151(4) 0.0167(4) 0.0132(4) -0.0078(3) 0.0007(3) -0.0058(3)
C4 0.0149(4) 0.0163(4) 0.0160(4) -0.0089(3) -0.0001(3) -0.0045(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.2291(11) . ?
O2 N4 1.2241(11) . ?
O3 N5 1.2296(11) . ?
O4 N5 1.2272(11) . ?
O5 N9 1.2291(11) . ?
O6 N9 1.2292(11) . ?
O7 N10 1.2212(12) . ?
O8 N10 1.2271(11) . ?
N1 C1 1.3299(12) . ?
N1 N2 1.3402(11) . ?
N2 N3 1.3332(12) . ?
N3 C2 1.3385(11) . ?
N4 C1 1.4412(12) . ?
N5 C2 1.4334(12) . ?
N6 C3 1.3343(12) . ?
N6 N7 1.3396(11) . ?
N7 N8 1.3403(11) . ?
N8 C4 1.3296(12) . ?
N9 C3 1.4362(12) . ?
N10 C4 1.4385(12) . ?
N11 H11A 0.902(14) . ?
N11 H11B 0.883(15) . ?
N11 H11C 0.856(16) . ?
N11 H11D 0.902(14) . ?
N12 H12A 0.846(16) . ?
N12 H12B 0.934(15) . ?
N12 H12C 0.921(17) . ?
N12 H12D 0.896(17) . ?
C1 C2 1.3828(12) . ?
C3 C4 1.3833(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 106.89(8) . . ?
N3 N2 N1 110.69(8) . . ?
N2 N3 C2 106.78(8) . . ?
O2 N4 O1 124.69(9) . . ?
O2 N4 C1 118.15(8) . . ?
O1 N4 C1 117.10(8) . . ?
O4 N5 O3 124.52(9) . . ?
O4 N5 C2 117.29(8) . . ?
O3 N5 C2 118.19(8) . . ?
C3 N6 N7 106.39(8) . . ?
N6 N7 N8 111.11(8) . . ?
C4 N8 N7 106.33(8) . . ?
O5 N9 O6 124.25(9) . . ?
O5 N9 C3 117.66(8) . . ?
O6 N9 C3 118.08(8) . . ?
O7 N10 O8 124.53(9) . . ?
O7 N10 C4 118.18(8) . . ?
O8 N10 C4 117.24(8) . . ?
H11A N11 H11B 106.9(12) . . ?
H11A N11 H11C 109.5(13) . . ?
H11B N11 H11C 115.9(14) . . ?
H11A N11 H11D 107.5(12) . . ?
H11B N11 H11D 106.1(13) . . ?
H11C N11 H11D 110.7(13) . . ?
H12A N12 H12B 109.6(13) . . ?
H12A N12 H12C 108.0(14) . . ?
H12B N12 H12C 111.8(13) . . ?
H12A N12 H12D 108.5(14) . . ?
H12B N12 H12D 108.1(13) . . ?
H12C N12 H12D 110.9(14) . . ?
N1 C1 C2 107.90(8) . . ?
N1 C1 N4 118.86(8) . . ?
C2 C1 N4 133.16(9) . . ?
N3 C2 C1 107.72(8) . . ?
N3 C2 N5 120.13(8) . . ?
C1 C2 N5 132.06(8) . . ?
N6 C3 C4 107.87(8) . . ?
N6 C3 N9 120.91(8) . . ?
C4 C3 N9 131.05(8) . . ?
N8 C4 C3 108.29(8) . . ?
N8 C4 N10 119.60(8) . . ?
C3 C4 N10 131.96(9) . . ?

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 0.96(11) . . . . ?
N1 N2 N3 C2 -1.11(11) . . . . ?
C3 N6 N7 N8 -0.96(10) . . . . ?
N6 N7 N8 C4 0.87(10) . . . . ?
N2 N1 C1 C2 -0.43(10) . . . . ?
N2 N1 C1 N4 176.78(8) . . . . ?
O2 N4 C1 N1 -140.81(9) . . . . ?
O1 N4 C1 N1 36.54(13) . . . . ?
O2 N4 C1 C2 35.54(15) . . . . ?
O1 N4 C1 C2 -147.10(10) . . . . ?
N2 N3 C2 C1 0.81(10) . . . . ?
N2 N3 C2 N5 177.83(8) . . . . ?
N1 C1 C2 N3 -0.24(11) . . . . ?
N4 C1 C2 N3 -176.88(9) . . . . ?
N1 C1 C2 N5 -176.77(9) . . . . ?
N4 C1 C2 N5 6.59(17) . . . . ?
O4 N5 C2 N3 5.76(13) . . . . ?
O3 N5 C2 N3 -174.67(9) . . . . ?
O4 N5 C2 C1 -178.06(10) . . . . ?
O3 N5 C2 C1 1.51(15) . . . . ?
N7 N6 C3 C4 0.66(10) . . . . ?
N7 N6 C3 N9 176.33(8) . . . . ?
O5 N9 C3 N6 15.71(13) . . . . ?
O6 N9 C3 N6 -163.33(9) . . . . ?
O5 N9 C3 C4 -169.75(9) . . . . ?
O6 N9 C3 C4 11.20(14) . . . . ?
N7 N8 C4 C3 -0.43(10) . . . . ?
N7 N8 C4 N10 175.70(8) . . . . ?
N6 C3 C4 N8 -0.14(10) . . . . ?
N9 C3 C4 N8 -175.22(9) . . . . ?
N6 C3 C4 N10 -175.62(9) . . . . ?
N9 C3 C4 N10 9.30(17) . . . . ?
O7 N10 C4 N8 -141.87(10) . . . . ?
O8 N10 C4 N8 35.70(13) . . . . ?
O7 N10 C4 C3 33.20(15) . . . . ?
O8 N10 C4 C3 -149.24(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_bo3194
_database_code_depnum_ccdc_archive 'CCDC 1046184'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-06-04 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 H7 N9 O4'
_chemical_formula_weight         233.18

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   7.304(2)
_cell_length_b                   6.3952(18)
_cell_length_c                   18.719(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.354(4)
_cell_angle_gamma                90.00
_cell_volume                     874.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    1315
_cell_measurement_theta_min      3.186
_cell_measurement_theta_max      31,492

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.158
_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      163(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            9955
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         31.49
_reflns_number_total             2891
_reflns_number_gt                2658
_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)+(0.0359P)²+0.3600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2891
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.48710(10) 0.22026(13) 0.21875(4) 0.02593(17) Uani 1 1 d . . .
O2 O 0.72627(10) 0.04605(13) 0.18475(4) 0.02436(17) Uani 1 1 d . . .
O3 O 1.07895(10) 0.16707(14) 0.22272(4) 0.02522(17) Uani 1 1 d . . .
O4 O 1.18998(10) 0.02255(12) 0.31885(4) 0.02265(16) Uani 1 1 d . . .
C1 C 0.71890(12) 0.16917(15) 0.29969(5) 0.01550(17) Uani 1 1 d . . .
C2 C 0.89970(12) 0.15387(14) 0.32253(5) 0.01488(16) Uani 1 1 d . . .
C3 C 0.34079(13) 0.23726(15) 0.02833(5) 0.01727(17) Uani 1 1 d . . .
N1 N 0.61571(11) 0.21073(14) 0.35682(4) 0.01907(17) Uani 1 1 d . . .
N2 N 0.73161(11) 0.22230(14) 0.41256(4) 0.02000(17) Uani 1 1 d . . .
N3 N 0.90532(11) 0.18833(13) 0.39282(4) 0.01763(16) Uani 1 1 d . . .
N4 N 0.63842(11) 0.14289(13) 0.22979(4) 0.01773(16) Uani 1 1 d . . .
N5 N 1.06781(10) 0.11183(13) 0.28533(4) 0.01621(15) Uani 1 1 d . . .
N6 N 0.03240(12) 0.20167(16) 0.06267(5) 0.02272(18) Uani 1 1 d . . .
N7 N 0.21928(12) 0.21280(14) 0.08080(5) 0.02003(17) Uani 1 1 d . . .
N8 N 0.28309(12) 0.26939(15) -0.03787(5) 0.02165(18) Uani 1 1 d . . .
N9 N 0.51875(12) 0.23111(17) 0.04439(5) 0.02411(19) Uani 1 1 d . . .
H9A H 0.600(2) 0.242(2) 0.0107(9) 0.035(4) Uiso 1 1 d . . .
H7 H 0.259(2) 0.183(3) 0.1235(9) 0.041(4) Uiso 1 1 d . . .
H6A H -0.031(2) 0.296(3) 0.0894(9) 0.040(4) Uiso 1 1 d . . .
H8A H 0.362(2) 0.281(2) -0.0713(8) 0.031(4) Uiso 1 1 d . . .
H9B H 0.554(2) 0.198(3) 0.0885(9) 0.036(4) Uiso 1 1 d . . .
H8B H 0.168(2) 0.281(2) -0.0455(8) 0.034(4) Uiso 1 1 d . . .
H6B H -0.011(2) 0.075(3) 0.0747(9) 0.043(4) 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 0.0167(3) 0.0362(4) 0.0249(4) 0.0035(3) -0.0060(3) 0.0016(3)
O2 0.0244(4) 0.0329(4) 0.0158(3) -0.0050(3) 0.0014(3) -0.0022(3)
O3 0.0206(3) 0.0406(4) 0.0145(3) 0.0039(3) 0.0044(3) 0.0005(3)
O4 0.0167(3) 0.0285(4) 0.0227(4) -0.0005(3) -0.0025(3) 0.0056(3)
C1 0.0139(4) 0.0192(4) 0.0135(4) 0.0003(3) 0.0001(3) -0.0009(3)
C2 0.0134(4) 0.0178(4) 0.0135(4) 0.0000(3) 0.0012(3) -0.0003(3)
C3 0.0188(4) 0.0185(4) 0.0145(4) -0.0004(3) 0.0011(3) 0.0001(3)
N1 0.0157(3) 0.0250(4) 0.0165(4) -0.0009(3) 0.0016(3) 0.0007(3)
N2 0.0170(4) 0.0279(4) 0.0151(4) -0.0023(3) 0.0022(3) 0.0004(3)
N3 0.0161(3) 0.0233(4) 0.0135(4) -0.0011(3) 0.0011(3) -0.0001(3)
N4 0.0155(3) 0.0224(4) 0.0153(4) 0.0018(3) -0.0008(3) -0.0035(3)
N5 0.0135(3) 0.0200(4) 0.0151(3) -0.0013(3) 0.0007(3) -0.0007(3)
N6 0.0181(4) 0.0285(4) 0.0215(4) -0.0011(3) 0.0025(3) -0.0038(3)
N7 0.0187(4) 0.0279(4) 0.0135(4) 0.0014(3) 0.0013(3) -0.0012(3)
N8 0.0178(4) 0.0335(5) 0.0136(4) 0.0032(3) 0.0008(3) 0.0008(3)
N9 0.0184(4) 0.0402(5) 0.0137(4) 0.0022(3) -0.0002(3) 0.0004(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.2273(11) . ?
O2 N4 1.2300(11) . ?
O3 N5 1.2273(11) . ?
O4 N5 1.2284(10) . ?
C1 N1 1.3387(12) . ?
C1 C2 1.3890(12) . ?
C1 N4 1.4408(12) . ?
C2 N3 1.3345(12) . ?
C2 N5 1.4406(12) . ?
C3 N8 1.3223(13) . ?
C3 N9 1.3329(13) . ?
C3 N7 1.3370(12) . ?
N1 N2 1.3417(12) . ?
N2 N3 1.3414(11) . ?
N6 N7 1.4063(13) . ?
N6 H6A 0.911(17) . ?
N6 H6B 0.902(18) . ?
N7 H7 0.869(18) . ?
N8 H8A 0.857(16) . ?
N8 H8B 0.856(16) . ?
N9 H9A 0.870(16) . ?
N9 H9B 0.889(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
N1 C1 C2 107.88(8) . . ?
N1 C1 N4 121.33(8) . . ?
C2 C1 N4 130.77(8) . . ?
N3 C2 C1 108.37(8) . . ?
N3 C2 N5 119.10(8) . . ?
C1 C2 N5 132.53(8) . . ?
N8 C3 N9 121.38(9) . . ?
N8 C3 N7 119.83(9) . . ?
N9 C3 N7 118.79(9) . . ?
C1 N1 N2 106.06(8) . . ?
N3 N2 N1 111.72(8) . . ?
C2 N3 N2 105.97(8) . . ?
O1 N4 O2 124.09(9) . . ?
O1 N4 C1 117.90(8) . . ?
O2 N4 C1 118.01(8) . . ?
O3 N5 O4 124.70(8) . . ?
O3 N5 C2 118.00(8) . . ?
O4 N5 C2 117.29(8) . . ?
N7 N6 H6A 109.2(10) . . ?
N7 N6 H6B 109.3(11) . . ?
H6A N6 H6B 106.0(14) . . ?
C3 N7 N6 118.44(8) . . ?
C3 N7 H7 118.9(11) . . ?
N6 N7 H7 121.8(11) . . ?
C3 N8 H8A 119.0(10) . . ?
C3 N8 H8B 118.5(11) . . ?
H8A N8 H8B 122.5(15) . . ?
C3 N9 H9A 120.0(10) . . ?
C3 N9 H9B 119.6(10) . . ?
H9A N9 H9B 119.8(15) . . ?

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
N1 C1 C2 N3 -0.68(11) . . . . ?
N4 C1 C2 N3 -178.98(9) . . . . ?
N1 C1 C2 N5 179.83(10) . . . . ?
N4 C1 C2 N5 1.53(18) . . . . ?
C2 C1 N1 N2 0.60(11) . . . . ?
N4 C1 N1 N2 179.10(8) . . . . ?
C1 N1 N2 N3 -0.33(11) . . . . ?
C1 C2 N3 N2 0.46(10) . . . . ?
N5 C2 N3 N2 -179.97(8) . . . . ?
N1 N2 N3 C2 -0.09(11) . . . . ?
N1 C1 N4 O1 22.08(14) . . . . ?
C2 C1 N4 O1 -159.81(10) . . . . ?
N1 C1 N4 O2 -158.57(9) . . . . ?
C2 C1 N4 O2 19.54(15) . . . . ?
N3 C2 N5 O3 -149.38(9) . . . . ?
C1 C2 N5 O3 30.07(15) . . . . ?
N3 C2 N5 O4 30.71(13) . . . . ?
C1 C2 N5 O4 -149.84(10) . . . . ?
N8 C3 N7 N6 6.14(14) . . . . ?
N9 C3 N7 N6 -174.67(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_bo3197
_database_code_depnum_ccdc_archive 'CCDC 1046185'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-06-04 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 H8 N10 O4'
_chemical_formula_weight         248.19

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.553(2)
_cell_length_b                   8.471(3)
_cell_length_c                   9.078(3)
_cell_angle_alpha                93.386(5)
_cell_angle_beta                 91.224(7)
_cell_angle_gamma                98.007(5)
_cell_volume                     497.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    1940
_cell_measurement_theta_min      2.433
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.147
_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      163(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            7378
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         31.51
_reflns_number_total             3255
_reflns_number_gt                2686
_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)+(0.0438P)²+0.0860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3255
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.26876(15) 0.56606(9) 0.58630(9) 0.0407(2) Uani 1 1 d . . .
O2 O 0.39678(12) 0.41188(9) 0.73289(8) 0.03112(17) Uani 1 1 d . . .
O3 O 0.32266(15) 0.09075(9) 0.74977(8) 0.0392(2) Uani 1 1 d . . .
O4 O 0.29167(13) -0.10522(9) 0.58511(9) 0.03434(19) Uani 1 1 d . . .
N1 N 0.20419(13) 0.33876(11) 0.37125(9) 0.02563(18) Uani 1 1 d . . .
N2 N 0.16778(14) 0.19870(12) 0.29205(9) 0.02897(19) Uani 1 1 d . . .
N3 N 0.19664(13) 0.07669(11) 0.37362(9) 0.02575(18) Uani 1 1 d . . .
N4 N 0.31029(12) 0.43564(10) 0.61643(9) 0.02328(17) Uani 1 1 d . . .
N5 N 0.29275(12) 0.03604(9) 0.62202(9) 0.02250(16) Uani 1 1 d . . .
N6 N 0.12728(13) 0.69371(12) 0.27844(9) 0.02574(18) Uani 1 1 d . . .
N7 N 0.23393(13) 0.71364(11) 0.14641(8) 0.02420(17) Uani 1 1 d . . .
N8 N 0.44616(14) 0.76177(14) -0.09788(10) 0.0314(2) Uani 1 1 d . . .
N9 N 0.22988(13) 0.74975(13) -0.10186(9) 0.0318(2) Uani 1 1 d . . .
N10 N -0.07381(14) 0.72126(14) 0.02096(10) 0.0342(2) Uani 1 1 d . . .
C1 C 0.25785(13) 0.30535(11) 0.50726(10) 0.02046(17) Uani 1 1 d . . .
C2 C 0.25381(13) 0.14098(11) 0.50864(9) 0.01999(17) Uani 1 1 d . . .
C3 C 0.12919(14) 0.72930(11) 0.02306(10) 0.02236(18) Uani 1 1 d . . .
H6A H 0.163(2) 0.6077(17) 0.3152(15) 0.032(3) Uiso 1 1 d . . .
H6B H 0.170(2) 0.7830(17) 0.3411(16) 0.035(3) Uiso 1 1 d . . .
H7 H 0.366(2) 0.7206(17) 0.1449(15) 0.037(4) Uiso 1 1 d . . .
H8A H 0.495(2) 0.8565(19) -0.1338(17) 0.044(4) Uiso 1 1 d . . .
H8B H 0.484(2) 0.683(2) -0.160(2) 0.057(5) Uiso 1 1 d . . .
H9 H 0.167(2) 0.7632(17) -0.1839(16) 0.038(4) Uiso 1 1 d . . .
H10A H -0.133(2) 0.7173(18) 0.1040(17) 0.041(4) Uiso 1 1 d . . .
H10B H -0.134(2) 0.7504(19) -0.0541(18) 0.047(4) 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 0.0655(6) 0.0226(4) 0.0359(4) 0.0066(3) -0.0069(4) 0.0127(4)
O2 0.0371(4) 0.0275(4) 0.0282(4) 0.0024(3) -0.0118(3) 0.0040(3)
O3 0.0700(6) 0.0272(4) 0.0199(3) 0.0026(3) -0.0097(4) 0.0057(4)
O4 0.0519(5) 0.0205(3) 0.0316(4) 0.0004(3) -0.0045(3) 0.0100(3)
N1 0.0248(4) 0.0326(4) 0.0207(4) 0.0093(3) 0.0003(3) 0.0048(3)
N2 0.0292(4) 0.0388(5) 0.0193(4) 0.0057(3) -0.0017(3) 0.0046(4)
N3 0.0268(4) 0.0316(4) 0.0188(3) 0.0008(3) -0.0012(3) 0.0048(3)
N4 0.0242(4) 0.0220(4) 0.0241(4) 0.0060(3) 0.0005(3) 0.0030(3)
N5 0.0254(4) 0.0211(4) 0.0211(3) 0.0029(3) -0.0019(3) 0.0036(3)
N6 0.0283(4) 0.0335(4) 0.0161(3) 0.0051(3) 0.0004(3) 0.0054(3)
N7 0.0207(4) 0.0360(4) 0.0168(3) 0.0053(3) -0.0012(3) 0.0060(3)
N8 0.0224(4) 0.0466(6) 0.0249(4) 0.0038(4) 0.0017(3) 0.0030(4)
N9 0.0231(4) 0.0550(6) 0.0185(4) 0.0104(4) -0.0010(3) 0.0068(4)
N10 0.0228(4) 0.0616(7) 0.0203(4) 0.0109(4) -0.0015(3) 0.0101(4)
C1 0.0187(4) 0.0241(4) 0.0193(4) 0.0055(3) 0.0011(3) 0.0035(3)
C2 0.0191(4) 0.0246(4) 0.0168(4) 0.0035(3) 0.0002(3) 0.0040(3)
C3 0.0233(4) 0.0266(4) 0.0178(4) 0.0041(3) -0.0015(3) 0.0050(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.2189(11) . ?
O2 N4 1.2291(11) . ?
O3 N5 1.2246(11) . ?
O4 N5 1.2224(12) . ?
N1 C1 1.3337(12) . ?
N1 N2 1.3395(13) . ?
N2 N3 1.3384(12) . ?
N3 C2 1.3356(13) . ?
N4 C1 1.4383(13) . ?
N5 C2 1.4404(12) . ?
N6 N7 1.4073(11) . ?
N6 H6A 0.877(14) . ?
N6 H6B 0.926(15) . ?
N7 C3 1.3239(12) . ?
N7 H7 0.862(14) . ?
N8 N9 1.4063(13) . ?
N8 H8A 0.905(16) . ?
N8 H8B 0.910(17) . ?
N9 C3 1.3322(12) . ?
N9 H9 0.865(15) . ?
N10 C3 1.3221(14) . ?
N10 H10A 0.856(16) . ?
N10 H10B 0.845(16) . ?
C1 C2 1.3897(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
C1 N1 N2 106.29(8) . . ?
N3 N2 N1 111.60(8) . . ?
C2 N3 N2 106.09(8) . . ?
O1 N4 O2 123.34(9) . . ?
O1 N4 C1 117.32(8) . . ?
O2 N4 C1 119.33(8) . . ?
O4 N5 O3 123.15(8) . . ?
O4 N5 C2 117.60(8) . . ?
O3 N5 C2 119.24(8) . . ?
N7 N6 H6A 106.4(9) . . ?
N7 N6 H6B 107.5(9) . . ?
H6A N6 H6B 110.8(12) . . ?
C3 N7 N6 119.16(8) . . ?
C3 N7 H7 119.3(9) . . ?
N6 N7 H7 121.5(9) . . ?
N9 N8 H8A 107.1(10) . . ?
N9 N8 H8B 108.9(10) . . ?
H8A N8 H8B 107.4(15) . . ?
C3 N9 N8 119.01(8) . . ?
C3 N9 H9 121.8(9) . . ?
N8 N9 H9 119.0(9) . . ?
C3 N10 H10A 117.3(10) . . ?
C3 N10 H10B 118.7(10) . . ?
H10A N10 H10B 120.8(14) . . ?
N1 C1 C2 107.90(8) . . ?
N1 C1 N4 118.36(8) . . ?
C2 C1 N4 133.72(8) . . ?
N3 C2 C1 108.12(8) . . ?
N3 C2 N5 118.45(9) . . ?
C1 C2 N5 133.42(8) . . ?
N10 C3 N7 121.21(9) . . ?
N10 C3 N9 119.45(9) . . ?
N7 C3 N9 119.33(9) . . ?

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 0.01(11) . . . . ?
N1 N2 N3 C2 -0.22(11) . . . . ?
N2 N1 C1 C2 0.19(10) . . . . ?
N2 N1 C1 N4 178.78(8) . . . . ?
O1 N4 C1 N1 12.43(13) . . . . ?
O2 N4 C1 N1 -166.31(9) . . . . ?
O1 N4 C1 C2 -169.44(10) . . . . ?
O2 N4 C1 C2 11.83(15) . . . . ?
N2 N3 C2 C1 0.33(10) . . . . ?
N2 N3 C2 N5 179.01(8) . . . . ?
N1 C1 C2 N3 -0.33(10) . . . . ?
N4 C1 C2 N3 -178.61(9) . . . . ?
N1 C1 C2 N5 -178.74(9) . . . . ?
N4 C1 C2 N5 2.98(18) . . . . ?
O4 N5 C2 N3 7.24(13) . . . . ?
O3 N5 C2 N3 -171.90(9) . . . . ?
O4 N5 C2 C1 -174.48(10) . . . . ?
O3 N5 C2 C1 6.38(16) . . . . ?
N6 N7 C3 N10 -2.25(15) . . . . ?
N6 N7 C3 N9 179.35(9) . . . . ?
N8 N9 C3 N10 178.58(10) . . . . ?
N8 N9 C3 N7 -3.00(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        31.51
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bo2676
_database_code_depnum_ccdc_archive 'CCDC 1046186'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 N10 O2'
_chemical_formula_weight         214.18

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   3.5714(10)
_cell_length_b                   9.496(3)
_cell_length_c                   12.886(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.883(4)
_cell_angle_gamma                90.00
_cell_volume                     437.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1820
_cell_measurement_theta_min      2.665
_cell_measurement_theta_max      31.497

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.137
_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            5011
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         31.50
_reflns_number_total             2201
_reflns_number_gt                2095
_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)+(0.0183P)²+0.0860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(11)
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     161
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0557
_refine_ls_wR_factor_gt          0.0548
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.000
_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 0.7274(3) 0.55587(9) 0.57047(8) 0.0326(2) Uani 1 1 d . . .
O2 O 1.0086(3) 0.49243(10) 0.42975(7) 0.0339(2) Uani 1 1 d . . .
N1 N 0.9328(3) 0.14543(11) 0.65987(9) 0.0237(2) Uani 1 1 d . . .
N2 N 1.0753(3) 0.11276(11) 0.56487(9) 0.0260(2) Uani 1 1 d . . .
N3 N 1.0747(3) 0.22315(11) 0.50288(9) 0.0229(2) Uani 1 1 d . . .
N4 N 0.6747(3) 0.35571(11) 0.73753(8) 0.0238(2) Uani 1 1 d . . .
N5 N 0.5956(3) 0.27927(12) 0.81329(8) 0.0254(2) Uani 1 1 d . . .
N6 N 0.5076(4) 0.22300(14) 0.88553(10) 0.0394(3) Uani 1 1 d . . .
N7 N 0.8856(3) 0.46664(11) 0.51677(8) 0.0229(2) Uani 1 1 d . . .
N8 N 0.3925(3) 0.67501(12) 0.76461(10) 0.0270(2) Uani 1 1 d . . .
N9 N 0.3738(3) 0.82925(13) 0.62639(8) 0.0257(2) Uani 1 1 d . . .
N10 N 0.1503(3) 0.89676(12) 0.78509(9) 0.0253(2) Uani 1 1 d . . .
C1 C 0.8360(3) 0.28113(12) 0.65601(9) 0.0190(2) Uani 1 1 d . . .
C2 C 0.9266(3) 0.33034(12) 0.55815(9) 0.0188(2) Uani 1 1 d . . .
C3 C 0.3039(3) 0.79990(12) 0.72489(9) 0.0205(2) Uani 1 1 d . . .
H8A H 0.496(5) 0.6122(19) 0.7263(15) 0.037(5) Uiso 1 1 d . . .
H8B H 0.320(5) 0.6534(19) 0.8275(16) 0.048(5) Uiso 1 1 d . . .
H9A H 0.468(5) 0.7687(19) 0.5879(14) 0.035(5) Uiso 1 1 d . . .
H9B H 0.307(5) 0.9067(18) 0.6006(13) 0.026(4) Uiso 1 1 d . . .
H10A H 0.072(4) 0.9774(17) 0.7583(12) 0.023(4) Uiso 1 1 d . . .
H10B H 0.099(5) 0.8681(19) 0.8468(15) 0.037(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 0.0511(6) 0.0212(4) 0.0256(5) 0.0007(4) 0.0085(4) 0.0122(4)
O2 0.0517(6) 0.0295(5) 0.0209(5) 0.0062(4) 0.0096(4) 0.0073(5)
N1 0.0310(5) 0.0199(5) 0.0202(5) -0.0005(4) 0.0019(4) 0.0038(4)
N2 0.0349(6) 0.0212(5) 0.0221(5) -0.0010(4) 0.0029(4) 0.0055(4)
N3 0.0278(5) 0.0220(5) 0.0191(5) -0.0018(4) 0.0019(4) 0.0062(4)
N4 0.0325(5) 0.0209(5) 0.0181(4) -0.0017(4) 0.0042(4) 0.0017(4)
N5 0.0317(5) 0.0238(5) 0.0208(5) -0.0046(4) 0.0033(4) -0.0003(4)
N6 0.0600(8) 0.0346(7) 0.0238(6) -0.0003(5) 0.0119(6) -0.0044(6)
N7 0.0277(5) 0.0217(5) 0.0193(5) 0.0009(4) 0.0006(4) 0.0035(4)
N8 0.0357(6) 0.0215(5) 0.0241(5) 0.0054(4) 0.0088(4) 0.0061(4)
N9 0.0386(6) 0.0196(5) 0.0191(5) 0.0014(4) 0.0073(4) 0.0076(4)
N10 0.0350(6) 0.0226(5) 0.0185(5) 0.0032(4) 0.0058(4) 0.0077(4)
C1 0.0220(5) 0.0187(5) 0.0162(5) -0.0008(4) 0.0002(4) 0.0014(4)
C2 0.0222(5) 0.0184(5) 0.0158(5) -0.0003(4) 0.0005(4) 0.0029(4)
C3 0.0218(5) 0.0194(5) 0.0203(5) 0.0016(4) 0.0021(4) 0.0004(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 N7 1.2362(13) . ?
O2 N7 1.2350(13) . ?
N1 C1 1.3349(16) . ?
N1 N2 1.3687(14) . ?
N2 N3 1.3179(15) . ?
N3 C2 1.3545(15) . ?
N4 N5 1.2522(15) . ?
N4 C1 1.3984(15) . ?
N5 N6 1.1224(15) . ?
N7 C2 1.4067(15) . ?
N8 C3 1.3281(16) . ?
N8 H8A 0.862(19) . ?
N8 H8B 0.88(2) . ?
N9 C3 1.3269(15) . ?
N9 H9A 0.833(18) . ?
N9 H9B 0.840(18) . ?
N10 C3 1.3273(15) . ?
N10 H10A 0.885(16) . ?
N10 H10B 0.863(18) . ?
C1 C2 1.3877(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 106.57(10) . . ?
N3 N2 N1 111.38(10) . . ?
N2 N3 C2 106.02(10) . . ?
N5 N4 C1 113.11(10) . . ?
N6 N5 N4 172.69(13) . . ?
O2 N7 O1 122.98(11) . . ?
O2 N7 C2 119.36(10) . . ?
O1 N7 C2 117.67(10) . . ?
C3 N8 H8A 120.0(12) . . ?
C3 N8 H8B 119.5(12) . . ?
H8A N8 H8B 120.1(17) . . ?
C3 N9 H9A 120.5(12) . . ?
C3 N9 H9B 120.4(11) . . ?
H9A N9 H9B 118.9(17) . . ?
C3 N10 H10A 120.2(10) . . ?
C3 N10 H10B 114.6(12) . . ?
H10A N10 H10B 124.2(16) . . ?
N1 C1 C2 107.16(10) . . ?
N1 C1 N4 124.77(11) . . ?
C2 C1 N4 128.07(10) . . ?
N3 C2 C1 108.86(10) . . ?
N3 C2 N7 122.09(10) . . ?
C1 C2 N7 129.05(10) . . ?
N9 C3 N10 119.94(11) . . ?
N9 C3 N8 120.59(11) . . ?
N10 C3 N8 119.46(11) . . ?

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 0.75(14) . . . . ?
N1 N2 N3 C2 -0.35(14) . . . . ?
C1 N4 N5 N6 -174.0(11) . . . . ?
N2 N1 C1 C2 -0.81(13) . . . . ?
N2 N1 C1 N4 179.34(12) . . . . ?
N5 N4 C1 N1 -6.21(18) . . . . ?
N5 N4 C1 C2 173.98(12) . . . . ?
N2 N3 C2 C1 -0.17(14) . . . . ?
N2 N3 C2 N7 179.27(11) . . . . ?
N1 C1 C2 N3 0.63(14) . . . . ?
N4 C1 C2 N3 -179.53(12) . . . . ?
N1 C1 C2 N7 -178.76(12) . . . . ?
N4 C1 C2 N7 1.1(2) . . . . ?
O2 N7 C2 N3 -4.53(18) . . . . ?
O1 N7 C2 N3 175.79(12) . . . . ?
O2 N7 C2 C1 174.78(13) . . . . ?
O1 N7 C2 C1 -4.90(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_bo2680
_database_code_depnum_ccdc_archive 'CCDC 1046187'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H5 N7 O4'
_chemical_formula_weight         191.13

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   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                   7.9369(18)
_cell_length_b                   9.884(2)
_cell_length_c                   8.6066(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.979(4)
_cell_angle_gamma                90.00
_cell_volume                     674.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2465
_cell_measurement_theta_min      2.060
_cell_measurement_theta_max      29.101

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9259
_exptl_absorpt_correction_T_max  0.9719
_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            5842
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         29.13
_reflns_number_total             1810
_reflns_number_gt                1606
_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)+(0.0239P)²+0.3560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1810
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.30320(10) 0.46575(8) 0.54374(10) 0.01926(19) Uani 1 1 d . . .
O2 O 0.10632(10) 0.48291(8) 0.36185(10) 0.0202(2) Uani 1 1 d . . .
O3 O 0.13689(11) 0.94660(9) 0.40587(10) 0.0238(2) Uani 1 1 d . . .
O4 O 0.27707(11) 1.09469(8) 0.54461(10) 0.0207(2) Uani 1 1 d . . .
N1 N 0.42985(11) 0.68294(10) 0.67064(11) 0.0147(2) Uani 1 1 d . . .
N2 N 0.51427(12) 0.78437(9) 0.74661(12) 0.0170(2) Uani 1 1 d . . .
N3 N 0.45260(11) 0.89927(10) 0.69690(11) 0.0158(2) Uani 1 1 d . . .
N4 N 0.19894(11) 0.67031(9) 0.46799(11) 0.0154(2) Uani 1 1 d . . .
N5 N 0.20607(11) 0.53578(9) 0.46076(11) 0.0143(2) Uani 1 1 d . . .
N6 N 0.24271(12) 0.97697(9) 0.50949(11) 0.0151(2) Uani 1 1 d . . .
N7 N 0.09883(13) 0.21823(10) 0.23857(13) 0.0174(2) Uani 1 1 d . . .
C1 C 0.31139(13) 0.73154(11) 0.56838(12) 0.0131(2) Uani 1 1 d . . .
C2 C 0.32955(13) 0.87145(11) 0.58855(12) 0.0137(2) Uani 1 1 d . . .
H1N H 0.457(2) 0.5969(18) 0.6900(19) 0.035(4) Uiso 1 1 d . . .
H7A H 0.006(2) 0.2228(16) 0.1743(19) 0.030(4) Uiso 1 1 d . . .
H7B H 0.107(2) 0.2993(17) 0.2940(19) 0.030(4) Uiso 1 1 d . . .
H7C H 0.193(2) 0.2087(16) 0.183(2) 0.036(4) Uiso 1 1 d . . .
H7D H 0.094(2) 0.148(2) 0.303(2) 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 0.0199(4) 0.0135(4) 0.0238(4) 0.0032(3) -0.0059(3) 0.0021(3)
O2 0.0219(4) 0.0152(4) 0.0230(4) -0.0049(3) -0.0074(3) -0.0018(3)
O3 0.0264(4) 0.0178(4) 0.0262(5) 0.0002(3) -0.0140(4) 0.0002(3)
O4 0.0275(4) 0.0100(4) 0.0243(4) -0.0016(3) -0.0015(3) -0.0011(3)
N1 0.0141(4) 0.0123(4) 0.0174(5) -0.0005(4) -0.0033(3) 0.0003(3)
N2 0.0163(4) 0.0142(5) 0.0203(5) -0.0022(4) -0.0042(4) -0.0012(3)
N3 0.0146(4) 0.0152(4) 0.0173(5) -0.0009(3) -0.0022(3) 0.0000(3)
N4 0.0167(4) 0.0100(4) 0.0192(5) -0.0012(3) -0.0043(4) -0.0004(3)
N5 0.0140(4) 0.0124(4) 0.0164(4) -0.0005(3) -0.0003(3) -0.0005(3)
N6 0.0163(4) 0.0128(4) 0.0161(4) 0.0000(4) 0.0000(3) 0.0000(3)
N7 0.0179(5) 0.0135(5) 0.0206(5) 0.0003(4) -0.0037(4) 0.0000(4)
C1 0.0120(4) 0.0131(5) 0.0141(5) 0.0000(4) 0.0000(4) -0.0001(4)
C2 0.0136(5) 0.0129(5) 0.0146(5) -0.0005(4) -0.0014(4) 0.0001(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 N5 1.2432(12) . ?
O2 N5 1.2561(12) . ?
O3 N6 1.2406(12) . ?
O4 N6 1.2304(12) . ?
N1 C1 1.3536(14) . ?
N1 N2 1.3606(13) . ?
N1 H1N 0.891(17) . ?
N2 N3 1.3031(13) . ?
N3 C2 1.3550(14) . ?
N4 N5 1.3325(13) . ?
N4 C1 1.3624(14) . ?
N6 C2 1.4120(14) . ?
N7 H7A 0.907(17) . ?
N7 H7B 0.934(17) . ?
N7 H7C 0.909(18) . ?
N7 H7D 0.89(2) . ?
C1 C2 1.4005(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 111.74(9) . . ?
C1 N1 H1N 128.1(11) . . ?
N2 N1 H1N 120.2(11) . . ?
N3 N2 N1 108.13(9) . . ?
N2 N3 C2 107.62(9) . . ?
N5 N4 C1 116.42(9) . . ?
O1 N5 O2 121.43(9) . . ?
O1 N5 N4 123.73(9) . . ?
O2 N5 N4 114.84(9) . . ?
O4 N6 O3 122.97(9) . . ?
O4 N6 C2 118.67(9) . . ?
O3 N6 C2 118.34(9) . . ?
H7A N7 H7B 108.1(13) . . ?
H7A N7 H7C 110.6(14) . . ?
H7B N7 H7C 108.3(14) . . ?
H7A N7 H7D 111.5(15) . . ?
H7B N7 H7D 110.7(15) . . ?
H7C N7 H7D 107.7(15) . . ?
N1 C1 N4 132.83(10) . . ?
N1 C1 C2 101.75(9) . . ?
N4 C1 C2 125.42(10) . . ?
N3 C2 C1 110.76(9) . . ?
N3 C2 N6 120.66(10) . . ?
C1 C2 N6 128.55(10) . . ?

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 0.44(12) . . . . ?
N1 N2 N3 C2 -0.37(12) . . . . ?
C1 N4 N5 O1 2.99(16) . . . . ?
C1 N4 N5 O2 -176.75(9) . . . . ?
N2 N1 C1 N4 179.68(11) . . . . ?
N2 N1 C1 C2 -0.31(12) . . . . ?
N5 N4 C1 N1 -2.85(18) . . . . ?
N5 N4 C1 C2 177.14(10) . . . . ?
N2 N3 C2 C1 0.18(12) . . . . ?
N2 N3 C2 N6 -177.88(9) . . . . ?
N1 C1 C2 N3 0.08(12) . . . . ?
N4 C1 C2 N3 -179.91(10) . . . . ?
N1 C1 C2 N6 177.95(10) . . . . ?
N4 C1 C2 N6 -2.04(19) . . . . ?
O4 N6 C2 N3 -2.40(15) . . . . ?
O3 N6 C2 N3 176.50(10) . . . . ?
O4 N6 C2 C1 179.92(11) . . . . ?
O3 N6 C2 C1 -1.19(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
