# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_publication_text _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _publ_contact_author_name J.M.Shreeve _publ_contact_author_address ;University Research Office, University of Idaho, Box 443010 Moscow, ID, 83844-3010 USA ; _publ_contact_author_email JSHREEVE@UIDAHO.EDU _publ_contact_author_phone '208 885 2847' _publ_contact_author_fax '208 885 2847' loop_ _publ_author_name _publ_author_address 'Chengfeng Ye.' ;Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA ; 'Haixiang Gao.' ;Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA ; B.Twamley ;Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA ; J.Shreeve ;Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA ; _publ_section_title ;Dense Energetic Salts of N,N'-dinitrourea (DNU) ; data_1 #####bt1066 _database_code_depnum_ccdc_archive 'CCDC 654504' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DNU _chemical_melting_point ? _chemical_formula_moiety 'C1 H2 N4 O5' _chemical_formula_sum 'C1 H2 N4 O5' _chemical_formula_weight 150.07 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 12.0015(9) _cell_length_b 17.6425(13) _cell_length_c 4.5555(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 964.57(13) _cell_formula_units_Z 8 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2824 _cell_measurement_theta_min 4.10 _cell_measurement_theta_max 29.99 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS-2004/1 ; Bruker, 2004' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker/Siemens SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3712 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0100 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 30.03 _reflns_number_total 389 _reflns_number_gt 379 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker, 2006; APEX2v2.1-RC12' _computing_cell_refinement 'Bruker, 2006; APEX2, SAINT+ v.7.23a' _computing_data_reduction 'Bruker, 2006; APEX2, SAINT+ v.7.23a' _computing_structure_solution 'Bruker, 2003; XS, SHELXTL v.6.14' _computing_structure_refinement "Bruker, 2003; XL,SHELXTL v.6.14'" _computing_molecular_graphics 'Bruker, 2003; XP, SHELXTL v.6.14' _computing_publication_material 'Bruker, 2001; APEX2, XCIF v.6.12' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0406P)^2^+0.7359P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 389 _refine_ls_number_parameters 47 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.095 _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 1.0000 0.0000 0.3458(5) 0.0102(4) Uani 1 2 d S . . O1 O 0.83007(9) 0.09249(6) 0.1687(3) 0.0172(3) Uani 1 1 d . . . O2 O 0.74402(8) 0.07043(6) 0.5793(3) 0.0174(3) Uani 1 1 d . . . O3 O 1.0000 0.0000 0.0808(4) 0.0135(3) Uani 1 2 d S . . N1 N 0.82298(9) 0.06486(6) 0.4120(3) 0.0113(2) Uani 1 1 d . . . N2 N 0.91170(9) 0.02257(7) 0.5221(3) 0.0113(2) Uani 1 1 d . . . H2A H 0.9117 0.0098 0.7088 0.014 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 C1 0.0099(8) 0.0110(7) 0.0097(9) 0.000 0.000 -0.0007(6) O1 0.0192(5) 0.0202(5) 0.0120(5) 0.0054(4) 0.0012(4) 0.0055(4) O2 0.0131(4) 0.0239(5) 0.0151(5) 0.0010(5) 0.0043(4) 0.0053(4) O3 0.0136(6) 0.0184(6) 0.0087(6) 0.000 0.000 0.0023(5) N1 0.0107(5) 0.0115(5) 0.0115(5) -0.0010(5) -0.0013(5) 0.0014(4) N2 0.0104(5) 0.0156(5) 0.0079(5) 0.0017(4) -0.0002(4) 0.0031(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 C1 O3 1.207(3) . ? C1 N2 1.3880(17) 2_755 ? C1 N2 1.3880(17) . ? O1 N1 1.2135(17) . ? O2 N1 1.2200(16) . ? N1 N2 1.3936(15) . ? N2 H2A 0.8800 . ? 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 C1 N2 125.35(9) . 2_755 ? O3 C1 N2 125.35(9) . . ? N2 C1 N2 109.29(18) 2_755 . ? O1 N1 O2 126.34(12) . . ? O1 N1 N2 119.34(12) . . ? O2 N1 N2 114.32(12) . . ? C1 N2 N1 121.92(12) . . ? C1 N2 H2A 119.0 . . ? N1 N2 H2A 119.0 . . ? 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 N2 H2A O3 0.88 2.01 2.786(2) 147.0 1_556 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.262 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.047 data_2a #####bt1076 _database_code_depnum_ccdc_archive 'CCDC 654505' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C H N4 O5, C2 H4 N3' _chemical_melting_point ? _chemical_formula_moiety 'C1 H1 N4 O5, C2 H4 N3' _chemical_formula_sum 'C3 H5 N7 O5' _chemical_formula_weight 219.14 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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6156(3) _cell_length_b 4.9837(2) _cell_length_c 10.3119(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.5300(10) _cell_angle_gamma 90.00 _cell_volume 389.55(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 4485 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 29.99 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'SADABS-2004/1 ; Bruker, 2004' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker/Siemens SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5716 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 29.00 _reflns_number_total 1151 _reflns_number_gt 1114 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker, 2006; SMART v. 5.632' _computing_cell_refinement 'Bruker, 2006; SAINT+ v. 7.23a' _computing_data_reduction 'Bruker, 2006; SAINT+ v. 7.23a' _computing_structure_solution 'Bruker, 2003; XS, SHELXTL v. 6.14' _computing_structure_refinement "Bruker, 2003; XL,SHELXTL v. 6.14'" _computing_molecular_graphics 'Bruker, 2003; XP, SHELXTL v. 6.14' _computing_publication_material 'Bruker, 2001; XCIF, SHELXTL, v. 6.14' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Friedel pairs merged using MERG 3. The value of the absolute structure parameter is meaningless because of its large s.u. value ; _refine_ls_abs_structure_Flack 0.5(12) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.0795P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 1151 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _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 C3 C 0.22660(19) 0.2497(3) 0.46405(14) 0.0146(3) Uani 1 1 d . . . H3 H 0.1562 0.3820 0.5005 0.018 Uiso 1 1 calc R . . C5 C 0.38193(19) 0.0267(3) 0.33598(14) 0.0141(3) Uani 1 1 d . . . H5 H 0.4402 -0.0200 0.2618 0.017 Uiso 1 1 calc R . . C10 C 0.15467(19) 0.6268(3) 0.81057(14) 0.0132(3) Uani 1 1 d . . . N1 N 0.38427(17) -0.1193(3) 0.44124(13) 0.0155(3) Uani 1 1 d . . . N2 N 0.28513(17) 0.0264(3) 0.51985(12) 0.0144(3) Uani 1 1 d . . . H2 H 0.2633 -0.0239 0.5985 0.017 Uiso 1 1 calc R . . N4 N 0.28506(16) 0.2550(3) 0.34608(12) 0.0139(3) Uani 1 1 d . . . H4 H 0.2651 0.3808 0.2866 0.017 Uiso 1 1 calc R . . N8 N -0.03549(16) 0.2665(3) 0.78495(11) 0.0124(3) Uani 1 1 d . . . N9 N 0.03977(17) 0.4515(3) 0.86353(12) 0.0143(3) Uani 1 1 d . . . N12 N 0.22400(17) 0.7824(3) 0.91718(12) 0.0166(3) Uani 1 1 d . . . H12 H 0.1894 0.7416 0.9938 0.020 Uiso 1 1 calc R . . N13 N 0.33984(17) 0.9908(3) 0.91336(13) 0.0146(3) Uani 1 1 d . . . O6 O -0.15525(15) 0.1320(3) 0.83356(10) 0.0158(2) Uani 1 1 d . . . O7 O 0.00179(15) 0.2148(3) 0.67315(10) 0.0191(3) Uani 1 1 d . . . O11 O 0.19092(16) 0.6578(3) 0.69942(11) 0.0200(3) Uani 1 1 d . . . O14 O 0.37897(16) 1.1019(3) 1.01829(11) 0.0188(3) Uani 1 1 d . . . O15 O 0.39662(16) 1.0524(3) 0.81003(11) 0.0215(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 C3 0.0151(6) 0.0152(8) 0.0137(7) -0.0007(6) 0.0018(5) -0.0007(6) C5 0.0147(6) 0.0147(7) 0.0129(6) -0.0015(6) 0.0010(5) -0.0004(6) C10 0.0135(6) 0.0120(7) 0.0139(6) -0.0003(6) 0.0002(5) 0.0010(6) N1 0.0159(6) 0.0151(6) 0.0154(6) -0.0012(5) 0.0014(5) -0.0001(5) N2 0.0169(6) 0.0147(7) 0.0118(5) 0.0002(5) 0.0019(4) -0.0010(5) N4 0.0156(5) 0.0145(6) 0.0115(5) 0.0017(5) 0.0018(4) 0.0007(5) N8 0.0130(5) 0.0125(6) 0.0115(5) 0.0007(5) 0.0001(4) 0.0016(5) N9 0.0169(6) 0.0155(6) 0.0108(6) -0.0013(5) 0.0015(5) -0.0017(5) N12 0.0186(6) 0.0197(7) 0.0118(6) -0.0010(5) 0.0030(4) -0.0064(6) N13 0.0152(6) 0.0146(7) 0.0141(6) 0.0015(5) 0.0008(4) -0.0002(5) O6 0.0176(5) 0.0167(6) 0.0136(5) -0.0005(4) 0.0032(4) -0.0036(4) O7 0.0216(5) 0.0234(6) 0.0131(5) -0.0061(5) 0.0057(4) -0.0049(5) O11 0.0305(6) 0.0190(6) 0.0111(5) 0.0002(5) 0.0048(4) -0.0062(5) O14 0.0225(5) 0.0175(6) 0.0158(5) -0.0033(5) -0.0009(4) -0.0031(5) O15 0.0245(6) 0.0248(7) 0.0157(5) 0.0029(5) 0.0045(4) -0.0081(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 C3 N2 1.311(2) . ? C3 N4 1.3353(18) . ? C3 H3 0.9500 . ? C5 N1 1.305(2) . ? C5 N4 1.365(2) . ? C5 H5 0.9500 . ? C10 O11 1.2143(18) . ? C10 N9 1.385(2) . ? C10 N12 1.406(2) . ? N1 N2 1.3682(18) . ? N2 H2 0.8800 . ? N4 H4 0.8800 . ? N8 O7 1.2406(16) . ? N8 O6 1.2729(17) . ? N8 N9 1.3212(19) . ? N12 N13 1.3656(19) . ? N12 H12 0.8800 . ? N13 O14 1.2264(18) . ? N13 O15 1.2270(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 C3 N4 106.72(14) . . ? N2 C3 H3 126.6 . . ? N4 C3 H3 126.6 . . ? N1 C5 N4 111.42(13) . . ? N1 C5 H5 124.3 . . ? N4 C5 H5 124.3 . . ? O11 C10 N9 131.44(14) . . ? O11 C10 N12 124.44(15) . . ? N9 C10 N12 104.09(12) . . ? C5 N1 N2 103.46(14) . . ? C3 N2 N1 111.96(13) . . ? C3 N2 H2 124.0 . . ? N1 N2 H2 124.0 . . ? C3 N4 C5 106.43(14) . . ? C3 N4 H4 126.8 . . ? C5 N4 H4 126.8 . . ? O7 N8 O6 119.56(14) . . ? O7 N8 N9 126.17(13) . . ? O6 N8 N9 114.26(12) . . ? N8 N9 C10 116.84(12) . . ? N13 N12 C10 126.28(13) . . ? N13 N12 H12 116.9 . . ? C10 N12 H12 116.9 . . ? O14 N13 O15 125.25(15) . . ? O14 N13 N12 114.87(13) . . ? O15 N13 N12 119.88(13) . . ? 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 N2 H2 O11 0.88 2.00 2.7521(18) 142 1_545 N2 H2 O15 0.88 2.35 3.0335(17) 135 1_545 N2 H2 O7 0.88 2.50 2.9487(17) 112 . N4 H4 O6 0.88 1.90 2.7542(18) 164 2_556 N4 H4 N8 0.88 2.65 3.3824(19) 141 2_556 N12 H12 O6 0.88 1.90 2.7752(17) 170 2_557 N12 H12 N9 0.88 2.61 3.2763(19) 134 2_557 N12 H12 N8 0.88 2.67 3.5145(18) 162 2_557 C3 H3 O7 0.95 2.38 2.8848(18) 113 . N2 H2 O7 0.88 2.50 2.9487(17) 112 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.191 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.046