# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shrv212 _database_code_depnum_ccdc_archive 'CCDC 906539' #TrackingRef 'shrv212.cif' _audit_creation_date 2012-09-17 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H3 N5 O3' _chemical_formula_sum 'C4 H3 N5 O3' _chemical_formula_weight 169.11 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7709(12) _cell_length_b 5.7826(8) _cell_length_c 13.3180(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.504(6) _cell_angle_gamma 90.00 _cell_volume 668.04(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9549 _exptl_absorpt_correction_T_max 0.9985 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6049 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 26.55 _reflns_number_total 1375 _reflns_number_gt 804 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0454P)^2^+0.0181P] 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_number_reflns 1375 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.01297(18) 0.5744(3) 0.34324(14) 0.0424(5) Uani 1 1 d . . . N2 N 0.1495(2) 0.6662(3) 0.32542(14) 0.0451(5) Uani 1 1 d . . . C3 C 0.2547(2) 0.5218(4) 0.36492(16) 0.0407(6) Uani 1 1 d . . . C4 C 0.1913(2) 0.3308(4) 0.40958(17) 0.0413(6) Uani 1 1 d . . . C5 C 0.0262(3) 0.3652(4) 0.39453(17) 0.0433(6) Uani 1 1 d . . . C6 C -0.1309(2) 0.6922(4) 0.3074(2) 0.0572(7) Uani 1 1 d . . . H6A H -0.1227 0.8517 0.3274 0.086 Uiso 1 1 calc R . . H6B H -0.2131 0.6206 0.3363 0.086 Uiso 1 1 calc R . . H6C H -0.1522 0.6822 0.2347 0.086 Uiso 1 1 calc R . . N7 N 0.4145(2) 0.5632(4) 0.36142(15) 0.0486(5) Uani 1 1 d . . . O8 O 0.45358(19) 0.7421(3) 0.32389(14) 0.0721(6) Uani 1 1 d . . . O9 O 0.50362(17) 0.4123(3) 0.39812(13) 0.0623(5) Uani 1 1 d . . . N10 N 0.2632(2) 0.1533(3) 0.45830(15) 0.0476(5) Uani 1 1 d . . . N11 N 0.3195(2) 0.0020(4) 0.50070(19) 0.0663(7) Uani 1 1 d . . . O12 O -0.07960(19) 0.2522(3) 0.41913(13) 0.0598(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 N1 0.0327(10) 0.0421(11) 0.0519(12) 0.0002(9) 0.0046(8) -0.0004(8) N2 0.0411(11) 0.0426(11) 0.0506(13) 0.0007(9) 0.0040(9) -0.0048(8) C3 0.0351(12) 0.0449(13) 0.0415(14) 0.0013(10) 0.0040(10) -0.0014(10) C4 0.0401(13) 0.0378(12) 0.0454(14) 0.0027(10) 0.0041(11) 0.0024(9) C5 0.0442(14) 0.0419(13) 0.0437(14) -0.0033(11) 0.0067(11) -0.0015(10) C6 0.0410(14) 0.0541(15) 0.0755(19) 0.0024(12) 0.0055(13) 0.0050(11) N7 0.0412(12) 0.0589(13) 0.0449(12) 0.0036(10) 0.0038(9) -0.0011(10) O8 0.0511(11) 0.0825(14) 0.0827(15) 0.0290(11) 0.0101(10) -0.0137(9) O9 0.0439(10) 0.0741(12) 0.0680(13) 0.0108(10) 0.0058(8) 0.0117(9) N10 0.0433(11) 0.0439(12) 0.0555(13) 0.0000(10) 0.0068(10) -0.0014(9) N11 0.0542(13) 0.0538(14) 0.0889(19) 0.0183(13) 0.0039(12) 0.0024(10) O12 0.0492(10) 0.0554(11) 0.0767(13) 0.0068(9) 0.0158(9) -0.0102(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.363(2) . ? N1 C5 1.386(3) . ? N1 C6 1.451(3) . ? N2 C3 1.297(3) . ? C3 C4 1.407(3) . ? C3 N7 1.429(3) . ? C4 N10 1.323(3) . ? C4 C5 1.446(3) . ? C5 O12 1.218(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N7 O8 1.220(2) . ? N7 O9 1.224(2) . ? N10 N11 1.116(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 114.47(17) . . ? N2 N1 C6 120.27(19) . . ? C5 N1 C6 125.24(18) . . ? C3 N2 N1 105.64(17) . . ? N2 C3 C4 112.02(19) . . ? N2 C3 N7 121.40(19) . . ? C4 C3 N7 126.59(19) . . ? N10 C4 C3 128.8(2) . . ? N10 C4 C5 124.71(19) . . ? C3 C4 C5 106.49(17) . . ? O12 C5 N1 126.1(2) . . ? O12 C5 C4 132.5(2) . . ? N1 C5 C4 101.37(18) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O8 N7 O9 124.52(19) . . ? O8 N7 C3 119.46(19) . . ? O9 N7 C3 116.0(2) . . ? N11 N10 C4 177.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C3 -0.5(2) . . . . ? C6 N1 N2 C3 -179.2(2) . . . . ? N1 N2 C3 C4 0.2(2) . . . . ? N1 N2 C3 N7 -179.44(18) . . . . ? N2 C3 C4 N10 -178.5(2) . . . . ? N7 C3 C4 N10 1.1(4) . . . . ? N2 C3 C4 C5 0.2(3) . . . . ? N7 C3 C4 C5 179.8(2) . . . . ? N2 N1 C5 O12 179.6(2) . . . . ? C6 N1 C5 O12 -1.8(4) . . . . ? N2 N1 C5 C4 0.6(2) . . . . ? C6 N1 C5 C4 179.2(2) . . . . ? N10 C4 C5 O12 -0.6(4) . . . . ? C3 C4 C5 O12 -179.3(2) . . . . ? N10 C4 C5 N1 178.3(2) . . . . ? C3 C4 C5 N1 -0.5(2) . . . . ? N2 C3 N7 O8 2.8(3) . . . . ? C4 C3 N7 O8 -176.8(2) . . . . ? N2 C3 N7 O9 -177.7(2) . . . . ? C4 C3 N7 O9 2.7(3) . . . . ? C3 C4 N10 N11 163(6) . . . . ? C5 C4 N10 N11 -15(6) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.55 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.154 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.041 data_shrv214 _database_code_depnum_ccdc_archive 'CCDC 906540' #TrackingRef 'shrv214.cif' _audit_creation_date 2012-10-16 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 3,5-dinitro-1H-pyrazole-1,4-diamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 H4 N6 O4' _chemical_formula_sum 'C3 H4 N6 O4' _chemical_formula_weight 188.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 6.4359(4) _cell_length_b 12.7184(7) _cell_length_c 15.8769(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1299.59(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9269 _exptl_absorpt_correction_T_max 0.9759 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11406 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.53 _reflns_number_total 1333 _reflns_number_gt 1246 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0445P)^2^+0.5345P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1333 _refine_ls_number_parameters 130 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.09111(15) 0.68916(7) 0.34426(6) 0.0160(2) Uani 1 1 d . . . N2 N 0.09361(16) 0.73938(7) 0.41600(6) 0.0168(2) Uani 1 1 d . . . C3 C 0.15431(17) 0.66657(9) 0.47309(7) 0.0165(3) Uani 1 1 d . . . C4 C 0.19505(17) 0.56724(9) 0.43769(8) 0.0171(3) Uani 1 1 d . . . C5 C 0.14942(18) 0.58561(9) 0.35256(7) 0.0175(3) Uani 1 1 d . . . N6 N 0.00051(17) 0.73497(8) 0.27367(6) 0.0195(2) Uani 1 1 d D . . H6A H 0.082(2) 0.7253(12) 0.2318(8) 0.029 Uiso 1 1 d D . . H6B H -0.012(3) 0.8006(8) 0.2856(9) 0.029 Uiso 1 1 d D . . N7 N 0.16112(15) 0.69308(8) 0.55897(6) 0.0189(2) Uani 1 1 d . . . O8 O 0.11993(15) 0.78394(7) 0.58127(6) 0.0251(2) Uani 1 1 d . . . O9 O 0.20803(15) 0.62170(7) 0.60881(6) 0.0264(2) Uani 1 1 d . . . N10 N 0.25880(18) 0.47844(8) 0.47453(7) 0.0226(2) Uani 1 1 d D . . H10A H 0.289(3) 0.4791(13) 0.5267(6) 0.034 Uiso 1 1 d D . . H10B H 0.293(3) 0.4263(10) 0.4448(9) 0.034 Uiso 1 1 d D . . N11 N 0.15911(16) 0.51429(8) 0.28568(7) 0.0206(2) Uani 1 1 d . . . O12 O 0.20391(15) 0.42238(7) 0.30448(6) 0.0279(2) Uani 1 1 d . . . O13 O 0.12374(16) 0.54475(8) 0.21330(6) 0.0290(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0186(5) 0.0150(5) 0.0144(5) 0.0001(3) -0.0005(4) 0.0002(4) N2 0.0192(5) 0.0164(5) 0.0147(5) -0.0010(4) -0.0002(4) -0.0005(4) C3 0.0172(5) 0.0170(6) 0.0151(6) 0.0015(4) -0.0004(4) -0.0013(4) C4 0.0147(5) 0.0167(6) 0.0200(6) 0.0013(4) 0.0002(4) -0.0022(4) C5 0.0190(6) 0.0149(6) 0.0186(6) -0.0006(4) 0.0008(4) 0.0000(4) N6 0.0262(6) 0.0182(5) 0.0141(5) 0.0025(4) -0.0014(4) 0.0018(4) N7 0.0191(5) 0.0215(5) 0.0161(5) 0.0009(4) -0.0014(4) -0.0026(4) O8 0.0314(5) 0.0247(5) 0.0192(5) -0.0049(4) -0.0013(4) 0.0028(4) O9 0.0342(5) 0.0266(5) 0.0185(4) 0.0075(4) -0.0060(4) -0.0035(4) N10 0.0255(5) 0.0170(5) 0.0252(6) 0.0031(4) -0.0035(4) 0.0023(4) N11 0.0208(5) 0.0184(5) 0.0226(6) -0.0039(4) 0.0011(4) -0.0004(4) O12 0.0351(6) 0.0154(4) 0.0334(5) -0.0044(4) 0.0000(4) 0.0030(4) O13 0.0408(6) 0.0281(5) 0.0181(5) -0.0049(4) -0.0017(4) 0.0040(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 N1 N2 1.3059(14) . ? N1 C5 1.3758(15) . ? N1 N6 1.3912(14) . ? N2 C3 1.3534(15) . ? C3 N7 1.4053(15) . ? C3 C4 1.4074(16) . ? C4 N10 1.3363(16) . ? C4 C5 1.4028(17) . ? C5 N11 1.3979(15) . ? N6 H6A 0.856(9) . ? N6 H6B 0.860(9) . ? N7 O8 1.2373(14) . ? N7 O9 1.2416(13) . ? N10 H10A 0.850(9) . ? N10 H10B 0.842(9) . ? N11 O13 1.2340(14) . ? N11 O12 1.2404(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 112.41(9) . . ? N2 N1 N6 120.20(9) . . ? C5 N1 N6 126.32(10) . . ? N1 N2 C3 104.66(9) . . ? N2 C3 N7 119.65(10) . . ? N2 C3 C4 113.61(10) . . ? N7 C3 C4 126.66(10) . . ? N10 C4 C5 128.81(11) . . ? N10 C4 C3 129.87(11) . . ? C5 C4 C3 101.31(10) . . ? N1 C5 N11 124.10(11) . . ? N1 C5 C4 107.99(10) . . ? N11 C5 C4 127.91(11) . . ? N1 N6 H6A 108.1(12) . . ? N1 N6 H6B 105.6(11) . . ? H6A N6 H6B 111.7(14) . . ? O8 N7 O9 123.55(10) . . ? O8 N7 C3 119.68(10) . . ? O9 N7 C3 116.78(10) . . ? C4 N10 H10A 119.2(11) . . ? C4 N10 H10B 119.9(12) . . ? H10A N10 H10B 119.7(16) . . ? O13 N11 O12 124.25(10) . . ? O13 N11 C5 119.70(10) . . ? O12 N11 C5 116.05(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 C5 N1 N2 C3 -0.30(12) . . . . ? N6 N1 N2 C3 168.62(10) . . . . ? N1 N2 C3 N7 -176.05(10) . . . . ? N1 N2 C3 C4 0.86(13) . . . . ? N2 C3 C4 N10 179.35(12) . . . . ? N7 C3 C4 N10 -4.0(2) . . . . ? N2 C3 C4 C5 -1.04(13) . . . . ? N7 C3 C4 C5 175.62(11) . . . . ? N2 N1 C5 N11 179.70(10) . . . . ? N6 N1 C5 N11 11.59(18) . . . . ? N2 N1 C5 C4 -0.34(13) . . . . ? N6 N1 C5 C4 -168.45(11) . . . . ? N10 C4 C5 N1 -179.59(12) . . . . ? C3 C4 C5 N1 0.79(12) . . . . ? N10 C4 C5 N11 0.4(2) . . . . ? C3 C4 C5 N11 -179.26(11) . . . . ? N2 C3 N7 O8 -2.99(16) . . . . ? C4 C3 N7 O8 -179.47(11) . . . . ? N2 C3 N7 O9 176.55(10) . . . . ? C4 C3 N7 O9 0.07(17) . . . . ? N1 C5 N11 O13 3.66(18) . . . . ? C4 C5 N11 O13 -176.29(12) . . . . ? N1 C5 N11 O12 -176.29(11) . . . . ? C4 C5 N11 O12 3.76(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 N6 H6A O8 0.856(9) 2.405(12) 3.1591(14) 147.4(16) 7_575 N6 H6B O12 0.860(9) 2.443(14) 2.9920(13) 122.3(13) 3 N10 H10A O9 0.850(9) 2.293(15) 2.8235(15) 120.7(14) . N10 H10B O12 0.842(9) 2.300(15) 2.8147(15) 119.7(14) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.287 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.046