# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'V. Bertolasi' 'V. Ferretti' 'P. Gilli' 'Gastone Gilli' 'L. Pretto' _publ_contact_author_name 'Prof V Bertolasi' _publ_contact_author_address ; Prof V Bertolasi Dipartimento di Chimica Universita di Ferrara Laboratorio di Chimica Inorganica e via L. Borsari 46 Ferrara 44100 ITALY ; _publ_contact_author_email 'M38@DNS.UNIFE.IT/V.BEROLASI@UNIFE.IT' _publ_section_title ; Hydrogen-bonded supramolecular structurs in co-crystals of beta- or zeta-diketone enols with 2,6-diaminopyridine or 2,4-diaminopyrimidine. ; data_(1) _database_code_CSD 193879 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-cyclopentanedionate, 2,6-diaminopyridinium, hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C5 H5 O2)-, (C5 N3 H8)+, H2 O' _chemical_formula_sum 'C10 H15 N3 O3' _chemical_formula_weight 225.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 7.394(2) _cell_length_b 19.603(2) _cell_length_c 8.107(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.56(1) _cell_angle_gamma 90.00 _cell_volume 1171.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.096 _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 296 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3631 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3413 _reflns_number_gt 2013 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN (Fair, Enraf-Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al.,1994) ' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995) ; _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^)+(0.0710P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3413 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.88015(15) 0.11221(5) 0.73551(13) 0.0600(3) Uani 1 1 d . . . O2 O 0.74121(16) 0.00156(5) 0.22875(13) 0.0636(3) Uani 1 1 d . . . C1 C 0.82575(17) 0.06853(6) 0.62729(17) 0.0449(3) Uani 1 1 d . . . C2 C 0.81584(19) 0.07522(7) 0.45774(18) 0.0466(3) Uani 1 1 d . . . C3 C 0.75914(17) 0.01434(7) 0.38043(17) 0.0454(3) Uani 1 1 d . . . C4 C 0.72039(19) -0.03778(7) 0.51026(18) 0.0466(3) Uani 1 1 d . . . C5 C 0.7635(2) -0.00173(7) 0.67429(19) 0.0493(3) Uani 1 1 d . . . N1 N 1.18602(16) 0.19417(5) 0.76709(14) 0.0471(3) Uani 1 1 d . . . N2 N 1.4124(2) 0.12350(7) 0.87868(19) 0.0640(4) Uani 1 1 d . . . N3 N 0.9392(2) 0.25563(8) 0.6570(2) 0.0660(4) Uani 1 1 d . . . C6 C 1.3597(2) 0.18594(7) 0.83145(18) 0.0502(3) Uani 1 1 d . . . C7 C 1.4700(3) 0.24370(8) 0.8445(2) 0.0630(4) Uani 1 1 d . . . C8 C 1.3996(3) 0.30512(8) 0.7923(2) 0.0679(5) Uani 1 1 d . . . C9 C 1.2239(2) 0.31229(8) 0.7277(2) 0.0613(4) Uani 1 1 d . . . C10 C 1.1133(2) 0.25539(7) 0.71579(17) 0.0488(3) Uani 1 1 d . . . O3 O 0.78588(18) 0.11523(6) 1.04722(15) 0.0638(3) Uani 1 1 d . . . H2 H 0.848(2) 0.1147(8) 0.4044(19) 0.053(4) Uiso 1 1 d . . . H41 H 0.799(2) -0.0779(8) 0.4950(18) 0.053(4) Uiso 1 1 d . . . H42 H 0.594(2) -0.0544(8) 0.4894(17) 0.054(4) Uiso 1 1 d . . . H51 H 0.865(2) -0.0236(8) 0.7413(18) 0.053(4) Uiso 1 1 d . . . H52 H 0.656(2) 0.0010(8) 0.742(2) 0.063(4) Uiso 1 1 d . . . H1 H 1.108(2) 0.1584(8) 0.7637(19) 0.057(4) Uiso 1 1 d . . . H21 H 1.340(3) 0.0818(11) 0.849(3) 0.094(6) Uiso 1 1 d . . . H22 H 1.522(3) 0.1161(9) 0.931(2) 0.075(6) Uiso 1 1 d . . . H31 H 0.879(3) 0.2981(10) 0.627(2) 0.081(6) Uiso 1 1 d . . . H32 H 0.877(2) 0.2180(10) 0.664(2) 0.070(5) Uiso 1 1 d . . . H7 H 1.588(3) 0.2390(9) 0.883(2) 0.072(5) Uiso 1 1 d . . . H8 H 1.477(3) 0.3453(10) 0.800(2) 0.087(6) Uiso 1 1 d . . . H9 H 1.169(2) 0.3563(9) 0.686(2) 0.071(5) Uiso 1 1 d . . . H301 H 0.779(3) 0.0723(11) 1.106(2) 0.082(6) Uiso 1 1 d . . . H302 H 0.829(3) 0.1057(10) 0.949(3) 0.092(7) 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 0.0728(7) 0.0509(6) 0.0568(6) -0.0052(5) 0.0077(5) -0.0176(5) O2 0.0842(8) 0.0538(6) 0.0520(6) -0.0014(5) 0.0011(5) -0.0163(5) C1 0.0399(7) 0.0390(6) 0.0562(8) 0.0008(6) 0.0065(5) -0.0037(5) C2 0.0485(7) 0.0378(6) 0.0539(8) 0.0065(6) 0.0062(6) -0.0065(5) C3 0.0392(7) 0.0419(7) 0.0551(8) 0.0026(6) 0.0031(5) -0.0020(5) C4 0.0416(7) 0.0365(6) 0.0615(8) 0.0023(6) 0.0029(6) -0.0056(5) C5 0.0494(8) 0.0432(7) 0.0555(8) 0.0060(6) 0.0064(6) -0.0069(6) N1 0.0510(7) 0.0363(5) 0.0537(7) -0.0040(5) 0.0029(5) -0.0066(5) N2 0.0600(9) 0.0471(7) 0.0820(10) -0.0081(6) -0.0128(7) 0.0040(6) N3 0.0646(9) 0.0455(7) 0.0855(11) 0.0060(7) -0.0095(7) -0.0004(7) C6 0.0529(8) 0.0449(7) 0.0523(8) -0.0102(6) 0.0018(6) -0.0020(6) C7 0.0540(10) 0.0563(9) 0.0779(11) -0.0135(8) -0.0005(8) -0.0099(7) C8 0.0715(11) 0.0488(9) 0.0841(12) -0.0130(8) 0.0097(9) -0.0194(8) C9 0.0735(11) 0.0374(7) 0.0732(10) -0.0019(7) 0.0081(8) -0.0078(7) C10 0.0572(9) 0.0392(7) 0.0503(8) -0.0026(5) 0.0067(6) -0.0008(6) O3 0.0892(9) 0.0494(6) 0.0527(6) -0.0014(5) 0.0045(6) -0.0070(5) _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 C1 1.2683(16) . ? O2 C3 1.2516(17) . ? C1 C2 1.377(2) . ? C1 C5 1.5108(18) . ? C2 C3 1.3967(19) . ? C2 H2 0.928(16) . ? C3 C4 1.5105(19) . ? C4 C5 1.517(2) . ? C4 H41 0.992(16) . ? C4 H42 0.990(15) . ? C5 H51 0.988(15) . ? C5 H52 1.004(18) . ? N1 C6 1.3567(19) . ? N1 C10 1.3663(17) . ? N1 H1 0.907(17) . ? N2 C6 1.3317(19) . ? N2 H21 0.99(2) . ? N2 H22 0.90(2) . ? N3 C10 1.337(2) . ? N3 H31 0.97(2) . ? N3 H32 0.874(19) . ? C6 C7 1.395(2) . ? C7 C8 1.365(3) . ? C7 H7 0.906(19) . ? C8 C9 1.369(3) . ? C8 H8 0.97(2) . ? C9 C10 1.382(2) . ? C9 H9 1.003(18) . ? O3 H301 0.97(2) . ? O3 H302 0.90(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 O1 C1 C2 127.96(12) . . ? O1 C1 C5 121.82(13) . . ? C2 C1 C5 110.21(12) . . ? C1 C2 C3 110.91(12) . . ? C1 C2 H2 123.3(9) . . ? C3 C2 H2 125.7(9) . . ? O2 C3 C2 128.06(13) . . ? O2 C3 C4 122.55(12) . . ? C2 C3 C4 109.39(12) . . ? C3 C4 C5 104.92(11) . . ? C3 C4 H41 107.6(9) . . ? C5 C4 H41 113.2(9) . . ? C3 C4 H42 109.4(9) . . ? C5 C4 H42 115.6(8) . . ? H41 C4 H42 105.9(12) . . ? C1 C5 C4 104.50(11) . . ? C1 C5 H51 107.5(9) . . ? C4 C5 H51 112.1(9) . . ? C1 C5 H52 111.1(9) . . ? C4 C5 H52 112.8(9) . . ? H51 C5 H52 108.6(13) . . ? C6 N1 C10 123.98(12) . . ? C6 N1 H1 120.1(10) . . ? C10 N1 H1 115.8(10) . . ? C6 N2 H21 123.2(12) . . ? C6 N2 H22 121.2(12) . . ? H21 N2 H22 115.4(17) . . ? C10 N3 H31 120.1(11) . . ? C10 N3 H32 118.3(12) . . ? H31 N3 H32 120.7(17) . . ? N2 C6 N1 117.80(13) . . ? N2 C6 C7 124.64(15) . . ? N1 C6 C7 117.56(14) . . ? C8 C7 C6 119.09(17) . . ? C8 C7 H7 121.9(12) . . ? C6 C7 H7 119.0(12) . . ? C7 C8 C9 122.41(15) . . ? C7 C8 H8 119.1(12) . . ? C9 C8 H8 118.5(12) . . ? C8 C9 C10 118.83(15) . . ? C8 C9 H9 124.6(11) . . ? C10 C9 H9 116.6(11) . . ? N3 C10 N1 117.14(13) . . ? N3 C10 C9 124.74(14) . . ? N1 C10 C9 118.13(15) . . ? H301 O3 H302 107.0(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.184 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.048 ##===END data_(2) _database_code_CSD 193880 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-cyclopentanedionate, 2,6-diaminopyrimidinium, hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C5 H5 O2)-, (C4 H7 N4)+, H2 O' _chemical_formula_sum 'C9 H14 N4 O3' _chemical_formula_weight 226.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.780(5) _cell_length_b 6.912(1) _cell_length_c 13.005(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.85(2) _cell_angle_gamma 90.00 _cell_volume 2265.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description 'irregular' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.102 _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 296 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2852 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2726 _reflns_number_gt 1967 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN (Fair, Enraf-Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995) ; _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^)+(0.0679P)^2^+0.7151P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2726 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.16722(4) 0.0609(2) 0.01684(11) 0.0584(4) Uani 1 1 d . . . O2 O 0.35275(4) 0.0552(2) 0.20546(10) 0.0583(4) Uani 1 1 d . . . O3 O 0.38447(6) -0.2350(3) 0.10087(14) 0.0695(4) Uani 1 1 d . . . C1 C 0.21471(6) 0.1063(2) 0.07836(13) 0.0415(4) Uani 1 1 d . . . C2 C 0.26054(6) 0.0127(3) 0.09015(13) 0.0416(4) Uani 1 1 d . . . C3 C 0.30511(6) 0.1042(3) 0.17008(13) 0.0417(4) Uani 1 1 d . . . N1 N 0.07730(6) 0.1829(2) 0.03503(12) 0.0482(4) Uani 1 1 d . . . N2 N -0.00425(5) 0.28802(19) -0.10632(10) 0.0381(3) Uani 1 1 d . . . N3 N 0.06810(6) 0.2434(3) -0.14513(15) 0.0597(4) Uani 1 1 d . . . N4 N -0.07574(6) 0.3272(2) -0.06604(14) 0.0477(3) Uani 1 1 d . . . C4 C 0.28820(8) 0.2821(3) 0.2130(2) 0.0609(5) Uani 1 1 d . . . C5 C 0.22817(7) 0.2800(3) 0.15443(18) 0.0561(5) Uani 1 1 d . . . C6 C 0.04658(6) 0.2395(2) -0.07183(13) 0.0416(4) Uani 1 1 d . . . C7 C -0.02548(6) 0.2814(2) -0.03117(13) 0.0385(3) Uani 1 1 d . . . C8 C 0.00613(8) 0.2265(3) 0.08417(15) 0.0493(4) Uani 1 1 d . . . C9 C 0.05698(7) 0.1787(3) 0.11227(15) 0.0510(4) Uani 1 1 d . . . H2 H 0.2607(8) -0.109(3) 0.0491(17) 0.063(6) Uiso 1 1 d . . . H401 H 0.3019(10) 0.271(3) 0.296(2) 0.085(8) Uiso 1 1 d . . . H402 H 0.3023(10) 0.393(4) 0.191(2) 0.077(7) Uiso 1 1 d . . . H501 H 0.2130(9) 0.264(3) 0.206(2) 0.066(6) Uiso 1 1 d . . . H502 H 0.2142(10) 0.397(4) 0.111(2) 0.087(8) Uiso 1 1 d . . . H1 H 0.1139(9) 0.143(3) 0.0551(18) 0.071(6) Uiso 1 1 d . . . H31 H 0.0466(10) 0.284(3) -0.225(2) 0.078(7) Uiso 1 1 d . . . H32 H 0.0996(10) 0.225(3) -0.1222(19) 0.066(6) Uiso 1 1 d . . . H41 H -0.0911(8) 0.324(3) -0.0196(18) 0.059(6) Uiso 1 1 d . . . H42 H -0.0958(8) 0.363(3) -0.1407(18) 0.055(5) Uiso 1 1 d . . . H8 H -0.0120(9) 0.228(3) 0.1248(19) 0.066(6) Uiso 1 1 d . . . H9 H 0.0808(8) 0.145(3) 0.1885(18) 0.065(6) Uiso 1 1 d . . . H301 H 0.3707(10) -0.157(5) 0.134(2) 0.100(9) Uiso 1 1 d . . . H302 H 0.3586(12) -0.314(4) 0.062(3) 0.098(9) 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 0.0320(6) 0.0678(9) 0.0643(7) -0.0072(6) 0.0094(5) 0.0027(5) O2 0.0314(6) 0.0827(10) 0.0595(7) -0.0194(6) 0.0179(5) -0.0029(6) O3 0.0599(9) 0.0805(11) 0.0826(10) -0.0279(8) 0.0442(8) -0.0118(8) C1 0.0352(7) 0.0472(9) 0.0410(7) 0.0013(6) 0.0150(6) 0.0005(6) C2 0.0374(8) 0.0431(9) 0.0434(8) -0.0059(7) 0.0161(6) 0.0005(6) C3 0.0353(7) 0.0531(9) 0.0405(7) -0.0065(7) 0.0195(6) -0.0044(6) N1 0.0371(7) 0.0495(8) 0.0481(8) -0.0002(6) 0.0082(6) 0.0044(6) N2 0.0316(6) 0.0389(7) 0.0415(6) 0.0035(5) 0.0130(5) 0.0001(5) N3 0.0336(7) 0.0859(13) 0.0619(10) 0.0097(9) 0.0222(7) 0.0076(8) N4 0.0416(7) 0.0552(9) 0.0515(8) 0.0017(7) 0.0248(7) 0.0021(6) C4 0.0488(10) 0.0642(13) 0.0687(13) -0.0277(10) 0.0237(9) -0.0070(9) C5 0.0475(10) 0.0597(12) 0.0629(11) -0.0131(9) 0.0251(9) 0.0062(8) C6 0.0341(7) 0.0370(8) 0.0465(8) 0.0008(6) 0.0100(6) 0.0005(6) C7 0.0413(8) 0.0309(7) 0.0425(8) -0.0024(6) 0.0169(6) -0.0025(6) C8 0.0633(11) 0.0446(9) 0.0426(8) -0.0013(7) 0.0247(8) -0.0023(8) C9 0.0520(10) 0.0458(9) 0.0390(8) -0.0003(7) 0.0034(7) 0.0019(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2618(18) . ? O2 C3 1.2514(18) . ? O3 H301 0.87(3) . ? O3 H302 0.87(3) . ? C1 C2 1.378(2) . ? C1 C5 1.500(2) . ? C2 C3 1.390(2) . ? C2 H2 1.00(2) . ? C3 C4 1.505(2) . ? N1 C9 1.344(2) . ? N1 C6 1.348(2) . ? N1 H1 0.98(2) . ? N2 C6 1.3322(19) . ? N2 C7 1.338(2) . ? N3 C6 1.321(2) . ? N3 H31 0.99(3) . ? N3 H32 0.81(2) . ? N4 C7 1.313(2) . ? N4 H41 0.87(2) . ? N4 H42 0.93(2) . ? C4 C5 1.514(3) . ? C4 H401 0.98(3) . ? C4 H402 0.96(3) . ? C5 H501 0.94(2) . ? C5 H502 0.97(3) . ? C7 C8 1.435(2) . ? C8 C9 1.343(3) . ? C8 H8 0.87(2) . ? C9 H9 0.96(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 H301 O3 H302 104(3) . . ? O1 C1 C2 128.64(16) . . ? O1 C1 C5 121.47(15) . . ? C2 C1 C5 109.88(14) . . ? C1 C2 C3 111.13(15) . . ? C1 C2 H2 123.2(11) . . ? C3 C2 H2 125.6(11) . . ? O2 C3 C2 128.61(16) . . ? O2 C3 C4 122.10(15) . . ? C2 C3 C4 109.29(14) . . ? C9 N1 C6 119.62(15) . . ? C9 N1 H1 120.7(13) . . ? C6 N1 H1 119.7(13) . . ? C6 N2 C7 118.41(13) . . ? C6 N3 H31 120.0(14) . . ? C6 N3 H32 118.6(16) . . ? H31 N3 H32 121(2) . . ? C7 N4 H41 120.8(14) . . ? C7 N4 H42 120.7(12) . . ? H41 N4 H42 118.5(19) . . ? C3 C4 C5 104.77(15) . . ? C3 C4 H401 107.8(15) . . ? C5 C4 H401 112.8(16) . . ? C3 C4 H402 108.0(14) . . ? C5 C4 H402 111.0(14) . . ? H401 C4 H402 112(2) . . ? C1 C5 C4 104.84(14) . . ? C1 C5 H501 108.4(14) . . ? C4 C5 H501 111.9(14) . . ? C1 C5 H502 110.7(15) . . ? C4 C5 H502 111.7(15) . . ? H501 C5 H502 109(2) . . ? N3 C6 N2 119.26(15) . . ? N3 C6 N1 117.87(15) . . ? N2 C6 N1 122.86(15) . . ? N4 C7 N2 118.10(14) . . ? N4 C7 C8 121.32(15) . . ? N2 C7 C8 120.58(15) . . ? C9 C8 C7 117.47(17) . . ? C9 C8 H8 130.5(14) . . ? C7 C8 H8 112.0(15) . . ? C8 C9 N1 121.04(16) . . ? C8 C9 H9 121.9(12) . . ? N1 C9 H9 117.0(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.385 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.041 ##===END data_(3) _database_code_CSD 193881 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-cyclohexanedionate, 2,6-diaminopyridinium, 1,3-cyclohexanedione enol, hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 O2, (C6 H7 O2)-, (C4 H7 N4)+, H2 O' _chemical_formula_sum 'C16 H23 H N4 O5' _chemical_formula_weight 352.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 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' _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 8.642(2) _cell_length_b 10.132(2) _cell_length_c 10.721(5) _cell_angle_alpha 91.37(3) _cell_angle_beta 92.95(2) _cell_angle_gamma 106.66(2) _cell_volume 897.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _exptl_crystal_description 'irregular' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.098 _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 296 _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 'Enraf-Nonius Cad-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4547 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.96 _reflns_number_total 4319 _reflns_number_gt 2759 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN (Fair, Enraf-Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.1007P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4319 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1731 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.48366(17) 0.26578(15) -0.04823(11) 0.0785(4) Uani 1 1 d . . . O31 O 0.8737(2) 0.21300(16) 0.24601(12) 0.0874(5) Uani 1 1 d . . . C11 C 0.5978(2) 0.21627(19) -0.01847(15) 0.0645(5) Uani 1 1 d . . . C21 C 0.6810(2) 0.2424(2) 0.09954(16) 0.0732(6) Uani 1 1 d . . . C31 C 0.8032(2) 0.18765(19) 0.13550(16) 0.0687(5) Uani 1 1 d . . . C41 C 0.8554(3) 0.0945(3) 0.04680(18) 0.0811(7) Uani 1 1 d . . . C51 C 0.8152(3) 0.1163(3) -0.0887(2) 0.0985(9) Uani 1 1 d . . . C61 C 0.6451(3) 0.1249(2) -0.11198(17) 0.0694(5) Uani 1 1 d . . . O12 O 1.17748(17) 0.34281(16) 0.69456(11) 0.0815(4) Uani 1 1 d . . . O32 O 1.0980(3) 0.1147(2) 0.30078(16) 0.1107(8) Uani 1 1 d . . . C12 C 1.1998(2) 0.2543(2) 0.62057(15) 0.0664(5) Uani 1 1 d . . . C22 C 1.1336(2) 0.2346(2) 0.49516(15) 0.0699(5) Uani 1 1 d . . . C32 C 1.1620(3) 0.1412(2) 0.41541(18) 0.0819(6) Uani 1 1 d . . . C42 C 1.2721(5) 0.0559(4) 0.4502(3) 0.1233(14) Uani 1 1 d . . . C52 C 1.3787(5) 0.1117(5) 0.5653(3) 0.1346(17) Uani 1 1 d . . . C62 C 1.2984(4) 0.1631(3) 0.6642(2) 0.1004(10) Uani 1 1 d . . . N1 N 0.14846(15) 0.50970(17) 0.14618(12) 0.0629(4) Uani 1 1 d . . . C2 C 0.22214(19) 0.44339(19) 0.07192(14) 0.0586(4) Uani 1 1 d . . . N2 N 0.1666(2) 0.4152(2) -0.04636(14) 0.0719(4) Uani 1 1 d . . . N3 N 0.35183(17) 0.40231(19) 0.11101(13) 0.0675(4) Uani 1 1 d . . . C4 C 0.4117(2) 0.4328(3) 0.23210(17) 0.0788(6) Uani 1 1 d . . . C5 C 0.3453(2) 0.5007(3) 0.31079(16) 0.0794(6) Uani 1 1 d . . . C6 C 0.20798(19) 0.5389(2) 0.26527(14) 0.0649(5) Uani 1 1 d . . . N6 N 0.1370(2) 0.6051(2) 0.34008(14) 0.0844(6) Uani 1 1 d . . . O1 O 0.75387(19) 0.3793(2) 0.40074(12) 0.0834(5) Uani 1 1 d . . . H32 H 1.017(4) 0.160(3) 0.278(2) 0.133(11) Uani 1 1 d . . . H21 H 0.654(2) 0.306(2) 0.158(2) 0.079(6) Uiso 1 1 d . . . H411 H 0.966(4) 0.098(3) 0.070(3) 0.122(9) Uiso 1 1 d . . . H412 H 0.778(4) -0.007(4) 0.061(3) 0.155(12) Uiso 1 1 d . . . H511 H 0.827(3) 0.036(3) -0.144(2) 0.106(8) Uiso 1 1 d . . . H512 H 0.896(6) 0.229(6) -0.109(5) 0.25(2) Uiso 1 1 d . . . H611 H 0.634(3) 0.158(2) -0.190(3) 0.099(7) Uiso 1 1 d . . . H612 H 0.558(3) 0.031(3) -0.111(2) 0.092(7) Uiso 1 1 d . . . H22 H 1.067(3) 0.287(2) 0.4714(19) 0.077(6) Uiso 1 1 d . . . H421 H 1.322(4) 0.044(3) 0.382(3) 0.133(11) Uiso 1 1 d . . . H422 H 1.219(7) -0.034(6) 0.482(5) 0.25(3) Uiso 1 1 d . . . H521 H 1.437(4) 0.058(3) 0.592(3) 0.130(10) Uiso 1 1 d . . . H522 H 1.462(5) 0.204(5) 0.537(4) 0.21(2) Uiso 1 1 d . . . H621 H 1.351(4) 0.197(3) 0.727(3) 0.112(9) Uiso 1 1 d . . . H622 H 1.212(4) 0.083(4) 0.694(3) 0.158(15) Uiso 1 1 d . . . H210 H 0.215(3) 0.378(2) -0.096(2) 0.089(7) Uiso 1 1 d . . . H220 H 0.089(3) 0.441(2) -0.074(2) 0.079(6) Uiso 1 1 d . . . H3 H 0.405(3) 0.355(2) 0.060(2) 0.080(6) Uiso 1 1 d . . . H4 H 0.498(3) 0.402(2) 0.254(2) 0.086(6) Uiso 1 1 d . . . H5 H 0.379(3) 0.526(2) 0.399(2) 0.091(7) Uiso 1 1 d . . . H61 H 0.047(3) 0.619(2) 0.3181(19) 0.073(6) Uiso 1 1 d . . . H62 H 0.163(2) 0.608(2) 0.422(2) 0.077(6) Uiso 1 1 d . . . H11 H 0.794(4) 0.464(4) 0.371(3) 0.141(13) Uiso 1 1 d . . . H12 H 0.798(3) 0.324(3) 0.355(3) 0.103(8) 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 O11 0.0896(9) 0.1078(10) 0.0532(7) -0.0183(6) -0.0287(6) 0.0602(8) O31 0.1172(11) 0.1074(10) 0.0566(7) -0.0295(7) -0.0448(7) 0.0738(9) C11 0.0769(11) 0.0718(10) 0.0501(8) -0.0103(7) -0.0222(7) 0.0354(9) C21 0.0951(13) 0.0857(12) 0.0521(9) -0.0244(8) -0.0310(9) 0.0554(11) C31 0.0915(12) 0.0726(11) 0.0500(8) -0.0174(7) -0.0304(8) 0.0440(9) C41 0.1081(16) 0.0939(15) 0.0588(10) -0.0224(10) -0.0337(10) 0.0657(13) C51 0.1116(17) 0.140(2) 0.0663(12) -0.0402(13) -0.0370(12) 0.0826(17) C61 0.0901(13) 0.0764(12) 0.0473(9) -0.0145(8) -0.0259(8) 0.0396(11) O12 0.0901(9) 0.1260(11) 0.0470(6) -0.0253(7) -0.0216(6) 0.0673(8) O32 0.1388(15) 0.1558(17) 0.0664(9) -0.0551(10) -0.0580(9) 0.1048(14) C12 0.0668(10) 0.0930(12) 0.0469(8) -0.0163(8) -0.0200(7) 0.0406(9) C22 0.0803(11) 0.0957(13) 0.0477(8) -0.0169(8) -0.0266(8) 0.0547(10) C32 0.0948(13) 0.1069(15) 0.0584(10) -0.0305(10) -0.0379(9) 0.0624(12) C42 0.157(3) 0.163(3) 0.0871(16) -0.0664(18) -0.0720(17) 0.125(2) C52 0.162(3) 0.199(4) 0.0887(17) -0.066(2) -0.072(2) 0.145(3) C62 0.131(2) 0.125(2) 0.0649(12) -0.0337(13) -0.0572(14) 0.0818(19) N1 0.0474(7) 0.1054(11) 0.0376(6) 0.0009(6) -0.0035(5) 0.0262(7) C2 0.0486(8) 0.0836(11) 0.0409(7) 0.0019(7) -0.0016(6) 0.0156(7) N2 0.0715(10) 0.1037(13) 0.0445(7) -0.0122(7) -0.0101(7) 0.0352(9) N3 0.0567(8) 0.1016(12) 0.0485(7) -0.0037(7) -0.0022(6) 0.0314(8) C4 0.0607(10) 0.1346(18) 0.0511(9) -0.0002(10) -0.0079(8) 0.0464(11) C5 0.0558(9) 0.1507(19) 0.0393(8) -0.0038(10) -0.0085(7) 0.0445(11) C6 0.0478(8) 0.1118(14) 0.0372(7) 0.0002(8) -0.0007(6) 0.0270(8) N6 0.0657(9) 0.1642(18) 0.0374(7) -0.0084(8) -0.0057(6) 0.0584(11) O1 0.0902(10) 0.1235(14) 0.0457(7) -0.0135(8) -0.0084(6) 0.0491(10) H32 0.18(3) 0.14(3) 0.069(19) -0.052(17) -0.013(19) 0.04(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C11 1.259(2) . ? O31 C31 1.2895(19) . ? C11 C21 1.403(2) . ? C11 C61 1.498(3) . ? C21 H21 0.97(2) . ? C21 C31 1.370(2) . ? C31 C41 1.498(3) . ? C41 H411 0.97(3) . ? C41 H412 1.07(4) . ? C41 C51 1.512(3) . ? C51 H511 1.03(3) . ? C51 H512 1.19(6) . ? C51 C61 1.505(3) . ? C61 H611 0.92(3) . ? C61 H612 1.03(2) . ? O12 C12 1.245(2) . ? O32 C32 1.310(2) . ? O32 H32 0.96(4) . ? C12 C22 1.420(2) . ? C12 C62 1.493(3) . ? C22 H22 0.91(2) . ? C22 C32 1.343(3) . ? C32 C42 1.497(3) . ? C42 H421 0.89(3) . ? C42 H422 0.98(5) . ? C42 C52 1.497(3) . ? C52 H521 0.88(3) . ? C52 H522 1.06(4) . ? C52 C62 1.460(4) . ? C62 H621 0.80(3) . ? C62 H622 1.01(3) . ? N1 C2 1.328(2) . ? N1 C6 1.345(2) . ? C2 N2 1.327(2) . ? C2 N3 1.354(2) . ? N2 H220 0.83(2) . ? N2 H210 0.84(3) . ? N3 H3 0.94(2) . ? N3 C4 1.367(2) . ? C4 H4 0.91(2) . ? C4 C5 1.328(3) . ? C5 H5 0.98(3) . ? C5 C6 1.417(2) . ? C6 N6 1.315(2) . ? N6 H61 0.85(2) . ? N6 H62 0.89(2) . ? O1 H11 0.90(4) . ? O1 H12 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C11 C21 122.34(16) . . ? O11 C11 C61 118.77(14) . . ? C21 C11 C61 118.89(15) . . ? H21 C21 C31 117.7(12) . . ? H21 C21 C11 118.6(12) . . ? C31 C21 C11 123.65(16) . . ? O31 C31 C21 121.17(16) . . ? O31 C31 C41 118.68(15) . . ? C21 C31 C41 120.15(14) . . ? H411 C41 H412 109(3) . . ? H411 C41 C31 108.7(17) . . ? H412 C41 C31 105.6(19) . . ? H411 C41 C51 117.1(18) . . ? H412 C41 C51 102.7(19) . . ? C31 C41 C51 112.89(16) . . ? H511 C51 H512 118(3) . . ? H511 C51 C61 107.5(14) . . ? H512 C51 C61 103(2) . . ? H511 C51 C41 109.9(15) . . ? H512 C51 C41 106(3) . . ? C61 C51 C41 112.9(2) . . ? H611 C61 H612 106(2) . . ? H611 C61 C11 108.1(15) . . ? H612 C61 C11 105.5(13) . . ? H611 C61 C51 109.6(16) . . ? H612 C61 C51 113.8(13) . . ? C11 C61 C51 113.67(15) . . ? C32 O32 H32 115.3(14) . . ? O12 C12 C22 122.77(15) . . ? O12 C12 C62 119.47(14) . . ? C22 C12 C62 117.76(15) . . ? H22 C22 C32 121.0(13) . . ? H22 C22 C12 116.8(13) . . ? C32 C22 C12 122.15(15) . . ? O32 C32 C22 124.47(16) . . ? O32 C32 C42 113.08(17) . . ? C22 C32 C42 122.45(16) . . ? H421 C42 H422 108(4) . . ? H421 C42 C32 107(2) . . ? H422 C42 C32 115(3) . . ? H421 C42 C52 116(2) . . ? H422 C42 C52 97(3) . . ? C32 C42 C52 112.70(19) . . ? H521 C52 H522 106(3) . . ? H521 C52 C62 114(2) . . ? H522 C52 C62 102(3) . . ? H521 C52 C42 114(2) . . ? H522 C52 C42 105(3) . . ? C62 C52 C42 114.4(3) . . ? H621 C62 H622 104(3) . . ? H621 C62 C52 118(2) . . ? H622 C62 C52 108(2) . . ? H621 C62 C12 109(2) . . ? H622 C62 C12 101(2) . . ? C52 C62 C12 114.4(2) . . ? C2 N1 C6 117.97(13) . . ? N2 C2 N1 118.90(15) . . ? N2 C2 N3 117.96(16) . . ? N1 C2 N3 123.14(14) . . ? H220 N2 H210 119(2) . . ? H220 N2 C2 120.4(16) . . ? H210 N2 C2 120.2(16) . . ? H3 N3 C2 124.3(13) . . ? H3 N3 C4 117.2(13) . . ? C2 N3 C4 118.45(16) . . ? H4 C4 C5 123.3(15) . . ? H4 C4 N3 115.2(15) . . ? C5 C4 N3 121.49(17) . . ? H5 C5 C4 127.2(14) . . ? H5 C5 C6 115.2(14) . . ? C4 C5 C6 117.56(16) . . ? N6 C6 N1 118.83(15) . . ? N6 C6 C5 119.80(15) . . ? N1 C6 C5 121.37(16) . . ? H61 N6 H62 117.2(19) . . ? H61 N6 C6 121.2(14) . . ? H62 N6 C6 117.8(14) . . ? H11 O1 H12 105(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.460 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.047 ##===END data_(4) _database_code_CSD 193882 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-Methyl-1,3-cyclohexanedionate, 2,6-diaminopyridinium, 5-methyl-1,3-cyclohexanedione enol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 O2, (C7 H9 O2)-, (C5 H8 N3)+' _chemical_formula_sum 'C19 H27 N3 O4' _chemical_formula_weight 361.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Mononlinic' _symmetry_space_group_name_H-M 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 17.474(2) _cell_length_b 5.270(2) _cell_length_c 22.478(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.420(10) _cell_angle_gamma 90.00 _cell_volume 1939.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max ?12 _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.087 _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 296 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4348 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.01 _reflns_number_total 4231 _reflns_number_gt 2124 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN (Fair, Enraf-Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0865P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4231 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1412 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1739 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.003 _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 O11 O 0.10205(13) -0.4901(4) 0.20334(10) 0.0646(6) Uani 1 1 d . . . O31 O 0.22382(12) 0.1364(4) 0.35012(10) 0.0601(6) Uani 1 1 d . . . C11 C 0.16366(17) -0.3629(5) 0.23337(13) 0.0448(7) Uani 1 1 d . . . C21 C 0.16035(17) -0.1650(6) 0.27372(14) 0.0507(8) Uani 1 1 d . . . C31 C 0.22800(16) -0.0352(5) 0.31046(12) 0.0434(7) Uani 1 1 d . . . C41 C 0.30973(17) -0.0952(7) 0.30666(14) 0.0481(7) Uani 1 1 d . . . C51 C 0.3046(2) -0.2081(7) 0.24392(17) 0.0617(9) Uani 1 1 d . . . C61 C 0.2437(2) -0.4259(6) 0.22715(17) 0.0536(8) Uani 1 1 d . . . C71 C 0.3879(3) -0.2960(15) 0.2440(4) 0.111(2) Uani 1 1 d . . . O12 O 0.21137(12) 0.4846(4) 0.56242(9) 0.0588(6) Uani 1 1 d . . . O32 O 0.34189(13) 0.3913(5) 0.41312(10) 0.0635(6) Uani 1 1 d . . . C12 C 0.26577(15) 0.5398(5) 0.54086(12) 0.0423(7) Uani 1 1 d . . . C22 C 0.27313(16) 0.4266(5) 0.48666(13) 0.0443(7) Uani 1 1 d . . . C32 C 0.33313(16) 0.4895(5) 0.46366(12) 0.0438(7) Uani 1 1 d . . . C42 C 0.3947(2) 0.6872(7) 0.49591(16) 0.0588(9) Uani 1 1 d . . . C52 C 0.4055(2) 0.7265(8) 0.56375(18) 0.0658(10) Uani 1 1 d . . . C62 C 0.3257(2) 0.7463(8) 0.57332(18) 0.0580(9) Uani 1 1 d . . . C72 C 0.4636(3) 0.9413(10) 0.5933(3) 0.0829(13) Uani 1 1 d . . . N1 N 0.03984(13) -0.8715(4) 0.12259(10) 0.0386(5) Uani 1 1 d . . . N2 N -0.05954(19) -0.7207(5) 0.15858(14) 0.0546(7) Uani 1 1 d . . . N6 N 0.14892(15) -0.9931(6) 0.09445(13) 0.0523(7) Uani 1 1 d . . . C2 C -0.03671(16) -0.8923(5) 0.12477(12) 0.0406(6) Uani 1 1 d . . . C3 C -0.08580(17) -1.0885(5) 0.09159(13) 0.0446(7) Uani 1 1 d . . . C4 C -0.05402(18) -1.2584(6) 0.06039(14) 0.0477(7) Uani 1 1 d . . . C5 C 0.02432(18) -1.2354(6) 0.05977(13) 0.0464(7) Uani 1 1 d . . . C6 C 0.07145(15) -1.0359(5) 0.09128(12) 0.0396(6) Uani 1 1 d . . . H21 H 0.1117(19) -0.125(6) 0.2830(14) 0.062(9) Uiso 1 1 d . . . H411 H 0.3418(18) 0.064(6) 0.3162(13) 0.059(9) Uiso 1 1 d . . . H421 H 0.340(2) -0.212(7) 0.3385(17) 0.075(11) Uiso 1 1 d . . . H51 H 0.276(3) -0.065(8) 0.2111(19) 0.109(14) Uiso 1 1 d . . . H611 H 0.2333(18) -0.479(6) 0.1886(15) 0.061(10) Uiso 1 1 d . . . H621 H 0.270(2) -0.567(7) 0.2601(16) 0.077(10) Uiso 1 1 d . . . H711 H 0.407(3) -0.416(10) 0.282(3) 0.13(2) Uiso 1 1 d . . . H721 H 0.425(3) -0.148(9) 0.251(2) 0.110(16) Uiso 1 1 d . . . H731 H 0.383(4) -0.368(12) 0.207(3) 0.17(3) Uiso 1 1 d . . . H22 H 0.2355(15) 0.297(5) 0.4650(11) 0.033(6) Uiso 1 1 d . . . H32 H 0.288(3) 0.254(8) 0.381(2) 0.111(13) Uiso 1 1 d . . . H412 H 0.442(2) 0.671(7) 0.4896(16) 0.082(11) Uiso 1 1 d . . . H422 H 0.373(2) 0.875(7) 0.4765(16) 0.084(11) Uiso 1 1 d . . . H52 H 0.437(2) 0.556(8) 0.5917(19) 0.107(14) Uiso 1 1 d . . . H612 H 0.3288(19) 0.752(6) 0.6125(16) 0.063(10) Uiso 1 1 d . . . H622 H 0.299(3) 0.918(10) 0.550(2) 0.129(17) Uiso 1 1 d . . . H712 H 0.517(3) 0.909(8) 0.5941(19) 0.106(14) Uiso 1 1 d . . . H722 H 0.470(3) 0.963(9) 0.639(2) 0.121(17) Uiso 1 1 d . . . H732 H 0.433(2) 1.114(8) 0.5738(17) 0.093(13) Uiso 1 1 d . . . H1 H 0.0718(17) -0.751(6) 0.1476(13) 0.051(8) Uiso 1 1 d . . . H201 H -0.022(2) -0.610(6) 0.1788(14) 0.061(10) Uiso 1 1 d . . . H202 H -0.111(2) -0.725(6) 0.1606(14) 0.068(10) Uiso 1 1 d . . . H3 H -0.1415(16) -1.097(5) 0.0924(12) 0.042(7) Uiso 1 1 d . . . H4 H -0.0879(17) -1.395(6) 0.0341(13) 0.052(8) Uiso 1 1 d . . . H5 H 0.0473(17) -1.350(6) 0.0372(14) 0.054(8) Uiso 1 1 d . . . H601 H 0.1670(19) -1.096(6) 0.0752(15) 0.057(10) Uiso 1 1 d . . . H602 H 0.169(2) -0.817(9) 0.0971(18) 0.104(15) 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 O11 0.0574(13) 0.0596(14) 0.0688(14) -0.0264(12) 0.0121(11) -0.0183(11) O31 0.0496(12) 0.0678(15) 0.0660(13) -0.0331(12) 0.0242(10) -0.0169(11) C11 0.0520(16) 0.0389(15) 0.0407(14) -0.0038(13) 0.0126(13) -0.0055(14) C21 0.0398(16) 0.0509(18) 0.0609(18) -0.0176(15) 0.0169(14) -0.0070(14) C31 0.0452(15) 0.0423(16) 0.0430(14) -0.0074(13) 0.0159(12) -0.0051(13) C41 0.0417(15) 0.0497(18) 0.0491(17) -0.0092(16) 0.0109(13) -0.0028(15) C51 0.0526(18) 0.072(2) 0.066(2) -0.021(2) 0.0277(16) -0.0083(18) C61 0.0595(19) 0.0510(19) 0.0509(18) -0.0122(17) 0.0200(15) -0.0021(16) C71 0.068(3) 0.153(6) 0.126(5) -0.069(5) 0.053(3) -0.017(3) O12 0.0588(12) 0.0646(14) 0.0630(13) 0.0025(11) 0.0338(11) -0.0120(11) O32 0.0563(12) 0.0791(16) 0.0624(13) -0.0266(12) 0.0298(10) -0.0200(12) C12 0.0384(14) 0.0426(16) 0.0437(15) 0.0058(13) 0.0116(12) 0.0010(12) C22 0.0409(14) 0.0395(15) 0.0485(16) -0.0034(14) 0.0107(12) -0.0105(13) C32 0.0405(14) 0.0464(16) 0.0445(15) -0.0065(14) 0.0150(12) -0.0067(13) C42 0.0481(18) 0.064(2) 0.072(2) -0.0216(18) 0.0297(17) -0.0189(16) C52 0.0510(18) 0.069(2) 0.075(2) -0.025(2) 0.0185(17) -0.0214(18) C62 0.0597(19) 0.067(2) 0.052(2) -0.0189(18) 0.0258(16) -0.0182(18) C72 0.063(2) 0.086(3) 0.097(3) -0.041(3) 0.024(2) -0.028(2) N1 0.0396(12) 0.0331(12) 0.0417(12) -0.0046(11) 0.0123(10) -0.0053(10) N2 0.0514(16) 0.0487(16) 0.0719(18) -0.0122(14) 0.0318(14) -0.0060(14) N6 0.0436(14) 0.0577(18) 0.0589(16) -0.0042(15) 0.0222(12) 0.0023(13) C2 0.0425(14) 0.0353(14) 0.0442(15) 0.0035(13) 0.0153(12) 0.0016(12) C3 0.0433(15) 0.0380(15) 0.0510(16) 0.0012(13) 0.0146(13) -0.0039(13) C4 0.0522(17) 0.0401(16) 0.0466(17) -0.0060(14) 0.0119(14) -0.0071(14) C5 0.0523(17) 0.0398(16) 0.0453(16) -0.0074(14) 0.0150(13) -0.0021(14) C6 0.0381(14) 0.0401(15) 0.0391(13) 0.0024(13) 0.0115(11) 0.0047(12) _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 O11 C11 1.247(3) . ? O31 C31 1.290(3) . ? O31 H32 1.25(5) . ? C11 C21 1.397(4) . ? C11 C61 1.491(4) . ? C21 C31 1.366(4) . ? C21 H21 0.97(3) . ? C31 C41 1.494(4) . ? C41 C51 1.505(4) . ? C41 H411 0.99(3) . ? C41 H421 0.96(4) . ? C51 C61 1.521(4) . ? C51 C71 1.527(5) . ? C51 H51 1.05(4) . ? C61 H611 0.87(3) . ? C61 H621 1.04(4) . ? C71 H711 1.03(5) . ? C71 H721 0.99(5) . ? C71 H731 0.90(7) . ? O12 C12 1.243(3) . ? O32 C32 1.305(3) . ? O32 H32 1.21(5) . ? C12 C22 1.402(4) . ? C12 C62 1.510(4) . ? C22 C32 1.362(4) . ? C22 H22 0.95(3) . ? C32 C42 1.491(4) . ? C42 C52 1.485(5) . ? C42 H412 0.89(4) . ? C42 H422 1.10(4) . ? C52 C62 1.485(5) . ? C52 C72 1.512(5) . ? C52 H52 1.13(4) . ? C62 H612 0.86(3) . ? C62 H622 1.07(5) . ? C72 H712 0.95(4) . ? C72 H722 1.00(5) . ? C72 H732 1.07(4) . ? N1 C6 1.350(3) . ? N1 C2 1.360(3) . ? N1 H1 0.90(3) . ? N2 C2 1.329(4) . ? N2 H201 0.88(3) . ? N2 H202 0.91(3) . ? N6 C6 1.349(3) . ? N6 H601 0.82(3) . ? N6 H602 0.99(5) . ? C2 C3 1.384(4) . ? C3 C4 1.369(4) . ? C3 H3 0.98(3) . ? C4 C5 1.379(4) . ? C4 H4 0.99(3) . ? C5 C6 1.371(4) . ? C5 H5 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 O31 H32 118.0(18) . . ? O11 C11 C21 121.9(3) . . ? O11 C11 C61 119.4(3) . . ? C21 C11 C61 118.7(3) . . ? C31 C21 C11 122.9(3) . . ? C31 C21 H21 113.7(18) . . ? C11 C21 H21 122.8(18) . . ? O31 C31 C21 121.5(3) . . ? O31 C31 C41 118.3(2) . . ? C21 C31 C41 120.2(3) . . ? C31 C41 C51 113.1(2) . . ? C31 C41 H411 106.7(17) . . ? C51 C41 H411 112.5(17) . . ? C31 C41 H421 113(2) . . ? C51 C41 H421 106(2) . . ? H411 C41 H421 105(3) . . ? C41 C51 C61 109.8(3) . . ? C41 C51 C71 112.0(3) . . ? C61 C51 C71 110.9(4) . . ? C41 C51 H51 103(2) . . ? C61 C51 H51 104(2) . . ? C71 C51 H51 116(2) . . ? C11 C61 C51 114.1(3) . . ? C11 C61 H611 107(2) . . ? C51 C61 H611 112(2) . . ? C11 C61 H621 107.3(18) . . ? C51 C61 H621 105.1(19) . . ? H611 C61 H621 112(3) . . ? C51 C71 H711 103(3) . . ? C51 C71 H721 109(3) . . ? H711 C71 H721 110(4) . . ? C51 C71 H731 110(4) . . ? H711 C71 H731 115(5) . . ? H721 C71 H731 110(5) . . ? C32 O32 H32 117.2(19) . . ? O12 C12 C22 123.6(3) . . ? O12 C12 C62 118.4(3) . . ? C22 C12 C62 117.9(2) . . ? C32 C22 C12 122.9(3) . . ? C32 C22 H22 117.7(14) . . ? C12 C22 H22 119.5(14) . . ? O32 C32 C22 125.0(3) . . ? O32 C32 C42 114.6(2) . . ? C22 C32 C42 120.4(3) . . ? C52 C42 C32 114.1(3) . . ? C52 C42 H412 113(2) . . ? C32 C42 H412 114(2) . . ? C52 C42 H422 100.5(18) . . ? C32 C42 H422 110.0(19) . . ? H412 C42 H422 104(3) . . ? C42 C52 C62 111.7(3) . . ? C42 C52 C72 112.4(3) . . ? C62 C52 C72 113.9(3) . . ? C42 C52 H52 109(2) . . ? C62 C52 H52 106(2) . . ? C72 C52 H52 103(2) . . ? C52 C62 C12 114.0(3) . . ? C52 C62 H612 115(2) . . ? C12 C62 H612 108(2) . . ? C52 C62 H622 105(3) . . ? C12 C62 H622 105(3) . . ? H612 C62 H622 109(3) . . ? C52 C72 H712 113(3) . . ? C52 C72 H722 111(3) . . ? H712 C72 H722 104(4) . . ? C52 C72 H732 107(2) . . ? H712 C72 H732 121(3) . . ? H722 C72 H732 101(3) . . ? C6 N1 C2 123.6(2) . . ? C6 N1 H1 120.1(18) . . ? C2 N1 H1 115.9(18) . . ? C2 N2 H201 115(2) . . ? C2 N2 H202 120(2) . . ? H201 N2 H202 124(3) . . ? C6 N6 H601 115(2) . . ? C6 N6 H602 119(2) . . ? H601 N6 H602 117(3) . . ? N2 C2 N1 117.5(3) . . ? N2 C2 C3 124.3(3) . . ? N1 C2 C3 118.2(2) . . ? C4 C3 C2 118.6(3) . . ? C4 C3 H3 124.2(16) . . ? C2 C3 H3 117.2(16) . . ? C3 C4 C5 122.0(3) . . ? C3 C4 H4 121.3(16) . . ? C5 C4 H4 116.6(16) . . ? C6 C5 C4 118.8(3) . . ? C6 C5 H5 118.0(17) . . ? C4 C5 H5 123.2(17) . . ? N6 C6 N1 116.8(3) . . ? N6 C6 C5 124.5(3) . . ? N1 C6 C5 118.7(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.234 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.050 ##===END data_(5) _database_code_CSD 193883 _audit_creation_method SHELXL-97 _chemical_name_systematic ; tropolonate, 2,6-diaminopyridinium, hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C7 H5 O2)-, (C5 H8 N3)+, H2O' _chemical_formula_sum 'C24 H30 N6 O6' _chemical_formula_weight 498.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 10.376(3) _cell_length_b 17.697(2) _cell_length_c 14.647(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.23(2) _cell_angle_gamma 90.00 _cell_volume 2539.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description 'prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.096 _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 296 _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 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7652 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7394 _reflns_number_gt 4146 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN (Fair, Enraf-Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0589P)^2^+0.1081P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7394 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.89360(11) 0.06806(6) 0.18605(8) 0.0642(3) Uani 1 1 d . . . O21 O 0.70722(10) 0.05159(6) 0.26497(8) 0.0671(3) Uani 1 1 d . . . C11 C 0.84496(13) 0.12912(8) 0.20720(9) 0.0477(3) Uani 1 1 d . . . C21 C 0.73894(13) 0.12054(8) 0.25217(9) 0.0501(3) Uani 1 1 d . . . C31 C 0.67190(18) 0.17946(12) 0.28006(13) 0.0717(5) Uani 1 1 d . . . C41 C 0.6828(2) 0.25702(13) 0.27469(14) 0.0827(6) Uani 1 1 d . . . C51 C 0.7654(2) 0.29889(12) 0.23921(14) 0.0807(6) Uani 1 1 d . . . C61 C 0.8594(2) 0.27190(11) 0.19977(15) 0.0826(5) Uani 1 1 d . . . C71 C 0.89345(18) 0.19886(10) 0.18641(13) 0.0680(4) Uani 1 1 d . . . N11 N 0.61888(13) -0.04523(7) 0.10316(8) 0.0511(3) Uani 1 1 d . . . N21 N 0.78113(14) -0.03354(9) 0.02885(11) 0.0675(4) Uani 1 1 d . . . N31 N 0.4695(2) -0.04556(11) 0.18900(13) 0.0817(5) Uani 1 1 d . . . C81 C 0.66828(15) -0.06691(8) 0.03175(10) 0.0518(3) Uani 1 1 d . . . C91 C 0.59701(17) -0.12279(9) -0.03185(11) 0.0613(4) Uani 1 1 d . . . C101 C 0.48318(19) -0.15361(10) -0.01918(13) 0.0666(4) Uani 1 1 d . . . C111 C 0.43433(19) -0.13056(10) 0.05302(13) 0.0691(4) Uani 1 1 d . . . C121 C 0.50434(16) -0.07444(9) 0.11565(11) 0.0599(4) Uani 1 1 d . . . O12 O 0.50559(11) -0.09425(6) 0.53348(7) 0.0665(3) Uani 1 1 d . . . O22 O 0.67362(14) -0.09218(6) 0.70633(9) 0.0913(4) Uani 1 1 d . . . C12 C 0.54299(14) -0.15850(8) 0.57105(10) 0.0499(3) Uani 1 1 d . . . C22 C 0.64242(14) -0.15713(8) 0.66962(11) 0.0566(4) Uani 1 1 d . . . C32 C 0.70162(18) -0.22150(10) 0.72401(15) 0.0721(5) Uani 1 1 d . . . C42 C 0.6832(2) -0.29743(11) 0.70451(19) 0.0826(6) Uani 1 1 d . . . C52 C 0.6002(3) -0.33383(12) 0.6254(2) 0.0894(7) Uani 1 1 d . . . C62 C 0.5123(3) -0.30030(11) 0.54367(17) 0.0873(6) Uani 1 1 d . . . C72 C 0.4882(2) -0.22462(10) 0.52029(13) 0.0694(4) Uani 1 1 d . . . N12 N 0.88535(11) -0.04310(6) 0.39367(8) 0.0463(3) Uani 1 1 d . . . N22 N 0.70226(14) -0.03350(9) 0.44810(12) 0.0673(4) Uani 1 1 d . . . N32 N 1.05512(15) -0.04375(9) 0.32519(10) 0.0624(3) Uani 1 1 d . . . C82 C 0.82142(14) -0.06604(8) 0.45682(10) 0.0502(3) Uani 1 1 d . . . C92 C 0.88438(17) -0.12096(9) 0.52417(11) 0.0603(4) Uani 1 1 d . . . C102 C 1.00794(17) -0.14943(9) 0.52455(11) 0.0601(4) Uani 1 1 d . . . C112 C 1.07150(16) -0.12514(8) 0.46131(11) 0.0573(4) Uani 1 1 d . . . C122 C 1.00750(13) -0.07056(8) 0.39278(10) 0.0481(3) Uani 1 1 d . . . O1 O 1.12858(15) 0.05382(8) 0.13090(9) 0.0755(4) Uani 1 1 d . . . O2 O 0.34353(11) -0.05565(7) 0.34797(8) 0.0551(3) Uani 1 1 d . . . H31 H 0.605(2) 0.1631(12) 0.3065(15) 0.103(7) Uiso 1 1 d . . . H41 H 0.624(2) 0.2834(12) 0.2989(16) 0.109(7) Uiso 1 1 d . . . H51 H 0.761(2) 0.3529(14) 0.2437(14) 0.098(6) Uiso 1 1 d . . . H61 H 0.914(2) 0.3074(12) 0.1773(15) 0.101(7) Uiso 1 1 d . . . H71 H 0.9593(18) 0.1927(10) 0.1554(13) 0.085(6) Uiso 1 1 d . . . H11 H 0.6653(16) -0.0115(10) 0.1444(12) 0.065(5) Uiso 1 1 d . . . H211 H 0.8173(16) 0.0013(9) 0.0745(12) 0.067(5) Uiso 1 1 d . . . H212 H 0.814(2) -0.0407(11) -0.0216(15) 0.094(6) Uiso 1 1 d . . . H311 H 0.523(2) -0.0070(13) 0.2245(15) 0.101(7) Uiso 1 1 d . . . H312 H 0.401(3) -0.0654(12) 0.2006(17) 0.109(8) Uiso 1 1 d . . . H91 H 0.6267(19) -0.1373(9) -0.0842(14) 0.084(5) Uiso 1 1 d . . . H101 H 0.4346(17) -0.1917(10) -0.0604(13) 0.072(5) Uiso 1 1 d . . . H111 H 0.3543(18) -0.1534(9) 0.0610(12) 0.070(5) Uiso 1 1 d . . . H32 H 0.768(2) -0.2076(11) 0.7841(15) 0.091(6) Uiso 1 1 d . . . H42 H 0.740(2) -0.3294(13) 0.7581(14) 0.101(6) Uiso 1 1 d . . . H52 H 0.598(2) -0.3824(13) 0.6295(15) 0.104(7) Uiso 1 1 d . . . H62 H 0.454(2) -0.3304(13) 0.4939(16) 0.104(7) Uiso 1 1 d . . . H72 H 0.4212(18) -0.2150(9) 0.4564(14) 0.075(5) Uiso 1 1 d . . . H12 H 0.8415(15) -0.0095(9) 0.3482(11) 0.057(4) Uiso 1 1 d . . . H221 H 0.6776(17) 0.0029(10) 0.4113(12) 0.064(5) Uiso 1 1 d . . . H222 H 0.6543(19) -0.0481(10) 0.4852(13) 0.078(6) Uiso 1 1 d . . . H321 H 1.0090(17) -0.0071(10) 0.2859(12) 0.074(5) Uiso 1 1 d . . . H322 H 1.140(2) -0.0538(9) 0.3263(12) 0.072(5) Uiso 1 1 d . . . H92 H 0.8409(19) -0.1362(10) 0.5725(14) 0.086(6) Uiso 1 1 d . . . H102 H 1.0523(18) -0.1888(10) 0.5712(13) 0.081(5) Uiso 1 1 d . . . H112 H 1.1553(18) -0.1453(9) 0.4591(12) 0.073(5) Uiso 1 1 d . . . H100 H 1.193(2) 0.0684(12) 0.1827(18) 0.098(7) Uiso 1 1 d . . . H200 H 1.057(2) 0.0641(12) 0.1410(16) 0.099(7) Uiso 1 1 d . . . H300 H 0.391(2) -0.0696(11) 0.4060(15) 0.088(6) Uiso 1 1 d . . . H400 H 0.3551(18) -0.0071(12) 0.3469(13) 0.079(6) 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 O11 0.0628(6) 0.0646(6) 0.0697(7) -0.0094(5) 0.0281(5) 0.0092(5) O21 0.0555(6) 0.0746(8) 0.0734(7) 0.0176(5) 0.0243(5) -0.0010(5) C11 0.0426(7) 0.0570(8) 0.0430(7) -0.0023(6) 0.0136(5) 0.0034(6) C21 0.0423(7) 0.0619(8) 0.0442(7) 0.0052(6) 0.0115(5) 0.0045(6) C31 0.0633(10) 0.0916(13) 0.0694(10) 0.0028(9) 0.0343(8) 0.0193(9) C41 0.0814(13) 0.0921(15) 0.0726(11) -0.0126(10) 0.0225(10) 0.0365(11) C51 0.0922(14) 0.0571(11) 0.0754(12) -0.0081(9) 0.0040(11) 0.0180(10) C61 0.0926(14) 0.0620(11) 0.0917(13) 0.0045(10) 0.0284(11) -0.0090(10) C71 0.0674(10) 0.0677(11) 0.0805(11) 0.0009(8) 0.0402(9) -0.0032(8) N11 0.0591(7) 0.0518(7) 0.0439(6) 0.0016(5) 0.0190(5) 0.0081(6) N21 0.0611(8) 0.0834(10) 0.0653(9) -0.0196(8) 0.0308(7) -0.0032(7) N31 0.0932(12) 0.0924(12) 0.0788(11) -0.0010(9) 0.0546(10) -0.0024(10) C81 0.0550(8) 0.0552(8) 0.0465(7) 0.0019(6) 0.0183(6) 0.0126(6) C91 0.0687(10) 0.0612(9) 0.0526(8) -0.0057(7) 0.0181(7) 0.0092(8) C101 0.0691(10) 0.0576(9) 0.0630(10) 0.0003(8) 0.0082(8) 0.0019(8) C111 0.0646(10) 0.0669(10) 0.0764(11) 0.0081(9) 0.0240(9) -0.0027(8) C121 0.0658(9) 0.0603(9) 0.0589(9) 0.0129(7) 0.0279(7) 0.0109(7) O12 0.0733(7) 0.0609(6) 0.0612(6) 0.0169(5) 0.0169(5) 0.0042(5) O22 0.0964(9) 0.0555(7) 0.0880(9) 0.0055(6) -0.0157(7) -0.0135(6) C12 0.0518(7) 0.0536(8) 0.0517(7) 0.0065(6) 0.0273(6) -0.0001(6) C22 0.0485(8) 0.0514(8) 0.0678(9) 0.0100(7) 0.0162(7) -0.0045(6) C32 0.0599(9) 0.0670(11) 0.0824(12) 0.0217(9) 0.0141(9) 0.0070(8) C42 0.0829(13) 0.0604(11) 0.1135(16) 0.0288(12) 0.0445(12) 0.0200(10) C52 0.1284(19) 0.0450(10) 0.123(2) 0.0058(11) 0.0804(17) 0.0061(11) C62 0.1292(18) 0.0631(12) 0.0882(14) -0.0220(11) 0.0612(14) -0.0218(12) C72 0.0904(12) 0.0672(10) 0.0566(10) -0.0070(8) 0.0321(9) -0.0112(9) N12 0.0445(6) 0.0451(6) 0.0495(6) 0.0005(5) 0.0157(5) -0.0003(5) N22 0.0543(8) 0.0737(10) 0.0818(10) 0.0099(8) 0.0332(7) 0.0040(7) N32 0.0561(8) 0.0731(9) 0.0653(8) 0.0075(7) 0.0299(7) 0.0088(7) C82 0.0479(7) 0.0504(7) 0.0540(8) -0.0052(6) 0.0193(6) -0.0081(6) C92 0.0680(10) 0.0589(9) 0.0565(9) 0.0027(7) 0.0239(7) -0.0085(7) C102 0.0671(9) 0.0525(8) 0.0537(8) 0.0041(7) 0.0103(7) -0.0010(7) C112 0.0526(8) 0.0531(8) 0.0633(9) -0.0030(7) 0.0151(7) 0.0066(7) C122 0.0462(7) 0.0475(7) 0.0507(7) -0.0069(6) 0.0163(6) -0.0028(6) O1 0.0570(7) 0.1178(11) 0.0561(7) -0.0140(6) 0.0245(6) -0.0025(7) O2 0.0551(6) 0.0533(7) 0.0547(6) -0.0036(5) 0.0151(5) -0.0035(5) _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 O11 C11 1.2734(16) . ? O21 C21 1.2934(17) . ? C11 C71 1.404(2) . ? C11 C21 1.4644(19) . ? C21 C31 1.387(2) . ? C31 C41 1.382(3) . ? C31 H31 0.94(2) . ? C41 C51 1.359(3) . ? C41 H41 0.93(2) . ? C51 C61 1.373(3) . ? C51 H51 0.96(2) . ? C61 C71 1.371(3) . ? C61 H61 0.97(2) . ? C71 H71 0.943(18) . ? N11 C81 1.3627(18) . ? N11 C121 1.363(2) . ? N11 H11 0.872(17) . ? N21 C81 1.324(2) . ? N21 H211 0.897(17) . ? N21 H212 0.92(2) . ? N31 C121 1.343(2) . ? N31 H311 0.93(2) . ? N31 H312 0.86(2) . ? C81 C91 1.392(2) . ? C91 C101 1.368(3) . ? C91 H91 0.952(19) . ? C101 C111 1.377(3) . ? C101 H101 0.934(18) . ? C111 C121 1.384(2) . ? C111 H111 0.964(17) . ? O12 C12 1.2670(17) . ? O22 C22 1.2651(18) . ? C12 C72 1.402(2) . ? C12 C22 1.472(2) . ? C22 C32 1.410(2) . ? C32 C42 1.374(3) . ? C32 H32 0.95(2) . ? C42 C52 1.357(3) . ? C42 H42 0.99(2) . ? C52 C62 1.378(3) . ? C52 H52 0.86(2) . ? C62 C72 1.385(3) . ? C62 H62 0.94(2) . ? C72 H72 0.979(18) . ? N12 C122 1.3615(18) . ? N12 C82 1.3655(18) . ? N12 H12 0.897(16) . ? N22 C82 1.331(2) . ? N22 H221 0.824(17) . ? N22 H222 0.89(2) . ? N32 C122 1.3310(19) . ? N32 H321 0.894(18) . ? N32 H322 0.893(19) . ? C82 C92 1.386(2) . ? C92 C102 1.376(2) . ? C92 H92 0.994(19) . ? C102 C112 1.371(2) . ? C102 H102 0.978(18) . ? C112 C122 1.394(2) . ? C112 H112 0.951(17) . ? O1 H100 0.87(3) . ? O1 H200 0.83(2) . ? O2 H300 0.87(2) . ? O2 H400 0.87(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 O11 C11 C71 119.63(13) . . ? O11 C11 C21 115.98(12) . . ? C71 C11 C21 124.39(13) . . ? O21 C21 C31 119.35(14) . . ? O21 C21 C11 115.32(12) . . ? C31 C21 C11 125.32(15) . . ? C41 C31 C21 132.19(18) . . ? C41 C31 H31 114.4(13) . . ? C21 C31 H31 113.4(13) . . ? C51 C41 C31 129.57(18) . . ? C51 C41 H41 116.7(14) . . ? C31 C41 H41 113.7(14) . . ? C41 C51 C61 126.60(19) . . ? C41 C51 H51 117.7(12) . . ? C61 C51 H51 115.6(12) . . ? C71 C61 C51 129.8(2) . . ? C71 C61 H61 110.9(12) . . ? C51 C61 H61 119.3(12) . . ? C61 C71 C11 132.10(17) . . ? C61 C71 H71 116.1(11) . . ? C11 C71 H71 111.8(11) . . ? C81 N11 C121 124.16(14) . . ? C81 N11 H11 117.6(11) . . ? C121 N11 H11 118.2(11) . . ? C81 N21 H211 116.1(10) . . ? C81 N21 H212 122.0(13) . . ? H211 N21 H212 121.3(16) . . ? C121 N31 H311 117.3(13) . . ? C121 N31 H312 117.5(16) . . ? H311 N31 H312 125(2) . . ? N21 C81 N11 117.32(14) . . ? N21 C81 C91 125.14(14) . . ? N11 C81 C91 117.54(14) . . ? C101 C91 C81 118.97(15) . . ? C101 C91 H91 121.7(11) . . ? C81 C91 H91 119.3(11) . . ? C91 C101 C111 122.61(17) . . ? C91 C101 H101 120.4(10) . . ? C111 C101 H101 117.0(10) . . ? C101 C111 C121 118.43(17) . . ? C101 C111 H111 121.2(10) . . ? C121 C111 H111 120.4(10) . . ? N31 C121 N11 116.09(17) . . ? N31 C121 C111 125.64(17) . . ? N11 C121 C111 118.27(15) . . ? O12 C12 C72 120.38(15) . . ? O12 C12 C22 115.25(13) . . ? C72 C12 C22 124.35(14) . . ? O22 C22 C32 119.42(15) . . ? O22 C22 C12 115.48(13) . . ? C32 C22 C12 125.10(15) . . ? C42 C32 C22 131.91(19) . . ? C42 C32 H32 116.9(12) . . ? C22 C32 H32 111.1(12) . . ? C52 C42 C32 130.3(2) . . ? C52 C42 H42 116.8(13) . . ? C32 C42 H42 112.8(13) . . ? C42 C52 C62 126.15(19) . . ? C42 C52 H52 115.8(15) . . ? C62 C52 H52 117.8(15) . . ? C52 C62 C72 130.2(2) . . ? C52 C62 H62 120.1(13) . . ? C72 C62 H62 109.6(14) . . ? C62 C72 C12 131.86(19) . . ? C62 C72 H72 114.8(10) . . ? C12 C72 H72 113.4(10) . . ? C122 N12 C82 124.19(12) . . ? C122 N12 H12 118.4(9) . . ? C82 N12 H12 117.4(9) . . ? C82 N22 H221 118.6(12) . . ? C82 N22 H222 120.4(12) . . ? H221 N22 H222 120.7(17) . . ? C122 N32 H321 119.1(11) . . ? C122 N32 H322 121.4(11) . . ? H321 N32 H322 118.1(15) . . ? N22 C82 N12 116.71(14) . . ? N22 C82 C92 125.23(15) . . ? N12 C82 C92 118.06(13) . . ? C102 C92 C82 118.68(15) . . ? C102 C92 H92 122.6(11) . . ? C82 C92 H92 118.6(11) . . ? C112 C102 C92 122.50(15) . . ? C112 C102 H102 118.3(10) . . ? C92 C102 H102 119.2(10) . . ? C102 C112 C122 118.87(14) . . ? C102 C112 H112 123.7(10) . . ? C122 C112 H112 117.4(10) . . ? N32 C122 N12 117.05(13) . . ? N32 C122 C112 125.25(14) . . ? N12 C122 C112 117.69(13) . . ? H100 O1 H200 105(2) . . ? H300 O2 H400 105.2(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.190 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.033