Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 222 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Satoshi Iwatsuki' 'Koji Ishihara' 'Hideaki Ito' 'Tomohiro Itou' 'Kazuko Matsumoto' 'Hiroki Mori' 'Kuzuhiro Uemura' 'Yoshinobu Yokomori' _publ_contact_author_name 'Satoshi Iwatsuki' _publ_contact_author_address ; Department of Chemistry Waseda University Okubo 3-4-1 Shinjuku-ku Tokyo 169-8555 JAPAN ; _publ_contact_author_email S-IWATSUKI@AONI.WASEDA.JP _publ_section_title ; Isomerization Reaction of Head-to-Head a-Pyridonato-Bridged Ethylenediaminepalladium(II) Binuclear Complex, [Pd2(en)2(C5H4NO)2]2+, in Aqueous Solution ; # Attachment 'HHPD2.CIF' data_HHPD2 _database_code_depnum_ccdc_archive 'CCDC 294745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Cl2 N6 O10 Pd2' _chemical_formula_weight 720.09 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.785(3) _cell_length_b 8.6908(17) _cell_length_c 21.083(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.215(4) _cell_angle_gamma 90.00 _cell_volume 2339.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1005 _cell_measurement_theta_min 2.967 _cell_measurement_theta_max 27.453 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.045 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.829 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3827 _exptl_absorpt_correction_T_max 0.7710 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 293 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 588 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13752 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5206 _reflns_number_gt 4499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0548P)^2^+0.3563P] 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 5206 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 Pd1 Pd 0.770312(18) 0.94535(3) 0.139061(10) 0.01358(9) Uani 1 1 d . . . Pd2 Pd 0.563028(18) 0.95486(3) 0.065052(10) 0.01395(9) Uani 1 1 d . . . Cl1 Cl 0.52944(6) 0.43342(8) 0.18415(4) 0.01728(17) Uani 1 1 d . . . Cl2 Cl 0.89936(7) 0.32301(10) 0.31620(4) 0.0277(2) Uani 1 1 d . . . O2 O 0.64559(17) 0.8181(3) 0.00908(10) 0.0209(5) Uani 1 1 d . . . O1 O 0.63457(17) 1.1540(3) 0.03804(10) 0.0203(5) Uani 1 1 d . . . N5 N 0.4570(2) 1.0664(3) 0.11567(13) 0.0180(6) Uani 1 1 d . . . H5A H 0.4866 1.0922 0.1550 0.022 Uiso 1 1 calc R . . H5B H 0.4363 1.1556 0.0951 0.022 Uiso 1 1 calc R . . O3 O 0.5984(2) 0.5411(3) 0.15626(14) 0.0361(7) Uani 1 1 d . . . O6 O 0.5831(2) 0.2904(3) 0.19488(12) 0.0282(6) Uani 1 1 d . . . N2 N 0.81286(19) 0.8657(3) 0.05240(12) 0.0153(5) Uani 1 1 d . . . O4 O 0.4385(2) 0.4124(3) 0.14169(12) 0.0303(6) Uani 1 1 d . . . O8 O 0.8088(2) 0.3303(3) 0.27273(12) 0.0330(6) Uani 1 1 d . . . N3 N 0.7379(2) 1.0168(3) 0.22808(12) 0.0189(6) Uani 1 1 d . . . H3A H 0.7640 1.1141 0.2356 0.023 Uiso 1 1 calc R . . H3B H 0.6666 1.0188 0.2323 0.023 Uiso 1 1 calc R . . N1 N 0.7789(2) 1.1652(3) 0.10878(11) 0.0159(5) Uani 1 1 d . . . O5 O 0.4964(2) 0.4934(4) 0.24316(12) 0.0398(7) Uani 1 1 d . . . C13 C 0.3637(3) 0.9638(4) 0.12307(16) 0.0213(7) Uani 1 1 d . . . H13A H 0.3157 0.9695 0.0846 0.026 Uiso 1 1 calc R . . H13B H 0.3251 0.9967 0.1601 0.026 Uiso 1 1 calc R . . C6 C 0.7453(2) 0.8131(3) 0.00563(14) 0.0177(6) Uani 1 1 d . . . N6 N 0.4745(2) 0.7699(3) 0.08097(12) 0.0180(5) Uani 1 1 d . . . H6A H 0.4357 0.7446 0.0444 0.022 Uiso 1 1 calc R . . H6B H 0.5170 0.6877 0.0921 0.022 Uiso 1 1 calc R . . C10 C 0.9173(3) 0.8602(4) 0.04442(15) 0.0219(7) Uani 1 1 d . . . H10 H 0.9635 0.9011 0.0770 0.026 Uiso 1 1 calc R . . N4 N 0.7871(2) 0.7339(3) 0.18248(12) 0.0203(6) Uani 1 1 d . . . H4A H 0.7441 0.6633 0.1616 0.024 Uiso 1 1 calc R . . H4B H 0.8552 0.7006 0.1808 0.024 Uiso 1 1 calc R . . C14 C 0.4034(3) 0.8016(4) 0.13258(15) 0.0200(7) Uani 1 1 d . . . H14A H 0.4415 0.7914 0.1745 0.024 Uiso 1 1 calc R . . H14B H 0.3441 0.7280 0.1305 0.024 Uiso 1 1 calc R . . C1 C 0.7150(2) 1.2273(4) 0.06226(14) 0.0176(6) Uani 1 1 d . . . C4 C 0.8840(3) 1.3941(4) 0.11635(15) 0.0215(7) Uani 1 1 d . . . H4 H 0.9401 1.4506 0.1366 0.026 Uiso 1 1 calc R . . C3 C 0.8221(3) 1.4565(4) 0.06646(18) 0.0255(8) Uani 1 1 d . . . H3 H 0.8377 1.5560 0.0508 0.031 Uiso 1 1 calc R . . C5 C 0.8606(3) 1.2472(4) 0.13517(15) 0.0202(6) Uani 1 1 d . . . H5 H 0.9036 1.2010 0.1681 0.024 Uiso 1 1 calc R . . C9 C 0.9597(3) 0.7987(4) -0.00804(16) 0.0284(8) Uani 1 1 d . . . H9 H 1.0334 0.7942 -0.0114 0.034 Uiso 1 1 calc R . . C2 C 0.7389(3) 1.3761(4) 0.03973(16) 0.0236(7) Uani 1 1 d . . . H2 H 0.6969 1.4202 0.0059 0.028 Uiso 1 1 calc R . . C12 C 0.7592(3) 0.7465(4) 0.25002(15) 0.0259(7) Uani 1 1 d . . . H12A H 0.7978 0.6682 0.2762 0.031 Uiso 1 1 calc R . . H12B H 0.6832 0.7289 0.2533 0.031 Uiso 1 1 calc R . . C7 C 0.7859(3) 0.7490(4) -0.04990(15) 0.0234(7) Uani 1 1 d . . . H7 H 0.7391 0.7101 -0.0826 0.028 Uiso 1 1 calc R . . O7 O 0.9480(3) 0.4701(4) 0.32181(18) 0.0611(11) Uani 1 1 d . . . C11 C 0.7881(3) 0.9059(4) 0.27349(15) 0.0240(7) Uani 1 1 d . . . H11A H 0.7629 0.9223 0.3165 0.029 Uiso 1 1 calc R . . H11B H 0.8651 0.9192 0.2755 0.029 Uiso 1 1 calc R . . C8 C 0.8905(3) 0.7426(4) -0.05671(16) 0.0273(7) Uani 1 1 d . . . H8 H 0.9169 0.7003 -0.0942 0.033 Uiso 1 1 calc R . . O10 O 0.9729(2) 0.2155(4) 0.29301(18) 0.0665(11) Uani 1 1 d . . . O9 O 0.8688(3) 0.2722(5) 0.37612(15) 0.0730(13) 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 Pd1 0.01615(15) 0.01145(15) 0.01312(14) 0.00108(8) 0.00057(10) -0.00008(8) Pd2 0.01587(15) 0.01159(15) 0.01432(15) -0.00018(8) 0.00032(10) -0.00012(8) Cl1 0.0205(4) 0.0127(4) 0.0185(4) -0.0003(3) 0.0000(3) -0.0005(3) Cl2 0.0228(4) 0.0278(5) 0.0320(4) -0.0070(3) -0.0029(3) -0.0017(3) O2 0.0199(12) 0.0219(12) 0.0209(11) -0.0051(9) 0.0005(9) 0.0011(9) O1 0.0229(12) 0.0182(12) 0.0193(11) 0.0056(9) -0.0032(9) -0.0059(9) N5 0.0197(14) 0.0132(13) 0.0211(14) -0.0009(10) 0.0017(11) 0.0025(10) O3 0.0243(14) 0.0299(16) 0.0537(18) 0.0185(12) -0.0014(13) -0.0055(11) O6 0.0322(14) 0.0159(12) 0.0355(14) 0.0008(10) -0.0068(11) 0.0051(10) N2 0.0166(13) 0.0117(13) 0.0179(12) 0.0015(10) 0.0020(10) 0.0018(10) O4 0.0288(14) 0.0221(13) 0.0385(14) -0.0030(11) -0.0131(11) 0.0010(11) O8 0.0272(13) 0.0399(16) 0.0312(14) -0.0115(12) -0.0052(11) 0.0015(12) N3 0.0218(14) 0.0203(14) 0.0145(13) 0.0013(11) 0.0003(11) -0.0013(11) N1 0.0170(13) 0.0146(13) 0.0164(12) -0.0009(10) 0.0017(10) 0.0004(10) O5 0.0482(17) 0.0481(18) 0.0233(13) -0.0093(13) 0.0045(12) 0.0161(15) C13 0.0235(17) 0.0159(16) 0.0251(17) 0.0026(12) 0.0064(14) 0.0004(12) C6 0.0211(16) 0.0111(15) 0.0210(15) 0.0020(12) 0.0021(12) 0.0017(12) N6 0.0204(13) 0.0154(13) 0.0183(12) -0.0004(10) 0.0005(10) -0.0018(10) C10 0.0227(17) 0.0195(17) 0.0231(16) -0.0008(13) -0.0011(13) -0.0025(13) N4 0.0215(14) 0.0176(14) 0.0217(13) 0.0047(11) -0.0008(11) 0.0008(11) C14 0.0242(17) 0.0154(16) 0.0208(16) 0.0013(12) 0.0049(13) 0.0010(13) C1 0.0208(15) 0.0136(15) 0.0187(15) -0.0005(12) 0.0041(12) 0.0004(12) C4 0.0184(16) 0.0185(17) 0.0278(17) -0.0067(13) 0.0027(13) -0.0031(13) C3 0.0303(19) 0.0118(17) 0.035(2) 0.0041(13) 0.0057(16) -0.0016(13) C5 0.0199(15) 0.0180(16) 0.0230(15) -0.0052(13) 0.0018(13) 0.0007(13) C9 0.0208(17) 0.033(2) 0.0323(19) -0.0061(15) 0.0086(15) -0.0007(14) C2 0.0297(18) 0.0179(17) 0.0230(16) 0.0060(13) -0.0015(14) 0.0015(14) C12 0.0310(19) 0.0246(19) 0.0224(17) 0.0097(14) 0.0030(14) 0.0010(15) C7 0.0254(17) 0.0260(18) 0.0186(15) -0.0057(13) 0.0009(13) 0.0057(14) O7 0.070(3) 0.0327(18) 0.076(2) 0.0029(16) -0.035(2) -0.0171(16) C11 0.0284(18) 0.0298(19) 0.0136(15) 0.0042(13) -0.0012(13) -0.0017(15) C8 0.0270(18) 0.032(2) 0.0236(17) -0.0044(15) 0.0052(14) 0.0029(15) O10 0.0337(17) 0.075(3) 0.089(3) -0.038(2) -0.0113(17) 0.0197(17) O9 0.0427(18) 0.131(4) 0.0439(18) 0.036(2) -0.0100(15) -0.024(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 Pd1 N1 2.019(3) . ? Pd1 N3 2.041(3) . ? Pd1 N2 2.055(2) . ? Pd1 N4 2.059(3) . ? Pd1 Pd2 3.0002(6) . ? Pd2 N6 2.005(3) . ? Pd2 O2 2.015(2) . ? Pd2 N5 2.019(3) . ? Pd2 O1 2.053(2) . ? Pd2 Pd2 3.2002(7) 3_675 ? Cl1 O6 1.432(2) . ? Cl1 O5 1.434(3) . ? Cl1 O3 1.434(3) . ? Cl1 O4 1.438(2) . ? Cl2 O9 1.414(3) . ? Cl2 O7 1.424(3) . ? Cl2 O10 1.431(3) . ? Cl2 O8 1.437(2) . ? O2 C6 1.282(4) . ? O1 C1 1.291(4) . ? N5 C13 1.504(4) . ? N5 H5A 0.9200 . ? N5 H5B 0.9200 . ? N2 C6 1.353(4) . ? N2 C10 1.356(4) . ? N3 C11 1.480(4) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? N1 C1 1.353(4) . ? N1 C5 1.358(4) . ? C13 C14 1.507(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C6 C7 1.421(4) . ? N6 C14 1.482(4) . ? N6 H6A 0.9200 . ? N6 H6B 0.9200 . ? C10 C9 1.367(5) . ? C10 H10 0.9500 . ? N4 C12 1.491(4) . ? N4 H4A 0.9200 . ? N4 H4B 0.9200 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C1 C2 1.416(4) . ? C4 C5 1.375(5) . ? C4 C3 1.391(5) . ? C4 H4 0.9500 . ? C3 C2 1.368(5) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C9 C8 1.404(5) . ? C9 H9 0.9500 . ? C2 H2 0.9500 . ? C12 C11 1.510(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C7 C8 1.354(5) . ? C7 H7 0.9500 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C8 H8 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Pd1 N3 91.18(10) . . ? N1 Pd1 N2 90.89(10) . . ? N3 Pd1 N2 175.73(10) . . ? N1 Pd1 N4 168.20(10) . . ? N3 Pd1 N4 83.34(11) . . ? N2 Pd1 N4 93.94(10) . . ? N1 Pd1 Pd2 82.63(7) . . ? N3 Pd1 Pd2 104.52(8) . . ? N2 Pd1 Pd2 79.46(7) . . ? N4 Pd1 Pd2 108.83(8) . . ? N6 Pd2 O2 86.81(10) . . ? N6 Pd2 N5 83.94(11) . . ? O2 Pd2 N5 169.10(10) . . ? N6 Pd2 O1 170.66(10) . . ? O2 Pd2 O1 94.51(9) . . ? N5 Pd2 O1 93.70(10) . . ? N6 Pd2 Pd1 112.41(8) . . ? O2 Pd2 Pd1 79.15(6) . . ? N5 Pd2 Pd1 109.75(8) . . ? O1 Pd2 Pd1 76.89(6) . . ? N6 Pd2 Pd2 94.49(7) . 3_675 ? O2 Pd2 Pd2 84.14(6) . 3_675 ? N5 Pd2 Pd2 90.83(8) . 3_675 ? O1 Pd2 Pd2 76.48(6) . 3_675 ? Pd1 Pd2 Pd2 147.165(13) . 3_675 ? O6 Cl1 O5 109.90(16) . . ? O6 Cl1 O3 109.33(16) . . ? O5 Cl1 O3 109.67(19) . . ? O6 Cl1 O4 110.57(15) . . ? O5 Cl1 O4 108.58(17) . . ? O3 Cl1 O4 108.77(16) . . ? O9 Cl2 O7 110.3(2) . . ? O9 Cl2 O10 108.7(3) . . ? O7 Cl2 O10 108.8(2) . . ? O9 Cl2 O8 109.29(18) . . ? O7 Cl2 O8 110.25(18) . . ? O10 Cl2 O8 109.39(17) . . ? C6 O2 Pd2 127.5(2) . . ? C1 O1 Pd2 131.60(19) . . ? C13 N5 Pd2 109.25(19) . . ? C13 N5 H5A 109.8 . . ? Pd2 N5 H5A 109.8 . . ? C13 N5 H5B 109.8 . . ? Pd2 N5 H5B 109.8 . . ? H5A N5 H5B 108.3 . . ? C6 N2 C10 119.3(3) . . ? C6 N2 Pd1 124.9(2) . . ? C10 N2 Pd1 115.7(2) . . ? C11 N3 Pd1 107.1(2) . . ? C11 N3 H3A 110.3 . . ? Pd1 N3 H3A 110.3 . . ? C11 N3 H3B 110.3 . . ? Pd1 N3 H3B 110.3 . . ? H3A N3 H3B 108.6 . . ? C1 N1 C5 120.4(3) . . ? C1 N1 Pd1 124.4(2) . . ? C5 N1 Pd1 114.9(2) . . ? N5 C13 C14 107.8(3) . . ? N5 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N5 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.5 . . ? O2 C6 N2 122.9(3) . . ? O2 C6 C7 118.1(3) . . ? N2 C6 C7 119.0(3) . . ? C14 N6 Pd2 110.45(19) . . ? C14 N6 H6A 109.6 . . ? Pd2 N6 H6A 109.6 . . ? C14 N6 H6B 109.6 . . ? Pd2 N6 H6B 109.6 . . ? H6A N6 H6B 108.1 . . ? N2 C10 C9 123.5(3) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C12 N4 Pd1 109.5(2) . . ? C12 N4 H4A 109.8 . . ? Pd1 N4 H4A 109.8 . . ? C12 N4 H4B 109.8 . . ? Pd1 N4 H4B 109.8 . . ? H4A N4 H4B 108.2 . . ? N6 C14 C13 106.9(3) . . ? N6 C14 H14A 110.3 . . ? C13 C14 H14A 110.3 . . ? N6 C14 H14B 110.3 . . ? C13 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? O1 C1 N1 121.7(3) . . ? O1 C1 C2 120.0(3) . . ? N1 C1 C2 118.4(3) . . ? C5 C4 C3 117.2(3) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? N1 C5 C4 123.0(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C10 C9 C8 117.7(3) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? N4 C12 C11 108.2(3) . . ? N4 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? N4 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N3 C11 C12 107.2(3) . . ? N3 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? N3 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.5 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 1.362 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.179