data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Prof A Jones' _publ_contact_author_address ; TJC Consultancy Rosetree Cottage Georgian Close Eccleston Park Prescot Merseyside L35 7JW UK ; _publ_contact_author_email TJCONSULTANCY@BTCONNECT.COM _publ_section_title ; Deposition of HfO2 and ZrO2 films by liquid injection MOCVD using new monomeric alkoxide precursors ; loop_ _publ_author_name 'A. Jones' 'H. Aspinall' 'Jamie F. Bickley' 'P. Chalker' 'Yim Fun Loo' O.Ruairi ; R.J.Potter ; 'Lesley M. Smith' 'Stephen Taylor' data_ro100m _database_code_depnum_ccdc_archive 'CCDC 255507' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H46 Hf N2 O6' _chemical_formula_weight 637.12 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' Hf Hf -0.5830 6.1852 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_Int_Tables_number 14 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 10.2341(4) _cell_length_b 18.9036(8) _cell_length_c 15.6521(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.0110(10) _cell_angle_gamma 90.00 _cell_volume 2924.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 3.602 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.4112 _exptl_absorpt_correction_T_max 0.7146 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18033 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.23 _reflns_number_total 6731 _reflns_number_gt 5710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0325P)^2^+6.3696P] 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 6731 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9054(4) 0.12446(18) 0.9151(2) 0.0190(7) Uani 1 1 d . . . C2 C 0.7751(4) 0.0828(2) 0.9113(3) 0.0263(8) Uani 1 1 d . . . H2A H 0.7189 0.0816 0.8502 0.039 Uiso 1 1 calc R . . H2B H 0.7249 0.1059 0.9491 0.039 Uiso 1 1 calc R . . H2C H 0.7982 0.0344 0.9321 0.039 Uiso 1 1 calc R . . C3 C 0.9910(4) 0.1298(2) 1.0106(2) 0.0277(8) Uani 1 1 d . . . H3A H 1.0135 0.0822 1.0347 0.042 Uiso 1 1 calc R . . H3B H 0.9400 0.1550 1.0462 0.042 Uiso 1 1 calc R . . H3C H 1.0746 0.1557 1.0122 0.042 Uiso 1 1 calc R . . C4 C 0.8672(3) 0.19752(18) 0.8777(2) 0.0170(7) Uani 1 1 d . . . C5 C 0.7741(4) 0.30486(19) 0.8626(3) 0.0272(8) Uani 1 1 d . . . H5A H 0.8125 0.3471 0.8975 0.033 Uiso 1 1 calc R . . H5B H 0.6757 0.3122 0.8378 0.033 Uiso 1 1 calc R . . C6 C 0.8442(4) 0.29183(17) 0.7879(2) 0.0196(7) Uani 1 1 d . . . C7 C 0.9635(5) 0.3408(2) 0.7951(4) 0.0418(12) Uani 1 1 d . . . H7A H 1.0195 0.3411 0.8563 0.063 Uiso 1 1 calc R . . H7B H 0.9308 0.3887 0.7779 0.063 Uiso 1 1 calc R . . H7C H 1.0176 0.3242 0.7558 0.063 Uiso 1 1 calc R . . C8 C 0.7461(6) 0.2951(3) 0.6974(3) 0.0480(13) Uani 1 1 d . . . H8A H 0.7925 0.2814 0.6525 0.072 Uiso 1 1 calc R . . H8B H 0.7112 0.3434 0.6858 0.072 Uiso 1 1 calc R . . H8C H 0.6707 0.2625 0.6952 0.072 Uiso 1 1 calc R . . C9 C 1.3088(3) 0.17981(19) 0.8740(2) 0.0201(7) Uani 1 1 d . . . C10 C 1.3292(4) 0.1099(2) 0.9237(3) 0.0286(8) Uani 1 1 d . . . H10A H 1.2465 0.0975 0.9408 0.043 Uiso 1 1 calc R . . H10B H 1.4045 0.1144 0.9768 0.043 Uiso 1 1 calc R . . H10C H 1.3499 0.0728 0.8855 0.043 Uiso 1 1 calc R . . C11 C 1.2757(4) 0.2403(2) 0.9290(2) 0.0243(8) Uani 1 1 d . . . H11A H 1.2730 0.2849 0.8965 0.036 Uiso 1 1 calc R . . H11B H 1.3452 0.2432 0.9852 0.036 Uiso 1 1 calc R . . H11C H 1.1873 0.2318 0.9405 0.036 Uiso 1 1 calc R . . C12 C 1.4285(4) 0.1992(2) 0.8359(2) 0.0270(8) Uani 1 1 d . . . H12A H 1.4861 0.2358 0.8726 0.032 Uiso 1 1 calc R . . H12B H 1.4846 0.1571 0.8330 0.032 Uiso 1 1 calc R . . C13 C 1.2365(3) 0.20384(18) 0.7292(2) 0.0185(7) Uani 1 1 d . . . C14 C 1.1448(3) 0.21225(18) 0.6373(2) 0.0177(7) Uani 1 1 d . . . C15 C 1.1919(4) 0.1617(2) 0.5746(2) 0.0253(8) Uani 1 1 d . . . H15A H 1.1892 0.1129 0.5954 0.038 Uiso 1 1 calc R . . H15B H 1.2846 0.1736 0.5735 0.038 Uiso 1 1 calc R . . H15C H 1.1319 0.1661 0.5149 0.038 Uiso 1 1 calc R . . C16 C 1.1495(4) 0.2886(2) 0.6057(2) 0.0257(8) Uani 1 1 d . . . H16A H 1.0910 0.2933 0.5456 0.038 Uiso 1 1 calc R . . H16B H 1.2427 0.3007 0.6059 0.038 Uiso 1 1 calc R . . H16C H 1.1180 0.3205 0.6455 0.038 Uiso 1 1 calc R . . C17 C 1.1071(4) -0.03109(19) 0.7082(3) 0.0260(8) Uani 1 1 d . . . C18 C 1.2578(5) -0.0316(3) 0.7184(3) 0.0432(11) Uani 1 1 d . . . H18A H 1.2785 -0.0038 0.6707 0.065 Uiso 1 1 calc R . . H18B H 1.2886 -0.0804 0.7155 0.065 Uiso 1 1 calc R . . H18C H 1.3040 -0.0109 0.7756 0.065 Uiso 1 1 calc R . . C19 C 1.0712(6) -0.0691(3) 0.7845(4) 0.0497(13) Uani 1 1 d . . . H19A H 1.1235 -0.0489 0.8406 0.075 Uiso 1 1 calc R . . H19B H 1.0925 -0.1195 0.7824 0.075 Uiso 1 1 calc R . . H19C H 0.9743 -0.0634 0.7796 0.075 Uiso 1 1 calc R . . C20 C 1.0316(5) -0.0656(2) 0.6217(3) 0.0416(11) Uani 1 1 d . . . H20A H 0.9342 -0.0650 0.6171 0.062 Uiso 1 1 calc R . . H20B H 1.0621 -0.1147 0.6205 0.062 Uiso 1 1 calc R . . H20C H 1.0498 -0.0395 0.5720 0.062 Uiso 1 1 calc R . . C21 C 0.6785(4) 0.08093(19) 0.6091(2) 0.0217(7) Uani 1 1 d . . . C22 C 0.7251(6) 0.0684(3) 0.5248(3) 0.0565(14) Uani 1 1 d . . . H22A H 0.7544 0.1133 0.5046 0.085 Uiso 1 1 calc R . . H22B H 0.6499 0.0490 0.4786 0.085 Uiso 1 1 calc R . . H22C H 0.8006 0.0348 0.5373 0.085 Uiso 1 1 calc R . . C23 C 0.5634(6) 0.1335(3) 0.5862(5) 0.073(2) Uani 1 1 d . . . H23A H 0.5294 0.1421 0.6384 0.109 Uiso 1 1 calc R . . H23B H 0.4903 0.1145 0.5383 0.109 Uiso 1 1 calc R . . H23C H 0.5957 0.1781 0.5671 0.109 Uiso 1 1 calc R . . C24 C 0.6409(7) 0.0130(3) 0.6416(4) 0.080(2) Uani 1 1 d . . . H24A H 0.7225 -0.0153 0.6651 0.120 Uiso 1 1 calc R . . H24B H 0.5798 -0.0125 0.5929 0.120 Uiso 1 1 calc R . . H24C H 0.5954 0.0216 0.6885 0.120 Uiso 1 1 calc R . . Hf1 Hf 0.976331(12) 0.124593(7) 0.735303(8) 0.01307(5) Uani 1 1 d . . . N1 N 0.8956(3) 0.21848(14) 0.80740(18) 0.0152(5) Uani 1 1 d . . . N2 N 1.1961(3) 0.17477(15) 0.79134(18) 0.0163(6) Uani 1 1 d . . . O1 O 0.9780(2) 0.09287(12) 0.86094(15) 0.0173(5) Uani 1 1 d . . . O2 O 0.7991(3) 0.24163(13) 0.91756(17) 0.0248(6) Uani 1 1 d . . . O3 O 1.0146(2) 0.19381(12) 0.64295(15) 0.0166(5) Uani 1 1 d . . . O4 O 1.3660(2) 0.22623(14) 0.74733(17) 0.0253(6) Uani 1 1 d . . . O5 O 1.0625(3) 0.03989(12) 0.70776(16) 0.0211(5) Uani 1 1 d . . . O6 O 0.7884(3) 0.10913(13) 0.67321(17) 0.0229(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 C1 0.0202(17) 0.0201(16) 0.0188(16) 0.0025(13) 0.0086(13) -0.0006(14) C2 0.027(2) 0.0250(18) 0.031(2) 0.0012(15) 0.0149(16) -0.0036(15) C3 0.034(2) 0.036(2) 0.0141(16) 0.0029(15) 0.0073(15) 0.0035(17) C4 0.0169(16) 0.0198(16) 0.0138(15) -0.0036(12) 0.0032(13) 0.0000(13) C5 0.035(2) 0.0199(17) 0.032(2) -0.0001(15) 0.0186(18) 0.0048(16) C6 0.0224(18) 0.0175(15) 0.0200(17) 0.0002(13) 0.0078(14) 0.0044(14) C7 0.041(3) 0.0190(19) 0.076(3) 0.001(2) 0.034(3) 0.0004(18) C8 0.064(3) 0.044(3) 0.024(2) -0.0056(19) -0.010(2) 0.034(2) C9 0.0136(16) 0.0267(18) 0.0179(16) -0.0027(14) 0.0005(13) -0.0014(14) C10 0.026(2) 0.031(2) 0.0238(19) 0.0022(15) -0.0030(15) 0.0058(16) C11 0.0225(18) 0.0282(18) 0.0200(17) -0.0043(15) 0.0012(14) -0.0017(15) C12 0.0139(17) 0.041(2) 0.0238(18) -0.0002(16) 0.0014(14) -0.0014(16) C13 0.0140(16) 0.0219(16) 0.0200(16) -0.0008(14) 0.0047(13) -0.0003(13) C14 0.0162(16) 0.0223(16) 0.0149(15) 0.0016(13) 0.0045(13) -0.0027(13) C15 0.028(2) 0.0305(19) 0.0199(18) 0.0009(15) 0.0101(15) 0.0009(16) C16 0.028(2) 0.0269(18) 0.0229(18) 0.0051(15) 0.0080(15) -0.0045(16) C17 0.036(2) 0.0166(16) 0.0255(19) 0.0007(14) 0.0072(16) 0.0084(15) C18 0.035(2) 0.041(3) 0.053(3) -0.008(2) 0.012(2) 0.013(2) C19 0.066(3) 0.034(2) 0.053(3) 0.024(2) 0.024(3) 0.014(2) C20 0.052(3) 0.027(2) 0.043(3) -0.0090(19) 0.005(2) 0.009(2) C21 0.0160(17) 0.0215(17) 0.0239(18) -0.0069(14) -0.0019(14) -0.0027(14) C22 0.066(4) 0.061(3) 0.039(3) -0.003(2) 0.008(3) 0.004(3) C23 0.052(4) 0.076(4) 0.073(4) -0.019(3) -0.016(3) 0.015(3) C24 0.084(5) 0.061(4) 0.072(4) 0.014(3) -0.023(4) -0.044(4) Hf1 0.01252(8) 0.01423(7) 0.01281(7) -0.00097(5) 0.00392(5) -0.00058(5) N1 0.0155(13) 0.0160(13) 0.0142(13) 0.0008(10) 0.0041(11) 0.0033(11) N2 0.0123(13) 0.0199(13) 0.0148(13) 0.0010(11) 0.0003(11) 0.0010(11) O1 0.0183(12) 0.0187(11) 0.0165(11) -0.0008(9) 0.0076(9) 0.0022(10) O2 0.0335(15) 0.0223(12) 0.0241(13) 0.0007(10) 0.0172(11) 0.0065(11) O3 0.0146(11) 0.0198(11) 0.0153(11) 0.0021(9) 0.0035(9) -0.0004(9) O4 0.0151(12) 0.0382(15) 0.0220(13) 0.0013(11) 0.0039(10) -0.0068(11) O5 0.0288(14) 0.0138(11) 0.0236(13) -0.0009(10) 0.0121(11) 0.0044(10) O6 0.0174(12) 0.0299(13) 0.0213(13) -0.0049(10) 0.0048(10) -0.0073(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.398(4) . ? C1 C4 1.511(5) . ? C1 C3 1.528(5) . ? C1 C2 1.536(5) . ? C4 N1 1.272(4) . ? C4 O2 1.340(4) . ? C5 O2 1.456(4) . ? C5 C6 1.542(5) . ? C6 N1 1.486(4) . ? C6 C8 1.511(5) . ? C6 C7 1.512(5) . ? C9 N2 1.498(4) . ? C9 C10 1.520(5) . ? C9 C11 1.521(5) . ? C9 C12 1.539(5) . ? C12 O4 1.460(4) . ? C13 N2 1.276(4) . ? C13 O4 1.349(4) . ? C13 C14 1.509(5) . ? C14 O3 1.402(4) . ? C14 C16 1.529(5) . ? C14 C15 1.534(5) . ? C17 O5 1.417(4) . ? C17 C18 1.508(6) . ? C17 C19 1.518(6) . ? C17 C20 1.520(6) . ? C21 O6 1.403(4) . ? C21 C24 1.468(6) . ? C21 C23 1.512(7) . ? C21 C22 1.534(6) . ? Hf1 O5 1.930(2) . ? Hf1 O6 1.940(3) . ? Hf1 O1 2.052(2) . ? Hf1 O3 2.061(2) . ? Hf1 N1 2.364(3) . ? Hf1 N2 2.388(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 O1 C1 C4 106.3(3) . . ? O1 C1 C3 111.2(3) . . ? C4 C1 C3 110.1(3) . . ? O1 C1 C2 110.5(3) . . ? C4 C1 C2 108.6(3) . . ? C3 C1 C2 110.1(3) . . ? N1 C4 O2 118.2(3) . . ? N1 C4 C1 121.7(3) . . ? O2 C4 C1 120.1(3) . . ? O2 C5 C6 105.8(3) . . ? N1 C6 C8 110.1(3) . . ? N1 C6 C7 108.7(3) . . ? C8 C6 C7 111.9(4) . . ? N1 C6 C5 101.7(3) . . ? C8 C6 C5 112.1(3) . . ? C7 C6 C5 111.8(3) . . ? N2 C9 C10 111.1(3) . . ? N2 C9 C11 107.5(3) . . ? C10 C9 C11 112.7(3) . . ? N2 C9 C12 101.1(3) . . ? C10 C9 C12 112.8(3) . . ? C11 C9 C12 110.9(3) . . ? O4 C12 C9 104.8(3) . . ? N2 C13 O4 118.0(3) . . ? N2 C13 C14 121.9(3) . . ? O4 C13 C14 120.1(3) . . ? O3 C14 C13 106.2(3) . . ? O3 C14 C16 111.4(3) . . ? C13 C14 C16 110.1(3) . . ? O3 C14 C15 110.3(3) . . ? C13 C14 C15 108.8(3) . . ? C16 C14 C15 109.9(3) . . ? O5 C17 C18 109.0(3) . . ? O5 C17 C19 107.9(3) . . ? C18 C17 C19 111.3(4) . . ? O5 C17 C20 108.3(3) . . ? C18 C17 C20 111.2(4) . . ? C19 C17 C20 109.0(4) . . ? O6 C21 C24 108.5(3) . . ? O6 C21 C23 110.5(3) . . ? C24 C21 C23 113.5(5) . . ? O6 C21 C22 107.7(3) . . ? C24 C21 C22 109.3(4) . . ? C23 C21 C22 107.1(4) . . ? O5 Hf1 O6 102.37(11) . . ? O5 Hf1 O1 94.63(10) . . ? O6 Hf1 O1 101.37(10) . . ? O5 Hf1 O3 100.92(9) . . ? O6 Hf1 O3 95.05(10) . . ? O1 Hf1 O3 154.40(9) . . ? O5 Hf1 N1 165.00(10) . . ? O6 Hf1 N1 85.89(10) . . ? O1 Hf1 N1 71.28(9) . . ? O3 Hf1 N1 90.66(9) . . ? O5 Hf1 N2 88.30(10) . . ? O6 Hf1 N2 163.98(10) . . ? O1 Hf1 N2 89.47(9) . . ? O3 Hf1 N2 70.96(9) . . ? N1 Hf1 N2 86.50(10) . . ? C4 N1 C6 108.7(3) . . ? C4 N1 Hf1 111.4(2) . . ? C6 N1 Hf1 138.7(2) . . ? C13 N2 C9 107.6(3) . . ? C13 N2 Hf1 110.6(2) . . ? C9 N2 Hf1 141.7(2) . . ? C1 O1 Hf1 125.6(2) . . ? C4 O2 C5 105.6(3) . . ? C14 O3 Hf1 124.0(2) . . ? C13 O4 C12 104.8(3) . . ? C17 O5 Hf1 161.8(2) . . ? C21 O6 Hf1 157.2(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 O1 C1 C4 N1 3.2(4) . . . . ? C3 C1 C4 N1 123.7(4) . . . . ? C2 C1 C4 N1 -115.7(4) . . . . ? O1 C1 C4 O2 -178.2(3) . . . . ? C3 C1 C4 O2 -57.8(4) . . . . ? C2 C1 C4 O2 62.9(4) . . . . ? O2 C5 C6 N1 3.2(4) . . . . ? O2 C5 C6 C8 120.9(4) . . . . ? O2 C5 C6 C7 -112.5(4) . . . . ? N2 C9 C12 O4 19.0(4) . . . . ? C10 C9 C12 O4 137.7(3) . . . . ? C11 C9 C12 O4 -94.8(3) . . . . ? N2 C13 C14 O3 9.4(4) . . . . ? O4 C13 C14 O3 -171.7(3) . . . . ? N2 C13 C14 C16 130.2(3) . . . . ? O4 C13 C14 C16 -50.9(4) . . . . ? N2 C13 C14 C15 -109.3(4) . . . . ? O4 C13 C14 C15 69.5(4) . . . . ? O2 C4 N1 C6 1.1(4) . . . . ? C1 C4 N1 C6 179.7(3) . . . . ? O2 C4 N1 Hf1 -168.9(2) . . . . ? C1 C4 N1 Hf1 9.7(4) . . . . ? C8 C6 N1 C4 -121.7(4) . . . . ? C7 C6 N1 C4 115.3(4) . . . . ? C5 C6 N1 C4 -2.7(4) . . . . ? C8 C6 N1 Hf1 44.0(5) . . . . ? C7 C6 N1 Hf1 -78.9(4) . . . . ? C5 C6 N1 Hf1 163.1(3) . . . . ? O5 Hf1 N1 C4 -34.6(5) . . . . ? O6 Hf1 N1 C4 89.6(2) . . . . ? O1 Hf1 N1 C4 -13.9(2) . . . . ? O3 Hf1 N1 C4 -175.4(2) . . . . ? N2 Hf1 N1 C4 -104.5(2) . . . . ? O5 Hf1 N1 C6 159.9(4) . . . . ? O6 Hf1 N1 C6 -75.9(3) . . . . ? O1 Hf1 N1 C6 -179.4(3) . . . . ? O3 Hf1 N1 C6 19.1(3) . . . . ? N2 Hf1 N1 C6 90.0(3) . . . . ? O4 C13 N2 C9 5.0(4) . . . . ? C14 C13 N2 C9 -176.2(3) . . . . ? O4 C13 N2 Hf1 -171.1(2) . . . . ? C14 C13 N2 Hf1 7.7(4) . . . . ? C10 C9 N2 C13 -134.8(3) . . . . ? C11 C9 N2 C13 101.4(3) . . . . ? C12 C9 N2 C13 -14.9(4) . . . . ? C10 C9 N2 Hf1 39.3(5) . . . . ? C11 C9 N2 Hf1 -84.5(4) . . . . ? C12 C9 N2 Hf1 159.2(3) . . . . ? O5 Hf1 N2 C13 86.4(2) . . . . ? O6 Hf1 N2 C13 -46.0(5) . . . . ? O1 Hf1 N2 C13 -179.0(2) . . . . ? O3 Hf1 N2 C13 -15.8(2) . . . . ? N1 Hf1 N2 C13 -107.7(2) . . . . ? O5 Hf1 N2 C9 -87.7(3) . . . . ? O6 Hf1 N2 C9 140.0(4) . . . . ? O1 Hf1 N2 C9 7.0(3) . . . . ? O3 Hf1 N2 C9 170.2(4) . . . . ? N1 Hf1 N2 C9 78.3(3) . . . . ? C4 C1 O1 Hf1 -18.8(4) . . . . ? C3 C1 O1 Hf1 -138.5(2) . . . . ? C2 C1 O1 Hf1 98.8(3) . . . . ? O5 Hf1 O1 C1 -166.7(3) . . . . ? O6 Hf1 O1 C1 -63.1(3) . . . . ? O3 Hf1 O1 C1 65.8(3) . . . . ? N1 Hf1 O1 C1 18.6(2) . . . . ? N2 Hf1 O1 C1 105.1(3) . . . . ? N1 C4 O2 C5 1.2(4) . . . . ? C1 C4 O2 C5 -177.4(3) . . . . ? C6 C5 O2 C4 -2.8(4) . . . . ? C13 C14 O3 Hf1 -27.3(3) . . . . ? C16 C14 O3 Hf1 -147.2(2) . . . . ? C15 C14 O3 Hf1 90.5(3) . . . . ? O5 Hf1 O3 C14 -59.7(2) . . . . ? O6 Hf1 O3 C14 -163.4(2) . . . . ? O1 Hf1 O3 C14 66.6(3) . . . . ? N1 Hf1 O3 C14 110.7(2) . . . . ? N2 Hf1 O3 C14 24.6(2) . . . . ? N2 C13 O4 C12 8.1(4) . . . . ? C14 C13 O4 C12 -170.8(3) . . . . ? C9 C12 O4 C13 -16.9(4) . . . . ? C18 C17 O5 Hf1 -129.0(7) . . . . ? C19 C17 O5 Hf1 -8.0(10) . . . . ? C20 C17 O5 Hf1 109.9(8) . . . . ? O6 Hf1 O5 C17 -77.2(8) . . . . ? O1 Hf1 O5 C17 25.5(8) . . . . ? O3 Hf1 O5 C17 -174.9(8) . . . . ? N1 Hf1 O5 C17 45.1(10) . . . . ? N2 Hf1 O5 C17 114.8(8) . . . . ? C24 C21 O6 Hf1 86.9(7) . . . . ? C23 C21 O6 Hf1 -148.0(6) . . . . ? C22 C21 O6 Hf1 -31.3(8) . . . . ? O5 Hf1 O6 C21 -24.2(6) . . . . ? O1 Hf1 O6 C21 -121.6(6) . . . . ? O3 Hf1 O6 C21 78.2(6) . . . . ? N1 Hf1 O6 C21 168.5(6) . . . . ? N2 Hf1 O6 C21 106.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 2.500 _refine_diff_density_min -1.057 _refine_diff_density_rms 0.119 data_ro101m _database_code_depnum_ccdc_archive 'CCDC 255508' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H46 N2 O6 Zr' _chemical_formula_weight 549.85 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' Zr Zr -2.9673 0.5597 '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 10.2627(9) _cell_length_b 18.9374(17) _cell_length_c 15.6465(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.772(2) _cell_angle_gamma 90.00 _cell_volume 2940.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.409 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17985 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.53 _reflns_number_total 6732 _reflns_number_gt 6015 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of 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^)+(0.0384P)^2^+1.6785P] 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 6732 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 C1 C 0.0400(2) 0.33894(11) 0.20701(19) 0.0450(6) Uani 1 1 d . . . H1A H -0.0230 0.3360 0.1484 0.068 Uiso 1 1 calc R . . H1B H 0.0728 0.3875 0.2181 0.068 Uiso 1 1 calc R . . H1C H -0.0061 0.3250 0.2520 0.068 Uiso 1 1 calc R . . C2 C 0.2581(3) 0.29231(13) 0.30076(14) 0.0492(7) Uani 1 1 d . . . H2A H 0.2132 0.2780 0.3463 0.074 Uiso 1 1 calc R . . H2B H 0.2929 0.3405 0.3128 0.074 Uiso 1 1 calc R . . H2C H 0.3328 0.2600 0.3013 0.074 Uiso 1 1 calc R . . C3 C 0.15796(17) 0.28993(9) 0.21094(11) 0.0214(3) Uani 1 1 d . . . C4 C 0.2258(2) 0.30342(10) 0.13504(13) 0.0309(4) Uani 1 1 d . . . H4A H 0.1862 0.3454 0.1004 0.037 Uiso 1 1 calc R . . H4B H 0.3238 0.3111 0.1586 0.037 Uiso 1 1 calc R . . C5 C 0.13300(16) 0.19588(9) 0.12104(11) 0.0184(3) Uani 1 1 d . . . C6 C 0.09399(18) 0.12325(9) 0.08322(11) 0.0208(3) Uani 1 1 d . . . C7 C 0.2231(2) 0.08131(10) 0.08500(14) 0.0317(4) Uani 1 1 d . . . H7A H 0.2782 0.0778 0.1460 0.048 Uiso 1 1 calc R . . H7B H 0.2742 0.1056 0.0488 0.048 Uiso 1 1 calc R . . H7C H 0.1989 0.0338 0.0614 0.048 Uiso 1 1 calc R . . C8 C 0.0071(2) 0.12938(11) -0.01177(12) 0.0301(4) Uani 1 1 d . . . H8A H -0.0175 0.0821 -0.0359 0.045 Uiso 1 1 calc R . . H8B H 0.0580 0.1539 -0.0480 0.045 Uiso 1 1 calc R . . H8C H -0.0748 0.1561 -0.0123 0.045 Uiso 1 1 calc R . . C9 C -0.3306(2) 0.11002(11) 0.07439(13) 0.0307(4) Uani 1 1 d . . . H9A H -0.2471 0.0970 0.0588 0.046 Uiso 1 1 calc R . . H9B H -0.4034 0.1154 0.0204 0.046 Uiso 1 1 calc R . . H9C H -0.3545 0.0730 0.1114 0.046 Uiso 1 1 calc R . . C10 C -0.27641(19) 0.23997(11) 0.06973(12) 0.0286(4) Uani 1 1 d . . . H10A H -0.2685 0.2840 0.1035 0.043 Uiso 1 1 calc R . . H10B H -0.3482 0.2447 0.0151 0.043 Uiso 1 1 calc R . . H10C H -0.1909 0.2300 0.0551 0.043 Uiso 1 1 calc R . . C11 C -0.31016(17) 0.17947(10) 0.12500(11) 0.0233(4) Uani 1 1 d . . . C12 C -0.42982(18) 0.19920(12) 0.16306(13) 0.0326(4) Uani 1 1 d . . . H12A H -0.4865 0.2360 0.1265 0.039 Uiso 1 1 calc R . . H12B H -0.4864 0.1573 0.1658 0.039 Uiso 1 1 calc R . . C13 C -0.23849(17) 0.20282(9) 0.26937(11) 0.0217(3) Uani 1 1 d . . . C14 C -0.14733(17) 0.21052(9) 0.36185(11) 0.0219(3) Uani 1 1 d . . . C15 C -0.1515(2) 0.28688(10) 0.39399(13) 0.0304(4) Uani 1 1 d . . . H15A H -0.0929 0.2913 0.4539 0.046 Uiso 1 1 calc R . . H15B H -0.2441 0.2992 0.3944 0.046 Uiso 1 1 calc R . . H15C H -0.1201 0.3189 0.3542 0.046 Uiso 1 1 calc R . . C16 C -0.1964(2) 0.16011(11) 0.42351(12) 0.0296(4) Uani 1 1 d . . . H16A H -0.1966 0.1117 0.4015 0.044 Uiso 1 1 calc R . . H16B H -0.2880 0.1733 0.4255 0.044 Uiso 1 1 calc R . . H16C H -0.1361 0.1631 0.4831 0.044 Uiso 1 1 calc R . . C17 C 0.32506(17) 0.07853(10) 0.38752(12) 0.0239(4) Uani 1 1 d . . . C18 C 0.3674(4) 0.0143(2) 0.3539(3) 0.0320(9) Uiso 0.500(3) 1 d P A 1 H18A H 0.2925 -0.0194 0.3410 0.048 Uiso 0.500(3) 1 calc PR A 1 H18B H 0.4435 -0.0059 0.3981 0.048 Uiso 0.500(3) 1 calc PR A 1 H18C H 0.3949 0.0245 0.2996 0.048 Uiso 0.500(3) 1 calc PR A 1 C19 C 0.2846(4) 0.06564(19) 0.4784(2) 0.0255(8) Uiso 0.500(3) 1 d P A 1 H19A H 0.2547 0.1102 0.4988 0.038 Uiso 0.500(3) 1 calc PR A 1 H19B H 0.3629 0.0478 0.5229 0.038 Uiso 0.500(3) 1 calc PR A 1 H19C H 0.2114 0.0310 0.4691 0.038 Uiso 0.500(3) 1 calc PR A 1 C20 C 0.4362(4) 0.1361(2) 0.4091(3) 0.0348(10) Uiso 0.500(3) 1 d P A 1 H20A H 0.4604 0.1499 0.3548 0.052 Uiso 0.500(3) 1 calc PR A 1 H20B H 0.5159 0.1173 0.4516 0.052 Uiso 0.500(3) 1 calc PR A 1 H20C H 0.4025 0.1774 0.4346 0.052 Uiso 0.500(3) 1 calc PR A 1 C18' C 0.3012(4) 0.0011(2) 0.4109(3) 0.0302(9) Uiso 0.500(3) 1 d P A 2 H18D H 0.2340 -0.0003 0.4455 0.045 Uiso 0.500(3) 1 calc PR A 2 H18E H 0.3860 -0.0193 0.4456 0.045 Uiso 0.500(3) 1 calc PR A 2 H18F H 0.2685 -0.0262 0.3564 0.045 Uiso 0.500(3) 1 calc PR A 2 C19' C 0.3654(5) 0.1244(2) 0.4621(3) 0.0383(11) Uiso 0.500(3) 1 d P A 2 H19D H 0.3872 0.1711 0.4424 0.057 Uiso 0.500(3) 1 calc PR A 2 H19E H 0.4449 0.1048 0.5039 0.057 Uiso 0.500(3) 1 calc PR A 2 H19F H 0.2917 0.1289 0.4911 0.057 Uiso 0.500(3) 1 calc PR A 2 C20' C 0.4381(4) 0.0743(2) 0.3338(3) 0.0371(10) Uiso 0.500(3) 1 d P A 2 H20D H 0.4086 0.0420 0.2838 0.056 Uiso 0.500(3) 1 calc PR A 2 H20E H 0.5225 0.0571 0.3729 0.056 Uiso 0.500(3) 1 calc PR A 2 H20F H 0.4526 0.1214 0.3120 0.056 Uiso 0.500(3) 1 calc PR A 2 C21 C -0.1106(2) -0.03322(9) 0.29349(12) 0.0298(4) Uani 1 1 d . . . C22 C -0.0401(4) -0.06409(14) 0.38310(18) 0.0692(10) Uani 1 1 d . . . H22A H 0.0577 -0.0607 0.3919 0.104 Uiso 1 1 calc R . . H22B H -0.0658 -0.1138 0.3854 0.104 Uiso 1 1 calc R . . H22C H -0.0668 -0.0377 0.4298 0.104 Uiso 1 1 calc R . . C23 C -0.2602(3) -0.03509(14) 0.27950(19) 0.0531(7) Uani 1 1 d . . . H23A H -0.2859 -0.0048 0.3233 0.080 Uiso 1 1 calc R . . H23B H -0.2890 -0.0837 0.2860 0.080 Uiso 1 1 calc R . . H23C H -0.3037 -0.0180 0.2199 0.080 Uiso 1 1 calc R . . C24 C -0.0670(3) -0.07430(14) 0.2219(2) 0.0610(8) Uani 1 1 d . . . H24A H -0.1191 -0.0583 0.1637 0.091 Uiso 1 1 calc R . . H24B H -0.0830 -0.1248 0.2285 0.091 Uiso 1 1 calc R . . H24C H 0.0292 -0.0663 0.2275 0.091 Uiso 1 1 calc R . . N1 N 0.10555(13) 0.21670(7) 0.19189(9) 0.0170(3) Uani 1 1 d . A . N2 N -0.19841(14) 0.17412(8) 0.20714(9) 0.0194(3) Uani 1 1 d . A . O1 O 0.20047(13) 0.24015(7) 0.08036(8) 0.0261(3) Uani 1 1 d . . . O2 O 0.02253(12) 0.09129(6) 0.13785(8) 0.0200(2) Uani 1 1 d . A . O3 O -0.36753(12) 0.22586(8) 0.25163(9) 0.0295(3) Uani 1 1 d . . . O4 O -0.01795(11) 0.19158(6) 0.35615(7) 0.0193(2) Uani 1 1 d . A . O5 O 0.20893(12) 0.10491(7) 0.32749(8) 0.0234(3) Uani 1 1 d . A . O6 O -0.06708(13) 0.03723(6) 0.29069(8) 0.0237(3) Uani 1 1 d . A . Zr1 Zr 0.022235(15) 0.121829(8) 0.264407(10) 0.01444(6) 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 C1 0.0450(13) 0.0195(9) 0.0794(17) -0.0041(10) 0.0321(12) -0.0006(8) C2 0.0609(15) 0.0504(14) 0.0256(10) 0.0044(9) -0.0082(10) -0.0347(12) C3 0.0230(8) 0.0214(8) 0.0202(8) -0.0003(6) 0.0065(7) -0.0060(7) C4 0.0417(11) 0.0240(9) 0.0319(10) -0.0024(8) 0.0186(9) -0.0097(8) C5 0.0165(8) 0.0217(8) 0.0163(8) 0.0029(6) 0.0033(6) 0.0014(6) C6 0.0241(9) 0.0214(8) 0.0186(8) -0.0013(6) 0.0085(7) -0.0006(6) C7 0.0347(11) 0.0281(10) 0.0392(11) 0.0019(8) 0.0216(9) 0.0062(8) C8 0.0372(11) 0.0367(10) 0.0171(9) -0.0032(7) 0.0085(8) -0.0045(8) C9 0.0255(10) 0.0375(10) 0.0243(9) -0.0043(8) -0.0022(8) -0.0066(8) C10 0.0232(9) 0.0360(10) 0.0240(9) 0.0043(8) 0.0012(7) -0.0009(7) C11 0.0148(8) 0.0317(9) 0.0208(8) 0.0004(7) -0.0003(6) -0.0004(7) C12 0.0161(9) 0.0508(12) 0.0283(10) 0.0021(9) 0.0007(7) 0.0015(8) C13 0.0158(8) 0.0263(9) 0.0232(9) 0.0007(7) 0.0053(7) 0.0016(6) C14 0.0215(8) 0.0261(9) 0.0186(8) -0.0043(7) 0.0063(7) 0.0027(7) C15 0.0356(11) 0.0300(10) 0.0258(9) -0.0070(8) 0.0082(8) 0.0088(8) C16 0.0304(10) 0.0396(11) 0.0222(9) -0.0003(8) 0.0128(8) 0.0007(8) C17 0.0161(8) 0.0260(9) 0.0255(9) 0.0080(7) -0.0019(7) 0.0020(6) C21 0.0443(11) 0.0179(8) 0.0260(9) -0.0011(7) 0.0067(8) -0.0117(8) C22 0.109(3) 0.0361(13) 0.0452(15) 0.0148(11) -0.0124(15) -0.0309(14) C23 0.0448(14) 0.0496(14) 0.0677(17) 0.0030(12) 0.0192(13) -0.0217(11) C24 0.0755(19) 0.0361(13) 0.078(2) -0.0309(13) 0.0315(16) -0.0185(13) N1 0.0163(7) 0.0182(7) 0.0160(6) 0.0003(5) 0.0029(5) -0.0010(5) N2 0.0150(7) 0.0252(7) 0.0168(7) -0.0012(5) 0.0018(5) -0.0009(5) O1 0.0343(7) 0.0246(6) 0.0234(6) 0.0006(5) 0.0150(6) -0.0054(5) O2 0.0241(6) 0.0199(6) 0.0175(6) -0.0019(5) 0.0081(5) -0.0035(5) O3 0.0172(6) 0.0448(8) 0.0270(7) 0.0004(6) 0.0066(5) 0.0084(5) O4 0.0170(6) 0.0232(6) 0.0169(6) -0.0031(4) 0.0030(4) 0.0012(4) O5 0.0165(6) 0.0297(6) 0.0227(6) 0.0049(5) 0.0024(5) 0.0064(5) O6 0.0309(7) 0.0181(6) 0.0252(6) -0.0020(5) 0.0131(5) -0.0067(5) Zr1 0.01359(9) 0.01576(9) 0.01417(9) 0.00038(5) 0.00388(6) -0.00003(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 C1 C3 1.514(3) . ? C2 C3 1.515(3) . ? C3 N1 1.490(2) . ? C3 C4 1.543(2) . ? C4 O1 1.457(2) . ? C5 N1 1.274(2) . ? C5 O1 1.346(2) . ? C5 C6 1.511(2) . ? C6 O2 1.398(2) . ? C6 C8 1.530(3) . ? C6 C7 1.539(2) . ? C9 C11 1.522(3) . ? C10 C11 1.527(3) . ? C11 N2 1.492(2) . ? C11 C12 1.541(3) . ? C12 O3 1.460(2) . ? C13 N2 1.272(2) . ? C13 O3 1.354(2) . ? C13 C14 1.517(2) . ? C14 O4 1.400(2) . ? C14 C16 1.531(3) . ? C14 C15 1.535(2) . ? C17 O5 1.407(2) . ? C17 C19' 1.429(5) . ? C17 C18 1.435(4) . ? C17 C18' 1.546(4) . ? C17 C20 1.551(5) . ? C17 C19 1.598(4) . ? C17 C20' 1.598(5) . ? C21 O6 1.411(2) . ? C21 C23 1.495(3) . ? C21 C22 1.521(3) . ? C21 C24 1.521(3) . ? N1 Zr1 2.3960(14) . ? N2 Zr1 2.4241(14) . ? O2 Zr1 2.0636(12) . ? O4 Zr1 2.0682(11) . ? O5 Zr1 1.9452(12) . ? O6 Zr1 1.9413(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C3 C1 108.57(14) . . ? N1 C3 C2 109.76(15) . . ? C1 C3 C2 111.43(19) . . ? N1 C3 C4 102.17(13) . . ? C1 C3 C4 112.32(17) . . ? C2 C3 C4 112.13(17) . . ? O1 C4 C3 105.55(14) . . ? N1 C5 O1 118.25(15) . . ? N1 C5 C6 121.83(15) . . ? O1 C5 C6 119.91(14) . . ? O2 C6 C5 106.42(13) . . ? O2 C6 C8 111.11(15) . . ? C5 C6 C8 109.99(14) . . ? O2 C6 C7 110.42(14) . . ? C5 C6 C7 108.78(15) . . ? C8 C6 C7 110.04(15) . . ? N2 C11 C9 111.30(15) . . ? N2 C11 C10 107.65(14) . . ? C9 C11 C10 112.01(16) . . ? N2 C11 C12 101.36(14) . . ? C9 C11 C12 113.13(16) . . ? C10 C11 C12 110.78(16) . . ? O3 C12 C11 104.55(14) . . ? N2 C13 O3 118.10(15) . . ? N2 C13 C14 122.04(15) . . ? O3 C13 C14 119.85(15) . . ? O4 C14 C13 106.19(13) . . ? O4 C14 C16 110.50(14) . . ? C13 C14 C16 108.61(15) . . ? O4 C14 C15 111.60(15) . . ? C13 C14 C15 109.96(15) . . ? C16 C14 C15 109.87(15) . . ? O5 C17 C19' 110.4(2) . . ? O5 C17 C18 109.9(2) . . ? C19' C17 C18 139.7(3) . . ? O5 C17 C18' 109.65(19) . . ? C19' C17 C18' 114.5(3) . . ? C18 C17 C18' 50.5(2) . . ? O5 C17 C20 110.3(2) . . ? C19' C17 C20 49.5(3) . . ? C18 C17 C20 113.6(3) . . ? C18' C17 C20 140.1(2) . . ? O5 C17 C19 106.25(18) . . ? C19' C17 C19 56.9(2) . . ? C18 C17 C19 111.6(2) . . ? C18' C17 C19 63.4(2) . . ? C20 C17 C19 104.9(2) . . ? O5 C17 C20' 105.8(2) . . ? C19' C17 C20' 111.2(3) . . ? C18 C17 C20' 55.7(2) . . ? C18' C17 C20' 104.9(2) . . ? C20 C17 C20' 63.7(2) . . ? C19 C17 C20' 148.0(2) . . ? O6 C21 C23 109.82(18) . . ? O6 C21 C22 108.20(16) . . ? C23 C21 C22 110.8(2) . . ? O6 C21 C24 107.81(17) . . ? C23 C21 C24 111.3(2) . . ? C22 C21 C24 108.8(2) . . ? C5 N1 C3 108.27(14) . . ? C5 N1 Zr1 111.40(11) . . ? C3 N1 Zr1 139.24(10) . . ? C13 N2 C11 107.63(14) . . ? C13 N2 Zr1 110.22(11) . . ? C11 N2 Zr1 141.87(11) . . ? C5 O1 C4 105.69(13) . . ? C6 O2 Zr1 126.49(10) . . ? C13 O3 C12 104.58(13) . . ? C14 O4 Zr1 124.62(10) . . ? C17 O5 Zr1 162.55(12) . . ? C21 O6 Zr1 163.16(12) . . ? O6 Zr1 O5 102.34(5) . . ? O6 Zr1 O2 95.06(5) . . ? O5 Zr1 O2 101.45(5) . . ? O6 Zr1 O4 101.05(5) . . ? O5 Zr1 O4 95.62(5) . . ? O2 Zr1 O4 153.42(5) . . ? O6 Zr1 N1 164.57(5) . . ? O5 Zr1 N1 86.53(5) . . ? O2 Zr1 N1 70.59(5) . . ? O4 Zr1 N1 90.47(5) . . ? O6 Zr1 N2 88.19(5) . . ? O5 Zr1 N2 164.01(5) . . ? O2 Zr1 N2 89.40(5) . . ? O4 Zr1 N2 70.30(5) . . ? N1 Zr1 N2 86.06(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 O1 2.48(18) . . . . ? C1 C3 C4 O1 -113.67(18) . . . . ? C2 C3 C4 O1 119.94(18) . . . . ? N1 C5 C6 O2 2.8(2) . . . . ? O1 C5 C6 O2 -178.21(14) . . . . ? N1 C5 C6 C8 123.27(18) . . . . ? O1 C5 C6 C8 -57.8(2) . . . . ? N1 C5 C6 C7 -116.15(18) . . . . ? O1 C5 C6 C7 62.8(2) . . . . ? N2 C11 C12 O3 18.87(19) . . . . ? C9 C11 C12 O3 138.13(16) . . . . ? C10 C11 C12 O3 -95.15(17) . . . . ? N2 C13 C14 O4 9.3(2) . . . . ? O3 C13 C14 O4 -171.83(15) . . . . ? N2 C13 C14 C16 -109.59(19) . . . . ? O3 C13 C14 C16 69.3(2) . . . . ? N2 C13 C14 C15 130.15(18) . . . . ? O3 C13 C14 C15 -51.0(2) . . . . ? O1 C5 N1 C3 0.8(2) . . . . ? C6 C5 N1 C3 179.75(15) . . . . ? O1 C5 N1 Zr1 -169.66(11) . . . . ? C6 C5 N1 Zr1 9.32(19) . . . . ? C1 C3 N1 C5 116.83(18) . . . . ? C2 C3 N1 C5 -121.15(18) . . . . ? C4 C3 N1 C5 -2.00(18) . . . . ? C1 C3 N1 Zr1 -76.9(2) . . . . ? C2 C3 N1 Zr1 45.1(2) . . . . ? C4 C3 N1 Zr1 164.28(13) . . . . ? O3 C13 N2 C11 4.5(2) . . . . ? C14 C13 N2 C11 -176.56(16) . . . . ? O3 C13 N2 Zr1 -170.82(12) . . . . ? C14 C13 N2 Zr1 8.1(2) . . . . ? C9 C11 N2 C13 -135.12(16) . . . . ? C10 C11 N2 C13 101.77(17) . . . . ? C12 C11 N2 C13 -14.57(19) . . . . ? C9 C11 N2 Zr1 37.8(2) . . . . ? C10 C11 N2 Zr1 -85.3(2) . . . . ? C12 C11 N2 Zr1 158.35(15) . . . . ? N1 C5 O1 C4 1.0(2) . . . . ? C6 C5 O1 C4 -178.04(16) . . . . ? C3 C4 O1 C5 -2.15(19) . . . . ? C5 C6 O2 Zr1 -17.83(18) . . . . ? C8 C6 O2 Zr1 -137.55(12) . . . . ? C7 C6 O2 Zr1 100.06(15) . . . . ? N2 C13 O3 C12 8.5(2) . . . . ? C14 C13 O3 C12 -170.44(16) . . . . ? C11 C12 O3 C13 -16.93(19) . . . . ? C13 C14 O4 Zr1 -27.90(18) . . . . ? C16 C14 O4 Zr1 89.70(15) . . . . ? C15 C14 O4 Zr1 -147.73(12) . . . . ? C19' C17 O5 Zr1 -94.9(4) . . . . ? C18 C17 O5 Zr1 86.0(4) . . . . ? C18' C17 O5 Zr1 32.1(5) . . . . ? C20 C17 O5 Zr1 -148.0(4) . . . . ? C19 C17 O5 Zr1 -34.9(5) . . . . ? C20' C17 O5 Zr1 144.7(4) . . . . ? C23 C21 O6 Zr1 -133.3(4) . . . . ? C22 C21 O6 Zr1 105.7(4) . . . . ? C24 C21 O6 Zr1 -11.8(5) . . . . ? C21 O6 Zr1 O5 -69.8(4) . . . . ? C21 O6 Zr1 O2 33.1(4) . . . . ? C21 O6 Zr1 O4 -168.1(4) . . . . ? C21 O6 Zr1 N1 54.3(5) . . . . ? C21 O6 Zr1 N2 122.3(4) . . . . ? C17 O5 Zr1 O6 -21.3(4) . . . . ? C17 O5 Zr1 O2 -119.2(4) . . . . ? C17 O5 Zr1 O4 81.3(4) . . . . ? C17 O5 Zr1 N1 171.4(4) . . . . ? C17 O5 Zr1 N2 108.9(4) . . . . ? C6 O2 Zr1 O6 -168.23(13) . . . . ? C6 O2 Zr1 O5 -64.53(13) . . . . ? C6 O2 Zr1 O4 64.39(17) . . . . ? C6 O2 Zr1 N1 17.61(12) . . . . ? C6 O2 Zr1 N2 103.64(13) . . . . ? C14 O4 Zr1 O6 -58.86(13) . . . . ? C14 O4 Zr1 O5 -162.64(12) . . . . ? C14 O4 Zr1 O2 67.38(17) . . . . ? C14 O4 Zr1 N1 110.80(12) . . . . ? C14 O4 Zr1 N2 25.16(12) . . . . ? C5 N1 Zr1 O6 -35.5(2) . . . . ? C3 N1 Zr1 O6 158.47(18) . . . . ? C5 N1 Zr1 O5 90.31(12) . . . . ? C3 N1 Zr1 O5 -75.70(16) . . . . ? C5 N1 Zr1 O2 -13.12(11) . . . . ? C3 N1 Zr1 O2 -179.12(17) . . . . ? C5 N1 Zr1 O4 -174.09(11) . . . . ? C3 N1 Zr1 O4 19.91(16) . . . . ? C5 N1 Zr1 N2 -103.88(11) . . . . ? C3 N1 Zr1 N2 90.12(16) . . . . ? C13 N2 Zr1 O6 86.28(12) . . . . ? C11 N2 Zr1 O6 -86.53(18) . . . . ? C13 N2 Zr1 O5 -45.5(2) . . . . ? C11 N2 Zr1 O5 141.72(19) . . . . ? C13 N2 Zr1 O2 -178.64(12) . . . . ? C11 N2 Zr1 O2 8.55(18) . . . . ? C13 N2 Zr1 O4 -16.14(12) . . . . ? C11 N2 Zr1 O4 171.05(19) . . . . ? C13 N2 Zr1 N1 -108.05(12) . . . . ? C11 N2 Zr1 N1 79.14(18) . . . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.605 _refine_diff_density_min -0.592 _refine_diff_density_rms 0.062