Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Anjana Devi' 'Hans-Werner Becker' 'Urmila Patil' 'Manuela Winter' _publ_contact_author_name 'Dr Anjana Devi' _publ_contact_author_address ; Lehrstuhl für Anorganische Chemie II Inorganic Materials Chemistry Group Ruhr-Universität Bochum Bochum NRW 44780 GERMANY ; _publ_contact_author_email ANJANA.DEVI@RUHR-UNI-BOCHUM.DE _publ_section_title ; Synthesis and structure of mixed isopropoxide-beta-ketoester and beta-ketoamide zirconium complexes: Potential precursors for MOCVD of ZrO2 ; data_962 _database_code_CSD 197510 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H42 N2 O6 Zr' _chemical_formula_weight 521.80 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 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 9.3444(15) _cell_length_b 16.030(3) _cell_length_c 17.888(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.768(4) _cell_angle_gamma 90.00 _cell_volume 2678.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 15.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 axs CCD 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14566 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4648 _reflns_number_gt 3880 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker axs SHELXTL-PLUS' _computing_publication_material SHELXL-97 _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^)+(0.0364P)^2^+1.7701P] 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 4648 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Zr1 Zr 0.31116(2) 0.248625(13) 0.075029(11) 0.02702(9) Uani 1 1 d . . . O11 O 0.44533(16) 0.14418(9) 0.05713(8) 0.0321(3) Uani 1 1 d . . . C12 C 0.5815(2) 0.13464(14) 0.07305(12) 0.0315(5) Uani 1 1 d . . . C121 C 0.6273(3) 0.04516(16) 0.08316(16) 0.0455(6) Uani 1 1 d . . . H12A H 0.5718 0.0195 0.1219 0.068 Uiso 1 1 calc R . . H12B H 0.7282 0.0432 0.0976 0.068 Uiso 1 1 calc R . . H12C H 0.6115 0.0152 0.0365 0.068 Uiso 1 1 calc R . . C13 C 0.6785(2) 0.19737(14) 0.08254(12) 0.0332(5) Uani 1 1 d . . . H13 H 0.7742 0.1831 0.0943 0.040 Uiso 1 1 calc R . . C14 C 0.6425(2) 0.28409(15) 0.07558(12) 0.0295(5) Uani 1 1 d . . . N14 N 0.74007(19) 0.34405(12) 0.08907(10) 0.0321(4) Uani 1 1 d . . . C141 C 0.6964(3) 0.43204(15) 0.08699(14) 0.0401(6) Uani 1 1 d . . . H14A H 0.7528 0.4631 0.1248 0.048 Uiso 1 1 calc R . . H14B H 0.5954 0.4362 0.0997 0.048 Uiso 1 1 calc R . . C142 C 0.7166(4) 0.47121(19) 0.01153(17) 0.0649(8) Uani 1 1 d . . . H14A H 0.8169 0.4686 -0.0007 0.097 Uiso 1 1 calc R . . H14B H 0.6861 0.5290 0.0127 0.097 Uiso 1 1 calc R . . H14C H 0.6599 0.4413 -0.0260 0.097 Uiso 1 1 calc R . . C143 C 0.8887(2) 0.32636(16) 0.11442(13) 0.0360(5) Uani 1 1 d . . . H14D H 0.9507 0.3721 0.0988 0.043 Uiso 1 1 calc R . . H14E H 0.9212 0.2751 0.0903 0.043 Uiso 1 1 calc R . . C144 C 0.9029(3) 0.31625(19) 0.19830(14) 0.0483(7) Uani 1 1 d . . . H14D H 0.8707 0.3668 0.2224 0.072 Uiso 1 1 calc R . . H14E H 1.0024 0.3060 0.2125 0.072 Uiso 1 1 calc R . . H14F H 0.8449 0.2695 0.2138 0.072 Uiso 1 1 calc R . . O15 O 0.51561(15) 0.30785(10) 0.05603(8) 0.0314(3) Uani 1 1 d . . . O21 O 0.24235(16) 0.36032(9) 0.12355(8) 0.0316(3) Uani 1 1 d . . . C22 C 0.2684(2) 0.39807(14) 0.18657(13) 0.0307(5) Uani 1 1 d . . . C221 C 0.1930(3) 0.48064(16) 0.19362(15) 0.0430(6) Uani 1 1 d . . . H22A H 0.2200 0.5171 0.1531 0.065 Uiso 1 1 calc R . . H22B H 0.2203 0.5062 0.2411 0.065 Uiso 1 1 calc R . . H22C H 0.0903 0.4719 0.1912 0.065 Uiso 1 1 calc R . . C23 C 0.3534(2) 0.36887(14) 0.24421(12) 0.0337(5) Uani 1 1 d . . . H23 H 0.3683 0.4033 0.2863 0.040 Uiso 1 1 calc R . . C24 C 0.4215(2) 0.28861(14) 0.24423(12) 0.0293(5) Uani 1 1 d . . . N24 N 0.5003(2) 0.26207(12) 0.30369(11) 0.0341(4) Uani 1 1 d . . . C241 C 0.5223(3) 0.31086(17) 0.37287(13) 0.0406(6) Uani 1 1 d . . . H24A H 0.5366 0.2726 0.4152 0.049 Uiso 1 1 calc R . . H24B H 0.4362 0.3439 0.3817 0.049 Uiso 1 1 calc R . . C242 C 0.6497(3) 0.3684(2) 0.36901(16) 0.0591(8) Uani 1 1 d . . . H24A H 0.7356 0.3358 0.3619 0.089 Uiso 1 1 calc R . . H24B H 0.6597 0.3998 0.4152 0.089 Uiso 1 1 calc R . . H24C H 0.6357 0.4067 0.3274 0.089 Uiso 1 1 calc R . . C243 C 0.5684(3) 0.18011(16) 0.30212(14) 0.0400(6) Uani 1 1 d . . . H24D H 0.6590 0.1822 0.3312 0.048 Uiso 1 1 calc R . . H24E H 0.5903 0.1661 0.2504 0.048 Uiso 1 1 calc R . . C244 C 0.4743(3) 0.1128(2) 0.3336(2) 0.0690(9) Uani 1 1 d . . . H24D H 0.4522 0.1265 0.3848 0.103 Uiso 1 1 calc R . . H24E H 0.5241 0.0598 0.3326 0.103 Uiso 1 1 calc R . . H24F H 0.3862 0.1090 0.3037 0.103 Uiso 1 1 calc R . . O25 O 0.40773(17) 0.23918(9) 0.18878(8) 0.0316(4) Uani 1 1 d . . . O30 O 0.23647(17) 0.27267(11) -0.02522(9) 0.0372(4) Uani 1 1 d . . . C31 C 0.1485(3) 0.26676(16) -0.08999(14) 0.0384(6) Uani 1 1 d . . . H31 H 0.2089 0.2747 -0.1340 0.046 Uiso 1 1 calc R . . C32 C 0.0372(3) 0.3350(2) -0.09014(17) 0.0642(9) Uani 1 1 d . . . H32A H -0.0240 0.3277 -0.0478 0.096 Uiso 1 1 calc R . . H32B H -0.0202 0.3324 -0.1362 0.096 Uiso 1 1 calc R . . H32C H 0.0843 0.3889 -0.0865 0.096 Uiso 1 1 calc R . . C33 C 0.0822(3) 0.1811(2) -0.09484(17) 0.0624(8) Uani 1 1 d . . . H33A H 0.1569 0.1392 -0.0910 0.094 Uiso 1 1 calc R . . H33B H 0.0303 0.1752 -0.1423 0.094 Uiso 1 1 calc R . . H33C H 0.0168 0.1739 -0.0543 0.094 Uiso 1 1 calc R . . O40 O 0.15964(17) 0.17424(10) 0.10709(9) 0.0387(4) Uani 1 1 d . . . C41 C 0.1305(6) 0.0998(2) 0.1424(2) 0.1053(17) Uani 1 1 d . . . H41 H 0.2305 0.0792 0.1449 0.126 Uiso 1 1 calc R . . C42 C 0.1111(8) 0.0985(4) 0.2143(2) 0.168(3) Uani 1 1 d . . . H42A H 0.1565 0.1469 0.2373 0.253 Uiso 1 1 calc R . . H42B H 0.1530 0.0482 0.2356 0.253 Uiso 1 1 calc R . . H42C H 0.0093 0.0995 0.2235 0.253 Uiso 1 1 calc R . . C43 C 0.0758(4) 0.0364(2) 0.0897(2) 0.0770(10) Uani 1 1 d . . . H43A H 0.0586 -0.0151 0.1164 0.116 Uiso 1 1 calc R . . H43B H 0.1456 0.0267 0.0516 0.116 Uiso 1 1 calc R . . H43C H -0.0131 0.0558 0.0662 0.116 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.02332(13) 0.02850(14) 0.02880(13) -0.00108(8) -0.00618(9) -0.00098(8) O11 0.0299(8) 0.0295(8) 0.0365(9) -0.0051(6) -0.0053(6) -0.0008(6) C12 0.0338(12) 0.0320(12) 0.0283(11) -0.0020(9) -0.0028(9) 0.0029(10) C121 0.0422(14) 0.0345(14) 0.0594(17) 0.0023(12) -0.0079(12) 0.0041(11) C13 0.0271(11) 0.0358(13) 0.0363(12) -0.0006(10) -0.0049(9) 0.0036(10) C14 0.0258(11) 0.0361(12) 0.0265(11) -0.0010(9) 0.0005(9) -0.0007(10) N14 0.0243(9) 0.0348(11) 0.0372(11) -0.0020(8) -0.0018(8) -0.0035(8) C141 0.0355(13) 0.0332(13) 0.0512(15) -0.0045(11) -0.0024(11) -0.0050(10) C142 0.084(2) 0.0461(18) 0.064(2) 0.0136(14) -0.0050(17) -0.0029(16) C143 0.0233(11) 0.0454(14) 0.0393(13) -0.0025(10) -0.0014(9) -0.0060(10) C144 0.0383(14) 0.0650(19) 0.0411(14) 0.0010(13) -0.0050(11) -0.0066(13) O15 0.0239(8) 0.0311(8) 0.0390(9) 0.0021(7) -0.0042(6) -0.0018(6) O21 0.0287(8) 0.0308(8) 0.0351(9) -0.0002(7) -0.0058(6) 0.0035(6) C22 0.0254(11) 0.0278(12) 0.0391(13) -0.0014(9) 0.0032(9) -0.0028(9) C221 0.0429(14) 0.0337(14) 0.0523(15) -0.0055(11) -0.0008(11) 0.0067(11) C23 0.0374(12) 0.0328(12) 0.0308(12) -0.0046(9) -0.0006(9) -0.0012(10) C24 0.0257(11) 0.0345(12) 0.0276(12) 0.0028(9) 0.0002(9) -0.0045(9) N24 0.0362(11) 0.0388(12) 0.0271(10) 0.0022(8) -0.0041(8) 0.0007(8) C241 0.0415(13) 0.0541(16) 0.0260(12) 0.0001(10) -0.0034(10) -0.0009(12) C242 0.0511(17) 0.077(2) 0.0485(17) -0.0186(15) -0.0029(13) -0.0171(15) C243 0.0356(13) 0.0472(15) 0.0368(13) 0.0068(11) -0.0048(10) 0.0066(11) C244 0.0576(19) 0.0480(18) 0.102(3) 0.0282(17) 0.0114(18) 0.0090(15) O25 0.0357(9) 0.0308(9) 0.0280(8) -0.0018(6) -0.0061(7) 0.0032(6) O30 0.0334(9) 0.0439(10) 0.0335(9) 0.0012(7) -0.0115(7) -0.0021(7) C31 0.0322(12) 0.0551(16) 0.0275(12) 0.0054(10) -0.0065(10) -0.0020(11) C32 0.0544(18) 0.082(2) 0.0559(18) 0.0115(16) -0.0125(14) 0.0196(16) C33 0.0636(19) 0.073(2) 0.0496(17) -0.0057(15) -0.0164(14) -0.0233(17) O40 0.0344(9) 0.0341(9) 0.0473(10) 0.0058(7) -0.0052(7) -0.0092(7) C41 0.214(5) 0.048(2) 0.053(2) 0.0107(16) -0.009(3) -0.056(3) C42 0.301(8) 0.148(5) 0.057(3) 0.020(3) 0.016(4) -0.144(6) C43 0.087(3) 0.0459(19) 0.098(3) -0.0100(18) -0.011(2) -0.0188(17) _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 Zr1 O30 1.9427(16) . ? Zr1 O40 1.9508(16) . ? Zr1 O21 2.0992(15) . ? Zr1 O11 2.1219(15) . ? Zr1 O15 2.1695(15) . ? Zr1 O25 2.2055(15) . ? O11 C12 1.304(3) . ? C12 C13 1.361(3) . ? C12 C121 1.506(3) . ? C121 H12A 0.9700 . ? C121 H12B 0.9700 . ? C121 H12C 0.9700 . ? C13 C14 1.435(3) . ? C13 H13 0.9400 . ? C14 O15 1.283(3) . ? C14 N14 1.342(3) . ? N14 C141 1.468(3) . ? N14 C143 1.475(3) . ? C141 C142 1.506(4) . ? C141 H14A 0.9800 . ? C141 H14B 0.9800 . ? C142 H14A 0.9700 . ? C142 H14B 0.9700 . ? C142 H14C 0.9700 . ? C143 C144 1.511(3) . ? C143 H14D 0.9800 . ? C143 H14E 0.9800 . ? C144 H14D 0.9700 . ? C144 H14E 0.9700 . ? C144 H14F 0.9700 . ? O21 C22 1.296(3) . ? C22 C23 1.365(3) . ? C22 C221 1.506(3) . ? C221 H22A 0.9700 . ? C221 H22B 0.9700 . ? C221 H22C 0.9700 . ? C23 C24 1.435(3) . ? C23 H23 0.9400 . ? C24 O25 1.273(3) . ? C24 N24 1.344(3) . ? N24 C243 1.461(3) . ? N24 C241 1.473(3) . ? C241 C242 1.510(4) . ? C241 H24A 0.9800 . ? C241 H24B 0.9800 . ? C242 H24A 0.9700 . ? C242 H24B 0.9700 . ? C242 H24C 0.9700 . ? C243 C244 1.512(4) . ? C243 H24D 0.9800 . ? C243 H24E 0.9800 . ? C244 H24D 0.9700 . ? C244 H24E 0.9700 . ? C244 H24F 0.9700 . ? O30 C31 1.403(3) . ? C31 C33 1.508(4) . ? C31 C32 1.510(4) . ? C31 H31 0.9900 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? O40 C41 1.381(3) . ? C41 C42 1.305(5) . ? C41 C43 1.467(5) . ? C41 H41 0.9900 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C42 H42C 0.9700 . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C43 H43C 0.9700 . ? 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 O30 Zr1 O40 98.59(7) . . ? O30 Zr1 O21 96.12(7) . . ? O40 Zr1 O21 99.52(7) . . ? O30 Zr1 O11 102.38(7) . . ? O40 Zr1 O11 89.98(7) . . ? O21 Zr1 O11 157.71(6) . . ? O30 Zr1 O15 93.53(6) . . ? O40 Zr1 O15 164.61(6) . . ? O21 Zr1 O15 88.51(6) . . ? O11 Zr1 O15 78.13(6) . . ? O30 Zr1 O25 172.03(6) . . ? O40 Zr1 O25 88.10(6) . . ? O21 Zr1 O25 78.40(6) . . ? O11 Zr1 O25 81.84(6) . . ? O15 Zr1 O25 80.64(6) . . ? C12 O11 Zr1 129.54(14) . . ? O11 C12 C13 125.6(2) . . ? O11 C12 C121 114.2(2) . . ? C13 C12 C121 120.2(2) . . ? C12 C121 H12A 109.5 . . ? C12 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? C12 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? C12 C13 C14 123.4(2) . . ? C12 C13 H13 118.3 . . ? C14 C13 H13 118.3 . . ? O15 C14 N14 117.0(2) . . ? O15 C14 C13 121.6(2) . . ? N14 C14 C13 121.47(19) . . ? C14 N14 C141 119.80(19) . . ? C14 N14 C143 123.1(2) . . ? C141 N14 C143 116.78(18) . . ? N14 C141 C142 112.4(2) . . ? N14 C141 H14A 109.1 . . ? C142 C141 H14A 109.1 . . ? N14 C141 H14B 109.1 . . ? C142 C141 H14B 109.1 . . ? H14A C141 H14B 107.9 . . ? C141 C142 H14A 109.5 . . ? C141 C142 H14B 109.5 . . ? H14A C142 H14B 109.5 . . ? C141 C142 H14C 109.5 . . ? H14A C142 H14C 109.5 . . ? H14B C142 H14C 109.5 . . ? N14 C143 C144 112.30(19) . . ? N14 C143 H14D 109.1 . . ? C144 C143 H14D 109.1 . . ? N14 C143 H14E 109.1 . . ? C144 C143 H14E 109.1 . . ? H14D C143 H14E 107.9 . . ? C143 C144 H14D 109.5 . . ? C143 C144 H14E 109.5 . . ? H14D C144 H14E 109.5 . . ? C143 C144 H14F 109.5 . . ? H14D C144 H14F 109.5 . . ? H14E C144 H14F 109.5 . . ? C14 O15 Zr1 129.64(14) . . ? C22 O21 Zr1 134.94(14) . . ? O21 C22 C23 125.9(2) . . ? O21 C22 C221 114.1(2) . . ? C23 C22 C221 120.0(2) . . ? C22 C221 H22A 109.5 . . ? C22 C221 H22B 109.5 . . ? H22A C221 H22B 109.5 . . ? C22 C221 H22C 109.5 . . ? H22A C221 H22C 109.5 . . ? H22B C221 H22C 109.5 . . ? C22 C23 C24 123.7(2) . . ? C22 C23 H23 118.1 . . ? C24 C23 H23 118.1 . . ? O25 C24 N24 117.3(2) . . ? O25 C24 C23 121.58(19) . . ? N24 C24 C23 121.1(2) . . ? C24 N24 C243 119.87(19) . . ? C24 N24 C241 123.8(2) . . ? C243 N24 C241 116.37(19) . . ? N24 C241 C242 112.1(2) . . ? N24 C241 H24A 109.2 . . ? C242 C241 H24A 109.2 . . ? N24 C241 H24B 109.2 . . ? C242 C241 H24B 109.2 . . ? H24A C241 H24B 107.9 . . ? C241 C242 H24A 109.5 . . ? C241 C242 H24B 109.5 . . ? H24A C242 H24B 109.5 . . ? C241 C242 H24C 109.5 . . ? H24A C242 H24C 109.5 . . ? H24B C242 H24C 109.5 . . ? N24 C243 C244 112.1(2) . . ? N24 C243 H24D 109.2 . . ? C244 C243 H24D 109.2 . . ? N24 C243 H24E 109.2 . . ? C244 C243 H24E 109.2 . . ? H24D C243 H24E 107.9 . . ? C243 C244 H24D 109.5 . . ? C243 C244 H24E 109.5 . . ? H24D C244 H24E 109.5 . . ? C243 C244 H24F 109.5 . . ? H24D C244 H24F 109.5 . . ? H24E C244 H24F 109.5 . . ? C24 O25 Zr1 134.81(14) . . ? C31 O30 Zr1 159.00(16) . . ? O30 C31 C33 109.8(2) . . ? O30 C31 C32 109.8(2) . . ? C33 C31 C32 112.2(3) . . ? O30 C31 H31 108.3 . . ? C33 C31 H31 108.3 . . ? C32 C31 H31 108.3 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C41 O40 Zr1 144.8(3) . . ? C42 C41 O40 119.9(4) . . ? C42 C41 C43 124.5(4) . . ? O40 C41 C43 112.0(3) . . ? C42 C41 H41 96.3 . . ? O40 C41 H41 96.3 . . ? C43 C41 H41 96.3 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? 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 O30 Zr1 O11 C12 122.85(18) . . . . ? O40 Zr1 O11 C12 -138.36(18) . . . . ? O21 Zr1 O11 C12 -22.6(3) . . . . ? O15 Zr1 O11 C12 31.80(18) . . . . ? O25 Zr1 O11 C12 -50.28(18) . . . . ? Zr1 O11 C12 C13 -22.8(3) . . . . ? Zr1 O11 C12 C121 155.39(16) . . . . ? O11 C12 C13 C14 -0.4(4) . . . . ? C121 C12 C13 C14 -178.5(2) . . . . ? C12 C13 C14 O15 -3.5(3) . . . . ? C12 C13 C14 N14 176.6(2) . . . . ? O15 C14 N14 C141 4.9(3) . . . . ? C13 C14 N14 C141 -175.3(2) . . . . ? O15 C14 N14 C143 177.87(19) . . . . ? C13 C14 N14 C143 -2.3(3) . . . . ? C14 N14 C141 C142 -93.7(3) . . . . ? C143 N14 C141 C142 92.9(3) . . . . ? C14 N14 C143 C144 -85.1(3) . . . . ? C141 N14 C143 C144 88.1(3) . . . . ? N14 C14 O15 Zr1 -149.76(15) . . . . ? C13 C14 O15 Zr1 30.4(3) . . . . ? O30 Zr1 O15 C14 -138.27(18) . . . . ? O40 Zr1 O15 C14 3.7(4) . . . . ? O21 Zr1 O15 C14 125.69(18) . . . . ? O11 Zr1 O15 C14 -36.35(18) . . . . ? O25 Zr1 O15 C14 47.20(18) . . . . ? O30 Zr1 O21 C22 -167.6(2) . . . . ? O40 Zr1 O21 C22 92.6(2) . . . . ? O11 Zr1 O21 C22 -21.5(3) . . . . ? O15 Zr1 O21 C22 -74.2(2) . . . . ? O25 Zr1 O21 C22 6.50(19) . . . . ? Zr1 O21 C22 C23 -2.7(3) . . . . ? Zr1 O21 C22 C221 178.19(15) . . . . ? O21 C22 C23 C24 -3.3(4) . . . . ? C221 C22 C23 C24 175.7(2) . . . . ? C22 C23 C24 O25 1.0(3) . . . . ? C22 C23 C24 N24 -177.8(2) . . . . ? O25 C24 N24 C243 1.3(3) . . . . ? C23 C24 N24 C243 -179.9(2) . . . . ? O25 C24 N24 C241 -178.0(2) . . . . ? C23 C24 N24 C241 0.8(3) . . . . ? C24 N24 C241 C242 -88.2(3) . . . . ? C243 N24 C241 C242 92.6(3) . . . . ? C24 N24 C243 C244 -91.6(3) . . . . ? C241 N24 C243 C244 87.7(3) . . . . ? N24 C24 O25 Zr1 -174.03(14) . . . . ? C23 C24 O25 Zr1 7.2(3) . . . . ? O30 Zr1 O25 C24 38.1(6) . . . . ? O40 Zr1 O25 C24 -109.1(2) . . . . ? O21 Zr1 O25 C24 -8.93(19) . . . . ? O11 Zr1 O25 C24 160.7(2) . . . . ? O15 Zr1 O25 C24 81.5(2) . . . . ? O40 Zr1 O30 C31 -9.1(5) . . . . ? O21 Zr1 O30 C31 -109.8(5) . . . . ? O11 Zr1 O30 C31 82.7(5) . . . . ? O15 Zr1 O30 C31 161.3(5) . . . . ? O25 Zr1 O30 C31 -155.9(4) . . . . ? Zr1 O30 C31 C33 -24.0(6) . . . . ? Zr1 O30 C31 C32 99.8(5) . . . . ? O30 Zr1 O40 C41 134.8(3) . . . . ? O21 Zr1 O40 C41 -127.5(3) . . . . ? O11 Zr1 O40 C41 32.3(3) . . . . ? O15 Zr1 O40 C41 -6.8(5) . . . . ? O25 Zr1 O40 C41 -49.6(3) . . . . ? Zr1 O40 C41 C42 91.8(7) . . . . ? Zr1 O40 C41 C43 -108.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.538 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.051 data_raf02t _database_code_CSD 197511 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H40 O8 Zr' _chemical_formula_weight 523.76 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' 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 C2/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 9.85(2) _cell_length_b 15.40(3) _cell_length_c 18.71(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.15(5) _cell_angle_gamma 90.00 _cell_volume 2816(9) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 15.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 axs CCD 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3492 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.15 _reflns_number_total 2254 _reflns_number_gt 1955 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker axs SHELXTL-PLUS' _computing_publication_material SHELXL-97 _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^)+(0.0591P)^2^+9.5732P] 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 2254 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.005 _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 Zr1 Zr 0.0000 0.29663(4) 0.2500 0.0420(3) Uani 1 2 d S . . C4 C -0.4131(6) 0.3751(5) 0.1488(4) 0.0735(19) Uani 1 1 d . . . H1A H -0.4395 0.3186 0.1287 0.110 Uiso 1 1 calc R . . H1B H -0.4497 0.4202 0.1157 0.110 Uiso 1 1 calc R . . H1C H -0.4491 0.3822 0.1944 0.110 Uiso 1 1 calc R . . C1 C -0.2593(5) 0.3817(4) 0.1607(3) 0.0469(13) Uani 1 1 d . . . O1 O -0.2004(4) 0.3236(2) 0.2039(2) 0.0494(9) Uani 1 1 d . . . C2 C -0.1927(5) 0.4452(4) 0.1287(3) 0.0474(13) Uani 1 1 d . . . H3 H -0.2444 0.4836 0.0972 0.057 Uiso 1 1 calc R . . C3 C -0.0487(5) 0.4562(3) 0.1406(3) 0.0442(12) Uani 1 1 d . . . O2 O 0.0322(3) 0.4095(2) 0.1791(2) 0.0455(9) Uani 1 1 d . . . O7 O -0.0060(4) 0.5242(2) 0.1050(2) 0.0514(9) Uani 1 1 d . . . C5 C 0.1380(6) 0.5528(4) 0.1127(3) 0.0567(15) Uani 1 1 d . . . C8 C 0.1295(8) 0.6317(4) 0.0629(4) 0.074(2) Uani 1 1 d . . . H51A H 0.1053 0.6130 0.0135 0.111 Uiso 1 1 calc R . . H51B H 0.2175 0.6608 0.0675 0.111 Uiso 1 1 calc R . . H51C H 0.0604 0.6714 0.0762 0.111 Uiso 1 1 calc R . . C7 C 0.2226(7) 0.4813(4) 0.0837(5) 0.081(2) Uani 1 1 d . . . H52A H 0.2320 0.4332 0.1174 0.121 Uiso 1 1 calc R . . H52B H 0.3124 0.5036 0.0776 0.121 Uiso 1 1 calc R . . H52C H 0.1772 0.4614 0.0376 0.121 Uiso 1 1 calc R . . C6 C 0.1822(10) 0.5787(6) 0.1891(4) 0.102(3) Uani 1 1 d . . . H53A H 0.1136 0.6162 0.2057 0.154 Uiso 1 1 calc R . . H53B H 0.2687 0.6094 0.1920 0.154 Uiso 1 1 calc R . . H53C H 0.1931 0.5271 0.2191 0.154 Uiso 1 1 calc R . . O6 O 0.0541(4) 0.2195(2) 0.1789(2) 0.0548(10) Uani 1 1 d . B . C20 C 0.1295(8) 0.1751(5) 0.1308(4) 0.079(2) Uani 1 1 d . . . H6 H 0.1286 0.1110 0.1350 0.095 Uiso 1 1 calc R A 1 C22 C 0.2654(8) 0.2140(6) 0.1307(5) 0.098(3) Uani 1 1 d . B . H61A H 0.2575 0.2669 0.1023 0.147 Uiso 1 1 calc R . . H61B H 0.3247 0.1734 0.1098 0.147 Uiso 1 1 calc R . . H61C H 0.3038 0.2274 0.1797 0.147 Uiso 1 1 calc R . . C21 C 0.057(5) 0.212(5) 0.059(3) 0.117(17) Uiso 0.27(5) 1 d P B 1 H21A H -0.0408 0.2017 0.0563 0.176 Uiso 0.27(5) 1 calc PR B 1 H21B H 0.0918 0.1827 0.0189 0.176 Uiso 0.27(5) 1 calc PR B 1 H21C H 0.0744 0.2735 0.0564 0.176 Uiso 0.27(5) 1 calc PR B 1 C21 C 0.0525(12) 0.1580(15) 0.0610(6) 0.080(6) Uani 0.73(5) 1 d P B 2 H21D H -0.0229 0.1192 0.0667 0.121 Uiso 0.73(5) 1 calc PR B 2 H21E H 0.1120 0.1313 0.0297 0.121 Uiso 0.73(5) 1 calc PR B 2 H21F H 0.0170 0.2122 0.0398 0.121 Uiso 0.73(5) 1 calc PR B 2 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 Zr1 0.0470(4) 0.0294(4) 0.0519(5) 0.000 0.0147(3) 0.000 C4 0.043(3) 0.085(5) 0.092(5) -0.006(4) 0.006(3) 0.002(3) C1 0.046(3) 0.046(3) 0.050(3) -0.013(3) 0.008(2) 0.003(2) O1 0.045(2) 0.045(2) 0.060(2) 0.0000(18) 0.0111(18) -0.0094(16) C2 0.048(3) 0.044(3) 0.051(3) 0.003(2) 0.012(2) 0.010(2) C3 0.051(3) 0.039(3) 0.045(3) -0.004(2) 0.019(2) 0.002(2) O2 0.0413(19) 0.0371(18) 0.059(2) 0.0100(17) 0.0075(16) -0.0034(16) O7 0.057(2) 0.040(2) 0.060(2) 0.0101(17) 0.0191(18) 0.0057(17) C5 0.061(3) 0.048(3) 0.064(4) 0.012(3) 0.017(3) -0.001(3) C8 0.084(5) 0.050(4) 0.095(5) 0.019(3) 0.038(4) 0.004(3) C7 0.063(4) 0.055(4) 0.131(7) 0.024(4) 0.039(4) 0.008(3) C6 0.138(8) 0.092(6) 0.074(5) 0.009(4) -0.003(5) -0.066(6) O6 0.065(2) 0.043(2) 0.061(3) -0.0103(18) 0.025(2) -0.0039(18) C20 0.079(5) 0.071(4) 0.095(6) -0.020(4) 0.039(4) -0.001(4) C22 0.065(5) 0.111(7) 0.125(7) -0.019(6) 0.040(5) 0.003(5) C21 0.078(7) 0.095(13) 0.067(8) -0.028(7) 0.007(5) 0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 O6 1.908(4) . ? Zr1 O6 1.908(4) 6_556 ? Zr1 O1 2.095(5) . ? Zr1 O1 2.095(5) 6_556 ? Zr1 O2 2.233(4) 6_556 ? Zr1 O2 2.233(4) . ? C4 C1 1.507(8) . ? C1 O1 1.294(7) . ? C1 C2 1.357(8) . ? C2 C3 1.419(8) . ? C3 O2 1.236(6) . ? C3 O7 1.337(6) . ? O7 C5 1.475(7) . ? C5 C6 1.495(10) . ? C5 C7 1.521(9) . ? C5 C8 1.526(8) . ? O6 C20 1.411(8) . ? C20 C21 1.451(13) . ? C20 C22 1.467(11) . ? C20 C21 1.55(5) . ? 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 O6 Zr1 O6 103.0(3) . 6_556 ? O6 Zr1 O1 99.61(19) . . ? O6 Zr1 O1 94.56(19) 6_556 . ? O6 Zr1 O1 94.56(19) . 6_556 ? O6 Zr1 O1 99.61(19) 6_556 6_556 ? O1 Zr1 O1 157.2(2) . 6_556 ? O6 Zr1 O2 166.21(14) . 6_556 ? O6 Zr1 O2 89.9(2) 6_556 6_556 ? O1 Zr1 O2 83.90(15) . 6_556 ? O1 Zr1 O2 78.33(15) 6_556 6_556 ? O6 Zr1 O2 89.9(2) . . ? O6 Zr1 O2 166.21(14) 6_556 . ? O1 Zr1 O2 78.33(15) . . ? O1 Zr1 O2 83.90(15) 6_556 . ? O2 Zr1 O2 77.7(2) 6_556 . ? O1 C1 C2 124.7(5) . . ? O1 C1 C4 114.2(5) . . ? C2 C1 C4 121.0(6) . . ? C1 O1 Zr1 136.1(3) . . ? C1 C2 C3 123.1(5) . . ? O2 C3 O7 121.7(5) . . ? O2 C3 C2 125.6(5) . . ? O7 C3 C2 112.7(5) . . ? C3 O2 Zr1 132.0(3) . . ? C3 O7 C5 123.0(4) . . ? O7 C5 C6 109.5(5) . . ? O7 C5 C7 108.1(5) . . ? C6 C5 C7 115.2(7) . . ? O7 C5 C8 101.5(5) . . ? C6 C5 C8 111.0(6) . . ? C7 C5 C8 110.5(5) . . ? C20 O6 Zr1 163.8(4) . . ? O6 C20 C21 113.8(7) . . ? O6 C20 C22 110.9(6) . . ? C21 C20 C22 116.5(9) . . ? O6 C20 C21 99(2) . . ? C21 C20 C21 32(2) . . ? C22 C20 C21 100(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 C2 C1 O1 Zr1 3.5(9) . . . . ? C4 C1 O1 Zr1 -175.4(4) . . . . ? O6 Zr1 O1 C1 -91.4(5) . . . . ? O6 Zr1 O1 C1 164.5(5) 6_556 . . . ? O1 Zr1 O1 C1 36.1(5) 6_556 . . . ? O2 Zr1 O1 C1 75.1(5) 6_556 . . . ? O2 Zr1 O1 C1 -3.6(5) . . . . ? O1 C1 C2 C3 -1.5(9) . . . . ? C4 C1 C2 C3 177.3(5) . . . . ? C1 C2 C3 O2 1.8(9) . . . . ? C1 C2 C3 O7 -178.3(5) . . . . ? O7 C3 O2 Zr1 176.5(3) . . . . ? C2 C3 O2 Zr1 -3.7(8) . . . . ? O6 Zr1 O2 C3 103.4(5) . . . . ? O6 Zr1 O2 C3 -56.3(9) 6_556 . . . ? O1 Zr1 O2 C3 3.6(5) . . . . ? O1 Zr1 O2 C3 -162.0(5) 6_556 . . . ? O2 Zr1 O2 C3 -82.6(5) 6_556 . . . ? O2 C3 O7 C5 -4.6(8) . . . . ? C2 C3 O7 C5 175.6(5) . . . . ? C3 O7 C5 C6 -61.5(7) . . . . ? C3 O7 C5 C7 64.8(7) . . . . ? C3 O7 C5 C8 -178.9(5) . . . . ? O6 Zr1 O6 C20 -121.0(17) 6_556 . . . ? O1 Zr1 O6 C20 142.0(16) . . . . ? O1 Zr1 O6 C20 -20.0(16) 6_556 . . . ? O2 Zr1 O6 C20 38(2) 6_556 . . . ? O2 Zr1 O6 C20 63.8(16) . . . . ? Zr1 O6 C20 C21 -139.0(17) . . . . ? Zr1 O6 C20 C22 -5(2) . . . . ? Zr1 O6 C20 C21 -110(3) . . . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 25.15 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.832 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.086 data_3t _database_code_CSD 207421 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H68 O12 Zr2' _chemical_formula_weight 851.32 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' 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.977(3) _cell_length_b 13.192(4) _cell_length_c 16.218(5) _cell_angle_alpha 74.74(2) _cell_angle_beta 89.86(2) _cell_angle_gamma 89.86(3) _cell_volume 2265.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 15.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.603 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 axs CCD 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12972 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.1961 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.08 _reflns_number_total 7891 _reflns_number_gt 5157 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker axs SHELXL-PLUS' _computing_publication_material SHELXL-97 _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^)+(0.0000P)^2^+0.0000P] 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 7891 _refine_ls_number_parameters 428 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.2415 _refine_ls_wR_factor_gt 0.1890 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.078 _refine_ls_shift/su_mean 0.002 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 Zr1 Zr 0.41371(6) 0.55247(5) 0.07050(4) 0.0344(2) Uani 1 1 d . . . Zr2 Zr 0.92467(7) 0.90996(5) 0.45642(4) 0.0421(2) Uani 1 1 d . . . O11 O 0.2995(5) 0.6307(4) -0.0370(3) 0.0446(12) Uani 1 1 d . . . O12 O 0.3550(5) 0.8822(4) 0.0702(3) 0.0461(12) Uani 1 1 d . . . C12 C 0.2414(7) 0.7174(6) -0.0576(5) 0.0457(18) Uani 1 1 d . . . O13 O 0.4100(4) 0.7159(3) 0.0786(3) 0.0398(11) Uani 1 1 d . . . C13 C 0.1474(8) 0.7258(7) -0.1269(6) 0.065(2) Uani 1 1 d . . . H13A H 0.1880 0.7279 -0.1806 0.097 Uiso 1 1 calc R . . H13B H 0.1001 0.7895 -0.1330 0.097 Uiso 1 1 calc R . . H13C H 0.0938 0.6654 -0.1117 0.097 Uiso 1 1 calc R . . O14 O 0.2662(5) 0.5105(4) 0.1351(3) 0.0478(13) Uani 1 1 d . . . C14 C 0.2625(7) 0.7998(5) -0.0220(5) 0.0444(17) Uani 1 1 d . . . H14 H 0.2194 0.8629 -0.0436 0.053 Uiso 1 1 calc . . . C15 C 0.3447(6) 0.7941(5) 0.0446(4) 0.0359(15) Uani 1 1 d . . . O15 O 0.5280(5) 0.5273(4) 0.1638(3) 0.0538(14) Uani 1 1 d . . . O16 O 0.4405(4) 0.4163(3) 0.0283(3) 0.0367(11) Uani 1 1 d . . . C16 C 0.4327(8) 0.8880(6) 0.1424(6) 0.055(2) Uani 1 1 d . . . C17 C 0.3935(10) 0.8100(8) 0.2242(6) 0.073(3) Uani 1 1 d . . . H17A H 0.3082 0.8211 0.2351 0.109 Uiso 1 1 calc R . . H17B H 0.4423 0.8197 0.2713 0.109 Uiso 1 1 calc R . . H17C H 0.4048 0.7391 0.2187 0.109 Uiso 1 1 calc R . . C18 C 0.5678(9) 0.8770(8) 0.1194(7) 0.072(3) Uani 1 1 d . . . H18A H 0.5847 0.8046 0.1199 0.108 Uiso 1 1 calc R . . H18B H 0.6193 0.8972 0.1609 0.108 Uiso 1 1 calc R . . H18C H 0.5844 0.9223 0.0629 0.108 Uiso 1 1 calc R . . C19 C 0.4102(10) 1.0024(8) 0.1460(7) 0.080(3) Uani 1 1 d . . . H19A H 0.4376 1.0503 0.0930 0.120 Uiso 1 1 calc R . . H19B H 0.4551 1.0157 0.1935 0.120 Uiso 1 1 calc R . . H19C H 0.3239 1.0129 0.1537 0.120 Uiso 1 1 calc R . . O21 O 0.7884(5) 1.0331(4) 0.4141(3) 0.0547(14) Uani 1 1 d . . . O22 O 0.8432(5) 0.9527(4) 0.1844(3) 0.0500(13) Uani 1 1 d . . . C22 C 0.7217(8) 1.0634(7) 0.3496(5) 0.053(2) Uani 1 1 d . . . O23 O 0.9094(5) 0.9228(4) 0.3196(3) 0.0463(12) Uani 1 1 d . . . C23 C 0.6193(10) 1.1346(9) 0.3562(6) 0.088(4) Uani 1 1 d . . . H23A H 0.5862 1.1145 0.4137 0.132 Uiso 1 1 calc R . . H23B H 0.5562 1.1294 0.3157 0.132 Uiso 1 1 calc R . . H23C H 0.6486 1.2064 0.3435 0.132 Uiso 1 1 calc R . . O24 O 1.0573(5) 0.8106(5) 0.4626(4) 0.0611(15) Uani 1 1 d D . . C24 C 0.7404(8) 1.0329(6) 0.2737(5) 0.0516(19) Uani 1 1 d . . . H24 H 0.6865 1.0578 0.2278 0.062 Uiso 1 1 calc . . . O25 O 0.7947(6) 0.8101(5) 0.4898(4) 0.0642(16) Uani 1 1 d . . . C25 C 0.8356(7) 0.9673(6) 0.2641(4) 0.0397(16) Uani 1 1 d . . . O26 O 0.9434(5) 0.9569(4) 0.5697(3) 0.0448(12) Uani 1 1 d . . . C26 C 0.9294(8) 0.8774(8) 0.1631(5) 0.060(2) Uani 1 1 d . . . C27 C 1.0590(9) 0.9143(13) 0.1683(7) 0.113(5) Uani 1 1 d . . . H27A H 1.0657 0.9875 0.1365 0.170 Uiso 1 1 calc R . . H27B H 1.1140 0.8722 0.1440 0.170 Uiso 1 1 calc R . . H27C H 1.0802 0.9070 0.2276 0.170 Uiso 1 1 calc R . . C28 C 0.8963(10) 0.8869(9) 0.0705(6) 0.085(3) Uani 1 1 d . . . H28A H 0.8142 0.8611 0.0676 0.128 Uiso 1 1 calc R . . H28B H 0.9529 0.8457 0.0465 0.128 Uiso 1 1 calc R . . H28C H 0.9007 0.9600 0.0382 0.128 Uiso 1 1 calc R . . C29 C 0.9058(14) 0.7688(8) 0.2190(7) 0.104(4) Uani 1 1 d . . . H29A H 0.9161 0.7685 0.2784 0.156 Uiso 1 1 calc R . . H29B H 0.9630 0.7198 0.2046 0.156 Uiso 1 1 calc R . . H29C H 0.8233 0.7479 0.2100 0.156 Uiso 1 1 calc R . . C110 C 0.1483(9) 0.4931(8) 0.1711(7) 0.072(3) Uani 1 1 d . . . H110 H 0.1295 0.4171 0.1840 0.087 Uiso 1 1 calc R . . C111 C 0.0560(9) 0.5528(10) 0.1094(8) 0.088(3) Uani 1 1 d . . . H11A H 0.0772 0.6267 0.0931 0.132 Uiso 1 1 calc R . . H11B H -0.0238 0.5439 0.1361 0.132 Uiso 1 1 calc R . . H11C H 0.0548 0.5264 0.0589 0.132 Uiso 1 1 calc R . . C112 C 0.1507(14) 0.5266(12) 0.2561(8) 0.123(5) Uani 1 1 d . . . H11D H 0.2139 0.4878 0.2930 0.185 Uiso 1 1 calc R . . H11E H 0.0724 0.5117 0.2845 0.185 Uiso 1 1 calc R . . H11F H 0.1673 0.6013 0.2438 0.185 Uiso 1 1 calc R . . C113 C 0.5991(11) 0.5230(16) 0.2332(7) 0.134(7) Uani 1 1 d . . . H113 H 0.6020 0.5985 0.2313 0.161 Uiso 1 1 calc R . . C114 C 0.7182(12) 0.5038(15) 0.2278(10) 0.154(7) Uani 1 1 d . . . H11G H 0.7342 0.4298 0.2533 0.231 Uiso 1 1 calc R . . H11H H 0.7641 0.5456 0.2579 0.231 Uiso 1 1 calc R . . H11I H 0.7427 0.5221 0.1682 0.231 Uiso 1 1 calc R . . C115 C 0.5305(14) 0.4826(15) 0.3139(6) 0.153(8) Uani 1 1 d . . . H11J H 0.4805 0.4237 0.3096 0.229 Uiso 1 1 calc R . . H11K H 0.4788 0.5379 0.3240 0.229 Uiso 1 1 calc R . . H11L H 0.5873 0.4598 0.3609 0.229 Uiso 1 1 calc R . . C116 C 0.3931(8) 0.3116(5) 0.0644(5) 0.053(2) Uani 1 1 d . . . H116 H 0.4389 0.2625 0.0390 0.063 Uiso 1 1 calc R . . C117 C 0.2615(9) 0.3088(8) 0.0393(7) 0.073(3) Uani 1 1 d . . . H11M H 0.2134 0.3512 0.0679 0.109 Uiso 1 1 calc R . . H11N H 0.2325 0.2368 0.0560 0.109 Uiso 1 1 calc R . . H11O H 0.2538 0.3364 -0.0221 0.109 Uiso 1 1 calc R . . C118 C 0.4142(10) 0.2793(7) 0.1597(6) 0.075(3) Uani 1 1 d . . . H11P H 0.4989 0.2909 0.1715 0.112 Uiso 1 1 calc R . . H11Q H 0.3947 0.2055 0.1821 0.112 Uiso 1 1 calc R . . H11R H 0.3625 0.3210 0.1868 0.112 Uiso 1 1 calc R . . C213 C 0.6927(12) 0.7418(9) 0.5047(8) 0.094(4) Uani 1 1 d . . . H213 H 0.6679 0.7311 0.5651 0.113 Uiso 1 1 calc R . . C215 C 0.5893(18) 0.7937(14) 0.4502(11) 0.146(6) Uiso 1 1 d . . . H21A H 0.5777 0.8639 0.4571 0.219 Uiso 1 1 calc R . . H21B H 0.5157 0.7530 0.4672 0.219 Uiso 1 1 calc R . . H21C H 0.6073 0.7980 0.3908 0.219 Uiso 1 1 calc R . . C216 C 0.8755(11) 0.9278(9) 0.6487(5) 0.077(3) Uani 1 1 d . . . H216 H 0.9060 0.9725 0.6846 0.093 Uiso 1 1 calc R . . C217 C 0.7433(11) 0.9542(10) 0.6325(8) 0.095(4) Uani 1 1 d . . . H21D H 0.7344 1.0292 0.6076 0.143 Uiso 1 1 calc R . . H21E H 0.6987 0.9341 0.6861 0.143 Uiso 1 1 calc R . . H21F H 0.7111 0.9165 0.5935 0.143 Uiso 1 1 calc R . . C218 C 0.8983(13) 0.8203(11) 0.6957(7) 0.121(5) Uani 1 1 d . . . H21G H 0.8347 0.7755 0.6834 0.182 Uiso 1 1 calc R . . H21H H 0.8988 0.8152 0.7565 0.182 Uiso 1 1 calc R . . H21I H 0.9766 0.7979 0.6789 0.182 Uiso 1 1 calc R . . C214 C 0.7287(17) 0.6371(13) 0.4929(11) 0.152(6) Uiso 1 1 d . . . H21J H 0.7382 0.6425 0.4324 0.229 Uiso 1 1 calc R . . H21K H 0.6661 0.5860 0.5166 0.229 Uiso 1 1 calc R . . H21L H 0.8052 0.6151 0.5220 0.229 Uiso 1 1 calc R . . C210 C 1.1523(15) 0.7372(13) 0.4826(12) 0.170(7) Uiso 1 1 d D . . H210 H 1.2265 0.7677 0.5010 0.205 Uiso 1 1 calc R . . C211 C 1.102(3) 0.646(2) 0.5537(16) 0.285(15) Uiso 1 1 d D . . H21M H 1.0949 0.6677 0.6062 0.428 Uiso 1 1 calc R . . H21N H 1.1564 0.5862 0.5625 0.428 Uiso 1 1 calc R . . H21O H 1.0220 0.6265 0.5373 0.428 Uiso 1 1 calc R . . C212 C 1.179(2) 0.686(2) 0.4130(15) 0.234(12) Uiso 1 1 d D . . H21P H 1.1336 0.6213 0.4227 0.351 Uiso 1 1 calc R . . H21Q H 1.2654 0.6716 0.4121 0.351 Uiso 1 1 calc R . . H21R H 1.1552 0.7331 0.3585 0.351 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.0346(4) 0.0295(4) 0.0396(4) -0.0105(3) 0.0006(3) 0.0045(3) Zr2 0.0392(5) 0.0483(5) 0.0380(4) -0.0097(3) -0.0028(3) 0.0009(3) O11 0.042(3) 0.040(3) 0.053(3) -0.015(2) -0.012(2) 0.010(2) O12 0.048(3) 0.034(3) 0.061(3) -0.022(2) -0.005(3) 0.009(2) C12 0.045(5) 0.045(4) 0.045(4) -0.008(3) -0.007(3) 0.004(4) O13 0.038(3) 0.036(3) 0.047(3) -0.015(2) -0.002(2) 0.007(2) C13 0.051(5) 0.058(5) 0.087(6) -0.021(5) -0.034(5) 0.012(4) O14 0.044(3) 0.045(3) 0.055(3) -0.014(2) 0.015(2) 0.004(2) C14 0.038(4) 0.035(4) 0.059(5) -0.010(3) -0.002(4) 0.007(3) C15 0.031(4) 0.033(4) 0.047(4) -0.017(3) 0.008(3) -0.005(3) O15 0.060(4) 0.057(3) 0.046(3) -0.017(3) -0.005(3) 0.008(3) O16 0.040(3) 0.024(2) 0.046(3) -0.008(2) 0.009(2) -0.0020(19) C16 0.048(5) 0.047(4) 0.083(6) -0.040(4) 0.003(4) 0.004(4) C17 0.082(7) 0.086(7) 0.055(5) -0.028(5) 0.000(5) 0.001(6) C18 0.055(6) 0.078(6) 0.102(7) -0.055(6) -0.004(5) -0.005(5) C19 0.082(8) 0.072(6) 0.107(8) -0.059(6) -0.008(6) 0.013(5) O21 0.047(3) 0.073(4) 0.049(3) -0.023(3) -0.007(3) 0.018(3) O22 0.045(3) 0.063(3) 0.045(3) -0.021(3) -0.008(2) 0.004(3) C22 0.041(5) 0.063(5) 0.057(5) -0.019(4) -0.007(4) 0.008(4) O23 0.042(3) 0.057(3) 0.042(3) -0.016(2) -0.005(2) 0.007(2) C23 0.077(7) 0.127(9) 0.069(6) -0.042(6) -0.019(5) 0.058(7) O24 0.049(4) 0.062(3) 0.068(4) -0.009(3) -0.013(3) 0.016(3) C24 0.052(5) 0.057(5) 0.048(4) -0.018(4) -0.014(4) 0.011(4) O25 0.057(4) 0.074(4) 0.066(4) -0.026(3) 0.007(3) -0.018(3) C25 0.038(4) 0.050(4) 0.035(4) -0.019(3) -0.003(3) -0.008(3) O26 0.044(3) 0.056(3) 0.033(2) -0.008(2) 0.004(2) -0.014(2) C26 0.056(6) 0.080(6) 0.053(5) -0.034(5) 0.000(4) 0.008(5) C27 0.030(5) 0.250(17) 0.093(8) -0.106(10) 0.001(5) -0.005(7) C28 0.068(7) 0.136(10) 0.073(6) -0.068(7) 0.000(5) 0.007(7) C29 0.152(13) 0.072(7) 0.094(8) -0.034(7) -0.007(8) 0.034(8) C110 0.058(6) 0.067(6) 0.093(7) -0.024(5) 0.036(6) -0.007(5) C111 0.039(6) 0.119(9) 0.115(9) -0.047(8) 0.005(6) 0.001(6) C112 0.117(12) 0.167(14) 0.080(8) -0.023(9) 0.047(8) 0.027(10) C113 0.054(7) 0.28(2) 0.065(7) -0.036(10) -0.024(6) 0.022(10) C114 0.066(9) 0.24(2) 0.127(12) 0.005(12) -0.043(8) -0.006(11) C115 0.114(12) 0.29(2) 0.043(6) -0.022(9) -0.018(7) 0.026(13) C116 0.069(6) 0.031(4) 0.061(5) -0.016(4) 0.029(4) -0.004(4) C117 0.065(7) 0.075(6) 0.085(7) -0.034(5) 0.013(5) -0.028(5) C118 0.097(8) 0.043(5) 0.067(6) 0.016(4) 0.023(5) 0.006(5) C213 0.098(9) 0.096(8) 0.092(8) -0.031(7) 0.016(7) -0.036(8) C216 0.094(8) 0.097(8) 0.041(5) -0.019(5) 0.019(5) -0.040(7) C217 0.086(9) 0.114(9) 0.098(8) -0.051(7) 0.059(7) -0.030(7) C218 0.102(10) 0.148(12) 0.073(7) 0.045(8) -0.007(7) -0.036(9) _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 Zr1 O14 1.928(5) . ? Zr1 O15 1.928(6) . ? Zr1 O16 2.104(4) . ? Zr1 O11 2.175(5) . ? Zr1 O13 2.195(4) . ? Zr1 O16 2.223(4) 2_665 ? Zr1 Zr1 3.5168(15) 2_665 ? Zr2 O25 1.922(5) . ? Zr2 O24 1.942(6) . ? Zr2 O26 2.098(5) . ? Zr2 O21 2.180(6) . ? Zr2 O23 2.187(5) . ? Zr2 O26 2.231(5) 2_776 ? Zr2 Zr2 3.4891(17) 2_776 ? O11 C12 1.273(9) . ? O12 C15 1.337(8) . ? O12 C16 1.469(10) . ? C12 C14 1.380(10) . ? C12 C13 1.510(11) . ? O13 C15 1.257(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? O14 C110 1.413(10) . ? C14 C15 1.396(11) . ? C14 H14 0.9400 . ? O15 C113 1.360(12) . ? O16 C116 1.448(8) . ? O16 Zr1 2.223(4) 2_665 ? C16 C17 1.512(12) . ? C16 C19 1.544(11) . ? C16 C18 1.545(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? O21 C22 1.255(10) . ? O22 C25 1.357(8) . ? O22 C26 1.476(10) . ? C22 C24 1.407(11) . ? C22 C23 1.484(12) . ? O23 C25 1.239(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? O24 C210 1.400(9) . ? C24 C25 1.390(11) . ? C24 H24 0.9400 . ? O25 C213 1.418(12) . ? O26 C216 1.444(9) . ? O26 Zr2 2.231(5) 2_776 ? C26 C29 1.503(14) . ? C26 C27 1.515(13) . ? C26 C28 1.518(12) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C110 C111 1.494(15) . ? C110 C112 1.556(15) . ? C110 H110 0.9900 . ? C111 H11A 0.9700 . ? C111 H11B 0.9700 . ? C111 H11C 0.9700 . ? C112 H11D 0.9700 . ? C112 H11E 0.9700 . ? C112 H11F 0.9700 . ? C113 C114 1.338(18) . ? C113 C115 1.481(17) . ? C113 H113 0.9900 . ? C114 H11G 0.9700 . ? C114 H11H 0.9700 . ? C114 H11I 0.9700 . ? C115 H11J 0.9700 . ? C115 H11K 0.9700 . ? C115 H11L 0.9700 . ? C116 C117 1.505(13) . ? C116 C118 1.510(12) . ? C116 H116 0.9900 . ? C117 H11M 0.9700 . ? C117 H11N 0.9700 . ? C117 H11O 0.9700 . ? C118 H11P 0.9700 . ? C118 H11Q 0.9700 . ? C118 H11R 0.9700 . ? C213 C215 1.49(2) . ? C213 C214 1.495(19) . ? C213 H213 0.9900 . ? C215 H21A 0.9700 . ? C215 H21B 0.9700 . ? C215 H21C 0.9700 . ? C216 C218 1.444(16) . ? C216 C217 1.499(17) . ? C216 H216 0.9900 . ? C217 H21D 0.9700 . ? C217 H21E 0.9700 . ? C217 H21F 0.9700 . ? C218 H21G 0.9700 . ? C218 H21H 0.9700 . ? C218 H21I 0.9700 . ? C214 H21J 0.9700 . ? C214 H21K 0.9700 . ? C214 H21L 0.9700 . ? C210 C212 1.485(9) . ? C210 C211 1.535(10) . ? C210 H210 0.9900 . ? C211 H21M 0.9700 . ? C211 H21N 0.9700 . ? C211 H21O 0.9700 . ? C212 H21P 0.9700 . ? C212 H21Q 0.9700 . ? C212 H21R 0.9700 . ? 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 O14 Zr1 O15 98.9(2) . . ? O14 Zr1 O16 98.28(19) . . ? O15 Zr1 O16 100.4(2) . . ? O14 Zr1 O11 87.7(2) . . ? O15 Zr1 O11 162.3(2) . . ? O16 Zr1 O11 94.80(18) . . ? O14 Zr1 O13 95.74(19) . . ? O15 Zr1 O13 86.1(2) . . ? O16 Zr1 O13 163.38(17) . . ? O11 Zr1 O13 76.85(18) . . ? O14 Zr1 O16 165.26(19) . 2_665 ? O15 Zr1 O16 93.3(2) . 2_665 ? O16 Zr1 O16 71.29(18) . 2_665 ? O11 Zr1 O16 83.00(19) . 2_665 ? O13 Zr1 O16 93.22(16) . 2_665 ? O14 Zr1 Zr1 134.22(15) . 2_665 ? O15 Zr1 Zr1 98.34(17) . 2_665 ? O16 Zr1 Zr1 36.77(12) . 2_665 ? O11 Zr1 Zr1 88.46(13) . 2_665 ? O13 Zr1 Zr1 127.51(13) . 2_665 ? O16 Zr1 Zr1 34.52(10) 2_665 2_665 ? O25 Zr2 O24 97.9(3) . . ? O25 Zr2 O26 99.6(2) . . ? O24 Zr2 O26 103.3(2) . . ? O25 Zr2 O21 88.8(3) . . ? O24 Zr2 O21 165.0(2) . . ? O26 Zr2 O21 88.7(2) . . ? O25 Zr2 O23 95.3(2) . . ? O24 Zr2 O23 89.0(2) . . ? O26 Zr2 O23 159.1(2) . . ? O21 Zr2 O23 76.96(19) . . ? O25 Zr2 O26 169.7(2) . 2_776 ? O24 Zr2 O26 90.6(2) . 2_776 ? O26 Zr2 O26 72.62(19) . 2_776 ? O21 Zr2 O26 84.4(2) . 2_776 ? O23 Zr2 O26 90.68(18) . 2_776 ? O25 Zr2 Zr2 136.82(17) . 2_776 ? O24 Zr2 Zr2 98.34(18) . 2_776 ? O26 Zr2 Zr2 37.61(12) . 2_776 ? O21 Zr2 Zr2 85.62(15) . 2_776 ? O23 Zr2 Zr2 124.69(14) . 2_776 ? O26 Zr2 Zr2 35.02(11) 2_776 2_776 ? C12 O11 Zr1 134.6(4) . . ? C15 O12 C16 122.0(6) . . ? O11 C12 C14 123.9(7) . . ? O11 C12 C13 115.0(6) . . ? C14 C12 C13 121.1(7) . . ? C15 O13 Zr1 133.5(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C110 O14 Zr1 170.1(6) . . ? C12 C14 C15 123.1(7) . . ? C12 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? O13 C15 O12 119.6(6) . . ? O13 C15 C14 125.4(6) . . ? O12 C15 C14 115.0(7) . . ? C113 O15 Zr1 170.5(9) . . ? C116 O16 Zr1 128.6(4) . . ? C116 O16 Zr1 121.8(4) . 2_665 ? Zr1 O16 Zr1 108.71(18) . 2_665 ? O12 C16 C17 111.5(7) . . ? O12 C16 C19 101.3(7) . . ? C17 C16 C19 111.6(7) . . ? O12 C16 C18 109.8(7) . . ? C17 C16 C18 113.5(9) . . ? C19 C16 C18 108.4(7) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 O21 Zr2 135.3(5) . . ? C25 O22 C26 122.2(6) . . ? O21 C22 C24 123.0(8) . . ? O21 C22 C23 116.8(7) . . ? C24 C22 C23 120.2(8) . . ? C25 O23 Zr2 133.2(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C210 O24 Zr2 169.9(9) . . ? C25 C24 C22 122.4(7) . . ? C25 C24 H24 118.8 . . ? C22 C24 H24 118.8 . . ? C213 O25 Zr2 173.2(7) . . ? O23 C25 O22 119.7(7) . . ? O23 C25 C24 126.8(6) . . ? O22 C25 C24 113.5(6) . . ? C216 O26 Zr2 130.9(5) . . ? C216 O26 Zr2 121.0(5) . 2_776 ? Zr2 O26 Zr2 107.38(19) . 2_776 ? O22 C26 C29 110.0(8) . . ? O22 C26 C27 109.9(8) . . ? C29 C26 C27 113.5(11) . . ? O22 C26 C28 101.1(7) . . ? C29 C26 C28 111.9(8) . . ? C27 C26 C28 109.7(8) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O14 C110 C111 110.2(8) . . ? O14 C110 C112 107.1(9) . . ? C111 C110 C112 112.6(9) . . ? O14 C110 H110 109.0 . . ? C111 C110 H110 109.0 . . ? C112 C110 H110 109.0 . . ? C110 C111 H11A 109.5 . . ? C110 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? C110 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? C110 C112 H11D 109.5 . . ? C110 C112 H11E 109.5 . . ? H11D C112 H11E 109.5 . . ? C110 C112 H11F 109.5 . . ? H11D C112 H11F 109.5 . . ? H11E C112 H11F 109.5 . . ? C114 C113 O15 118.4(12) . . ? C114 C113 C115 121.6(13) . . ? O15 C113 C115 111.4(11) . . ? C114 C113 H113 99.8 . . ? O15 C113 H113 99.8 . . ? C115 C113 H113 99.8 . . ? C113 C114 H11G 109.5 . . ? C113 C114 H11H 109.5 . . ? H11G C114 H11H 109.5 . . ? C113 C114 H11I 109.5 . . ? H11G C114 H11I 109.5 . . ? H11H C114 H11I 109.5 . . ? C113 C115 H11J 109.5 . . ? C113 C115 H11K 109.5 . . ? H11J C115 H11K 109.5 . . ? C113 C115 H11L 109.5 . . ? H11J C115 H11L 109.5 . . ? H11K C115 H11L 109.5 . . ? O16 C116 C117 109.0(7) . . ? O16 C116 C118 109.9(7) . . ? C117 C116 C118 113.9(7) . . ? O16 C116 H116 108.0 . . ? C117 C116 H116 108.0 . . ? C118 C116 H116 108.0 . . ? C116 C117 H11M 109.5 . . ? C116 C117 H11N 109.5 . . ? H11M C117 H11N 109.5 . . ? C116 C117 H11O 109.5 . . ? H11M C117 H11O 109.5 . . ? H11N C117 H11O 109.5 . . ? C116 C118 H11P 109.5 . . ? C116 C118 H11Q 109.5 . . ? H11P C118 H11Q 109.5 . . ? C116 C118 H11R 109.5 . . ? H11P C118 H11R 109.5 . . ? H11Q C118 H11R 109.5 . . ? O25 C213 C215 109.2(11) . . ? O25 C213 C214 109.8(12) . . ? C215 C213 C214 114.8(13) . . ? O25 C213 H213 107.6 . . ? C215 C213 H213 107.6 . . ? C214 C213 H213 107.6 . . ? C213 C215 H21A 109.5 . . ? C213 C215 H21B 109.5 . . ? H21A C215 H21B 109.5 . . ? C213 C215 H21C 109.5 . . ? H21A C215 H21C 109.5 . . ? H21B C215 H21C 109.5 . . ? C218 C216 O26 112.0(10) . . ? C218 C216 C217 114.2(9) . . ? O26 C216 C217 110.3(8) . . ? C218 C216 H216 106.6 . . ? O26 C216 H216 106.6 . . ? C217 C216 H216 106.6 . . ? C216 C217 H21D 109.5 . . ? C216 C217 H21E 109.5 . . ? H21D C217 H21E 109.5 . . ? C216 C217 H21F 109.5 . . ? H21D C217 H21F 109.5 . . ? H21E C217 H21F 109.5 . . ? C216 C218 H21G 109.5 . . ? C216 C218 H21H 109.5 . . ? H21G C218 H21H 109.5 . . ? C216 C218 H21I 109.5 . . ? H21G C218 H21I 109.5 . . ? H21H C218 H21I 109.5 . . ? C213 C214 H21J 109.5 . . ? C213 C214 H21K 109.5 . . ? H21J C214 H21K 109.5 . . ? C213 C214 H21L 109.5 . . ? H21J C214 H21L 109.5 . . ? H21K C214 H21L 109.5 . . ? O24 C210 C212 113.0(17) . . ? O24 C210 C211 105.2(18) . . ? C212 C210 C211 102.7(18) . . ? O24 C210 H210 111.8 . . ? C212 C210 H210 111.8 . . ? C211 C210 H210 111.8 . . ? C210 C211 H21M 109.4 . . ? C210 C211 H21N 109.5 . . ? H21M C211 H21N 109.5 . . ? C210 C211 H21O 109.5 . . ? H21M C211 H21O 109.5 . . ? H21N C211 H21O 109.5 . . ? C210 C212 H21P 109.4 . . ? C210 C212 H21Q 109.5 . . ? H21P C212 H21Q 109.5 . . ? C210 C212 H21R 109.5 . . ? H21P C212 H21R 109.5 . . ? H21Q C212 H21R 109.5 . . ? 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 O14 Zr1 O11 C12 78.8(7) . . . . ? O15 Zr1 O11 C12 -33.7(11) . . . . ? O16 Zr1 O11 C12 176.9(7) . . . . ? O13 Zr1 O11 C12 -17.6(7) . . . . ? O16 Zr1 O11 C12 -112.6(7) 2_665 . . . ? Zr1 Zr1 O11 C12 -146.8(7) 2_665 . . . ? Zr1 O11 C12 C14 17.1(12) . . . . ? Zr1 O11 C12 C13 -164.4(6) . . . . ? O14 Zr1 O13 C15 -72.1(6) . . . . ? O15 Zr1 O13 C15 -170.6(6) . . . . ? O16 Zr1 O13 C15 75.4(9) . . . . ? O11 Zr1 O13 C15 14.2(6) . . . . ? O16 Zr1 O13 C15 96.2(6) 2_665 . . . ? Zr1 Zr1 O13 C15 91.8(6) 2_665 . . . ? O15 Zr1 O14 C110 148(3) . . . . ? O16 Zr1 O14 C110 -110(3) . . . . ? O11 Zr1 O14 C110 -15(3) . . . . ? O13 Zr1 O14 C110 61(3) . . . . ? O16 Zr1 O14 C110 -66(3) 2_665 . . . ? Zr1 Zr1 O14 C110 -101(3) 2_665 . . . ? O11 C12 C14 C15 -4.3(12) . . . . ? C13 C12 C14 C15 177.2(7) . . . . ? Zr1 O13 C15 O12 171.9(4) . . . . ? Zr1 O13 C15 C14 -10.6(10) . . . . ? C16 O12 C15 O13 -5.4(9) . . . . ? C16 O12 C15 C14 176.8(6) . . . . ? C12 C14 C15 O13 1.3(12) . . . . ? C12 C14 C15 O12 178.9(7) . . . . ? O14 Zr1 O15 C113 -67(5) . . . . ? O16 Zr1 O15 C113 -168(5) . . . . ? O11 Zr1 O15 C113 44(5) . . . . ? O13 Zr1 O15 C113 28(5) . . . . ? O16 Zr1 O15 C113 121(5) 2_665 . . . ? Zr1 Zr1 O15 C113 155(5) 2_665 . . . ? O14 Zr1 O16 C116 -21.5(6) . . . . ? O15 Zr1 O16 C116 79.2(6) . . . . ? O11 Zr1 O16 C116 -109.9(6) . . . . ? O13 Zr1 O16 C116 -168.8(7) . . . . ? O16 Zr1 O16 C116 169.2(7) 2_665 . . . ? Zr1 Zr1 O16 C116 169.2(7) 2_665 . . . ? O14 Zr1 O16 Zr1 169.3(2) . . . 2_665 ? O15 Zr1 O16 Zr1 -90.0(2) . . . 2_665 ? O11 Zr1 O16 Zr1 80.9(2) . . . 2_665 ? O13 Zr1 O16 Zr1 22.0(8) . . . 2_665 ? O16 Zr1 O16 Zr1 0.0 2_665 . . 2_665 ? C15 O12 C16 C17 -60.1(9) . . . . ? C15 O12 C16 C19 -179.0(7) . . . . ? C15 O12 C16 C18 66.6(9) . . . . ? O25 Zr2 O21 C22 -78.5(8) . . . . ? O24 Zr2 O21 C22 38.3(13) . . . . ? O26 Zr2 O21 C22 -178.2(8) . . . . ? O23 Zr2 O21 C22 17.2(8) . . . . ? O26 Zr2 O21 C22 109.2(8) 2_776 . . . ? Zr2 Zr2 O21 C22 144.3(8) 2_776 . . . ? Zr2 O21 C22 C24 -14.6(13) . . . . ? Zr2 O21 C22 C23 165.4(7) . . . . ? O25 Zr2 O23 C25 75.2(7) . . . . ? O24 Zr2 O23 C25 173.0(7) . . . . ? O26 Zr2 O23 C25 -60.1(9) . . . . ? O21 Zr2 O23 C25 -12.3(6) . . . . ? O26 Zr2 O23 C25 -96.4(7) 2_776 . . . ? Zr2 Zr2 O23 C25 -87.5(7) 2_776 . . . ? O25 Zr2 O24 C210 -80(5) . . . . ? O26 Zr2 O24 C210 22(5) . . . . ? O21 Zr2 O24 C210 164(5) . . . . ? O23 Zr2 O24 C210 -175(5) . . . . ? O26 Zr2 O24 C210 94(5) 2_776 . . . ? Zr2 Zr2 O24 C210 60(5) 2_776 . . . ? O21 C22 C24 C25 -0.7(13) . . . . ? C23 C22 C24 C25 179.3(9) . . . . ? O24 Zr2 O25 C213 -118(6) . . . . ? O26 Zr2 O25 C213 137(6) . . . . ? O21 Zr2 O25 C213 49(6) . . . . ? O23 Zr2 O25 C213 -28(6) . . . . ? O26 Zr2 O25 C213 97(6) 2_776 . . . ? Zr2 Zr2 O25 C213 131(6) 2_776 . . . ? Zr2 O23 C25 O22 -173.5(4) . . . . ? Zr2 O23 C25 C24 5.8(12) . . . . ? C26 O22 C25 O23 5.9(10) . . . . ? C26 O22 C25 C24 -173.4(7) . . . . ? C22 C24 C25 O23 4.9(13) . . . . ? C22 C24 C25 O22 -175.8(7) . . . . ? O25 Zr2 O26 C216 -2.8(8) . . . . ? O24 Zr2 O26 C216 -103.4(8) . . . . ? O21 Zr2 O26 C216 85.7(8) . . . . ? O23 Zr2 O26 C216 131.9(8) . . . . ? O26 Zr2 O26 C216 170.2(9) 2_776 . . . ? Zr2 Zr2 O26 C216 170.2(9) 2_776 . . . ? O25 Zr2 O26 Zr2 -173.0(3) . . . 2_776 ? O24 Zr2 O26 Zr2 86.4(3) . . . 2_776 ? O21 Zr2 O26 Zr2 -84.5(2) . . . 2_776 ? O23 Zr2 O26 Zr2 -38.3(7) . . . 2_776 ? O26 Zr2 O26 Zr2 0.0 2_776 . . 2_776 ? C25 O22 C26 C29 58.5(10) . . . . ? C25 O22 C26 C27 -67.2(10) . . . . ? C25 O22 C26 C28 176.9(7) . . . . ? Zr1 O14 C110 C111 9(4) . . . . ? Zr1 O14 C110 C112 -114(3) . . . . ? Zr1 O15 C113 C114 -141(4) . . . . ? Zr1 O15 C113 C115 71(5) . . . . ? Zr1 O16 C116 C117 77.2(8) . . . . ? Zr1 O16 C116 C117 -114.8(6) 2_665 . . . ? Zr1 O16 C116 C118 -48.2(9) . . . . ? Zr1 O16 C116 C118 119.7(6) 2_665 . . . ? Zr2 O25 C213 C215 -26(6) . . . . ? Zr2 O25 C213 C214 101(6) . . . . ? Zr2 O26 C216 C218 69.8(11) . . . . ? Zr2 O26 C216 C218 -121.0(8) 2_776 . . . ? Zr2 O26 C216 C217 -58.6(11) . . . . ? Zr2 O26 C216 C217 110.6(8) 2_776 . . . ? Zr2 O24 C210 C212 163(4) . . . . ? Zr2 O24 C210 C211 52(6) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.978 _refine_diff_density_min -0.921 _refine_diff_density_rms 0.099