#Supplementary Material (ESI) for Chemical Communications #This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Shuangfeng Yin' _publ_contact_author_email 'SF YIN@HNU.CN' _publ_section_title ; Synthesis and structure of air-stable Lewis acidic binuclear complex of zirconocene pentafluorophenylsulfonate and its catalytic application in the allylation of carbonyl compounds with tetraallyltin ; loop_ _publ_author_name 'Shuangfeng Yin' 'Delie An' 'Yinhui Li' 'Renhua Qiu' 'Lingling Shao' ; Xinhua Xu ; 'Guoping Zhang' # Attachment 'Zirconcene_pentafluorophenylsulfonate_binuclear.cif' data_cd27276 _database_code_depnum_ccdc_archive 'CCDC 660033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '[Zr2Cp2(/n2-OH)2(H2O)6(OSO2C6F5)4(H2O)6]' ; _chemical_name_common (Zr2Cp2(/n2-OH)2(H2O)6(OSO2C6F5)4(H2O)6) _chemical_melting_point ? _chemical_formula_moiety 'ZrCp2,OH, H2O, OSO2C6F5' _chemical_formula_sum 'C34 H36 F20 O26 S4 Zr2' _chemical_formula_weight 1551.31 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.4274(9) _cell_length_b 12.0826(7) _cell_length_c 29.1463(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5433.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9214 _cell_measurement_theta_min 4.504 _cell_measurement_theta_max 54.783 _exptl_crystal_description prismatic _exptl_crystal_colour ? _exptl_crystal_size_max 0.491 _exptl_crystal_size_mid 0.405 _exptl_crystal_size_min 0.227 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3088 _exptl_absorpt_coefficient_mu 0.689 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6919 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30851 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6169 _reflns_number_gt 4815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.7773P] 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 SHELXL _refine_ls_extinction_coef 0.00096(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6169 _refine_ls_number_parameters 441 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zr Zr 0.013287(18) 0.42228(2) 0.049960(9) 0.02734(11) Uani 1 1 d . . . S1 S 0.14996(5) 0.02424(7) 0.10035(3) 0.0411(2) Uani 1 1 d . . . S2 S 0.85346(5) 0.84935(6) 0.07933(3) 0.03589(19) Uani 1 1 d . . . F1 F 0.0946(2) -0.1514(2) 0.16348(13) 0.1024(10) Uani 1 1 d . . . F2 F 0.1122(3) -0.1624(3) 0.25549(15) 0.1554(19) Uani 1 1 d . . . F3 F 0.2000(2) -0.0010(4) 0.30138(10) 0.1424(17) Uani 1 1 d . . . F4 F 0.2610(2) 0.1722(4) 0.25558(11) 0.1309(16) Uani 1 1 d . . . F5 F 0.2391(2) 0.1907(2) 0.16619(10) 0.0954(9) Uani 1 1 d . . . F6 F 0.86440(18) 0.72428(17) 0.16608(9) 0.0726(7) Uani 1 1 d . . . F7 F 0.9071(2) 0.7940(3) 0.25006(9) 0.0961(9) Uani 1 1 d . . . F8 F 0.9444(2) 1.0103(3) 0.26457(8) 0.1001(10) Uani 1 1 d . . . F9 F 0.9371(2) 1.15526(19) 0.19445(9) 0.0831(8) Uani 1 1 d . . . F10 F 0.88810(16) 1.09158(15) 0.11184(8) 0.0565(6) Uani 1 1 d . . . O1 O -0.01505(13) 0.57952(15) 0.02387(7) 0.0280(4) Uani 1 1 d D . . O2 O 0.14951(15) 0.43809(19) 0.03490(9) 0.0395(5) Uani 1 1 d D . . O3 O 0.04385(17) 0.24696(18) 0.03916(9) 0.0422(5) Uani 1 1 d D . . O4 O -0.11611(14) 0.36055(19) 0.03445(9) 0.0387(5) Uani 1 1 d D . . O5 O 0.20737(17) -0.0612(2) 0.08377(10) 0.0587(7) Uani 1 1 d . . . O6 O 0.05971(16) 0.0025(3) 0.09200(10) 0.0665(8) Uani 1 1 d . . . O7 O 0.17580(17) 0.1332(2) 0.08587(10) 0.0604(7) Uani 1 1 d . . . O8 O 0.91854(15) 0.76661(19) 0.07221(8) 0.0486(6) Uani 1 1 d . . . O9 O 0.76640(15) 0.8050(2) 0.08275(9) 0.0499(6) Uani 1 1 d . . . O10 O 0.85918(18) 0.9407(2) 0.04771(8) 0.0486(6) Uani 1 1 d . . . O11 O 0.2183(2) 0.4151(2) -0.04512(11) 0.0618(8) Uani 1 1 d D . . O12 O -0.05694(18) 0.1120(2) -0.00344(10) 0.0546(7) Uani 1 1 d D . . O13 O -0.1663(2) 0.2930(3) -0.04678(13) 0.0680(9) Uani 1 1 d D . . C1 C 0.0275(4) 0.3521(4) 0.13055(14) 0.0815(17) Uani 1 1 d . . . H1 H 0.0429 0.2784 0.1347 0.098 Uiso 1 1 calc R . . C2 C 0.0833(3) 0.4379(9) 0.12687(15) 0.117(3) Uani 1 1 d . . . H2 H 0.1434 0.4340 0.1282 0.140 Uiso 1 1 calc R . . C3 C 0.0349(7) 0.5315(5) 0.12074(15) 0.118(3) Uani 1 1 d . . . H3 H 0.0558 0.6032 0.1169 0.141 Uiso 1 1 calc R . . C4 C -0.0491(4) 0.4997(5) 0.12136(13) 0.089(2) Uani 1 1 d . . . H4 H -0.0966 0.5465 0.1182 0.107 Uiso 1 1 calc R . . C5 C -0.0527(3) 0.3907(5) 0.12729(14) 0.0717(13) Uani 1 1 d . . . H5 H -0.1031 0.3486 0.1289 0.086 Uiso 1 1 calc R . . C6 C 0.1640(2) 0.0199(3) 0.16121(13) 0.0471(8) Uani 1 1 d . . . C7 C 0.1340(3) -0.0694(4) 0.18521(18) 0.0685(13) Uani 1 1 d . . . C8 C 0.1465(4) -0.0766(5) 0.2336(2) 0.0905(19) Uani 1 1 d . . . C9 C 0.1895(3) 0.0091(6) 0.25533(19) 0.0903(18) Uani 1 1 d . . . C10 C 0.2193(3) 0.0943(5) 0.23277(19) 0.0797(14) Uani 1 1 d . . . C11 C 0.2066(3) 0.1028(4) 0.18639(14) 0.0601(10) Uani 1 1 d . . . C12 C 0.8762(2) 0.9036(3) 0.13525(11) 0.0360(7) Uani 1 1 d . . . C13 C 0.8808(2) 0.8318(3) 0.17225(13) 0.0465(8) Uani 1 1 d . . . C14 C 0.9027(3) 0.8662(4) 0.21493(14) 0.0609(11) Uani 1 1 d . . . C15 C 0.9227(3) 0.9760(4) 0.22279(13) 0.0625(11) Uani 1 1 d . . . C16 C 0.9176(3) 1.0489(3) 0.18716(14) 0.0530(9) Uani 1 1 d . . . C17 C 0.8935(2) 1.0141(3) 0.14425(11) 0.0408(8) Uani 1 1 d . . . H1A H -0.028(2) 0.636(2) 0.0413(10) 0.039(9) Uiso 1 1 d D . . H2A H 0.195(2) 0.439(4) 0.0530(14) 0.086(17) Uiso 1 1 d D . . H2B H 0.168(2) 0.427(3) 0.0068(8) 0.042(10) Uiso 1 1 d D . . H3A H 0.087(3) 0.217(4) 0.0545(17) 0.11(2) Uiso 1 1 d D . . H3B H 0.005(2) 0.200(3) 0.0267(15) 0.073(15) Uiso 1 1 d D . . H4A H -0.136(2) 0.337(3) 0.0078(9) 0.057(12) Uiso 1 1 d D . . H4B H -0.156(2) 0.344(3) 0.0536(11) 0.057(12) Uiso 1 1 d D . . H11A H 0.245(3) 0.356(3) -0.0536(17) 0.094(18) Uiso 1 1 d D . . H11B H 0.2701(18) 0.442(4) -0.0444(18) 0.091(18) Uiso 1 1 d D . . H12A H -0.074(3) 0.056(3) 0.0152(15) 0.098(18) Uiso 1 1 d D . . H12B H -0.038(3) 0.087(3) -0.0309(9) 0.074(15) Uiso 1 1 d D . . H13A H -0.196(2) 0.272(3) -0.0242(10) 0.050(13) Uiso 1 1 d D . . H13B H -0.167(4) 0.226(3) -0.060(2) 0.13(2) Uiso 1 1 d 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 Zr 0.03074(18) 0.02454(17) 0.02673(17) 0.00089(11) -0.00185(11) 0.00153(11) S1 0.0332(4) 0.0453(5) 0.0449(5) 0.0016(4) 0.0065(3) 0.0042(3) S2 0.0378(4) 0.0305(4) 0.0393(4) -0.0044(3) -0.0005(3) 0.0038(3) F1 0.100(2) 0.0596(16) 0.147(3) 0.0289(18) 0.019(2) -0.0162(16) F2 0.146(3) 0.151(4) 0.169(4) 0.114(3) 0.050(3) 0.018(3) F3 0.104(2) 0.266(5) 0.0564(18) 0.043(3) 0.0047(17) 0.034(3) F4 0.109(3) 0.201(5) 0.083(2) -0.041(2) -0.0241(19) -0.020(3) F5 0.114(2) 0.0860(19) 0.086(2) -0.0012(16) -0.0161(17) -0.0383(18) F6 0.114(2) 0.0376(11) 0.0657(15) 0.0081(11) 0.0046(14) -0.0072(12) F7 0.144(3) 0.0912(19) 0.0532(15) 0.0208(15) -0.0085(16) -0.0100(19) F8 0.141(3) 0.115(2) 0.0441(14) -0.0207(15) -0.0098(16) -0.020(2) F9 0.121(2) 0.0535(14) 0.0744(17) -0.0279(13) 0.0114(16) -0.0247(15) F10 0.0783(16) 0.0310(10) 0.0602(14) 0.0005(9) 0.0039(12) -0.0002(10) O1 0.0336(11) 0.0217(10) 0.0286(11) -0.0045(8) -0.0017(8) 0.0025(8) O2 0.0307(12) 0.0474(14) 0.0404(13) -0.0053(11) -0.0039(10) 0.0004(10) O3 0.0501(14) 0.0266(11) 0.0500(14) 0.0006(10) -0.0109(12) 0.0045(11) O4 0.0328(12) 0.0403(13) 0.0430(13) -0.0005(11) 0.0022(11) -0.0050(10) O5 0.0454(14) 0.0599(16) 0.0708(19) -0.0098(14) 0.0154(13) 0.0069(12) O6 0.0362(14) 0.094(2) 0.0690(18) -0.0094(17) 0.0036(13) 0.0032(14) O7 0.0619(17) 0.0572(16) 0.0620(17) 0.0175(14) 0.0006(13) 0.0015(13) O8 0.0533(14) 0.0401(13) 0.0524(15) -0.0134(11) -0.0002(12) 0.0129(11) O9 0.0397(13) 0.0482(13) 0.0618(16) -0.0005(12) -0.0050(11) -0.0033(11) O10 0.0598(16) 0.0451(14) 0.0409(14) 0.0028(11) 0.0006(11) 0.0039(11) O11 0.0567(19) 0.0509(17) 0.078(2) -0.0210(14) 0.0224(15) -0.0117(14) O12 0.0598(17) 0.0425(14) 0.0616(18) -0.0074(14) 0.0035(14) -0.0058(13) O13 0.077(2) 0.0472(17) 0.080(2) -0.0102(17) -0.0215(19) 0.0050(16) C1 0.141(5) 0.073(3) 0.030(2) 0.011(2) 0.004(3) 0.049(3) C2 0.046(3) 0.278(10) 0.027(2) 0.003(4) -0.0086(19) -0.023(4) C3 0.249(9) 0.079(4) 0.025(2) -0.004(2) -0.005(4) -0.093(5) C4 0.146(5) 0.093(4) 0.028(2) 0.000(2) 0.008(3) 0.072(4) C5 0.072(3) 0.105(4) 0.037(2) 0.001(2) 0.011(2) -0.024(3) C6 0.0358(18) 0.057(2) 0.049(2) 0.0113(17) 0.0060(15) 0.0095(16) C7 0.056(3) 0.066(3) 0.084(3) 0.025(2) 0.015(2) 0.003(2) C8 0.071(3) 0.104(4) 0.097(4) 0.060(4) 0.035(3) 0.017(3) C9 0.053(3) 0.142(6) 0.076(4) 0.035(4) 0.012(3) 0.026(3) C10 0.058(3) 0.109(4) 0.073(3) -0.009(3) -0.005(3) 0.004(3) C11 0.051(2) 0.083(3) 0.047(2) 0.000(2) 0.0020(18) 0.004(2) C12 0.0346(16) 0.0351(16) 0.0384(17) -0.0065(13) 0.0063(13) 0.0018(13) C13 0.054(2) 0.0393(18) 0.046(2) -0.0009(16) 0.0049(16) -0.0025(16) C14 0.074(3) 0.064(3) 0.044(2) 0.008(2) 0.0041(19) -0.001(2) C15 0.071(3) 0.076(3) 0.040(2) -0.013(2) 0.0020(19) -0.005(2) C16 0.062(2) 0.044(2) 0.053(2) -0.0139(18) 0.0100(19) -0.0074(18) C17 0.0424(18) 0.0351(17) 0.0449(19) -0.0041(15) 0.0060(15) 0.0024(14) _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 Zr O1 2.0926(19) . ? Zr O1 2.152(2) 5_565 ? Zr O2 2.155(2) . ? Zr O4 2.178(2) . ? Zr O3 2.193(2) . ? Zr C3 2.472(4) . ? Zr C4 2.476(4) . ? Zr C2 2.495(4) . ? Zr C5 2.503(4) . ? Zr C1 2.507(4) . ? Zr Zr 3.4896(6) 5_565 ? S1 O6 1.438(3) . ? S1 O7 1.439(3) . ? S1 O5 1.443(3) . ? S1 C6 1.788(4) . ? S2 O8 1.432(2) . ? S2 O10 1.441(3) . ? S2 O9 1.450(2) . ? S2 C12 1.792(3) . ? F1 C7 1.324(6) . ? F2 C8 1.327(6) . ? F3 C9 1.357(6) . ? F4 C10 1.320(6) . ? F5 C11 1.314(5) . ? F6 C13 1.335(4) . ? F7 C14 1.347(5) . ? F8 C15 1.330(4) . ? F9 C16 1.337(4) . ? F10 C17 1.333(4) . ? O1 Zr 2.152(2) 5_565 ? O1 H1A 0.876(18) . ? O2 H2A 0.882(19) . ? O2 H2B 0.879(18) . ? O3 H3A 0.88(2) . ? O3 H3B 0.895(19) . ? O4 H4A 0.879(19) . ? O4 H4B 0.857(19) . ? O11 H11A 0.861(19) . ? O11 H11B 0.86(2) . ? O12 H12A 0.903(19) . ? O12 H12B 0.903(19) . ? O13 H13A 0.844(18) . ? O13 H13B 0.89(2) . ? C1 C5 1.327(7) . ? C1 C2 1.351(9) . ? C1 H1 0.9300 . ? C2 C3 1.367(10) . ? C2 H2 0.9300 . ? C3 C4 1.353(9) . ? C3 H3 0.9300 . ? C4 C5 1.330(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.366(5) . ? C6 C11 1.405(6) . ? C7 C8 1.426(8) . ? C8 C9 1.383(9) . ? C9 C10 1.305(8) . ? C10 C11 1.370(6) . ? C12 C17 1.386(4) . ? C12 C13 1.386(5) . ? C13 C14 1.355(5) . ? C14 C15 1.380(6) . ? C15 C16 1.364(6) . ? C16 C17 1.371(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 O1 Zr O1 69.42(8) . 5_565 ? O1 Zr O2 92.82(8) . . ? O1 Zr O2 77.58(9) 5_565 . ? O1 Zr O4 92.52(8) . . ? O1 Zr O4 78.50(8) 5_565 . ? O2 Zr O4 151.83(9) . . ? O1 Zr O3 150.44(9) . . ? O1 Zr O3 81.02(8) 5_565 . ? O2 Zr O3 81.18(9) . . ? O4 Zr O3 80.59(9) . . ? O1 Zr C3 81.17(18) . . ? O1 Zr C3 146.94(13) 5_565 . ? O2 Zr C3 89.5(2) . . ? O4 Zr C3 118.7(2) . . ? O3 Zr C3 127.4(2) . . ? O1 Zr C4 83.16(13) . . ? O1 Zr C4 148.09(12) 5_565 . ? O2 Zr C4 121.11(19) . . ? O4 Zr C4 86.99(19) . . ? O3 Zr C4 124.70(15) . . ? C3 Zr C4 31.7(2) . . ? O1 Zr C2 110.4(3) . . ? O1 Zr C2 153.31(13) 5_565 . ? O2 Zr C2 75.78(13) . . ? O4 Zr C2 127.51(16) . . ? O3 Zr C2 96.3(3) . . ? C3 Zr C2 31.9(2) . . ? C4 Zr C2 52.0(2) . . ? O1 Zr C5 112.37(15) . . ? O1 Zr C5 154.70(12) 5_565 . ? O2 Zr C5 126.43(13) . . ? O4 Zr C5 76.22(13) . . ? O3 Zr C5 93.99(15) . . ? C3 Zr C5 52.03(17) . . ? C4 Zr C5 30.98(17) . . ? C2 Zr C5 51.58(17) . . ? O1 Zr C1 131.74(12) . . ? O1 Zr C1 158.81(12) 5_565 . ? O2 Zr C1 97.78(17) . . ? O4 Zr C1 99.15(18) . . ? O3 Zr C1 77.83(13) . . ? C3 Zr C1 52.17(18) . . ? C4 Zr C1 51.28(15) . . ? C2 Zr C1 31.3(2) . . ? C5 Zr C1 30.71(17) . . ? O1 Zr Zr 35.27(6) . 5_565 ? O1 Zr Zr 34.15(5) 5_565 5_565 ? O2 Zr Zr 84.08(7) . 5_565 ? O4 Zr Zr 84.46(6) . 5_565 ? O3 Zr Zr 115.17(7) . 5_565 ? C3 Zr Zr 115.15(15) . 5_565 ? C4 Zr Zr 116.88(11) . 5_565 ? C2 Zr Zr 139.4(2) . 5_565 ? C5 Zr Zr 141.80(14) . 5_565 ? C1 Zr Zr 166.97(11) . 5_565 ? O6 S1 O7 112.69(17) . . ? O6 S1 O5 114.03(17) . . ? O7 S1 O5 112.69(16) . . ? O6 S1 C6 106.25(16) . . ? O7 S1 C6 106.53(18) . . ? O5 S1 C6 103.71(17) . . ? O8 S2 O10 113.53(15) . . ? O8 S2 O9 113.66(15) . . ? O10 S2 O9 112.59(15) . . ? O8 S2 C12 104.48(14) . . ? O10 S2 C12 106.82(15) . . ? O9 S2 C12 104.75(15) . . ? Zr O1 Zr 110.58(9) . 5_565 ? Zr O1 H1A 123(2) . . ? Zr O1 H1A 126(2) 5_565 . ? Zr O2 H2A 131(3) . . ? Zr O2 H2B 120(2) . . ? H2A O2 H2B 107(4) . . ? Zr O3 H3A 119(4) . . ? Zr O3 H3B 122(3) . . ? H3A O3 H3B 116(5) . . ? Zr O4 H4A 127(3) . . ? Zr O4 H4B 127(3) . . ? H4A O4 H4B 105(4) . . ? H2B O11 H11A 123(4) . . ? H2B O11 H11B 112(4) . . ? H11A O11 H11B 83(4) . . ? H3B O12 H12A 109(4) . . ? H3B O12 H12B 119(3) . . ? H12A O12 H12B 112(4) . . ? H4A O13 H13A 62(3) . . ? H4A O13 H13B 132(4) . . ? H13A O13 H13B 94(5) . . ? C5 C1 C2 108.6(5) . . ? C5 C1 Zr 74.5(2) . . ? C2 C1 Zr 73.9(3) . . ? C5 C1 H1 125.7 . . ? C2 C1 H1 125.7 . . ? Zr C1 H1 117.9 . . ? C1 C2 C3 107.3(5) . . ? C1 C2 Zr 74.8(3) . . ? C3 C2 Zr 73.1(3) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? Zr C2 H2 117.8 . . ? C4 C3 C2 106.6(5) . . ? C4 C3 Zr 74.3(3) . . ? C2 C3 Zr 75.0(3) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? Zr C3 H3 116.3 . . ? C5 C4 C3 108.9(5) . . ? C5 C4 Zr 75.6(3) . . ? C3 C4 Zr 73.9(3) . . ? C5 C4 H4 125.6 . . ? C3 C4 H4 125.6 . . ? Zr C4 H4 116.8 . . ? C1 C5 C4 108.5(5) . . ? C1 C5 Zr 74.8(3) . . ? C4 C5 Zr 73.4(3) . . ? C1 C5 H5 125.7 . . ? C4 C5 H5 125.7 . . ? Zr C5 H5 117.9 . . ? C7 C6 C11 117.0(4) . . ? C7 C6 S1 119.4(4) . . ? C11 C6 S1 123.6(3) . . ? F1 C7 C6 120.1(5) . . ? F1 C7 C8 119.3(4) . . ? C6 C7 C8 120.6(5) . . ? F2 C8 C9 123.7(6) . . ? F2 C8 C7 118.0(6) . . ? C9 C8 C7 118.2(5) . . ? C10 C9 F3 121.8(7) . . ? C10 C9 C8 121.9(5) . . ? F3 C9 C8 116.3(6) . . ? C9 C10 F4 118.7(6) . . ? C9 C10 C11 120.4(5) . . ? F4 C10 C11 120.9(5) . . ? F5 C11 C10 116.6(4) . . ? F5 C11 C6 121.4(4) . . ? C10 C11 C6 121.9(4) . . ? C17 C12 C13 116.5(3) . . ? C17 C12 S2 124.2(3) . . ? C13 C12 S2 119.2(2) . . ? F6 C13 C14 118.0(3) . . ? F6 C13 C12 119.7(3) . . ? C14 C13 C12 122.3(3) . . ? F7 C14 C13 120.8(4) . . ? F7 C14 C15 119.0(4) . . ? C13 C14 C15 120.2(4) . . ? F8 C15 C16 120.7(4) . . ? F8 C15 C14 120.5(4) . . ? C16 C15 C14 118.8(4) . . ? F9 C16 C15 119.2(4) . . ? F9 C16 C17 120.1(4) . . ? C15 C16 C17 120.8(3) . . ? F10 C17 C16 116.6(3) . . ? F10 C17 C12 122.0(3) . . ? C16 C17 C12 121.4(3) . . ? 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 Zr O1 Zr 0.0 5_565 . . 5_565 ? O2 Zr O1 Zr 75.61(10) . . . 5_565 ? O4 Zr O1 Zr -76.72(10) . . . 5_565 ? O3 Zr O1 Zr -1.4(2) . . . 5_565 ? C3 Zr O1 Zr 164.6(2) . . . 5_565 ? C4 Zr O1 Zr -163.39(19) . . . 5_565 ? C2 Zr O1 Zr 151.48(14) . . . 5_565 ? C5 Zr O1 Zr -152.85(13) . . . 5_565 ? C1 Zr O1 Zr 178.6(2) . . . 5_565 ? O1 Zr C1 C5 59.8(5) . . . . ? O1 Zr C1 C5 -123.7(4) 5_565 . . . ? O2 Zr C1 C5 160.6(3) . . . . ? O4 Zr C1 C5 -41.9(4) . . . . ? O3 Zr C1 C5 -120.2(4) . . . . ? C3 Zr C1 C5 77.4(4) . . . . ? C4 Zr C1 C5 36.7(3) . . . . ? C2 Zr C1 C5 115.2(5) . . . . ? Zr Zr C1 C5 63.3(10) 5_565 . . . ? O1 Zr C1 C2 -55.4(5) . . . . ? O1 Zr C1 C2 121.1(5) 5_565 . . . ? O2 Zr C1 C2 45.5(4) . . . . ? O4 Zr C1 C2 -157.1(4) . . . . ? O3 Zr C1 C2 124.7(5) . . . . ? C3 Zr C1 C2 -37.8(4) . . . . ? C4 Zr C1 C2 -78.5(4) . . . . ? C5 Zr C1 C2 -115.2(5) . . . . ? Zr Zr C1 C2 -51.9(10) 5_565 . . . ? C5 C1 C2 C3 -0.6(6) . . . . ? Zr C1 C2 C3 66.4(3) . . . . ? C5 C1 C2 Zr -67.0(3) . . . . ? O1 Zr C2 C1 139.1(4) . . . . ? O1 Zr C2 C1 -136.4(3) 5_565 . . . ? O2 Zr C2 C1 -133.2(5) . . . . ? O4 Zr C2 C1 28.9(6) . . . . ? O3 Zr C2 C1 -54.0(4) . . . . ? C3 Zr C2 C1 113.9(5) . . . . ? C4 Zr C2 C1 75.9(4) . . . . ? C5 Zr C2 C1 36.2(3) . . . . ? Zr Zr C2 C1 164.2(3) 5_565 . . . ? O1 Zr C2 C3 25.2(5) . . . . ? O1 Zr C2 C3 109.7(4) 5_565 . . . ? O2 Zr C2 C3 112.9(5) . . . . ? O4 Zr C2 C3 -85.0(6) . . . . ? O3 Zr C2 C3 -167.9(5) . . . . ? C4 Zr C2 C3 -38.0(4) . . . . ? C5 Zr C2 C3 -77.8(4) . . . . ? C1 Zr C2 C3 -113.9(5) . . . . ? Zr Zr C2 C3 50.3(5) 5_565 . . . ? C1 C2 C3 C4 0.6(6) . . . . ? Zr C2 C3 C4 68.2(3) . . . . ? C1 C2 C3 Zr -67.5(4) . . . . ? O1 Zr C3 C4 91.3(4) . . . . ? O1 Zr C3 C4 118.3(3) 5_565 . . . ? O2 Zr C3 C4 -175.8(4) . . . . ? O4 Zr C3 C4 3.2(5) . . . . ? O3 Zr C3 C4 -97.3(5) . . . . ? C2 Zr C3 C4 -112.5(5) . . . . ? C5 Zr C3 C4 -36.3(3) . . . . ? C1 Zr C3 C4 -75.5(3) . . . . ? Zr Zr C3 C4 101.0(3) 5_565 . . . ? O1 Zr C3 C2 -156.2(5) . . . . ? O1 Zr C3 C2 -129.2(3) 5_565 . . . ? O2 Zr C3 C2 -63.3(5) . . . . ? O4 Zr C3 C2 115.8(5) . . . . ? O3 Zr C3 C2 15.2(6) . . . . ? C4 Zr C3 C2 112.5(5) . . . . ? C5 Zr C3 C2 76.2(4) . . . . ? C1 Zr C3 C2 37.0(3) . . . . ? Zr Zr C3 C2 -146.5(4) 5_565 . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? Zr C3 C4 C5 68.2(3) . . . . ? C2 C3 C4 Zr -68.6(4) . . . . ? O1 Zr C4 C5 160.8(4) . . . . ? O1 Zr C4 C5 130.4(3) 5_565 . . . ? O2 Zr C4 C5 -110.0(4) . . . . ? O4 Zr C4 C5 67.9(4) . . . . ? O3 Zr C4 C5 -8.5(5) . . . . ? C3 Zr C4 C5 -114.9(5) . . . . ? C2 Zr C4 C5 -76.6(4) . . . . ? C1 Zr C4 C5 -36.3(3) . . . . ? Zr Zr C4 C5 150.2(3) 5_565 . . . ? O1 Zr C4 C3 -84.3(4) . . . . ? O1 Zr C4 C3 -114.7(4) 5_565 . . . ? O2 Zr C4 C3 4.9(5) . . . . ? O4 Zr C4 C3 -177.2(4) . . . . ? O3 Zr C4 C3 106.5(5) . . . . ? C2 Zr C4 C3 38.3(4) . . . . ? C5 Zr C4 C3 114.9(5) . . . . ? C1 Zr C4 C3 78.6(4) . . . . ? Zr Zr C4 C3 -94.9(4) 5_565 . . . ? C2 C1 C5 C4 0.3(5) . . . . ? Zr C1 C5 C4 -66.2(3) . . . . ? C2 C1 C5 Zr 66.5(3) . . . . ? C3 C4 C5 C1 0.1(5) . . . . ? Zr C4 C5 C1 67.2(3) . . . . ? C3 C4 C5 Zr -67.1(3) . . . . ? O1 Zr C5 C1 -135.8(3) . . . . ? O1 Zr C5 C1 135.3(3) 5_565 . . . ? O2 Zr C5 C1 -24.1(4) . . . . ? O4 Zr C5 C1 137.2(4) . . . . ? O3 Zr C5 C1 57.9(4) . . . . ? C3 Zr C5 C1 -77.9(4) . . . . ? C4 Zr C5 C1 -115.1(5) . . . . ? C2 Zr C5 C1 -36.9(4) . . . . ? Zr Zr C5 C1 -161.0(3) 5_565 . . . ? O1 Zr C5 C4 -20.7(4) . . . . ? O1 Zr C5 C4 -109.6(4) 5_565 . . . ? O2 Zr C5 C4 91.0(4) . . . . ? O4 Zr C5 C4 -107.7(4) . . . . ? O3 Zr C5 C4 173.0(4) . . . . ? C3 Zr C5 C4 37.2(4) . . . . ? C2 Zr C5 C4 78.2(4) . . . . ? C1 Zr C5 C4 115.1(5) . . . . ? Zr Zr C5 C4 -45.9(4) 5_565 . . . ? O6 S1 C6 C7 51.4(3) . . . . ? O7 S1 C6 C7 171.8(3) . . . . ? O5 S1 C6 C7 -69.1(3) . . . . ? O6 S1 C6 C11 -130.3(3) . . . . ? O7 S1 C6 C11 -9.9(4) . . . . ? O5 S1 C6 C11 109.2(3) . . . . ? C11 C6 C7 F1 -178.8(4) . . . . ? S1 C6 C7 F1 -0.4(5) . . . . ? C11 C6 C7 C8 -0.2(6) . . . . ? S1 C6 C7 C8 178.2(3) . . . . ? F1 C7 C8 F2 -4.8(7) . . . . ? C6 C7 C8 F2 176.6(4) . . . . ? F1 C7 C8 C9 178.6(4) . . . . ? C6 C7 C8 C9 0.0(7) . . . . ? F2 C8 C9 C10 -177.2(5) . . . . ? C7 C8 C9 C10 -0.8(8) . . . . ? F2 C8 C9 F3 3.6(8) . . . . ? C7 C8 C9 F3 180.0(4) . . . . ? F3 C9 C10 F4 0.3(8) . . . . ? C8 C9 C10 F4 -178.9(5) . . . . ? F3 C9 C10 C11 -179.1(4) . . . . ? C8 C9 C10 C11 1.7(8) . . . . ? C9 C10 C11 F5 -179.6(4) . . . . ? F4 C10 C11 F5 1.0(7) . . . . ? C9 C10 C11 C6 -1.9(7) . . . . ? F4 C10 C11 C6 178.7(4) . . . . ? C7 C6 C11 F5 178.7(4) . . . . ? S1 C6 C11 F5 0.3(6) . . . . ? C7 C6 C11 C10 1.2(6) . . . . ? S1 C6 C11 C10 -177.2(3) . . . . ? O8 S2 C12 C17 122.0(3) . . . . ? O10 S2 C12 C17 1.4(3) . . . . ? O9 S2 C12 C17 -118.3(3) . . . . ? O8 S2 C12 C13 -55.2(3) . . . . ? O10 S2 C12 C13 -175.8(3) . . . . ? O9 S2 C12 C13 64.6(3) . . . . ? C17 C12 C13 F6 179.6(3) . . . . ? S2 C12 C13 F6 -3.0(5) . . . . ? C17 C12 C13 C14 -1.3(5) . . . . ? S2 C12 C13 C14 176.1(3) . . . . ? F6 C13 C14 F7 -0.4(6) . . . . ? C12 C13 C14 F7 -179.5(4) . . . . ? F6 C13 C14 C15 178.2(4) . . . . ? C12 C13 C14 C15 -0.9(6) . . . . ? F7 C14 C15 F8 -1.2(6) . . . . ? C13 C14 C15 F8 -179.8(4) . . . . ? F7 C14 C15 C16 -179.7(4) . . . . ? C13 C14 C15 C16 1.7(6) . . . . ? F8 C15 C16 F9 1.7(6) . . . . ? C14 C15 C16 F9 -179.8(4) . . . . ? F8 C15 C16 C17 -178.7(4) . . . . ? C14 C15 C16 C17 -0.3(6) . . . . ? F9 C16 C17 F10 -2.2(5) . . . . ? C15 C16 C17 F10 178.2(3) . . . . ? F9 C16 C17 C12 177.5(3) . . . . ? C15 C16 C17 C12 -2.1(6) . . . . ? C13 C12 C17 F10 -177.5(3) . . . . ? S2 C12 C17 F10 5.2(5) . . . . ? C13 C12 C17 C16 2.8(5) . . . . ? S2 C12 C17 C16 -174.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O8 0.876(18) 1.99(2) 2.854(3) 167(3) 1_455 O2 H2A O5 0.882(19) 1.75(2) 2.628(3) 174(5) 8_665 O2 H2A S1 0.882(19) 2.94(3) 3.781(2) 159(4) 8_665 O2 H2B O11 0.879(18) 1.70(2) 2.577(4) 171(4) . O3 H3A O7 0.88(2) 1.93(2) 2.808(4) 173(5) . O3 H3A S1 0.88(2) 2.85(4) 3.620(2) 147(5) . O3 H3B O12 0.895(19) 1.68(2) 2.573(4) 172(5) . O4 H4A O13 0.879(19) 1.74(2) 2.621(4) 175(4) . O4 H4B O9 0.857(19) 1.96(2) 2.794(3) 165(4) 8_655 O11 H11A O9 0.861(19) 2.13(3) 2.886(4) 147(5) 5_665 O11 H11A S2 0.861(19) 3.00(5) 3.526(3) 122(4) 5_665 O11 H11B O10 0.86(2) 1.97(3) 2.787(4) 156(5) 4_465 O11 H11B S2 0.86(2) 3.01(4) 3.666(3) 135(4) 4_465 O12 H12A O10 0.903(19) 1.98(2) 2.860(4) 165(5) 1_445 O12 H12B O6 0.903(19) 2.11(3) 2.929(4) 150(4) 5 O12 H12B S1 0.903(19) 2.98(4) 3.570(3) 124(4) 5 O13 H13B O5 0.89(2) 2.20(3) 3.068(4) 163(6) 5 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.749 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.083