# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Kehr, Gerald' 'Erker, G.' 'Frohlich, Roland' 'Xu, Boahua' 'Nauha, Elisa' _publ_contact_author_name 'Kehr, Gerald ' _publ_contact_author_email kehrald@uni-muenster.de _publ_section_title ; Zirconocene Complexes Bearing Novel 3-Dimethylamino-1,2-dihydropentalene Derived Ligand Systems ; # Attachment '- 2a.cif' data_erk5097 _database_code_depnum_ccdc_archive 'CCDC 778226' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 N' _chemical_formula_weight 161.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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/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 8.2200(12) _cell_length_b 13.0061(12) _cell_length_c 18.295(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.899(5) _cell_angle_gamma 90.00 _cell_volume 1913.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2466 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _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 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8670 _exptl_absorpt_correction_T_max 0.9527 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10363 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 66.12 _reflns_number_total 2744 _reflns_number_gt 1671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrcik, 1997)' _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. Quality of the crystals was poor, the mosaicity was high (about 2 degree), leading to a great amount of rejections in scaling (see: completeness). ; _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^)+(0.0850P)^2^+1.2748P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2744 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1274 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2124 _refine_ls_wR_factor_gt 0.1790 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N1A N 0.3613(4) 0.0808(2) 0.15275(17) 0.0686(9) Uani 1 1 d . . . C1A C 0.4679(5) 0.2517(3) 0.0067(2) 0.0753(11) Uani 1 1 d . . . H1A H 0.5870 0.2622 0.0063 0.090 Uiso 1 1 calc R . . C2A C 0.4467(5) 0.1440(3) 0.03838(19) 0.0689(11) Uani 1 1 d . . . H2A1 H 0.3644 0.1043 0.0031 0.083 Uiso 1 1 calc R . . H2A2 H 0.5526 0.1067 0.0474 0.083 Uiso 1 1 calc R . . C3A C 0.3884(4) 0.1593(3) 0.11111(19) 0.0605(9) Uani 1 1 d . . . C4A C 0.3753(4) 0.2638(3) 0.12422(19) 0.0607(10) Uani 1 1 d . . . C5A C 0.3346(5) 0.3357(3) 0.1770(2) 0.0722(11) Uani 1 1 d . . . H5A H 0.3000 0.3202 0.2216 0.087 Uiso 1 1 calc R . . C6A C 0.3561(5) 0.4320(3) 0.1493(2) 0.0775(12) Uani 1 1 d . . . H6A H 0.3385 0.4942 0.1726 0.093 Uiso 1 1 calc R . . C7A C 0.4092(5) 0.4234(3) 0.0800(2) 0.0734(11) Uani 1 1 d . . . H7A H 0.4314 0.4781 0.0500 0.088 Uiso 1 1 calc R . . C8A C 0.4217(4) 0.3214(3) 0.0653(2) 0.0646(10) Uani 1 1 d . . . C9A C 0.3687(6) 0.2693(4) -0.0709(2) 0.1032(16) Uani 1 1 d . . . H9A1 H 0.2518 0.2576 -0.0717 0.155 Uiso 1 1 calc R . . H9A2 H 0.4058 0.2222 -0.1052 0.155 Uiso 1 1 calc R . . H9A3 H 0.3844 0.3396 -0.0859 0.155 Uiso 1 1 calc R . . C10A C 0.3779(5) -0.0257(3) 0.1305(2) 0.0885(13) Uani 1 1 d . . . H10A H 0.2697 -0.0521 0.1065 0.133 Uiso 1 1 calc R . . H10B H 0.4226 -0.0667 0.1743 0.133 Uiso 1 1 calc R . . H10C H 0.4525 -0.0290 0.0958 0.133 Uiso 1 1 calc R . . C11A C 0.3015(5) 0.0981(3) 0.2216(2) 0.0800(12) Uani 1 1 d . . . H11A H 0.3666 0.1522 0.2503 0.120 Uiso 1 1 calc R . . H11B H 0.3127 0.0353 0.2507 0.120 Uiso 1 1 calc R . . H11C H 0.1855 0.1185 0.2094 0.120 Uiso 1 1 calc R . . N1B N 0.1072(4) 0.8504(3) 0.41198(18) 0.0752(10) Uani 1 1 d . . . C1B C 0.2147(5) 0.7047(3) 0.2561(2) 0.0765(12) Uani 1 1 d . . . H1B H 0.3317 0.6951 0.2516 0.092 Uiso 1 1 calc R . . C2B C 0.1986(5) 0.8053(3) 0.2963(2) 0.0689(11) Uani 1 1 d . . . H2B1 H 0.3066 0.8400 0.3094 0.083 Uiso 1 1 calc R . . H2B2 H 0.1198 0.8512 0.2644 0.083 Uiso 1 1 calc R . . C3B C 0.1366(4) 0.7775(3) 0.36568(19) 0.0640(10) Uani 1 1 d . . . C4B C 0.1229(4) 0.6719(3) 0.37167(18) 0.0608(10) Uani 1 1 d . . . C5B C 0.0794(5) 0.5918(3) 0.4178(2) 0.0730(11) Uani 1 1 d . . . H5B H 0.0426 0.6000 0.4628 0.088 Uiso 1 1 calc R . . C6B C 0.1019(5) 0.5010(4) 0.3835(3) 0.0842(13) Uani 1 1 d . . . H6B H 0.0824 0.4353 0.4013 0.101 Uiso 1 1 calc R . . C7B C 0.1599(5) 0.5212(3) 0.3160(2) 0.0800(12) Uani 1 1 d . . . H7B H 0.1859 0.4719 0.2827 0.096 Uiso 1 1 calc R . . C8B C 0.1702(4) 0.6242(3) 0.3095(2) 0.0680(10) Uani 1 1 d . . . C9B C 0.1042(6) 0.7019(4) 0.1797(2) 0.1115(18) Uani 1 1 d . . . H9B1 H -0.0100 0.7140 0.1838 0.167 Uiso 1 1 calc R . . H9B2 H 0.1128 0.6351 0.1572 0.167 Uiso 1 1 calc R . . H9B3 H 0.1386 0.7549 0.1487 0.167 Uiso 1 1 calc R . . C10B C 0.1204(6) 0.9596(3) 0.3962(3) 0.0978(15) Uani 1 1 d . . . H10D H 0.1952 0.9690 0.3621 0.147 Uiso 1 1 calc R . . H10E H 0.1634 0.9961 0.4424 0.147 Uiso 1 1 calc R . . H10F H 0.0114 0.9863 0.3737 0.147 Uiso 1 1 calc R . . C11B C 0.0439(5) 0.8231(4) 0.4778(2) 0.0986(15) Uani 1 1 d . . . H11D H -0.0764 0.8191 0.4650 0.148 Uiso 1 1 calc R . . H11E H 0.0771 0.8750 0.5161 0.148 Uiso 1 1 calc R . . H11F H 0.0888 0.7569 0.4964 0.148 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 N1A 0.071(2) 0.067(2) 0.067(2) 0.0038(18) 0.0147(16) -0.0009(16) C1A 0.084(3) 0.085(3) 0.058(2) 0.000(2) 0.018(2) -0.003(2) C2A 0.074(3) 0.074(3) 0.060(2) -0.010(2) 0.016(2) 0.002(2) C3A 0.058(2) 0.066(3) 0.056(2) -0.003(2) 0.0090(18) 0.0020(18) C4A 0.065(2) 0.062(2) 0.055(2) -0.0005(19) 0.0127(18) -0.0014(18) C5A 0.077(3) 0.073(3) 0.069(3) -0.007(2) 0.021(2) 0.003(2) C6A 0.085(3) 0.066(3) 0.082(3) -0.017(2) 0.019(2) 0.003(2) C7A 0.077(3) 0.069(3) 0.074(3) 0.009(2) 0.013(2) -0.004(2) C8A 0.070(3) 0.064(3) 0.059(2) -0.001(2) 0.0100(19) -0.0003(19) C9A 0.144(4) 0.095(4) 0.067(3) 0.000(2) 0.014(3) 0.017(3) C10A 0.106(3) 0.064(3) 0.096(3) 0.001(2) 0.021(3) -0.002(2) C11A 0.092(3) 0.089(3) 0.064(2) 0.009(2) 0.027(2) 0.001(2) N1B 0.076(2) 0.080(3) 0.069(2) -0.0108(19) 0.0135(17) 0.0093(18) C1B 0.088(3) 0.081(3) 0.063(2) -0.008(2) 0.020(2) -0.003(2) C2B 0.082(3) 0.063(3) 0.060(2) -0.0011(19) 0.011(2) -0.005(2) C3B 0.057(2) 0.077(3) 0.055(2) -0.009(2) 0.0049(18) 0.0034(19) C4B 0.062(2) 0.068(3) 0.053(2) -0.0013(19) 0.0142(18) 0.0003(18) C5B 0.072(3) 0.085(3) 0.063(2) 0.008(2) 0.017(2) 0.000(2) C6B 0.080(3) 0.070(3) 0.097(3) 0.018(3) 0.006(3) 0.000(2) C7B 0.077(3) 0.076(3) 0.089(3) -0.010(2) 0.021(2) 0.009(2) C8B 0.066(3) 0.068(3) 0.068(2) -0.003(2) 0.011(2) 0.001(2) C9B 0.176(5) 0.090(3) 0.059(3) 0.000(2) 0.001(3) -0.020(3) C10B 0.107(4) 0.072(3) 0.106(4) -0.018(3) 0.003(3) 0.014(3) C11B 0.101(3) 0.129(4) 0.070(3) -0.019(3) 0.028(2) 0.011(3) _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 N1A C3A 1.320(5) . ? N1A C10A 1.457(5) . ? N1A C11A 1.460(5) . ? C1A C9A 1.501(5) . ? C1A C8A 1.511(5) . ? C1A C2A 1.540(5) . ? C1A H1A 0.9900 . ? C2A C3A 1.517(5) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C3A C4A 1.388(5) . ? C4A C8A 1.428(5) . ? C4A C5A 1.432(5) . ? C5A C6A 1.375(5) . ? C5A H5A 0.9400 . ? C6A C7A 1.428(5) . ? C6A H6A 0.9400 . ? C7A C8A 1.361(5) . ? C7A H7A 0.9400 . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C9A H9A3 0.9700 . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C10A H10C 0.9700 . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C11A H11C 0.9700 . ? N1B C3B 1.327(5) . ? N1B C11B 1.451(5) . ? N1B C10B 1.457(5) . ? C1B C9B 1.502(5) . ? C1B C2B 1.520(5) . ? C1B C8B 1.527(5) . ? C1B H1B 0.9900 . ? C2B C3B 1.507(5) . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C3B C4B 1.385(5) . ? C4B C8B 1.419(5) . ? C4B C5B 1.432(5) . ? C5B C6B 1.368(6) . ? C5B H5B 0.9400 . ? C6B C7B 1.436(6) . ? C6B H6B 0.9400 . ? C7B C8B 1.349(5) . ? C7B H7B 0.9400 . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C9B H9B3 0.9700 . ? C10B H10D 0.9700 . ? C10B H10E 0.9700 . ? C10B H10F 0.9700 . ? C11B H11D 0.9700 . ? C11B H11E 0.9700 . ? C11B H11F 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 C3A N1A C10A 122.5(3) . . ? C3A N1A C11A 120.3(3) . . ? C10A N1A C11A 117.1(3) . . ? C9A C1A C8A 114.3(4) . . ? C9A C1A C2A 114.4(4) . . ? C8A C1A C2A 102.4(3) . . ? C9A C1A H1A 108.5 . . ? C8A C1A H1A 108.5 . . ? C2A C1A H1A 108.5 . . ? C3A C2A C1A 107.0(3) . . ? C3A C2A H2A1 110.3 . . ? C1A C2A H2A1 110.3 . . ? C3A C2A H2A2 110.3 . . ? C1A C2A H2A2 110.3 . . ? H2A1 C2A H2A2 108.6 . . ? N1A C3A C4A 129.0(3) . . ? N1A C3A C2A 121.7(3) . . ? C4A C3A C2A 109.2(3) . . ? C3A C4A C8A 110.0(3) . . ? C3A C4A C5A 142.5(4) . . ? C8A C4A C5A 107.5(3) . . ? C6A C5A C4A 106.3(3) . . ? C6A C5A H5A 126.8 . . ? C4A C5A H5A 126.8 . . ? C5A C6A C7A 109.9(3) . . ? C5A C6A H6A 125.0 . . ? C7A C6A H6A 125.0 . . ? C8A C7A C6A 107.5(4) . . ? C8A C7A H7A 126.2 . . ? C6A C7A H7A 126.2 . . ? C7A C8A C4A 108.6(3) . . ? C7A C8A C1A 139.9(4) . . ? C4A C8A C1A 111.5(3) . . ? C1A C9A H9A1 109.5 . . ? C1A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C1A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N1A C10A H10A 109.5 . . ? N1A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? N1A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? N1A C11A H11A 109.5 . . ? N1A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? N1A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C3B N1B C11B 119.9(4) . . ? C3B N1B C10B 122.7(4) . . ? C11B N1B C10B 117.2(4) . . ? C9B C1B C2B 112.0(4) . . ? C9B C1B C8B 113.6(4) . . ? C2B C1B C8B 103.0(3) . . ? C9B C1B H1B 109.4 . . ? C2B C1B H1B 109.4 . . ? C8B C1B H1B 109.4 . . ? C3B C2B C1B 106.2(3) . . ? C3B C2B H2B1 110.5 . . ? C1B C2B H2B1 110.5 . . ? C3B C2B H2B2 110.5 . . ? C1B C2B H2B2 110.5 . . ? H2B1 C2B H2B2 108.7 . . ? N1B C3B C4B 129.1(4) . . ? N1B C3B C2B 120.3(4) . . ? C4B C3B C2B 110.6(3) . . ? C3B C4B C8B 109.3(3) . . ? C3B C4B C5B 143.4(4) . . ? C8B C4B C5B 107.3(3) . . ? C6B C5B C4B 106.5(4) . . ? C6B C5B H5B 126.8 . . ? C4B C5B H5B 126.8 . . ? C5B C6B C7B 109.7(4) . . ? C5B C6B H6B 125.2 . . ? C7B C6B H6B 125.2 . . ? C8B C7B C6B 107.2(4) . . ? C8B C7B H7B 126.4 . . ? C6B C7B H7B 126.4 . . ? C7B C8B C4B 109.3(4) . . ? C7B C8B C1B 140.0(4) . . ? C4B C8B C1B 110.8(3) . . ? C1B C9B H9B1 109.5 . . ? C1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N1B C10B H10D 109.5 . . ? N1B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? N1B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? N1B C11B H11D 109.5 . . ? N1B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? N1B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 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 C9A C1A C2A C3A -123.4(4) . . . . ? C8A C1A C2A C3A 0.8(4) . . . . ? C10A N1A C3A C4A 179.0(4) . . . . ? C11A N1A C3A C4A 3.2(6) . . . . ? C10A N1A C3A C2A -2.9(5) . . . . ? C11A N1A C3A C2A -178.6(3) . . . . ? C1A C2A C3A N1A -178.9(3) . . . . ? C1A C2A C3A C4A -0.4(4) . . . . ? N1A C3A C4A C8A 178.1(3) . . . . ? C2A C3A C4A C8A -0.3(4) . . . . ? N1A C3A C4A C5A -0.2(8) . . . . ? C2A C3A C4A C5A -178.5(5) . . . . ? C3A C4A C5A C6A 178.5(5) . . . . ? C8A C4A C5A C6A 0.2(4) . . . . ? C4A C5A C6A C7A 0.2(5) . . . . ? C5A C6A C7A C8A -0.5(5) . . . . ? C6A C7A C8A C4A 0.6(5) . . . . ? C6A C7A C8A C1A -179.8(4) . . . . ? C3A C4A C8A C7A -179.4(3) . . . . ? C5A C4A C8A C7A -0.6(4) . . . . ? C3A C4A C8A C1A 0.8(4) . . . . ? C5A C4A C8A C1A 179.7(3) . . . . ? C9A C1A C8A C7A -56.3(7) . . . . ? C2A C1A C8A C7A 179.4(5) . . . . ? C9A C1A C8A C4A 123.3(4) . . . . ? C2A C1A C8A C4A -1.0(4) . . . . ? C9B C1B C2B C3B 118.8(4) . . . . ? C8B C1B C2B C3B -3.6(4) . . . . ? C11B N1B C3B C4B -3.3(6) . . . . ? C10B N1B C3B C4B -177.2(4) . . . . ? C11B N1B C3B C2B 178.6(3) . . . . ? C10B N1B C3B C2B 4.7(5) . . . . ? C1B C2B C3B N1B -178.7(3) . . . . ? C1B C2B C3B C4B 2.9(4) . . . . ? N1B C3B C4B C8B -179.0(4) . . . . ? C2B C3B C4B C8B -0.8(4) . . . . ? N1B C3B C4B C5B 0.5(8) . . . . ? C2B C3B C4B C5B 178.7(5) . . . . ? C3B C4B C5B C6B -179.1(5) . . . . ? C8B C4B C5B C6B 0.4(4) . . . . ? C4B C5B C6B C7B 0.2(5) . . . . ? C5B C6B C7B C8B -0.7(5) . . . . ? C6B C7B C8B C4B 1.0(5) . . . . ? C6B C7B C8B C1B -178.2(5) . . . . ? C3B C4B C8B C7B 178.8(3) . . . . ? C5B C4B C8B C7B -0.9(4) . . . . ? C3B C4B C8B C1B -1.7(4) . . . . ? C5B C4B C8B C1B 178.6(3) . . . . ? C9B C1B C8B C7B 61.2(7) . . . . ? C2B C1B C8B C7B -177.4(5) . . . . ? C9B C1B C8B C4B -118.0(4) . . . . ? C2B C1B C8B C4B 3.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.821 _diffrn_reflns_theta_full 66.12 _diffrn_measured_fraction_theta_full 0.821 _refine_diff_density_max 0.254 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.039 # Attachment '- 9a.CIF' data_erk5206 _database_code_depnum_ccdc_archive 'CCDC 778227' #TrackingRef '- 9a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 N2 Zr' _chemical_formula_weight 482.58 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' Cl Cl 0.1484 0.1585 '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 9.1539(2) _cell_length_b 10.5147(2) _cell_length_c 12.1510(3) _cell_angle_alpha 66.631(1) _cell_angle_beta 81.662(1) _cell_angle_gamma 84.245(2) _cell_volume 1061.08(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2458 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7998 _exptl_absorpt_correction_T_max 0.8920 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9087 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 27.85 _reflns_number_total 4883 _reflns_number_gt 4565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0424P)^2^+2.0667P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4883 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Zr Zr 0.19416(3) 0.17175(3) 0.26653(2) 0.03079(10) Uani 1 1 d . . . Cl1 Cl 0.00112(9) 0.07607(11) 0.20663(9) 0.0527(2) Uani 1 1 d . . . Cl2 Cl 0.29823(9) -0.04308(9) 0.41100(8) 0.0467(2) Uani 1 1 d . . . C1 C 0.3065(4) 0.4756(3) 0.2709(3) 0.0403(7) Uani 1 1 d . . . C2 C 0.4106(4) 0.3996(4) 0.3731(3) 0.0515(9) Uani 1 1 d . . . H2A H 0.5053 0.3722 0.3377 0.062 Uiso 1 1 calc R . . H2B H 0.4299 0.4633 0.4097 0.062 Uiso 1 1 calc R . . C3 C 0.3376(4) 0.2682(4) 0.4725(3) 0.0498(8) Uani 1 1 d . . . H3 H 0.3998 0.1846 0.4754 0.060 Uiso 1 1 calc R . . C4 C 0.1953(4) 0.2679(3) 0.4238(3) 0.0384(6) Uani 1 1 d . . . C5 C 0.0668(4) 0.1894(4) 0.4600(3) 0.0421(7) Uani 1 1 d . . . H5 H 0.0493 0.1086 0.5299 0.050 Uiso 1 1 calc R . . C6 C -0.0292(3) 0.2556(4) 0.3715(3) 0.0408(7) Uani 1 1 d . . . H6 H -0.1235 0.2267 0.3726 0.049 Uiso 1 1 calc R . . C7 C 0.0390(3) 0.3732(3) 0.2800(3) 0.0372(6) Uani 1 1 d . . . H7 H -0.0003 0.4341 0.2093 0.045 Uiso 1 1 calc R . . C8 C 0.1770(3) 0.3813(3) 0.3153(3) 0.0328(6) Uani 1 1 d . . . N1 N 0.2547(4) 0.6180(3) 0.2582(3) 0.0501(7) Uani 1 1 d . . . C9 C 0.3754(6) 0.7139(5) 0.2158(5) 0.0722(13) Uani 1 1 d . . . H9A H 0.3372 0.8045 0.2130 0.108 Uiso 1 1 calc R . . H9B H 0.4183 0.7216 0.1358 0.108 Uiso 1 1 calc R . . H9C H 0.4506 0.6791 0.2707 0.108 Uiso 1 1 calc R . . C10 C 0.1668(6) 0.6268(5) 0.3655(4) 0.0688(12) Uani 1 1 d . . . H10A H 0.2282 0.5984 0.4307 0.103 Uiso 1 1 calc R . . H10B H 0.0847 0.5663 0.3893 0.103 Uiso 1 1 calc R . . H10C H 0.1292 0.7216 0.3477 0.103 Uiso 1 1 calc R . . C11 C 0.3095(7) 0.2706(6) 0.5978(4) 0.0815(15) Uani 1 1 d . . . H11A H 0.2520 0.3544 0.5946 0.122 Uiso 1 1 calc R . . H11B H 0.4031 0.2687 0.6271 0.122 Uiso 1 1 calc R . . H11C H 0.2554 0.1901 0.6520 0.122 Uiso 1 1 calc R . . C1A C 0.3767(3) 0.4784(3) 0.1458(3) 0.0395(7) Uani 1 1 d . . . H1A H 0.4769 0.5151 0.1251 0.047 Uiso 1 1 calc R . . C2A C 0.2772(4) 0.5631(4) 0.0487(3) 0.0433(7) Uani 1 1 d . . . H2A1 H 0.2581 0.6593 0.0237 0.052 Uiso 1 1 calc R . . C3A C 0.2205(4) 0.4849(4) 0.0034(3) 0.0428(7) Uani 1 1 d . . . H3A H 0.1537 0.5171 -0.0549 0.051 Uiso 1 1 calc R . . C4A C 0.2781(3) 0.3404(3) 0.0583(3) 0.0362(6) Uani 1 1 d . . . C5A C 0.2958(3) 0.2144(4) 0.0386(3) 0.0383(7) Uani 1 1 d . . . C6A C 0.3971(3) 0.1288(3) 0.1212(3) 0.0380(6) Uani 1 1 d . . . H6A H 0.4204 0.0345 0.1375 0.046 Uiso 1 1 calc R . . C7A C 0.4571(3) 0.2071(3) 0.1751(3) 0.0377(6) Uani 1 1 d . . . C8A C 0.3798(3) 0.3365(3) 0.1390(3) 0.0350(6) Uani 1 1 d . . . N1A N 0.2317(3) 0.1804(3) -0.0395(3) 0.0484(7) Uani 1 1 d . . . C9A C 0.1139(5) 0.2700(5) -0.1017(4) 0.0631(11) Uani 1 1 d . . . H9A1 H 0.0407 0.2903 -0.0439 0.095 Uiso 1 1 calc R . . H9A2 H 0.0678 0.2241 -0.1421 0.095 Uiso 1 1 calc R . . H9A3 H 0.1540 0.3558 -0.1608 0.095 Uiso 1 1 calc R . . C10A C 0.2445(5) 0.0387(5) -0.0309(4) 0.0630(11) Uani 1 1 d . . . H10D H 0.3478 0.0073 -0.0324 0.095 Uiso 1 1 calc R . . H10E H 0.2042 0.0338 -0.0986 0.095 Uiso 1 1 calc R . . H10F H 0.1901 -0.0200 0.0440 0.095 Uiso 1 1 calc R . . C11A C 0.5865(3) 0.1571(4) 0.2481(3) 0.0474(8) Uani 1 1 d . . . H11D H 0.6730 0.2069 0.2014 0.071 Uiso 1 1 calc R . . H11E H 0.6061 0.0586 0.2679 0.071 Uiso 1 1 calc R . . H11F H 0.5635 0.1738 0.3219 0.071 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 Zr 0.02503(15) 0.03908(17) 0.02866(15) -0.01430(12) -0.00010(10) -0.00269(10) Cl1 0.0367(4) 0.0803(6) 0.0543(5) -0.0386(5) -0.0010(3) -0.0146(4) Cl2 0.0442(4) 0.0436(4) 0.0429(4) -0.0081(3) -0.0030(3) -0.0002(3) C1 0.0397(16) 0.0420(16) 0.0418(17) -0.0178(13) -0.0053(13) -0.0065(13) C2 0.0473(19) 0.061(2) 0.053(2) -0.0245(18) -0.0163(16) -0.0070(16) C3 0.056(2) 0.057(2) 0.0400(18) -0.0189(16) -0.0181(16) -0.0003(17) C4 0.0412(16) 0.0469(17) 0.0287(14) -0.0168(13) -0.0017(12) -0.0037(13) C5 0.0474(18) 0.0461(17) 0.0296(14) -0.0149(13) 0.0093(13) -0.0077(14) C6 0.0290(14) 0.0534(18) 0.0438(17) -0.0255(15) 0.0060(12) -0.0056(13) C7 0.0277(14) 0.0478(17) 0.0353(15) -0.0177(13) 0.0003(11) 0.0026(12) C8 0.0324(14) 0.0387(15) 0.0278(13) -0.0146(11) 0.0004(11) -0.0020(11) N1 0.0588(19) 0.0423(15) 0.0550(18) -0.0244(14) -0.0045(15) -0.0074(13) C9 0.080(3) 0.051(2) 0.090(3) -0.027(2) -0.012(3) -0.022(2) C10 0.095(3) 0.058(2) 0.063(3) -0.036(2) -0.002(2) -0.003(2) C11 0.104(4) 0.108(4) 0.043(2) -0.033(2) -0.026(2) -0.014(3) C1A 0.0312(14) 0.0422(16) 0.0401(16) -0.0115(13) 0.0023(12) -0.0071(12) C2A 0.0399(17) 0.0436(17) 0.0361(16) -0.0070(13) 0.0018(13) -0.0001(13) C3A 0.0377(16) 0.0527(19) 0.0292(14) -0.0094(13) -0.0020(12) 0.0067(14) C4A 0.0285(13) 0.0479(17) 0.0289(14) -0.0138(12) 0.0006(11) 0.0026(12) C5A 0.0303(14) 0.0523(18) 0.0317(14) -0.0187(13) 0.0029(11) 0.0017(13) C6A 0.0301(14) 0.0464(17) 0.0362(15) -0.0175(13) 0.0015(12) 0.0028(12) C7A 0.0263(13) 0.0472(17) 0.0339(15) -0.0120(13) 0.0012(11) 0.0006(12) C8A 0.0250(13) 0.0443(16) 0.0344(14) -0.0148(12) -0.0003(11) -0.0028(11) N1A 0.0485(16) 0.0667(19) 0.0388(15) -0.0311(14) -0.0085(12) 0.0084(14) C9A 0.063(2) 0.087(3) 0.053(2) -0.042(2) -0.027(2) 0.022(2) C10A 0.058(2) 0.082(3) 0.070(3) -0.054(2) -0.014(2) 0.015(2) C11A 0.0289(15) 0.059(2) 0.0496(19) -0.0168(16) -0.0067(14) 0.0034(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 Cl1 2.4444(9) . ? Zr C8A 2.447(3) . ? Zr Cl2 2.4493(8) . ? Zr C7 2.477(3) . ? Zr C8 2.484(3) . ? Zr C4 2.493(3) . ? Zr C7A 2.499(3) . ? Zr C6A 2.507(3) . ? Zr C4A 2.507(3) . ? Zr C6 2.522(3) . ? Zr C5 2.536(3) . ? Zr C5A 2.662(3) . ? C1 N1 1.479(4) . ? C1 C8 1.518(4) . ? C1 C1A 1.552(5) . ? C1 C2 1.579(5) . ? C2 C3 1.562(5) . ? C3 C4 1.507(5) . ? C3 C11 1.517(5) . ? C4 C8 1.401(4) . ? C4 C5 1.420(5) . ? C5 C6 1.404(5) . ? C6 C7 1.421(5) . ? C7 C8 1.413(4) . ? N1 C10 1.460(5) . ? N1 C9 1.466(5) . ? C1A C8A 1.524(4) . ? C1A C2A 1.527(5) . ? C2A C3A 1.332(5) . ? C3A C4A 1.472(4) . ? C4A C5A 1.427(5) . ? C4A C8A 1.434(4) . ? C5A N1A 1.358(4) . ? C5A C6A 1.436(4) . ? C6A C7A 1.425(5) . ? C7A C8A 1.403(4) . ? C7A C11A 1.508(4) . ? N1A C10A 1.445(5) . ? N1A C9A 1.446(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 Cl1 Zr C8A 128.95(7) . . ? Cl1 Zr Cl2 99.45(3) . . ? C8A Zr Cl2 113.83(7) . . ? Cl1 Zr C7 95.12(8) . . ? C8A Zr C7 87.30(10) . . ? Cl2 Zr C7 135.64(8) . . ? Cl1 Zr C8 128.18(7) . . ? C8A Zr C8 68.64(10) . . ? Cl2 Zr C8 117.34(7) . . ? C7 Zr C8 33.10(10) . . ? Cl1 Zr C4 132.95(8) . . ? C8A Zr C4 88.66(10) . . ? Cl2 Zr C4 85.93(8) . . ? C7 Zr C4 54.63(10) . . ? C8 Zr C4 32.70(10) . . ? Cl1 Zr C7A 128.01(8) . . ? C8A Zr C7A 32.94(10) . . ? Cl2 Zr C7A 83.37(7) . . ? C7 Zr C7A 118.78(11) . . ? C8 Zr C7A 93.17(10) . . ? C4 Zr C7A 99.02(11) . . ? Cl1 Zr C6A 95.23(8) . . ? C8A Zr C6A 54.43(11) . . ? Cl2 Zr C6A 83.25(8) . . ? C7 Zr C6A 136.84(11) . . ? C8 Zr C6A 122.71(10) . . ? C4 Zr C6A 131.75(11) . . ? C7A Zr C6A 33.08(11) . . ? Cl1 Zr C4A 95.86(8) . . ? C8A Zr C4A 33.61(10) . . ? Cl2 Zr C4A 135.39(7) . . ? C7 Zr C4A 83.62(10) . . ? C8 Zr C4A 83.02(10) . . ? C4 Zr C4A 112.74(11) . . ? C7A Zr C4A 54.76(10) . . ? C6A Zr C4A 53.68(10) . . ? Cl1 Zr C6 80.90(8) . . ? C8A Zr C6 119.32(11) . . ? Cl2 Zr C6 109.15(8) . . ? C7 Zr C6 33.01(10) . . ? C8 Zr C6 54.13(10) . . ? C4 Zr C6 53.78(10) . . ? C7A Zr C6 147.29(11) . . ? C6A Zr C6 167.42(11) . . ? C4A Zr C6 114.54(11) . . ? Cl1 Zr C5 101.39(8) . . ? C8A Zr C5 120.32(11) . . ? Cl2 Zr C5 81.39(8) . . ? C7 Zr C5 54.64(11) . . ? C8 Zr C5 54.37(10) . . ? C4 Zr C5 32.79(10) . . ? C7A Zr C5 130.04(11) . . ? C6A Zr C5 158.96(11) . . ? C4A Zr C5 135.73(11) . . ? C6 Zr C5 32.24(11) . . ? Cl1 Zr C5A 78.16(7) . . ? C8A Zr C5A 54.13(10) . . ? Cl2 Zr C5A 112.63(7) . . ? C7 Zr C5A 111.30(10) . . ? C8 Zr C5A 114.80(10) . . ? C4 Zr C5A 142.31(11) . . ? C7A Zr C5A 54.08(10) . . ? C6A Zr C5A 32.09(9) . . ? C4A Zr C5A 31.86(10) . . ? C6 Zr C5A 135.60(10) . . ? C5 Zr C5A 165.94(11) . . ? N1 C1 C8 110.0(3) . . ? N1 C1 C1A 109.0(3) . . ? C8 C1 C1A 108.9(3) . . ? N1 C1 C2 114.8(3) . . ? C8 C1 C2 101.2(3) . . ? C1A C1 C2 112.7(3) . . ? C3 C2 C1 110.7(3) . . ? C4 C3 C11 111.6(4) . . ? C4 C3 C2 102.1(3) . . ? C11 C3 C2 114.8(4) . . ? C8 C4 C5 108.8(3) . . ? C8 C4 C3 113.0(3) . . ? C5 C4 C3 138.1(3) . . ? C8 C4 Zr 73.29(17) . . ? C5 C4 Zr 75.26(18) . . ? C3 C4 Zr 120.0(2) . . ? C6 C5 C4 106.8(3) . . ? C6 C5 Zr 73.33(18) . . ? C4 C5 Zr 71.95(17) . . ? C5 C6 C7 109.1(3) . . ? C5 C6 Zr 74.43(18) . . ? C7 C6 Zr 71.76(17) . . ? C8 C7 C6 107.0(3) . . ? C8 C7 Zr 73.71(17) . . ? C6 C7 Zr 75.23(18) . . ? C4 C8 C7 108.3(3) . . ? C4 C8 C1 113.1(3) . . ? C7 C8 C1 138.7(3) . . ? C4 C8 Zr 74.01(18) . . ? C7 C8 Zr 73.19(18) . . ? C1 C8 Zr 118.5(2) . . ? C10 N1 C9 111.0(3) . . ? C10 N1 C1 114.4(3) . . ? C9 N1 C1 112.4(3) . . ? C8A C1A C2A 100.9(3) . . ? C8A C1A C1 112.1(3) . . ? C2A C1A C1 110.5(3) . . ? C3A C2A C1A 112.3(3) . . ? C2A C3A C4A 109.8(3) . . ? C5A C4A C8A 109.3(3) . . ? C5A C4A C3A 141.1(3) . . ? C8A C4A C3A 107.3(3) . . ? C5A C4A Zr 80.07(18) . . ? C8A C4A Zr 70.87(17) . . ? C3A C4A Zr 125.1(2) . . ? N1A C5A C4A 128.6(3) . . ? N1A C5A C6A 126.9(3) . . ? C4A C5A C6A 104.5(3) . . ? N1A C5A Zr 127.3(2) . . ? C4A C5A Zr 68.07(16) . . ? C6A C5A Zr 67.98(16) . . ? C7A C6A C5A 110.5(3) . . ? C7A C6A Zr 73.15(17) . . ? C5A C6A Zr 79.94(17) . . ? C8A C7A C6A 106.5(3) . . ? C8A C7A C11A 129.3(3) . . ? C6A C7A C11A 124.1(3) . . ? C8A C7A Zr 71.49(16) . . ? C6A C7A Zr 73.77(17) . . ? C11A C7A Zr 123.3(2) . . ? C7A C8A C4A 108.5(3) . . ? C7A C8A C1A 141.9(3) . . ? C4A C8A C1A 109.2(3) . . ? C7A C8A Zr 75.57(18) . . ? C4A C8A Zr 75.51(17) . . ? C1A C8A Zr 119.28(19) . . ? C5A N1A C10A 119.6(3) . . ? C5A N1A C9A 119.3(3) . . ? C10A N1A C9A 118.0(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 N1 C1 C2 C3 117.2(3) . . . . ? C8 C1 C2 C3 -1.2(4) . . . . ? C1A C1 C2 C3 -117.3(3) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? C1 C2 C3 C11 -119.1(4) . . . . ? C11 C3 C4 C8 121.1(4) . . . . ? C2 C3 C4 C8 -2.0(4) . . . . ? C11 C3 C4 C5 -53.7(6) . . . . ? C2 C3 C4 C5 -176.8(4) . . . . ? C11 C3 C4 Zr -155.5(3) . . . . ? C2 C3 C4 Zr 81.3(3) . . . . ? Cl1 Zr C4 C8 -96.51(18) . . . . ? C8A Zr C4 C8 50.36(18) . . . . ? Cl2 Zr C4 C8 164.36(18) . . . . ? C7 Zr C4 C8 -37.27(17) . . . . ? C7A Zr C4 C8 81.75(19) . . . . ? C6A Zr C4 C8 87.2(2) . . . . ? C4A Zr C4 C8 26.3(2) . . . . ? C6 Zr C4 C8 -78.3(2) . . . . ? C5 Zr C4 C8 -115.2(3) . . . . ? C5A Zr C4 C8 41.8(3) . . . . ? Cl1 Zr C4 C5 18.7(2) . . . . ? C8A Zr C4 C5 165.6(2) . . . . ? Cl2 Zr C4 C5 -80.40(19) . . . . ? C7 Zr C4 C5 78.0(2) . . . . ? C8 Zr C4 C5 115.2(3) . . . . ? C7A Zr C4 C5 -163.0(2) . . . . ? C6A Zr C4 C5 -157.60(19) . . . . ? C4A Zr C4 C5 141.53(19) . . . . ? C6 Zr C4 C5 36.98(19) . . . . ? C5A Zr C4 C5 157.01(19) . . . . ? Cl1 Zr C4 C3 156.2(2) . . . . ? C8A Zr C4 C3 -56.9(3) . . . . ? Cl2 Zr C4 C3 57.1(3) . . . . ? C7 Zr C4 C3 -144.5(3) . . . . ? C8 Zr C4 C3 -107.3(3) . . . . ? C7A Zr C4 C3 -25.5(3) . . . . ? C6A Zr C4 C3 -20.1(3) . . . . ? C4A Zr C4 C3 -81.0(3) . . . . ? C6 Zr C4 C3 174.5(3) . . . . ? C5 Zr C4 C3 137.5(4) . . . . ? C5A Zr C4 C3 -65.5(3) . . . . ? C8 C4 C5 C6 0.7(4) . . . . ? C3 C4 C5 C6 175.6(4) . . . . ? Zr C4 C5 C6 -65.5(2) . . . . ? C8 C4 C5 Zr 66.2(2) . . . . ? C3 C4 C5 Zr -118.8(4) . . . . ? Cl1 Zr C5 C6 -51.6(2) . . . . ? C8A Zr C5 C6 97.8(2) . . . . ? Cl2 Zr C5 C6 -149.5(2) . . . . ? C7 Zr C5 C6 36.64(19) . . . . ? C8 Zr C5 C6 77.6(2) . . . . ? C4 Zr C5 C6 114.6(3) . . . . ? C7A Zr C5 C6 136.7(2) . . . . ? C6A Zr C5 C6 166.9(3) . . . . ? C4A Zr C5 C6 59.3(3) . . . . ? C5A Zr C5 C6 35.1(5) . . . . ? Cl1 Zr C5 C4 -166.13(18) . . . . ? C8A Zr C5 C4 -16.7(2) . . . . ? Cl2 Zr C5 C4 95.89(19) . . . . ? C7 Zr C5 C4 -77.9(2) . . . . ? C8 Zr C5 C4 -36.97(18) . . . . ? C7A Zr C5 C4 22.1(3) . . . . ? C6A Zr C5 C4 52.4(4) . . . . ? C4A Zr C5 C4 -55.3(3) . . . . ? C6 Zr C5 C4 -114.6(3) . . . . ? C5A Zr C5 C4 -79.4(5) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? Zr C5 C6 C7 -63.9(2) . . . . ? C4 C5 C6 Zr 64.6(2) . . . . ? Cl1 Zr C6 C5 129.0(2) . . . . ? C8A Zr C6 C5 -101.2(2) . . . . ? Cl2 Zr C6 C5 32.0(2) . . . . ? C7 Zr C6 C5 -116.7(3) . . . . ? C8 Zr C6 C5 -78.4(2) . . . . ? C4 Zr C6 C5 -37.63(19) . . . . ? C7A Zr C6 C5 -76.3(3) . . . . ? C6A Zr C6 C5 -158.1(4) . . . . ? C4A Zr C6 C5 -138.72(19) . . . . ? C5A Zr C6 C5 -168.47(18) . . . . ? Cl1 Zr C6 C7 -114.35(19) . . . . ? C8A Zr C6 C7 15.5(2) . . . . ? Cl2 Zr C6 C7 148.73(17) . . . . ? C8 Zr C6 C7 38.31(17) . . . . ? C4 Zr C6 C7 79.1(2) . . . . ? C7A Zr C6 C7 40.4(3) . . . . ? C6A Zr C6 C7 -41.4(6) . . . . ? C4A Zr C6 C7 -22.0(2) . . . . ? C5 Zr C6 C7 116.7(3) . . . . ? C5A Zr C6 C7 -51.8(2) . . . . ? C5 C6 C7 C8 -1.8(4) . . . . ? Zr C6 C7 C8 -67.4(2) . . . . ? C5 C6 C7 Zr 65.6(2) . . . . ? Cl1 Zr C7 C8 177.65(16) . . . . ? C8A Zr C7 C8 -53.47(18) . . . . ? Cl2 Zr C7 C8 68.5(2) . . . . ? C4 Zr C7 C8 36.81(17) . . . . ? C7A Zr C7 C8 -43.4(2) . . . . ? C6A Zr C7 C8 -79.1(2) . . . . ? C4A Zr C7 C8 -87.00(18) . . . . ? C6 Zr C7 C8 113.1(3) . . . . ? C5 Zr C7 C8 77.31(19) . . . . ? C5A Zr C7 C8 -103.08(18) . . . . ? Cl1 Zr C7 C6 64.58(18) . . . . ? C8A Zr C7 C6 -166.5(2) . . . . ? Cl2 Zr C7 C6 -44.5(2) . . . . ? C8 Zr C7 C6 -113.1(3) . . . . ? C4 Zr C7 C6 -76.3(2) . . . . ? C7A Zr C7 C6 -156.44(18) . . . . ? C6A Zr C7 C6 167.84(18) . . . . ? C4A Zr C7 C6 159.9(2) . . . . ? C5 Zr C7 C6 -35.77(19) . . . . ? C5A Zr C7 C6 143.84(18) . . . . ? C5 C4 C8 C7 -1.8(4) . . . . ? C3 C4 C8 C7 -178.2(3) . . . . ? Zr C4 C8 C7 65.7(2) . . . . ? C5 C4 C8 C1 177.8(3) . . . . ? C3 C4 C8 C1 1.4(4) . . . . ? Zr C4 C8 C1 -114.7(2) . . . . ? C5 C4 C8 Zr -67.5(2) . . . . ? C3 C4 C8 Zr 116.1(3) . . . . ? C6 C7 C8 C4 2.2(3) . . . . ? Zr C7 C8 C4 -66.2(2) . . . . ? C6 C7 C8 C1 -177.2(4) . . . . ? Zr C7 C8 C1 114.3(4) . . . . ? C6 C7 C8 Zr 68.5(2) . . . . ? N1 C1 C8 C4 -121.9(3) . . . . ? C1A C1 C8 C4 118.8(3) . . . . ? C2 C1 C8 C4 -0.1(4) . . . . ? N1 C1 C8 C7 57.5(5) . . . . ? C1A C1 C8 C7 -61.8(5) . . . . ? C2 C1 C8 C7 179.3(4) . . . . ? N1 C1 C8 Zr 154.4(2) . . . . ? C1A C1 C8 Zr 35.0(3) . . . . ? C2 C1 C8 Zr -83.8(3) . . . . ? Cl1 Zr C8 C4 112.31(17) . . . . ? C8A Zr C8 C4 -124.2(2) . . . . ? Cl2 Zr C8 C4 -17.6(2) . . . . ? C7 Zr C8 C4 115.3(3) . . . . ? C7A Zr C8 C4 -101.79(19) . . . . ? C6A Zr C8 C4 -117.68(19) . . . . ? C4A Zr C8 C4 -155.70(19) . . . . ? C6 Zr C8 C4 77.1(2) . . . . ? C5 Zr C8 C4 37.06(18) . . . . ? C5A Zr C8 C4 -153.34(17) . . . . ? Cl1 Zr C8 C7 -3.0(2) . . . . ? C8A Zr C8 C7 120.47(19) . . . . ? Cl2 Zr C8 C7 -132.90(16) . . . . ? C4 Zr C8 C7 -115.3(3) . . . . ? C7A Zr C8 C7 142.93(18) . . . . ? C6A Zr C8 C7 127.04(18) . . . . ? C4A Zr C8 C7 89.02(18) . . . . ? C6 Zr C8 C7 -38.20(18) . . . . ? C5 Zr C8 C7 -78.22(19) . . . . ? C5A Zr C8 C7 91.37(18) . . . . ? Cl1 Zr C8 C1 -139.75(19) . . . . ? C8A Zr C8 C1 -16.3(2) . . . . ? Cl2 Zr C8 C1 90.3(2) . . . . ? C7 Zr C8 C1 -136.8(3) . . . . ? C4 Zr C8 C1 107.9(3) . . . . ? C7A Zr C8 C1 6.2(2) . . . . ? C6A Zr C8 C1 -9.7(3) . . . . ? C4A Zr C8 C1 -47.8(2) . . . . ? C6 Zr C8 C1 -175.0(3) . . . . ? C5 Zr C8 C1 145.0(3) . . . . ? C5A Zr C8 C1 -45.4(2) . . . . ? C8 C1 N1 C10 52.1(4) . . . . ? C1A C1 N1 C10 171.4(3) . . . . ? C2 C1 N1 C10 -61.2(4) . . . . ? C8 C1 N1 C9 179.8(3) . . . . ? C1A C1 N1 C9 -60.9(4) . . . . ? C2 C1 N1 C9 66.5(4) . . . . ? N1 C1 C1A C8A -158.5(3) . . . . ? C8 C1 C1A C8A -38.5(3) . . . . ? C2 C1 C1A C8A 72.9(3) . . . . ? N1 C1 C1A C2A -46.8(3) . . . . ? C8 C1 C1A C2A 73.2(3) . . . . ? C2 C1 C1A C2A -175.4(3) . . . . ? C8A C1A C2A C3A 5.7(3) . . . . ? C1 C1A C2A C3A -113.0(3) . . . . ? C1A C2A C3A C4A -2.6(4) . . . . ? C2A C3A C4A C5A -161.1(4) . . . . ? C2A C3A C4A C8A -1.9(4) . . . . ? C2A C3A C4A Zr 76.5(3) . . . . ? Cl1 Zr C4A C5A -56.22(17) . . . . ? C8A Zr C4A C5A 114.5(3) . . . . ? Cl2 Zr C4A C5A 53.6(2) . . . . ? C7 Zr C4A C5A -150.73(19) . . . . ? C8 Zr C4A C5A 175.94(18) . . . . ? C4 Zr C4A C5A 161.99(17) . . . . ? C7A Zr C4A C5A 77.05(19) . . . . ? C6A Zr C4A C5A 35.98(17) . . . . ? C6 Zr C4A C5A -138.87(17) . . . . ? C5 Zr C4A C5A -169.15(17) . . . . ? Cl1 Zr C4A C8A -170.76(17) . . . . ? Cl2 Zr C4A C8A -60.9(2) . . . . ? C7 Zr C4A C8A 94.72(19) . . . . ? C8 Zr C4A C8A 61.40(18) . . . . ? C4 Zr C4A C8A 47.4(2) . . . . ? C7A Zr C4A C8A -37.50(18) . . . . ? C6A Zr C4A C8A -78.57(19) . . . . ? C6 Zr C4A C8A 106.59(18) . . . . ? C5 Zr C4A C8A 76.3(2) . . . . ? C5A Zr C4A C8A -114.5(3) . . . . ? Cl1 Zr C4A C3A 91.2(3) . . . . ? C8A Zr C4A C3A -98.0(3) . . . . ? Cl2 Zr C4A C3A -159.0(2) . . . . ? C7 Zr C4A C3A -3.3(3) . . . . ? C8 Zr C4A C3A -36.6(3) . . . . ? C4 Zr C4A C3A -50.6(3) . . . . ? C7A Zr C4A C3A -135.5(3) . . . . ? C6A Zr C4A C3A -176.6(3) . . . . ? C6 Zr C4A C3A 8.6(3) . . . . ? C5 Zr C4A C3A -21.7(3) . . . . ? C5A Zr C4A C3A 147.4(4) . . . . ? C8A C4A C5A N1A -173.4(3) . . . . ? C3A C4A C5A N1A -14.5(6) . . . . ? Zr C4A C5A N1A 121.0(3) . . . . ? C8A C4A C5A C6A 7.0(3) . . . . ? C3A C4A C5A C6A 165.9(4) . . . . ? Zr C4A C5A C6A -58.6(2) . . . . ? C8A C4A C5A Zr 65.6(2) . . . . ? C3A C4A C5A Zr -135.5(4) . . . . ? Cl1 Zr C5A N1A -0.2(3) . . . . ? C8A Zr C5A N1A -161.0(3) . . . . ? Cl2 Zr C5A N1A 95.2(3) . . . . ? C7 Zr C5A N1A -91.2(3) . . . . ? C8 Zr C5A N1A -127.0(3) . . . . ? C4 Zr C5A N1A -150.4(3) . . . . ? C7A Zr C5A N1A 158.0(3) . . . . ? C6A Zr C5A N1A 120.4(4) . . . . ? C4A Zr C5A N1A -122.6(4) . . . . ? C6 Zr C5A N1A -63.8(3) . . . . ? C5 Zr C5A N1A -89.8(5) . . . . ? Cl1 Zr C5A C4A 122.35(17) . . . . ? C8A Zr C5A C4A -38.42(17) . . . . ? Cl2 Zr C5A C4A -142.23(16) . . . . ? C7 Zr C5A C4A 31.4(2) . . . . ? C8 Zr C5A C4A -4.4(2) . . . . ? C4 Zr C5A C4A -27.8(3) . . . . ? C7A Zr C5A C4A -79.39(19) . . . . ? C6A Zr C5A C4A -117.0(3) . . . . ? C6 Zr C5A C4A 58.8(2) . . . . ? C5 Zr C5A C4A 32.7(5) . . . . ? Cl1 Zr C5A C6A -120.7(2) . . . . ? C8A Zr C5A C6A 78.6(2) . . . . ? Cl2 Zr C5A C6A -25.2(2) . . . . ? C7 Zr C5A C6A 148.43(19) . . . . ? C8 Zr C5A C6A 112.6(2) . . . . ? C4 Zr C5A C6A 89.2(2) . . . . ? C7A Zr C5A C6A 37.60(19) . . . . ? C4A Zr C5A C6A 117.0(3) . . . . ? C6 Zr C5A C6A 175.77(18) . . . . ? C5 Zr C5A C6A 149.7(4) . . . . ? N1A C5A C6A C7A 171.4(3) . . . . ? C4A C5A C6A C7A -9.0(3) . . . . ? Zr C5A C6A C7A -67.6(2) . . . . ? N1A C5A C6A Zr -121.0(3) . . . . ? C4A C5A C6A Zr 58.6(2) . . . . ? Cl1 Zr C6A C7A 172.87(17) . . . . ? C8A Zr C6A C7A 37.59(18) . . . . ? Cl2 Zr C6A C7A -88.20(17) . . . . ? C7 Zr C6A C7A 69.7(2) . . . . ? C8 Zr C6A C7A 30.1(2) . . . . ? C4 Zr C6A C7A -9.8(2) . . . . ? C4A Zr C6A C7A 79.4(2) . . . . ? C6 Zr C6A C7A 101.4(5) . . . . ? C5 Zr C6A C7A -44.9(4) . . . . ? C5A Zr C6A C7A 115.1(3) . . . . ? Cl1 Zr C6A C5A 57.72(19) . . . . ? C8A Zr C6A C5A -77.6(2) . . . . ? Cl2 Zr C6A C5A 156.65(19) . . . . ? C7 Zr C6A C5A -45.5(3) . . . . ? C8 Zr C6A C5A -85.1(2) . . . . ? C4 Zr C6A C5A -125.0(2) . . . . ? C7A Zr C6A C5A -115.1(3) . . . . ? C4A Zr C6A C5A -35.72(18) . . . . ? C6 Zr C6A C5A -13.7(6) . . . . ? C5 Zr C6A C5A -160.1(3) . . . . ? C5A C6A C7A C8A 7.6(3) . . . . ? Zr C6A C7A C8A -64.5(2) . . . . ? C5A C6A C7A C11A -168.4(3) . . . . ? Zr C6A C7A C11A 119.5(3) . . . . ? C5A C6A C7A Zr 72.1(2) . . . . ? Cl1 Zr C7A C8A 105.13(18) . . . . ? Cl2 Zr C7A C8A -158.04(18) . . . . ? C7 Zr C7A C8A -18.8(2) . . . . ? C8 Zr C7A C8A -40.86(19) . . . . ? C4 Zr C7A C8A -73.24(19) . . . . ? C6A Zr C7A C8A 114.2(3) . . . . ? C4A Zr C7A C8A 38.30(18) . . . . ? C6 Zr C7A C8A -42.6(3) . . . . ? C5 Zr C7A C8A -85.2(2) . . . . ? C5A Zr C7A C8A 77.7(2) . . . . ? Cl1 Zr C7A C6A -9.0(2) . . . . ? C8A Zr C7A C6A -114.2(3) . . . . ? Cl2 Zr C7A C6A 87.80(18) . . . . ? C7 Zr C7A C6A -132.97(18) . . . . ? C8 Zr C7A C6A -155.03(18) . . . . ? C4 Zr C7A C6A 172.59(18) . . . . ? C4A Zr C7A C6A -75.87(19) . . . . ? C6 Zr C7A C6A -156.7(2) . . . . ? C5 Zr C7A C6A 160.67(18) . . . . ? C5A Zr C7A C6A -36.43(18) . . . . ? Cl1 Zr C7A C11A -129.5(3) . . . . ? C8A Zr C7A C11A 125.4(4) . . . . ? Cl2 Zr C7A C11A -32.7(3) . . . . ? C7 Zr C7A C11A 106.6(3) . . . . ? C8 Zr C7A C11A 84.5(3) . . . . ? C4 Zr C7A C11A 52.1(3) . . . . ? C6A Zr C7A C11A -120.5(4) . . . . ? C4A Zr C7A C11A 163.7(3) . . . . ? C6 Zr C7A C11A 82.8(3) . . . . ? C5 Zr C7A C11A 40.2(3) . . . . ? C5A Zr C7A C11A -156.9(3) . . . . ? C6A C7A C8A C4A -3.0(3) . . . . ? C11A C7A C8A C4A 172.7(3) . . . . ? Zr C7A C8A C4A -69.0(2) . . . . ? C6A C7A C8A C1A -174.6(4) . . . . ? C11A C7A C8A C1A 1.1(6) . . . . ? Zr C7A C8A C1A 119.3(4) . . . . ? C6A C7A C8A Zr 66.0(2) . . . . ? C11A C7A C8A Zr -118.3(3) . . . . ? C5A C4A C8A C7A -2.6(3) . . . . ? C3A C4A C8A C7A -169.0(2) . . . . ? Zr C4A C8A C7A 69.0(2) . . . . ? C5A C4A C8A C1A 171.9(2) . . . . ? C3A C4A C8A C1A 5.6(3) . . . . ? Zr C4A C8A C1A -116.4(2) . . . . ? C5A C4A C8A Zr -71.7(2) . . . . ? C3A C4A C8A Zr 122.0(2) . . . . ? C2A C1A C8A C7A 165.0(4) . . . . ? C1 C1A C8A C7A -77.5(5) . . . . ? C2A C1A C8A C4A -6.7(3) . . . . ? C1 C1A C8A C4A 110.9(3) . . . . ? C2A C1A C8A Zr -90.5(2) . . . . ? C1 C1A C8A Zr 27.1(3) . . . . ? Cl1 Zr C8A C7A -102.04(18) . . . . ? Cl2 Zr C8A C7A 24.0(2) . . . . ? C7 Zr C8A C7A 163.57(19) . . . . ? C8 Zr C8A C7A 135.5(2) . . . . ? C4 Zr C8A C7A 108.92(19) . . . . ? C6A Zr C8A C7A -37.75(18) . . . . ? C4A Zr C8A C7A -113.9(3) . . . . ? C6 Zr C8A C7A 155.21(18) . . . . ? C5 Zr C8A C7A 117.9(2) . . . . ? C5A Zr C8A C7A -77.6(2) . . . . ? Cl1 Zr C8A C4A 11.9(2) . . . . ? Cl2 Zr C8A C4A 137.85(16) . . . . ? C7 Zr C8A C4A -82.54(18) . . . . ? C8 Zr C8A C4A -110.65(19) . . . . ? C4 Zr C8A C4A -137.19(19) . . . . ? C7A Zr C8A C4A 113.9(3) . . . . ? C6A Zr C8A C4A 76.14(19) . . . . ? C6 Zr C8A C4A -90.9(2) . . . . ? C5 Zr C8A C4A -128.21(18) . . . . ? C5A Zr C8A C4A 36.34(17) . . . . ? Cl1 Zr C8A C1A 116.1(2) . . . . ? Cl2 Zr C8A C1A -117.9(2) . . . . ? C7 Zr C8A C1A 21.7(2) . . . . ? C8 Zr C8A C1A -6.4(2) . . . . ? C4 Zr C8A C1A -33.0(2) . . . . ? C7A Zr C8A C1A -141.9(3) . . . . ? C6A Zr C8A C1A -179.7(3) . . . . ? C4A Zr C8A C1A 104.2(3) . . . . ? C6 Zr C8A C1A 13.3(3) . . . . ? C5 Zr C8A C1A -24.0(3) . . . . ? C5A Zr C8A C1A 140.5(3) . . . . ? C4A C5A N1A C10A -169.4(3) . . . . ? C6A C5A N1A C10A 10.1(5) . . . . ? Zr C5A N1A C10A -78.9(4) . . . . ? C4A C5A N1A C9A -9.7(5) . . . . ? C6A C5A N1A C9A 169.8(4) . . . . ? Zr C5A N1A C9A 80.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.749 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.081 # Attachment '- 10b.cif' data_erk5328 _database_code_depnum_ccdc_archive 'CCDC 778228' #TrackingRef '- 10b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H32 Cl2 N2 Zr' _chemical_formula_weight 510.64 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' Cl Cl 0.1484 0.1585 '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 P21/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 11.8693(2) _cell_length_b 14.3085(3) _cell_length_c 13.9687(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.501(2) _cell_angle_gamma 90.00 _cell_volume 2370.07(8) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5052 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8170 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15123 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 27.92 _reflns_number_total 5503 _reflns_number_gt 4679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0660P)^2^+5.5273P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5503 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1426 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Zr Zr 0.51204(3) 0.35856(2) 1.26462(3) 0.03329(13) Uani 1 1 d . . . Cl1 Cl 0.45022(9) 0.24587(7) 1.14313(7) 0.0459(2) Uani 1 1 d . . . Cl2 Cl 0.61860(9) 0.24980(8) 1.36832(8) 0.0485(3) Uani 1 1 d . . . N1A N 0.8565(3) 0.4306(3) 1.3976(3) 0.0459(8) Uani 1 1 d . . . C1A C 0.7911(3) 0.3226(3) 1.1572(3) 0.0383(8) Uani 1 1 d . . . C2A C 0.8588(4) 0.3358(3) 1.2507(3) 0.0410(8) Uani 1 1 d . . . H2A H 0.9258 0.3031 1.2663 0.049 Uiso 1 1 calc R . . C3A C 0.8136(3) 0.3990(3) 1.3094(3) 0.0380(8) Uani 1 1 d . . . C4A C 0.7103(3) 0.4351(3) 1.2612(3) 0.0374(8) Uani 1 1 d . . . C5A C 0.6263(4) 0.5054(3) 1.2660(3) 0.0445(9) Uani 1 1 d . . . H5A H 0.6157 0.5464 1.3173 0.053 Uiso 1 1 calc R . . C6A C 0.5611(4) 0.5017(3) 1.1780(3) 0.0467(10) Uani 1 1 d . . . H6A H 0.5002 0.5411 1.1608 0.056 Uiso 1 1 calc R . . C7A C 0.6029(3) 0.4292(3) 1.1208(3) 0.0417(9) Uani 1 1 d . . . H7A H 0.5750 0.4118 1.0594 0.050 Uiso 1 1 calc R . . C8A C 0.6939(3) 0.3880(3) 1.1728(3) 0.0366(8) Uani 1 1 d . . . C9A C 0.7559(4) 0.2200(3) 1.1399(3) 0.0484(10) Uani 1 1 d . . . H9A1 H 0.7152 0.1976 1.1941 0.073 Uiso 1 1 calc R . . H9A2 H 0.8226 0.1820 1.1325 0.073 Uiso 1 1 calc R . . H9A3 H 0.7077 0.2160 1.0821 0.073 Uiso 1 1 calc R . . C10A C 0.8575(4) 0.3566(3) 1.0718(3) 0.0495(10) Uani 1 1 d . . . H10A H 0.8110 0.3504 1.0133 0.074 Uiso 1 1 calc R . . H10B H 0.9252 0.3193 1.0670 0.074 Uiso 1 1 calc R . . H10C H 0.8780 0.4217 1.0813 0.074 Uiso 1 1 calc R . . C11A C 0.9515(4) 0.3788(4) 1.4374(3) 0.0564(12) Uani 1 1 d . . . H11A H 0.9299 0.3141 1.4464 0.085 Uiso 1 1 calc R . . H11B H 0.9757 0.4056 1.4986 0.085 Uiso 1 1 calc R . . H11C H 1.0130 0.3818 1.3939 0.085 Uiso 1 1 calc R . . C12A C 0.7791(4) 0.4692(4) 1.4643(3) 0.0554(11) Uani 1 1 d . . . H12A H 0.7429 0.5242 1.4364 0.083 Uiso 1 1 calc R . . H12B H 0.8202 0.4863 1.5233 0.083 Uiso 1 1 calc R . . H12C H 0.7223 0.4229 1.4780 0.083 Uiso 1 1 calc R . . N1B N 0.1937(3) 0.1889(3) 1.2637(3) 0.0584(10) Uani 1 1 d . . . C1B C 0.2278(4) 0.4376(3) 1.1866(3) 0.0434(9) Uani 1 1 d . . . C2B C 0.1772(4) 0.3406(3) 1.1827(3) 0.0467(10) Uani 1 1 d . . . H2B H 0.1220 0.3224 1.1361 0.056 Uiso 1 1 calc R . . C3B C 0.2180(3) 0.2826(3) 1.2514(3) 0.0430(9) Uani 1 1 d . . . C4B C 0.3028(3) 0.3350(3) 1.3102(3) 0.0401(8) Uani 1 1 d . . . C5B C 0.3720(4) 0.3298(4) 1.3932(3) 0.0495(10) Uani 1 1 d . . . H5B H 0.3827 0.2773 1.4330 0.059 Uiso 1 1 calc R . . C6B C 0.4227(4) 0.4179(4) 1.4062(3) 0.0524(11) Uani 1 1 d . . . H6B H 0.4745 0.4340 1.4563 0.063 Uiso 1 1 calc R . . C7B C 0.3836(4) 0.4785(3) 1.3323(3) 0.0481(10) Uani 1 1 d . . . H7B H 0.4021 0.5420 1.3253 0.058 Uiso 1 1 calc R . . C8B C 0.3111(3) 0.4252(3) 1.2708(3) 0.0374(8) Uani 1 1 d . . . C9B C 0.2802(5) 0.4640(4) 1.0921(3) 0.0583(12) Uani 1 1 d . . . H9B1 H 0.3382 0.4191 1.0777 0.087 Uiso 1 1 calc R . . H9B2 H 0.3132 0.5259 1.0977 0.087 Uiso 1 1 calc R . . H9B3 H 0.2222 0.4638 1.0409 0.087 Uiso 1 1 calc R . . C10B C 0.1378(4) 0.5110(3) 1.2102(4) 0.0572(12) Uani 1 1 d . . . H10D H 0.0768 0.5090 1.1617 0.086 Uiso 1 1 calc R . . H10E H 0.1716 0.5727 1.2113 0.086 Uiso 1 1 calc R . . H10F H 0.1085 0.4974 1.2724 0.086 Uiso 1 1 calc R . . C11B C 0.1110(5) 0.1503(4) 1.1959(6) 0.081(2) Uani 1 1 d . . . H11D H 0.0378 0.1776 1.2064 0.122 Uiso 1 1 calc R . . H11E H 0.1071 0.0831 1.2044 0.122 Uiso 1 1 calc R . . H11F H 0.1325 0.1642 1.1312 0.122 Uiso 1 1 calc R . . C12B C 0.1883(6) 0.1537(4) 1.3602(5) 0.085(2) Uani 1 1 d . . . H12D H 0.2526 0.1765 1.3987 0.128 Uiso 1 1 calc R . . H12E H 0.1894 0.0859 1.3591 0.128 Uiso 1 1 calc R . . H12F H 0.1192 0.1751 1.3877 0.128 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 Zr 0.0397(2) 0.02468(19) 0.0355(2) -0.00203(13) 0.00093(14) 0.00075(13) Cl1 0.0591(6) 0.0369(5) 0.0419(5) -0.0094(4) 0.0034(4) -0.0063(4) Cl2 0.0528(6) 0.0408(5) 0.0514(6) 0.0121(4) -0.0027(4) 0.0038(4) N1A 0.053(2) 0.0393(19) 0.0451(19) -0.0013(15) -0.0032(15) -0.0026(16) C1A 0.044(2) 0.0306(18) 0.041(2) 0.0002(15) 0.0027(16) 0.0035(16) C2A 0.044(2) 0.035(2) 0.044(2) 0.0031(16) 0.0006(16) 0.0049(16) C3A 0.043(2) 0.0271(18) 0.044(2) 0.0041(15) 0.0020(16) -0.0019(15) C4A 0.0413(19) 0.0241(17) 0.047(2) 0.0009(15) 0.0024(16) -0.0025(14) C5A 0.049(2) 0.0204(16) 0.064(3) -0.0054(16) 0.0008(19) 0.0014(16) C6A 0.046(2) 0.0261(18) 0.068(3) 0.0127(18) 0.0045(19) 0.0041(16) C7A 0.044(2) 0.0337(19) 0.047(2) 0.0110(17) 0.0009(17) 0.0002(16) C8A 0.042(2) 0.0269(17) 0.041(2) 0.0050(15) 0.0043(15) -0.0005(15) C9A 0.062(3) 0.034(2) 0.049(2) -0.0049(18) 0.000(2) 0.0059(19) C10A 0.049(2) 0.054(3) 0.046(2) 0.0014(19) 0.0036(18) 0.005(2) C11A 0.055(3) 0.062(3) 0.051(3) 0.007(2) -0.008(2) -0.003(2) C12A 0.064(3) 0.057(3) 0.046(2) -0.005(2) 0.008(2) -0.012(2) N1B 0.051(2) 0.0314(19) 0.093(3) 0.0031(19) 0.009(2) -0.0033(16) C1B 0.049(2) 0.033(2) 0.048(2) -0.0010(17) -0.0017(18) 0.0042(17) C2B 0.042(2) 0.034(2) 0.064(3) -0.0055(18) -0.0067(19) 0.0023(16) C3B 0.040(2) 0.033(2) 0.056(2) -0.0037(17) 0.0051(17) 0.0012(16) C4B 0.043(2) 0.036(2) 0.042(2) 0.0012(16) 0.0077(16) 0.0010(16) C5B 0.055(3) 0.057(3) 0.037(2) 0.0045(19) 0.0072(18) 0.003(2) C6B 0.056(3) 0.058(3) 0.043(2) -0.017(2) -0.0002(19) 0.008(2) C7B 0.045(2) 0.039(2) 0.061(3) -0.0186(19) 0.0045(19) 0.0028(18) C8B 0.0428(19) 0.0311(18) 0.0386(19) -0.0055(15) 0.0048(15) 0.0040(15) C9B 0.070(3) 0.054(3) 0.051(3) 0.012(2) -0.006(2) 0.008(2) C10B 0.052(3) 0.036(2) 0.082(3) -0.001(2) -0.005(2) 0.009(2) C11B 0.056(3) 0.036(3) 0.151(6) -0.028(3) -0.001(3) -0.003(2) C12B 0.105(5) 0.048(3) 0.106(5) 0.026(3) 0.039(4) -0.002(3) _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 Cl1 2.4309(10) . ? Zr C6B 2.437(4) . ? Zr Cl2 2.4413(11) . ? Zr C6A 2.461(4) . ? Zr C5A 2.500(4) . ? Zr C7B 2.508(4) . ? Zr C7A 2.532(4) . ? Zr C5B 2.534(4) . ? Zr C8B 2.574(4) . ? Zr C8A 2.593(4) . ? Zr C4A 2.598(4) . ? Zr C4B 2.612(4) . ? N1A C3A 1.388(5) . ? N1A C11A 1.441(6) . ? N1A C12A 1.446(6) . ? C1A C8A 1.509(5) . ? C1A C2A 1.515(6) . ? C1A C10A 1.537(6) . ? C1A C9A 1.542(6) . ? C2A C3A 1.348(6) . ? C2A H2A 0.9400 . ? C3A C4A 1.467(5) . ? C4A C8A 1.413(5) . ? C4A C5A 1.419(5) . ? C5A C6A 1.424(6) . ? C5A H5A 0.9400 . ? C6A C7A 1.412(6) . ? C6A H6A 0.9400 . ? C7A C8A 1.405(5) . ? C7A H7A 0.9400 . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C9A H9A3 0.9700 . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C10A H10C 0.9700 . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C11A H11C 0.9700 . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C12A H12C 0.9700 . ? N1B C3B 1.384(5) . ? N1B C12B 1.443(7) . ? N1B C11B 1.445(7) . ? C1B C2B 1.513(6) . ? C1B C8B 1.513(6) . ? C1B C9B 1.531(6) . ? C1B C10B 1.543(6) . ? C2B C3B 1.342(6) . ? C2B H2B 0.9400 . ? C3B C4B 1.476(6) . ? C4B C5B 1.393(6) . ? C4B C8B 1.409(6) . ? C5B C6B 1.406(7) . ? C5B H5B 0.9400 . ? C6B C7B 1.412(7) . ? C6B H6B 0.9400 . ? C7B C8B 1.413(6) . ? C7B H7B 0.9400 . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C9B H9B3 0.9700 . ? C10B H10D 0.9700 . ? C10B H10E 0.9700 . ? C10B H10F 0.9700 . ? C11B H11D 0.9700 . ? C11B H11E 0.9700 . ? C11B H11F 0.9700 . ? C12B H12D 0.9700 . ? C12B H12E 0.9700 . ? C12B H12F 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 Cl1 Zr C6B 131.98(13) . . ? Cl1 Zr Cl2 97.13(4) . . ? C6B Zr Cl2 88.46(12) . . ? Cl1 Zr C6A 106.22(12) . . ? C6B Zr C6A 103.29(17) . . ? Cl2 Zr C6A 133.98(11) . . ? Cl1 Zr C5A 135.21(11) . . ? C6B Zr C5A 87.50(16) . . ? Cl2 Zr C5A 105.32(10) . . ? C6A Zr C5A 33.35(15) . . ? Cl1 Zr C7B 123.16(10) . . ? C6B Zr C7B 33.14(16) . . ? Cl2 Zr C7B 121.37(12) . . ? C6A Zr C7B 77.09(15) . . ? C5A Zr C7B 76.15(14) . . ? Cl1 Zr C7A 80.62(10) . . ? C6B Zr C7A 136.08(17) . . ? Cl2 Zr C7A 119.85(10) . . ? C6A Zr C7A 32.81(14) . . ? C5A Zr C7A 54.60(15) . . ? C7B Zr C7A 108.22(15) . . ? Cl1 Zr C5B 101.52(12) . . ? C6B Zr C5B 32.78(16) . . ? Cl2 Zr C5B 79.33(11) . . ? C6A Zr C5B 131.33(15) . . ? C5A Zr C5B 120.25(15) . . ? C7B Zr C5B 54.25(16) . . ? C7A Zr C5B 160.52(14) . . ? Cl1 Zr C8B 90.99(9) . . ? C6B Zr C8B 53.64(14) . . ? Cl2 Zr C8B 132.33(9) . . ? C6A Zr C8B 87.00(13) . . ? C5A Zr C8B 101.05(13) . . ? C7B Zr C8B 32.24(13) . . ? C7A Zr C8B 107.81(13) . . ? C5B Zr C8B 53.05(14) . . ? Cl1 Zr C8A 89.69(9) . . ? C6B Zr C8A 138.25(15) . . ? Cl2 Zr C8A 88.64(9) . . ? C6A Zr C8A 53.25(13) . . ? C5A Zr C8A 53.43(13) . . ? C7B Zr C8A 127.46(14) . . ? C7A Zr C8A 31.78(12) . . ? C5B Zr C8A 164.41(14) . . ? C8B Zr C8A 138.50(12) . . ? Cl1 Zr C4A 120.85(9) . . ? C6B Zr C4A 107.13(15) . . ? Cl2 Zr C4A 80.41(9) . . ? C6A Zr C4A 53.56(13) . . ? C5A Zr C4A 32.25(12) . . ? C7B Zr C4A 106.52(13) . . ? C7A Zr C4A 53.09(13) . . ? C5B Zr C4A 134.78(14) . . ? C8B Zr C4A 133.30(13) . . ? C8A Zr C4A 31.60(12) . . ? Cl1 Zr C4B 79.84(10) . . ? C6B Zr C4B 52.78(15) . . ? Cl2 Zr C4B 104.27(10) . . ? C6A Zr C4B 118.37(13) . . ? C5A Zr C4B 128.88(13) . . ? C7B Zr C4B 52.87(14) . . ? C7A Zr C4B 133.42(13) . . ? C5B Zr C4B 31.36(14) . . ? C8B Zr C4B 31.51(12) . . ? C8A Zr C4B 164.21(13) . . ? C4A Zr C4B 158.48(13) . . ? C3A N1A C11A 115.1(4) . . ? C3A N1A C12A 118.5(4) . . ? C11A N1A C12A 117.1(4) . . ? C8A C1A C2A 100.3(3) . . ? C8A C1A C10A 109.6(3) . . ? C2A C1A C10A 111.0(3) . . ? C8A C1A C9A 114.1(3) . . ? C2A C1A C9A 112.6(3) . . ? C10A C1A C9A 109.0(3) . . ? C3A C2A C1A 113.5(4) . . ? C3A C2A H2A 123.3 . . ? C1A C2A H2A 123.3 . . ? C2A C3A N1A 128.2(4) . . ? C2A C3A C4A 107.7(4) . . ? N1A C3A C4A 124.0(4) . . ? C8A C4A C5A 108.0(4) . . ? C8A C4A C3A 108.3(3) . . ? C5A C4A C3A 143.4(4) . . ? C8A C4A Zr 74.0(2) . . ? C5A C4A Zr 70.1(2) . . ? C3A C4A Zr 125.6(3) . . ? C4A C5A C6A 106.8(4) . . ? C4A C5A Zr 77.7(2) . . ? C6A C5A Zr 71.8(2) . . ? C4A C5A H5A 126.6 . . ? C6A C5A H5A 126.6 . . ? Zr C5A H5A 116.1 . . ? C7A C6A C5A 108.9(4) . . ? C7A C6A Zr 76.3(2) . . ? C5A C6A Zr 74.8(2) . . ? C7A C6A H6A 125.5 . . ? C5A C6A H6A 125.5 . . ? Zr C6A H6A 115.4 . . ? C8A C7A C6A 107.3(4) . . ? C8A C7A Zr 76.5(2) . . ? C6A C7A Zr 70.9(2) . . ? C8A C7A H7A 126.4 . . ? C6A C7A H7A 126.4 . . ? Zr C7A H7A 118.3 . . ? C7A C8A C4A 108.9(4) . . ? C7A C8A C1A 139.6(4) . . ? C4A C8A C1A 110.2(3) . . ? C7A C8A Zr 71.7(2) . . ? C4A C8A Zr 74.4(2) . . ? C1A C8A Zr 129.0(2) . . ? C1A C9A H9A1 109.5 . . ? C1A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C1A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C1A C10A H10A 109.5 . . ? C1A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C1A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? N1A C11A H11A 109.5 . . ? N1A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? N1A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? N1A C12A H12A 109.5 . . ? N1A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? N1A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C3B N1B C12B 118.2(5) . . ? C3B N1B C11B 115.3(4) . . ? C12B N1B C11B 115.0(5) . . ? C2B C1B C8B 99.5(3) . . ? C2B C1B C9B 111.8(4) . . ? C8B C1B C9B 115.0(4) . . ? C2B C1B C10B 110.8(4) . . ? C8B C1B C10B 110.4(4) . . ? C9B C1B C10B 109.1(4) . . ? C3B C2B C1B 114.3(4) . . ? C3B C2B H2B 122.8 . . ? C1B C2B H2B 122.8 . . ? C2B C3B N1B 128.1(4) . . ? C2B C3B C4B 107.5(4) . . ? N1B C3B C4B 124.3(4) . . ? C5B C4B C8B 109.0(4) . . ? C5B C4B C3B 143.0(4) . . ? C8B C4B C3B 107.7(4) . . ? C5B C4B Zr 71.2(2) . . ? C8B C4B Zr 72.7(2) . . ? C3B C4B Zr 124.2(3) . . ? C4B C5B C6B 107.0(4) . . ? C4B C5B Zr 77.4(2) . . ? C6B C5B Zr 69.8(2) . . ? C4B C5B H5B 126.5 . . ? C6B C5B H5B 126.5 . . ? Zr C5B H5B 118.2 . . ? C5B C6B C7B 109.3(4) . . ? C5B C6B Zr 77.4(2) . . ? C7B C6B Zr 76.2(2) . . ? C5B C6B H6B 125.3 . . ? C7B C6B H6B 125.3 . . ? Zr C6B H6B 113.3 . . ? C6B C7B C8B 106.6(4) . . ? C6B C7B Zr 70.7(2) . . ? C8B C7B Zr 76.4(2) . . ? C6B C7B H7B 126.7 . . ? C8B C7B H7B 126.7 . . ? Zr C7B H7B 118.2 . . ? C4B C8B C7B 107.9(4) . . ? C4B C8B C1B 110.9(3) . . ? C7B C8B C1B 140.3(4) . . ? C4B C8B Zr 75.8(2) . . ? C7B C8B Zr 71.3(2) . . ? C1B C8B Zr 126.3(3) . . ? C1B C9B H9B1 109.5 . . ? C1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? C1B C10B H10D 109.5 . . ? C1B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C1B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? N1B C11B H11D 109.5 . . ? N1B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? N1B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? N1B C12B H12D 109.5 . . ? N1B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? N1B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 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 C8A C1A C2A C3A -1.9(4) . . . . ? C10A C1A C2A C3A 113.9(4) . . . . ? C9A C1A C2A C3A -123.6(4) . . . . ? C1A C2A C3A N1A -176.7(4) . . . . ? C1A C2A C3A C4A -0.1(5) . . . . ? C11A N1A C3A C2A -10.6(6) . . . . ? C12A N1A C3A C2A -156.6(4) . . . . ? C11A N1A C3A C4A 173.3(4) . . . . ? C12A N1A C3A C4A 27.3(6) . . . . ? C2A C3A C4A C8A 2.2(4) . . . . ? N1A C3A C4A C8A 179.0(4) . . . . ? C2A C3A C4A C5A -169.6(5) . . . . ? N1A C3A C4A C5A 7.2(8) . . . . ? C2A C3A C4A Zr 85.3(4) . . . . ? N1A C3A C4A Zr -97.9(4) . . . . ? Cl1 Zr C4A C8A 10.6(2) . . . . ? C6B Zr C4A C8A -171.4(2) . . . . ? Cl2 Zr C4A C8A 103.2(2) . . . . ? C6A Zr C4A C8A -77.3(2) . . . . ? C5A Zr C4A C8A -116.5(3) . . . . ? C7B Zr C4A C8A -136.8(2) . . . . ? C7A Zr C4A C8A -36.1(2) . . . . ? C5B Zr C4A C8A 167.6(2) . . . . ? C8B Zr C4A C8A -115.6(2) . . . . ? C4B Zr C4A C8A -152.1(3) . . . . ? Cl1 Zr C4A C5A 127.0(2) . . . . ? C6B Zr C4A C5A -55.0(3) . . . . ? Cl2 Zr C4A C5A -140.3(3) . . . . ? C6A Zr C4A C5A 39.1(3) . . . . ? C7B Zr C4A C5A -20.3(3) . . . . ? C7A Zr C4A C5A 80.4(3) . . . . ? C5B Zr C4A C5A -75.9(3) . . . . ? C8B Zr C4A C5A 0.9(3) . . . . ? C8A Zr C4A C5A 116.5(3) . . . . ? C4B Zr C4A C5A -35.7(5) . . . . ? Cl1 Zr C4A C3A -90.7(3) . . . . ? C6B Zr C4A C3A 87.3(3) . . . . ? Cl2 Zr C4A C3A 1.9(3) . . . . ? C6A Zr C4A C3A -178.6(4) . . . . ? C5A Zr C4A C3A 142.2(5) . . . . ? C7B Zr C4A C3A 121.9(3) . . . . ? C7A Zr C4A C3A -137.4(4) . . . . ? C5B Zr C4A C3A 66.3(4) . . . . ? C8B Zr C4A C3A 143.1(3) . . . . ? C8A Zr C4A C3A -101.3(4) . . . . ? C4B Zr C4A C3A 106.6(4) . . . . ? C8A C4A C5A C6A -1.7(4) . . . . ? C3A C4A C5A C6A 170.2(5) . . . . ? Zr C4A C5A C6A -66.5(3) . . . . ? C8A C4A C5A Zr 64.8(3) . . . . ? C3A C4A C5A Zr -123.4(6) . . . . ? Cl1 Zr C5A C4A -76.6(3) . . . . ? C6B Zr C5A C4A 128.4(3) . . . . ? Cl2 Zr C5A C4A 40.7(3) . . . . ? C6A Zr C5A C4A -112.6(4) . . . . ? C7B Zr C5A C4A 160.0(3) . . . . ? C7A Zr C5A C4A -75.3(3) . . . . ? C5B Zr C5A C4A 127.1(3) . . . . ? C8B Zr C5A C4A -179.4(2) . . . . ? C8A Zr C5A C4A -35.7(2) . . . . ? C4B Zr C5A C4A 164.1(2) . . . . ? Cl1 Zr C5A C6A 36.0(3) . . . . ? C6B Zr C5A C6A -119.0(3) . . . . ? Cl2 Zr C5A C6A 153.3(2) . . . . ? C7B Zr C5A C6A -87.5(3) . . . . ? C7A Zr C5A C6A 37.3(2) . . . . ? C5B Zr C5A C6A -120.3(3) . . . . ? C8B Zr C5A C6A -66.8(3) . . . . ? C8A Zr C5A C6A 76.8(3) . . . . ? C4A Zr C5A C6A 112.6(4) . . . . ? C4B Zr C5A C6A -83.4(3) . . . . ? C4A C5A C6A C7A 1.1(5) . . . . ? Zr C5A C6A C7A -69.4(3) . . . . ? C4A C5A C6A Zr 70.5(3) . . . . ? Cl1 Zr C6A C7A -40.1(3) . . . . ? C6B Zr C6A C7A 178.2(3) . . . . ? Cl2 Zr C6A C7A 77.3(3) . . . . ? C5A Zr C6A C7A 114.3(4) . . . . ? C7B Zr C6A C7A -161.3(3) . . . . ? C5B Zr C6A C7A -162.3(2) . . . . ? C8B Zr C6A C7A -130.3(3) . . . . ? C8A Zr C6A C7A 36.9(2) . . . . ? C4A Zr C6A C7A 76.6(3) . . . . ? C4B Zr C6A C7A -127.2(2) . . . . ? Cl1 Zr C6A C5A -154.5(2) . . . . ? C6B Zr C6A C5A 63.9(3) . . . . ? Cl2 Zr C6A C5A -37.0(3) . . . . ? C7B Zr C6A C5A 84.4(3) . . . . ? C7A Zr C6A C5A -114.3(4) . . . . ? C5B Zr C6A C5A 83.3(3) . . . . ? C8B Zr C6A C5A 115.4(2) . . . . ? C8A Zr C6A C5A -77.4(3) . . . . ? C4A Zr C6A C5A -37.8(2) . . . . ? C4B Zr C6A C5A 118.5(2) . . . . ? C5A C6A C7A C8A -0.1(5) . . . . ? Zr C6A C7A C8A -68.5(3) . . . . ? C5A C6A C7A Zr 68.4(3) . . . . ? Cl1 Zr C7A C8A -104.9(2) . . . . ? C6B Zr C7A C8A 111.5(3) . . . . ? Cl2 Zr C7A C8A -12.0(3) . . . . ? C6A Zr C7A C8A 114.0(4) . . . . ? C5A Zr C7A C8A 76.1(3) . . . . ? C7B Zr C7A C8A 133.2(2) . . . . ? C5B Zr C7A C8A 157.1(4) . . . . ? C8B Zr C7A C8A 167.1(2) . . . . ? C4A Zr C7A C8A 35.9(2) . . . . ? C4B Zr C7A C8A -171.1(2) . . . . ? Cl1 Zr C7A C6A 141.1(3) . . . . ? C6B Zr C7A C6A -2.5(4) . . . . ? Cl2 Zr C7A C6A -126.0(2) . . . . ? C5A Zr C7A C6A -37.9(2) . . . . ? C7B Zr C7A C6A 19.2(3) . . . . ? C5B Zr C7A C6A 43.1(6) . . . . ? C8B Zr C7A C6A 53.1(3) . . . . ? C8A Zr C7A C6A -114.0(4) . . . . ? C4A Zr C7A C6A -78.1(3) . . . . ? C4B Zr C7A C6A 74.9(3) . . . . ? C6A C7A C8A C4A -0.9(4) . . . . ? Zr C7A C8A C4A -65.6(3) . . . . ? C6A C7A C8A C1A -166.0(5) . . . . ? Zr C7A C8A C1A 129.3(5) . . . . ? C6A C7A C8A Zr 64.7(3) . . . . ? C5A C4A C8A C7A 1.6(4) . . . . ? C3A C4A C8A C7A -173.2(3) . . . . ? Zr C4A C8A C7A 63.9(3) . . . . ? C5A C4A C8A C1A 171.4(3) . . . . ? C3A C4A C8A C1A -3.5(4) . . . . ? Zr C4A C8A C1A -126.4(3) . . . . ? C5A C4A C8A Zr -62.2(3) . . . . ? C3A C4A C8A Zr 122.9(3) . . . . ? C2A C1A C8A C7A 168.2(5) . . . . ? C10A C1A C8A C7A 51.3(6) . . . . ? C9A C1A C8A C7A -71.3(6) . . . . ? C2A C1A C8A C4A 3.2(4) . . . . ? C10A C1A C8A C4A -113.7(4) . . . . ? C9A C1A C8A C4A 123.8(4) . . . . ? C2A C1A C8A Zr -82.7(4) . . . . ? C10A C1A C8A Zr 160.4(3) . . . . ? C9A C1A C8A Zr 37.9(5) . . . . ? Cl1 Zr C8A C7A 72.5(2) . . . . ? C6B Zr C8A C7A -104.2(3) . . . . ? Cl2 Zr C8A C7A 169.6(2) . . . . ? C6A Zr C8A C7A -38.2(3) . . . . ? C5A Zr C8A C7A -80.1(3) . . . . ? C7B Zr C8A C7A -60.7(3) . . . . ? C5B Zr C8A C7A -151.1(5) . . . . ? C8B Zr C8A C7A -18.6(3) . . . . ? C4A Zr C8A C7A -116.6(3) . . . . ? C4B Zr C8A C7A 24.4(6) . . . . ? Cl1 Zr C8A C4A -170.9(2) . . . . ? C6B Zr C8A C4A 12.4(3) . . . . ? Cl2 Zr C8A C4A -73.8(2) . . . . ? C6A Zr C8A C4A 78.4(3) . . . . ? C5A Zr C8A C4A 36.5(2) . . . . ? C7B Zr C8A C4A 55.8(3) . . . . ? C7A Zr C8A C4A 116.6(3) . . . . ? C5B Zr C8A C4A -34.6(6) . . . . ? C8B Zr C8A C4A 97.9(3) . . . . ? C4B Zr C8A C4A 140.9(4) . . . . ? Cl1 Zr C8A C1A -67.4(3) . . . . ? C6B Zr C8A C1A 115.9(4) . . . . ? Cl2 Zr C8A C1A 29.8(3) . . . . ? C6A Zr C8A C1A -178.0(4) . . . . ? C5A Zr C8A C1A 140.1(4) . . . . ? C7B Zr C8A C1A 159.4(3) . . . . ? C7A Zr C8A C1A -139.9(5) . . . . ? C5B Zr C8A C1A 69.0(6) . . . . ? C8B Zr C8A C1A -158.5(3) . . . . ? C4A Zr C8A C1A 103.6(4) . . . . ? C4B Zr C8A C1A -115.5(5) . . . . ? C8B C1B C2B C3B 1.8(5) . . . . ? C9B C1B C2B C3B 123.7(4) . . . . ? C10B C1B C2B C3B -114.4(4) . . . . ? C1B C2B C3B N1B -176.0(4) . . . . ? C1B C2B C3B C4B -0.3(5) . . . . ? C12B N1B C3B C2B -144.2(5) . . . . ? C11B N1B C3B C2B -2.5(7) . . . . ? C12B N1B C3B C4B 40.8(7) . . . . ? C11B N1B C3B C4B -177.6(4) . . . . ? C2B C3B C4B C5B 172.9(6) . . . . ? N1B C3B C4B C5B -11.2(9) . . . . ? C2B C3B C4B C8B -1.4(5) . . . . ? N1B C3B C4B C8B 174.5(4) . . . . ? C2B C3B C4B Zr -82.3(4) . . . . ? N1B C3B C4B Zr 93.7(5) . . . . ? Cl1 Zr C4B C5B 133.2(3) . . . . ? C6B Zr C4B C5B -38.5(3) . . . . ? Cl2 Zr C4B C5B 38.3(3) . . . . ? C6A Zr C4B C5B -123.8(3) . . . . ? C5A Zr C4B C5B -85.4(3) . . . . ? C7B Zr C4B C5B -80.4(3) . . . . ? C7A Zr C4B C5B -160.3(3) . . . . ? C8B Zr C4B C5B -117.8(4) . . . . ? C8A Zr C4B C5B -177.7(4) . . . . ? C4A Zr C4B C5B -61.9(5) . . . . ? Cl1 Zr C4B C8B -109.0(2) . . . . ? C6B Zr C4B C8B 79.3(3) . . . . ? Cl2 Zr C4B C8B 156.1(2) . . . . ? C6A Zr C4B C8B -6.0(3) . . . . ? C5A Zr C4B C8B 32.4(3) . . . . ? C7B Zr C4B C8B 37.4(2) . . . . ? C7A Zr C4B C8B -42.5(3) . . . . ? C5B Zr C4B C8B 117.8(4) . . . . ? C8A Zr C4B C8B -59.9(5) . . . . ? C4A Zr C4B C8B 56.0(4) . . . . ? Cl1 Zr C4B C3B -9.0(3) . . . . ? C6B Zr C4B C3B 179.4(4) . . . . ? Cl2 Zr C4B C3B -103.8(3) . . . . ? C6A Zr C4B C3B 94.1(4) . . . . ? C5A Zr C4B C3B 132.5(3) . . . . ? C7B Zr C4B C3B 137.4(4) . . . . ? C7A Zr C4B C3B 57.6(4) . . . . ? C5B Zr C4B C3B -142.1(5) . . . . ? C8B Zr C4B C3B 100.1(4) . . . . ? C8A Zr C4B C3B 40.2(6) . . . . ? C4A Zr C4B C3B 156.0(3) . . . . ? C8B C4B C5B C6B 0.7(5) . . . . ? C3B C4B C5B C6B -173.6(5) . . . . ? Zr C4B C5B C6B 64.0(3) . . . . ? C8B C4B C5B Zr -63.3(3) . . . . ? C3B C4B C5B Zr 122.4(6) . . . . ? Cl1 Zr C5B C4B -47.1(3) . . . . ? C6B Zr C5B C4B 113.7(4) . . . . ? Cl2 Zr C5B C4B -142.3(3) . . . . ? C6A Zr C5B C4B 76.9(3) . . . . ? C5A Zr C5B C4B 116.1(3) . . . . ? C7B Zr C5B C4B 75.6(3) . . . . ? C7A Zr C5B C4B 47.3(6) . . . . ? C8B Zr C5B C4B 35.3(2) . . . . ? C8A Zr C5B C4B 177.7(4) . . . . ? C4A Zr C5B C4B 152.9(2) . . . . ? Cl1 Zr C5B C6B -160.8(3) . . . . ? Cl2 Zr C5B C6B 104.0(3) . . . . ? C6A Zr C5B C6B -36.8(3) . . . . ? C5A Zr C5B C6B 2.4(3) . . . . ? C7B Zr C5B C6B -38.0(3) . . . . ? C7A Zr C5B C6B -66.4(5) . . . . ? C8B Zr C5B C6B -78.3(3) . . . . ? C8A Zr C5B C6B 64.0(6) . . . . ? C4A Zr C5B C6B 39.2(4) . . . . ? C4B Zr C5B C6B -113.7(4) . . . . ? C4B C5B C6B C7B 1.0(5) . . . . ? Zr C5B C6B C7B 70.2(3) . . . . ? C4B C5B C6B Zr -69.2(3) . . . . ? Cl1 Zr C6B C5B 25.7(3) . . . . ? Cl2 Zr C6B C5B -72.5(3) . . . . ? C6A Zr C6B C5B 152.5(3) . . . . ? C5A Zr C6B C5B -177.9(3) . . . . ? C7B Zr C6B C5B 113.9(4) . . . . ? C7A Zr C6B C5B 153.9(3) . . . . ? C8B Zr C6B C5B 76.4(3) . . . . ? C8A Zr C6B C5B -158.7(2) . . . . ? C4A Zr C6B C5B -152.0(3) . . . . ? C4B Zr C6B C5B 36.8(3) . . . . ? Cl1 Zr C6B C7B -88.2(3) . . . . ? Cl2 Zr C6B C7B 173.6(3) . . . . ? C6A Zr C6B C7B 38.6(3) . . . . ? C5A Zr C6B C7B 68.2(3) . . . . ? C7A Zr C6B C7B 40.0(4) . . . . ? C5B Zr C6B C7B -113.9(4) . . . . ? C8B Zr C6B C7B -37.5(2) . . . . ? C8A Zr C6B C7B 87.4(3) . . . . ? C4A Zr C6B C7B 94.1(3) . . . . ? C4B Zr C6B C7B -77.1(3) . . . . ? C5B C6B C7B C8B -2.4(5) . . . . ? Zr C6B C7B C8B 68.7(3) . . . . ? C5B C6B C7B Zr -71.1(3) . . . . ? Cl1 Zr C7B C6B 117.4(3) . . . . ? Cl2 Zr C7B C6B -7.5(3) . . . . ? C6A Zr C7B C6B -141.5(3) . . . . ? C5A Zr C7B C6B -107.2(3) . . . . ? C7A Zr C7B C6B -152.0(3) . . . . ? C5B Zr C7B C6B 37.6(3) . . . . ? C8B Zr C7B C6B 113.3(4) . . . . ? C8A Zr C7B C6B -123.1(3) . . . . ? C4A Zr C7B C6B -96.2(3) . . . . ? C4B Zr C7B C6B 76.8(3) . . . . ? Cl1 Zr C7B C8B 4.1(3) . . . . ? C6B Zr C7B C8B -113.3(4) . . . . ? Cl2 Zr C7B C8B -120.8(2) . . . . ? C6A Zr C7B C8B 105.2(3) . . . . ? C5A Zr C7B C8B 139.5(3) . . . . ? C7A Zr C7B C8B 94.7(3) . . . . ? C5B Zr C7B C8B -75.7(3) . . . . ? C8A Zr C7B C8B 123.6(3) . . . . ? C4A Zr C7B C8B 150.5(2) . . . . ? C4B Zr C7B C8B -36.5(2) . . . . ? C5B C4B C8B C7B -2.2(5) . . . . ? C3B C4B C8B C7B 174.2(3) . . . . ? Zr C4B C8B C7B -64.6(3) . . . . ? C5B C4B C8B C1B -173.8(3) . . . . ? C3B C4B C8B C1B 2.6(4) . . . . ? Zr C4B C8B C1B 123.9(3) . . . . ? C5B C4B C8B Zr 62.3(3) . . . . ? C3B C4B C8B Zr -121.3(3) . . . . ? C6B C7B C8B C4B 2.8(5) . . . . ? Zr C7B C8B C4B 67.5(3) . . . . ? C6B C7B C8B C1B 170.4(5) . . . . ? Zr C7B C8B C1B -124.9(5) . . . . ? C6B C7B C8B Zr -64.7(3) . . . . ? C2B C1B C8B C4B -2.6(4) . . . . ? C9B C1B C8B C4B -122.1(4) . . . . ? C10B C1B C8B C4B 113.9(4) . . . . ? C2B C1B C8B C7B -170.0(5) . . . . ? C9B C1B C8B C7B 70.5(7) . . . . ? C10B C1B C8B C7B -53.5(7) . . . . ? C2B C1B C8B Zr 84.8(4) . . . . ? C9B C1B C8B Zr -34.8(5) . . . . ? C10B C1B C8B Zr -158.7(3) . . . . ? Cl1 Zr C8B C4B 68.5(2) . . . . ? C6B Zr C8B C4B -76.3(3) . . . . ? Cl2 Zr C8B C4B -32.0(3) . . . . ? C6A Zr C8B C4B 174.7(3) . . . . ? C5A Zr C8B C4B -154.9(2) . . . . ? C7B Zr C8B C4B -114.9(4) . . . . ? C7A Zr C8B C4B 149.0(2) . . . . ? C5B Zr C8B C4B -35.2(2) . . . . ? C8A Zr C8B C4B 159.2(2) . . . . ? C4A Zr C8B C4B -155.3(2) . . . . ? Cl1 Zr C8B C7B -176.6(3) . . . . ? C6B Zr C8B C7B 38.6(3) . . . . ? Cl2 Zr C8B C7B 82.9(3) . . . . ? C6A Zr C8B C7B -70.4(3) . . . . ? C5A Zr C8B C7B -40.0(3) . . . . ? C7A Zr C8B C7B -96.1(3) . . . . ? C5B Zr C8B C7B 79.7(3) . . . . ? C8A Zr C8B C7B -85.9(3) . . . . ? C4A Zr C8B C7B -40.4(3) . . . . ? C4B Zr C8B C7B 114.9(4) . . . . ? Cl1 Zr C8B C1B -37.2(3) . . . . ? C6B Zr C8B C1B 178.0(4) . . . . ? Cl2 Zr C8B C1B -137.7(3) . . . . ? C6A Zr C8B C1B 69.0(3) . . . . ? C5A Zr C8B C1B 99.4(3) . . . . ? C7B Zr C8B C1B 139.4(5) . . . . ? C7A Zr C8B C1B 43.3(4) . . . . ? C5B Zr C8B C1B -140.9(4) . . . . ? C8A Zr C8B C1B 53.5(4) . . . . ? C4A Zr C8B C1B 99.0(3) . . . . ? C4B Zr C8B C1B -105.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.202 _refine_diff_density_min -0.740 _refine_diff_density_rms 0.098 # Attachment '- 11a.cif' data_erk5269 _database_code_depnum_ccdc_archive 'CCDC 778229' #TrackingRef '- 11a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 Cl2 N Zr' _chemical_formula_weight 387.44 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' Cl Cl 0.1484 0.1585 '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 P21/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 13.5034(3) _cell_length_b 6.6071(2) _cell_length_c 19.0188(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.548(1) _cell_angle_gamma 90.00 _cell_volume 1617.86(9) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3290 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7212 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10618 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 27.90 _reflns_number_total 3772 _reflns_number_gt 2985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0136P)^2^+6.4653P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3772 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Zr1 Zr 0.81354(3) 0.46675(6) 0.10672(2) 0.03009(12) Uani 1 1 d . . . N1 N 1.1147(4) 0.1430(7) 0.1728(3) 0.0639(14) Uani 1 1 d . . . C1 C 0.9890(4) 0.4123(9) 0.2957(3) 0.0462(12) Uani 1 1 d . . . H1 H 0.9250 0.3547 0.3028 0.055 Uiso 1 1 calc R . . Cl1 Cl 0.85345(10) 0.2391(2) 0.01711(7) 0.0488(3) Uani 1 1 d . . . Cl2 Cl 0.77854(10) 0.20760(18) 0.18778(7) 0.0437(3) Uani 1 1 d . . . C2 C 1.0518(4) 0.2479(8) 0.2762(3) 0.0525(14) Uani 1 1 d . . . H2 H 1.0800 0.1398 0.3081 0.063 Uiso 1 1 calc R . . C3 C 1.0645(3) 0.2679(7) 0.2088(3) 0.0420(11) Uani 1 1 d . . . C4 C 1.0090(3) 0.4568(7) 0.1759(2) 0.0317(9) Uani 1 1 d . . . C5 C 0.9914(4) 0.5932(8) 0.1156(3) 0.0442(12) Uani 1 1 d . . . H5 H 1.0138 0.5780 0.0737 0.053 Uiso 1 1 calc R . . C6 C 0.9336(4) 0.7556(7) 0.1310(3) 0.0504(14) Uani 1 1 d . . . H6 H 0.9119 0.8701 0.1010 0.061 Uiso 1 1 calc R . . C7 C 0.9138(4) 0.7203(7) 0.1979(3) 0.0438(12) Uani 1 1 d . . . H7 H 0.8753 0.8038 0.2201 0.053 Uiso 1 1 calc R . . C8 C 0.9618(3) 0.5375(7) 0.2258(2) 0.0356(9) Uani 1 1 d . . . C9 C 1.0465(5) 0.5363(11) 0.3629(3) 0.0697(18) Uani 1 1 d . . . H9A H 1.0675 0.4490 0.4059 0.105 Uiso 1 1 calc R . . H9B H 1.0013 0.6419 0.3709 0.105 Uiso 1 1 calc R . . H9C H 1.1076 0.5971 0.3548 0.105 Uiso 1 1 calc R . . C10 C 1.1742(5) -0.0201(10) 0.2163(5) 0.091(3) Uani 1 1 d . . . H10A H 1.2296 0.0357 0.2568 0.137 Uiso 1 1 calc R . . H10B H 1.2039 -0.1026 0.1855 0.137 Uiso 1 1 calc R . . H10C H 1.1292 -0.1029 0.2357 0.137 Uiso 1 1 calc R . . C11 C 1.1418(5) 0.2085(13) 0.1096(4) 0.085(2) Uani 1 1 d . . . H11A H 1.0831 0.2774 0.0759 0.128 Uiso 1 1 calc R . . H11B H 1.1605 0.0922 0.0852 0.128 Uiso 1 1 calc R . . H11C H 1.2004 0.3006 0.1248 0.128 Uiso 1 1 calc R . . C12 C 0.6795(4) 0.7348(8) 0.0924(3) 0.0528(14) Uani 1 1 d . . . H12 H 0.6942 0.8426 0.1262 0.063 Uiso 1 1 calc R . . C13 C 0.7033(4) 0.7281(9) 0.0256(4) 0.0591(16) Uani 1 1 d . . . H13 H 0.7374 0.8293 0.0070 0.071 Uiso 1 1 calc R . . C14 C 0.6671(4) 0.5431(10) -0.0081(3) 0.0594(16) Uani 1 1 d . . . H14 H 0.6714 0.4990 -0.0541 0.071 Uiso 1 1 calc R . . C15 C 0.6234(4) 0.4357(9) 0.0381(3) 0.0512(13) Uani 1 1 d . . . H15 H 0.5943 0.3055 0.0291 0.061 Uiso 1 1 calc R . . C16 C 0.6303(4) 0.5542(8) 0.1001(3) 0.0465(12) Uani 1 1 d . . . H16 H 0.6061 0.5188 0.1399 0.056 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 0.0313(2) 0.0262(2) 0.0331(2) -0.00027(18) 0.01004(16) 0.00079(17) N1 0.050(3) 0.048(3) 0.096(4) -0.007(3) 0.025(3) 0.015(2) C1 0.042(3) 0.066(3) 0.032(2) 0.002(2) 0.014(2) -0.012(2) Cl1 0.0602(8) 0.0434(7) 0.0494(8) -0.0106(6) 0.0264(6) 0.0002(6) Cl2 0.0509(7) 0.0350(6) 0.0459(7) 0.0054(5) 0.0153(5) -0.0077(5) C2 0.046(3) 0.046(3) 0.060(4) 0.017(3) 0.006(3) 0.003(2) C3 0.031(2) 0.035(2) 0.058(3) -0.001(2) 0.010(2) -0.0023(19) C4 0.028(2) 0.032(2) 0.034(2) 0.0011(19) 0.0087(17) -0.0026(18) C5 0.036(2) 0.051(3) 0.046(3) 0.004(2) 0.013(2) -0.014(2) C6 0.047(3) 0.029(2) 0.066(4) 0.007(2) 0.003(3) -0.007(2) C7 0.040(3) 0.032(2) 0.055(3) -0.012(2) 0.008(2) 0.003(2) C8 0.038(2) 0.038(2) 0.031(2) -0.0042(19) 0.0107(18) -0.005(2) C9 0.066(4) 0.100(5) 0.039(3) -0.010(3) 0.010(3) -0.013(4) C10 0.051(4) 0.050(4) 0.160(8) -0.005(4) 0.012(4) 0.019(3) C11 0.068(4) 0.120(7) 0.075(5) -0.024(5) 0.033(4) 0.025(4) C12 0.046(3) 0.039(3) 0.070(4) -0.006(3) 0.014(3) 0.011(2) C13 0.044(3) 0.054(3) 0.074(4) 0.026(3) 0.010(3) 0.011(3) C14 0.052(3) 0.081(4) 0.037(3) 0.000(3) 0.000(2) 0.020(3) C15 0.038(3) 0.047(3) 0.060(3) -0.004(3) 0.002(2) 0.002(2) C16 0.032(2) 0.055(3) 0.055(3) -0.003(3) 0.017(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 Cl2 2.4436(12) . ? Zr1 Cl1 2.4515(13) . ? Zr1 C6 2.457(5) . ? Zr1 C12 2.488(5) . ? Zr1 C13 2.488(5) . ? Zr1 C7 2.496(5) . ? Zr1 C5 2.500(4) . ? Zr1 C16 2.507(4) . ? Zr1 C15 2.513(5) . ? Zr1 C14 2.517(5) . ? Zr1 C4 2.571(4) . ? Zr1 C8 2.573(4) . ? N1 C3 1.373(7) . ? N1 C11 1.426(8) . ? N1 C10 1.446(8) . ? C1 C2 1.492(8) . ? C1 C8 1.514(7) . ? C1 C9 1.520(7) . ? C1 H1 0.9900 . ? C2 C3 1.351(7) . ? C2 H2 0.9400 . ? C3 C4 1.492(6) . ? C4 C8 1.398(6) . ? C4 C5 1.422(6) . ? C5 C6 1.408(7) . ? C5 H5 0.9400 . ? C6 C7 1.397(8) . ? C6 H6 0.9400 . ? C7 C8 1.397(7) . ? C7 H7 0.9400 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 C16 1.394(7) . ? C12 C13 1.401(8) . ? C12 H12 0.9400 . ? C13 C14 1.399(8) . ? C13 H13 0.9400 . ? C14 C15 1.392(8) . ? C14 H14 0.9400 . ? C15 C16 1.394(7) . ? C15 H15 0.9400 . ? C16 H16 0.9400 . ? 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 Cl2 Zr1 Cl1 97.68(5) . . ? Cl2 Zr1 C6 131.91(14) . . ? Cl1 Zr1 C6 109.66(15) . . ? Cl2 Zr1 C12 107.16(15) . . ? Cl1 Zr1 C12 131.73(15) . . ? C6 Zr1 C12 83.39(18) . . ? Cl2 Zr1 C13 133.15(14) . . ? Cl1 Zr1 C13 102.16(17) . . ? C6 Zr1 C13 79.35(19) . . ? C12 Zr1 C13 32.71(19) . . ? Cl2 Zr1 C7 101.49(13) . . ? Cl1 Zr1 C7 135.06(12) . . ? C6 Zr1 C7 32.75(18) . . ? C12 Zr1 C7 79.79(17) . . ? C13 Zr1 C7 93.60(19) . . ? Cl2 Zr1 C5 123.80(12) . . ? Cl1 Zr1 C5 81.02(13) . . ? C6 Zr1 C5 33.00(17) . . ? C12 Zr1 C5 114.95(18) . . ? C13 Zr1 C5 101.12(18) . . ? C7 Zr1 C5 54.56(17) . . ? Cl2 Zr1 C16 79.49(13) . . ? Cl1 Zr1 C16 121.80(13) . . ? C6 Zr1 C16 114.58(18) . . ? C12 Zr1 C16 32.42(17) . . ? C13 Zr1 C16 53.97(19) . . ? C7 Zr1 C16 101.57(17) . . ? C5 Zr1 C16 147.12(18) . . ? Cl2 Zr1 C15 84.76(14) . . ? Cl1 Zr1 C15 89.62(13) . . ? C6 Zr1 C15 132.39(18) . . ? C12 Zr1 C15 53.52(18) . . ? C13 Zr1 C15 53.72(19) . . ? C7 Zr1 C15 132.11(17) . . ? C5 Zr1 C15 150.75(18) . . ? C16 Zr1 C15 32.25(17) . . ? Cl2 Zr1 C14 115.93(16) . . ? Cl1 Zr1 C14 78.44(14) . . ? C6 Zr1 C14 108.0(2) . . ? C12 Zr1 C14 53.61(19) . . ? C13 Zr1 C14 32.4(2) . . ? C7 Zr1 C14 126.04(19) . . ? C5 Zr1 C14 118.63(19) . . ? C16 Zr1 C14 53.45(19) . . ? C15 Zr1 C14 32.13(19) . . ? Cl2 Zr1 C4 91.32(10) . . ? Cl1 Zr1 C4 86.18(10) . . ? C6 Zr1 C4 53.55(15) . . ? C12 Zr1 C4 132.47(16) . . ? C13 Zr1 C4 131.69(17) . . ? C7 Zr1 C4 53.37(15) . . ? C5 Zr1 C4 32.53(14) . . ? C16 Zr1 C4 151.30(16) . . ? C15 Zr1 C4 173.83(16) . . ? C14 Zr1 C4 150.06(18) . . ? Cl2 Zr1 C8 79.58(11) . . ? Cl1 Zr1 C8 116.59(11) . . ? C6 Zr1 C8 53.05(17) . . ? C12 Zr1 C8 108.32(17) . . ? C13 Zr1 C8 125.49(19) . . ? C7 Zr1 C8 31.94(15) . . ? C5 Zr1 C8 53.37(15) . . ? C16 Zr1 C8 119.77(16) . . ? C15 Zr1 C8 150.88(17) . . ? C14 Zr1 C8 157.94(19) . . ? C4 Zr1 C8 31.55(13) . . ? C3 N1 C11 121.9(5) . . ? C3 N1 C10 115.9(6) . . ? C11 N1 C10 117.9(5) . . ? C2 C1 C8 100.7(4) . . ? C2 C1 C9 114.6(5) . . ? C8 C1 C9 111.8(5) . . ? C2 C1 H1 109.8 . . ? C8 C1 H1 109.8 . . ? C9 C1 H1 109.8 . . ? C3 C2 C1 114.1(5) . . ? C3 C2 H2 122.9 . . ? C1 C2 H2 122.9 . . ? C2 C3 N1 129.5(5) . . ? C2 C3 C4 106.7(4) . . ? N1 C3 C4 123.7(5) . . ? C8 C4 C5 107.8(4) . . ? C8 C4 C3 108.0(4) . . ? C5 C4 C3 144.0(5) . . ? C8 C4 Zr1 74.3(2) . . ? C5 C4 Zr1 71.0(2) . . ? C3 C4 Zr1 123.0(3) . . ? C6 C5 C4 106.5(5) . . ? C6 C5 Zr1 71.8(3) . . ? C4 C5 Zr1 76.5(2) . . ? C6 C5 H5 126.8 . . ? C4 C5 H5 126.8 . . ? Zr1 C5 H5 117.1 . . ? C7 C6 C5 109.4(4) . . ? C7 C6 Zr1 75.2(3) . . ? C5 C6 Zr1 75.2(3) . . ? C7 C6 H6 125.3 . . ? C5 C6 H6 125.3 . . ? Zr1 C6 H6 116.3 . . ? C6 C7 C8 107.2(4) . . ? C6 C7 Zr1 72.1(3) . . ? C8 C7 Zr1 77.1(3) . . ? C6 C7 H7 126.4 . . ? C8 C7 H7 126.4 . . ? Zr1 C7 H7 116.6 . . ? C7 C8 C4 109.1(4) . . ? C7 C8 C1 140.1(5) . . ? C4 C8 C1 110.3(4) . . ? C7 C8 Zr1 71.0(3) . . ? C4 C8 Zr1 74.1(2) . . ? C1 C8 Zr1 126.3(3) . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C12 C13 108.4(5) . . ? C16 C12 Zr1 74.6(3) . . ? C13 C12 Zr1 73.7(3) . . ? C16 C12 H12 125.8 . . ? C13 C12 H12 125.8 . . ? Zr1 C12 H12 117.9 . . ? C14 C13 C12 107.4(5) . . ? C14 C13 Zr1 74.9(3) . . ? C12 C13 Zr1 73.6(3) . . ? C14 C13 H13 126.3 . . ? C12 C13 H13 126.3 . . ? Zr1 C13 H13 117.3 . . ? C15 C14 C13 108.1(5) . . ? C15 C14 Zr1 73.8(3) . . ? C13 C14 Zr1 72.6(3) . . ? C15 C14 H14 125.9 . . ? C13 C14 H14 125.9 . . ? Zr1 C14 H14 119.5 . . ? C14 C15 C16 108.4(5) . . ? C14 C15 Zr1 74.1(3) . . ? C16 C15 Zr1 73.6(3) . . ? C14 C15 H15 125.8 . . ? C16 C15 H15 125.8 . . ? Zr1 C15 H15 118.4 . . ? C15 C16 C12 107.7(5) . . ? C15 C16 Zr1 74.1(3) . . ? C12 C16 Zr1 73.0(3) . . ? C15 C16 H16 126.1 . . ? C12 C16 H16 126.1 . . ? Zr1 C16 H16 118.6 . . ? 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 C8 C1 C2 C3 1.6(6) . . . . ? C9 C1 C2 C3 -118.6(5) . . . . ? C1 C2 C3 N1 -178.0(5) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C11 N1 C3 C2 -165.1(6) . . . . ? C10 N1 C3 C2 -9.0(8) . . . . ? C11 N1 C3 C4 17.1(8) . . . . ? C10 N1 C3 C4 173.1(5) . . . . ? C2 C3 C4 C8 -2.1(5) . . . . ? N1 C3 C4 C8 176.2(4) . . . . ? C2 C3 C4 C5 171.8(6) . . . . ? N1 C3 C4 C5 -9.9(9) . . . . ? C2 C3 C4 Zr1 -84.8(5) . . . . ? N1 C3 C4 Zr1 93.5(5) . . . . ? Cl2 Zr1 C4 C8 -67.5(3) . . . . ? Cl1 Zr1 C4 C8 -165.1(3) . . . . ? C6 Zr1 C4 C8 77.0(3) . . . . ? C12 Zr1 C4 C8 47.4(4) . . . . ? C13 Zr1 C4 C8 92.0(3) . . . . ? C7 Zr1 C4 C8 35.9(3) . . . . ? C5 Zr1 C4 C8 115.6(4) . . . . ? C16 Zr1 C4 C8 2.8(5) . . . . ? C15 Zr1 C4 C8 -117.9(16) . . . . ? C14 Zr1 C4 C8 136.1(4) . . . . ? Cl2 Zr1 C4 C5 176.9(3) . . . . ? Cl1 Zr1 C4 C5 79.3(3) . . . . ? C6 Zr1 C4 C5 -38.7(3) . . . . ? C12 Zr1 C4 C5 -68.2(4) . . . . ? C13 Zr1 C4 C5 -23.6(4) . . . . ? C7 Zr1 C4 C5 -79.7(3) . . . . ? C16 Zr1 C4 C5 -112.9(4) . . . . ? C15 Zr1 C4 C5 126.4(16) . . . . ? C14 Zr1 C4 C5 20.5(5) . . . . ? C8 Zr1 C4 C5 -115.6(4) . . . . ? Cl2 Zr1 C4 C3 34.1(4) . . . . ? Cl1 Zr1 C4 C3 -63.5(4) . . . . ? C6 Zr1 C4 C3 178.6(5) . . . . ? C12 Zr1 C4 C3 149.1(4) . . . . ? C13 Zr1 C4 C3 -166.4(4) . . . . ? C7 Zr1 C4 C3 137.5(4) . . . . ? C5 Zr1 C4 C3 -142.7(5) . . . . ? C16 Zr1 C4 C3 104.4(5) . . . . ? C15 Zr1 C4 C3 -16.3(18) . . . . ? C14 Zr1 C4 C3 -122.2(5) . . . . ? C8 Zr1 C4 C3 101.6(5) . . . . ? C8 C4 C5 C6 0.3(5) . . . . ? C3 C4 C5 C6 -173.6(6) . . . . ? Zr1 C4 C5 C6 66.1(3) . . . . ? C8 C4 C5 Zr1 -65.7(3) . . . . ? C3 C4 C5 Zr1 120.3(6) . . . . ? Cl2 Zr1 C5 C6 -116.4(3) . . . . ? Cl1 Zr1 C5 C6 150.3(3) . . . . ? C12 Zr1 C5 C6 18.3(4) . . . . ? C13 Zr1 C5 C6 49.6(4) . . . . ? C7 Zr1 C5 C6 -36.9(3) . . . . ? C16 Zr1 C5 C6 12.7(5) . . . . ? C15 Zr1 C5 C6 77.5(5) . . . . ? C14 Zr1 C5 C6 78.8(4) . . . . ? C4 Zr1 C5 C6 -112.7(5) . . . . ? C8 Zr1 C5 C6 -76.7(3) . . . . ? Cl2 Zr1 C5 C4 -3.7(3) . . . . ? Cl1 Zr1 C5 C4 -97.0(3) . . . . ? C6 Zr1 C5 C4 112.7(5) . . . . ? C12 Zr1 C5 C4 130.9(3) . . . . ? C13 Zr1 C5 C4 162.2(3) . . . . ? C7 Zr1 C5 C4 75.8(3) . . . . ? C16 Zr1 C5 C4 125.4(3) . . . . ? C15 Zr1 C5 C4 -169.8(3) . . . . ? C14 Zr1 C5 C4 -168.5(3) . . . . ? C8 Zr1 C5 C4 36.0(3) . . . . ? C4 C5 C6 C7 -1.3(5) . . . . ? Zr1 C5 C6 C7 68.1(4) . . . . ? C4 C5 C6 Zr1 -69.3(3) . . . . ? Cl2 Zr1 C6 C7 -25.8(4) . . . . ? Cl1 Zr1 C6 C7 -146.5(3) . . . . ? C12 Zr1 C6 C7 81.4(3) . . . . ? C13 Zr1 C6 C7 114.2(3) . . . . ? C5 Zr1 C6 C7 -115.2(4) . . . . ? C16 Zr1 C6 C7 72.3(3) . . . . ? C15 Zr1 C6 C7 105.0(3) . . . . ? C14 Zr1 C6 C7 129.7(3) . . . . ? C4 Zr1 C6 C7 -77.1(3) . . . . ? C8 Zr1 C6 C7 -37.5(3) . . . . ? Cl2 Zr1 C6 C5 89.5(3) . . . . ? Cl1 Zr1 C6 C5 -31.3(3) . . . . ? C12 Zr1 C6 C5 -163.4(3) . . . . ? C13 Zr1 C6 C5 -130.5(4) . . . . ? C7 Zr1 C6 C5 115.2(4) . . . . ? C16 Zr1 C6 C5 -172.4(3) . . . . ? C15 Zr1 C6 C5 -139.8(3) . . . . ? C14 Zr1 C6 C5 -115.1(3) . . . . ? C4 Zr1 C6 C5 38.1(3) . . . . ? C8 Zr1 C6 C5 77.7(3) . . . . ? C5 C6 C7 C8 1.7(6) . . . . ? Zr1 C6 C7 C8 69.7(3) . . . . ? C5 C6 C7 Zr1 -68.0(3) . . . . ? Cl2 Zr1 C7 C6 160.7(3) . . . . ? Cl1 Zr1 C7 C6 47.3(4) . . . . ? C12 Zr1 C7 C6 -93.7(3) . . . . ? C13 Zr1 C7 C6 -63.9(3) . . . . ? C5 Zr1 C7 C6 37.2(3) . . . . ? C16 Zr1 C7 C6 -117.8(3) . . . . ? C15 Zr1 C7 C6 -105.9(4) . . . . ? C14 Zr1 C7 C6 -64.9(4) . . . . ? C4 Zr1 C7 C6 77.7(3) . . . . ? C8 Zr1 C7 C6 113.2(4) . . . . ? Cl2 Zr1 C7 C8 47.6(3) . . . . ? Cl1 Zr1 C7 C8 -65.8(4) . . . . ? C6 Zr1 C7 C8 -113.2(4) . . . . ? C12 Zr1 C7 C8 153.2(3) . . . . ? C13 Zr1 C7 C8 -177.0(3) . . . . ? C5 Zr1 C7 C8 -75.9(3) . . . . ? C16 Zr1 C7 C8 129.0(3) . . . . ? C15 Zr1 C7 C8 140.9(3) . . . . ? C14 Zr1 C7 C8 -178.0(3) . . . . ? C4 Zr1 C7 C8 -35.4(3) . . . . ? C6 C7 C8 C4 -1.5(5) . . . . ? Zr1 C7 C8 C4 64.8(3) . . . . ? C6 C7 C8 C1 169.4(6) . . . . ? Zr1 C7 C8 C1 -124.3(6) . . . . ? C6 C7 C8 Zr1 -66.3(3) . . . . ? C5 C4 C8 C7 0.7(5) . . . . ? C3 C4 C8 C7 176.9(4) . . . . ? Zr1 C4 C8 C7 -62.8(3) . . . . ? C5 C4 C8 C1 -173.0(4) . . . . ? C3 C4 C8 C1 3.2(5) . . . . ? Zr1 C4 C8 C1 123.4(3) . . . . ? C5 C4 C8 Zr1 63.5(3) . . . . ? C3 C4 C8 Zr1 -120.2(3) . . . . ? C2 C1 C8 C7 -173.7(6) . . . . ? C9 C1 C8 C7 -51.5(8) . . . . ? C2 C1 C8 C4 -2.9(5) . . . . ? C9 C1 C8 C4 119.2(5) . . . . ? C2 C1 C8 Zr1 81.9(4) . . . . ? C9 C1 C8 Zr1 -155.9(4) . . . . ? Cl2 Zr1 C8 C7 -132.7(3) . . . . ? Cl1 Zr1 C8 C7 133.9(3) . . . . ? C6 Zr1 C8 C7 38.5(3) . . . . ? C12 Zr1 C8 C7 -27.9(3) . . . . ? C13 Zr1 C8 C7 3.6(4) . . . . ? C5 Zr1 C8 C7 80.0(3) . . . . ? C16 Zr1 C8 C7 -61.3(3) . . . . ? C15 Zr1 C8 C7 -74.0(5) . . . . ? C14 Zr1 C8 C7 4.2(6) . . . . ? C4 Zr1 C8 C7 117.2(4) . . . . ? Cl2 Zr1 C8 C4 110.1(3) . . . . ? Cl1 Zr1 C8 C4 16.7(3) . . . . ? C6 Zr1 C8 C4 -78.7(3) . . . . ? C12 Zr1 C8 C4 -145.1(3) . . . . ? C13 Zr1 C8 C4 -113.6(3) . . . . ? C7 Zr1 C8 C4 -117.2(4) . . . . ? C5 Zr1 C8 C4 -37.2(3) . . . . ? C16 Zr1 C8 C4 -178.5(3) . . . . ? C15 Zr1 C8 C4 168.8(3) . . . . ? C14 Zr1 C8 C4 -113.0(5) . . . . ? Cl2 Zr1 C8 C1 6.3(4) . . . . ? Cl1 Zr1 C8 C1 -87.1(4) . . . . ? C6 Zr1 C8 C1 177.5(5) . . . . ? C12 Zr1 C8 C1 111.1(4) . . . . ? C13 Zr1 C8 C1 142.6(4) . . . . ? C7 Zr1 C8 C1 139.0(6) . . . . ? C5 Zr1 C8 C1 -141.0(5) . . . . ? C16 Zr1 C8 C1 77.7(4) . . . . ? C15 Zr1 C8 C1 64.9(6) . . . . ? C14 Zr1 C8 C1 143.2(5) . . . . ? C4 Zr1 C8 C1 -103.8(5) . . . . ? Cl2 Zr1 C12 C16 -32.6(4) . . . . ? Cl1 Zr1 C12 C16 85.0(4) . . . . ? C6 Zr1 C12 C16 -164.5(4) . . . . ? C13 Zr1 C12 C16 114.9(5) . . . . ? C7 Zr1 C12 C16 -131.6(4) . . . . ? C5 Zr1 C12 C16 -174.4(3) . . . . ? C15 Zr1 C12 C16 37.1(3) . . . . ? C14 Zr1 C12 C16 77.3(4) . . . . ? C4 Zr1 C12 C16 -141.0(3) . . . . ? C8 Zr1 C12 C16 -117.0(3) . . . . ? Cl2 Zr1 C12 C13 -147.5(3) . . . . ? Cl1 Zr1 C12 C13 -30.0(4) . . . . ? C6 Zr1 C12 C13 80.6(4) . . . . ? C7 Zr1 C12 C13 113.5(4) . . . . ? C5 Zr1 C12 C13 70.7(4) . . . . ? C16 Zr1 C12 C13 -114.9(5) . . . . ? C15 Zr1 C12 C13 -77.8(4) . . . . ? C14 Zr1 C12 C13 -37.6(3) . . . . ? C4 Zr1 C12 C13 104.1(4) . . . . ? C8 Zr1 C12 C13 128.0(3) . . . . ? C16 C12 C13 C14 0.8(6) . . . . ? Zr1 C12 C13 C14 67.9(4) . . . . ? C16 C12 C13 Zr1 -67.1(4) . . . . ? Cl2 Zr1 C13 C14 -69.1(4) . . . . ? Cl1 Zr1 C13 C14 43.9(4) . . . . ? C6 Zr1 C13 C14 151.9(4) . . . . ? C12 Zr1 C13 C14 -113.7(5) . . . . ? C7 Zr1 C13 C14 -178.5(4) . . . . ? C5 Zr1 C13 C14 126.9(4) . . . . ? C16 Zr1 C13 C14 -76.8(4) . . . . ? C15 Zr1 C13 C14 -36.6(3) . . . . ? C4 Zr1 C13 C14 139.6(3) . . . . ? C8 Zr1 C13 C14 179.6(3) . . . . ? Cl2 Zr1 C13 C12 44.7(4) . . . . ? Cl1 Zr1 C13 C12 157.6(3) . . . . ? C6 Zr1 C13 C12 -94.4(4) . . . . ? C7 Zr1 C13 C12 -64.7(4) . . . . ? C5 Zr1 C13 C12 -119.3(3) . . . . ? C16 Zr1 C13 C12 36.9(3) . . . . ? C15 Zr1 C13 C12 77.2(4) . . . . ? C14 Zr1 C13 C12 113.7(5) . . . . ? C4 Zr1 C13 C12 -106.6(3) . . . . ? C8 Zr1 C13 C12 -66.7(4) . . . . ? C12 C13 C14 C15 -1.2(6) . . . . ? Zr1 C13 C14 C15 65.8(4) . . . . ? C12 C13 C14 Zr1 -67.0(4) . . . . ? Cl2 Zr1 C14 C15 15.2(4) . . . . ? Cl1 Zr1 C14 C15 108.2(4) . . . . ? C6 Zr1 C14 C15 -144.6(4) . . . . ? C12 Zr1 C14 C15 -77.6(4) . . . . ? C13 Zr1 C14 C15 -115.5(5) . . . . ? C7 Zr1 C14 C15 -113.6(4) . . . . ? C5 Zr1 C14 C15 -178.8(3) . . . . ? C16 Zr1 C14 C15 -37.0(3) . . . . ? C4 Zr1 C14 C15 168.8(3) . . . . ? C8 Zr1 C14 C15 -116.4(5) . . . . ? Cl2 Zr1 C14 C13 130.7(3) . . . . ? Cl1 Zr1 C14 C13 -136.3(4) . . . . ? C6 Zr1 C14 C13 -29.1(4) . . . . ? C12 Zr1 C14 C13 37.9(3) . . . . ? C7 Zr1 C14 C13 1.9(5) . . . . ? C5 Zr1 C14 C13 -63.3(4) . . . . ? C16 Zr1 C14 C13 78.5(4) . . . . ? C15 Zr1 C14 C13 115.5(5) . . . . ? C4 Zr1 C14 C13 -75.7(5) . . . . ? C8 Zr1 C14 C13 -0.9(7) . . . . ? C13 C14 C15 C16 1.2(6) . . . . ? Zr1 C14 C15 C16 66.2(4) . . . . ? C13 C14 C15 Zr1 -65.0(4) . . . . ? Cl2 Zr1 C15 C14 -166.3(4) . . . . ? Cl1 Zr1 C15 C14 -68.5(4) . . . . ? C6 Zr1 C15 C14 48.2(5) . . . . ? C12 Zr1 C15 C14 77.9(4) . . . . ? C13 Zr1 C15 C14 36.9(4) . . . . ? C7 Zr1 C15 C14 93.0(4) . . . . ? C5 Zr1 C15 C14 2.1(6) . . . . ? C16 Zr1 C15 C14 115.2(5) . . . . ? C4 Zr1 C15 C14 -115.5(16) . . . . ? C8 Zr1 C15 C14 136.3(4) . . . . ? Cl2 Zr1 C15 C16 78.6(3) . . . . ? Cl1 Zr1 C15 C16 176.3(3) . . . . ? C6 Zr1 C15 C16 -67.0(4) . . . . ? C12 Zr1 C15 C16 -37.3(3) . . . . ? C13 Zr1 C15 C16 -78.2(4) . . . . ? C7 Zr1 C15 C16 -22.2(5) . . . . ? C5 Zr1 C15 C16 -113.0(4) . . . . ? C14 Zr1 C15 C16 -115.2(5) . . . . ? C4 Zr1 C15 C16 129.3(15) . . . . ? C8 Zr1 C15 C16 21.1(6) . . . . ? C14 C15 C16 C12 -0.7(6) . . . . ? Zr1 C15 C16 C12 65.8(3) . . . . ? C14 C15 C16 Zr1 -66.5(4) . . . . ? C13 C12 C16 C15 -0.1(6) . . . . ? Zr1 C12 C16 C15 -66.6(3) . . . . ? C13 C12 C16 Zr1 66.5(4) . . . . ? Cl2 Zr1 C16 C15 -96.9(3) . . . . ? Cl1 Zr1 C16 C15 -4.3(4) . . . . ? C6 Zr1 C16 C15 131.6(3) . . . . ? C12 Zr1 C16 C15 114.7(5) . . . . ? C13 Zr1 C16 C15 77.4(4) . . . . ? C7 Zr1 C16 C15 163.4(3) . . . . ? C5 Zr1 C16 C15 124.1(4) . . . . ? C14 Zr1 C16 C15 36.8(3) . . . . ? C4 Zr1 C16 C15 -170.0(3) . . . . ? C8 Zr1 C16 C15 -168.4(3) . . . . ? Cl2 Zr1 C16 C12 148.4(3) . . . . ? Cl1 Zr1 C16 C12 -119.0(3) . . . . ? C6 Zr1 C16 C12 17.0(4) . . . . ? C13 Zr1 C16 C12 -37.3(3) . . . . ? C7 Zr1 C16 C12 48.7(4) . . . . ? C5 Zr1 C16 C12 9.4(5) . . . . ? C15 Zr1 C16 C12 -114.7(5) . . . . ? C14 Zr1 C16 C12 -77.9(4) . . . . ? C4 Zr1 C16 C12 75.3(5) . . . . ? C8 Zr1 C16 C12 77.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.681 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.094 # Attachment '- 11c.cif' data_erk5291 _database_code_depnum_ccdc_archive 'CCDC 778230' #TrackingRef '- 11c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl2 N Zr' _chemical_formula_weight 373.42 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' Cl Cl 0.1484 0.1585 '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 P212121 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' _cell_length_a 6.6449(2) _cell_length_b 11.6187(3) _cell_length_c 19.6379(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1516.15(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2430 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour red-yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7073 _exptl_absorpt_correction_T_max 0.9198 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7197 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3548 _reflns_number_gt 3433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & MInor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0169P)^2^+2.3908P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(7) _refine_ls_number_reflns 3548 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 Zr1 Zr 0.80452(5) 0.60147(3) 0.853906(18) 0.03728(9) Uani 1 1 d . . . Cl1 Cl 1.06671(17) 0.63321(11) 0.93814(6) 0.0594(3) Uani 1 1 d . . . Cl2 Cl 1.03160(17) 0.57522(11) 0.75678(6) 0.0562(3) Uani 1 1 d . . . N1 N 0.8334(9) 0.4237(4) 1.0573(2) 0.0832(14) Uani 1 1 d . . . C1 C 1.0293(8) 0.3235(4) 0.8909(3) 0.0663(14) Uani 1 1 d . . . H1A H 1.1453 0.3605 0.8692 0.080 Uiso 1 1 calc R . . H1B H 1.0249 0.2423 0.8774 0.080 Uiso 1 1 calc R . . C2 C 1.0370(8) 0.3359(4) 0.9668(3) 0.0604(12) Uani 1 1 d . . . H2 H 1.1396 0.3055 0.9944 0.072 Uiso 1 1 calc R . . C3 C 0.8764(7) 0.3970(4) 0.9908(2) 0.0563(11) Uani 1 1 d . . . C4 C 0.7487(6) 0.4255(3) 0.9327(2) 0.0469(10) Uani 1 1 d . . . C5 C 0.5587(7) 0.4746(4) 0.9129(3) 0.0640(15) Uani 1 1 d . . . H5 H 0.4659 0.5120 0.9415 0.077 Uiso 1 1 calc R . . C6 C 0.5393(9) 0.4560(5) 0.8434(3) 0.0724(17) Uani 1 1 d . . . H6 H 0.4275 0.4780 0.8171 0.087 Uiso 1 1 calc R . . C7 C 0.7101(9) 0.3998(4) 0.8180(3) 0.0691(14) Uani 1 1 d . . . H7 H 0.7334 0.3774 0.7727 0.083 Uiso 1 1 calc R . . C8 C 0.8386(7) 0.3835(4) 0.8733(2) 0.0537(11) Uani 1 1 d . . . C9 C 0.9894(13) 0.3952(7) 1.1074(3) 0.110(3) Uani 1 1 d . . . H9A H 1.0034 0.3123 1.1105 0.165 Uiso 1 1 calc R . . H9B H 0.9516 0.4258 1.1515 0.165 Uiso 1 1 calc R . . H9C H 1.1165 0.4288 1.0933 0.165 Uiso 1 1 calc R . . C10 C 0.6889(12) 0.5080(5) 1.0741(3) 0.092(2) Uani 1 1 d . . . H10A H 0.7356 0.5829 1.0590 0.138 Uiso 1 1 calc R . . H10B H 0.6693 0.5093 1.1230 0.138 Uiso 1 1 calc R . . H10C H 0.5625 0.4899 1.0518 0.138 Uiso 1 1 calc R . . C11 C 0.8095(10) 0.8109(4) 0.8239(3) 0.0672(13) Uani 1 1 d . . . H11 H 0.9336 0.8444 0.8123 0.081 Uiso 1 1 calc R . . C12 C 0.7296(10) 0.8055(4) 0.8877(3) 0.0728(17) Uani 1 1 d . . . H12 H 0.7890 0.8368 0.9270 0.087 Uiso 1 1 calc R . . C13 C 0.5516(10) 0.7484(5) 0.8861(4) 0.080(2) Uani 1 1 d . . . H13 H 0.4695 0.7314 0.9238 0.096 Uiso 1 1 calc R . . C14 C 0.5130(9) 0.7198(5) 0.8189(5) 0.089(2) Uani 1 1 d . . . H14 H 0.3985 0.6812 0.8025 0.107 Uiso 1 1 calc R . . C15 C 0.6785(12) 0.7594(5) 0.7795(3) 0.0805(18) Uani 1 1 d . . . H15 H 0.6948 0.7518 0.7322 0.097 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 0.03117(15) 0.04029(17) 0.04038(16) 0.00220(16) -0.00282(16) -0.00468(16) Cl1 0.0489(6) 0.0773(8) 0.0521(6) 0.0058(5) -0.0144(5) -0.0167(5) Cl2 0.0510(6) 0.0655(7) 0.0521(6) -0.0086(5) 0.0074(5) 0.0007(5) N1 0.112(4) 0.075(3) 0.063(3) 0.014(2) 0.003(3) 0.021(3) C1 0.060(3) 0.042(2) 0.097(4) -0.002(2) 0.014(3) 0.004(2) C2 0.049(3) 0.051(3) 0.081(3) 0.014(2) -0.001(2) 0.009(2) C3 0.063(3) 0.046(2) 0.060(2) 0.011(2) 0.008(2) 0.008(2) C4 0.040(2) 0.0336(19) 0.067(3) 0.0086(18) 0.0066(18) -0.0021(14) C5 0.032(2) 0.052(3) 0.108(4) 0.026(3) 0.020(3) 0.0012(19) C6 0.059(3) 0.066(3) 0.092(4) 0.020(3) -0.029(3) -0.029(3) C7 0.082(4) 0.052(3) 0.073(3) -0.002(2) -0.011(3) -0.036(3) C8 0.052(2) 0.043(2) 0.066(3) 0.0021(19) 0.001(2) -0.014(2) C9 0.167(7) 0.097(5) 0.066(4) 0.027(4) -0.023(4) -0.001(6) C10 0.124(6) 0.073(3) 0.078(4) -0.005(3) 0.041(4) 0.004(4) C11 0.063(3) 0.045(2) 0.094(4) 0.020(2) 0.016(3) -0.001(3) C12 0.098(5) 0.046(3) 0.075(3) -0.008(2) -0.009(3) 0.005(3) C13 0.062(4) 0.060(3) 0.118(5) 0.000(3) 0.039(4) 0.011(3) C14 0.048(3) 0.049(3) 0.171(7) 0.003(4) -0.037(4) 0.003(2) C15 0.121(5) 0.064(3) 0.056(3) 0.009(2) -0.021(4) 0.036(4) _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 Cl1 2.4306(11) . ? Zr1 C6 2.451(5) . ? Zr1 Cl2 2.4511(12) . ? Zr1 C14 2.473(5) . ? Zr1 C13 2.478(6) . ? Zr1 C5 2.487(4) . ? Zr1 C15 2.491(5) . ? Zr1 C11 2.504(5) . ? Zr1 C12 2.512(5) . ? Zr1 C7 2.526(5) . ? Zr1 C8 2.571(5) . ? Zr1 C4 2.591(4) . ? N1 C3 1.373(6) . ? N1 C10 1.411(8) . ? N1 C9 1.467(8) . ? C1 C8 1.487(7) . ? C1 C2 1.498(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 C3 1.366(6) . ? C2 H2 0.9400 . ? C3 C4 1.460(6) . ? C4 C8 1.400(6) . ? C4 C5 1.439(6) . ? C5 C6 1.389(8) . ? C5 H5 0.9400 . ? C6 C7 1.401(8) . ? C6 H6 0.9400 . ? C7 C8 1.393(7) . ? C7 H7 0.9400 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 C12 1.362(7) . ? C11 C15 1.369(8) . ? C11 H11 0.9400 . ? C12 C13 1.357(9) . ? C12 H12 0.9400 . ? C13 C14 1.385(9) . ? C13 H13 0.9400 . ? C14 C15 1.422(10) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? 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 Cl1 Zr1 C6 132.66(14) . . ? Cl1 Zr1 Cl2 96.15(4) . . ? C6 Zr1 Cl2 106.93(17) . . ? Cl1 Zr1 C14 131.78(18) . . ? C6 Zr1 C14 78.2(2) . . ? Cl2 Zr1 C14 109.6(2) . . ? Cl1 Zr1 C13 102.0(2) . . ? C6 Zr1 C13 90.5(2) . . ? Cl2 Zr1 C13 134.59(17) . . ? C14 Zr1 C13 32.5(2) . . ? Cl1 Zr1 C5 104.09(15) . . ? C6 Zr1 C5 32.7(2) . . ? Cl2 Zr1 C5 133.91(14) . . ? C14 Zr1 C5 86.8(2) . . ? C13 Zr1 C5 81.00(18) . . ? Cl1 Zr1 C15 121.89(17) . . ? C6 Zr1 C15 102.5(2) . . ? Cl2 Zr1 C15 80.93(16) . . ? C14 Zr1 C15 33.3(2) . . ? C13 Zr1 C15 54.1(2) . . ? C5 Zr1 C15 119.3(2) . . ? Cl1 Zr1 C11 90.19(16) . . ? C6 Zr1 C11 131.3(2) . . ? Cl2 Zr1 C11 85.96(14) . . ? C14 Zr1 C11 53.5(2) . . ? C13 Zr1 C11 53.1(2) . . ? C5 Zr1 C11 133.97(18) . . ? C15 Zr1 C11 31.82(19) . . ? Cl1 Zr1 C12 79.58(15) . . ? C6 Zr1 C12 122.1(2) . . ? Cl2 Zr1 C12 116.42(15) . . ? C14 Zr1 C12 52.7(2) . . ? C13 Zr1 C12 31.5(2) . . ? C5 Zr1 C12 107.8(2) . . ? C15 Zr1 C12 52.60(19) . . ? C11 Zr1 C12 31.51(17) . . ? Cl1 Zr1 C7 120.56(14) . . ? C6 Zr1 C7 32.65(19) . . ? Cl2 Zr1 C7 79.66(14) . . ? C14 Zr1 C7 104.1(2) . . ? C13 Zr1 C7 122.8(2) . . ? C5 Zr1 C7 54.35(19) . . ? C15 Zr1 C7 115.9(2) . . ? C11 Zr1 C7 147.1(2) . . ? C12 Zr1 C7 154.2(2) . . ? Cl1 Zr1 C8 89.18(11) . . ? C6 Zr1 C8 52.88(17) . . ? Cl2 Zr1 C8 86.46(11) . . ? C14 Zr1 C8 131.12(18) . . ? C13 Zr1 C8 134.48(18) . . ? C5 Zr1 C8 53.51(15) . . ? C15 Zr1 C8 147.37(19) . . ? C11 Zr1 C8 172.28(17) . . ? C12 Zr1 C8 155.27(17) . . ? C7 Zr1 C8 31.70(16) . . ? Cl1 Zr1 C4 79.39(10) . . ? C6 Zr1 C4 53.36(16) . . ? Cl2 Zr1 C4 117.05(10) . . ? C14 Zr1 C4 119.5(2) . . ? C13 Zr1 C4 107.09(18) . . ? C5 Zr1 C4 32.84(14) . . ? C15 Zr1 C4 152.1(2) . . ? C11 Zr1 C4 155.42(17) . . ? C12 Zr1 C4 123.97(18) . . ? C7 Zr1 C4 53.05(16) . . ? C8 Zr1 C4 31.46(14) . . ? C3 N1 C10 121.4(5) . . ? C3 N1 C9 116.1(5) . . ? C10 N1 C9 118.8(6) . . ? C8 C1 C2 102.5(4) . . ? C8 C1 H1A 111.3 . . ? C2 C1 H1A 111.3 . . ? C8 C1 H1B 111.3 . . ? C2 C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? C3 C2 C1 111.5(4) . . ? C3 C2 H2 124.2 . . ? C1 C2 H2 124.2 . . ? C2 C3 N1 127.5(5) . . ? C2 C3 C4 107.6(4) . . ? N1 C3 C4 124.8(4) . . ? C8 C4 C5 106.7(4) . . ? C8 C4 C3 108.9(4) . . ? C5 C4 C3 144.2(5) . . ? C8 C4 Zr1 73.5(3) . . ? C5 C4 Zr1 69.6(2) . . ? C3 C4 Zr1 124.2(3) . . ? C6 C5 C4 106.6(5) . . ? C6 C5 Zr1 72.2(3) . . ? C4 C5 Zr1 77.6(2) . . ? C6 C5 H5 126.7 . . ? C4 C5 H5 126.7 . . ? Zr1 C5 H5 115.8 . . ? C5 C6 C7 110.3(5) . . ? C5 C6 Zr1 75.1(3) . . ? C7 C6 Zr1 76.6(3) . . ? C5 C6 H6 124.9 . . ? C7 C6 H6 124.9 . . ? Zr1 C6 H6 115.3 . . ? C8 C7 C6 106.5(5) . . ? C8 C7 Zr1 75.9(3) . . ? C6 C7 Zr1 70.7(3) . . ? C8 C7 H7 126.8 . . ? C6 C7 H7 126.8 . . ? Zr1 C7 H7 118.6 . . ? C7 C8 C4 109.9(5) . . ? C7 C8 C1 140.1(5) . . ? C4 C8 C1 109.4(4) . . ? C7 C8 Zr1 72.4(3) . . ? C4 C8 Zr1 75.1(2) . . ? C1 C8 Zr1 124.8(3) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C15 108.5(6) . . ? C12 C11 Zr1 74.6(3) . . ? C15 C11 Zr1 73.5(3) . . ? C12 C11 H11 125.8 . . ? C15 C11 H11 125.8 . . ? Zr1 C11 H11 118.1 . . ? C13 C12 C11 110.0(6) . . ? C13 C12 Zr1 72.8(3) . . ? C11 C12 Zr1 73.9(3) . . ? C13 C12 H12 125.0 . . ? C11 C12 H12 125.0 . . ? Zr1 C12 H12 119.9 . . ? C12 C13 C14 107.5(6) . . ? C12 C13 Zr1 75.6(3) . . ? C14 C13 Zr1 73.5(3) . . ? C12 C13 H13 126.3 . . ? C14 C13 H13 126.3 . . ? Zr1 C13 H13 116.7 . . ? C13 C14 C15 107.3(5) . . ? C13 C14 Zr1 74.0(4) . . ? C15 C14 Zr1 74.1(3) . . ? C13 C14 H14 126.4 . . ? C15 C14 H14 126.4 . . ? Zr1 C14 H14 117.7 . . ? C11 C15 C14 106.7(5) . . ? C11 C15 Zr1 74.6(3) . . ? C14 C15 Zr1 72.7(3) . . ? C11 C15 H15 126.7 . . ? C14 C15 H15 126.7 . . ? Zr1 C15 H15 118.1 . . ? 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 C8 C1 C2 C3 -1.3(6) . . . . ? C1 C2 C3 N1 179.1(5) . . . . ? C1 C2 C3 C4 1.9(6) . . . . ? C10 N1 C3 C2 165.7(6) . . . . ? C9 N1 C3 C2 7.8(9) . . . . ? C10 N1 C3 C4 -17.5(9) . . . . ? C9 N1 C3 C4 -175.4(5) . . . . ? C2 C3 C4 C8 -1.8(5) . . . . ? N1 C3 C4 C8 -179.1(5) . . . . ? C2 C3 C4 C5 172.9(6) . . . . ? N1 C3 C4 C5 -4.4(10) . . . . ? C2 C3 C4 Zr1 -84.3(5) . . . . ? N1 C3 C4 Zr1 98.4(5) . . . . ? Cl1 Zr1 C4 C8 -106.2(3) . . . . ? C6 Zr1 C4 C8 77.0(3) . . . . ? Cl2 Zr1 C4 C8 -14.6(3) . . . . ? C14 Zr1 C4 C8 121.6(3) . . . . ? C13 Zr1 C4 C8 154.4(3) . . . . ? C5 Zr1 C4 C8 115.5(4) . . . . ? C15 Zr1 C4 C8 111.2(4) . . . . ? C11 Zr1 C4 C8 -172.5(4) . . . . ? C12 Zr1 C4 C8 -175.8(3) . . . . ? C7 Zr1 C4 C8 35.9(3) . . . . ? Cl1 Zr1 C4 C5 138.3(3) . . . . ? C6 Zr1 C4 C5 -38.5(3) . . . . ? Cl2 Zr1 C4 C5 -130.1(3) . . . . ? C14 Zr1 C4 C5 6.0(4) . . . . ? C13 Zr1 C4 C5 38.9(4) . . . . ? C15 Zr1 C4 C5 -4.3(5) . . . . ? C11 Zr1 C4 C5 72.0(6) . . . . ? C12 Zr1 C4 C5 68.7(4) . . . . ? C7 Zr1 C4 C5 -79.7(4) . . . . ? C8 Zr1 C4 C5 -115.5(4) . . . . ? Cl1 Zr1 C4 C3 -4.2(3) . . . . ? C6 Zr1 C4 C3 179.0(5) . . . . ? Cl2 Zr1 C4 C3 87.4(4) . . . . ? C14 Zr1 C4 C3 -136.5(4) . . . . ? C13 Zr1 C4 C3 -103.6(4) . . . . ? C5 Zr1 C4 C3 -142.5(6) . . . . ? C15 Zr1 C4 C3 -146.8(4) . . . . ? C11 Zr1 C4 C3 -70.5(5) . . . . ? C12 Zr1 C4 C3 -73.8(4) . . . . ? C7 Zr1 C4 C3 137.8(4) . . . . ? C8 Zr1 C4 C3 102.0(4) . . . . ? C8 C4 C5 C6 2.3(5) . . . . ? C3 C4 C5 C6 -172.4(6) . . . . ? Zr1 C4 C5 C6 66.9(3) . . . . ? C8 C4 C5 Zr1 -64.6(3) . . . . ? C3 C4 C5 Zr1 120.6(6) . . . . ? Cl1 Zr1 C5 C6 -154.5(3) . . . . ? Cl2 Zr1 C5 C6 -41.2(4) . . . . ? C14 Zr1 C5 C6 73.1(4) . . . . ? C13 Zr1 C5 C6 105.3(4) . . . . ? C15 Zr1 C5 C6 65.6(4) . . . . ? C11 Zr1 C5 C6 101.2(4) . . . . ? C12 Zr1 C5 C6 122.1(3) . . . . ? C7 Zr1 C5 C6 -36.8(3) . . . . ? C8 Zr1 C5 C6 -76.3(4) . . . . ? C4 Zr1 C5 C6 -112.2(5) . . . . ? Cl1 Zr1 C5 C4 -42.4(3) . . . . ? C6 Zr1 C5 C4 112.2(5) . . . . ? Cl2 Zr1 C5 C4 70.9(4) . . . . ? C14 Zr1 C5 C4 -174.7(4) . . . . ? C13 Zr1 C5 C4 -142.6(4) . . . . ? C15 Zr1 C5 C4 177.7(3) . . . . ? C11 Zr1 C5 C4 -146.7(3) . . . . ? C12 Zr1 C5 C4 -125.7(3) . . . . ? C7 Zr1 C5 C4 75.4(3) . . . . ? C8 Zr1 C5 C4 35.9(3) . . . . ? C4 C5 C6 C7 -1.3(5) . . . . ? Zr1 C5 C6 C7 69.3(3) . . . . ? C4 C5 C6 Zr1 -70.7(3) . . . . ? Cl1 Zr1 C6 C5 34.6(4) . . . . ? Cl2 Zr1 C6 C5 150.2(3) . . . . ? C14 Zr1 C6 C5 -102.6(4) . . . . ? C13 Zr1 C6 C5 -72.3(4) . . . . ? C15 Zr1 C6 C5 -125.6(3) . . . . ? C11 Zr1 C6 C5 -110.0(3) . . . . ? C12 Zr1 C6 C5 -72.1(4) . . . . ? C7 Zr1 C6 C5 115.6(5) . . . . ? C8 Zr1 C6 C5 78.4(3) . . . . ? C4 Zr1 C6 C5 38.8(3) . . . . ? Cl1 Zr1 C6 C7 -81.0(4) . . . . ? Cl2 Zr1 C6 C7 34.6(3) . . . . ? C14 Zr1 C6 C7 141.8(4) . . . . ? C13 Zr1 C6 C7 172.1(4) . . . . ? C5 Zr1 C6 C7 -115.6(5) . . . . ? C15 Zr1 C6 C7 118.8(3) . . . . ? C11 Zr1 C6 C7 134.4(3) . . . . ? C12 Zr1 C6 C7 172.3(3) . . . . ? C8 Zr1 C6 C7 -37.2(3) . . . . ? C4 Zr1 C6 C7 -76.8(3) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? Zr1 C6 C7 C8 68.1(3) . . . . ? C5 C6 C7 Zr1 -68.3(3) . . . . ? Cl1 Zr1 C7 C8 9.0(4) . . . . ? C6 Zr1 C7 C8 -113.4(5) . . . . ? Cl2 Zr1 C7 C8 100.1(3) . . . . ? C14 Zr1 C7 C8 -152.1(4) . . . . ? C13 Zr1 C7 C8 -122.9(4) . . . . ? C5 Zr1 C7 C8 -76.6(3) . . . . ? C15 Zr1 C7 C8 174.7(3) . . . . ? C11 Zr1 C7 C8 165.7(3) . . . . ? C12 Zr1 C7 C8 -128.5(4) . . . . ? C4 Zr1 C7 C8 -35.6(3) . . . . ? Cl1 Zr1 C7 C6 122.5(3) . . . . ? Cl2 Zr1 C7 C6 -146.4(3) . . . . ? C14 Zr1 C7 C6 -38.6(4) . . . . ? C13 Zr1 C7 C6 -9.4(4) . . . . ? C5 Zr1 C7 C6 36.8(3) . . . . ? C15 Zr1 C7 C6 -71.9(4) . . . . ? C11 Zr1 C7 C6 -80.8(5) . . . . ? C12 Zr1 C7 C6 -15.1(6) . . . . ? C8 Zr1 C7 C6 113.4(5) . . . . ? C4 Zr1 C7 C6 77.9(3) . . . . ? C6 C7 C8 C4 1.7(5) . . . . ? Zr1 C7 C8 C4 66.3(3) . . . . ? C6 C7 C8 C1 171.7(5) . . . . ? Zr1 C7 C8 C1 -123.7(6) . . . . ? C6 C7 C8 Zr1 -64.6(3) . . . . ? C5 C4 C8 C7 -2.5(5) . . . . ? C3 C4 C8 C7 174.3(4) . . . . ? Zr1 C4 C8 C7 -64.5(3) . . . . ? C5 C4 C8 C1 -175.8(4) . . . . ? C3 C4 C8 C1 1.0(5) . . . . ? Zr1 C4 C8 C1 122.2(3) . . . . ? C5 C4 C8 Zr1 62.0(3) . . . . ? C3 C4 C8 Zr1 -121.2(3) . . . . ? C2 C1 C8 C7 -170.0(6) . . . . ? C2 C1 C8 C4 0.1(5) . . . . ? C2 C1 C8 Zr1 85.1(5) . . . . ? Cl1 Zr1 C8 C7 -172.2(3) . . . . ? C6 Zr1 C8 C7 38.4(3) . . . . ? Cl2 Zr1 C8 C7 -76.0(3) . . . . ? C14 Zr1 C8 C7 37.1(5) . . . . ? C13 Zr1 C8 C7 81.7(4) . . . . ? C5 Zr1 C8 C7 79.5(4) . . . . ? C15 Zr1 C8 C7 -8.9(5) . . . . ? C11 Zr1 C8 C7 -86.8(14) . . . . ? C12 Zr1 C8 C7 125.4(5) . . . . ? C4 Zr1 C8 C7 117.0(4) . . . . ? Cl1 Zr1 C8 C4 70.8(2) . . . . ? C6 Zr1 C8 C4 -78.6(3) . . . . ? Cl2 Zr1 C8 C4 167.0(3) . . . . ? C14 Zr1 C8 C4 -79.9(4) . . . . ? C13 Zr1 C8 C4 -35.3(4) . . . . ? C5 Zr1 C8 C4 -37.5(3) . . . . ? C15 Zr1 C8 C4 -126.0(4) . . . . ? C11 Zr1 C8 C4 156.1(13) . . . . ? C12 Zr1 C8 C4 8.4(6) . . . . ? C7 Zr1 C8 C4 -117.0(4) . . . . ? Cl1 Zr1 C8 C1 -32.7(4) . . . . ? C6 Zr1 C8 C1 177.9(5) . . . . ? Cl2 Zr1 C8 C1 63.5(4) . . . . ? C14 Zr1 C8 C1 176.6(5) . . . . ? C13 Zr1 C8 C1 -138.8(5) . . . . ? C5 Zr1 C8 C1 -141.0(5) . . . . ? C15 Zr1 C8 C1 130.5(5) . . . . ? C11 Zr1 C8 C1 52.6(16) . . . . ? C12 Zr1 C8 C1 -95.1(6) . . . . ? C7 Zr1 C8 C1 139.5(6) . . . . ? C4 Zr1 C8 C1 -103.5(5) . . . . ? Cl1 Zr1 C11 C12 -69.4(4) . . . . ? C6 Zr1 C11 C12 85.4(4) . . . . ? Cl2 Zr1 C11 C12 -165.6(4) . . . . ? C14 Zr1 C11 C12 76.3(4) . . . . ? C13 Zr1 C11 C12 35.5(4) . . . . ? C5 Zr1 C11 C12 40.5(5) . . . . ? C15 Zr1 C11 C12 115.1(6) . . . . ? C7 Zr1 C11 C12 130.5(4) . . . . ? C8 Zr1 C11 C12 -154.7(13) . . . . ? C4 Zr1 C11 C12 -5.2(7) . . . . ? Cl1 Zr1 C11 C15 175.4(4) . . . . ? C6 Zr1 C11 C15 -29.8(5) . . . . ? Cl2 Zr1 C11 C15 79.3(4) . . . . ? C14 Zr1 C11 C15 -38.8(4) . . . . ? C13 Zr1 C11 C15 -79.7(4) . . . . ? C5 Zr1 C11 C15 -74.6(5) . . . . ? C12 Zr1 C11 C15 -115.1(6) . . . . ? C7 Zr1 C11 C15 15.4(6) . . . . ? C8 Zr1 C11 C15 90.1(15) . . . . ? C4 Zr1 C11 C15 -120.4(5) . . . . ? C15 C11 C12 C13 1.8(7) . . . . ? Zr1 C11 C12 C13 -64.4(4) . . . . ? C15 C11 C12 Zr1 66.3(4) . . . . ? Cl1 Zr1 C12 C13 -134.7(4) . . . . ? C6 Zr1 C12 C13 -0.5(5) . . . . ? Cl2 Zr1 C12 C13 133.6(4) . . . . ? C14 Zr1 C12 C13 38.3(4) . . . . ? C5 Zr1 C12 C13 -33.1(5) . . . . ? C15 Zr1 C12 C13 80.5(5) . . . . ? C11 Zr1 C12 C13 117.5(6) . . . . ? C7 Zr1 C12 C13 9.1(7) . . . . ? C8 Zr1 C12 C13 -70.4(6) . . . . ? C4 Zr1 C12 C13 -65.2(5) . . . . ? Cl1 Zr1 C12 C11 107.8(4) . . . . ? C6 Zr1 C12 C11 -117.9(4) . . . . ? Cl2 Zr1 C12 C11 16.1(4) . . . . ? C14 Zr1 C12 C11 -79.2(4) . . . . ? C13 Zr1 C12 C11 -117.5(6) . . . . ? C5 Zr1 C12 C11 -150.6(4) . . . . ? C15 Zr1 C12 C11 -36.9(4) . . . . ? C7 Zr1 C12 C11 -108.4(5) . . . . ? C8 Zr1 C12 C11 172.1(4) . . . . ? C4 Zr1 C12 C11 177.4(3) . . . . ? C11 C12 C13 C14 -2.1(7) . . . . ? Zr1 C12 C13 C14 -67.2(4) . . . . ? C11 C12 C13 Zr1 65.1(4) . . . . ? Cl1 Zr1 C13 C12 45.6(4) . . . . ? C6 Zr1 C13 C12 179.6(4) . . . . ? Cl2 Zr1 C13 C12 -65.7(5) . . . . ? C14 Zr1 C13 C12 -113.5(6) . . . . ? C5 Zr1 C13 C12 148.2(5) . . . . ? C15 Zr1 C13 C12 -75.2(4) . . . . ? C11 Zr1 C13 C12 -35.5(4) . . . . ? C7 Zr1 C13 C12 -175.3(3) . . . . ? C8 Zr1 C13 C12 146.5(3) . . . . ? C4 Zr1 C13 C12 128.1(4) . . . . ? Cl1 Zr1 C13 C14 159.2(4) . . . . ? C6 Zr1 C13 C14 -66.8(4) . . . . ? Cl2 Zr1 C13 C14 47.9(5) . . . . ? C5 Zr1 C13 C14 -98.2(4) . . . . ? C15 Zr1 C13 C14 38.3(4) . . . . ? C11 Zr1 C13 C14 78.1(4) . . . . ? C12 Zr1 C13 C14 113.5(6) . . . . ? C7 Zr1 C13 C14 -61.8(4) . . . . ? C8 Zr1 C13 C14 -100.0(4) . . . . ? C4 Zr1 C13 C14 -118.4(4) . . . . ? C12 C13 C14 C15 1.5(7) . . . . ? Zr1 C13 C14 C15 -67.1(4) . . . . ? C12 C13 C14 Zr1 68.6(4) . . . . ? Cl1 Zr1 C14 C13 -27.8(5) . . . . ? C6 Zr1 C14 C13 110.1(4) . . . . ? Cl2 Zr1 C14 C13 -145.9(4) . . . . ? C5 Zr1 C14 C13 78.2(4) . . . . ? C15 Zr1 C14 C13 -113.8(5) . . . . ? C11 Zr1 C14 C13 -76.8(4) . . . . ? C12 Zr1 C14 C13 -37.1(3) . . . . ? C7 Zr1 C14 C13 130.2(4) . . . . ? C8 Zr1 C14 C13 111.2(4) . . . . ? C4 Zr1 C14 C13 75.0(4) . . . . ? Cl1 Zr1 C14 C15 86.0(5) . . . . ? C6 Zr1 C14 C15 -136.1(4) . . . . ? Cl2 Zr1 C14 C15 -32.1(4) . . . . ? C13 Zr1 C14 C15 113.8(5) . . . . ? C5 Zr1 C14 C15 -167.9(4) . . . . ? C11 Zr1 C14 C15 37.0(3) . . . . ? C12 Zr1 C14 C15 76.7(4) . . . . ? C7 Zr1 C14 C15 -116.0(4) . . . . ? C8 Zr1 C14 C15 -135.0(3) . . . . ? C4 Zr1 C14 C15 -171.2(3) . . . . ? C12 C11 C15 C14 -0.8(6) . . . . ? Zr1 C11 C15 C14 66.1(4) . . . . ? C12 C11 C15 Zr1 -66.9(4) . . . . ? C13 C14 C15 C11 -0.4(6) . . . . ? Zr1 C14 C15 C11 -67.5(4) . . . . ? C13 C14 C15 Zr1 67.0(4) . . . . ? Cl1 Zr1 C15 C11 -5.4(5) . . . . ? C6 Zr1 C15 C11 157.5(4) . . . . ? Cl2 Zr1 C15 C11 -97.0(4) . . . . ? C14 Zr1 C15 C11 113.4(6) . . . . ? C13 Zr1 C15 C11 76.1(4) . . . . ? C5 Zr1 C15 C11 127.3(4) . . . . ? C12 Zr1 C15 C11 36.6(3) . . . . ? C7 Zr1 C15 C11 -170.8(4) . . . . ? C8 Zr1 C15 C11 -165.6(3) . . . . ? C4 Zr1 C15 C11 130.0(4) . . . . ? Cl1 Zr1 C15 C14 -118.8(4) . . . . ? C6 Zr1 C15 C14 44.1(4) . . . . ? Cl2 Zr1 C15 C14 149.5(4) . . . . ? C13 Zr1 C15 C14 -37.3(4) . . . . ? C5 Zr1 C15 C14 13.9(5) . . . . ? C11 Zr1 C15 C14 -113.4(6) . . . . ? C12 Zr1 C15 C14 -76.9(4) . . . . ? C7 Zr1 C15 C14 75.8(4) . . . . ? C8 Zr1 C15 C14 81.0(5) . . . . ? C4 Zr1 C15 C14 16.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.483 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.062