# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_sad _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '2011lkf.CIF.txt' #================================================================ # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Liu, Kefeng Key Laboratory of Biofuels, Qingdao Institute of Bioenergy and Bioprocess Technology Chinese Academy of Sciences Qingdao, 266101 P.R. China ; _publ_contact_author_phone 86(532)80662725 _publ_contact_author_fax 86(532)80662724 _publ_contact_author_email liukf@qibebt.ac.cn _publ_requested_coeditor_name ? #=============================================================== # 2. TITLE AND AUTHOR LIST _publ_section_title ; New Half-sandwich Zirconium(IV) Complexes Bearing N,N-dimethylaniline-amido Ligands: Synthesis, Characterization, and Catalytic Properties for Ethylene Polymerization and Copolymerization with 1-hexene ; loop_ _publ_author_name _publ_author_address #<--'Last name, first name' 'Kefeng Liu' ; State Key Laboratory for Supramolecular Structure and Materials School of Chemistry, Jilin University Changchun, Jilin. 130012 P.R.China Key Laboratory of Biofuels Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences Qingdao, Shandong. 266101 P.R.China ; 'Qiaolin Wu' ; State Key Laboratory for Supramolecular Structure and Materials School of Chemistry, Jilin University Changchun, Jilin. 130012 P.R.China ; 'Xuyang Luo' ; School of Chemistry, Jilin University Changchun, Jilin. 130012 P.R.China ; 'Wei Gao' ; State Key Laboratory for Supramolecular Structure and Materials School of Chemistry, Jilin University Changchun, Jilin. 130012 P.R.China ; 'Ying Mu' ; State Key Laboratory for Supramolecular Structure and Materials School of Chemistry, Jilin University Changchun, Jilin. 130012 P.R.China ; #=============================================================== # 3. CIF files data_C1 _database_code_depnum_ccdc_archive 'CCDC 851873' #TrackingRef '2011lkf.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H36 Cl2 N2 Zr' _chemical_formula_weight 550.70 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5545(5) _cell_length_b 13.5020(8) _cell_length_c 23.1132(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.1080(10) _cell_angle_gamma 90.00 _cell_volume 2665.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour courless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16223 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.03 _reflns_number_total 5247 _reflns_number_gt 4445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.6766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5247 _refine_ls_number_parameters 306 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zr1 Zr 0.32477(2) 0.885496(15) 0.812246(9) 0.02065(8) Uani 1 1 d . . . Cl1 Cl 0.14989(7) 1.02577(5) 0.81424(3) 0.03603(16) Uani 1 1 d . . . Cl2 Cl 0.58837(7) 0.94922(5) 0.82389(3) 0.03713(16) Uani 1 1 d . . . N1 N 0.2867(2) 0.81038(13) 0.88562(8) 0.0231(4) Uani 1 1 d . . . N2 N 0.1798(2) 0.83505(15) 1.03947(9) 0.0308(5) Uani 1 1 d . . . C1 C 0.3986(3) 0.84628(17) 0.71168(10) 0.0261(5) Uani 1 1 d . . . C2 C 0.4052(3) 0.75533(17) 0.74248(10) 0.0249(5) Uani 1 1 d . . . C3 C 0.2503(3) 0.72982(17) 0.75615(10) 0.0252(5) Uani 1 1 d . . . C4 C 0.1492(3) 0.80661(18) 0.73452(10) 0.0284(5) Uani 1 1 d . . . C5 C 0.2410(3) 0.87773(17) 0.70702(10) 0.0289(5) Uani 1 1 d . . . C6 C 0.5342(3) 0.89551(19) 0.68380(11) 0.0392(7) Uani 1 1 d . . . H6A H 0.5336 0.8771 0.6437 0.059 Uiso 1 1 calc R . . H6B H 0.6308 0.8746 0.7031 0.059 Uiso 1 1 calc R . . H6C H 0.5245 0.9661 0.6869 0.059 Uiso 1 1 calc R . . C7 C 0.5498(3) 0.69381(19) 0.75403(12) 0.0372(6) Uani 1 1 d . . . H7A H 0.5293 0.6433 0.7818 0.056 Uiso 1 1 calc R . . H7B H 0.6336 0.7353 0.7690 0.056 Uiso 1 1 calc R . . H7C H 0.5789 0.6635 0.7186 0.056 Uiso 1 1 calc R . . C8 C 0.1993(3) 0.63115(17) 0.77856(11) 0.0354(6) Uani 1 1 d . . . H8A H 0.1822 0.5860 0.7467 0.053 Uiso 1 1 calc R . . H8B H 0.1039 0.6391 0.7981 0.053 Uiso 1 1 calc R . . H8C H 0.2792 0.6053 0.8052 0.053 Uiso 1 1 calc R . . C9 C -0.0262(3) 0.8069(2) 0.73522(13) 0.0465(7) Uani 1 1 d . . . H9A H -0.0619 0.8727 0.7433 0.070 Uiso 1 1 calc R . . H9B H -0.0587 0.7624 0.7647 0.070 Uiso 1 1 calc R . . H9C H -0.0703 0.7859 0.6981 0.070 Uiso 1 1 calc R . . C10 C 0.1811(4) 0.9669(2) 0.67339(12) 0.0467(7) Uani 1 1 d . . . H10A H 0.2434 1.0237 0.6844 0.070 Uiso 1 1 calc R . . H10B H 0.0740 0.9790 0.6817 0.070 Uiso 1 1 calc R . . H10C H 0.1877 0.9549 0.6327 0.070 Uiso 1 1 calc R . . C11 C 0.2330(3) 0.71766(17) 0.90751(10) 0.0267(5) Uani 1 1 d . . . C12 C 0.3398(3) 0.64160(18) 0.92096(10) 0.0327(6) Uani 1 1 d . . . C13 C 0.2813(4) 0.5502(2) 0.93899(12) 0.0472(7) Uani 1 1 d . . . H13 H 0.3501 0.4983 0.9478 0.057 Uiso 1 1 calc R . . C14 C 0.1225(4) 0.5364(2) 0.94377(13) 0.0543(9) Uani 1 1 d . . . H14 H 0.0851 0.4751 0.9552 0.065 Uiso 1 1 calc R . . C15 C 0.0201(4) 0.6125(2) 0.93180(12) 0.0467(8) Uani 1 1 d . . . H15 H -0.0863 0.6025 0.9359 0.056 Uiso 1 1 calc R . . C16 C 0.0712(3) 0.7041(2) 0.91371(11) 0.0347(6) Uani 1 1 d . . . C17 C 0.5136(3) 0.6532(2) 0.91655(12) 0.0409(7) Uani 1 1 d . . . H17A H 0.5338 0.7047 0.8894 0.061 Uiso 1 1 calc R . . H17B H 0.5571 0.5920 0.9036 0.061 Uiso 1 1 calc R . . H17C H 0.5609 0.6701 0.9539 0.061 Uiso 1 1 calc R . . C18 C -0.0453(3) 0.7858(2) 0.90102(13) 0.0474(7) Uani 1 1 d . . . H18A H -0.1460 0.7576 0.8907 0.071 Uiso 1 1 calc R . . H18B H -0.0118 0.8253 0.8695 0.071 Uiso 1 1 calc R . . H18C H -0.0525 0.8267 0.9348 0.071 Uiso 1 1 calc R . . C19 C 0.2982(3) 0.89150(17) 0.93017(10) 0.0259(5) Uani 1 1 d D . . C20 C 0.4062(3) 0.86781(16) 0.98203(10) 0.0247(5) Uani 1 1 d . . . C21 C 0.3473(3) 0.83796(17) 1.03438(10) 0.0274(5) Uani 1 1 d . . . C22 C 0.4506(3) 0.8144(2) 1.08114(11) 0.0387(6) Uani 1 1 d . . . H22 H 0.4114 0.7948 1.1161 0.046 Uiso 1 1 calc R . . C23 C 0.6102(3) 0.8199(2) 1.07599(12) 0.0404(6) Uani 1 1 d . . . H23 H 0.6781 0.8032 1.1073 0.049 Uiso 1 1 calc R . . C24 C 0.6693(3) 0.8501(2) 1.02449(12) 0.0371(6) Uani 1 1 d . . . H24 H 0.7769 0.8537 1.0209 0.044 Uiso 1 1 calc R . . C25 C 0.5678(3) 0.87509(17) 0.97821(11) 0.0315(6) Uani 1 1 d . . . H25 H 0.6081 0.8971 0.9439 0.038 Uiso 1 1 calc R . . C26 C 0.1234(3) 0.9251(2) 1.06604(15) 0.0567(9) Uani 1 1 d . . . H26A H 0.1633 0.9285 1.1056 0.085 Uiso 1 1 calc R . . H26B H 0.0111 0.9245 1.0647 0.085 Uiso 1 1 calc R . . H26C H 0.1587 0.9817 1.0453 0.085 Uiso 1 1 calc R . . C27 C 0.1266(3) 0.7458(2) 1.06802(14) 0.0565(9) Uani 1 1 d . . . H27A H 0.1731 0.6887 1.0512 0.085 Uiso 1 1 calc R . . H27B H 0.0146 0.7413 1.0631 0.085 Uiso 1 1 calc R . . H27C H 0.1569 0.7488 1.1086 0.085 Uiso 1 1 calc R . . H19A H 0.1941(11) 0.9065(15) 0.9413(9) 0.014(5) Uiso 1 1 d D . . H19B H 0.338(2) 0.9492(10) 0.9115(9) 0.028(6) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.02100(12) 0.02157(13) 0.01934(13) -0.00020(9) 0.00061(8) -0.00093(8) Cl1 0.0400(3) 0.0332(3) 0.0346(4) -0.0019(3) -0.0009(3) 0.0122(3) Cl2 0.0304(3) 0.0488(4) 0.0321(4) -0.0005(3) 0.0008(3) -0.0152(3) N1 0.0246(9) 0.0258(10) 0.0189(10) -0.0015(8) 0.0012(8) -0.0032(8) N2 0.0308(11) 0.0365(12) 0.0252(11) 0.0011(9) 0.0016(9) -0.0042(9) C1 0.0316(12) 0.0278(12) 0.0193(12) -0.0019(10) 0.0052(10) -0.0034(10) C2 0.0264(11) 0.0257(12) 0.0226(12) -0.0053(10) 0.0011(9) 0.0003(9) C3 0.0277(12) 0.0266(12) 0.0212(12) -0.0061(10) 0.0003(10) -0.0052(9) C4 0.0230(11) 0.0354(14) 0.0263(13) -0.0082(11) -0.0033(10) -0.0017(10) C5 0.0361(13) 0.0295(13) 0.0204(12) -0.0025(10) -0.0051(10) 0.0032(10) C6 0.0476(16) 0.0403(15) 0.0311(15) -0.0048(12) 0.0159(13) -0.0118(12) C7 0.0332(14) 0.0343(14) 0.0439(16) -0.0051(12) 0.0014(12) 0.0084(11) C8 0.0450(15) 0.0299(14) 0.0318(15) -0.0065(11) 0.0059(12) -0.0119(11) C9 0.0237(13) 0.0614(19) 0.0534(19) -0.0137(15) -0.0073(12) 0.0002(12) C10 0.066(2) 0.0422(17) 0.0301(15) 0.0049(13) -0.0091(14) 0.0135(14) C11 0.0322(12) 0.0298(13) 0.0182(12) -0.0016(10) 0.0013(10) -0.0072(10) C12 0.0471(15) 0.0318(14) 0.0191(13) -0.0023(10) 0.0010(11) -0.0037(11) C13 0.080(2) 0.0294(15) 0.0323(16) 0.0025(12) 0.0050(15) -0.0009(14) C14 0.086(2) 0.0425(18) 0.0361(17) -0.0007(14) 0.0159(16) -0.0313(17) C15 0.0517(17) 0.0540(19) 0.0355(16) -0.0031(14) 0.0130(14) -0.0269(15) C16 0.0376(14) 0.0452(16) 0.0219(13) -0.0042(11) 0.0064(11) -0.0132(12) C17 0.0432(15) 0.0355(15) 0.0434(17) -0.0014(13) -0.0024(13) 0.0098(12) C18 0.0275(14) 0.069(2) 0.0458(18) -0.0005(15) 0.0054(13) -0.0067(13) C19 0.0283(12) 0.0278(13) 0.0219(12) 0.0002(10) 0.0038(10) -0.0004(10) C20 0.0291(12) 0.0208(12) 0.0238(13) -0.0043(9) -0.0032(10) -0.0017(9) C21 0.0326(13) 0.0265(13) 0.0230(13) -0.0017(10) -0.0006(10) -0.0028(10) C22 0.0436(15) 0.0490(17) 0.0232(14) 0.0030(12) -0.0016(11) -0.0038(13) C23 0.0417(15) 0.0481(17) 0.0300(15) 0.0026(13) -0.0126(12) 0.0004(13) C24 0.0284(13) 0.0456(16) 0.0364(16) -0.0059(13) -0.0056(11) -0.0016(11) C25 0.0319(13) 0.0351(14) 0.0275(14) -0.0024(11) 0.0012(11) -0.0046(10) C26 0.0333(15) 0.067(2) 0.069(2) -0.0299(18) 0.0041(15) -0.0026(15) C27 0.0475(17) 0.069(2) 0.052(2) 0.0262(17) -0.0013(15) -0.0179(16) _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 N1 2.0177(18) . ? Zr1 Cl2 2.4149(6) . ? Zr1 Cl1 2.4155(6) . ? Zr1 C1 2.498(2) . ? Zr1 C5 2.500(2) . ? Zr1 C2 2.507(2) . ? Zr1 C4 2.515(2) . ? Zr1 C3 2.533(2) . ? N1 C11 1.435(3) . ? N1 C19 1.503(3) . ? N2 C21 1.444(3) . ? N2 C26 1.456(3) . ? N2 C27 1.458(3) . ? C1 C5 1.412(3) . ? C1 C2 1.419(3) . ? C1 C6 1.511(3) . ? C2 C3 1.421(3) . ? C2 C7 1.502(3) . ? C3 C4 1.424(3) . ? C3 C8 1.503(3) . ? C4 C5 1.413(3) . ? C4 C9 1.501(3) . ? C5 C10 1.508(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.398(3) . ? C11 C16 1.411(3) . ? C12 C13 1.404(4) . ? C12 C17 1.504(4) . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 C15 1.370(4) . ? C14 H14 0.9300 . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 C18 1.505(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.507(3) . ? C19 H19A 0.962(5) . ? C19 H19B 0.961(5) . ? C20 C25 1.394(3) . ? C20 C21 1.395(3) . ? C21 C22 1.395(3) . ? C22 C23 1.379(4) . ? C22 H22 0.9300 . ? C23 C24 1.380(4) . ? C23 H23 0.9300 . ? C24 C25 1.382(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zr1 Cl2 106.13(5) . . ? N1 Zr1 Cl1 104.46(5) . . ? Cl2 Zr1 Cl1 107.10(2) . . ? N1 Zr1 C1 137.39(8) . . ? Cl2 Zr1 C1 84.12(6) . . ? Cl1 Zr1 C1 111.84(6) . . ? N1 Zr1 C5 138.23(8) . . ? Cl2 Zr1 C5 109.88(6) . . ? Cl1 Zr1 C5 84.62(6) . . ? C1 Zr1 C5 32.82(8) . . ? N1 Zr1 C2 104.52(7) . . ? Cl2 Zr1 C2 91.96(5) . . ? Cl1 Zr1 C2 138.94(6) . . ? C1 Zr1 C2 32.94(7) . . ? C5 Zr1 C2 54.48(7) . . ? N1 Zr1 C4 105.67(8) . . ? Cl2 Zr1 C4 138.46(5) . . ? Cl1 Zr1 C4 89.95(6) . . ? C1 Zr1 C4 54.34(7) . . ? C5 Zr1 C4 32.73(8) . . ? C2 Zr1 C4 54.39(7) . . ? N1 Zr1 C3 88.03(7) . . ? Cl2 Zr1 C3 124.06(5) . . ? Cl1 Zr1 C3 121.45(6) . . ? C1 Zr1 C3 54.34(7) . . ? C5 Zr1 C3 54.30(8) . . ? C2 Zr1 C3 32.75(7) . . ? C4 Zr1 C3 32.76(7) . . ? C11 N1 C19 113.87(17) . . ? C11 N1 Zr1 143.53(15) . . ? C19 N1 Zr1 101.65(13) . . ? C21 N2 C26 111.4(2) . . ? C21 N2 C27 113.3(2) . . ? C26 N2 C27 112.3(2) . . ? C5 C1 C2 108.1(2) . . ? C5 C1 C6 125.9(2) . . ? C2 C1 C6 125.7(2) . . ? C5 C1 Zr1 73.66(13) . . ? C2 C1 Zr1 73.85(13) . . ? C6 C1 Zr1 122.83(16) . . ? C1 C2 C3 108.0(2) . . ? C1 C2 C7 125.3(2) . . ? C3 C2 C7 126.5(2) . . ? C1 C2 Zr1 73.21(13) . . ? C3 C2 Zr1 74.64(12) . . ? C7 C2 Zr1 121.72(16) . . ? C2 C3 C4 107.6(2) . . ? C2 C3 C8 125.7(2) . . ? C4 C3 C8 125.7(2) . . ? C2 C3 Zr1 72.61(13) . . ? C4 C3 Zr1 72.94(13) . . ? C8 C3 Zr1 128.98(16) . . ? C5 C4 C3 108.09(19) . . ? C5 C4 C9 125.7(2) . . ? C3 C4 C9 126.0(2) . . ? C5 C4 Zr1 73.05(13) . . ? C3 C4 Zr1 74.30(13) . . ? C9 C4 Zr1 123.34(17) . . ? C1 C5 C4 108.2(2) . . ? C1 C5 C10 125.2(2) . . ? C4 C5 C10 126.4(2) . . ? C1 C5 Zr1 73.51(13) . . ? C4 C5 Zr1 74.22(14) . . ? C10 C5 Zr1 122.64(17) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 121.0(2) . . ? C12 C11 N1 120.1(2) . . ? C16 C11 N1 118.9(2) . . ? C11 C12 C13 118.2(2) . . ? C11 C12 C17 123.0(2) . . ? C13 C12 C17 118.7(2) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 121.5(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C11 118.3(3) . . ? C15 C16 C18 119.8(2) . . ? C11 C16 C18 121.8(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 113.89(18) . . ? N1 C19 H19A 108.0(13) . . ? C20 C19 H19A 111.6(13) . . ? N1 C19 H19B 107.1(14) . . ? C20 C19 H19B 108.4(14) . . ? H19A C19 H19B 107.5(18) . . ? C25 C20 C21 118.8(2) . . ? C25 C20 C19 120.1(2) . . ? C21 C20 C19 121.1(2) . . ? C22 C21 C20 119.7(2) . . ? C22 C21 N2 121.3(2) . . ? C20 C21 N2 119.0(2) . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 119.7(2) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C20 121.2(2) . . ? C24 C25 H25 119.4 . . ? C20 C25 H25 119.4 . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 H27A 109.5 . . ? N2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.370 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.062 #========================================================end data_C2 _database_code_depnum_ccdc_archive 'CCDC 851874' #TrackingRef '2011lkf.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H44 Cl2 N2 Zr' _chemical_formula_weight 606.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.13(2) _cell_length_b 8.833(10) _cell_length_c 19.65(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.601(15) _cell_angle_gamma 90.00 _cell_volume 3125(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4559 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 21.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27146 _diffrn_reflns_av_R_equivalents 0.1307 _diffrn_reflns_av_sigmaI/netI 0.1063 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.25 _reflns_number_total 5539 _reflns_number_gt 3377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+42.7448P] 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 SHELXL _refine_ls_extinction_coef 0.0041(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5539 _refine_ls_number_parameters 337 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1605 _refine_ls_R_factor_gt 0.1051 _refine_ls_wR_factor_ref 0.2709 _refine_ls_wR_factor_gt 0.2428 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.135 _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 0.69383(5) 0.43640(12) 0.87004(6) 0.0387(4) Uani 1 1 d . . . Cl1 Cl 0.63546(18) 0.1959(4) 0.8286(2) 0.0796(13) Uani 1 1 d . . . Cl2 Cl 0.78738(17) 0.4494(5) 0.8254(2) 0.0742(11) Uani 1 1 d . . . N1 N 0.7549(4) 0.4112(9) 0.9848(5) 0.036(2) Uani 1 1 d . . . N2 N 0.8562(5) 0.4899(13) 1.1975(6) 0.060(3) Uani 1 1 d . . . C1 C 0.6175(6) 0.6539(13) 0.8793(7) 0.053(3) Uani 1 1 d . . . C2 C 0.6600(5) 0.7072(12) 0.8426(7) 0.041(3) Uani 1 1 d U . . C3 C 0.6327(6) 0.6419(13) 0.7693(7) 0.051(3) Uani 1 1 d . . . C4 C 0.5754(6) 0.5434(13) 0.7611(7) 0.048(3) Uani 1 1 d . . . C5 C 0.5662(5) 0.5444(12) 0.8289(7) 0.044(3) Uani 1 1 d . . . C6 C 0.6183(7) 0.7139(17) 0.9502(8) 0.076(5) Uani 1 1 d . . . H6A H 0.5711 0.7595 0.9386 0.114 Uiso 1 1 calc R . . H6B H 0.6568 0.7885 0.9721 0.114 Uiso 1 1 calc R . . H6C H 0.6274 0.6326 0.9857 0.114 Uiso 1 1 calc R . . C7 C 0.7205(8) 0.8301(17) 0.8728(9) 0.083(5) Uani 1 1 d U . . H7A H 0.7685 0.7838 0.8900 0.125 Uiso 1 1 calc R . . H7B H 0.7180 0.8824 0.9144 0.125 Uiso 1 1 calc R . . H7C H 0.7129 0.9007 0.8328 0.125 Uiso 1 1 calc R . . C8 C 0.6570(8) 0.6834(16) 0.7098(9) 0.081(5) Uani 1 1 d . . . H8A H 0.6531 0.5964 0.6788 0.121 Uiso 1 1 calc R . . H8B H 0.7077 0.7173 0.7340 0.121 Uiso 1 1 calc R . . H8C H 0.6259 0.7630 0.6783 0.121 Uiso 1 1 calc R . . C9 C 0.5292(7) 0.4520(16) 0.6914(7) 0.068(4) Uani 1 1 d . . . H9A H 0.4866 0.5099 0.6582 0.102 Uiso 1 1 calc R . . H9B H 0.5131 0.3607 0.7061 0.102 Uiso 1 1 calc R . . H9C H 0.5583 0.4268 0.6654 0.102 Uiso 1 1 calc R . . C10 C 0.5051(6) 0.4707(15) 0.8399(7) 0.060(4) Uani 1 1 d . . . H10A H 0.4601 0.5277 0.8136 0.091 Uiso 1 1 calc R . . H10B H 0.5180 0.4673 0.8932 0.091 Uiso 1 1 calc R . . H10C H 0.4977 0.3695 0.8200 0.091 Uiso 1 1 calc R . . C11 C 0.7665(6) 0.2705(13) 1.0249(7) 0.045(3) Uani 1 1 d . . . C12 C 0.7174(8) 0.2284(15) 1.0547(8) 0.062(4) Uani 1 1 d . . . C13 C 0.7282(10) 0.0908(16) 1.0936(9) 0.083(5) Uani 1 1 d . . . H13 H 0.6968 0.0649 1.1149 0.099 Uiso 1 1 calc R . . C14 C 0.7845(11) -0.0073(18) 1.1011(9) 0.092(6) Uani 1 1 d . . . H14 H 0.7907 -0.0985 1.1269 0.111 Uiso 1 1 calc R . . C15 C 0.8323(10) 0.0316(14) 1.0694(8) 0.074(4) Uani 1 1 d . . . H15 H 0.8695 -0.0355 1.0735 0.089 Uiso 1 1 calc R . . C16 C 0.8251(6) 0.1689(13) 1.0319(6) 0.049(3) Uani 1 1 d . . . C17 C 0.6507(7) 0.3265(17) 1.0456(9) 0.070(4) Uani 1 1 d . . . H17 H 0.6461 0.4105 1.0112 0.084 Uiso 1 1 calc R . . C18 C 0.6618(8) 0.393(2) 1.1220(9) 0.089(5) Uani 1 1 d . . . H18A H 0.6610 0.3129 1.1546 0.133 Uiso 1 1 calc R . . H18B H 0.6227 0.4636 1.1137 0.133 Uiso 1 1 calc R . . H18C H 0.7088 0.4442 1.1456 0.133 Uiso 1 1 calc R . . C19 C 0.5768(8) 0.233(2) 1.0098(9) 0.089(5) Uani 1 1 d . . . H19A H 0.5703 0.1900 0.9623 0.133 Uiso 1 1 calc R . . H19B H 0.5356 0.2980 1.0012 0.133 Uiso 1 1 calc R . . H19C H 0.5792 0.1530 1.0440 0.133 Uiso 1 1 calc R . . C20 C 0.8772(5) 0.2041(12) 0.9988(6) 0.044(3) Uani 1 1 d . . . H20 H 0.8686 0.3089 0.9805 0.053 Uiso 1 1 calc R . . C21 C 0.9601(6) 0.1901(16) 1.0613(8) 0.076(5) Uani 1 1 d . . . H21A H 0.9662 0.2438 1.1062 0.114 Uiso 1 1 calc R . . H21B H 0.9925 0.2326 1.0423 0.114 Uiso 1 1 calc R . . H21C H 0.9722 0.0852 1.0735 0.114 Uiso 1 1 calc R . . C22 C 0.8667(6) 0.1002(13) 0.9317(7) 0.057(3) Uani 1 1 d . . . H22A H 0.8779 -0.0024 0.9493 0.085 Uiso 1 1 calc R . . H22B H 0.8994 0.1319 0.9109 0.085 Uiso 1 1 calc R . . H22C H 0.8162 0.1063 0.8931 0.085 Uiso 1 1 calc R . . C23 C 0.7859(5) 0.5450(12) 1.0355(7) 0.047(3) Uani 1 1 d . . . H23A H 0.7630 0.5503 1.0696 0.056 Uiso 1 1 calc R . . H23B H 0.7716 0.6356 1.0043 0.056 Uiso 1 1 calc R . . C24 C 0.8715(6) 0.5466(13) 1.0842(7) 0.050(3) Uani 1 1 d . . . C25 C 0.9032(6) 0.5178(13) 1.1621(7) 0.047(3) Uani 1 1 d . . . C26 C 0.9819(6) 0.5161(15) 1.2034(8) 0.064(4) Uani 1 1 d . . . H26 H 1.0041 0.4951 1.2552 0.076 Uiso 1 1 calc R . . C27 C 1.0255(6) 0.5451(17) 1.1678(8) 0.070(4) Uani 1 1 d . . . H27 H 1.0769 0.5421 1.1959 0.084 Uiso 1 1 calc R . . C28 C 0.9944(6) 0.5793(15) 1.0900(9) 0.065(4) Uani 1 1 d . . . H28 H 1.0244 0.6014 1.0665 0.079 Uiso 1 1 calc R . . C29 C 0.9159(6) 0.5793(14) 1.0481(8) 0.056(3) Uani 1 1 d . . . H29 H 0.8939 0.6013 0.9964 0.068 Uiso 1 1 calc R . . C30 C 0.8719(9) 0.3460(17) 1.2384(10) 0.086(5) Uani 1 1 d . . . H30A H 0.8744 0.2668 1.2062 0.130 Uiso 1 1 calc R . . H30B H 0.8330 0.3239 1.2526 0.130 Uiso 1 1 calc R . . H30C H 0.9185 0.3528 1.2834 0.130 Uiso 1 1 calc R . . C31 C 0.8583(8) 0.6125(16) 1.2487(8) 0.071(4) Uani 1 1 d . . . H31A H 0.9074 0.6198 1.2901 0.107 Uiso 1 1 calc R . . H31B H 0.8235 0.5917 1.2685 0.107 Uiso 1 1 calc R . . H31C H 0.8456 0.7064 1.2212 0.107 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 0.0219(5) 0.0328(6) 0.0449(7) 0.0012(5) 0.0002(4) 0.0069(4) Cl1 0.0595(19) 0.0372(17) 0.082(3) -0.0101(17) -0.0217(17) 0.0047(15) Cl2 0.0505(17) 0.108(3) 0.065(2) 0.034(2) 0.0267(16) 0.042(2) N1 0.028(4) 0.034(5) 0.038(5) -0.002(4) 0.007(4) -0.002(4) N2 0.044(6) 0.063(7) 0.062(7) -0.006(6) 0.014(5) -0.006(5) C1 0.048(7) 0.041(7) 0.062(8) -0.003(6) 0.018(6) 0.023(6) C2 0.020(4) 0.038(4) 0.049(5) 0.004(4) 0.000(3) 0.002(3) C3 0.042(6) 0.035(6) 0.063(9) 0.017(6) 0.013(6) 0.019(5) C4 0.033(5) 0.038(7) 0.060(8) 0.015(6) 0.009(5) 0.015(5) C5 0.021(5) 0.039(6) 0.058(7) 0.009(6) 0.006(5) 0.009(5) C6 0.057(8) 0.073(10) 0.069(10) -0.016(8) 0.002(7) 0.028(7) C7 0.072(6) 0.073(6) 0.092(6) 0.002(4) 0.026(4) 0.000(4) C8 0.065(9) 0.060(9) 0.112(13) 0.037(9) 0.035(9) 0.035(7) C9 0.059(8) 0.064(9) 0.046(8) -0.008(7) -0.007(6) 0.017(7) C10 0.033(6) 0.075(9) 0.061(8) 0.018(7) 0.009(6) 0.007(6) C11 0.044(6) 0.043(7) 0.039(7) 0.000(5) 0.010(5) -0.004(5) C12 0.066(8) 0.054(8) 0.061(9) 0.002(7) 0.024(7) -0.006(7) C13 0.115(13) 0.049(9) 0.074(11) 0.001(8) 0.033(10) -0.017(9) C14 0.147(17) 0.046(9) 0.064(11) 0.012(8) 0.030(11) 0.000(10) C15 0.117(13) 0.033(7) 0.060(9) 0.003(6) 0.028(9) 0.001(7) C16 0.048(7) 0.041(7) 0.037(7) 0.004(5) 0.000(5) 0.005(5) C17 0.064(8) 0.070(9) 0.088(12) -0.009(8) 0.044(8) -0.013(7) C18 0.058(9) 0.124(15) 0.090(12) -0.032(11) 0.038(9) -0.025(9) C19 0.062(9) 0.117(14) 0.067(11) 0.018(10) 0.010(8) -0.027(9) C20 0.032(5) 0.038(6) 0.038(7) 0.004(5) -0.006(5) 0.012(5) C21 0.035(6) 0.070(9) 0.078(10) 0.001(8) -0.016(6) 0.009(6) C22 0.040(6) 0.047(7) 0.058(8) -0.006(6) 0.000(6) -0.001(5) C23 0.033(5) 0.038(6) 0.065(8) 0.000(6) 0.017(5) 0.003(5) C24 0.031(5) 0.038(6) 0.068(8) -0.003(6) 0.011(6) -0.007(5) C25 0.034(6) 0.044(7) 0.048(7) -0.007(5) 0.006(5) -0.007(5) C26 0.037(6) 0.073(9) 0.057(8) -0.010(7) 0.000(6) -0.003(6) C27 0.024(6) 0.089(11) 0.077(10) -0.019(9) 0.006(6) -0.012(7) C28 0.035(6) 0.066(9) 0.088(11) -0.014(8) 0.021(7) -0.016(6) C29 0.047(7) 0.048(7) 0.067(9) -0.006(7) 0.019(6) -0.016(6) C30 0.096(12) 0.059(10) 0.096(13) 0.003(9) 0.036(10) -0.017(9) C31 0.064(9) 0.075(10) 0.058(9) 0.007(8) 0.013(7) 0.009(7) _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 N1 2.040(9) . ? Zr1 Cl1 2.387(4) . ? Zr1 Cl2 2.410(4) . ? Zr1 C2 2.479(11) . ? Zr1 C5 2.512(10) . ? Zr1 C1 2.517(11) . ? Zr1 C3 2.558(11) . ? Zr1 C4 2.567(10) . ? N1 C11 1.434(14) . ? N1 C23 1.491(13) . ? N2 C25 1.425(16) . ? N2 C30 1.461(17) . ? N2 C31 1.466(17) . ? C1 C2 1.424(17) . ? C1 C5 1.438(16) . ? C1 C6 1.483(18) . ? C2 C3 1.415(16) . ? C2 C7 1.539(17) . ? C3 C4 1.395(16) . ? C3 C8 1.502(18) . ? C4 C5 1.427(16) . ? C4 C9 1.500(16) . ? C5 C10 1.491(15) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.405(17) . ? C11 C16 1.439(16) . ? C12 C13 1.399(19) . ? C12 C17 1.541(19) . ? C13 C14 1.38(2) . ? C13 H13 0.9300 . ? C14 C15 1.40(2) . ? C14 H14 0.9300 . ? C15 C16 1.392(17) . ? C15 H15 0.9300 . ? C16 C20 1.495(17) . ? C17 C18 1.533(19) . ? C17 C19 1.568(18) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.543(16) . ? C20 C21 1.573(13) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.553(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.393(16) . ? C24 C29 1.398(17) . ? C25 C26 1.421(15) . ? C26 C27 1.370(18) . ? C26 H26 0.9300 . ? C27 C28 1.400(19) . ? C27 H27 0.9300 . ? C28 C29 1.417(16) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zr1 Cl1 103.9(3) . . ? N1 Zr1 Cl2 103.0(3) . . ? Cl1 Zr1 Cl2 105.30(17) . . ? N1 Zr1 C2 108.5(4) . . ? Cl1 Zr1 C2 137.6(3) . . ? Cl2 Zr1 C2 93.3(3) . . ? N1 Zr1 C5 114.9(4) . . ? Cl1 Zr1 C5 87.2(3) . . ? Cl2 Zr1 C5 136.0(3) . . ? C2 Zr1 C5 54.7(3) . . ? N1 Zr1 C1 95.1(4) . . ? Cl1 Zr1 C1 118.7(3) . . ? Cl2 Zr1 C1 126.3(3) . . ? C2 Zr1 C1 33.1(4) . . ? C5 Zr1 C1 33.2(4) . . ? N1 Zr1 C3 140.9(4) . . ? Cl1 Zr1 C3 112.0(3) . . ? Cl2 Zr1 C3 82.4(3) . . ? C2 Zr1 C3 32.6(4) . . ? C5 Zr1 C3 54.1(4) . . ? C1 Zr1 C3 54.3(4) . . ? N1 Zr1 C4 146.8(4) . . ? Cl1 Zr1 C4 84.9(3) . . ? Cl2 Zr1 C4 105.3(3) . . ? C2 Zr1 C4 53.2(3) . . ? C5 Zr1 C4 32.6(4) . . ? C1 Zr1 C4 53.9(4) . . ? C3 Zr1 C4 31.6(4) . . ? C11 N1 C23 113.7(8) . . ? C11 N1 Zr1 124.9(7) . . ? C23 N1 Zr1 121.1(7) . . ? C25 N2 C30 113.1(11) . . ? C25 N2 C31 112.7(10) . . ? C30 N2 C31 109.4(11) . . ? C2 C1 C5 106.5(11) . . ? C2 C1 C6 126.9(12) . . ? C5 C1 C6 126.1(12) . . ? C2 C1 Zr1 72.0(6) . . ? C5 C1 Zr1 73.2(6) . . ? C6 C1 Zr1 126.2(8) . . ? C3 C2 C1 109.5(10) . . ? C3 C2 C7 124.0(12) . . ? C1 C2 C7 126.1(12) . . ? C3 C2 Zr1 76.8(6) . . ? C1 C2 Zr1 74.9(6) . . ? C7 C2 Zr1 120.3(8) . . ? C4 C3 C2 107.2(11) . . ? C4 C3 C8 127.1(13) . . ? C2 C3 C8 125.5(12) . . ? C4 C3 Zr1 74.6(6) . . ? C2 C3 Zr1 70.6(6) . . ? C8 C3 Zr1 124.4(7) . . ? C3 C4 C5 109.6(11) . . ? C3 C4 C9 125.8(13) . . ? C5 C4 C9 124.7(11) . . ? C3 C4 Zr1 73.9(6) . . ? C5 C4 Zr1 71.6(6) . . ? C9 C4 Zr1 121.9(7) . . ? C4 C5 C1 107.1(10) . . ? C4 C5 C10 126.5(11) . . ? C1 C5 C10 125.4(12) . . ? C4 C5 Zr1 75.8(6) . . ? C1 C5 Zr1 73.6(5) . . ? C10 C5 Zr1 125.4(7) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N1 119.2(10) . . ? C12 C11 C16 119.6(11) . . ? N1 C11 C16 121.1(10) . . ? C13 C12 C11 119.4(14) . . ? C13 C12 C17 117.8(14) . . ? C11 C12 C17 122.8(12) . . ? C14 C13 C12 121.5(16) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 119.5(14) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 121.2(15) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 118.7(13) . . ? C15 C16 C20 118.9(12) . . ? C11 C16 C20 122.3(10) . . ? C18 C17 C12 111.4(13) . . ? C18 C17 C19 109.6(12) . . ? C12 C17 C19 111.0(12) . . ? C18 C17 H17 108.3 . . ? C12 C17 H17 108.3 . . ? C19 C17 H17 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 C22 113.2(10) . . ? C16 C20 C21 110.5(10) . . ? C22 C20 C21 108.2(10) . . ? C16 C20 H20 108.2 . . ? C22 C20 H20 108.2 . . ? C21 C20 H20 108.2 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C23 C24 115.8(9) . . ? N1 C23 H23A 108.3 . . ? C24 C23 H23A 108.3 . . ? N1 C23 H23B 108.3 . . ? C24 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C25 C24 C29 120.9(10) . . ? C25 C24 C23 120.7(11) . . ? C29 C24 C23 118.4(11) . . ? C24 C25 C26 118.3(12) . . ? C24 C25 N2 119.5(10) . . ? C26 C25 N2 122.3(11) . . ? C27 C26 C25 120.9(12) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 121.4(11) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C27 C28 C29 118.2(12) . . ? C27 C28 H28 120.9 . . ? C29 C28 H28 120.9 . . ? C24 C29 C28 120.3(13) . . ? C24 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? N2 C30 H30A 109.5 . . ? N2 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N2 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N2 C31 H31A 109.5 . . ? N2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.987 _refine_diff_density_min -1.436 _refine_diff_density_rms 0.134 #========================================================end data_C3 _database_code_depnum_ccdc_archive 'CCDC 851875' #TrackingRef '2011lkf.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cl2 N2 Zr' _chemical_formula_weight 488.63 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2590(6) _cell_length_b 14.6848(8) _cell_length_c 16.2009(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.5010(10) _cell_angle_gamma 90.00 _cell_volume 2399.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4451 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.9 _exptl_crystal_description block _exptl_crystal_colour courless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13582 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4227 _reflns_number_gt 3489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.6316P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4227 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.68240(2) 0.271996(17) 0.803183(15) 0.02587(9) Uani 1 1 d . . . Cl1 Cl 0.78473(7) 0.35193(5) 0.92920(4) 0.04224(19) Uani 1 1 d . . . Cl2 Cl 0.66975(8) 0.11502(5) 0.84646(5) 0.0484(2) Uani 1 1 d . . . N1 N 0.4914(2) 0.30934(14) 0.77305(13) 0.0291(5) Uani 1 1 d . . . N2 N 0.1439(2) 0.36686(16) 0.58967(13) 0.0361(6) Uani 1 1 d . . . C1 C 0.7630(3) 0.36696(18) 0.69434(16) 0.0325(6) Uani 1 1 d . . . C2 C 0.8778(3) 0.33491(19) 0.74948(17) 0.0336(6) Uani 1 1 d . . . C3 C 0.8822(3) 0.23904(19) 0.74168(18) 0.0349(6) Uani 1 1 d . . . C4 C 0.7725(3) 0.21179(18) 0.67983(17) 0.0340(6) Uani 1 1 d . . . C5 C 0.6993(3) 0.29095(19) 0.64971(16) 0.0330(6) Uani 1 1 d . . . C6 C 0.7232(3) 0.46509(19) 0.67889(19) 0.0488(8) Uani 1 1 d . . . H6A H 0.7521 0.4862 0.6291 0.073 Uiso 1 1 calc R . . H6B H 0.7637 0.5013 0.7260 0.073 Uiso 1 1 calc R . . H6C H 0.6286 0.4703 0.6717 0.073 Uiso 1 1 calc R . . C7 C 0.9843(3) 0.3936(2) 0.7991(2) 0.0513(8) Uani 1 1 d . . . H7A H 1.0264 0.3613 0.8483 0.077 Uiso 1 1 calc R . . H7B H 0.9455 0.4487 0.8155 0.077 Uiso 1 1 calc R . . H7C H 1.0489 0.4084 0.7652 0.077 Uiso 1 1 calc R . . C8 C 0.9872(3) 0.1761(2) 0.7858(2) 0.0538(9) Uani 1 1 d . . . H8A H 1.0550 0.1688 0.7526 0.081 Uiso 1 1 calc R . . H8B H 0.9485 0.1179 0.7936 0.081 Uiso 1 1 calc R . . H8C H 1.0253 0.2013 0.8395 0.081 Uiso 1 1 calc R . . C9 C 0.7462(4) 0.1165(2) 0.6471(2) 0.0539(9) Uani 1 1 d . . . H9A H 0.6566 0.1121 0.6172 0.081 Uiso 1 1 calc R . . H9B H 0.7591 0.0745 0.6933 0.081 Uiso 1 1 calc R . . H9C H 0.8062 0.1020 0.6100 0.081 Uiso 1 1 calc R . . C10 C 0.5949(3) 0.2952(2) 0.57189(17) 0.0487(8) Uani 1 1 d . . . H10A H 0.5472 0.3515 0.5709 0.073 Uiso 1 1 calc R . . H10B H 0.5346 0.2451 0.5716 0.073 Uiso 1 1 calc R . . H10C H 0.6361 0.2915 0.5233 0.073 Uiso 1 1 calc R . . C11 C 0.3863(3) 0.33636(18) 0.70419(16) 0.0324(6) Uani 1 1 d . . . H11A H 0.4248 0.3744 0.6659 0.039 Uiso 1 1 calc R . . H11B H 0.3229 0.3733 0.7269 0.039 Uiso 1 1 calc R . . C12 C 0.3118(2) 0.25826(18) 0.65407(17) 0.0301(6) Uani 1 1 d . . . C13 C 0.1910(3) 0.27504(19) 0.59977(16) 0.0319(6) Uani 1 1 d . . . C14 C 0.1199(3) 0.2022(2) 0.55788(18) 0.0430(7) Uani 1 1 d . . . H14 H 0.0391 0.2131 0.5227 0.052 Uiso 1 1 calc R . . C15 C 0.1678(3) 0.1142(2) 0.5679(2) 0.0494(8) Uani 1 1 d . . . H15 H 0.1193 0.0663 0.5400 0.059 Uiso 1 1 calc R . . C16 C 0.2876(3) 0.0980(2) 0.61924(19) 0.0452(8) Uani 1 1 d . . . H16 H 0.3213 0.0391 0.6253 0.054 Uiso 1 1 calc R . . C17 C 0.3580(3) 0.16921(19) 0.66197(18) 0.0400(7) Uani 1 1 d . . . H17 H 0.4386 0.1572 0.6970 0.048 Uiso 1 1 calc R . . C18 C 0.2109(3) 0.41997(19) 0.53381(18) 0.0416(7) Uani 1 1 d . . . H18A H 0.3049 0.4109 0.5488 0.062 Uiso 1 1 calc R . . H18B H 0.1909 0.4834 0.5389 0.062 Uiso 1 1 calc R . . H18C H 0.1809 0.4007 0.4769 0.062 Uiso 1 1 calc R . . C19 C 0.0008(3) 0.3770(3) 0.5648(2) 0.0569(9) Uani 1 1 d . . . H19A H -0.0252 0.3618 0.5065 0.085 Uiso 1 1 calc R . . H19B H -0.0237 0.4388 0.5737 0.085 Uiso 1 1 calc R . . H19C H -0.0429 0.3370 0.5979 0.085 Uiso 1 1 calc R . . C20 C 0.4512(3) 0.30223(19) 0.85648(17) 0.0343(6) Uani 1 1 d D . . C21 C 0.3429(3) 0.2324(2) 0.8599(2) 0.0513(8) Uani 1 1 d . . . H21A H 0.2639 0.2499 0.8218 0.077 Uiso 1 1 calc R . . H21B H 0.3249 0.2295 0.9159 0.077 Uiso 1 1 calc R . . H21C H 0.3717 0.1738 0.8441 0.077 Uiso 1 1 calc R . . C22 C 0.4183(3) 0.3939(2) 0.8911(2) 0.0478(8) Uani 1 1 d . . . H22A H 0.4902 0.4355 0.8902 0.072 Uiso 1 1 calc R . . H22B H 0.4048 0.3865 0.9478 0.072 Uiso 1 1 calc R . . H22C H 0.3390 0.4177 0.8573 0.072 Uiso 1 1 calc R . . H20 H 0.5307(13) 0.2813(14) 0.8921(12) 0.019(6) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.02249(14) 0.03012(15) 0.02345(15) 0.00582(11) 0.00010(10) 0.00087(11) Cl1 0.0357(4) 0.0589(5) 0.0290(4) -0.0035(3) -0.0024(3) -0.0033(3) Cl2 0.0551(5) 0.0366(4) 0.0543(5) 0.0196(3) 0.0126(4) 0.0078(3) N1 0.0240(11) 0.0320(12) 0.0287(12) 0.0052(10) -0.0025(9) -0.0005(9) N2 0.0311(13) 0.0498(15) 0.0253(12) 0.0032(10) -0.0003(10) 0.0125(11) C1 0.0385(15) 0.0325(15) 0.0290(15) 0.0066(12) 0.0130(12) 0.0026(12) C2 0.0305(15) 0.0380(16) 0.0335(16) 0.0023(12) 0.0093(12) -0.0068(12) C3 0.0283(14) 0.0415(16) 0.0354(16) 0.0042(13) 0.0074(12) 0.0036(12) C4 0.0377(15) 0.0332(15) 0.0322(15) -0.0020(12) 0.0094(12) -0.0018(12) C5 0.0334(15) 0.0428(17) 0.0229(14) 0.0017(12) 0.0050(11) 0.0009(12) C6 0.064(2) 0.0372(17) 0.0493(19) 0.0119(14) 0.0224(16) 0.0065(15) C7 0.0411(18) 0.061(2) 0.051(2) -0.0037(16) 0.0080(15) -0.0216(16) C8 0.0332(17) 0.063(2) 0.064(2) 0.0154(18) 0.0080(15) 0.0138(15) C9 0.077(2) 0.0407(18) 0.047(2) -0.0068(15) 0.0197(18) -0.0043(17) C10 0.0445(18) 0.075(2) 0.0243(15) 0.0020(15) -0.0003(13) 0.0026(16) C11 0.0283(14) 0.0330(15) 0.0319(15) 0.0051(12) -0.0047(11) 0.0023(12) C12 0.0254(14) 0.0329(15) 0.0309(15) 0.0058(11) 0.0021(11) 0.0003(11) C13 0.0267(14) 0.0406(16) 0.0281(15) 0.0053(12) 0.0040(11) 0.0004(12) C14 0.0307(16) 0.058(2) 0.0367(17) 0.0015(15) -0.0030(13) -0.0075(14) C15 0.052(2) 0.047(2) 0.0455(19) -0.0057(15) -0.0017(15) -0.0176(16) C16 0.0507(19) 0.0327(16) 0.050(2) 0.0026(14) 0.0024(15) -0.0013(14) C17 0.0338(16) 0.0357(16) 0.0467(18) 0.0048(13) -0.0028(13) 0.0025(13) C18 0.0469(18) 0.0337(16) 0.0390(17) 0.0034(13) -0.0058(14) 0.0033(13) C19 0.0385(18) 0.090(3) 0.0420(19) 0.0175(18) 0.0073(15) 0.0271(18) C20 0.0253(14) 0.0451(17) 0.0320(16) 0.0104(13) 0.0035(12) 0.0023(12) C21 0.0384(17) 0.061(2) 0.056(2) 0.0121(17) 0.0138(15) -0.0115(16) C22 0.0450(19) 0.0530(19) 0.0476(19) -0.0006(15) 0.0141(15) 0.0080(15) _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 N1 2.007(2) . ? Zr1 Cl2 2.4198(7) . ? Zr1 Cl1 2.4221(7) . ? Zr1 C3 2.485(3) . ? Zr1 C2 2.503(2) . ? Zr1 C1 2.504(2) . ? Zr1 C4 2.511(3) . ? Zr1 C5 2.539(3) . ? Zr1 H20 2.31(2) . ? N1 C11 1.458(3) . ? N1 C20 1.487(3) . ? N2 C13 1.431(3) . ? N2 C19 1.458(4) . ? N2 C18 1.458(4) . ? C1 C5 1.422(4) . ? C1 C2 1.422(4) . ? C1 C6 1.506(4) . ? C2 C3 1.415(4) . ? C2 C7 1.505(4) . ? C3 C4 1.421(4) . ? C3 C8 1.498(4) . ? C4 C5 1.421(4) . ? C4 C9 1.503(4) . ? C5 C10 1.499(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.528(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.389(4) . ? C12 C13 1.405(4) . ? C13 C14 1.399(4) . ? C14 C15 1.380(4) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.383(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.520(4) . ? C20 C22 1.521(4) . ? C20 H20 0.959(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zr1 Cl2 103.25(6) . . ? N1 Zr1 Cl1 109.05(6) . . ? Cl2 Zr1 Cl1 104.80(3) . . ? N1 Zr1 C3 142.73(9) . . ? Cl2 Zr1 C3 91.28(7) . . ? Cl1 Zr1 C3 99.78(7) . . ? N1 Zr1 C2 128.51(9) . . ? Cl2 Zr1 C2 122.75(7) . . ? Cl1 Zr1 C2 82.10(7) . . ? C3 Zr1 C2 32.96(9) . . ? N1 Zr1 C1 96.29(8) . . ? Cl2 Zr1 C1 140.96(6) . . ? Cl1 Zr1 C1 100.12(7) . . ? C3 Zr1 C1 54.81(9) . . ? C2 Zr1 C1 33.01(9) . . ? N1 Zr1 C4 112.79(9) . . ? Cl2 Zr1 C4 86.68(6) . . ? Cl1 Zr1 C4 132.50(7) . . ? C3 Zr1 C4 33.05(9) . . ? C2 Zr1 C4 54.47(9) . . ? C1 Zr1 C4 54.47(8) . . ? N1 Zr1 C5 88.27(8) . . ? Cl2 Zr1 C5 113.89(7) . . ? Cl1 Zr1 C5 132.51(7) . . ? C3 Zr1 C5 54.55(9) . . ? C2 Zr1 C5 54.35(9) . . ? C1 Zr1 C5 32.75(8) . . ? C4 Zr1 C5 32.68(8) . . ? N1 Zr1 H20 52.9(2) . . ? Cl2 Zr1 H20 78.3(5) . . ? Cl1 Zr1 H20 71.6(4) . . ? C3 Zr1 H20 163.9(2) . . ? C2 Zr1 H20 150.3(5) . . ? C1 Zr1 H20 138.8(4) . . ? C4 Zr1 H20 154.8(5) . . ? C5 Zr1 H20 141.1(2) . . ? C11 N1 C20 115.2(2) . . ? C11 N1 Zr1 144.40(17) . . ? C20 N1 Zr1 100.35(15) . . ? C13 N2 C19 115.4(2) . . ? C13 N2 C18 112.8(2) . . ? C19 N2 C18 109.8(2) . . ? C5 C1 C2 108.1(2) . . ? C5 C1 C6 125.5(3) . . ? C2 C1 C6 126.1(3) . . ? C5 C1 Zr1 74.99(14) . . ? C2 C1 Zr1 73.45(14) . . ? C6 C1 Zr1 122.41(17) . . ? C3 C2 C1 108.0(2) . . ? C3 C2 C7 125.9(3) . . ? C1 C2 C7 125.7(3) . . ? C3 C2 Zr1 72.82(14) . . ? C1 C2 Zr1 73.53(14) . . ? C7 C2 Zr1 125.14(18) . . ? C2 C3 C4 108.0(2) . . ? C2 C3 C8 127.1(3) . . ? C4 C3 C8 124.8(3) . . ? C2 C3 Zr1 74.22(15) . . ? C4 C3 Zr1 74.47(15) . . ? C8 C3 Zr1 120.17(19) . . ? C5 C4 C3 108.2(2) . . ? C5 C4 C9 126.2(3) . . ? C3 C4 C9 125.4(3) . . ? C5 C4 Zr1 74.76(14) . . ? C3 C4 Zr1 72.47(15) . . ? C9 C4 Zr1 122.68(18) . . ? C4 C5 C1 107.6(2) . . ? C4 C5 C10 125.0(3) . . ? C1 C5 C10 125.9(3) . . ? C4 C5 Zr1 72.56(14) . . ? C1 C5 Zr1 72.26(14) . . ? C10 C5 Zr1 131.46(18) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 115.5(2) . . ? N1 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N1 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C17 C12 C13 118.1(3) . . ? C17 C12 C11 121.9(2) . . ? C13 C12 C11 120.0(2) . . ? C14 C13 C12 119.5(3) . . ? C14 C13 N2 122.0(2) . . ? C12 C13 N2 118.5(2) . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 121.8(3) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 C21 113.9(2) . . ? N1 C20 C22 113.0(2) . . ? C21 C20 C22 111.8(2) . . ? N1 C20 H20 102.9(14) . . ? C21 C20 H20 108.0(14) . . ? C22 C20 H20 106.5(14) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.477 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.063 #========================================================end data_C4 _database_code_depnum_ccdc_archive 'CCDC 851876' #TrackingRef '2011lkf.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H36 Cl2 N2 Zr' _chemical_formula_weight 502.66 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 8.0251(6) _cell_length_b 11.4954(8) _cell_length_c 13.8983(10) _cell_angle_alpha 105.0150(10) _cell_angle_beta 94.0820(10) _cell_angle_gamma 98.1910(10) _cell_volume 1217.87(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4900 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour courless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.682 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7365 _diffrn_reflns_av_R_equivalents 0.0113 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4682 _reflns_number_gt 4348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.6365P] 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 4682 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.64784(2) 0.832421(15) 0.674909(13) 0.02160(7) Uani 1 1 d . . . Cl1 Cl 0.52392(7) 1.01539(4) 0.72703(4) 0.03364(12) Uani 1 1 d . . . Cl2 Cl 0.41375(7) 0.69835(5) 0.56192(4) 0.03682(13) Uani 1 1 d . . . N1 N 0.6641(2) 0.77675(14) 0.80134(12) 0.0249(3) Uani 1 1 d . . . N2 N 0.7190(2) 0.43055(14) 0.82019(12) 0.0286(4) Uani 1 1 d . . . C1 C 0.8745(3) 0.75750(18) 0.57339(16) 0.0311(4) Uani 1 1 d . . . C2 C 0.7890(3) 0.81902(18) 0.51349(15) 0.0301(4) Uani 1 1 d . . . C3 C 0.8156(2) 0.94434(17) 0.56552(15) 0.0270(4) Uani 1 1 d . . . C4 C 0.9175(2) 0.96048(17) 0.65784(14) 0.0258(4) Uani 1 1 d . . . C5 C 0.9566(2) 0.84526(18) 0.66191(15) 0.0285(4) Uani 1 1 d . . . C6 C 0.8943(4) 0.6251(2) 0.5401(2) 0.0510(7) Uani 1 1 d . . . H6A H 0.9783 0.6156 0.4941 0.076 Uiso 1 1 calc R . . H6B H 0.7881 0.5765 0.5077 0.076 Uiso 1 1 calc R . . H6C H 0.9293 0.5988 0.5974 0.076 Uiso 1 1 calc R . . C7 C 0.6989(3) 0.7608(2) 0.41029(16) 0.0460(6) Uani 1 1 d . . . H7A H 0.6311 0.8155 0.3915 0.069 Uiso 1 1 calc R . . H7B H 0.6272 0.6862 0.4097 0.069 Uiso 1 1 calc R . . H7C H 0.7806 0.7435 0.3636 0.069 Uiso 1 1 calc R . . C8 C 0.7583(3) 1.0453(2) 0.52785(17) 0.0372(5) Uani 1 1 d . . . H8A H 0.8550 1.0961 0.5149 0.056 Uiso 1 1 calc R . . H8B H 0.7003 1.0935 0.5776 0.056 Uiso 1 1 calc R . . H8C H 0.6829 1.0107 0.4671 0.056 Uiso 1 1 calc R . . C9 C 0.9875(3) 1.08177(19) 0.73210(17) 0.0376(5) Uani 1 1 d . . . H9A H 0.9053 1.1048 0.7773 0.056 Uiso 1 1 calc R . . H9B H 1.0124 1.1427 0.6969 0.056 Uiso 1 1 calc R . . H9C H 1.0894 1.0750 0.7694 0.056 Uiso 1 1 calc R . . C10 C 1.0807(3) 0.8231(2) 0.73902(19) 0.0424(5) Uani 1 1 d . . . H10A H 1.1922 0.8314 0.7181 0.064 Uiso 1 1 calc R . . H10B H 1.0487 0.7422 0.7458 0.064 Uiso 1 1 calc R . . H10C H 1.0804 0.8818 0.8023 0.064 Uiso 1 1 calc R . . C11 C 0.6641(2) 0.64488(17) 0.76088(15) 0.0262(4) Uani 1 1 d . . . H11A H 0.7703 0.6264 0.7859 0.031 Uiso 1 1 calc R . . H11B H 0.6601 0.6266 0.6885 0.031 Uiso 1 1 calc R . . C12 C 0.5197(2) 0.56054(17) 0.78592(14) 0.0253(4) Uani 1 1 d . . . C13 C 0.5518(2) 0.45904(16) 0.81884(14) 0.0253(4) Uani 1 1 d . . . C14 C 0.4186(3) 0.39068(18) 0.85034(16) 0.0328(4) Uani 1 1 d . . . H14 H 0.4391 0.3251 0.8743 0.039 Uiso 1 1 calc R . . C15 C 0.2580(3) 0.4189(2) 0.84641(17) 0.0360(5) Uani 1 1 d . . . H15 H 0.1714 0.3727 0.8681 0.043 Uiso 1 1 calc R . . C16 C 0.2239(3) 0.51580(19) 0.81037(16) 0.0344(5) Uani 1 1 d . . . H16 H 0.1147 0.5339 0.8065 0.041 Uiso 1 1 calc R . . C17 C 0.3553(3) 0.58501(18) 0.78027(16) 0.0315(4) Uani 1 1 d . . . H17 H 0.3328 0.6497 0.7556 0.038 Uiso 1 1 calc R . . C18 C 0.7591(3) 0.3708(2) 0.72008(17) 0.0375(5) Uani 1 1 d . . . H18A H 0.6954 0.2895 0.6977 0.056 Uiso 1 1 calc R . . H18B H 0.8780 0.3671 0.7225 0.056 Uiso 1 1 calc R . . H18C H 0.7300 0.4165 0.6744 0.056 Uiso 1 1 calc R . . C19 C 0.7603(3) 0.3623(2) 0.89166(19) 0.0426(5) Uani 1 1 d . . . H19A H 0.7276 0.4006 0.9558 0.064 Uiso 1 1 calc R . . H19B H 0.8800 0.3615 0.8978 0.064 Uiso 1 1 calc R . . H19C H 0.7003 0.2800 0.8682 0.064 Uiso 1 1 calc R . . C20 C 0.7009(3) 0.82873(18) 0.91214(15) 0.0314(4) Uani 1 1 d . . . C21 C 0.7800(3) 0.96332(19) 0.93190(16) 0.0370(5) Uani 1 1 d . . . H21A H 0.8843 0.9689 0.9024 0.055 Uiso 1 1 calc R . . H21B H 0.8019 1.0003 1.0029 0.055 Uiso 1 1 calc R . . H21C H 0.7032 1.0050 0.9028 0.055 Uiso 1 1 calc R . . C22 C 0.8254(3) 0.7638(2) 0.95897(18) 0.0462(6) Uani 1 1 d . . . H22A H 0.7778 0.6791 0.9464 0.069 Uiso 1 1 calc R . . H22B H 0.8463 0.8008 1.0300 0.069 Uiso 1 1 calc R . . H22C H 0.9300 0.7709 0.9298 0.069 Uiso 1 1 calc R . . C23 C 0.5365(3) 0.8232(2) 0.96160(18) 0.0478(6) Uani 1 1 d . . . H23A H 0.4572 0.8608 0.9300 0.072 Uiso 1 1 calc R . . H23B H 0.5602 0.8658 1.0315 0.072 Uiso 1 1 calc R . . H23C H 0.4889 0.7394 0.9543 0.072 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 0.02085(10) 0.02163(10) 0.02291(10) 0.00703(7) 0.00318(7) 0.00341(7) Cl1 0.0360(3) 0.0313(2) 0.0372(3) 0.0101(2) 0.0078(2) 0.0143(2) Cl2 0.0306(3) 0.0428(3) 0.0314(3) 0.0077(2) -0.0029(2) -0.0050(2) N1 0.0262(8) 0.0235(8) 0.0256(8) 0.0087(6) 0.0031(6) 0.0023(6) N2 0.0287(9) 0.0262(8) 0.0319(9) 0.0085(7) 0.0021(7) 0.0072(7) C1 0.0299(11) 0.0275(10) 0.0385(11) 0.0086(8) 0.0167(9) 0.0077(8) C2 0.0308(11) 0.0319(10) 0.0267(10) 0.0057(8) 0.0114(8) 0.0018(8) C3 0.0253(10) 0.0288(10) 0.0293(10) 0.0114(8) 0.0077(8) 0.0043(8) C4 0.0220(9) 0.0267(9) 0.0292(10) 0.0089(8) 0.0068(7) 0.0016(7) C5 0.0222(10) 0.0320(10) 0.0356(11) 0.0141(8) 0.0100(8) 0.0064(8) C6 0.0627(17) 0.0296(11) 0.0647(17) 0.0087(11) 0.0315(13) 0.0166(11) C7 0.0505(14) 0.0525(14) 0.0273(11) 0.0038(10) 0.0090(10) -0.0055(11) C8 0.0402(12) 0.0399(12) 0.0398(12) 0.0217(10) 0.0097(10) 0.0115(10) C9 0.0360(12) 0.0312(11) 0.0392(12) 0.0056(9) 0.0026(9) -0.0069(9) C10 0.0264(11) 0.0571(14) 0.0540(14) 0.0281(12) 0.0069(10) 0.0152(10) C11 0.0255(10) 0.0262(9) 0.0292(10) 0.0111(8) 0.0039(8) 0.0046(7) C12 0.0249(10) 0.0244(9) 0.0253(10) 0.0061(7) 0.0029(7) 0.0013(7) C13 0.0266(10) 0.0240(9) 0.0232(9) 0.0040(7) 0.0000(7) 0.0033(7) C14 0.0369(12) 0.0279(10) 0.0350(11) 0.0134(8) 0.0017(9) 0.0021(8) C15 0.0288(11) 0.0383(11) 0.0413(12) 0.0146(9) 0.0074(9) -0.0016(9) C16 0.0235(10) 0.0373(11) 0.0418(12) 0.0099(9) 0.0044(9) 0.0040(8) C17 0.0278(10) 0.0300(10) 0.0389(11) 0.0130(9) 0.0027(8) 0.0053(8) C18 0.0323(11) 0.0347(11) 0.0416(12) 0.0016(9) 0.0054(9) 0.0083(9) C19 0.0394(13) 0.0455(13) 0.0502(14) 0.0233(11) 0.0007(10) 0.0146(10) C20 0.0368(11) 0.0322(10) 0.0248(10) 0.0095(8) 0.0019(8) 0.0022(9) C21 0.0436(13) 0.0323(11) 0.0303(11) 0.0041(8) -0.0016(9) 0.0017(9) C22 0.0616(16) 0.0421(13) 0.0339(12) 0.0158(10) -0.0113(11) 0.0040(11) C23 0.0529(15) 0.0532(14) 0.0324(12) 0.0055(10) 0.0150(11) -0.0006(12) _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 N1 2.0218(16) . ? Zr1 Cl1 2.4180(5) . ? Zr1 Cl2 2.4231(5) . ? Zr1 C5 2.4832(19) . ? Zr1 C1 2.4944(19) . ? Zr1 C4 2.5008(19) . ? Zr1 C2 2.5636(19) . ? Zr1 C3 2.5673(19) . ? N1 C11 1.474(2) . ? N1 C20 1.491(2) . ? N2 C13 1.426(3) . ? N2 C18 1.464(3) . ? N2 C19 1.464(3) . ? C1 C5 1.420(3) . ? C1 C2 1.423(3) . ? C1 C6 1.507(3) . ? C2 C3 1.412(3) . ? C2 C7 1.498(3) . ? C3 C4 1.426(3) . ? C3 C8 1.505(3) . ? C4 C5 1.418(3) . ? C4 C9 1.508(3) . ? C5 C10 1.506(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.522(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.389(3) . ? C12 C13 1.408(3) . ? C13 C14 1.399(3) . ? C14 C15 1.374(3) . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 C17 1.384(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C23 1.531(3) . ? C20 C21 1.532(3) . ? C20 C22 1.533(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zr1 Cl1 102.42(5) . . ? N1 Zr1 Cl2 107.45(5) . . ? Cl1 Zr1 Cl2 100.18(2) . . ? N1 Zr1 C5 93.10(6) . . ? Cl1 Zr1 C5 120.81(5) . . ? Cl2 Zr1 C5 128.84(5) . . ? N1 Zr1 C1 108.09(7) . . ? Cl1 Zr1 C1 139.30(5) . . ? Cl2 Zr1 C1 95.74(5) . . ? C5 Zr1 C1 33.16(7) . . ? N1 Zr1 C4 111.89(6) . . ? Cl1 Zr1 C4 89.47(5) . . ? Cl2 Zr1 C4 136.27(5) . . ? C5 Zr1 C4 33.05(6) . . ? C1 Zr1 C4 54.52(6) . . ? N1 Zr1 C2 140.73(7) . . ? Cl1 Zr1 C2 112.81(5) . . ? Cl2 Zr1 C2 83.45(5) . . ? C5 Zr1 C2 54.37(7) . . ? C1 Zr1 C2 32.65(7) . . ? C4 Zr1 C2 53.89(6) . . ? N1 Zr1 C3 144.25(6) . . ? Cl1 Zr1 C3 85.81(5) . . ? Cl2 Zr1 C3 105.11(5) . . ? C5 Zr1 C3 54.28(6) . . ? C1 Zr1 C3 53.81(6) . . ? C4 Zr1 C3 32.65(6) . . ? C2 Zr1 C3 31.95(6) . . ? C11 N1 C20 117.19(15) . . ? C11 N1 Zr1 101.86(11) . . ? C20 N1 Zr1 140.00(12) . . ? C13 N2 C18 112.36(16) . . ? C13 N2 C19 114.88(17) . . ? C18 N2 C19 110.89(17) . . ? C5 C1 C2 108.44(17) . . ? C5 C1 C6 126.2(2) . . ? C2 C1 C6 124.7(2) . . ? C5 C1 Zr1 72.99(11) . . ? C2 C1 Zr1 76.35(11) . . ? C6 C1 Zr1 123.66(15) . . ? C3 C2 C1 107.83(17) . . ? C3 C2 C7 126.8(2) . . ? C1 C2 C7 125.23(19) . . ? C3 C2 Zr1 74.17(11) . . ? C1 C2 Zr1 71.00(11) . . ? C7 C2 Zr1 124.00(14) . . ? C2 C3 C4 107.97(17) . . ? C2 C3 C8 126.47(19) . . ? C4 C3 C8 125.42(18) . . ? C2 C3 Zr1 73.88(11) . . ? C4 C3 Zr1 71.11(11) . . ? C8 C3 Zr1 124.03(14) . . ? C5 C4 C3 108.30(17) . . ? C5 C4 C9 126.12(18) . . ? C3 C4 C9 125.24(18) . . ? C5 C4 Zr1 72.79(11) . . ? C3 C4 Zr1 76.24(11) . . ? C9 C4 Zr1 122.35(14) . . ? C4 C5 C1 107.44(17) . . ? C4 C5 C10 125.92(19) . . ? C1 C5 C10 126.18(19) . . ? C4 C5 Zr1 74.15(11) . . ? C1 C5 Zr1 73.85(11) . . ? C10 C5 Zr1 123.74(14) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 115.71(16) . . ? N1 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? N1 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? C17 C12 C13 118.96(18) . . ? C17 C12 C11 120.54(17) . . ? C13 C12 C11 120.45(17) . . ? C14 C13 C12 118.65(18) . . ? C14 C13 N2 122.37(17) . . ? C12 C13 N2 118.97(17) . . ? C15 C14 C13 121.06(19) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 118.77(19) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C12 121.83(19) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 C23 110.37(17) . . ? N1 C20 C21 107.33(16) . . ? C23 C20 C21 108.07(19) . . ? N1 C20 C22 112.41(17) . . ? C23 C20 C22 109.88(19) . . ? C21 C20 C22 108.65(18) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.338 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.054 #========================================================end