# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email schafer@chem.ubc.ca _publ_contact_author_name 'Laurel Schafer' loop_ _publ_author_name 'Rashidat Ayinla' 'Laurel Schafer' data_ls037_pnma _database_code_depnum_ccdc_archive 'CCDC 817776' #TrackingRef 'figure3-complex5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 N4 O Zr' _chemical_formula_sum 'C18 H36 N4 O Zr' _chemical_formula_weight 415.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 17.2760(12) _cell_length_b 13.5998(9) _cell_length_c 9.8227(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2307.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.358 _cell_measurement_theta_max 23.826 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46460 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.74 _reflns_number_total 2818 _reflns_number_gt 2294 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+1.0458P] 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 2818 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0712 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C1A C 0.8273(2) 0.2203(5) 0.2793(4) 0.068(3) Uani 0.50 1 d P . . H1A H 0.8226 0.1485 0.2762 0.081 Uiso 0.50 1 calc PR . . C2A C 0.9010(3) 0.234(3) 0.3338(5) 0.151(8) Uani 0.50 1 d P . . H2A1 H 0.9124 0.3032 0.3368 0.227 Uiso 0.50 1 calc PR . . H2A2 H 0.9385 0.2013 0.2778 0.227 Uiso 0.50 1 calc PR . . H2A3 H 0.9027 0.2075 0.4242 0.227 Uiso 0.50 1 calc PR . . C3 C 0.75991(18) 0.2500 0.3632(3) 0.0723(11) Uani 1 2 d S . . H3A H 0.7616 0.2164 0.4503 0.087 Uiso 0.50 1 calc PR . . H3B H 0.7617 0.3202 0.3801 0.087 Uiso 0.50 1 calc PR . . C4A C 0.62104(19) 0.2500 0.3725(3) 0.0911(15) Uani 1 2 d S . . H4A1 H 0.6218 0.2148 0.4572 0.137 Uiso 0.50 1 calc PR . . H4A2 H 0.5758 0.2317 0.3217 0.137 Uiso 0.50 1 calc PR . . H4A3 H 0.6200 0.3194 0.3901 0.137 Uiso 0.50 1 calc PR . . C5 C 0.87478(15) 0.2500 0.0442(3) 0.0461(7) Uani 1 2 d S . . C6 C 0.90539(13) 0.3388(2) -0.0034(2) 0.0639(7) Uani 1 1 d . . . C7 C 0.96752(14) 0.3364(3) -0.0968(3) 0.0856(10) Uani 1 1 d . . . H7 H 0.9883 0.3953 -0.1282 0.103 Uiso 1 1 calc R . . C8 C 0.9976(2) 0.2500 -0.1417(4) 0.0944(17) Uani 1 2 d S . . H8 H 1.0386 0.2500 -0.2029 0.113 Uiso 1 2 calc SR . . C9 C 0.87277(19) 0.4367(2) 0.0413(3) 0.0951(10) Uani 1 1 d . . . H9A H 0.8175 0.4358 0.0321 0.143 Uiso 1 1 calc R . . H9B H 0.8939 0.4880 -0.0144 0.143 Uiso 1 1 calc R . . H9C H 0.8862 0.4483 0.1348 0.143 Uiso 1 1 calc R . . C10A C 0.7355(2) 0.1634(2) -0.2312(3) 0.0916(10) Uani 1 1 d . . . H10A H 0.7023 0.1627 -0.3095 0.137 Uiso 1 1 calc R . . H10B H 0.7262 0.1057 -0.1773 0.137 Uiso 1 1 calc R . . H10C H 0.7886 0.1642 -0.2602 0.137 Uiso 1 1 calc R . . C11A C 0.5667(2) 0.3935(3) -0.0321(4) 0.1317(17) Uani 1 1 d . . . H11A H 0.5207 0.4064 0.0196 0.198 Uiso 1 1 calc R . . H11B H 0.5592 0.3358 -0.0868 0.198 Uiso 1 1 calc R . . H11C H 0.5776 0.4487 -0.0901 0.198 Uiso 1 1 calc R . . C12 C 0.6425(2) 0.4655(2) 0.1399(3) 0.1041(11) Uani 1 1 d . . . H12A H 0.6498 0.5208 0.0805 0.156 Uiso 1 1 calc R . . H12B H 0.6875 0.4576 0.1963 0.156 Uiso 1 1 calc R . . H12C H 0.5979 0.4765 0.1963 0.156 Uiso 1 1 calc R . . N1 N 0.80989(12) 0.2500 0.1357(2) 0.0435(5) Uani 1 2 d S . . N2 N 0.71974(13) 0.2500 -0.1507(2) 0.0418(5) Uani 1 2 d S . . N3 N 0.63105(10) 0.37803(13) 0.05983(18) 0.0545(4) Uani 1 1 d . . . O1A O 0.69038(13) 0.2257(3) 0.2938(2) 0.0504(13) Uani 0.50 1 d P . . Zr1 Zr 0.695658(13) 0.2500 0.05510(2) 0.03062(9) Uani 1 2 d S . . 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 C1A 0.0447(18) 0.131(8) 0.0275(17) 0.007(2) -0.0052(14) 0.008(2) C2A 0.057(3) 0.36(2) 0.040(2) 0.020(9) -0.0134(19) 0.061(11) C3 0.0510(18) 0.139(4) 0.0273(15) 0.000 -0.0047(13) 0.000 C4A 0.0488(19) 0.183(5) 0.0420(19) 0.000 0.0176(15) 0.000 C5 0.0337(13) 0.076(2) 0.0284(13) 0.000 -0.0054(11) 0.000 C6 0.0464(12) 0.098(2) 0.0473(12) 0.0087(13) -0.0053(10) -0.0123(13) C7 0.0521(14) 0.150(3) 0.0543(14) 0.0269(18) -0.0006(12) -0.0247(17) C8 0.0431(19) 0.200(6) 0.040(2) 0.000 0.0019(15) 0.000 C9 0.094(2) 0.084(2) 0.107(2) 0.0162(19) -0.0004(18) -0.0216(18) C10A 0.150(3) 0.0800(19) 0.0451(13) -0.0035(13) 0.0194(16) 0.0499(19) C11A 0.106(2) 0.082(2) 0.207(4) -0.064(3) -0.086(3) 0.052(2) C12 0.143(3) 0.0671(18) 0.102(2) -0.0431(17) -0.026(2) 0.0258(19) N1 0.0355(11) 0.0689(15) 0.0262(11) 0.000 -0.0005(8) 0.000 N2 0.0459(12) 0.0518(13) 0.0276(11) 0.000 -0.0025(9) 0.000 N3 0.0557(10) 0.0440(9) 0.0640(11) -0.0171(9) -0.0064(8) 0.0106(8) O1A 0.0398(11) 0.083(4) 0.0282(11) 0.0008(13) 0.0043(9) -0.0019(14) Zr1 0.03378(13) 0.03329(13) 0.02479(13) 0.000 -0.00189(10) 0.000 _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 C1A C2A 1.393(8) . ? C1A C3 1.483(5) . ? C1A N1 1.497(4) . ? C1A H1A 0.9800 . ? C2A H2A1 0.9600 . ? C2A H2A2 0.9600 . ? C2A H2A3 0.9600 . ? C3 O1A 1.420(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4A O1A 1.463(4) . ? C4A H4A1 0.9600 . ? C4A H4A2 0.9600 . ? C4A H4A3 0.9600 . ? C5 C6 1.399(3) . ? C5 C6 1.399(3) 8_565 ? C5 N1 1.437(3) . ? C6 C7 1.412(3) . ? C6 C9 1.511(4) . ? C7 C8 1.358(4) . ? C7 H7 0.9300 . ? C8 C7 1.358(4) 8_565 ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10A N2 1.445(3) . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C11A N3 1.447(3) . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C12 N3 1.440(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N1 C1A 1.497(4) 8_565 ? N1 Zr1 2.127(2) . ? N2 C10A 1.445(3) 8_565 ? N2 Zr1 2.064(2) . ? N3 Zr1 2.0687(17) . ? O1A C4A 1.463(4) 8_565 ? O1A Zr1 2.370(2) . ? Zr1 N3 2.0687(17) 8_565 ? Zr1 O1A 2.370(2) 8_565 ? 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 C2A C1A C3 117.8(7) . . ? C2A C1A N1 120.6(7) . . ? C3 C1A N1 107.0(3) . . ? C2A C1A H1A 102.9 . . ? C3 C1A H1A 102.9 . . ? N1 C1A H1A 102.9 . . ? C1A C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C1A C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? O1A C3 C1A 109.5(3) . . ? O1A C3 H3A 109.8 . . ? C1A C3 H3A 109.8 . . ? O1A C3 H3B 109.8 . . ? C1A C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? O1A C4A H4A1 109.5 . . ? O1A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? O1A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C6 C5 C6 119.4(3) . 8_565 ? C6 C5 N1 120.27(14) . . ? C6 C5 N1 120.27(14) 8_565 . ? C5 C6 C7 119.0(3) . . ? C5 C6 C9 121.5(2) . . ? C7 C6 C9 119.5(3) . . ? C8 C7 C6 121.4(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C7 119.8(4) 8_565 . ? C7 C8 H8 120.1 8_565 . ? C7 C8 H8 120.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10A H10A 109.5 . . ? N2 C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? N2 C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? N3 C11A H11A 109.5 . . ? N3 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? N3 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 N1 C1A 115.6(2) . 8_565 ? C5 N1 C1A 115.6(2) . . ? C1A N1 C1A 31.3(5) 8_565 . ? C5 N1 Zr1 119.39(16) . . ? C1A N1 Zr1 122.51(19) 8_565 . ? C1A N1 Zr1 122.51(19) . . ? C10A N2 C10A 109.3(3) . 8_565 ? C10A N2 Zr1 125.02(13) . . ? C10A N2 Zr1 125.02(13) 8_565 . ? C12 N3 C11A 109.0(2) . . ? C12 N3 Zr1 129.31(17) . . ? C11A N3 Zr1 121.53(16) . . ? C3 O1A C4A 112.7(2) . 8_565 ? C3 O1A C4A 112.7(2) . . ? C4A O1A C4A 0.00(15) 8_565 . ? C3 O1A Zr1 114.20(18) . . ? C4A O1A Zr1 121.5(2) 8_565 . ? C4A O1A Zr1 121.5(2) . . ? N2 Zr1 N3 97.52(6) . 8_565 ? N2 Zr1 N3 97.52(6) . . ? N3 Zr1 N3 114.63(11) 8_565 . ? N2 Zr1 N1 100.24(8) . . ? N3 Zr1 N1 119.50(5) 8_565 . ? N3 Zr1 N1 119.50(5) . . ? N2 Zr1 O1A 167.67(8) . 8_565 ? N3 Zr1 O1A 94.27(9) 8_565 8_565 ? N3 Zr1 O1A 80.77(9) . 8_565 ? N1 Zr1 O1A 70.56(8) . 8_565 ? N2 Zr1 O1A 167.67(8) . . ? N3 Zr1 O1A 80.77(9) 8_565 . ? N3 Zr1 O1A 94.27(9) . . ? N1 Zr1 O1A 70.56(8) . . ? O1A Zr1 O1A 16.04(17) 8_565 . ? 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 C2A C1A C3 O1A -177.1(17) . . . . ? N1 C1A C3 O1A 43.2(4) . . . . ? C6 C5 C6 C7 -1.1(4) 8_565 . . . ? N1 C5 C6 C7 -177.9(2) . . . . ? C6 C5 C6 C9 178.05(19) 8_565 . . . ? N1 C5 C6 C9 1.2(4) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C9 C6 C7 C8 -178.7(3) . . . . ? C6 C7 C8 C7 0.2(6) . . . 8_565 ? C6 C5 N1 C1A -74.2(4) . . . 8_565 ? C6 C5 N1 C1A 109.0(3) 8_565 . . 8_565 ? C6 C5 N1 C1A -109.0(3) . . . . ? C6 C5 N1 C1A 74.2(4) 8_565 . . . ? C6 C5 N1 Zr1 88.4(2) . . . . ? C6 C5 N1 Zr1 -88.4(2) 8_565 . . . ? C2A C1A N1 C5 26.9(17) . . . . ? C3 C1A N1 C5 165.3(2) . . . . ? C2A C1A N1 C1A -70.8(17) . . . 8_565 ? C3 C1A N1 C1A 67.6(3) . . . 8_565 ? C2A C1A N1 Zr1 -171.1(17) . . . . ? C3 C1A N1 Zr1 -32.7(5) . . . . ? C1A C3 O1A C4A 178.2(3) . . . 8_565 ? C1A C3 O1A C4A 178.2(3) . . . . ? C1A C3 O1A Zr1 -37.8(3) . . . . ? C10A N2 Zr1 N3 -37.1(2) . . . 8_565 ? C10A N2 Zr1 N3 153.3(2) 8_565 . . 8_565 ? C10A N2 Zr1 N3 -153.3(2) . . . . ? C10A N2 Zr1 N3 37.1(2) 8_565 . . . ? C10A N2 Zr1 N1 84.8(2) . . . . ? C10A N2 Zr1 N1 -84.8(2) 8_565 . . . ? C10A N2 Zr1 O1A 125.5(4) . . . 8_565 ? C10A N2 Zr1 O1A -44.0(5) 8_565 . . 8_565 ? C10A N2 Zr1 O1A 44.0(5) . . . . ? C10A N2 Zr1 O1A -125.5(4) 8_565 . . . ? C12 N3 Zr1 N2 -123.6(3) . . . . ? C11A N3 Zr1 N2 51.6(3) . . . . ? C12 N3 Zr1 N3 134.5(2) . . . 8_565 ? C11A N3 Zr1 N3 -50.3(3) . . . 8_565 ? C12 N3 Zr1 N1 -17.3(3) . . . . ? C11A N3 Zr1 N1 157.9(3) . . . . ? C12 N3 Zr1 O1A 44.1(3) . . . 8_565 ? C11A N3 Zr1 O1A -140.7(3) . . . 8_565 ? C12 N3 Zr1 O1A 52.8(3) . . . . ? C11A N3 Zr1 O1A -132.0(3) . . . . ? C5 N1 Zr1 N2 0.0 . . . . ? C1A N1 Zr1 N2 161.3(3) 8_565 . . . ? C1A N1 Zr1 N2 -161.3(3) . . . . ? C5 N1 Zr1 N3 104.77(7) . . . 8_565 ? C1A N1 Zr1 N3 -93.9(3) 8_565 . . 8_565 ? C1A N1 Zr1 N3 -56.6(3) . . . 8_565 ? C5 N1 Zr1 N3 -104.77(7) . . . . ? C1A N1 Zr1 N3 56.6(3) 8_565 . . . ? C1A N1 Zr1 N3 93.9(3) . . . . ? C5 N1 Zr1 O1A -171.49(9) . . . 8_565 ? C1A N1 Zr1 O1A -10.2(3) 8_565 . . 8_565 ? C1A N1 Zr1 O1A 27.2(3) . . . 8_565 ? C5 N1 Zr1 O1A 171.49(9) . . . . ? C1A N1 Zr1 O1A -27.2(3) 8_565 . . . ? C1A N1 Zr1 O1A 10.2(3) . . . . ? C3 O1A Zr1 N2 58.8(5) . . . . ? C4A O1A Zr1 N2 -160.6(3) 8_565 . . . ? C4A O1A Zr1 N2 -160.6(3) . . . . ? C3 O1A Zr1 N3 141.8(2) . . . 8_565 ? C4A O1A Zr1 N3 -77.7(2) 8_565 . . 8_565 ? C4A O1A Zr1 N3 -77.7(2) . . . 8_565 ? C3 O1A Zr1 N3 -103.9(2) . . . . ? C4A O1A Zr1 N3 36.6(2) 8_565 . . . ? C4A O1A Zr1 N3 36.6(2) . . . . ? C3 O1A Zr1 N1 15.87(17) . . . . ? C4A O1A Zr1 N1 156.4(2) 8_565 . . . ? C4A O1A Zr1 N1 156.4(2) . . . . ? C3 O1A Zr1 O1A -71.3(2) . . . 8_565 ? C4A O1A Zr1 O1A 69.3(2) 8_565 . . 8_565 ? C4A O1A Zr1 O1A 69.3(2) . . . 8_565 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.309 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.049 # Attachment 'figure4-complex6.cif' data_ls061_pnma _database_code_depnum_ccdc_archive 'CCDC 817777' #TrackingRef 'figure4-complex6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 N4 O Ti' _chemical_formula_sum 'C18 H36 N4 O Ti' _chemical_formula_weight 372.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 17.289(2) _cell_length_b 13.0762(13) _cell_length_c 9.6677(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2185.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.356 _cell_measurement_theta_max 22.633 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.132 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.403 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17022 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.23 _reflns_number_total 2046 _reflns_number_gt 1534 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+1.0032P] 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 2046 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8165(3) 0.2167(4) 0.7810(4) 0.0489(16) Uani 0.50 1 d P . . H1 H 0.8166 0.1402 0.7812 0.059 Uiso 0.50 1 calc PR . . C2 C 0.8917(3) 0.2500 0.8378(4) 0.0927(19) Uani 1 2 d S . . H2A H 0.9336 0.2154 0.7883 0.139 Uiso 0.50 1 calc PR . . H2B H 0.8943 0.2326 0.9363 0.139 Uiso 0.50 1 calc PR . . H2C H 0.8970 0.3241 0.8265 0.139 Uiso 0.50 1 calc PR . . C3 C 0.7497(2) 0.2500 0.8652(3) 0.0519(10) Uani 1 2 d S . . H3A H 0.7499 0.2144 0.9556 0.062 Uiso 0.50 1 calc PR . . H3B H 0.7523 0.3246 0.8820 0.062 Uiso 0.50 1 calc PR . . C4 C 0.6112(2) 0.2500 0.8634(4) 0.0666(13) Uani 1 2 d S . . H4A H 0.6101 0.2136 0.9520 0.100 Uiso 0.50 1 calc PR . . H4B H 0.5666 0.2293 0.8075 0.100 Uiso 0.50 1 calc PR . . H4C H 0.6090 0.3238 0.8803 0.100 Uiso 0.50 1 calc PR . . C5 C 0.8652(2) 0.2500 0.5452(3) 0.0412(8) Uani 1 2 d S . . C6 C 0.89683(17) 0.3424(2) 0.4988(3) 0.0587(8) Uani 1 1 d . . . C7 C 0.95930(18) 0.3407(3) 0.4073(3) 0.0772(11) Uani 1 1 d . . . H7 H 0.9810 0.4033 0.3760 0.093 Uiso 1 1 calc R . . C8 C 0.9899(3) 0.2500 0.3617(4) 0.091(2) Uani 1 2 d S . . H8 H 1.0321 0.2500 0.2988 0.110 Uiso 1 2 calc SR . . C9 C 0.8641(2) 0.4440(2) 0.5456(3) 0.0760(10) Uani 1 1 d . . . H9A H 0.8872 0.4992 0.4909 0.114 Uiso 1 1 calc R . . H9B H 0.8760 0.4545 0.6436 0.114 Uiso 1 1 calc R . . H9C H 0.8079 0.4441 0.5324 0.114 Uiso 1 1 calc R . . C10 C 0.6453(2) 0.4639(2) 0.6426(3) 0.0793(11) Uani 1 1 d . . . H10A H 0.6544 0.5229 0.5821 0.119 Uiso 1 1 calc R . . H10B H 0.6903 0.4537 0.7026 0.119 Uiso 1 1 calc R . . H10C H 0.5994 0.4764 0.6995 0.119 Uiso 1 1 calc R . . C11 C 0.5695(2) 0.3919(3) 0.4659(5) 0.1142(18) Uani 1 1 d . . . H11A H 0.5214 0.3979 0.5189 0.171 Uiso 1 1 calc R . . H11B H 0.5653 0.3346 0.4010 0.171 Uiso 1 1 calc R . . H11C H 0.5785 0.4553 0.4144 0.171 Uiso 1 1 calc R . . C12 C 0.7327(2) 0.3393(2) 0.2844(3) 0.0705(10) Uani 1 1 d . . . H12A H 0.7873 0.3388 0.2568 0.106 Uiso 1 1 calc R . . H12B H 0.7220 0.4008 0.3390 0.106 Uiso 1 1 calc R . . H12C H 0.7000 0.3390 0.2016 0.106 Uiso 1 1 calc R . . N1 N 0.80004(16) 0.2500 0.6358(3) 0.0359(7) Uani 1 2 d S . . N2 N 0.63333(13) 0.37398(14) 0.5595(2) 0.0447(5) Uani 1 1 d . . . N3 N 0.71643(16) 0.2500 0.3661(3) 0.0341(6) Uani 1 2 d S . . O1 O 0.68185(18) 0.2253(3) 0.7904(3) 0.0441(15) Uani 0.50 1 d P . . Ti1 Ti 0.69332(3) 0.2500 0.56044(5) 0.0299(2) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.040(3) 0.077(5) 0.030(2) 0.005(2) -0.0044(19) 0.004(2) C2 0.048(3) 0.193(6) 0.037(2) 0.000 -0.013(2) 0.000 C3 0.044(2) 0.083(3) 0.0283(18) 0.000 -0.0029(17) 0.000 C4 0.042(3) 0.114(4) 0.043(2) 0.000 0.0153(19) 0.000 C5 0.0279(19) 0.071(2) 0.0247(17) 0.000 -0.0034(14) 0.000 C6 0.0414(18) 0.094(2) 0.0411(15) 0.0151(15) -0.0054(13) -0.0081(16) C7 0.0394(19) 0.142(4) 0.0503(18) 0.030(2) -0.0010(15) -0.017(2) C8 0.036(3) 0.203(7) 0.035(2) 0.000 0.004(2) 0.000 C9 0.065(2) 0.072(2) 0.091(2) 0.0232(18) -0.0010(18) -0.0173(18) C10 0.118(3) 0.0452(17) 0.074(2) -0.0235(15) -0.009(2) 0.0109(18) C11 0.082(3) 0.066(2) 0.195(4) -0.059(3) -0.072(3) 0.037(2) C12 0.120(3) 0.0514(17) 0.0400(16) 0.0046(12) 0.0116(17) -0.0241(18) N1 0.0313(17) 0.0516(16) 0.0249(14) 0.000 0.0009(12) 0.000 N2 0.0441(13) 0.0367(11) 0.0532(13) -0.0153(9) -0.0024(10) 0.0049(9) N3 0.0413(17) 0.0311(14) 0.0300(14) 0.000 0.0009(12) 0.000 O1 0.0357(17) 0.067(5) 0.0292(14) -0.0019(15) 0.0064(12) -0.0010(16) Ti1 0.0314(4) 0.0320(3) 0.0262(3) 0.000 -0.0003(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.476(6) . ? C1 C3 1.479(6) . ? C1 N1 1.497(5) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 O1 1.416(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O1 1.448(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.400(3) 8_565 ? C5 C6 1.400(3) . ? C5 N1 1.427(4) . ? C6 C7 1.397(4) . ? C6 C9 1.513(4) . ? C7 C8 1.371(4) . ? C7 H7 0.9500 . ? C8 C7 1.371(4) 8_565 ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.439(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.446(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N3 1.437(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N1 C1 1.497(5) 8_565 ? N1 Ti1 1.984(3) . ? N2 Ti1 1.925(2) . ? N3 C12 1.437(3) 8_565 ? N3 Ti1 1.921(3) . ? O1 C4 1.448(4) 8_565 ? O1 Ti1 2.255(3) . ? Ti1 N2 1.925(2) 8_565 ? Ti1 O1 2.255(3) 8_565 ? 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 C2 C1 C3 113.3(4) . . ? C2 C1 N1 115.5(4) . . ? C3 C1 N1 106.4(3) . . ? C2 C1 H1 107.1 . . ? C3 C1 H1 107.1 . . ? N1 C1 H1 107.1 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C1 107.4(3) . . ? O1 C3 H3A 110.2 . . ? C1 C3 H3A 110.2 . . ? O1 C3 H3B 110.2 . . ? C1 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? O1 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C6 119.3(3) 8_565 . ? C6 C5 N1 120.32(17) 8_565 . ? C6 C5 N1 120.32(17) . . ? C7 C6 C5 119.4(3) . . ? C7 C6 C9 119.5(3) . . ? C5 C6 C9 121.1(3) . . ? C8 C7 C6 121.1(4) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C7 119.8(4) 8_565 . ? C7 C8 H8 120.1 8_565 . ? C7 C8 H8 120.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 N1 C1 115.1(3) . 8_565 ? C5 N1 C1 115.1(3) . . ? C1 N1 C1 33.8(4) 8_565 . ? C5 N1 Ti1 120.6(2) . . ? C1 N1 Ti1 121.4(2) 8_565 . ? C1 N1 Ti1 121.4(2) . . ? C10 N2 C11 109.1(2) . . ? C10 N2 Ti1 127.4(2) . . ? C11 N2 Ti1 123.42(17) . . ? C12 N3 C12 108.6(3) 8_565 . ? C12 N3 Ti1 125.33(14) 8_565 . ? C12 N3 Ti1 125.33(14) . . ? C3 O1 C4 113.6(3) . 8_565 ? C3 O1 C4 113.6(3) . . ? C4 O1 C4 0.00(17) 8_565 . ? C3 O1 Ti1 113.4(2) . . ? C4 O1 Ti1 121.5(2) 8_565 . ? C4 O1 Ti1 121.5(2) . . ? N3 Ti1 N2 96.17(8) . 8_565 ? N3 Ti1 N2 96.17(8) . . ? N2 Ti1 N2 114.78(13) 8_565 . ? N3 Ti1 N1 99.53(12) . . ? N2 Ti1 N1 120.20(7) 8_565 . ? N2 Ti1 N1 120.20(7) . . ? N3 Ti1 O1 169.27(11) . 8_565 ? N2 Ti1 O1 94.47(11) 8_565 8_565 ? N2 Ti1 O1 80.60(11) . 8_565 ? N1 Ti1 O1 73.73(11) . 8_565 ? N3 Ti1 O1 169.27(11) . . ? N2 Ti1 O1 80.60(11) 8_565 . ? N2 Ti1 O1 94.47(11) . . ? N1 Ti1 O1 73.73(11) . . ? O1 Ti1 O1 16.5(2) 8_565 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C3 O1 172.3(3) . . . . ? N1 C1 C3 O1 44.3(4) . . . . ? C6 C5 C6 C7 -0.1(5) 8_565 . . . ? N1 C5 C6 C7 -178.3(3) . . . . ? C6 C5 C6 C9 179.6(2) 8_565 . . . ? N1 C5 C6 C9 1.4(4) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C9 C6 C7 C8 -179.3(3) . . . . ? C6 C7 C8 C7 -0.5(7) . . . 8_565 ? C6 C5 N1 C1 109.7(3) 8_565 . . 8_565 ? C6 C5 N1 C1 -72.2(4) . . . 8_565 ? C6 C5 N1 C1 72.2(4) 8_565 . . . ? C6 C5 N1 C1 -109.7(3) . . . . ? C6 C5 N1 Ti1 -89.1(3) 8_565 . . . ? C6 C5 N1 Ti1 89.1(3) . . . . ? C2 C1 N1 C5 37.3(4) . . . . ? C3 C1 N1 C5 164.0(2) . . . . ? C2 C1 N1 C1 -60.9(4) . . . 8_565 ? C3 C1 N1 C1 65.8(3) . . . 8_565 ? C2 C1 N1 Ti1 -161.6(2) . . . . ? C3 C1 N1 Ti1 -34.9(4) . . . . ? C1 C3 O1 C4 177.6(3) . . . 8_565 ? C1 C3 O1 C4 177.6(3) . . . . ? C1 C3 O1 Ti1 -38.2(3) . . . . ? C12 N3 Ti1 N2 -37.5(3) 8_565 . . 8_565 ? C12 N3 Ti1 N2 153.4(3) . . . 8_565 ? C12 N3 Ti1 N2 -153.4(3) 8_565 . . . ? C12 N3 Ti1 N2 37.5(3) . . . . ? C12 N3 Ti1 N1 84.6(3) 8_565 . . . ? C12 N3 Ti1 N1 -84.6(3) . . . . ? C12 N3 Ti1 O1 134.8(5) 8_565 . . 8_565 ? C12 N3 Ti1 O1 -34.3(8) . . . 8_565 ? C12 N3 Ti1 O1 34.3(8) 8_565 . . . ? C12 N3 Ti1 O1 -134.8(5) . . . . ? C10 N2 Ti1 N3 -124.8(3) . . . . ? C11 N2 Ti1 N3 51.9(3) . . . . ? C10 N2 Ti1 N2 135.5(2) . . . 8_565 ? C11 N2 Ti1 N2 -47.9(3) . . . 8_565 ? C10 N2 Ti1 N1 -20.0(3) . . . . ? C11 N2 Ti1 N1 156.7(3) . . . . ? C10 N2 Ti1 O1 44.9(3) . . . 8_565 ? C11 N2 Ti1 O1 -138.5(3) . . . 8_565 ? C10 N2 Ti1 O1 53.8(3) . . . . ? C11 N2 Ti1 O1 -129.6(3) . . . . ? C5 N1 Ti1 N3 0.0 . . . . ? C1 N1 Ti1 N3 160.1(2) 8_565 . . . ? C1 N1 Ti1 N3 -160.1(2) . . . . ? C5 N1 Ti1 N2 102.93(9) . . . 8_565 ? C1 N1 Ti1 N2 -97.0(2) 8_565 . . 8_565 ? C1 N1 Ti1 N2 -57.1(3) . . . 8_565 ? C5 N1 Ti1 N2 -102.93(9) . . . . ? C1 N1 Ti1 N2 57.1(3) 8_565 . . . ? C1 N1 Ti1 N2 97.0(2) . . . . ? C5 N1 Ti1 O1 -171.42(10) . . . 8_565 ? C1 N1 Ti1 O1 -11.4(3) 8_565 . . 8_565 ? C1 N1 Ti1 O1 28.5(3) . . . 8_565 ? C5 N1 Ti1 O1 171.42(10) . . . . ? C1 N1 Ti1 O1 -28.5(3) 8_565 . . . ? C1 N1 Ti1 O1 11.4(3) . . . . ? C3 O1 Ti1 N3 68.0(7) . . . . ? C4 O1 Ti1 N3 -150.9(5) 8_565 . . . ? C4 O1 Ti1 N3 -150.9(5) . . . . ? C3 O1 Ti1 N2 141.3(2) . . . 8_565 ? C4 O1 Ti1 N2 -77.7(3) 8_565 . . 8_565 ? C4 O1 Ti1 N2 -77.7(3) . . . 8_565 ? C3 O1 Ti1 N2 -104.3(2) . . . . ? C4 O1 Ti1 N2 36.7(3) 8_565 . . . ? C4 O1 Ti1 N2 36.7(3) . . . . ? C3 O1 Ti1 N1 15.88(19) . . . . ? C4 O1 Ti1 N1 156.9(3) 8_565 . . . ? C4 O1 Ti1 N1 156.9(3) . . . . ? C3 O1 Ti1 O1 -71.7(2) . . . 8_565 ? C4 O1 Ti1 O1 69.3(3) 8_565 . . 8_565 ? C4 O1 Ti1 O1 69.3(3) . . . 8_565 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.284 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 # Attachment 'figure5-complex7.cif' data_ls036_0m _database_code_depnum_ccdc_archive 'CCDC 817778' #TrackingRef 'figure5-complex7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H42 N4 O Zr' _chemical_formula_sum 'C25 H42 N4 O Zr' _chemical_formula_weight 505.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.5820(15) _cell_length_b 17.7264(4) _cell_length_c 18.8172(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5531.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.298 _cell_measurement_theta_max 24.549 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.959 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 154892 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.73 _reflns_number_total 6474 _reflns_number_gt 4514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+2.5423P] 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 6474 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.82039(13) 0.21268(13) 0.23624(15) 0.0567(7) Uani 1 1 d . . . H1A H 0.8542 0.2071 0.1952 0.085 Uiso 1 1 calc R . . H1B H 0.8161 0.1651 0.2604 0.085 Uiso 1 1 calc R . . H1C H 0.8435 0.2494 0.2677 0.085 Uiso 1 1 calc R . . C2 C 0.73614(11) 0.23891(10) 0.21300(10) 0.0321(4) Uani 1 1 d . . . H2 H 0.7014 0.2418 0.2550 0.038 Uiso 1 1 calc R . . C3 C 0.70204(11) 0.18029(10) 0.16250(10) 0.0316(4) Uani 1 1 d . . . H3A H 0.7410 0.1688 0.1256 0.038 Uiso 1 1 calc R . . H3B H 0.6900 0.1341 0.1881 0.038 Uiso 1 1 calc R . . C4 C 0.76769(11) 0.37328(11) 0.21977(9) 0.0296(4) Uani 1 1 d . . . C5 C 0.72185(12) 0.40309(11) 0.27687(10) 0.0354(5) Uani 1 1 d . . . C6 C 0.75591(15) 0.45917(13) 0.31957(12) 0.0493(6) Uani 1 1 d . . . H6 H 0.7268 0.4774 0.3581 0.059 Uiso 1 1 calc R . . C7 C 0.83167(15) 0.48817(13) 0.30596(13) 0.0546(6) Uani 1 1 d . . . H7 H 0.8534 0.5253 0.3352 0.065 Uiso 1 1 calc R . . C8 C 0.87475(14) 0.46158(12) 0.24860(13) 0.0493(6) Uani 1 1 d . . . H8 H 0.9250 0.4823 0.2386 0.059 Uiso 1 1 calc R . . C9 C 0.84442(12) 0.40388(12) 0.20494(11) 0.0389(5) Uani 1 1 d . . . C10 C 0.89517(15) 0.37491(16) 0.14404(13) 0.0622(7) Uani 1 1 d . . . H10A H 0.9142 0.3251 0.1550 0.093 Uiso 1 1 calc R . . H10B H 0.9403 0.4079 0.1369 0.093 Uiso 1 1 calc R . . H10C H 0.8631 0.3733 0.1016 0.093 Uiso 1 1 calc R . . C11 C 0.63657(13) 0.37686(13) 0.29123(12) 0.0475(6) Uani 1 1 d . . . H11A H 0.6379 0.3312 0.3187 0.071 Uiso 1 1 calc R . . H11B H 0.6096 0.3676 0.2469 0.071 Uiso 1 1 calc R . . H11C H 0.6081 0.4151 0.3172 0.071 Uiso 1 1 calc R . . C12 C 0.56458(11) 0.15875(10) 0.12126(10) 0.0298(4) Uani 1 1 d . . . C13 C 0.52059(12) 0.13482(11) 0.18093(10) 0.0325(4) Uani 1 1 d . . . C14 C 0.45645(12) 0.08470(12) 0.16887(12) 0.0412(5) Uani 1 1 d . . . H14 H 0.4265 0.0672 0.2073 0.049 Uiso 1 1 calc R . . C15 C 0.43693(13) 0.06091(12) 0.10109(12) 0.0444(5) Uani 1 1 d . . . H15 H 0.3938 0.0282 0.0942 0.053 Uiso 1 1 calc R . . C16 C 0.48138(13) 0.08560(11) 0.04370(12) 0.0418(5) Uani 1 1 d . . . H16 H 0.4676 0.0693 -0.0017 0.050 Uiso 1 1 calc R . . C17 C 0.54678(12) 0.13456(11) 0.05230(11) 0.0351(4) Uani 1 1 d . . . C18 C 0.59490(16) 0.15986(13) -0.01158(11) 0.0526(6) Uani 1 1 d . . . H18A H 0.5793 0.2102 -0.0244 0.079 Uiso 1 1 calc R . . H18B H 0.5847 0.1264 -0.0507 0.079 Uiso 1 1 calc R . . H18C H 0.6513 0.1590 -0.0002 0.079 Uiso 1 1 calc R . . C19 C 0.53901(13) 0.16166(12) 0.25533(11) 0.0417(5) Uani 1 1 d . . . H19A H 0.4979 0.1441 0.2872 0.063 Uiso 1 1 calc R . . H19B H 0.5405 0.2158 0.2561 0.063 Uiso 1 1 calc R . . H19C H 0.5904 0.1422 0.2700 0.063 Uiso 1 1 calc R . . C20 C 0.47561(14) 0.32134(13) 0.12900(13) 0.0521(6) Uani 1 1 d . . . H20A H 0.4420 0.3632 0.1421 0.078 Uiso 1 1 calc R . . H20B H 0.5007 0.3009 0.1708 0.078 Uiso 1 1 calc R . . H20C H 0.4434 0.2831 0.1067 0.078 Uiso 1 1 calc R . . C21 C 0.49973(19) 0.38779(19) 0.02046(17) 0.0870(10) Uani 1 1 d . . . H21A H 0.4668 0.3537 -0.0065 0.131 Uiso 1 1 calc R . . H21B H 0.5407 0.4087 -0.0097 0.131 Uiso 1 1 calc R . . H21C H 0.4668 0.4277 0.0390 0.131 Uiso 1 1 calc R . . C22 C 0.79672(16) 0.26358(15) -0.01000(14) 0.0650(8) Uani 1 1 d . . . H22A H 0.7860 0.2187 -0.0369 0.098 Uiso 1 1 calc R . . H22B H 0.8147 0.2500 0.0368 0.098 Uiso 1 1 calc R . . H22C H 0.8378 0.2925 -0.0334 0.098 Uiso 1 1 calc R . . C23 C 0.6962(2) 0.33115(18) -0.07537(12) 0.0823(10) Uani 1 1 d . . . H23A H 0.7368 0.3619 -0.0973 0.123 Uiso 1 1 calc R . . H23B H 0.6470 0.3594 -0.0713 0.123 Uiso 1 1 calc R . . H23C H 0.6869 0.2871 -0.1039 0.123 Uiso 1 1 calc R . . C24 C 0.64014(17) 0.50753(13) 0.12687(14) 0.0616(7) Uani 1 1 d . . . H24A H 0.6730 0.5232 0.1662 0.092 Uiso 1 1 calc R . . H24B H 0.5923 0.4833 0.1444 0.092 Uiso 1 1 calc R . . H24C H 0.6254 0.5508 0.0991 0.092 Uiso 1 1 calc R . . C25 C 0.75187(18) 0.49342(15) 0.04731(15) 0.0723(8) Uani 1 1 d . . . H25A H 0.7312 0.5354 0.0208 0.108 Uiso 1 1 calc R . . H25B H 0.7788 0.4592 0.0157 0.108 Uiso 1 1 calc R . . H25C H 0.7894 0.5113 0.0824 0.108 Uiso 1 1 calc R . . N1 N 0.73532(9) 0.31322(8) 0.17642(8) 0.0279(3) Uani 1 1 d . . . N2 N 0.68550(12) 0.45453(10) 0.08247(9) 0.0428(4) Uani 1 1 d . . . N3 N 0.72329(12) 0.30837(10) -0.00472(9) 0.0457(5) Uani 1 1 d . . . N4 N 0.53780(11) 0.34697(10) 0.07947(9) 0.0427(4) Uani 1 1 d . . . O O 0.62837(7) 0.21126(7) 0.13109(6) 0.0285(3) Uani 1 1 d . . . Zr Zr 0.662899(11) 0.339398(10) 0.086488(9) 0.02950(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0508(14) 0.0418(13) 0.0774(18) -0.0026(12) -0.0273(13) 0.0059(11) C2 0.0348(10) 0.0287(10) 0.0327(10) -0.0009(8) -0.0048(8) 0.0033(8) C3 0.0306(10) 0.0275(10) 0.0368(11) -0.0017(8) 0.0020(9) 0.0044(8) C4 0.0347(10) 0.0280(10) 0.0261(9) 0.0010(8) -0.0028(8) -0.0008(8) C5 0.0399(11) 0.0332(11) 0.0330(11) -0.0044(8) 0.0003(9) -0.0004(9) C6 0.0590(15) 0.0449(13) 0.0439(13) -0.0168(11) 0.0010(11) 0.0015(11) C7 0.0618(16) 0.0426(13) 0.0593(15) -0.0160(11) -0.0103(13) -0.0095(12) C8 0.0454(13) 0.0441(13) 0.0585(15) -0.0010(12) -0.0044(11) -0.0172(11) C9 0.0388(12) 0.0398(12) 0.0382(11) -0.0006(9) 0.0010(9) -0.0069(10) C10 0.0494(15) 0.0825(19) 0.0548(15) -0.0110(14) 0.0167(12) -0.0215(14) C11 0.0462(13) 0.0513(14) 0.0450(13) -0.0153(11) 0.0119(10) -0.0003(11) C12 0.0330(10) 0.0208(9) 0.0358(10) 0.0011(8) -0.0023(8) 0.0012(8) C13 0.0341(10) 0.0257(9) 0.0377(11) 0.0018(8) 0.0014(9) 0.0044(8) C14 0.0369(11) 0.0338(11) 0.0529(13) 0.0080(10) 0.0061(10) 0.0006(9) C15 0.0371(12) 0.0344(12) 0.0617(15) 0.0011(10) -0.0087(11) -0.0045(9) C16 0.0497(13) 0.0321(11) 0.0437(12) -0.0041(9) -0.0133(10) 0.0000(10) C17 0.0425(11) 0.0279(10) 0.0349(11) -0.0020(9) -0.0050(9) 0.0005(9) C18 0.0747(17) 0.0525(14) 0.0305(11) -0.0074(10) -0.0001(11) -0.0152(13) C19 0.0468(12) 0.0422(11) 0.0361(11) 0.0028(10) 0.0087(9) 0.0009(10) C20 0.0420(13) 0.0477(14) 0.0666(16) 0.0022(12) -0.0009(12) 0.0104(11) C21 0.073(2) 0.106(3) 0.082(2) 0.0423(19) -0.0236(17) 0.0069(18) C22 0.0753(18) 0.0636(18) 0.0561(16) -0.0156(13) 0.0308(14) -0.0145(15) C23 0.130(3) 0.086(2) 0.0309(13) 0.0091(13) 0.0107(15) -0.010(2) C24 0.0849(19) 0.0338(13) 0.0660(17) -0.0015(12) 0.0007(14) 0.0026(13) C25 0.091(2) 0.0462(15) 0.079(2) -0.0006(14) 0.0163(17) -0.0240(15) N1 0.0325(8) 0.0253(8) 0.0257(8) -0.0019(6) 0.0010(7) -0.0017(7) N2 0.0611(12) 0.0292(9) 0.0380(10) 0.0035(8) -0.0009(9) -0.0055(8) N3 0.0664(13) 0.0429(10) 0.0279(9) -0.0011(8) 0.0125(9) -0.0126(10) N4 0.0440(10) 0.0372(10) 0.0467(11) 0.0090(8) -0.0112(8) 0.0021(8) O 0.0322(7) 0.0250(6) 0.0282(7) 0.0017(5) -0.0032(6) -0.0010(6) Zr 0.03916(11) 0.02652(10) 0.02282(9) 0.00145(8) -0.00059(8) -0.00244(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.536(3) . ? C2 N1 1.486(2) . ? C2 C3 1.517(3) . ? C3 O 1.464(2) . ? C4 C9 1.411(3) . ? C4 C5 1.418(3) . ? C4 N1 1.445(2) . ? C5 C6 1.397(3) . ? C5 C11 1.513(3) . ? C6 C7 1.381(3) . ? C7 C8 1.377(3) . ? C8 C9 1.405(3) . ? C9 C10 1.512(3) . ? C12 C17 1.398(3) . ? C12 C13 1.405(3) . ? C12 O 1.421(2) . ? C13 C14 1.404(3) . ? C13 C19 1.510(3) . ? C14 C15 1.382(3) . ? C15 C16 1.379(3) . ? C16 C17 1.398(3) . ? C17 C18 1.511(3) . ? C20 N4 1.462(3) . ? C21 N4 1.468(3) . ? C22 N3 1.457(3) . ? C23 N3 1.460(3) . ? C24 N2 1.465(3) . ? C25 N2 1.458(3) . ? N1 Zr 2.1263(15) . ? N2 Zr 2.0763(17) . ? N3 Zr 2.0617(17) . ? N4 Zr 2.0830(18) . ? O Zr 2.4882(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 108.26(15) . . ? N1 C2 C1 114.11(17) . . ? C3 C2 C1 108.05(16) . . ? O C3 C2 107.88(14) . . ? C9 C4 C5 119.33(17) . . ? C9 C4 N1 120.44(17) . . ? C5 C4 N1 120.21(16) . . ? C6 C5 C4 118.94(19) . . ? C6 C5 C11 119.59(19) . . ? C4 C5 C11 121.45(17) . . ? C7 C6 C5 121.7(2) . . ? C8 C7 C6 119.3(2) . . ? C7 C8 C9 121.4(2) . . ? C8 C9 C4 119.14(19) . . ? C8 C9 C10 119.43(19) . . ? C4 C9 C10 121.42(19) . . ? C17 C12 C13 122.67(17) . . ? C17 C12 O 118.60(16) . . ? C13 C12 O 118.71(16) . . ? C14 C13 C12 117.08(18) . . ? C14 C13 C19 120.16(18) . . ? C12 C13 C19 122.75(18) . . ? C15 C14 C13 121.3(2) . . ? C16 C15 C14 120.0(2) . . ? C15 C16 C17 121.4(2) . . ? C12 C17 C16 117.47(19) . . ? C12 C17 C18 122.41(18) . . ? C16 C17 C18 120.12(18) . . ? C4 N1 C2 112.84(14) . . ? C4 N1 Zr 119.90(11) . . ? C2 N1 Zr 124.55(11) . . ? C25 N2 C24 110.07(19) . . ? C25 N2 Zr 128.15(16) . . ? C24 N2 Zr 121.12(15) . . ? C22 N3 C23 110.2(2) . . ? C22 N3 Zr 127.46(15) . . ? C23 N3 Zr 122.31(18) . . ? C20 N4 C21 109.39(19) . . ? C20 N4 Zr 129.93(14) . . ? C21 N4 Zr 120.53(17) . . ? C12 O C3 115.34(13) . . ? C12 O Zr 136.49(10) . . ? C3 O Zr 106.65(10) . . ? N3 Zr N2 98.29(7) . . ? N3 Zr N4 116.62(7) . . ? N2 Zr N4 96.55(7) . . ? N3 Zr N1 109.26(7) . . ? N2 Zr N1 98.14(6) . . ? N4 Zr N1 128.83(6) . . ? N3 Zr O 98.57(6) . . ? N2 Zr O 162.00(5) . . ? N4 Zr O 81.43(5) . . ? N1 Zr O 70.27(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O -46.40(19) . . . . ? C1 C2 C3 O -170.45(16) . . . . ? C9 C4 C5 C6 -3.6(3) . . . . ? N1 C4 C5 C6 177.60(18) . . . . ? C9 C4 C5 C11 174.84(19) . . . . ? N1 C4 C5 C11 -3.9(3) . . . . ? C4 C5 C6 C7 2.4(3) . . . . ? C11 C5 C6 C7 -176.1(2) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C6 C7 C8 C9 -2.1(4) . . . . ? C7 C8 C9 C4 0.8(3) . . . . ? C7 C8 C9 C10 -178.0(2) . . . . ? C5 C4 C9 C8 2.1(3) . . . . ? N1 C4 C9 C8 -179.18(18) . . . . ? C5 C4 C9 C10 -179.1(2) . . . . ? N1 C4 C9 C10 -0.3(3) . . . . ? C17 C12 C13 C14 -0.1(3) . . . . ? O C12 C13 C14 178.11(16) . . . . ? C17 C12 C13 C19 -179.17(18) . . . . ? O C12 C13 C19 -0.9(3) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C19 C13 C14 C15 178.19(19) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C13 C12 C17 C16 1.1(3) . . . . ? O C12 C17 C16 -177.12(16) . . . . ? C13 C12 C17 C18 -179.32(19) . . . . ? O C12 C17 C18 2.4(3) . . . . ? C15 C16 C17 C12 -1.2(3) . . . . ? C15 C16 C17 C18 179.3(2) . . . . ? C9 C4 N1 C2 106.6(2) . . . . ? C5 C4 N1 C2 -74.6(2) . . . . ? C9 C4 N1 Zr -91.19(19) . . . . ? C5 C4 N1 Zr 87.56(19) . . . . ? C3 C2 N1 C4 -179.28(15) . . . . ? C1 C2 N1 C4 -58.9(2) . . . . ? C3 C2 N1 Zr 19.5(2) . . . . ? C1 C2 N1 Zr 139.85(15) . . . . ? C17 C12 O C3 -106.93(19) . . . . ? C13 C12 O C3 74.8(2) . . . . ? C17 C12 O Zr 56.7(2) . . . . ? C13 C12 O Zr -121.61(16) . . . . ? C2 C3 O C12 -141.81(15) . . . . ? C2 C3 O Zr 49.87(15) . . . . ? C22 N3 Zr N2 112.02(19) . . . . ? C23 N3 Zr N2 -67.0(2) . . . . ? C22 N3 Zr N4 -146.32(18) . . . . ? C23 N3 Zr N4 34.6(2) . . . . ? C22 N3 Zr N1 10.3(2) . . . . ? C23 N3 Zr N1 -168.71(19) . . . . ? C22 N3 Zr O -61.65(19) . . . . ? C23 N3 Zr O 119.30(19) . . . . ? C25 N2 Zr N3 -24.6(2) . . . . ? C24 N2 Zr N3 165.63(18) . . . . ? C25 N2 Zr N4 -142.8(2) . . . . ? C24 N2 Zr N4 47.43(18) . . . . ? C25 N2 Zr N1 86.4(2) . . . . ? C24 N2 Zr N1 -83.41(18) . . . . ? C25 N2 Zr O 134.8(2) . . . . ? C24 N2 Zr O -35.0(3) . . . . ? C20 N4 Zr N3 137.15(18) . . . . ? C21 N4 Zr N3 -47.8(2) . . . . ? C20 N4 Zr N2 -120.15(19) . . . . ? C21 N4 Zr N2 54.9(2) . . . . ? C20 N4 Zr N1 -14.2(2) . . . . ? C21 N4 Zr N1 160.85(19) . . . . ? C20 N4 Zr O 41.81(18) . . . . ? C21 N4 Zr O -143.2(2) . . . . ? C4 N1 Zr N3 113.15(13) . . . . ? C2 N1 Zr N3 -86.87(15) . . . . ? C4 N1 Zr N2 11.36(14) . . . . ? C2 N1 Zr N2 171.34(14) . . . . ? C4 N1 Zr N4 -93.89(14) . . . . ? C2 N1 Zr N4 66.09(16) . . . . ? C4 N1 Zr O -154.42(14) . . . . ? C2 N1 Zr O 5.55(13) . . . . ? C12 O Zr N3 -87.51(16) . . . . ? C3 O Zr N3 77.07(11) . . . . ? C12 O Zr N2 113.1(2) . . . . ? C3 O Zr N2 -82.3(2) . . . . ? C12 O Zr N4 28.31(16) . . . . ? C3 O Zr N4 -167.10(11) . . . . ? C12 O Zr N1 165.01(16) . . . . ? C3 O Zr N1 -30.41(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.340 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.050