Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Erker, G.' 'Frohlich, Roland' 'Huerlander, Doris' _publ_contact_author_name 'Prof G Erker' _publ_contact_author_address ; Organisch-Chemisches Institut der Universitat Munster Corrensstrasse 40 Munster D-48149 GERMANY ; _publ_contact_author_email 'ERKER@UNI-MUENSTER.DE' _publ_section_title ; Synthesis and structural characterization of Group 4 metallocene complexes that contain remote carboxamide functionalities at the Cp-side chains ; data_erk1178 _database_code_CSD 179005 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H40 Fe N2 O2' _chemical_formula_weight 468.45 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' 'Fe' 'Fe' 0.3463 0.8444 '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 6.001(1) _cell_length_b 8.113(1) _cell_length_c 12.399(1) _cell_angle_alpha 99.19(1) _cell_angle_beta 94.36(1) _cell_angle_gamma 93.36(1) _cell_volume 592.65(13) _cell_formula_units_Z 1 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.661 _exptl_absorpt_correction_type 'SORTAV (Blessing, 1995 & 1997)' _exptl_absorpt_correction_T_min 0.8791 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4789 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2720 _reflns_number_gt 2611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Shedlrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+0.2638P] 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 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2720 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 Fe1 Fe 0.0000 0.0000 0.0000 0.02273(10) Uani 1 2 d S . . C1 C 0.1523(2) 0.13437(17) 0.14681(11) 0.0227(3) Uani 1 1 d . . . C2 C -0.0607(2) 0.05930(19) 0.16253(11) 0.0270(3) Uani 1 1 d . . . H2 H -0.1827 0.1176 0.1900 0.032 Uiso 1 1 calc R . . C3 C -0.0614(3) -0.1167(2) 0.13059(12) 0.0334(4) Uani 1 1 d . . . H3 H -0.1830 -0.1960 0.1330 0.040 Uiso 1 1 calc R . . C4 C 0.1499(3) -0.15272(19) 0.09470(12) 0.0339(4) Uani 1 1 d . . . H4 H 0.1960 -0.2608 0.0685 0.041 Uiso 1 1 calc R . . C5 C 0.2823(3) 0.00079(19) 0.10450(12) 0.0283(3) Uani 1 1 d . . . H5 H 0.4325 0.0126 0.0860 0.034 Uiso 1 1 calc R . . C6 C 0.2352(2) 0.31676(18) 0.18135(12) 0.0258(3) Uani 1 1 d . . . C7 C 0.3695(3) 0.3790(2) 0.09343(14) 0.0378(4) Uani 1 1 d . . . H7A H 0.4864 0.3027 0.0745 0.057 Uiso 1 1 calc R . . H7B H 0.4389 0.4915 0.1218 0.057 Uiso 1 1 calc R . . H7C H 0.2689 0.3826 0.0279 0.057 Uiso 1 1 calc R . . C8 C 0.0393(3) 0.4273(2) 0.20164(14) 0.0355(4) Uani 1 1 d . . . H8A H -0.0589 0.4182 0.1338 0.053 Uiso 1 1 calc R . . H8B H 0.0973 0.5440 0.2252 0.053 Uiso 1 1 calc R . . H8C H -0.0458 0.3904 0.2589 0.053 Uiso 1 1 calc R . . C9 C 0.3964(2) 0.33217(19) 0.28670(12) 0.0287(3) Uani 1 1 d . . . H9A H 0.5197 0.2584 0.2710 0.034 Uiso 1 1 calc R . . H9B H 0.4636 0.4487 0.3047 0.034 Uiso 1 1 calc R . . C10 C 0.2911(2) 0.2883(2) 0.38656(12) 0.0297(3) Uani 1 1 d . . . H10A H 0.1877 0.1868 0.3644 0.036 Uiso 1 1 calc R . . H10B H 0.2022 0.3810 0.4170 0.036 Uiso 1 1 calc R . . C11 C 0.4660(3) 0.2569(2) 0.47483(13) 0.0312(3) Uani 1 1 d . . . O12 O 0.6663(2) 0.2701(2) 0.46217(12) 0.0552(4) Uani 1 1 d . . . N13 N 0.3912(2) 0.20995(18) 0.56579(11) 0.0353(3) Uani 1 1 d . . . C14 C 0.1588(3) 0.1975(3) 0.58875(16) 0.0544(5) Uani 1 1 d . . . H14A H 0.0649 0.2280 0.5279 0.082 Uiso 1 1 calc R . . H14B H 0.1387 0.2736 0.6565 0.082 Uiso 1 1 calc R . . H14C H 0.1154 0.0823 0.5974 0.082 Uiso 1 1 calc R . . C15 C 0.5484(3) 0.1682(2) 0.65031(15) 0.0449(4) Uani 1 1 d . . . H15A H 0.6986 0.1665 0.6244 0.067 Uiso 1 1 calc R . . H15B H 0.5026 0.0578 0.6670 0.067 Uiso 1 1 calc R . . H15C H 0.5500 0.2523 0.7166 0.067 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 Fe1 0.02712(16) 0.02605(16) 0.01587(15) 0.00606(11) 0.00108(10) 0.00279(11) C1 0.0249(6) 0.0285(7) 0.0152(6) 0.0056(5) -0.0005(5) 0.0033(5) C2 0.0292(7) 0.0353(8) 0.0168(6) 0.0050(6) 0.0040(5) 0.0001(6) C3 0.0477(9) 0.0345(8) 0.0179(7) 0.0096(6) -0.0005(6) -0.0087(7) C4 0.0543(10) 0.0269(7) 0.0210(7) 0.0071(6) -0.0051(7) 0.0101(7) C5 0.0293(7) 0.0364(8) 0.0201(7) 0.0065(6) -0.0009(5) 0.0099(6) C6 0.0270(7) 0.0280(7) 0.0223(7) 0.0049(6) -0.0002(5) 0.0009(5) C7 0.0451(9) 0.0384(9) 0.0299(8) 0.0100(7) 0.0030(7) -0.0087(7) C8 0.0383(8) 0.0298(8) 0.0370(9) 0.0034(7) -0.0045(7) 0.0074(6) C9 0.0269(7) 0.0329(8) 0.0250(7) 0.0032(6) -0.0017(6) 0.0003(6) C10 0.0272(7) 0.0389(8) 0.0223(7) 0.0031(6) -0.0013(6) 0.0054(6) C11 0.0303(8) 0.0349(8) 0.0268(8) 0.0031(6) -0.0044(6) 0.0023(6) O12 0.0271(6) 0.0931(11) 0.0493(8) 0.0304(8) -0.0064(5) -0.0005(6) N13 0.0340(7) 0.0470(8) 0.0243(6) 0.0064(6) -0.0043(5) 0.0051(6) C14 0.0422(10) 0.0933(16) 0.0307(9) 0.0152(10) 0.0080(8) 0.0101(10) C15 0.0510(10) 0.0505(10) 0.0328(9) 0.0115(8) -0.0113(8) 0.0065(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 Fe1 C4 2.0390(14) 2 ? Fe1 C4 2.0390(14) . ? Fe1 C3 2.0476(14) . ? Fe1 C3 2.0476(14) 2 ? Fe1 C5 2.0522(14) 2 ? Fe1 C5 2.0522(14) . ? Fe1 C2 2.0610(14) . ? Fe1 C2 2.0610(14) 2 ? Fe1 C1 2.0817(13) 2 ? Fe1 C1 2.0817(13) . ? C1 C2 1.424(2) . ? C1 C5 1.428(2) . ? C1 C6 1.5164(19) . ? C2 C3 1.419(2) . ? C3 C4 1.407(2) . ? C4 C5 1.421(2) . ? C6 C8 1.532(2) . ? C6 C7 1.534(2) . ? C6 C9 1.5488(19) . ? C9 C10 1.514(2) . ? C10 C11 1.520(2) . ? C11 O12 1.225(2) . ? C11 N13 1.346(2) . ? N13 C14 1.445(2) . ? N13 C15 1.450(2) . ? 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 C4 Fe1 C4 180.00(11) 2 . ? C4 Fe1 C3 139.73(7) 2 . ? C4 Fe1 C3 40.27(7) . . ? C4 Fe1 C3 40.27(7) 2 2 ? C4 Fe1 C3 139.73(7) . 2 ? C3 Fe1 C3 180.00(7) . 2 ? C4 Fe1 C5 40.64(6) 2 2 ? C4 Fe1 C5 139.36(6) . 2 ? C3 Fe1 C5 112.14(6) . 2 ? C3 Fe1 C5 67.86(6) 2 2 ? C4 Fe1 C5 139.36(6) 2 . ? C4 Fe1 C5 40.64(6) . . ? C3 Fe1 C5 67.86(6) . . ? C3 Fe1 C5 112.14(6) 2 . ? C5 Fe1 C5 180.00(7) 2 . ? C4 Fe1 C2 112.29(6) 2 . ? C4 Fe1 C2 67.71(6) . . ? C3 Fe1 C2 40.40(6) . . ? C3 Fe1 C2 139.60(6) 2 . ? C5 Fe1 C2 112.58(6) 2 . ? C5 Fe1 C2 67.42(6) . . ? C4 Fe1 C2 67.71(6) 2 2 ? C4 Fe1 C2 112.29(6) . 2 ? C3 Fe1 C2 139.60(6) . 2 ? C3 Fe1 C2 40.40(6) 2 2 ? C5 Fe1 C2 67.42(6) 2 2 ? C5 Fe1 C2 112.58(6) . 2 ? C2 Fe1 C2 180.00(2) . 2 ? C4 Fe1 C1 68.33(6) 2 2 ? C4 Fe1 C1 111.67(6) . 2 ? C3 Fe1 C1 111.83(6) . 2 ? C3 Fe1 C1 68.17(6) 2 2 ? C5 Fe1 C1 40.40(6) 2 2 ? C5 Fe1 C1 139.60(6) . 2 ? C2 Fe1 C1 139.80(5) . 2 ? C2 Fe1 C1 40.20(5) 2 2 ? C4 Fe1 C1 111.67(6) 2 . ? C4 Fe1 C1 68.33(6) . . ? C3 Fe1 C1 68.17(6) . . ? C3 Fe1 C1 111.83(6) 2 . ? C5 Fe1 C1 139.60(6) 2 . ? C5 Fe1 C1 40.40(6) . . ? C2 Fe1 C1 40.20(5) . . ? C2 Fe1 C1 139.80(5) 2 . ? C1 Fe1 C1 180.00(8) 2 . ? C2 C1 C5 106.37(13) . . ? C2 C1 C6 126.87(13) . . ? C5 C1 C6 126.35(13) . . ? C2 C1 Fe1 69.12(8) . . ? C5 C1 Fe1 68.69(8) . . ? C6 C1 Fe1 132.51(9) . . ? C3 C2 C1 109.00(14) . . ? C3 C2 Fe1 69.29(8) . . ? C1 C2 Fe1 70.68(8) . . ? C4 C3 C2 107.88(13) . . ? C4 C3 Fe1 69.54(8) . . ? C2 C3 Fe1 70.31(8) . . ? C3 C4 C5 108.06(14) . . ? C3 C4 Fe1 70.19(9) . . ? C5 C4 Fe1 70.18(8) . . ? C4 C5 C1 108.69(13) . . ? C4 C5 Fe1 69.18(8) . . ? C1 C5 Fe1 70.91(8) . . ? C1 C6 C8 111.02(12) . . ? C1 C6 C7 111.02(12) . . ? C8 C6 C7 108.69(13) . . ? C1 C6 C9 108.37(11) . . ? C8 C6 C9 110.55(12) . . ? C7 C6 C9 107.12(12) . . ? C10 C9 C6 115.44(12) . . ? C9 C10 C11 111.99(12) . . ? O12 C11 N13 121.65(14) . . ? O12 C11 C10 121.07(14) . . ? N13 C11 C10 117.26(13) . . ? C11 N13 C14 125.01(14) . . ? C11 N13 C15 120.12(14) . . ? C14 N13 C15 114.87(15) . . ? 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 C4 Fe1 C1 C2 99.33(10) 2 . . . ? C4 Fe1 C1 C2 -80.67(10) . . . . ? C3 Fe1 C1 C2 -37.17(9) . . . . ? C3 Fe1 C1 C2 142.83(9) 2 . . . ? C5 Fe1 C1 C2 61.80(12) 2 . . . ? C5 Fe1 C1 C2 -118.20(12) . . . . ? C2 Fe1 C1 C2 180.0 2 . . . ? C1 Fe1 C1 C2 -161(100) 2 . . . ? C4 Fe1 C1 C5 -142.47(9) 2 . . . ? C4 Fe1 C1 C5 37.53(9) . . . . ? C3 Fe1 C1 C5 81.04(10) . . . . ? C3 Fe1 C1 C5 -98.96(10) 2 . . . ? C5 Fe1 C1 C5 180.0 2 . . . ? C2 Fe1 C1 C5 118.20(12) . . . . ? C2 Fe1 C1 C5 -61.80(12) 2 . . . ? C1 Fe1 C1 C5 -42(100) 2 . . . ? C4 Fe1 C1 C6 -22.11(15) 2 . . . ? C4 Fe1 C1 C6 157.89(15) . . . . ? C3 Fe1 C1 C6 -158.60(15) . . . . ? C3 Fe1 C1 C6 21.40(15) 2 . . . ? C5 Fe1 C1 C6 -59.64(17) 2 . . . ? C5 Fe1 C1 C6 120.36(17) . . . . ? C2 Fe1 C1 C6 -121.43(17) . . . . ? C2 Fe1 C1 C6 58.57(17) 2 . . . ? C1 Fe1 C1 C6 78(100) 2 . . . ? C5 C1 C2 C3 0.03(15) . . . . ? C6 C1 C2 C3 -172.97(12) . . . . ? Fe1 C1 C2 C3 58.86(10) . . . . ? C5 C1 C2 Fe1 -58.84(9) . . . . ? C6 C1 C2 Fe1 128.17(13) . . . . ? C4 Fe1 C2 C3 142.25(10) 2 . . . ? C4 Fe1 C2 C3 -37.75(10) . . . . ? C3 Fe1 C2 C3 180.0 2 . . . ? C5 Fe1 C2 C3 98.12(10) 2 . . . ? C5 Fe1 C2 C3 -81.88(10) . . . . ? C2 Fe1 C2 C3 -151(100) 2 . . . ? C1 Fe1 C2 C3 59.91(13) 2 . . . ? C1 Fe1 C2 C3 -120.09(13) . . . . ? C4 Fe1 C2 C1 -97.66(9) 2 . . . ? C4 Fe1 C2 C1 82.34(9) . . . . ? C3 Fe1 C2 C1 120.09(13) . . . . ? C3 Fe1 C2 C1 -59.91(13) 2 . . . ? C5 Fe1 C2 C1 -141.78(8) 2 . . . ? C5 Fe1 C2 C1 38.22(8) . . . . ? C2 Fe1 C2 C1 -31(100) 2 . . . ? C1 Fe1 C2 C1 180.0 2 . . . ? C1 C2 C3 C4 -0.09(16) . . . . ? Fe1 C2 C3 C4 59.63(10) . . . . ? C1 C2 C3 Fe1 -59.72(10) . . . . ? C4 Fe1 C3 C4 180.0 2 . . . ? C3 Fe1 C3 C4 -27(100) 2 . . . ? C5 Fe1 C3 C4 141.92(9) 2 . . . ? C5 Fe1 C3 C4 -38.08(9) . . . . ? C2 Fe1 C3 C4 -118.79(13) . . . . ? C2 Fe1 C3 C4 61.21(13) 2 . . . ? C1 Fe1 C3 C4 98.19(9) 2 . . . ? C1 Fe1 C3 C4 -81.81(9) . . . . ? C4 Fe1 C3 C2 -61.21(13) 2 . . . ? C4 Fe1 C3 C2 118.79(13) . . . . ? C3 Fe1 C3 C2 92(100) 2 . . . ? C5 Fe1 C3 C2 -99.29(9) 2 . . . ? C5 Fe1 C3 C2 80.71(9) . . . . ? C2 Fe1 C3 C2 180.0 2 . . . ? C1 Fe1 C3 C2 -143.02(8) 2 . . . ? C1 Fe1 C3 C2 36.98(8) . . . . ? C2 C3 C4 C5 0.12(16) . . . . ? Fe1 C3 C4 C5 60.23(10) . . . . ? C2 C3 C4 Fe1 -60.11(10) . . . . ? C4 Fe1 C4 C3 59(100) 2 . . . ? C3 Fe1 C4 C3 180.0 2 . . . ? C5 Fe1 C4 C3 -61.31(13) 2 . . . ? C5 Fe1 C4 C3 118.69(13) . . . . ? C2 Fe1 C4 C3 37.87(9) . . . . ? C2 Fe1 C4 C3 -142.13(9) 2 . . . ? C1 Fe1 C4 C3 -98.63(9) 2 . . . ? C1 Fe1 C4 C3 81.37(9) . . . . ? C4 Fe1 C4 C5 -59(100) 2 . . . ? C3 Fe1 C4 C5 -118.69(13) . . . . ? C3 Fe1 C4 C5 61.31(13) 2 . . . ? C5 Fe1 C4 C5 180.0 2 . . . ? C2 Fe1 C4 C5 -80.82(9) . . . . ? C2 Fe1 C4 C5 99.18(9) 2 . . . ? C1 Fe1 C4 C5 142.68(9) 2 . . . ? C1 Fe1 C4 C5 -37.32(9) . . . . ? C3 C4 C5 C1 -0.10(16) . . . . ? Fe1 C4 C5 C1 60.14(10) . . . . ? C3 C4 C5 Fe1 -60.24(10) . . . . ? C2 C1 C5 C4 0.05(15) . . . . ? C6 C1 C5 C4 173.09(12) . . . . ? Fe1 C1 C5 C4 -59.07(10) . . . . ? C2 C1 C5 Fe1 59.11(9) . . . . ? C6 C1 C5 Fe1 -127.84(13) . . . . ? C4 Fe1 C5 C4 180.0 2 . . . ? C3 Fe1 C5 C4 37.75(9) . . . . ? C3 Fe1 C5 C4 -142.25(9) 2 . . . ? C5 Fe1 C5 C4 1(21) 2 . . . ? C2 Fe1 C5 C4 81.60(10) . . . . ? C2 Fe1 C5 C4 -98.40(10) 2 . . . ? C1 Fe1 C5 C4 -60.38(13) 2 . . . ? C1 Fe1 C5 C4 119.62(13) . . . . ? C4 Fe1 C5 C1 60.38(13) 2 . . . ? C4 Fe1 C5 C1 -119.62(13) . . . . ? C3 Fe1 C5 C1 -81.88(9) . . . . ? C3 Fe1 C5 C1 98.12(9) 2 . . . ? C5 Fe1 C5 C1 -118(21) 2 . . . ? C2 Fe1 C5 C1 -38.03(8) . . . . ? C2 Fe1 C5 C1 141.97(8) 2 . . . ? C1 Fe1 C5 C1 180.0 2 . . . ? C2 C1 C6 C8 -19.13(19) . . . . ? C5 C1 C6 C8 169.23(13) . . . . ? Fe1 C1 C6 C8 75.64(16) . . . . ? C2 C1 C6 C7 -140.16(14) . . . . ? C5 C1 C6 C7 48.19(18) . . . . ? Fe1 C1 C6 C7 -45.39(18) . . . . ? C2 C1 C6 C9 102.46(16) . . . . ? C5 C1 C6 C9 -69.19(17) . . . . ? Fe1 C1 C6 C9 -162.77(11) . . . . ? C1 C6 C9 C10 -64.35(16) . . . . ? C8 C6 C9 C10 57.52(17) . . . . ? C7 C6 C9 C10 175.79(13) . . . . ? C6 C9 C10 C11 163.26(13) . . . . ? C9 C10 C11 O12 1.0(2) . . . . ? C9 C10 C11 N13 -177.34(14) . . . . ? O12 C11 N13 C14 177.55(19) . . . . ? C10 C11 N13 C14 -4.1(3) . . . . ? O12 C11 N13 C15 -2.1(3) . . . . ? C10 C11 N13 C15 176.30(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.316 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.044 data_erk_979 _database_code_CSD 179006 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Cl2 N O Zr' _chemical_formula_weight 461.56 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' '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 6.975(1) _cell_length_b 12.127(1) _cell_length_c 12.384(1) _cell_angle_alpha 95.65(1) _cell_angle_beta 91.35(1) _cell_angle_gamma 90.44(1) _cell_volume 1042.08(19) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.7971 _exptl_absorpt_correction_T_max 0.9250 _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14680 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 30.52 _reflns_number_total 6265 _reflns_number_gt 5834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.2998P] 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 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6265 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0549 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zr Zr 0.026928(15) 0.171560(8) 0.258311(8) 0.01808(4) Uani 1 d . . . Cl1 Cl 0.25187(4) 0.04066(2) 0.17198(3) 0.02672(7) Uani 1 d . . . Cl2 Cl -0.16930(5) 0.03306(3) 0.33590(3) 0.03348(8) Uani 1 d . . . C11 C 0.1877(2) 0.18043(10) 0.44415(11) 0.0329(3) Uani 1 d . . . H11 H 0.1935 0.1149 0.4803 0.040 Uiso 1 calc R . . C12 C 0.0397(2) 0.25903(11) 0.45181(11) 0.0343(3) Uani 1 d . . . H12 H -0.0718 0.2559 0.4941 0.041 Uiso 1 calc R . . C13 C 0.0860(2) 0.34270(10) 0.38608(11) 0.0324(3) Uani 1 d . . . H13 H 0.0124 0.4068 0.3768 0.039 Uiso 1 calc R . . C14 C 0.2598(2) 0.31511(10) 0.33657(11) 0.0303(3) Uani 1 d . . . H14 H 0.3233 0.3562 0.2863 0.036 Uiso 1 calc R . . C15 C 0.3242(2) 0.21562(11) 0.37435(11) 0.0315(3) Uani 1 d . . . H15 H 0.4403 0.1789 0.3555 0.038 Uiso 1 calc R . . C21 C -0.07812(18) 0.32621(9) 0.15154(10) 0.0250(2) Uani 1 d . . . H21 H -0.0237 0.3977 0.1709 0.030 Uiso 1 calc R . . C22 C -0.23963(19) 0.28154(10) 0.19923(11) 0.0295(3) Uani 1 d . . . H22 H -0.3116 0.3173 0.2565 0.035 Uiso 1 calc R . . C23 C -0.27513(18) 0.17486(11) 0.14698(11) 0.0290(3) Uani 1 d . . . H23 H -0.3772 0.1265 0.1614 0.035 Uiso 1 calc R . . C24 C -0.13350(18) 0.15253(9) 0.07001(10) 0.0236(2) Uani 1 d . . . H24 H -0.1211 0.0851 0.0248 0.028 Uiso 1 calc R . . C25 C -0.01119(17) 0.24676(9) 0.07031(10) 0.0216(2) Uani 1 d . . . C26 C 0.13598(19) 0.26793(10) -0.01366(11) 0.0267(2) Uani 1 d . . . C27 C 0.2108(2) 0.16046(12) -0.07276(12) 0.0377(3) Uani 1 d . . . H27A H 0.2855 0.1201 -0.0217 0.057 Uiso 1 calc R . . H27B H 0.2924 0.1782 -0.1321 0.057 Uiso 1 calc R . . H27C H 0.1022 0.1143 -0.1023 0.057 Uiso 1 calc R . . C28 C 0.3055(2) 0.33640(13) 0.03780(13) 0.0390(3) Uani 1 d . . . H28A H 0.2586 0.4058 0.0748 0.058 Uiso 1 calc R . . H28B H 0.3940 0.3531 -0.0189 0.058 Uiso 1 calc R . . H28C H 0.3727 0.2942 0.0904 0.058 Uiso 1 calc R . . C29 C 0.0363(2) 0.33763(10) -0.09676(11) 0.0304(3) Uani 1 d . . . H29A H -0.0070 0.4079 -0.0577 0.036 Uiso 1 calc R . . H29B H 0.1323 0.3567 -0.1497 0.036 Uiso 1 calc R . . C30 C -0.1345(2) 0.28212(10) -0.15897(11) 0.0318(3) Uani 1 d . . . H30A H -0.0939 0.2107 -0.1968 0.038 Uiso 1 calc R . . H30B H -0.2347 0.2662 -0.1072 0.038 Uiso 1 calc R . . C31 C -0.2179(2) 0.35389(10) -0.24119(11) 0.0300(3) Uani 1 d . . . O31 O -0.15918(19) 0.44892(8) -0.24607(9) 0.0492(3) Uani 1 d . . . N32 N -0.35862(17) 0.31030(8) -0.30939(9) 0.0272(2) Uani 1 d . . . C33 C -0.43926(19) 0.19832(9) -0.30928(11) 0.0261(2) Uani 1 d . . . H33A H -0.5798 0.2011 -0.3217 0.031 Uiso 1 calc R . . H33B H -0.4156 0.1721 -0.2370 0.031 Uiso 1 calc R . . C34 C -0.3552(2) 0.11656(10) -0.39477(12) 0.0325(3) Uani 1 d . . . H34A H -0.3738 0.1434 -0.4663 0.049 Uiso 1 calc R . . H34B H -0.4195 0.0445 -0.3941 0.049 Uiso 1 calc R . . H34C H -0.2178 0.1087 -0.3794 0.049 Uiso 1 calc R . . C35 C -0.4414(2) 0.37900(10) -0.38882(11) 0.0337(3) Uani 1 d . . . H35A H -0.4742 0.3316 -0.4565 0.040 Uiso 1 calc R . . H35B H -0.3446 0.4343 -0.4062 0.040 Uiso 1 calc R . . C36 C -0.6188(3) 0.43849(14) -0.34841(16) 0.0530(5) Uani 1 d . . . H36A H -0.7178 0.3840 -0.3349 0.079 Uiso 1 calc R . . H36B H -0.6665 0.4853 -0.4032 0.079 Uiso 1 calc R . . H36C H -0.5875 0.4848 -0.2808 0.079 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr 0.02002(6) 0.01702(5) 0.01719(6) 0.00262(4) -0.00303(4) -0.00245(4) Cl1 0.02678(15) 0.02603(13) 0.02698(16) 0.00134(11) -0.00257(12) 0.00352(10) Cl2 0.03835(18) 0.03310(15) 0.02984(17) 0.00796(12) 0.00277(14) -0.01280(12) C11 0.0497(9) 0.0273(6) 0.0215(6) 0.0045(5) -0.0133(6) -0.0065(5) C12 0.0423(8) 0.0369(7) 0.0220(6) -0.0052(5) 0.0015(6) -0.0082(6) C13 0.0426(8) 0.0230(5) 0.0296(7) -0.0045(5) -0.0103(6) -0.0010(5) C14 0.0356(7) 0.0294(6) 0.0250(6) 0.0030(5) -0.0099(6) -0.0128(5) C15 0.0290(7) 0.0356(6) 0.0284(7) -0.0014(5) -0.0135(5) -0.0029(5) C21 0.0285(6) 0.0200(5) 0.0266(6) 0.0053(4) -0.0069(5) 0.0014(4) C22 0.0246(6) 0.0328(6) 0.0312(7) 0.0035(5) -0.0015(5) 0.0071(5) C23 0.0203(6) 0.0355(6) 0.0318(7) 0.0085(5) -0.0070(5) -0.0047(5) C24 0.0251(6) 0.0234(5) 0.0221(6) 0.0037(4) -0.0080(5) -0.0031(4) C25 0.0227(6) 0.0225(5) 0.0201(6) 0.0066(4) -0.0070(4) -0.0013(4) C26 0.0274(6) 0.0311(6) 0.0224(6) 0.0087(5) -0.0042(5) -0.0039(5) C27 0.0417(8) 0.0448(8) 0.0285(7) 0.0105(6) 0.0096(6) 0.0096(6) C28 0.0287(7) 0.0562(9) 0.0335(8) 0.0145(6) -0.0070(6) -0.0125(6) C29 0.0381(7) 0.0292(6) 0.0245(6) 0.0100(5) -0.0091(6) -0.0097(5) C30 0.0419(8) 0.0260(6) 0.0283(7) 0.0111(5) -0.0128(6) -0.0089(5) C31 0.0422(8) 0.0232(5) 0.0244(6) 0.0053(4) -0.0103(6) -0.0047(5) O31 0.0765(9) 0.0259(5) 0.0456(7) 0.0150(4) -0.0334(6) -0.0191(5) N32 0.0367(6) 0.0216(4) 0.0234(5) 0.0057(4) -0.0100(5) -0.0041(4) C33 0.0276(6) 0.0252(5) 0.0256(6) 0.0041(4) -0.0034(5) -0.0052(4) C34 0.0401(8) 0.0257(6) 0.0311(7) 0.0003(5) -0.0023(6) -0.0018(5) C35 0.0472(8) 0.0277(6) 0.0262(7) 0.0079(5) -0.0149(6) -0.0028(5) C36 0.0606(12) 0.0450(9) 0.0545(11) 0.0124(8) -0.0113(9) 0.0160(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 Zr Cl1 2.4306(4) . ? Zr C22 2.4366(13) . ? Zr Cl2 2.4417(4) . ? Zr C14 2.4817(12) . ? Zr C23 2.4933(13) . ? Zr C21 2.5032(12) . ? Zr C13 2.5080(12) . ? Zr C15 2.5180(13) . ? Zr C12 2.5225(13) . ? Zr C11 2.5286(13) . ? Zr C24 2.5516(12) . ? Zr C25 2.5914(12) . ? C11 C15 1.393(2) . ? C11 C12 1.409(2) . ? C12 C13 1.402(2) . ? C13 C14 1.400(2) . ? C14 C15 1.4091(18) . ? C21 C25 1.4130(16) . ? C21 C22 1.4128(19) . ? C22 C23 1.4059(18) . ? C23 C24 1.3984(19) . ? C24 C25 1.4204(16) . ? C25 C26 1.5165(18) . ? C26 C28 1.5296(19) . ? C26 C27 1.5320(18) . ? C26 C29 1.5503(18) . ? C29 C30 1.5193(18) . ? C30 C31 1.5122(18) . ? C31 O31 1.2276(15) . ? C31 N32 1.3496(17) . ? N32 C35 1.4619(16) . ? N32 C33 1.4660(15) . ? C33 C34 1.5096(18) . ? C35 C36 1.508(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Zr C22 136.34(3) . . ? Cl1 Zr Cl2 95.818(14) . . ? C22 Zr Cl2 96.15(4) . . ? Cl1 Zr C14 98.70(4) . . ? C22 Zr C14 102.71(5) . . ? Cl2 Zr C14 133.71(3) . . ? Cl1 Zr C23 110.62(3) . . ? C22 Zr C23 33.11(4) . . ? Cl2 Zr C23 78.28(3) . . ? C14 Zr C23 134.39(4) . . ? Cl1 Zr C21 116.59(3) . . ? C22 Zr C21 33.20(4) . . ? Cl2 Zr C21 128.79(3) . . ? C14 Zr C21 81.72(4) . . ? C23 Zr C21 54.29(4) . . ? Cl1 Zr C13 130.29(4) . . ? C22 Zr C13 81.65(5) . . ? Cl2 Zr C13 113.03(4) . . ? C14 Zr C13 32.57(5) . . ? C23 Zr C13 114.23(5) . . ? C21 Zr C13 75.97(4) . . ? Cl1 Zr C15 79.00(3) . . ? C22 Zr C15 133.96(4) . . ? Cl2 Zr C15 110.32(4) . . ? C14 Zr C15 32.73(4) . . ? C23 Zr C15 166.89(4) . . ? C21 Zr C15 113.87(4) . . ? C13 Zr C15 53.75(5) . . ? Cl1 Zr C12 127.32(4) . . ? C22 Zr C12 95.81(5) . . ? Cl2 Zr C12 82.70(4) . . ? C14 Zr C12 53.84(5) . . ? C23 Zr C12 120.33(5) . . ? C21 Zr C12 103.74(4) . . ? C13 Zr C12 32.37(5) . . ? C15 Zr C12 53.46(5) . . ? Cl1 Zr C11 95.09(4) . . ? C22 Zr C11 128.20(5) . . ? Cl2 Zr C11 81.33(4) . . ? C14 Zr C11 53.81(4) . . ? C23 Zr C11 148.47(5) . . ? C21 Zr C11 129.37(4) . . ? C13 Zr C11 53.66(4) . . ? C15 Zr C11 32.04(5) . . ? C12 Zr C11 32.39(5) . . ? Cl1 Zr C24 82.94(3) . . ? C22 Zr C24 53.99(4) . . ? Cl2 Zr C24 96.93(3) . . ? C14 Zr C24 128.31(4) . . ? C23 Zr C24 32.16(4) . . ? C21 Zr C24 53.37(4) . . ? C13 Zr C24 129.08(4) . . ? C15 Zr C24 148.51(5) . . ? C12 Zr C24 149.70(5) . . ? C11 Zr C24 177.25(4) . . ? Cl1 Zr C25 86.16(3) . . ? C22 Zr C25 54.19(4) . . ? Cl2 Zr C25 128.50(3) . . ? C14 Zr C25 96.26(4) . . ? C23 Zr C25 53.65(4) . . ? C21 Zr C25 32.14(4) . . ? C13 Zr C25 103.65(4) . . ? C15 Zr C25 120.45(4) . . ? C12 Zr C25 134.55(4) . . ? C11 Zr C25 149.95(4) . . ? C24 Zr C25 32.05(4) . . ? C15 C11 C12 108.03(12) . . ? C15 C11 Zr 73.56(8) . . ? C12 C11 Zr 73.57(8) . . ? C13 C12 C11 107.95(13) . . ? C13 C12 Zr 73.25(8) . . ? C11 C12 Zr 74.04(8) . . ? C14 C13 C12 107.95(12) . . ? C14 C13 Zr 72.68(7) . . ? C12 C13 Zr 74.39(7) . . ? C13 C14 C15 107.99(12) . . ? C13 C14 Zr 74.75(7) . . ? C15 C14 Zr 75.05(7) . . ? C11 C15 C14 108.06(12) . . ? C11 C15 Zr 74.40(8) . . ? C14 C15 Zr 72.22(7) . . ? C25 C21 C22 108.55(10) . . ? C25 C21 Zr 77.36(6) . . ? C22 C21 Zr 70.81(7) . . ? C23 C22 C21 107.96(11) . . ? C23 C22 Zr 75.66(7) . . ? C21 C22 Zr 75.99(7) . . ? C24 C23 C22 107.85(11) . . ? C24 C23 Zr 76.21(7) . . ? C22 C23 Zr 71.23(7) . . ? C23 C24 C25 109.08(11) . . ? C23 C24 Zr 71.63(7) . . ? C25 C24 Zr 75.52(7) . . ? C21 C25 C24 106.52(11) . . ? C21 C25 C26 125.59(10) . . ? C24 C25 C26 126.86(11) . . ? C21 C25 Zr 70.49(7) . . ? C24 C25 Zr 72.43(7) . . ? C26 C25 Zr 130.99(8) . . ? C25 C26 C28 111.18(11) . . ? C25 C26 C27 112.43(10) . . ? C28 C26 C27 109.16(12) . . ? C25 C26 C29 107.03(10) . . ? C28 C26 C29 107.41(10) . . ? C27 C26 C29 109.48(11) . . ? C30 C29 C26 115.41(10) . . ? C31 C30 C29 111.87(10) . . ? O31 C31 N32 120.88(12) . . ? O31 C31 C30 121.09(12) . . ? N32 C31 C30 118.03(11) . . ? C31 N32 C35 118.62(10) . . ? C31 N32 C33 124.91(10) . . ? C35 N32 C33 116.46(10) . . ? N32 C33 C34 112.92(11) . . ? N32 C35 C36 112.43(13) . . ? 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 Cl1 Zr C11 C15 59.79(8) . . . . ? C22 Zr C11 C15 -114.05(9) . . . . ? Cl2 Zr C11 C15 154.92(8) . . . . ? C14 Zr C11 C15 -37.27(8) . . . . ? C23 Zr C11 C15 -154.98(9) . . . . ? C21 Zr C11 C15 -71.08(10) . . . . ? C13 Zr C11 C15 -77.97(9) . . . . ? C12 Zr C11 C15 -115.05(11) . . . . ? C24 Zr C11 C15 103.9(9) . . . . ? C25 Zr C11 C15 -31.33(13) . . . . ? Cl1 Zr C11 C12 174.84(8) . . . . ? C22 Zr C11 C12 1.00(11) . . . . ? Cl2 Zr C11 C12 -90.03(8) . . . . ? C14 Zr C11 C12 77.78(9) . . . . ? C23 Zr C11 C12 -39.92(12) . . . . ? C21 Zr C11 C12 43.98(11) . . . . ? C13 Zr C11 C12 37.08(8) . . . . ? C15 Zr C11 C12 115.05(11) . . . . ? C24 Zr C11 C12 -141.1(9) . . . . ? C25 Zr C11 C12 83.72(12) . . . . ? C15 C11 C12 C13 0.09(15) . . . . ? Zr C11 C12 C13 -65.93(9) . . . . ? C15 C11 C12 Zr 66.03(9) . . . . ? Cl1 Zr C12 C13 108.42(9) . . . . ? C22 Zr C12 C13 -64.33(9) . . . . ? Cl2 Zr C12 C13 -159.81(9) . . . . ? C14 Zr C12 C13 37.19(8) . . . . ? C23 Zr C12 C13 -87.99(10) . . . . ? C21 Zr C12 C13 -31.57(10) . . . . ? C15 Zr C12 C13 78.14(10) . . . . ? C11 Zr C12 C13 114.88(13) . . . . ? C24 Zr C12 C13 -68.54(13) . . . . ? C25 Zr C12 C13 -20.81(12) . . . . ? Cl1 Zr C12 C11 -6.46(10) . . . . ? C22 Zr C12 C11 -179.21(8) . . . . ? Cl2 Zr C12 C11 85.31(8) . . . . ? C14 Zr C12 C11 -77.69(9) . . . . ? C23 Zr C12 C11 157.12(8) . . . . ? C21 Zr C12 C11 -146.45(8) . . . . ? C13 Zr C12 C11 -114.88(13) . . . . ? C15 Zr C12 C11 -36.74(8) . . . . ? C24 Zr C12 C11 176.58(8) . . . . ? C25 Zr C12 C11 -135.69(8) . . . . ? C11 C12 C13 C14 1.01(15) . . . . ? Zr C12 C13 C14 -65.45(9) . . . . ? C11 C12 C13 Zr 66.46(9) . . . . ? Cl1 Zr C13 C14 16.51(10) . . . . ? C22 Zr C13 C14 -130.01(9) . . . . ? Cl2 Zr C13 C14 136.82(7) . . . . ? C23 Zr C13 C14 -136.09(8) . . . . ? C21 Zr C13 C14 -96.63(9) . . . . ? C15 Zr C13 C14 37.83(8) . . . . ? C12 Zr C13 C14 114.98(13) . . . . ? C11 Zr C13 C14 77.88(9) . . . . ? C24 Zr C13 C14 -102.24(9) . . . . ? C25 Zr C13 C14 -80.12(8) . . . . ? Cl1 Zr C13 C12 -98.47(9) . . . . ? C22 Zr C13 C12 115.00(10) . . . . ? Cl2 Zr C13 C12 21.84(10) . . . . ? C14 Zr C13 C12 -114.98(13) . . . . ? C23 Zr C13 C12 108.93(9) . . . . ? C21 Zr C13 C12 148.39(10) . . . . ? C15 Zr C13 C12 -77.16(10) . . . . ? C11 Zr C13 C12 -37.11(9) . . . . ? C24 Zr C13 C12 142.78(9) . . . . ? C25 Zr C13 C12 164.90(9) . . . . ? C12 C13 C14 C15 -1.72(15) . . . . ? Zr C13 C14 C15 -68.31(9) . . . . ? C12 C13 C14 Zr 66.58(9) . . . . ? Cl1 Zr C14 C13 -167.33(8) . . . . ? C22 Zr C14 C13 50.97(9) . . . . ? Cl2 Zr C14 C13 -60.59(9) . . . . ? C23 Zr C14 C13 62.25(10) . . . . ? C21 Zr C14 C13 76.86(8) . . . . ? C15 Zr C14 C13 -113.83(12) . . . . ? C12 Zr C14 C13 -36.95(8) . . . . ? C11 Zr C14 C13 -77.37(9) . . . . ? C24 Zr C14 C13 104.83(9) . . . . ? C25 Zr C14 C13 105.61(8) . . . . ? Cl1 Zr C14 C15 -53.50(8) . . . . ? C22 Zr C14 C15 164.80(8) . . . . ? Cl2 Zr C14 C15 53.24(10) . . . . ? C23 Zr C14 C15 176.08(8) . . . . ? C21 Zr C14 C15 -169.31(9) . . . . ? C13 Zr C14 C15 113.83(12) . . . . ? C12 Zr C14 C15 76.89(9) . . . . ? C11 Zr C14 C15 36.46(8) . . . . ? C24 Zr C14 C15 -141.34(8) . . . . ? C25 Zr C14 C15 -140.56(8) . . . . ? C12 C11 C15 C14 -1.16(15) . . . . ? Zr C11 C15 C14 64.88(9) . . . . ? C12 C11 C15 Zr -66.03(9) . . . . ? C13 C14 C15 C11 1.79(14) . . . . ? Zr C14 C15 C11 -66.32(9) . . . . ? C13 C14 C15 Zr 68.10(9) . . . . ? Cl1 Zr C15 C11 -118.73(8) . . . . ? C22 Zr C15 C11 94.51(9) . . . . ? Cl2 Zr C15 C11 -26.54(8) . . . . ? C14 Zr C15 C11 115.32(12) . . . . ? C23 Zr C15 C11 102.9(2) . . . . ? C21 Zr C15 C11 126.90(8) . . . . ? C13 Zr C15 C11 77.68(9) . . . . ? C12 Zr C15 C11 37.16(8) . . . . ? C24 Zr C15 C11 -174.88(7) . . . . ? C25 Zr C15 C11 162.42(7) . . . . ? Cl1 Zr C15 C14 125.96(9) . . . . ? C22 Zr C15 C14 -20.81(11) . . . . ? Cl2 Zr C15 C14 -141.86(8) . . . . ? C23 Zr C15 C14 -12.4(3) . . . . ? C21 Zr C15 C14 11.58(10) . . . . ? C13 Zr C15 C14 -37.64(8) . . . . ? C12 Zr C15 C14 -78.16(9) . . . . ? C11 Zr C15 C14 -115.32(12) . . . . ? C24 Zr C15 C14 69.80(11) . . . . ? C25 Zr C15 C14 47.10(10) . . . . ? Cl1 Zr C21 C25 20.39(8) . . . . ? C22 Zr C21 C25 -115.04(11) . . . . ? Cl2 Zr C21 C25 -102.82(7) . . . . ? C14 Zr C21 C25 116.02(8) . . . . ? C23 Zr C21 C25 -76.81(8) . . . . ? C13 Zr C21 C25 148.73(8) . . . . ? C15 Zr C21 C25 109.72(8) . . . . ? C12 Zr C21 C25 165.52(7) . . . . ? C11 Zr C21 C25 143.01(8) . . . . ? C24 Zr C21 C25 -36.69(7) . . . . ? Cl1 Zr C21 C22 135.44(7) . . . . ? Cl2 Zr C21 C22 12.22(9) . . . . ? C14 Zr C21 C22 -128.94(8) . . . . ? C23 Zr C21 C22 38.24(8) . . . . ? C13 Zr C21 C22 -96.22(8) . . . . ? C15 Zr C21 C22 -135.23(8) . . . . ? C12 Zr C21 C22 -79.43(8) . . . . ? C11 Zr C21 C22 -101.95(9) . . . . ? C24 Zr C21 C22 78.35(8) . . . . ? C25 Zr C21 C22 115.04(11) . . . . ? C25 C21 C22 C23 -0.73(14) . . . . ? Zr C21 C22 C23 -69.56(9) . . . . ? C25 C21 C22 Zr 68.83(8) . . . . ? Cl1 Zr C22 C23 47.72(10) . . . . ? Cl2 Zr C22 C23 -57.38(8) . . . . ? C14 Zr C22 C23 165.17(8) . . . . ? C21 Zr C22 C23 113.07(11) . . . . ? C13 Zr C22 C23 -169.83(9) . . . . ? C15 Zr C22 C23 176.53(8) . . . . ? C12 Zr C22 C23 -140.64(8) . . . . ? C11 Zr C22 C23 -141.17(8) . . . . ? C24 Zr C22 C23 36.74(8) . . . . ? C25 Zr C22 C23 76.60(8) . . . . ? Cl1 Zr C22 C21 -65.35(9) . . . . ? Cl2 Zr C22 C21 -170.45(7) . . . . ? C14 Zr C22 C21 52.10(8) . . . . ? C23 Zr C22 C21 -113.07(11) . . . . ? C13 Zr C22 C21 77.11(8) . . . . ? C15 Zr C22 C21 63.46(10) . . . . ? C12 Zr C22 C21 106.30(8) . . . . ? C11 Zr C22 C21 105.76(8) . . . . ? C24 Zr C22 C21 -76.33(8) . . . . ? C25 Zr C22 C21 -36.47(7) . . . . ? C21 C22 C23 C24 1.74(14) . . . . ? Zr C22 C23 C24 -68.05(9) . . . . ? C21 C22 C23 Zr 69.78(9) . . . . ? Cl1 Zr C23 C24 -32.29(7) . . . . ? C22 Zr C23 C24 114.63(11) . . . . ? Cl2 Zr C23 C24 -124.16(7) . . . . ? C14 Zr C23 C24 94.18(9) . . . . ? C21 Zr C23 C24 76.28(8) . . . . ? C13 Zr C23 C24 125.68(7) . . . . ? C15 Zr C23 C24 103.5(2) . . . . ? C12 Zr C23 C24 161.60(7) . . . . ? C11 Zr C23 C24 -174.93(7) . . . . ? C25 Zr C23 C24 36.25(7) . . . . ? Cl1 Zr C23 C22 -146.92(7) . . . . ? Cl2 Zr C23 C22 121.21(8) . . . . ? C14 Zr C23 C22 -20.45(11) . . . . ? C21 Zr C23 C22 -38.35(8) . . . . ? C13 Zr C23 C22 11.05(10) . . . . ? C15 Zr C23 C22 -11.1(2) . . . . ? C12 Zr C23 C22 46.97(10) . . . . ? C11 Zr C23 C22 70.45(11) . . . . ? C24 Zr C23 C22 -114.63(11) . . . . ? C25 Zr C23 C22 -78.38(8) . . . . ? C22 C23 C24 C25 -2.10(14) . . . . ? Zr C23 C24 C25 -66.81(9) . . . . ? C22 C23 C24 Zr 64.72(9) . . . . ? Cl1 Zr C24 C23 149.75(7) . . . . ? C22 Zr C24 C23 -37.87(7) . . . . ? Cl2 Zr C24 C23 54.71(7) . . . . ? C14 Zr C24 C23 -114.73(8) . . . . ? C21 Zr C24 C23 -79.40(8) . . . . ? C13 Zr C24 C23 -72.62(9) . . . . ? C15 Zr C24 C23 -155.02(8) . . . . ? C12 Zr C24 C23 -32.69(12) . . . . ? C11 Zr C24 C23 105.5(9) . . . . ? C25 Zr C24 C23 -116.20(10) . . . . ? Cl1 Zr C24 C25 -94.05(7) . . . . ? C22 Zr C24 C25 78.33(8) . . . . ? Cl2 Zr C24 C25 170.91(6) . . . . ? C14 Zr C24 C25 1.47(9) . . . . ? C23 Zr C24 C25 116.20(10) . . . . ? C21 Zr C24 C25 36.80(7) . . . . ? C13 Zr C24 C25 43.58(9) . . . . ? C15 Zr C24 C25 -38.81(11) . . . . ? C12 Zr C24 C25 83.51(11) . . . . ? C11 Zr C24 C25 -138.3(9) . . . . ? C22 C21 C25 C24 -0.54(13) . . . . ? Zr C21 C25 C24 63.95(8) . . . . ? C22 C21 C25 C26 168.48(11) . . . . ? Zr C21 C25 C26 -127.03(11) . . . . ? C22 C21 C25 Zr -64.49(9) . . . . ? C23 C24 C25 C21 1.63(13) . . . . ? Zr C24 C25 C21 -62.66(8) . . . . ? C23 C24 C25 C26 -167.21(11) . . . . ? Zr C24 C25 C26 128.50(11) . . . . ? C23 C24 C25 Zr 64.29(9) . . . . ? Cl1 Zr C25 C21 -161.80(7) . . . . ? C22 Zr C25 C21 37.72(7) . . . . ? Cl2 Zr C25 C21 103.82(7) . . . . ? C14 Zr C25 C21 -63.46(8) . . . . ? C23 Zr C25 C21 79.01(8) . . . . ? C13 Zr C25 C21 -31.21(8) . . . . ? C15 Zr C25 C21 -86.94(8) . . . . ? C12 Zr C25 C21 -19.92(10) . . . . ? C11 Zr C25 C21 -68.28(12) . . . . ? C24 Zr C25 C21 115.38(11) . . . . ? Cl1 Zr C25 C24 82.82(7) . . . . ? C22 Zr C25 C24 -77.66(8) . . . . ? Cl2 Zr C25 C24 -11.56(8) . . . . ? C14 Zr C25 C24 -178.84(7) . . . . ? C23 Zr C25 C24 -36.37(7) . . . . ? C21 Zr C25 C24 -115.38(11) . . . . ? C13 Zr C25 C24 -146.59(7) . . . . ? C15 Zr C25 C24 157.68(7) . . . . ? C12 Zr C25 C24 -135.30(8) . . . . ? C11 Zr C25 C24 176.35(8) . . . . ? Cl1 Zr C25 C26 -41.13(10) . . . . ? C22 Zr C25 C26 158.39(12) . . . . ? Cl2 Zr C25 C26 -135.51(9) . . . . ? C14 Zr C25 C26 57.21(11) . . . . ? C23 Zr C25 C26 -160.32(12) . . . . ? C21 Zr C25 C26 120.67(13) . . . . ? C13 Zr C25 C26 89.46(11) . . . . ? C15 Zr C25 C26 33.73(11) . . . . ? C12 Zr C25 C26 100.75(11) . . . . ? C11 Zr C25 C26 52.40(14) . . . . ? C24 Zr C25 C26 -123.95(13) . . . . ? C21 C25 C26 C28 44.25(16) . . . . ? C24 C25 C26 C28 -148.95(12) . . . . ? Zr C25 C26 C28 -50.22(14) . . . . ? C21 C25 C26 C27 166.98(12) . . . . ? C24 C25 C26 C27 -26.22(17) . . . . ? Zr C25 C26 C27 72.51(14) . . . . ? C21 C25 C26 C29 -72.77(15) . . . . ? C24 C25 C26 C29 94.04(13) . . . . ? Zr C25 C26 C29 -167.24(8) . . . . ? C25 C26 C29 C30 -61.92(15) . . . . ? C28 C26 C29 C30 178.60(12) . . . . ? C27 C26 C29 C30 60.20(16) . . . . ? C26 C29 C30 C31 -177.72(12) . . . . ? C29 C30 C31 O31 -6.1(2) . . . . ? C29 C30 C31 N32 173.71(13) . . . . ? O31 C31 N32 C35 -0.6(2) . . . . ? C30 C31 N32 C35 179.61(13) . . . . ? O31 C31 N32 C33 -179.45(14) . . . . ? C30 C31 N32 C33 0.7(2) . . . . ? C31 N32 C33 C34 -98.73(16) . . . . ? C35 N32 C33 C34 82.36(15) . . . . ? C31 N32 C35 C36 -93.89(16) . . . . ? C33 N32 C35 C36 85.09(15) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.337 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.052 data_erk1255 _database_code_CSD 179007 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18.50 H26 B Cl2 F4 N O Ti' _chemical_formula_weight 484.01 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' 'B' 'B' 0.0013 0.0007 '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' 'F' 'F' 0.0171 0.0103 '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' 'Ti' 'Ti' 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.967(1) _cell_length_b 13.167(1) _cell_length_c 12.702(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.07(1) _cell_angle_gamma 90.00 _cell_volume 2160.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow-orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 0.687 _exptl_absorpt_correction_type 'SORTAV (Blessing, 1995 & 1997)' _exptl_absorpt_correction_T_min 0.8748 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17676 _diffrn_reflns_av_R_equivalents 0.1250 _diffrn_reflns_av_sigmaI/netI 0.1260 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3801 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+2.2878P] 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 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3801 _refine_ls_number_parameters 275 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1417 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Ti Ti 0.78190(6) 0.10537(6) 0.14672(6) 0.0305(2) Uani 1 1 d . . . Cl1 Cl 0.87057(10) 0.18845(10) 0.29411(9) 0.0473(4) Uani 1 1 d . . . C10 C 0.6056(5) 0.1384(5) 0.0921(7) 0.080(2) Uani 1 1 d . . . H10 H 0.5548 0.0868 0.0952 0.096 Uiso 1 1 calc R . . C11 C 0.6349(5) 0.2067(5) 0.1702(5) 0.0634(18) Uani 1 1 d . . . H11 H 0.6095 0.2097 0.2380 0.076 Uiso 1 1 calc R . . C12 C 0.7068(5) 0.2693(4) 0.1331(5) 0.0630(17) Uani 1 1 d . . . H12 H 0.7382 0.3254 0.1705 0.076 Uiso 1 1 calc R . . C13 C 0.7268(6) 0.2397(5) 0.0348(5) 0.072(2) Uani 1 1 d . . . H13 H 0.7755 0.2696 -0.0075 0.087 Uiso 1 1 calc R . . C14 C 0.6634(7) 0.1580(6) 0.0074(5) 0.086(3) Uani 1 1 d . . . H14 H 0.6599 0.1218 -0.0575 0.103 Uiso 1 1 calc R . . C15 C 0.8275(4) 0.0047(4) 0.0059(3) 0.0345(12) Uani 1 1 d . . . H15 H 0.7760 -0.0085 -0.0503 0.041 Uiso 1 1 calc R . . C16 C 0.8946(4) 0.0888(4) 0.0127(3) 0.0387(13) Uani 1 1 d . . . H16 H 0.8979 0.1407 -0.0388 0.046 Uiso 1 1 calc R . . C17 C 0.9549(4) 0.0822(4) 0.1084(4) 0.0403(13) Uani 1 1 d . . . H17 H 1.0063 0.1296 0.1344 0.048 Uiso 1 1 calc R . . C18 C 0.9268(4) -0.0069(4) 0.1603(4) 0.0368(12) Uani 1 1 d . . . H18 H 0.9557 -0.0294 0.2276 0.044 Uiso 1 1 calc R . . C19 C 0.8490(4) -0.0571(3) 0.0960(3) 0.0311(11) Uani 1 1 d . . . C20 C 0.8029(4) -0.1609(4) 0.1128(3) 0.0359(12) Uani 1 1 d . . . C21 C 0.8457(4) -0.2077(4) 0.2182(4) 0.0446(13) Uani 1 1 d . . . H21A H 0.8276 -0.1643 0.2765 0.067 Uiso 1 1 calc R . . H21B H 0.9212 -0.2132 0.2199 0.067 Uiso 1 1 calc R . . H21C H 0.8158 -0.2754 0.2256 0.067 Uiso 1 1 calc R . . C22 C 0.8351(4) -0.2292(4) 0.0224(4) 0.0495(14) Uani 1 1 d . . . H22A H 0.8112 -0.2988 0.0329 0.074 Uiso 1 1 calc R . . H22B H 0.9107 -0.2289 0.0225 0.074 Uiso 1 1 calc R . . H22C H 0.8040 -0.2033 -0.0454 0.074 Uiso 1 1 calc R . . C23 C 0.6822(4) -0.1577(4) 0.1023(3) 0.0383(13) Uani 1 1 d . . . H23A H 0.6602 -0.0999 0.0558 0.046 Uiso 1 1 calc R . . H23B H 0.6569 -0.2205 0.0656 0.046 Uiso 1 1 calc R . . C24 C 0.6273(4) -0.1481(3) 0.2032(3) 0.0372(12) Uani 1 1 d . . . H24A H 0.5519 -0.1420 0.1835 0.045 Uiso 1 1 calc R . . H24B H 0.6387 -0.2114 0.2447 0.045 Uiso 1 1 calc R . . C25 C 0.6612(3) -0.0601(3) 0.2722(3) 0.0293(11) Uani 1 1 d . . . N26 N 0.6373(3) -0.0557(3) 0.3699(3) 0.0314(9) Uani 1 1 d . . . C27 C 0.5681(4) -0.1289(4) 0.4133(3) 0.0413(13) Uani 1 1 d . . . H27A H 0.4969 -0.1166 0.3833 0.062 Uiso 1 1 calc R . . H27B H 0.5718 -0.1215 0.4903 0.062 Uiso 1 1 calc R . . H27C H 0.5890 -0.1979 0.3954 0.062 Uiso 1 1 calc R . . C28 C 0.6683(4) 0.0332(4) 0.4352(3) 0.0447(14) Uani 1 1 d . . . H28A H 0.7280 0.0660 0.4074 0.067 Uiso 1 1 calc R . . H28B H 0.6869 0.0114 0.5082 0.067 Uiso 1 1 calc R . . H28C H 0.6106 0.0814 0.4336 0.067 Uiso 1 1 calc R . . O29 O 0.7145(2) 0.0105(2) 0.2363(2) 0.0347(8) Uani 1 1 d . . . B B 0.3685(5) 0.0541(5) 0.2468(5) 0.0484(17) Uani 1 1 d . . . F1 F 0.2819(4) 0.0365(4) 0.2946(4) 0.157(2) Uani 1 1 d . . . F2 F 0.4021(4) -0.0329(3) 0.2106(3) 0.1317(19) Uani 1 1 d . . . F3 F 0.4400(3) 0.0937(3) 0.3197(2) 0.0998(13) Uani 1 1 d . . . F4 F 0.3458(3) 0.1220(2) 0.1672(2) 0.0712(10) Uani 1 1 d . . . C31 C 1.022(4) 0.4935(18) -0.010(3) 0.27(2) Uani 0.50 1 d PD . . H31A H 1.0882 0.4781 0.0325 0.325 Uiso 0.50 1 calc PR . . H31B H 1.0128 0.4397 -0.0647 0.325 Uiso 0.50 1 calc PR . . Cl2A Cl 1.0400(4) 0.5989(3) -0.0719(3) 0.0795(14) Uani 0.50 1 d PD . . Cl2B Cl 0.9305(4) 0.4799(6) 0.0671(4) 0.137(2) Uani 0.50 1 d PD . . 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 Ti 0.0342(5) 0.0269(5) 0.0309(4) 0.0016(4) 0.0069(3) -0.0001(4) Cl1 0.0501(9) 0.0478(9) 0.0449(7) -0.0144(6) 0.0087(6) -0.0132(7) C10 0.045(4) 0.063(5) 0.127(6) 0.010(5) -0.019(4) 0.013(4) C11 0.070(5) 0.053(4) 0.070(4) 0.022(4) 0.028(4) 0.031(4) C12 0.072(5) 0.025(3) 0.089(5) 0.000(3) -0.004(4) 0.017(3) C13 0.088(6) 0.060(5) 0.074(5) 0.037(4) 0.034(4) 0.044(4) C14 0.113(7) 0.086(6) 0.052(4) -0.022(4) -0.032(4) 0.070(5) C15 0.040(3) 0.037(3) 0.028(2) 0.001(2) 0.007(2) 0.008(3) C16 0.046(3) 0.036(3) 0.037(3) 0.005(2) 0.019(2) 0.002(3) C17 0.034(3) 0.040(4) 0.049(3) -0.004(2) 0.013(2) -0.004(3) C18 0.038(3) 0.036(3) 0.037(3) 0.000(2) 0.003(2) 0.006(3) C19 0.038(3) 0.026(3) 0.029(2) -0.003(2) 0.007(2) 0.002(2) C20 0.045(3) 0.032(3) 0.031(3) -0.003(2) 0.008(2) 0.002(3) C21 0.041(3) 0.039(3) 0.055(3) 0.010(2) 0.008(2) 0.005(3) C22 0.061(4) 0.032(3) 0.060(3) -0.018(3) 0.027(3) -0.009(3) C23 0.045(4) 0.036(3) 0.034(3) -0.011(2) 0.004(2) -0.007(3) C24 0.042(3) 0.029(3) 0.040(3) -0.007(2) 0.003(2) -0.004(2) C25 0.028(3) 0.028(3) 0.033(3) 0.003(2) 0.005(2) 0.005(2) N26 0.036(3) 0.030(2) 0.029(2) 0.0020(17) 0.0086(17) -0.0038(19) C27 0.046(3) 0.044(3) 0.035(3) 0.008(2) 0.014(2) -0.007(3) C28 0.052(4) 0.049(4) 0.034(3) -0.012(2) 0.011(2) -0.007(3) O29 0.043(2) 0.0244(19) 0.0386(18) -0.0050(14) 0.0169(15) -0.0084(17) B 0.055(5) 0.054(5) 0.036(3) 0.000(3) 0.008(3) 0.014(4) F1 0.102(4) 0.196(6) 0.183(5) 0.091(4) 0.060(4) 0.015(4) F2 0.186(5) 0.082(3) 0.117(3) -0.043(3) -0.041(3) 0.068(3) F3 0.127(4) 0.099(3) 0.063(2) -0.006(2) -0.043(2) -0.007(3) F4 0.103(3) 0.059(2) 0.0477(18) 0.0116(16) -0.0166(16) -0.003(2) C31 0.26(5) 0.39(4) 0.20(3) -0.20(3) 0.22(3) -0.21(4) Cl2A 0.111(4) 0.062(2) 0.060(2) -0.0168(19) -0.0241(19) 0.029(2) Cl2B 0.088(4) 0.204(7) 0.113(4) -0.009(5) -0.028(3) -0.037(5) _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 Ti O29 1.948(3) . ? Ti C13 2.341(5) . ? Ti C14 2.344(6) . ? Ti C15 2.344(4) . ? Ti C16 2.349(4) . ? Ti C17 2.357(5) . ? Ti C11 2.367(6) . ? Ti C12 2.369(5) . ? Ti C10 2.370(6) . ? Ti Cl1 2.3755(14) . ? Ti C18 2.386(5) . ? Ti C19 2.419(5) . ? C10 C11 1.367(9) . ? C10 C14 1.388(10) . ? C11 C12 1.360(8) . ? C12 C13 1.356(8) . ? C13 C14 1.380(9) . ? C15 C16 1.406(6) . ? C15 C19 1.411(6) . ? C16 C17 1.389(6) . ? C17 C18 1.410(6) . ? C18 C19 1.406(6) . ? C19 C20 1.515(6) . ? C20 C21 1.532(6) . ? C20 C22 1.545(6) . ? C20 C23 1.560(6) . ? C23 C24 1.526(6) . ? C24 C25 1.495(6) . ? C25 O29 1.268(5) . ? C25 N26 1.306(5) . ? N26 C27 1.459(5) . ? N26 C28 1.469(5) . ? B F2 1.322(7) . ? B F1 1.343(7) . ? B F3 1.355(7) . ? B F4 1.363(7) . ? C31 Cl2A 1.619(19) . ? C31 Cl2B 1.621(17) . ? Cl2A Cl2B 1.105(7) 3_765 ? Cl2A C31 1.837(12) 3_765 ? Cl2B C31 1.046(11) 3_765 ? Cl2B Cl2A 1.105(7) 3_765 ? 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 O29 Ti C13 135.3(2) . . ? O29 Ti C14 109.4(3) . . ? C13 Ti C14 34.3(2) . . ? O29 Ti C15 103.85(15) . . ? C13 Ti C15 92.8(2) . . ? C14 Ti C15 77.52(19) . . ? O29 Ti C16 134.72(15) . . ? C13 Ti C16 78.82(19) . . ? C14 Ti C16 83.6(2) . . ? C15 Ti C16 34.88(15) . . ? O29 Ti C17 121.48(15) . . ? C13 Ti C17 102.6(2) . . ? C14 Ti C17 117.1(3) . . ? C15 Ti C17 57.34(17) . . ? C16 Ti C17 34.33(15) . . ? O29 Ti C11 83.09(18) . . ? C13 Ti C11 56.3(2) . . ? C14 Ti C11 56.4(2) . . ? C15 Ti C11 132.5(2) . . ? C16 Ti C11 134.66(18) . . ? C17 Ti C11 153.0(2) . . ? O29 Ti C12 115.1(2) . . ? C13 Ti C12 33.5(2) . . ? C14 Ti C12 55.8(2) . . ? C15 Ti C12 126.2(2) . . ? C16 Ti C12 108.1(2) . . ? C17 Ti C12 119.7(2) . . ? C11 Ti C12 33.4(2) . . ? O29 Ti C10 79.5(2) . . ? C13 Ti C10 56.5(2) . . ? C14 Ti C10 34.2(2) . . ? C15 Ti C10 100.5(2) . . ? C16 Ti C10 116.8(3) . . ? C17 Ti C10 151.0(2) . . ? C11 Ti C10 33.5(2) . . ? C12 Ti C10 55.3(2) . . ? O29 Ti Cl1 92.63(9) . . ? C13 Ti Cl1 103.4(2) . . ? C14 Ti Cl1 134.3(2) . . ? C15 Ti Cl1 136.44(13) . . ? C16 Ti Cl1 108.97(13) . . ? C17 Ti Cl1 79.58(12) . . ? C11 Ti Cl1 88.88(19) . . ? C12 Ti Cl1 78.76(15) . . ? C10 Ti Cl1 122.2(2) . . ? O29 Ti C18 87.23(15) . . ? C13 Ti C18 135.11(19) . . ? C14 Ti C18 134.23(19) . . ? C15 Ti C18 56.92(16) . . ? C16 Ti C18 57.21(16) . . ? C17 Ti C18 34.58(15) . . ? C11 Ti C18 168.05(18) . . ? C12 Ti C18 152.4(2) . . ? C10 Ti C18 150.3(2) . . ? Cl1 Ti C18 84.56(12) . . ? O29 Ti C19 77.24(14) . . ? C13 Ti C19 127.2(2) . . ? C14 Ti C19 106.72(19) . . ? C15 Ti C19 34.43(14) . . ? C16 Ti C19 57.54(16) . . ? C17 Ti C19 57.25(16) . . ? C11 Ti C19 147.7(2) . . ? C12 Ti C19 160.44(19) . . ? C10 Ti C19 116.4(2) . . ? Cl1 Ti C19 117.18(11) . . ? C18 Ti C19 34.02(15) . . ? C11 C10 C14 107.8(7) . . ? C11 C10 Ti 73.1(4) . . ? C14 C10 Ti 71.9(4) . . ? C12 C11 C10 107.6(6) . . ? C12 C11 Ti 73.4(3) . . ? C10 C11 Ti 73.3(4) . . ? C13 C12 C11 109.7(6) . . ? C13 C12 Ti 72.2(3) . . ? C11 C12 Ti 73.3(3) . . ? C12 C13 C14 107.4(6) . . ? C12 C13 Ti 74.4(3) . . ? C14 C13 Ti 73.0(3) . . ? C13 C14 C10 107.4(6) . . ? C13 C14 Ti 72.8(3) . . ? C10 C14 Ti 73.9(4) . . ? C16 C15 C19 109.1(4) . . ? C16 C15 Ti 72.8(3) . . ? C19 C15 Ti 75.7(2) . . ? C17 C16 C15 107.6(4) . . ? C17 C16 Ti 73.2(3) . . ? C15 C16 Ti 72.4(2) . . ? C16 C17 C18 108.2(4) . . ? C16 C17 Ti 72.5(3) . . ? C18 C17 Ti 73.8(3) . . ? C19 C18 C17 108.8(4) . . ? C19 C18 Ti 74.3(3) . . ? C17 C18 Ti 71.6(3) . . ? C18 C19 C15 106.3(4) . . ? C18 C19 C20 127.9(4) . . ? C15 C19 C20 125.6(4) . . ? C18 C19 Ti 71.7(3) . . ? C15 C19 Ti 69.9(3) . . ? C20 C19 Ti 127.2(3) . . ? C19 C20 C21 111.6(4) . . ? C19 C20 C22 106.5(4) . . ? C21 C20 C22 108.3(4) . . ? C19 C20 C23 111.7(4) . . ? C21 C20 C23 111.7(4) . . ? C22 C20 C23 106.7(4) . . ? C24 C23 C20 118.0(4) . . ? C25 C24 C23 115.0(4) . . ? O29 C25 N26 119.4(4) . . ? O29 C25 C24 119.9(4) . . ? N26 C25 C24 120.7(4) . . ? C25 N26 C27 122.3(4) . . ? C25 N26 C28 119.8(4) . . ? C27 N26 C28 117.4(3) . . ? C25 O29 Ti 165.5(3) . . ? F2 B F1 108.8(6) . . ? F2 B F3 110.2(5) . . ? F1 B F3 107.9(5) . . ? F2 B F4 111.5(5) . . ? F1 B F4 108.3(5) . . ? F3 B F4 110.1(6) . . ? Cl2A C31 Cl2B 122(2) . . ? Cl2B Cl2A C31 39.8(8) 3_765 . ? Cl2B Cl2A C31 61.0(12) 3_765 3_765 ? C31 Cl2A C31 22(2) . 3_765 ? C31 Cl2B Cl2A 97.7(16) 3_765 3_765 ? C31 Cl2B C31 16(4) 3_765 . ? Cl2A Cl2B C31 82.4(13) 3_765 . ? 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 O29 Ti C10 C11 93.3(4) . . . . ? C13 Ti C10 C11 -78.0(4) . . . . ? C14 Ti C10 C11 -115.9(6) . . . . ? C15 Ti C10 C11 -164.4(4) . . . . ? C16 Ti C10 C11 -131.6(4) . . . . ? C17 Ti C10 C11 -127.2(5) . . . . ? C12 Ti C10 C11 -37.4(4) . . . . ? Cl1 Ti C10 C11 6.9(5) . . . . ? C18 Ti C10 C11 158.3(4) . . . . ? C19 Ti C10 C11 163.3(4) . . . . ? O29 Ti C10 C14 -150.8(5) . . . . ? C13 Ti C10 C14 37.9(4) . . . . ? C15 Ti C10 C14 -48.5(5) . . . . ? C16 Ti C10 C14 -15.7(6) . . . . ? C17 Ti C10 C14 -11.3(8) . . . . ? C11 Ti C10 C14 115.9(6) . . . . ? C12 Ti C10 C14 78.5(5) . . . . ? Cl1 Ti C10 C14 122.7(5) . . . . ? C18 Ti C10 C14 -85.8(6) . . . . ? C19 Ti C10 C14 -80.9(5) . . . . ? C14 C10 C11 C12 2.0(7) . . . . ? Ti C10 C11 C12 65.9(4) . . . . ? C14 C10 C11 Ti -63.9(4) . . . . ? O29 Ti C11 C12 163.8(4) . . . . ? C13 Ti C11 C12 -35.9(4) . . . . ? C14 Ti C11 C12 -77.3(4) . . . . ? C15 Ti C11 C12 -93.7(5) . . . . ? C16 Ti C11 C12 -44.9(6) . . . . ? C17 Ti C11 C12 6.9(7) . . . . ? C10 Ti C11 C12 -114.8(6) . . . . ? Cl1 Ti C11 C12 71.0(4) . . . . ? C18 Ti C11 C12 127.7(10) . . . . ? C19 Ti C11 C12 -143.6(4) . . . . ? O29 Ti C11 C10 -81.4(4) . . . . ? C13 Ti C11 C10 78.9(4) . . . . ? C14 Ti C11 C10 37.4(4) . . . . ? C15 Ti C11 C10 21.1(6) . . . . ? C16 Ti C11 C10 69.8(6) . . . . ? C17 Ti C11 C10 121.7(6) . . . . ? C12 Ti C11 C10 114.8(6) . . . . ? Cl1 Ti C11 C10 -174.2(4) . . . . ? C18 Ti C11 C10 -117.6(10) . . . . ? C19 Ti C11 C10 -28.8(6) . . . . ? C10 C11 C12 C13 -2.5(7) . . . . ? Ti C11 C12 C13 63.4(4) . . . . ? C10 C11 C12 Ti -65.9(4) . . . . ? O29 Ti C12 C13 -135.6(5) . . . . ? C14 Ti C12 C13 -38.4(4) . . . . ? C15 Ti C12 C13 -3.6(6) . . . . ? C16 Ti C12 C13 30.3(5) . . . . ? C17 Ti C12 C13 65.8(5) . . . . ? C11 Ti C12 C13 -117.8(6) . . . . ? C10 Ti C12 C13 -80.2(5) . . . . ? Cl1 Ti C12 C13 136.8(5) . . . . ? C18 Ti C12 C13 82.9(6) . . . . ? C19 Ti C12 C13 -9.5(9) . . . . ? O29 Ti C12 C11 -17.8(4) . . . . ? C13 Ti C12 C11 117.8(6) . . . . ? C14 Ti C12 C11 79.4(5) . . . . ? C15 Ti C12 C11 114.3(4) . . . . ? C16 Ti C12 C11 148.1(4) . . . . ? C17 Ti C12 C11 -176.4(4) . . . . ? C10 Ti C12 C11 37.6(4) . . . . ? Cl1 Ti C12 C11 -105.4(4) . . . . ? C18 Ti C12 C11 -159.2(4) . . . . ? C19 Ti C12 C11 108.3(7) . . . . ? C11 C12 C13 C14 2.0(7) . . . . ? Ti C12 C13 C14 66.1(4) . . . . ? C11 C12 C13 Ti -64.1(4) . . . . ? O29 Ti C13 C12 64.2(6) . . . . ? C14 Ti C13 C12 114.2(6) . . . . ? C15 Ti C13 C12 177.1(5) . . . . ? C16 Ti C13 C12 -150.7(5) . . . . ? C17 Ti C13 C12 -125.7(4) . . . . ? C11 Ti C13 C12 35.8(4) . . . . ? C10 Ti C13 C12 76.4(4) . . . . ? Cl1 Ti C13 C12 -43.7(5) . . . . ? C18 Ti C13 C12 -139.4(4) . . . . ? C19 Ti C13 C12 176.0(4) . . . . ? O29 Ti C13 C14 -50.0(6) . . . . ? C15 Ti C13 C14 62.9(5) . . . . ? C16 Ti C13 C14 95.1(5) . . . . ? C17 Ti C13 C14 120.1(4) . . . . ? C11 Ti C13 C14 -78.4(4) . . . . ? C12 Ti C13 C14 -114.2(6) . . . . ? C10 Ti C13 C14 -37.8(4) . . . . ? Cl1 Ti C13 C14 -157.8(4) . . . . ? C18 Ti C13 C14 106.4(5) . . . . ? C19 Ti C13 C14 61.8(5) . . . . ? C12 C13 C14 C10 -0.7(7) . . . . ? Ti C13 C14 C10 66.3(4) . . . . ? C12 C13 C14 Ti -67.0(4) . . . . ? C11 C10 C14 C13 -0.8(7) . . . . ? Ti C10 C14 C13 -65.5(4) . . . . ? C11 C10 C14 Ti 64.8(4) . . . . ? O29 Ti C14 C13 145.2(4) . . . . ? C15 Ti C14 C13 -114.4(5) . . . . ? C16 Ti C14 C13 -79.5(5) . . . . ? C17 Ti C14 C13 -71.6(4) . . . . ? C11 Ti C14 C13 77.9(4) . . . . ? C12 Ti C14 C13 37.5(4) . . . . ? C10 Ti C14 C13 114.6(6) . . . . ? Cl1 Ti C14 C13 30.8(6) . . . . ? C18 Ti C14 C13 -109.1(4) . . . . ? C19 Ti C14 C13 -132.8(4) . . . . ? O29 Ti C14 C10 30.6(5) . . . . ? C13 Ti C14 C10 -114.6(6) . . . . ? C15 Ti C14 C10 131.1(5) . . . . ? C16 Ti C14 C10 165.9(5) . . . . ? C17 Ti C14 C10 173.9(4) . . . . ? C11 Ti C14 C10 -36.6(4) . . . . ? C12 Ti C14 C10 -77.1(4) . . . . ? Cl1 Ti C14 C10 -83.7(6) . . . . ? C18 Ti C14 C10 136.3(4) . . . . ? C19 Ti C14 C10 112.6(5) . . . . ? O29 Ti C15 C16 -156.0(3) . . . . ? C13 Ti C15 C16 65.9(3) . . . . ? C14 Ti C15 C16 96.8(4) . . . . ? C17 Ti C15 C16 -37.3(3) . . . . ? C11 Ti C15 C16 110.7(3) . . . . ? C12 Ti C15 C16 67.8(4) . . . . ? C10 Ti C15 C16 122.3(3) . . . . ? Cl1 Ti C15 C16 -46.9(3) . . . . ? C18 Ti C15 C16 -78.7(3) . . . . ? C19 Ti C15 C16 -115.7(4) . . . . ? O29 Ti C15 C19 -40.3(3) . . . . ? C13 Ti C15 C19 -178.5(3) . . . . ? C14 Ti C15 C19 -147.6(4) . . . . ? C16 Ti C15 C19 115.7(4) . . . . ? C17 Ti C15 C19 78.4(3) . . . . ? C11 Ti C15 C19 -133.7(3) . . . . ? C12 Ti C15 C19 -176.5(3) . . . . ? C10 Ti C15 C19 -122.0(3) . . . . ? Cl1 Ti C15 C19 68.8(3) . . . . ? C18 Ti C15 C19 36.9(3) . . . . ? C19 C15 C16 C17 -2.4(5) . . . . ? Ti C15 C16 C17 65.2(3) . . . . ? C19 C15 C16 Ti -67.6(3) . . . . ? O29 Ti C16 C17 -81.5(3) . . . . ? C13 Ti C16 C17 133.0(4) . . . . ? C14 Ti C16 C17 167.4(4) . . . . ? C15 Ti C16 C17 -115.3(4) . . . . ? C11 Ti C16 C17 140.7(4) . . . . ? C12 Ti C16 C17 116.6(3) . . . . ? C10 Ti C16 C17 176.2(3) . . . . ? Cl1 Ti C16 C17 32.6(3) . . . . ? C18 Ti C16 C17 -37.5(3) . . . . ? C19 Ti C16 C17 -78.1(3) . . . . ? O29 Ti C16 C15 33.8(4) . . . . ? C13 Ti C16 C15 -111.7(3) . . . . ? C14 Ti C16 C15 -77.3(3) . . . . ? C17 Ti C16 C15 115.3(4) . . . . ? C11 Ti C16 C15 -104.0(4) . . . . ? C12 Ti C16 C15 -128.1(3) . . . . ? C10 Ti C16 C15 -68.5(3) . . . . ? Cl1 Ti C16 C15 147.9(2) . . . . ? C18 Ti C16 C15 77.8(3) . . . . ? C19 Ti C16 C15 37.2(3) . . . . ? C15 C16 C17 C18 1.1(5) . . . . ? Ti C16 C17 C18 65.7(3) . . . . ? C15 C16 C17 Ti -64.7(3) . . . . ? O29 Ti C17 C16 124.5(3) . . . . ? C13 Ti C17 C16 -47.3(4) . . . . ? C14 Ti C17 C16 -14.1(4) . . . . ? C15 Ti C17 C16 37.9(3) . . . . ? C11 Ti C17 C16 -82.7(5) . . . . ? C12 Ti C17 C16 -78.3(3) . . . . ? C10 Ti C17 C16 -7.0(6) . . . . ? Cl1 Ti C17 C16 -148.8(3) . . . . ? C18 Ti C17 C16 115.6(4) . . . . ? C19 Ti C17 C16 79.1(3) . . . . ? O29 Ti C17 C18 8.9(3) . . . . ? C13 Ti C17 C18 -162.9(3) . . . . ? C14 Ti C17 C18 -129.7(3) . . . . ? C15 Ti C17 C18 -77.7(3) . . . . ? C16 Ti C17 C18 -115.6(4) . . . . ? C11 Ti C17 C18 161.7(4) . . . . ? C12 Ti C17 C18 166.1(3) . . . . ? C10 Ti C17 C18 -122.6(5) . . . . ? Cl1 Ti C17 C18 95.6(3) . . . . ? C19 Ti C17 C18 -36.5(3) . . . . ? C16 C17 C18 C19 0.6(5) . . . . ? Ti C17 C18 C19 65.5(3) . . . . ? C16 C17 C18 Ti -64.9(3) . . . . ? O29 Ti C18 C19 71.1(3) . . . . ? C13 Ti C18 C19 -92.5(4) . . . . ? C14 Ti C18 C19 -43.6(5) . . . . ? C15 Ti C18 C19 -37.4(3) . . . . ? C16 Ti C18 C19 -79.2(3) . . . . ? C17 Ti C18 C19 -116.5(4) . . . . ? C11 Ti C18 C19 107.0(11) . . . . ? C12 Ti C18 C19 -143.3(4) . . . . ? C10 Ti C18 C19 8.0(6) . . . . ? Cl1 Ti C18 C19 164.0(3) . . . . ? O29 Ti C18 C17 -172.4(3) . . . . ? C13 Ti C18 C17 24.0(5) . . . . ? C14 Ti C18 C17 72.9(5) . . . . ? C15 Ti C18 C17 79.1(3) . . . . ? C16 Ti C18 C17 37.2(3) . . . . ? C11 Ti C18 C17 -136.5(11) . . . . ? C12 Ti C18 C17 -26.8(5) . . . . ? C10 Ti C18 C17 124.5(5) . . . . ? Cl1 Ti C18 C17 -79.5(3) . . . . ? C19 Ti C18 C17 116.5(4) . . . . ? C17 C18 C19 C15 -2.1(5) . . . . ? Ti C18 C19 C15 61.7(3) . . . . ? C17 C18 C19 C20 172.9(4) . . . . ? Ti C18 C19 C20 -123.3(5) . . . . ? C17 C18 C19 Ti -63.8(3) . . . . ? C16 C15 C19 C18 2.8(5) . . . . ? Ti C15 C19 C18 -62.9(3) . . . . ? C16 C15 C19 C20 -172.4(4) . . . . ? Ti C15 C19 C20 122.0(4) . . . . ? C16 C15 C19 Ti 65.7(3) . . . . ? O29 Ti C19 C18 -104.3(3) . . . . ? C13 Ti C19 C18 117.8(4) . . . . ? C14 Ti C19 C18 149.0(4) . . . . ? C15 Ti C19 C18 115.8(4) . . . . ? C16 Ti C19 C18 78.2(3) . . . . ? C17 Ti C19 C18 37.2(3) . . . . ? C11 Ti C19 C18 -158.3(3) . . . . ? C12 Ti C19 C18 124.3(6) . . . . ? C10 Ti C19 C18 -175.6(3) . . . . ? Cl1 Ti C19 C18 -17.9(3) . . . . ? O29 Ti C19 C15 139.9(3) . . . . ? C13 Ti C19 C15 1.9(4) . . . . ? C14 Ti C19 C15 33.1(4) . . . . ? C16 Ti C19 C15 -37.7(3) . . . . ? C17 Ti C19 C15 -78.7(3) . . . . ? C11 Ti C19 C15 85.9(4) . . . . ? C12 Ti C19 C15 8.5(7) . . . . ? C10 Ti C19 C15 68.6(4) . . . . ? Cl1 Ti C19 C15 -133.8(3) . . . . ? C18 Ti C19 C15 -115.8(4) . . . . ? O29 Ti C19 C20 19.8(3) . . . . ? C13 Ti C19 C20 -118.1(4) . . . . ? C14 Ti C19 C20 -86.9(5) . . . . ? C15 Ti C19 C20 -120.0(5) . . . . ? C16 Ti C19 C20 -157.7(4) . . . . ? C17 Ti C19 C20 161.3(4) . . . . ? C11 Ti C19 C20 -34.1(5) . . . . ? C12 Ti C19 C20 -111.6(7) . . . . ? C10 Ti C19 C20 -51.4(4) . . . . ? Cl1 Ti C19 C20 106.2(4) . . . . ? C18 Ti C19 C20 124.1(5) . . . . ? C18 C19 C20 C21 4.4(6) . . . . ? C15 C19 C20 C21 178.4(4) . . . . ? Ti C19 C20 C21 -90.9(4) . . . . ? C18 C19 C20 C22 -113.7(5) . . . . ? C15 C19 C20 C22 60.4(6) . . . . ? Ti C19 C20 C22 151.1(3) . . . . ? C18 C19 C20 C23 130.2(5) . . . . ? C15 C19 C20 C23 -55.7(6) . . . . ? Ti C19 C20 C23 35.0(5) . . . . ? C19 C20 C23 C24 -96.3(5) . . . . ? C21 C20 C23 C24 29.6(6) . . . . ? C22 C20 C23 C24 147.7(4) . . . . ? C20 C23 C24 C25 54.1(6) . . . . ? C23 C24 C25 O29 14.2(6) . . . . ? C23 C24 C25 N26 -165.2(4) . . . . ? O29 C25 N26 C27 173.9(4) . . . . ? C24 C25 N26 C27 -6.7(7) . . . . ? O29 C25 N26 C28 2.8(6) . . . . ? C24 C25 N26 C28 -177.8(4) . . . . ? N26 C25 O29 Ti -160.6(10) . . . . ? C24 C25 O29 Ti 20.1(15) . . . . ? C13 Ti O29 C25 69.7(13) . . . . ? C14 Ti O29 C25 42.5(12) . . . . ? C15 Ti O29 C25 -38.9(12) . . . . ? C16 Ti O29 C25 -58.0(13) . . . . ? C17 Ti O29 C25 -98.9(12) . . . . ? C11 Ti O29 C25 93.2(12) . . . . ? C12 Ti O29 C25 102.9(12) . . . . ? C10 Ti O29 C25 59.4(12) . . . . ? Cl1 Ti O29 C25 -178.3(12) . . . . ? C18 Ti O29 C25 -93.8(12) . . . . ? C19 Ti O29 C25 -61.0(12) . . . . ? Cl2B C31 Cl2A Cl2B -174(6) . . . 3_765 ? Cl2B C31 Cl2A C31 -6(6) . . . 3_765 ? Cl2A C31 Cl2B C31 15(12) . . . 3_765 ? Cl2A C31 Cl2B Cl2A 176(4) . . . 3_765 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.071 data_erk1550 _database_code_CSD 179008 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 N O' _chemical_formula_weight 191.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'Pbca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.715(1) _cell_length_b 11.021(1) _cell_length_c 26.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2225.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.35 _cell_measurement_theta_max 45.84 _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.563 _exptl_absorpt_correction_type 'empirical via \y scan data' _exptl_absorpt_correction_T_min 0.8272 _exptl_absorpt_correction_T_max 0.9203 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method '\w/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.3 _diffrn_reflns_number 2268 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 74.29 _reflns_number_total 2268 _reflns_number_gt 1898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express (Nonius B.V., 1994)' _computing_cell_refinement 'Express (Nonius B.V., 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1280P)^2^+0.5048P] 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 'refined as riding atoms' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0077(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2268 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1819 _refine_ls_wR_factor_gt 0.1701 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 N1 N 0.42673(18) 0.73986(13) 0.20058(5) 0.0440(4) Uani 1 1 d . . . C11 C 0.5715(3) 0.82402(18) 0.20615(8) 0.0596(6) Uani 1 1 d . . . H11A H 0.6722 0.7918 0.1886 0.089 Uiso 1 1 calc R . . H11B H 0.5982 0.8343 0.2421 0.089 Uiso 1 1 calc R . . H11C H 0.5405 0.9019 0.1915 0.089 Uiso 1 1 calc R . . C12 C 0.4390(3) 0.62693(17) 0.22903(7) 0.0535(5) Uani 1 1 d . . . H12A H 0.3257 0.5889 0.2306 0.080 Uiso 1 1 calc R . . H12B H 0.4795 0.6437 0.2634 0.080 Uiso 1 1 calc R . . H12C H 0.5198 0.5729 0.2121 0.080 Uiso 1 1 calc R . . C2 C 0.29624(19) 0.75500(14) 0.16654(6) 0.0370(4) Uani 1 1 d . . . O2 O 0.18228(15) 0.67787(11) 0.16188(5) 0.0480(4) Uani 1 1 d . . . C3 C 0.29556(19) 0.87062(14) 0.13532(6) 0.0388(4) Uani 1 1 d . . . H3A H 0.4046 0.8770 0.1163 0.047 Uiso 1 1 calc R . . H3B H 0.2875 0.9407 0.1583 0.047 Uiso 1 1 calc R . . C4 C 0.1435(2) 0.87257(15) 0.09796(7) 0.0443(4) Uani 1 1 d . . . H4A H 0.1598 0.8083 0.0725 0.053 Uiso 1 1 calc R . . H4B H 0.0362 0.8552 0.1166 0.053 Uiso 1 1 calc R . . C5 C 0.1253(2) 0.99198(15) 0.07100(5) 0.0382(4) Uani 1 1 d . . . C51 C 0.2742(2) 1.02862(17) 0.03769(7) 0.0471(5) Uani 1 1 d . . . H51A H 0.2488 1.1059 0.0217 0.071 Uiso 1 1 calc R . . H51B H 0.2922 0.9675 0.0115 0.071 Uiso 1 1 calc R . . H51C H 0.3782 1.0361 0.0583 0.071 Uiso 1 1 calc R . . C6 C -0.0178(2) 1.06223(14) 0.07645(6) 0.0379(4) Uani 1 1 d . . . C7 C -0.0548(2) 1.17902(15) 0.05214(6) 0.0432(4) Uani 1 1 d . . . H7 H 0.0177 1.2197 0.0289 0.052 Uiso 1 1 calc R . . C8 C -0.2101(2) 1.21830(16) 0.06877(7) 0.0497(5) Uani 1 1 d . . . H8 H -0.2636 1.2913 0.0590 0.060 Uiso 1 1 calc R . . C9 C -0.2818(2) 1.13057(16) 0.10397(7) 0.0495(5) Uani 1 1 d . . . H9 H -0.3889 1.1373 0.1208 0.059 Uiso 1 1 calc R . . C10 C -0.1697(2) 1.03774(15) 0.10861(6) 0.0437(4) Uani 1 1 d . . . H10 H -0.1860 0.9686 0.1291 0.052 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 N1 0.0425(8) 0.0462(8) 0.0433(8) 0.0032(5) -0.0066(6) -0.0007(6) C11 0.0566(11) 0.0576(11) 0.0645(11) 0.0022(9) -0.0204(9) -0.0112(9) C12 0.0548(10) 0.0570(11) 0.0488(9) 0.0100(8) -0.0069(8) 0.0037(8) C2 0.0355(7) 0.0400(8) 0.0353(7) -0.0050(6) 0.0020(6) 0.0034(6) O2 0.0432(7) 0.0471(7) 0.0538(7) 0.0073(5) -0.0042(5) -0.0061(5) C3 0.0355(8) 0.0400(9) 0.0411(8) -0.0019(6) -0.0026(6) 0.0023(6) C4 0.0385(8) 0.0405(9) 0.0538(9) 0.0007(7) -0.0096(7) -0.0005(6) C5 0.0364(8) 0.0403(8) 0.0379(8) -0.0019(6) -0.0081(6) -0.0035(6) C51 0.0410(9) 0.0531(10) 0.0471(9) 0.0013(7) -0.0007(7) -0.0011(7) C6 0.0387(8) 0.0381(8) 0.0370(7) -0.0008(6) -0.0069(6) -0.0029(6) C7 0.0491(9) 0.0415(9) 0.0391(8) 0.0019(6) -0.0072(6) -0.0018(7) C8 0.0559(10) 0.0442(9) 0.0492(10) -0.0020(7) -0.0097(8) 0.0111(8) C9 0.0435(9) 0.0552(11) 0.0498(9) -0.0071(8) -0.0014(7) 0.0040(8) C10 0.0413(8) 0.0435(9) 0.0463(9) 0.0014(6) -0.0024(7) -0.0038(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 N1 C2 1.355(2) . ? N1 C12 1.453(2) . ? N1 C11 1.459(2) . ? C2 O2 1.2290(19) . ? C2 C3 1.514(2) . ? C3 C4 1.527(2) . ? C4 C5 1.500(2) . ? C5 C6 1.356(2) . ? C5 C51 1.498(2) . ? C6 C7 1.464(2) . ? C6 C10 1.468(2) . ? C7 C8 1.347(3) . ? C8 C9 1.446(3) . ? C9 C10 1.345(2) . ? 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 N1 C12 119.39(14) . . ? C2 N1 C11 123.80(14) . . ? C12 N1 C11 116.32(14) . . ? O2 C2 N1 120.78(15) . . ? O2 C2 C3 121.75(13) . . ? N1 C2 C3 117.47(13) . . ? C2 C3 C4 111.10(13) . . ? C5 C4 C3 112.69(13) . . ? C6 C5 C51 122.14(15) . . ? C6 C5 C4 121.87(15) . . ? C51 C5 C4 116.00(14) . . ? C5 C6 C7 127.94(15) . . ? C5 C6 C10 127.25(15) . . ? C7 C6 C10 104.81(14) . . ? C8 C7 C6 108.39(16) . . ? C7 C8 C9 109.35(15) . . ? C10 C9 C8 108.69(16) . . ? C9 C10 C6 108.76(15) . . ? 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 C12 N1 C2 O2 4.7(2) . . . . ? C11 N1 C2 O2 176.36(16) . . . . ? C12 N1 C2 C3 -176.07(13) . . . . ? C11 N1 C2 C3 -4.4(2) . . . . ? O2 C2 C3 C4 -2.2(2) . . . . ? N1 C2 C3 C4 178.58(14) . . . . ? C2 C3 C4 C5 172.82(13) . . . . ? C3 C4 C5 C6 -117.55(16) . . . . ? C3 C4 C5 C51 62.58(19) . . . . ? C51 C5 C6 C7 0.9(2) . . . . ? C4 C5 C6 C7 -178.98(14) . . . . ? C51 C5 C6 C10 -178.57(14) . . . . ? C4 C5 C6 C10 1.6(2) . . . . ? C5 C6 C7 C8 -179.04(15) . . . . ? C10 C6 C7 C8 0.50(17) . . . . ? C6 C7 C8 C9 -0.25(18) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C8 C9 C10 C6 0.46(19) . . . . ? C5 C6 C10 C9 178.96(15) . . . . ? C7 C6 C10 C9 -0.59(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.275 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.061 data_erk_923 _database_code_CSD 179009 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 N O' _chemical_formula_weight 205.29 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.916(3) _cell_length_b 10.601(3) _cell_length_c 11.246(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.37(3) _cell_angle_gamma 90.00 _cell_volume 1227.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 13 _cell_measurement_theta_min 8.58 _cell_measurement_theta_max 19.15 _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'Enraf Nonius CAD4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 3.8 _diffrn_reflns_number 2188 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.1111 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 24.62 _reflns_number_total 2072 _reflns_number_gt 1095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Express (Nonius B.V., 1994)' _computing_cell_refinement 'Express (Nonius B.V., 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1181P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2072 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1650 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1969 _refine_ls_wR_factor_gt 0.1648 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 C1 C 1.3072(3) 0.2663(3) 0.4047(3) 0.0360(8) Uani 1 1 d . . . C2 C 1.1624(3) 0.2571(3) 0.3935(3) 0.0421(8) Uani 1 1 d . . . H2A H 1.1216 0.1903 0.3330 0.050 Uiso 1 1 calc R . . H2B H 1.1570 0.2321 0.4755 0.050 Uiso 1 1 calc R . . C3 C 1.0859(3) 0.3782(3) 0.3518(3) 0.0426(8) Uani 1 1 d . . . H3A H 1.1053 0.4129 0.2792 0.051 Uiso 1 1 calc R . . H3B H 1.1139 0.4400 0.4203 0.051 Uiso 1 1 calc R . . C4 C 0.9403(3) 0.3585(3) 0.3158(3) 0.0358(8) Uani 1 1 d . . . O4 O 0.8932(2) 0.2534(2) 0.3129(2) 0.0505(7) Uani 1 1 d . . . N5 N 0.8642(2) 0.4630(2) 0.2869(2) 0.0403(7) Uani 1 1 d . . . C11 C 1.3183(3) 0.2942(3) 0.2774(3) 0.0325(7) Uani 1 1 d . . . C12 C 1.2502(3) 0.2224(4) 0.1635(3) 0.0513(10) Uani 1 1 d . . . H12 H 1.1926 0.1552 0.1590 0.062 Uiso 1 1 calc R . . C13 C 1.2824(4) 0.2671(4) 0.0667(3) 0.0646(12) Uani 1 1 d . . . H13 H 1.2497 0.2371 -0.0165 0.078 Uiso 1 1 calc R . . C14 C 1.3753(4) 0.3687(4) 0.1093(4) 0.0602(11) Uani 1 1 d . . . H14A H 1.3419 0.4471 0.0640 0.072 Uiso 1 1 calc R . . H14B H 1.4580 0.3474 0.0977 0.072 Uiso 1 1 calc R . . C15 C 1.3911(3) 0.3807(3) 0.2457(3) 0.0470(9) Uani 1 1 d . . . H15 H 1.4443 0.4401 0.3012 0.056 Uiso 1 1 calc R . . C21 C 1.3715(3) 0.1376(3) 0.4503(3) 0.0496(9) Uani 1 1 d . . . H21A H 1.3344 0.0742 0.3862 0.074 Uiso 1 1 calc R . . H21B H 1.3564 0.1139 0.5276 0.074 Uiso 1 1 calc R . . H21C H 1.4642 0.1437 0.4658 0.074 Uiso 1 1 calc R . . C22 C 1.3768(4) 0.3655(3) 0.5016(3) 0.0517(9) Uani 1 1 d . . . H22A H 1.4685 0.3659 0.5111 0.078 Uiso 1 1 calc R . . H22B H 1.3665 0.3458 0.5819 0.078 Uiso 1 1 calc R . . H22C H 1.3399 0.4479 0.4735 0.078 Uiso 1 1 calc R . . C51 C 0.7239(3) 0.4469(3) 0.2430(3) 0.0492(9) Uani 1 1 d . . . H51A H 0.6969 0.4023 0.1632 0.074 Uiso 1 1 calc R . . H51B H 0.6824 0.5290 0.2320 0.074 Uiso 1 1 calc R . . H51C H 0.6989 0.3987 0.3046 0.074 Uiso 1 1 calc R . . C52 C 0.9131(4) 0.5899(3) 0.2853(4) 0.0612(11) Uani 1 1 d . . . H52A H 0.9938 0.6001 0.3547 0.092 Uiso 1 1 calc R . . H52B H 0.8498 0.6503 0.2941 0.092 Uiso 1 1 calc R . . H52C H 0.9283 0.6044 0.2062 0.092 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 C1 0.0304(17) 0.0361(18) 0.0396(18) -0.0002(14) 0.0089(13) 0.0015(14) C2 0.0406(19) 0.0386(19) 0.052(2) 0.0039(16) 0.0215(15) 0.0020(16) C3 0.0358(19) 0.0388(19) 0.054(2) 0.0023(16) 0.0158(15) 0.0018(15) C4 0.0376(19) 0.038(2) 0.0352(17) -0.0041(15) 0.0170(14) -0.0003(16) O4 0.0441(14) 0.0343(14) 0.0766(17) 0.0013(12) 0.0247(12) -0.0034(11) N5 0.0345(16) 0.0334(16) 0.0551(18) 0.0004(12) 0.0177(13) 0.0006(13) C11 0.0240(15) 0.0366(17) 0.0359(17) 0.0004(14) 0.0086(13) 0.0066(14) C12 0.040(2) 0.061(2) 0.047(2) -0.0057(18) 0.0078(16) -0.0084(17) C13 0.061(3) 0.091(3) 0.039(2) -0.001(2) 0.0129(18) 0.022(3) C14 0.059(2) 0.068(3) 0.066(3) 0.021(2) 0.036(2) 0.021(2) C15 0.043(2) 0.046(2) 0.056(2) -0.0012(17) 0.0206(17) 0.0016(17) C21 0.045(2) 0.048(2) 0.053(2) 0.0083(18) 0.0134(17) 0.0102(17) C22 0.047(2) 0.056(2) 0.046(2) -0.0042(17) 0.0064(16) 0.0019(18) C51 0.033(2) 0.052(2) 0.063(2) -0.0038(18) 0.0171(17) 0.0010(17) C52 0.045(2) 0.037(2) 0.103(3) 0.007(2) 0.026(2) 0.0020(18) _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 C11 1.505(4) . ? C1 C22 1.523(4) . ? C1 C21 1.543(4) . ? C1 C2 1.546(4) . ? C2 C3 1.518(4) . ? C3 C4 1.519(4) . ? C4 O4 1.223(4) . ? C4 N5 1.357(4) . ? N5 C52 1.450(4) . ? N5 C51 1.455(4) . ? C11 C15 1.337(4) . ? C11 C12 1.464(4) . ? C12 C13 1.337(5) . ? C13 C14 1.448(6) . ? C14 C15 1.491(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C22 111.5(3) . . ? C11 C1 C21 108.6(2) . . ? C22 C1 C21 108.0(3) . . ? C11 C1 C2 109.7(3) . . ? C22 C1 C2 110.9(3) . . ? C21 C1 C2 108.1(3) . . ? C3 C2 C1 114.5(3) . . ? C2 C3 C4 112.7(3) . . ? O4 C4 N5 121.3(3) . . ? O4 C4 C3 121.6(3) . . ? N5 C4 C3 117.1(3) . . ? C4 N5 C52 124.2(3) . . ? C4 N5 C51 118.5(3) . . ? C52 N5 C51 117.0(3) . . ? C15 C11 C12 107.3(3) . . ? C15 C11 C1 129.1(3) . . ? C12 C11 C1 123.6(3) . . ? C13 C12 C11 109.5(3) . . ? C12 C13 C14 109.8(3) . . ? C13 C14 C15 103.5(3) . . ? C11 C15 C14 109.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 -62.9(4) . . . . ? C22 C1 C2 C3 60.6(4) . . . . ? C21 C1 C2 C3 178.8(3) . . . . ? C1 C2 C3 C4 168.1(3) . . . . ? C2 C3 C4 O4 -5.1(4) . . . . ? C2 C3 C4 N5 174.9(3) . . . . ? O4 C4 N5 C52 -178.4(3) . . . . ? C3 C4 N5 C52 1.6(5) . . . . ? O4 C4 N5 C51 -4.5(4) . . . . ? C3 C4 N5 C51 175.5(3) . . . . ? C22 C1 C11 C15 9.0(4) . . . . ? C21 C1 C11 C15 -109.8(4) . . . . ? C2 C1 C11 C15 132.3(3) . . . . ? C22 C1 C11 C12 -173.7(3) . . . . ? C21 C1 C11 C12 67.5(4) . . . . ? C2 C1 C11 C12 -50.4(4) . . . . ? C15 C11 C12 C13 -0.4(4) . . . . ? C1 C11 C12 C13 -178.2(3) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C15 -1.6(4) . . . . ? C12 C11 C15 C14 -0.6(4) . . . . ? C1 C11 C15 C14 177.0(3) . . . . ? C13 C14 C15 C11 1.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.62 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.248 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.060