# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jie Zhang' _publ_contact_author_email ZSHI@PKU.EDU.CN _publ_section_title ; Synthesis and Structures of Titanium and Yttrium Complexes with the N, N'-Tetramethylguanidinate Ligands: Different Reactivity of the M?N Bonds toward Phenyl Isocyanate ; loop_ _publ_author_name 'Jie Zhang.' 'Zhen-Xia Chen.' 'Fuyan Han.' 'Yanan Han.' 'Xigeng Zhou.' # Attachment 'complex_4.cif' data_f40524a _database_code_depnum_ccdc_archive 'CCDC 695032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H35 N4 O2 Y' _chemical_formula_weight 524.49 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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.832(3) _cell_length_b 10.901(4) _cell_length_c 13.927(5) _cell_angle_alpha 97.490(5) _cell_angle_beta 92.561(5) _cell_angle_gamma 99.995(4) _cell_volume 1306.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 729 _cell_measurement_theta_min 2.686 _cell_measurement_theta_max 21.617 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6606 _exptl_absorpt_correction_T_max 0.8055 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.23 _diffrn_reflns_number 6036 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.01 _reflns_number_total 5033 _reflns_number_gt 3790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5033 _refine_ls_number_parameters 298 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.028 _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 Y1 Y 1.07093(5) 1.09179(4) 0.12717(3) 0.03915(17) Uani 1 1 d . . . O1 O 0.9165(3) 0.9100(2) 0.03603(19) 0.0421(7) Uani 1 1 d . . . N1 N 0.8935(4) 0.9327(3) 0.1925(2) 0.0410(8) Uani 1 1 d . . . N2 N 0.7282(4) 0.7660(3) 0.0860(2) 0.0438(8) Uani 1 1 d . . . N3 N 0.5509(5) 0.6134(4) 0.1388(3) 0.0587(11) Uani 1 1 d . . . N4 N 0.8089(5) 0.6283(4) 0.1875(3) 0.0586(10) Uani 1 1 d . . . C1 C 1.0712(11) 1.3168(7) 0.2245(7) 0.108(3) Uani 1 1 d . . . H1A H 1.1556 1.3661 0.2689 0.129 Uiso 1 1 calc R . . C2 C 1.0460(9) 1.3296(5) 0.1290(6) 0.087(2) Uani 1 1 d . . . H2A H 1.1099 1.3897 0.0943 0.104 Uiso 1 1 calc R . . C3 C 0.9037(8) 1.2674(6) 0.0980(5) 0.0767(17) Uani 1 1 d . . . H3A H 0.8501 1.2732 0.0360 0.092 Uiso 1 1 calc R . . C4 C 0.8357(8) 1.2120(5) 0.1725(7) 0.089(2) Uani 1 1 d . . . H4A H 0.7272 1.1731 0.1732 0.107 Uiso 1 1 calc R . . C5 C 0.9431(13) 1.2419(7) 0.2515(5) 0.102(3) Uani 1 1 d . . . H5A H 0.9222 1.2287 0.3182 0.123 Uiso 1 1 calc R . . C6 C 1.3464(8) 1.1572(8) 0.2239(7) 0.101(2) Uani 1 1 d . . . H6A H 1.3820 1.2381 0.2650 0.121 Uiso 1 1 calc R . . C7 C 1.3790(6) 1.1328(7) 0.1323(6) 0.0809(19) Uani 1 1 d . . . H7A H 1.4426 1.1917 0.0965 0.097 Uiso 1 1 calc R . . C8 C 1.3338(7) 1.0080(8) 0.1025(5) 0.088(2) Uani 1 1 d . . . H8A H 1.3619 0.9602 0.0434 0.106 Uiso 1 1 calc R . . C9 C 1.2699(7) 0.9572(6) 0.1850(8) 0.101(3) Uani 1 1 d . . . H9A H 1.2472 0.8680 0.1930 0.121 Uiso 1 1 calc R . . C10 C 1.2817(8) 1.0555(11) 0.2560(5) 0.099(3) Uani 1 1 d . . . H10A H 1.2651 1.0487 0.3243 0.119 Uiso 1 1 calc R . . C11 C 0.8444(5) 0.8662(4) 0.1080(3) 0.0392(9) Uani 1 1 d . . . C12 C 0.6994(5) 0.6746(4) 0.1388(3) 0.0485(11) Uani 1 1 d . . . C13 C 0.9683(6) 0.6512(5) 0.1638(5) 0.0727(16) Uani 1 1 d . . . H13A H 0.9757 0.6865 0.1041 0.109 Uiso 1 1 calc R . . H13B H 1.0062 0.5734 0.1565 0.109 Uiso 1 1 calc R . . H13C H 1.0287 0.7090 0.2149 0.109 Uiso 1 1 calc R . . C14 C 0.7818(8) 0.5752(5) 0.2769(4) 0.0843(19) Uani 1 1 d . . . H14A H 0.6737 0.5626 0.2868 0.126 Uiso 1 1 calc R . . H14B H 0.8376 0.6319 0.3304 0.126 Uiso 1 1 calc R . . H14C H 0.8163 0.4960 0.2726 0.126 Uiso 1 1 calc R . . C15 C 0.4263(7) 0.6744(6) 0.1115(5) 0.0806(17) Uani 1 1 d . . . H15A H 0.4643 0.7627 0.1126 0.121 Uiso 1 1 calc R . . H15B H 0.3474 0.6630 0.1564 0.121 Uiso 1 1 calc R . . H15C H 0.3843 0.6382 0.0473 0.121 Uiso 1 1 calc R . . C16 C 0.5108(8) 0.4783(5) 0.1405(5) 0.0832(18) Uani 1 1 d . . . H16A H 0.6009 0.4469 0.1598 0.125 Uiso 1 1 calc R . . H16B H 0.4715 0.4370 0.0769 0.125 Uiso 1 1 calc R . . H16C H 0.4336 0.4619 0.1859 0.125 Uiso 1 1 calc R . . C17 C 0.8176(5) 0.9155(4) 0.2787(3) 0.0439(10) Uani 1 1 d . . . C18 C 0.8992(6) 0.8980(5) 0.3597(3) 0.0601(13) Uani 1 1 d . . . H18A H 1.0030 0.8931 0.3569 0.072 Uiso 1 1 calc R . . C19 C 0.8289(7) 0.8875(6) 0.4469(4) 0.0748(16) Uani 1 1 d . . . H19A H 0.8853 0.8745 0.5015 0.090 Uiso 1 1 calc R . . C20 C 0.6769(8) 0.8964(6) 0.4517(4) 0.0822(18) Uani 1 1 d . . . H20A H 0.6294 0.8896 0.5095 0.099 Uiso 1 1 calc R . . C21 C 0.5955(7) 0.9153(7) 0.3714(4) 0.0822(18) Uani 1 1 d . . . H21A H 0.4919 0.9210 0.3745 0.099 Uiso 1 1 calc R . . C22 C 0.6647(6) 0.9261(5) 0.2857(4) 0.0596(13) Uani 1 1 d . . . H22A H 0.6080 0.9408 0.2318 0.072 Uiso 1 1 calc R . . O2 O 0.285(3) 0.5308(17) 0.4802(17) 0.463(15) Uani 1 1 d D . . C23 C 0.338(2) 0.572(2) 0.3966(15) 0.278(11) Uani 1 1 d D . . H23A H 0.3205 0.5054 0.3421 0.333 Uiso 1 1 calc R . . H23B H 0.4463 0.6098 0.4049 0.333 Uiso 1 1 calc R . . C24 C 0.239(2) 0.668(2) 0.3850(11) 0.289(14) Uani 1 1 d D . . H24A H 0.2920 0.7335 0.3509 0.346 Uiso 1 1 calc R . . H24B H 0.1431 0.6295 0.3486 0.346 Uiso 1 1 calc R . . C25 C 0.212(2) 0.7194(15) 0.4803(15) 0.255(9) Uani 1 1 d D . . H25A H 0.1025 0.7072 0.4894 0.306 Uiso 1 1 calc R . . H25B H 0.2543 0.8087 0.4928 0.306 Uiso 1 1 calc R . . C26 C 0.288(3) 0.652(2) 0.5427(8) 0.288(11) Uani 1 1 d D . . H26A H 0.2334 0.6405 0.6006 0.346 Uiso 1 1 calc R . . H26B H 0.3934 0.6947 0.5616 0.346 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 Y1 0.0402(3) 0.0341(2) 0.0433(3) 0.00429(16) 0.00540(16) 0.00761(16) O1 0.0504(18) 0.0336(15) 0.0422(15) 0.0084(12) 0.0083(13) 0.0038(13) N1 0.043(2) 0.0382(18) 0.0433(19) 0.0098(15) 0.0080(16) 0.0059(15) N2 0.044(2) 0.0372(19) 0.048(2) 0.0102(16) 0.0045(16) 0.0007(16) N3 0.051(3) 0.045(2) 0.080(3) 0.015(2) 0.019(2) -0.0001(18) N4 0.062(3) 0.048(2) 0.072(3) 0.026(2) 0.010(2) 0.014(2) C1 0.123(7) 0.061(4) 0.127(7) -0.045(5) -0.025(6) 0.036(4) C2 0.094(5) 0.039(3) 0.130(6) 0.008(3) 0.037(5) 0.014(3) C3 0.088(5) 0.062(3) 0.090(4) 0.006(3) 0.006(4) 0.044(3) C4 0.065(4) 0.052(3) 0.163(7) 0.020(4) 0.052(5) 0.028(3) C5 0.171(9) 0.081(5) 0.074(4) 0.005(4) 0.047(5) 0.071(6) C6 0.063(4) 0.110(6) 0.115(6) -0.021(5) -0.029(4) 0.011(4) C7 0.042(3) 0.088(5) 0.117(6) 0.048(4) 0.003(3) -0.001(3) C8 0.057(4) 0.129(6) 0.080(4) -0.022(4) -0.015(3) 0.054(4) C9 0.039(3) 0.062(4) 0.213(9) 0.069(5) -0.011(5) 0.008(3) C10 0.065(5) 0.177(9) 0.069(4) 0.047(5) -0.001(3) 0.036(5) C11 0.039(2) 0.035(2) 0.048(2) 0.0133(19) 0.0083(19) 0.0127(18) C12 0.054(3) 0.036(2) 0.056(3) 0.005(2) 0.015(2) 0.008(2) C13 0.063(4) 0.056(3) 0.109(5) 0.026(3) 0.013(3) 0.024(3) C14 0.116(5) 0.066(4) 0.074(4) 0.037(3) 0.004(4) 0.006(3) C15 0.059(4) 0.072(4) 0.110(5) 0.012(3) 0.016(3) 0.007(3) C16 0.095(5) 0.047(3) 0.101(5) 0.011(3) 0.025(4) -0.011(3) C17 0.048(3) 0.040(2) 0.042(2) 0.0061(19) 0.005(2) 0.0029(19) C18 0.058(3) 0.073(3) 0.049(3) 0.011(2) 0.006(2) 0.007(3) C19 0.079(4) 0.095(4) 0.049(3) 0.015(3) 0.003(3) 0.006(3) C20 0.085(5) 0.107(5) 0.050(3) 0.011(3) 0.024(3) 0.000(4) C21 0.063(4) 0.122(5) 0.063(4) 0.014(3) 0.022(3) 0.017(4) C22 0.055(3) 0.072(3) 0.053(3) 0.010(2) 0.012(2) 0.010(3) O2 0.71(4) 0.45(3) 0.32(2) 0.12(2) 0.20(3) 0.29(3) C23 0.21(2) 0.42(3) 0.170(16) -0.034(18) 0.053(14) 0.03(2) C24 0.177(16) 0.52(4) 0.148(14) 0.156(19) -0.056(12) -0.063(19) C25 0.33(2) 0.28(2) 0.199(17) 0.115(17) 0.052(16) 0.106(16) C26 0.48(3) 0.30(2) 0.132(12) 0.056(14) 0.106(16) 0.18(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Y1 O1 2.278(3) 2_775 ? Y1 O1 2.377(3) . ? Y1 N1 2.426(3) . ? Y1 C2 2.637(6) . ? Y1 C9 2.640(5) . ? Y1 C10 2.642(6) . ? Y1 C1 2.643(6) . ? Y1 C5 2.651(6) . ? Y1 C8 2.659(5) . ? Y1 C6 2.664(6) . ? Y1 C3 2.673(5) . ? Y1 C7 2.676(6) . ? O1 C11 1.309(5) . ? O1 Y1 2.278(3) 2_775 ? N1 C11 1.312(5) . ? N1 C17 1.420(5) . ? N2 C12 1.311(5) . ? N2 C11 1.355(5) . ? N3 C12 1.364(6) . ? N3 C15 1.443(7) . ? N3 C16 1.457(6) . ? N4 C12 1.360(6) . ? N4 C13 1.448(7) . ? N4 C14 1.452(6) . ? C1 C2 1.368(10) . ? C1 C5 1.373(11) . ? C2 C3 1.344(9) . ? C3 C4 1.376(9) . ? C4 C5 1.386(10) . ? C6 C10 1.298(11) . ? C6 C7 1.323(10) . ? C7 C8 1.353(9) . ? C8 C9 1.436(10) . ? C9 C10 1.346(11) . ? C17 C18 1.363(6) . ? C17 C22 1.382(7) . ? C18 C19 1.397(7) . ? C19 C20 1.367(8) . ? C20 C21 1.360(8) . ? C21 C22 1.374(7) . ? O2 C23 1.376(15) . ? O2 C26 1.480(15) . ? C23 C24 1.488(15) . ? C24 C25 1.419(14) . ? C25 C26 1.427(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Y1 O1 67.37(11) 2_775 . ? O1 Y1 N1 121.09(11) 2_775 . ? O1 Y1 N1 54.06(10) . . ? O1 Y1 C2 84.63(19) 2_775 . ? O1 Y1 C2 128.6(2) . . ? N1 Y1 C2 126.20(17) . . ? O1 Y1 C9 107.7(3) 2_775 . ? O1 Y1 C9 91.3(2) . . ? N1 Y1 C9 81.09(17) . . ? C2 Y1 C9 139.3(2) . . ? O1 Y1 C10 128.91(18) 2_775 . ? O1 Y1 C10 117.2(3) . . ? N1 Y1 C10 86.8(2) . . ? C2 Y1 C10 114.0(3) . . ? C9 Y1 C10 29.5(2) . . ? O1 Y1 C1 114.0(3) 2_775 . ? O1 Y1 C1 145.3(2) . . ? N1 Y1 C1 110.5(3) . . ? C2 Y1 C1 30.0(2) . . ? C9 Y1 C1 118.7(3) . . ? C10 Y1 C1 89.5(3) . . ? O1 Y1 C5 128.52(18) 2_775 . ? O1 Y1 C5 119.9(3) . . ? N1 Y1 C5 81.3(2) . . ? C2 Y1 C5 49.6(2) . . ? C9 Y1 C5 122.0(3) . . ? C10 Y1 C5 94.9(3) . . ? C1 Y1 C5 30.1(2) . . ? O1 Y1 C8 80.03(17) 2_775 . ? O1 Y1 C8 94.24(18) . . ? N1 Y1 C8 108.1(2) . . ? C2 Y1 C8 123.4(3) . . ? C9 Y1 C8 31.4(2) . . ? C10 Y1 C8 49.5(2) . . ? C1 Y1 C8 120.4(3) . . ? C5 Y1 C8 140.9(3) . . ? O1 Y1 C6 112.8(2) 2_775 . ? O1 Y1 C6 138.59(19) . . ? N1 Y1 C6 114.5(2) . . ? C2 Y1 C6 91.4(3) . . ? C9 Y1 C6 48.0(2) . . ? C10 Y1 C6 28.3(2) . . ? C1 Y1 C6 74.9(2) . . ? C5 Y1 C6 93.0(3) . . ? C8 Y1 C6 48.2(2) . . ? O1 Y1 C3 79.60(16) 2_775 . ? O1 Y1 C3 101.02(17) . . ? N1 Y1 C3 104.14(18) . . ? C2 Y1 C3 29.31(19) . . ? C9 Y1 C3 167.5(3) . . ? C10 Y1 C3 138.3(3) . . ? C1 Y1 C3 48.8(2) . . ? C5 Y1 C3 49.1(2) . . ? C8 Y1 C3 147.4(3) . . ? C6 Y1 C3 120.1(2) . . ? O1 Y1 C7 84.93(18) 2_775 . ? O1 Y1 C7 122.26(19) . . ? N1 Y1 C7 130.04(15) . . ? C2 Y1 C7 95.5(2) . . ? C9 Y1 C7 49.31(18) . . ? C10 Y1 C7 47.9(2) . . ? C1 Y1 C7 91.8(3) . . ? C5 Y1 C7 117.0(3) . . ? C8 Y1 C7 29.4(2) . . ? C6 Y1 C7 28.7(2) . . ? C3 Y1 C7 123.3(2) . . ? C11 O1 Y1 148.4(3) . 2_775 ? C11 O1 Y1 97.7(2) . . ? Y1 O1 Y1 112.63(11) 2_775 . ? C11 N1 C17 122.9(4) . . ? C11 N1 Y1 95.3(2) . . ? C17 N1 Y1 139.6(3) . . ? C12 N2 C11 124.0(4) . . ? C12 N3 C15 119.5(4) . . ? C12 N3 C16 122.7(5) . . ? C15 N3 C16 115.9(5) . . ? C12 N4 C13 121.2(4) . . ? C12 N4 C14 122.8(5) . . ? C13 N4 C14 115.0(5) . . ? C2 C1 C5 107.9(7) . . ? C2 C1 Y1 74.8(3) . . ? C5 C1 Y1 75.3(4) . . ? C3 C2 C1 108.2(7) . . ? C3 C2 Y1 76.8(3) . . ? C1 C2 Y1 75.2(4) . . ? C2 C3 C4 109.5(6) . . ? C2 C3 Y1 73.9(3) . . ? C4 C3 Y1 76.2(3) . . ? C3 C4 C5 106.4(6) . . ? C3 C4 Y1 74.1(3) . . ? C5 C4 Y1 73.1(3) . . ? C1 C5 C4 107.9(7) . . ? C1 C5 Y1 74.6(4) . . ? C4 C5 Y1 76.9(3) . . ? C10 C6 C7 111.0(7) . . ? C10 C6 Y1 74.9(4) . . ? C7 C6 Y1 76.2(4) . . ? C6 C7 C8 108.5(7) . . ? C6 C7 Y1 75.2(4) . . ? C8 C7 Y1 74.6(3) . . ? C7 C8 C9 105.3(6) . . ? C7 C8 Y1 76.0(3) . . ? C9 C8 Y1 73.5(3) . . ? C10 C9 C8 105.9(6) . . ? C10 C9 Y1 75.3(4) . . ? C8 C9 Y1 75.0(3) . . ? C6 C10 C9 109.3(7) . . ? C6 C10 Y1 76.8(4) . . ? C9 C10 Y1 75.1(4) . . ? O1 C11 N1 112.8(4) . . ? O1 C11 N2 117.6(4) . . ? N1 C11 N2 129.5(4) . . ? O1 C11 Y1 55.38(19) . . ? N1 C11 Y1 57.5(2) . . ? N2 C11 Y1 170.7(3) . . ? N2 C12 N4 124.7(4) . . ? N2 C12 N3 118.3(4) . . ? N4 C12 N3 116.8(4) . . ? C18 C17 C22 118.4(4) . . ? C18 C17 N1 119.8(4) . . ? C22 C17 N1 121.6(4) . . ? C17 C18 C19 120.8(5) . . ? C20 C19 C18 119.8(5) . . ? C21 C20 C19 119.6(5) . . ? C20 C21 C22 120.7(6) . . ? C21 C22 C17 120.7(5) . . ? C23 O2 C26 100.6(12) . . ? O2 C23 C24 100.3(11) . . ? C25 C24 C23 106.1(9) . . ? C24 C25 C26 104.8(9) . . ? C25 C26 O2 101.9(11) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.784 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.091 # Attachment 'complex_2.cif' data_f50315b _database_code_depnum_ccdc_archive 'CCDC 695033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H29 Cl N6 Ti' _chemical_formula_weight 376.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/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 8.225(4) _cell_length_b 14.125(6) _cell_length_c 16.190(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.004(7) _cell_angle_gamma 90.00 _cell_volume 1880.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 777 _cell_measurement_theta_min 2.758 _cell_measurement_theta_max 22.705 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.605 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9147 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.04 _diffrn_reflns_number 8457 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3680 _reflns_number_gt 2624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+1.9232P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3680 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 Ti1 Ti 0.00013(8) 0.24342(5) 0.89215(4) 0.0334(2) Uani 1 1 d . . . Cl1 Cl -0.28735(13) 0.24223(9) 0.90000(8) 0.0618(4) Uani 1 1 d . . . N1 N 0.0352(4) 0.1661(2) 0.80515(19) 0.0419(8) Uani 1 1 d . . . N2 N 0.2340(5) 0.1278(3) 0.7120(2) 0.0531(9) Uani 1 1 d . . . N3 N -0.0369(5) 0.1224(3) 0.6726(2) 0.0508(9) Uani 1 1 d . . . N4 N 0.0659(4) 0.1793(2) 0.98408(19) 0.0413(8) Uani 1 1 d . . . N5 N 0.2741(4) 0.1242(3) 1.0701(2) 0.0507(9) Uani 1 1 d . . . N6 N 0.0057(4) 0.0976(3) 1.1026(2) 0.0495(9) Uani 1 1 d . . . C1 C -0.0315(7) 0.3988(3) 0.8338(3) 0.0623(13) Uani 1 1 d . . . H1A H -0.1197 0.4196 0.7966 0.075 Uiso 1 1 calc R . . C2 C 0.1185(7) 0.3651(3) 0.8104(3) 0.0667(15) Uani 1 1 d . . . H2A H 0.1544 0.3579 0.7534 0.080 Uiso 1 1 calc R . . C3 C 0.2160(6) 0.3518(3) 0.8812(4) 0.0658(14) Uani 1 1 d . . . H3A H 0.3323 0.3368 0.8827 0.079 Uiso 1 1 calc R . . C4 C 0.1239(7) 0.3834(3) 0.9470(3) 0.0638(14) Uani 1 1 d . . . H4A H 0.1642 0.3911 1.0039 0.077 Uiso 1 1 calc R . . C5 C -0.0257(7) 0.4095(3) 0.9188(3) 0.0603(13) Uani 1 1 d . . . H5A H -0.1104 0.4388 0.9520 0.072 Uiso 1 1 calc R . . C6 C 0.0766(5) 0.1398(3) 0.7327(2) 0.0407(9) Uani 1 1 d . . . C7 C 0.3575(6) 0.1238(4) 0.7769(3) 0.0645(13) Uani 1 1 d . . . H7A H 0.3068 0.1123 0.8289 0.097 Uiso 1 1 calc R . . H7B H 0.4150 0.1829 0.7793 0.097 Uiso 1 1 calc R . . H7C H 0.4324 0.0736 0.7655 0.097 Uiso 1 1 calc R . . C8 C 0.2956(7) 0.1456(4) 0.6308(3) 0.0720(15) Uani 1 1 d . . . H8A H 0.2068 0.1474 0.5916 0.108 Uiso 1 1 calc R . . H8B H 0.3695 0.0960 0.6161 0.108 Uiso 1 1 calc R . . H8C H 0.3516 0.2052 0.6305 0.108 Uiso 1 1 calc R . . C9 C -0.2033(6) 0.1479(4) 0.6892(3) 0.0661(14) Uani 1 1 d . . . H9A H -0.2048 0.1995 0.7278 0.099 Uiso 1 1 calc R . . H9B H -0.2587 0.0945 0.7121 0.099 Uiso 1 1 calc R . . H9C H -0.2570 0.1667 0.6387 0.099 Uiso 1 1 calc R . . C10 C -0.0202(7) 0.0444(4) 0.6142(3) 0.0737(16) Uani 1 1 d . . . H10A H 0.0930 0.0319 0.6058 0.111 Uiso 1 1 calc R . . H10B H -0.0714 0.0612 0.5625 0.111 Uiso 1 1 calc R . . H10C H -0.0712 -0.0112 0.6359 0.111 Uiso 1 1 calc R . . C11 C 0.1137(5) 0.1360(3) 1.0494(2) 0.0377(9) Uani 1 1 d . . . C12 C 0.3926(6) 0.1775(5) 1.0249(3) 0.0713(15) Uani 1 1 d . . . H12A H 0.3443 0.2353 1.0051 0.107 Uiso 1 1 calc R . . H12B H 0.4287 0.1407 0.9788 0.107 Uiso 1 1 calc R . . H12C H 0.4837 0.1920 1.0605 0.107 Uiso 1 1 calc R . . C13 C 0.3329(7) 0.0345(4) 1.1038(3) 0.0714(15) Uani 1 1 d . . . H13A H 0.2471 0.0039 1.1330 0.107 Uiso 1 1 calc R . . H13B H 0.4229 0.0460 1.1410 0.107 Uiso 1 1 calc R . . H13C H 0.3675 -0.0055 1.0595 0.107 Uiso 1 1 calc R . . C14 C 0.0351(7) 0.0965(4) 1.1909(3) 0.0650(14) Uani 1 1 d . . . H14A H 0.1493 0.1041 1.2022 0.097 Uiso 1 1 calc R . . H14B H -0.0009 0.0372 1.2131 0.097 Uiso 1 1 calc R . . H14C H -0.0237 0.1473 1.2160 0.097 Uiso 1 1 calc R . . C15 C -0.1591(6) 0.0861(4) 1.0762(3) 0.0712(15) Uani 1 1 d . . . H15A H -0.1656 0.0877 1.0170 0.107 Uiso 1 1 calc R . . H15B H -0.2237 0.1363 1.0984 0.107 Uiso 1 1 calc R . . H15C H -0.1991 0.0263 1.0955 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ti1 0.0357(4) 0.0361(4) 0.0284(3) 0.0016(3) 0.0019(3) -0.0020(3) Cl1 0.0363(6) 0.0825(9) 0.0668(8) 0.0042(6) 0.0045(5) 0.0008(6) N1 0.043(2) 0.0476(19) 0.0348(17) -0.0067(15) -0.0003(14) 0.0011(16) N2 0.046(2) 0.067(2) 0.047(2) -0.0044(18) 0.0058(17) 0.0087(19) N3 0.055(2) 0.060(2) 0.0370(19) -0.0118(17) -0.0041(16) 0.0115(18) N4 0.0375(19) 0.0488(19) 0.0376(18) 0.0030(15) 0.0008(14) -0.0034(15) N5 0.039(2) 0.067(2) 0.046(2) 0.0072(18) -0.0031(16) 0.0074(18) N6 0.050(2) 0.061(2) 0.0370(19) 0.0118(17) -0.0016(15) -0.0100(18) C1 0.079(4) 0.051(3) 0.057(3) 0.018(2) -0.009(3) -0.005(3) C2 0.090(4) 0.056(3) 0.055(3) 0.007(2) 0.021(3) -0.021(3) C3 0.051(3) 0.050(3) 0.096(4) 0.005(3) 0.004(3) -0.016(2) C4 0.084(4) 0.049(3) 0.058(3) 0.000(2) -0.019(3) -0.016(3) C5 0.077(4) 0.039(2) 0.065(3) -0.005(2) 0.004(3) 0.003(2) C6 0.048(3) 0.035(2) 0.038(2) 0.0009(16) -0.0006(18) 0.0037(18) C7 0.045(3) 0.078(3) 0.070(3) -0.009(3) -0.005(2) 0.009(3) C8 0.070(4) 0.086(4) 0.060(3) 0.002(3) 0.023(3) 0.003(3) C9 0.048(3) 0.092(4) 0.058(3) -0.011(3) -0.013(2) 0.013(3) C10 0.085(4) 0.078(4) 0.057(3) -0.032(3) -0.014(3) 0.015(3) C11 0.044(2) 0.039(2) 0.0310(19) -0.0009(16) 0.0020(16) -0.0007(17) C12 0.035(3) 0.107(4) 0.073(3) 0.006(3) 0.002(2) -0.003(3) C13 0.078(4) 0.078(4) 0.058(3) -0.004(3) -0.011(3) 0.033(3) C14 0.076(4) 0.081(4) 0.038(2) 0.013(2) 0.003(2) -0.004(3) C15 0.058(3) 0.091(4) 0.065(3) 0.018(3) -0.002(2) -0.030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ti1 N1 1.809(3) . ? Ti1 N4 1.817(3) . ? Ti1 C3 2.354(5) . ? Ti1 Cl1 2.3702(16) . ? Ti1 C2 2.388(5) . ? Ti1 C4 2.388(5) . ? Ti1 C5 2.395(5) . ? Ti1 C1 2.401(5) . ? N1 C6 1.283(5) . ? N2 C6 1.354(5) . ? N2 C8 1.439(6) . ? N2 C7 1.450(6) . ? N3 C6 1.359(5) . ? N3 C9 1.445(6) . ? N3 C10 1.460(6) . ? N4 C11 1.277(5) . ? N5 C11 1.366(5) . ? N5 C12 1.441(6) . ? N5 C13 1.459(6) . ? N6 C11 1.362(5) . ? N6 C15 1.424(6) . ? N6 C14 1.445(5) . ? C1 C2 1.381(8) . ? C1 C5 1.384(7) . ? C2 C3 1.400(8) . ? C3 C4 1.392(7) . ? C4 C5 1.356(7) . ? 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 Ti1 N4 106.71(16) . . ? N1 Ti1 C3 101.73(18) . . ? N4 Ti1 C3 99.93(18) . . ? N1 Ti1 Cl1 102.13(12) . . ? N4 Ti1 Cl1 103.62(11) . . ? C3 Ti1 Cl1 139.74(14) . . ? N1 Ti1 C2 86.05(18) . . ? N4 Ti1 C2 134.02(19) . . ? C3 Ti1 C2 34.32(19) . . ? Cl1 Ti1 C2 116.85(16) . . ? N1 Ti1 C4 135.76(18) . . ? N4 Ti1 C4 89.39(16) . . ? C3 Ti1 C4 34.12(18) . . ? Cl1 Ti1 C4 113.91(15) . . ? C2 Ti1 C4 55.57(18) . . ? N1 Ti1 C5 138.34(17) . . ? N4 Ti1 C5 111.53(17) . . ? C3 Ti1 C5 56.33(19) . . ? Cl1 Ti1 C5 84.59(14) . . ? C2 Ti1 C5 55.44(18) . . ? C4 Ti1 C5 32.94(18) . . ? N1 Ti1 C1 105.25(17) . . ? N4 Ti1 C1 143.78(17) . . ? C3 Ti1 C1 56.80(19) . . ? Cl1 Ti1 C1 85.77(14) . . ? C2 Ti1 C1 33.52(18) . . ? C4 Ti1 C1 55.41(18) . . ? C5 Ti1 C1 33.55(17) . . ? C6 N1 Ti1 159.3(3) . . ? C6 N2 C8 123.9(4) . . ? C6 N2 C7 119.1(4) . . ? C8 N2 C7 114.6(4) . . ? C6 N3 C9 117.6(3) . . ? C6 N3 C10 121.9(4) . . ? C9 N3 C10 114.1(4) . . ? C11 N4 Ti1 178.6(3) . . ? C11 N5 C12 118.0(4) . . ? C11 N5 C13 120.7(4) . . ? C12 N5 C13 114.9(4) . . ? C11 N6 C15 118.9(4) . . ? C11 N6 C14 122.1(4) . . ? C15 N6 C14 115.9(4) . . ? C2 C1 C5 107.1(5) . . ? C2 C1 Ti1 72.7(3) . . ? C5 C1 Ti1 73.0(3) . . ? C1 C2 C3 108.9(5) . . ? C1 C2 Ti1 73.8(3) . . ? C3 C2 Ti1 71.5(3) . . ? C4 C3 C2 105.8(5) . . ? C4 C3 Ti1 74.3(3) . . ? C2 C3 Ti1 74.2(3) . . ? C5 C4 C3 109.4(5) . . ? C5 C4 Ti1 73.8(3) . . ? C3 C4 Ti1 71.6(3) . . ? C4 C5 C1 108.7(5) . . ? C4 C5 Ti1 73.3(3) . . ? C1 C5 Ti1 73.5(3) . . ? N1 C6 N2 122.2(4) . . ? N1 C6 N3 121.1(4) . . ? N2 C6 N3 116.7(4) . . ? N4 C11 N6 121.3(4) . . ? N4 C11 N5 123.0(4) . . ? N6 C11 N5 115.7(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.468 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.064 # Attachment 'complex_1.cif' data_f50329b _database_code_depnum_ccdc_archive 'CCDC 695034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 Cl N3 Ti' _chemical_formula_weight 327.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 13.595(4) _cell_length_b 15.297(4) _cell_length_c 15.395(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3201.7(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 872 _cell_measurement_theta_min 2.974 _cell_measurement_theta_max 20.511 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8453 _exptl_absorpt_correction_T_max 0.9337 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.63 _diffrn_reflns_number 13972 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3153 _reflns_number_gt 1981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+1.8995P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3153 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 Ti1 Ti 0.77638(4) 0.02420(4) 0.39752(4) 0.0391(2) Uani 1 1 d . . . Cl1 Cl 0.80133(10) 0.04477(9) 0.55507(8) 0.0811(4) Uani 1 1 d . . . N1 N 0.8546(2) 0.11491(18) 0.35853(19) 0.0397(7) Uani 1 1 d . . . N2 N 0.8978(3) 0.1933(2) 0.23477(19) 0.0525(9) Uani 1 1 d . . . N3 N 0.9460(2) 0.24334(17) 0.37121(18) 0.0382(7) Uani 1 1 d . . . C1 C 0.7763(3) -0.1284(3) 0.3607(3) 0.0644(12) Uani 1 1 d . . . H1A H 0.7173 -0.1645 0.3538 0.077 Uiso 1 1 calc R . . C2 C 0.8236(4) -0.0849(3) 0.2943(4) 0.0801(15) Uani 1 1 d . . . H2A H 0.8059 -0.0863 0.2326 0.096 Uiso 1 1 calc R . . C3 C 0.9091(4) -0.0523(3) 0.3289(6) 0.104(2) Uani 1 1 d . . . H3A H 0.9618 -0.0246 0.2954 0.125 Uiso 1 1 calc R . . C4 C 0.9137(4) -0.0712(3) 0.4151(6) 0.106(3) Uani 1 1 d . . . H4A H 0.9703 -0.0615 0.4533 0.127 Uiso 1 1 calc R . . C5 C 0.8286(4) -0.1197(3) 0.4357(4) 0.0862(17) Uani 1 1 d . . . H5A H 0.8154 -0.1498 0.4907 0.103 Uiso 1 1 calc R . . C6 C 0.6107(3) 0.0452(4) 0.4489(4) 0.0746(15) Uani 1 1 d . . . H6A H 0.5871 0.0337 0.5080 0.090 Uiso 1 1 calc R . . C7 C 0.6443(3) 0.1257(3) 0.4173(4) 0.0722(14) Uani 1 1 d . . . H7A H 0.6475 0.1805 0.4501 0.087 Uiso 1 1 calc R . . C8 C 0.6576(3) 0.1168(3) 0.3301(4) 0.0727(14) Uani 1 1 d . . . H8A H 0.6727 0.1646 0.2899 0.087 Uiso 1 1 calc R . . C9 C 0.6365(3) 0.0324(4) 0.3062(4) 0.0743(14) Uani 1 1 d . . . H9A H 0.6324 0.0106 0.2464 0.089 Uiso 1 1 calc R . . C10 C 0.6050(3) -0.0115(3) 0.3796(4) 0.0731(14) Uani 1 1 d . . . H10A H 0.5768 -0.0704 0.3810 0.088 Uiso 1 1 calc R . . C11 C 0.8968(2) 0.1792(2) 0.3223(2) 0.0353(8) Uani 1 1 d . . . C12 C 0.8644(4) 0.1262(3) 0.1752(3) 0.0788(15) Uani 1 1 d . . . H12A H 0.8542 0.0727 0.2064 0.118 Uiso 1 1 calc R . . H12B H 0.9131 0.1174 0.1309 0.118 Uiso 1 1 calc R . . H12C H 0.8037 0.1443 0.1489 0.118 Uiso 1 1 calc R . . C13 C 0.9153(4) 0.2772(3) 0.1947(3) 0.0756(15) Uani 1 1 d . . . H13A H 0.9386 0.3177 0.2377 0.113 Uiso 1 1 calc R . . H13B H 0.8551 0.2986 0.1700 0.113 Uiso 1 1 calc R . . H13C H 0.9637 0.2710 0.1498 0.113 Uiso 1 1 calc R . . C14 C 0.9271(3) 0.2395(2) 0.4644(2) 0.0505(10) Uani 1 1 d . . . H14A H 0.8577 0.2335 0.4743 0.076 Uiso 1 1 calc R . . H14B H 0.9502 0.2922 0.4913 0.076 Uiso 1 1 calc R . . H14C H 0.9609 0.1902 0.4888 0.076 Uiso 1 1 calc R . . C15 C 1.0509(3) 0.2522(3) 0.3531(3) 0.0721(14) Uani 1 1 d . . . H15A H 1.0610 0.2551 0.2914 0.108 Uiso 1 1 calc R . . H15B H 1.0854 0.2027 0.3762 0.108 Uiso 1 1 calc R . . H15C H 1.0752 0.3047 0.3797 0.108 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 Ti1 0.0334(3) 0.0325(3) 0.0514(4) 0.0051(3) 0.0022(3) -0.0009(3) Cl1 0.0944(10) 0.0966(9) 0.0522(7) 0.0154(6) -0.0028(6) -0.0291(7) N1 0.0417(17) 0.0406(17) 0.0368(17) -0.0010(13) 0.0047(14) -0.0031(13) N2 0.076(2) 0.0501(19) 0.0318(18) 0.0004(15) 0.0049(16) -0.0172(17) N3 0.0468(17) 0.0354(15) 0.0323(17) 0.0007(12) 0.0046(13) -0.0059(13) C1 0.057(3) 0.037(2) 0.099(4) 0.001(2) -0.008(3) 0.003(2) C2 0.100(4) 0.048(3) 0.093(4) -0.017(3) 0.025(3) 0.016(3) C3 0.058(4) 0.052(3) 0.203(8) -0.030(4) 0.045(5) 0.006(3) C4 0.056(3) 0.052(3) 0.211(8) -0.035(4) -0.060(5) 0.026(3) C5 0.109(5) 0.039(3) 0.111(5) 0.014(3) -0.031(4) 0.014(3) C6 0.040(2) 0.097(4) 0.087(4) 0.009(3) 0.024(2) 0.005(2) C7 0.046(3) 0.060(3) 0.111(5) -0.021(3) 0.006(3) 0.015(2) C8 0.052(3) 0.074(3) 0.092(4) 0.027(3) -0.012(3) 0.017(2) C9 0.040(2) 0.101(4) 0.081(4) -0.014(3) -0.017(2) 0.005(3) C10 0.034(2) 0.062(3) 0.123(5) -0.001(3) -0.001(3) -0.005(2) C11 0.0389(19) 0.0334(18) 0.034(2) -0.0003(15) 0.0052(15) 0.0016(15) C12 0.103(4) 0.092(4) 0.041(3) -0.015(2) 0.010(3) -0.037(3) C13 0.130(4) 0.059(3) 0.038(3) 0.012(2) 0.003(3) -0.002(3) C14 0.065(3) 0.051(2) 0.036(2) 0.0017(18) -0.0011(19) -0.004(2) C15 0.057(3) 0.097(3) 0.062(3) -0.015(3) 0.011(2) -0.031(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ti1 N1 1.848(3) . ? Ti1 C9 2.369(4) . ? Ti1 C8 2.385(4) . ? Ti1 C4 2.385(5) . ? Ti1 C5 2.387(4) . ? Ti1 C2 2.392(4) . ? Ti1 C7 2.393(4) . ? Ti1 C3 2.396(5) . ? Ti1 C1 2.402(4) . ? Ti1 C10 2.409(4) . ? Ti1 C6 2.409(4) . ? Ti1 Cl1 2.4693(15) . ? N1 C11 1.267(4) . ? N2 C11 1.365(4) . ? N2 C13 1.443(5) . ? N2 C12 1.449(5) . ? N3 C11 1.406(4) . ? N3 C14 1.458(4) . ? N3 C15 1.459(5) . ? C1 C5 1.362(7) . ? C1 C2 1.380(6) . ? C2 C3 1.372(8) . ? C3 C4 1.359(9) . ? C4 C5 1.411(8) . ? C6 C10 1.377(7) . ? C6 C7 1.401(6) . ? C7 C8 1.361(7) . ? C8 C9 1.373(6) . ? C9 C10 1.384(7) . ? 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 Ti1 C9 103.25(17) . . ? N1 Ti1 C8 78.60(15) . . ? C9 Ti1 C8 33.57(16) . . ? N1 Ti1 C4 92.6(2) . . ? C9 Ti1 C4 136.7(2) . . ? C8 Ti1 C4 160.5(3) . . ? N1 Ti1 C5 126.98(18) . . ? C9 Ti1 C5 115.7(2) . . ? C8 Ti1 C5 148.9(2) . . ? C4 Ti1 C5 34.4(2) . . ? N1 Ti1 C2 98.82(16) . . ? C9 Ti1 C2 81.8(2) . . ? C8 Ti1 C2 107.9(2) . . ? C4 Ti1 C2 55.8(2) . . ? C5 Ti1 C2 55.98(19) . . ? N1 Ti1 C7 89.18(15) . . ? C9 Ti1 C7 55.87(18) . . ? C8 Ti1 C7 33.10(17) . . ? C4 Ti1 C7 165.9(2) . . ? C5 Ti1 C7 142.2(2) . . ? C2 Ti1 C7 137.6(2) . . ? N1 Ti1 C3 77.92(17) . . ? C9 Ti1 C3 111.6(3) . . ? C8 Ti1 C3 127.5(3) . . ? C4 Ti1 C3 33.0(2) . . ? C5 Ti1 C3 55.5(2) . . ? C2 Ti1 C3 33.3(2) . . ? C7 Ti1 C3 159.7(3) . . ? N1 Ti1 C1 130.78(15) . . ? C9 Ti1 C1 84.90(18) . . ? C8 Ti1 C1 118.31(18) . . ? C4 Ti1 C1 55.42(17) . . ? C5 Ti1 C1 33.05(16) . . ? C2 Ti1 C1 33.45(15) . . ? C7 Ti1 C1 131.32(16) . . ? C3 Ti1 C1 54.65(17) . . ? N1 Ti1 C10 133.60(16) . . ? C9 Ti1 C10 33.66(17) . . ? C8 Ti1 C10 55.27(17) . . ? C4 Ti1 C10 129.14(18) . . ? C5 Ti1 C10 96.11(19) . . ? C2 Ti1 C10 91.5(2) . . ? C7 Ti1 C10 55.68(16) . . ? C3 Ti1 C10 124.5(2) . . ? C1 Ti1 C10 75.65(16) . . ? N1 Ti1 C6 122.99(16) . . ? C9 Ti1 C6 55.76(18) . . ? C8 Ti1 C6 55.31(18) . . ? C4 Ti1 C6 140.9(2) . . ? C5 Ti1 C6 108.7(2) . . ? C2 Ti1 C6 124.2(2) . . ? C7 Ti1 C6 33.92(15) . . ? C3 Ti1 C6 156.1(2) . . ? C1 Ti1 C6 101.93(17) . . ? C10 Ti1 C6 33.22(16) . . ? N1 Ti1 Cl1 98.30(10) . . ? C9 Ti1 Cl1 133.38(14) . . ? C8 Ti1 Cl1 116.39(15) . . ? C4 Ti1 Cl1 81.9(2) . . ? C5 Ti1 Cl1 80.49(15) . . ? C2 Ti1 Cl1 134.81(15) . . ? C7 Ti1 Cl1 83.99(14) . . ? C3 Ti1 Cl1 113.1(2) . . ? C1 Ti1 Cl1 110.83(13) . . ? C10 Ti1 Cl1 105.90(16) . . ? C6 Ti1 Cl1 77.80(14) . . ? C11 N1 Ti1 170.2(3) . . ? C11 N2 C13 124.4(3) . . ? C11 N2 C12 120.6(3) . . ? C13 N2 C12 114.2(3) . . ? C11 N3 C14 114.4(3) . . ? C11 N3 C15 115.3(3) . . ? C14 N3 C15 111.4(3) . . ? C5 C1 C2 109.8(5) . . ? C5 C1 Ti1 72.9(3) . . ? C2 C1 Ti1 72.9(2) . . ? C3 C2 C1 106.3(6) . . ? C3 C2 Ti1 73.5(3) . . ? C1 C2 Ti1 73.6(3) . . ? C4 C3 C2 110.0(6) . . ? C4 C3 Ti1 73.1(3) . . ? C2 C3 Ti1 73.2(3) . . ? C3 C4 C5 107.0(5) . . ? C3 C4 Ti1 73.9(3) . . ? C5 C4 Ti1 72.9(3) . . ? C1 C5 C4 106.8(6) . . ? C1 C5 Ti1 74.1(3) . . ? C4 C5 Ti1 72.7(3) . . ? C10 C6 C7 107.6(5) . . ? C10 C6 Ti1 73.4(2) . . ? C7 C6 Ti1 72.4(2) . . ? C8 C7 C6 107.3(5) . . ? C8 C7 Ti1 73.1(3) . . ? C6 C7 Ti1 73.7(2) . . ? C7 C8 C9 109.4(5) . . ? C7 C8 Ti1 73.8(3) . . ? C9 C8 Ti1 72.6(3) . . ? C8 C9 C10 107.6(5) . . ? C8 C9 Ti1 73.9(3) . . ? C10 C9 Ti1 74.8(3) . . ? C6 C10 C9 108.1(4) . . ? C6 C10 Ti1 73.4(3) . . ? C9 C10 Ti1 71.6(2) . . ? N1 C11 N2 124.2(3) . . ? N1 C11 N3 121.4(3) . . ? N2 C11 N3 114.4(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.339 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.061 # Attachment 'complex_3.cif' data_f50627a _database_code_depnum_ccdc_archive 'CCDC 695035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H52 N6 Y2' _chemical_formula_weight 758.67 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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 14.655(8) _cell_length_b 15.235(8) _cell_length_c 16.563(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3698(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 788 _cell_measurement_theta_min 2.780 _cell_measurement_theta_max 19.725 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 3.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4511 _exptl_absorpt_correction_T_max 0.5059 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 7.61 _diffrn_reflns_number 11330 _diffrn_reflns_av_R_equivalents 0.1485 _diffrn_reflns_av_sigmaI/netI 0.1958 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3138 _reflns_number_gt 1295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0103P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3138 _refine_ls_number_parameters 209 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1691 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.048 _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 Y1 Y 0.13959(5) 0.30980(5) 0.10356(4) 0.0400(2) Uani 1 1 d . . . N1 N 0.2077(4) 0.1694(4) 0.1003(3) 0.0459(18) Uani 1 1 d . . . N2 N 0.1166(4) 0.0429(4) 0.0757(3) 0.051(2) Uani 1 1 d . . . N3 N 0.0655(4) 0.1577(3) 0.1600(3) 0.0388(18) Uani 1 1 d . . . C1 C 0.1013(9) 0.4710(6) 0.1662(5) 0.073(3) Uani 1 1 d . . . H1 H 0.1058 0.5166 0.1290 0.087 Uiso 1 1 calc R . . C2 C 0.1695(7) 0.4410(7) 0.2155(6) 0.072(3) Uani 1 1 d . . . H2 H 0.2278 0.4647 0.2201 0.086 Uiso 1 1 calc R . . C3 C 0.1362(9) 0.3689(7) 0.2572(5) 0.067(3) Uani 1 1 d . . . H3 H 0.1692 0.3344 0.2931 0.080 Uiso 1 1 calc R . . C4 C 0.0463(8) 0.3569(7) 0.2366(7) 0.072(3) Uani 1 1 d . . . H4 H 0.0076 0.3134 0.2560 0.086 Uiso 1 1 calc R . . C5 C 0.0245(7) 0.4212(8) 0.1818(6) 0.077(3) Uani 1 1 d . . . H5 H -0.0328 0.4298 0.1589 0.092 Uiso 1 1 calc R . . C6 C 0.0160(9) 0.3713(10) -0.0080(5) 0.077(4) Uani 1 1 d . . . H6 H -0.0284 0.4095 0.0114 0.093 Uiso 1 1 calc R . . C7 C 0.0100(9) 0.2810(10) -0.0134(6) 0.076(4) Uani 1 1 d . . . H7 H -0.0399 0.2472 0.0019 0.091 Uiso 1 1 calc R . . C8 C 0.0897(11) 0.2497(7) -0.0451(5) 0.070(4) Uani 1 1 d . . . H8 H 0.1033 0.1913 -0.0560 0.084 Uiso 1 1 calc R . . C9 C 0.1455(7) 0.3198(11) -0.0577(4) 0.064(3) Uani 1 1 d . . . H9 H 0.2049 0.3178 -0.0775 0.076 Uiso 1 1 calc R . . C10 C 0.0992(11) 0.3928(7) -0.0363(6) 0.067(3) Uani 1 1 d . . . H10 H 0.1215 0.4498 -0.0405 0.080 Uiso 1 1 calc R . . C11 C 0.1396(6) 0.1240(5) 0.1075(4) 0.0397(18) Uani 1 1 d . . . C12 C 0.0669(5) -0.0284(4) 0.1127(4) 0.079(3) Uani 1 1 d . . . H12A H 0.1074 -0.0770 0.1215 0.118 Uiso 1 1 calc R . . H12B H 0.0181 -0.0463 0.0777 0.118 Uiso 1 1 calc R . . H12C H 0.0422 -0.0093 0.1634 0.118 Uiso 1 1 calc R . . C13 C 0.1791(5) 0.0137(4) 0.0133(4) 0.072(3) Uani 1 1 d . . . H13A H 0.2002 0.0634 -0.0170 0.108 Uiso 1 1 calc R . . H13B H 0.1483 -0.0264 -0.0222 0.108 Uiso 1 1 calc R . . H13C H 0.2303 -0.0153 0.0378 0.108 Uiso 1 1 calc R . . C14 C 0.0856(4) 0.1455(4) 0.2484(4) 0.059(3) Uani 1 1 d . . . H14A H 0.0874 0.0839 0.2608 0.089 Uiso 1 1 calc R . . H14B H 0.0386 0.1731 0.2798 0.089 Uiso 1 1 calc R . . H14C H 0.1435 0.1716 0.2610 0.089 Uiso 1 1 calc R . . C15 C -0.0320(5) 0.1392(5) 0.1455(4) 0.068(3) Uani 1 1 d . . . H15A H -0.0421 0.1304 0.0888 0.102 Uiso 1 1 calc R . . H15B H -0.0680 0.1880 0.1639 0.102 Uiso 1 1 calc R . . H15C H -0.0494 0.0873 0.1745 0.102 Uiso 1 1 calc R . . C16 C 0.7500 0.2500 0.3294(12) 0.305(15) Uani 1 2 d SD . . H16A H 0.8076 0.2714 0.3487 0.458 Uiso 0.50 1 calc PR . . H16B H 0.7404 0.1913 0.3487 0.458 Uiso 0.50 1 calc PR . . H16C H 0.7019 0.2873 0.3487 0.458 Uiso 0.50 1 calc PR . . C17 C 0.7500 0.2500 0.2382(12) 0.119(7) Uani 1 2 d SD . . C18 C 0.7266(9) 0.1768(9) 0.1990(10) 0.149(6) Uani 1 1 d D . . H18 H 0.7084 0.1271 0.2274 0.178 Uiso 1 1 calc R . . C19 C 0.7298(15) 0.1757(19) 0.1155(10) 0.187(12) Uani 1 1 d D . . H19 H 0.7181 0.1237 0.0879 0.224 Uiso 1 1 calc R . . C20 C 0.7500 0.2500 0.073(3) 0.23(3) Uani 1 2 d SD . . H20 H 0.7500 0.2500 0.0171 0.270 Uiso 1 2 calc SR . . 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 Y1 0.0485(4) 0.0420(4) 0.0294(3) -0.0022(5) -0.0015(6) 0.0055(6) N1 0.063(4) 0.064(5) 0.011(3) 0.006(4) -0.010(4) -0.037(4) N2 0.049(6) 0.048(5) 0.057(5) -0.006(4) 0.013(4) -0.009(4) N3 0.045(5) 0.040(5) 0.031(4) -0.004(3) -0.007(4) -0.020(4) C1 0.100(10) 0.070(8) 0.048(7) 0.011(5) 0.000(7) 0.019(8) C2 0.089(10) 0.061(8) 0.065(7) -0.041(5) -0.001(7) -0.013(7) C3 0.099(9) 0.064(8) 0.037(5) -0.007(5) -0.010(8) 0.028(8) C4 0.078(10) 0.060(9) 0.077(8) -0.022(6) 0.031(7) -0.016(7) C5 0.073(9) 0.095(10) 0.062(8) -0.021(6) 0.012(7) 0.034(9) C6 0.061(10) 0.132(14) 0.038(7) 0.003(7) -0.015(7) 0.044(9) C7 0.084(11) 0.101(11) 0.043(6) 0.018(6) -0.037(7) -0.026(8) C8 0.119(12) 0.059(9) 0.031(6) -0.009(5) -0.035(7) 0.019(9) C9 0.060(7) 0.106(9) 0.024(4) 0.015(6) -0.015(5) 0.017(10) C10 0.095(11) 0.068(9) 0.038(6) 0.013(5) -0.043(7) 0.006(9) C11 0.064(6) 0.041(5) 0.014(4) -0.008(4) -0.004(7) 0.021(6) C12 0.100(7) 0.058(7) 0.079(6) 0.007(6) -0.019(7) -0.016(5) C13 0.074(7) 0.069(7) 0.072(6) -0.019(5) 0.012(6) -0.016(5) C14 0.068(6) 0.068(6) 0.041(5) -0.001(4) 0.012(5) 0.000(5) C15 0.041(6) 0.086(7) 0.077(7) 0.010(5) 0.001(5) -0.014(5) C16 0.36(4) 0.38(4) 0.18(2) 0.000 0.000 -0.08(2) C17 0.082(15) 0.16(2) 0.116(17) 0.000 0.000 0.005(17) C18 0.087(10) 0.100(13) 0.26(2) -0.036(14) 0.027(16) -0.011(10) C19 0.077(11) 0.27(3) 0.21(3) -0.13(2) 0.03(2) 0.041(16) C20 0.07(3) 0.48(9) 0.12(3) 0.000 0.000 0.07(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Y1 N1 2.261(6) 2 ? Y1 N1 2.361(6) . ? Y1 C9 2.677(6) . ? Y1 C4 2.690(8) . ? Y1 C3 2.699(8) . ? Y1 C10 2.705(8) . ? Y1 C5 2.721(9) . ? Y1 N3 2.724(5) . ? Y1 C1 2.725(9) . ? Y1 C8 2.727(8) . ? Y1 C7 2.748(9) . ? Y1 C6 2.752(8) . ? N1 C11 1.220(8) . ? N1 Y1 2.261(6) 2 ? N2 C11 1.386(8) . ? N2 C12 1.444(7) . ? N2 C13 1.451(7) . ? N3 C15 1.476(7) . ? N3 C11 1.482(8) . ? N3 C14 1.506(7) . ? C1 C2 1.369(9) . ? C1 C5 1.382(10) . ? C1 H1 0.9300 . ? C2 C3 1.387(9) . ? C2 H2 0.9300 . ? C3 C4 1.373(11) . ? C3 H3 0.9300 . ? C4 C5 1.372(10) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.347(10) . ? C6 C7 1.382(10) . ? C6 H6 0.9300 . ? C7 C8 1.365(11) . ? C7 H7 0.9300 . ? C8 C9 1.362(10) . ? C8 H8 0.9300 . ? C9 C10 1.350(10) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.510(15) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.336(10) . ? C17 C18 1.336(10) 2_655 ? C18 C19 1.384(14) . ? C18 H18 0.9300 . ? C19 C20 1.363(15) . ? C19 H19 0.9300 . ? C20 C19 1.363(15) 2_655 ? C20 H20 0.9300 . ? 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 Y1 N1 73.0(2) 2 . ? N1 Y1 C9 86.3(3) 2 . ? N1 Y1 C9 90.9(4) . . ? N1 Y1 C4 119.0(3) 2 . ? N1 Y1 C4 118.4(3) . . ? C9 Y1 C4 144.9(4) . . ? N1 Y1 C3 89.7(3) 2 . ? N1 Y1 C3 109.4(2) . . ? C9 Y1 C3 157.2(4) . . ? C4 Y1 C3 29.5(2) . . ? N1 Y1 C10 97.5(4) 2 . ? N1 Y1 C10 119.8(3) . . ? C9 Y1 C10 29.0(2) . . ? C4 Y1 C10 117.7(5) . . ? C3 Y1 C10 130.3(4) . . ? N1 Y1 C5 122.5(3) 2 . ? N1 Y1 C5 146.9(3) . . ? C9 Y1 C5 117.4(4) . . ? C4 Y1 C5 29.4(2) . . ? C3 Y1 C5 48.1(3) . . ? C10 Y1 C5 88.9(4) . . ? N1 Y1 N3 121.4(2) 2 . ? N1 Y1 N3 53.53(18) . . ? C9 Y1 N3 113.8(4) . . ? C4 Y1 N3 75.2(2) . . ? C3 Y1 N3 87.3(3) . . ? C10 Y1 N3 127.2(2) . . ? C5 Y1 N3 96.9(3) . . ? N1 Y1 C1 95.0(3) 2 . ? N1 Y1 C1 155.9(3) . . ? C9 Y1 C1 109.6(4) . . ? C4 Y1 C1 48.9(3) . . ? C3 Y1 C1 48.4(2) . . ? C10 Y1 C1 81.9(3) . . ? C5 Y1 C1 29.4(2) . . ? N3 Y1 C1 123.7(3) . . ? N1 Y1 C8 106.9(4) 2 . ? N1 Y1 C8 77.8(3) . . ? C9 Y1 C8 29.2(2) . . ? C4 Y1 C8 133.8(5) . . ? C3 Y1 C8 163.4(5) . . ? C10 Y1 C8 47.5(3) . . ? C5 Y1 C8 118.2(3) . . ? N3 Y1 C8 85.2(3) . . ? C1 Y1 C8 126.2(3) . . ? N1 Y1 C7 133.6(3) 2 . ? N1 Y1 C7 97.5(4) . . ? C9 Y1 C7 47.8(3) . . ? C4 Y1 C7 105.6(4) . . ? C3 Y1 C7 134.8(4) . . ? C10 Y1 C7 47.1(3) . . ? C5 Y1 C7 90.4(4) . . ? N3 Y1 C7 80.3(3) . . ? C1 Y1 C7 105.7(5) . . ? C8 Y1 C7 28.9(2) . . ? N1 Y1 C6 126.0(4) 2 . ? N1 Y1 C6 124.8(3) . . ? C9 Y1 C6 48.1(3) . . ? C4 Y1 C6 97.2(4) . . ? C3 Y1 C6 120.5(3) . . ? C10 Y1 C6 28.6(2) . . ? C5 Y1 C6 72.5(3) . . ? N3 Y1 C6 104.9(4) . . ? C1 Y1 C6 79.2(4) . . ? C8 Y1 C6 48.0(3) . . ? C7 Y1 C6 29.1(2) . . ? C11 N1 Y1 152.4(6) . 2 ? C11 N1 Y1 99.5(5) . . ? Y1 N1 Y1 106.9(2) 2 . ? C11 N2 C12 129.2(7) . . ? C11 N2 C13 113.0(6) . . ? C12 N2 C13 113.0(6) . . ? C15 N3 C11 123.3(6) . . ? C15 N3 C14 108.8(6) . . ? C11 N3 C14 112.6(6) . . ? C15 N3 Y1 119.5(4) . . ? C11 N3 Y1 78.5(4) . . ? C14 N3 Y1 111.1(3) . . ? C2 C1 C5 107.4(9) . . ? C2 C1 Y1 77.0(5) . . ? C5 C1 Y1 75.2(6) . . ? C2 C1 H1 126.3 . . ? C5 C1 H1 126.3 . . ? Y1 C1 H1 114.0 . . ? C1 C2 C3 107.7(9) . . ? C1 C2 Y1 74.1(5) . . ? C3 C2 Y1 72.8(5) . . ? C1 C2 H2 126.2 . . ? C3 C2 H2 126.2 . . ? Y1 C2 H2 118.9 . . ? C4 C3 C2 108.6(10) . . ? C4 C3 Y1 74.9(5) . . ? C2 C3 Y1 77.8(5) . . ? C4 C3 H3 125.7 . . ? C2 C3 H3 125.7 . . ? Y1 C3 H3 113.9 . . ? C5 C4 C3 107.0(10) . . ? C5 C4 Y1 76.6(6) . . ? C3 C4 Y1 75.6(5) . . ? C5 C4 H4 126.5 . . ? C3 C4 H4 126.5 . . ? Y1 C4 H4 113.9 . . ? C4 C5 C1 109.0(10) . . ? C4 C5 Y1 74.1(6) . . ? C1 C5 Y1 75.4(6) . . ? C4 C5 H5 125.5 . . ? C1 C5 H5 125.5 . . ? Y1 C5 H5 116.9 . . ? C10 C6 C7 106.1(11) . . ? C10 C6 Y1 73.8(5) . . ? C7 C6 Y1 75.3(6) . . ? C10 C6 H6 127.0 . . ? C7 C6 H6 127.0 . . ? Y1 C6 H6 116.3 . . ? C8 C7 C6 108.6(11) . . ? C8 C7 Y1 74.7(5) . . ? C6 C7 Y1 75.6(6) . . ? C8 C7 H7 125.7 . . ? C6 C7 H7 125.7 . . ? Y1 C7 H7 116.1 . . ? C9 C8 C7 107.4(10) . . ? C9 C8 Y1 73.4(4) . . ? C7 C8 Y1 76.4(5) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? Y1 C8 H8 116.1 . . ? C10 C9 C8 107.7(10) . . ? C10 C9 Y1 76.6(5) . . ? C8 C9 Y1 77.4(4) . . ? C10 C9 H9 126.2 . . ? C8 C9 H9 126.2 . . ? Y1 C9 H9 112.3 . . ? C6 C10 C9 110.3(11) . . ? C6 C10 Y1 77.6(5) . . ? C9 C10 Y1 74.3(5) . . ? C6 C10 H10 124.9 . . ? C9 C10 H10 124.9 . . ? Y1 C10 H10 115.1 . . ? N1 C11 N2 131.9(8) . . ? N1 C11 N3 117.5(7) . . ? N2 C11 N3 110.7(7) . . ? N1 C11 Y1 55.3(4) . . ? N2 C11 Y1 152.0(5) . . ? N3 C11 Y1 70.6(3) . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C18 122(2) . 2_655 ? C18 C17 C16 119.1(11) . . ? C18 C17 C16 119.1(11) 2_655 . ? C17 C18 C19 119(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 121(4) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C19 118(5) . 2_655 ? C19 C20 H20 120.9 . . ? C19 C20 H20 120.9 2_655 . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.192 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.092