# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_page_first ? _journal_year ? _journal_volume ? _journal_page_last 2 loop_ _publ_author_name 'Amila Dissanayake' 'A. Odom' _publ_contact_author_email odom@chemistry.msu.edu _publ_contact_author_name 'Aaron Odom' data_aad9sept11_0m _database_code_depnum_ccdc_archive 'CCDC 845078' #TrackingRef '- AAD9sept11_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C26 H34 N6 Ti' _chemical_formula_sum 'C26 H34 N6 Ti' _chemical_melting_point ? _exptl_crystal_description cut _exptl_crystal_colour red _diffrn_ambient_temperature 173(2) _chemical_formula_weight 478.49 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7933(11) _cell_length_b 14.4889(14) _cell_length_c 15.8761(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.0720(10) _cell_angle_gamma 90.00 _cell_volume 2463.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7982 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.33 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8594 _exptl_absorpt_correction_T_max 0.9184 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 22406 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.36 _reflns_number_total 4497 _reflns_number_gt 3816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0464P)^2^+1.0285P] 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 4497 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Ti1 Ti 0.74246(3) 0.08816(2) 0.246813(18) 0.02352(11) Uani 1 1 d . . . N1 N 0.75966(13) 0.23843(9) 0.28357(9) 0.0262(3) Uani 1 1 d . . . N2 N 0.90652(13) 0.09568(9) 0.33486(9) 0.0268(3) Uani 1 1 d . . . N3 N 0.55918(13) 0.11981(10) 0.19387(9) 0.0274(3) Uani 1 1 d . . . N4 N 0.63488(14) 0.10371(9) 0.35969(9) 0.0275(3) Uani 1 1 d . . . N5 N 0.71490(14) -0.04184(10) 0.24954(9) 0.0301(3) Uani 1 1 d . . . N6 N 0.82501(14) 0.10706(10) 0.14841(9) 0.0306(3) Uani 1 1 d . . . C1 C 0.67739(16) 0.30567(12) 0.25716(12) 0.0319(4) Uani 1 1 d . . . H1 H 0.6090 0.2907 0.2159 0.038 Uiso 1 1 calc R . . C2 C 0.68761(18) 0.39477(13) 0.28696(13) 0.0374(4) Uani 1 1 d . . . H2 H 0.6280 0.4404 0.2668 0.045 Uiso 1 1 calc R . . C3 C 0.78765(18) 0.41614(12) 0.34742(13) 0.0373(4) Uani 1 1 d . . . H3 H 0.7972 0.4770 0.3696 0.045 Uiso 1 1 calc R . . C4 C 0.87257(17) 0.34897(12) 0.37499(11) 0.0322(4) Uani 1 1 d . . . H4 H 0.9417 0.3634 0.4159 0.039 Uiso 1 1 calc R . . C5 C 0.85757(15) 0.25876(11) 0.34287(10) 0.0256(4) Uani 1 1 d . . . C6 C 0.93799(15) 0.18250(12) 0.36959(10) 0.0256(4) Uani 1 1 d . . . C7 C 1.04832(16) 0.17619(13) 0.42575(11) 0.0302(4) Uani 1 1 d . . . C8 C 1.08399(17) 0.08364(13) 0.42445(11) 0.0331(4) Uani 1 1 d . . . H8 H 1.1556 0.0575 0.4565 0.040 Uiso 1 1 calc R . . C9 C 0.99756(16) 0.03610(12) 0.36862(11) 0.0298(4) Uani 1 1 d . . . C10 C 1.12073(18) 0.25000(14) 0.47627(13) 0.0408(5) Uani 1 1 d . . . H10A H 1.1464 0.2972 0.4378 0.061 Uiso 1 1 calc R . . H10B H 1.1949 0.2228 0.5087 0.061 Uiso 1 1 calc R . . H10C H 1.0683 0.2782 0.5154 0.061 Uiso 1 1 calc R . . C11 C 1.00461(19) -0.06349(13) 0.34517(13) 0.0417(5) Uani 1 1 d . . . H11A H 0.9838 -0.1018 0.3923 0.063 Uiso 1 1 calc R . . H11B H 1.0894 -0.0780 0.3332 0.063 Uiso 1 1 calc R . . H11C H 0.9453 -0.0759 0.2946 0.063 Uiso 1 1 calc R . . C12 C 0.68198(19) 0.09887(12) 0.44218(11) 0.0330(4) Uani 1 1 d . . . H12 H 0.7685 0.0864 0.4560 0.040 Uiso 1 1 calc R . . C13 C 0.6106(2) 0.11120(14) 0.50740(12) 0.0420(5) Uani 1 1 d . . . H13 H 0.6466 0.1070 0.5650 0.050 Uiso 1 1 calc R . . C14 C 0.4847(2) 0.12982(15) 0.48675(14) 0.0489(5) Uani 1 1 d . . . H14 H 0.4332 0.1388 0.5305 0.059 Uiso 1 1 calc R . . C15 C 0.43422(19) 0.13535(14) 0.40322(13) 0.0412(5) Uani 1 1 d . . . H15 H 0.3478 0.1479 0.3889 0.049 Uiso 1 1 calc R . . C16 C 0.51116(16) 0.12231(12) 0.33913(11) 0.0295(4) Uani 1 1 d . . . C17 C 0.46935(16) 0.12836(11) 0.24963(11) 0.0280(4) Uani 1 1 d . . . C18 C 0.35129(17) 0.14096(12) 0.20405(12) 0.0332(4) Uani 1 1 d . . . C19 C 0.37074(18) 0.13929(12) 0.11874(12) 0.0361(4) Uani 1 1 d . . . H19 H 0.3077 0.1458 0.0718 0.043 Uiso 1 1 calc R . . C20 C 0.49689(17) 0.12659(12) 0.11359(11) 0.0308(4) Uani 1 1 d . . . C21 C 0.22659(18) 0.15105(15) 0.23565(15) 0.0453(5) Uani 1 1 d . . . H21A H 0.2093 0.0960 0.2681 0.068 Uiso 1 1 calc R . . H21B H 0.1616 0.1582 0.1873 0.068 Uiso 1 1 calc R . . H21C H 0.2275 0.2056 0.2723 0.068 Uiso 1 1 calc R . . C22 C 0.55776(19) 0.12170(15) 0.03413(12) 0.0408(5) Uani 1 1 d . . . H22A H 0.6063 0.1780 0.0285 0.061 Uiso 1 1 calc R . . H22B H 0.4936 0.1159 -0.0149 0.061 Uiso 1 1 calc R . . H22C H 0.6133 0.0680 0.0367 0.061 Uiso 1 1 calc R . . C23 C 0.6651(2) -0.08917(14) 0.17179(12) 0.0421(5) Uani 1 1 d . . . H23A H 0.7128 -0.1458 0.1658 0.063 Uiso 1 1 calc R . . H23B H 0.6716 -0.0488 0.1230 0.063 Uiso 1 1 calc R . . H23C H 0.5772 -0.1048 0.1742 0.063 Uiso 1 1 calc R . . C24 C 0.6982(2) -0.09847(13) 0.32273(13) 0.0450(5) Uani 1 1 d . . . H24A H 0.6088 -0.1063 0.3264 0.068 Uiso 1 1 calc R . . H24B H 0.7378 -0.0683 0.3744 0.068 Uiso 1 1 calc R . . H24C H 0.7366 -0.1590 0.3168 0.068 Uiso 1 1 calc R . . C25 C 0.9013(2) 0.03672(15) 0.11524(14) 0.0477(5) Uani 1 1 d . . . H25A H 0.8737 0.0276 0.0547 0.072 Uiso 1 1 calc R . . H25B H 0.8931 -0.0213 0.1457 0.072 Uiso 1 1 calc R . . H25C H 0.9889 0.0564 0.1229 0.072 Uiso 1 1 calc R . . C26 C 0.8457(2) 0.19584(14) 0.10945(13) 0.0436(5) Uani 1 1 d . . . H26A H 0.9300 0.2179 0.1297 0.065 Uiso 1 1 calc R . . H26B H 0.7841 0.2405 0.1248 0.065 Uiso 1 1 calc R . . H26C H 0.8370 0.1888 0.0476 0.065 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 0.02581(18) 0.02119(17) 0.02282(17) -0.00096(11) 0.00003(12) 0.00011(11) N1 0.0263(7) 0.0236(7) 0.0283(7) 0.0006(6) 0.0020(6) -0.0001(6) N2 0.0270(7) 0.0249(7) 0.0277(7) 0.0003(6) -0.0001(6) 0.0013(6) N3 0.0282(8) 0.0260(7) 0.0273(7) -0.0011(6) -0.0002(6) -0.0021(6) N4 0.0337(8) 0.0234(7) 0.0250(7) -0.0022(6) 0.0025(6) -0.0029(6) N5 0.0374(8) 0.0240(8) 0.0285(8) -0.0014(6) 0.0022(6) -0.0023(6) N6 0.0312(8) 0.0322(8) 0.0283(8) 0.0017(6) 0.0031(6) 0.0004(6) C1 0.0277(9) 0.0279(9) 0.0393(10) 0.0032(8) 0.0005(8) 0.0016(7) C2 0.0361(11) 0.0259(9) 0.0502(12) 0.0047(8) 0.0053(9) 0.0056(8) C3 0.0429(11) 0.0223(9) 0.0475(12) -0.0036(8) 0.0086(9) -0.0022(8) C4 0.0348(10) 0.0282(9) 0.0334(10) -0.0029(7) 0.0032(8) -0.0064(7) C5 0.0263(9) 0.0267(9) 0.0247(8) 0.0003(7) 0.0063(7) -0.0023(7) C6 0.0255(9) 0.0269(9) 0.0243(8) -0.0004(7) 0.0027(7) -0.0022(7) C7 0.0272(9) 0.0370(10) 0.0260(9) 0.0007(7) 0.0020(7) -0.0031(7) C8 0.0277(9) 0.0401(11) 0.0304(9) 0.0059(8) -0.0005(7) 0.0052(8) C9 0.0294(9) 0.0317(9) 0.0282(9) 0.0047(7) 0.0029(7) 0.0059(7) C10 0.0337(10) 0.0459(12) 0.0401(11) -0.0030(9) -0.0059(8) -0.0052(9) C11 0.0443(12) 0.0329(10) 0.0465(12) 0.0002(9) -0.0004(9) 0.0127(9) C12 0.0424(11) 0.0285(9) 0.0275(9) -0.0014(7) 0.0015(8) -0.0050(8) C13 0.0614(14) 0.0382(11) 0.0271(10) -0.0017(8) 0.0085(9) -0.0074(10) C14 0.0578(14) 0.0528(13) 0.0407(12) -0.0051(10) 0.0240(10) -0.0057(11) C15 0.0378(11) 0.0429(12) 0.0452(12) -0.0016(9) 0.0143(9) -0.0014(9) C16 0.0316(10) 0.0225(9) 0.0351(10) -0.0025(7) 0.0068(7) -0.0059(7) C17 0.0274(9) 0.0211(8) 0.0352(9) -0.0009(7) 0.0031(7) -0.0027(7) C18 0.0286(9) 0.0208(9) 0.0490(11) 0.0022(8) 0.0000(8) -0.0012(7) C19 0.0342(10) 0.0286(9) 0.0418(11) 0.0053(8) -0.0102(8) -0.0006(8) C20 0.0350(10) 0.0240(9) 0.0309(9) 0.0016(7) -0.0058(7) -0.0029(7) C21 0.0296(10) 0.0407(12) 0.0654(14) 0.0019(10) 0.0049(9) 0.0022(9) C22 0.0447(12) 0.0461(12) 0.0289(10) 0.0003(8) -0.0063(8) 0.0005(9) C23 0.0561(13) 0.0359(11) 0.0333(10) -0.0065(8) 0.0014(9) -0.0114(9) C24 0.0713(15) 0.0291(10) 0.0348(11) 0.0020(8) 0.0072(10) -0.0065(10) C25 0.0456(12) 0.0455(12) 0.0557(13) 0.0040(10) 0.0211(10) 0.0089(10) C26 0.0554(13) 0.0382(11) 0.0396(11) 0.0054(9) 0.0153(10) -0.0038(9) _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 N5 1.9081(15) . ? Ti1 N6 1.9111(15) . ? Ti1 N3 2.1025(14) . ? Ti1 N2 2.1195(14) . ? Ti1 N1 2.2559(14) . ? Ti1 N4 2.2634(15) . ? N1 C1 1.350(2) . ? N1 C5 1.358(2) . ? N2 C9 1.367(2) . ? N2 C6 1.398(2) . ? N3 C20 1.369(2) . ? N3 C17 1.397(2) . ? N4 C12 1.347(2) . ? N4 C16 1.362(2) . ? N5 C24 1.452(2) . ? N5 C23 1.456(2) . ? N6 C25 1.450(2) . ? N6 C26 1.457(2) . ? C1 C2 1.375(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 C4 1.371(3) . ? C3 H3 0.9500 . ? C4 C5 1.405(2) . ? C4 H4 0.9500 . ? C5 C6 1.437(2) . ? C6 C7 1.400(2) . ? C7 C8 1.396(3) . ? C7 C10 1.498(2) . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 C11 1.495(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.376(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.373(3) . ? C14 H14 0.9500 . ? C15 C16 1.403(3) . ? C15 H15 0.9500 . ? C16 C17 1.440(2) . ? C17 C18 1.398(2) . ? C18 C19 1.396(3) . ? C18 C21 1.500(3) . ? C19 C20 1.386(3) . ? C19 H19 0.9500 . ? C20 C22 1.494(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 N5 Ti1 N6 104.45(6) . . ? N5 Ti1 N3 94.75(6) . . ? N6 Ti1 N3 98.76(6) . . ? N5 Ti1 N2 98.96(6) . . ? N6 Ti1 N2 95.51(6) . . ? N3 Ti1 N2 157.07(6) . . ? N5 Ti1 N1 162.73(6) . . ? N6 Ti1 N1 92.37(6) . . ? N3 Ti1 N1 86.35(5) . . ? N2 Ti1 N1 75.18(5) . . ? N5 Ti1 N4 89.07(6) . . ? N6 Ti1 N4 165.75(6) . . ? N3 Ti1 N4 75.27(5) . . ? N2 Ti1 N4 86.62(5) . . ? N1 Ti1 N4 74.51(5) . . ? C1 N1 C5 119.00(15) . . ? C1 N1 Ti1 125.89(11) . . ? C5 N1 Ti1 114.89(11) . . ? C9 N2 C6 106.59(14) . . ? C9 N2 Ti1 136.73(12) . . ? C6 N2 Ti1 116.67(10) . . ? C20 N3 C17 106.50(14) . . ? C20 N3 Ti1 135.86(12) . . ? C17 N3 Ti1 117.28(11) . . ? C12 N4 C16 119.00(16) . . ? C12 N4 Ti1 126.55(13) . . ? C16 N4 Ti1 114.42(11) . . ? C24 N5 C23 110.06(15) . . ? C24 N5 Ti1 127.67(12) . . ? C23 N5 Ti1 119.22(12) . . ? C25 N6 C26 110.05(16) . . ? C25 N6 Ti1 122.63(13) . . ? C26 N6 Ti1 125.81(12) . . ? N1 C1 C2 123.30(17) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.03(17) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 119.66(17) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.11(17) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 119.90(15) . . ? N1 C5 C6 115.35(14) . . ? C4 C5 C6 124.74(15) . . ? N2 C6 C7 109.79(15) . . ? N2 C6 C5 117.83(14) . . ? C7 C6 C5 132.37(16) . . ? C8 C7 C6 105.54(15) . . ? C8 C7 C10 124.55(16) . . ? C6 C7 C10 129.88(17) . . ? C9 C8 C7 108.73(15) . . ? C9 C8 H8 125.6 . . ? C7 C8 H8 125.6 . . ? N2 C9 C8 109.34(16) . . ? N2 C9 C11 124.63(16) . . ? C8 C9 C11 125.97(16) . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N4 C12 C13 123.04(18) . . ? N4 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 118.12(19) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C15 C14 C13 120.09(19) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.52(19) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N4 C16 C15 120.21(17) . . ? N4 C16 C17 115.31(16) . . ? C15 C16 C17 124.47(17) . . ? N3 C17 C18 110.07(16) . . ? N3 C17 C16 117.55(15) . . ? C18 C17 C16 132.37(17) . . ? C19 C18 C17 105.29(17) . . ? C19 C18 C21 125.05(18) . . ? C17 C18 C21 129.63(18) . . ? C20 C19 C18 109.00(16) . . ? C20 C19 H19 125.5 . . ? C18 C19 H19 125.5 . . ? N3 C20 C19 109.14(16) . . ? N3 C20 C22 124.47(16) . . ? C19 C20 C22 126.38(16) . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 H23A 109.5 . . ? N5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N5 C24 H24A 109.5 . . ? N5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N6 C25 H25A 109.5 . . ? N6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Ti1 N1 C1 -104.8(2) . . . . ? N6 Ti1 N1 C1 88.13(15) . . . . ? N3 Ti1 N1 C1 -10.51(14) . . . . ? N2 Ti1 N1 C1 -176.80(15) . . . . ? N4 Ti1 N1 C1 -86.22(14) . . . . ? N5 Ti1 N1 C5 69.7(2) . . . . ? N6 Ti1 N1 C5 -97.41(12) . . . . ? N3 Ti1 N1 C5 163.96(12) . . . . ? N2 Ti1 N1 C5 -2.33(11) . . . . ? N4 Ti1 N1 C5 88.24(12) . . . . ? N5 Ti1 N2 C9 19.29(18) . . . . ? N6 Ti1 N2 C9 -86.31(18) . . . . ? N3 Ti1 N2 C9 145.30(17) . . . . ? N1 Ti1 N2 C9 -177.32(18) . . . . ? N4 Ti1 N2 C9 107.82(17) . . . . ? N5 Ti1 N2 C6 -162.12(12) . . . . ? N6 Ti1 N2 C6 92.27(12) . . . . ? N3 Ti1 N2 C6 -36.1(2) . . . . ? N1 Ti1 N2 C6 1.27(11) . . . . ? N4 Ti1 N2 C6 -73.60(12) . . . . ? N5 Ti1 N3 C20 -87.73(17) . . . . ? N6 Ti1 N3 C20 17.71(17) . . . . ? N2 Ti1 N3 C20 145.58(16) . . . . ? N1 Ti1 N3 C20 109.55(17) . . . . ? N4 Ti1 N3 C20 -175.51(17) . . . . ? N5 Ti1 N3 C17 84.36(12) . . . . ? N6 Ti1 N3 C17 -170.20(12) . . . . ? N2 Ti1 N3 C17 -42.3(2) . . . . ? N1 Ti1 N3 C17 -78.36(12) . . . . ? N4 Ti1 N3 C17 -3.43(11) . . . . ? N5 Ti1 N4 C12 88.39(14) . . . . ? N6 Ti1 N4 C12 -109.8(2) . . . . ? N3 Ti1 N4 C12 -176.45(15) . . . . ? N2 Ti1 N4 C12 -10.64(14) . . . . ? N1 Ti1 N4 C12 -86.19(14) . . . . ? N5 Ti1 N4 C16 -93.55(12) . . . . ? N6 Ti1 N4 C16 68.3(3) . . . . ? N3 Ti1 N4 C16 1.60(11) . . . . ? N2 Ti1 N4 C16 167.42(12) . . . . ? N1 Ti1 N4 C16 91.86(12) . . . . ? N6 Ti1 N5 C24 155.79(17) . . . . ? N3 Ti1 N5 C24 -103.89(17) . . . . ? N2 Ti1 N5 C24 57.68(17) . . . . ? N1 Ti1 N5 C24 -10.9(3) . . . . ? N4 Ti1 N5 C24 -28.75(17) . . . . ? N6 Ti1 N5 C23 -46.05(15) . . . . ? N3 Ti1 N5 C23 54.28(15) . . . . ? N2 Ti1 N5 C23 -144.16(14) . . . . ? N1 Ti1 N5 C23 147.25(18) . . . . ? N4 Ti1 N5 C23 129.41(15) . . . . ? N5 Ti1 N6 C25 -27.53(16) . . . . ? N3 Ti1 N6 C25 -124.78(15) . . . . ? N2 Ti1 N6 C25 73.21(15) . . . . ? N1 Ti1 N6 C25 148.55(15) . . . . ? N4 Ti1 N6 C25 171.2(2) . . . . ? N5 Ti1 N6 C26 167.90(15) . . . . ? N3 Ti1 N6 C26 70.65(15) . . . . ? N2 Ti1 N6 C26 -91.35(15) . . . . ? N1 Ti1 N6 C26 -16.02(15) . . . . ? N4 Ti1 N6 C26 6.7(3) . . . . ? C5 N1 C1 C2 0.4(3) . . . . ? Ti1 N1 C1 C2 174.61(14) . . . . ? N1 C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C1 N1 C5 C4 -0.7(2) . . . . ? Ti1 N1 C5 C4 -175.57(12) . . . . ? C1 N1 C5 C6 177.85(15) . . . . ? Ti1 N1 C5 C6 2.98(18) . . . . ? C3 C4 C5 N1 0.9(3) . . . . ? C3 C4 C5 C6 -177.52(17) . . . . ? C9 N2 C6 C7 -0.63(19) . . . . ? Ti1 N2 C6 C7 -179.62(11) . . . . ? C9 N2 C6 C5 178.83(15) . . . . ? Ti1 N2 C6 C5 -0.15(19) . . . . ? N1 C5 C6 N2 -2.0(2) . . . . ? C4 C5 C6 N2 176.51(16) . . . . ? N1 C5 C6 C7 177.36(17) . . . . ? C4 C5 C6 C7 -4.2(3) . . . . ? N2 C6 C7 C8 0.2(2) . . . . ? C5 C6 C7 C8 -179.17(18) . . . . ? N2 C6 C7 C10 178.18(18) . . . . ? C5 C6 C7 C10 -1.2(3) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C10 C7 C8 C9 -177.80(17) . . . . ? C6 N2 C9 C8 0.8(2) . . . . ? Ti1 N2 C9 C8 179.51(13) . . . . ? C6 N2 C9 C11 -176.52(17) . . . . ? Ti1 N2 C9 C11 2.2(3) . . . . ? C7 C8 C9 N2 -0.7(2) . . . . ? C7 C8 C9 C11 176.57(18) . . . . ? C16 N4 C12 C13 0.5(3) . . . . ? Ti1 N4 C12 C13 178.48(13) . . . . ? N4 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C12 N4 C16 C15 -0.6(2) . . . . ? Ti1 N4 C16 C15 -178.77(13) . . . . ? C12 N4 C16 C17 178.60(15) . . . . ? Ti1 N4 C16 C17 0.39(18) . . . . ? C14 C15 C16 N4 0.4(3) . . . . ? C14 C15 C16 C17 -178.65(18) . . . . ? C20 N3 C17 C18 -0.33(19) . . . . ? Ti1 N3 C17 C18 -174.59(11) . . . . ? C20 N3 C17 C16 179.20(15) . . . . ? Ti1 N3 C17 C16 4.94(19) . . . . ? N4 C16 C17 N3 -3.4(2) . . . . ? C15 C16 C17 N3 175.73(16) . . . . ? N4 C16 C17 C18 176.01(17) . . . . ? C15 C16 C17 C18 -4.9(3) . . . . ? N3 C17 C18 C19 0.41(19) . . . . ? C16 C17 C18 C19 -179.02(18) . . . . ? N3 C17 C18 C21 178.36(17) . . . . ? C16 C17 C18 C21 -1.1(3) . . . . ? C17 C18 C19 C20 -0.3(2) . . . . ? C21 C18 C19 C20 -178.41(17) . . . . ? C17 N3 C20 C19 0.11(19) . . . . ? Ti1 N3 C20 C19 172.77(12) . . . . ? C17 N3 C20 C22 179.60(17) . . . . ? Ti1 N3 C20 C22 -7.7(3) . . . . ? C18 C19 C20 N3 0.1(2) . . . . ? C18 C19 C20 C22 -179.33(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.255 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.044 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com