# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yoshihiko Yamamoto' _publ_contact_author_email yamamoto@apchem.nagoya-u.ac.jp loop_ _publ_author_name Y.Yamamoto K.Yamashita H.Nishiyama data_ky51 _database_code_depnum_ccdc_archive 'CCDC 766961' #TrackingRef 'ky51.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 O2 Ru' _chemical_formula_weight 499.59 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 '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 8.2716(8) _cell_length_b 23.868(2) _cell_length_c 11.4379(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.401(2) _cell_angle_gamma 90.00 _cell_volume 2254.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6649 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.20 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.799653 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16230 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5576 _reflns_number_gt 4709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+7.4963P] 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 5576 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1451 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 Ru1 Ru 0.26364(4) 0.144669(12) 0.81637(3) 0.01888(12) Uani 1 1 d . . . C6 C 0.2141(8) 0.1559(3) 0.5265(5) 0.0535(15) Uani 1 1 d . . . H6A H 0.1427 0.1884 0.5339 0.080 Uiso 1 1 calc R . . H6B H 0.1488 0.1217 0.5194 0.080 Uiso 1 1 calc R . . H6C H 0.2760 0.1603 0.4566 0.080 Uiso 1 1 calc R . . C5 C 0.3908(6) 0.19848(18) 0.6981(4) 0.0294(9) Uani 1 1 d . . . C14 C 0.1384(5) 0.20223(17) 0.9358(4) 0.0252(8) Uani 1 1 d . . . H14 H 0.0629 0.1932 0.8729 0.030 Uiso 1 1 calc R . . C1 C 0.3293(5) 0.15200(19) 0.6337(4) 0.0278(9) Uani 1 1 d . . . C17 C 0.0721(5) 0.02168(17) 0.8263(4) 0.0232(8) Uani 1 1 d . . . C13 C 0.2119(5) 0.15670(18) 1.0003(4) 0.0247(8) Uani 1 1 d . . . C16 C 0.3387(6) 0.1575(2) 1.0997(4) 0.0317(9) Uani 1 1 d . . . H16A H 0.4217 0.1863 1.0858 0.038 Uiso 1 1 calc R . . H16B H 0.2890 0.1664 1.1741 0.038 Uiso 1 1 calc R . . O1 O 0.4102(5) 0.10345(16) 1.1056(3) 0.0435(9) Uani 1 1 d . . . C23 C 0.1705(5) 0.26308(18) 0.9592(4) 0.0289(9) Uani 1 1 d . . . C3 C 0.5044(6) 0.1178(2) 0.7786(4) 0.0356(11) Uani 1 1 d . . . C12 C 0.1880(5) 0.09876(17) 0.9689(4) 0.0244(8) Uani 1 1 d . . . C11 C 0.0903(5) 0.08021(16) 0.8700(4) 0.0231(8) Uani 1 1 d . . . C24 C 0.0991(6) 0.30061(19) 0.8787(5) 0.0347(10) Uani 1 1 d . . . H24 H 0.0353 0.2867 0.8132 0.042 Uiso 1 1 calc R . . C4 C 0.5010(6) 0.1767(2) 0.7887(4) 0.0357(11) Uani 1 1 d . . . C25 C 0.1195(7) 0.3581(2) 0.8922(5) 0.0423(12) Uani 1 1 d . . . H25 H 0.0716 0.3831 0.8355 0.051 Uiso 1 1 calc R . . C10 C 0.3587(8) 0.2587(2) 0.6711(6) 0.0501(15) Uani 1 1 d . . . H10A H 0.4367 0.2722 0.6164 0.075 Uiso 1 1 calc R . . H10B H 0.3697 0.2806 0.7436 0.075 Uiso 1 1 calc R . . H10C H 0.2486 0.2629 0.6356 0.075 Uiso 1 1 calc R . . C18 C -0.0126(6) 0.0137(2) 0.7193(4) 0.0370(11) Uani 1 1 d . . . H18 H -0.0551 0.0452 0.6773 0.044 Uiso 1 1 calc R . . C21 C 0.1034(7) -0.07900(19) 0.8393(5) 0.0390(11) Uani 1 1 d . . . H21 H 0.1429 -0.1109 0.8816 0.047 Uiso 1 1 calc R . . C22 C 0.1276(6) -0.02563(19) 0.8867(4) 0.0326(10) Uani 1 1 d . . . H22 H 0.1829 -0.0216 0.9614 0.039 Uiso 1 1 calc R . . C2 C 0.3990(6) 0.10249(18) 0.6816(4) 0.0304(9) Uani 1 1 d . . . C15 C 0.3010(6) 0.06452(19) 1.0488(4) 0.0316(9) Uani 1 1 d . . . H15A H 0.2396 0.0441 1.1071 0.038 Uiso 1 1 calc R . . H15B H 0.3607 0.0370 1.0032 0.038 Uiso 1 1 calc R . . C27 C 0.2777(6) 0.3427(2) 1.0703(5) 0.0384(11) Uani 1 1 d . . . H27 H 0.3389 0.3571 1.1365 0.046 Uiso 1 1 calc R . . C28 C 0.2576(6) 0.2847(2) 1.0569(4) 0.0338(10) Uani 1 1 d . . . H28 H 0.3038 0.2600 1.1148 0.041 Uiso 1 1 calc R . . C9 C 0.6052(8) 0.2119(4) 0.8730(6) 0.066(2) Uani 1 1 d . . . H9A H 0.6418 0.1891 0.9407 0.100 Uiso 1 1 calc R . . H9B H 0.5421 0.2438 0.8993 0.100 Uiso 1 1 calc R . . H9C H 0.6995 0.2257 0.8336 0.100 Uiso 1 1 calc R . . C26 C 0.2092(7) 0.3789(2) 0.9879(5) 0.0419(12) Uani 1 1 d . . . H26 H 0.2238 0.4181 0.9970 0.050 Uiso 1 1 calc R . . C8 C 0.6119(8) 0.0784(3) 0.8499(6) 0.067(2) Uani 1 1 d . . . H8A H 0.7159 0.0748 0.8138 0.101 Uiso 1 1 calc R . . H8B H 0.5599 0.0416 0.8529 0.101 Uiso 1 1 calc R . . H8C H 0.6301 0.0932 0.9296 0.101 Uiso 1 1 calc R . . C20 C 0.0229(7) -0.0858(2) 0.7319(5) 0.0383(11) Uani 1 1 d . . . H20 H 0.0081 -0.1221 0.6989 0.046 Uiso 1 1 calc R . . C19 C -0.0363(7) -0.0391(2) 0.6728(5) 0.0447(13) Uani 1 1 d . . . H19 H -0.0941 -0.0434 0.5990 0.054 Uiso 1 1 calc R . . C7 C 0.3731(8) 0.0445(2) 0.6310(6) 0.0542(16) Uani 1 1 d . . . H7A H 0.3839 0.0167 0.6940 0.081 Uiso 1 1 calc R . . H7B H 0.4542 0.0371 0.5738 0.081 Uiso 1 1 calc R . . H7C H 0.2644 0.0421 0.5922 0.081 Uiso 1 1 calc R . . O2 O 0.0116(6) 0.1193(2) 0.8072(4) 0.0617(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.01794(17) 0.01905(17) 0.01953(17) -0.00004(11) 0.00006(11) -0.00020(11) C6 0.058(4) 0.077(4) 0.025(3) 0.005(3) 0.000(2) 0.000(3) C5 0.035(2) 0.024(2) 0.031(2) 0.0023(17) 0.0150(18) 0.0016(17) C14 0.0219(19) 0.0259(19) 0.028(2) -0.0056(16) 0.0026(16) -0.0003(15) C1 0.023(2) 0.038(2) 0.023(2) -0.0010(17) 0.0060(16) 0.0003(17) C17 0.0226(19) 0.0220(18) 0.0254(19) 0.0001(15) 0.0044(15) -0.0009(15) C13 0.025(2) 0.028(2) 0.0206(18) -0.0019(15) 0.0029(15) -0.0023(16) C16 0.030(2) 0.041(2) 0.024(2) -0.0009(18) 0.0005(17) -0.0016(19) O1 0.044(2) 0.0416(19) 0.042(2) -0.0007(16) -0.0195(16) 0.0010(16) C23 0.030(2) 0.026(2) 0.032(2) -0.0075(17) 0.0105(17) -0.0020(17) C3 0.025(2) 0.042(3) 0.041(3) 0.016(2) 0.0092(19) 0.0074(19) C12 0.025(2) 0.026(2) 0.0224(18) 0.0020(15) 0.0022(15) -0.0017(16) C11 0.0215(19) 0.0210(18) 0.0267(19) 0.0045(15) 0.0009(15) -0.0015(14) C24 0.035(2) 0.028(2) 0.042(3) -0.0062(19) 0.006(2) 0.0048(18) C4 0.025(2) 0.054(3) 0.028(2) -0.007(2) 0.0061(17) -0.012(2) C25 0.045(3) 0.030(2) 0.053(3) -0.002(2) 0.012(2) 0.006(2) C10 0.067(4) 0.026(2) 0.061(4) 0.005(2) 0.034(3) 0.002(2) C18 0.047(3) 0.026(2) 0.037(2) 0.0012(19) -0.010(2) -0.004(2) C21 0.050(3) 0.023(2) 0.044(3) 0.0007(19) 0.000(2) 0.004(2) C22 0.037(3) 0.027(2) 0.033(2) 0.0009(18) -0.0035(19) 0.0003(18) C2 0.030(2) 0.026(2) 0.037(2) -0.0011(18) 0.0156(18) 0.0000(17) C15 0.036(2) 0.032(2) 0.026(2) 0.0041(17) -0.0040(17) -0.0002(19) C27 0.040(3) 0.034(2) 0.042(3) -0.015(2) 0.011(2) -0.011(2) C28 0.039(3) 0.030(2) 0.033(2) -0.0071(18) 0.0072(19) -0.0050(19) C9 0.046(3) 0.107(6) 0.047(3) -0.023(4) 0.006(3) -0.039(4) C26 0.043(3) 0.025(2) 0.060(3) -0.011(2) 0.024(3) -0.007(2) C8 0.039(3) 0.096(5) 0.068(4) 0.039(4) 0.015(3) 0.032(3) C20 0.048(3) 0.025(2) 0.043(3) -0.0099(19) 0.007(2) -0.003(2) C19 0.059(3) 0.036(3) 0.038(3) -0.007(2) -0.011(2) -0.005(2) C7 0.071(4) 0.029(2) 0.066(4) -0.013(3) 0.034(3) -0.002(3) O2 0.062(3) 0.056(3) 0.066(3) 0.004(2) -0.004(2) 0.002(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 Ru1 C4 2.148(5) . ? Ru1 C3 2.160(5) . ? Ru1 O2 2.167(5) . ? Ru1 C5 2.180(4) . ? Ru1 C12 2.183(4) . ? Ru1 C13 2.190(4) . ? Ru1 C1 2.197(4) . ? Ru1 C2 2.202(4) . ? Ru1 C11 2.215(4) . ? Ru1 C14 2.235(4) . ? C6 C1 1.510(7) . ? C5 C1 1.410(6) . ? C5 C4 1.436(7) . ? C5 C10 1.491(6) . ? C14 C13 1.428(6) . ? C14 C23 1.498(6) . ? C1 C2 1.411(6) . ? C17 C18 1.387(6) . ? C17 C22 1.387(6) . ? C17 C11 1.488(5) . ? C13 C12 1.439(6) . ? C13 C16 1.501(6) . ? C16 O1 1.419(6) . ? O1 C15 1.425(6) . ? C23 C24 1.391(7) . ? C23 C28 1.392(6) . ? C3 C4 1.410(8) . ? C3 C2 1.418(7) . ? C3 C8 1.501(7) . ? C12 C11 1.421(6) . ? C12 C15 1.509(6) . ? C11 O2 1.325(6) . ? C24 C25 1.391(7) . ? C4 C9 1.510(7) . ? C25 C26 1.377(8) . ? C18 C19 1.377(7) . ? C21 C20 1.371(7) . ? C21 C22 1.394(6) . ? C2 C7 1.511(7) . ? C27 C26 1.374(8) . ? C27 C28 1.402(7) . ? C20 C19 1.379(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 C4 Ru1 C3 38.2(2) . . ? C4 Ru1 O2 167.76(19) . . ? C3 Ru1 O2 143.4(2) . . ? C4 Ru1 C5 38.74(19) . . ? C3 Ru1 C5 64.29(17) . . ? O2 Ru1 C5 129.23(18) . . ? C4 Ru1 C12 127.19(17) . . ? C3 Ru1 C12 108.81(17) . . ? O2 Ru1 C12 65.04(17) . . ? C5 Ru1 C12 164.40(17) . . ? C4 Ru1 C13 109.11(17) . . ? C3 Ru1 C13 117.77(18) . . ? O2 Ru1 C13 80.86(17) . . ? C5 Ru1 C13 130.35(16) . . ? C12 Ru1 C13 38.43(15) . . ? C4 Ru1 C1 63.38(17) . . ? C3 Ru1 C1 63.30(17) . . ? O2 Ru1 C1 105.49(18) . . ? C5 Ru1 C1 37.59(17) . . ? C12 Ru1 C1 154.01(16) . . ? C13 Ru1 C1 167.54(17) . . ? C4 Ru1 C2 63.40(18) . . ? C3 Ru1 C2 37.93(19) . . ? O2 Ru1 C2 111.45(18) . . ? C5 Ru1 C2 63.32(16) . . ? C12 Ru1 C2 120.79(17) . . ? C13 Ru1 C2 150.32(17) . . ? C1 Ru1 C2 37.43(16) . . ? C4 Ru1 C11 154.26(18) . . ? C3 Ru1 C11 117.99(17) . . ? O2 Ru1 C11 35.17(16) . . ? C5 Ru1 C11 157.71(17) . . ? C12 Ru1 C11 37.70(15) . . ? C13 Ru1 C11 70.02(16) . . ? C1 Ru1 C11 121.30(16) . . ? C2 Ru1 C11 103.94(16) . . ? C4 Ru1 C14 109.40(17) . . ? C3 Ru1 C14 140.42(19) . . ? O2 Ru1 C14 73.87(17) . . ? C5 Ru1 C14 105.97(16) . . ? C12 Ru1 C14 69.80(16) . . ? C13 Ru1 C14 37.65(16) . . ? C1 Ru1 C14 133.01(16) . . ? C2 Ru1 C14 169.24(16) . . ? C11 Ru1 C14 85.78(15) . . ? C1 C5 C4 106.6(4) . . ? C1 C5 C10 126.6(5) . . ? C4 C5 C10 126.6(5) . . ? C1 C5 Ru1 71.9(2) . . ? C4 C5 Ru1 69.4(2) . . ? C10 C5 Ru1 127.6(3) . . ? C13 C14 C23 125.5(4) . . ? C13 C14 Ru1 69.5(2) . . ? C23 C14 Ru1 128.4(3) . . ? C5 C1 C2 109.2(4) . . ? C5 C1 C6 124.5(5) . . ? C2 C1 C6 126.2(5) . . ? C5 C1 Ru1 70.6(2) . . ? C2 C1 Ru1 71.5(2) . . ? C6 C1 Ru1 126.7(4) . . ? C18 C17 C22 117.5(4) . . ? C18 C17 C11 117.5(4) . . ? C22 C17 C11 125.0(4) . . ? C14 C13 C12 123.7(4) . . ? C14 C13 C16 129.6(4) . . ? C12 C13 C16 106.3(4) . . ? C14 C13 Ru1 72.9(2) . . ? C12 C13 Ru1 70.5(2) . . ? C16 C13 Ru1 124.2(3) . . ? O1 C16 C13 107.1(4) . . ? C16 O1 C15 108.7(4) . . ? C24 C23 C28 118.1(4) . . ? C24 C23 C14 116.3(4) . . ? C28 C23 C14 125.5(4) . . ? C4 C3 C2 107.9(4) . . ? C4 C3 C8 126.4(6) . . ? C2 C3 C8 125.5(5) . . ? C4 C3 Ru1 70.4(3) . . ? C2 C3 Ru1 72.6(3) . . ? C8 C3 Ru1 126.9(4) . . ? C11 C12 C13 124.1(4) . . ? C11 C12 C15 128.0(4) . . ? C13 C12 C15 107.3(4) . . ? C11 C12 Ru1 72.4(2) . . ? C13 C12 Ru1 71.0(2) . . ? C15 C12 Ru1 124.0(3) . . ? O2 C11 C12 116.8(4) . . ? O2 C11 C17 116.2(4) . . ? C12 C11 C17 126.9(4) . . ? O2 C11 Ru1 70.5(3) . . ? C12 C11 Ru1 69.9(2) . . ? C17 C11 Ru1 127.8(3) . . ? C25 C24 C23 121.2(5) . . ? C3 C4 C5 108.5(4) . . ? C3 C4 C9 126.4(5) . . ? C5 C4 C9 125.0(5) . . ? C3 C4 Ru1 71.4(3) . . ? C5 C4 Ru1 71.8(3) . . ? C9 C4 Ru1 126.6(4) . . ? C26 C25 C24 120.0(5) . . ? C19 C18 C17 121.4(5) . . ? C20 C21 C22 120.5(5) . . ? C17 C22 C21 120.9(4) . . ? C1 C2 C3 107.8(4) . . ? C1 C2 C7 124.9(5) . . ? C3 C2 C7 127.1(5) . . ? C1 C2 Ru1 71.1(2) . . ? C3 C2 Ru1 69.4(3) . . ? C7 C2 Ru1 128.4(3) . . ? O1 C15 C12 106.0(4) . . ? C26 C27 C28 120.2(5) . . ? C23 C28 C27 120.4(5) . . ? C27 C26 C25 120.0(5) . . ? C21 C20 C19 118.8(4) . . ? C18 C19 C20 120.8(5) . . ? C11 O2 Ru1 74.4(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 5.061 _refine_diff_density_min -1.023 _refine_diff_density_rms 0.141