# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 #======================================================================= #======================================================================= data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jun-ichi Ito' _publ_contact_author_email jito@apchem.nagoya-u.ac.jp _publ_author_name Nishiyama data_ugi04b _database_code_depnum_ccdc_archive 'CCDC 673251' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34.33 N2 O5.17 Ru' _chemical_formula_weight 558.62 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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(5) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 21.191(5) _cell_length_b 21.191(5) _cell_length_c 10.778(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4192(2) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7810 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 26.11 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1738 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.563508 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29361 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.59 _reflns_number_total 6074 _reflns_number_gt 5343 _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^)+(0.0435P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2706 Friedel pairs' _refine_ls_abs_structure_Flack -0.03(3) _chemical_absolute_configuration rm _refine_ls_number_reflns 6074 _refine_ls_number_parameters 319 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.878672(15) 0.586389(14) -0.00607(3) 0.02460(8) Uani 1 1 d . . . N1 N 0.78786(15) 0.60030(16) -0.0221(3) 0.0278(7) Uani 1 1 d . . . N2 N 0.93533(16) 0.52852(16) 0.0235(3) 0.0282(7) Uani 1 1 d . . . O1 O 0.66572(14) 0.54385(14) -0.0211(3) 0.0380(7) Uani 1 1 d . . . O2 O 0.92299(16) 0.41657(15) 0.0422(3) 0.0361(7) Uani 1 1 d . . . O3 O 0.85875(17) 0.58251(14) 0.1878(3) 0.0358(7) Uani 1 1 d . . . O4 O 0.96235(14) 0.70097(14) 0.0249(3) 0.0358(7) Uani 1 1 d . . . O5 O 0.89483(15) 0.58043(16) -0.2783(3) 0.0427(8) Uani 1 1 d . . . C1 C 0.79818(18) 0.48431(18) -0.0130(4) 0.0269(7) Uani 1 1 d . . . C2 C 0.72619(18) 0.47039(19) -0.0151(4) 0.0276(8) Uani 1 1 d . . . C3 C 0.66788(19) 0.3982(2) -0.0122(4) 0.0325(8) Uani 1 1 d . . . C4 C 0.6862(2) 0.3427(2) -0.0105(5) 0.0384(10) Uani 1 1 d . . . H4 H 0.6472 0.2937 -0.0130 0.046 Uiso 1 1 calc R . . C5 C 0.7569(2) 0.35389(19) -0.0053(4) 0.0329(8) Uani 1 1 d . . . C6 C 0.81373(19) 0.42727(18) -0.0011(4) 0.0282(8) Uani 1 1 d . . . C7 C 0.5895(2) 0.3776(2) -0.0079(5) 0.0466(10) Uani 1 1 d . . . H7A H 0.5599 0.3305 -0.0491 0.070 Uiso 1 1 calc R . . H7B H 0.5830 0.4149 -0.0504 0.070 Uiso 1 1 calc R . . H7C H 0.5739 0.3740 0.0788 0.070 Uiso 1 1 calc R . . C8 C 0.7702(2) 0.2902(2) -0.0037(5) 0.0453(10) Uani 1 1 d . . . H8A H 0.8031 0.2954 -0.0717 0.068 Uiso 1 1 calc R . . H8B H 0.7238 0.2448 -0.0139 0.068 Uiso 1 1 calc R . . H8C H 0.7924 0.2893 0.0756 0.068 Uiso 1 1 calc R . . C9 C 0.72700(18) 0.5390(2) -0.0201(4) 0.0287(8) Uani 1 1 d . . . C10 C 0.6899(2) 0.6220(2) -0.0319(4) 0.0412(11) Uani 1 1 d . . . H10A H 0.6696 0.6377 0.0363 0.049 Uiso 1 1 calc R . . H10B H 0.6742 0.6324 -0.1121 0.049 Uiso 1 1 calc R . . C11 C 0.7736(2) 0.6614(2) -0.0238(4) 0.0342(9) Uani 1 1 d . . . H11 H 0.7888 0.6871 0.0578 0.041 Uiso 1 1 calc R . . C12 C 0.7947(3) 0.6830(3) -0.2568(5) 0.0575(14) Uani 1 1 d . . . H12A H 0.8006 0.6400 -0.2599 0.086 Uiso 1 1 calc R . . H12B H 0.8271 0.7188 -0.3180 0.086 Uiso 1 1 calc R . . H12C H 0.7441 0.6687 -0.2758 0.086 Uiso 1 1 calc R . . C13 C 0.8143(2) 0.7168(2) -0.1267(5) 0.0436(11) Uani 1 1 d . . . H13 H 0.8676 0.7364 -0.1139 0.052 Uiso 1 1 calc R . . C14 C 0.7997(3) 0.7804(3) -0.1145(6) 0.0703(18) Uani 1 1 d . . . H14A H 0.7492 0.7642 -0.1381 0.105 Uiso 1 1 calc R . . H14B H 0.8328 0.8203 -0.1692 0.105 Uiso 1 1 calc R . . H14C H 0.8078 0.7976 -0.0284 0.105 Uiso 1 1 calc R . . C15 C 0.8922(2) 0.4587(2) 0.0205(3) 0.0301(9) Uani 1 1 d . . . C16 C 0.9990(2) 0.4677(2) 0.0730(5) 0.0429(11) Uani 1 1 d . . . H16A H 1.0320 0.4568 0.0240 0.051 Uiso 1 1 calc R . . H16B H 1.0081 0.4647 0.1623 0.051 Uiso 1 1 calc R . . C17 C 1.0113(2) 0.5435(2) 0.0405(4) 0.0316(9) Uani 1 1 d . . . H17 H 1.0379 0.5597 -0.0403 0.038 Uiso 1 1 calc R . . C18 C 1.0162(3) 0.5811(3) 0.2650(4) 0.0557(13) Uani 1 1 d . . . H18A H 0.9640 0.5632 0.2564 0.083 Uiso 1 1 calc R . . H18B H 1.0381 0.6240 0.3192 0.083 Uiso 1 1 calc R . . H18C H 1.0235 0.5428 0.3012 0.083 Uiso 1 1 calc R . . C19 C 1.0522(2) 0.6017(2) 0.1381(4) 0.0393(10) Uani 1 1 d . . . H19 H 1.0516 0.6465 0.1109 0.047 Uiso 1 1 calc R . . C20 C 1.1328(2) 0.6209(3) 0.1427(5) 0.0569(13) Uani 1 1 d . . . H20A H 1.1586 0.6579 0.2068 0.085 Uiso 1 1 calc R . . H20B H 1.1557 0.6400 0.0619 0.085 Uiso 1 1 calc R . . H20C H 1.1353 0.5771 0.1624 0.085 Uiso 1 1 calc R . . C21 C 0.8530(3) 0.6169(3) 0.3924(5) 0.0642(15) Uani 1 1 d . . . H21A H 0.7999 0.5951 0.3885 0.096 Uiso 1 1 calc R . . H21B H 0.8736 0.6612 0.4432 0.096 Uiso 1 1 calc R . . H21C H 0.8651 0.5821 0.4294 0.096 Uiso 1 1 calc R . . C22 C 0.8843(2) 0.6361(3) 0.2624(4) 0.0404(10) Uani 1 1 d . . . C23 C 0.9361(2) 0.7078(2) 0.2362(4) 0.0459(11) Uani 1 1 d . . . H23 H 0.9488 0.7416 0.3026 0.055 Uiso 1 1 calc R . . C24 C 0.9719(2) 0.7364(2) 0.1223(4) 0.0422(11) Uani 1 1 d . . . C25 C 1.0269(3) 0.8156(3) 0.1161(6) 0.0741(19) Uani 1 1 d . . . H25A H 1.0753 0.8216 0.1020 0.111 Uiso 1 1 calc R . . H25B H 1.0268 0.8390 0.1944 0.111 Uiso 1 1 calc R . . H25C H 1.0146 0.8381 0.0477 0.111 Uiso 1 1 calc R . . C26 C 0.88914(19) 0.58438(18) -0.1727(4) 0.0259(9) Uani 1 1 d . . . O6 O 0.0116(15) 0.0156(13) 0.115(2) 0.079(8) Uiso 0.17 1 d P . . 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 0.02131(14) 0.02092(14) 0.03086(14) 0.00043(13) 0.00015(13) 0.01003(12) N1 0.0251(15) 0.0291(15) 0.0326(18) 0.0004(14) 0.0026(14) 0.0160(13) N2 0.0298(16) 0.0262(15) 0.0317(19) 0.0005(13) -0.0038(13) 0.0162(13) O1 0.0271(13) 0.0413(16) 0.0462(18) 0.0018(14) 0.0054(14) 0.0175(12) O2 0.0457(17) 0.0343(15) 0.0373(17) 0.0034(12) 0.0006(13) 0.0268(14) O3 0.0358(15) 0.0323(16) 0.035(2) 0.0000(13) 0.0034(15) 0.0141(12) O4 0.0288(14) 0.0261(13) 0.046(2) -0.0037(12) 0.0039(12) 0.0088(11) O5 0.0303(15) 0.057(2) 0.0382(19) -0.0031(15) 0.0017(13) 0.0196(14) C1 0.0297(18) 0.0255(17) 0.0219(18) 0.0006(17) 0.0012(17) 0.0111(14) C2 0.0243(17) 0.0297(18) 0.0260(19) -0.0027(17) -0.0004(17) 0.0114(15) C3 0.0279(18) 0.0334(19) 0.0223(19) -0.0006(18) -0.0011(18) 0.0051(15) C4 0.041(2) 0.0262(18) 0.0255(19) 0.0017(18) 0.003(2) 0.0003(16) C5 0.041(2) 0.0241(17) 0.0252(19) 0.0023(18) 0.002(2) 0.0096(16) C6 0.0326(19) 0.0237(17) 0.026(2) 0.0005(17) 0.0006(18) 0.0126(15) C7 0.030(2) 0.046(2) 0.047(3) 0.004(2) -0.001(2) 0.0066(18) C8 0.061(3) 0.0250(19) 0.043(3) 0.003(2) 0.004(3) 0.0169(19) C9 0.0214(17) 0.039(2) 0.024(2) 0.0010(17) 0.0021(16) 0.0138(15) C10 0.039(2) 0.044(2) 0.050(3) 0.008(2) 0.008(2) 0.028(2) C11 0.033(2) 0.039(2) 0.037(2) -0.0026(19) 0.0027(18) 0.0221(17) C12 0.072(4) 0.061(3) 0.051(3) 0.019(3) 0.015(3) 0.042(3) C13 0.036(2) 0.033(2) 0.063(3) 0.010(2) 0.010(2) 0.0187(19) C14 0.081(4) 0.039(3) 0.101(5) 0.010(3) 0.010(3) 0.038(3) C15 0.039(2) 0.035(2) 0.023(2) 0.0041(16) 0.0023(16) 0.0237(18) C16 0.044(2) 0.049(3) 0.049(3) -0.005(2) -0.012(2) 0.033(2) C17 0.031(2) 0.035(2) 0.033(2) 0.0029(17) -0.0025(16) 0.0200(18) C18 0.059(3) 0.074(4) 0.044(3) -0.009(3) -0.012(2) 0.041(3) C19 0.039(2) 0.042(2) 0.040(3) 0.0001(19) -0.0095(19) 0.0220(19) C20 0.042(3) 0.070(3) 0.057(3) -0.006(3) -0.014(2) 0.027(2) C21 0.084(4) 0.058(3) 0.040(3) -0.006(3) 0.005(3) 0.028(3) C22 0.041(2) 0.046(3) 0.038(3) -0.006(2) -0.002(2) 0.024(2) C23 0.043(3) 0.041(3) 0.050(3) -0.021(2) -0.003(2) 0.018(2) C24 0.030(2) 0.033(2) 0.060(3) -0.010(2) -0.002(2) 0.0128(18) C25 0.070(4) 0.034(3) 0.087(5) -0.021(3) 0.010(3) 0.002(3) C26 0.0192(16) 0.0261(19) 0.032(3) 0.0032(18) 0.0025(18) 0.0106(14) _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 C26 1.813(5) . ? Ru1 C1 1.976(3) . ? Ru1 N1 2.095(3) . ? Ru1 O3 2.125(3) . ? Ru1 N2 2.126(3) . ? Ru1 O4 2.201(3) . ? N1 C9 1.294(4) . ? N1 C11 1.470(5) . ? N2 C15 1.293(5) . ? N2 C17 1.488(5) . ? O1 C9 1.353(4) . ? O1 C10 1.473(5) . ? O2 C15 1.365(4) . ? O2 C16 1.461(5) . ? O3 C22 1.271(5) . ? O4 C24 1.247(5) . ? O5 C26 1.151(6) . ? C1 C2 1.402(5) . ? C1 C6 1.409(5) . ? C2 C3 1.406(5) . ? C2 C9 1.447(5) . ? C3 C4 1.412(6) . ? C3 C7 1.493(5) . ? C4 C5 1.397(6) . ? C5 C6 1.413(5) . ? C5 C8 1.510(5) . ? C6 C15 1.468(5) . ? C10 C11 1.539(5) . ? C11 C13 1.529(6) . ? C12 C13 1.534(7) . ? C13 C14 1.534(6) . ? C16 C17 1.536(5) . ? C17 C19 1.519(6) . ? C18 C19 1.519(7) . ? C19 C20 1.547(6) . ? C21 C22 1.516(6) . ? C22 C23 1.388(6) . ? C23 C24 1.411(6) . ? C24 C25 1.490(6) . ? 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 C26 Ru1 C1 89.17(16) . . ? C26 Ru1 N1 93.04(15) . . ? C1 Ru1 N1 78.46(13) . . ? C26 Ru1 O3 175.94(15) . . ? C1 Ru1 O3 87.07(14) . . ? N1 Ru1 O3 84.72(12) . . ? C26 Ru1 N2 91.37(15) . . ? C1 Ru1 N2 78.55(13) . . ? N1 Ru1 N2 156.52(11) . . ? O3 Ru1 N2 89.37(12) . . ? C26 Ru1 O4 97.80(12) . . ? C1 Ru1 O4 172.57(14) . . ? N1 Ru1 O4 98.48(11) . . ? O3 Ru1 O4 85.89(10) . . ? N2 Ru1 O4 103.76(11) . . ? C9 N1 C11 110.1(3) . . ? C9 N1 Ru1 112.5(2) . . ? C11 N1 Ru1 137.2(2) . . ? C15 N2 C17 108.6(3) . . ? C15 N2 Ru1 112.0(2) . . ? C17 N2 Ru1 139.3(2) . . ? C9 O1 C10 106.1(3) . . ? C15 O2 C16 105.4(3) . . ? C22 O3 Ru1 126.9(3) . . ? C24 O4 Ru1 126.2(3) . . ? C2 C1 C6 121.2(3) . . ? C2 C1 Ru1 118.9(3) . . ? C6 C1 Ru1 119.4(2) . . ? C1 C2 C3 120.0(3) . . ? C1 C2 C9 108.9(3) . . ? C3 C2 C9 131.0(3) . . ? C2 C3 C4 116.7(3) . . ? C2 C3 C7 124.3(4) . . ? C4 C3 C7 119.0(3) . . ? C5 C4 C3 125.3(3) . . ? C4 C5 C6 116.1(3) . . ? C4 C5 C8 120.8(3) . . ? C6 C5 C8 123.1(4) . . ? C1 C6 C5 120.3(3) . . ? C1 C6 C15 108.8(3) . . ? C5 C6 C15 130.8(3) . . ? N1 C9 O1 115.9(3) . . ? N1 C9 C2 120.9(3) . . ? O1 C9 C2 123.2(3) . . ? O1 C10 C11 105.3(3) . . ? N1 C11 C13 113.5(3) . . ? N1 C11 C10 102.2(3) . . ? C13 C11 C10 115.5(4) . . ? C11 C13 C14 109.2(4) . . ? C11 C13 C12 112.9(4) . . ? C14 C13 C12 111.2(4) . . ? N2 C15 O2 116.6(3) . . ? N2 C15 C6 121.1(3) . . ? O2 C15 C6 122.3(3) . . ? O2 C16 C17 105.7(3) . . ? N2 C17 C19 112.1(3) . . ? N2 C17 C16 101.9(3) . . ? C19 C17 C16 114.9(3) . . ? C17 C19 C18 112.9(4) . . ? C17 C19 C20 110.1(4) . . ? C18 C19 C20 112.0(4) . . ? O3 C22 C23 126.9(4) . . ? O3 C22 C21 114.3(4) . . ? C23 C22 C21 118.8(4) . . ? C22 C23 C24 127.5(4) . . ? O4 C24 C23 125.7(4) . . ? O4 C24 C25 116.1(4) . . ? C23 C24 C25 118.2(4) . . ? O5 C26 Ru1 177.5(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.638 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.089