# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_General _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_date 2006-05-25 _audit_creation_method 'by CrystalStructure 3.7.0' _audit_update_record ? _publ_contact_author_name 'Prof. Motoi Kawatsura' _publ_contact_author_email KAWATSUR@CHEM.TOTTORI-U.AC.JP _publ_requested_category CM _publ_requested_coeditor_name ? _publ_section_title ; Ruthenium-catalysed linear-selective allylic alkylation of allyl acetates ; loop_ _publ_author_name 'Motoi Kawatsura' 'Fumio Ata' 'Shuichi Hayase' 'Toshiyuki Itoh' 'Hidemitsu Uno' 'Shohei Wada' #============================================================================== data_Ata _database_code_depnum_ccdc_archive 'CCDC 622374' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C34 H31 O6 P Ru ' _chemical_formula_moiety 'C30 H23 O4 P Ru, C4 H8 O2 ' _chemical_formula_weight 667.66 _chemical_melting_point ? #============================================================================== 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' #------------------------------------------------------------------------------ _cell_length_a 12.846(2) _cell_length_b 16.061(3) _cell_length_c 14.566(4) _cell_angle_alpha 90.000 _cell_angle_beta 90.612(11) _cell_angle_gamma 90.000 _cell_volume 3005.1(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 15515 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.3 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368.00 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.402 _exptl_absorpt_correction_T_max 0.940 _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 25583 _diffrn_reflns_av_R_equivalents 0.1253 _diffrn_reflns_av_sigmaI/netI 0.0804 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.38 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.982 #============================================================================== # REFINEMENT DATA _reflns_number_total 6696 _reflns_number_gt 4775 _reflns_threshold_expression >2sigma(I) _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. Hydrogen atoms at the coordinated allylic moiety are placed by the differential Fourier map with 1.2 x Beq values of the attached carbons. ; _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^)+(0.0757P)^2^+4.3584P] 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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 6696 _refine_ls_number_parameters 381 _refine_ls_number_restraints 605 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.1735 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.925 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.086 #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL-97 _computing_publication_material 'CrystalStructure 3.7.0' _computing_molecular_graphics ? #============================================================================== 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 0.18098(3) 0.19382(2) 0.74017(3) 0.05089(15) Uani 1 1 d U . . P1 P 0.17774(9) 0.04899(8) 0.75346(9) 0.0481(3) Uani 1 1 d U . . O1 O 0.2370(3) 0.1653(2) 0.6074(2) 0.0585(8) Uani 1 1 d U . . O2 O 0.3115(3) 0.1012(2) 0.4907(3) 0.0643(9) Uani 1 1 d U . . O3 O 0.0939(4) 0.2179(3) 0.9278(3) 0.0812(13) Uani 1 1 d U . . O4 O -0.0327(4) 0.2225(3) 0.6528(4) 0.0970(16) Uani 1 1 d U . . O5 O 0.6849(10) 0.2148(8) 0.6765(10) 0.222(4) Uani 1 1 d DU . . O6 O 0.7670(8) 0.1148(7) 0.7510(8) 0.175(3) Uani 1 1 d U . . C1 C 0.2342(5) 0.3212(3) 0.7033(4) 0.0631(12) Uani 1 1 d U . . H1A H 0.1814 0.3633 0.6982 0.076 Uiso 1 1 calc . . . H1B H 0.2521 0.3098 0.6419 0.076 Uiso 1 1 calc . . . C2 C 0.2934(4) 0.2945(3) 0.7797(4) 0.0615(11) Uani 1 1 d U . . H2 H 0.2786 0.3186 0.8381 0.074 Uiso 1 1 calc . . . C3 C 0.3525(4) 0.2202(4) 0.7757(4) 0.0591(11) Uani 1 1 d U . . H3 H 0.3702 0.2061 0.7130 0.071 Uiso 1 1 calc . . . C4 C 0.4115(4) 0.1866(4) 0.8536(4) 0.0609(11) Uani 1 1 d U . . C5 C 0.3969(5) 0.2108(4) 0.9446(4) 0.0690(13) Uani 1 1 d U . . H5 H 0.3469 0.2525 0.9585 0.083 Uiso 1 1 calc R . . C6 C 0.4544(5) 0.1747(5) 1.0147(5) 0.0802(15) Uani 1 1 d U . . H6 H 0.4445 0.1928 1.0761 0.096 Uiso 1 1 calc R . . C7 C 0.5256(6) 0.1132(5) 0.9972(5) 0.0924(18) Uani 1 1 d U . . H7 H 0.5627 0.0873 1.0463 0.111 Uiso 1 1 calc R . . C8 C 0.5426(6) 0.0896(5) 0.9084(5) 0.0937(19) Uani 1 1 d U . . H8 H 0.5931 0.0481 0.8955 0.112 Uiso 1 1 calc R . . C9 C 0.4865(5) 0.1259(4) 0.8368(5) 0.0736(14) Uani 1 1 d U . . H9 H 0.4995 0.1091 0.7754 0.088 Uiso 1 1 calc R . . C10 C 0.3028(4) 0.0105(3) 0.7146(3) 0.0523(10) Uani 1 1 d U . . C11 C 0.3543(4) -0.0527(4) 0.7620(4) 0.0609(12) Uani 1 1 d U . . H11 H 0.3232 -0.0769 0.8145 0.073 Uiso 1 1 calc R . . C12 C 0.4516(5) -0.0809(4) 0.7329(4) 0.0731(14) Uani 1 1 d U . . H12 H 0.4865 -0.1241 0.7653 0.088 Uiso 1 1 calc R . . C13 C 0.4958(5) -0.0459(5) 0.6578(4) 0.0754(15) Uani 1 1 d U . . H13 H 0.5624 -0.0643 0.6387 0.090 Uiso 1 1 calc R . . C14 C 0.4451(4) 0.0161(4) 0.6089(4) 0.0671(13) Uani 1 1 d U . . H14 H 0.4769 0.0392 0.5561 0.081 Uiso 1 1 calc R . . C15 C 0.3481(4) 0.0452(3) 0.6359(3) 0.0543(10) Uani 1 1 d U . . C16 C 0.2951(4) 0.1079(3) 0.5736(3) 0.0545(10) Uani 1 1 d U . . C17 C 0.1597(4) 0.0020(3) 0.8657(4) 0.0539(10) Uani 1 1 d U . . C18 C 0.2125(4) 0.0359(3) 0.9401(4) 0.0596(11) Uani 1 1 d U . . H18 H 0.2569 0.0825 0.9315 0.072 Uiso 1 1 calc R . . C19 C 0.2013(5) 0.0029(4) 1.0262(4) 0.0712(13) Uani 1 1 d U . . H19 H 0.2382 0.0262 1.0769 0.085 Uiso 1 1 calc R . . C20 C 0.1368(6) -0.0638(4) 1.0392(5) 0.0817(16) Uani 1 1 d U . . H20 H 0.1283 -0.0860 1.0991 0.098 Uiso 1 1 calc R . . C21 C 0.0838(6) -0.0990(4) 0.9658(5) 0.0820(16) Uani 1 1 d U . . H21 H 0.0396 -0.1457 0.9750 0.098 Uiso 1 1 calc R . . C22 C 0.0955(5) -0.0660(4) 0.8795(4) 0.0690(13) Uani 1 1 d U . . H22 H 0.0592 -0.0900 0.8289 0.083 Uiso 1 1 calc R . . C23 C 0.0837(4) -0.0035(3) 0.6797(4) 0.0575(11) Uani 1 1 d U . . C24 C 0.1121(5) -0.0627(4) 0.6167(4) 0.0689(13) Uani 1 1 d U . . H24 H 0.1835 -0.0767 0.6099 0.083 Uiso 1 1 calc R . . C25 C 0.0372(6) -0.1024(4) 0.5628(5) 0.0809(16) Uani 1 1 d U . . H25 H 0.0579 -0.1422 0.5183 0.097 Uiso 1 1 calc R . . C26 C -0.0646(5) -0.0848(4) 0.5732(5) 0.0818(16) Uani 1 1 d U . . H26 H -0.1151 -0.1134 0.5370 0.098 Uiso 1 1 calc R . . C27 C -0.0959(5) -0.0268(4) 0.6348(5) 0.0762(15) Uani 1 1 d U . . H27 H -0.1677 -0.0140 0.6406 0.091 Uiso 1 1 calc R . . C28 C -0.0229(4) 0.0136(4) 0.6890(5) 0.0688(13) Uani 1 1 d U . . H28 H -0.0450 0.0533 0.7330 0.083 Uiso 1 1 calc R . . C29 C 0.1278(4) 0.2108(3) 0.8565(4) 0.0607(12) Uani 1 1 d U . . C30 C 0.0464(5) 0.2087(3) 0.6848(5) 0.0693(14) Uani 1 1 d U . . C31 C 0.7312(17) 0.1848(12) 0.7509(16) 0.195(4) Uani 1 1 d U . . C32 C 0.7415(14) 0.2416(9) 0.8231(11) 0.202(5) Uani 1 1 d U . . H32A H 0.7311 0.2128 0.8816 0.303 Uiso 1 1 calc R . . H32B H 0.6893 0.2857 0.8160 0.303 Uiso 1 1 calc R . . H32C H 0.8113 0.2661 0.8224 0.303 Uiso 1 1 calc R . . C33 C 0.6568(19) 0.1481(12) 0.6089(13) 0.245(5) Uani 1 1 d DU . . H33A H 0.6950 0.0961 0.6231 0.294 Uiso 1 1 calc R . . H33B H 0.5812 0.1366 0.6102 0.294 Uiso 1 1 calc R . . C34 C 0.6861(19) 0.1795(13) 0.5213(14) 0.274(8) Uani 1 1 d DU . . H34A H 0.6298 0.2141 0.4962 0.411 Uiso 1 1 calc R . . H34B H 0.6991 0.1328 0.4795 0.411 Uiso 1 1 calc R . . H34C H 0.7495 0.2130 0.5278 0.411 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 Ru1 0.0520(2) 0.0476(2) 0.0531(2) 0.00085(17) 0.00080(16) 0.00075(17) P1 0.0478(6) 0.0475(6) 0.0489(6) -0.0004(5) -0.0035(5) 0.0004(5) O1 0.067(2) 0.0597(19) 0.0484(18) 0.0033(15) -0.0032(15) 0.0035(17) O2 0.074(2) 0.075(2) 0.0436(18) 0.0000(17) 0.0011(17) 0.0013(19) O3 0.105(3) 0.060(2) 0.079(3) -0.004(2) 0.040(3) 0.001(2) O4 0.072(3) 0.088(3) 0.130(5) 0.014(3) -0.031(3) 0.017(2) O5 0.254(9) 0.187(8) 0.223(9) 0.013(7) -0.086(7) 0.003(7) O6 0.177(7) 0.171(7) 0.177(8) -0.001(6) 0.000(6) 0.027(6) C1 0.071(3) 0.049(2) 0.069(3) 0.004(2) 0.011(2) -0.005(2) C2 0.070(3) 0.051(2) 0.064(3) -0.002(2) 0.009(2) -0.014(2) C3 0.056(2) 0.063(3) 0.058(3) -0.005(2) 0.004(2) -0.008(2) C4 0.057(2) 0.072(3) 0.053(2) -0.007(2) 0.003(2) -0.008(2) C5 0.077(3) 0.075(3) 0.055(3) -0.009(2) 0.001(2) -0.007(3) C6 0.087(4) 0.098(4) 0.055(3) -0.009(3) -0.009(3) -0.004(3) C7 0.087(4) 0.119(5) 0.071(3) -0.004(3) -0.023(3) 0.013(3) C8 0.082(4) 0.118(5) 0.081(4) -0.013(4) -0.017(3) 0.024(3) C9 0.064(3) 0.096(4) 0.060(3) -0.014(3) -0.007(2) 0.008(3) C10 0.055(2) 0.057(2) 0.045(2) -0.0070(19) -0.0054(18) 0.005(2) C11 0.067(3) 0.071(3) 0.045(2) -0.004(2) -0.003(2) 0.015(2) C12 0.070(3) 0.092(4) 0.057(3) -0.005(3) -0.008(2) 0.030(3) C13 0.065(3) 0.100(4) 0.061(3) -0.006(3) 0.003(2) 0.027(3) C14 0.064(3) 0.089(3) 0.048(3) -0.009(2) -0.002(2) 0.012(3) C15 0.058(2) 0.063(3) 0.042(2) -0.0082(19) -0.0059(18) 0.004(2) C16 0.055(2) 0.063(3) 0.045(2) 0.000(2) -0.0049(19) -0.002(2) C17 0.057(2) 0.054(2) 0.052(2) 0.0024(19) 0.0037(19) 0.004(2) C18 0.067(3) 0.060(3) 0.053(2) -0.001(2) -0.001(2) 0.007(2) C19 0.086(3) 0.074(3) 0.053(3) -0.003(2) 0.004(3) 0.017(3) C20 0.106(4) 0.084(4) 0.056(3) 0.011(3) 0.020(3) 0.011(3) C21 0.097(4) 0.082(4) 0.067(3) 0.015(3) 0.015(3) -0.011(3) C22 0.077(3) 0.066(3) 0.064(3) 0.007(2) 0.004(3) -0.006(3) C23 0.058(2) 0.053(2) 0.061(3) 0.010(2) -0.011(2) -0.008(2) C24 0.075(3) 0.059(3) 0.072(3) -0.005(2) -0.017(3) -0.003(2) C25 0.096(4) 0.063(3) 0.084(4) -0.003(3) -0.027(3) -0.006(3) C26 0.089(3) 0.064(3) 0.091(4) 0.014(3) -0.041(3) -0.017(3) C27 0.066(3) 0.068(3) 0.094(4) 0.023(3) -0.026(3) -0.011(3) C28 0.059(2) 0.066(3) 0.081(3) 0.012(3) -0.017(2) -0.007(2) C29 0.063(3) 0.044(2) 0.075(3) 0.002(2) 0.013(2) 0.001(2) C30 0.064(3) 0.060(3) 0.085(4) 0.005(3) -0.004(3) 0.003(2) C31 0.227(9) 0.148(8) 0.208(10) 0.015(7) -0.061(8) 0.011(7) C32 0.270(14) 0.121(8) 0.213(12) 0.012(7) -0.073(12) 0.017(10) C33 0.290(11) 0.212(10) 0.231(11) -0.006(9) -0.071(10) -0.008(10) C34 0.318(17) 0.253(16) 0.251(13) -0.038(13) 0.028(16) 0.009(15) _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 C29 1.853(6) . ? Ru1 C30 1.914(6) . ? Ru1 O1 2.121(4) . ? Ru1 C1 2.224(5) . ? Ru1 C2 2.239(5) . ? Ru1 C3 2.298(5) . ? Ru1 P1 2.3345(14) . ? P1 C23 1.815(5) . ? P1 C10 1.817(5) . ? P1 C17 1.818(5) . ? O1 C16 1.287(6) . ? O2 C16 1.231(6) . ? O3 C29 1.137(7) . ? O4 C30 1.136(7) . ? O5 C31 1.32(2) . ? O5 C33 1.496(15) . ? O6 C31 1.215(18) . ? C1 C2 1.408(9) . ? C1 H1A 0.960 . ? C1 H1B 0.944 . ? C2 C3 1.416(8) . ? C2 H2 0.956 . ? C3 C4 1.460(8) . ? C3 H3 0.970 . ? C4 C9 1.393(8) . ? C4 C5 1.397(8) . ? C5 C6 1.381(9) . ? C5 H5 0.9500 . ? C6 C7 1.372(10) . ? C6 H6 0.9500 . ? C7 C8 1.368(11) . ? C7 H7 0.9500 . ? C8 C9 1.390(10) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.390(7) . ? C10 C15 1.406(7) . ? C11 C12 1.400(8) . ? C11 H11 0.9500 . ? C12 C13 1.358(9) . ? C12 H12 0.9500 . ? C13 C14 1.384(9) . ? C13 H13 0.9500 . ? C14 C15 1.391(7) . ? C14 H14 0.9500 . ? C15 C16 1.513(7) . ? C17 C18 1.384(8) . ? C17 C22 1.385(8) . ? C18 C19 1.371(8) . ? C18 H18 0.9500 . ? C19 C20 1.368(9) . ? C19 H19 0.9500 . ? C20 C21 1.382(10) . ? C20 H20 0.9500 . ? C21 C22 1.374(9) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.374(8) . ? C23 C28 1.405(8) . ? C24 C25 1.390(9) . ? C24 H24 0.9500 . ? C25 C26 1.349(10) . ? C25 H25 0.9500 . ? C26 C27 1.357(10) . ? C26 H26 0.9500 . ? C27 C28 1.381(8) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C31 C32 1.40(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.426(16) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 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 C29 Ru1 C30 91.5(3) . . ? C29 Ru1 O1 175.71(18) . . ? C30 Ru1 O1 87.5(2) . . ? C29 Ru1 C1 101.7(2) . . ? C30 Ru1 C1 93.6(2) . . ? O1 Ru1 C1 82.55(18) . . ? C29 Ru1 C2 84.4(2) . . ? C30 Ru1 C2 126.5(2) . . ? O1 Ru1 C2 99.56(18) . . ? C1 Ru1 C2 36.8(2) . . ? C29 Ru1 C3 97.4(2) . . ? C30 Ru1 C3 158.6(2) . . ? O1 Ru1 C3 84.90(17) . . ? C1 Ru1 C3 65.7(2) . . ? C2 Ru1 C3 36.3(2) . . ? C29 Ru1 P1 93.64(16) . . ? C30 Ru1 P1 98.17(17) . . ? O1 Ru1 P1 82.35(10) . . ? C1 Ru1 P1 160.41(15) . . ? C2 Ru1 P1 135.25(16) . . ? C3 Ru1 P1 100.56(15) . . ? C23 P1 C10 104.0(2) . . ? C23 P1 C17 104.4(2) . . ? C10 P1 C17 105.1(2) . . ? C23 P1 Ru1 115.20(17) . . ? C10 P1 Ru1 107.25(17) . . ? C17 P1 Ru1 119.38(17) . . ? C16 O1 Ru1 135.1(3) . . ? C31 O5 C33 112.4(15) . . ? C2 C1 Ru1 72.2(3) . . ? C2 C1 H1A 130.6 . . ? Ru1 C1 H1A 116.6 . . ? C2 C1 H1B 123.7 . . ? Ru1 C1 H1B 97.4 . . ? H1A C1 H1B 104.0 . . ? C1 C2 C3 120.7(5) . . ? C1 C2 Ru1 71.1(3) . . ? C3 C2 Ru1 74.1(3) . . ? C1 C2 H2 118.0 . . ? C3 C2 H2 119.3 . . ? Ru1 C2 H2 112.8 . . ? C2 C3 C4 123.7(5) . . ? C2 C3 Ru1 69.6(3) . . ? C4 C3 Ru1 126.5(4) . . ? C2 C3 H3 111.5 . . ? C4 C3 H3 121.3 . . ? Ru1 C3 H3 88.7 . . ? C9 C4 C5 117.5(6) . . ? C9 C4 C3 118.5(5) . . ? C5 C4 C3 124.1(5) . . ? C6 C5 C4 120.6(6) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 121.2(6) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 119.2(7) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.5(7) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 121.0(6) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? C11 C10 C15 119.7(4) . . ? C11 C10 P1 120.7(4) . . ? C15 C10 P1 119.6(4) . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.5(6) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.9(5) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 120.9(6) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C10 118.5(5) . . ? C14 C15 C16 116.9(5) . . ? C10 C15 C16 124.5(4) . . ? O2 C16 O1 122.9(5) . . ? O2 C16 C15 116.7(5) . . ? O1 C16 C15 120.4(4) . . ? C18 C17 C22 118.9(5) . . ? C18 C17 P1 118.4(4) . . ? C22 C17 P1 122.6(4) . . ? C19 C18 C17 120.6(5) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 119.9(6) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.6(6) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 119.4(6) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C17 120.6(6) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C24 C23 C28 117.7(5) . . ? C24 C23 P1 122.5(4) . . ? C28 C23 P1 119.7(4) . . ? C23 C24 C25 120.5(6) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 120.4(7) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 120.8(6) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C26 C27 C28 119.7(6) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C23 120.7(6) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? O3 C29 Ru1 177.2(5) . . ? O4 C30 Ru1 175.8(5) . . ? O6 C31 O5 120(2) . . ? O6 C31 C32 124.8(19) . . ? O5 C31 C32 114.6(17) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 O5 105.8(18) . . ? C34 C33 H33A 110.6 . . ? O5 C33 H33A 110.6 . . ? C34 C33 H33B 110.6 . . ? O5 C33 H33B 110.6 . . ? H33A C33 H33B 108.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 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 C29 Ru1 P1 C23 111.6(3) . . . . ? C30 Ru1 P1 C23 19.6(3) . . . . ? O1 Ru1 P1 C23 -66.8(2) . . . . ? C1 Ru1 P1 C23 -106.7(6) . . . . ? C2 Ru1 P1 C23 -162.7(3) . . . . ? C3 Ru1 P1 C23 -150.1(2) . . . . ? C29 Ru1 P1 C10 -133.1(3) . . . . ? C30 Ru1 P1 C10 134.8(3) . . . . ? O1 Ru1 P1 C10 48.4(2) . . . . ? C1 Ru1 P1 C10 8.6(6) . . . . ? C2 Ru1 P1 C10 -47.4(3) . . . . ? C3 Ru1 P1 C10 -34.9(2) . . . . ? C29 Ru1 P1 C17 -13.9(3) . . . . ? C30 Ru1 P1 C17 -106.0(3) . . . . ? O1 Ru1 P1 C17 167.6(2) . . . . ? C1 Ru1 P1 C17 127.8(6) . . . . ? C2 Ru1 P1 C17 71.8(3) . . . . ? C3 Ru1 P1 C17 84.3(2) . . . . ? C30 Ru1 O1 C16 -133.1(5) . . . . ? C1 Ru1 O1 C16 132.9(5) . . . . ? C2 Ru1 O1 C16 100.2(5) . . . . ? C3 Ru1 O1 C16 66.8(5) . . . . ? P1 Ru1 O1 C16 -34.6(5) . . . . ? C29 Ru1 C1 C2 63.6(4) . . . . ? C30 Ru1 C1 C2 155.9(4) . . . . ? O1 Ru1 C1 C2 -117.0(3) . . . . ? C3 Ru1 C1 C2 -29.3(3) . . . . ? P1 Ru1 C1 C2 -77.2(6) . . . . ? Ru1 C1 C2 C3 57.3(4) . . . . ? C29 Ru1 C2 C1 -118.2(4) . . . . ? C30 Ru1 C2 C1 -30.5(5) . . . . ? O1 Ru1 C2 C1 63.6(3) . . . . ? C3 Ru1 C2 C1 131.2(5) . . . . ? P1 Ru1 C2 C1 152.3(3) . . . . ? C29 Ru1 C2 C3 110.6(4) . . . . ? C30 Ru1 C2 C3 -161.6(4) . . . . ? O1 Ru1 C2 C3 -67.6(3) . . . . ? C1 Ru1 C2 C3 -131.2(5) . . . . ? P1 Ru1 C2 C3 21.1(4) . . . . ? C1 C2 C3 C4 -176.8(5) . . . . ? Ru1 C2 C3 C4 -120.9(5) . . . . ? C1 C2 C3 Ru1 -55.9(4) . . . . ? C29 Ru1 C3 C2 -69.9(4) . . . . ? C30 Ru1 C3 C2 44.1(8) . . . . ? O1 Ru1 C3 C2 113.7(3) . . . . ? C1 Ru1 C3 C2 29.6(3) . . . . ? P1 Ru1 C3 C2 -165.0(3) . . . . ? C29 Ru1 C3 C4 47.5(5) . . . . ? C30 Ru1 C3 C4 161.5(6) . . . . ? O1 Ru1 C3 C4 -128.8(5) . . . . ? C1 Ru1 C3 C4 147.0(5) . . . . ? C2 Ru1 C3 C4 117.4(6) . . . . ? P1 Ru1 C3 C4 -47.6(5) . . . . ? C2 C3 C4 C9 -164.3(5) . . . . ? Ru1 C3 C4 C9 107.4(6) . . . . ? C2 C3 C4 C5 16.3(8) . . . . ? Ru1 C3 C4 C5 -72.0(7) . . . . ? C9 C4 C5 C6 -0.7(9) . . . . ? C3 C4 C5 C6 178.7(6) . . . . ? C4 C5 C6 C7 -1.3(10) . . . . ? C5 C6 C7 C8 2.5(12) . . . . ? C6 C7 C8 C9 -1.7(13) . . . . ? C7 C8 C9 C4 -0.4(12) . . . . ? C5 C4 C9 C8 1.6(10) . . . . ? C3 C4 C9 C8 -177.9(6) . . . . ? C23 P1 C10 C11 -99.7(5) . . . . ? C17 P1 C10 C11 9.8(5) . . . . ? Ru1 P1 C10 C11 137.8(4) . . . . ? C23 P1 C10 C15 80.4(4) . . . . ? C17 P1 C10 C15 -170.1(4) . . . . ? Ru1 P1 C10 C15 -42.1(4) . . . . ? C15 C10 C11 C12 1.2(8) . . . . ? P1 C10 C11 C12 -178.7(5) . . . . ? C10 C11 C12 C13 0.1(9) . . . . ? C11 C12 C13 C14 -1.1(10) . . . . ? C12 C13 C14 C15 0.8(10) . . . . ? C13 C14 C15 C10 0.5(8) . . . . ? C13 C14 C15 C16 -175.0(6) . . . . ? C11 C10 C15 C14 -1.4(8) . . . . ? P1 C10 C15 C14 178.4(4) . . . . ? C11 C10 C15 C16 173.7(5) . . . . ? P1 C10 C15 C16 -6.5(7) . . . . ? Ru1 O1 C16 O2 174.8(4) . . . . ? Ru1 O1 C16 C15 -5.9(7) . . . . ? C14 C15 C16 O2 32.5(7) . . . . ? C10 C15 C16 O2 -142.7(5) . . . . ? C14 C15 C16 O1 -146.9(5) . . . . ? C10 C15 C16 O1 37.9(7) . . . . ? C23 P1 C17 C18 -172.6(4) . . . . ? C10 P1 C17 C18 78.2(4) . . . . ? Ru1 P1 C17 C18 -42.1(5) . . . . ? C23 P1 C17 C22 7.4(5) . . . . ? C10 P1 C17 C22 -101.8(5) . . . . ? Ru1 P1 C17 C22 137.9(4) . . . . ? C22 C17 C18 C19 -0.1(8) . . . . ? P1 C17 C18 C19 179.8(4) . . . . ? C17 C18 C19 C20 -0.5(9) . . . . ? C18 C19 C20 C21 1.0(10) . . . . ? C19 C20 C21 C22 -0.7(10) . . . . ? C20 C21 C22 C17 0.0(10) . . . . ? C18 C17 C22 C21 0.4(9) . . . . ? P1 C17 C22 C21 -179.6(5) . . . . ? C10 P1 C23 C24 4.6(5) . . . . ? C17 P1 C23 C24 -105.4(5) . . . . ? Ru1 P1 C23 C24 121.7(4) . . . . ? C10 P1 C23 C28 -178.2(4) . . . . ? C17 P1 C23 C28 71.8(5) . . . . ? Ru1 P1 C23 C28 -61.1(5) . . . . ? C28 C23 C24 C25 1.6(9) . . . . ? P1 C23 C24 C25 178.8(5) . . . . ? C23 C24 C25 C26 -1.7(10) . . . . ? C24 C25 C26 C27 1.6(11) . . . . ? C25 C26 C27 C28 -1.5(10) . . . . ? C26 C27 C28 C23 1.4(9) . . . . ? C24 C23 C28 C27 -1.4(8) . . . . ? P1 C23 C28 C27 -178.8(5) . . . . ? C33 O5 C31 O6 16(3) . . . . ? C33 O5 C31 C32 -168.6(19) . . . . ? C31 O5 C33 C34 -136(2) . . . . ?