# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_EVBA013 _database_code_depnum_ccdc_archive 'CCDC 918728' #TrackingRef 'EVBA013.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(Chlorido)(3-(3-methylbut-2-en-1-yl)-1,4-dioxo-kappaO1-1,4-dihydronaphthalen-2-olato-kappaO2) (p-cymene)ruthenium(II)] ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 Cl O3 Ru' _chemical_formula_sum 'C25 H27 Cl O3 Ru' _chemical_formula_weight 511.99 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' Cl Cl 0.1484 0.1585 '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 P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 12.8956(5) _cell_length_b 11.8913(4) _cell_length_c 14.2756(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.501(2) _cell_angle_gamma 90.00 _cell_volume 2165.05(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9668 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 29.96 _exptl_crystal_description stick _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6227 _exptl_absorpt_correction_T_max 0.9179 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50326 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.07 _reflns_number_total 6286 _reflns_number_gt 5542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0288P)^2^+1.3191P] 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 6286 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C15 C -0.40492(15) 0.47130(17) 0.15950(15) 0.0363(4) Uani 1 1 d . . . H15A H -0.3554 0.4331 0.1244 0.054 Uiso 1 1 calc R . . H15B H -0.4654 0.4974 0.1151 0.054 Uiso 1 1 calc R . . H15C H -0.4286 0.4189 0.2049 0.054 Uiso 1 1 calc R . . C16 C 0.25085(12) 0.49049(14) 0.06169(11) 0.0206(3) Uani 1 1 d . . . C17 C 0.15430(12) 0.51611(14) 0.00314(10) 0.0200(3) Uani 1 1 d . . . H17 H 0.1188 0.4589 -0.0356 0.024 Uiso 1 1 calc R . . C18 C 0.11082(12) 0.62414(13) 0.00168(10) 0.0186(3) Uani 1 1 d . . . H18 H 0.0468 0.6387 -0.0386 0.022 Uiso 1 1 calc R . . C19 C 0.16032(12) 0.71321(13) 0.05925(10) 0.0176(3) Uani 1 1 d . . . C20 C 0.25476(11) 0.68675(13) 0.11836(11) 0.0186(3) Uani 1 1 d . . . H20 H 0.2892 0.7432 0.1586 0.022 Uiso 1 1 calc R . . C21 C 0.29954(12) 0.57714(14) 0.11907(11) 0.0201(3) Uani 1 1 d . . . H21 H 0.3637 0.5623 0.1592 0.024 Uiso 1 1 calc R . . C22 C 0.29437(14) 0.37360(15) 0.06508(13) 0.0286(4) Uani 1 1 d . . . H22A H 0.3264 0.3595 0.0080 0.043 Uiso 1 1 calc R . . H22B H 0.2377 0.3194 0.0682 0.043 Uiso 1 1 calc R . . H22C H 0.3475 0.3653 0.1213 0.043 Uiso 1 1 calc R . . C23 C 0.11169(13) 0.82960(13) 0.05833(12) 0.0225(3) Uani 1 1 d . . . H23 H 0.1471 0.8767 0.0144 0.027 Uiso 1 1 calc R . . C24 C -0.00558(14) 0.83051(15) 0.01998(13) 0.0280(4) Uani 1 1 d . . . H24A H -0.0173 0.7941 -0.0423 0.042 Uiso 1 1 calc R . . H24B H -0.0306 0.9084 0.0140 0.042 Uiso 1 1 calc R . . H24C H -0.0439 0.7896 0.0637 0.042 Uiso 1 1 calc R . . C25 C 0.13053(15) 0.88675(16) 0.15478(14) 0.0322(4) Uani 1 1 d . . . H25A H 0.0978 0.9613 0.1501 0.048 Uiso 1 1 calc R . . H25B H 0.2061 0.8946 0.1754 0.048 Uiso 1 1 calc R . . H25C H 0.0998 0.8411 0.2008 0.048 Uiso 1 1 calc R . . Ru1 Ru 0.139229(9) 0.565311(10) 0.146578(8) 0.01386(4) Uani 1 1 d . . . Cl1 Cl 0.08811(3) 0.38235(3) 0.19549(3) 0.02155(8) Uani 1 1 d . . . O1 O -0.00377(8) 0.62121(10) 0.17913(7) 0.0182(2) Uani 1 1 d . . . O2 O 0.17116(8) 0.59174(9) 0.29398(7) 0.0177(2) Uani 1 1 d . . . O3 O -0.16902(10) 0.70369(12) 0.44344(9) 0.0306(3) Uani 1 1 d . . . C1 C 0.09204(11) 0.61133(12) 0.33209(10) 0.0152(3) Uani 1 1 d . . . C2 C 0.09760(12) 0.61464(12) 0.43453(10) 0.0164(3) Uani 1 1 d . . . C3 C 0.18924(13) 0.58461(13) 0.49373(11) 0.0202(3) Uani 1 1 d . . . H3 H 0.2500 0.5638 0.4675 0.024 Uiso 1 1 calc R . . C4 C 0.19111(14) 0.58526(14) 0.59082(12) 0.0240(3) Uani 1 1 d . . . H4 H 0.2532 0.5645 0.6316 0.029 Uiso 1 1 calc R . . C5 C 0.10229(15) 0.61629(14) 0.62869(11) 0.0257(3) Uani 1 1 d . . . H5 H 0.1039 0.6168 0.6954 0.031 Uiso 1 1 calc R . . C6 C 0.01106(14) 0.64662(14) 0.56997(11) 0.0236(3) Uani 1 1 d . . . H6 H -0.0492 0.6682 0.5967 0.028 Uiso 1 1 calc R . . C7 C 0.00757(12) 0.64547(12) 0.47228(11) 0.0184(3) Uani 1 1 d . . . C8 C -0.09166(12) 0.67481(13) 0.40843(11) 0.0199(3) Uani 1 1 d . . . C9 C -0.09413(12) 0.66770(13) 0.30661(11) 0.0181(3) Uani 1 1 d . . . C10 C -0.00761(11) 0.63248(12) 0.26934(10) 0.0157(3) Uani 1 1 d . . . C11 C -0.19302(12) 0.69837(14) 0.24219(11) 0.0212(3) Uani 1 1 d . . . H11A H -0.1747 0.7450 0.1896 0.025 Uiso 1 1 calc R . . H11B H -0.2377 0.7444 0.2780 0.025 Uiso 1 1 calc R . . C12 C -0.25458(12) 0.59804(14) 0.20152(11) 0.0221(3) Uani 1 1 d . . . H12 H -0.2198 0.5487 0.1640 0.027 Uiso 1 1 calc R . . C13 C -0.35188(13) 0.57019(14) 0.21179(12) 0.0232(3) Uani 1 1 d . . . C14 C -0.41728(15) 0.63276(17) 0.27368(15) 0.0345(4) Uani 1 1 d . . . H14A H -0.3735 0.6882 0.3120 0.052 Uiso 1 1 calc R . . H14B H -0.4461 0.5795 0.3155 0.052 Uiso 1 1 calc R . . H14C H -0.4749 0.6714 0.2339 0.052 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 C15 0.0267(9) 0.0340(10) 0.0470(12) -0.0066(9) 0.0016(8) -0.0013(8) C16 0.0206(7) 0.0244(7) 0.0184(7) -0.0001(6) 0.0084(6) 0.0017(6) C17 0.0229(7) 0.0251(7) 0.0130(7) -0.0024(6) 0.0061(5) -0.0016(6) C18 0.0189(7) 0.0263(8) 0.0108(7) 0.0015(6) 0.0033(5) -0.0022(6) C19 0.0182(7) 0.0210(7) 0.0144(7) 0.0014(5) 0.0055(5) -0.0026(5) C20 0.0163(7) 0.0231(7) 0.0171(7) -0.0008(6) 0.0050(5) -0.0054(6) C21 0.0131(6) 0.0293(8) 0.0185(7) 0.0007(6) 0.0046(5) -0.0004(6) C22 0.0309(9) 0.0261(8) 0.0305(9) -0.0014(7) 0.0099(7) 0.0078(7) C23 0.0244(8) 0.0207(7) 0.0227(8) 0.0029(6) 0.0048(6) -0.0014(6) C24 0.0265(8) 0.0255(8) 0.0308(9) 0.0046(7) 0.0002(7) 0.0041(7) C25 0.0346(10) 0.0257(9) 0.0350(10) -0.0084(7) 0.0011(8) 0.0038(7) Ru1 0.01267(6) 0.01833(6) 0.01071(6) -0.00030(4) 0.00211(4) -0.00106(4) Cl1 0.02470(18) 0.02152(17) 0.01807(17) 0.00242(13) 0.00194(13) -0.00470(14) O1 0.0144(5) 0.0277(6) 0.0127(5) 0.0018(4) 0.0025(4) 0.0015(4) O2 0.0144(5) 0.0250(5) 0.0136(5) -0.0010(4) 0.0014(4) -0.0001(4) O3 0.0263(6) 0.0420(7) 0.0258(6) -0.0030(5) 0.0120(5) 0.0058(5) C1 0.0162(6) 0.0142(6) 0.0152(7) 0.0004(5) 0.0028(5) -0.0018(5) C2 0.0204(7) 0.0154(6) 0.0137(7) -0.0007(5) 0.0035(5) -0.0026(5) C3 0.0229(7) 0.0202(7) 0.0168(7) -0.0002(5) 0.0007(6) -0.0020(6) C4 0.0309(9) 0.0231(7) 0.0163(8) 0.0007(6) -0.0022(6) -0.0043(6) C5 0.0390(9) 0.0254(8) 0.0127(7) -0.0020(6) 0.0040(6) -0.0066(7) C6 0.0299(8) 0.0246(8) 0.0173(8) -0.0035(6) 0.0073(6) -0.0042(6) C7 0.0234(7) 0.0160(6) 0.0163(7) -0.0020(5) 0.0049(6) -0.0035(5) C8 0.0216(7) 0.0188(7) 0.0208(8) -0.0006(6) 0.0082(6) 0.0000(6) C9 0.0175(7) 0.0183(7) 0.0189(7) 0.0009(5) 0.0041(5) 0.0007(5) C10 0.0169(6) 0.0161(6) 0.0142(7) 0.0014(5) 0.0023(5) -0.0008(5) C11 0.0161(7) 0.0257(8) 0.0222(8) 0.0033(6) 0.0044(6) 0.0044(6) C12 0.0205(7) 0.0282(8) 0.0178(8) -0.0008(6) 0.0030(6) 0.0047(6) C13 0.0216(8) 0.0242(8) 0.0233(8) 0.0020(6) 0.0023(6) 0.0037(6) C14 0.0258(9) 0.0326(9) 0.0487(12) -0.0043(8) 0.0178(8) -0.0030(7) _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 C15 C13 1.502(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C21 1.405(2) . ? C16 C17 1.426(2) . ? C16 C22 1.497(2) . ? C16 Ru1 2.2017(15) . ? C17 C18 1.401(2) . ? C17 Ru1 2.1658(15) . ? C17 H17 0.9500 . ? C18 C19 1.432(2) . ? C18 Ru1 2.1629(15) . ? C18 H18 0.9500 . ? C19 C20 1.411(2) . ? C19 C23 1.519(2) . ? C19 Ru1 2.1957(15) . ? C20 C21 1.425(2) . ? C20 Ru1 2.1551(14) . ? C20 H20 0.9500 . ? C21 Ru1 2.1651(15) . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.522(2) . ? C23 C24 1.530(2) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Ru1 O1 2.0764(10) . ? Ru1 O2 2.1072(11) . ? Ru1 Cl1 2.4065(4) . ? O1 C10 1.3031(17) . ? O2 C1 1.2470(17) . ? O3 C8 1.2289(19) . ? C1 C2 1.454(2) . ? C1 C10 1.475(2) . ? C2 C3 1.394(2) . ? C2 C7 1.399(2) . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C8 1.498(2) . ? C8 C9 1.452(2) . ? C9 C10 1.371(2) . ? C9 C11 1.503(2) . ? C11 C12 1.502(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.327(2) . ? C12 H12 0.9500 . ? C13 C14 1.505(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 117.46(14) . . ? C21 C16 C22 121.93(15) . . ? C17 C16 C22 120.52(15) . . ? C21 C16 Ru1 69.82(9) . . ? C17 C16 Ru1 69.58(8) . . ? C22 C16 Ru1 129.04(11) . . ? C18 C17 C16 121.17(14) . . ? C18 C17 Ru1 71.01(8) . . ? C16 C17 Ru1 72.31(9) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? Ru1 C17 H17 129.8 . . ? C17 C18 C19 121.77(14) . . ? C17 C18 Ru1 71.24(8) . . ? C19 C18 Ru1 72.07(8) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? Ru1 C18 H18 130.3 . . ? C20 C19 C18 116.78(14) . . ? C20 C19 C23 121.82(14) . . ? C18 C19 C23 121.38(14) . . ? C20 C19 Ru1 69.52(8) . . ? C18 C19 Ru1 69.59(8) . . ? C23 C19 Ru1 130.48(10) . . ? C19 C20 C21 121.42(14) . . ? C19 C20 Ru1 72.65(8) . . ? C21 C20 Ru1 71.12(9) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? Ru1 C20 H20 129.5 . . ? C16 C21 C20 121.39(14) . . ? C16 C21 Ru1 72.65(9) . . ? C20 C21 Ru1 70.36(8) . . ? C16 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? Ru1 C21 H21 130.4 . . ? C16 C22 H22A 109.5 . . ? C16 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C16 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 C25 112.86(14) . . ? C19 C23 C24 113.24(13) . . ? C25 C23 C24 109.72(14) . . ? C19 C23 H23 106.9 . . ? C25 C23 H23 106.9 . . ? C24 C23 H23 106.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 Ru1 O2 77.15(4) . . ? O1 Ru1 C20 119.25(5) . . ? O2 Ru1 C20 92.77(5) . . ? O1 Ru1 C18 94.59(5) . . ? O2 Ru1 C18 152.53(5) . . ? C20 Ru1 C18 68.20(6) . . ? O1 Ru1 C17 120.32(5) . . ? O2 Ru1 C17 162.34(5) . . ? C20 Ru1 C17 80.98(6) . . ? C18 Ru1 C17 37.76(6) . . ? O1 Ru1 C21 157.39(5) . . ? O2 Ru1 C21 96.93(5) . . ? C20 Ru1 C21 38.52(6) . . ? C18 Ru1 C21 80.61(6) . . ? C17 Ru1 C21 67.95(6) . . ? O1 Ru1 C19 93.40(5) . . ? O2 Ru1 C19 115.16(5) . . ? C20 Ru1 C19 37.83(6) . . ? C18 Ru1 C19 38.34(6) . . ? C17 Ru1 C19 69.12(6) . . ? C21 Ru1 C19 69.10(6) . . ? O1 Ru1 C16 157.97(5) . . ? O2 Ru1 C16 124.25(5) . . ? C20 Ru1 C16 69.00(6) . . ? C18 Ru1 C16 68.68(6) . . ? C17 Ru1 C16 38.11(6) . . ? C21 Ru1 C16 37.53(6) . . ? C19 Ru1 C16 82.25(6) . . ? O1 Ru1 Cl1 86.22(3) . . ? O2 Ru1 Cl1 82.33(3) . . ? C20 Ru1 Cl1 152.44(4) . . ? C18 Ru1 Cl1 123.71(4) . . ? C17 Ru1 Cl1 95.56(4) . . ? C21 Ru1 Cl1 114.91(4) . . ? C19 Ru1 Cl1 162.00(4) . . ? C16 Ru1 Cl1 91.36(4) . . ? C10 O1 Ru1 114.77(9) . . ? C1 O2 Ru1 114.32(9) . . ? O2 C1 C2 121.46(13) . . ? O2 C1 C10 117.54(13) . . ? C2 C1 C10 121.00(13) . . ? C3 C2 C7 120.73(14) . . ? C3 C2 C1 120.94(14) . . ? C7 C2 C1 118.30(13) . . ? C4 C3 C2 119.60(15) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.95(16) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.60(15) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.19(15) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 118.93(15) . . ? C6 C7 C8 120.43(14) . . ? C2 C7 C8 120.63(13) . . ? O3 C8 C9 121.64(15) . . ? O3 C8 C7 119.30(14) . . ? C9 C8 C7 119.07(13) . . ? C10 C9 C8 120.52(14) . . ? C10 C9 C11 120.16(14) . . ? C8 C9 C11 119.32(13) . . ? O1 C10 C9 124.55(14) . . ? O1 C10 C1 115.18(12) . . ? C9 C10 C1 120.15(13) . . ? C9 C11 C12 113.34(13) . . ? C9 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C9 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 127.61(15) . . ? C13 C12 H12 116.2 . . ? C11 C12 H12 116.2 . . ? C12 C13 C15 120.60(16) . . ? C12 C13 C14 124.24(16) . . ? C15 C13 C14 115.15(15) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C21 C16 C17 C18 1.2(2) . . . . ? C22 C16 C17 C18 177.80(14) . . . . ? Ru1 C16 C17 C18 53.70(13) . . . . ? C21 C16 C17 Ru1 -52.53(12) . . . . ? C22 C16 C17 Ru1 124.10(14) . . . . ? C16 C17 C18 C19 -0.6(2) . . . . ? Ru1 C17 C18 C19 53.65(13) . . . . ? C16 C17 C18 Ru1 -54.29(13) . . . . ? C17 C18 C19 C20 -0.6(2) . . . . ? Ru1 C18 C19 C20 52.70(12) . . . . ? C17 C18 C19 C23 -179.03(14) . . . . ? Ru1 C18 C19 C23 -125.76(13) . . . . ? C17 C18 C19 Ru1 -53.27(13) . . . . ? C18 C19 C20 C21 1.2(2) . . . . ? C23 C19 C20 C21 179.70(14) . . . . ? Ru1 C19 C20 C21 53.98(13) . . . . ? C18 C19 C20 Ru1 -52.73(12) . . . . ? C23 C19 C20 Ru1 125.72(14) . . . . ? C17 C16 C21 C20 -0.5(2) . . . . ? C22 C16 C21 C20 -177.07(14) . . . . ? Ru1 C16 C21 C20 -52.90(13) . . . . ? C17 C16 C21 Ru1 52.42(12) . . . . ? C22 C16 C21 Ru1 -124.17(15) . . . . ? C19 C20 C21 C16 -0.7(2) . . . . ? Ru1 C20 C21 C16 53.94(13) . . . . ? C19 C20 C21 Ru1 -54.68(13) . . . . ? C20 C19 C23 C25 -33.3(2) . . . . ? C18 C19 C23 C25 145.09(15) . . . . ? Ru1 C19 C23 C25 56.04(19) . . . . ? C20 C19 C23 C24 -158.71(14) . . . . ? C18 C19 C23 C24 19.7(2) . . . . ? Ru1 C19 C23 C24 -69.38(18) . . . . ? C19 C20 Ru1 O1 -52.37(10) . . . . ? C21 C20 Ru1 O1 174.47(8) . . . . ? C19 C20 Ru1 O2 -129.19(9) . . . . ? C21 C20 Ru1 O2 97.65(9) . . . . ? C19 C20 Ru1 C18 30.43(9) . . . . ? C21 C20 Ru1 C18 -102.73(10) . . . . ? C19 C20 Ru1 C17 67.42(9) . . . . ? C21 C20 Ru1 C17 -65.73(9) . . . . ? C19 C20 Ru1 C21 133.16(13) . . . . ? C21 C20 Ru1 C19 -133.16(13) . . . . ? C19 C20 Ru1 C16 105.01(10) . . . . ? C21 C20 Ru1 C16 -28.15(9) . . . . ? C19 C20 Ru1 Cl1 152.12(8) . . . . ? C21 C20 Ru1 Cl1 18.97(14) . . . . ? C17 C18 Ru1 O1 -136.34(9) . . . . ? C19 C18 Ru1 O1 89.68(9) . . . . ? C17 C18 Ru1 O2 152.88(10) . . . . ? C19 C18 Ru1 O2 18.90(15) . . . . ? C17 C18 Ru1 C20 103.93(10) . . . . ? C19 C18 Ru1 C20 -30.05(9) . . . . ? C19 C18 Ru1 C17 -133.97(13) . . . . ? C17 C18 Ru1 C21 65.92(9) . . . . ? C19 C18 Ru1 C21 -68.05(9) . . . . ? C17 C18 Ru1 C19 133.97(13) . . . . ? C17 C18 Ru1 C16 28.89(9) . . . . ? C19 C18 Ru1 C16 -105.08(10) . . . . ? C17 C18 Ru1 Cl1 -47.83(10) . . . . ? C19 C18 Ru1 Cl1 178.19(7) . . . . ? C18 C17 Ru1 O1 52.86(10) . . . . ? C16 C17 Ru1 O1 -173.97(8) . . . . ? C18 C17 Ru1 O2 -136.12(16) . . . . ? C16 C17 Ru1 O2 -2.9(2) . . . . ? C18 C17 Ru1 C20 -65.85(9) . . . . ? C16 C17 Ru1 C20 67.33(10) . . . . ? C16 C17 Ru1 C18 133.18(14) . . . . ? C18 C17 Ru1 C21 -103.62(10) . . . . ? C16 C17 Ru1 C21 29.55(9) . . . . ? C18 C17 Ru1 C19 -28.54(9) . . . . ? C16 C17 Ru1 C19 104.63(10) . . . . ? C18 C17 Ru1 C16 -133.18(14) . . . . ? C18 C17 Ru1 Cl1 141.72(8) . . . . ? C16 C17 Ru1 Cl1 -85.10(9) . . . . ? C16 C21 Ru1 O1 -146.33(12) . . . . ? C20 C21 Ru1 O1 -12.63(18) . . . . ? C16 C21 Ru1 O2 140.57(9) . . . . ? C20 C21 Ru1 O2 -85.73(9) . . . . ? C16 C21 Ru1 C20 -133.70(14) . . . . ? C16 C21 Ru1 C18 -67.07(10) . . . . ? C20 C21 Ru1 C18 66.63(9) . . . . ? C16 C21 Ru1 C17 -29.98(9) . . . . ? C20 C21 Ru1 C17 103.72(10) . . . . ? C16 C21 Ru1 C19 -105.09(10) . . . . ? C20 C21 Ru1 C19 28.61(9) . . . . ? C20 C21 Ru1 C16 133.70(14) . . . . ? C16 C21 Ru1 Cl1 55.84(10) . . . . ? C20 C21 Ru1 Cl1 -170.46(7) . . . . ? C20 C19 Ru1 O1 136.19(9) . . . . ? C18 C19 Ru1 O1 -93.10(9) . . . . ? C23 C19 Ru1 O1 21.28(14) . . . . ? C20 C19 Ru1 O2 58.79(10) . . . . ? C18 C19 Ru1 O2 -170.50(8) . . . . ? C23 C19 Ru1 O2 -56.12(15) . . . . ? C18 C19 Ru1 C20 130.71(13) . . . . ? C23 C19 Ru1 C20 -114.91(17) . . . . ? C20 C19 Ru1 C18 -130.71(13) . . . . ? C23 C19 Ru1 C18 114.38(17) . . . . ? C20 C19 Ru1 C17 -102.57(10) . . . . ? C18 C19 Ru1 C17 28.14(9) . . . . ? C23 C19 Ru1 C17 142.52(15) . . . . ? C20 C19 Ru1 C21 -29.10(9) . . . . ? C18 C19 Ru1 C21 101.61(10) . . . . ? C23 C19 Ru1 C21 -144.01(15) . . . . ? C20 C19 Ru1 C16 -65.51(9) . . . . ? C18 C19 Ru1 C16 65.20(9) . . . . ? C23 C19 Ru1 C16 179.58(15) . . . . ? C20 C19 Ru1 Cl1 -135.57(12) . . . . ? C18 C19 Ru1 Cl1 -4.87(18) . . . . ? C23 C19 Ru1 Cl1 109.51(16) . . . . ? C21 C16 Ru1 O1 145.38(13) . . . . ? C17 C16 Ru1 O1 14.00(19) . . . . ? C22 C16 Ru1 O1 -99.32(19) . . . . ? C21 C16 Ru1 O2 -49.70(11) . . . . ? C17 C16 Ru1 O2 178.92(8) . . . . ? C22 C16 Ru1 O2 65.60(16) . . . . ? C21 C16 Ru1 C20 28.83(9) . . . . ? C17 C16 Ru1 C20 -102.54(10) . . . . ? C22 C16 Ru1 C20 144.14(16) . . . . ? C21 C16 Ru1 C18 102.74(10) . . . . ? C17 C16 Ru1 C18 -28.64(9) . . . . ? C22 C16 Ru1 C18 -141.96(16) . . . . ? C21 C16 Ru1 C17 131.38(14) . . . . ? C22 C16 Ru1 C17 -113.32(19) . . . . ? C17 C16 Ru1 C21 -131.38(14) . . . . ? C22 C16 Ru1 C21 115.30(19) . . . . ? C21 C16 Ru1 C19 65.54(10) . . . . ? C17 C16 Ru1 C19 -65.83(10) . . . . ? C22 C16 Ru1 C19 -179.15(16) . . . . ? C21 C16 Ru1 Cl1 -131.35(9) . . . . ? C17 C16 Ru1 Cl1 97.28(9) . . . . ? C22 C16 Ru1 Cl1 -16.04(15) . . . . ? O2 Ru1 O1 C10 -6.92(10) . . . . ? C20 Ru1 O1 C10 -92.85(11) . . . . ? C18 Ru1 O1 C10 -160.39(11) . . . . ? C17 Ru1 O1 C10 170.30(10) . . . . ? C21 Ru1 O1 C10 -83.87(16) . . . . ? C19 Ru1 O1 C10 -121.97(10) . . . . ? C16 Ru1 O1 C10 160.33(14) . . . . ? Cl1 Ru1 O1 C10 76.06(10) . . . . ? O1 Ru1 O2 C1 9.31(10) . . . . ? C20 Ru1 O2 C1 128.71(11) . . . . ? C18 Ru1 O2 C1 84.20(14) . . . . ? C17 Ru1 O2 C1 -162.74(16) . . . . ? C21 Ru1 O2 C1 167.15(11) . . . . ? C19 Ru1 O2 C1 97.03(11) . . . . ? C16 Ru1 O2 C1 -164.94(10) . . . . ? Cl1 Ru1 O2 C1 -78.53(10) . . . . ? Ru1 O2 C1 C2 170.55(10) . . . . ? Ru1 O2 C1 C10 -10.16(16) . . . . ? O2 C1 C2 C3 -6.7(2) . . . . ? C10 C1 C2 C3 174.07(14) . . . . ? O2 C1 C2 C7 175.23(14) . . . . ? C10 C1 C2 C7 -4.0(2) . . . . ? C7 C2 C3 C4 0.0(2) . . . . ? C1 C2 C3 C4 -178.00(14) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C2 -0.7(2) . . . . ? C5 C6 C7 C8 178.17(15) . . . . ? C3 C2 C7 C6 0.5(2) . . . . ? C1 C2 C7 C6 178.61(14) . . . . ? C3 C2 C7 C8 -178.40(14) . . . . ? C1 C2 C7 C8 -0.3(2) . . . . ? C6 C7 C8 O3 2.5(2) . . . . ? C2 C7 C8 O3 -178.62(15) . . . . ? C6 C7 C8 C9 -177.13(14) . . . . ? C2 C7 C8 C9 1.8(2) . . . . ? O3 C8 C9 C10 -178.31(15) . . . . ? C7 C8 C9 C10 1.3(2) . . . . ? O3 C8 C9 C11 1.1(2) . . . . ? C7 C8 C9 C11 -179.26(13) . . . . ? Ru1 O1 C10 C9 -179.70(12) . . . . ? Ru1 O1 C10 C1 4.09(16) . . . . ? C8 C9 C10 O1 178.37(14) . . . . ? C11 C9 C10 O1 -1.1(2) . . . . ? C8 C9 C10 C1 -5.6(2) . . . . ? C11 C9 C10 C1 174.96(13) . . . . ? O2 C1 C10 O1 4.2(2) . . . . ? C2 C1 C10 O1 -176.47(13) . . . . ? O2 C1 C10 C9 -172.15(14) . . . . ? C2 C1 C10 C9 7.1(2) . . . . ? C10 C9 C11 C12 77.07(18) . . . . ? C8 C9 C11 C12 -102.38(17) . . . . ? C9 C11 C12 C13 119.75(18) . . . . ? C11 C12 C13 C15 175.03(17) . . . . ? C11 C12 C13 C14 -4.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.645 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.067 data_EVBA017 _database_code_depnum_ccdc_archive 'CCDC 918729' #TrackingRef 'EVBA017.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(Chlorido)(3-(3-methylbut-2-en-1-yl)-1,4-dioxo-kappaO1-1,4-dihydronaphthalen-2-olato-kappaO2) (p-cymene)osmium(II)] ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 Cl O3 Os' _chemical_formula_sum 'C25 H27 Cl O3 Os' _chemical_formula_weight 601.12 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Os Os -1.2165 7.6030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 13.4764(4) _cell_length_b 8.4120(2) _cell_length_c 21.0225(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.9860(10) _cell_angle_gamma 90.00 _cell_volume 2266.72(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5792 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 29.74 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 5.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5445 _exptl_absorpt_correction_T_max 0.8934 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17682 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5455 _reflns_number_gt 4378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Buker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0177P)^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 5455 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0507 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.002 _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 Os1 Os 0.520242(10) 0.053152(15) 0.207543(6) 0.01806(4) Uani 1 1 d . . . Cl1 Cl 0.45963(7) 0.32056(10) 0.20527(4) 0.02670(19) Uani 1 1 d . . . O1 O 0.59922(17) 0.1486(3) 0.14275(10) 0.0200(5) Uani 1 1 d . . . O2 O 0.41232(18) 0.0359(3) 0.11278(11) 0.0250(5) Uani 1 1 d . . . O3 O 0.33932(19) 0.2620(3) -0.10168(11) 0.0288(6) Uani 1 1 d . . . C1 C 0.4348(3) 0.1150(4) 0.06568(15) 0.0185(7) Uani 1 1 d . . . C2 C 0.5417(2) 0.1780(4) 0.08428(15) 0.0181(7) Uani 1 1 d . . . C3 C 0.5789(3) 0.2678(4) 0.03797(16) 0.0187(7) Uani 1 1 d . . . C4 C 0.6809(3) 0.3284(4) 0.05622(17) 0.0231(8) Uani 1 1 d . . . H4 H 0.7282 0.3072 0.0993 0.028 Uiso 1 1 calc R . . C5 C 0.7116(3) 0.4188(4) 0.01115(17) 0.0253(8) Uani 1 1 d . . . H5 H 0.7807 0.4594 0.0231 0.030 Uiso 1 1 calc R . . C6 C 0.6427(3) 0.4512(4) -0.05163(17) 0.0275(8) Uani 1 1 d . . . H6 H 0.6647 0.5136 -0.0825 0.033 Uiso 1 1 calc R . . C7 C 0.5419(3) 0.3928(4) -0.06942(17) 0.0248(8) Uani 1 1 d . . . H7 H 0.4946 0.4176 -0.1122 0.030 Uiso 1 1 calc R . . C8 C 0.5090(3) 0.2989(4) -0.02579(16) 0.0185(7) Uani 1 1 d . . . C9 C 0.4001(3) 0.2321(4) -0.04535(16) 0.0202(7) Uani 1 1 d . . . C10 C 0.3678(3) 0.1361(4) 0.00180(16) 0.0199(7) Uani 1 1 d . . . C11 C 0.2614(3) 0.0605(4) -0.01924(17) 0.0251(8) Uani 1 1 d . . . H11A H 0.2646 -0.0380 0.0071 0.030 Uiso 1 1 calc R . . H11B H 0.2439 0.0296 -0.0669 0.030 Uiso 1 1 calc R . . C12 C 0.1744(3) 0.1632(4) -0.01094(17) 0.0266(8) Uani 1 1 d . . . H12 H 0.1929 0.2425 0.0229 0.032 Uiso 1 1 calc R . . C13 C 0.0745(3) 0.1529(5) -0.04657(19) 0.0321(9) Uani 1 1 d . . . C14 C -0.0071(3) 0.2556(6) -0.0318(2) 0.0511(13) Uani 1 1 d . . . H14A H 0.0264 0.3284 0.0050 0.077 Uiso 1 1 calc R . . H14B H -0.0571 0.1881 -0.0189 0.077 Uiso 1 1 calc R . . H14C H -0.0438 0.3170 -0.0717 0.077 Uiso 1 1 calc R . . C15 C 0.0330(3) 0.0365(5) -0.1024(2) 0.0519(13) Uani 1 1 d . . . H15A H 0.0867 -0.0430 -0.1014 0.078 Uiso 1 1 calc R . . H15B H 0.0139 0.0929 -0.1453 0.078 Uiso 1 1 calc R . . H15C H -0.0287 -0.0165 -0.0972 0.078 Uiso 1 1 calc R . . C16 C 0.6616(3) -0.0680(4) 0.26428(17) 0.0230(7) Uani 1 1 d . . . C17 C 0.6306(3) 0.0378(4) 0.30777(17) 0.0264(8) Uani 1 1 d . . . H17 H 0.6788 0.1125 0.3341 0.032 Uiso 1 1 calc R . . C18 C 0.5279(3) 0.0305(4) 0.31129(17) 0.0269(8) Uani 1 1 d . . . H18 H 0.5085 0.1009 0.3408 0.032 Uiso 1 1 calc R . . C19 C 0.4518(3) -0.0780(4) 0.27249(17) 0.0232(8) Uani 1 1 d . . . C20 C 0.4856(3) -0.1851(4) 0.23116(16) 0.0217(7) Uani 1 1 d . . . H20 H 0.4377 -0.2607 0.2051 0.026 Uiso 1 1 calc R . . C21 C 0.5887(3) -0.1822(4) 0.22784(16) 0.0224(7) Uani 1 1 d . . . H21 H 0.6095 -0.2578 0.2008 0.027 Uiso 1 1 calc R . . C22 C 0.7657(3) -0.0514(4) 0.2532(2) 0.0335(9) Uani 1 1 d . . . H22A H 0.8174 -0.1154 0.2864 0.050 Uiso 1 1 calc R . . H22B H 0.7870 0.0604 0.2579 0.050 Uiso 1 1 calc R . . H22C H 0.7608 -0.0885 0.2082 0.050 Uiso 1 1 calc R . . C23 C 0.3409(3) -0.0766(5) 0.2749(2) 0.0351(10) Uani 1 1 d . . . H23 H 0.3247 0.0337 0.2865 0.042 Uiso 1 1 calc R . . C24 C 0.3342(3) -0.1873(7) 0.3313(2) 0.0687(18) Uani 1 1 d . . . H24A H 0.2631 -0.1856 0.3343 0.103 Uiso 1 1 calc R . . H24B H 0.3831 -0.1512 0.3738 0.103 Uiso 1 1 calc R . . H24C H 0.3521 -0.2958 0.3219 0.103 Uiso 1 1 calc R . . C25 C 0.2611(3) -0.1219(6) 0.2096(2) 0.0520(13) Uani 1 1 d . . . H25A H 0.1911 -0.1167 0.2144 0.078 Uiso 1 1 calc R . . H25B H 0.2749 -0.2303 0.1975 0.078 Uiso 1 1 calc R . . H25C H 0.2656 -0.0480 0.1746 0.078 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 Os1 0.01584(6) 0.02058(7) 0.01607(7) 0.00166(6) 0.00243(5) -0.00028(6) Cl1 0.0258(4) 0.0256(5) 0.0295(5) 0.0049(4) 0.0096(4) 0.0058(4) O1 0.0170(11) 0.0248(13) 0.0171(11) 0.0014(10) 0.0035(9) 0.0010(10) O2 0.0195(12) 0.0322(15) 0.0202(12) 0.0029(11) 0.0017(10) -0.0059(11) O3 0.0276(14) 0.0377(15) 0.0168(12) 0.0041(11) 0.0006(11) 0.0045(12) C1 0.0207(17) 0.0178(16) 0.0166(16) -0.0013(13) 0.0052(14) 0.0009(13) C2 0.0206(17) 0.0164(17) 0.0165(16) -0.0035(13) 0.0044(14) 0.0016(14) C3 0.0203(17) 0.0166(17) 0.0213(17) -0.0050(13) 0.0095(14) 0.0012(14) C4 0.0238(18) 0.0230(19) 0.0217(17) -0.0008(14) 0.0057(15) -0.0003(15) C5 0.0254(18) 0.022(2) 0.0308(19) -0.0015(14) 0.0117(16) -0.0030(15) C6 0.038(2) 0.0231(19) 0.0263(18) 0.0036(15) 0.0171(16) 0.0034(17) C7 0.033(2) 0.0216(18) 0.0203(17) 0.0015(14) 0.0084(16) 0.0034(15) C8 0.0243(18) 0.0127(16) 0.0200(16) -0.0010(12) 0.0090(15) 0.0071(13) C9 0.0213(17) 0.0208(18) 0.0163(16) -0.0050(13) 0.0028(14) 0.0033(14) C10 0.0203(17) 0.0157(17) 0.0224(17) -0.0021(13) 0.0045(14) 0.0012(14) C11 0.0233(17) 0.0265(19) 0.0214(17) -0.0010(15) 0.0011(14) -0.0049(16) C12 0.0241(18) 0.031(2) 0.0254(19) -0.0003(16) 0.0091(16) -0.0031(17) C13 0.0229(19) 0.037(2) 0.035(2) 0.0149(18) 0.0057(17) -0.0001(18) C14 0.027(2) 0.076(3) 0.054(3) 0.023(3) 0.018(2) 0.011(2) C15 0.033(2) 0.053(3) 0.053(3) 0.004(2) -0.011(2) -0.009(2) C16 0.0178(16) 0.0210(18) 0.0258(18) 0.0067(14) 0.0002(14) -0.0003(14) C17 0.0300(19) 0.025(2) 0.0177(17) 0.0028(14) -0.0028(15) 0.0006(16) C18 0.038(2) 0.025(2) 0.0177(17) 0.0037(14) 0.0089(16) 0.0053(17) C19 0.0275(18) 0.0210(19) 0.0230(17) 0.0080(14) 0.0106(15) 0.0036(15) C20 0.0241(18) 0.0211(18) 0.0195(17) 0.0036(14) 0.0062(15) -0.0052(14) C21 0.0243(18) 0.0206(18) 0.0208(17) 0.0036(14) 0.0047(15) 0.0054(15) C22 0.0194(17) 0.033(2) 0.043(2) 0.0110(19) 0.0019(16) 0.0009(17) C23 0.029(2) 0.041(3) 0.041(2) 0.0124(18) 0.0179(18) 0.0114(18) C24 0.032(2) 0.125(5) 0.055(3) 0.049(3) 0.021(2) 0.007(3) C25 0.023(2) 0.078(4) 0.055(3) 0.024(3) 0.011(2) 0.000(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 Os1 O2 2.077(2) . ? Os1 O1 2.128(2) . ? Os1 C20 2.151(3) . ? Os1 C18 2.160(3) . ? Os1 C16 2.165(3) . ? Os1 C19 2.170(3) . ? Os1 C21 2.170(3) . ? Os1 C17 2.175(3) . ? Os1 Cl1 2.3886(9) . ? O1 C2 1.259(4) . ? O2 C1 1.304(4) . ? O3 C9 1.240(4) . ? C1 C10 1.379(4) . ? C1 C2 1.470(4) . ? C2 C3 1.439(5) . ? C3 C4 1.404(4) . ? C3 C8 1.405(4) . ? C4 C5 1.375(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(5) . ? C5 H5 0.9500 . ? C6 C7 1.383(5) . ? C6 H6 0.9500 . ? C7 C8 1.384(5) . ? C7 H7 0.9500 . ? C8 C9 1.504(5) . ? C9 C10 1.446(5) . ? C10 C11 1.504(4) . ? C11 C12 1.509(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.326(5) . ? C12 H12 0.9500 . ? C13 C15 1.498(6) . ? C13 C14 1.505(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C21 1.418(5) . ? C16 C17 1.428(5) . ? C16 C22 1.497(5) . ? C17 C18 1.410(5) . ? C17 H17 0.9500 . ? C18 C19 1.425(5) . ? C18 H18 0.9500 . ? C19 C20 1.421(5) . ? C19 C23 1.512(5) . ? C20 C21 1.412(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.508(6) . ? C23 C24 1.532(5) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 O2 Os1 O1 75.70(9) . . ? O2 Os1 C20 91.08(11) . . ? O1 Os1 C20 133.36(11) . . ? O2 Os1 C18 139.73(12) . . ? O1 Os1 C18 143.36(12) . . ? C20 Os1 C18 68.33(13) . . ? O2 Os1 C16 137.04(12) . . ? O1 Os1 C16 90.08(11) . . ? C20 Os1 C16 69.56(12) . . ? C18 Os1 C16 69.07(14) . . ? O2 Os1 C19 105.08(11) . . ? O1 Os1 C19 171.23(11) . . ? C20 Os1 C19 38.41(12) . . ? C18 Os1 C19 38.44(13) . . ? C16 Os1 C19 83.50(13) . . ? O2 Os1 C21 104.72(11) . . ? O1 Os1 C21 101.77(11) . . ? C20 Os1 C21 38.15(12) . . ? C18 Os1 C21 80.57(13) . . ? C16 Os1 C21 38.18(12) . . ? C19 Os1 C21 69.52(13) . . ? O2 Os1 C17 172.49(11) . . ? O1 Os1 C17 108.36(11) . . ? C20 Os1 C17 81.55(13) . . ? C18 Os1 C17 37.97(14) . . ? C16 Os1 C17 38.41(13) . . ? C19 Os1 C17 69.92(14) . . ? C21 Os1 C17 68.49(13) . . ? O2 Os1 Cl1 84.99(7) . . ? O1 Os1 Cl1 82.37(6) . . ? C20 Os1 Cl1 141.74(10) . . ? C18 Os1 Cl1 90.72(9) . . ? C16 Os1 Cl1 133.76(9) . . ? C19 Os1 Cl1 106.38(9) . . ? C21 Os1 Cl1 170.08(9) . . ? C17 Os1 Cl1 101.69(9) . . ? C2 O1 Os1 114.8(2) . . ? C1 O2 Os1 115.78(19) . . ? O2 C1 C10 124.7(3) . . ? O2 C1 C2 114.8(3) . . ? C10 C1 C2 120.4(3) . . ? O1 C2 C3 121.7(3) . . ? O1 C2 C1 116.5(3) . . ? C3 C2 C1 121.8(3) . . ? C4 C3 C8 120.3(3) . . ? C4 C3 C2 121.5(3) . . ? C8 C3 C2 118.1(3) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.9(3) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C3 118.7(3) . . ? C7 C8 C9 121.2(3) . . ? C3 C8 C9 120.1(3) . . ? O3 C9 C10 121.2(3) . . ? O3 C9 C8 119.1(3) . . ? C10 C9 C8 119.7(3) . . ? C1 C10 C9 119.6(3) . . ? C1 C10 C11 120.6(3) . . ? C9 C10 C11 119.7(3) . . ? C10 C11 C12 115.3(3) . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 125.9(3) . . ? C13 C12 H12 117.0 . . ? C11 C12 H12 117.0 . . ? C12 C13 C15 123.6(4) . . ? C12 C13 C14 121.7(4) . . ? C15 C13 C14 114.7(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 118.5(3) . . ? C21 C16 C22 120.3(3) . . ? C17 C16 C22 121.0(3) . . ? C21 C16 Os1 71.11(18) . . ? C17 C16 Os1 71.19(19) . . ? C22 C16 Os1 125.3(2) . . ? C18 C17 C16 119.5(3) . . ? C18 C17 Os1 70.42(19) . . ? C16 C17 Os1 70.40(18) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? Os1 C17 H17 131.7 . . ? C17 C18 C19 122.8(3) . . ? C17 C18 Os1 71.6(2) . . ? C19 C18 Os1 71.2(2) . . ? C17 C18 H18 118.6 . . ? C19 C18 H18 118.6 . . ? Os1 C18 H18 131.8 . . ? C20 C19 C18 116.5(3) . . ? C20 C19 C23 122.2(3) . . ? C18 C19 C23 121.3(3) . . ? C20 C19 Os1 70.05(19) . . ? C18 C19 Os1 70.4(2) . . ? C23 C19 Os1 129.4(2) . . ? C21 C20 C19 121.7(3) . . ? C21 C20 Os1 71.68(19) . . ? C19 C20 Os1 71.54(19) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? Os1 C20 H20 130.4 . . ? C20 C21 C16 120.9(3) . . ? C20 C21 Os1 70.17(19) . . ? C16 C21 Os1 70.71(19) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? Os1 C21 H21 132.7 . . ? C16 C22 H22A 109.5 . . ? C16 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C16 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C19 113.6(3) . . ? C25 C23 C24 110.8(4) . . ? C19 C23 C24 108.5(3) . . ? C25 C23 H23 107.9 . . ? C19 C23 H23 107.9 . . ? C24 C23 H23 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 O2 Os1 O1 C2 13.1(2) . . . . ? C20 Os1 O1 C2 90.7(3) . . . . ? C18 Os1 O1 C2 -154.6(2) . . . . ? C16 Os1 O1 C2 152.1(2) . . . . ? C21 Os1 O1 C2 115.5(2) . . . . ? C17 Os1 O1 C2 -173.5(2) . . . . ? Cl1 Os1 O1 C2 -73.7(2) . . . . ? O1 Os1 O2 C1 -12.9(2) . . . . ? C20 Os1 O2 C1 -147.6(2) . . . . ? C18 Os1 O2 C1 155.7(2) . . . . ? C16 Os1 O2 C1 -87.1(3) . . . . ? C19 Os1 O2 C1 176.1(2) . . . . ? C21 Os1 O2 C1 -111.6(2) . . . . ? Cl1 Os1 O2 C1 70.5(2) . . . . ? Os1 O2 C1 C10 -171.1(3) . . . . ? Os1 O2 C1 C2 11.3(4) . . . . ? Os1 O1 C2 C3 169.0(2) . . . . ? Os1 O1 C2 C1 -11.4(4) . . . . ? O2 C1 C2 O1 0.3(4) . . . . ? C10 C1 C2 O1 -177.4(3) . . . . ? O2 C1 C2 C3 179.9(3) . . . . ? C10 C1 C2 C3 2.2(5) . . . . ? O1 C2 C3 C4 -0.8(5) . . . . ? C1 C2 C3 C4 179.6(3) . . . . ? O1 C2 C3 C8 -178.4(3) . . . . ? C1 C2 C3 C8 2.0(5) . . . . ? C8 C3 C4 C5 0.1(5) . . . . ? C2 C3 C4 C5 -177.4(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C8 -1.4(5) . . . . ? C6 C7 C8 C3 2.0(5) . . . . ? C6 C7 C8 C9 -178.7(3) . . . . ? C4 C3 C8 C7 -1.3(5) . . . . ? C2 C3 C8 C7 176.3(3) . . . . ? C4 C3 C8 C9 179.3(3) . . . . ? C2 C3 C8 C9 -3.1(4) . . . . ? C7 C8 C9 O3 0.1(5) . . . . ? C3 C8 C9 O3 179.4(3) . . . . ? C7 C8 C9 C10 -179.1(3) . . . . ? C3 C8 C9 C10 0.2(5) . . . . ? O2 C1 C10 C9 177.4(3) . . . . ? C2 C1 C10 C9 -5.1(5) . . . . ? O2 C1 C10 C11 -2.5(5) . . . . ? C2 C1 C10 C11 174.9(3) . . . . ? O3 C9 C10 C1 -175.2(3) . . . . ? C8 C9 C10 C1 4.0(5) . . . . ? O3 C9 C10 C11 4.7(5) . . . . ? C8 C9 C10 C11 -176.0(3) . . . . ? C1 C10 C11 C12 93.1(4) . . . . ? C9 C10 C11 C12 -86.9(4) . . . . ? C10 C11 C12 C13 153.0(4) . . . . ? C11 C12 C13 C15 -1.2(6) . . . . ? C11 C12 C13 C14 176.6(3) . . . . ? O2 Os1 C16 C21 -40.3(3) . . . . ? O1 Os1 C16 C21 -109.2(2) . . . . ? C20 Os1 C16 C21 27.9(2) . . . . ? C18 Os1 C16 C21 101.7(2) . . . . ? C19 Os1 C16 C21 64.9(2) . . . . ? C17 Os1 C16 C21 130.5(3) . . . . ? Cl1 Os1 C16 C21 171.36(16) . . . . ? O2 Os1 C16 C17 -170.81(18) . . . . ? O1 Os1 C16 C17 120.4(2) . . . . ? C20 Os1 C16 C17 -102.6(2) . . . . ? C18 Os1 C16 C17 -28.8(2) . . . . ? C19 Os1 C16 C17 -65.6(2) . . . . ? C21 Os1 C16 C17 -130.5(3) . . . . ? Cl1 Os1 C16 C17 40.9(3) . . . . ? O2 Os1 C16 C22 74.0(3) . . . . ? O1 Os1 C16 C22 5.2(3) . . . . ? C20 Os1 C16 C22 142.2(3) . . . . ? C18 Os1 C16 C22 -144.0(3) . . . . ? C19 Os1 C16 C22 179.2(3) . . . . ? C21 Os1 C16 C22 114.3(4) . . . . ? C17 Os1 C16 C22 -115.2(4) . . . . ? Cl1 Os1 C16 C22 -74.3(3) . . . . ? C21 C16 C17 C18 -2.6(5) . . . . ? C22 C16 C17 C18 172.9(3) . . . . ? Os1 C16 C17 C18 52.4(3) . . . . ? C21 C16 C17 Os1 -55.0(3) . . . . ? C22 C16 C17 Os1 120.5(3) . . . . ? O1 Os1 C17 C18 161.62(19) . . . . ? C20 Os1 C17 C18 -65.4(2) . . . . ? C16 Os1 C17 C18 -133.0(3) . . . . ? C19 Os1 C17 C18 -27.5(2) . . . . ? C21 Os1 C17 C18 -102.6(2) . . . . ? Cl1 Os1 C17 C18 75.9(2) . . . . ? O1 Os1 C17 C16 -65.4(2) . . . . ? C20 Os1 C17 C16 67.6(2) . . . . ? C18 Os1 C17 C16 133.0(3) . . . . ? C19 Os1 C17 C16 105.5(2) . . . . ? C21 Os1 C17 C16 30.4(2) . . . . ? Cl1 Os1 C17 C16 -151.14(18) . . . . ? C16 C17 C18 C19 -0.6(5) . . . . ? Os1 C17 C18 C19 51.7(3) . . . . ? C16 C17 C18 Os1 -52.4(3) . . . . ? O2 Os1 C18 C17 168.65(18) . . . . ? O1 Os1 C18 C17 -30.1(3) . . . . ? C20 Os1 C18 C17 104.6(2) . . . . ? C16 Os1 C18 C17 29.1(2) . . . . ? C19 Os1 C18 C17 135.8(3) . . . . ? C21 Os1 C18 C17 67.0(2) . . . . ? Cl1 Os1 C18 C17 -108.2(2) . . . . ? O2 Os1 C18 C19 32.9(3) . . . . ? O1 Os1 C18 C19 -165.89(18) . . . . ? C20 Os1 C18 C19 -31.2(2) . . . . ? C16 Os1 C18 C19 -106.7(2) . . . . ? C21 Os1 C18 C19 -68.8(2) . . . . ? C17 Os1 C18 C19 -135.8(3) . . . . ? Cl1 Os1 C18 C19 116.0(2) . . . . ? C17 C18 C19 C20 2.5(5) . . . . ? Os1 C18 C19 C20 54.4(3) . . . . ? C17 C18 C19 C23 -176.8(3) . . . . ? Os1 C18 C19 C23 -124.9(3) . . . . ? C17 C18 C19 Os1 -51.9(3) . . . . ? O2 Os1 C19 C20 72.0(2) . . . . ? C18 Os1 C19 C20 -129.3(3) . . . . ? C16 Os1 C19 C20 -65.0(2) . . . . ? C21 Os1 C19 C20 -28.35(19) . . . . ? C17 Os1 C19 C20 -102.1(2) . . . . ? Cl1 Os1 C19 C20 161.18(17) . . . . ? O2 Os1 C19 C18 -158.7(2) . . . . ? C20 Os1 C19 C18 129.3(3) . . . . ? C16 Os1 C19 C18 64.2(2) . . . . ? C21 Os1 C19 C18 100.9(2) . . . . ? C17 Os1 C19 C18 27.2(2) . . . . ? Cl1 Os1 C19 C18 -69.6(2) . . . . ? O2 Os1 C19 C23 -43.8(4) . . . . ? C20 Os1 C19 C23 -115.8(4) . . . . ? C18 Os1 C19 C23 114.9(4) . . . . ? C16 Os1 C19 C23 179.1(4) . . . . ? C21 Os1 C19 C23 -144.2(4) . . . . ? C17 Os1 C19 C23 142.1(4) . . . . ? Cl1 Os1 C19 C23 45.3(4) . . . . ? C18 C19 C20 C21 -1.1(5) . . . . ? C23 C19 C20 C21 178.1(3) . . . . ? Os1 C19 C20 C21 53.5(3) . . . . ? C18 C19 C20 Os1 -54.6(3) . . . . ? C23 C19 C20 Os1 124.7(3) . . . . ? O2 Os1 C20 C21 112.80(19) . . . . ? O1 Os1 C20 C21 41.6(2) . . . . ? C18 Os1 C20 C21 -102.7(2) . . . . ? C16 Os1 C20 C21 -27.93(19) . . . . ? C19 Os1 C20 C21 -133.9(3) . . . . ? C17 Os1 C20 C21 -65.7(2) . . . . ? Cl1 Os1 C20 C21 -163.93(15) . . . . ? O2 Os1 C20 C19 -113.3(2) . . . . ? O1 Os1 C20 C19 175.52(17) . . . . ? C18 Os1 C20 C19 31.2(2) . . . . ? C16 Os1 C20 C19 106.0(2) . . . . ? C21 Os1 C20 C19 133.9(3) . . . . ? C17 Os1 C20 C19 68.2(2) . . . . ? Cl1 Os1 C20 C19 -30.0(3) . . . . ? C19 C20 C21 C16 -2.1(5) . . . . ? Os1 C20 C21 C16 51.3(3) . . . . ? C19 C20 C21 Os1 -53.4(3) . . . . ? C17 C16 C21 C20 3.9(5) . . . . ? C22 C16 C21 C20 -171.6(3) . . . . ? Os1 C16 C21 C20 -51.1(3) . . . . ? C17 C16 C21 Os1 55.0(3) . . . . ? C22 C16 C21 Os1 -120.5(3) . . . . ? O2 Os1 C21 C20 -72.4(2) . . . . ? O1 Os1 C21 C20 -150.47(18) . . . . ? C18 Os1 C21 C20 66.8(2) . . . . ? C16 Os1 C21 C20 134.8(3) . . . . ? C19 Os1 C21 C20 28.53(19) . . . . ? C17 Os1 C21 C20 104.2(2) . . . . ? O2 Os1 C21 C16 152.9(2) . . . . ? O1 Os1 C21 C16 74.8(2) . . . . ? C20 Os1 C21 C16 -134.8(3) . . . . ? C18 Os1 C21 C16 -68.0(2) . . . . ? C19 Os1 C21 C16 -106.2(2) . . . . ? C17 Os1 C21 C16 -30.5(2) . . . . ? C20 C19 C23 C25 -31.9(5) . . . . ? C18 C19 C23 C25 147.3(4) . . . . ? Os1 C19 C23 C25 57.8(5) . . . . ? C20 C19 C23 C24 91.8(4) . . . . ? C18 C19 C23 C24 -89.0(4) . . . . ? Os1 C19 C23 C24 -178.5(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.806 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.119