# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 890355' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 Cl F Ir N O, C H2 Cl2' _chemical_formula_sum 'C27 H30 Cl3 F Ir N O' _chemical_formula_weight 702.07 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' F F 0.0171 0.0103 '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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5225(9) _cell_length_b 14.1788(16) _cell_length_c 22.958(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2774.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7552 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 33.23 _exptl_crystal_description fragment _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 5.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3095 _exptl_absorpt_correction_T_max 0.8697 _exptl_absorpt_process_details ; Sheldrick, G.M. (2002). SADABS v. 2.03. University of Gottingen, Germany. ; _exptl_special_details ; Rotating anode power 4 kW. ; _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 X8 Apex diffractometer' _diffrn_measurement_method 'Rotation images' _diffrn_detector_area_resol_mean '120 microns' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 56356 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 35.69 _reflns_number_total 11067 _reflns_number_gt 10010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 software, Bruker Nonius 2004' _computing_cell_refinement 'APEX 2 software, Bruker Nonius 2004' _computing_data_reduction 'SAINT, Bruker Nonius 2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _refine_special_details ; Data completeness is 90% complete to 0.6 angstroms F39 bound to aromatic ring C35-C40 was disordered over two positions, C39A and C37B F39A C39A C37A and H37A were refined as part 1 at 61% occupancy F39B C37B C39A and H39B were refined as part 2 at 39% occupancy Highest peak 1.76 at 0.7559 0.9857 0.1908 '[' 0.72 A from IR1 ] Deepest hole -1.11 at 0.8118 0.4722 0.0847 '[' 0.63 A from CL3 ] There was slight disorder present at the cp ring. The following restraints were used during refinement. DFIX 1.43 0.02 C1 C2 DFIX 1.43 0.02 C1 C5 SIMU C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 DELU C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 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^)+(0.0403P)^2^+0.1443P] 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' _refine_ls_abs_structure_Flack 0.003(5) _refine_ls_number_reflns 11067 _refine_ls_number_parameters 319 _refine_ls_number_restraints 87 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.031 _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 Ir1 Ir 0.687600(13) 0.956241(7) 0.188733(5) 0.02592(3) Uani 1 1 d . . . Cl1 Cl 0.95113(10) 1.00843(6) 0.22175(4) 0.03490(15) Uani 1 1 d . . . Cl2 Cl -0.11989(18) 0.99078(11) 0.40823(7) 0.0736(4) Uani 1 1 d . . . Cl3 Cl 0.21221(17) 0.93713(13) 0.40132(7) 0.0814(4) Uani 1 1 d . . . F39A F 0.8256(5) 0.5860(3) 0.44614(17) 0.0556(10) Uani 0.61 1 d P A 1 O31 O 0.6762(3) 0.88072(15) 0.26733(9) 0.0328(4) Uani 1 1 d . . . N31 N 0.8145(3) 0.84185(17) 0.15215(11) 0.0270(4) Uani 1 1 d . . . C1 C 0.5834(5) 1.0967(3) 0.1939(2) 0.0522(10) Uani 1 1 d DU . . C2 C 0.6275(4) 1.0735(3) 0.13202(17) 0.0396(8) Uani 1 1 d DU . . C3 C 0.5302(4) 0.9946(3) 0.11617(16) 0.0402(8) Uani 1 1 d U . . C4 C 0.4411(4) 0.9648(3) 0.16558(18) 0.0421(7) Uani 1 1 d U . . C5 C 0.4714(4) 1.0296(3) 0.21257(17) 0.0453(9) Uani 1 1 d DU . . C6 C 0.7343(6) 1.1295(4) 0.0931(3) 0.0757(18) Uani 1 1 d U . . H6A H 0.7703 1.0896 0.0609 0.114 Uiso 1 1 calc R . . H6B H 0.8250 1.1515 0.1155 0.114 Uiso 1 1 calc R . . H6C H 0.6772 1.1838 0.0774 0.114 Uiso 1 1 calc R . . C7 C 0.5159(5) 0.9519(4) 0.05464(19) 0.0568(11) Uani 1 1 d U . . H7A H 0.4940 0.8842 0.0577 0.085 Uiso 1 1 calc R . . H7B H 0.6145 0.9613 0.0334 0.085 Uiso 1 1 calc R . . H7C H 0.4302 0.9829 0.0336 0.085 Uiso 1 1 calc R . . C8 C 0.3180(5) 0.8842(3) 0.1661(3) 0.0633(12) Uani 1 1 d U . . H8A H 0.2976 0.8648 0.2063 0.095 Uiso 1 1 calc R . . H8B H 0.3583 0.8304 0.1439 0.095 Uiso 1 1 calc R . . H8C H 0.2203 0.9066 0.1483 0.095 Uiso 1 1 calc R . . C9 C 0.3973(6) 1.0251(4) 0.2730(2) 0.0652(14) Uani 1 1 d U . . H9A H 0.4766 1.0402 0.3025 0.098 Uiso 1 1 calc R . . H9B H 0.3563 0.9616 0.2799 0.098 Uiso 1 1 calc R . . H9C H 0.3113 1.0709 0.2754 0.098 Uiso 1 1 calc R . . C10 C 0.6551(7) 1.1803(4) 0.2259(3) 0.083(2) Uani 1 1 d U . . H10C H 0.5821 1.2337 0.2247 0.124 Uiso 1 1 calc R . . H10A H 0.7540 1.1982 0.2071 0.124 Uiso 1 1 calc R . . H10B H 0.6752 1.1629 0.2665 0.124 Uiso 1 1 calc R . . C24 C 0.0278(7) 0.9283(4) 0.3699(2) 0.0637(13) Uani 1 1 d . . . H24A H -0.0022 0.8610 0.3678 0.076 Uiso 1 1 calc R . . H24B H 0.0331 0.9527 0.3295 0.076 Uiso 1 1 calc R . . C31 C 0.9804(5) 0.6977(3) 0.15164(18) 0.0450(9) Uani 1 1 d . . . H31A H 0.9161 0.6577 0.1262 0.067 Uiso 1 1 calc R . . H31B H 1.0328 0.6583 0.1808 0.067 Uiso 1 1 calc R . . H31C H 1.0594 0.7306 0.1282 0.067 Uiso 1 1 calc R . . C32 C 0.8753(3) 0.7701(2) 0.18234(15) 0.0289(6) Uani 1 1 d . . . C33 C 0.8506(4) 0.7542(2) 0.24360(15) 0.0335(7) Uani 1 1 d . . . H33 H 0.9097 0.7047 0.2608 0.040 Uiso 1 1 calc R . . C34 C 0.7510(3) 0.8027(2) 0.27987(14) 0.0282(6) Uani 1 1 d . . . C35 C 0.7207(4) 0.7686(2) 0.34172(15) 0.0319(6) Uani 1 1 d . C . C36 C 0.6227(5) 0.8211(3) 0.37833(16) 0.0392(7) Uani 1 1 d . . . H36 H 0.5727 0.8761 0.3638 0.047 Uiso 1 1 calc R B 1 C37A C 0.5976(5) 0.7936(3) 0.43586(18) 0.0439(8) Uani 0.61 1 d P C 1 H37A H 0.5306 0.8306 0.4598 0.053 Uiso 0.61 1 calc PR C 1 C37B C 0.5976(5) 0.7936(3) 0.43586(18) 0.0439(8) Uani 0.39 1 d P C 2 C38 C 0.6676(5) 0.7139(3) 0.45915(16) 0.0442(8) Uani 1 1 d . . . H38 H 0.6507 0.6959 0.4985 0.053 Uiso 1 1 calc R C 1 C39A C 0.7634(5) 0.6614(3) 0.42267(17) 0.0418(8) Uani 0.61 1 d P A 1 C39B C 0.7634(5) 0.6614(3) 0.42267(17) 0.0418(8) Uani 0.39 1 d P C 2 H39B H 0.8121 0.6063 0.4378 0.050 Uiso 0.39 1 calc PR C 2 C40 C 0.7914(4) 0.6859(2) 0.36467(14) 0.0334(6) Uani 1 1 d . . . H40 H 0.8569 0.6477 0.3409 0.040 Uiso 1 1 calc R C 1 C51 C 0.8382(3) 0.8436(2) 0.09003(14) 0.0285(6) Uani 1 1 d . . . C52 C 0.9377(4) 0.9126(2) 0.06553(16) 0.0350(6) Uani 1 1 d . . . H52 H 0.9902 0.9569 0.0897 0.042 Uiso 1 1 calc R . . C53 C 0.9579(5) 0.9147(3) 0.00472(18) 0.0459(9) Uani 1 1 d . . . H53 H 1.0249 0.9609 -0.0120 0.055 Uiso 1 1 calc R . . C54 C 0.8818(5) 0.8506(3) -0.03138(18) 0.0507(10) Uani 1 1 d . . . H54 H 0.8953 0.8533 -0.0724 0.061 Uiso 1 1 calc R . . C55 C 0.7839(5) 0.7813(3) -0.00603(17) 0.0483(10) Uani 1 1 d . . . H55 H 0.7338 0.7361 -0.0303 0.058 Uiso 1 1 calc R . . C56 C 0.7602(4) 0.7783(2) 0.05289(13) 0.0379(7) Uani 1 1 d . . . H56 H 0.6915 0.7325 0.0691 0.045 Uiso 1 1 calc R . . F39B F 0.5122(4) 0.8416(2) 0.46881(13) 0.0432(13) Uani 0.39 1 d PR C 2 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 Ir1 0.02786(5) 0.02817(5) 0.02172(5) 0.00267(4) -0.00106(4) 0.00709(4) Cl1 0.0352(3) 0.0336(3) 0.0359(4) 0.0001(3) -0.0062(3) -0.0025(3) Cl2 0.0812(8) 0.0729(8) 0.0668(8) -0.0091(6) 0.0180(6) -0.0276(7) Cl3 0.0692(8) 0.1130(12) 0.0619(8) 0.0245(8) -0.0134(6) -0.0191(8) F39A 0.068(3) 0.054(2) 0.045(2) 0.0231(17) 0.007(2) 0.022(2) O31 0.0371(11) 0.0342(10) 0.0271(10) 0.0072(8) 0.0019(9) 0.0098(10) N31 0.0270(10) 0.0291(10) 0.0248(11) 0.0014(8) -0.0030(10) 0.0012(10) C1 0.057(2) 0.0382(16) 0.061(2) -0.0136(17) -0.0282(19) 0.0227(16) C2 0.0327(14) 0.0442(17) 0.042(2) 0.0168(14) 0.0038(13) 0.0128(13) C3 0.0388(17) 0.0473(18) 0.0344(17) 0.0009(14) -0.0120(13) 0.0184(15) C4 0.0321(14) 0.0425(18) 0.052(2) 0.0098(15) -0.0028(14) 0.0096(15) C5 0.0375(16) 0.064(2) 0.0344(17) 0.0089(16) 0.0033(13) 0.0289(16) C6 0.057(3) 0.057(3) 0.113(5) 0.048(3) 0.016(3) 0.017(2) C7 0.054(2) 0.072(3) 0.045(2) -0.007(2) -0.0190(17) 0.025(2) C8 0.0371(18) 0.057(2) 0.096(4) 0.013(2) 0.001(2) 0.008(2) C9 0.060(3) 0.089(4) 0.046(2) 0.005(2) 0.0118(19) 0.032(3) C10 0.085(4) 0.047(2) 0.116(5) -0.032(3) -0.044(4) 0.021(3) C24 0.074(3) 0.073(3) 0.044(3) -0.005(2) -0.010(2) 0.001(3) C31 0.053(2) 0.045(2) 0.0362(19) 0.0060(15) 0.0079(16) 0.0222(17) C32 0.0272(12) 0.0291(13) 0.0304(16) 0.0008(11) 0.0003(11) 0.0023(10) C33 0.0384(16) 0.0329(14) 0.0292(16) 0.0071(12) -0.0008(12) 0.0051(12) C34 0.0252(12) 0.0311(14) 0.0284(15) 0.0049(11) -0.0049(11) 0.0017(11) C35 0.0307(15) 0.0354(15) 0.0297(16) 0.0070(12) -0.0034(11) -0.0022(12) C36 0.0450(17) 0.0406(17) 0.0320(18) 0.0089(14) 0.0034(13) 0.0074(15) C37A 0.048(2) 0.051(2) 0.0325(18) 0.0058(16) 0.0030(15) 0.0010(16) C37B 0.048(2) 0.051(2) 0.0325(18) 0.0058(16) 0.0030(15) 0.0010(16) C38 0.057(2) 0.0478(19) 0.0275(16) 0.0105(14) -0.0023(16) -0.0068(19) C39A 0.0475(19) 0.0437(18) 0.0341(19) 0.0150(15) -0.0049(14) -0.0046(15) C39B 0.0475(19) 0.0437(18) 0.0341(19) 0.0150(15) -0.0049(14) -0.0046(15) C40 0.0356(16) 0.0351(14) 0.0295(15) 0.0073(12) -0.0046(12) 0.0010(13) C51 0.0265(13) 0.0292(13) 0.0299(15) -0.0006(11) 0.0000(10) 0.0079(11) C52 0.0395(15) 0.0322(14) 0.0334(16) 0.0031(12) 0.0039(14) 0.0031(13) C53 0.051(2) 0.0454(19) 0.041(2) 0.0121(16) 0.0146(17) 0.0140(18) C54 0.058(2) 0.069(3) 0.0249(18) -0.0008(17) 0.0055(15) 0.025(2) C55 0.050(2) 0.063(2) 0.0322(18) -0.0136(17) -0.0107(15) 0.0182(19) C56 0.0355(15) 0.0429(18) 0.0352(19) -0.0021(14) -0.0033(13) 0.0033(14) F39B 0.050(3) 0.056(3) 0.024(3) -0.001(2) 0.014(2) 0.015(3) _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 Ir1 O31 2.100(2) . ? Ir1 N31 2.123(3) . ? Ir1 C4 2.171(4) . ? Ir1 C2 2.173(3) . ? Ir1 C1 2.183(3) . ? Ir1 C5 2.185(3) . ? Ir1 C3 2.207(3) . ? Ir1 Cl1 2.4832(9) . ? Cl2 C24 1.773(6) . ? Cl3 C24 1.734(6) . ? F39A C39A 1.308(5) . ? O31 C34 1.308(4) . ? N31 C32 1.335(4) . ? N31 C51 1.441(4) . ? C1 C5 1.414(6) . ? C1 C2 1.506(6) . ? C1 C10 1.523(6) . ? C2 C3 1.439(6) . ? C2 C6 1.503(6) . ? C3 C4 1.429(6) . ? C3 C7 1.542(6) . ? C4 C5 1.441(6) . ? C4 C8 1.551(6) . ? C5 C9 1.526(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C31 C32 1.535(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.440(5) . ? C33 C34 1.374(5) . ? C33 H33 0.9500 . ? C34 C35 1.522(5) . ? C35 C36 1.399(5) . ? C35 C40 1.420(4) . ? C36 C37A 1.393(5) . ? C36 H36 0.9500 . ? C37A C38 1.386(6) . ? C37A H37A 0.9500 . ? C38 C39A 1.386(6) . ? C38 H38 0.9500 . ? C39A C40 1.397(5) . ? C40 H40 0.9500 . ? C51 C52 1.413(5) . ? C51 C56 1.423(4) . ? C52 C53 1.407(5) . ? C52 H52 0.9500 . ? C53 C54 1.391(7) . ? C53 H53 0.9500 . ? C54 C55 1.414(7) . ? C54 H54 0.9500 . ? C55 C56 1.368(5) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? 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 O31 Ir1 N31 88.51(9) . . ? O31 Ir1 C4 101.18(12) . . ? N31 Ir1 C4 116.03(13) . . ? O31 Ir1 C2 153.37(12) . . ? N31 Ir1 C2 117.88(12) . . ? C4 Ir1 C2 65.31(14) . . ? O31 Ir1 C1 113.55(15) . . ? N31 Ir1 C1 157.75(15) . . ? C4 Ir1 C1 64.46(15) . . ? C2 Ir1 C1 40.44(17) . . ? O31 Ir1 C5 89.34(12) . . ? N31 Ir1 C5 153.15(14) . . ? C4 Ir1 C5 38.62(16) . . ? C2 Ir1 C5 65.62(14) . . ? C1 Ir1 C5 37.77(17) . . ? O31 Ir1 C3 138.24(13) . . ? N31 Ir1 C3 101.49(12) . . ? C4 Ir1 C3 38.11(15) . . ? C2 Ir1 C3 38.34(16) . . ? C1 Ir1 C3 64.47(15) . . ? C5 Ir1 C3 63.86(14) . . ? O31 Ir1 Cl1 86.08(7) . . ? N31 Ir1 Cl1 83.55(7) . . ? C4 Ir1 Cl1 159.01(11) . . ? C2 Ir1 Cl1 99.69(11) . . ? C1 Ir1 Cl1 94.56(11) . . ? C5 Ir1 Cl1 122.98(12) . . ? C3 Ir1 Cl1 134.97(11) . . ? C34 O31 Ir1 126.7(2) . . ? C32 N31 C51 118.2(3) . . ? C32 N31 Ir1 125.0(2) . . ? C51 N31 Ir1 116.75(18) . . ? C5 C1 C2 107.9(3) . . ? C5 C1 C10 130.4(5) . . ? C2 C1 C10 121.7(5) . . ? C5 C1 Ir1 71.2(2) . . ? C2 C1 Ir1 69.39(19) . . ? C10 C1 Ir1 125.0(3) . . ? C3 C2 C6 127.5(4) . . ? C3 C2 C1 105.4(3) . . ? C6 C2 C1 126.6(5) . . ? C3 C2 Ir1 72.1(2) . . ? C6 C2 Ir1 128.2(3) . . ? C1 C2 Ir1 70.17(19) . . ? C4 C3 C2 109.6(3) . . ? C4 C3 C7 124.7(4) . . ? C2 C3 C7 125.6(4) . . ? C4 C3 Ir1 69.6(2) . . ? C2 C3 Ir1 69.54(19) . . ? C7 C3 Ir1 130.0(2) . . ? C3 C4 C5 108.1(3) . . ? C3 C4 C8 125.7(4) . . ? C5 C4 C8 125.9(4) . . ? C3 C4 Ir1 72.3(2) . . ? C5 C4 Ir1 71.2(2) . . ? C8 C4 Ir1 127.7(3) . . ? C1 C5 C4 108.9(3) . . ? C1 C5 C9 125.7(4) . . ? C4 C5 C9 125.5(4) . . ? C1 C5 Ir1 71.05(19) . . ? C4 C5 Ir1 70.1(2) . . ? C9 C5 Ir1 123.9(3) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 H10C 109.5 . . ? C1 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Cl3 C24 Cl2 113.6(3) . . ? Cl3 C24 H24A 108.8 . . ? Cl2 C24 H24A 108.8 . . ? Cl3 C24 H24B 108.8 . . ? Cl2 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C32 C31 H31A 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C32 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N31 C32 C33 124.7(3) . . ? N31 C32 C31 119.9(3) . . ? C33 C32 C31 115.4(3) . . ? C34 C33 C32 127.1(3) . . ? C34 C33 H33 116.4 . . ? C32 C33 H33 116.4 . . ? O31 C34 C33 126.2(3) . . ? O31 C34 C35 113.1(3) . . ? C33 C34 C35 120.7(3) . . ? C36 C35 C40 118.0(3) . . ? C36 C35 C34 119.5(3) . . ? C40 C35 C34 122.5(3) . . ? C37A C36 C35 120.8(3) . . ? C37A C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C38 C37A C36 121.8(4) . . ? C38 C37A H37A 119.1 . . ? C36 C37A H37A 119.1 . . ? C37A C38 C39A 117.3(3) . . ? C37A C38 H38 121.4 . . ? C39A C38 H38 121.4 . . ? F39A C39A C38 115.3(4) . . ? F39A C39A C40 121.8(4) . . ? C38 C39A C40 122.9(3) . . ? C39A C40 C35 119.1(3) . . ? C39A C40 H40 120.4 . . ? C35 C40 H40 120.4 . . ? C52 C51 C56 119.5(3) . . ? C52 C51 N31 119.3(3) . . ? C56 C51 N31 121.1(3) . . ? C53 C52 C51 118.9(4) . . ? C53 C52 H52 120.6 . . ? C51 C52 H52 120.6 . . ? C54 C53 C52 121.4(4) . . ? C54 C53 H53 119.3 . . ? C52 C53 H53 119.3 . . ? C53 C54 C55 119.0(4) . . ? C53 C54 H54 120.5 . . ? C55 C54 H54 120.5 . . ? C56 C55 C54 121.0(4) . . ? C56 C55 H55 119.5 . . ? C54 C55 H55 119.5 . . ? C55 C56 C51 120.2(3) . . ? C55 C56 H56 119.9 . . ? C51 C56 H56 119.9 . . ? 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 N31 Ir1 O31 C34 9.2(3) . . . . ? C4 Ir1 O31 C34 125.5(3) . . . . ? C2 Ir1 O31 C34 -178.3(3) . . . . ? C1 Ir1 O31 C34 -167.7(3) . . . . ? C5 Ir1 O31 C34 162.5(3) . . . . ? C3 Ir1 O31 C34 114.9(3) . . . . ? Cl1 Ir1 O31 C34 -74.4(3) . . . . ? O31 Ir1 N31 C32 -11.8(3) . . . . ? C4 Ir1 N31 C32 -113.5(3) . . . . ? C2 Ir1 N31 C32 172.0(3) . . . . ? C1 Ir1 N31 C32 160.8(3) . . . . ? C5 Ir1 N31 C32 -97.3(3) . . . . ? C3 Ir1 N31 C32 -150.9(3) . . . . ? Cl1 Ir1 N31 C32 74.5(2) . . . . ? O31 Ir1 N31 C51 169.4(2) . . . . ? C4 Ir1 N31 C51 67.6(2) . . . . ? C2 Ir1 N31 C51 -6.8(3) . . . . ? C1 Ir1 N31 C51 -18.1(4) . . . . ? C5 Ir1 N31 C51 83.8(3) . . . . ? C3 Ir1 N31 C51 30.2(2) . . . . ? Cl1 Ir1 N31 C51 -104.4(2) . . . . ? O31 Ir1 C1 C5 -54.3(3) . . . . ? N31 Ir1 C1 C5 133.8(3) . . . . ? C4 Ir1 C1 C5 37.2(2) . . . . ? C2 Ir1 C1 C5 118.4(3) . . . . ? C3 Ir1 C1 C5 79.6(2) . . . . ? Cl1 Ir1 C1 C5 -142.0(2) . . . . ? O31 Ir1 C1 C2 -172.7(2) . . . . ? N31 Ir1 C1 C2 15.5(5) . . . . ? C4 Ir1 C1 C2 -81.2(2) . . . . ? C5 Ir1 C1 C2 -118.4(3) . . . . ? C3 Ir1 C1 C2 -38.8(2) . . . . ? Cl1 Ir1 C1 C2 99.6(2) . . . . ? O31 Ir1 C1 C10 72.3(5) . . . . ? N31 Ir1 C1 C10 -99.5(6) . . . . ? C4 Ir1 C1 C10 163.8(6) . . . . ? C2 Ir1 C1 C10 -115.0(6) . . . . ? C5 Ir1 C1 C10 126.7(6) . . . . ? C3 Ir1 C1 C10 -153.7(6) . . . . ? Cl1 Ir1 C1 C10 -15.4(5) . . . . ? C5 C1 C2 C3 3.0(4) . . . . ? C10 C1 C2 C3 -176.8(3) . . . . ? Ir1 C1 C2 C3 64.0(2) . . . . ? C5 C1 C2 C6 175.5(3) . . . . ? C10 C1 C2 C6 -4.2(6) . . . . ? Ir1 C1 C2 C6 -123.4(4) . . . . ? C5 C1 C2 Ir1 -61.1(2) . . . . ? C10 C1 C2 Ir1 119.2(4) . . . . ? O31 Ir1 C2 C3 -99.3(3) . . . . ? N31 Ir1 C2 C3 72.2(2) . . . . ? C4 Ir1 C2 C3 -35.4(2) . . . . ? C1 Ir1 C2 C3 -114.3(3) . . . . ? C5 Ir1 C2 C3 -78.1(2) . . . . ? Cl1 Ir1 C2 C3 160.00(19) . . . . ? O31 Ir1 C2 C6 136.6(4) . . . . ? N31 Ir1 C2 C6 -51.9(5) . . . . ? C4 Ir1 C2 C6 -159.5(5) . . . . ? C1 Ir1 C2 C6 121.6(6) . . . . ? C5 Ir1 C2 C6 157.8(5) . . . . ? C3 Ir1 C2 C6 -124.1(6) . . . . ? Cl1 Ir1 C2 C6 35.9(5) . . . . ? O31 Ir1 C2 C1 15.1(4) . . . . ? N31 Ir1 C2 C1 -173.4(2) . . . . ? C4 Ir1 C2 C1 78.9(2) . . . . ? C5 Ir1 C2 C1 36.3(2) . . . . ? C3 Ir1 C2 C1 114.3(3) . . . . ? Cl1 Ir1 C2 C1 -85.6(2) . . . . ? C6 C2 C3 C4 -177.1(3) . . . . ? C1 C2 C3 C4 -4.6(4) . . . . ? Ir1 C2 C3 C4 58.1(2) . . . . ? C6 C2 C3 C7 -0.4(6) . . . . ? C1 C2 C3 C7 172.1(3) . . . . ? Ir1 C2 C3 C7 -125.2(3) . . . . ? C6 C2 C3 Ir1 124.8(4) . . . . ? C1 C2 C3 Ir1 -62.7(2) . . . . ? O31 Ir1 C3 C4 17.0(3) . . . . ? N31 Ir1 C3 C4 117.8(2) . . . . ? C2 Ir1 C3 C4 -121.4(3) . . . . ? C1 Ir1 C3 C4 -80.5(3) . . . . ? C5 Ir1 C3 C4 -38.3(2) . . . . ? Cl1 Ir1 C3 C4 -149.85(19) . . . . ? O31 Ir1 C3 C2 138.4(2) . . . . ? N31 Ir1 C3 C2 -120.8(2) . . . . ? C4 Ir1 C3 C2 121.4(3) . . . . ? C1 Ir1 C3 C2 40.9(2) . . . . ? C5 Ir1 C3 C2 83.1(2) . . . . ? Cl1 Ir1 C3 C2 -28.5(3) . . . . ? O31 Ir1 C3 C7 -101.7(4) . . . . ? N31 Ir1 C3 C7 -0.9(4) . . . . ? C4 Ir1 C3 C7 -118.7(5) . . . . ? C2 Ir1 C3 C7 119.9(5) . . . . ? C1 Ir1 C3 C7 160.8(5) . . . . ? C5 Ir1 C3 C7 -157.0(5) . . . . ? Cl1 Ir1 C3 C7 91.5(4) . . . . ? C2 C3 C4 C5 4.6(4) . . . . ? C7 C3 C4 C5 -172.1(3) . . . . ? Ir1 C3 C4 C5 62.7(2) . . . . ? C2 C3 C4 C8 177.7(3) . . . . ? C7 C3 C4 C8 1.0(6) . . . . ? Ir1 C3 C4 C8 -124.2(4) . . . . ? C2 C3 C4 Ir1 -58.1(2) . . . . ? C7 C3 C4 Ir1 125.2(3) . . . . ? O31 Ir1 C4 C3 -168.6(2) . . . . ? N31 Ir1 C4 C3 -74.7(2) . . . . ? C2 Ir1 C4 C3 35.6(2) . . . . ? C1 Ir1 C4 C3 80.5(3) . . . . ? C5 Ir1 C4 C3 116.9(3) . . . . ? Cl1 Ir1 C4 C3 82.7(4) . . . . ? O31 Ir1 C4 C5 74.6(2) . . . . ? N31 Ir1 C4 C5 168.4(2) . . . . ? C2 Ir1 C4 C5 -81.2(2) . . . . ? C1 Ir1 C4 C5 -36.4(2) . . . . ? C3 Ir1 C4 C5 -116.9(3) . . . . ? Cl1 Ir1 C4 C5 -34.1(4) . . . . ? O31 Ir1 C4 C8 -46.8(4) . . . . ? N31 Ir1 C4 C8 47.1(4) . . . . ? C2 Ir1 C4 C8 157.5(5) . . . . ? C1 Ir1 C4 C8 -157.7(5) . . . . ? C5 Ir1 C4 C8 -121.3(5) . . . . ? C3 Ir1 C4 C8 121.8(5) . . . . ? Cl1 Ir1 C4 C8 -155.5(3) . . . . ? C2 C1 C5 C4 -0.3(4) . . . . ? C10 C1 C5 C4 179.4(4) . . . . ? Ir1 C1 C5 C4 -60.2(2) . . . . ? C2 C1 C5 C9 178.6(3) . . . . ? C10 C1 C5 C9 -1.7(6) . . . . ? Ir1 C1 C5 C9 118.6(4) . . . . ? C2 C1 C5 Ir1 59.9(2) . . . . ? C10 C1 C5 Ir1 -120.3(4) . . . . ? C3 C4 C5 C1 -2.6(4) . . . . ? C8 C4 C5 C1 -175.7(3) . . . . ? Ir1 C4 C5 C1 60.8(2) . . . . ? C3 C4 C5 C9 178.6(3) . . . . ? C8 C4 C5 C9 5.5(6) . . . . ? Ir1 C4 C5 C9 -118.1(4) . . . . ? C3 C4 C5 Ir1 -63.4(2) . . . . ? C8 C4 C5 Ir1 123.5(4) . . . . ? O31 Ir1 C5 C1 131.9(2) . . . . ? N31 Ir1 C5 C1 -142.8(3) . . . . ? C4 Ir1 C5 C1 -119.2(3) . . . . ? C2 Ir1 C5 C1 -38.8(2) . . . . ? C3 Ir1 C5 C1 -81.4(3) . . . . ? Cl1 Ir1 C5 C1 47.0(3) . . . . ? O31 Ir1 C5 C4 -109.0(2) . . . . ? N31 Ir1 C5 C4 -23.6(4) . . . . ? C2 Ir1 C5 C4 80.4(2) . . . . ? C1 Ir1 C5 C4 119.2(3) . . . . ? C3 Ir1 C5 C4 37.8(2) . . . . ? Cl1 Ir1 C5 C4 166.13(18) . . . . ? O31 Ir1 C5 C9 11.1(4) . . . . ? N31 Ir1 C5 C9 96.4(5) . . . . ? C4 Ir1 C5 C9 120.0(5) . . . . ? C2 Ir1 C5 C9 -159.6(5) . . . . ? C1 Ir1 C5 C9 -120.8(5) . . . . ? C3 Ir1 C5 C9 157.9(5) . . . . ? Cl1 Ir1 C5 C9 -73.8(4) . . . . ? C51 N31 C32 C33 -174.5(3) . . . . ? Ir1 N31 C32 C33 6.6(4) . . . . ? C51 N31 C32 C31 5.8(5) . . . . ? Ir1 N31 C32 C31 -173.1(3) . . . . ? N31 C32 C33 C34 6.8(6) . . . . ? C31 C32 C33 C34 -173.5(4) . . . . ? Ir1 O31 C34 C33 -0.8(5) . . . . ? Ir1 O31 C34 C35 177.83(19) . . . . ? C32 C33 C34 O31 -10.2(6) . . . . ? C32 C33 C34 C35 171.2(3) . . . . ? O31 C34 C35 C36 -0.8(4) . . . . ? C33 C34 C35 C36 177.9(3) . . . . ? O31 C34 C35 C40 -179.3(3) . . . . ? C33 C34 C35 C40 -0.6(5) . . . . ? C40 C35 C36 C37A 1.0(6) . . . . ? C34 C35 C36 C37A -177.5(3) . . . . ? C35 C36 C37A C38 -0.1(6) . . . . ? C36 C37A C38 C39A -0.6(6) . . . . ? C37A C38 C39A F39A -179.2(4) . . . . ? C37A C38 C39A C40 0.2(6) . . . . ? F39A C39A C40 C35 -179.9(4) . . . . ? C38 C39A C40 C35 0.7(6) . . . . ? C36 C35 C40 C39A -1.3(5) . . . . ? C34 C35 C40 C39A 177.2(3) . . . . ? C32 N31 C51 C52 -110.6(3) . . . . ? Ir1 N31 C51 C52 68.4(3) . . . . ? C32 N31 C51 C56 70.9(4) . . . . ? Ir1 N31 C51 C56 -110.2(3) . . . . ? C56 C51 C52 C53 -0.3(5) . . . . ? N31 C51 C52 C53 -178.9(3) . . . . ? C51 C52 C53 C54 0.1(5) . . . . ? C52 C53 C54 C55 -0.8(6) . . . . ? C53 C54 C55 C56 1.7(6) . . . . ? C54 C55 C56 C51 -1.9(5) . . . . ? C52 C51 C56 C55 1.2(4) . . . . ? N31 C51 C56 C55 179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 35.69 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 1.806 _refine_diff_density_min -0.980 _refine_diff_density_rms 0.115 data_2 _database_code_depnum_ccdc_archive 'CCDC 890356' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H27 Cl F N O Ru' _chemical_formula_sum 'C26 H27 Cl F N O Ru' _chemical_formula_weight 525.01 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8410(5) _cell_length_b 10.4805(6) _cell_length_c 12.3289(7) _cell_angle_alpha 100.643(2) _cell_angle_beta 102.502(2) _cell_angle_gamma 104.424(2) _cell_volume 1163.39(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8144 _cell_measurement_theta_min 2.5425 _cell_measurement_theta_max 30.4825 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8693 _exptl_absorpt_correction_T_max 0.9100 _exptl_absorpt_process_details ; Sheldrick, G.M. (2002). SADABS v. 2.03. University of Gottingen, Germany. ; _exptl_special_details ; Rotating anode power 4 kW. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex diffractometer' _diffrn_measurement_method 'Rotation images' _diffrn_detector_area_resol_mean '120 microns' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19953 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 30.55 _reflns_number_total 6819 _reflns_number_gt 6192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 software, Bruker Nonius 2004' _computing_cell_refinement 'APEX 2 software, Bruker Nonius 2004' _computing_data_reduction 'SAINT, Bruker Nonius 2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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^)+(0.0440P)^2^+0.7204P] 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 6819 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.527291(15) 0.132765(14) 0.325257(11) 0.01890(5) Uani 1 1 d . . . Cl1 Cl 0.32042(5) 0.17000(5) 0.39095(4) 0.02542(10) Uani 1 1 d . . . F1 F 0.9729(2) 0.6921(2) 0.89983(15) 0.0686(5) Uani 1 1 d . . . O1 O 0.65677(15) 0.23567(13) 0.48949(11) 0.0232(3) Uani 1 1 d . . . N1 N 0.54296(18) 0.32088(16) 0.28706(13) 0.0221(3) Uani 1 1 d . . . C25 C 0.9369(3) 0.2111(3) 0.3591(3) 0.0487(6) Uani 1 1 d . . . H25C H 0.9416 0.2000 0.2794 0.073 Uiso 1 1 calc R . . H25A H 1.0360 0.2401 0.4106 0.073 Uiso 1 1 calc R . . H25B H 0.8885 0.2801 0.3776 0.073 Uiso 1 1 calc R . . C11 C 0.8126(2) 0.4106(2) 0.64764(16) 0.0249(4) Uani 1 1 d . . . C8 C 0.5961(2) 0.44105(19) 0.36097(16) 0.0244(4) Uani 1 1 d . . . C6 C 0.3412(2) 0.2643(2) 0.11371(17) 0.0304(4) Uani 1 1 d . . . H6 H 0.2739 0.2413 0.1569 0.037 Uiso 1 1 calc R . . C1 C 0.4903(2) 0.31388(19) 0.16757(16) 0.0249(4) Uani 1 1 d . . . C10 C 0.7034(2) 0.36590(19) 0.53136(15) 0.0217(3) Uani 1 1 d . . . C9 C 0.6687(2) 0.4625(2) 0.47828(16) 0.0267(4) Uani 1 1 d . . . H9 H 0.6963 0.5527 0.5250 0.032 Uiso 1 1 calc R . . C22 C 0.5870(2) -0.04895(19) 0.35431(16) 0.0252(4) Uani 1 1 d . . . H21 H 0.6201 -0.0750 0.4227 0.030 Uiso 1 1 calc R . . C5 C 0.2916(3) 0.2487(2) -0.00388(19) 0.0374(5) Uani 1 1 d . . . H5 H 0.1898 0.2153 -0.0408 0.045 Uiso 1 1 calc R . . C4 C 0.3885(3) 0.2813(2) -0.06752(18) 0.0396(5) Uani 1 1 d . . . H4 H 0.3536 0.2693 -0.1480 0.047 Uiso 1 1 calc R . . C18 C 0.3840(2) -0.0541(2) 0.19503(17) 0.0296(4) Uani 1 1 d . . . C7 C 0.5878(3) 0.5689(2) 0.32251(18) 0.0341(5) Uani 1 1 d . . . H7B H 0.6735 0.6038 0.2960 0.051 Uiso 1 1 calc R . . H7C H 0.5857 0.6380 0.3870 0.051 Uiso 1 1 calc R . . H7A H 0.4990 0.5476 0.2596 0.051 Uiso 1 1 calc R . . C21 C 0.6916(2) 0.02979(19) 0.30825(16) 0.0246(4) Uani 1 1 d . . . C2 C 0.5881(3) 0.3477(2) 0.10392(18) 0.0321(4) Uani 1 1 d . . . H2 H 0.6900 0.3819 0.1406 0.038 Uiso 1 1 calc R . . C24 C 0.8513(2) 0.0768(2) 0.37386(19) 0.0314(4) Uani 1 1 d . . . H24 H 0.8570 0.0891 0.4573 0.038 Uiso 1 1 calc R . . C13 C 1.0037(3) 0.3679(3) 0.78290(19) 0.0408(5) Uani 1 1 d . . . H13 H 1.0616 0.3107 0.8018 0.049 Uiso 1 1 calc R . . C15 C 0.9419(3) 0.5698(3) 0.82750(19) 0.0411(6) Uani 1 1 d . . . C3 C 0.5366(3) 0.3315(2) -0.01391(19) 0.0382(5) Uani 1 1 d . . . H3 H 0.6034 0.3549 -0.0575 0.046 Uiso 1 1 calc R . . C23 C 0.4377(2) -0.08780(19) 0.30038(18) 0.0283(4) Uani 1 1 d . . . H22 H 0.3707 -0.1373 0.3339 0.034 Uiso 1 1 calc R . . C12 C 0.8972(2) 0.3282(2) 0.67804(18) 0.0339(5) Uani 1 1 d . . . H12 H 0.8823 0.2432 0.6265 0.041 Uiso 1 1 calc R . . C26 C 0.9185(3) -0.0370(3) 0.3395(2) 0.0420(6) Uani 1 1 d . . . H26B H 0.8661 -0.1202 0.3564 0.063 Uiso 1 1 calc R . . H26C H 1.0215 -0.0089 0.3829 0.063 Uiso 1 1 calc R . . H26A H 0.9105 -0.0543 0.2571 0.063 Uiso 1 1 calc R . . C20 C 0.6395(2) 0.0625(2) 0.20413(16) 0.0269(4) Uani 1 1 d . . . H20 H 0.7063 0.1134 0.1712 0.032 Uiso 1 1 calc R . . C19 C 0.4867(2) 0.0193(2) 0.14816(16) 0.0286(4) Uani 1 1 d . . . H19 H 0.4535 0.0406 0.0774 0.034 Uiso 1 1 calc R . . C16 C 0.8358(3) 0.5347(2) 0.72441(18) 0.0351(5) Uani 1 1 d . . . H16 H 0.7798 0.5937 0.7062 0.042 Uiso 1 1 calc R . . C14 C 1.0256(2) 0.4906(3) 0.85994(18) 0.0371(5) Uani 1 1 d . . . H14 H 1.0962 0.5181 0.9325 0.044 Uiso 1 1 calc R . . C17 C 0.2231(3) -0.0913(3) 0.1388(2) 0.0439(6) Uani 1 1 d . . . H17C H 0.2068 -0.0451 0.0772 0.066 Uiso 1 1 calc R . . H17B H 0.1739 -0.0631 0.1959 0.066 Uiso 1 1 calc R . . H17A H 0.1838 -0.1901 0.1067 0.066 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 0.02196(8) 0.02040(8) 0.01295(8) 0.00320(5) 0.00242(5) 0.00672(5) Cl1 0.0258(2) 0.0303(2) 0.0219(2) 0.00702(17) 0.00731(16) 0.01062(18) F1 0.0715(12) 0.0646(11) 0.0435(9) -0.0191(8) -0.0114(8) 0.0223(10) O1 0.0279(7) 0.0232(6) 0.0151(6) 0.0029(5) 0.0000(5) 0.0083(5) N1 0.0267(8) 0.0242(7) 0.0144(7) 0.0065(6) 0.0026(6) 0.0072(6) C25 0.0311(12) 0.0368(12) 0.0726(19) 0.0101(12) 0.0086(12) 0.0081(10) C11 0.0245(9) 0.0290(9) 0.0162(8) 0.0049(7) 0.0030(7) 0.0020(7) C8 0.0295(9) 0.0228(8) 0.0189(8) 0.0069(7) 0.0043(7) 0.0056(7) C6 0.0345(11) 0.0349(10) 0.0202(9) 0.0066(8) 0.0020(8) 0.0126(9) C1 0.0332(10) 0.0239(8) 0.0165(8) 0.0059(7) 0.0034(7) 0.0091(7) C10 0.0221(8) 0.0258(8) 0.0144(7) 0.0032(6) 0.0032(6) 0.0055(7) C9 0.0332(10) 0.0224(8) 0.0184(8) 0.0031(7) 0.0007(7) 0.0045(7) C22 0.0346(10) 0.0206(8) 0.0215(8) 0.0053(7) 0.0065(7) 0.0111(7) C5 0.0436(13) 0.0396(12) 0.0229(10) 0.0064(9) -0.0053(9) 0.0152(10) C4 0.0658(16) 0.0359(11) 0.0150(9) 0.0080(8) 0.0033(9) 0.0174(11) C18 0.0328(10) 0.0252(9) 0.0220(9) -0.0047(7) -0.0007(8) 0.0079(8) C7 0.0518(13) 0.0250(9) 0.0212(9) 0.0075(7) 0.0038(9) 0.0085(9) C21 0.0279(9) 0.0237(8) 0.0235(9) 0.0033(7) 0.0057(7) 0.0129(7) C2 0.0404(12) 0.0320(10) 0.0219(9) 0.0076(8) 0.0081(8) 0.0073(9) C24 0.0288(10) 0.0325(10) 0.0321(11) 0.0047(8) 0.0050(8) 0.0135(8) C13 0.0317(11) 0.0583(15) 0.0264(11) 0.0081(10) -0.0016(9) 0.0133(11) C15 0.0477(14) 0.0390(12) 0.0198(10) -0.0036(8) -0.0024(9) 0.0017(10) C3 0.0583(15) 0.0365(11) 0.0216(10) 0.0106(8) 0.0153(10) 0.0116(11) C23 0.0333(10) 0.0208(8) 0.0265(9) 0.0013(7) 0.0072(8) 0.0051(8) C12 0.0313(11) 0.0423(12) 0.0231(10) 0.0032(8) -0.0007(8) 0.0130(9) C26 0.0347(12) 0.0417(13) 0.0482(14) 0.0040(11) 0.0040(10) 0.0209(10) C20 0.0353(10) 0.0290(9) 0.0205(9) 0.0051(7) 0.0111(8) 0.0147(8) C19 0.0397(11) 0.0309(9) 0.0148(8) 0.0003(7) 0.0042(7) 0.0169(9) C16 0.0421(12) 0.0328(10) 0.0218(9) 0.0017(8) -0.0017(8) 0.0088(9) C14 0.0290(10) 0.0529(13) 0.0175(9) 0.0081(9) -0.0010(8) -0.0014(9) C17 0.0340(12) 0.0397(12) 0.0398(13) -0.0055(10) -0.0067(10) 0.0053(10) _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 O1 2.0684(13) . ? Ru1 N1 2.0870(16) . ? Ru1 C20 2.1691(19) . ? Ru1 C21 2.1808(19) . ? Ru1 C19 2.1835(18) . ? Ru1 C22 2.1953(18) . ? Ru1 C23 2.196(2) . ? Ru1 C18 2.2099(19) . ? Ru1 Cl1 2.4384(5) . ? F1 C15 1.340(3) . ? O1 C10 1.290(2) . ? N1 C8 1.316(2) . ? N1 C1 1.433(2) . ? C25 C24 1.514(3) . ? C25 H25C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C11 C12 1.387(3) . ? C11 C16 1.394(3) . ? C11 C10 1.505(2) . ? C8 C9 1.416(3) . ? C8 C7 1.516(3) . ? C6 C5 1.390(3) . ? C6 C1 1.391(3) . ? C6 H6 0.9500 . ? C1 C2 1.388(3) . ? C10 C9 1.374(3) . ? C9 H9 0.9500 . ? C22 C23 1.395(3) . ? C22 C21 1.437(3) . ? C22 H21 0.9500 . ? C5 C4 1.380(4) . ? C5 H5 0.9500 . ? C4 C3 1.382(4) . ? C4 H4 0.9500 . ? C18 C19 1.406(3) . ? C18 C23 1.434(3) . ? C18 C17 1.502(3) . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 H7A 0.9800 . ? C21 C20 1.412(3) . ? C21 C24 1.511(3) . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C24 C26 1.538(3) . ? C24 H24 1.0000 . ? C13 C14 1.387(4) . ? C13 C12 1.393(3) . ? C13 H13 0.9500 . ? C15 C14 1.359(4) . ? C15 C16 1.380(3) . ? C3 H3 0.9500 . ? C23 H22 0.9500 . ? C12 H12 0.9500 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C26 H26A 0.9800 . ? C20 C19 1.428(3) . ? C20 H20 0.9500 . ? C19 H19 0.9500 . ? C16 H16 0.9500 . ? C14 H14 0.9500 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C17 H17A 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 O1 Ru1 N1 88.40(6) . . ? O1 Ru1 C20 116.09(7) . . ? N1 Ru1 C20 95.71(7) . . ? O1 Ru1 C21 87.78(6) . . ? N1 Ru1 C21 121.50(7) . . ? C20 Ru1 C21 37.88(7) . . ? O1 Ru1 C19 154.34(7) . . ? N1 Ru1 C19 95.20(7) . . ? C20 Ru1 C19 38.30(8) . . ? C21 Ru1 C19 68.67(7) . . ? O1 Ru1 C22 88.09(6) . . ? N1 Ru1 C22 159.68(7) . . ? C20 Ru1 C22 68.10(7) . . ? C21 Ru1 C22 38.35(7) . . ? C19 Ru1 C22 79.75(7) . . ? O1 Ru1 C23 114.32(7) . . ? N1 Ru1 C23 156.32(7) . . ? C20 Ru1 C23 80.69(8) . . ? C21 Ru1 C23 68.63(8) . . ? C19 Ru1 C23 67.46(8) . . ? C22 Ru1 C23 37.04(8) . . ? O1 Ru1 C18 152.28(7) . . ? N1 Ru1 C18 118.91(7) . . ? C20 Ru1 C18 68.82(8) . . ? C21 Ru1 C18 81.88(8) . . ? C19 Ru1 C18 37.31(8) . . ? C22 Ru1 C18 67.95(8) . . ? C23 Ru1 C18 38.00(8) . . ? O1 Ru1 Cl1 87.14(4) . . ? N1 Ru1 Cl1 83.65(5) . . ? C20 Ru1 Cl1 156.76(6) . . ? C21 Ru1 Cl1 154.18(5) . . ? C19 Ru1 Cl1 118.50(6) . . ? C22 Ru1 Cl1 116.14(6) . . ? C23 Ru1 Cl1 90.60(6) . . ? C18 Ru1 Cl1 91.07(6) . . ? C10 O1 Ru1 126.53(12) . . ? C8 N1 C1 118.83(16) . . ? C8 N1 Ru1 126.41(12) . . ? C1 N1 Ru1 114.76(12) . . ? C24 C25 H25C 109.5 . . ? C24 C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25C C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C12 C11 C16 118.70(18) . . ? C12 C11 C10 118.99(18) . . ? C16 C11 C10 122.26(19) . . ? N1 C8 C9 123.99(17) . . ? N1 C8 C7 120.69(17) . . ? C9 C8 C7 115.27(17) . . ? C5 C6 C1 119.5(2) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C2 C1 C6 119.95(18) . . ? C2 C1 N1 120.14(18) . . ? C6 C1 N1 119.77(18) . . ? O1 C10 C9 126.66(17) . . ? O1 C10 C11 113.87(16) . . ? C9 C10 C11 119.38(17) . . ? C10 C9 C8 126.57(18) . . ? C10 C9 H9 116.7 . . ? C8 C9 H9 116.7 . . ? C23 C22 C21 121.18(18) . . ? C23 C22 Ru1 71.49(11) . . ? C21 C22 Ru1 70.28(10) . . ? C23 C22 H21 119.4 . . ? C21 C22 H21 119.4 . . ? Ru1 C22 H21 131.8 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C19 C18 C23 117.79(19) . . ? C19 C18 C17 121.0(2) . . ? C23 C18 C17 121.2(2) . . ? C19 C18 Ru1 70.33(11) . . ? C23 C18 Ru1 70.46(11) . . ? C17 C18 Ru1 128.63(15) . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C20 C21 C22 118.11(18) . . ? C20 C21 C24 122.75(19) . . ? C22 C21 C24 119.13(18) . . ? C20 C21 Ru1 70.61(11) . . ? C22 C21 Ru1 71.37(11) . . ? C24 C21 Ru1 128.07(13) . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C21 C24 C25 114.16(19) . . ? C21 C24 C26 108.52(18) . . ? C25 C24 C26 111.5(2) . . ? C21 C24 H24 107.5 . . ? C25 C24 H24 107.5 . . ? C26 C24 H24 107.5 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? F1 C15 C14 116.0(2) . . ? F1 C15 C16 119.6(2) . . ? C14 C15 C16 124.2(2) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C22 C23 C18 120.97(19) . . ? C22 C23 Ru1 71.47(11) . . ? C18 C23 Ru1 71.54(11) . . ? C22 C23 H22 119.5 . . ? C18 C23 H22 119.5 . . ? Ru1 C23 H22 130.1 . . ? C11 C12 C13 121.0(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C24 C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C26 H26A 109.5 . . ? H26B C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? C21 C20 C19 120.19(19) . . ? C21 C20 Ru1 71.51(11) . . ? C19 C20 Ru1 71.40(11) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? Ru1 C20 H20 129.6 . . ? C18 C19 C20 121.71(18) . . ? C18 C19 Ru1 72.36(11) . . ? C20 C19 Ru1 70.30(11) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? Ru1 C19 H19 131.1 . . ? C15 C16 C11 118.4(2) . . ? C15 C16 H16 120.8 . . ? C11 C16 H16 120.8 . . ? C15 C14 C13 117.4(2) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C18 C17 H17C 109.5 . . ? C18 C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C18 C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? H17B C17 H17A 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 N1 Ru1 O1 C10 4.58(16) . . . . ? C20 Ru1 O1 C10 100.16(16) . . . . ? C21 Ru1 O1 C10 126.19(16) . . . . ? C19 Ru1 O1 C10 103.3(2) . . . . ? C22 Ru1 O1 C10 164.57(16) . . . . ? C23 Ru1 O1 C10 -168.50(15) . . . . ? C18 Ru1 O1 C10 -166.00(16) . . . . ? Cl1 Ru1 O1 C10 -79.13(15) . . . . ? O1 Ru1 N1 C8 -10.77(17) . . . . ? C20 Ru1 N1 C8 -126.83(17) . . . . ? C21 Ru1 N1 C8 -97.18(18) . . . . ? C19 Ru1 N1 C8 -165.31(18) . . . . ? C22 Ru1 N1 C8 -90.9(2) . . . . ? C23 Ru1 N1 C8 153.36(19) . . . . ? C18 Ru1 N1 C8 164.24(16) . . . . ? Cl1 Ru1 N1 C8 76.53(17) . . . . ? O1 Ru1 N1 C1 168.81(14) . . . . ? C20 Ru1 N1 C1 52.75(14) . . . . ? C21 Ru1 N1 C1 82.40(15) . . . . ? C19 Ru1 N1 C1 14.27(15) . . . . ? C22 Ru1 N1 C1 88.7(2) . . . . ? C23 Ru1 N1 C1 -27.1(3) . . . . ? C18 Ru1 N1 C1 -16.18(16) . . . . ? Cl1 Ru1 N1 C1 -103.89(13) . . . . ? C1 N1 C8 C9 -171.24(19) . . . . ? Ru1 N1 C8 C9 8.3(3) . . . . ? C1 N1 C8 C7 6.2(3) . . . . ? Ru1 N1 C8 C7 -174.24(15) . . . . ? C5 C6 C1 C2 0.2(3) . . . . ? C5 C6 C1 N1 -175.47(19) . . . . ? C8 N1 C1 C2 75.3(3) . . . . ? Ru1 N1 C1 C2 -104.30(19) . . . . ? C8 N1 C1 C6 -109.0(2) . . . . ? Ru1 N1 C1 C6 71.4(2) . . . . ? Ru1 O1 C10 C9 4.7(3) . . . . ? Ru1 O1 C10 C11 -171.78(12) . . . . ? C12 C11 C10 O1 26.4(3) . . . . ? C16 C11 C10 O1 -156.1(2) . . . . ? C12 C11 C10 C9 -150.4(2) . . . . ? C16 C11 C10 C9 27.1(3) . . . . ? O1 C10 C9 C8 -11.8(4) . . . . ? C11 C10 C9 C8 164.6(2) . . . . ? N1 C8 C9 C10 4.5(4) . . . . ? C7 C8 C9 C10 -173.1(2) . . . . ? O1 Ru1 C22 C23 136.74(12) . . . . ? N1 Ru1 C22 C23 -143.09(18) . . . . ? C20 Ru1 C22 C23 -104.07(13) . . . . ? C21 Ru1 C22 C23 -134.42(17) . . . . ? C19 Ru1 C22 C23 -65.96(13) . . . . ? C18 Ru1 C22 C23 -28.98(12) . . . . ? Cl1 Ru1 C22 C23 50.87(12) . . . . ? O1 Ru1 C22 C21 -88.84(11) . . . . ? N1 Ru1 C22 C21 -8.7(2) . . . . ? C20 Ru1 C22 C21 30.35(11) . . . . ? C19 Ru1 C22 C21 68.46(12) . . . . ? C23 Ru1 C22 C21 134.42(17) . . . . ? C18 Ru1 C22 C21 105.44(13) . . . . ? Cl1 Ru1 C22 C21 -174.71(9) . . . . ? C1 C6 C5 C4 0.3(3) . . . . ? C6 C5 C4 C3 -0.7(4) . . . . ? O1 Ru1 C18 C19 -134.41(15) . . . . ? N1 Ru1 C18 C19 56.36(14) . . . . ? C20 Ru1 C18 C19 -28.35(12) . . . . ? C21 Ru1 C18 C19 -65.24(12) . . . . ? C22 Ru1 C18 C19 -102.41(13) . . . . ? C23 Ru1 C18 C19 -130.71(18) . . . . ? Cl1 Ru1 C18 C19 139.70(11) . . . . ? O1 Ru1 C18 C23 -3.7(2) . . . . ? N1 Ru1 C18 C23 -172.93(11) . . . . ? C20 Ru1 C18 C23 102.36(13) . . . . ? C21 Ru1 C18 C23 65.47(13) . . . . ? C19 Ru1 C18 C23 130.71(18) . . . . ? C22 Ru1 C18 C23 28.30(12) . . . . ? Cl1 Ru1 C18 C23 -89.60(12) . . . . ? O1 Ru1 C18 C17 111.1(2) . . . . ? N1 Ru1 C18 C17 -58.1(2) . . . . ? C20 Ru1 C18 C17 -142.9(2) . . . . ? C21 Ru1 C18 C17 -179.7(2) . . . . ? C19 Ru1 C18 C17 -114.5(3) . . . . ? C22 Ru1 C18 C17 143.1(2) . . . . ? C23 Ru1 C18 C17 114.8(3) . . . . ? Cl1 Ru1 C18 C17 25.2(2) . . . . ? C23 C22 C21 C20 -2.4(3) . . . . ? Ru1 C22 C21 C20 -54.74(15) . . . . ? C23 C22 C21 C24 176.18(18) . . . . ? Ru1 C22 C21 C24 123.85(17) . . . . ? C23 C22 C21 Ru1 52.34(16) . . . . ? O1 Ru1 C21 C20 -140.05(12) . . . . ? N1 Ru1 C21 C20 -53.29(14) . . . . ? C19 Ru1 C21 C20 29.52(12) . . . . ? C22 Ru1 C21 C20 130.22(17) . . . . ? C23 Ru1 C21 C20 102.71(13) . . . . ? C18 Ru1 C21 C20 65.74(13) . . . . ? Cl1 Ru1 C21 C20 141.17(12) . . . . ? O1 Ru1 C21 C22 89.72(11) . . . . ? N1 Ru1 C21 C22 176.48(10) . . . . ? C20 Ru1 C21 C22 -130.22(17) . . . . ? C19 Ru1 C21 C22 -100.70(12) . . . . ? C23 Ru1 C21 C22 -27.51(11) . . . . ? C18 Ru1 C21 C22 -64.48(12) . . . . ? Cl1 Ru1 C21 C22 10.95(19) . . . . ? O1 Ru1 C21 C24 -23.13(18) . . . . ? N1 Ru1 C21 C24 63.6(2) . . . . ? C20 Ru1 C21 C24 116.9(2) . . . . ? C19 Ru1 C21 C24 146.4(2) . . . . ? C22 Ru1 C21 C24 -112.9(2) . . . . ? C23 Ru1 C21 C24 -140.4(2) . . . . ? C18 Ru1 C21 C24 -177.34(19) . . . . ? Cl1 Ru1 C21 C24 -101.9(2) . . . . ? C6 C1 C2 C3 -0.2(3) . . . . ? N1 C1 C2 C3 175.44(19) . . . . ? C20 C21 C24 C25 29.7(3) . . . . ? C22 C21 C24 C25 -148.8(2) . . . . ? Ru1 C21 C24 C25 -60.4(3) . . . . ? C20 C21 C24 C26 -95.2(2) . . . . ? C22 C21 C24 C26 86.3(2) . . . . ? Ru1 C21 C24 C26 174.64(16) . . . . ? C5 C4 C3 C2 0.7(4) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C21 C22 C23 C18 2.0(3) . . . . ? Ru1 C22 C23 C18 53.80(17) . . . . ? C21 C22 C23 Ru1 -51.80(16) . . . . ? C19 C18 C23 C22 0.0(3) . . . . ? C17 C18 C23 C22 -177.80(19) . . . . ? Ru1 C18 C23 C22 -53.77(17) . . . . ? C19 C18 C23 Ru1 53.79(16) . . . . ? C17 C18 C23 Ru1 -124.03(19) . . . . ? O1 Ru1 C23 C22 -48.73(13) . . . . ? N1 Ru1 C23 C22 148.72(16) . . . . ? C20 Ru1 C23 C22 65.78(12) . . . . ? C21 Ru1 C23 C22 28.42(11) . . . . ? C19 Ru1 C23 C22 103.32(13) . . . . ? C18 Ru1 C23 C22 133.16(18) . . . . ? Cl1 Ru1 C23 C22 -135.86(11) . . . . ? O1 Ru1 C23 C18 178.11(11) . . . . ? N1 Ru1 C23 C18 15.6(2) . . . . ? C20 Ru1 C23 C18 -67.37(13) . . . . ? C21 Ru1 C23 C18 -104.74(13) . . . . ? C19 Ru1 C23 C18 -29.84(12) . . . . ? C22 Ru1 C23 C18 -133.16(18) . . . . ? Cl1 Ru1 C23 C18 90.98(12) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? C10 C11 C12 C13 177.5(2) . . . . ? C14 C13 C12 C11 1.0(4) . . . . ? C22 C21 C20 C19 0.8(3) . . . . ? C24 C21 C20 C19 -177.71(18) . . . . ? Ru1 C21 C20 C19 -54.29(16) . . . . ? C22 C21 C20 Ru1 55.11(15) . . . . ? C24 C21 C20 Ru1 -123.42(18) . . . . ? O1 Ru1 C20 C21 45.59(13) . . . . ? N1 Ru1 C20 C21 136.61(12) . . . . ? C19 Ru1 C20 C21 -132.23(18) . . . . ? C22 Ru1 C20 C21 -30.70(11) . . . . ? C23 Ru1 C20 C21 -67.01(12) . . . . ? C18 Ru1 C20 C21 -104.55(13) . . . . ? Cl1 Ru1 C20 C21 -136.20(13) . . . . ? O1 Ru1 C20 C19 177.82(11) . . . . ? N1 Ru1 C20 C19 -91.17(12) . . . . ? C21 Ru1 C20 C19 132.23(18) . . . . ? C22 Ru1 C20 C19 101.52(13) . . . . ? C23 Ru1 C20 C19 65.22(12) . . . . ? C18 Ru1 C20 C19 27.67(12) . . . . ? Cl1 Ru1 C20 C19 -4.0(2) . . . . ? C23 C18 C19 C20 -1.6(3) . . . . ? C17 C18 C19 C20 176.21(19) . . . . ? Ru1 C18 C19 C20 52.25(17) . . . . ? C23 C18 C19 Ru1 -53.85(16) . . . . ? C17 C18 C19 Ru1 123.97(19) . . . . ? C21 C20 C19 C18 1.2(3) . . . . ? Ru1 C20 C19 C18 -53.16(17) . . . . ? C21 C20 C19 Ru1 54.34(16) . . . . ? O1 Ru1 C19 C18 129.88(16) . . . . ? N1 Ru1 C19 C18 -132.96(12) . . . . ? C20 Ru1 C19 C18 134.40(18) . . . . ? C21 Ru1 C19 C18 105.19(13) . . . . ? C22 Ru1 C19 C18 66.91(13) . . . . ? C23 Ru1 C19 C18 30.35(12) . . . . ? Cl1 Ru1 C19 C18 -47.38(13) . . . . ? O1 Ru1 C19 C20 -4.5(2) . . . . ? N1 Ru1 C19 C20 92.63(12) . . . . ? C21 Ru1 C19 C20 -29.21(12) . . . . ? C22 Ru1 C19 C20 -67.50(12) . . . . ? C23 Ru1 C19 C20 -104.05(13) . . . . ? C18 Ru1 C19 C20 -134.40(18) . . . . ? Cl1 Ru1 C19 C20 178.22(10) . . . . ? F1 C15 C16 C11 175.8(2) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? C10 C11 C16 C15 -177.6(2) . . . . ? F1 C15 C14 C13 -175.2(2) . . . . ? C16 C15 C14 C13 1.2(4) . . . . ? C12 C13 C14 C15 -1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 2.241 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.084 data_3 _database_code_depnum_ccdc_archive 'CCDC 890357' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Cl Ir O3' _chemical_formula_sum 'C20 H20 Cl Ir O3' _chemical_formula_weight 536.01 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 26.532(3) _cell_length_b 8.4190(11) _cell_length_c 16.576(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3702.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7723 _cell_measurement_theta_min 2.818 _cell_measurement_theta_max 32.209 _exptl_crystal_description fragment _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 7.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1823 _exptl_absorpt_correction_T_max 0.3066 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_device_type 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 139966 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10682 _reflns_number_gt 10133 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; All H atoms were placed in calculated positions and refined using a riding model. C-H distances: CH3, 0.98\A, CH2 0.99\A, aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq of the parent atom. The crytal was refined as a racemic twin (BASF 0.288) Highest q-peaks are fourrier ripples q-peak = 5.62 is 1.53 angstrom from Ir1 q-peak = 5.59 is 1.53 angstron from Ir2 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^)+(0.0364P)^2^+3.0275P] 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' _refine_ls_abs_structure_Flack 0.288(5) _refine_ls_number_reflns 10682 _refine_ls_number_parameters 462 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 Ir1 Ir 0.476137(5) 0.403029(13) 0.467498(7) 0.01877(4) Uani 1 1 d . . . Ir2 Ir 0.774988(5) 1.085304(14) 0.628252(8) 0.02037(4) Uani 1 1 d . . . Cl1 Cl 0.44742(4) 0.36086(15) 0.60228(6) 0.0330(2) Uani 1 1 d . . . Cl2 Cl 0.79848(4) 1.12624(14) 0.48981(6) 0.0293(2) Uani 1 1 d . . . O1 O 0.49947(10) 0.6322(3) 0.51693(16) 0.0220(5) Uani 1 1 d . . . O2 O 0.54900(10) 0.3613(3) 0.51605(17) 0.0227(5) Uani 1 1 d . . . O3 O 0.66129(14) 0.5791(4) 0.7110(2) 0.0368(8) Uani 1 1 d . . . O4 O 0.70020(11) 1.1217(4) 0.58711(19) 0.0263(6) Uani 1 1 d . . . O5 O 0.75095(11) 0.8525(3) 0.58233(16) 0.0254(6) Uani 1 1 d . . . O6 O 0.57987(13) 0.8953(4) 0.4085(2) 0.0371(8) Uani 1 1 d . . . C1 C 0.59616(14) 0.7463(4) 0.6609(2) 0.0208(7) Uani 1 1 d . . . C2 C 0.61283(17) 0.8767(5) 0.7063(3) 0.0273(8) Uani 1 1 d . . . H2 H 0.6412 0.8658 0.7409 0.033 Uiso 1 1 calc R . . C3 C 0.58772(17) 1.0235(5) 0.7010(3) 0.0300(9) Uani 1 1 d . . . H3 H 0.5992 1.1114 0.7319 0.036 Uiso 1 1 calc R . . C4 C 0.54526(17) 1.0406(5) 0.6495(2) 0.0279(8) Uani 1 1 d . . . H4 H 0.5285 1.1401 0.6454 0.033 Uiso 1 1 calc R . . C5 C 0.52827(17) 0.9106(4) 0.6050(3) 0.0261(9) Uani 1 1 d . . . H5 H 0.4996 0.9210 0.5711 0.031 Uiso 1 1 calc R . . C6 C 0.55349(14) 0.7643(4) 0.6104(2) 0.0194(7) Uani 1 1 d . . . C7 C 0.53700(14) 0.6233(4) 0.5632(2) 0.0176(6) Uani 1 1 d . . . C8 C 0.56523(14) 0.4709(4) 0.5656(2) 0.0198(7) Uani 1 1 d . . . C9 C 0.60666(14) 0.4586(4) 0.6156(2) 0.0208(7) Uani 1 1 d . . . H9 H 0.6247 0.3611 0.6174 0.025 Uiso 1 1 calc R . . C10 C 0.62369(16) 0.5904(4) 0.6657(3) 0.0231(8) Uani 1 1 d . . . C11 C 0.47043(16) 0.4604(6) 0.3400(3) 0.0278(9) Uani 1 1 d . . . C12 C 0.42126(16) 0.4733(5) 0.3779(3) 0.0281(9) Uani 1 1 d . . . C13 C 0.40701(16) 0.3199(6) 0.4102(3) 0.0303(9) Uani 1 1 d . . . C14 C 0.44883(19) 0.2113(5) 0.3954(3) 0.0301(9) Uani 1 1 d . . . C15 C 0.48732(18) 0.2986(6) 0.3492(3) 0.0314(9) Uani 1 1 d . . . C16 C 0.4968(3) 0.5931(6) 0.2974(4) 0.0502(15) Uani 1 1 d . . . H16A H 0.4753 0.6334 0.2539 0.075 Uiso 1 1 calc R . . H16B H 0.5286 0.5539 0.2746 0.075 Uiso 1 1 calc R . . H16C H 0.5039 0.6789 0.3357 0.075 Uiso 1 1 calc R . . C17 C 0.3895(2) 0.6222(7) 0.3820(4) 0.0506(15) Uani 1 1 d . . . H17A H 0.4108 0.7124 0.3974 0.076 Uiso 1 1 calc R . . H17B H 0.3628 0.6082 0.4222 0.076 Uiso 1 1 calc R . . H17C H 0.3744 0.6426 0.3290 0.076 Uiso 1 1 calc R . . C18 C 0.3584(2) 0.2810(8) 0.4522(4) 0.0556(15) Uani 1 1 d . . . H18A H 0.3339 0.2415 0.4127 0.083 Uiso 1 1 calc R . . H18B H 0.3451 0.3768 0.4782 0.083 Uiso 1 1 calc R . . H18C H 0.3645 0.1993 0.4932 0.083 Uiso 1 1 calc R . . C19 C 0.4503(3) 0.0367(6) 0.4156(4) 0.0591(18) Uani 1 1 d . . . H19A H 0.4227 0.0110 0.4525 0.089 Uiso 1 1 calc R . . H19B H 0.4826 0.0112 0.4415 0.089 Uiso 1 1 calc R . . H19C H 0.4468 -0.0257 0.3660 0.089 Uiso 1 1 calc R . . C20 C 0.5353(2) 0.2286(8) 0.3196(3) 0.0505(14) Uani 1 1 d . . . H20A H 0.5287 0.1652 0.2712 0.076 Uiso 1 1 calc R . . H20B H 0.5497 0.1605 0.3616 0.076 Uiso 1 1 calc R . . H20C H 0.5590 0.3139 0.3066 0.076 Uiso 1 1 calc R . . C21 C 0.69292(14) 0.7154(5) 0.4963(2) 0.0219(7) Uani 1 1 d . . . C22 C 0.71965(17) 0.5726(5) 0.4978(3) 0.0282(9) Uani 1 1 d . . . H22 H 0.7501 0.5644 0.5276 0.034 Uiso 1 1 calc R . . C23 C 0.70097(17) 0.4404(5) 0.4547(3) 0.0315(9) Uani 1 1 d . . . H23 H 0.7180 0.3412 0.4572 0.038 Uiso 1 1 calc R . . C24 C 0.65717(17) 0.4568(6) 0.4082(3) 0.0294(8) Uani 1 1 d . . . H24 H 0.6451 0.3690 0.3778 0.035 Uiso 1 1 calc R . . C25 C 0.63111(18) 0.6001(5) 0.4060(3) 0.0277(9) Uani 1 1 d . . . H25 H 0.6014 0.6092 0.3742 0.033 Uiso 1 1 calc R . . C26 C 0.64816(14) 0.7311(4) 0.4501(2) 0.0209(7) Uani 1 1 d . . . C27 C 0.61919(16) 0.8862(5) 0.4482(2) 0.0261(8) Uani 1 1 d . . . C28 C 0.63829(14) 1.0200(5) 0.4949(2) 0.0242(8) Uani 1 1 d . . . H28 H 0.6200 1.1170 0.4944 0.029 Uiso 1 1 calc R . . C29 C 0.68205(14) 1.0104(4) 0.5397(2) 0.0198(7) Uani 1 1 d . . . C30 C 0.71104(14) 0.8550(4) 0.5419(2) 0.0199(7) Uani 1 1 d . . . C31 C 0.83434(16) 1.0233(6) 0.7112(3) 0.0279(9) Uani 1 1 d . . . C32 C 0.84357(16) 1.1800(6) 0.6789(3) 0.0303(9) Uani 1 1 d . . . C33 C 0.80106(18) 1.2820(5) 0.6987(3) 0.0305(9) Uani 1 1 d . . . C34 C 0.76603(16) 1.1873(5) 0.7467(2) 0.0279(9) Uani 1 1 d . . . C35 C 0.78618(17) 1.0294(5) 0.7551(2) 0.0262(8) Uani 1 1 d . . . C36 C 0.71657(17) 1.2434(6) 0.7811(3) 0.0398(11) Uani 1 1 d . . . H36A H 0.6924 1.1555 0.7810 0.060 Uiso 1 1 calc R . . H36B H 0.7035 1.3308 0.7481 0.060 Uiso 1 1 calc R . . H36C H 0.7217 1.2805 0.8365 0.060 Uiso 1 1 calc R . . C37 C 0.7623(2) 0.8907(6) 0.7992(3) 0.0380(11) Uani 1 1 d . . . H37A H 0.7459 0.9291 0.8485 0.057 Uiso 1 1 calc R . . H37B H 0.7883 0.8131 0.8133 0.057 Uiso 1 1 calc R . . H37C H 0.7371 0.8404 0.7643 0.057 Uiso 1 1 calc R . . C38 C 0.8689(2) 0.8841(7) 0.7072(4) 0.0466(14) Uani 1 1 d . . . H38A H 0.8920 0.8968 0.6616 0.070 Uiso 1 1 calc R . . H38B H 0.8491 0.7868 0.7001 0.070 Uiso 1 1 calc R . . H38C H 0.8883 0.8772 0.7574 0.070 Uiso 1 1 calc R . . C39 C 0.88938(19) 1.2321(8) 0.6301(4) 0.0559(15) Uani 1 1 d . . . H39A H 0.9100 1.3047 0.6625 0.084 Uiso 1 1 calc R . . H39B H 0.8782 1.2863 0.5810 0.084 Uiso 1 1 calc R . . H39C H 0.9094 1.1386 0.6155 0.084 Uiso 1 1 calc R . . C40 C 0.7962(3) 1.4585(6) 0.6823(3) 0.0535(16) Uani 1 1 d . . . H40A H 0.7604 1.4872 0.6792 0.080 Uiso 1 1 calc R . . H40B H 0.8127 1.4841 0.6310 0.080 Uiso 1 1 calc R . . H40C H 0.8123 1.5184 0.7260 0.080 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 Ir1 0.02013(7) 0.01893(6) 0.01726(7) 0.00108(6) -0.00193(5) -0.00090(4) Ir2 0.02062(7) 0.02375(7) 0.01675(7) -0.00020(6) -0.00041(5) 0.00133(4) Cl1 0.0309(5) 0.0456(6) 0.0225(5) 0.0072(4) 0.0027(4) -0.0068(5) Cl2 0.0313(5) 0.0385(5) 0.0182(4) 0.0024(4) 0.0026(3) -0.0020(4) O1 0.0237(13) 0.0217(12) 0.0205(13) 0.0007(10) -0.0079(10) -0.0018(11) O2 0.0238(13) 0.0213(12) 0.0230(14) -0.0002(11) -0.0018(11) 0.0039(11) O3 0.0356(18) 0.0387(18) 0.0362(19) -0.0034(13) -0.0192(14) 0.0078(13) O4 0.0227(14) 0.0279(13) 0.0284(16) -0.0019(12) -0.0042(11) 0.0027(11) O5 0.0300(14) 0.0246(13) 0.0214(13) -0.0009(11) -0.0058(11) 0.0062(12) O6 0.0305(17) 0.0453(19) 0.0356(19) -0.0049(13) -0.0132(14) 0.0069(13) C1 0.0244(18) 0.0208(17) 0.0171(16) 0.0043(13) 0.0003(13) -0.0029(13) C2 0.031(2) 0.0304(19) 0.0204(19) 0.0009(15) -0.0066(16) -0.0059(17) C3 0.037(2) 0.028(2) 0.025(2) -0.0054(16) -0.0003(17) -0.0021(17) C4 0.037(2) 0.0208(18) 0.026(2) -0.0015(15) -0.0001(16) 0.0026(16) C5 0.029(2) 0.026(2) 0.023(2) -0.0003(13) -0.0027(15) 0.0019(14) C6 0.0209(16) 0.0197(15) 0.0178(18) -0.0005(12) 0.0018(12) -0.0003(13) C7 0.0198(16) 0.0178(15) 0.0152(16) 0.0046(13) 0.0019(13) -0.0033(13) C8 0.0200(18) 0.0188(16) 0.0205(19) 0.0018(14) 0.0009(14) 0.0029(13) C9 0.0261(17) 0.0187(16) 0.0176(18) 0.0012(14) -0.0002(14) 0.0008(13) C10 0.025(2) 0.0231(18) 0.0209(19) 0.0010(13) 0.0011(15) -0.0025(13) C11 0.028(2) 0.037(2) 0.018(2) 0.0038(17) -0.0049(16) -0.0043(17) C12 0.026(2) 0.033(2) 0.026(2) -0.0054(17) -0.0134(16) 0.0037(17) C13 0.028(2) 0.037(2) 0.026(2) -0.0041(17) -0.0060(16) -0.0104(17) C14 0.046(3) 0.0203(18) 0.024(2) -0.0004(15) -0.0136(18) -0.0007(16) C15 0.036(2) 0.038(2) 0.0197(19) -0.0088(16) -0.0097(17) 0.0072(19) C16 0.062(4) 0.049(3) 0.040(3) 0.023(2) -0.015(3) -0.021(2) C17 0.057(4) 0.046(3) 0.049(3) -0.010(2) -0.023(3) 0.024(3) C18 0.033(2) 0.085(4) 0.049(3) -0.007(3) -0.002(2) -0.027(3) C19 0.092(5) 0.029(3) 0.056(4) -0.004(3) -0.040(3) -0.006(3) C20 0.052(3) 0.068(4) 0.031(3) -0.013(2) -0.005(2) 0.019(3) C21 0.0210(17) 0.0247(18) 0.0202(17) 0.0029(14) 0.0038(13) 0.0001(14) C22 0.028(2) 0.027(2) 0.029(2) 0.0016(15) -0.0018(17) 0.0003(15) C23 0.036(2) 0.0251(17) 0.033(2) -0.0011(17) 0.0064(19) 0.0000(16) C24 0.034(2) 0.033(2) 0.0210(19) -0.0017(17) 0.0024(16) -0.0042(18) C25 0.029(2) 0.029(2) 0.025(2) -0.0025(14) -0.0017(17) -0.0054(15) C26 0.0238(16) 0.0249(16) 0.0139(16) 0.0026(12) 0.0005(12) -0.0034(13) C27 0.0245(19) 0.0340(19) 0.0197(19) 0.0045(15) -0.0012(14) 0.0006(15) C28 0.0217(18) 0.0283(19) 0.0226(18) 0.0017(15) 0.0010(14) 0.0039(15) C29 0.0209(18) 0.0247(17) 0.0139(17) 0.0022(13) 0.0036(14) 0.0004(13) C30 0.0221(16) 0.0201(17) 0.0174(17) 0.0053(13) 0.0027(13) 0.0034(14) C31 0.0228(19) 0.039(2) 0.022(2) -0.0048(17) -0.0048(15) 0.0048(17) C32 0.026(2) 0.046(2) 0.0193(18) -0.0019(17) -0.0050(15) -0.0099(18) C33 0.040(2) 0.029(2) 0.022(2) -0.0018(16) -0.0105(18) -0.0028(18) C34 0.029(2) 0.038(2) 0.0165(18) -0.0030(16) -0.0048(15) 0.0072(17) C35 0.029(2) 0.034(2) 0.0153(19) 0.0032(16) -0.0037(15) 0.0047(17) C36 0.036(2) 0.059(3) 0.023(2) -0.014(2) -0.0049(18) 0.021(2) C37 0.040(2) 0.045(2) 0.029(2) 0.015(2) -0.011(2) -0.0024(19) C38 0.045(3) 0.053(3) 0.042(3) -0.012(2) -0.014(2) 0.021(2) C39 0.033(2) 0.091(4) 0.043(3) 0.001(3) -0.001(3) -0.024(3) C40 0.093(5) 0.032(3) 0.035(3) 0.004(2) -0.023(3) -0.007(3) _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 Ir1 O2 2.123(3) . ? Ir1 C14 2.135(4) . ? Ir1 C12 2.162(4) . ? Ir1 C15 2.170(4) . ? Ir1 C11 2.173(4) . ? Ir1 C13 2.181(4) . ? Ir1 O1 2.186(3) . ? Ir1 Cl1 2.3870(10) . ? Ir2 O4 2.120(3) . ? Ir2 C33 2.141(4) . ? Ir2 C31 2.154(4) . ? Ir2 C34 2.156(4) . ? Ir2 C32 2.156(4) . ? Ir2 C35 2.175(4) . ? Ir2 O5 2.197(3) . ? Ir2 Cl2 2.4028(10) . ? O1 C7 1.259(4) . ? O2 C8 1.308(5) . ? O3 C10 1.252(5) . ? O4 C29 1.315(5) . ? O5 C30 1.253(5) . ? O6 C27 1.237(5) . ? C1 C2 1.402(6) . ? C1 C6 1.416(5) . ? C1 C10 1.504(5) . ? C2 C3 1.407(6) . ? C2 H2 0.9500 . ? C3 C4 1.421(6) . ? C3 H3 0.9500 . ? C4 C5 1.395(6) . ? C4 H4 0.9500 . ? C5 C6 1.405(5) . ? C5 H5 0.9500 . ? C6 C7 1.488(5) . ? C7 C8 1.486(5) . ? C8 C9 1.380(5) . ? C9 C10 1.459(5) . ? C9 H9 0.9500 . ? C11 C15 1.442(6) . ? C11 C12 1.452(6) . ? C11 C16 1.497(7) . ? C12 C13 1.449(7) . ? C12 C17 1.512(7) . ? C13 C14 1.458(7) . ? C13 C18 1.501(7) . ? C14 C15 1.473(7) . ? C14 C19 1.509(7) . ? C15 C20 1.485(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.396(5) . ? C21 C26 1.419(5) . ? C21 C30 1.478(5) . ? C22 C23 1.412(6) . ? C22 H22 0.9500 . ? C23 C24 1.402(6) . ? C23 H23 0.9500 . ? C24 C25 1.391(6) . ? C24 H24 0.9500 . ? C25 C26 1.398(5) . ? C25 H25 0.9500 . ? C26 C27 1.515(5) . ? C27 C28 1.457(6) . ? C28 C29 1.381(6) . ? C28 H28 0.9500 . ? C29 C30 1.518(5) . ? C31 C32 1.444(7) . ? C31 C35 1.472(6) . ? C31 C38 1.489(7) . ? C32 C33 1.455(7) . ? C32 C39 1.524(7) . ? C33 C34 1.460(7) . ? C33 C40 1.517(6) . ? C34 C35 1.440(6) . ? C34 C36 1.507(6) . ? C35 C37 1.517(6) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 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 Ir1 C14 113.34(14) . . ? O2 Ir1 C12 156.73(15) . . ? C14 Ir1 C12 66.04(16) . . ? O2 Ir1 C15 98.69(14) . . ? C14 Ir1 C15 40.03(18) . . ? C12 Ir1 C15 65.28(17) . . ? O2 Ir1 C11 117.96(14) . . ? C14 Ir1 C11 66.44(17) . . ? C12 Ir1 C11 39.13(17) . . ? C15 Ir1 C11 38.78(17) . . ? O2 Ir1 C13 151.37(15) . . ? C14 Ir1 C13 39.49(18) . . ? C12 Ir1 C13 38.97(18) . . ? C15 Ir1 C13 65.89(18) . . ? C11 Ir1 C13 65.76(17) . . ? O2 Ir1 O1 75.28(11) . . ? C14 Ir1 O1 166.74(13) . . ? C12 Ir1 O1 101.94(14) . . ? C15 Ir1 O1 131.13(15) . . ? C11 Ir1 O1 100.84(15) . . ? C13 Ir1 O1 133.22(15) . . ? O2 Ir1 Cl1 84.91(8) . . ? C14 Ir1 Cl1 107.63(13) . . ? C12 Ir1 Cl1 117.95(13) . . ? C15 Ir1 Cl1 146.04(14) . . ? C11 Ir1 Cl1 157.07(12) . . ? C13 Ir1 Cl1 95.22(12) . . ? O1 Ir1 Cl1 82.58(8) . . ? O4 Ir2 C33 111.47(15) . . ? O4 Ir2 C31 157.56(15) . . ? C33 Ir2 C31 66.63(17) . . ? O4 Ir2 C34 97.59(14) . . ? C33 Ir2 C34 39.71(18) . . ? C31 Ir2 C34 66.19(16) . . ? O4 Ir2 C32 149.47(16) . . ? C33 Ir2 C32 39.58(18) . . ? C31 Ir2 C32 39.15(19) . . ? C34 Ir2 C32 65.88(17) . . ? O4 Ir2 C35 118.03(14) . . ? C33 Ir2 C35 66.15(17) . . ? C31 Ir2 C35 39.74(17) . . ? C34 Ir2 C35 38.83(17) . . ? C32 Ir2 C35 65.70(17) . . ? O4 Ir2 O5 75.28(11) . . ? C33 Ir2 O5 166.55(13) . . ? C31 Ir2 O5 102.53(15) . . ? C34 Ir2 O5 129.70(15) . . ? C32 Ir2 O5 135.18(15) . . ? C35 Ir2 O5 100.46(14) . . ? O4 Ir2 Cl2 85.12(9) . . ? C33 Ir2 Cl2 109.05(12) . . ? C31 Ir2 Cl2 117.02(13) . . ? C34 Ir2 Cl2 147.26(13) . . ? C32 Ir2 Cl2 95.73(12) . . ? C35 Ir2 Cl2 156.76(12) . . ? O5 Ir2 Cl2 82.67(8) . . ? C7 O1 Ir1 113.5(2) . . ? C8 O2 Ir1 114.9(2) . . ? C29 O4 Ir2 115.6(2) . . ? C30 O5 Ir2 114.5(2) . . ? C2 C1 C6 119.1(3) . . ? C2 C1 C10 120.1(4) . . ? C6 C1 C10 120.8(3) . . ? C1 C2 C3 120.3(4) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 C7 121.7(3) . . ? C1 C6 C7 117.5(3) . . ? O1 C7 C8 117.9(3) . . ? O1 C7 C6 120.4(3) . . ? C8 C7 C6 121.7(3) . . ? O2 C8 C9 125.9(3) . . ? O2 C8 C7 115.2(3) . . ? C9 C8 C7 118.9(3) . . ? C8 C9 C10 122.1(3) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? O3 C10 C9 122.0(3) . . ? O3 C10 C1 119.0(3) . . ? C9 C10 C1 118.9(3) . . ? C15 C11 C12 107.7(4) . . ? C15 C11 C16 127.5(5) . . ? C12 C11 C16 124.7(5) . . ? C15 C11 Ir1 70.5(2) . . ? C12 C11 Ir1 70.1(2) . . ? C16 C11 Ir1 126.4(4) . . ? C13 C12 C11 109.2(4) . . ? C13 C12 C17 125.3(5) . . ? C11 C12 C17 125.6(5) . . ? C13 C12 Ir1 71.2(2) . . ? C11 C12 Ir1 70.8(2) . . ? C17 C12 Ir1 124.8(3) . . ? C12 C13 C14 107.3(4) . . ? C12 C13 C18 126.2(5) . . ? C14 C13 C18 126.5(5) . . ? C12 C13 Ir1 69.8(2) . . ? C14 C13 Ir1 68.6(2) . . ? C18 C13 Ir1 126.2(3) . . ? C13 C14 C15 107.6(4) . . ? C13 C14 C19 126.4(5) . . ? C15 C14 C19 125.7(5) . . ? C13 C14 Ir1 72.0(2) . . ? C15 C14 Ir1 71.3(2) . . ? C19 C14 Ir1 127.1(3) . . ? C11 C15 C14 108.1(4) . . ? C11 C15 C20 127.3(5) . . ? C14 C15 C20 124.6(5) . . ? C11 C15 Ir1 70.7(2) . . ? C14 C15 Ir1 68.7(2) . . ? C20 C15 Ir1 125.2(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 121.0(4) . . ? C22 C21 C30 120.7(4) . . ? C26 C21 C30 118.3(3) . . ? C21 C22 C23 119.4(4) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 119.5(4) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C25 C24 C23 120.7(4) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 120.7(4) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 118.6(4) . . ? C25 C26 C27 120.3(3) . . ? C21 C26 C27 121.1(3) . . ? O6 C27 C28 121.9(4) . . ? O6 C27 C26 119.5(4) . . ? C28 C27 C26 118.6(3) . . ? C29 C28 C27 122.2(4) . . ? C29 C28 H28 118.9 . . ? C27 C28 H28 118.9 . . ? O4 C29 C28 126.0(4) . . ? O4 C29 C30 114.5(3) . . ? C28 C29 C30 119.3(4) . . ? O5 C30 C21 122.3(3) . . ? O5 C30 C29 117.1(3) . . ? C21 C30 C29 120.5(3) . . ? C32 C31 C35 107.4(4) . . ? C32 C31 C38 126.7(5) . . ? C35 C31 C38 125.7(5) . . ? C32 C31 Ir2 70.5(2) . . ? C35 C31 Ir2 70.9(2) . . ? C38 C31 Ir2 127.8(3) . . ? C31 C32 C33 108.9(4) . . ? C31 C32 C39 126.5(5) . . ? C33 C32 C39 124.6(5) . . ? C31 C32 Ir2 70.3(2) . . ? C33 C32 Ir2 69.7(2) . . ? C39 C32 Ir2 125.0(3) . . ? C32 C33 C34 107.1(4) . . ? C32 C33 C40 127.1(5) . . ? C34 C33 C40 125.4(5) . . ? C32 C33 Ir2 70.8(2) . . ? C34 C33 Ir2 70.7(2) . . ? C40 C33 Ir2 129.2(3) . . ? C35 C34 C33 108.7(4) . . ? C35 C34 C36 125.2(4) . . ? C33 C34 C36 126.1(4) . . ? C35 C34 Ir2 71.3(2) . . ? C33 C34 Ir2 69.6(2) . . ? C36 C34 Ir2 124.4(3) . . ? C34 C35 C31 107.9(4) . . ? C34 C35 C37 127.0(4) . . ? C31 C35 C37 125.1(4) . . ? C34 C35 Ir2 69.9(2) . . ? C31 C35 Ir2 69.4(2) . . ? C37 C35 Ir2 125.1(3) . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C31 C38 H38A 109.5 . . ? C31 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C31 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C32 C39 H39A 109.5 . . ? C32 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C32 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C33 C40 H40A 109.5 . . ? C33 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C33 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 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 Ir1 O1 C7 -14.2(2) . . . . ? C14 Ir1 O1 C7 -146.4(6) . . . . ? C12 Ir1 O1 C7 -170.5(3) . . . . ? C15 Ir1 O1 C7 -103.0(3) . . . . ? C11 Ir1 O1 C7 -130.5(3) . . . . ? C13 Ir1 O1 C7 162.6(3) . . . . ? Cl1 Ir1 O1 C7 72.4(2) . . . . ? C14 Ir1 O2 C8 -174.9(3) . . . . ? C12 Ir1 O2 C8 101.8(4) . . . . ? C15 Ir1 O2 C8 146.2(3) . . . . ? C11 Ir1 O2 C8 110.4(3) . . . . ? C13 Ir1 O2 C8 -159.4(3) . . . . ? O1 Ir1 O2 C8 15.8(3) . . . . ? Cl1 Ir1 O2 C8 -67.9(3) . . . . ? C33 Ir2 O4 C29 176.6(3) . . . . ? C31 Ir2 O4 C29 -102.9(4) . . . . ? C34 Ir2 O4 C29 -144.8(3) . . . . ? C32 Ir2 O4 C29 161.0(3) . . . . ? C35 Ir2 O4 C29 -109.9(3) . . . . ? O5 Ir2 O4 C29 -15.7(3) . . . . ? Cl2 Ir2 O4 C29 68.0(3) . . . . ? O4 Ir2 O5 C30 12.3(3) . . . . ? C33 Ir2 O5 C30 134.2(6) . . . . ? C31 Ir2 O5 C30 169.3(3) . . . . ? C34 Ir2 O5 C30 100.0(3) . . . . ? C32 Ir2 O5 C30 -165.3(3) . . . . ? C35 Ir2 O5 C30 128.8(3) . . . . ? Cl2 Ir2 O5 C30 -74.5(3) . . . . ? C6 C1 C2 C3 -0.7(6) . . . . ? C10 C1 C2 C3 178.9(4) . . . . ? C1 C2 C3 C4 0.0(7) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C3 C4 C5 C6 -0.9(7) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C4 C5 C6 C7 -179.2(4) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? C10 C1 C6 C5 -179.0(4) . . . . ? C2 C1 C6 C7 180.0(3) . . . . ? C10 C1 C6 C7 0.4(5) . . . . ? Ir1 O1 C7 C8 11.1(4) . . . . ? Ir1 O1 C7 C6 -171.8(2) . . . . ? C5 C6 C7 O1 -0.2(6) . . . . ? C1 C6 C7 O1 -179.7(3) . . . . ? C5 C6 C7 C8 176.8(4) . . . . ? C1 C6 C7 C8 -2.6(5) . . . . ? Ir1 O2 C8 C9 167.7(3) . . . . ? Ir1 O2 C8 C7 -15.4(4) . . . . ? O1 C7 C8 O2 2.6(5) . . . . ? C6 C7 C8 O2 -174.5(3) . . . . ? O1 C7 C8 C9 179.7(3) . . . . ? C6 C7 C8 C9 2.6(5) . . . . ? O2 C8 C9 C10 176.5(4) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 O3 -180.0(4) . . . . ? C8 C9 C10 C1 -1.9(6) . . . . ? C2 C1 C10 O3 0.4(6) . . . . ? C6 C1 C10 O3 179.9(4) . . . . ? C2 C1 C10 C9 -177.7(4) . . . . ? C6 C1 C10 C9 1.8(5) . . . . ? O2 Ir1 C11 C15 67.2(3) . . . . ? C14 Ir1 C11 C15 -37.7(3) . . . . ? C12 Ir1 C11 C15 -118.2(4) . . . . ? C13 Ir1 C11 C15 -81.1(3) . . . . ? O1 Ir1 C11 C15 146.2(3) . . . . ? Cl1 Ir1 C11 C15 -117.2(3) . . . . ? O2 Ir1 C11 C12 -174.6(2) . . . . ? C14 Ir1 C11 C12 80.4(3) . . . . ? C15 Ir1 C11 C12 118.2(4) . . . . ? C13 Ir1 C11 C12 37.1(3) . . . . ? O1 Ir1 C11 C12 -95.6(3) . . . . ? Cl1 Ir1 C11 C12 1.0(5) . . . . ? O2 Ir1 C11 C16 -55.6(5) . . . . ? C14 Ir1 C11 C16 -160.5(5) . . . . ? C12 Ir1 C11 C16 119.0(6) . . . . ? C15 Ir1 C11 C16 -122.8(6) . . . . ? C13 Ir1 C11 C16 156.1(5) . . . . ? O1 Ir1 C11 C16 23.4(5) . . . . ? Cl1 Ir1 C11 C16 120.0(5) . . . . ? C15 C11 C12 C13 -0.4(5) . . . . ? C16 C11 C12 C13 177.8(4) . . . . ? Ir1 C11 C12 C13 -61.2(3) . . . . ? C15 C11 C12 C17 -179.6(4) . . . . ? C16 C11 C12 C17 -1.4(7) . . . . ? Ir1 C11 C12 C17 119.6(5) . . . . ? C15 C11 C12 Ir1 60.7(3) . . . . ? C16 C11 C12 Ir1 -121.0(5) . . . . ? O2 Ir1 C12 C13 131.1(3) . . . . ? C14 Ir1 C12 C13 37.5(3) . . . . ? C15 Ir1 C12 C13 81.6(3) . . . . ? C11 Ir1 C12 C13 119.0(4) . . . . ? O1 Ir1 C12 C13 -148.4(3) . . . . ? Cl1 Ir1 C12 C13 -60.5(3) . . . . ? O2 Ir1 C12 C11 12.1(5) . . . . ? C14 Ir1 C12 C11 -81.6(3) . . . . ? C15 Ir1 C12 C11 -37.4(3) . . . . ? C13 Ir1 C12 C11 -119.0(4) . . . . ? O1 Ir1 C12 C11 92.6(3) . . . . ? Cl1 Ir1 C12 C11 -179.6(2) . . . . ? O2 Ir1 C12 C17 -108.4(5) . . . . ? C14 Ir1 C12 C17 157.9(5) . . . . ? C15 Ir1 C12 C17 -158.0(5) . . . . ? C11 Ir1 C12 C17 -120.5(6) . . . . ? C13 Ir1 C12 C17 120.4(6) . . . . ? O1 Ir1 C12 C17 -28.0(5) . . . . ? Cl1 Ir1 C12 C17 59.9(5) . . . . ? C11 C12 C13 C14 2.4(5) . . . . ? C17 C12 C13 C14 -178.4(4) . . . . ? Ir1 C12 C13 C14 -58.5(3) . . . . ? C11 C12 C13 C18 -178.3(4) . . . . ? C17 C12 C13 C18 0.9(8) . . . . ? Ir1 C12 C13 C18 120.7(5) . . . . ? C11 C12 C13 Ir1 60.9(3) . . . . ? C17 C12 C13 Ir1 -119.9(5) . . . . ? O2 Ir1 C13 C12 -141.6(3) . . . . ? C14 Ir1 C13 C12 -119.0(4) . . . . ? C15 Ir1 C13 C12 -79.9(3) . . . . ? C11 Ir1 C13 C12 -37.2(3) . . . . ? O1 Ir1 C13 C12 44.7(3) . . . . ? Cl1 Ir1 C13 C12 129.4(3) . . . . ? O2 Ir1 C13 C14 -22.6(5) . . . . ? C12 Ir1 C13 C14 119.0(4) . . . . ? C15 Ir1 C13 C14 39.1(3) . . . . ? C11 Ir1 C13 C14 81.8(3) . . . . ? O1 Ir1 C13 C14 163.7(2) . . . . ? Cl1 Ir1 C13 C14 -111.6(2) . . . . ? O2 Ir1 C13 C18 97.7(5) . . . . ? C14 Ir1 C13 C18 120.3(6) . . . . ? C12 Ir1 C13 C18 -120.7(6) . . . . ? C15 Ir1 C13 C18 159.4(5) . . . . ? C11 Ir1 C13 C18 -157.9(5) . . . . ? O1 Ir1 C13 C18 -76.0(5) . . . . ? Cl1 Ir1 C13 C18 8.8(5) . . . . ? C12 C13 C14 C15 -3.5(5) . . . . ? C18 C13 C14 C15 177.3(4) . . . . ? Ir1 C13 C14 C15 -62.8(3) . . . . ? C12 C13 C14 C19 -177.4(4) . . . . ? C18 C13 C14 C19 3.4(7) . . . . ? Ir1 C13 C14 C19 123.3(5) . . . . ? C12 C13 C14 Ir1 59.3(3) . . . . ? C18 C13 C14 Ir1 -119.9(5) . . . . ? O2 Ir1 C14 C13 168.4(2) . . . . ? C12 Ir1 C14 C13 -37.0(3) . . . . ? C15 Ir1 C14 C13 -116.5(3) . . . . ? C11 Ir1 C14 C13 -79.9(3) . . . . ? O1 Ir1 C14 C13 -62.9(8) . . . . ? Cl1 Ir1 C14 C13 76.4(3) . . . . ? O2 Ir1 C14 C15 -75.1(2) . . . . ? C12 Ir1 C14 C15 79.5(3) . . . . ? C11 Ir1 C14 C15 36.6(2) . . . . ? C13 Ir1 C14 C15 116.5(3) . . . . ? O1 Ir1 C14 C15 53.6(8) . . . . ? Cl1 Ir1 C14 C15 -167.1(2) . . . . ? O2 Ir1 C14 C19 46.0(6) . . . . ? C12 Ir1 C14 C19 -159.5(6) . . . . ? C15 Ir1 C14 C19 121.0(6) . . . . ? C11 Ir1 C14 C19 157.6(6) . . . . ? C13 Ir1 C14 C19 -122.4(6) . . . . ? O1 Ir1 C14 C19 174.6(5) . . . . ? Cl1 Ir1 C14 C19 -46.1(5) . . . . ? C12 C11 C15 C14 -1.7(5) . . . . ? C16 C11 C15 C14 -179.9(5) . . . . ? Ir1 C11 C15 C14 58.7(3) . . . . ? C12 C11 C15 C20 179.5(4) . . . . ? C16 C11 C15 C20 1.4(8) . . . . ? Ir1 C11 C15 C20 -120.0(5) . . . . ? C12 C11 C15 Ir1 -60.5(3) . . . . ? C16 C11 C15 Ir1 121.4(5) . . . . ? C13 C14 C15 C11 3.2(5) . . . . ? C19 C14 C15 C11 177.2(4) . . . . ? Ir1 C14 C15 C11 -60.0(3) . . . . ? C13 C14 C15 C20 -178.0(4) . . . . ? C19 C14 C15 C20 -3.9(7) . . . . ? Ir1 C14 C15 C20 118.8(4) . . . . ? C13 C14 C15 Ir1 63.2(3) . . . . ? C19 C14 C15 Ir1 -122.8(4) . . . . ? O2 Ir1 C15 C11 -124.5(3) . . . . ? C14 Ir1 C15 C11 119.3(4) . . . . ? C12 Ir1 C15 C11 37.8(3) . . . . ? C13 Ir1 C15 C11 80.7(3) . . . . ? O1 Ir1 C15 C11 -46.5(3) . . . . ? Cl1 Ir1 C15 C11 141.7(2) . . . . ? O2 Ir1 C15 C14 116.2(2) . . . . ? C12 Ir1 C15 C14 -81.5(3) . . . . ? C11 Ir1 C15 C14 -119.3(4) . . . . ? C13 Ir1 C15 C14 -38.6(2) . . . . ? O1 Ir1 C15 C14 -165.8(2) . . . . ? Cl1 Ir1 C15 C14 22.4(4) . . . . ? O2 Ir1 C15 C20 -1.9(5) . . . . ? C14 Ir1 C15 C20 -118.0(6) . . . . ? C12 Ir1 C15 C20 160.4(5) . . . . ? C11 Ir1 C15 C20 122.7(6) . . . . ? C13 Ir1 C15 C20 -156.6(5) . . . . ? O1 Ir1 C15 C20 76.1(5) . . . . ? Cl1 Ir1 C15 C20 -95.7(5) . . . . ? C26 C21 C22 C23 -2.0(6) . . . . ? C30 C21 C22 C23 179.0(4) . . . . ? C21 C22 C23 C24 2.9(7) . . . . ? C22 C23 C24 C25 -2.0(7) . . . . ? C23 C24 C25 C26 0.1(7) . . . . ? C24 C25 C26 C21 0.8(6) . . . . ? C24 C25 C26 C27 -179.2(4) . . . . ? C22 C21 C26 C25 0.2(6) . . . . ? C30 C21 C26 C25 179.2(4) . . . . ? C22 C21 C26 C27 -179.8(4) . . . . ? C30 C21 C26 C27 -0.8(5) . . . . ? C25 C26 C27 O6 1.3(6) . . . . ? C21 C26 C27 O6 -178.8(4) . . . . ? C25 C26 C27 C28 -179.8(4) . . . . ? C21 C26 C27 C28 0.1(5) . . . . ? O6 C27 C28 C29 179.7(4) . . . . ? C26 C27 C28 C29 0.8(6) . . . . ? Ir2 O4 C29 C28 -168.3(3) . . . . ? Ir2 O4 C29 C30 16.9(4) . . . . ? C27 C28 C29 O4 -175.6(4) . . . . ? C27 C28 C29 C30 -1.0(6) . . . . ? Ir2 O5 C30 C21 170.9(3) . . . . ? Ir2 O5 C30 C29 -7.6(4) . . . . ? C22 C21 C30 O5 1.1(6) . . . . ? C26 C21 C30 O5 -177.9(4) . . . . ? C22 C21 C30 C29 179.6(4) . . . . ? C26 C21 C30 C29 0.6(5) . . . . ? O4 C29 C30 O5 -5.9(5) . . . . ? C28 C29 C30 O5 178.9(4) . . . . ? O4 C29 C30 C21 175.5(3) . . . . ? C28 C29 C30 C21 0.3(5) . . . . ? O4 Ir2 C31 C32 -126.9(4) . . . . ? C33 Ir2 C31 C32 -37.0(3) . . . . ? C34 Ir2 C31 C32 -80.5(3) . . . . ? C35 Ir2 C31 C32 -117.2(4) . . . . ? O5 Ir2 C31 C32 151.4(2) . . . . ? Cl2 Ir2 C31 C32 63.3(3) . . . . ? O4 Ir2 C31 C35 -9.6(5) . . . . ? C33 Ir2 C31 C35 80.3(3) . . . . ? C34 Ir2 C31 C35 36.8(3) . . . . ? C32 Ir2 C31 C35 117.2(4) . . . . ? O5 Ir2 C31 C35 -91.4(3) . . . . ? Cl2 Ir2 C31 C35 -179.4(2) . . . . ? O4 Ir2 C31 C38 111.2(5) . . . . ? C33 Ir2 C31 C38 -158.9(5) . . . . ? C34 Ir2 C31 C38 157.6(5) . . . . ? C32 Ir2 C31 C38 -121.9(6) . . . . ? C35 Ir2 C31 C38 120.9(6) . . . . ? O5 Ir2 C31 C38 29.5(5) . . . . ? Cl2 Ir2 C31 C38 -58.6(5) . . . . ? C35 C31 C32 C33 -2.5(5) . . . . ? C38 C31 C32 C33 -177.7(4) . . . . ? Ir2 C31 C32 C33 59.2(3) . . . . ? C35 C31 C32 C39 178.8(4) . . . . ? C38 C31 C32 C39 3.7(8) . . . . ? Ir2 C31 C32 C39 -119.5(5) . . . . ? C35 C31 C32 Ir2 -61.7(3) . . . . ? C38 C31 C32 Ir2 123.2(5) . . . . ? O4 Ir2 C32 C31 143.0(3) . . . . ? C33 Ir2 C32 C31 120.0(4) . . . . ? C34 Ir2 C32 C31 81.3(3) . . . . ? C35 Ir2 C32 C31 38.6(3) . . . . ? O5 Ir2 C32 C31 -41.5(3) . . . . ? Cl2 Ir2 C32 C31 -126.9(2) . . . . ? O4 Ir2 C32 C33 23.1(4) . . . . ? C31 Ir2 C32 C33 -120.0(4) . . . . ? C34 Ir2 C32 C33 -38.6(2) . . . . ? C35 Ir2 C32 C33 -81.4(3) . . . . ? O5 Ir2 C32 C33 -161.5(2) . . . . ? Cl2 Ir2 C32 C33 113.2(2) . . . . ? O4 Ir2 C32 C39 -95.6(5) . . . . ? C33 Ir2 C32 C39 -118.7(6) . . . . ? C31 Ir2 C32 C39 121.3(6) . . . . ? C34 Ir2 C32 C39 -157.3(5) . . . . ? C35 Ir2 C32 C39 159.9(5) . . . . ? O5 Ir2 C32 C39 79.8(5) . . . . ? Cl2 Ir2 C32 C39 -5.5(5) . . . . ? C31 C32 C33 C34 2.1(5) . . . . ? C39 C32 C33 C34 -179.2(4) . . . . ? Ir2 C32 C33 C34 61.7(3) . . . . ? C31 C32 C33 C40 175.3(4) . . . . ? C39 C32 C33 C40 -6.0(7) . . . . ? Ir2 C32 C33 C40 -125.1(4) . . . . ? C31 C32 C33 Ir2 -59.6(3) . . . . ? C39 C32 C33 Ir2 119.1(4) . . . . ? O4 Ir2 C33 C32 -167.6(2) . . . . ? C31 Ir2 C33 C32 36.6(3) . . . . ? C34 Ir2 C33 C32 116.9(3) . . . . ? C35 Ir2 C33 C32 80.1(3) . . . . ? O5 Ir2 C33 C32 74.3(7) . . . . ? Cl2 Ir2 C33 C32 -75.4(2) . . . . ? O4 Ir2 C33 C34 75.4(3) . . . . ? C31 Ir2 C33 C34 -80.3(3) . . . . ? C32 Ir2 C33 C34 -116.9(3) . . . . ? C35 Ir2 C33 C34 -36.8(2) . . . . ? O5 Ir2 C33 C34 -42.6(8) . . . . ? Cl2 Ir2 C33 C34 167.7(2) . . . . ? O4 Ir2 C33 C40 -44.9(5) . . . . ? C31 Ir2 C33 C40 159.3(6) . . . . ? C34 Ir2 C33 C40 -120.4(6) . . . . ? C32 Ir2 C33 C40 122.7(6) . . . . ? C35 Ir2 C33 C40 -157.2(6) . . . . ? O5 Ir2 C33 C40 -163.0(5) . . . . ? Cl2 Ir2 C33 C40 47.3(5) . . . . ? C32 C33 C34 C35 -0.9(5) . . . . ? C40 C33 C34 C35 -174.2(4) . . . . ? Ir2 C33 C34 C35 60.9(3) . . . . ? C32 C33 C34 C36 179.9(4) . . . . ? C40 C33 C34 C36 6.5(7) . . . . ? Ir2 C33 C34 C36 -118.4(4) . . . . ? C32 C33 C34 Ir2 -61.8(3) . . . . ? C40 C33 C34 Ir2 124.9(4) . . . . ? O4 Ir2 C34 C35 126.2(3) . . . . ? C33 Ir2 C34 C35 -119.1(4) . . . . ? C31 Ir2 C34 C35 -37.6(3) . . . . ? C32 Ir2 C34 C35 -80.6(3) . . . . ? O5 Ir2 C34 C35 49.1(3) . . . . ? Cl2 Ir2 C34 C35 -141.0(2) . . . . ? O4 Ir2 C34 C33 -114.7(2) . . . . ? C31 Ir2 C34 C33 81.5(3) . . . . ? C32 Ir2 C34 C33 38.5(3) . . . . ? C35 Ir2 C34 C33 119.1(4) . . . . ? O5 Ir2 C34 C33 168.2(2) . . . . ? Cl2 Ir2 C34 C33 -21.9(4) . . . . ? O4 Ir2 C34 C36 5.8(4) . . . . ? C33 Ir2 C34 C36 120.5(5) . . . . ? C31 Ir2 C34 C36 -158.0(5) . . . . ? C32 Ir2 C34 C36 159.0(5) . . . . ? C35 Ir2 C34 C36 -120.4(5) . . . . ? O5 Ir2 C34 C36 -71.3(4) . . . . ? Cl2 Ir2 C34 C36 98.6(4) . . . . ? C33 C34 C35 C31 -0.6(5) . . . . ? C36 C34 C35 C31 178.6(4) . . . . ? Ir2 C34 C35 C31 59.2(3) . . . . ? C33 C34 C35 C37 -179.3(4) . . . . ? C36 C34 C35 C37 0.0(7) . . . . ? Ir2 C34 C35 C37 -119.4(5) . . . . ? C33 C34 C35 Ir2 -59.8(3) . . . . ? C36 C34 C35 Ir2 119.4(4) . . . . ? C32 C31 C35 C34 1.9(5) . . . . ? C38 C31 C35 C34 177.2(4) . . . . ? Ir2 C31 C35 C34 -59.5(3) . . . . ? C32 C31 C35 C37 -179.4(4) . . . . ? C38 C31 C35 C37 -4.2(7) . . . . ? Ir2 C31 C35 C37 119.2(5) . . . . ? C32 C31 C35 Ir2 61.4(3) . . . . ? C38 C31 C35 Ir2 -123.3(5) . . . . ? O4 Ir2 C35 C34 -65.0(3) . . . . ? C33 Ir2 C35 C34 37.6(3) . . . . ? C31 Ir2 C35 C34 119.2(4) . . . . ? C32 Ir2 C35 C34 81.1(3) . . . . ? O5 Ir2 C35 C34 -143.8(3) . . . . ? Cl2 Ir2 C35 C34 120.4(3) . . . . ? O4 Ir2 C35 C31 175.9(2) . . . . ? C33 Ir2 C35 C31 -81.6(3) . . . . ? C34 Ir2 C35 C31 -119.2(4) . . . . ? C32 Ir2 C35 C31 -38.0(3) . . . . ? O5 Ir2 C35 C31 97.1(3) . . . . ? Cl2 Ir2 C35 C31 1.3(5) . . . . ? O4 Ir2 C35 C37 56.8(4) . . . . ? C33 Ir2 C35 C37 159.4(4) . . . . ? C31 Ir2 C35 C37 -119.1(5) . . . . ? C34 Ir2 C35 C37 121.8(5) . . . . ? C32 Ir2 C35 C37 -157.1(4) . . . . ? O5 Ir2 C35 C37 -22.0(4) . . . . ? Cl2 Ir2 C35 C37 -117.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 5.620 _refine_diff_density_min -1.372 _refine_diff_density_rms 0.132