# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ola Wendt' _publ_contact_author_email OLA.WENDT@ORGANIC.LU.SE _publ_section_title ; Synthesis and characterisation of PCsp3P phosphine and phosphinite iridium complexes. Cyclometallation and dehydrogenation of a cyclohexyl ring ; loop_ _publ_author_name 'Ola Wendt' 'Athimoolam Arunachalampillai' 'Daniel Olsson' # Attachment 'cif.CIF' data_dan11b_complex3 _database_code_depnum_ccdc_archive 'CCDC 658487' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H49 Cl Ir P2' _chemical_formula_weight 628.22 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' P P 0.1023 0.0942 '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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.3722(2) _cell_length_b 15.0811(2) _cell_length_c 28.6246(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5340.96(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16991 _cell_measurement_theta_min 2.1283 _cell_measurement_theta_max 33.1768 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2536 _exptl_absorpt_coefficient_mu 5.228 _exptl_absorpt_correction_T_min 0.37698 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1829 _diffrn_measurement_device_type 'Oxford Diffraction XCalibur 3' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50780 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 33.25 _reflns_number_total 9705 _reflns_number_gt 5606 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0608P)^2^+8.6510P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9705 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.496472(13) 0.334412(11) 0.137393(5) 0.01668(6) Uani 1 1 d . . . P1 P 0.63335(10) 0.41407(8) 0.10236(4) 0.0208(2) Uani 1 1 d . . . P2 P 0.35658(10) 0.23900(9) 0.15580(5) 0.0251(3) Uani 1 1 d . . . Cl1 Cl 0.46965(13) 0.43558(10) 0.20269(5) 0.0393(3) Uani 1 1 d . . . C1 C 0.4934(4) 0.2669(3) 0.07346(16) 0.0222(9) Uani 1 1 d . . . H1 H 0.4430 0.3009 0.0540 0.027 Uiso 1 1 calc R . . C9 C 0.7713(4) 0.4083(4) 0.12938(19) 0.0273(11) Uani 1 1 d . . . C7 C 0.6450(4) 0.3612(3) 0.04472(17) 0.0264(10) Uani 1 1 d . . . H7A H 0.6059 0.3959 0.0217 0.032 Uiso 1 1 calc R . . H7B H 0.7204 0.3591 0.0354 0.032 Uiso 1 1 calc R . . C10 C 0.5951(4) 0.5307(3) 0.08796(17) 0.0246(10) Uani 1 1 d . . . C8 C 0.3425(4) 0.1710(4) 0.10268(18) 0.0301(11) Uani 1 1 d . . . H8A H 0.3258 0.1103 0.1113 0.036 Uiso 1 1 calc R . . H8B H 0.2835 0.1935 0.0838 0.036 Uiso 1 1 calc R . . C4 C 0.5419(5) 0.1333(4) 0.0003(2) 0.0351(12) Uani 1 1 d . . . H4A H 0.5295 0.1118 -0.0312 0.042 Uiso 1 1 calc R . . H4B H 0.5929 0.0937 0.0153 0.042 Uiso 1 1 calc R . . C11 C 0.2209(4) 0.2948(4) 0.1612(2) 0.0358(13) Uani 1 1 d . . . C6 C 0.5996(4) 0.2683(4) 0.04639(18) 0.0284(11) Uani 1 1 d . . . H6 H 0.6512 0.2322 0.0641 0.034 Uiso 1 1 calc R . . C2 C 0.4462(5) 0.1734(3) 0.07489(19) 0.0304(12) Uani 1 1 d . . . H2 H 0.4983 0.1369 0.0920 0.036 Uiso 1 1 calc R . . C5 C 0.5898(4) 0.2262(3) -0.00188(17) 0.0264(10) Uani 1 1 d . . . H5A H 0.5444 0.2633 -0.0214 0.032 Uiso 1 1 calc R . . H5B H 0.6608 0.2234 -0.0162 0.032 Uiso 1 1 calc R . . C3 C 0.4357(4) 0.1325(4) 0.02720(18) 0.0285(11) Uani 1 1 d . . . H3A H 0.3816 0.1648 0.0095 0.034 Uiso 1 1 calc R . . H3B H 0.4110 0.0718 0.0305 0.034 Uiso 1 1 calc R . . C20 C 0.2040(5) 0.3346(4) 0.2095(2) 0.0415(15) Uani 1 1 d . . . H20A H 0.1408 0.3715 0.2092 0.062 Uiso 1 1 calc R . . H20B H 0.2659 0.3695 0.2179 0.062 Uiso 1 1 calc R . . H20C H 0.1946 0.2879 0.2319 0.062 Uiso 1 1 calc R . . C13 C 0.8070(5) 0.3128(5) 0.1268(3) 0.0493(17) Uani 1 1 d . . . H13A H 0.8709 0.3048 0.1454 0.074 Uiso 1 1 calc R . . H13B H 0.8222 0.2975 0.0950 0.074 Uiso 1 1 calc R . . H13C H 0.7505 0.2753 0.1386 0.074 Uiso 1 1 calc R . . C12 C 0.3802(5) 0.1596(4) 0.20513(19) 0.0333(12) Uani 1 1 d . . . C19 C 0.2230(5) 0.3737(5) 0.1263(2) 0.0425(15) Uani 1 1 d . . . H19A H 0.1541 0.4030 0.1266 0.064 Uiso 1 1 calc R . . H19B H 0.2378 0.3521 0.0955 0.064 Uiso 1 1 calc R . . H19C H 0.2783 0.4149 0.1354 0.064 Uiso 1 1 calc R . . C17 C 0.6083(5) 0.5919(4) 0.13081(19) 0.0345(13) Uani 1 1 d . . . H17A H 0.6837 0.6019 0.1365 0.052 Uiso 1 1 calc R . . H17B H 0.5762 0.5642 0.1577 0.052 Uiso 1 1 calc R . . H17C H 0.5731 0.6475 0.1249 0.052 Uiso 1 1 calc R . . C14 C 0.8560(4) 0.4652(4) 0.1035(2) 0.0397(14) Uani 1 1 d . . . H14A H 0.8380 0.5268 0.1068 0.060 Uiso 1 1 calc R . . H14B H 0.8563 0.4496 0.0710 0.060 Uiso 1 1 calc R . . H14C H 0.9262 0.4545 0.1166 0.060 Uiso 1 1 calc R . . C21 C 0.1264(5) 0.2358(5) 0.1494(2) 0.0505(18) Uani 1 1 d . . . H21A H 0.1266 0.1850 0.1696 0.076 Uiso 1 1 calc R . . H21B H 0.1321 0.2166 0.1175 0.076 Uiso 1 1 calc R . . H21C H 0.0603 0.2681 0.1535 0.076 Uiso 1 1 calc R . . C18 C 0.4741(5) 0.5292(4) 0.0757(2) 0.0385(14) Uani 1 1 d . . . H18A H 0.4511 0.5877 0.0670 0.058 Uiso 1 1 calc R . . H18B H 0.4334 0.5097 0.1024 0.058 Uiso 1 1 calc R . . H18C H 0.4621 0.4892 0.0501 0.058 Uiso 1 1 calc R . . C16 C 0.6563(5) 0.5710(4) 0.0466(2) 0.0364(13) Uani 1 1 d . . . H16A H 0.6512 0.5319 0.0202 0.055 Uiso 1 1 calc R . . H16B H 0.7308 0.5789 0.0549 0.055 Uiso 1 1 calc R . . H16C H 0.6251 0.6273 0.0388 0.055 Uiso 1 1 calc R . . C15 C 0.7656(4) 0.4358(4) 0.1797(2) 0.0379(13) Uani 1 1 d . . . H15A H 0.8323 0.4211 0.1950 0.057 Uiso 1 1 calc R . . H15B H 0.7071 0.4053 0.1947 0.057 Uiso 1 1 calc R . . H15C H 0.7538 0.4986 0.1815 0.057 Uiso 1 1 calc R . . C23 C 0.4734(6) 0.0968(5) 0.1888(2) 0.0478(16) Uani 1 1 d . . . H23A H 0.5356 0.1316 0.1807 0.072 Uiso 1 1 calc R . . H23B H 0.4500 0.0635 0.1621 0.072 Uiso 1 1 calc R . . H23C H 0.4917 0.0569 0.2137 0.072 Uiso 1 1 calc R . . C24 C 0.4162(6) 0.2098(4) 0.2478(2) 0.0492(17) Uani 1 1 d . . . H24A H 0.3574 0.2452 0.2593 0.074 Uiso 1 1 calc R . . H24B H 0.4758 0.2476 0.2398 0.074 Uiso 1 1 calc R . . H24C H 0.4383 0.1686 0.2715 0.074 Uiso 1 1 calc R . . C22 C 0.2838(6) 0.1015(5) 0.2172(2) 0.0552(19) Uani 1 1 d . . . H22A H 0.3069 0.0540 0.2372 0.083 Uiso 1 1 calc R . . H22B H 0.2536 0.0773 0.1891 0.083 Uiso 1 1 calc R . . H22C H 0.2302 0.1364 0.2330 0.083 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 0.01684(9) 0.01595(9) 0.01726(9) -0.00151(6) 0.00037(6) -0.00179(7) P1 0.0180(5) 0.0172(6) 0.0272(6) -0.0010(5) 0.0022(5) -0.0016(5) P2 0.0211(6) 0.0269(7) 0.0273(6) -0.0026(5) 0.0017(5) -0.0074(5) Cl1 0.0411(7) 0.0401(8) 0.0368(7) -0.0140(6) 0.0128(6) -0.0131(6) C1 0.025(2) 0.020(2) 0.021(2) 0.0005(17) -0.0001(18) 0.0029(19) C9 0.017(2) 0.027(3) 0.038(3) -0.002(2) -0.0029(19) -0.003(2) C7 0.027(2) 0.023(2) 0.029(2) -0.002(2) 0.007(2) -0.005(2) C10 0.027(2) 0.019(2) 0.029(2) 0.0011(19) 0.003(2) -0.0004(19) C8 0.029(3) 0.033(3) 0.029(2) -0.006(2) 0.004(2) -0.007(2) C4 0.036(3) 0.032(3) 0.038(3) -0.010(2) -0.003(3) 0.000(2) C11 0.015(2) 0.048(4) 0.044(3) 0.000(3) 0.001(2) -0.004(2) C6 0.026(2) 0.029(3) 0.030(3) -0.008(2) 0.002(2) -0.001(2) C2 0.037(3) 0.020(3) 0.034(3) -0.005(2) 0.011(2) -0.006(2) C5 0.028(2) 0.025(2) 0.026(2) 0.001(2) 0.003(2) -0.003(2) C3 0.030(3) 0.022(3) 0.033(3) -0.006(2) -0.004(2) 0.000(2) C20 0.026(3) 0.046(4) 0.053(4) -0.016(3) 0.009(2) -0.002(3) C13 0.024(3) 0.039(4) 0.085(5) 0.005(4) -0.013(3) 0.008(3) C12 0.040(3) 0.027(3) 0.033(3) 0.005(2) 0.006(2) -0.010(2) C19 0.025(3) 0.058(4) 0.045(3) 0.000(3) -0.001(2) 0.008(3) C17 0.047(3) 0.018(3) 0.039(3) -0.003(2) 0.006(2) 0.001(2) C14 0.019(2) 0.046(4) 0.054(4) -0.005(3) 0.008(2) -0.008(2) C21 0.022(3) 0.068(5) 0.062(4) -0.022(4) 0.007(3) -0.011(3) C18 0.034(3) 0.035(3) 0.046(3) 0.009(3) -0.006(3) 0.005(2) C16 0.039(3) 0.025(3) 0.045(3) 0.007(2) 0.009(3) -0.002(2) C15 0.022(3) 0.052(4) 0.039(3) -0.002(3) -0.007(2) -0.003(2) C23 0.060(4) 0.040(4) 0.043(4) 0.009(3) -0.003(3) 0.007(3) C24 0.063(5) 0.045(4) 0.040(3) 0.009(3) -0.006(3) -0.003(3) C22 0.073(5) 0.045(4) 0.048(4) 0.005(3) 0.013(3) -0.025(4) _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 C1 2.094(5) . ? Ir1 P1 2.3059(12) . ? Ir1 P2 2.3116(13) . ? Ir1 Cl1 2.4354(14) . ? P1 C7 1.838(5) . ? P1 C10 1.868(5) . ? P1 C9 1.876(5) . ? P2 C8 1.842(5) . ? P2 C12 1.874(6) . ? P2 C11 1.884(6) . ? C1 C2 1.527(7) . ? C1 C6 1.526(7) . ? C1 H1 0.9800 . ? C9 C15 1.500(8) . ? C9 C13 1.508(8) . ? C9 C14 1.543(7) . ? C7 C6 1.510(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C10 C16 1.530(7) . ? C10 C18 1.538(7) . ? C10 C17 1.543(7) . ? C8 C2 1.511(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 C3 1.523(8) . ? C4 C5 1.523(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C11 C21 1.508(8) . ? C11 C20 1.522(8) . ? C11 C19 1.554(9) . ? C6 C5 1.525(7) . ? C6 H6 0.9800 . ? C2 C3 1.504(7) . ? C2 H2 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C12 C24 1.504(8) . ? C12 C22 1.520(8) . ? C12 C23 1.564(9) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C1 Ir1 P1 83.47(13) . . ? C1 Ir1 P2 83.29(13) . . ? P1 Ir1 P2 166.74(5) . . ? C1 Ir1 Cl1 166.55(14) . . ? P1 Ir1 Cl1 96.17(5) . . ? P2 Ir1 Cl1 96.49(5) . . ? C7 P1 C10 103.3(2) . . ? C7 P1 C9 106.2(2) . . ? C10 P1 C9 111.4(2) . . ? C7 P1 Ir1 102.84(16) . . ? C10 P1 Ir1 113.60(16) . . ? C9 P1 Ir1 117.69(18) . . ? C8 P2 C12 106.3(3) . . ? C8 P2 C11 103.4(3) . . ? C12 P2 C11 111.2(3) . . ? C8 P2 Ir1 103.27(17) . . ? C12 P2 Ir1 116.92(19) . . ? C11 P2 Ir1 114.1(2) . . ? C2 C1 C6 110.8(4) . . ? C2 C1 Ir1 115.6(3) . . ? C6 C1 Ir1 114.9(3) . . ? C2 C1 H1 104.7 . . ? C6 C1 H1 104.7 . . ? Ir1 C1 H1 104.7 . . ? C15 C9 C13 108.9(5) . . ? C15 C9 C14 109.8(4) . . ? C13 C9 C14 108.0(5) . . ? C15 C9 P1 109.9(4) . . ? C13 C9 P1 106.9(4) . . ? C14 C9 P1 113.2(4) . . ? C6 C7 P1 110.2(3) . . ? C6 C7 H7A 109.6 . . ? P1 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? P1 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C16 C10 C18 108.2(5) . . ? C16 C10 C17 109.0(4) . . ? C18 C10 C17 107.0(4) . . ? C16 C10 P1 114.7(4) . . ? C18 C10 P1 106.4(4) . . ? C17 C10 P1 111.1(3) . . ? C2 C8 P2 109.9(4) . . ? C2 C8 H8A 109.7 . . ? P2 C8 H8A 109.7 . . ? C2 C8 H8B 109.7 . . ? P2 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C3 C4 C5 111.3(4) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C21 C11 C20 109.2(5) . . ? C21 C11 C19 108.7(5) . . ? C20 C11 C19 106.5(5) . . ? C21 C11 P2 114.2(5) . . ? C20 C11 P2 111.9(4) . . ? C19 C11 P2 106.0(4) . . ? C7 C6 C5 112.8(4) . . ? C7 C6 C1 110.4(4) . . ? C5 C6 C1 112.7(4) . . ? C7 C6 H6 106.8 . . ? C5 C6 H6 106.8 . . ? C1 C6 H6 106.8 . . ? C3 C2 C8 113.2(5) . . ? C3 C2 C1 112.8(4) . . ? C8 C2 C1 111.2(4) . . ? C3 C2 H2 106.3 . . ? C8 C2 H2 106.3 . . ? C1 C2 H2 106.3 . . ? C4 C5 C6 112.2(4) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C2 C3 C4 112.4(4) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C24 C12 C22 109.7(5) . . ? C24 C12 C23 109.2(5) . . ? C22 C12 C23 107.3(5) . . ? C24 C12 P2 109.7(4) . . ? C22 C12 P2 114.7(5) . . ? C23 C12 P2 106.1(4) . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C17 H17A 109.5 . . ? C10 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C10 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C21 H21A 109.5 . . ? C11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 C18 H18A 109.5 . . ? C10 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C10 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C23 H23A 109.5 . . ? C12 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C12 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 C24 H24A 109.5 . . ? C12 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C12 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.761 _refine_diff_density_min -1.583 _refine_diff_density_rms 0.227 # Attachment 'complex4.CIF' data_complex4 _database_code_depnum_ccdc_archive 'CCDC 658489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H49 Ir N2 P2' _chemical_formula_weight 619.79 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' Ir Ir -1.4442 7.9887 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 29.3338(7) _cell_length_b 12.4022(3) _cell_length_c 15.3075(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5568.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5090 _cell_measurement_theta_min 2.1112 _cell_measurement_theta_max 33.0568 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 4.922 _exptl_absorpt_correction_T_min 0.75171 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction XCalibur 3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 33522 _diffrn_reflns_av_R_equivalents 0.0732 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4917 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0100P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4917 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0456 _refine_ls_wR_factor_gt 0.0405 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _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 0.862830(7) 0.50637(2) 0.832764(13) 0.04446(8) Uani 1 1 d . . . P2 P 0.89679(6) 0.36906(14) 0.90951(10) 0.0488(5) Uani 1 1 d . . . P1 P 0.84643(6) 0.64634(14) 0.73976(11) 0.0587(5) Uani 1 1 d . . . N1 N 0.8109(2) 0.5181(8) 0.9035(5) 0.117(3) Uani 1 1 d . . . C19 C 0.8932(2) 0.1432(5) 0.9523(4) 0.089(3) Uani 1 1 d . . . H19A H 0.8882 0.1537 1.0137 0.134 Uiso 1 1 calc R . . H19B H 0.9253 0.1448 0.9402 0.134 Uiso 1 1 calc R . . H19C H 0.8809 0.0746 0.9351 0.134 Uiso 1 1 calc R . . C2 C 0.9252(2) 0.5569(5) 0.6765(4) 0.073(2) Uani 1 1 d . . . H2 H 0.9089 0.5063 0.6386 0.088 Uiso 1 1 calc R . . C14 C 0.8784(2) 0.7858(6) 0.8644(5) 0.122(4) Uani 1 1 d . . . H14A H 0.9081 0.7838 0.8381 0.183 Uiso 1 1 calc R . . H14B H 0.8747 0.7243 0.9019 0.183 Uiso 1 1 calc R . . H14C H 0.8753 0.8507 0.8982 0.183 Uiso 1 1 calc R . . C3 C 0.9727(2) 0.5655(5) 0.6354(4) 0.072(2) Uani 1 1 d . . . H3A H 0.9694 0.5880 0.5751 0.087 Uiso 1 1 calc R . . H3B H 0.9897 0.6213 0.6658 0.087 Uiso 1 1 calc R . . C24 C 0.9286(2) 0.5183(5) 1.0252(4) 0.093(2) Uani 1 1 d . . . H24A H 0.9041 0.5656 1.0088 0.139 Uiso 1 1 calc R . . H24B H 0.9530 0.5251 0.9838 0.139 Uiso 1 1 calc R . . H24C H 0.9394 0.5375 1.0823 0.139 Uiso 1 1 calc R . . N2 N 0.7796(3) 0.5228(8) 0.9384(5) 0.145(3) Uani 1 1 d . . . C8 C 0.95230(19) 0.3527(5) 0.8579(3) 0.062(2) Uani 1 1 d . . . H8A H 0.9757 0.3846 0.8945 0.074 Uiso 1 1 calc R . . H8B H 0.9591 0.2765 0.8515 0.074 Uiso 1 1 calc R . . C4 C 0.9989(3) 0.4672(6) 0.6377(5) 0.111(3) Uani 1 1 d . . . H4A H 1.0301 0.4832 0.6211 0.133 Uiso 1 1 calc R . . H4B H 0.9866 0.4174 0.5949 0.133 Uiso 1 1 calc R . . C21 C 0.9115(2) 0.4022(5) 1.0261(4) 0.058(2) Uani 1 1 d . . . C7 C 0.8978(2) 0.6587(5) 0.6712(4) 0.080(2) Uani 1 1 d . . . H7A H 0.8890 0.6721 0.6111 0.096 Uiso 1 1 calc R . . H7B H 0.9160 0.7191 0.6911 0.096 Uiso 1 1 calc R . . C23 C 0.8692(2) 0.3967(5) 1.0837(4) 0.090(2) Uani 1 1 d . . . H23A H 0.8763 0.4242 1.1407 0.136 Uiso 1 1 calc R . . H23B H 0.8593 0.3232 1.0885 0.136 Uiso 1 1 calc R . . H23C H 0.8454 0.4394 1.0581 0.136 Uiso 1 1 calc R . . C5 C 0.9990(2) 0.4133(5) 0.7263(4) 0.071(2) Uani 1 1 d . . . H5A H 1.0112 0.3411 0.7198 0.085 Uiso 1 1 calc R . . H5B H 1.0194 0.4530 0.7645 0.085 Uiso 1 1 calc R . . C1 C 0.92453(16) 0.5044(6) 0.7643(3) 0.0550(15) Uani 1 1 d . . . H1 H 0.9428 0.5552 0.7987 0.066 Uiso 1 1 calc R . . C18 C 0.8676(3) 0.2021(5) 0.8049(4) 0.109(3) Uani 1 1 d . . . H18A H 0.8511 0.1356 0.7987 0.164 Uiso 1 1 calc R . . H18B H 0.8981 0.1931 0.7833 0.164 Uiso 1 1 calc R . . H18C H 0.8525 0.2577 0.7723 0.164 Uiso 1 1 calc R . . C6 C 0.9527(2) 0.4055(5) 0.7702(5) 0.078(2) Uani 1 1 d . . . H6 H 0.9362 0.3540 0.7333 0.094 Uiso 1 1 calc R . . C17 C 0.8692(2) 0.2335(5) 0.9008(4) 0.0578(19) Uani 1 1 d . . . C9 C 0.7985(3) 0.6239(6) 0.6609(5) 0.084(2) Uani 1 1 d . . . C22 C 0.9495(2) 0.3295(5) 1.0653(4) 0.101(3) Uani 1 1 d . . . H22A H 0.9759 0.3321 1.0284 0.152 Uiso 1 1 calc R . . H22B H 0.9387 0.2566 1.0690 0.152 Uiso 1 1 calc R . . H22C H 0.9573 0.3549 1.1226 0.152 Uiso 1 1 calc R . . C20 C 0.8200(2) 0.2401(5) 0.9324(4) 0.095(3) Uani 1 1 d . . . H20A H 0.8035 0.1779 0.9125 0.143 Uiso 1 1 calc R . . H20B H 0.8060 0.3041 0.9095 0.143 Uiso 1 1 calc R . . H20C H 0.8194 0.2424 0.9951 0.143 Uiso 1 1 calc R . . C12 C 0.7883(2) 0.7202(6) 0.6007(5) 0.146(4) Uani 1 1 d . . . H12A H 0.7621 0.7043 0.5655 0.219 Uiso 1 1 calc R . . H12B H 0.8141 0.7333 0.5635 0.219 Uiso 1 1 calc R . . H12C H 0.7824 0.7830 0.6355 0.219 Uiso 1 1 calc R . . C11 C 0.7554(2) 0.5937(6) 0.7101(4) 0.115(3) Uani 1 1 d . . . H11A H 0.7475 0.6505 0.7499 0.173 Uiso 1 1 calc R . . H11B H 0.7604 0.5282 0.7421 0.173 Uiso 1 1 calc R . . H11C H 0.7309 0.5834 0.6692 0.173 Uiso 1 1 calc R . . C16 C 0.8507(3) 0.8784(5) 0.7333(5) 0.135(4) Uani 1 1 d . . . H16A H 0.8438 0.9440 0.7639 0.203 Uiso 1 1 calc R . . H16B H 0.8318 0.8733 0.6821 0.203 Uiso 1 1 calc R . . H16C H 0.8822 0.8784 0.7164 0.203 Uiso 1 1 calc R . . C13 C 0.8415(3) 0.7836(6) 0.7921(5) 0.076(3) Uani 1 1 d . . . C15 C 0.7957(2) 0.7963(5) 0.8384(5) 0.102(3) Uani 1 1 d . . . H15A H 0.7964 0.8597 0.8743 0.153 Uiso 1 1 calc R . . H15B H 0.7901 0.7341 0.8742 0.153 Uiso 1 1 calc R . . H15C H 0.7719 0.8030 0.7957 0.153 Uiso 1 1 calc R . . C10 C 0.8109(3) 0.5293(7) 0.6048(4) 0.141(4) Uani 1 1 d . . . H10A H 0.8075 0.4639 0.6377 0.211 Uiso 1 1 calc R . . H10B H 0.8420 0.5361 0.5859 0.211 Uiso 1 1 calc R . . H10C H 0.7912 0.5272 0.5547 0.211 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 0.04123(12) 0.04902(14) 0.04315(11) 0.0037(2) 0.00614(14) 0.0023(2) P2 0.0533(12) 0.0477(12) 0.0453(11) -0.0015(9) 0.0024(9) 0.0038(10) P1 0.0587(14) 0.0597(13) 0.0576(12) 0.0135(10) 0.0100(10) 0.0106(10) N1 0.101(6) 0.117(7) 0.132(6) 0.062(6) 0.052(4) 0.071(6) C19 0.101(7) 0.054(5) 0.113(6) 0.040(5) 0.007(5) 0.011(5) C2 0.071(5) 0.096(6) 0.053(4) 0.021(4) 0.031(4) 0.051(4) C14 0.105(8) 0.062(6) 0.200(11) -0.041(7) -0.004(8) -0.005(6) C3 0.060(6) 0.069(6) 0.087(6) 0.008(4) 0.039(4) -0.003(4) C24 0.131(7) 0.085(7) 0.063(5) -0.008(5) -0.019(4) -0.017(6) N2 0.162(8) 0.137(8) 0.137(7) 0.039(6) 0.036(6) 0.055(8) C8 0.056(5) 0.067(5) 0.062(5) 0.010(4) 0.005(3) 0.013(4) C4 0.096(7) 0.120(9) 0.118(7) 0.029(6) 0.060(6) 0.021(6) C21 0.071(5) 0.052(5) 0.051(5) 0.006(4) 0.002(4) 0.008(4) C7 0.076(5) 0.085(6) 0.079(5) 0.018(5) 0.024(5) -0.003(4) C23 0.106(6) 0.118(7) 0.047(4) 0.002(4) 0.010(5) -0.006(6) C5 0.048(5) 0.087(6) 0.077(5) -0.009(4) 0.022(4) 0.024(4) C1 0.056(4) 0.061(4) 0.048(4) 0.014(5) 0.009(3) 0.008(5) C18 0.179(10) 0.081(6) 0.069(6) -0.025(4) -0.021(6) -0.035(6) C6 0.068(6) 0.072(6) 0.093(6) 0.031(5) 0.021(5) 0.022(4) C17 0.056(5) 0.047(5) 0.071(5) 0.008(4) -0.010(4) -0.001(4) C9 0.086(6) 0.115(7) 0.052(5) 0.017(6) -0.010(5) 0.018(5) C22 0.111(7) 0.120(7) 0.073(6) 0.025(5) -0.037(5) 0.018(6) C20 0.086(6) 0.067(6) 0.133(7) 0.007(5) -0.011(6) -0.014(5) C12 0.109(7) 0.213(11) 0.117(7) 0.095(7) -0.026(6) 0.029(7) C11 0.074(6) 0.172(9) 0.099(7) 0.027(6) -0.014(5) -0.022(6) C16 0.187(10) 0.070(6) 0.150(8) 0.025(6) 0.066(7) 0.018(6) C13 0.084(6) 0.048(5) 0.098(7) 0.014(5) 0.024(5) 0.003(5) C15 0.106(7) 0.075(6) 0.126(7) -0.021(6) 0.038(6) 0.023(5) C10 0.136(8) 0.203(11) 0.083(6) -0.049(7) -0.035(5) 0.014(8) _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 N1 1.874(6) . ? Ir1 C1 2.092(5) . ? Ir1 P1 2.2960(17) . ? Ir1 P2 2.2961(17) . ? P2 C8 1.821(5) . ? P2 C17 1.870(6) . ? P2 C21 1.882(6) . ? P1 C7 1.842(6) . ? P1 C9 1.873(7) . ? P1 C13 1.887(7) . ? N1 N2 1.064(7) . ? C19 C17 1.540(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C2 C1 1.494(7) . ? C2 C7 1.499(7) . ? C2 C3 1.533(7) . ? C2 H2 0.9800 . ? C14 C13 1.549(8) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C3 C4 1.441(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C24 C21 1.525(8) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C8 C6 1.494(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 C5 1.512(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C21 C23 1.524(8) . ? C21 C22 1.552(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C5 C6 1.516(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C1 C6 1.482(8) . ? C1 H1 0.9800 . ? C18 C17 1.520(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C6 H6 0.9800 . ? C17 C20 1.526(8) . ? C9 C10 1.499(9) . ? C9 C11 1.519(8) . ? C9 C12 1.538(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C16 C13 1.505(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C13 C15 1.525(8) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 N1 Ir1 C1 173.5(3) . . ? N1 Ir1 P1 97.4(2) . . ? C1 Ir1 P1 83.08(17) . . ? N1 Ir1 P2 96.6(2) . . ? C1 Ir1 P2 82.66(17) . . ? P1 Ir1 P2 165.67(6) . . ? C8 P2 C17 104.8(3) . . ? C8 P2 C21 103.3(3) . . ? C17 P2 C21 111.3(3) . . ? C8 P2 Ir1 104.39(19) . . ? C17 P2 Ir1 116.3(2) . . ? C21 P2 Ir1 115.0(2) . . ? C7 P1 C9 105.0(3) . . ? C7 P1 C13 103.3(3) . . ? C9 P1 C13 110.5(4) . . ? C7 P1 Ir1 104.2(2) . . ? C9 P1 Ir1 116.4(3) . . ? C13 P1 Ir1 115.8(3) . . ? N2 N1 Ir1 174.7(11) . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 C2 C7 114.1(5) . . ? C1 C2 C3 114.2(5) . . ? C7 C2 C3 114.1(5) . . ? C1 C2 H2 104.3 . . ? C7 C2 H2 104.3 . . ? C3 C2 H2 104.3 . . ? 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 . . ? C4 C3 C2 114.6(6) . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C6 C8 P2 110.4(4) . . ? C6 C8 H8A 109.6 . . ? P2 C8 H8A 109.6 . . ? C6 C8 H8B 109.6 . . ? P2 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C3 C4 C5 113.3(6) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C24 C21 C23 108.3(5) . . ? C24 C21 C22 108.5(6) . . ? C23 C21 C22 109.6(5) . . ? C24 C21 P2 105.8(4) . . ? C23 C21 P2 110.6(5) . . ? C22 C21 P2 113.9(4) . . ? C2 C7 P1 109.7(4) . . ? C2 C7 H7A 109.7 . . ? P1 C7 H7A 109.7 . . ? C2 C7 H7B 109.7 . . ? P1 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C6 C5 C4 115.2(6) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C6 C1 C2 114.1(5) . . ? C6 C1 Ir1 117.5(4) . . ? C2 C1 Ir1 117.2(4) . . ? C6 C1 H1 101.3 . . ? C2 C1 H1 101.3 . . ? Ir1 C1 H1 101.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 C6 C8 114.4(5) . . ? C1 C6 C5 114.8(5) . . ? C8 C6 C5 115.7(6) . . ? C1 C6 H6 103.2 . . ? C8 C6 H6 103.2 . . ? C5 C6 H6 103.2 . . ? C20 C17 C18 106.8(6) . . ? C20 C17 C19 108.0(6) . . ? C18 C17 C19 108.8(6) . . ? C20 C17 P2 109.8(5) . . ? C18 C17 P2 108.2(5) . . ? C19 C17 P2 114.9(5) . . ? C10 C9 C11 107.0(7) . . ? C10 C9 C12 108.1(6) . . ? C11 C9 C12 109.0(6) . . ? C10 C9 P1 107.7(5) . . ? C11 C9 P1 110.1(5) . . ? C12 C9 P1 114.7(6) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C16 C13 C15 110.8(6) . . ? C16 C13 C14 106.8(7) . . ? C15 C13 C14 106.3(6) . . ? C16 C13 P1 115.9(5) . . ? C15 C13 P1 111.0(5) . . ? C14 C13 P1 105.4(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 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.471 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.089 #===END data_athi53_complex5 _database_code_depnum_ccdc_archive 'CCDC 728028' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H39 Cl Ir O2 P2' _chemical_formula_weight 625.12 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' P P 0.1023 0.0942 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2429(5) _cell_length_b 12.2217(8) _cell_length_c 13.4226(8) _cell_angle_alpha 100.461(5) _cell_angle_beta 95.623(5) _cell_angle_gamma 104.395(6) _cell_volume 1273.38(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4494 _cell_measurement_theta_min 2.5704 _cell_measurement_theta_max 33.1231 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_absorpt_coefficient_mu 5.488 _exptl_absorpt_correction_T_min 0.93492 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction XCalibur 3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13293 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.1780 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 33.20 _reflns_number_total 8453 _reflns_number_gt 4229 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0253P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8453 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0643 _refine_ls_goodness_of_fit_ref 0.768 _refine_ls_restrained_S_all 0.768 _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 0.96122(2) 0.757722(15) 0.723475(13) 0.03648(6) Uani 1 1 d . . . P1 P 1.15872(14) 0.93302(9) 0.74995(8) 0.0334(3) Uani 1 1 d . . . P2 P 0.81332(14) 0.58346(9) 0.75157(8) 0.0351(3) Uani 1 1 d . . . Cl1 Cl 0.79526(18) 0.76366(12) 0.56880(9) 0.0693(4) Uani 1 1 d . . . C1 C 1.0980(5) 0.7525(3) 0.8533(3) 0.0276(9) Uani 1 1 d . . . O2 O 1.2818(3) 0.9399(2) 0.85614(19) 0.0405(7) Uani 1 1 d . . . O1 O 0.9181(3) 0.5694(2) 0.8568(2) 0.0425(7) Uani 1 1 d . . . C6 C 1.2395(5) 0.8457(3) 0.9022(3) 0.0355(10) Uani 1 1 d . . . C2 C 1.0602(5) 0.6615(3) 0.9019(3) 0.0347(10) Uani 1 1 d . . . C15 C 1.3171(5) 0.9535(4) 0.6611(3) 0.0411(11) Uani 1 1 d . . . C7 C 0.8153(6) 0.4502(4) 0.6622(3) 0.0434(11) Uani 1 1 d . . . C19 C 1.0809(6) 1.0618(4) 0.7869(3) 0.0501(12) Uani 1 1 d . . . C3 C 1.1510(5) 0.6570(4) 0.9926(3) 0.0421(11) Uani 1 1 d . . . H3 H 1.1203 0.5942 1.0235 0.051 Uiso 1 1 calc R . . C11 C 0.6042(6) 0.5804(4) 0.7919(4) 0.0509(12) Uani 1 1 d . . . C5 C 1.3356(5) 0.8444(3) 0.9918(3) 0.0354(10) Uani 1 1 d . . . H5 H 1.4292 0.9060 1.0220 0.042 Uiso 1 1 calc R . . C4 C 1.2899(6) 0.7502(4) 1.0353(3) 0.0455(12) Uani 1 1 d . . . H4 H 1.3544 0.7487 1.0957 0.055 Uiso 1 1 calc R . . C9 C 0.7400(9) 0.3393(4) 0.6961(4) 0.098(2) Uani 1 1 d . . . H9A H 0.7672 0.2761 0.6538 0.146 Uiso 1 1 calc R . . H9B H 0.6192 0.3252 0.6899 0.146 Uiso 1 1 calc R . . H9C H 0.7860 0.3462 0.7663 0.146 Uiso 1 1 calc R . . C10 C 0.7272(9) 0.4469(5) 0.5566(4) 0.100(2) Uani 1 1 d . . . H10A H 0.7703 0.5197 0.5378 0.150 Uiso 1 1 calc R . . H10B H 0.6075 0.4328 0.5574 0.150 Uiso 1 1 calc R . . H10C H 0.7481 0.3862 0.5076 0.150 Uiso 1 1 calc R . . C18 C 1.2282(7) 0.9472(6) 0.5558(4) 0.096(2) Uani 1 1 d . . . H18A H 1.1866 1.0140 0.5564 0.144 Uiso 1 1 calc R . . H18B H 1.1351 0.8786 0.5365 0.144 Uiso 1 1 calc R . . H18C H 1.3064 0.9450 0.5074 0.144 Uiso 1 1 calc R . . C21 C 0.9810(8) 1.0828(5) 0.6959(4) 0.092(2) Uani 1 1 d . . . H21A H 0.9247 1.1408 0.7185 0.138 Uiso 1 1 calc R . . H21B H 0.8983 1.0123 0.6616 0.138 Uiso 1 1 calc R . . H21C H 1.0561 1.1088 0.6495 0.138 Uiso 1 1 calc R . . C13 C 0.4745(6) 0.5726(6) 0.6996(5) 0.093(2) Uani 1 1 d . . . H13A H 0.4505 0.4977 0.6551 0.140 Uiso 1 1 calc R . . H13B H 0.5194 0.6312 0.6631 0.140 Uiso 1 1 calc R . . H13C H 0.3721 0.5840 0.7227 0.140 Uiso 1 1 calc R . . C17 C 1.4618(8) 1.0592(6) 0.6960(5) 0.114(3) Uani 1 1 d . . . H17A H 1.5576 1.0480 0.6643 0.171 Uiso 1 1 calc R . . H17B H 1.4910 1.0739 0.7691 0.171 Uiso 1 1 calc R . . H17C H 1.4302 1.1240 0.6771 0.171 Uiso 1 1 calc R . . C20 C 1.2172(8) 1.1718(5) 0.8360(6) 0.127(3) Uani 1 1 d . . . H20A H 1.2903 1.1932 0.7872 0.190 Uiso 1 1 calc R . . H20B H 1.2822 1.1595 0.8942 0.190 Uiso 1 1 calc R . . H20C H 1.1655 1.2326 0.8578 0.190 Uiso 1 1 calc R . . C8 C 1.0003(8) 0.4584(6) 0.6528(5) 0.118(3) Uani 1 1 d . . . H8A H 1.0074 0.3923 0.6042 0.177 Uiso 1 1 calc R . . H8B H 1.0607 0.4606 0.7183 0.177 Uiso 1 1 calc R . . H8C H 1.0495 0.5276 0.6299 0.177 Uiso 1 1 calc R . . C12 C 0.5350(8) 0.4823(6) 0.8451(5) 0.112(3) Uani 1 1 d . . . H12A H 0.6221 0.4786 0.8964 0.167 Uiso 1 1 calc R . . H12B H 0.4990 0.4104 0.7956 0.167 Uiso 1 1 calc R . . H12C H 0.4405 0.4960 0.8769 0.167 Uiso 1 1 calc R . . C16 C 1.3880(11) 0.8485(6) 0.6562(6) 0.129(3) Uani 1 1 d . . . H16A H 1.2961 0.7794 0.6443 0.194 Uiso 1 1 calc R . . H16B H 1.4581 0.8560 0.7199 0.194 Uiso 1 1 calc R . . H16C H 1.4542 0.8442 0.6014 0.194 Uiso 1 1 calc R . . C14 C 0.6270(9) 0.6944(7) 0.8617(6) 0.140(4) Uani 1 1 d . . . H14A H 0.5190 0.7015 0.8785 0.211 Uiso 1 1 calc R . . H14B H 0.6755 0.7552 0.8284 0.211 Uiso 1 1 calc R . . H14C H 0.7010 0.6998 0.9233 0.211 Uiso 1 1 calc R . . C22 C 0.9592(11) 1.0285(7) 0.8599(6) 0.152(4) Uani 1 1 d . . . H22A H 1.0179 1.0104 0.9175 0.228 Uiso 1 1 calc R . . H22B H 0.8690 0.9620 0.8255 0.228 Uiso 1 1 calc R . . H22C H 0.9131 1.0917 0.8833 0.228 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 0.03758(10) 0.03542(10) 0.03242(9) 0.01459(6) -0.00553(6) 0.00147(7) P1 0.0383(6) 0.0288(6) 0.0311(6) 0.0125(4) -0.0029(5) 0.0040(5) P2 0.0347(6) 0.0340(6) 0.0319(6) 0.0138(4) -0.0045(5) -0.0004(5) Cl1 0.0731(9) 0.0691(9) 0.0539(8) 0.0291(6) -0.0227(7) -0.0011(7) C1 0.029(2) 0.026(2) 0.0257(19) 0.0183(16) 0.0042(16) -0.0048(16) O2 0.0470(18) 0.0341(16) 0.0346(15) 0.0170(12) -0.0067(13) -0.0018(13) O1 0.0433(18) 0.0338(16) 0.0424(16) 0.0206(13) -0.0086(13) -0.0071(13) C6 0.041(3) 0.032(2) 0.031(2) 0.0103(17) -0.0025(18) 0.0051(19) C2 0.038(2) 0.032(2) 0.031(2) 0.0136(17) -0.0021(18) 0.0016(18) C15 0.043(3) 0.041(3) 0.035(2) 0.0098(19) 0.006(2) 0.003(2) C7 0.053(3) 0.038(3) 0.039(2) 0.0132(19) 0.007(2) 0.009(2) C19 0.057(3) 0.048(3) 0.047(3) 0.012(2) -0.002(2) 0.019(2) C3 0.042(3) 0.047(3) 0.037(2) 0.025(2) -0.005(2) 0.002(2) C11 0.037(3) 0.059(3) 0.060(3) 0.022(2) 0.009(2) 0.011(2) C5 0.035(2) 0.035(2) 0.029(2) 0.0051(17) -0.0066(18) 0.0014(18) C4 0.052(3) 0.044(3) 0.035(2) 0.019(2) -0.010(2) 0.001(2) C9 0.170(7) 0.039(3) 0.088(4) 0.020(3) 0.043(4) 0.024(4) C10 0.172(7) 0.067(4) 0.045(3) 0.000(3) -0.026(4) 0.029(4) C18 0.086(5) 0.160(7) 0.046(3) 0.038(4) 0.019(3) 0.023(4) C21 0.116(5) 0.073(4) 0.087(4) 0.013(3) -0.034(4) 0.050(4) C13 0.044(3) 0.144(6) 0.108(5) 0.074(4) 0.003(3) 0.023(4) C17 0.079(5) 0.119(6) 0.092(5) -0.014(4) 0.043(4) -0.050(4) C20 0.090(5) 0.066(4) 0.187(8) -0.050(5) -0.044(5) 0.033(4) C8 0.073(5) 0.135(7) 0.123(6) -0.038(5) 0.031(4) 0.026(4) C12 0.100(5) 0.136(6) 0.149(6) 0.104(5) 0.077(5) 0.051(5) C16 0.209(9) 0.130(7) 0.122(6) 0.058(5) 0.096(6) 0.131(7) C14 0.091(6) 0.122(7) 0.184(8) -0.051(6) 0.014(5) 0.048(5) C22 0.206(9) 0.181(8) 0.179(8) 0.116(7) 0.151(7) 0.152(8) _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 C1 2.000(3) . ? Ir1 P1 2.2897(10) . ? Ir1 P2 2.2925(11) . ? Ir1 Cl1 2.3947(12) . ? P1 O2 1.643(3) . ? P1 C19 1.847(5) . ? P1 C15 1.855(4) . ? P2 O1 1.641(3) . ? P2 C7 1.844(4) . ? P2 C11 1.850(5) . ? C1 C2 1.375(5) . ? C1 C6 1.416(5) . ? O2 C6 1.389(4) . ? O1 C2 1.401(4) . ? C6 C5 1.379(5) . ? C2 C3 1.383(5) . ? C15 C17 1.488(6) . ? C15 C18 1.507(6) . ? C15 C16 1.531(7) . ? C7 C10 1.517(6) . ? C7 C8 1.523(7) . ? C7 C9 1.514(7) . ? C19 C22 1.507(8) . ? C19 C20 1.512(7) . ? C19 C21 1.503(6) . ? C3 C4 1.386(5) . ? C3 H3 0.9300 . ? C11 C14 1.489(7) . ? C11 C12 1.525(7) . ? C11 C13 1.527(7) . ? C5 C4 1.372(5) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C1 Ir1 P1 80.53(10) . . ? C1 Ir1 P2 79.45(10) . . ? P1 Ir1 P2 159.90(4) . . ? C1 Ir1 Cl1 179.50(11) . . ? P1 Ir1 Cl1 99.75(4) . . ? P2 Ir1 Cl1 100.26(4) . . ? O2 P1 C19 100.83(17) . . ? O2 P1 C15 100.49(17) . . ? C19 P1 C15 112.7(2) . . ? O2 P1 Ir1 104.49(10) . . ? C19 P1 Ir1 116.05(16) . . ? C15 P1 Ir1 118.62(14) . . ? O1 P2 C7 100.89(17) . . ? O1 P2 C11 100.72(19) . . ? C7 P2 C11 113.6(2) . . ? O1 P2 Ir1 104.54(9) . . ? C7 P2 Ir1 118.47(14) . . ? C11 P2 Ir1 115.13(16) . . ? C2 C1 C6 115.8(3) . . ? C2 C1 Ir1 123.1(3) . . ? C6 C1 Ir1 121.1(3) . . ? C6 O2 P1 116.1(2) . . ? C2 O1 P2 115.8(2) . . ? C5 C6 O2 120.0(3) . . ? C5 C6 C1 122.2(4) . . ? O2 C6 C1 117.8(3) . . ? C1 C2 C3 124.1(3) . . ? C1 C2 O1 117.1(3) . . ? C3 C2 O1 118.8(3) . . ? C17 C15 C18 112.0(5) . . ? C17 C15 C16 107.7(6) . . ? C18 C15 C16 108.0(5) . . ? C17 C15 P1 115.0(3) . . ? C18 C15 P1 109.3(3) . . ? C16 C15 P1 104.3(4) . . ? C10 C7 C8 106.9(5) . . ? C10 C7 C9 110.2(4) . . ? C8 C7 C9 108.3(5) . . ? C10 C7 P2 109.9(4) . . ? C8 C7 P2 106.4(3) . . ? C9 C7 P2 114.8(3) . . ? C22 C19 C20 110.9(6) . . ? C22 C19 C21 107.3(5) . . ? C20 C19 C21 108.6(5) . . ? C22 C19 P1 104.2(4) . . ? C20 C19 P1 114.9(4) . . ? C21 C19 P1 110.7(3) . . ? C2 C3 C4 117.1(4) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? C14 C11 C12 110.4(6) . . ? C14 C11 C13 107.1(5) . . ? C12 C11 C13 108.6(5) . . ? C14 C11 P2 105.8(4) . . ? C12 C11 P2 114.5(4) . . ? C13 C11 P2 110.2(3) . . ? C4 C5 C6 118.4(4) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C4 C3 122.4(4) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 2.236 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.122