Supplementary Material (ESI) for Dalton Transactions This journal is © 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 'ProfD Shiuh-Tzung Liu' _publ_contact_author_email STLIU@NTU.EDU.TW _publ_section_title ; Synthesis, Characterization and Catalytic Activity of Saturated and Unsaturated N-Heterocyclic Carbene Iridium(I) Complexes ; loop_ _publ_author_name 'Shiuh-Tzung Liu' 'Yung-Hung Chang' 'Jwu-Ting Chen' 'Ching-Feng Fu' ; Yi-Hong Liu ; 'Shei-Ming Peng' # Attachment 'Complex4a-ic12848.cif' data_ic12848 _database_code_depnum_ccdc_archive 'CCDC 698437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H33 Cl Ir N2 O P' _chemical_formula_weight 768.26 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2700(3) _cell_length_b 32.3955(7) _cell_length_c 10.8716(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.3970(10) _cell_angle_gamma 90.00 _cell_volume 3211.31(15) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 38153 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 4.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.422 _exptl_absorpt_correction_T_max 0.534 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22873 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7295 _reflns_number_gt 6205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.3845P] 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 SHELXL _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7295 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.789953(12) 0.116979(3) 0.822146(12) 0.04285(7) Uani 1 1 d . . . Cl1 Cl 0.74462(11) 0.07323(3) 0.97273(11) 0.0671(2) Uani 1 1 d . . . P1 P 0.63324(8) 0.16639(2) 0.83525(8) 0.04176(17) Uani 1 1 d . . . O1 O 0.8526(4) 0.16755(12) 0.6316(5) 0.1161(15) Uani 1 1 d . . . N1 N 1.0817(3) 0.07402(8) 0.9002(3) 0.0546(7) Uani 1 1 d . . . N2 N 0.9002(3) 0.03476(8) 0.7714(3) 0.0563(7) Uani 1 1 d . . . C1 C 0.8280(4) 0.14860(12) 0.7055(5) 0.0673(10) Uani 1 1 d . . . C2 C 0.9361(3) 0.07200(9) 0.8284(3) 0.0466(7) Uani 1 1 d . . . C3 C 1.0288(4) 0.00901(12) 0.8002(5) 0.0720(11) Uani 1 1 d . . . H3A H 1.0382 0.0040 0.7167 0.086 Uiso 1 1 calc R . . H3B H 1.0235 -0.0172 0.8406 0.086 Uiso 1 1 calc R . . C4 C 1.1536(4) 0.03489(11) 0.9018(4) 0.0617(9) Uani 1 1 d . . . H4A H 1.1977 0.0226 0.9935 0.074 Uiso 1 1 calc R . . H4B H 1.2285 0.0386 0.8720 0.074 Uiso 1 1 calc R . . C5 C 1.1670(4) 0.11031(10) 0.9696(4) 0.0565(9) Uani 1 1 d . . . H5A H 1.1015 0.1338 0.9464 0.068 Uiso 1 1 calc R . . H5B H 1.2364 0.1158 0.9342 0.068 Uiso 1 1 calc R . . C6 C 1.2499(4) 0.10674(10) 1.1247(4) 0.0526(8) Uani 1 1 d . . . C7 C 1.3980(5) 0.11461(12) 1.1933(5) 0.0695(11) Uani 1 1 d . . . H7A H 1.4480 0.1204 1.1426 0.083 Uiso 1 1 calc R . . C8 C 1.4744(6) 0.11409(14) 1.3373(5) 0.0853(15) Uani 1 1 d . . . H8A H 1.5742 0.1200 1.3826 0.102 Uiso 1 1 calc R . . C9 C 1.4004(7) 0.10474(15) 1.4117(5) 0.0912(16) Uani 1 1 d . . . H9A H 1.4506 0.1042 1.5080 0.109 Uiso 1 1 calc R . . C10 C 1.2535(7) 0.09628(15) 1.3453(5) 0.0896(14) Uani 1 1 d . . . H10A H 1.2045 0.0899 1.3966 0.108 Uiso 1 1 calc R . . C11 C 1.1771(5) 0.09722(13) 1.2013(4) 0.0707(10) Uani 1 1 d . . . H11A H 1.0772 0.0915 1.1565 0.085 Uiso 1 1 calc R . . C12 C 0.7543(4) 0.02272(12) 0.6687(4) 0.0585(8) Uani 1 1 d . . . H12A H 0.6832 0.0406 0.6775 0.070 Uiso 1 1 calc R . . H12B H 0.7356 -0.0053 0.6880 0.070 Uiso 1 1 calc R . . C13 C 0.7316(4) 0.02479(10) 0.5216(4) 0.0533(8) Uani 1 1 d . . . C14 C 0.6257(4) -0.00031(11) 0.4199(4) 0.0579(8) Uani 1 1 d . . . H14A H 0.5776 -0.0202 0.4458 0.069 Uiso 1 1 calc R . . C15 C 0.5914(5) 0.00394(13) 0.2818(4) 0.0687(10) Uani 1 1 d . . . H15A H 0.5186 -0.0125 0.2156 0.082 Uiso 1 1 calc R . . C16 C 0.6636(5) 0.03209(14) 0.2418(5) 0.0753(12) Uani 1 1 d . . . H16A H 0.6406 0.0348 0.1489 0.090 Uiso 1 1 calc R . . C17 C 0.7712(5) 0.05657(15) 0.3411(5) 0.0825(13) Uani 1 1 d . . . H17A H 0.8215 0.0757 0.3149 0.099 Uiso 1 1 calc R . . C18 C 0.8041(5) 0.05271(13) 0.4794(5) 0.0723(11) Uani 1 1 d . . . H18A H 0.8767 0.0693 0.5451 0.087 Uiso 1 1 calc R . . C19 C 0.6742(4) 0.18065(10) 1.0120(4) 0.0521(8) Uani 1 1 d . . . C20 C 0.8160(5) 0.17575(14) 1.1162(4) 0.0743(11) Uani 1 1 d . . . H20A H 0.8872 0.1649 1.0952 0.089 Uiso 1 1 calc R . . C21 C 0.8533(6) 0.18672(16) 1.2512(5) 0.0955(15) Uani 1 1 d . . . H21A H 0.9491 0.1833 1.3204 0.115 Uiso 1 1 calc R . . C22 C 0.7485(7) 0.20266(18) 1.2831(5) 0.0959(16) Uani 1 1 d . . . H22A H 0.7732 0.2098 1.3740 0.115 Uiso 1 1 calc R . . C23 C 0.6072(6) 0.20808(18) 1.1806(5) 0.0997(17) Uani 1 1 d . . . H23A H 0.5366 0.2192 1.2021 0.120 Uiso 1 1 calc R . . C24 C 0.5703(5) 0.19704(14) 1.0460(5) 0.0762(12) Uani 1 1 d . . . H24A H 0.4744 0.2006 0.9772 0.091 Uiso 1 1 calc R . . C25 C 0.6388(3) 0.21538(9) 0.7540(4) 0.0471(7) Uani 1 1 d . . . C26 C 0.7093(4) 0.24981(11) 0.8300(4) 0.0679(10) Uani 1 1 d . . . H26A H 0.7463 0.2498 0.9258 0.082 Uiso 1 1 calc R . . C27 C 0.7249(6) 0.28466(14) 0.7624(6) 0.0973(17) Uani 1 1 d . . . H27A H 0.7729 0.3079 0.8135 0.117 Uiso 1 1 calc R . . C28 C 0.6704(6) 0.28495(15) 0.6222(6) 0.0942(16) Uani 1 1 d . . . H28A H 0.6836 0.3081 0.5784 0.113 Uiso 1 1 calc R . . C29 C 0.5969(5) 0.25168(13) 0.5458(5) 0.0715(11) Uani 1 1 d . . . H29A H 0.5561 0.2524 0.4497 0.086 Uiso 1 1 calc R . . C30 C 0.5831(4) 0.21665(11) 0.6118(4) 0.0575(8) Uani 1 1 d . . . H30A H 0.5356 0.1936 0.5594 0.069 Uiso 1 1 calc R . . C31 C 0.4364(3) 0.15456(10) 0.7508(3) 0.0461(7) Uani 1 1 d . . . C32 C 0.3307(4) 0.18516(11) 0.6993(4) 0.0592(9) Uani 1 1 d . . . H32A H 0.3590 0.2127 0.7084 0.071 Uiso 1 1 calc R . . C33 C 0.1828(4) 0.17514(14) 0.6342(5) 0.0691(10) Uani 1 1 d . . . H33A H 0.1125 0.1959 0.6017 0.083 Uiso 1 1 calc R . . C34 C 0.1405(4) 0.13448(14) 0.6179(4) 0.0670(10) Uani 1 1 d . . . H34A H 0.0414 0.1278 0.5725 0.080 Uiso 1 1 calc R . . C35 C 0.2440(4) 0.10362(13) 0.6684(4) 0.0626(9) Uani 1 1 d . . . H35A H 0.2150 0.0761 0.6572 0.075 Uiso 1 1 calc R . . C36 C 0.3917(4) 0.11373(10) 0.7359(4) 0.0538(8) Uani 1 1 d . . . H36A H 0.4615 0.0929 0.7717 0.065 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 0.04531(9) 0.03768(9) 0.04532(9) 0.00368(5) 0.02064(6) 0.00617(4) Cl1 0.0767(6) 0.0582(5) 0.0728(6) 0.0214(4) 0.0399(5) 0.0105(4) P1 0.0412(4) 0.0373(4) 0.0465(4) 0.0006(3) 0.0199(3) 0.0017(3) O1 0.122(3) 0.123(3) 0.156(4) 0.075(3) 0.109(3) 0.059(2) N1 0.0460(15) 0.0438(15) 0.0600(17) -0.0062(13) 0.0125(13) 0.0065(11) N2 0.0468(15) 0.0443(15) 0.0657(18) -0.0101(13) 0.0155(13) 0.0059(12) C1 0.067(2) 0.059(2) 0.088(3) 0.026(2) 0.046(2) 0.0301(18) C2 0.0487(17) 0.0405(16) 0.0479(17) -0.0001(13) 0.0200(14) 0.0043(13) C3 0.063(2) 0.050(2) 0.087(3) -0.0172(19) 0.020(2) 0.0121(17) C4 0.0506(19) 0.053(2) 0.071(2) -0.0027(17) 0.0189(17) 0.0144(15) C5 0.056(2) 0.0495(19) 0.056(2) -0.0054(15) 0.0187(17) -0.0033(15) C6 0.059(2) 0.0366(16) 0.0547(19) -0.0025(14) 0.0191(16) 0.0028(14) C7 0.057(2) 0.076(3) 0.062(2) -0.0054(18) 0.0151(19) 0.0099(18) C8 0.070(3) 0.084(3) 0.064(3) -0.011(2) -0.002(2) 0.014(2) C9 0.135(5) 0.059(3) 0.053(2) 0.002(2) 0.021(3) 0.013(3) C10 0.137(5) 0.073(3) 0.067(3) -0.002(2) 0.055(3) -0.005(3) C11 0.082(3) 0.060(2) 0.072(3) 0.002(2) 0.037(2) -0.002(2) C12 0.0546(19) 0.055(2) 0.063(2) -0.0128(16) 0.0243(17) -0.0065(16) C13 0.0487(18) 0.0457(18) 0.066(2) -0.0092(15) 0.0263(16) -0.0016(14) C14 0.061(2) 0.0450(18) 0.066(2) -0.0056(16) 0.0288(18) -0.0060(15) C15 0.079(3) 0.062(2) 0.062(2) -0.0105(19) 0.030(2) 0.0020(19) C16 0.096(3) 0.071(3) 0.073(3) 0.000(2) 0.051(3) 0.010(2) C17 0.093(3) 0.073(3) 0.105(4) 0.004(3) 0.065(3) -0.007(2) C18 0.070(2) 0.068(3) 0.085(3) -0.010(2) 0.041(2) -0.016(2) C19 0.0588(19) 0.0474(18) 0.0497(18) -0.0012(15) 0.0245(16) -0.0034(15) C20 0.073(3) 0.081(3) 0.052(2) -0.007(2) 0.0146(19) 0.009(2) C21 0.107(4) 0.098(4) 0.053(2) -0.004(2) 0.013(3) 0.003(3) C22 0.138(5) 0.096(4) 0.060(3) -0.016(3) 0.051(3) -0.025(3) C23 0.110(4) 0.127(5) 0.084(3) -0.037(3) 0.064(3) -0.025(3) C24 0.072(3) 0.099(3) 0.069(3) -0.021(2) 0.041(2) -0.007(2) C25 0.0411(15) 0.0383(16) 0.0604(19) 0.0031(14) 0.0219(14) 0.0053(12) C26 0.068(2) 0.049(2) 0.070(2) -0.0002(18) 0.0165(19) -0.0081(17) C27 0.099(4) 0.047(2) 0.110(4) 0.006(2) 0.018(3) -0.020(2) C28 0.090(3) 0.061(3) 0.112(4) 0.032(3) 0.030(3) -0.004(2) C29 0.074(3) 0.065(2) 0.075(3) 0.023(2) 0.033(2) 0.008(2) C30 0.064(2) 0.0460(19) 0.058(2) 0.0048(16) 0.0249(17) 0.0009(15) C31 0.0463(16) 0.0455(17) 0.0488(17) -0.0017(13) 0.0238(14) -0.0018(13) C32 0.0497(18) 0.0483(19) 0.075(2) -0.0039(17) 0.0250(17) 0.0014(15) C33 0.0429(18) 0.076(3) 0.084(3) 0.001(2) 0.0252(18) 0.0074(17) C34 0.0466(19) 0.083(3) 0.071(2) -0.007(2) 0.0263(18) -0.0144(19) C35 0.059(2) 0.063(2) 0.070(2) -0.0057(19) 0.0334(19) -0.0165(18) C36 0.0542(19) 0.051(2) 0.058(2) -0.0004(15) 0.0268(17) -0.0034(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 1.807(4) . ? Ir1 C2 2.070(3) . ? Ir1 P1 2.3204(8) . ? Ir1 Cl1 2.3680(9) . ? P1 C19 1.827(3) . ? P1 C25 1.830(3) . ? P1 C31 1.835(3) . ? O1 C1 1.128(5) . ? N1 C2 1.333(4) . ? N1 C5 1.453(4) . ? N1 C4 1.464(4) . ? N2 C2 1.328(4) . ? N2 C12 1.451(4) . ? N2 C3 1.469(4) . ? C3 C4 1.505(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.503(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.375(5) . ? C6 C11 1.386(6) . ? C7 C8 1.391(6) . ? C7 H7A 0.9300 . ? C8 C9 1.375(8) . ? C8 H8A 0.9300 . ? C9 C10 1.367(8) . ? C9 H9A 0.9300 . ? C10 C11 1.392(6) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.507(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.378(5) . ? C13 C14 1.400(5) . ? C14 C15 1.382(5) . ? C14 H14A 0.9300 . ? C15 C16 1.367(6) . ? C15 H15A 0.9300 . ? C16 C17 1.385(6) . ? C16 H16A 0.9300 . ? C17 C18 1.387(6) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C20 1.383(5) . ? C19 C24 1.386(5) . ? C20 C21 1.382(6) . ? C20 H20A 0.9300 . ? C21 C22 1.374(8) . ? C21 H21A 0.9300 . ? C22 C23 1.374(8) . ? C22 H22A 0.9300 . ? C23 C24 1.379(6) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C26 1.379(5) . ? C25 C30 1.380(5) . ? C26 C27 1.396(6) . ? C26 H26A 0.9300 . ? C27 C28 1.361(8) . ? C27 H27A 0.9300 . ? C28 C29 1.358(7) . ? C28 H28A 0.9300 . ? C29 C30 1.384(5) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 C32 1.384(5) . ? C31 C36 1.385(4) . ? C32 C33 1.387(5) . ? C32 H32A 0.9300 . ? C33 C34 1.372(6) . ? C33 H33A 0.9300 . ? C34 C35 1.376(6) . ? C34 H34A 0.9300 . ? C35 C36 1.387(5) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? 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 C2 91.98(14) . . ? C1 Ir1 P1 91.84(11) . . ? C2 Ir1 P1 175.10(9) . . ? C1 Ir1 Cl1 177.65(12) . . ? C2 Ir1 Cl1 85.77(9) . . ? P1 Ir1 Cl1 90.45(3) . . ? C19 P1 C25 104.19(15) . . ? C19 P1 C31 104.27(15) . . ? C25 P1 C31 102.20(14) . . ? C19 P1 Ir1 114.11(12) . . ? C25 P1 Ir1 113.09(10) . . ? C31 P1 Ir1 117.42(10) . . ? C2 N1 C5 126.2(3) . . ? C2 N1 C4 112.9(3) . . ? C5 N1 C4 120.9(3) . . ? C2 N2 C12 124.7(3) . . ? C2 N2 C3 112.8(3) . . ? C12 N2 C3 121.4(3) . . ? O1 C1 Ir1 178.4(4) . . ? N2 C2 N1 108.3(3) . . ? N2 C2 Ir1 125.6(2) . . ? N1 C2 Ir1 125.8(2) . . ? N2 C3 C4 102.6(3) . . ? N2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.2 . . ? N1 C4 C3 102.6(3) . . ? N1 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.2 . . ? N1 C5 C6 114.6(3) . . ? N1 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? N1 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C11 118.9(4) . . ? C7 C6 C5 120.6(4) . . ? C11 C6 C5 120.5(4) . . ? C6 C7 C8 121.3(5) . . ? C6 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C9 C8 C7 119.1(5) . . ? C9 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C10 C9 C8 120.5(4) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C6 C11 C10 120.0(5) . . ? C6 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? N2 C12 C13 113.9(3) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C18 C13 C14 117.5(4) . . ? C18 C13 C12 122.6(3) . . ? C14 C13 C12 119.8(3) . . ? C15 C14 C13 121.1(4) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C16 C15 C14 120.5(4) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C13 C18 C17 121.4(4) . . ? C13 C18 H18A 119.3 . . ? C17 C18 H18A 119.3 . . ? C20 C19 C24 118.3(4) . . ? C20 C19 P1 118.6(3) . . ? C24 C19 P1 123.0(3) . . ? C21 C20 C19 120.9(4) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C22 C21 C20 119.8(5) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C21 C22 C23 120.1(4) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C22 C23 C24 119.9(5) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C23 C24 C19 120.9(4) . . ? C23 C24 H24A 119.6 . . ? C19 C24 H24A 119.6 . . ? C26 C25 C30 118.7(3) . . ? C26 C25 P1 122.4(3) . . ? C30 C25 P1 118.5(2) . . ? C25 C26 C27 119.6(4) . . ? C25 C26 H26A 120.2 . . ? C27 C26 H26A 120.2 . . ? C28 C27 C26 120.5(4) . . ? C28 C27 H27A 119.7 . . ? C26 C27 H27A 119.7 . . ? C29 C28 C27 120.4(4) . . ? C29 C28 H28A 119.8 . . ? C27 C28 H28A 119.8 . . ? C28 C29 C30 119.7(4) . . ? C28 C29 H29A 120.2 . . ? C30 C29 H29A 120.2 . . ? C25 C30 C29 121.1(4) . . ? C25 C30 H30A 119.5 . . ? C29 C30 H30A 119.5 . . ? C32 C31 C36 118.7(3) . . ? C32 C31 P1 122.1(2) . . ? C36 C31 P1 119.2(2) . . ? C31 C32 C33 120.7(3) . . ? C31 C32 H32A 119.7 . . ? C33 C32 H32A 119.7 . . ? C34 C33 C32 119.8(4) . . ? C34 C33 H33A 120.1 . . ? C32 C33 H33A 120.1 . . ? C33 C34 C35 120.4(4) . . ? C33 C34 H34A 119.8 . . ? C35 C34 H34A 119.8 . . ? C34 C35 C36 119.7(4) . . ? C34 C35 H35A 120.1 . . ? C36 C35 H35A 120.1 . . ? C31 C36 C35 120.7(3) . . ? C31 C36 H36A 119.7 . . ? C35 C36 H36A 119.7 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.224 _refine_diff_density_min -1.189 _refine_diff_density_rms 0.071 # Attachment 'Complex7a-ic13085.cif' data_ic13085 _database_code_depnum_ccdc_archive 'CCDC 698438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H31 Cl Ir N2 O P' _chemical_formula_weight 766.25 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1220(5) _cell_length_b 32.2279(14) _cell_length_c 10.7193(6) _cell_angle_alpha 90.00 _cell_angle_beta 117.211(6) _cell_angle_gamma 90.00 _cell_volume 3109.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16066 _cell_measurement_theta_min 2.5829 _cell_measurement_theta_max 28.0962 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 4.462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62674 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18105 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6807 _reflns_number_gt 5745 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0152P)^2^+3.2556P] 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 6807 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0485 _refine_ls_wR_factor_gt 0.0469 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.783687(13) 0.117522(4) 0.330809(12) 0.01624(4) Uani 1 1 d . . . Cl1 Cl 0.73814(10) 0.07440(3) 0.48557(9) 0.0309(2) Uani 1 1 d . . . P1 P 0.62428(8) 0.16680(2) 0.34238(8) 0.01512(16) Uani 1 1 d . . . O1 O 0.8437(3) 0.16855(10) 0.1351(3) 0.0559(9) Uani 1 1 d . . . N1 N 0.9037(3) 0.03330(8) 0.2899(3) 0.0231(6) Uani 1 1 d . . . N2 N 1.0827(3) 0.07406(8) 0.4136(3) 0.0226(6) Uani 1 1 d . . . C1 C 0.8211(4) 0.14907(12) 0.2106(4) 0.0302(8) Uani 1 1 d . . . C2 C 0.9333(3) 0.07242(10) 0.3398(3) 0.0181(7) Uani 1 1 d . . . C3 C 1.0328(4) 0.01076(11) 0.3333(4) 0.0325(9) Uani 1 1 d . . . H3A H 1.0407 -0.0174 0.3117 0.039 Uiso 1 1 calc R . . C4 C 1.1449(4) 0.03613(11) 0.4115(4) 0.0320(9) Uani 1 1 d . . . H4A H 1.2476 0.0293 0.4569 0.038 Uiso 1 1 calc R . . C5 C 0.7584(3) 0.01894(11) 0.1865(3) 0.0247(7) Uani 1 1 d . . . H5A H 0.6809 0.0359 0.1942 0.030 Uiso 1 1 calc R . . H5B H 0.7448 -0.0102 0.2078 0.030 Uiso 1 1 calc R . . C6 C 0.7373(4) 0.02134(10) 0.0380(3) 0.0238(7) Uani 1 1 d . . . C7 C 0.6289(4) -0.00263(10) -0.0660(3) 0.0244(7) Uani 1 1 d . . . H7A H 0.5750 -0.0223 -0.0413 0.029 Uiso 1 1 calc R . . C8 C 0.5983(4) 0.00168(11) -0.2043(4) 0.0291(8) Uani 1 1 d . . . H8A H 0.5221 -0.0146 -0.2744 0.035 Uiso 1 1 calc R . . C9 C 0.6774(4) 0.02935(12) -0.2415(4) 0.0374(9) Uani 1 1 d . . . H9A H 0.6555 0.0326 -0.3372 0.045 Uiso 1 1 calc R . . C10 C 0.7887(5) 0.05241(14) -0.1390(4) 0.0463(11) Uani 1 1 d . . . H10A H 0.8455 0.0711 -0.1638 0.056 Uiso 1 1 calc R . . C11 C 0.8184(4) 0.04854(13) -0.0002(4) 0.0386(10) Uani 1 1 d . . . H11A H 0.8950 0.0647 0.0697 0.046 Uiso 1 1 calc R . . C12 C 1.1685(4) 0.11112(10) 0.4805(3) 0.0244(7) Uani 1 1 d . . . H12A H 1.1000 0.1351 0.4571 0.029 Uiso 1 1 calc R . . H12B H 1.2385 0.1168 0.4415 0.029 Uiso 1 1 calc R . . C13 C 1.2551(4) 0.10764(9) 0.6375(3) 0.0220(7) Uani 1 1 d . . . C14 C 1.4061(4) 0.11442(12) 0.7036(4) 0.0316(8) Uani 1 1 d . . . H14A H 1.4567 0.1198 0.6495 0.038 Uiso 1 1 calc R . . C15 C 1.4849(4) 0.11351(12) 0.8492(4) 0.0423(10) Uani 1 1 d . . . H15A H 1.5890 0.1184 0.8943 0.051 Uiso 1 1 calc R . . C16 C 1.4126(5) 0.10558(11) 0.9270(4) 0.0418(11) Uani 1 1 d . . . H16A H 1.4665 0.1050 1.0265 0.050 Uiso 1 1 calc R . . C17 C 1.2613(5) 0.09840(12) 0.8620(4) 0.0423(10) Uani 1 1 d . . . H17A H 1.2115 0.0927 0.9168 0.051 Uiso 1 1 calc R . . C18 C 1.1822(4) 0.09957(11) 0.7173(4) 0.0323(8) Uani 1 1 d . . . H18A H 1.0780 0.0949 0.6726 0.039 Uiso 1 1 calc R . . C19 C 0.4263(3) 0.15424(10) 0.2581(3) 0.0176(7) Uani 1 1 d . . . C20 C 0.3176(3) 0.18486(10) 0.2038(3) 0.0214(7) Uani 1 1 d . . . H20A H 0.3457 0.2132 0.2116 0.026 Uiso 1 1 calc R . . C21 C 0.1686(4) 0.17403(11) 0.1383(3) 0.0259(8) Uani 1 1 d . . . H21A H 0.0949 0.1951 0.1023 0.031 Uiso 1 1 calc R . . C22 C 0.1268(4) 0.13293(11) 0.1250(3) 0.0276(8) Uani 1 1 d . . . H22A H 0.0245 0.1257 0.0784 0.033 Uiso 1 1 calc R . . C23 C 0.2333(4) 0.10241(11) 0.1793(3) 0.0266(8) Uani 1 1 d . . . H23A H 0.2045 0.0741 0.1711 0.032 Uiso 1 1 calc R . . C24 C 0.3827(3) 0.11299(10) 0.2459(3) 0.0214(7) Uani 1 1 d . . . H24A H 0.4558 0.0918 0.2836 0.026 Uiso 1 1 calc R . . C25 C 0.6293(3) 0.21577(9) 0.2597(3) 0.0175(7) Uani 1 1 d . . . C26 C 0.7017(4) 0.25040(11) 0.3361(4) 0.0292(8) Uani 1 1 d . . . H26A H 0.7396 0.2504 0.4352 0.035 Uiso 1 1 calc R . . C27 C 0.7192(4) 0.28518(12) 0.2688(4) 0.0462(11) Uani 1 1 d . . . H27A H 0.7705 0.3088 0.3220 0.055 Uiso 1 1 calc R . . C28 C 0.6626(4) 0.28558(13) 0.1256(4) 0.0449(11) Uani 1 1 d . . . H28A H 0.6761 0.3093 0.0799 0.054 Uiso 1 1 calc R . . C29 C 0.5866(4) 0.25176(11) 0.0481(4) 0.0308(8) Uani 1 1 d . . . H29A H 0.5445 0.2524 -0.0513 0.037 Uiso 1 1 calc R . . C30 C 0.5713(3) 0.21692(10) 0.1145(3) 0.0216(7) Uani 1 1 d . . . H30A H 0.5206 0.1934 0.0606 0.026 Uiso 1 1 calc R . . C31 C 0.6644(3) 0.18191(10) 0.5208(3) 0.0205(7) Uani 1 1 d . . . C32 C 0.8074(4) 0.17663(12) 0.6267(3) 0.0342(9) Uani 1 1 d . . . H32A H 0.8810 0.1647 0.6060 0.041 Uiso 1 1 calc R . . C33 C 0.8443(5) 0.18849(13) 0.7625(4) 0.0442(11) Uani 1 1 d . . . H33A H 0.9433 0.1852 0.8344 0.053 Uiso 1 1 calc R . . C34 C 0.7380(5) 0.20505(13) 0.7936(4) 0.0426(11) Uani 1 1 d . . . H34A H 0.7626 0.2126 0.8874 0.051 Uiso 1 1 calc R . . C35 C 0.5951(5) 0.21069(13) 0.6884(4) 0.0421(10) Uani 1 1 d . . . H35A H 0.5218 0.2226 0.7096 0.051 Uiso 1 1 calc R . . C36 C 0.5584(4) 0.19917(12) 0.5525(4) 0.0316(9) Uani 1 1 d . . . H36A H 0.4599 0.2031 0.4804 0.038 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 0.01690(6) 0.01507(6) 0.01628(6) 0.00197(5) 0.00717(5) 0.00348(6) Cl1 0.0354(5) 0.0275(5) 0.0338(5) 0.0146(4) 0.0192(4) 0.0085(4) P1 0.0141(4) 0.0146(4) 0.0156(4) 0.0005(3) 0.0059(3) 0.0006(3) O1 0.0577(19) 0.064(2) 0.073(2) 0.0451(18) 0.0529(18) 0.0363(16) N1 0.0196(14) 0.0193(15) 0.0264(15) -0.0038(12) 0.0070(12) 0.0024(11) N2 0.0198(14) 0.0171(14) 0.0241(14) -0.0027(11) 0.0043(12) 0.0036(11) C1 0.0261(19) 0.034(2) 0.037(2) 0.0062(17) 0.0196(17) 0.0184(16) C2 0.0187(16) 0.0161(16) 0.0148(15) 0.0001(12) 0.0036(13) 0.0019(12) C3 0.030(2) 0.0198(19) 0.042(2) -0.0053(16) 0.0116(18) 0.0091(15) C4 0.0224(19) 0.025(2) 0.040(2) -0.0033(16) 0.0066(17) 0.0120(15) C5 0.0219(18) 0.0221(18) 0.0296(19) -0.0061(14) 0.0115(16) -0.0052(13) C6 0.0244(18) 0.0189(17) 0.0301(18) -0.0057(14) 0.0141(16) 0.0001(14) C7 0.0243(18) 0.0186(18) 0.0304(18) -0.0020(14) 0.0127(15) -0.0019(14) C8 0.035(2) 0.0231(19) 0.0290(19) -0.0050(15) 0.0149(17) -0.0006(15) C9 0.050(3) 0.039(2) 0.034(2) -0.0040(18) 0.028(2) -0.0018(19) C10 0.059(3) 0.047(3) 0.054(3) -0.011(2) 0.044(2) -0.021(2) C11 0.039(2) 0.042(2) 0.042(2) -0.0140(18) 0.025(2) -0.0197(19) C12 0.0248(18) 0.0203(19) 0.0211(17) -0.0019(13) 0.0046(14) -0.0017(14) C13 0.0261(18) 0.0139(17) 0.0225(17) -0.0021(12) 0.0080(15) 0.0023(13) C14 0.0265(19) 0.035(2) 0.0267(18) -0.0016(16) 0.0062(15) 0.0024(16) C15 0.036(2) 0.036(2) 0.033(2) -0.0041(18) -0.0034(18) -0.0008(18) C16 0.067(3) 0.022(2) 0.0195(19) 0.0006(14) 0.005(2) 0.0075(19) C17 0.072(3) 0.029(2) 0.034(2) 0.0049(17) 0.032(2) 0.005(2) C18 0.037(2) 0.027(2) 0.032(2) 0.0024(16) 0.0146(18) 0.0015(17) C19 0.0175(16) 0.0212(17) 0.0154(15) -0.0027(12) 0.0088(13) -0.0017(13) C20 0.0177(16) 0.0188(17) 0.0264(17) -0.0005(13) 0.0089(14) -0.0019(13) C21 0.0162(16) 0.031(2) 0.0273(18) -0.0005(15) 0.0074(15) 0.0042(14) C22 0.0182(18) 0.038(2) 0.0276(19) -0.0078(15) 0.0110(15) -0.0077(15) C23 0.0267(19) 0.0252(18) 0.0315(19) -0.0032(15) 0.0165(16) -0.0078(15) C24 0.0216(16) 0.0212(18) 0.0235(16) 0.0002(13) 0.0121(14) 0.0016(14) C25 0.0133(15) 0.0144(16) 0.0245(17) 0.0018(12) 0.0083(13) 0.0030(12) C26 0.0270(19) 0.0213(19) 0.0280(19) 0.0001(14) 0.0030(16) -0.0004(15) C27 0.047(3) 0.022(2) 0.045(2) 0.0026(18) 0.000(2) -0.0115(18) C28 0.042(2) 0.030(2) 0.049(2) 0.0196(19) 0.009(2) -0.0062(18) C29 0.030(2) 0.031(2) 0.0290(19) 0.0108(16) 0.0116(17) 0.0047(16) C30 0.0226(17) 0.0171(17) 0.0235(17) 0.0009(13) 0.0092(14) 0.0024(13) C31 0.0216(17) 0.0208(17) 0.0175(16) -0.0010(13) 0.0076(14) -0.0015(13) C32 0.031(2) 0.041(2) 0.0231(19) -0.0035(16) 0.0055(16) 0.0087(17) C33 0.047(3) 0.047(3) 0.0196(19) -0.0031(17) -0.0003(19) 0.003(2) C34 0.068(3) 0.041(3) 0.0196(19) -0.0056(16) 0.022(2) -0.012(2) C35 0.050(3) 0.055(3) 0.035(2) -0.0175(19) 0.031(2) -0.011(2) C36 0.0256(19) 0.045(2) 0.0262(19) -0.0091(16) 0.0131(16) -0.0025(16) _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 1.812(4) . ? Ir1 C2 2.069(3) . ? Ir1 P1 2.3075(8) . ? Ir1 Cl1 2.3655(8) . ? P1 C25 1.822(3) . ? P1 C19 1.827(3) . ? P1 C31 1.830(3) . ? O1 C1 1.128(4) . ? N1 C2 1.348(4) . ? N1 C3 1.377(4) . ? N1 C5 1.455(4) . ? N2 C2 1.350(4) . ? N2 C4 1.380(4) . ? N2 C12 1.458(4) . ? C3 C4 1.338(5) . ? C5 C6 1.509(4) . ? C6 C11 1.384(5) . ? C6 C7 1.387(4) . ? C7 C8 1.376(5) . ? C8 C9 1.374(5) . ? C9 C10 1.378(5) . ? C10 C11 1.383(5) . ? C12 C13 1.505(4) . ? C13 C14 1.376(5) . ? C13 C18 1.386(5) . ? C14 C15 1.391(5) . ? C15 C16 1.362(6) . ? C16 C17 1.382(6) . ? C17 C18 1.384(5) . ? C19 C24 1.388(4) . ? C19 C20 1.392(4) . ? C20 C21 1.386(4) . ? C21 C22 1.378(5) . ? C22 C23 1.377(5) . ? C23 C24 1.388(4) . ? C25 C26 1.380(4) . ? C25 C30 1.389(4) . ? C26 C27 1.388(5) . ? C27 C28 1.371(5) . ? C28 C29 1.373(5) . ? C29 C30 1.376(4) . ? C31 C36 1.382(4) . ? C31 C32 1.382(4) . ? C32 C33 1.381(5) . ? C33 C34 1.372(6) . ? C34 C35 1.380(5) . ? C35 C36 1.379(5) . ? 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 C2 92.34(13) . . ? C1 Ir1 P1 91.76(10) . . ? C2 Ir1 P1 174.77(8) . . ? C1 Ir1 Cl1 178.08(11) . . ? C2 Ir1 Cl1 85.86(9) . . ? P1 Ir1 Cl1 90.08(3) . . ? C25 P1 C19 102.66(14) . . ? C25 P1 C31 103.64(14) . . ? C19 P1 C31 104.19(14) . . ? C25 P1 Ir1 113.22(10) . . ? C19 P1 Ir1 117.16(10) . . ? C31 P1 Ir1 114.38(11) . . ? C2 N1 C3 110.8(3) . . ? C2 N1 C5 124.3(3) . . ? C3 N1 C5 124.2(3) . . ? C2 N2 C4 110.7(3) . . ? C2 N2 C12 125.2(3) . . ? C4 N2 C12 124.1(3) . . ? O1 C1 Ir1 179.5(4) . . ? N1 C2 N2 104.8(3) . . ? N1 C2 Ir1 127.8(2) . . ? N2 C2 Ir1 126.8(2) . . ? C4 C3 N1 106.9(3) . . ? C3 C4 N2 106.8(3) . . ? N1 C5 C6 113.2(3) . . ? C11 C6 C7 118.2(3) . . ? C11 C6 C5 121.8(3) . . ? C7 C6 C5 119.9(3) . . ? C8 C7 C6 121.0(3) . . ? C9 C8 C7 120.3(3) . . ? C8 C9 C10 119.4(3) . . ? C9 C10 C11 120.4(4) . . ? C10 C11 C6 120.6(3) . . ? N2 C12 C13 113.6(3) . . ? C14 C13 C18 119.4(3) . . ? C14 C13 C12 120.4(3) . . ? C18 C13 C12 120.1(3) . . ? C13 C14 C15 120.5(4) . . ? C16 C15 C14 119.8(4) . . ? C15 C16 C17 120.3(3) . . ? C16 C17 C18 120.0(4) . . ? C17 C18 C13 119.9(4) . . ? C24 C19 C20 118.9(3) . . ? C24 C19 P1 119.2(2) . . ? C20 C19 P1 121.9(2) . . ? C21 C20 C19 120.2(3) . . ? C22 C21 C20 120.4(3) . . ? C23 C22 C21 119.9(3) . . ? C22 C23 C24 120.0(3) . . ? C23 C24 C19 120.6(3) . . ? C26 C25 C30 118.7(3) . . ? C26 C25 P1 122.5(2) . . ? C30 C25 P1 118.4(2) . . ? C25 C26 C27 120.3(3) . . ? C28 C27 C26 120.2(4) . . ? C27 C28 C29 120.1(3) . . ? C28 C29 C30 120.0(3) . . ? C29 C30 C25 120.8(3) . . ? C36 C31 C32 119.1(3) . . ? C36 C31 P1 122.5(2) . . ? C32 C31 P1 118.3(2) . . ? C33 C32 C31 120.6(4) . . ? C34 C33 C32 120.0(4) . . ? C33 C34 C35 119.9(3) . . ? C36 C35 C34 120.2(4) . . ? C35 C36 C31 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 1.202 _refine_diff_density_min -1.053 _refine_diff_density_rms 0.102