# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'John M. Brown' _publ_contact_author_address ;Chemistry Research Laboratory 12 Mansfield Road Oxford OX1 3TA ; _publ_contact_author_email john.brown@chemistry.oxford.ac.uk _publ_contact_author_phone '01865 275642' _publ_contact_author_fax '01865 285002' loop_ _publ_author_name _publ_author_address J.M.Brown ;Chemistry Research Laboratory 12 Mansfield Road Oxford OX1 3TA ; D.Mingos . 'Yingjian Xu.' . _publ_section_title ; Crabtree's Catalyst Revisited; Ligand Effects on Stability and Durability ; data_arc1365 _database_code_depnum_ccdc_archive 'CCDC 654176' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'CRYSTALS (Watkin et al, 2001)' _chemical_name_systematic ; Iridium(1+)[(1,2,5,6-eta)(1,5-COD](5,6,7,8-THQ)(P(Cyclohexyl)3)PF6(1-). ; _chemical_melting_point ? _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled to 120K at a rate of 120 K hr^-1^ for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary heavy _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The hydrogen atoms of the coordinated alkene groups were located in a difference Fourier map and their coordinates and isotropic displacement parameters subsequently refined. Other hydrogen atoms were positioned geometrically. ; #============================================================= _cell_length_a 10.0545(2) _cell_angle_alpha 97.6584(8) _cell_length_b 11.8176(2) _cell_angle_beta 103.4087(9) _cell_length_c 15.5293(3) _cell_angle_gamma 99.2889(11) _cell_volume 1743.13(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B 'Ir ' -1.4442 7.9887 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011 11.4722 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'P ' 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C35 H56 F6 Ir N P2 ' _chemical_formula_moiety ' C35 H56 Ir N P, F6 P ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 858.99 _cell_measurement_reflns_used 25277 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 120 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' orange-red ' _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.12 _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 3.980 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.92 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 120 _diffrn_reflns_number 25277 _reflns_number_total 7896 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_theta_min 5.098 _diffrn_reflns_theta_max 27.493 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.493 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _refine_diff_density_min -3.33 _refine_diff_density_max 2.87 _refine_ls_number_reflns 6887 _refine_ls_number_restraints 0 _refine_ls_number_parameters 422 #_refine_ls_R_factor_ref 0.0415 _refine_ls_wR_factor_ref 0.0489 _refine_ls_goodness_of_fit_ref 1.0801 #_reflns_number_all 7869 _refine_ls_R_factor_all 0.0476 _refine_ls_wR_factor_all 0.0538 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 6887 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_gt 0.0489 _refine_ls_shift/su_max 0.006071 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.986 0.255 0.632 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type Ir1 Ir 0.475094(16) 0.286596(14) 0.297810(10) 0.0211 1.0000 Uani C1 C 0.5698(6) 0.4693(5) 0.3317(4) 0.0328 1.0000 Uani C2 C 0.6395(5) 0.4168(4) 0.3990(3) 0.0238 1.0000 Uani C3 C 0.7833(5) 0.3900(5) 0.4049(4) 0.0346 1.0000 Uani C4 C 0.7742(5) 0.2633(5) 0.3587(4) 0.0348 1.0000 Uani C5 C 0.6538(5) 0.2240(5) 0.2747(4) 0.0294 1.0000 Uani C6 C 0.6129(5) 0.2898(5) 0.2085(3) 0.0290 1.0000 Uani C7 C 0.6875(6) 0.4130(5) 0.2070(4) 0.0386 1.0000 Uani C8 C 0.6264(6) 0.5068(5) 0.2550(4) 0.0402 1.0000 Uani N1 N 0.3447(4) 0.3083(3) 0.3847(3) 0.0213 1.0000 Uani C9 C 0.2462(5) 0.3727(4) 0.3671(3) 0.0235 1.0000 Uani C10 C 0.1501(5) 0.3812(4) 0.4177(3) 0.0271 1.0000 Uani C11 C 0.1539(5) 0.3182(4) 0.4869(3) 0.0299 1.0000 Uani C12 C 0.2559(5) 0.2515(4) 0.5068(3) 0.0290 1.0000 Uani C13 C 0.2565(6) 0.1789(6) 0.5799(4) 0.0382 1.0000 Uani C14 C 0.3409(7) 0.0824(6) 0.5711(4) 0.0431 1.0000 Uani C15 C 0.4825(7) 0.1360(5) 0.5631(4) 0.0407 1.0000 Uani C16 C 0.4718(5) 0.1870(4) 0.4764(3) 0.0270 1.0000 Uani C17 C 0.3534(5) 0.2516(4) 0.4556(3) 0.0236 1.0000 Uani P1 P 0.29995(11) 0.15137(10) 0.18711(7) 0.0195 1.0000 Uani C18 C 0.1369(4) 0.1049(4) 0.2222(3) 0.0221 1.0000 Uani C19 C 0.0008(5) 0.0557(5) 0.1479(3) 0.0284 1.0000 Uani C20 C -0.1241(5) 0.0478(5) 0.1891(3) 0.0299 1.0000 Uani C21 C -0.1105(5) -0.0245(5) 0.2639(3) 0.0295 1.0000 Uani C22 C 0.0280(5) 0.0193(5) 0.3351(3) 0.0298 1.0000 Uani C23 C 0.1503(5) 0.0236(4) 0.2917(3) 0.0241 1.0000 Uani C24 C 0.3555(5) 0.0204(4) 0.1371(3) 0.0230 1.0000 Uani C25 C 0.4071(5) -0.0560(4) 0.2060(3) 0.0277 1.0000 Uani C26 C 0.4753(5) -0.1479(5) 0.1638(4) 0.0332 1.0000 Uani C27 C 0.3748(6) -0.2241(5) 0.0792(4) 0.0353 1.0000 Uani C28 C 0.3173(6) -0.1500(5) 0.0121(4) 0.0336 1.0000 Uani C29 C 0.2510(5) -0.0565(4) 0.0548(3) 0.0304 1.0000 Uani C30 C 0.2318(5) 0.2222(4) 0.0902(3) 0.0239 1.0000 Uani C31 C 0.3313(5) 0.2544(5) 0.0316(3) 0.0294 1.0000 Uani C32 C 0.2550(6) 0.3002(5) -0.0505(4) 0.0362 1.0000 Uani C33 C 0.1970(7) 0.4068(5) -0.0211(4) 0.0384 1.0000 Uani C34 C 0.1014(6) 0.3791(5) 0.0399(4) 0.0376 1.0000 Uani C35 C 0.1746(6) 0.3297(4) 0.1205(3) 0.0301 1.0000 Uani P2 P 0.11476(18) 0.66461(13) 0.30257(11) 0.0407 1.0000 Uani F1 F 0.0652(6) 0.5378(4) 0.2440(3) 0.0659 1.0000 Uani F2 F 0.1643(7) 0.7893(4) 0.3645(4) 0.0944 1.0000 Uani F3 F 0.1833(15) 0.7126(7) 0.2337(7) 0.1869 1.0000 Uani F4 F 0.0311(7) 0.6146(5) 0.3709(4) 0.0806 1.0000 Uani F5 F 0.2467(5) 0.6259(4) 0.3610(5) 0.0948 1.0000 Uani F6 F -0.0233(8) 0.7017(5) 0.2547(5) 0.1157 1.0000 Uani H11 H 0.495(6) 0.510(5) 0.340(4) 0.028(14) 1.0000 Uiso H21 H 0.607(6) 0.421(5) 0.448(4) 0.025(14) 1.0000 Uiso H51 H 0.630(7) 0.139(6) 0.260(4) 0.033(16) 1.0000 Uiso H61 H 0.558(5) 0.236(4) 0.150(3) 0.020(11) 1.0000 Uiso H31 H 0.8349 0.4003 0.4696 0.0398 1.0000 Uiso H32 H 0.8348 0.4451 0.3746 0.0398 1.0000 Uiso H41 H 0.8633 0.2584 0.3416 0.0402 1.0000 Uiso H42 H 0.7615 0.2100 0.4023 0.0402 1.0000 Uiso H71 H 0.7887 0.4228 0.2380 0.0467 1.0000 Uiso H72 H 0.6772 0.4233 0.1431 0.0467 1.0000 Uiso H81 H 0.7016 0.5779 0.2798 0.0495 1.0000 Uiso H82 H 0.5486 0.5259 0.2098 0.0495 1.0000 Uiso H91 H 0.2421 0.4160 0.3158 0.0281 1.0000 Uiso H101 H 0.0798 0.4317 0.4044 0.0323 1.0000 Uiso H111 H 0.0833 0.3204 0.5228 0.0360 1.0000 Uiso H131 H 0.2985 0.2310 0.6396 0.0482 1.0000 Uiso H132 H 0.1581 0.1420 0.5762 0.0482 1.0000 Uiso H141 H 0.3511 0.0446 0.6255 0.0540 1.0000 Uiso H142 H 0.2918 0.0226 0.5162 0.0540 1.0000 Uiso H151 H 0.5279 0.1997 0.6160 0.0537 1.0000 Uiso H152 H 0.5405 0.0748 0.5624 0.0537 1.0000 Uiso H161 H 0.5614 0.2423 0.4826 0.0337 1.0000 Uiso H162 H 0.4577 0.1216 0.4250 0.0337 1.0000 Uiso H181 H 0.1268 0.1831 0.2505 0.0276 1.0000 Uiso H191 H -0.0095 0.1083 0.1024 0.0343 1.0000 Uiso H192 H 0.0042 -0.0237 0.1180 0.0343 1.0000 Uiso H201 H -0.1311 0.1283 0.2145 0.0355 1.0000 Uiso H202 H -0.2108 0.0110 0.1408 0.0355 1.0000 Uiso H211 H -0.1887 -0.0194 0.2930 0.0363 1.0000 Uiso H212 H -0.1160 -0.1075 0.2372 0.0363 1.0000 Uiso H221 H 0.0374 -0.0345 0.3797 0.0371 1.0000 Uiso H222 H 0.0296 0.0993 0.3664 0.0371 1.0000 Uiso H231 H 0.2398 0.0533 0.3393 0.0302 1.0000 Uiso H232 H 0.1499 -0.0566 0.2612 0.0302 1.0000 Uiso H241 H 0.4357 0.0571 0.1156 0.0274 1.0000 Uiso H251 H 0.4769 -0.0057 0.2596 0.0350 1.0000 Uiso H252 H 0.3261 -0.0957 0.2253 0.0350 1.0000 Uiso H261 H 0.5047 -0.1984 0.2086 0.0422 1.0000 Uiso H262 H 0.5591 -0.1078 0.1476 0.0422 1.0000 Uiso H271 H 0.4254 -0.2783 0.0507 0.0431 1.0000 Uiso H272 H 0.2955 -0.2703 0.0963 0.0431 1.0000 Uiso H281 H 0.3952 -0.1109 -0.0103 0.0400 1.0000 Uiso H282 H 0.2450 -0.2016 -0.0395 0.0400 1.0000 Uiso H291 H 0.1688 -0.0954 0.0735 0.0359 1.0000 Uiso H292 H 0.2194 -0.0071 0.0097 0.0359 1.0000 Uiso H301 H 0.1554 0.1593 0.0503 0.0294 1.0000 Uiso H311 H 0.4122 0.3162 0.0681 0.0381 1.0000 Uiso H312 H 0.3659 0.1837 0.0105 0.0381 1.0000 Uiso H321 H 0.3219 0.3224 -0.0869 0.0458 1.0000 Uiso H322 H 0.1761 0.2373 -0.0880 0.0458 1.0000 Uiso H331 H 0.2764 0.4718 0.0123 0.0492 1.0000 Uiso H332 H 0.1428 0.4313 -0.0757 0.0492 1.0000 Uiso H341 H 0.0727 0.4522 0.0627 0.0492 1.0000 Uiso H342 H 0.0167 0.3205 0.0043 0.0492 1.0000 Uiso H351 H 0.2538 0.3912 0.1593 0.0393 1.0000 Uiso H352 H 0.1063 0.3069 0.1558 0.0393 1.0000 Uiso 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 0.01908(10) 0.02524(10) 0.01955(10) 0.00139(6) 0.00845(6) 0.00360(6) C1 0.029(2) 0.032(2) 0.037(3) 0.001(2) 0.015(2) 0.001(2) C2 0.020(2) 0.026(2) 0.025(2) -0.0055(16) 0.0113(17) 0.0043(16) C3 0.020(2) 0.043(3) 0.036(3) -0.006(2) 0.0070(19) 0.005(2) C4 0.020(2) 0.043(3) 0.037(3) -0.005(2) 0.0067(19) 0.006(2) C5 0.0136(19) 0.038(3) 0.038(3) -0.005(2) 0.0125(18) 0.0094(17) C6 0.021(2) 0.038(3) 0.027(2) -0.0037(19) 0.0119(18) 0.0035(19) C7 0.036(3) 0.043(3) 0.038(3) 0.007(2) 0.023(2) -0.009(2) C8 0.043(3) 0.033(3) 0.048(3) 0.011(2) 0.022(3) 0.000(2) N1 0.0189(16) 0.0251(17) 0.0208(17) 0.0014(14) 0.0083(13) 0.0043(14) C9 0.022(2) 0.026(2) 0.022(2) -0.0022(16) 0.0079(16) 0.0062(16) C10 0.020(2) 0.027(2) 0.033(2) 0.0003(18) 0.0098(18) 0.0035(17) C11 0.030(2) 0.030(2) 0.030(2) -0.0019(18) 0.0153(19) 0.0015(18) C12 0.030(2) 0.032(2) 0.027(2) 0.0017(18) 0.0148(19) 0.0032(19) C13 0.037(3) 0.052(3) 0.031(3) 0.013(2) 0.019(2) 0.007(2) C14 0.043(3) 0.054(3) 0.039(3) 0.018(3) 0.014(2) 0.014(3) C15 0.051(3) 0.048(3) 0.035(3) 0.018(2) 0.021(2) 0.022(3) C16 0.025(2) 0.035(2) 0.024(2) 0.0104(18) 0.0096(17) 0.0069(18) C17 0.025(2) 0.027(2) 0.0183(19) 0.0013(16) 0.0059(16) 0.0051(17) P1 0.0187(5) 0.0242(5) 0.0176(5) 0.0036(4) 0.0084(4) 0.0047(4) C18 0.0184(19) 0.031(2) 0.0197(19) 0.0044(16) 0.0085(15) 0.0070(16) C19 0.021(2) 0.042(3) 0.022(2) 0.0050(18) 0.0100(17) 0.0017(18) C20 0.017(2) 0.045(3) 0.027(2) 0.004(2) 0.0075(17) 0.0025(18) C21 0.023(2) 0.040(3) 0.028(2) 0.0059(19) 0.0145(18) 0.0021(19) C22 0.028(2) 0.039(3) 0.026(2) 0.0092(19) 0.0119(18) 0.0059(19) C23 0.023(2) 0.028(2) 0.025(2) 0.0081(17) 0.0104(17) 0.0050(17) C24 0.023(2) 0.0230(19) 0.022(2) -0.0017(16) 0.0088(16) 0.0033(16) C25 0.026(2) 0.032(2) 0.030(2) 0.0072(18) 0.0114(18) 0.0106(18) C26 0.030(2) 0.034(2) 0.041(3) 0.007(2) 0.016(2) 0.013(2) C27 0.031(3) 0.031(2) 0.045(3) -0.001(2) 0.019(2) 0.005(2) C28 0.032(2) 0.037(3) 0.031(2) -0.005(2) 0.012(2) 0.008(2) C29 0.031(2) 0.032(2) 0.026(2) -0.0016(18) 0.0066(19) 0.0088(19) C30 0.025(2) 0.030(2) 0.0188(19) 0.0051(16) 0.0082(16) 0.0064(17) C31 0.030(2) 0.038(3) 0.028(2) 0.0132(19) 0.0159(19) 0.009(2) C32 0.041(3) 0.045(3) 0.028(2) 0.013(2) 0.015(2) 0.011(2) C33 0.054(3) 0.042(3) 0.027(2) 0.018(2) 0.016(2) 0.015(3) C34 0.043(3) 0.048(3) 0.032(3) 0.017(2) 0.016(2) 0.021(2) C35 0.039(3) 0.032(2) 0.027(2) 0.0090(19) 0.016(2) 0.016(2) P2 0.0528(9) 0.0334(7) 0.0399(8) 0.0118(6) 0.0159(7) 0.0101(6) F1 0.092(3) 0.043(2) 0.055(2) -0.0041(18) 0.011(2) 0.014(2) F2 0.121(5) 0.038(2) 0.096(4) -0.004(2) -0.026(4) 0.024(3) F3 0.365(16) 0.089(5) 0.188(9) 0.057(5) 0.226(11) 0.028(7) F4 0.107(4) 0.083(3) 0.076(3) 0.024(3) 0.059(3) 0.029(3) F5 0.049(3) 0.043(2) 0.174(6) 0.012(3) -0.005(3) 0.0089(19) F6 0.120(5) 0.072(4) 0.124(5) 0.012(3) -0.039(4) 0.041(4) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ir1 . C1 . 2.155(5) yes Ir1 . C2 . 2.214(4) yes Ir1 . C5 . 2.136(4) yes Ir1 . C6 . 2.176(5) yes Ir1 . N1 . 2.108(4) yes Ir1 . P1 . 2.3592(11) yes C1 . C2 . 1.394(8) yes C1 . C8 . 1.520(8) yes C1 . H11 . 0.98(6) no C2 . C3 . 1.514(6) yes C2 . H21 . 0.90(6) no C3 . C4 . 1.550(7) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.519(7) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.397(8) yes C5 . H51 . 0.97(7) no C6 . C7 . 1.532(7) yes C6 . H61 . 1.02(5) no C7 . C8 . 1.540(9) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . H81 . 1.000 no C8 . H82 . 1.000 no N1 . C9 . 1.345(6) yes N1 . C17 . 1.356(6) yes C9 . C10 . 1.386(6) yes C9 . H91 . 1.000 no C10 . C11 . 1.385(7) yes C10 . H101 . 1.000 no C11 . C12 . 1.395(7) yes C11 . H111 . 1.000 no C12 . C13 . 1.511(7) yes C12 . C17 . 1.398(6) yes C13 . C14 . 1.538(9) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . C15 . 1.501(9) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . C16 . 1.536(7) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . C17 . 1.512(6) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no P1 . C18 . 1.868(4) yes P1 . C24 . 1.863(4) yes P1 . C30 . 1.865(5) yes C18 . C19 . 1.541(6) yes C18 . C23 . 1.535(6) yes C18 . H181 . 1.000 no C19 . C20 . 1.532(6) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . C21 . 1.524(7) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . C22 . 1.526(7) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C23 . 1.530(6) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . C25 . 1.543(7) yes C24 . C29 . 1.524(6) yes C24 . H241 . 1.000 no C25 . C26 . 1.529(7) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.527(8) yes C26 . H261 . 1.000 no C26 . H262 . 1.000 no C27 . C28 . 1.521(8) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C28 . C29 . 1.534(7) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . C31 . 1.538(6) yes C30 . C35 . 1.538(6) yes C30 . H301 . 1.000 no C31 . C32 . 1.540(7) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . C33 . 1.531(8) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C33 . C34 . 1.528(8) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no C34 . C35 . 1.534(7) yes C34 . H341 . 1.000 no C34 . H342 . 1.000 no C35 . H351 . 1.000 no C35 . H352 . 1.000 no P2 . F1 . 1.583(4) yes P2 . F2 . 1.584(5) yes P2 . F3 . 1.522(6) yes P2 . F4 . 1.613(5) yes P2 . F5 . 1.594(5) yes P2 . F6 . 1.574(6) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . Ir1 . C2 . 37.2(2) yes C1 . Ir1 . C5 . 97.1(2) yes C2 . Ir1 . C5 . 81.11(18) yes C1 . Ir1 . C6 . 81.2(2) yes C2 . Ir1 . C6 . 88.61(17) yes C5 . Ir1 . C6 . 37.8(2) yes C1 . Ir1 . N1 . 91.42(17) yes C2 . Ir1 . N1 . 87.09(15) yes C5 . Ir1 . N1 . 147.25(19) yes C6 . Ir1 . N1 . 172.14(17) yes C1 . Ir1 . P1 . 141.34(15) yes C2 . Ir1 . P1 . 178.44(13) yes C5 . Ir1 . P1 . 98.99(14) yes C6 . Ir1 . P1 . 90.54(13) yes N1 . Ir1 . P1 . 93.61(10) yes Ir1 . C1 . C2 . 73.7(3) yes Ir1 . C1 . C8 . 109.8(4) yes C2 . C1 . C8 . 125.1(5) yes Ir1 . C1 . H11 . 106(4) no C2 . C1 . H11 . 121(4) no C8 . C1 . H11 . 111(4) no Ir1 . C2 . C1 . 69.1(3) yes Ir1 . C2 . C3 . 112.0(3) yes C1 . C2 . C3 . 123.7(5) yes Ir1 . C2 . H21 . 103(4) no C1 . C2 . H21 . 114(4) no C3 . C2 . H21 . 120(4) no C2 . C3 . C4 . 111.3(4) yes C2 . C3 . H31 . 109.023 no C4 . C3 . H31 . 109.023 no C2 . C3 . H32 . 109.023 no C4 . C3 . H32 . 109.023 no H31 . C3 . H32 . 109.467 no C3 . C4 . C5 . 112.7(4) yes C3 . C4 . H41 . 108.650 no C5 . C4 . H41 . 108.650 no C3 . C4 . H42 . 108.650 no C5 . C4 . H42 . 108.650 no H41 . C4 . H42 . 109.467 no Ir1 . C5 . C4 . 109.5(3) yes Ir1 . C5 . C6 . 72.6(3) yes C4 . C5 . C6 . 126.3(5) yes Ir1 . C5 . H51 . 108(4) no C4 . C5 . H51 . 110(4) no C6 . C5 . H51 . 120(4) no Ir1 . C6 . C5 . 69.6(3) yes Ir1 . C6 . C7 . 113.2(3) yes C5 . C6 . C7 . 125.0(5) yes Ir1 . C6 . H61 . 106(3) no C5 . C6 . H61 . 110(3) no C7 . C6 . H61 . 120(3) no C6 . C7 . C8 . 111.7(4) yes C6 . C7 . H71 . 108.912 no C8 . C7 . H71 . 108.912 no C6 . C7 . H72 . 108.912 no C8 . C7 . H72 . 108.911 no H71 . C7 . H72 . 109.467 no C1 . C8 . C7 . 113.6(5) yes C1 . C8 . H81 . 108.425 no C7 . C8 . H81 . 108.425 no C1 . C8 . H82 . 108.425 no C7 . C8 . H82 . 108.425 no H81 . C8 . H82 . 109.467 no Ir1 . N1 . C9 . 120.2(3) yes Ir1 . N1 . C17 . 120.3(3) yes C9 . N1 . C17 . 119.3(4) yes N1 . C9 . C10 . 122.3(4) yes N1 . C9 . H91 . 118.832 no C10 . C9 . H91 . 118.832 no C9 . C10 . C11 . 118.4(4) yes C9 . C10 . H101 . 120.800 no C11 . C10 . H101 . 120.800 no C10 . C11 . C12 . 120.2(4) yes C10 . C11 . H111 . 119.911 no C12 . C11 . H111 . 119.911 no C11 . C12 . C13 . 120.2(4) yes C11 . C12 . C17 . 118.2(5) yes C13 . C12 . C17 . 121.6(5) yes C12 . C13 . C14 . 112.3(4) yes C12 . C13 . H131 . 108.760 no C14 . C13 . H131 . 108.760 no C12 . C13 . H132 . 108.760 no C14 . C13 . H132 . 108.760 no H131 . C13 . H132 . 109.467 no C13 . C14 . C15 . 108.7(5) yes C13 . C14 . H141 . 109.665 no C15 . C14 . H141 . 109.665 no C13 . C14 . H142 . 109.665 no C15 . C14 . H142 . 109.665 no H141 . C14 . H142 . 109.467 no C14 . C15 . C16 . 111.2(5) yes C14 . C15 . H151 . 109.035 no C16 . C15 . H151 . 109.035 no C14 . C15 . H152 . 109.035 no C16 . C15 . H152 . 109.035 no H151 . C15 . H152 . 109.467 no C15 . C16 . C17 . 113.7(4) yes C15 . C16 . H161 . 108.405 no C17 . C16 . H161 . 108.406 no C15 . C16 . H162 . 108.406 no C17 . C16 . H162 . 108.406 no H161 . C16 . H162 . 109.467 no N1 . C17 . C12 . 121.4(4) yes N1 . C17 . C16 . 117.3(4) yes C12 . C17 . C16 . 121.3(4) yes Ir1 . P1 . C18 . 114.23(14) yes Ir1 . P1 . C24 . 115.81(15) yes C18 . P1 . C24 . 109.5(2) yes Ir1 . P1 . C30 . 109.94(15) yes C18 . P1 . C30 . 100.8(2) yes C24 . P1 . C30 . 105.2(2) yes P1 . C18 . C19 . 118.0(3) yes P1 . C18 . C23 . 114.6(3) yes C19 . C18 . C23 . 108.7(4) yes P1 . C18 . H181 . 98.557 no C19 . C18 . H181 . 105.946 no C23 . C18 . H181 . 110.102 no C18 . C19 . C20 . 109.8(4) yes C18 . C19 . H191 . 109.403 no C20 . C19 . H191 . 109.402 no C18 . C19 . H192 . 109.403 no C20 . C19 . H192 . 109.402 no H191 . C19 . H192 . 109.467 no C19 . C20 . C21 . 112.3(4) yes C19 . C20 . H201 . 108.763 no C21 . C20 . H201 . 108.763 no C19 . C20 . H202 . 108.763 no C21 . C20 . H202 . 108.763 no H201 . C20 . H202 . 109.467 no C20 . C21 . C22 . 111.4(4) yes C20 . C21 . H211 . 108.987 no C22 . C21 . H211 . 108.987 no C20 . C21 . H212 . 108.987 no C22 . C21 . H212 . 108.987 no H211 . C21 . H212 . 109.467 no C21 . C22 . C23 . 110.6(4) yes C21 . C22 . H221 . 109.196 no C23 . C22 . H221 . 109.196 no C21 . C22 . H222 . 109.196 no C23 . C22 . H222 . 109.196 no H221 . C22 . H222 . 109.467 no C18 . C23 . C22 . 109.9(4) yes C18 . C23 . H231 . 109.359 no C22 . C23 . H231 . 109.359 no C18 . C23 . H232 . 109.359 no C22 . C23 . H232 . 109.359 no H231 . C23 . H232 . 109.467 no P1 . C24 . C25 . 113.6(3) yes P1 . C24 . C29 . 116.1(3) yes C25 . C24 . C29 . 109.3(4) yes P1 . C24 . H241 . 101.339 no C25 . C24 . H241 . 109.378 no C29 . C24 . H241 . 106.415 no C24 . C25 . C26 . 110.1(4) yes C24 . C25 . H251 . 109.312 no C26 . C25 . H251 . 109.312 no C24 . C25 . H252 . 109.312 no C26 . C25 . H252 . 109.312 no H251 . C25 . H252 . 109.467 no C25 . C26 . C27 . 111.4(4) yes C25 . C26 . H261 . 108.976 no C27 . C26 . H261 . 108.976 no C25 . C26 . H262 . 108.976 no C27 . C26 . H262 . 108.976 no H261 . C26 . H262 . 109.467 no C26 . C27 . C28 . 111.0(4) yes C26 . C27 . H271 . 109.093 no C28 . C27 . H271 . 109.093 no C26 . C27 . H272 . 109.093 no C28 . C27 . H272 . 109.093 no H271 . C27 . H272 . 109.467 no C27 . C28 . C29 . 111.7(4) yes C27 . C28 . H281 . 108.924 no C29 . C28 . H281 . 108.925 no C27 . C28 . H282 . 108.924 no C29 . C28 . H282 . 108.924 no H281 . C28 . H282 . 109.467 no C24 . C29 . C28 . 110.8(4) yes C24 . C29 . H291 . 109.144 no C28 . C29 . H291 . 109.144 no C24 . C29 . H292 . 109.144 no C28 . C29 . H292 . 109.144 no H291 . C29 . H292 . 109.467 no P1 . C30 . C31 . 116.8(3) yes P1 . C30 . C35 . 111.4(3) yes C31 . C30 . C35 . 109.5(4) yes P1 . C30 . H301 . 102.768 no C31 . C30 . H301 . 104.944 no C35 . C30 . H301 . 111.097 no C30 . C31 . C32 . 110.3(4) yes C30 . C31 . H311 . 109.262 no C32 . C31 . H311 . 109.262 no C30 . C31 . H312 . 109.262 no C32 . C31 . H312 . 109.262 no H311 . C31 . H312 . 109.467 no C31 . C32 . C33 . 111.0(4) yes C31 . C32 . H321 . 109.090 no C33 . C32 . H321 . 109.090 no C31 . C32 . H322 . 109.090 no C33 . C32 . H322 . 109.090 no H321 . C32 . H322 . 109.467 no C32 . C33 . C34 . 110.9(5) yes C32 . C33 . H331 . 109.108 no C34 . C33 . H331 . 109.108 no C32 . C33 . H332 . 109.108 no C34 . C33 . H332 . 109.108 no H331 . C33 . H332 . 109.467 no C33 . C34 . C35 . 111.6(5) yes C33 . C34 . H341 . 108.942 no C35 . C34 . H341 . 108.942 no C33 . C34 . H342 . 108.942 no C35 . C34 . H342 . 108.942 no H341 . C34 . H342 . 109.467 no C30 . C35 . C34 . 111.7(4) yes C30 . C35 . H351 . 108.919 no C34 . C35 . H351 . 108.919 no C30 . C35 . H352 . 108.919 no C34 . C35 . H352 . 108.919 no H351 . C35 . H352 . 109.467 no F1 . P2 . F2 . 177.8(3) yes F1 . P2 . F3 . 93.1(4) yes F2 . P2 . F3 . 88.9(5) yes F1 . P2 . F4 . 86.1(3) yes F2 . P2 . F4 . 92.0(4) yes F3 . P2 . F4 . 175.7(6) yes F1 . P2 . F5 . 90.1(3) yes F2 . P2 . F5 . 88.6(3) yes F3 . P2 . F5 . 97.9(6) yes F4 . P2 . F5 . 86.3(4) yes F1 . P2 . F6 . 91.4(3) yes F2 . P2 . F6 . 89.6(3) yes F3 . P2 . F6 . 88.6(7) yes F4 . P2 . F6 . 87.2(4) yes F5 . P2 . F6 . 173.1(5) yes _chemical_name_common ;Iridium(1+)((1,2,5,6-eta)(1,5-COD)(5,6,7,8- THQ)(P(Cyclohexyl)3)PF6(1-). ; # Attachment 'CC arc1460a.cif' data_arc1460 _database_code_depnum_ccdc_archive 'CCDC 654177' _audit_update_record ; 2007-08-06 # Formatted by publCIF ; #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic ; Iridium(1+),[(1,2,5,6-?)-1,5-cyclooctadiene](5,6,7,8-tetrahydroquinoline) (tris(4-fluorophenyl)phosphine) (hexafluorophosphate)(1-) ; _chemical_melting_point ? _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The hydrogen atoms of the coordinated alkene groups were located in a difference Fourier map and their coordinates and isotropic displacement parameters subsequently refined. Other hydrogen atoms were positioned geometrically. ; #============================================================= _cell_length_a 15.2914(2) _cell_angle_alpha 90 _cell_length_b 12.2710(2) _cell_angle_beta 91.7169(6) _cell_length_c 17.6370(3) _cell_angle_gamma 90 _cell_volume 3307.93(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B 'Ir ' -1.4442 7.9887 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011 11.4722 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'P ' 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C35 H35 F9 Ir N P2 ' _chemical_formula_moiety ' C35 H35 F3 Ir N P, F6 P ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 894.82 _cell_measurement_reflns_used 44293 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' block ' _exptl_crystal_colour ' orange ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.18 _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 4.211 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.71 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 44293 _reflns_number_total 7534 # 7880 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_theta_min 5.117 _diffrn_reflns_theta_max 27.496 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.496 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _refine_diff_density_min -0.97 _refine_diff_density_max 1.45 _refine_ls_number_reflns 5480 _refine_ls_number_restraints 42 _refine_ls_number_parameters 468 #_refine_ls_R_factor_ref 0.0278 _refine_ls_wR_factor_ref 0.0293 _refine_ls_goodness_of_fit_ref 1.1134 #_reflns_number_all 7534 _refine_ls_R_factor_all 0.0455 _refine_ls_wR_factor_all 0.0497 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 5480 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_gt 0.0293 _refine_ls_shift/su_max 0.031432 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.201 0.0470 0.0278 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group Ir1 Ir 0.183761(10) 0.201294(13) 0.546431(9) 0.0204 1.0000 Uani . . . . . C1 C 0.0613(3) 0.1670(4) 0.6045(3) 0.0300 1.0000 Uani . . . . . C2 C 0.1105(3) 0.0720(4) 0.6025(3) 0.0263 1.0000 Uani . . . . . C3 C 0.1600(3) 0.0238(4) 0.6697(3) 0.0313 1.0000 Uani . . . . . C4 C 0.2558(3) 0.0597(4) 0.6749(3) 0.0338 1.0000 Uani . . . . . C5 C 0.2703(3) 0.1721(4) 0.6420(2) 0.0266 1.0000 Uani . . . . . C6 C 0.2192(3) 0.2640(4) 0.6570(2) 0.0274 1.0000 Uani . . . . . C7 C 0.1432(3) 0.2640(4) 0.7113(2) 0.0346 1.0000 Uani . . . . . C8 C 0.0547(3) 0.2411(4) 0.6720(3) 0.0364 1.0000 Uani . . . . . N1 N 0.1154(2) 0.1717(3) 0.4430(2) 0.0250 1.0000 Uani . . . . . C9 C 0.1253(3) 0.0724(4) 0.4101(3) 0.0284 1.0000 Uani . . . . . C10 C 0.0847(3) 0.0455(4) 0.3425(3) 0.0366 1.0000 Uani . . . . . C11 C 0.0326(3) 0.1227(5) 0.3067(3) 0.0386 1.0000 Uani . . . . . C12 C 0.0206(3) 0.2241(4) 0.3386(3) 0.0329 1.0000 Uani . . . . . C13 C -0.0367(4) 0.3086(5) 0.2998(3) 0.0463 0.51(4) Uani . U P 1 1 C14 C -0.0477(15) 0.4119(11) 0.3436(11) 0.0484 0.51(4) Uani . U P 1 1 C15 C 0.0268(15) 0.4461(12) 0.3924(10) 0.0435 0.51(4) Uani . U P 1 1 C16 C 0.0549(3) 0.3554(4) 0.4469(3) 0.0311 0.51(4) Uani . U P 1 1 C63 C -0.0367(4) 0.3086(5) 0.2998(3) 0.0463 0.49(4) Uani . U P 1 2 C64 C -0.0093(14) 0.4211(12) 0.3198(9) 0.0403 0.49(4) Uani . U P 1 2 C65 C -0.0080(15) 0.4351(12) 0.4079(9) 0.0341 0.49(4) Uani . U P 1 2 C66 C 0.0549(3) 0.3554(4) 0.4469(3) 0.0311 0.49(4) Uani . U P 1 2 C17 C 0.0642(3) 0.2467(4) 0.4082(2) 0.0249 1.0000 Uani . . . . . P1 P 0.30138(7) 0.27135(8) 0.48113(6) 0.0188 1.0000 Uani . . . . . C18 C 0.2755(3) 0.3454(3) 0.3932(2) 0.0219 1.0000 Uani . . . . . C19 C 0.2696(3) 0.4587(3) 0.3910(2) 0.0245 1.0000 Uani . . . . . C20 C 0.2480(3) 0.5140(3) 0.3240(3) 0.0281 1.0000 Uani . . . . . C21 C 0.2322(3) 0.4528(4) 0.2597(2) 0.0277 1.0000 Uani . . . . . C22 C 0.2360(3) 0.3411(4) 0.2592(2) 0.0316 1.0000 Uani . . . . . C23 C 0.2577(3) 0.2870(4) 0.3259(2) 0.0276 1.0000 Uani . . . . . F1 F 0.21087(19) 0.5057(2) 0.19431(15) 0.0405 1.0000 Uani . . . . . C24 C 0.3715(3) 0.1620(3) 0.4486(2) 0.0206 1.0000 Uani . . . . . C25 C 0.4374(3) 0.1830(3) 0.3966(3) 0.0310 1.0000 Uani . . . . . C26 C 0.4886(3) 0.0976(4) 0.3713(2) 0.0304 1.0000 Uani . . . . . C27 C 0.4722(3) -0.0066(4) 0.3967(2) 0.0259 1.0000 Uani . . . . . C28 C 0.4077(3) -0.0304(3) 0.4461(2) 0.0247 1.0000 Uani . . . . . C29 C 0.3571(3) 0.0553(3) 0.4722(2) 0.0210 1.0000 Uani . . . . . F2 F 0.52172(18) -0.0888(2) 0.37052(16) 0.0382 1.0000 Uani . . . . . C30 C 0.3734(3) 0.3630(3) 0.5353(2) 0.0220 1.0000 Uani . . . . . C31 C 0.4623(3) 0.3410(3) 0.5484(2) 0.0246 1.0000 Uani . . . . . C32 C 0.5141(3) 0.4103(4) 0.5930(2) 0.0281 1.0000 Uani . . . . . C33 C 0.4763(3) 0.5017(4) 0.6224(2) 0.0275 1.0000 Uani . . . . . C34 C 0.3891(3) 0.5281(3) 0.6103(2) 0.0279 1.0000 Uani . . . . . C35 C 0.3375(3) 0.4565(3) 0.5671(2) 0.0250 1.0000 Uani . . . . . F3 F 0.52593(19) 0.5689(2) 0.66797(15) 0.0387 1.0000 Uani . . . . . P2 P 0.78859(9) 0.24500(10) 0.49893(8) 0.0371 1.0000 Uani . . . . . F4 F 0.7730(3) 0.3097(4) 0.4219(3) 0.0961 1.0000 Uani . . . . . F5 F 0.8012(4) 0.1776(5) 0.5731(3) 0.1118 1.0000 Uani . . . . . F6 F 0.7393(3) 0.1443(4) 0.4621(3) 0.0976 1.0000 Uani . . . . . F7 F 0.8375(3) 0.3464(4) 0.5327(3) 0.1130 1.0000 Uani . . . . . F8 F 0.87840(19) 0.2003(3) 0.46748(19) 0.0488 1.0000 Uani . . . . . F9 F 0.6983(2) 0.2898(3) 0.5306(3) 0.0718 1.0000 Uani . . . . . H11 H 0.018(3) 0.170(4) 0.568(3) 0.031(13) 1.0000 Uiso . . . . . H21 H 0.098(3) 0.021(4) 0.564(3) 0.029(13) 1.0000 Uiso . . . . . H51 H 0.330(3) 0.184(4) 0.629(3) 0.028(12) 1.0000 Uiso . . . . . H61 H 0.244(4) 0.332(5) 0.650(3) 0.050(17) 1.0000 Uiso . . . . . H31 H 0.1307 0.0471 0.7170 0.0376 1.0000 Uiso . . . . . H32 H 0.1580 -0.0574 0.6654 0.0376 1.0000 Uiso . . . . . H41 H 0.2753 0.0604 0.7295 0.0406 1.0000 Uiso . . . . . H42 H 0.2916 0.0061 0.6466 0.0406 1.0000 Uiso . . . . . H71 H 0.1406 0.3370 0.7363 0.0418 1.0000 Uiso . . . . . H72 H 0.1544 0.2066 0.7507 0.0418 1.0000 Uiso . . . . . H81 H 0.0155 0.2062 0.7094 0.0440 1.0000 Uiso . . . . . H82 H 0.0287 0.3119 0.6547 0.0440 1.0000 Uiso . . . . . H91 H 0.1636 0.0171 0.4363 0.0341 1.0000 Uiso . . . . . H101 H 0.0927 -0.0282 0.3196 0.0440 1.0000 Uiso . . . . . H111 H 0.0030 0.1050 0.2569 0.0464 1.0000 Uiso . . . . . H131 H -0.0959 0.2759 0.2903 0.0552 0.51 Uiso . . . 1 1 H132 H -0.0104 0.3274 0.2502 0.0552 0.51 Uiso . . . 1 1 H141 H -0.0992 0.4023 0.3766 0.0580 0.51 Uiso . . . 1 1 H142 H -0.0600 0.4717 0.3063 0.0580 0.51 Uiso . . . 1 1 H151 H 0.0095 0.5114 0.4224 0.0523 0.51 Uiso . . . 1 1 H152 H 0.0770 0.4654 0.3600 0.0523 0.51 Uiso . . . 1 1 H161 H 0.1126 0.3755 0.4712 0.0373 0.51 Uiso . . . 1 1 H162 H 0.0101 0.3485 0.4867 0.0373 0.51 Uiso . . . 1 1 H631 H -0.0984 0.2976 0.3154 0.0552 0.49 Uiso . . . 1 2 H632 H -0.0334 0.2990 0.2436 0.0552 0.49 Uiso . . . 1 2 H641 H -0.0515 0.4742 0.2960 0.0484 0.49 Uiso . . . 1 2 H642 H 0.0505 0.4350 0.3006 0.0484 0.49 Uiso . . . 1 2 H651 H 0.0106 0.5112 0.4209 0.0409 0.49 Uiso . . . 1 2 H652 H -0.0683 0.4221 0.4266 0.0409 0.49 Uiso . . . 1 2 H661 H 0.0340 0.3419 0.4992 0.0373 0.49 Uiso . . . 1 2 H662 H 0.1140 0.3903 0.4500 0.0373 0.49 Uiso . . . 1 2 H191 H 0.2812 0.5013 0.4386 0.0293 1.0000 Uiso . . . . . H201 H 0.2441 0.5953 0.3227 0.0336 1.0000 Uiso . . . . . H221 H 0.2233 0.2995 0.2114 0.0379 1.0000 Uiso . . . . . H231 H 0.2608 0.2056 0.3263 0.0330 1.0000 Uiso . . . . . H251 H 0.4474 0.2589 0.3780 0.0371 1.0000 Uiso . . . . . H261 H 0.5366 0.1115 0.3352 0.0367 1.0000 Uiso . . . . . H281 H 0.3971 -0.1070 0.4630 0.0295 1.0000 Uiso . . . . . H291 H 0.3096 0.0400 0.5085 0.0252 1.0000 Uiso . . . . . H311 H 0.4889 0.2747 0.5254 0.0295 1.0000 Uiso . . . . . H321 H 0.5774 0.3939 0.6033 0.0336 1.0000 Uiso . . . . . H341 H 0.3640 0.5963 0.6318 0.0335 1.0000 Uiso . . . . . H351 H 0.2737 0.4723 0.5587 0.0300 1.0000 Uiso . . . . . 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 0.02065(7) 0.02122(7) 0.01927(8) 0.00119(7) 0.00166(5) 0.00037(7) C1 0.0199(19) 0.041(3) 0.030(2) 0.0070(19) 0.0066(17) -0.0048(18) C2 0.024(2) 0.027(2) 0.029(2) 0.0033(18) 0.0106(17) -0.0059(17) C3 0.037(2) 0.026(2) 0.030(2) 0.0097(18) 0.0037(19) -0.0010(19) C4 0.034(2) 0.035(3) 0.032(2) 0.010(2) 0.0010(19) 0.005(2) C5 0.023(2) 0.039(3) 0.0177(19) 0.0052(17) -0.0041(15) -0.0021(17) C6 0.038(2) 0.029(2) 0.0151(19) -0.0065(16) -0.0031(17) -0.0066(19) C7 0.047(3) 0.038(3) 0.019(2) -0.0023(18) 0.0138(19) -0.003(2) C8 0.038(3) 0.038(3) 0.034(3) 0.004(2) 0.014(2) 0.007(2) N1 0.0208(16) 0.0304(19) 0.0239(17) 0.0005(14) 0.0017(13) -0.0038(14) C9 0.029(2) 0.027(2) 0.029(2) -0.0065(18) 0.0025(17) -0.0056(18) C10 0.035(2) 0.038(3) 0.038(3) -0.012(2) 0.006(2) -0.007(2) C11 0.037(3) 0.053(3) 0.026(2) -0.009(2) 0.0034(19) -0.014(2) C12 0.026(2) 0.047(3) 0.025(2) 0.0070(19) 0.0016(17) -0.0037(19) C13 0.043(3) 0.056(3) 0.039(3) 0.010(2) -0.015(2) 0.000(3) C14 0.050(9) 0.049(5) 0.046(7) 0.017(4) -0.004(7) 0.005(5) C15 0.041(7) 0.040(6) 0.050(7) 0.017(4) 0.001(5) 0.005(6) C16 0.026(2) 0.030(2) 0.037(2) 0.0059(19) 0.0024(18) 0.0026(18) C63 0.043(3) 0.056(3) 0.039(3) 0.010(2) -0.015(2) 0.000(3) C64 0.041(8) 0.052(4) 0.028(5) 0.007(5) 0.002(6) 0.006(5) C65 0.044(8) 0.028(5) 0.030(5) 0.001(4) -0.002(5) 0.009(5) C66 0.026(2) 0.030(2) 0.037(2) 0.0059(19) 0.0024(18) 0.0026(18) C17 0.0221(19) 0.031(2) 0.022(2) 0.0032(17) -0.0002(16) -0.0006(17) P1 0.0215(5) 0.0173(5) 0.0178(5) -0.0001(4) 0.0022(4) 0.0005(4) C18 0.0213(18) 0.0201(19) 0.024(2) 0.0002(16) 0.0048(15) -0.0028(15) C19 0.029(2) 0.022(2) 0.022(2) 0.0013(16) -0.0022(16) -0.0011(16) C20 0.032(2) 0.018(2) 0.034(2) 0.0045(18) -0.0013(18) -0.0010(17) C21 0.027(2) 0.035(2) 0.020(2) 0.0103(18) -0.0026(16) -0.0009(19) C22 0.043(3) 0.031(2) 0.021(2) 0.0017(18) -0.0021(19) -0.006(2) C23 0.039(2) 0.023(2) 0.0206(19) -0.0007(17) -0.0028(17) -0.0005(18) F1 0.0506(17) 0.0417(16) 0.0284(14) 0.0135(12) -0.0097(12) -0.0013(14) C24 0.0244(19) 0.0208(18) 0.0166(18) -0.0005(15) 0.0023(15) 0.0020(15) C25 0.028(2) 0.022(2) 0.043(3) -0.0050(19) -0.0008(18) 0.0048(17) C26 0.034(2) 0.033(2) 0.024(2) -0.0003(19) 0.0090(17) 0.004(2) C27 0.029(2) 0.026(2) 0.023(2) -0.0068(17) -0.0022(16) 0.0095(17) C28 0.029(2) 0.0193(19) 0.026(2) -0.0005(16) -0.0030(16) 0.0018(16) C29 0.0216(19) 0.023(2) 0.0186(19) -0.0015(15) -0.0002(15) 0.0015(16) F2 0.0433(16) 0.0334(15) 0.0381(15) -0.0079(12) 0.0062(12) 0.0195(13) C30 0.030(2) 0.0185(19) 0.0175(19) 0.0026(15) 0.0006(15) -0.0015(16) C31 0.026(2) 0.0228(19) 0.025(2) 0.0017(16) 0.0001(16) -0.0021(16) C32 0.027(2) 0.029(2) 0.029(2) -0.0003(18) -0.0028(17) -0.0057(18) C33 0.036(2) 0.024(2) 0.023(2) 0.0022(17) -0.0050(17) -0.0124(18) C34 0.042(2) 0.0181(19) 0.023(2) -0.0003(17) 0.0015(18) -0.0032(18) C35 0.032(2) 0.021(2) 0.022(2) -0.0030(16) -0.0016(16) 0.0036(17) F3 0.0480(16) 0.0305(14) 0.0368(15) -0.0041(12) -0.0107(12) -0.0144(12) P2 0.0354(6) 0.0211(6) 0.0555(8) 0.0002(6) 0.0159(6) 0.0024(5) F4 0.065(3) 0.117(4) 0.107(4) 0.063(3) 0.022(2) 0.034(3) F5 0.129(4) 0.140(5) 0.069(3) 0.050(3) 0.047(3) 0.066(4) F6 0.077(3) 0.079(3) 0.141(4) -0.053(3) 0.057(3) -0.042(2) F7 0.079(3) 0.087(3) 0.176(5) -0.088(4) 0.055(3) -0.035(3) F8 0.0400(15) 0.0465(17) 0.0610(19) -0.0020(16) 0.0172(14) 0.0138(15) F9 0.049(2) 0.0392(19) 0.129(4) -0.007(2) 0.046(2) 0.0064(16) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ir1 . P1 . 2.3291(10) yes Ir1 . N1 . 2.107(3) yes Ir1 . C6 . 2.151(4) yes Ir1 . C5 . 2.142(4) yes Ir1 . C2 . 2.194(4) yes Ir1 . C1 . 2.202(4) yes C1 . H11 . 0.91(5) no C1 . C8 . 1.505(7) yes C1 . C2 . 1.389(6) yes C2 . H21 . 0.94(5) no C2 . C3 . 1.507(6) yes C3 . H32 . 1.000 no C3 . H31 . 1.000 no C3 . C4 . 1.530(7) yes C4 . H42 . 1.000 no C4 . H41 . 1.000 no C4 . C5 . 1.515(6) yes C5 . H51 . 0.95(5) no C5 . C6 . 1.402(6) yes C6 . H61 . 0.93(6) no C6 . C7 . 1.529(6) yes C7 . H72 . 1.000 no C7 . H71 . 1.000 no C7 . C8 . 1.528(7) yes C8 . H82 . 1.000 no C8 . H81 . 1.000 no N1 . C17 . 1.344(5) yes N1 . C9 . 1.360(6) yes C9 . H91 . 1.000 no C9 . C10 . 1.368(6) yes C10 . H101 . 1.000 no C10 . C11 . 1.379(8) yes C11 . H111 . 1.000 no C11 . C12 . 1.380(7) yes C12 . C17 . 1.407(6) yes C12 . C13 . 1.508(7) yes C12 . C17 . 1.407(6) yes C12 . C63 . 1.508(7) yes C13 . H132 . 1.000 no C13 . H131 . 1.000 no C13 . C14 . 1.497(17) yes C14 . H142 . 1.000 no C14 . H141 . 1.000 no C14 . C15 . 1.47(3) yes C15 . H152 . 1.000 no C15 . H151 . 1.000 no C15 . C16 . 1.523(15) yes C16 . H162 . 1.000 no C16 . H161 . 1.000 no C16 . C17 . 1.506(6) yes C63 . H632 . 1.000 no C63 . H631 . 1.000 no C63 . C64 . 1.482(16) yes C64 . H642 . 1.000 no C64 . H641 . 1.000 no C64 . C65 . 1.56(3) yes C65 . H652 . 1.000 no C65 . H651 . 1.000 no C65 . C66 . 1.521(14) yes C66 . H662 . 1.000 no C66 . H661 . 1.000 no C66 . C17 . 1.506(6) yes P1 . C30 . 1.825(4) yes P1 . C24 . 1.821(4) yes P1 . C18 . 1.830(4) yes C18 . C23 . 1.405(6) yes C18 . C19 . 1.394(6) yes C19 . H191 . 1.000 no C19 . C20 . 1.394(6) yes C20 . H201 . 1.000 no C20 . C21 . 1.376(6) yes C21 . F1 . 1.354(5) yes C21 . C22 . 1.372(6) yes C22 . H221 . 1.000 no C22 . C23 . 1.382(6) yes C23 . H231 . 1.000 no C24 . C29 . 1.394(6) yes C24 . C25 . 1.407(6) yes C25 . H251 . 1.000 no C25 . C26 . 1.389(6) yes C26 . H261 . 1.000 no C26 . C27 . 1.381(6) yes C27 . F2 . 1.351(5) yes C27 . C28 . 1.368(6) yes C28 . H281 . 1.000 no C28 . C29 . 1.391(6) yes C29 . H291 . 1.000 no C30 . C35 . 1.397(6) yes C30 . C31 . 1.398(6) yes C31 . H311 . 1.000 no C31 . C32 . 1.390(6) yes C32 . H321 . 1.000 no C32 . C33 . 1.371(6) yes C33 . F3 . 1.366(5) yes C33 . C34 . 1.383(6) yes C34 . H341 . 1.000 no C34 . C35 . 1.393(6) yes C35 . H351 . 1.000 no P2 . F9 . 1.602(3) yes P2 . F8 . 1.594(3) yes P2 . F7 . 1.560(4) yes P2 . F6 . 1.578(4) yes P2 . F5 . 1.555(4) yes P2 . F4 . 1.585(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag P1 . Ir1 . N1 . 90.33(9) yes P1 . Ir1 . C6 . 97.97(13) yes N1 . Ir1 . C6 . 162.16(16) yes P1 . Ir1 . C5 . 89.02(12) yes N1 . Ir1 . C5 . 158.68(16) yes C6 . Ir1 . C5 . 38.12(17) yes P1 . Ir1 . C2 . 154.39(12) yes N1 . Ir1 . C2 . 91.09(15) yes C6 . Ir1 . C2 . 88.20(18) yes C5 . Ir1 . C2 . 80.56(17) yes P1 . Ir1 . C1 . 168.75(13) yes N1 . Ir1 . C1 . 87.88(16) yes C6 . Ir1 . C1 . 80.89(18) yes C5 . Ir1 . C1 . 96.65(17) yes C2 . Ir1 . C1 . 36.82(17) yes H11 . C1 . C8 . 118(3) no H11 . C1 . C2 . 113(3) no C8 . C1 . C2 . 125.3(4) yes H11 . C1 . Ir1 . 106(3) no C8 . C1 . Ir1 . 109.3(3) yes C2 . C1 . Ir1 . 71.3(2) yes H21 . C2 . C3 . 113(3) no H21 . C2 . C1 . 119(3) no C3 . C2 . C1 . 124.6(4) yes H21 . C2 . Ir1 . 104(3) no C3 . C2 . Ir1 . 112.8(3) yes C1 . C2 . Ir1 . 71.9(2) yes H32 . C3 . H31 . 109.467 no H32 . C3 . C4 . 108.570 no H31 . C3 . C4 . 108.569 no H32 . C3 . C2 . 108.570 no H31 . C3 . C2 . 108.570 no C4 . C3 . C2 . 113.1(4) yes H42 . C4 . H41 . 109.467 no H42 . C4 . C5 . 108.592 no H41 . C4 . C5 . 108.593 no H42 . C4 . C3 . 108.593 no H41 . C4 . C3 . 108.593 no C5 . C4 . C3 . 113.0(4) yes H51 . C5 . C6 . 118(3) no H51 . C5 . Ir1 . 111(3) no C6 . C5 . Ir1 . 71.3(2) yes H51 . C5 . C4 . 113(3) no C6 . C5 . C4 . 124.8(4) yes Ir1 . C5 . C4 . 111.1(3) yes H61 . C6 . C7 . 114(4) no H61 . C6 . C5 . 118(4) no C7 . C6 . C5 . 123.8(4) yes H61 . C6 . Ir1 . 107(4) no C7 . C6 . Ir1 . 113.1(3) yes C5 . C6 . Ir1 . 70.6(2) yes H72 . C7 . H71 . 109.467 no H72 . C7 . C8 . 108.506 no H71 . C7 . C8 . 108.506 no H72 . C7 . C6 . 108.507 no H71 . C7 . C6 . 108.506 no C8 . C7 . C6 . 113.3(4) yes H82 . C8 . H81 . 109.467 no H82 . C8 . C1 . 108.586 no H81 . C8 . C1 . 108.586 no H82 . C8 . C7 . 108.586 no H81 . C8 . C7 . 108.586 no C1 . C8 . C7 . 113.0(4) yes C17 . N1 . C9 . 119.4(4) yes C17 . N1 . Ir1 . 122.9(3) yes C9 . N1 . Ir1 . 117.7(3) yes H91 . C9 . C10 . 118.858 no H91 . C9 . N1 . 118.858 no C10 . C9 . N1 . 122.3(4) yes H101 . C10 . C11 . 120.846 no H101 . C10 . C9 . 120.845 no C11 . C10 . C9 . 118.3(5) yes H111 . C11 . C12 . 119.508 no H111 . C11 . C10 . 119.508 no C12 . C11 . C10 . 121.0(4) yes C17 . C12 . C13 . 120.9(5) yes C17 . C12 . C11 . 117.9(4) yes C13 . C12 . C11 . 121.1(4) yes C17 . C12 . C63 . 120.9(5) yes C17 . C12 . C11 . 117.9(4) yes C63 . C12 . C11 . 121.1(4) yes H132 . C13 . H131 . 109.467 no H132 . C13 . C14 . 108.115 no H131 . C13 . C14 . 108.113 no H132 . C13 . C12 . 108.115 no H131 . C13 . C12 . 108.114 no C14 . C13 . C12 . 114.8(6) yes H142 . C14 . H141 . 109.469 no H142 . C14 . C15 . 107.648 no H141 . C14 . C15 . 107.649 no H142 . C14 . C13 . 107.653 no H141 . C14 . C13 . 107.653 no C15 . C14 . C13 . 116.6(17) yes H152 . C15 . H151 . 109.465 no H152 . C15 . C16 . 109.067 no H151 . C15 . C16 . 109.066 no H152 . C15 . C14 . 109.076 no H151 . C15 . C14 . 109.075 no C16 . C15 . C14 . 111.1(15) yes H162 . C16 . H161 . 109.467 no H162 . C16 . C17 . 108.578 no H161 . C16 . C17 . 108.578 no H162 . C16 . C15 . 108.577 no H161 . C16 . C15 . 108.580 no C17 . C16 . C15 . 113.0(7) yes H632 . C63 . H631 . 109.466 no H632 . C63 . C64 . 108.817 no H631 . C63 . C64 . 108.815 no H632 . C63 . C12 . 108.815 no H631 . C63 . C12 . 108.814 no C64 . C63 . C12 . 112.1(6) yes H642 . C64 . H641 . 109.464 no H642 . C64 . C65 . 109.466 no H641 . C64 . C65 . 109.463 no H642 . C64 . C63 . 109.461 no H641 . C64 . C63 . 109.459 no C65 . C64 . C63 . 109.5(17) yes H652 . C65 . H651 . 109.470 no H652 . C65 . C66 . 108.963 no H651 . C65 . C66 . 108.961 no H652 . C65 . C64 . 108.957 no H651 . C65 . C64 . 108.955 no C66 . C65 . C64 . 111.5(13) yes H662 . C66 . H661 . 109.467 no H662 . C66 . C17 . 107.914 no H661 . C66 . C17 . 107.914 no H662 . C66 . C65 . 107.915 no H661 . C66 . C65 . 107.912 no C17 . C66 . C65 . 115.6(6) yes N1 . C17 . C12 . 121.1(4) yes N1 . C17 . C16 . 117.5(4) yes C12 . C17 . C16 . 121.4(4) yes N1 . C17 . C12 . 121.1(4) yes N1 . C17 . C66 . 117.5(4) yes C12 . C17 . C66 . 121.4(4) yes C30 . P1 . C24 . 105.50(18) yes C30 . P1 . C18 . 104.47(18) yes C24 . P1 . C18 . 102.30(18) yes C30 . P1 . Ir1 . 115.56(13) yes C24 . P1 . Ir1 . 110.77(13) yes C18 . P1 . Ir1 . 116.85(13) yes C23 . C18 . C19 . 118.3(4) yes C23 . C18 . P1 . 119.6(3) yes C19 . C18 . P1 . 122.1(3) yes H191 . C19 . C20 . 119.235 no H191 . C19 . C18 . 119.236 no C20 . C19 . C18 . 121.5(4) yes H201 . C20 . C21 . 121.163 no H201 . C20 . C19 . 121.163 no C21 . C20 . C19 . 117.7(4) yes F1 . C21 . C22 . 118.9(4) yes F1 . C21 . C20 . 118.2(4) yes C22 . C21 . C20 . 122.9(4) yes H221 . C22 . C23 . 120.530 no H221 . C22 . C21 . 120.530 no C23 . C22 . C21 . 118.9(4) yes H231 . C23 . C22 . 119.689 no H231 . C23 . C18 . 119.688 no C22 . C23 . C18 . 120.6(4) yes C29 . C24 . C25 . 119.3(4) yes C29 . C24 . P1 . 119.9(3) yes C25 . C24 . P1 . 120.7(3) yes H251 . C25 . C26 . 120.234 no H251 . C25 . C24 . 120.233 no C26 . C25 . C24 . 119.5(4) yes H261 . C26 . C27 . 120.511 no H261 . C26 . C25 . 120.510 no C27 . C26 . C25 . 119.0(4) yes F2 . C27 . C28 . 118.7(4) yes F2 . C27 . C26 . 118.2(4) yes C28 . C27 . C26 . 123.1(4) yes H281 . C28 . C29 . 121.040 no H281 . C28 . C27 . 121.041 no C29 . C28 . C27 . 117.9(4) yes H291 . C29 . C28 . 119.437 no H291 . C29 . C24 . 119.437 no C28 . C29 . C24 . 121.1(4) yes C35 . C30 . C31 . 119.0(4) yes C35 . C30 . P1 . 118.5(3) yes C31 . C30 . P1 . 122.4(3) yes H311 . C31 . C32 . 119.690 no H311 . C31 . C30 . 119.689 no C32 . C31 . C30 . 120.6(4) yes H321 . C32 . C33 . 120.809 no H321 . C32 . C31 . 120.809 no C33 . C32 . C31 . 118.4(4) yes F3 . C33 . C34 . 117.7(4) yes F3 . C33 . C32 . 119.0(4) yes C34 . C33 . C32 . 123.3(4) yes H341 . C34 . C35 . 121.171 no H341 . C34 . C33 . 121.171 no C35 . C34 . C33 . 117.7(4) yes H351 . C35 . C34 . 119.522 no H351 . C35 . C30 . 119.522 no C34 . C35 . C30 . 121.0(4) yes F9 . P2 . F8 . 179.9(2) yes F9 . P2 . F7 . 90.1(2) yes F8 . P2 . F7 . 89.9(2) yes F9 . P2 . F6 . 90.4(2) yes F8 . P2 . F6 . 89.6(2) yes F7 . P2 . F6 . 178.1(3) yes F9 . P2 . F5 . 88.6(2) yes F8 . P2 . F5 . 91.3(2) yes F7 . P2 . F5 . 93.3(4) yes F6 . P2 . F5 . 88.6(3) yes F9 . P2 . F4 . 91.0(2) yes F8 . P2 . F4 . 89.0(2) yes F7 . P2 . F4 . 89.2(3) yes F6 . P2 . F4 . 88.9(3) yes F5 . P2 . F4 . 177.5(4) yes _chemical_name_common ; Iridium(1+),((1,2,5,6-?)-1,5-cyclooctadiene)(5,6,7,8- tetrahydroquinoline) (tris(4-fluorophenyl)phosphine) (hexafluorophosphate)(1-) ;