# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Thomas Braun' _publ_contact_author_email THOMAS.BRAUN@CMS.HU-BERLIN.DE _publ_section_title ; Iridium Derivatives of Fluorinated Aromatics by C-H activation: Isolation of Classical and Non-classical Hydrides ; loop_ _publ_author_name 'Thomas Braun' 'Ingo Krossing' 'Marcel Ahijado Salomon' # Attachment 'Braun_cif' data_complex2 _database_code_depnum_ccdc_archive 'CCDC 686375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H44 F4 Ir N P2' _chemical_formula_sum 'C23 H44 F4 Ir N P2' _chemical_formula_weight 664.73 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' F F 0.0171 0.0103 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1550(12) _cell_length_b 16.7400(11) _cell_length_c 13.5350(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.313(8) _cell_angle_gamma 90.00 _cell_volume 2717.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 70 _cell_measurement_theta_min 3.035 _cell_measurement_theta_max 19.666 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 5.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.586656 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'sadabs bruker nonius ccd v2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Kappa CCD' _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 43911 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6233 _reflns_number_gt 4780 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^2^+5.9492P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6233 _refine_ls_number_parameters 300 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0474 _refine_ls_wR_factor_gt 0.0420 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.005 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.220992(11) 0.091524(8) 0.245583(10) 0.01224(4) Uani 1 1 d D . . H19 H 0.173(3) 0.091(2) 0.1325(14) 0.024(10) Uiso 1 1 d D . . H20 H 0.204(4) 0.1838(12) 0.242(3) 0.043(13) Uiso 1 1 d D . . P1 P 0.03625(7) 0.08749(7) 0.26945(7) 0.01543(18) Uani 1 1 d . . . P2 P 0.39920(8) 0.12563(5) 0.21745(7) 0.01296(19) Uani 1 1 d . . . F1 F 0.25146(19) -0.06307(13) 0.08699(16) 0.0247(5) Uani 1 1 d . . . F2 F 0.2921(2) -0.21831(14) 0.12408(19) 0.0347(6) Uani 1 1 d . . . F3 F 0.2979(2) -0.18723(14) 0.45837(18) 0.0317(6) Uani 1 1 d . . . F4 F 0.25281(18) -0.03003(13) 0.43860(15) 0.0227(5) Uani 1 1 d . . . N1 N 0.2958(3) -0.20295(18) 0.2914(3) 0.0243(8) Uani 1 1 d . . . C1 C -0.0549(3) 0.1691(2) 0.2098(3) 0.0221(9) Uani 1 1 d . . . H1 H -0.1302 0.1618 0.2292 0.026 Uiso 1 1 calc R . . C2 C -0.0121(4) 0.2525(2) 0.2462(4) 0.0301(10) Uani 1 1 d . . . H2A H 0.0592 0.2630 0.2237 0.045 Uiso 1 1 calc R . . H2B H -0.0018 0.2543 0.3195 0.045 Uiso 1 1 calc R . . H2C H -0.0666 0.2931 0.2184 0.045 Uiso 1 1 calc R . . C3 C -0.0693(4) 0.1659(3) 0.0950(3) 0.0371(11) Uani 1 1 d . . . H3A H -0.1150 0.2111 0.0666 0.056 Uiso 1 1 calc R . . H3B H -0.1062 0.1158 0.0712 0.056 Uiso 1 1 calc R . . H3C H 0.0039 0.1686 0.0738 0.056 Uiso 1 1 calc R . . C4 C 0.0307(3) 0.0938(3) 0.4075(3) 0.0233(8) Uani 1 1 d . . . H4 H 0.0380 0.0378 0.4334 0.028 Uiso 1 1 calc R . . C5 C -0.0765(4) 0.1275(3) 0.4381(4) 0.0365(11) Uani 1 1 d . . . H5A H -0.0720 0.1234 0.5109 0.055 Uiso 1 1 calc R . . H5B H -0.1408 0.0968 0.4051 0.055 Uiso 1 1 calc R . . H5C H -0.0852 0.1836 0.4179 0.055 Uiso 1 1 calc R . . C6 C 0.1330(4) 0.1399(3) 0.4622(3) 0.0335(10) Uani 1 1 d . . . H6A H 0.1262 0.1965 0.4440 0.050 Uiso 1 1 calc R . . H6B H 0.2011 0.1180 0.4426 0.050 Uiso 1 1 calc R . . H6C H 0.1365 0.1342 0.5347 0.050 Uiso 1 1 calc R . . C7 C -0.0368(3) -0.0104(2) 0.2336(3) 0.0208(9) Uani 1 1 d . . . H7 H 0.0055 -0.0512 0.2784 0.025 Uiso 1 1 calc R . . C8 C -0.1575(4) -0.0171(3) 0.2523(4) 0.0355(11) Uani 1 1 d . . . H8A H -0.2027 0.0248 0.2148 0.053 Uiso 1 1 calc R . . H8B H -0.1596 -0.0107 0.3239 0.053 Uiso 1 1 calc R . . H8C H -0.1875 -0.0696 0.2300 0.053 Uiso 1 1 calc R . . C9 C -0.0274(3) -0.0372(2) 0.1263(3) 0.0263(9) Uani 1 1 d . . . H9A H -0.0392 -0.0951 0.1204 0.040 Uiso 1 1 calc R . . H9B H 0.0469 -0.0241 0.1119 0.040 Uiso 1 1 calc R . . H9C H -0.0839 -0.0097 0.0785 0.040 Uiso 1 1 calc R . . C10 C 0.4278(3) 0.2351(2) 0.2107(3) 0.0191(8) Uani 1 1 d . . . H10 H 0.5058 0.2412 0.1972 0.023 Uiso 1 1 calc R . . C11 C 0.4206(3) 0.2792(2) 0.3094(3) 0.0247(9) Uani 1 1 d . . . H11A H 0.4246 0.3369 0.2987 0.037 Uiso 1 1 calc R . . H11B H 0.4828 0.2626 0.3607 0.037 Uiso 1 1 calc R . . H11C H 0.3500 0.2660 0.3316 0.037 Uiso 1 1 calc R . . C12 C 0.3504(4) 0.2763(2) 0.1245(3) 0.0269(9) Uani 1 1 d . . . H12A H 0.2726 0.2664 0.1313 0.040 Uiso 1 1 calc R . . H12B H 0.3648 0.2550 0.0604 0.040 Uiso 1 1 calc R . . H12C H 0.3647 0.3340 0.1269 0.040 Uiso 1 1 calc R . . C13 C 0.4433(3) 0.0848(2) 0.1018(3) 0.0184(8) Uani 1 1 d . . . H13 H 0.4553 0.0263 0.1143 0.022 Uiso 1 1 calc R . . C14 C 0.3544(3) 0.0910(3) 0.0067(3) 0.0248(8) Uani 1 1 d . . . H14A H 0.3463 0.1469 -0.0146 0.037 Uiso 1 1 calc R . . H14B H 0.2829 0.0711 0.0213 0.037 Uiso 1 1 calc R . . H14C H 0.3776 0.0589 -0.0469 0.037 Uiso 1 1 calc R . . C15 C 0.5567(3) 0.1178(2) 0.0818(3) 0.0257(10) Uani 1 1 d . . . H15A H 0.5826 0.0860 0.0293 0.039 Uiso 1 1 calc R . . H15B H 0.6114 0.1147 0.1433 0.039 Uiso 1 1 calc R . . H15C H 0.5477 0.1735 0.0600 0.039 Uiso 1 1 calc R . . C16 C 0.5128(3) 0.0926(2) 0.3210(3) 0.0182(7) Uani 1 1 d . . . H16 H 0.5772 0.1300 0.3231 0.022 Uiso 1 1 calc R . . C17 C 0.4702(3) 0.0977(3) 0.4224(3) 0.0232(8) Uani 1 1 d . . . H17A H 0.4107 0.0584 0.4238 0.035 Uiso 1 1 calc R . . H17B H 0.4411 0.1515 0.4309 0.035 Uiso 1 1 calc R . . H17C H 0.5318 0.0866 0.4769 0.035 Uiso 1 1 calc R . . C18 C 0.5545(3) 0.0073(2) 0.3075(3) 0.0244(9) Uani 1 1 d . . . H18A H 0.6104 -0.0071 0.3653 0.037 Uiso 1 1 calc R . . H18B H 0.5881 0.0047 0.2464 0.037 Uiso 1 1 calc R . . H18C H 0.4917 -0.0300 0.3020 0.037 Uiso 1 1 calc R . . C19 C 0.2506(3) -0.0344(2) 0.2612(3) 0.0160(8) Uani 1 1 d . . . C20 C 0.2616(3) -0.0888(2) 0.1845(3) 0.0191(7) Uani 1 1 d . . . C21 C 0.2828(3) -0.1692(2) 0.2016(3) 0.0226(9) Uani 1 1 d . . . C22 C 0.2852(3) -0.1543(2) 0.3656(3) 0.0218(9) Uani 1 1 d . . . C23 C 0.2630(3) -0.0731(2) 0.3538(3) 0.0182(8) Uani 1 1 d . . . 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 0.01015(6) 0.01249(6) 0.01446(6) 0.00068(7) 0.00313(4) -0.00018(7) P1 0.0106(4) 0.0168(4) 0.0194(4) -0.0008(5) 0.0041(3) 0.0005(4) P2 0.0119(5) 0.0133(4) 0.0142(4) 0.0008(4) 0.0036(4) -0.0009(4) F1 0.0290(13) 0.0250(12) 0.0204(11) -0.0056(9) 0.0054(10) -0.0006(10) F2 0.0308(14) 0.0250(13) 0.0483(15) -0.0166(12) 0.0068(12) 0.0018(11) F3 0.0285(14) 0.0263(13) 0.0387(14) 0.0183(11) 0.0010(11) 0.0009(11) F4 0.0241(13) 0.0242(12) 0.0205(11) 0.0025(10) 0.0056(10) -0.0006(10) N1 0.0138(17) 0.0148(16) 0.044(2) 0.0012(16) 0.0028(15) -0.0023(13) C1 0.015(2) 0.019(2) 0.033(2) 0.0025(18) 0.0052(17) 0.0053(16) C2 0.023(2) 0.021(2) 0.048(3) 0.001(2) 0.009(2) 0.0026(17) C3 0.043(3) 0.028(2) 0.036(3) 0.005(2) -0.006(2) 0.010(2) C4 0.022(2) 0.0249(19) 0.0239(19) -0.003(2) 0.0074(16) -0.004(2) C5 0.032(3) 0.044(3) 0.038(3) -0.009(2) 0.022(2) -0.001(2) C6 0.037(3) 0.035(3) 0.027(2) -0.007(2) 0.000(2) -0.004(2) C7 0.018(2) 0.0183(19) 0.026(2) 0.0003(17) 0.0030(17) -0.0030(16) C8 0.024(2) 0.032(2) 0.052(3) -0.007(2) 0.011(2) -0.007(2) C9 0.025(2) 0.024(2) 0.029(2) -0.0062(18) 0.0005(18) -0.0012(18) C10 0.017(2) 0.0179(19) 0.024(2) 0.0006(16) 0.0072(16) -0.0039(16) C11 0.026(2) 0.0177(19) 0.031(2) -0.0068(18) 0.0050(18) -0.0023(17) C12 0.033(2) 0.019(2) 0.029(2) 0.0072(18) 0.0064(19) 0.0026(18) C13 0.0198(19) 0.0189(19) 0.0181(17) -0.0055(17) 0.0082(14) 0.0014(17) C14 0.030(2) 0.029(2) 0.0162(17) 0.000(2) 0.0067(15) -0.003(2) C15 0.029(2) 0.022(2) 0.030(2) -0.0059(18) 0.0189(19) -0.0053(17) C16 0.0111(16) 0.0209(17) 0.0213(17) 0.0037(18) -0.0013(14) -0.0046(17) C17 0.0209(19) 0.029(2) 0.0185(18) 0.0040(19) -0.0008(15) -0.0011(19) C18 0.014(2) 0.023(2) 0.036(2) 0.0069(18) 0.0047(18) 0.0070(16) C19 0.0080(19) 0.0144(17) 0.026(2) 0.0023(16) 0.0028(16) -0.0031(13) C20 0.0132(17) 0.0202(17) 0.0231(18) 0.0011(19) 0.0009(14) -0.0013(18) C21 0.0134(19) 0.0150(19) 0.040(2) -0.0060(18) 0.0057(17) -0.0012(15) C22 0.0133(19) 0.022(2) 0.030(2) 0.0100(18) 0.0035(17) -0.0024(16) C23 0.0128(18) 0.019(2) 0.0230(19) -0.0012(15) 0.0029(15) 0.0008(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 C19 2.144(4) . ? Ir1 P1 2.3209(9) . ? Ir1 P2 2.3303(9) . ? Ir1 H19 1.548(18) . ? Ir1 H20 1.558(19) . ? P1 C1 1.859(4) . ? P1 C4 1.883(4) . ? P1 C7 1.889(4) . ? P2 C13 1.865(3) . ? P2 C10 1.870(4) . ? P2 C16 1.884(3) . ? F1 C20 1.374(4) . ? F2 C21 1.352(4) . ? F3 C22 1.357(4) . ? F4 C23 1.378(4) . ? N1 C22 1.316(5) . ? N1 C21 1.327(5) . ? C1 C3 1.536(6) . ? C1 C2 1.543(5) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.537(6) . ? C4 C6 1.546(6) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.533(5) . ? C7 C9 1.541(5) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.538(5) . ? C10 C11 1.541(5) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.544(5) . ? C13 C15 1.548(5) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.535(5) . ? C16 C17 1.546(5) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C23 1.396(5) . ? C19 C20 1.404(5) . ? C20 C21 1.382(5) . ? C22 C23 1.390(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 C19 Ir1 P1 96.21(9) . . ? C19 Ir1 P2 96.41(9) . . ? P1 Ir1 P2 167.37(4) . . ? C19 Ir1 H19 96.9(15) . . ? P1 Ir1 H19 85.3(13) . . ? P2 Ir1 H19 93.1(14) . . ? C19 Ir1 H20 175.8(17) . . ? P1 Ir1 H20 84.6(17) . . ? P2 Ir1 H20 82.8(17) . . ? H19 Ir1 H20 87(2) . . ? C1 P1 C4 105.98(19) . . ? C1 P1 C7 107.64(18) . . ? C4 P1 C7 102.30(18) . . ? C1 P1 Ir1 116.11(13) . . ? C4 P1 Ir1 109.10(12) . . ? C7 P1 Ir1 114.50(13) . . ? C13 P2 C10 103.74(17) . . ? C13 P2 C16 103.96(16) . . ? C10 P2 C16 101.82(17) . . ? C13 P2 Ir1 116.65(12) . . ? C10 P2 Ir1 115.65(12) . . ? C16 P2 Ir1 113.25(11) . . ? C22 N1 C21 115.1(3) . . ? C3 C1 C2 109.4(3) . . ? C3 C1 P1 112.1(3) . . ? C2 C1 P1 112.3(3) . . ? C3 C1 H1 107.6 . . ? C2 C1 H1 107.6 . . ? P1 C1 H1 107.6 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C6 109.8(4) . . ? C5 C4 P1 117.1(3) . . ? C6 C4 P1 110.4(3) . . ? C5 C4 H4 106.3 . . ? C6 C4 H4 106.3 . . ? P1 C4 H4 106.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 110.7(3) . . ? C8 C7 P1 116.4(3) . . ? C9 C7 P1 113.1(3) . . ? C8 C7 H7 105.2 . . ? C9 C7 H7 105.2 . . ? P1 C7 H7 105.2 . . ? 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 . . ? 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 . . ? C12 C10 C11 109.2(3) . . ? C12 C10 P2 112.4(3) . . ? C11 C10 P2 112.9(3) . . ? C12 C10 H10 107.3 . . ? C11 C10 H10 107.3 . . ? P2 C10 H10 107.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 110.7(3) . . ? C14 C13 P2 114.7(3) . . ? C15 C13 P2 113.6(3) . . ? C14 C13 H13 105.7 . . ? C15 C13 H13 105.7 . . ? P2 C13 H13 105.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C17 108.8(3) . . ? C18 C16 P2 113.6(3) . . ? C17 C16 P2 109.5(2) . . ? C18 C16 H16 108.2 . . ? C17 C16 H16 108.2 . . ? P2 C16 H16 108.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C23 C19 C20 110.7(3) . . ? C23 C19 Ir1 122.4(3) . . ? C20 C19 Ir1 126.8(3) . . ? F1 C20 C21 116.9(3) . . ? F1 C20 C19 120.1(3) . . ? C21 C20 C19 123.0(4) . . ? N1 C21 F2 116.1(3) . . ? N1 C21 C20 124.0(4) . . ? F2 C21 C20 119.9(4) . . ? N1 C22 F3 116.3(3) . . ? N1 C22 C23 124.0(4) . . ? F3 C22 C23 119.7(4) . . ? F4 C23 C22 117.2(3) . . ? F4 C23 C19 119.6(3) . . ? C22 C23 C19 123.2(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.945 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.138 data_complex7 _database_code_depnum_ccdc_archive 'CCDC 686376' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H42 F4 Ir N O P2' _chemical_formula_sum 'C24 H42 F4 Ir N O P2' _chemical_formula_weight 690.73 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' F F 0.0171 0.0103 '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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.4740(3) _cell_length_b 13.0700(2) _cell_length_c 17.2910(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2819.04(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3619 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 4.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5082 _exptl_absorpt_correction_T_max 0.7578 _exptl_absorpt_process_details 'Denzo and Scalpack (Otwinowski & Minor 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 'Kappa CCD' _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 33849 _diffrn_reflns_av_R_equivalents 0.083 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6464 _reflns_number_gt 5858 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCCD _computing_cell_refinement 'HKL Scalepack(Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalpack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0199P)^2^+5.6561P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(7) _refine_ls_number_reflns 6464 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.562410(15) 0.975776(15) 0.573625(11) 0.01955(5) Uani 1 1 d . . . P1 P 0.38551(10) 0.99302(10) 0.61642(8) 0.0231(3) Uani 1 1 d . . . P2 P 0.74950(9) 0.98505(10) 0.56222(7) 0.0192(3) Uani 1 1 d . . . F1 F 0.5041(3) 0.8619(2) 0.40438(19) 0.0352(8) Uani 1 1 d . . . F2 F 0.4643(3) 0.9358(3) 0.2652(2) 0.0418(9) Uani 1 1 d . . . F3 F 0.5210(3) 1.2614(3) 0.3417(2) 0.0360(8) Uani 1 1 d . . . F4 F 0.5476(3) 1.2080(2) 0.48725(18) 0.0311(7) Uani 1 1 d . . . O1 O 0.5485(3) 0.7439(3) 0.5488(2) 0.0339(9) Uani 1 1 d . . . N1 N 0.4939(4) 1.0989(4) 0.3031(3) 0.0295(11) Uani 1 1 d . . . C1 C 0.3314(4) 0.8733(4) 0.6603(4) 0.0301(13) Uani 1 1 d . . . H1 H 0.3236 0.8242 0.6163 0.036 Uiso 1 1 calc R . . C2 C 0.4050(5) 0.8204(4) 0.7176(4) 0.0351(14) Uani 1 1 d . . . H2A H 0.3966 0.8518 0.7687 0.053 Uiso 1 1 calc R . . H2B H 0.4796 0.8277 0.7005 0.053 Uiso 1 1 calc R . . H2C H 0.3865 0.7476 0.7206 0.053 Uiso 1 1 calc R . . C3 C 0.2204(5) 0.8832(6) 0.6943(5) 0.056(2) Uani 1 1 d . . . H3A H 0.1937 0.8153 0.7088 0.084 Uiso 1 1 calc R . . H3B H 0.1723 0.9138 0.6560 0.084 Uiso 1 1 calc R . . H3C H 0.2233 0.9269 0.7403 0.084 Uiso 1 1 calc R . . C4 C 0.3633(4) 1.0958(4) 0.6877(3) 0.0277(13) Uani 1 1 d . . . H4 H 0.2847 1.0968 0.6993 0.033 Uiso 1 1 calc R . . C5 C 0.4210(5) 1.0785(5) 0.7644(3) 0.0350(14) Uani 1 1 d . . . H5A H 0.4979 1.0696 0.7549 0.052 Uiso 1 1 calc R . . H5B H 0.3923 1.0171 0.7894 0.052 Uiso 1 1 calc R . . H5C H 0.4098 1.1378 0.7981 0.052 Uiso 1 1 calc R . . C6 C 0.3917(5) 1.2015(4) 0.6539(4) 0.0336(14) Uani 1 1 d . . . H6A H 0.3630 1.2552 0.6877 0.050 Uiso 1 1 calc R . . H6B H 0.3603 1.2082 0.6022 0.050 Uiso 1 1 calc R . . H6C H 0.4697 1.2084 0.6505 0.050 Uiso 1 1 calc R . . C7 C 0.2898(4) 1.0266(5) 0.5358(3) 0.0304(11) Uani 1 1 d . . . H7 H 0.3296 1.0747 0.5011 0.037 Uiso 1 1 calc R . . C8 C 0.2664(5) 0.9305(5) 0.4866(4) 0.0419(16) Uani 1 1 d . . . H8A H 0.2149 0.8868 0.5139 0.063 Uiso 1 1 calc R . . H8B H 0.3331 0.8925 0.4782 0.063 Uiso 1 1 calc R . . H8C H 0.2363 0.9511 0.4366 0.063 Uiso 1 1 calc R . . C9 C 0.1856(4) 1.0811(5) 0.5571(4) 0.0392(16) Uani 1 1 d . . . H9A H 0.1484 1.1022 0.5098 0.059 Uiso 1 1 calc R . . H9B H 0.2018 1.1415 0.5885 0.059 Uiso 1 1 calc R . . H9C H 0.1397 1.0344 0.5866 0.059 Uiso 1 1 calc R . . C10 C 0.8216(4) 0.8688(4) 0.5971(3) 0.0228(12) Uani 1 1 d . . . H10 H 0.8131 0.8166 0.5553 0.027 Uiso 1 1 calc R . . C11 C 0.9437(5) 0.8847(4) 0.6062(3) 0.0254(11) Uani 1 1 d . . . H11A H 0.9572 0.9364 0.6461 0.038 Uiso 1 1 calc R . . H11B H 0.9740 0.9078 0.5569 0.038 Uiso 1 1 calc R . . H11C H 0.9774 0.8200 0.6213 0.038 Uiso 1 1 calc R . . C12 C 0.7768(5) 0.8193(5) 0.6701(4) 0.0345(14) Uani 1 1 d . . . H12A H 0.8156 0.7556 0.6806 0.052 Uiso 1 1 calc R . . H12B H 0.7005 0.8043 0.6627 0.052 Uiso 1 1 calc R . . H12C H 0.7855 0.8662 0.7138 0.052 Uiso 1 1 calc R . . C13 C 0.8103(4) 1.0956(4) 0.6133(3) 0.0229(11) Uani 1 1 d . . . H13 H 0.8896 1.0916 0.6056 0.028 Uiso 1 1 calc R . . C14 C 0.7722(4) 1.1985(4) 0.5797(4) 0.0330(13) Uani 1 1 d . . . H14A H 0.6952 1.2067 0.5894 0.049 Uiso 1 1 calc R . . H14B H 0.7855 1.1997 0.5238 0.049 Uiso 1 1 calc R . . H14C H 0.8115 1.2545 0.6044 0.049 Uiso 1 1 calc R . . C15 C 0.7892(4) 1.0917(5) 0.6995(3) 0.0296(13) Uani 1 1 d . . . H15A H 0.8243 1.1499 0.7247 0.044 Uiso 1 1 calc R . . H15B H 0.8178 1.0277 0.7207 0.044 Uiso 1 1 calc R . . H15C H 0.7118 1.0949 0.7090 0.044 Uiso 1 1 calc R . . C16 C 0.7946(4) 1.0009(4) 0.4601(3) 0.0262(13) Uani 1 1 d . . . H16 H 0.7449 1.0525 0.4369 0.031 Uiso 1 1 calc R . . C17 C 0.9090(4) 1.0430(4) 0.4454(3) 0.0341(14) Uani 1 1 d . . . H17A H 0.9618 0.9891 0.4557 0.051 Uiso 1 1 calc R . . H17B H 0.9224 1.1012 0.4799 0.051 Uiso 1 1 calc R . . H17C H 0.9152 1.0653 0.3915 0.051 Uiso 1 1 calc R . . C18 C 0.7777(5) 0.9028(5) 0.4131(3) 0.0359(14) Uani 1 1 d . . . H18A H 0.7768 0.9194 0.3578 0.054 Uiso 1 1 calc R . . H18B H 0.7093 0.8715 0.4276 0.054 Uiso 1 1 calc R . . H18C H 0.8363 0.8548 0.4237 0.054 Uiso 1 1 calc R . . C19 C 0.5530(5) 0.8313(4) 0.5539(3) 0.0250(11) Uani 1 1 d . . . C20 C 0.5312(3) 1.0294(5) 0.4587(3) 0.0230(10) Uani 1 1 d . . . C21 C 0.5082(4) 0.9657(5) 0.3954(3) 0.0266(11) Uani 1 1 d . . . C22 C 0.4893(4) 1.0026(4) 0.3233(3) 0.0332(15) Uani 1 1 d . . . C23 C 0.5159(4) 1.1606(4) 0.3603(3) 0.0255(12) Uani 1 1 d . . . C24 C 0.5312(4) 1.1305(4) 0.4354(3) 0.0234(11) Uani 1 1 d . . . 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 0.01770(7) 0.01825(9) 0.02271(9) 0.00155(9) -0.00086(9) -0.00092(8) P1 0.0176(6) 0.0193(8) 0.0325(7) 0.0033(5) -0.0013(5) -0.0012(5) P2 0.0183(5) 0.0179(6) 0.0214(7) 0.0007(6) 0.0001(5) 0.0001(5) F1 0.048(2) 0.0223(17) 0.035(2) -0.0057(14) -0.0100(16) 0.0014(15) F2 0.048(2) 0.044(2) 0.0334(19) -0.0120(16) -0.0119(15) 0.0035(16) F3 0.0347(18) 0.0336(19) 0.040(2) 0.0113(16) -0.0003(15) 0.0022(14) F4 0.044(2) 0.0186(15) 0.0306(17) 0.0018(13) -0.0032(16) 0.0007(15) O1 0.038(2) 0.0199(19) 0.044(2) -0.0033(16) 0.0006(19) -0.0012(18) N1 0.025(2) 0.035(3) 0.029(3) 0.005(2) 0.002(2) 0.002(2) C1 0.023(3) 0.019(3) 0.049(4) 0.008(3) 0.003(3) -0.002(2) C2 0.030(3) 0.027(3) 0.048(4) 0.010(3) 0.005(3) 0.003(2) C3 0.027(3) 0.045(4) 0.095(6) 0.030(4) 0.021(4) 0.002(3) C4 0.021(3) 0.025(3) 0.037(3) -0.002(2) 0.005(2) 0.002(2) C5 0.038(4) 0.037(3) 0.029(3) -0.004(3) 0.009(3) 0.005(3) C6 0.039(3) 0.023(3) 0.039(4) -0.004(3) 0.005(3) 0.000(3) C7 0.022(2) 0.026(3) 0.043(3) 0.006(3) -0.007(2) -0.002(3) C8 0.028(3) 0.044(4) 0.053(4) -0.001(3) -0.010(3) -0.001(3) C9 0.025(3) 0.033(3) 0.060(5) 0.015(3) -0.005(3) 0.004(2) C10 0.026(3) 0.019(3) 0.023(3) -0.002(2) -0.002(2) 0.005(2) C11 0.022(2) 0.025(3) 0.028(3) -0.001(2) 0.001(2) 0.004(3) C12 0.031(3) 0.032(3) 0.041(4) 0.011(3) -0.001(3) -0.003(3) C13 0.018(2) 0.019(3) 0.032(3) -0.010(2) 0.001(2) -0.001(2) C14 0.028(3) 0.020(3) 0.051(4) 0.001(3) -0.002(3) -0.005(2) C15 0.024(3) 0.035(3) 0.031(3) -0.008(3) -0.004(2) -0.002(2) C16 0.022(2) 0.032(4) 0.024(2) 0.007(2) 0.002(2) 0.002(2) C17 0.028(3) 0.037(4) 0.038(3) 0.011(3) 0.007(2) 0.004(2) C18 0.036(3) 0.045(4) 0.027(4) -0.014(3) 0.002(2) 0.003(3) C19 0.024(2) 0.023(3) 0.028(3) -0.004(2) -0.003(2) -0.002(2) C20 0.018(2) 0.023(3) 0.028(2) -0.001(3) -0.0015(17) 0.004(2) C21 0.024(2) 0.023(3) 0.032(3) 0.001(3) -0.002(2) 0.002(2) C22 0.025(3) 0.046(5) 0.029(3) -0.010(3) 0.000(2) 0.003(2) C23 0.022(2) 0.026(3) 0.028(3) 0.006(2) 0.005(2) 0.005(2) C24 0.019(2) 0.028(3) 0.023(3) 0.000(2) -0.001(2) -0.0001(18) _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 C19 1.923(5) . ? Ir1 C20 2.143(5) . ? Ir1 P1 2.3383(13) . ? Ir1 P2 2.3452(11) . ? P1 C4 1.844(6) . ? P1 C1 1.866(5) . ? P1 C7 1.888(5) . ? P2 C13 1.855(5) . ? P2 C16 1.865(5) . ? P2 C10 1.866(5) . ? F1 C21 1.367(7) . ? F2 C22 1.368(6) . ? F3 C23 1.357(6) . ? F4 C24 1.368(6) . ? O1 C19 1.146(6) . ? N1 C23 1.306(8) . ? N1 C22 1.309(8) . ? C1 C3 1.509(8) . ? C1 C2 1.518(8) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.526(8) . ? C4 C6 1.541(8) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C9 1.527(8) . ? C7 C8 1.545(9) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.524(8) . ? C10 C11 1.545(8) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.515(8) . ? C13 C14 1.540(7) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.533(7) . ? C16 C17 1.550(7) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C24 1.381(8) . ? C20 C21 1.404(8) . ? C21 C22 1.356(8) . ? C23 C24 1.371(8) . ? 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 C19 Ir1 C20 98.4(2) . . ? C19 Ir1 P1 95.33(17) . . ? C20 Ir1 P1 95.19(12) . . ? C19 Ir1 P2 95.55(17) . . ? C20 Ir1 P2 94.93(12) . . ? P1 Ir1 P2 163.89(5) . . ? C4 P1 C1 106.6(3) . . ? C4 P1 C7 103.2(3) . . ? C1 P1 C7 105.5(3) . . ? C4 P1 Ir1 115.06(18) . . ? C1 P1 Ir1 112.92(18) . . ? C7 P1 Ir1 112.69(18) . . ? C13 P2 C16 103.9(2) . . ? C13 P2 C10 106.5(2) . . ? C16 P2 C10 104.5(2) . . ? C13 P2 Ir1 114.01(17) . . ? C16 P2 Ir1 112.69(16) . . ? C10 P2 Ir1 114.24(18) . . ? C23 N1 C22 113.7(5) . . ? C3 C1 C2 109.8(5) . . ? C3 C1 P1 114.7(4) . . ? C2 C1 P1 115.3(4) . . ? C3 C1 H1 105.3 . . ? C2 C1 H1 105.3 . . ? P1 C1 H1 105.3 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C6 110.7(5) . . ? C5 C4 P1 113.7(4) . . ? C6 C4 P1 111.5(4) . . ? C5 C4 H4 106.8 . . ? C6 C4 H4 106.8 . . ? P1 C4 H4 106.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C7 C8 110.5(4) . . ? C9 C7 P1 117.9(4) . . ? C8 C7 P1 109.7(4) . . ? C9 C7 H7 105.9 . . ? C8 C7 H7 105.9 . . ? P1 C7 H7 105.9 . . ? 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 . . ? 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 . . ? C12 C10 C11 109.5(4) . . ? C12 C10 P2 115.9(4) . . ? C11 C10 P2 113.5(4) . . ? C12 C10 H10 105.7 . . ? C11 C10 H10 105.7 . . ? P2 C10 H10 105.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C14 110.3(5) . . ? C15 C13 P2 111.8(4) . . ? C14 C13 P2 112.0(4) . . ? C15 C13 H13 107.5 . . ? C14 C13 H13 107.5 . . ? P2 C13 H13 107.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C17 109.7(4) . . ? C18 C16 P2 111.6(4) . . ? C17 C16 P2 118.2(4) . . ? C18 C16 H16 105.5 . . ? C17 C16 H16 105.5 . . ? P2 C16 H16 105.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 Ir1 174.3(4) . . ? C24 C20 C21 109.9(5) . . ? C24 C20 Ir1 125.6(4) . . ? C21 C20 Ir1 124.5(4) . . ? C22 C21 F1 116.8(5) . . ? C22 C21 C20 122.8(5) . . ? F1 C21 C20 120.5(5) . . ? N1 C22 C21 125.4(5) . . ? N1 C22 F2 115.3(5) . . ? C21 C22 F2 119.2(5) . . ? N1 C23 F3 115.4(5) . . ? N1 C23 C24 124.7(5) . . ? F3 C23 C24 119.8(5) . . ? F4 C24 C23 115.4(5) . . ? F4 C24 C20 121.2(5) . . ? C23 C24 C20 123.5(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.105 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.115 data_complex9 _database_code_depnum_ccdc_archive 'CCDC 686377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H47 F2 Ir O P2' _chemical_formula_sum 'C25 H47 F2 Ir O P2' _chemical_formula_weight 655.77 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.0680(6) _cell_length_b 12.7220(9) _cell_length_c 16.8010(13) _cell_angle_alpha 90.000(5) _cell_angle_beta 92.181(6) _cell_angle_gamma 90.000(4) _cell_volume 2791.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 184 _cell_measurement_theta_min 3.684 _cell_measurement_theta_max 20.940 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 4.926 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.690969 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'sadabs bruker nonius ccd v2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 'Kappa CCD' _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 54355 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8070 _reflns_number_gt 6748 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0008P)^2^+3.4788P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8070 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0181 _refine_ls_wR_factor_ref 0.0358 _refine_ls_wR_factor_gt 0.0316 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.004 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.770964(5) 0.055653(6) 0.187354(4) 0.01100(2) Uani 1 1 d . . . P1 P 0.76206(4) -0.11899(4) 0.14517(3) 0.01363(10) Uani 1 1 d . . . P2 P 0.74995(4) 0.23736(4) 0.19664(3) 0.01201(9) Uani 1 1 d . . . F1 F 0.89674(10) 0.01752(11) 0.36111(7) 0.0259(3) Uani 1 1 d . . . F2 F 0.54614(9) 0.02015(11) 0.27452(8) 0.0276(3) Uani 1 1 d . . . O1 O 1.00371(11) 0.05919(14) 0.21170(10) 0.0288(4) Uani 1 1 d . . . C1 C 0.88667(15) -0.16852(17) 0.11023(12) 0.0174(4) Uani 1 1 d . . . H1 H 0.9347 -0.1673 0.1580 0.021 Uiso 1 1 calc R . . C2 C 0.93586(17) -0.09762(18) 0.04798(13) 0.0222(4) Uani 1 1 d . . . H2A H 1.0091 -0.1136 0.0461 0.033 Uiso 1 1 calc R . . H2B H 0.9269 -0.0237 0.0627 0.033 Uiso 1 1 calc R . . H2C H 0.9029 -0.1104 -0.0045 0.033 Uiso 1 1 calc R . . C3 C 0.88608(18) -0.28233(18) 0.08064(15) 0.0275(5) Uani 1 1 d . . . H3A H 0.8378 -0.2891 0.0349 0.041 Uiso 1 1 calc R . . H3B H 0.8652 -0.3291 0.1235 0.041 Uiso 1 1 calc R . . H3C H 0.9549 -0.3017 0.0647 0.041 Uiso 1 1 calc R . . C4 C 0.66480(17) -0.14569(18) 0.06448(14) 0.0237(5) Uani 1 1 d . . . H4 H 0.6667 -0.2228 0.0532 0.028 Uiso 1 1 calc R . . C5 C 0.6839(2) -0.0887(2) -0.01368(15) 0.0346(6) Uani 1 1 d . . . H5A H 0.6266 -0.1019 -0.0517 0.052 Uiso 1 1 calc R . . H5B H 0.7475 -0.1146 -0.0357 0.052 Uiso 1 1 calc R . . H5C H 0.6898 -0.0130 -0.0037 0.052 Uiso 1 1 calc R . . C6 C 0.55672(17) -0.1198(2) 0.09229(17) 0.0339(6) Uani 1 1 d . . . H6A H 0.5481 -0.0434 0.0948 0.051 Uiso 1 1 calc R . . H6B H 0.5478 -0.1501 0.1452 0.051 Uiso 1 1 calc R . . H6C H 0.5055 -0.1495 0.0546 0.051 Uiso 1 1 calc R . . C7 C 0.72671(17) -0.21221(17) 0.22558(14) 0.0223(5) Uani 1 1 d . . . H7 H 0.6746 -0.1743 0.2568 0.027 Uiso 1 1 calc R . . C8 C 0.81805(19) -0.2307(2) 0.28423(14) 0.0305(6) Uani 1 1 d . . . H8A H 0.7933 -0.2583 0.3344 0.046 Uiso 1 1 calc R . . H8B H 0.8540 -0.1641 0.2943 0.046 Uiso 1 1 calc R . . H8C H 0.8651 -0.2815 0.2614 0.046 Uiso 1 1 calc R . . C9 C 0.6762(2) -0.31753(19) 0.20124(18) 0.0349(6) Uani 1 1 d . . . H9A H 0.7251 -0.3604 0.1726 0.052 Uiso 1 1 calc R . . H9B H 0.6156 -0.3040 0.1666 0.052 Uiso 1 1 calc R . . H9C H 0.6558 -0.3551 0.2490 0.052 Uiso 1 1 calc R . . C10 C 0.72885(16) 0.28503(17) 0.29974(12) 0.0176(4) Uani 1 1 d . . . H10 H 0.6807 0.2335 0.3232 0.021 Uiso 1 1 calc R . . C11 C 0.68005(18) 0.39338(19) 0.31097(14) 0.0256(5) Uani 1 1 d . . . H11A H 0.6594 0.4008 0.3662 0.038 Uiso 1 1 calc R . . H11B H 0.6198 0.4003 0.2749 0.038 Uiso 1 1 calc R . . H11C H 0.7298 0.4483 0.2991 0.038 Uiso 1 1 calc R . . C12 C 0.82825(17) 0.27784(19) 0.35130(12) 0.0233(5) Uani 1 1 d . . . H12A H 0.8740 0.3355 0.3376 0.035 Uiso 1 1 calc R . . H12B H 0.8619 0.2105 0.3415 0.035 Uiso 1 1 calc R . . H12C H 0.8122 0.2829 0.4077 0.035 Uiso 1 1 calc R . . C13 C 0.86374(14) 0.31352(15) 0.16477(11) 0.0137(4) Uani 1 1 d . . . H13 H 0.9176 0.3031 0.2079 0.016 Uiso 1 1 calc R . . C14 C 0.84674(16) 0.43242(17) 0.15938(13) 0.0205(4) Uani 1 1 d . . . H14A H 0.9096 0.4665 0.1427 0.031 Uiso 1 1 calc R . . H14B H 0.8288 0.4595 0.2116 0.031 Uiso 1 1 calc R . . H14C H 0.7910 0.4473 0.1204 0.031 Uiso 1 1 calc R . . C15 C 0.91149(17) 0.27489(18) 0.08781(13) 0.0229(5) Uani 1 1 d . . . H15A H 0.8668 0.2940 0.0419 0.034 Uiso 1 1 calc R . . H15B H 0.9194 0.1983 0.0899 0.034 Uiso 1 1 calc R . . H15C H 0.9787 0.3077 0.0826 0.034 Uiso 1 1 calc R . . C16 C 0.63739(15) 0.28901(17) 0.13865(13) 0.0183(4) Uani 1 1 d . . . H16 H 0.6367 0.3670 0.1459 0.022 Uiso 1 1 calc R . . C17 C 0.53718(16) 0.24607(19) 0.17073(15) 0.0256(5) Uani 1 1 d . . . H17A H 0.4789 0.2805 0.1432 0.038 Uiso 1 1 calc R . . H17B H 0.5353 0.2602 0.2280 0.038 Uiso 1 1 calc R . . H17C H 0.5334 0.1701 0.1615 0.038 Uiso 1 1 calc R . . C18 C 0.64255(19) 0.26748(19) 0.04938(13) 0.0259(5) Uani 1 1 d . . . H18A H 0.6478 0.1916 0.0404 0.039 Uiso 1 1 calc R . . H18B H 0.7027 0.3027 0.0286 0.039 Uiso 1 1 calc R . . H18C H 0.5805 0.2944 0.0219 0.039 Uiso 1 1 calc R . . C19 C 0.72525(16) 0.02276(16) 0.30710(12) 0.0159(4) Uani 1 1 d . . . C20 C 0.79307(17) 0.00883(17) 0.37256(13) 0.0197(4) Uani 1 1 d . . . C21 C 0.76929(19) -0.01624(19) 0.44986(13) 0.0256(5) Uani 1 1 d . . . H21 H 0.8216 -0.0252 0.4901 0.031 Uiso 1 1 calc R . . C22 C 0.6672(2) -0.02785(18) 0.46687(14) 0.0289(5) Uani 1 1 d . . . H22 H 0.6481 -0.0452 0.5193 0.035 Uiso 1 1 calc R . . C23 C 0.59347(18) -0.01394(19) 0.40675(14) 0.0254(5) Uani 1 1 d . . . H23 H 0.5228 -0.0206 0.4172 0.030 Uiso 1 1 calc R . . C24 C 0.62464(16) 0.01004(17) 0.33072(13) 0.0193(4) Uani 1 1 d . . . C25 C 0.91601(15) 0.05702(18) 0.20698(12) 0.0183(4) Uani 1 1 d . . . H1A H 0.661(2) 0.054(2) 0.1595(16) 0.038(8) Uiso 1 1 d . . . H1B H 0.784(2) 0.081(2) 0.0961(16) 0.038(8) Uiso 1 1 d . . . 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 0.01117(3) 0.00802(3) 0.01381(3) 0.00077(3) 0.00043(2) 0.00057(3) P1 0.0132(2) 0.0083(2) 0.0195(2) 0.00021(19) 0.00213(18) 0.00082(18) P2 0.0125(2) 0.0093(2) 0.0142(2) -0.00013(18) 0.00034(17) 0.00066(18) F1 0.0205(7) 0.0335(8) 0.0232(6) 0.0046(6) -0.0045(5) 0.0033(6) F2 0.0164(6) 0.0366(8) 0.0298(7) -0.0003(6) 0.0026(5) -0.0045(6) O1 0.0136(7) 0.0335(10) 0.0391(9) 0.0051(8) -0.0024(6) -0.0021(7) C1 0.0161(10) 0.0124(10) 0.0240(10) -0.0005(8) 0.0062(8) 0.0021(8) C2 0.0230(11) 0.0190(11) 0.0251(11) 0.0024(9) 0.0083(9) 0.0015(9) C3 0.0289(12) 0.0139(11) 0.0407(14) -0.0027(10) 0.0149(10) 0.0035(9) C4 0.0201(11) 0.0160(11) 0.0345(12) -0.0097(9) -0.0049(9) 0.0007(8) C5 0.0386(15) 0.0367(15) 0.0274(12) -0.0050(11) -0.0131(10) 0.0032(12) C6 0.0176(11) 0.0298(14) 0.0536(16) -0.0164(12) -0.0088(10) 0.0009(10) C7 0.0236(11) 0.0120(10) 0.0322(12) 0.0048(9) 0.0144(9) 0.0024(8) C8 0.0410(14) 0.0226(13) 0.0283(12) 0.0107(10) 0.0092(10) 0.0111(11) C9 0.0347(14) 0.0114(12) 0.0601(17) 0.0018(11) 0.0229(12) -0.0022(10) C10 0.0192(10) 0.0155(10) 0.0184(10) -0.0019(8) 0.0044(8) -0.0023(8) C11 0.0284(12) 0.0199(12) 0.0292(12) -0.0068(9) 0.0097(9) 0.0015(9) C12 0.0287(12) 0.0254(13) 0.0156(10) -0.0017(9) -0.0017(8) -0.0037(10) C13 0.0138(9) 0.0114(10) 0.0160(9) 0.0002(7) 0.0012(7) -0.0017(7) C14 0.0227(10) 0.0128(11) 0.0262(10) -0.0007(8) 0.0033(8) -0.0030(8) C15 0.0269(12) 0.0163(11) 0.0262(11) -0.0022(9) 0.0109(9) -0.0029(9) C16 0.0164(10) 0.0111(10) 0.0271(11) -0.0005(8) -0.0050(8) 0.0012(8) C17 0.0122(10) 0.0196(12) 0.0446(14) -0.0001(10) -0.0040(9) 0.0012(8) C18 0.0320(13) 0.0179(12) 0.0269(11) -0.0003(9) -0.0124(9) 0.0035(10) C19 0.0190(10) 0.0102(9) 0.0187(9) 0.0007(8) 0.0024(7) -0.0012(8) C20 0.0223(11) 0.0142(10) 0.0228(10) 0.0008(8) 0.0020(8) 0.0012(8) C21 0.0388(14) 0.0198(11) 0.0181(10) 0.0019(9) 0.0003(9) 0.0037(10) C22 0.0488(15) 0.0188(12) 0.0200(11) 0.0004(9) 0.0116(10) -0.0015(10) C23 0.0304(12) 0.0187(11) 0.0280(12) -0.0031(9) 0.0140(9) -0.0061(9) C24 0.0215(11) 0.0146(10) 0.0222(10) -0.0018(8) 0.0039(8) -0.0022(8) C25 0.0197(10) 0.0140(10) 0.0210(9) 0.0022(9) -0.0013(7) -0.0015(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 C25 1.912(2) . ? Ir1 C19 2.161(2) . ? Ir1 P1 2.3337(5) . ? Ir1 P2 2.3339(5) . ? Ir1 H1A 1.50(3) . ? Ir1 H1B 1.58(3) . ? P1 C4 1.854(2) . ? P1 C1 1.862(2) . ? P1 C7 1.869(2) . ? P2 C16 1.854(2) . ? P2 C10 1.866(2) . ? P2 C13 1.8701(19) . ? F1 C20 1.380(2) . ? F2 C24 1.374(3) . ? O1 C25 1.146(2) . ? C1 C3 1.531(3) . ? C1 C2 1.540(3) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.529(4) . ? C4 C6 1.540(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.537(3) . ? C7 C9 1.542(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.533(3) . ? C10 C12 1.536(3) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.531(3) . ? C13 C15 1.538(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.529(3) . ? C16 C17 1.535(3) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.397(3) . ? C19 C20 1.397(3) . ? C20 C21 1.384(3) . ? C21 C22 1.383(3) . ? C21 H21 0.9500 . ? C22 C23 1.381(4) . ? C22 H22 0.9500 . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 Ir1 C19 98.54(8) . . ? C25 Ir1 P1 95.67(7) . . ? C19 Ir1 P1 94.93(5) . . ? C25 Ir1 P2 95.62(7) . . ? C19 Ir1 P2 95.29(5) . . ? P1 Ir1 P2 163.474(18) . . ? C25 Ir1 H1A 171.8(10) . . ? C19 Ir1 H1A 89.5(10) . . ? P1 Ir1 H1A 81.7(11) . . ? P2 Ir1 H1A 85.5(11) . . ? C25 Ir1 H1B 91.3(10) . . ? C19 Ir1 H1B 170.2(10) . . ? P1 Ir1 H1B 84.8(10) . . ? P2 Ir1 H1B 83.0(10) . . ? H1A Ir1 H1B 80.7(14) . . ? C4 P1 C1 106.92(10) . . ? C4 P1 C7 103.35(11) . . ? C1 P1 C7 104.85(10) . . ? C4 P1 Ir1 114.92(8) . . ? C1 P1 Ir1 112.58(7) . . ? C7 P1 Ir1 113.29(7) . . ? C16 P2 C10 103.32(10) . . ? C16 P2 C13 106.83(9) . . ? C10 P2 C13 104.16(9) . . ? C16 P2 Ir1 114.14(7) . . ? C10 P2 Ir1 113.95(7) . . ? C13 P2 Ir1 113.40(6) . . ? C3 C1 C2 109.30(17) . . ? C3 C1 P1 115.40(15) . . ? C2 C1 P1 114.12(15) . . ? C3 C1 H1 105.7 . . ? C2 C1 H1 105.7 . . ? P1 C1 H1 105.7 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C6 109.9(2) . . ? C5 C4 P1 114.30(16) . . ? C6 C4 P1 110.49(16) . . ? C5 C4 H4 107.3 . . ? C6 C4 H4 107.3 . . ? P1 C4 H4 107.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 110.6(2) . . ? C8 C7 P1 110.69(15) . . ? C9 C7 P1 118.34(18) . . ? C8 C7 H7 105.4 . . ? C9 C7 H7 105.4 . . ? P1 C7 H7 105.4 . . ? 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 . . ? 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 . . ? C11 C10 C12 109.32(18) . . ? C11 C10 P2 118.90(15) . . ? C12 C10 P2 110.64(14) . . ? C11 C10 H10 105.7 . . ? C12 C10 H10 105.7 . . ? P2 C10 H10 105.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 109.18(17) . . ? C14 C13 P2 114.44(14) . . ? C15 C13 P2 115.33(14) . . ? C14 C13 H13 105.7 . . ? C15 C13 H13 105.7 . . ? P2 C13 H13 105.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C17 110.53(18) . . ? C18 C16 P2 112.86(15) . . ? C17 C16 P2 111.09(15) . . ? C18 C16 H16 107.4 . . ? C17 C16 H16 107.4 . . ? P2 C16 H16 107.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 109.71(19) . . ? C24 C19 Ir1 125.68(15) . . ? C20 C19 Ir1 124.59(15) . . ? F1 C20 C21 113.95(19) . . ? F1 C20 C19 118.47(18) . . ? C21 C20 C19 127.5(2) . . ? C22 C21 C20 118.1(2) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? C23 C22 C21 119.1(2) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 118.7(2) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? F2 C24 C23 114.53(19) . . ? F2 C24 C19 118.69(18) . . ? C23 C24 C19 126.8(2) . . ? O1 C25 Ir1 173.98(18) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.927 _refine_diff_density_min -0.933 _refine_diff_density_rms 0.108 data_complex10 _database_code_depnum_ccdc_archive 'CCDC 686378' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H46 F4 Ir N P2' _chemical_formula_sum 'C25 H46 F4 Ir N P2' _chemical_formula_weight 690.77 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' F F 0.0171 0.0103 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.18500(10) _cell_length_b 23.4600(2) _cell_length_c 12.79200(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.4370(4) _cell_angle_gamma 90.00 _cell_volume 2756.34(4) _cell_formula_units_Z 4 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used 8230 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 5.001 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1888 _exptl_absorpt_correction_T_max 0.3799 _exptl_absorpt_process_details 'Denzo and Scalpack (Otwinowski & Minor 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 95(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 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 101272 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6287 _reflns_number_gt 5986 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCCD _computing_cell_refinement 'HKL Scalepack(Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalpack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0129P)^2^+2.3313P] 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 6287 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0167 _refine_ls_R_factor_gt 0.0151 _refine_ls_wR_factor_ref 0.0349 _refine_ls_wR_factor_gt 0.0345 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.258266(7) 0.112540(3) 0.629422(5) 0.01510(3) Uani 1 1 d . . . P1 P 0.25550(5) 0.119017(19) 0.44465(4) 0.01584(9) Uani 1 1 d . . . P2 P 0.26130(5) 0.107205(19) 0.81428(4) 0.01568(9) Uani 1 1 d . . . F1 F 0.16867(16) 0.24643(6) 0.63725(10) 0.0374(3) Uani 1 1 d . . . F2 F 0.3262(3) 0.34115(6) 0.64078(13) 0.0692(6) Uani 1 1 d . . . F3 F 0.74985(18) 0.24407(9) 0.63177(11) 0.0655(6) Uani 1 1 d . . . F4 F 0.61763(14) 0.14471(7) 0.63157(11) 0.0407(3) Uani 1 1 d . . . N1 N 0.5388(3) 0.29316(10) 0.63680(15) 0.0530(7) Uani 1 1 d . . . C1 C 0.1384(2) 0.17592(9) 0.38698(16) 0.0264(4) Uani 1 1 d . . . H1 H 0.1267 0.1663 0.3112 0.032 Uiso 1 1 calc R . . C2 C -0.0135(3) 0.17410(12) 0.4333(2) 0.0429(6) Uani 1 1 d . . . H2A H -0.0075 0.1815 0.5086 0.064 Uiso 1 1 calc R . . H2B H -0.0564 0.1364 0.4214 0.064 Uiso 1 1 calc R . . H2C H -0.0745 0.2032 0.3998 0.064 Uiso 1 1 calc R . . C3 C 0.2017(3) 0.23655(9) 0.39108(17) 0.0329(5) Uani 1 1 d . . . H3A H 0.1377 0.2626 0.3522 0.049 Uiso 1 1 calc R . . H3B H 0.2987 0.2367 0.3596 0.049 Uiso 1 1 calc R . . H3C H 0.2091 0.2491 0.4640 0.049 Uiso 1 1 calc R . . C4 C 0.4365(2) 0.13593(9) 0.38850(15) 0.0229(4) Uani 1 1 d . . . H4 H 0.4639 0.1739 0.4184 0.028 Uiso 1 1 calc R . . C5 C 0.5573(2) 0.09457(11) 0.42475(18) 0.0327(5) Uani 1 1 d . . . H5A H 0.5548 0.0602 0.3812 0.049 Uiso 1 1 calc R . . H5B H 0.5414 0.0841 0.4979 0.049 Uiso 1 1 calc R . . H5C H 0.6523 0.1132 0.4181 0.049 Uiso 1 1 calc R . . C6 C 0.4424(3) 0.14352(10) 0.26949(16) 0.0320(5) Uani 1 1 d . . . H6A H 0.5384 0.1580 0.2499 0.048 Uiso 1 1 calc R . . H6B H 0.3672 0.1707 0.2473 0.048 Uiso 1 1 calc R . . H6C H 0.4252 0.1067 0.2353 0.048 Uiso 1 1 calc R . . C7 C 0.1835(2) 0.05495(8) 0.37280(15) 0.0224(4) Uani 1 1 d . . . H7 H 0.1041 0.0391 0.4173 0.027 Uiso 1 1 calc R . . C8 C 0.2973(3) 0.00776(9) 0.36404(18) 0.0319(5) Uani 1 1 d . . . H8A H 0.2485 -0.0287 0.3504 0.048 Uiso 1 1 calc R . . H8B H 0.3528 0.0052 0.4296 0.048 Uiso 1 1 calc R . . H8C H 0.3636 0.0165 0.3065 0.048 Uiso 1 1 calc R . . C9 C 0.1146(3) 0.06533(10) 0.26443(16) 0.0314(5) Uani 1 1 d . . . H9A H 0.1833 0.0863 0.2206 0.047 Uiso 1 1 calc R . . H9B H 0.0251 0.0876 0.2721 0.047 Uiso 1 1 calc R . . H9C H 0.0917 0.0287 0.2316 0.047 Uiso 1 1 calc R . . C10 C 0.1240(2) 0.15095(8) 0.88487(15) 0.0229(4) Uani 1 1 d . . . H10 H 0.1372 0.1427 0.9610 0.027 Uiso 1 1 calc R . . C11 C 0.1448(3) 0.21491(9) 0.87150(17) 0.0328(5) Uani 1 1 d . . . H11A H 0.1211 0.2257 0.7994 0.049 Uiso 1 1 calc R . . H11B H 0.2463 0.2249 0.8870 0.049 Uiso 1 1 calc R . . H11C H 0.0805 0.2353 0.9195 0.049 Uiso 1 1 calc R . . C12 C -0.0333(2) 0.13506(12) 0.8571(2) 0.0376(5) Uani 1 1 d . . . H12A H -0.0997 0.1541 0.9054 0.056 Uiso 1 1 calc R . . H12B H -0.0456 0.0937 0.8626 0.056 Uiso 1 1 calc R . . H12C H -0.0552 0.1472 0.7854 0.056 Uiso 1 1 calc R . . C13 C 0.2232(2) 0.03508(9) 0.86985(15) 0.0221(4) Uani 1 1 d . . . H13 H 0.1352 0.0208 0.8315 0.026 Uiso 1 1 calc R . . C14 C 0.1855(3) 0.03156(10) 0.98647(17) 0.0352(5) Uani 1 1 d . . . H14A H 0.1637 -0.0081 1.0050 0.053 Uiso 1 1 calc R . . H14B H 0.1003 0.0554 1.0005 0.053 Uiso 1 1 calc R . . H14C H 0.2684 0.0450 1.0283 0.053 Uiso 1 1 calc R . . C15 C 0.3442(3) -0.00856(9) 0.84817(19) 0.0336(5) Uani 1 1 d . . . H15A H 0.4222 -0.0042 0.9003 0.050 Uiso 1 1 calc R . . H15B H 0.3835 -0.0021 0.7781 0.050 Uiso 1 1 calc R . . H15C H 0.3041 -0.0472 0.8523 0.050 Uiso 1 1 calc R . . C16 C 0.4346(2) 0.13312(9) 0.87436(15) 0.0217(4) Uani 1 1 d . . . H16 H 0.4517 0.1714 0.8424 0.026 Uiso 1 1 calc R . . C17 C 0.4371(3) 0.14333(11) 0.99248(16) 0.0348(5) Uani 1 1 d . . . H17A H 0.4318 0.1067 1.0290 0.052 Uiso 1 1 calc R . . H17B H 0.3537 0.1670 1.0119 0.052 Uiso 1 1 calc R . . H17C H 0.5276 0.1629 1.0122 0.052 Uiso 1 1 calc R . . C18 C 0.5664(2) 0.09717(11) 0.8433(2) 0.0348(5) Uani 1 1 d . . . H18A H 0.6549 0.1203 0.8487 0.052 Uiso 1 1 calc R . . H18B H 0.5540 0.0839 0.7711 0.052 Uiso 1 1 calc R . . H18C H 0.5747 0.0643 0.8901 0.052 Uiso 1 1 calc R . . C19 C 0.0613(2) 0.06318(9) 0.62457(16) 0.0261(4) Uani 1 1 d . . . H19A H 0.0040 0.0620 0.6898 0.031 Uiso 1 1 calc R . . H19B H 0.0004 0.0672 0.5608 0.031 Uiso 1 1 calc R . . C20 C 0.1774(2) 0.02534(9) 0.61845(16) 0.0264(4) Uani 1 1 d . . . H20A H 0.1909 0.0057 0.5507 0.032 Uiso 1 1 calc R . . H20B H 0.1946 0.0005 0.6799 0.032 Uiso 1 1 calc R . . C21 C 0.3809(2) 0.18718(9) 0.63491(14) 0.0229(4) Uani 1 1 d . . . C22 C 0.3168(3) 0.24101(9) 0.63829(15) 0.0318(5) Uani 1 1 d . . . C23 C 0.3965(4) 0.29063(10) 0.63877(17) 0.0466(7) Uani 1 1 d . . . C24 C 0.6032(3) 0.24366(13) 0.63417(17) 0.0453(7) Uani 1 1 d . . . C25 C 0.5321(2) 0.19153(10) 0.63391(16) 0.0312(5) Uani 1 1 d . . . 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 0.01650(4) 0.01525(4) 0.01356(4) 0.00012(2) -0.00048(2) -0.00163(2) P1 0.0188(2) 0.0147(2) 0.0140(2) 0.00024(16) -0.00164(17) 0.00011(17) P2 0.0165(2) 0.0166(2) 0.0139(2) 0.00002(17) 0.00033(17) -0.00117(17) F1 0.0608(9) 0.0277(7) 0.0238(6) 0.0000(5) 0.0040(6) 0.0140(6) F2 0.1481(18) 0.0184(7) 0.0413(9) -0.0029(6) 0.0020(10) -0.0090(9) F3 0.0616(10) 0.1053(15) 0.0296(8) -0.0075(8) 0.0054(7) -0.0615(10) F4 0.0262(6) 0.0587(10) 0.0373(7) -0.0059(7) 0.0006(5) -0.0090(6) N1 0.098(2) 0.0415(13) 0.0194(9) -0.0022(9) 0.0033(11) -0.0437(14) C1 0.0317(11) 0.0258(10) 0.0216(9) 0.0009(8) -0.0055(8) 0.0091(8) C2 0.0297(12) 0.0494(16) 0.0497(15) 0.0054(12) -0.0041(10) 0.0161(11) C3 0.0553(14) 0.0202(10) 0.0231(10) 0.0005(8) -0.0069(10) 0.0102(10) C4 0.0229(9) 0.0255(10) 0.0204(9) 0.0001(8) 0.0023(7) -0.0044(8) C5 0.0221(10) 0.0433(13) 0.0327(12) -0.0047(10) 0.0004(9) 0.0038(9) C6 0.0386(12) 0.0360(12) 0.0216(10) 0.0019(9) 0.0062(9) -0.0067(10) C7 0.0280(10) 0.0190(9) 0.0203(9) -0.0022(7) 0.0000(7) -0.0051(8) C8 0.0410(12) 0.0200(10) 0.0348(12) -0.0037(8) 0.0073(9) -0.0015(9) C9 0.0422(12) 0.0289(11) 0.0230(10) -0.0017(8) -0.0070(9) -0.0093(9) C10 0.0235(9) 0.0250(10) 0.0201(9) -0.0012(7) 0.0028(7) 0.0053(8) C11 0.0454(13) 0.0251(11) 0.0281(11) 0.0012(9) 0.0106(9) 0.0093(10) C12 0.0222(10) 0.0490(15) 0.0416(13) -0.0119(11) 0.0014(9) 0.0084(10) C13 0.0261(10) 0.0210(9) 0.0191(9) 0.0015(7) -0.0006(7) -0.0041(8) C14 0.0517(14) 0.0310(12) 0.0229(10) 0.0062(9) 0.0043(10) -0.0104(10) C15 0.0378(12) 0.0233(11) 0.0398(13) 0.0043(9) -0.0004(10) 0.0036(9) C16 0.0209(9) 0.0261(10) 0.0182(9) 0.0002(8) -0.0031(7) -0.0049(8) C17 0.0354(12) 0.0495(14) 0.0196(10) 0.0002(9) -0.0069(9) -0.0130(10) C18 0.0202(10) 0.0403(13) 0.0440(13) -0.0016(10) -0.0044(9) 0.0004(9) C19 0.0256(10) 0.0299(11) 0.0227(9) 0.0002(8) 0.0000(8) -0.0136(8) C20 0.0383(11) 0.0212(10) 0.0196(9) 0.0015(7) -0.0023(8) -0.0111(8) C21 0.0351(11) 0.0233(10) 0.0102(8) -0.0003(7) 0.0019(7) -0.0084(8) C22 0.0550(14) 0.0269(11) 0.0137(9) -0.0019(8) 0.0017(9) -0.0068(10) C23 0.100(2) 0.0231(12) 0.0168(10) -0.0031(8) 0.0014(12) -0.0163(13) C24 0.0598(16) 0.0626(18) 0.0136(10) -0.0043(10) 0.0039(10) -0.0423(14) C25 0.0379(12) 0.0395(13) 0.0162(9) -0.0023(8) 0.0013(8) -0.0176(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C21 2.0830(19) . ? Ir1 C19 2.1487(19) . ? Ir1 C20 2.1805(19) . ? Ir1 P2 2.3679(5) . ? Ir1 P1 2.3684(5) . ? P1 C4 1.859(2) . ? P1 C1 1.863(2) . ? P1 C7 1.8793(19) . ? P2 C16 1.8641(19) . ? P2 C10 1.8647(19) . ? P2 C13 1.869(2) . ? F1 C22 1.367(3) . ? F2 C23 1.350(3) . ? F3 C24 1.348(3) . ? F4 C25 1.351(3) . ? N1 C24 1.304(4) . ? N1 C23 1.309(4) . ? C1 C2 1.521(3) . ? C1 C3 1.537(3) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C6 1.534(3) . ? C4 C5 1.543(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.527(3) . ? C7 C9 1.539(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.522(3) . ? C10 C12 1.531(3) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.536(3) . ? C13 C15 1.538(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.530(3) . ? C16 C18 1.531(3) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.390(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C25 1.392(3) . ? C21 C22 1.394(3) . ? C22 C23 1.375(3) . ? C24 C25 1.386(3) . ? 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 C21 Ir1 C19 155.38(8) . . ? C21 Ir1 C20 167.08(8) . . ? C19 Ir1 C20 37.45(8) . . ? C21 Ir1 P2 90.49(5) . . ? C19 Ir1 P2 90.22(5) . . ? C20 Ir1 P2 90.92(5) . . ? C21 Ir1 P1 88.93(5) . . ? C19 Ir1 P1 90.18(5) . . ? C20 Ir1 P1 89.71(5) . . ? P2 Ir1 P1 179.349(16) . . ? C4 P1 C1 102.08(9) . . ? C4 P1 C7 107.10(9) . . ? C1 P1 C7 100.35(9) . . ? C4 P1 Ir1 113.36(6) . . ? C1 P1 Ir1 116.29(7) . . ? C7 P1 Ir1 115.96(6) . . ? C16 P2 C10 101.50(9) . . ? C16 P2 C13 107.47(9) . . ? C10 P2 C13 100.64(9) . . ? C16 P2 Ir1 113.46(6) . . ? C10 P2 Ir1 116.85(6) . . ? C13 P2 Ir1 115.27(6) . . ? C24 N1 C23 114.4(2) . . ? C2 C1 C3 111.13(19) . . ? C2 C1 P1 110.74(15) . . ? C3 C1 P1 115.62(15) . . ? C2 C1 H1 106.2 . . ? C3 C1 H1 106.2 . . ? P1 C1 H1 106.2 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C6 C4 C5 109.91(17) . . ? C6 C4 P1 116.53(14) . . ? C5 C4 P1 113.13(14) . . ? C6 C4 H4 105.4 . . ? C5 C4 H4 105.4 . . ? P1 C4 H4 105.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 109.00(17) . . ? C8 C7 P1 112.17(14) . . ? C9 C7 P1 117.04(14) . . ? C8 C7 H7 105.9 . . ? C9 C7 H7 105.9 . . ? P1 C7 H7 105.9 . . ? 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 . . ? 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 . . ? C11 C10 C12 109.46(18) . . ? C11 C10 P2 113.70(14) . . ? C12 C10 P2 113.20(14) . . ? C11 C10 H10 106.7 . . ? C12 C10 H10 106.7 . . ? P2 C10 H10 106.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 107.94(18) . . ? C14 C13 P2 117.53(15) . . ? C15 C13 P2 113.34(14) . . ? C14 C13 H13 105.7 . . ? C15 C13 H13 105.7 . . ? P2 C13 H13 105.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C18 109.67(18) . . ? C17 C16 P2 117.70(14) . . ? C18 C16 P2 112.81(14) . . ? C17 C16 H16 105.2 . . ? C18 C16 H16 105.2 . . ? P2 C16 H16 105.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 Ir1 72.52(11) . . ? C20 C19 H19A 116.3 . . ? Ir1 C19 H19A 116.3 . . ? C20 C19 H19B 116.3 . . ? Ir1 C19 H19B 116.3 . . ? H19A C19 H19B 113.3 . . ? C19 C20 Ir1 70.03(11) . . ? C19 C20 H20A 116.6 . . ? Ir1 C20 H20A 116.6 . . ? C19 C20 H20B 116.6 . . ? Ir1 C20 H20B 116.6 . . ? H20A C20 H20B 113.6 . . ? C25 C21 C22 110.80(19) . . ? C25 C21 Ir1 126.90(16) . . ? C22 C21 Ir1 122.28(16) . . ? F1 C22 C23 116.8(2) . . ? F1 C22 C21 120.31(19) . . ? C23 C22 C21 122.8(2) . . ? N1 C23 F2 116.0(2) . . ? N1 C23 C22 124.7(3) . . ? F2 C23 C22 119.3(3) . . ? N1 C24 F3 116.6(2) . . ? N1 C24 C25 124.9(3) . . ? F3 C24 C25 118.5(3) . . ? F4 C25 C24 116.3(2) . . ? F4 C25 C21 121.39(19) . . ? C24 C25 C21 122.3(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.827 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.061