# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Thomas Braun' _publ_contact_author_email THOMAS.BRAUN@CMS.HU-BERLIN.DE _publ_section_title ; Activation of Ethylene and Ammonia at Iridium: C-H versus N-H Oxidative Addition ; loop_ _publ_author_name 'Thomas Braun' 'Ann-Katrin Jungton' 'Marcel Ahijado Salomon' data_akju19_complex3 _database_code_depnum_ccdc_archive 'CCDC 725696' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H47 F4 Ir N2 P2' _chemical_formula_sum 'C23 H47 F4 Ir N2 P2' _chemical_formula_weight 681.77 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7052(14) _cell_length_b 10.2909(19) _cell_length_c 16.232(3) _cell_angle_alpha 75.886(15) _cell_angle_beta 86.624(14) _cell_angle_gamma 73.932(13) _cell_volume 1355.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method none _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 5.086 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4295 _exptl_absorpt_correction_T_max 0.6864 _exptl_absorpt_process_details ; The crystal faces were indexed by microscope on the diffractometer. After that a numerical absorption correction basing on a Gaussian algorithsm was applied, which is implemented in the X-RED program (Stoe, 2002). ; _exptl_special_details ; During data collection the crystal was in cold N~2~ gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a 2-circle goniometer supplied with an area detector. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long fine focus sealed X-ray tube' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_collimation '0.5 mm diameter monocapillary' _diffrn_measurement_device 'Stoe IPDS-2t diffractometer' _diffrn_measurement_method '\w-rotation,\w-incr.=1\%,321 exposures' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22666 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6215 _reflns_number_gt 5845 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (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^)+(0.0435P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6215 _refine_ls_number_parameters 309 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0504 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6613(3) 0.2706(3) 0.35746(16) 0.0144(5) Uani 1 1 d . . . H1 H 0.7160 0.2730 0.3014 0.017 Uiso 1 1 calc R . . C2 C 0.6912(3) 0.3912(3) 0.38861(18) 0.0196(5) Uani 1 1 d . . . H2A H 0.8053 0.3866 0.3842 0.029 Uiso 1 1 calc R . . H2B H 0.6582 0.3839 0.4480 0.029 Uiso 1 1 calc R . . H2C H 0.6293 0.4800 0.3535 0.029 Uiso 1 1 calc R . . C3 C 0.7508(3) 0.1325(3) 0.41640(18) 0.0207(5) Uani 1 1 d . . . H3A H 0.7513 0.0554 0.3908 0.031 Uiso 1 1 calc R . . H3B H 0.6972 0.1204 0.4714 0.031 Uiso 1 1 calc R . . H3C H 0.8611 0.1335 0.4246 0.031 Uiso 1 1 calc R . . C4 C 0.4521(3) 0.1403(3) 0.28803(15) 0.0141(4) Uani 1 1 d . . . H4 H 0.3438 0.1621 0.2621 0.017 Uiso 1 1 calc R . . C5 C 0.5686(3) 0.1374(3) 0.21380(16) 0.0168(5) Uani 1 1 d . . . H5A H 0.5531 0.0724 0.1819 0.025 Uiso 1 1 calc R . . H5B H 0.6786 0.1071 0.2356 0.025 Uiso 1 1 calc R . . H5C H 0.5487 0.2309 0.1763 0.025 Uiso 1 1 calc R . . C6 C 0.4794(4) -0.0060(3) 0.34657(17) 0.0196(5) Uani 1 1 d . . . H6A H 0.3969 -0.0051 0.3903 0.029 Uiso 1 1 calc R . . H6B H 0.5850 -0.0342 0.3737 0.029 Uiso 1 1 calc R . . H6C H 0.4739 -0.0720 0.3131 0.029 Uiso 1 1 calc R . . C7 C 0.3548(3) 0.2406(3) 0.43986(16) 0.0155(5) Uani 1 1 d . . . H7 H 0.4191 0.1453 0.4690 0.019 Uiso 1 1 calc R . . C8 C 0.1838(3) 0.2336(3) 0.42883(18) 0.0207(5) Uani 1 1 d . . . H8A H 0.1153 0.3276 0.4060 0.031 Uiso 1 1 calc R . . H8B H 0.1430 0.1937 0.4840 0.031 Uiso 1 1 calc R . . H8C H 0.1836 0.1751 0.3894 0.031 Uiso 1 1 calc R . . C9 C 0.3536(4) 0.3382(3) 0.49764(17) 0.0221(5) Uani 1 1 d . . . H9A H 0.4632 0.3263 0.5155 0.033 Uiso 1 1 calc R . . H9B H 0.2887 0.3160 0.5478 0.033 Uiso 1 1 calc R . . H9C H 0.3080 0.4348 0.4666 0.033 Uiso 1 1 calc R . . C10 C -0.0366(3) 0.7511(3) 0.16702(16) 0.0155(5) Uani 1 1 d . . . H10 H -0.0274 0.6773 0.1354 0.019 Uiso 1 1 calc R . . C11 C -0.1449(3) 0.7191(3) 0.24271(19) 0.0220(5) Uani 1 1 d . . . H11A H -0.2390 0.7000 0.2233 0.033 Uiso 1 1 calc R . . H11B H -0.1789 0.7994 0.2684 0.033 Uiso 1 1 calc R . . H11C H -0.0859 0.6376 0.2850 0.033 Uiso 1 1 calc R . . C12 C -0.1210(3) 0.8889(3) 0.10607(17) 0.0182(5) Uani 1 1 d . . . H12A H -0.0635 0.8989 0.0521 0.027 Uiso 1 1 calc R . . H12B H -0.1223 0.9666 0.1313 0.027 Uiso 1 1 calc R . . H12C H -0.2309 0.8893 0.0958 0.027 Uiso 1 1 calc R . . C13 C 0.1615(3) 0.8372(3) 0.28116(16) 0.0164(5) Uani 1 1 d . . . H13 H 0.2751 0.8356 0.2893 0.020 Uiso 1 1 calc R . . C14 C 0.1071(4) 0.7740(3) 0.36970(17) 0.0232(6) Uani 1 1 d . . . H14A H -0.0085 0.7864 0.3688 0.035 Uiso 1 1 calc R . . H14B H 0.1328 0.8208 0.4108 0.035 Uiso 1 1 calc R . . H14C H 0.1624 0.6745 0.3861 0.035 Uiso 1 1 calc R . . C15 C 0.0727(4) 0.9919(3) 0.25362(18) 0.0215(5) Uani 1 1 d . . . H15A H 0.1089 1.0315 0.1972 0.032 Uiso 1 1 calc R . . H15B H 0.0947 1.0408 0.2945 0.032 Uiso 1 1 calc R . . H15C H -0.0425 1.0023 0.2516 0.032 Uiso 1 1 calc R . . C16 C 0.2451(3) 0.8408(3) 0.10696(16) 0.0153(5) Uani 1 1 d . . . H16 H 0.1606 0.9310 0.0904 0.018 Uiso 1 1 calc R . . C17 C 0.3976(3) 0.8754(3) 0.12559(19) 0.0221(5) Uani 1 1 d . . . H17A H 0.4437 0.9153 0.0721 0.033 Uiso 1 1 calc R . . H17B H 0.4750 0.7902 0.1554 0.033 Uiso 1 1 calc R . . H17C H 0.3719 0.9427 0.1612 0.033 Uiso 1 1 calc R . . C18 C 0.2655(3) 0.7722(3) 0.03175(17) 0.0188(5) Uani 1 1 d . . . H18A H 0.3489 0.6837 0.0453 0.028 Uiso 1 1 calc R . . H18B H 0.2963 0.8340 -0.0186 0.028 Uiso 1 1 calc R . . H18C H 0.1644 0.7551 0.0205 0.028 Uiso 1 1 calc R . . C19 C 0.2131(3) 0.4246(2) 0.16467(15) 0.0121(4) Uani 1 1 d . . . C20 C 0.2737(3) 0.4022(3) 0.08586(16) 0.0142(5) Uani 1 1 d . . . C21 C 0.1998(3) 0.3512(3) 0.03330(16) 0.0172(5) Uani 1 1 d . . . C22 C 0.0032(3) 0.3360(3) 0.12319(16) 0.0149(5) Uani 1 1 d . . . C23 C 0.0701(3) 0.3866(3) 0.17942(15) 0.0140(4) Uani 1 1 d . . . Ir1 Ir 0.317598(10) 0.504484(9) 0.251075(5) 0.01015(4) Uani 1 1 d D . . H1A H 0.394(4) 0.552(3) 0.3086(19) 0.012 Uiso 1 1 d D . . H1B H 0.222(4) 0.443(3) 0.3105(18) 0.012 Uiso 1 1 d D . . N1 N 0.5435(3) 0.5127(2) 0.17751(14) 0.0151(4) Uani 1 1 d . . . H1C H 0.5875 0.4297 0.1638 0.023 Uiso 1 1 calc R . . H1D H 0.6140 0.5301 0.2099 0.023 Uiso 1 1 calc R . . H1E H 0.5203 0.5818 0.1292 0.023 Uiso 1 1 calc R . . N2 N 0.0652(3) 0.3169(2) 0.04997(14) 0.0180(4) Uani 1 1 d . . . P1 P 0.44672(7) 0.29022(6) 0.33537(4) 0.01135(11) Uani 1 1 d . . . P2 P 0.17052(7) 0.73270(6) 0.20115(4) 0.01146(11) Uani 1 1 d . . . F1 F 0.41349(19) 0.43055(17) 0.05671(10) 0.0186(3) Uani 1 1 d . . . F2 F 0.2674(2) 0.3335(2) -0.04156(11) 0.0284(4) Uani 1 1 d . . . F3 F -0.13506(19) 0.30078(17) 0.14304(10) 0.0202(3) Uani 1 1 d . . . F4 F -0.01350(19) 0.39655(18) 0.25175(10) 0.0212(3) 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 C1 0.0133(11) 0.0181(11) 0.0122(11) -0.0036(9) -0.0014(8) -0.0046(9) C2 0.0185(12) 0.0222(13) 0.0212(13) -0.0081(10) -0.0034(10) -0.0073(10) C3 0.0171(12) 0.0207(13) 0.0217(13) -0.0012(10) -0.0070(10) -0.0029(10) C4 0.0161(11) 0.0149(11) 0.0126(11) -0.0039(9) -0.0006(9) -0.0057(9) C5 0.0184(12) 0.0185(12) 0.0157(11) -0.0080(9) 0.0025(9) -0.0055(10) C6 0.0266(13) 0.0155(11) 0.0180(12) -0.0036(9) -0.0011(10) -0.0079(10) C7 0.0174(12) 0.0171(11) 0.0117(11) -0.0033(9) 0.0021(9) -0.0049(9) C8 0.0177(12) 0.0264(13) 0.0182(12) -0.0025(10) 0.0048(10) -0.0096(10) C9 0.0308(15) 0.0243(13) 0.0130(12) -0.0079(10) 0.0051(10) -0.0083(11) C10 0.0143(11) 0.0161(11) 0.0174(12) -0.0052(9) -0.0018(9) -0.0048(9) C11 0.0146(12) 0.0225(13) 0.0274(14) -0.0020(11) 0.0025(10) -0.0062(10) C12 0.0154(11) 0.0176(12) 0.0197(12) -0.0047(10) -0.0051(9) -0.0004(9) C13 0.0170(11) 0.0178(12) 0.0156(11) -0.0062(9) -0.0015(9) -0.0046(9) C14 0.0315(15) 0.0245(13) 0.0143(12) -0.0108(10) 0.0027(10) -0.0036(11) C15 0.0263(14) 0.0174(12) 0.0227(13) -0.0099(10) -0.0012(11) -0.0044(10) C16 0.0163(11) 0.0141(11) 0.0147(11) -0.0012(9) 0.0009(9) -0.0050(9) C17 0.0200(13) 0.0243(13) 0.0253(14) -0.0047(11) 0.0031(10) -0.0131(11) C18 0.0224(13) 0.0192(12) 0.0133(11) -0.0031(9) 0.0011(9) -0.0038(10) C19 0.0132(11) 0.0116(10) 0.0113(10) -0.0028(8) 0.0008(8) -0.0033(8) C20 0.0139(11) 0.0162(11) 0.0136(11) -0.0025(9) 0.0031(9) -0.0075(9) C21 0.0215(13) 0.0213(12) 0.0117(11) -0.0065(9) 0.0043(9) -0.0092(10) C22 0.0129(11) 0.0166(11) 0.0175(12) -0.0057(9) 0.0019(9) -0.0065(9) C23 0.0150(11) 0.0174(11) 0.0107(10) -0.0055(9) 0.0031(9) -0.0049(9) Ir1 0.01058(6) 0.01190(6) 0.00886(6) -0.00300(3) 0.00068(3) -0.00415(3) N1 0.0120(9) 0.0172(10) 0.0164(10) -0.0031(8) 0.0026(8) -0.0056(8) N2 0.0198(11) 0.0229(11) 0.0150(10) -0.0070(8) 0.0015(8) -0.0103(9) P1 0.0125(3) 0.0137(3) 0.0092(3) -0.0035(2) 0.0008(2) -0.0051(2) P2 0.0126(3) 0.0130(3) 0.0102(3) -0.0037(2) 0.0004(2) -0.0050(2) F1 0.0181(7) 0.0259(8) 0.0170(7) -0.0090(6) 0.0086(6) -0.0128(6) F2 0.0344(10) 0.0479(11) 0.0172(8) -0.0201(8) 0.0134(7) -0.0262(9) F3 0.0147(7) 0.0280(8) 0.0241(8) -0.0118(7) 0.0041(6) -0.0117(6) F4 0.0199(8) 0.0352(9) 0.0158(7) -0.0139(7) 0.0089(6) -0.0146(7) _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 C1 C3 1.534(4) . ? C1 C2 1.538(4) . ? C1 P1 1.869(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(3) . ? C4 C6 1.535(3) . ? C4 P1 1.873(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 C9 1.530(4) . ? C7 C8 1.534(4) . ? C7 P1 1.850(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 1.531(4) . ? C10 C12 1.534(4) . ? C10 P2 1.863(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 C15 1.531(4) . ? C13 C14 1.532(4) . ? C13 P2 1.863(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(4) . ? C16 C18 1.531(4) . ? C16 P2 1.857(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 C23 1.396(3) . ? C19 C20 1.402(3) . ? C19 Ir1 2.144(2) . ? C20 F1 1.361(3) . ? C20 C21 1.374(4) . ? C21 N2 1.310(3) . ? C21 F2 1.349(3) . ? C22 N2 1.312(3) . ? C22 F3 1.350(3) . ? C22 C23 1.380(4) . ? C23 F4 1.355(3) . ? Ir1 N1 2.251(2) . ? Ir1 P1 2.3098(8) . ? Ir1 P2 2.3111(8) . ? Ir1 H1A 1.43(2) . ? Ir1 H1B 1.38(2) . ? N1 H1C 0.9100 . ? N1 H1D 0.9100 . ? N1 H1E 0.9100 . ? 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 C3 C1 C2 108.8(2) . . ? C3 C1 P1 116.01(18) . . ? C2 C1 P1 114.43(18) . . ? C3 C1 H1 105.5 . . ? C2 C1 H1 105.5 . . ? P1 C1 H1 105.5 . . ? 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 110.2(2) . . ? C5 C4 P1 110.33(17) . . ? C6 C4 P1 119.11(18) . . ? C5 C4 H4 105.4 . . ? C6 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 . . ? C9 C7 C8 109.4(2) . . ? C9 C7 P1 113.30(18) . . ? C8 C7 P1 110.70(18) . . ? C9 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? P1 C7 H7 107.7 . . ? 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 109.6(2) . . ? C11 C10 P2 112.08(18) . . ? C12 C10 P2 116.73(18) . . ? C11 C10 H10 105.9 . . ? C12 C10 H10 105.9 . . ? P2 C10 H10 105.9 . . ? 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 110.1(2) . . ? C15 C13 P2 116.14(18) . . ? C14 C13 P2 114.98(19) . . ? C15 C13 H13 104.8 . . ? C14 C13 H13 104.8 . . ? P2 C13 H13 104.8 . . ? 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 112.0(2) . . ? C17 C16 P2 112.98(18) . . ? C18 C16 P2 110.48(18) . . ? C17 C16 H16 107.0 . . ? C18 C16 H16 107.0 . . ? P2 C16 H16 107.0 . . ? 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 109.1(2) . . ? C23 C19 Ir1 124.06(18) . . ? C20 C19 Ir1 126.83(18) . . ? F1 C20 C21 115.5(2) . . ? F1 C20 C19 120.7(2) . . ? C21 C20 C19 123.8(2) . . ? N2 C21 F2 115.7(2) . . ? N2 C21 C20 124.9(2) . . ? F2 C21 C20 119.4(2) . . ? N2 C22 F3 115.6(2) . . ? N2 C22 C23 124.8(2) . . ? F3 C22 C23 119.6(2) . . ? F4 C23 C22 114.9(2) . . ? F4 C23 C19 121.5(2) . . ? C22 C23 C19 123.7(2) . . ? C19 Ir1 N1 96.44(9) . . ? C19 Ir1 P1 95.98(7) . . ? N1 Ir1 P1 90.38(6) . . ? C19 Ir1 P2 94.87(7) . . ? N1 Ir1 P2 98.92(6) . . ? P1 Ir1 P2 164.82(2) . . ? C19 Ir1 H1A 177.2(13) . . ? N1 Ir1 H1A 81.8(13) . . ? P1 Ir1 H1A 81.9(13) . . ? P2 Ir1 H1A 87.5(13) . . ? C19 Ir1 H1B 84.1(13) . . ? N1 Ir1 H1B 155.1(13) . . ? P1 Ir1 H1B 64.9(13) . . ? P2 Ir1 H1B 105.8(13) . . ? H1A Ir1 H1B 96.6(19) . . ? Ir1 N1 H1C 109.5 . . ? Ir1 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? Ir1 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C21 N2 C22 113.8(2) . . ? C7 P1 C1 106.13(12) . . ? C7 P1 C4 101.99(12) . . ? C1 P1 C4 104.17(11) . . ? C7 P1 Ir1 115.54(9) . . ? C1 P1 Ir1 113.87(8) . . ? C4 P1 Ir1 113.81(8) . . ? C16 P2 C13 101.06(12) . . ? C16 P2 C10 101.91(12) . . ? C13 P2 C10 109.09(12) . . ? C16 P2 Ir1 118.31(9) . . ? C13 P2 Ir1 111.51(8) . . ? C10 P2 Ir1 113.78(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 C19 C20 F1 -179.6(2) . . . . ? Ir1 C19 C20 F1 0.5(3) . . . . ? C23 C19 C20 C21 0.2(3) . . . . ? Ir1 C19 C20 C21 -179.7(2) . . . . ? F1 C20 C21 N2 179.6(2) . . . . ? C19 C20 C21 N2 -0.2(4) . . . . ? F1 C20 C21 F2 -0.4(4) . . . . ? C19 C20 C21 F2 179.8(2) . . . . ? N2 C22 C23 F4 -179.3(2) . . . . ? F3 C22 C23 F4 -0.2(3) . . . . ? N2 C22 C23 C19 0.4(4) . . . . ? F3 C22 C23 C19 179.5(2) . . . . ? C20 C19 C23 F4 179.4(2) . . . . ? Ir1 C19 C23 F4 -0.7(3) . . . . ? C20 C19 C23 C22 -0.3(3) . . . . ? Ir1 C19 C23 C22 179.61(19) . . . . ? C23 C19 Ir1 N1 175.1(2) . . . . ? C20 C19 Ir1 N1 -5.0(2) . . . . ? C23 C19 Ir1 P1 84.1(2) . . . . ? C20 C19 Ir1 P1 -96.0(2) . . . . ? C23 C19 Ir1 P2 -85.3(2) . . . . ? C20 C19 Ir1 P2 94.6(2) . . . . ? F2 C21 N2 C22 -179.8(2) . . . . ? C20 C21 N2 C22 0.2(4) . . . . ? F3 C22 N2 C21 -179.5(2) . . . . ? C23 C22 N2 C21 -0.3(4) . . . . ? C9 C7 P1 C1 64.4(2) . . . . ? C8 C7 P1 C1 -172.30(18) . . . . ? C9 C7 P1 C4 173.14(19) . . . . ? C8 C7 P1 C4 -63.5(2) . . . . ? C9 C7 P1 Ir1 -62.9(2) . . . . ? C8 C7 P1 Ir1 60.5(2) . . . . ? C3 C1 P1 C7 49.2(2) . . . . ? C2 C1 P1 C7 -78.8(2) . . . . ? C3 C1 P1 C4 -58.0(2) . . . . ? C2 C1 P1 C4 173.99(18) . . . . ? C3 C1 P1 Ir1 177.42(17) . . . . ? C2 C1 P1 Ir1 49.4(2) . . . . ? C5 C4 P1 C7 -162.69(17) . . . . ? C6 C4 P1 C7 -33.9(2) . . . . ? C5 C4 P1 C1 -52.41(19) . . . . ? C6 C4 P1 C1 76.4(2) . . . . ? C5 C4 P1 Ir1 72.17(18) . . . . ? C6 C4 P1 Ir1 -159.00(17) . . . . ? C19 Ir1 P1 C7 -105.19(12) . . . . ? N1 Ir1 P1 C7 158.29(11) . . . . ? P2 Ir1 P1 C7 30.21(13) . . . . ? C19 Ir1 P1 C1 131.56(11) . . . . ? N1 Ir1 P1 C1 35.04(11) . . . . ? P2 Ir1 P1 C1 -93.04(12) . . . . ? C19 Ir1 P1 C4 12.36(11) . . . . ? N1 Ir1 P1 C4 -84.16(11) . . . . ? P2 Ir1 P1 C4 147.76(11) . . . . ? C17 C16 P2 C13 52.6(2) . . . . ? C18 C16 P2 C13 178.90(18) . . . . ? C17 C16 P2 C10 165.05(19) . . . . ? C18 C16 P2 C10 -68.6(2) . . . . ? C17 C16 P2 Ir1 -69.4(2) . . . . ? C18 C16 P2 Ir1 56.9(2) . . . . ? C15 C13 P2 C16 51.0(2) . . . . ? C14 C13 P2 C16 -178.4(2) . . . . ? C15 C13 P2 C10 -55.9(2) . . . . ? C14 C13 P2 C10 74.7(2) . . . . ? C15 C13 P2 Ir1 177.60(17) . . . . ? C14 C13 P2 Ir1 -51.8(2) . . . . ? C11 C10 P2 C16 -158.41(19) . . . . ? C12 C10 P2 C16 -30.9(2) . . . . ? C11 C10 P2 C13 -52.1(2) . . . . ? C12 C10 P2 C13 75.4(2) . . . . ? C11 C10 P2 Ir1 73.1(2) . . . . ? C12 C10 P2 Ir1 -159.37(17) . . . . ? C19 Ir1 P2 C16 -84.64(12) . . . . ? N1 Ir1 P2 C16 12.68(11) . . . . ? P1 Ir1 P2 C16 139.86(12) . . . . ? C19 Ir1 P2 C13 158.85(11) . . . . ? N1 Ir1 P2 C13 -103.84(11) . . . . ? P1 Ir1 P2 C13 23.34(13) . . . . ? C19 Ir1 P2 C10 34.94(11) . . . . ? N1 Ir1 P2 C10 132.25(11) . . . . ? P1 Ir1 P2 C10 -100.57(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.545 _refine_diff_density_min -1.920 _refine_diff_density_rms 0.113 data_akju6_complex4 _database_code_depnum_ccdc_archive 'CCDC 725697' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H50 F4 Ir N O4 P2' _chemical_formula_sum 'C29 H50 F4 Ir N O4 P2' _chemical_formula_weight 806.84 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 10.7834(16) _cell_length_b 14.3514(16) _cell_length_c 21.382(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3309.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method none _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 4.187 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4331 _exptl_absorpt_correction_T_max 0.7305 _exptl_absorpt_process_details ; The program XSHAPE1.02 (Stoe, 1997) was used for crystal optimisation before the numerical absorption correction basing on a Gaussian algorithsm and implemented in XRED1.08 (Stoe, 1997) was applied. In XSHAPE 150 strong reflections with 4 symmetry equivalents in each case were used for that optimisation. XSHAPE bases on the program HABITUS (Herrendorf, W. (1993). PhD thesis. Universit\"at Karlsruhe, Germany). ; _exptl_special_details ; During data collection the crystal was in cold N~2~ gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a \f-axis diffractometer supplied with an area detector. ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_monochromator 'planar graphite' _diffrn_measurement_device 'Stoe IPDS diffractometer' _diffrn_measurement_method '\f-rotation,\f-incr.=1.2\%,180 exposures' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32822 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6150 _reflns_number_gt 5505 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'IPDS2.87 (Stoe & Cie, 1997)' _computing_cell_refinement 'IPDS2.87 (Stoe & Cie, 1997)' _computing_data_reduction 'IPDS2.87 (Stoe & Cie, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL97 (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^)+(0.0098P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.00013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.014(3) _refine_ls_number_reflns 6150 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0158 _refine_ls_wR_factor_ref 0.0276 _refine_ls_wR_factor_gt 0.0272 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5102(4) 1.0575(3) 0.48758(15) 0.0227(9) Uani 1 1 d . . . H1 H 0.4195 1.0611 0.4782 0.027 Uiso 1 1 calc R . . C2 C 0.5528(4) 0.9631(3) 0.46185(16) 0.0379(11) Uani 1 1 d . . . H2A H 0.6434 0.9627 0.4579 0.057 Uiso 1 1 calc R . . H2B H 0.5154 0.9526 0.4207 0.057 Uiso 1 1 calc R . . H2C H 0.5270 0.9134 0.4905 0.057 Uiso 1 1 calc R . . C3 C 0.5703(4) 1.1371(3) 0.44967(17) 0.0471(12) Uani 1 1 d . . . H3A H 0.5298 1.1962 0.4601 0.071 Uiso 1 1 calc R . . H3B H 0.5607 1.1246 0.4049 0.071 Uiso 1 1 calc R . . H3C H 0.6587 1.1410 0.4600 0.071 Uiso 1 1 calc R . . C4 C 0.5039(3) 1.1939(2) 0.58743(16) 0.0184(8) Uani 1 1 d . . . H4 H 0.5643 1.2263 0.5594 0.022 Uiso 1 1 calc R . . C5 C 0.3742(4) 1.2274(2) 0.56921(17) 0.0301(8) Uani 1 1 d . . . H5A H 0.3712 1.2956 0.5712 0.045 Uiso 1 1 calc R . . H5B H 0.3131 1.2011 0.5982 0.045 Uiso 1 1 calc R . . H5C H 0.3553 1.2069 0.5265 0.045 Uiso 1 1 calc R . . C6 C 0.5329(4) 1.2237(2) 0.65419(16) 0.0251(9) Uani 1 1 d . . . H6A H 0.6161 1.2020 0.6656 0.038 Uiso 1 1 calc R . . H6B H 0.4718 1.1964 0.6827 0.038 Uiso 1 1 calc R . . H6C H 0.5296 1.2918 0.6572 0.038 Uiso 1 1 calc R . . C7 C 0.6863(3) 1.04621(19) 0.59682(15) 0.0155(7) Uani 1 1 d . . . H7 H 0.6878 1.0520 0.6434 0.019 Uiso 1 1 calc R . . C8 C 0.7849(3) 1.1164(2) 0.57344(17) 0.0260(8) Uani 1 1 d . . . H8A H 0.7956 1.1094 0.5282 0.039 Uiso 1 1 calc R . . H8B H 0.8640 1.1042 0.5945 0.039 Uiso 1 1 calc R . . H8C H 0.7576 1.1800 0.5829 0.039 Uiso 1 1 calc R . . C9 C 0.7302(3) 0.9465(2) 0.58353(17) 0.0253(8) Uani 1 1 d . . . H9A H 0.6602 0.9035 0.5878 0.038 Uiso 1 1 calc R . . H9B H 0.7953 0.9295 0.6134 0.038 Uiso 1 1 calc R . . H9C H 0.7631 0.9429 0.5409 0.038 Uiso 1 1 calc R . . C10 C 0.0735(3) 1.00300(19) 0.68969(14) 0.0157(8) Uani 1 1 d . . . H10 H 0.0441 0.9932 0.6458 0.019 Uiso 1 1 calc R . . C11 C 0.0981(3) 1.1084(2) 0.69439(16) 0.0214(8) Uani 1 1 d . . . H11A H 0.1123 1.1254 0.7382 0.032 Uiso 1 1 calc R . . H11B H 0.0261 1.1427 0.6784 0.032 Uiso 1 1 calc R . . H11C H 0.1715 1.1244 0.6696 0.032 Uiso 1 1 calc R . . C12 C -0.0385(3) 0.9775(3) 0.73088(15) 0.0300(8) Uani 1 1 d . . . H12A H -0.0571 0.9111 0.7262 0.045 Uiso 1 1 calc R . . H12B H -0.1106 1.0143 0.7179 0.045 Uiso 1 1 calc R . . H12C H -0.0191 0.9910 0.7747 0.045 Uiso 1 1 calc R . . C13 C 0.1486(3) 0.8097(2) 0.68267(16) 0.0195(8) Uani 1 1 d . . . H13 H 0.0912 0.7958 0.7182 0.023 Uiso 1 1 calc R . . C14 C 0.2508(3) 0.7364(2) 0.68498(18) 0.0289(9) Uani 1 1 d . . . H14A H 0.3013 0.7405 0.6470 0.043 Uiso 1 1 calc R . . H14B H 0.2134 0.6743 0.6877 0.043 Uiso 1 1 calc R . . H14C H 0.3032 0.7472 0.7217 0.043 Uiso 1 1 calc R . . C15 C 0.0721(3) 0.7993(2) 0.62229(18) 0.0308(9) Uani 1 1 d . . . H15A H 0.0057 0.8460 0.6219 0.046 Uiso 1 1 calc R . . H15B H 0.0357 0.7368 0.6206 0.046 Uiso 1 1 calc R . . H15C H 0.1260 0.8086 0.5859 0.046 Uiso 1 1 calc R . . C16 C 0.2553(3) 0.9202(2) 0.78190(15) 0.0179(8) Uani 1 1 d . . . H16 H 0.3409 0.8935 0.7829 0.021 Uiso 1 1 calc R . . C17 C 0.2655(3) 1.0164(3) 0.81172(14) 0.0295(8) Uani 1 1 d . . . H17A H 0.3117 1.0117 0.8511 0.044 Uiso 1 1 calc R . . H17B H 0.1823 1.0408 0.8201 0.044 Uiso 1 1 calc R . . H17C H 0.3092 1.0586 0.7832 0.044 Uiso 1 1 calc R . . C18 C 0.1761(4) 0.8562(3) 0.82372(16) 0.0312(9) Uani 1 1 d . . . H18A H 0.0901 0.8784 0.8239 0.047 Uiso 1 1 calc R . . H18B H 0.2089 0.8571 0.8665 0.047 Uiso 1 1 calc R . . H18C H 0.1788 0.7925 0.8074 0.047 Uiso 1 1 calc R . . C19 C 0.2489(3) 0.99467(18) 0.56011(12) 0.0107(7) Uani 1 1 d . . . C20 C 0.2855(3) 0.9065(2) 0.52801(15) 0.0151(7) Uani 1 1 d . . . C21 C 0.2812(4) 0.8004(2) 0.44375(17) 0.0358(10) Uani 1 1 d . . . H21A H 0.2320 0.7526 0.4651 0.054 Uiso 1 1 calc R . . H21B H 0.3697 0.7876 0.4499 0.054 Uiso 1 1 calc R . . H21C H 0.2622 0.7996 0.3989 0.054 Uiso 1 1 calc R . . C22 C 0.1553(3) 1.0471(2) 0.53878(14) 0.0165(8) Uani 1 1 d . . . H22 H 0.1405 1.1039 0.5603 0.020 Uiso 1 1 calc R . . C23 C 0.0727(3) 1.0264(3) 0.48557(14) 0.0210(7) Uani 1 1 d . . . C24 C -0.0569(4) 0.9119(3) 0.43921(17) 0.0394(11) Uani 1 1 d . . . H24A H -0.0989 0.8535 0.4498 0.059 Uiso 1 1 calc R . . H24B H -0.0007 0.9015 0.4039 0.059 Uiso 1 1 calc R . . H24C H -0.1187 0.9590 0.4278 0.059 Uiso 1 1 calc R . . C25 C 0.5105(3) 0.9342(2) 0.69647(16) 0.0153(8) Uani 1 1 d . . . C26 C 0.5667(3) 0.9821(3) 0.74675(13) 0.0151(6) Uani 1 1 d . . . C27 C 0.6583(3) 0.9454(2) 0.78261(14) 0.0176(8) Uani 1 1 d . . . C28 C 0.6578(3) 0.8151(2) 0.72903(16) 0.0191(8) Uani 1 1 d . . . C29 C 0.5649(3) 0.8459(2) 0.69129(15) 0.0147(7) Uani 1 1 d . . . F1 F 0.5304(2) 1.07124(14) 0.76017(10) 0.0255(5) Uani 1 1 d . . . F2 F 0.70956(17) 0.99724(13) 0.82885(8) 0.0301(5) Uani 1 1 d . . . F3 F 0.7078(2) 0.72964(13) 0.71873(10) 0.0390(6) Uani 1 1 d . . . F4 F 0.52846(17) 0.78760(12) 0.64420(9) 0.0240(5) Uani 1 1 d . . . Ir1 Ir 0.376174(11) 0.979854(8) 0.632794(5) 0.00959(3) Uani 1 1 d . . . H1M H 0.363(3) 1.0702(19) 0.6714(14) 0.028(8) Uiso 1 1 d . . . N1 N 0.7069(3) 0.86191(19) 0.77550(13) 0.0210(6) Uani 1 1 d . . . O1 O 0.3531(2) 0.85300(14) 0.55730(10) 0.0214(6) Uani 1 1 d . . . O2 O 0.2514(2) 0.89115(15) 0.46938(10) 0.0214(6) Uani 1 1 d . . . O3 O 0.0576(3) 1.07706(18) 0.44117(12) 0.0378(7) Uani 1 1 d . . . O4 O 0.0135(2) 0.94416(18) 0.49263(11) 0.0267(6) Uani 1 1 d . . . P1 P 0.52281(8) 1.06664(6) 0.57472(4) 0.01299(18) Uani 1 1 d . . . P2 P 0.21238(8) 0.92817(6) 0.69712(4) 0.01247(19) 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 C1 0.021(2) 0.035(2) 0.0116(18) 0.0003(16) -0.0012(15) -0.0111(16) C2 0.031(2) 0.061(3) 0.021(2) -0.016(2) 0.0031(16) -0.006(2) C3 0.045(3) 0.080(3) 0.016(2) 0.020(2) -0.0018(18) -0.033(2) C4 0.0188(19) 0.0107(16) 0.026(2) 0.0069(14) 0.0005(15) -0.0040(14) C5 0.0253(18) 0.0160(16) 0.049(2) 0.0078(15) -0.006(2) -0.001(2) C6 0.031(2) 0.0135(18) 0.031(2) -0.0040(15) 0.0054(17) -0.0023(15) C7 0.0122(16) 0.021(2) 0.0130(16) 0.0002(13) 0.0018(14) -0.0036(13) C8 0.0119(18) 0.035(2) 0.031(2) 0.0046(17) 0.0014(16) -0.0051(16) C9 0.021(2) 0.026(2) 0.029(2) 0.0019(15) 0.0053(17) 0.0067(15) C10 0.0109(14) 0.017(2) 0.0187(16) -0.0016(12) 0.0032(12) -0.0008(12) C11 0.015(2) 0.0218(18) 0.0272(19) -0.0060(15) 0.0002(15) 0.0060(14) C12 0.0164(17) 0.041(2) 0.032(2) 0.004(2) 0.0065(15) 0.000(2) C13 0.015(2) 0.0152(17) 0.0280(19) 0.0004(14) -0.0003(16) -0.0052(14) C14 0.033(2) 0.0130(17) 0.041(2) 0.0001(16) -0.0019(18) 0.0007(16) C15 0.031(2) 0.0202(17) 0.041(3) -0.0038(17) -0.0066(18) -0.0075(14) C16 0.0142(19) 0.0243(19) 0.0151(17) 0.0068(15) -0.0005(15) 0.0009(15) C17 0.034(2) 0.0376(19) 0.0169(16) -0.0039(19) -0.0052(15) 0.000(2) C18 0.027(2) 0.044(2) 0.023(2) 0.0138(17) 0.0049(16) -0.0021(17) C19 0.0139(15) 0.0065(19) 0.0116(14) -0.0016(12) 0.0052(13) -0.0018(12) C20 0.0122(17) 0.0210(18) 0.0121(17) 0.0015(14) -0.0008(14) -0.0013(14) C21 0.045(3) 0.032(2) 0.030(2) -0.0216(18) -0.0042(19) 0.0108(19) C22 0.0143(19) 0.0202(17) 0.0150(16) -0.0002(12) 0.0012(13) 0.0014(12) C23 0.0187(16) 0.0267(18) 0.0176(16) -0.0059(19) 0.0016(13) 0.0064(18) C24 0.033(2) 0.065(3) 0.020(2) -0.008(2) -0.0071(18) -0.017(2) C25 0.0097(18) 0.0166(17) 0.0196(18) -0.0007(15) 0.0050(14) -0.0033(14) C26 0.0129(14) 0.0178(14) 0.0145(15) 0.0037(16) 0.0012(12) -0.0021(17) C27 0.0157(19) 0.0262(17) 0.0108(16) 0.0026(13) -0.0011(13) -0.0046(13) C28 0.020(2) 0.0132(16) 0.0244(19) 0.0054(14) 0.0004(14) 0.0028(13) C29 0.0143(17) 0.0156(17) 0.0141(17) 0.0000(14) 0.0009(14) 0.0009(14) F1 0.0290(13) 0.0205(11) 0.0269(12) -0.0078(9) -0.0094(10) 0.0039(10) F2 0.0287(10) 0.0394(16) 0.0223(9) -0.0041(9) -0.0121(8) -0.0020(9) F3 0.0422(13) 0.0250(11) 0.0497(14) 0.0013(10) -0.0124(11) 0.0199(10) F4 0.0268(11) 0.0170(10) 0.0282(13) -0.0052(9) -0.0080(10) 0.0066(8) Ir1 0.00891(4) 0.00969(4) 0.01018(5) -0.00033(6) -0.00088(6) 0.00074(6) N1 0.0156(15) 0.0280(16) 0.0195(15) 0.0089(13) -0.0022(12) 0.0004(13) O1 0.0242(16) 0.0216(12) 0.0184(12) -0.0012(10) -0.0032(11) 0.0077(11) O2 0.0282(15) 0.0228(13) 0.0133(12) -0.0073(10) -0.0046(11) 0.0063(11) O3 0.0561(19) 0.0337(15) 0.0237(15) 0.0093(12) -0.0177(13) 0.0106(13) O4 0.0205(14) 0.0431(16) 0.0165(13) -0.0025(11) -0.0061(11) -0.0081(12) P1 0.0109(4) 0.0160(4) 0.0121(4) 0.0007(4) -0.0010(3) -0.0009(4) P2 0.0114(4) 0.0126(4) 0.0134(4) 0.0012(4) 0.0004(3) -0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.533(5) . ? C1 C3 1.544(5) . ? C1 P1 1.873(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 1.523(5) . ? C4 C5 1.529(5) . ? C4 P1 1.858(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 C9 1.533(4) . ? C7 C8 1.547(4) . ? C7 P1 1.849(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 C12 1.539(4) . ? C10 C11 1.540(4) . ? C10 P2 1.850(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 1.524(5) . ? C13 C15 1.540(5) . ? C13 P2 1.859(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 1.524(5) . ? C16 C18 1.540(5) . ? C16 P2 1.875(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 C22 1.339(4) . ? C19 C20 1.492(4) . ? C19 Ir1 2.084(3) . ? C20 O1 1.230(4) . ? C20 O2 1.325(4) . ? C21 O2 1.450(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.475(4) . ? C22 H22 0.9500 . ? C23 O3 1.206(4) . ? C23 O4 1.351(4) . ? C24 O4 1.447(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C29 1.402(4) . ? C25 C26 1.412(5) . ? C25 Ir1 2.093(3) . ? C26 C27 1.357(4) . ? C26 F1 1.369(4) . ? C27 N1 1.316(4) . ? C27 F2 1.356(3) . ? C28 N1 1.311(4) . ? C28 F3 1.357(3) . ? C28 C29 1.360(4) . ? C29 F4 1.366(4) . ? Ir1 P2 2.3583(9) . ? Ir1 P1 2.3651(9) . ? Ir1 O1 2.446(2) . ? Ir1 H1M 1.54(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 C2 C1 C3 109.9(3) . . ? C2 C1 P1 113.4(3) . . ? C3 C1 P1 116.1(3) . . ? C2 C1 H1 105.5 . . ? C3 C1 H1 105.5 . . ? P1 C1 H1 105.5 . . ? 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 109.8(3) . . ? C6 C4 P1 113.0(2) . . ? C5 C4 P1 111.8(2) . . ? C6 C4 H4 107.3 . . ? C5 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 . . ? C9 C7 C8 109.6(3) . . ? C9 C7 P1 113.2(2) . . ? C8 C7 P1 118.0(2) . . ? C9 C7 H7 104.9 . . ? C8 C7 H7 104.9 . . ? P1 C7 H7 104.9 . . ? 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 109.4(3) . . ? C12 C10 P2 116.6(2) . . ? C11 C10 P2 115.2(2) . . ? C12 C10 H10 104.8 . . ? C11 C10 H10 104.8 . . ? P2 C10 H10 104.8 . . ? 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 110.4(3) . . ? C14 C13 P2 111.0(2) . . ? C15 C13 P2 115.2(2) . . ? C14 C13 H13 106.6 . . ? C15 C13 H13 106.6 . . ? P2 C13 H13 106.6 . . ? 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 109.7(3) . . ? C17 C16 P2 111.6(2) . . ? C18 C16 P2 117.4(2) . . ? C17 C16 H16 105.8 . . ? C18 C16 H16 105.8 . . ? P2 C16 H16 105.8 . . ? 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 . . ? C22 C19 C20 121.3(3) . . ? C22 C19 Ir1 143.9(2) . . ? C20 C19 Ir1 94.72(19) . . ? O1 C20 O2 122.8(3) . . ? O1 C20 C19 116.9(3) . . ? O2 C20 C19 120.2(3) . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 C23 127.2(3) . . ? C19 C22 H22 116.4 . . ? C23 C22 H22 116.4 . . ? O3 C23 O4 123.4(3) . . ? O3 C23 C22 124.6(4) . . ? O4 C23 C22 112.0(3) . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C29 C25 C26 108.7(3) . . ? C29 C25 Ir1 121.4(2) . . ? C26 C25 Ir1 129.8(3) . . ? C27 C26 F1 116.9(3) . . ? C27 C26 C25 123.6(3) . . ? F1 C26 C25 119.4(3) . . ? N1 C27 F2 114.9(3) . . ? N1 C27 C26 125.3(3) . . ? F2 C27 C26 119.7(3) . . ? N1 C28 F3 115.2(3) . . ? N1 C28 C29 125.5(3) . . ? F3 C28 C29 119.3(3) . . ? C28 C29 F4 116.8(3) . . ? C28 C29 C25 123.7(3) . . ? F4 C29 C25 119.4(3) . . ? C19 Ir1 C25 166.57(12) . . ? C19 Ir1 P2 88.50(8) . . ? C25 Ir1 P2 92.32(9) . . ? C19 Ir1 P1 89.71(8) . . ? C25 Ir1 P1 92.50(9) . . ? P2 Ir1 P1 166.55(3) . . ? C19 Ir1 O1 61.11(9) . . ? C25 Ir1 O1 105.47(11) . . ? P2 Ir1 O1 94.28(6) . . ? P1 Ir1 O1 96.51(6) . . ? C19 Ir1 H1M 104.5(12) . . ? C25 Ir1 H1M 88.9(12) . . ? P2 Ir1 H1M 83.2(13) . . ? P1 Ir1 H1M 84.4(12) . . ? O1 Ir1 H1M 165.5(13) . . ? C28 N1 C27 113.2(3) . . ? C20 O1 Ir1 86.07(18) . . ? C20 O2 C21 116.5(3) . . ? C23 O4 C24 116.0(3) . . ? C7 P1 C4 102.90(14) . . ? C7 P1 C1 108.21(16) . . ? C4 P1 C1 101.92(16) . . ? C7 P1 Ir1 114.83(10) . . ? C4 P1 Ir1 111.55(11) . . ? C1 P1 Ir1 115.91(12) . . ? C10 P2 C13 102.54(14) . . ? C10 P2 C16 108.56(15) . . ? C13 P2 C16 101.33(15) . . ? C10 P2 Ir1 111.95(9) . . ? C13 P2 Ir1 117.87(11) . . ? C16 P2 Ir1 113.46(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 C19 C20 O1 -164.9(3) . . . . ? Ir1 C19 C20 O1 11.7(3) . . . . ? C22 C19 C20 O2 18.9(4) . . . . ? Ir1 C19 C20 O2 -164.5(3) . . . . ? C20 C19 C22 C23 3.4(5) . . . . ? Ir1 C19 C22 C23 -170.9(3) . . . . ? C19 C22 C23 O3 -123.8(4) . . . . ? C19 C22 C23 O4 57.2(4) . . . . ? C29 C25 C26 C27 0.2(4) . . . . ? Ir1 C25 C26 C27 -176.3(2) . . . . ? C29 C25 C26 F1 178.6(3) . . . . ? Ir1 C25 C26 F1 2.2(4) . . . . ? F1 C26 C27 N1 -178.2(3) . . . . ? C25 C26 C27 N1 0.3(5) . . . . ? F1 C26 C27 F2 -0.4(4) . . . . ? C25 C26 C27 F2 178.1(3) . . . . ? N1 C28 C29 F4 178.3(3) . . . . ? F3 C28 C29 F4 -0.6(4) . . . . ? N1 C28 C29 C25 1.5(5) . . . . ? F3 C28 C29 C25 -177.4(3) . . . . ? C26 C25 C29 C28 -1.0(4) . . . . ? Ir1 C25 C29 C28 175.8(2) . . . . ? C26 C25 C29 F4 -177.7(3) . . . . ? Ir1 C25 C29 F4 -0.9(4) . . . . ? C22 C19 Ir1 C25 167.2(5) . . . . ? C20 C19 Ir1 C25 -8.0(6) . . . . ? C22 C19 Ir1 P2 73.4(4) . . . . ? C20 C19 Ir1 P2 -101.69(16) . . . . ? C22 C19 Ir1 P1 -93.2(4) . . . . ? C20 C19 Ir1 P1 91.63(16) . . . . ? C22 C19 Ir1 O1 169.2(4) . . . . ? C20 C19 Ir1 O1 -5.97(15) . . . . ? C29 C25 Ir1 C19 0.3(7) . . . . ? C26 C25 Ir1 C19 176.4(4) . . . . ? C29 C25 Ir1 P2 93.6(3) . . . . ? C26 C25 Ir1 P2 -90.3(3) . . . . ? C29 C25 Ir1 P1 -98.9(3) . . . . ? C26 C25 Ir1 P1 77.1(3) . . . . ? C29 C25 Ir1 O1 -1.5(3) . . . . ? C26 C25 Ir1 O1 174.6(3) . . . . ? F3 C28 N1 C27 178.0(3) . . . . ? C29 C28 N1 C27 -0.9(5) . . . . ? F2 C27 N1 C28 -177.8(3) . . . . ? C26 C27 N1 C28 0.0(5) . . . . ? O2 C20 O1 Ir1 166.1(3) . . . . ? C19 C20 O1 Ir1 -9.9(3) . . . . ? C19 Ir1 O1 C20 7.24(19) . . . . ? C25 Ir1 O1 C20 -173.2(2) . . . . ? P2 Ir1 O1 C20 93.15(18) . . . . ? P1 Ir1 O1 C20 -78.82(18) . . . . ? O1 C20 O2 C21 9.5(5) . . . . ? C19 C20 O2 C21 -174.6(3) . . . . ? O3 C23 O4 C24 8.9(5) . . . . ? C22 C23 O4 C24 -172.1(3) . . . . ? C9 C7 P1 C4 -173.7(2) . . . . ? C8 C7 P1 C4 -43.7(3) . . . . ? C9 C7 P1 C1 -66.3(3) . . . . ? C8 C7 P1 C1 63.6(3) . . . . ? C9 C7 P1 Ir1 64.9(2) . . . . ? C8 C7 P1 Ir1 -165.2(2) . . . . ? C6 C4 P1 C7 -57.8(3) . . . . ? C5 C4 P1 C7 177.7(2) . . . . ? C6 C4 P1 C1 -169.8(3) . . . . ? C5 C4 P1 C1 65.6(3) . . . . ? C6 C4 P1 Ir1 65.9(3) . . . . ? C5 C4 P1 Ir1 -58.7(3) . . . . ? C2 C1 P1 C7 58.3(3) . . . . ? C3 C1 P1 C7 -70.4(3) . . . . ? C2 C1 P1 C4 166.3(3) . . . . ? C3 C1 P1 C4 37.7(3) . . . . ? C2 C1 P1 Ir1 -72.4(3) . . . . ? C3 C1 P1 Ir1 159.0(3) . . . . ? C19 Ir1 P1 C7 -157.23(13) . . . . ? C25 Ir1 P1 C7 9.52(14) . . . . ? P2 Ir1 P1 C7 120.44(16) . . . . ? O1 Ir1 P1 C7 -96.37(12) . . . . ? C19 Ir1 P1 C4 86.20(14) . . . . ? C25 Ir1 P1 C4 -107.05(15) . . . . ? P2 Ir1 P1 C4 3.87(19) . . . . ? O1 Ir1 P1 C4 147.06(13) . . . . ? C19 Ir1 P1 C1 -29.83(16) . . . . ? C25 Ir1 P1 C1 136.92(17) . . . . ? P2 Ir1 P1 C1 -112.15(18) . . . . ? O1 Ir1 P1 C1 31.04(15) . . . . ? C12 C10 P2 C13 54.3(3) . . . . ? C11 C10 P2 C13 -175.5(2) . . . . ? C12 C10 P2 C16 -52.4(3) . . . . ? C11 C10 P2 C16 77.8(2) . . . . ? C12 C10 P2 Ir1 -178.4(2) . . . . ? C11 C10 P2 Ir1 -48.2(2) . . . . ? C14 C13 P2 C10 178.5(2) . . . . ? C15 C13 P2 C10 52.1(3) . . . . ? C14 C13 P2 C16 -69.4(3) . . . . ? C15 C13 P2 C16 164.3(3) . . . . ? C14 C13 P2 Ir1 55.0(3) . . . . ? C15 C13 P2 Ir1 -71.3(3) . . . . ? C17 C16 P2 C10 -51.6(3) . . . . ? C18 C16 P2 C10 76.3(3) . . . . ? C17 C16 P2 C13 -159.1(2) . . . . ? C18 C16 P2 C13 -31.2(3) . . . . ? C17 C16 P2 Ir1 73.6(3) . . . . ? C18 C16 P2 Ir1 -158.6(2) . . . . ? C19 Ir1 P2 C10 -45.78(13) . . . . ? C25 Ir1 P2 C10 147.63(15) . . . . ? P1 Ir1 P2 C10 36.68(18) . . . . ? O1 Ir1 P2 C10 -106.67(12) . . . . ? C19 Ir1 P2 C13 72.76(14) . . . . ? C25 Ir1 P2 C13 -93.83(16) . . . . ? P1 Ir1 P2 C13 155.23(16) . . . . ? O1 Ir1 P2 C13 11.88(13) . . . . ? C19 Ir1 P2 C16 -169.08(14) . . . . ? C25 Ir1 P2 C16 24.33(14) . . . . ? P1 Ir1 P2 C16 -86.61(17) . . . . ? O1 Ir1 P2 C16 130.04(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.599 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.065 data_d:\ziemer\akaju7_complex5 _database_code_depnum_ccdc_archive 'CCDC 725698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H35 F4 Ir N3 O4 P, C6 H6' _chemical_formula_sum 'C26 H41 F4 Ir N3 O4 P' _chemical_formula_weight 758.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 10.7140(3) _cell_length_b 13.1461(3) _cell_length_c 21.3446(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.574(2) _cell_angle_gamma 90.00 _cell_volume 3000.48(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method none _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 4.563 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4622 _exptl_absorpt_correction_T_max 0.6105 _exptl_absorpt_process_details ; The crystal faces were indexed by microscope on the diffractometer. After that a numerical absorption correction basing on a Gaussian algorithsm was applied, which is implemented in the X-RED program (Stoe, 2002). ; _exptl_special_details ; During data collection the crystal was in cold N~2~ gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a 2-circle goniometer supplied with an area detector. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long fine focus sealed X-ray tube' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_collimation '0.5 mm diameter monocapillary' _diffrn_measurement_device 'Stoe IPDS-2t diffractometer' _diffrn_measurement_method '\w-rotation,\w-incr.=1\%,332 exposures' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 49585 _diffrn_reflns_av_R_equivalents 0.1414 _diffrn_reflns_av_sigmaI/netI 0.1249 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 29.00 _reflns_number_total 7955 _reflns_number_gt 4591 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (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. C15 can not refined anisotropicially, not even when its thermal parameters are restrained to those of neighbouring atoms by SIMU. ; _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^)+(0.0231P)^2^] 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 7955 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 0.836 _refine_ls_restrained_S_all 0.836 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3502(7) 0.8484(5) 0.0766(3) 0.0171(13) Uani 1 1 d . . . H1 H 0.3569 0.8996 0.1114 0.020 Uiso 1 1 calc R . . C2 C 0.4264(9) 0.8923(6) 0.0247(4) 0.0255(18) Uani 1 1 d . . . H2A H 0.4075 0.8545 -0.0143 0.038 Uiso 1 1 calc R . . H2B H 0.5158 0.8863 0.0370 0.038 Uiso 1 1 calc R . . H2C H 0.4048 0.9641 0.0182 0.038 Uiso 1 1 calc R . . C3 C 0.2108(7) 0.8473(5) 0.0535(4) 0.0254(16) Uani 1 1 d . . . H3A H 0.1868 0.9145 0.0370 0.038 Uiso 1 1 calc R . . H3B H 0.1597 0.8303 0.0886 0.038 Uiso 1 1 calc R . . H3C H 0.1974 0.7963 0.0203 0.038 Uiso 1 1 calc R . . C4 C 0.4248(8) 0.6321(5) 0.0480(3) 0.0174(16) Uani 1 1 d . . . H4 H 0.4495 0.5676 0.0703 0.021 Uiso 1 1 calc R . . C5 C 0.5241(8) 0.6496(5) 0.0018(3) 0.0254(16) Uani 1 1 d . . . H5A H 0.5295 0.5900 -0.0255 0.038 Uiso 1 1 d R . . H5B H 0.6050 0.6608 0.0248 0.038 Uiso 1 1 d R . . H5C H 0.5021 0.7096 -0.0239 0.038 Uiso 1 1 d R . . C6 C 0.2981(8) 0.6081(6) 0.0113(4) 0.0294(19) Uani 1 1 d . . . H6A H 0.2739 0.6654 -0.0161 0.044 Uiso 1 1 d R . . H6B H 0.2335 0.5967 0.0411 0.044 Uiso 1 1 d R . . H6C H 0.3073 0.5468 -0.0141 0.044 Uiso 1 1 d R . . C7 C 0.2868(6) 0.6842(5) 0.1552(3) 0.0188(14) Uani 1 1 d . . . H7 H 0.2127 0.6798 0.1244 0.023 Uiso 1 1 calc R . . C8 C 0.3071(7) 0.5777(5) 0.1821(3) 0.0216(14) Uani 1 1 d . . . H8A H 0.2297 0.5538 0.1995 0.026 Uiso 1 1 calc R . . H8B H 0.3742 0.5795 0.2154 0.026 Uiso 1 1 calc R . . H8C H 0.3302 0.5314 0.1488 0.026 Uiso 1 1 calc R . . C9 C 0.2508(6) 0.7573(8) 0.2066(3) 0.0247(13) Uani 1 1 d . . . H9A H 0.3179 0.7594 0.2399 0.030 Uiso 1 1 calc R . . H9B H 0.1733 0.7340 0.2240 0.030 Uiso 1 1 calc R . . H9C H 0.2381 0.8255 0.1888 0.030 Uiso 1 1 calc R . . C10 C 0.5922(6) 0.9128(4) 0.1709(3) 0.0132(14) Uani 1 1 d . . . C11 C 0.6624(7) 0.9808(5) 0.1394(3) 0.0170(14) Uani 1 1 d . . . C12 C 0.6680(7) 1.0834(5) 0.1533(3) 0.0203(15) Uani 1 1 d . . . C13 C 0.5415(6) 1.0647(5) 0.2297(3) 0.0192(14) Uani 1 1 d . . . C14 C 0.5265(6) 0.9630(5) 0.2166(3) 0.0152(13) Uani 1 1 d . . . C15 C 0.6759(6) 0.6053(4) 0.1522(3) 0.0110(11) Uiso 1 1 d . . . C16 C 0.6198(6) 0.5205(5) 0.1872(3) 0.0138(13) Uani 1 1 d . . . C17 C 0.4963(8) 0.3710(5) 0.1749(3) 0.0249(16) Uani 1 1 d . . . H17A H 0.4662 0.3898 0.2158 0.030 Uiso 1 1 calc R . . H17B H 0.5584 0.3165 0.1806 0.030 Uiso 1 1 calc R . . H17C H 0.4259 0.3474 0.1472 0.030 Uiso 1 1 calc R . . C18 C 0.7795(6) 0.5842(5) 0.1226(3) 0.0151(13) Uani 1 1 d . . . H18 H 0.8148 0.6377 0.0996 0.018 Uiso 1 1 calc R . . C19 C 0.8431(7) 0.4850(5) 0.1229(3) 0.0212(15) Uani 1 1 d . . . C20 C 1.0086(12) 0.3937(8) 0.0810(6) 0.036(3) Uani 1 1 d . . . H20A H 1.0646 0.3986 0.0465 0.043 Uiso 1 1 calc R . . H20B H 0.9514 0.3362 0.0735 0.043 Uiso 1 1 calc R . . H20C H 1.0580 0.3834 0.1207 0.043 Uiso 1 1 calc R . . C21 C 0.2844(8) 0.1307(7) 0.0980(4) 0.0302(19) Uani 1 1 d . . . H21 H 0.3710 0.1453 0.1050 0.036 Uiso 1 1 calc R . . C22 C 0.2231(8) 0.1545(6) 0.0412(4) 0.0298(17) Uani 1 1 d . . . H22 H 0.2674 0.1849 0.0088 0.036 Uiso 1 1 calc R . . C23 C 0.0968(8) 0.1339(6) 0.0316(4) 0.0279(17) Uani 1 1 d . . . H23 H 0.0546 0.1502 -0.0076 0.034 Uiso 1 1 calc R . . C24 C 0.0323(11) 0.0904(7) 0.0776(6) 0.029(2) Uani 1 1 d . . . H24 H -0.0545 0.0767 0.0706 0.035 Uiso 1 1 calc R . . C25 C 0.0943(8) 0.0664(6) 0.1347(4) 0.0307(17) Uani 1 1 d . . . H25 H 0.0496 0.0364 0.1671 0.037 Uiso 1 1 calc R . . C26 C 0.2206(8) 0.0859(6) 0.1446(4) 0.0314(18) Uani 1 1 d . . . H26 H 0.2632 0.0684 0.1835 0.038 Uiso 1 1 calc R . . F1 F 0.7365(4) 0.9483(3) 0.09349(19) 0.0214(9) Uani 1 1 d . . . F2 F 0.7427(4) 1.1442(3) 0.12117(19) 0.0260(10) Uani 1 1 d . . . F3 F 0.4842(4) 1.1068(3) 0.2776(2) 0.0274(10) Uani 1 1 d . . . F4 F 0.4468(4) 0.9122(3) 0.25356(18) 0.0197(8) Uani 1 1 d . . . Ir1 Ir 0.60938(2) 0.75570(2) 0.160960(11) 0.01067(5) Uani 1 1 d . . . N1 N 0.7994(5) 0.7884(4) 0.1967(3) 0.0163(12) Uani 1 1 d . . . H1A H 0.8226 0.7433 0.2276 0.025 Uiso 1 1 calc R . . H1B H 0.8032 0.8527 0.2125 0.025 Uiso 1 1 calc R . . H1C H 0.8520 0.7829 0.1650 0.025 Uiso 1 1 calc R . . N2 N 0.5796(5) 0.7278(4) 0.2622(2) 0.0170(12) Uani 1 1 d . . . H2D H 0.4963 0.7299 0.2683 0.026 Uiso 1 1 calc R . . H2E H 0.6198 0.7767 0.2860 0.026 Uiso 1 1 calc R . . H2F H 0.6106 0.6656 0.2736 0.026 Uiso 1 1 calc R . . N3 N 0.6125(6) 1.1262(4) 0.1986(3) 0.0178(12) Uani 1 1 d . . . O1 O 0.6278(5) 0.5079(3) 0.2432(2) 0.0195(10) Uani 1 1 d . . . O2 O 0.5529(5) 0.4584(3) 0.1473(2) 0.0185(10) Uani 1 1 d . . . O3 O 0.8186(5) 0.4117(4) 0.1548(2) 0.0239(11) Uani 1 1 d . . . O4 O 0.9374(5) 0.4864(4) 0.0843(2) 0.0275(12) Uani 1 1 d . . . P1 P 0.41925(16) 0.72963(11) 0.11069(7) 0.0139(4) 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 C1 0.021(4) 0.010(3) 0.021(3) -0.001(2) 0.002(3) 0.003(3) C2 0.033(5) 0.020(4) 0.022(4) 0.005(3) -0.005(4) 0.003(3) C3 0.018(4) 0.022(3) 0.034(4) 0.000(3) -0.010(3) 0.007(3) C4 0.027(4) 0.008(3) 0.017(4) 0.001(2) -0.009(3) -0.001(3) C5 0.037(5) 0.014(3) 0.025(3) -0.007(3) 0.000(3) 0.000(3) C6 0.029(4) 0.023(4) 0.033(4) -0.008(3) -0.021(4) 0.002(3) C7 0.012(3) 0.019(3) 0.026(3) 0.000(3) 0.001(3) -0.005(3) C8 0.017(3) 0.020(3) 0.029(4) -0.001(3) 0.007(3) -0.001(3) C9 0.022(3) 0.021(3) 0.031(3) -0.002(4) 0.003(2) -0.007(4) C10 0.009(3) 0.014(3) 0.015(3) 0.000(2) -0.007(3) -0.005(2) C11 0.020(4) 0.013(3) 0.017(3) -0.001(2) -0.006(3) 0.001(3) C12 0.028(4) 0.014(3) 0.017(3) 0.002(2) -0.013(3) -0.001(3) C13 0.013(3) 0.015(3) 0.029(4) -0.005(3) -0.007(3) 0.003(3) C14 0.013(3) 0.013(3) 0.019(3) -0.001(2) -0.001(3) -0.001(3) C16 0.007(3) 0.015(3) 0.018(3) -0.006(2) -0.006(2) 0.005(2) C17 0.035(5) 0.013(3) 0.026(4) 0.001(3) -0.004(3) -0.010(3) C18 0.016(3) 0.013(3) 0.016(3) -0.003(2) -0.002(3) 0.004(3) C19 0.021(4) 0.019(3) 0.021(3) -0.004(3) -0.010(3) 0.003(3) C20 0.037(7) 0.038(5) 0.032(6) -0.010(4) 0.003(5) 0.016(5) C21 0.014(4) 0.036(4) 0.041(5) -0.014(4) 0.001(3) -0.002(3) C22 0.028(4) 0.023(4) 0.040(4) -0.007(3) 0.014(3) -0.006(3) C23 0.030(4) 0.027(4) 0.027(4) -0.003(3) 0.001(3) 0.006(3) C24 0.015(4) 0.031(4) 0.043(6) -0.008(4) 0.005(4) 0.003(4) C25 0.031(4) 0.032(4) 0.030(4) -0.004(3) 0.010(3) -0.001(4) C26 0.036(5) 0.034(4) 0.024(4) -0.008(3) -0.002(3) 0.010(4) F1 0.026(2) 0.0176(19) 0.021(2) 0.0014(16) 0.0060(18) -0.0050(18) F2 0.036(3) 0.0159(19) 0.026(2) 0.0031(17) -0.0022(19) -0.0101(19) F3 0.018(2) 0.020(2) 0.044(3) -0.0131(19) 0.0028(19) 0.0028(17) F4 0.014(2) 0.0163(18) 0.029(2) -0.0043(16) 0.0061(16) -0.0020(16) Ir1 0.01397(9) 0.00534(8) 0.01227(8) -0.00069(15) -0.00254(6) 0.00028(16) N1 0.012(3) 0.014(2) 0.023(3) -0.005(2) 0.001(2) -0.002(2) N2 0.020(3) 0.010(3) 0.020(2) -0.0033(19) -0.003(2) 0.001(2) N3 0.015(3) 0.012(3) 0.024(3) 0.000(2) -0.011(2) 0.001(2) O1 0.028(3) 0.011(2) 0.019(2) 0.0001(18) -0.005(2) 0.001(2) O2 0.024(3) 0.010(2) 0.020(2) 0.0021(18) -0.008(2) -0.0012(19) O3 0.025(3) 0.016(2) 0.029(3) -0.003(2) -0.008(2) 0.007(2) O4 0.026(3) 0.025(3) 0.032(3) -0.005(2) 0.006(2) 0.007(2) P1 0.0151(7) 0.0112(9) 0.0150(7) -0.0004(6) -0.0024(6) -0.0001(6) _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 C1 C2 1.529(11) . ? C1 C3 1.543(9) . ? C1 P1 1.857(6) . ? 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 1.513(12) . ? C4 C6 1.556(10) . ? C4 P1 1.857(7) . ? C4 H4 1.0000 . ? C5 H5A 0.9801 . ? C5 H5B 0.9800 . ? C5 H5C 0.9799 . ? C6 H6A 0.9799 . ? C6 H6B 0.9800 . ? C6 H6C 0.9801 . ? C7 C8 1.523(9) . ? C7 C9 1.526(10) . ? C7 P1 1.855(7) . ? 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 1.371(9) . ? C10 C14 1.403(9) . ? C10 Ir1 2.085(6) . ? C11 F1 1.368(8) . ? C11 C12 1.381(9) . ? C12 N3 1.295(10) . ? C12 F2 1.348(8) . ? C13 N3 1.318(9) . ? C13 F3 1.345(8) . ? C13 C14 1.373(9) . ? C14 F4 1.371(8) . ? C15 C18 1.341(9) . ? C15 C16 1.490(9) . ? C15 Ir1 2.113(6) . ? C16 O1 1.204(8) . ? C16 O2 1.353(7) . ? C17 O2 1.442(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.472(9) . ? C18 H18 0.9500 . ? C19 O3 1.219(9) . ? C19 O4 1.342(9) . ? C20 O4 1.441(11) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.375(12) . ? C21 C22 1.379(11) . ? C21 H21 0.9500 . ? C22 C23 1.382(11) . ? C22 H22 0.9500 . ? C23 C24 1.361(15) . ? C23 H23 0.9500 . ? C24 C25 1.389(14) . ? C24 H24 0.9500 . ? C25 C26 1.381(12) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? Ir1 N1 2.172(5) . ? Ir1 N2 2.235(5) . ? Ir1 P1 2.2684(16) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N2 H2D 0.9100 . ? N2 H2E 0.9100 . ? N2 H2F 0.9100 . ? 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 C2 C1 C3 108.8(6) . . ? C2 C1 P1 112.5(5) . . ? C3 C1 P1 118.1(5) . . ? C2 C1 H1 105.5 . . ? C3 C1 H1 105.5 . . ? P1 C1 H1 105.5 . . ? 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 109.2(6) . . ? C5 C4 P1 114.9(5) . . ? C6 C4 P1 115.9(6) . . ? C5 C4 H4 105.2 . . ? C6 C4 H4 105.2 . . ? P1 C4 H4 105.2 . . ? C4 C5 H5A 109.6 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.4 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.6 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.4 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 110.1(6) . . ? C8 C7 P1 113.2(5) . . ? C9 C7 P1 113.6(5) . . ? C8 C7 H7 106.5 . . ? C9 C7 H7 106.5 . . ? P1 C7 H7 106.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C14 110.4(6) . . ? C11 C10 Ir1 122.8(5) . . ? C14 C10 Ir1 126.0(5) . . ? F1 C11 C10 120.5(6) . . ? F1 C11 C12 116.0(6) . . ? C10 C11 C12 123.4(7) . . ? N3 C12 F2 115.9(6) . . ? N3 C12 C11 124.6(7) . . ? F2 C12 C11 119.3(7) . . ? N3 C13 F3 115.8(6) . . ? N3 C13 C14 124.0(7) . . ? F3 C13 C14 120.1(7) . . ? F4 C14 C13 115.2(6) . . ? F4 C14 C10 121.9(5) . . ? C13 C14 C10 122.8(7) . . ? C18 C15 C16 117.0(6) . . ? C18 C15 Ir1 121.9(5) . . ? C16 C15 Ir1 120.5(4) . . ? O1 C16 O2 123.0(6) . . ? O1 C16 C15 126.5(6) . . ? O2 C16 C15 110.5(5) . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 C19 125.4(6) . . ? C15 C18 H18 117.3 . . ? C19 C18 H18 117.3 . . ? O3 C19 O4 123.4(7) . . ? O3 C19 C18 125.9(7) . . ? O4 C19 C18 110.6(6) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 120.2(8) . . ? C26 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 119.5(8) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 120.8(8) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.5(10) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C24 120.2(9) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C21 C26 C25 119.7(7) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C10 Ir1 C15 165.4(2) . . ? C10 Ir1 N1 81.7(2) . . ? C15 Ir1 N1 84.4(2) . . ? C10 Ir1 N2 92.6(2) . . ? C15 Ir1 N2 90.1(2) . . ? N1 Ir1 N2 83.1(2) . . ? C10 Ir1 P1 96.64(18) . . ? C15 Ir1 P1 96.59(17) . . ? N1 Ir1 P1 172.07(16) . . ? N2 Ir1 P1 104.75(15) . . ? Ir1 N1 H1A 109.5 . . ? Ir1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? Ir1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? Ir1 N2 H2D 109.5 . . ? Ir1 N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? Ir1 N2 H2F 109.5 . . ? H2D N2 H2F 109.5 . . ? H2E N2 H2F 109.5 . . ? C12 N3 C13 114.6(6) . . ? C16 O2 C17 116.2(5) . . ? C19 O4 C20 116.1(7) . . ? C7 P1 C1 99.9(3) . . ? C7 P1 C4 101.9(3) . . ? C1 P1 C4 109.2(3) . . ? C7 P1 Ir1 120.0(2) . . ? C1 P1 Ir1 112.5(2) . . ? C4 P1 Ir1 112.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C10 C11 F1 178.6(5) . . . . ? Ir1 C10 C11 F1 8.4(8) . . . . ? C14 C10 C11 C12 1.7(9) . . . . ? Ir1 C10 C11 C12 -168.5(5) . . . . ? F1 C11 C12 N3 -174.2(6) . . . . ? C10 C11 C12 N3 2.9(11) . . . . ? F1 C11 C12 F2 0.8(9) . . . . ? C10 C11 C12 F2 177.8(6) . . . . ? N3 C13 C14 F4 -178.8(6) . . . . ? F3 C13 C14 F4 2.7(9) . . . . ? N3 C13 C14 C10 4.2(10) . . . . ? F3 C13 C14 C10 -174.3(6) . . . . ? C11 C10 C14 F4 178.3(5) . . . . ? Ir1 C10 C14 F4 -11.9(9) . . . . ? C11 C10 C14 C13 -4.9(9) . . . . ? Ir1 C10 C14 C13 164.9(5) . . . . ? C18 C15 C16 O1 102.9(8) . . . . ? Ir1 C15 C16 O1 -68.2(8) . . . . ? C18 C15 C16 O2 -79.0(7) . . . . ? Ir1 C15 C16 O2 109.9(5) . . . . ? C16 C15 C18 C19 -1.1(9) . . . . ? Ir1 C15 C18 C19 169.9(5) . . . . ? C15 C18 C19 O3 -8.0(11) . . . . ? C15 C18 C19 O4 174.5(6) . . . . ? C26 C21 C22 C23 0.6(12) . . . . ? C21 C22 C23 C24 0.0(12) . . . . ? C22 C23 C24 C25 -0.2(13) . . . . ? C23 C24 C25 C26 -0.4(13) . . . . ? C22 C21 C26 C25 -1.1(12) . . . . ? C24 C25 C26 C21 1.0(13) . . . . ? C11 C10 Ir1 C15 43.0(12) . . . . ? C14 C10 Ir1 C15 -125.6(9) . . . . ? C11 C10 Ir1 N1 60.6(5) . . . . ? C14 C10 Ir1 N1 -108.1(6) . . . . ? C11 C10 Ir1 N2 143.2(5) . . . . ? C14 C10 Ir1 N2 -25.4(6) . . . . ? C11 C10 Ir1 P1 -111.6(5) . . . . ? C14 C10 Ir1 P1 79.8(5) . . . . ? C18 C15 Ir1 C10 -33.9(12) . . . . ? C16 C15 Ir1 C10 136.7(9) . . . . ? C18 C15 Ir1 N1 -51.3(5) . . . . ? C16 C15 Ir1 N1 119.3(5) . . . . ? C18 C15 Ir1 N2 -134.4(5) . . . . ? C16 C15 Ir1 N2 36.3(5) . . . . ? C18 C15 Ir1 P1 120.7(5) . . . . ? C16 C15 Ir1 P1 -68.6(4) . . . . ? F2 C12 N3 C13 -179.0(5) . . . . ? C11 C12 N3 C13 -3.9(9) . . . . ? F3 C13 N3 C12 179.1(5) . . . . ? C14 C13 N3 C12 0.5(9) . . . . ? O1 C16 O2 C17 -3.6(9) . . . . ? C15 C16 O2 C17 178.2(6) . . . . ? O3 C19 O4 C20 1.6(10) . . . . ? C18 C19 O4 C20 179.2(7) . . . . ? C8 C7 P1 C1 171.9(5) . . . . ? C9 C7 P1 C1 -61.5(5) . . . . ? C8 C7 P1 C4 59.7(5) . . . . ? C9 C7 P1 C4 -173.7(5) . . . . ? C8 C7 P1 Ir1 -64.8(5) . . . . ? C9 C7 P1 Ir1 61.7(5) . . . . ? C2 C1 P1 C7 -166.9(5) . . . . ? C3 C1 P1 C7 -38.9(6) . . . . ? C2 C1 P1 C4 -60.5(6) . . . . ? C3 C1 P1 C4 67.6(6) . . . . ? C2 C1 P1 Ir1 64.7(5) . . . . ? C3 C1 P1 Ir1 -167.3(5) . . . . ? C5 C4 P1 C7 178.7(5) . . . . ? C6 C4 P1 C7 49.7(6) . . . . ? C5 C4 P1 C1 73.6(6) . . . . ? C6 C4 P1 C1 -55.4(6) . . . . ? C5 C4 P1 Ir1 -51.7(5) . . . . ? C6 C4 P1 Ir1 179.3(5) . . . . ? C10 Ir1 P1 C7 -98.9(3) . . . . ? C15 Ir1 P1 C7 87.3(3) . . . . ? N1 Ir1 P1 C7 -176.0(11) . . . . ? N2 Ir1 P1 C7 -4.5(3) . . . . ? C10 Ir1 P1 C1 18.1(3) . . . . ? C15 Ir1 P1 C1 -155.7(3) . . . . ? N1 Ir1 P1 C1 -59.0(11) . . . . ? N2 Ir1 P1 C1 112.5(3) . . . . ? C10 Ir1 P1 C4 141.6(3) . . . . ? C15 Ir1 P1 C4 -32.2(3) . . . . ? N1 Ir1 P1 C4 64.5(11) . . . . ? N2 Ir1 P1 C4 -124.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.812 _refine_diff_density_min -2.805 _refine_diff_density_rms 0.163 data_akju13_complex6 _database_code_depnum_ccdc_archive 'CCDC 725699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H32 F4 Ir N2 O4 P, 0.5(C6 H6)' _chemical_formula_sum 'C23 H35 F4 Ir N2 O4 P' _chemical_formula_weight 702.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M '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 14.7892(4) _cell_length_b 10.4836(2) _cell_length_c 17.1372(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.780(7) _cell_angle_gamma 90.00 _cell_volume 2625.89(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.777 _exptl_crystal_density_method none _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 5.205 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.3235 _exptl_absorpt_process_details ; The crystal faces were indexed by microscope on the diffractometer. After that a numerical absorption correction basing on a Gaussian algorithsm was applied, which is implemented in the X-RED program (Stoe, 2002). ; _exptl_special_details ; During data collection the crystal was in cold N~2~ gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a 2-circle goniometer supplied with an area detector. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long fine focus sealed X-ray tube' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_collimation '0.5 mm diameter monocapillary' _diffrn_measurement_device 'Stoe IPDS-2t diffractometer' _diffrn_measurement_method '\w-rotation,\w-incr.=1\%,360 exposures' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 47604 _diffrn_reflns_av_R_equivalents 0.0952 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 28.75 _reflns_number_total 6817 _reflns_number_gt 5946 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (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. The disorder of C21 was not modelled further, because it is part of a disordered benzene molecule at a special position, which was modelled with part-1. ; _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^)+(0.0290P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00202(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6817 _refine_ls_number_parameters 344 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0415 _refine_ls_wR_factor_gt 0.0403 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.49278(18) 0.2613(2) 0.32591(15) 0.0225(5) Uani 1 1 d . . . H1 H 0.5304 0.2641 0.3796 0.027 Uiso 1 1 calc R . . C2 C 0.4898(2) 0.3968(3) 0.29308(17) 0.0288(6) Uani 1 1 d . . . H2A H 0.4656 0.4547 0.3298 0.043 Uiso 1 1 calc R . . H2B H 0.4501 0.3990 0.2418 0.043 Uiso 1 1 calc R . . H2C H 0.5517 0.4236 0.2866 0.043 Uiso 1 1 calc R . . C3 C 0.39795(18) 0.2169(3) 0.33668(15) 0.0256(5) Uani 1 1 d . . . H3A H 0.4026 0.1361 0.3658 0.038 Uiso 1 1 calc R . . H3B H 0.3607 0.2045 0.2848 0.038 Uiso 1 1 calc R . . H3C H 0.3692 0.2813 0.3663 0.038 Uiso 1 1 calc R . . C4 C 0.54281(19) -0.0022(3) 0.31755(16) 0.0245(5) Uani 1 1 d . . . H4 H 0.4761 -0.0232 0.3090 0.029 Uiso 1 1 calc R . . C5 C 0.5707(2) 0.0026(3) 0.40754(17) 0.0322(6) Uani 1 1 d . . . H5A H 0.6373 0.0103 0.4203 0.048 Uiso 1 1 calc R . . H5B H 0.5507 -0.0758 0.4310 0.048 Uiso 1 1 calc R . . H5C H 0.5418 0.0763 0.4288 0.048 Uiso 1 1 calc R . . C6 C 0.5894(2) -0.1160(2) 0.28315(18) 0.0303(6) Uani 1 1 d . . . H6A H 0.5752 -0.1143 0.2254 0.036 Uiso 1 1 calc R . . H6B H 0.5668 -0.1958 0.3029 0.036 Uiso 1 1 calc R . . H6C H 0.6558 -0.1104 0.2992 0.036 Uiso 1 1 calc R . . C7 C 0.67083(18) 0.2098(3) 0.28118(16) 0.0255(5) Uani 1 1 d . . . H7 H 0.6719 0.2820 0.2432 0.031 Uiso 1 1 calc R . . C8 C 0.7076(2) 0.2670(3) 0.36320(17) 0.0329(6) Uani 1 1 d . . . H8A H 0.7704 0.2972 0.3637 0.049 Uiso 1 1 calc R . . H8B H 0.7070 0.2014 0.4038 0.049 Uiso 1 1 calc R . . H8C H 0.6687 0.3386 0.3740 0.049 Uiso 1 1 calc R . . C9 C 0.73820(19) 0.1098(3) 0.25664(19) 0.0353(7) Uani 1 1 d . . . H9A H 0.7507 0.0448 0.2980 0.053 Uiso 1 1 calc R . . H9B H 0.7955 0.1520 0.2494 0.053 Uiso 1 1 calc R . . H9C H 0.7110 0.0694 0.2070 0.053 Uiso 1 1 calc R . . C10 C 0.58141(15) 0.2739(2) 0.09656(13) 0.0140(4) Uani 1 1 d . . . C11 C 0.65734(16) 0.2416(2) 0.06228(15) 0.0185(4) Uani 1 1 d . . . C12 C 0.70695(17) 0.3297(2) 0.02733(16) 0.0228(5) Uani 1 1 d . . . C13 C 0.61914(17) 0.4873(2) 0.05592(15) 0.0192(5) Uani 1 1 d . . . C14 C 0.56457(15) 0.4048(2) 0.09061(13) 0.0155(4) Uani 1 1 d . . . C15 C 0.29905(15) 0.2008(2) 0.13768(14) 0.0161(4) Uani 1 1 d . . . C16 C 0.30451(16) 0.0631(2) 0.14626(14) 0.0172(4) Uani 1 1 d . . . H16 H 0.2523 0.0110 0.1482 0.021 Uiso 1 1 calc R . . C17 C 0.38994(16) 0.0152(2) 0.15126(13) 0.0149(4) Uani 1 1 d . . . C18 C 0.21082(18) 0.3889(2) 0.12669(18) 0.0261(5) Uani 1 1 d . . . H18A H 0.1466 0.4150 0.1146 0.039 Uiso 1 1 calc R . . H18B H 0.2436 0.4171 0.0842 0.039 Uiso 1 1 calc R . . H18C H 0.2387 0.4278 0.1766 0.039 Uiso 1 1 calc R . . C19 C 0.39999(16) -0.1252(2) 0.15007(14) 0.0182(4) Uani 1 1 d . . . C20 C 0.3789(3) -0.3236(3) 0.2089(2) 0.0390(8) Uani 1 1 d . . . H20A H 0.3552 -0.3602 0.2543 0.059 Uiso 1 1 calc R . . H20B H 0.4439 -0.3447 0.2121 0.059 Uiso 1 1 calc R . . H20C H 0.3450 -0.3587 0.1600 0.059 Uiso 1 1 calc R . . C21 C 0.9574(7) 0.0860(8) 0.0217(5) 0.073(4) Uani 0.50 1 d PGU A -1 H21 H 0.9238 0.1542 0.0399 0.088 Uiso 0.50 1 calc PR A -1 C22 C 0.9127(6) -0.0252(10) -0.0064(6) 0.062(4) Uani 0.50 1 d PGU A -1 H22 H 0.8485 -0.0331 -0.0074 0.075 Uiso 0.50 1 calc PR A -1 C23 C 0.9619(8) -0.1249(8) -0.0331(6) 0.094(6) Uani 0.50 1 d PGU A -1 H23 H 0.9313 -0.2009 -0.0523 0.113 Uiso 0.50 1 calc PR A -1 C24 C 1.0557(8) -0.1133(10) -0.0317(6) 0.066(4) Uani 0.50 1 d PGU A -1 H24 H 1.0893 -0.1815 -0.0500 0.079 Uiso 0.50 1 calc PR A -1 C25 C 1.1004(6) -0.0021(12) -0.0036(6) 0.074(5) Uani 0.50 1 d PGU A -1 H25 H 1.1646 0.0058 -0.0026 0.088 Uiso 0.50 1 calc PR A -1 C26 C 1.0513(7) 0.0976(9) 0.0231(6) 0.056(3) Uani 0.50 1 d PGU A -1 H26 H 1.0818 0.1736 0.0423 0.067 Uiso 0.50 1 calc PR A -1 N1 N 0.43702(13) 0.12556(18) 0.01132(11) 0.0152(3) Uani 1 1 d . . . H1A H 0.4833 0.1328 -0.0178 0.023 Uiso 1 1 calc R . . H1B H 0.3956 0.1890 -0.0022 0.023 Uiso 1 1 calc R . . H1C H 0.4091 0.0486 0.0018 0.023 Uiso 1 1 calc R . . N2 N 0.69019(15) 0.4530(2) 0.02401(13) 0.0229(4) Uani 1 1 d . . . O1 O 0.36725(11) 0.26767(15) 0.13425(10) 0.0151(3) Uani 1 1 d . . . O2 O 0.21610(12) 0.25137(17) 0.13354(11) 0.0219(4) Uani 1 1 d . . . O3 O 0.43355(13) -0.18213(17) 0.10011(11) 0.0236(4) Uani 1 1 d . . . O4 O 0.36791(14) -0.18570(16) 0.20913(12) 0.0266(4) Uani 1 1 d . . . F1 F 0.68475(10) 0.11787(13) 0.05863(10) 0.0247(3) Uani 1 1 d . . . F2 F 0.77767(12) 0.29078(18) -0.00806(12) 0.0366(4) Uani 1 1 d . . . F3 F 0.60001(11) 0.61317(13) 0.05394(10) 0.0264(3) Uani 1 1 d . . . F4 F 0.49181(10) 0.45724(13) 0.11754(9) 0.0209(3) Uani 1 1 d . . . P1 P 0.55201(4) 0.15132(6) 0.26451(3) 0.01628(11) Uani 1 1 d . . . Ir1 Ir 0.491741(5) 0.140658(7) 0.135248(5) 0.01138(3) Uani 1 1 d . . . H1D H 0.5668(18) 0.055(3) 0.1321(16) 0.014 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 C1 0.0268(12) 0.0222(12) 0.0185(11) -0.0053(9) 0.0032(9) 0.0020(10) C2 0.0385(15) 0.0208(12) 0.0266(13) -0.0047(10) 0.0032(11) 0.0038(10) C3 0.0285(13) 0.0299(13) 0.0193(12) -0.0050(10) 0.0072(10) -0.0012(11) C4 0.0273(13) 0.0238(12) 0.0233(12) 0.0027(10) 0.0063(10) 0.0025(10) C5 0.0387(16) 0.0344(15) 0.0230(13) 0.0084(11) 0.0033(11) 0.0007(12) C6 0.0406(15) 0.0181(12) 0.0319(14) 0.0039(10) 0.0045(12) 0.0075(10) C7 0.0224(12) 0.0295(13) 0.0241(12) 0.0018(10) 0.0021(9) -0.0035(10) C8 0.0252(13) 0.0462(18) 0.0253(13) -0.0041(12) -0.0027(10) -0.0060(12) C9 0.0198(12) 0.0484(18) 0.0370(16) 0.0035(13) 0.0019(11) 0.0003(12) C10 0.0163(10) 0.0123(9) 0.0133(10) -0.0013(8) 0.0022(8) -0.0013(8) C11 0.0189(11) 0.0154(10) 0.0221(11) -0.0016(9) 0.0059(9) 0.0001(8) C12 0.0198(11) 0.0243(12) 0.0266(12) -0.0031(10) 0.0109(9) -0.0023(9) C13 0.0209(11) 0.0133(10) 0.0226(11) 0.0009(9) 0.0011(9) -0.0042(8) C14 0.0155(9) 0.0142(10) 0.0167(10) -0.0017(8) 0.0028(8) -0.0013(8) C15 0.0170(10) 0.0158(10) 0.0163(10) 0.0003(8) 0.0052(8) 0.0003(8) C16 0.0201(10) 0.0133(10) 0.0190(10) 0.0001(8) 0.0057(8) -0.0039(8) C17 0.0217(11) 0.0117(9) 0.0128(10) -0.0005(8) 0.0069(8) -0.0028(8) C18 0.0235(12) 0.0178(12) 0.0400(15) 0.0062(10) 0.0143(11) 0.0061(9) C19 0.0238(11) 0.0145(10) 0.0173(10) 0.0001(8) 0.0067(8) -0.0029(9) C20 0.071(2) 0.0117(11) 0.0429(17) 0.0049(11) 0.0345(17) 0.0033(12) C21 0.126(9) 0.079(9) 0.016(3) 0.011(4) 0.017(5) 0.097(7) C22 0.012(3) 0.131(12) 0.039(5) 0.054(6) -0.012(3) -0.024(5) C23 0.111(12) 0.065(8) 0.085(11) 0.054(7) -0.048(9) -0.018(8) C24 0.101(8) 0.049(5) 0.038(5) -0.010(4) -0.021(5) 0.057(6) C25 0.070(9) 0.113(10) 0.042(6) 0.035(7) 0.020(6) 0.043(8) C26 0.092(9) 0.028(4) 0.033(4) 0.011(4) -0.036(5) -0.034(5) N1 0.0209(9) 0.0125(8) 0.0127(8) -0.0005(7) 0.0039(7) 0.0010(7) N2 0.0230(10) 0.0213(10) 0.0256(11) 0.0008(8) 0.0072(8) -0.0053(8) O1 0.0169(8) 0.0122(7) 0.0175(8) -0.0004(6) 0.0066(6) -0.0001(6) O2 0.0177(8) 0.0171(8) 0.0327(10) 0.0044(7) 0.0094(7) 0.0021(6) O3 0.0369(10) 0.0145(8) 0.0227(9) -0.0042(7) 0.0153(8) -0.0036(7) O4 0.0467(11) 0.0094(7) 0.0292(10) 0.0035(7) 0.0236(9) 0.0026(7) F1 0.0256(7) 0.0158(7) 0.0358(8) -0.0041(6) 0.0144(6) 0.0040(5) F2 0.0315(9) 0.0336(9) 0.0518(11) -0.0015(8) 0.0290(8) -0.0018(7) F3 0.0283(8) 0.0125(7) 0.0388(9) 0.0051(6) 0.0065(7) -0.0032(5) F4 0.0221(7) 0.0138(6) 0.0290(8) -0.0001(5) 0.0108(6) 0.0020(5) P1 0.0212(3) 0.0135(3) 0.0137(2) -0.0008(2) 0.0015(2) 0.0017(2) Ir1 0.01463(4) 0.00827(4) 0.01185(4) -0.00100(3) 0.00398(2) 0.00074(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.516(4) . ? C1 C2 1.525(4) . ? C1 P1 1.867(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 1.535(4) . ? C4 C6 1.540(4) . ? C4 P1 1.864(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 C9 1.548(4) . ? C7 C8 1.548(4) . ? C7 P1 1.842(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 1.386(3) . ? C10 C14 1.396(3) . ? C10 Ir1 2.102(2) . ? C11 F1 1.363(3) . ? C11 C12 1.373(3) . ? C12 N2 1.316(3) . ? C12 F2 1.350(3) . ? C13 N2 1.307(3) . ? C13 F3 1.349(3) . ? C13 C14 1.378(3) . ? C14 F4 1.351(3) . ? C15 O1 1.237(3) . ? C15 O2 1.328(3) . ? C15 C16 1.452(3) . ? C16 C17 1.350(3) . ? C16 H16 0.9500 . ? C17 C19 1.480(3) . ? C17 Ir1 2.049(2) . ? C18 O2 1.448(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O3 1.211(3) . ? C19 O4 1.341(3) . ? C20 O4 1.455(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C21 H21 0.9500 . ? C22 C23 1.3900 . ? C22 H22 0.9500 . ? C23 C24 1.3900 . ? C23 H23 0.9500 . ? C24 C25 1.3900 . ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 Ir1 2.1601(18) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? O1 Ir1 2.2700(16) . ? P1 Ir1 2.2608(6) . ? Ir1 H1D 1.44(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 C3 C1 C2 110.8(2) . . ? C3 C1 P1 113.65(18) . . ? C2 C1 P1 110.91(18) . . ? C3 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? P1 C1 H1 107.0 . . ? 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 110.0(2) . . ? C5 C4 P1 115.7(2) . . ? C6 C4 P1 114.35(19) . . ? C5 C4 H4 105.2 . . ? C6 C4 H4 105.2 . . ? P1 C4 H4 105.2 . . ? 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 110.9(2) . . ? C9 C7 P1 111.8(2) . . ? C8 C7 P1 117.66(19) . . ? C9 C7 H7 105.1 . . ? C8 C7 H7 105.1 . . ? P1 C7 H7 105.1 . . ? 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 C14 110.8(2) . . ? C11 C10 Ir1 124.23(16) . . ? C14 C10 Ir1 124.22(16) . . ? F1 C11 C12 116.0(2) . . ? F1 C11 C10 121.1(2) . . ? C12 C11 C10 122.8(2) . . ? N2 C12 F2 115.6(2) . . ? N2 C12 C11 124.8(2) . . ? F2 C12 C11 119.7(2) . . ? N2 C13 F3 115.9(2) . . ? N2 C13 C14 124.7(2) . . ? F3 C13 C14 119.3(2) . . ? F4 C14 C13 116.2(2) . . ? F4 C14 C10 121.2(2) . . ? C13 C14 C10 122.6(2) . . ? O1 C15 O2 121.6(2) . . ? O1 C15 C16 122.4(2) . . ? O2 C15 C16 116.0(2) . . ? C17 C16 C15 114.4(2) . . ? C17 C16 H16 122.8 . . ? C15 C16 H16 122.8 . . ? C16 C17 C19 117.6(2) . . ? C16 C17 Ir1 116.93(16) . . ? C19 C17 Ir1 124.00(17) . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 O4 122.1(2) . . ? O3 C19 C17 123.6(2) . . ? O4 C19 C17 114.3(2) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 120.0 . . ? C22 C21 H21 120.0 . . ? C26 C21 H21 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.0 . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.0 . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.0 . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? Ir1 N1 H1A 109.5 . . ? Ir1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? Ir1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C13 N2 C12 114.2(2) . . ? C15 O1 Ir1 109.47(14) . . ? C15 O2 C18 116.10(19) . . ? C19 O4 C20 114.5(2) . . ? C7 P1 C4 110.55(13) . . ? C7 P1 C1 103.03(12) . . ? C4 P1 C1 100.55(12) . . ? C7 P1 Ir1 113.11(9) . . ? C4 P1 Ir1 112.83(9) . . ? C1 P1 Ir1 115.72(8) . . ? C17 Ir1 C10 168.74(9) . . ? C17 Ir1 N1 84.95(8) . . ? C10 Ir1 N1 84.16(8) . . ? C17 Ir1 P1 95.07(6) . . ? C10 Ir1 P1 95.90(6) . . ? N1 Ir1 P1 178.20(5) . . ? C17 Ir1 O1 76.45(8) . . ? C10 Ir1 O1 99.08(7) . . ? N1 Ir1 O1 81.60(7) . . ? P1 Ir1 O1 100.16(4) . . ? C17 Ir1 H1D 100.9(11) . . ? C10 Ir1 H1D 83.0(11) . . ? N1 Ir1 H1D 95.3(11) . . ? P1 Ir1 H1D 82.9(11) . . ? O1 Ir1 H1D 176.0(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C10 C11 F1 -177.6(2) . . . . ? Ir1 C10 C11 F1 -6.9(3) . . . . ? C14 C10 C11 C12 -0.4(3) . . . . ? Ir1 C10 C11 C12 170.3(2) . . . . ? F1 C11 C12 N2 179.1(2) . . . . ? C10 C11 C12 N2 1.8(4) . . . . ? F1 C11 C12 F2 0.3(4) . . . . ? C10 C11 C12 F2 -177.0(2) . . . . ? N2 C13 C14 F4 -177.3(2) . . . . ? F3 C13 C14 F4 2.9(3) . . . . ? N2 C13 C14 C10 1.4(4) . . . . ? F3 C13 C14 C10 -178.4(2) . . . . ? C11 C10 C14 F4 177.6(2) . . . . ? Ir1 C10 C14 F4 6.9(3) . . . . ? C11 C10 C14 C13 -1.0(3) . . . . ? Ir1 C10 C14 C13 -171.73(18) . . . . ? O1 C15 C16 C17 0.9(3) . . . . ? O2 C15 C16 C17 -179.2(2) . . . . ? C15 C16 C17 C19 -172.6(2) . . . . ? C15 C16 C17 Ir1 -5.7(3) . . . . ? C16 C17 C19 O3 119.4(3) . . . . ? Ir1 C17 C19 O3 -46.4(3) . . . . ? C16 C17 C19 O4 -60.0(3) . . . . ? Ir1 C17 C19 O4 134.14(19) . . . . ? C26 C21 C22 C23 0.0 . . . . ? C21 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C21 0.0 . . . . ? C22 C21 C26 C25 0.0 . . . . ? F3 C13 N2 C12 179.7(2) . . . . ? C14 C13 N2 C12 0.0(4) . . . . ? F2 C12 N2 C13 177.4(2) . . . . ? C11 C12 N2 C13 -1.5(4) . . . . ? O2 C15 O1 Ir1 -176.18(18) . . . . ? C16 C15 O1 Ir1 3.7(3) . . . . ? O1 C15 O2 C18 -1.4(3) . . . . ? C16 C15 O2 C18 178.7(2) . . . . ? O3 C19 O4 C20 1.4(4) . . . . ? C17 C19 O4 C20 -179.1(2) . . . . ? C9 C7 P1 C4 56.2(2) . . . . ? C8 C7 P1 C4 -73.9(2) . . . . ? C9 C7 P1 C1 162.9(2) . . . . ? C8 C7 P1 C1 32.8(2) . . . . ? C9 C7 P1 Ir1 -71.5(2) . . . . ? C8 C7 P1 Ir1 158.5(2) . . . . ? C5 C4 P1 C7 60.0(2) . . . . ? C6 C4 P1 C7 -69.5(2) . . . . ? C5 C4 P1 C1 -48.4(2) . . . . ? C6 C4 P1 C1 -177.8(2) . . . . ? C5 C4 P1 Ir1 -172.25(18) . . . . ? C6 C4 P1 Ir1 58.3(2) . . . . ? C3 C1 P1 C7 -167.63(19) . . . . ? C2 C1 P1 C7 66.7(2) . . . . ? C3 C1 P1 C4 -53.5(2) . . . . ? C2 C1 P1 C4 -179.11(19) . . . . ? C3 C1 P1 Ir1 68.4(2) . . . . ? C2 C1 P1 Ir1 -57.3(2) . . . . ? C16 C17 Ir1 C10 -62.1(5) . . . . ? C19 C17 Ir1 C10 103.8(5) . . . . ? C16 C17 Ir1 N1 -76.87(18) . . . . ? C19 C17 Ir1 N1 89.0(2) . . . . ? C16 C17 Ir1 P1 104.94(18) . . . . ? C19 C17 Ir1 P1 -89.15(19) . . . . ? C16 C17 Ir1 O1 5.69(17) . . . . ? C19 C17 Ir1 O1 171.6(2) . . . . ? C11 C10 Ir1 C17 -92.8(5) . . . . ? C14 C10 Ir1 C17 76.7(5) . . . . ? C11 C10 Ir1 N1 -78.0(2) . . . . ? C14 C10 Ir1 N1 91.50(19) . . . . ? C11 C10 Ir1 P1 100.2(2) . . . . ? C14 C10 Ir1 P1 -90.31(19) . . . . ? C11 C10 Ir1 O1 -158.48(19) . . . . ? C14 C10 Ir1 O1 11.0(2) . . . . ? C7 P1 Ir1 C17 160.11(12) . . . . ? C4 P1 Ir1 C17 33.69(11) . . . . ? C1 P1 Ir1 C17 -81.35(11) . . . . ? C7 P1 Ir1 C10 -22.41(12) . . . . ? C4 P1 Ir1 C10 -148.83(11) . . . . ? C1 P1 Ir1 C10 96.12(11) . . . . ? C7 P1 Ir1 O1 -122.77(11) . . . . ? C4 P1 Ir1 O1 110.81(10) . . . . ? C1 P1 Ir1 O1 -4.23(10) . . . . ? C15 O1 Ir1 C17 -4.92(16) . . . . ? C15 O1 Ir1 C10 164.54(16) . . . . ? C15 O1 Ir1 N1 81.88(16) . . . . ? C15 O1 Ir1 P1 -97.74(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.75 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.545 _refine_diff_density_min -0.954 _refine_diff_density_rms 0.093 data_maah19_complex9 _database_code_depnum_ccdc_archive 'CCDC 725700' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H54 F8 Ir2 N6 P2, C6 H6' _chemical_formula_sum 'C34 H60 F8 Ir2 N6 P2' _chemical_formula_weight 1151.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' F F 0.0171 0.0103 '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 13.6890(2) _cell_length_b 9.9290(2) _cell_length_c 15.0110(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.8640(10) _cell_angle_gamma 90.00 _cell_volume 2037.72(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6231 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.876 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 6.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3091 _exptl_absorpt_correction_T_max 0.6174 _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 47134 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4653 _reflns_number_gt 4306 _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^)+(0.0074P)^2^+2.5212P] 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 4653 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0186 _refine_ls_R_factor_gt 0.0159 _refine_ls_wR_factor_ref 0.0340 _refine_ls_wR_factor_gt 0.0332 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.097720(6) 0.090567(8) 0.027407(5) 0.01170(3) Uani 1 1 d . . . H1D H 0.0849(18) 0.071(2) 0.1266(16) 0.014(6) Uiso 1 1 d . . . P1 P 0.25528(4) 0.03849(6) 0.06862(4) 0.01371(11) Uani 1 1 d . . . N1 N 0.05574(13) -0.11109(18) -0.00294(13) 0.0141(4) Uani 1 1 d . . . H1B H 0.0854 -0.1424 -0.0525 0.017 Uiso 1 1 calc R . . H1C H 0.0703 -0.1678 0.0443 0.017 Uiso 1 1 calc R . . N2 N 0.09422(15) 0.1127(2) -0.12116(13) 0.0207(4) Uani 1 1 d . . . H2D H 0.0703 0.1954 -0.1367 0.031 Uiso 1 1 calc R . . H2E H 0.0550 0.0479 -0.1467 0.031 Uiso 1 1 calc R . . H2F H 0.1559 0.1038 -0.1404 0.031 Uiso 1 1 calc R . . N3 N 0.09843(15) 0.5812(2) 0.07718(14) 0.0218(4) Uani 1 1 d . . . F1 F 0.01389(11) 0.28392(14) 0.18273(9) 0.0244(3) Uani 1 1 d . . . F2 F 0.01238(12) 0.54916(16) 0.19954(10) 0.0331(4) Uani 1 1 d . . . F3 F 0.18075(11) 0.61097(14) -0.04842(10) 0.0280(3) Uani 1 1 d . . . F4 F 0.19576(11) 0.34969(14) -0.07735(10) 0.0253(3) Uani 1 1 d . . . C1 C 0.34158(17) -0.0007(2) -0.02033(15) 0.0172(5) Uani 1 1 d . . . H1A H 0.4047 -0.0310 0.0095 0.021 Uiso 1 1 calc R . . C2 C 0.36277(18) 0.1241(3) -0.07630(16) 0.0227(5) Uani 1 1 d . . . H2A H 0.4059 0.0993 -0.1239 0.034 Uiso 1 1 calc R . . H2B H 0.3947 0.1928 -0.0381 0.034 Uiso 1 1 calc R . . H2C H 0.3012 0.1600 -0.1027 0.034 Uiso 1 1 calc R . . C3 C 0.30312(18) -0.1153(3) -0.08045(17) 0.0237(5) Uani 1 1 d . . . H3A H 0.2395 -0.0899 -0.1083 0.036 Uiso 1 1 calc R . . H3B H 0.2958 -0.1969 -0.0447 0.036 Uiso 1 1 calc R . . H3C H 0.3494 -0.1324 -0.1269 0.036 Uiso 1 1 calc R . . C4 C 0.32135(17) 0.1749(2) 0.13117(16) 0.0192(5) Uani 1 1 d . . . H4 H 0.3113 0.2572 0.0935 0.023 Uiso 1 1 calc R . . C5 C 0.2743(2) 0.2079(3) 0.21917(17) 0.0300(6) Uani 1 1 d . . . H5A H 0.2977 0.1440 0.2652 0.045 Uiso 1 1 calc R . . H5B H 0.2030 0.2011 0.2108 0.045 Uiso 1 1 calc R . . H5C H 0.2922 0.2996 0.2377 0.045 Uiso 1 1 calc R . . C6 C 0.43292(18) 0.1625(3) 0.14710(18) 0.0274(6) Uani 1 1 d . . . H6A H 0.4590 0.2463 0.1733 0.041 Uiso 1 1 calc R . . H6B H 0.4629 0.1458 0.0902 0.041 Uiso 1 1 calc R . . H6C H 0.4479 0.0875 0.1880 0.041 Uiso 1 1 calc R . . C7 C 0.26232(17) -0.1209(2) 0.13610(16) 0.0182(5) Uani 1 1 d . . . H7 H 0.2378 -0.1931 0.0943 0.022 Uiso 1 1 calc R . . C8 C 0.1949(2) -0.1261(3) 0.21395(18) 0.0314(6) Uani 1 1 d . . . H8A H 0.1951 -0.2174 0.2388 0.047 Uiso 1 1 calc R . . H8B H 0.1282 -0.1021 0.1929 0.047 Uiso 1 1 calc R . . H8C H 0.2180 -0.0623 0.2601 0.047 Uiso 1 1 calc R . . C9 C 0.36468(19) -0.1672(3) 0.16881(19) 0.0317(6) Uani 1 1 d . . . H9A H 0.3902 -0.1064 0.2158 0.048 Uiso 1 1 calc R . . H9B H 0.4083 -0.1659 0.1190 0.048 Uiso 1 1 calc R . . H9C H 0.3611 -0.2589 0.1925 0.048 Uiso 1 1 calc R . . C10 C 0.10719(15) 0.2922(2) 0.05101(15) 0.0148(4) Uani 1 1 d . . . C11 C 0.06104(17) 0.3572(2) 0.12092(15) 0.0184(5) Uani 1 1 d . . . C12 C 0.05912(18) 0.4940(2) 0.13102(16) 0.0214(5) Uani 1 1 d . . . C13 C 0.14136(17) 0.5248(2) 0.01007(17) 0.0199(5) Uani 1 1 d . . . C14 C 0.14780(17) 0.3889(2) -0.00401(16) 0.0182(5) Uani 1 1 d . . . C15 C 0.4117(2) 0.5323(3) 0.0337(2) 0.0376(7) Uani 1 1 d . . . H15 H 0.3507 0.5547 0.0575 0.045 Uiso 1 1 calc R . . C16 C 0.4946(2) 0.5226(3) 0.0898(2) 0.0401(7) Uani 1 1 d . . . H16 H 0.4904 0.5383 0.1520 0.048 Uiso 1 1 calc R . . C17 C 0.4168(2) 0.5097(3) -0.0562(2) 0.0366(7) Uani 1 1 d . . . H17 H 0.3598 0.5163 -0.0947 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01117(5) 0.01064(5) 0.01323(5) -0.00024(3) 0.00020(3) -0.00026(3) P1 0.0121(3) 0.0144(3) 0.0145(3) -0.0005(2) 0.0002(2) -0.0001(2) N1 0.0124(9) 0.0119(9) 0.0180(9) 0.0001(7) 0.0014(7) 0.0008(7) N2 0.0173(10) 0.0242(11) 0.0204(10) -0.0008(8) 0.0001(8) -0.0026(9) N3 0.0233(11) 0.0149(10) 0.0266(11) 0.0005(8) -0.0035(9) 0.0011(8) F1 0.0349(8) 0.0188(7) 0.0203(7) -0.0006(6) 0.0104(6) 0.0011(6) F2 0.0523(10) 0.0218(8) 0.0263(8) -0.0056(6) 0.0125(7) 0.0067(7) F3 0.0287(8) 0.0166(7) 0.0393(9) 0.0075(6) 0.0090(7) -0.0028(6) F4 0.0277(8) 0.0197(7) 0.0298(8) 0.0016(6) 0.0148(6) -0.0014(6) C1 0.0135(11) 0.0204(12) 0.0178(11) 0.0007(9) 0.0016(9) 0.0012(9) C2 0.0202(12) 0.0259(13) 0.0223(12) 0.0039(10) 0.0042(10) 0.0002(10) C3 0.0223(13) 0.0251(13) 0.0241(13) -0.0072(10) 0.0047(10) -0.0004(10) C4 0.0168(12) 0.0191(12) 0.0212(12) -0.0034(10) -0.0042(9) 0.0005(9) C5 0.0293(14) 0.0370(16) 0.0232(13) -0.0117(12) -0.0042(11) 0.0005(12) C6 0.0174(13) 0.0305(15) 0.0333(14) -0.0042(12) -0.0076(10) -0.0021(11) C7 0.0175(11) 0.0189(12) 0.0184(11) 0.0045(9) 0.0019(9) -0.0003(9) C8 0.0312(15) 0.0355(16) 0.0279(14) 0.0138(12) 0.0070(11) 0.0097(12) C9 0.0231(14) 0.0348(16) 0.0369(15) 0.0142(13) -0.0003(11) 0.0050(12) C10 0.0119(10) 0.0141(11) 0.0182(11) 0.0012(9) -0.0025(8) 0.0013(9) C11 0.0221(12) 0.0171(12) 0.0161(11) 0.0007(9) -0.0001(9) -0.0009(10) C12 0.0247(13) 0.0194(12) 0.0201(12) -0.0043(10) 0.0002(10) 0.0047(10) C13 0.0168(12) 0.0144(12) 0.0283(13) 0.0039(10) -0.0009(10) -0.0009(9) C14 0.0146(11) 0.0181(12) 0.0219(12) -0.0014(9) 0.0008(9) -0.0009(9) C15 0.0262(15) 0.0403(18) 0.0458(18) -0.0005(14) -0.0044(13) 0.0013(13) C16 0.0416(18) 0.0439(19) 0.0338(16) -0.0038(14) -0.0081(13) 0.0030(15) C17 0.0295(15) 0.0356(17) 0.0432(17) -0.0042(14) -0.0125(13) 0.0025(13) _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 C10 2.036(2) . ? Ir1 N1 2.1243(18) 3 ? Ir1 N1 2.1261(18) . ? Ir1 N2 2.239(2) . ? Ir1 P1 2.2735(6) . ? Ir1 H1D 1.52(2) . ? P1 C4 1.857(2) . ? P1 C1 1.867(2) . ? P1 C7 1.879(2) . ? N1 Ir1 2.1243(18) 3 ? N1 H1B 0.9200 . ? N1 H1C 0.9200 . ? N2 H2D 0.9100 . ? N2 H2E 0.9100 . ? N2 H2F 0.9100 . ? N3 C13 1.316(3) . ? N3 C12 1.317(3) . ? F1 C11 1.366(3) . ? F2 C12 1.354(3) . ? F3 C13 1.357(3) . ? F4 C14 1.366(3) . ? C1 C3 1.529(3) . ? C1 C2 1.533(3) . ? C1 H1A 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 1.534(3) . ? C4 C6 1.539(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 1.526(3) . ? C7 C9 1.532(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 C14 1.400(3) . ? C10 C11 1.408(3) . ? C11 C12 1.368(3) . ? C13 C14 1.369(3) . ? C15 C17 1.374(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9500 . ? C16 C17 1.374(4) 3_665 ? C16 H16 0.9500 . ? C17 C16 1.374(4) 3_665 ? C17 H17 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 C10 Ir1 N1 89.40(8) . 3 ? C10 Ir1 N1 167.80(8) . . ? N1 Ir1 N1 78.40(8) 3 . ? C10 Ir1 N2 94.29(8) . . ? N1 Ir1 N2 81.18(7) 3 . ? N1 Ir1 N2 83.51(7) . . ? C10 Ir1 P1 97.18(6) . . ? N1 Ir1 P1 170.20(5) 3 . ? N1 Ir1 P1 94.97(5) . . ? N2 Ir1 P1 105.44(5) . . ? C10 Ir1 H1D 87.8(9) . . ? N1 Ir1 H1D 91.1(9) 3 . ? N1 Ir1 H1D 92.8(9) . . ? N2 Ir1 H1D 172.0(9) . . ? P1 Ir1 H1D 81.9(9) . . ? C4 P1 C1 101.77(11) . . ? C4 P1 C7 109.33(11) . . ? C1 P1 C7 101.11(11) . . ? C4 P1 Ir1 113.78(8) . . ? C1 P1 Ir1 118.57(8) . . ? C7 P1 Ir1 111.14(7) . . ? Ir1 N1 Ir1 101.60(8) 3 . ? Ir1 N1 H1B 111.5 3 . ? Ir1 N1 H1B 111.5 . . ? Ir1 N1 H1C 111.5 3 . ? Ir1 N1 H1C 111.5 . . ? H1B N1 H1C 109.3 . . ? Ir1 N2 H2D 109.5 . . ? Ir1 N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? Ir1 N2 H2F 109.5 . . ? H2D N2 H2F 109.5 . . ? H2E N2 H2F 109.5 . . ? C13 N3 C12 113.7(2) . . ? C3 C1 C2 110.3(2) . . ? C3 C1 P1 111.44(16) . . ? C2 C1 P1 111.54(16) . . ? C3 C1 H1A 107.8 . . ? C2 C1 H1A 107.8 . . ? P1 C1 H1A 107.8 . . ? 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(2) . . ? C5 C4 P1 112.13(17) . . ? C6 C4 P1 118.35(17) . . ? C5 C4 H4 105.1 . . ? C6 C4 H4 105.1 . . ? P1 C4 H4 105.1 . . ? 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 108.8(2) . . ? C8 C7 P1 115.14(17) . . ? C9 C7 P1 116.56(17) . . ? C8 C7 H7 105.0 . . ? C9 C7 H7 105.0 . . ? P1 C7 H7 105.0 . . ? 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 . . ? C14 C10 C11 109.4(2) . . ? C14 C10 Ir1 126.56(17) . . ? C11 C10 Ir1 123.58(17) . . ? F1 C11 C12 116.2(2) . . ? F1 C11 C10 120.5(2) . . ? C12 C11 C10 123.3(2) . . ? N3 C12 F2 115.1(2) . . ? N3 C12 C11 125.0(2) . . ? F2 C12 C11 119.9(2) . . ? N3 C13 F3 115.7(2) . . ? N3 C13 C14 124.9(2) . . ? F3 C13 C14 119.4(2) . . ? F4 C14 C13 116.3(2) . . ? F4 C14 C10 120.0(2) . . ? C13 C14 C10 123.7(2) . . ? C17 C15 C16 120.4(3) . . ? C17 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.3(3) 3_665 . ? C17 C16 H16 119.8 3_665 . ? C15 C16 H16 119.8 . . ? C16 C17 C15 119.2(3) 3_665 . ? C16 C17 H17 120.4 3_665 . ? C15 C17 H17 120.4 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.956 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.084