# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. #TrackingRef '- compilation_djukic.cif' _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jean-Pierre Djukic' _publ_contact_author_address ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4 rue Blaise Pascal F-67000 Strasbourg France ; _publ_contact_author_email djukic@unistra.fr _publ_contact_author_phone +33(0)368851323 loop_ _publ_author_name _publ_author_address J.-P.Djukic ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4 rue Blaise Pascal F-67000 Strasbourg France ; W.Iali ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4 rue Blaise Pascal F-67000 Strasbourg France ; M.Pfeffer ;Institut de Chimie CNRS UMR 7177 Universite de Strasbourg 4 rue Blaise Pascal F-67000 Strasbourg France ; 'X.-F.Le Goff' ;Laboratoire Heteroelements et Coordination Ecole Polytechnique Route de Saclay, 91128 Palaiseau Cedex France ; data_2a _database_code_depnum_ccdc_archive 'CCDC 805113' #TrackingRef '- compilation_djukic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 Cl Ir N2' _chemical_formula_sum 'C23 H28 Cl Ir N2' _chemical_formula_weight 560.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.5371(6) _cell_length_b 7.5131(3) _cell_length_c 20.9885(6) _cell_angle_alpha 90.00 _cell_angle_beta 128.903(2) _cell_angle_gamma 90.00 _cell_volume 2029.35(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9910 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 32.08 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 6.721 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1844 _exptl_absorpt_correction_T_max 0.3467 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20707 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 32.08 _reflns_number_total 7014 _reflns_number_gt 6324 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+4.1026P] 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 7014 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0523 _refine_ls_wR_factor_gt 0.0504 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 Ir1 Ir -0.267470(6) -0.258435(10) -0.998843(5) 0.01386(3) Uani 1 1 d . . . Cl1 Cl -0.32964(5) -0.54194(8) -1.06777(4) 0.02188(11) Uani 1 1 d . . . N1 N -0.29354(16) -0.3639(3) -0.92061(13) 0.0166(4) Uani 1 1 d . . . N2 N 0.13504(18) -0.4641(4) -0.84389(16) 0.0290(5) Uani 1 1 d . . . C1 C -0.12850(18) -0.3758(3) -0.91031(14) 0.0150(4) Uani 1 1 d . . . C2 C -0.04238(19) -0.3782(3) -0.90755(15) 0.0181(4) Uani 1 1 d . . . H2 H -0.0467 -0.3205 -0.9499 0.022 Uiso 1 1 calc R . . C3 C 0.05145(19) -0.4634(3) -0.84412(15) 0.0198(4) Uani 1 1 d . . . C4 C 0.0559(2) -0.5514(3) -0.78263(16) 0.0227(5) Uani 1 1 d . . . H4 H 0.1179 -0.6103 -0.7394 0.027 Uiso 1 1 calc R . . C5 C -0.0293(2) -0.5524(3) -0.78481(15) 0.0207(5) Uani 1 1 d . . . H5 H -0.0257 -0.6139 -0.7435 0.025 Uiso 1 1 calc R . . C6 C -0.12093(18) -0.4639(3) -0.84718(14) 0.0158(4) Uani 1 1 d . . . C7 C -0.21354(19) -0.4569(3) -0.85414(14) 0.0170(4) Uani 1 1 d . . . C8 C -0.2266(2) -0.5366(3) -0.80067(16) 0.0229(5) Uani 1 1 d . . . H8 H -0.1706 -0.5990 -0.7537 0.027 Uiso 1 1 calc R . . C9 C -0.3209(2) -0.5245(4) -0.81630(17) 0.0270(5) Uani 1 1 d . . . H9 H -0.3301 -0.5788 -0.7804 0.032 Uiso 1 1 calc R . . C10 C -0.4024(2) -0.4322(4) -0.88505(18) 0.0268(5) Uani 1 1 d . . . H10 H -0.4680 -0.4227 -0.8971 0.032 Uiso 1 1 calc R . . C11 C -0.3852(2) -0.3550(4) -0.93532(17) 0.0228(5) Uani 1 1 d . . . H11 H -0.4408 -0.2926 -0.9825 0.027 Uiso 1 1 calc R . . C12 C 0.2370(2) -0.5113(5) -0.76996(19) 0.0338(7) Uani 1 1 d . . . H12A H 0.2564 -0.4307 -0.7256 0.051 Uiso 1 1 calc R . . H12B H 0.2878 -0.5011 -0.7794 0.051 Uiso 1 1 calc R . . H12C H 0.2359 -0.6340 -0.7547 0.051 Uiso 1 1 calc R . . C13 C 0.1321(2) -0.3572(5) -0.9026(2) 0.0342(7) Uani 1 1 d . . . H13A H 0.0746 -0.3968 -0.9581 0.051 Uiso 1 1 calc R . . H13B H 0.1978 -0.3702 -0.8932 0.051 Uiso 1 1 calc R . . H13C H 0.1219 -0.2319 -0.8962 0.051 Uiso 1 1 calc R . . C14 C -0.2426(2) -0.0894(3) -1.06843(14) 0.0182(4) Uani 1 1 d . . . C15 C -0.20860(19) 0.0023(3) -0.99487(14) 0.0165(4) Uani 1 1 d . . . C16 C -0.2977(2) 0.0214(3) -0.99808(15) 0.0177(4) Uani 1 1 d . . . C17 C -0.3885(2) -0.0456(3) -1.07653(16) 0.0209(5) Uani 1 1 d . . . C18 C -0.3538(2) -0.1134(3) -1.11821(15) 0.0202(4) Uani 1 1 d . . . C19 C -0.1779(2) -0.1286(4) -1.09422(18) 0.0267(5) Uani 1 1 d . . . H19A H -0.2017 -0.0550 -1.1417 0.040 Uiso 1 1 calc R . . H19B H -0.1848 -0.2547 -1.1089 0.040 Uiso 1 1 calc R . . H19C H -0.1049 -0.1017 -1.0490 0.040 Uiso 1 1 calc R . . C20 C -0.1043(2) 0.0796(4) -0.93120(16) 0.0246(5) Uani 1 1 d . . . H20A H -0.1026 0.2028 -0.9456 0.037 Uiso 1 1 calc R . . H20B H -0.0516 0.0096 -0.9277 0.037 Uiso 1 1 calc R . . H20C H -0.0897 0.0773 -0.8782 0.037 Uiso 1 1 calc R . . C21 C -0.3000(2) 0.1134(4) -0.93623(18) 0.0258(5) Uani 1 1 d . . . H21A H -0.2293 0.1211 -0.8841 0.039 Uiso 1 1 calc R . . H21B H -0.3438 0.0460 -0.9283 0.039 Uiso 1 1 calc R . . H21C H -0.3284 0.2336 -0.9556 0.039 Uiso 1 1 calc R . . C22 C -0.4982(2) -0.0315(4) -1.1086(2) 0.0337(7) Uani 1 1 d . . . H22A H -0.5303 0.0749 -1.1430 0.050 Uiso 1 1 calc R . . H22B H -0.4995 -0.0228 -1.0627 0.050 Uiso 1 1 calc R . . H22C H -0.5369 -0.1373 -1.1412 0.050 Uiso 1 1 calc R . . C23 C -0.4212(3) -0.1961(4) -1.20203(17) 0.0325(6) Uani 1 1 d . . . H23A H -0.4681 -0.2830 -1.2055 0.049 Uiso 1 1 calc R . . H23B H -0.3774 -0.2560 -1.2119 0.049 Uiso 1 1 calc R . . H23C H -0.4623 -0.1031 -1.2433 0.049 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 0.01495(4) 0.01173(4) 0.01424(4) 0.00074(3) 0.00886(3) 0.00102(3) Cl1 0.0270(3) 0.0162(2) 0.0246(3) -0.0042(2) 0.0172(2) -0.0030(2) N1 0.0184(9) 0.0156(8) 0.0198(9) -0.0007(7) 0.0139(8) -0.0009(7) N2 0.0181(10) 0.0367(13) 0.0314(12) 0.0041(10) 0.0151(10) 0.0064(9) C1 0.0172(10) 0.0113(9) 0.0160(9) 0.0005(7) 0.0102(8) -0.0001(7) C2 0.0193(10) 0.0168(10) 0.0199(10) 0.0032(8) 0.0132(9) 0.0033(8) C3 0.0161(10) 0.0182(10) 0.0214(11) -0.0012(8) 0.0100(9) 0.0015(8) C4 0.0195(11) 0.0208(11) 0.0189(11) 0.0032(9) 0.0078(9) 0.0047(9) C5 0.0238(11) 0.0183(10) 0.0163(10) 0.0025(8) 0.0107(9) 0.0007(9) C6 0.0184(10) 0.0129(9) 0.0151(9) -0.0005(7) 0.0101(8) -0.0008(7) C7 0.0224(11) 0.0133(9) 0.0176(10) -0.0030(7) 0.0136(9) -0.0033(8) C8 0.0306(13) 0.0215(11) 0.0203(11) -0.0013(9) 0.0178(10) -0.0041(10) C9 0.0374(15) 0.0276(13) 0.0275(13) -0.0069(10) 0.0260(12) -0.0106(11) C10 0.0294(13) 0.0284(13) 0.0344(14) -0.0079(11) 0.0257(12) -0.0068(10) C11 0.0229(12) 0.0233(11) 0.0281(12) -0.0031(9) 0.0189(11) -0.0018(9) C12 0.0184(12) 0.0434(17) 0.0301(14) -0.0067(13) 0.0106(11) 0.0049(12) C13 0.0284(14) 0.0371(16) 0.0467(18) 0.0014(13) 0.0282(14) 0.0003(12) C14 0.0259(11) 0.0154(10) 0.0172(10) 0.0037(8) 0.0154(9) 0.0019(8) C15 0.0221(11) 0.0117(9) 0.0161(9) 0.0005(7) 0.0122(9) -0.0006(8) C16 0.0238(11) 0.0112(9) 0.0201(10) 0.0024(8) 0.0148(9) 0.0037(8) C17 0.0199(11) 0.0165(10) 0.0216(11) 0.0028(8) 0.0107(9) 0.0043(8) C18 0.0234(11) 0.0168(10) 0.0164(10) 0.0038(8) 0.0105(9) 0.0038(8) C19 0.0363(15) 0.0265(13) 0.0291(13) 0.0021(10) 0.0262(12) 0.0021(11) C20 0.0276(13) 0.0208(11) 0.0225(11) -0.0025(9) 0.0144(10) -0.0064(10) C21 0.0367(15) 0.0201(11) 0.0306(13) -0.0013(10) 0.0259(12) 0.0032(10) C22 0.0211(13) 0.0325(15) 0.0390(16) 0.0057(12) 0.0148(12) 0.0088(11) C23 0.0354(15) 0.0303(14) 0.0168(11) -0.0014(10) 0.0091(11) 0.0020(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.037(2) . ? Ir1 N1 2.097(2) . ? Ir1 C14 2.161(2) . ? Ir1 C16 2.163(2) . ? Ir1 C15 2.166(2) . ? Ir1 C18 2.238(2) . ? Ir1 C17 2.263(2) . ? Ir1 Cl1 2.4122(6) . ? N1 C11 1.346(3) . ? N1 C7 1.366(3) . ? N2 C3 1.379(3) . ? N2 C13 1.446(4) . ? N2 C12 1.446(4) . ? C1 C2 1.389(3) . ? C1 C6 1.415(3) . ? C2 C3 1.413(3) . ? C2 H2 0.9500 . ? C3 C4 1.410(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.400(3) . ? C5 H5 0.9500 . ? C6 C7 1.445(3) . ? C7 C8 1.404(3) . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.392(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.443(3) . ? C14 C18 1.446(4) . ? C14 C19 1.501(4) . ? C15 C16 1.440(3) . ? C15 C20 1.484(4) . ? C16 C17 1.454(4) . ? C16 C21 1.492(3) . ? C17 C18 1.409(4) . ? C17 C22 1.491(4) . ? C18 C23 1.503(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 77.94(9) . . ? C1 Ir1 C14 106.65(9) . . ? N1 Ir1 C14 166.19(9) . . ? C1 Ir1 C16 123.20(9) . . ? N1 Ir1 C16 101.49(9) . . ? C14 Ir1 C16 64.96(9) . . ? C1 Ir1 C15 97.70(9) . . ? N1 Ir1 C15 128.32(8) . . ? C14 Ir1 C15 38.97(9) . . ? C16 Ir1 C15 38.85(9) . . ? C1 Ir1 C18 142.46(9) . . ? N1 Ir1 C18 139.48(9) . . ? C14 Ir1 C18 38.33(9) . . ? C16 Ir1 C18 63.09(9) . . ? C15 Ir1 C18 63.77(9) . . ? C1 Ir1 C17 160.69(10) . . ? N1 Ir1 C17 107.92(9) . . ? C14 Ir1 C17 63.57(10) . . ? C16 Ir1 C17 38.26(9) . . ? C15 Ir1 C17 63.98(9) . . ? C18 Ir1 C17 36.47(9) . . ? C1 Ir1 Cl1 88.67(7) . . ? N1 Ir1 Cl1 85.19(6) . . ? C14 Ir1 Cl1 107.70(7) . . ? C16 Ir1 Cl1 148.11(7) . . ? C15 Ir1 Cl1 146.49(6) . . ? C18 Ir1 Cl1 91.51(7) . . ? C17 Ir1 Cl1 109.92(7) . . ? C11 N1 C7 119.2(2) . . ? C11 N1 Ir1 123.89(18) . . ? C7 N1 Ir1 116.71(16) . . ? C3 N2 C13 119.8(2) . . ? C3 N2 C12 119.7(3) . . ? C13 N2 C12 116.3(3) . . ? C2 C1 C6 118.0(2) . . ? C2 C1 Ir1 125.72(17) . . ? C6 C1 Ir1 116.28(17) . . ? C1 C2 C3 122.4(2) . . ? C1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? N2 C3 C4 121.3(2) . . ? N2 C3 C2 120.7(2) . . ? C4 C3 C2 118.0(2) . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 C7 124.6(2) . . ? C1 C6 C7 115.0(2) . . ? N1 C7 C8 119.9(2) . . ? N1 C7 C6 114.0(2) . . ? C8 C7 C6 126.1(2) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 118.1(3) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? N1 C11 C10 123.1(3) . . ? N1 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C18 107.3(2) . . ? C15 C14 C19 126.3(2) . . ? C18 C14 C19 125.8(2) . . ? C15 C14 Ir1 70.70(13) . . ? C18 C14 Ir1 73.73(14) . . ? C19 C14 Ir1 127.56(18) . . ? C16 C15 C14 107.3(2) . . ? C16 C15 C20 125.5(2) . . ? C14 C15 C20 127.0(2) . . ? C16 C15 Ir1 70.48(13) . . ? C14 C15 Ir1 70.33(13) . . ? C20 C15 Ir1 128.94(17) . . ? C15 C16 C17 108.5(2) . . ? C15 C16 C21 126.1(2) . . ? C17 C16 C21 125.0(2) . . ? C15 C16 Ir1 70.67(13) . . ? C17 C16 Ir1 74.58(13) . . ? C21 C16 Ir1 126.10(17) . . ? C18 C17 C16 107.2(2) . . ? C18 C17 C22 126.9(3) . . ? C16 C17 C22 125.8(2) . . ? C18 C17 Ir1 70.82(14) . . ? C16 C17 Ir1 67.16(13) . . ? C22 C17 Ir1 130.6(2) . . ? C17 C18 C14 109.5(2) . . ? C17 C18 C23 125.7(3) . . ? C14 C18 C23 124.7(2) . . ? C17 C18 Ir1 72.71(14) . . ? C14 C18 Ir1 67.94(13) . . ? C23 C18 Ir1 126.29(19) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 C1 Ir1 N1 C11 -176.8(2) . . . . ? C14 Ir1 N1 C11 72.2(4) . . . . ? C16 Ir1 N1 C11 61.3(2) . . . . ? C15 Ir1 N1 C11 92.9(2) . . . . ? C18 Ir1 N1 C11 -0.4(3) . . . . ? C17 Ir1 N1 C11 22.3(2) . . . . ? Cl1 Ir1 N1 C11 -87.14(19) . . . . ? C1 Ir1 N1 C7 -1.37(17) . . . . ? C14 Ir1 N1 C7 -112.4(4) . . . . ? C16 Ir1 N1 C7 -123.23(17) . . . . ? C15 Ir1 N1 C7 -91.70(19) . . . . ? C18 Ir1 N1 C7 174.99(16) . . . . ? C17 Ir1 N1 C7 -162.30(16) . . . . ? Cl1 Ir1 N1 C7 88.30(16) . . . . ? N1 Ir1 C1 C2 -179.9(2) . . . . ? C14 Ir1 C1 C2 -13.4(2) . . . . ? C16 Ir1 C1 C2 -84.0(2) . . . . ? C15 Ir1 C1 C2 -52.3(2) . . . . ? C18 Ir1 C1 C2 4.0(3) . . . . ? C17 Ir1 C1 C2 -69.9(4) . . . . ? Cl1 Ir1 C1 C2 94.7(2) . . . . ? N1 Ir1 C1 C6 0.98(16) . . . . ? C14 Ir1 C1 C6 167.52(17) . . . . ? C16 Ir1 C1 C6 96.93(18) . . . . ? C15 Ir1 C1 C6 128.64(17) . . . . ? C18 Ir1 C1 C6 -175.14(16) . . . . ? C17 Ir1 C1 C6 111.0(3) . . . . ? Cl1 Ir1 C1 C6 -84.39(17) . . . . ? C6 C1 C2 C3 -0.6(3) . . . . ? Ir1 C1 C2 C3 -179.67(18) . . . . ? C13 N2 C3 C4 -173.4(3) . . . . ? C12 N2 C3 C4 -17.1(4) . . . . ? C13 N2 C3 C2 8.4(4) . . . . ? C12 N2 C3 C2 164.6(3) . . . . ? C1 C2 C3 N2 179.5(2) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? N2 C3 C4 C5 -178.6(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C1 1.7(4) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? Ir1 C1 C6 C5 178.32(18) . . . . ? C2 C1 C6 C7 -179.7(2) . . . . ? Ir1 C1 C6 C7 -0.5(3) . . . . ? C11 N1 C7 C8 -2.1(3) . . . . ? Ir1 N1 C7 C8 -177.76(18) . . . . ? C11 N1 C7 C6 177.1(2) . . . . ? Ir1 N1 C7 C6 1.5(3) . . . . ? C5 C6 C7 N1 -179.4(2) . . . . ? C1 C6 C7 N1 -0.6(3) . . . . ? C5 C6 C7 C8 -0.2(4) . . . . ? C1 C6 C7 C8 178.6(2) . . . . ? N1 C7 C8 C9 1.5(4) . . . . ? C6 C7 C8 C9 -177.7(2) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C7 N1 C11 C10 1.6(4) . . . . ? Ir1 N1 C11 C10 177.0(2) . . . . ? C9 C10 C11 N1 -0.4(4) . . . . ? C1 Ir1 C14 C15 -81.53(15) . . . . ? N1 Ir1 C14 C15 26.1(4) . . . . ? C16 Ir1 C14 C15 37.88(14) . . . . ? C18 Ir1 C14 C15 115.5(2) . . . . ? C17 Ir1 C14 C15 80.52(15) . . . . ? Cl1 Ir1 C14 C15 -175.54(12) . . . . ? C1 Ir1 C14 C18 162.97(14) . . . . ? N1 Ir1 C14 C18 -89.4(4) . . . . ? C16 Ir1 C14 C18 -77.62(15) . . . . ? C15 Ir1 C14 C18 -115.5(2) . . . . ? C17 Ir1 C14 C18 -34.98(14) . . . . ? Cl1 Ir1 C14 C18 68.96(14) . . . . ? C1 Ir1 C14 C19 39.9(3) . . . . ? N1 Ir1 C14 C19 147.6(3) . . . . ? C16 Ir1 C14 C19 159.4(3) . . . . ? C15 Ir1 C14 C19 121.5(3) . . . . ? C18 Ir1 C14 C19 -123.0(3) . . . . ? C17 Ir1 C14 C19 -158.0(3) . . . . ? Cl1 Ir1 C14 C19 -54.1(2) . . . . ? C18 C14 C15 C16 4.0(3) . . . . ? C19 C14 C15 C16 175.9(2) . . . . ? Ir1 C14 C15 C16 -61.12(15) . . . . ? C18 C14 C15 C20 -170.3(2) . . . . ? C19 C14 C15 C20 1.5(4) . . . . ? Ir1 C14 C15 C20 124.5(2) . . . . ? C18 C14 C15 Ir1 65.17(16) . . . . ? C19 C14 C15 Ir1 -123.0(2) . . . . ? C1 Ir1 C15 C16 -135.48(14) . . . . ? N1 Ir1 C15 C16 -54.79(17) . . . . ? C14 Ir1 C15 C16 117.5(2) . . . . ? C18 Ir1 C15 C16 78.90(15) . . . . ? C17 Ir1 C15 C16 38.11(14) . . . . ? Cl1 Ir1 C15 C16 125.22(13) . . . . ? C1 Ir1 C15 C14 107.02(15) . . . . ? N1 Ir1 C15 C14 -172.30(13) . . . . ? C16 Ir1 C15 C14 -117.5(2) . . . . ? C18 Ir1 C15 C14 -38.61(14) . . . . ? C17 Ir1 C15 C14 -79.40(15) . . . . ? Cl1 Ir1 C15 C14 7.7(2) . . . . ? C1 Ir1 C15 C20 -15.2(2) . . . . ? N1 Ir1 C15 C20 65.5(3) . . . . ? C14 Ir1 C15 C20 -122.2(3) . . . . ? C16 Ir1 C15 C20 120.3(3) . . . . ? C18 Ir1 C15 C20 -160.8(3) . . . . ? C17 Ir1 C15 C20 158.4(3) . . . . ? Cl1 Ir1 C15 C20 -114.5(2) . . . . ? C14 C15 C16 C17 -4.5(3) . . . . ? C20 C15 C16 C17 170.0(2) . . . . ? Ir1 C15 C16 C17 -65.53(16) . . . . ? C14 C15 C16 C21 -177.9(2) . . . . ? C20 C15 C16 C21 -3.4(4) . . . . ? Ir1 C15 C16 C21 121.1(2) . . . . ? C14 C15 C16 Ir1 61.02(15) . . . . ? C20 C15 C16 Ir1 -124.5(2) . . . . ? C1 Ir1 C16 C15 56.14(17) . . . . ? N1 Ir1 C16 C15 139.15(13) . . . . ? C14 Ir1 C16 C15 -38.01(13) . . . . ? C18 Ir1 C16 C15 -80.80(15) . . . . ? C17 Ir1 C16 C15 -116.4(2) . . . . ? Cl1 Ir1 C16 C15 -121.37(14) . . . . ? C1 Ir1 C16 C17 172.56(14) . . . . ? N1 Ir1 C16 C17 -104.43(15) . . . . ? C14 Ir1 C16 C17 78.41(16) . . . . ? C15 Ir1 C16 C17 116.4(2) . . . . ? C18 Ir1 C16 C17 35.63(15) . . . . ? Cl1 Ir1 C16 C17 -5.0(2) . . . . ? C1 Ir1 C16 C21 -65.0(3) . . . . ? N1 Ir1 C16 C21 18.0(2) . . . . ? C14 Ir1 C16 C21 -159.2(3) . . . . ? C15 Ir1 C16 C21 -121.2(3) . . . . ? C18 Ir1 C16 C21 158.0(3) . . . . ? C17 Ir1 C16 C21 122.4(3) . . . . ? Cl1 Ir1 C16 C21 117.5(2) . . . . ? C15 C16 C17 C18 3.2(3) . . . . ? C21 C16 C17 C18 176.7(2) . . . . ? Ir1 C16 C17 C18 -59.77(17) . . . . ? C15 C16 C17 C22 -172.5(2) . . . . ? C21 C16 C17 C22 0.9(4) . . . . ? Ir1 C16 C17 C22 124.5(3) . . . . ? C15 C16 C17 Ir1 62.99(15) . . . . ? C21 C16 C17 Ir1 -123.6(2) . . . . ? C1 Ir1 C17 C18 100.0(3) . . . . ? N1 Ir1 C17 C18 -155.04(15) . . . . ? C14 Ir1 C17 C18 36.74(15) . . . . ? C16 Ir1 C17 C18 119.1(2) . . . . ? C15 Ir1 C17 C18 80.40(16) . . . . ? Cl1 Ir1 C17 C18 -63.69(16) . . . . ? C1 Ir1 C17 C16 -19.1(4) . . . . ? N1 Ir1 C17 C16 85.88(15) . . . . ? C14 Ir1 C17 C16 -82.35(16) . . . . ? C15 Ir1 C17 C16 -38.69(14) . . . . ? C18 Ir1 C17 C16 -119.1(2) . . . . ? Cl1 Ir1 C17 C16 177.22(13) . . . . ? C1 Ir1 C17 C22 -137.5(3) . . . . ? N1 Ir1 C17 C22 -32.5(3) . . . . ? C14 Ir1 C17 C22 159.3(3) . . . . ? C16 Ir1 C17 C22 -118.3(3) . . . . ? C15 Ir1 C17 C22 -157.0(3) . . . . ? C18 Ir1 C17 C22 122.6(3) . . . . ? Cl1 Ir1 C17 C22 58.9(3) . . . . ? C16 C17 C18 C14 -0.7(3) . . . . ? C22 C17 C18 C14 175.0(3) . . . . ? Ir1 C17 C18 C14 -58.14(17) . . . . ? C16 C17 C18 C23 -179.9(2) . . . . ? C22 C17 C18 C23 -4.2(4) . . . . ? Ir1 C17 C18 C23 122.7(3) . . . . ? C16 C17 C18 Ir1 57.47(16) . . . . ? C22 C17 C18 Ir1 -126.8(3) . . . . ? C15 C14 C18 C17 -2.1(3) . . . . ? C19 C14 C18 C17 -174.0(2) . . . . ? Ir1 C14 C18 C17 61.05(18) . . . . ? C15 C14 C18 C23 177.1(2) . . . . ? C19 C14 C18 C23 5.2(4) . . . . ? Ir1 C14 C18 C23 -119.7(3) . . . . ? C15 C14 C18 Ir1 -63.16(15) . . . . ? C19 C14 C18 Ir1 124.9(2) . . . . ? C1 Ir1 C18 C17 -147.69(16) . . . . ? N1 Ir1 C18 C17 38.2(2) . . . . ? C14 Ir1 C18 C17 -120.3(2) . . . . ? C16 Ir1 C18 C17 -37.36(15) . . . . ? C15 Ir1 C18 C17 -81.01(16) . . . . ? Cl1 Ir1 C18 C17 122.53(14) . . . . ? C1 Ir1 C18 C14 -27.4(2) . . . . ? N1 Ir1 C18 C14 158.44(14) . . . . ? C16 Ir1 C18 C14 82.91(15) . . . . ? C15 Ir1 C18 C14 39.26(14) . . . . ? C17 Ir1 C18 C14 120.3(2) . . . . ? Cl1 Ir1 C18 C14 -117.20(13) . . . . ? C1 Ir1 C18 C23 90.3(3) . . . . ? N1 Ir1 C18 C23 -83.8(3) . . . . ? C14 Ir1 C18 C23 117.7(3) . . . . ? C16 Ir1 C18 C23 -159.4(3) . . . . ? C15 Ir1 C18 C23 157.0(3) . . . . ? C17 Ir1 C18 C23 -122.0(3) . . . . ? Cl1 Ir1 C18 C23 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 32.08 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.898 _refine_diff_density_min -1.453 _refine_diff_density_rms 0.115 ###END data_[endo-3a][PF6]2 _database_code_depnum_ccdc_archive 'CCDC 805114' #TrackingRef '- compilation_djukic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H43 Cl Ir2 N2, C3 H6 O, 2(F6 P)' _chemical_formula_sum 'C36 H49 Cl F12 Ir2 N2 O P2' _chemical_formula_weight 1235.56 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' Cl Cl 0.1484 0.1585 '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 'P21/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 13.019(1) _cell_length_b 20.090(1) _cell_length_c 17.132(1) _cell_angle_alpha 90.00 _cell_angle_beta 108.824(1) _cell_angle_gamma 90.00 _cell_volume 4241.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 6626 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 6.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2637 _exptl_absorpt_correction_T_max 0.5629 _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30593 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 30.02 _reflns_number_total 12327 _reflns_number_gt 8865 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12327 _refine_ls_number_parameters 519 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir -0.241172(18) 0.220138(10) -0.174957(13) 0.02312(7) Uani 1 1 d . . . Ir2 Ir -0.521503(18) 0.327974(10) -0.282627(14) 0.02540(7) Uani 1 1 d . . . Cl1 Cl -0.55595(16) 0.26161(9) -0.17918(13) 0.0521(5) Uani 1 1 d . . . N1 N -0.5395(4) 0.2388(2) -0.3482(3) 0.0323(11) Uani 1 1 d . . . N2 N -0.0771(4) 0.3580(2) -0.1753(3) 0.0321(11) Uani 1 1 d . . . C1 C -0.3652(5) 0.2998(3) -0.2579(4) 0.0244(11) Uani 1 1 d . . . C2 C -0.2694(5) 0.3295(3) -0.2032(4) 0.0240(11) Uani 1 1 d . . . H2 H -0.2751 0.3559 -0.1589 0.029 Uiso 1 1 calc R . . C3 C -0.1626(5) 0.3206(3) -0.2129(4) 0.0275(12) Uani 1 1 d . . . C4 C -0.1512(5) 0.2600(3) -0.2560(4) 0.0282(12) Uani 1 1 d . . . H4 H -0.0808 0.2445 -0.2523 0.034 Uiso 1 1 calc R . . C5 C -0.2429(5) 0.2242(3) -0.3029(4) 0.0289(13) Uani 1 1 d . . . H5 H -0.2340 0.1868 -0.3340 0.035 Uiso 1 1 calc R . . C6 C -0.3498(5) 0.2431(3) -0.3045(4) 0.0258(12) Uani 1 1 d . . . C7 C -0.4495(5) 0.2082(3) -0.3528(4) 0.0277(12) Uani 1 1 d . . . C8 C -0.4534(6) 0.1489(3) -0.3949(4) 0.0355(14) Uani 1 1 d . . . H8 H -0.3887 0.1278 -0.3963 0.043 Uiso 1 1 calc R . . C9 C -0.5539(7) 0.1209(3) -0.4349(5) 0.0487(19) Uani 1 1 d . . . H9 H -0.5593 0.0813 -0.4662 0.058 Uiso 1 1 calc R . . C10 C -0.6471(6) 0.1514(4) -0.4287(5) 0.056(2) Uani 1 1 d . . . H10 H -0.7164 0.1320 -0.4539 0.067 Uiso 1 1 calc R . . C11 C -0.6374(6) 0.2100(3) -0.3855(6) 0.050(2) Uani 1 1 d . . . H11 H -0.7011 0.2309 -0.3816 0.060 Uiso 1 1 calc R . . C12 C -0.0853(6) 0.4158(3) -0.1256(5) 0.0437(17) Uani 1 1 d . . . H12A H -0.1581 0.4351 -0.1477 0.065 Uiso 1 1 calc R . . H12B H -0.0312 0.4491 -0.1275 0.065 Uiso 1 1 calc R . . H12C H -0.0722 0.4018 -0.0684 0.065 Uiso 1 1 calc R . . C13 C 0.0299(6) 0.3437(4) -0.1805(6) 0.0486(19) Uani 1 1 d . . . H13A H 0.0633 0.3075 -0.1423 0.073 Uiso 1 1 calc R . . H13B H 0.0754 0.3836 -0.1657 0.073 Uiso 1 1 calc R . . H13C H 0.0233 0.3303 -0.2369 0.073 Uiso 1 1 calc R . . C14 C -0.1540(6) 0.2048(3) -0.0453(4) 0.0338(14) Uani 1 1 d . . . C15 C -0.1200(5) 0.1552(3) -0.0919(4) 0.0359(14) Uani 1 1 d . . . C16 C -0.2143(6) 0.1156(3) -0.1350(4) 0.0333(14) Uani 1 1 d . . . C17 C -0.3045(5) 0.1407(3) -0.1129(4) 0.0301(13) Uani 1 1 d . . . C18 C -0.2680(5) 0.1956(3) -0.0583(4) 0.0304(13) Uani 1 1 d . . . C19 C -0.0806(7) 0.2547(4) 0.0127(4) 0.054(2) Uani 1 1 d . . . H19A H -0.0452 0.2336 0.0662 0.081 Uiso 1 1 calc R . . H19B H -0.1238 0.2927 0.0200 0.081 Uiso 1 1 calc R . . H19C H -0.0253 0.2702 -0.0107 0.081 Uiso 1 1 calc R . . C20 C -0.0093(6) 0.1432(4) -0.0941(6) 0.056(2) Uani 1 1 d . . . H20A H 0.0340 0.1838 -0.0776 0.084 Uiso 1 1 calc R . . H20B H -0.0126 0.1309 -0.1502 0.084 Uiso 1 1 calc R . . H20C H 0.0242 0.1071 -0.0560 0.084 Uiso 1 1 calc R . . C21 C -0.2126(7) 0.0559(3) -0.1854(5) 0.052(2) Uani 1 1 d . . . H21A H -0.1883 0.0173 -0.1492 0.077 Uiso 1 1 calc R . . H21B H -0.1626 0.0634 -0.2168 0.077 Uiso 1 1 calc R . . H21C H -0.2857 0.0476 -0.2236 0.077 Uiso 1 1 calc R . . C22 C -0.4137(6) 0.1093(3) -0.1385(5) 0.0432(16) Uani 1 1 d . . . H22A H -0.4108 0.0680 -0.1074 0.065 Uiso 1 1 calc R . . H22B H -0.4364 0.0993 -0.1976 0.065 Uiso 1 1 calc R . . H22C H -0.4658 0.1400 -0.1273 0.065 Uiso 1 1 calc R . . C23 C -0.3316(7) 0.2316(3) -0.0118(4) 0.0425(17) Uani 1 1 d . . . H23A H -0.4094 0.2243 -0.0393 0.064 Uiso 1 1 calc R . . H23B H -0.3159 0.2794 -0.0107 0.064 Uiso 1 1 calc R . . H23C H -0.3111 0.2146 0.0447 0.064 Uiso 1 1 calc R . . C24 C -0.6551(6) 0.3871(3) -0.3692(4) 0.0397(16) Uani 1 1 d . . . C25 C -0.6629(6) 0.3951(3) -0.2900(5) 0.0386(16) Uani 1 1 d . . . C26 C -0.5613(6) 0.4226(3) -0.2378(4) 0.0396(16) Uani 1 1 d . . . C27 C -0.4934(6) 0.4351(3) -0.2871(5) 0.0400(17) Uani 1 1 d . . . C28 C -0.5495(6) 0.4093(3) -0.3681(5) 0.0406(16) Uani 1 1 d . . . C29 C -0.7427(9) 0.3623(4) -0.4445(6) 0.084(3) Uani 1 1 d . . . H29A H -0.7595 0.3158 -0.4362 0.127 Uiso 1 1 calc R . . H29B H -0.7176 0.3654 -0.4925 0.127 Uiso 1 1 calc R . . H29C H -0.8080 0.3896 -0.4539 0.127 Uiso 1 1 calc R . . C30 C -0.7557(7) 0.3782(4) -0.2616(7) 0.068(3) Uani 1 1 d . . . H30A H -0.7932 0.4191 -0.2552 0.101 Uiso 1 1 calc R . . H30B H -0.7292 0.3551 -0.2085 0.101 Uiso 1 1 calc R . . H30C H -0.8062 0.3492 -0.3022 0.101 Uiso 1 1 calc R . . C31 C -0.5382(10) 0.4405(4) -0.1481(6) 0.076(3) Uani 1 1 d . . . H31A H -0.4604 0.4493 -0.1227 0.114 Uiso 1 1 calc R . . H31B H -0.5596 0.4035 -0.1195 0.114 Uiso 1 1 calc R . . H31C H -0.5795 0.4804 -0.1441 0.114 Uiso 1 1 calc R . . C32 C -0.3891(6) 0.4707(4) -0.2589(8) 0.074(3) Uani 1 1 d . . . H32A H -0.3423 0.4549 -0.2898 0.111 Uiso 1 1 calc R . . H32B H -0.3537 0.4623 -0.1999 0.111 Uiso 1 1 calc R . . H32C H -0.4019 0.5185 -0.2681 0.111 Uiso 1 1 calc R . . C33 C -0.5107(10) 0.4162(5) -0.4423(6) 0.084(4) Uani 1 1 d . . . H33A H -0.5518 0.4516 -0.4784 0.126 Uiso 1 1 calc R . . H33B H -0.5220 0.3741 -0.4727 0.126 Uiso 1 1 calc R . . H33C H -0.4333 0.4275 -0.4237 0.126 Uiso 1 1 calc R . . P1 P -0.22671(16) 0.03281(8) -0.45914(11) 0.0355(4) Uani 1 1 d . . . F1 F -0.3530(4) 0.0261(2) -0.4697(3) 0.0512(11) Uani 1 1 d . . . F2 F -0.2054(5) -0.0365(3) -0.4127(4) 0.0853(19) Uani 1 1 d . . . F3 F -0.1018(4) 0.0386(2) -0.4489(3) 0.0636(13) Uani 1 1 d . . . F4 F -0.2496(4) 0.1013(2) -0.5077(4) 0.0686(15) Uani 1 1 d . . . F5 F -0.2473(4) -0.0045(2) -0.5453(3) 0.0652(13) Uani 1 1 d . . . F6 F -0.2097(5) 0.0711(3) -0.3758(3) 0.0880(19) Uani 1 1 d . . . P2 P -0.13704(19) 0.45203(9) -0.39359(13) 0.0452(5) Uani 1 1 d . . . F7 F -0.1086(9) 0.3775(3) -0.3868(5) 0.163(4) Uani 1 1 d . . . F8 F -0.1816(7) 0.4470(4) -0.3211(4) 0.115(3) Uani 1 1 d . . . F9 F -0.1546(10) 0.5262(3) -0.3986(5) 0.174(5) Uani 1 1 d . . . F10 F -0.0848(9) 0.4551(5) -0.4631(6) 0.171(4) Uani 1 1 d . . . F11 F -0.0231(6) 0.4665(5) -0.3253(6) 0.162(4) Uani 1 1 d . . . F12 F -0.2436(6) 0.4375(4) -0.4605(5) 0.148(4) Uani 1 1 d . . . O1 O -0.9219(7) 0.2052(4) -0.2762(6) 0.110(3) Uani 1 1 d . . . C34 C -0.8625(8) 0.1586(4) -0.2621(7) 0.064(2) Uani 1 1 d . . . C35 C -0.7712(12) 0.1556(8) -0.1859(9) 0.142(7) Uani 1 1 d . . . H35A H -0.7039 0.1491 -0.1988 0.214 Uiso 1 1 calc R . . H35B H -0.7815 0.1184 -0.1521 0.214 Uiso 1 1 calc R . . H35C H -0.7669 0.1974 -0.1553 0.214 Uiso 1 1 calc R . . C36 C -0.8736(15) 0.1052(6) -0.3206(9) 0.136(6) Uani 1 1 d . . . H36A H -0.9295 0.1169 -0.3726 0.204 Uiso 1 1 calc R . . H36B H -0.8948 0.0643 -0.2985 0.204 Uiso 1 1 calc R . . H36C H -0.8043 0.0982 -0.3303 0.204 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 0.02518(12) 0.02075(11) 0.02350(12) -0.00056(8) 0.00796(9) -0.00048(8) Ir2 0.02391(13) 0.02287(12) 0.02997(13) 0.00072(9) 0.00947(9) 0.00010(8) Cl1 0.0481(11) 0.0510(10) 0.0656(13) 0.0277(9) 0.0299(10) 0.0080(8) N1 0.024(3) 0.026(2) 0.040(3) -0.003(2) 0.002(2) -0.002(2) N2 0.026(3) 0.027(2) 0.045(3) -0.005(2) 0.013(2) -0.002(2) C1 0.023(3) 0.024(3) 0.027(3) 0.003(2) 0.009(2) -0.005(2) C2 0.024(3) 0.023(3) 0.027(3) 0.010(2) 0.011(2) 0.005(2) C3 0.025(3) 0.027(3) 0.032(3) 0.004(2) 0.011(3) -0.001(2) C4 0.023(3) 0.033(3) 0.031(3) -0.002(3) 0.013(2) -0.003(2) C5 0.042(4) 0.026(3) 0.025(3) -0.003(2) 0.020(3) -0.005(2) C6 0.026(3) 0.028(3) 0.023(3) 0.005(2) 0.008(2) 0.002(2) C7 0.028(3) 0.027(3) 0.028(3) 0.000(2) 0.008(2) -0.004(2) C8 0.041(4) 0.031(3) 0.034(4) -0.008(3) 0.011(3) -0.001(3) C9 0.055(5) 0.036(3) 0.047(4) -0.018(3) 0.006(4) -0.018(3) C10 0.033(4) 0.046(4) 0.075(6) -0.021(4) -0.001(4) -0.005(3) C11 0.032(4) 0.035(3) 0.077(6) -0.012(4) 0.011(4) -0.003(3) C12 0.047(4) 0.030(3) 0.051(5) -0.014(3) 0.012(4) -0.007(3) C13 0.035(4) 0.043(4) 0.072(6) -0.009(4) 0.024(4) -0.007(3) C14 0.040(4) 0.033(3) 0.024(3) 0.005(3) 0.005(3) -0.004(3) C15 0.027(3) 0.036(3) 0.041(4) 0.015(3) 0.005(3) 0.004(3) C16 0.040(4) 0.024(3) 0.035(4) -0.001(3) 0.012(3) 0.000(3) C17 0.037(3) 0.026(3) 0.026(3) 0.002(2) 0.009(3) -0.009(2) C18 0.041(4) 0.030(3) 0.022(3) 0.006(2) 0.012(3) 0.003(3) C19 0.071(6) 0.045(4) 0.030(4) 0.000(3) -0.006(4) -0.026(4) C20 0.034(4) 0.059(5) 0.073(6) 0.022(4) 0.013(4) 0.017(3) C21 0.081(6) 0.028(3) 0.050(5) -0.003(3) 0.027(4) 0.010(3) C22 0.035(4) 0.045(4) 0.047(4) 0.007(3) 0.009(3) -0.005(3) C23 0.060(5) 0.042(3) 0.032(4) -0.001(3) 0.022(3) 0.010(3) C24 0.042(4) 0.026(3) 0.039(4) 0.000(3) -0.004(3) 0.007(3) C25 0.038(4) 0.027(3) 0.057(5) 0.012(3) 0.024(3) 0.012(3) C26 0.047(4) 0.026(3) 0.043(4) -0.001(3) 0.010(3) 0.010(3) C27 0.029(3) 0.023(3) 0.070(5) 0.010(3) 0.018(3) 0.000(2) C28 0.054(5) 0.027(3) 0.046(4) 0.014(3) 0.024(4) 0.006(3) C29 0.088(8) 0.057(5) 0.064(6) 0.008(5) -0.037(5) 0.003(5) C30 0.046(5) 0.056(5) 0.112(8) 0.024(5) 0.041(5) 0.015(4) C31 0.116(9) 0.060(5) 0.048(5) -0.015(4) 0.022(6) 0.015(5) C32 0.033(4) 0.029(3) 0.151(10) 0.015(5) 0.016(5) -0.003(3) C33 0.121(10) 0.073(6) 0.083(8) 0.038(6) 0.070(7) 0.037(6) P1 0.0432(10) 0.0310(8) 0.0342(9) 0.0010(7) 0.0152(8) 0.0050(7) F1 0.047(3) 0.051(2) 0.061(3) -0.003(2) 0.026(2) -0.0016(19) F2 0.096(4) 0.076(3) 0.098(5) 0.056(3) 0.053(4) 0.039(3) F3 0.042(3) 0.077(3) 0.074(4) 0.009(3) 0.021(3) 0.012(2) F4 0.062(3) 0.037(2) 0.111(4) 0.019(2) 0.033(3) 0.006(2) F5 0.081(4) 0.068(3) 0.060(3) -0.022(2) 0.040(3) -0.011(3) F6 0.059(4) 0.135(5) 0.063(4) -0.053(3) 0.010(3) -0.001(3) P2 0.0639(14) 0.0374(9) 0.0414(11) -0.0081(8) 0.0268(10) -0.0129(9) F7 0.239(11) 0.080(4) 0.114(6) -0.047(4) -0.020(6) 0.052(5) F8 0.151(7) 0.137(6) 0.087(5) 0.020(4) 0.081(5) 0.011(5) F9 0.367(15) 0.049(3) 0.078(5) -0.006(3) 0.032(7) 0.004(5) F10 0.213(11) 0.213(9) 0.144(8) -0.061(7) 0.136(8) -0.067(8) F11 0.089(6) 0.174(8) 0.179(9) -0.099(7) -0.019(5) -0.009(5) F12 0.089(6) 0.185(8) 0.124(6) -0.084(6) -0.027(5) 0.018(5) O1 0.103(7) 0.087(5) 0.143(8) -0.010(5) 0.044(6) 0.043(5) C34 0.044(5) 0.059(5) 0.091(8) 0.006(5) 0.024(5) 0.004(4) C35 0.091(10) 0.158(12) 0.139(13) 0.079(10) -0.018(9) -0.056(9) C36 0.200(18) 0.079(8) 0.104(11) -0.038(7) 0.016(11) 0.015(9) _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 C14 2.166(6) . ? Ir1 C15 2.184(6) . ? Ir1 C5 2.186(6) . ? Ir1 C18 2.193(6) . ? Ir1 C16 2.202(6) . ? Ir1 C17 2.218(5) . ? Ir1 C4 2.234(5) . ? Ir1 C2 2.254(5) . ? Ir1 C6 2.261(6) . ? Ir1 C1 2.390(6) . ? Ir1 C3 2.444(5) . ? Ir2 C1 2.021(6) . ? Ir2 N1 2.087(5) . ? Ir2 C28 2.145(6) . ? Ir2 C26 2.175(6) . ? Ir2 C27 2.188(6) . ? Ir2 C24 2.230(6) . ? Ir2 C25 2.251(6) . ? Ir2 Cl1 2.3734(17) . ? N1 C7 1.349(8) . ? N1 C11 1.357(9) . ? N2 C3 1.326(7) . ? N2 C13 1.453(8) . ? N2 C12 1.464(8) . ? C1 C2 1.426(8) . ? C1 C6 1.443(8) . ? C2 C3 1.463(8) . ? C2 H2 0.9500 . ? C3 C4 1.456(8) . ? C4 C5 1.403(9) . ? C4 H4 0.9500 . ? C5 C6 1.434(8) . ? C5 H5 0.9500 . ? C6 C7 1.472(8) . ? C7 C8 1.385(8) . ? C8 C9 1.385(10) . ? C8 H8 0.9500 . ? C9 C10 1.394(11) . ? C9 H9 0.9500 . ? C10 C11 1.373(10) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.433(9) . ? C14 C18 1.440(9) . ? C14 C19 1.515(9) . ? C15 C16 1.449(9) . ? C15 C20 1.473(9) . ? C16 C17 1.437(9) . ? C16 C21 1.481(9) . ? C17 C18 1.425(8) . ? C17 C22 1.486(9) . ? C18 C23 1.506(8) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.402(10) . ? C24 C28 1.440(10) . ? C24 C29 1.504(10) . ? C25 C26 1.447(10) . ? C25 C30 1.481(10) . ? C26 C27 1.428(10) . ? C26 C31 1.510(11) . ? C27 C28 1.439(10) . ? C27 C32 1.471(10) . ? C28 C33 1.519(10) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? P1 F6 1.573(5) . ? P1 F3 1.582(5) . ? P1 F2 1.584(5) . ? P1 F4 1.586(5) . ? P1 F5 1.598(5) . ? P1 F1 1.601(5) . ? P2 F9 1.507(6) . ? P2 F12 1.516(7) . ? P2 F8 1.534(6) . ? P2 F7 1.538(7) . ? P2 F10 1.551(7) . ? P2 F11 1.592(8) . ? O1 C34 1.188(10) . ? C34 C36 1.443(14) . ? C34 C35 1.455(16) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 C14 Ir1 C15 38.5(2) . . ? C14 Ir1 C5 150.0(3) . . ? C15 Ir1 C5 116.6(2) . . ? C14 Ir1 C18 38.6(2) . . ? C15 Ir1 C18 64.3(2) . . ? C5 Ir1 C18 165.7(2) . . ? C14 Ir1 C16 64.4(2) . . ? C15 Ir1 C16 38.6(2) . . ? C5 Ir1 C16 107.2(2) . . ? C18 Ir1 C16 63.8(2) . . ? C14 Ir1 C17 63.8(2) . . ? C15 Ir1 C17 63.9(2) . . ? C5 Ir1 C17 128.5(2) . . ? C18 Ir1 C17 37.7(2) . . ? C16 Ir1 C17 37.9(2) . . ? C14 Ir1 C4 118.8(2) . . ? C15 Ir1 C4 101.9(2) . . ? C5 Ir1 C4 37.0(2) . . ? C18 Ir1 C4 156.4(2) . . ? C16 Ir1 C4 118.2(2) . . ? C17 Ir1 C4 155.0(2) . . ? C14 Ir1 C2 110.8(2) . . ? C15 Ir1 C2 139.1(2) . . ? C5 Ir1 C2 78.5(2) . . ? C18 Ir1 C2 110.6(2) . . ? C16 Ir1 C2 174.3(2) . . ? C17 Ir1 C2 138.1(2) . . ? C4 Ir1 C2 66.3(2) . . ? C14 Ir1 C6 172.1(2) . . ? C15 Ir1 C6 148.5(2) . . ? C5 Ir1 C6 37.6(2) . . ? C18 Ir1 C6 135.0(2) . . ? C16 Ir1 C6 119.1(2) . . ? C17 Ir1 C6 113.9(2) . . ? C4 Ir1 C6 66.7(2) . . ? C2 Ir1 C6 65.4(2) . . ? C14 Ir1 C1 137.4(2) . . ? C15 Ir1 C1 174.6(2) . . ? C5 Ir1 C1 65.9(2) . . ? C18 Ir1 C1 114.6(2) . . ? C16 Ir1 C1 146.4(2) . . ? C17 Ir1 C1 118.9(2) . . ? C4 Ir1 C1 77.2(2) . . ? C2 Ir1 C1 35.6(2) . . ? C6 Ir1 C1 36.0(2) . . ? C14 Ir1 C3 105.4(2) . . ? C15 Ir1 C3 113.0(2) . . ? C5 Ir1 C3 64.7(2) . . ? C18 Ir1 C3 129.2(2) . . ? C16 Ir1 C3 146.3(2) . . ? C17 Ir1 C3 166.8(2) . . ? C4 Ir1 C3 35.9(2) . . ? C2 Ir1 C3 36.00(19) . . ? C6 Ir1 C3 75.7(2) . . ? C1 Ir1 C3 63.16(19) . . ? C1 Ir2 N1 78.7(2) . . ? C1 Ir2 C28 107.1(2) . . ? N1 Ir2 C28 108.8(2) . . ? C1 Ir2 C26 120.6(3) . . ? N1 Ir2 C26 160.4(2) . . ? C28 Ir2 C26 64.4(3) . . ? C1 Ir2 C27 96.5(2) . . ? N1 Ir2 C27 144.7(3) . . ? C28 Ir2 C27 38.8(3) . . ? C26 Ir2 C27 38.2(3) . . ? C1 Ir2 C24 143.6(3) . . ? N1 Ir2 C24 99.8(2) . . ? C28 Ir2 C24 38.4(3) . . ? C26 Ir2 C24 63.0(3) . . ? C27 Ir2 C24 63.7(3) . . ? C1 Ir2 C25 158.2(2) . . ? N1 Ir2 C25 122.4(2) . . ? C28 Ir2 C25 63.2(2) . . ? C26 Ir2 C25 38.1(3) . . ? C27 Ir2 C25 63.4(2) . . ? C24 Ir2 C25 36.5(3) . . ? C1 Ir2 Cl1 96.13(16) . . ? N1 Ir2 Cl1 84.52(16) . . ? C28 Ir2 Cl1 154.97(19) . . ? C26 Ir2 Cl1 95.95(19) . . ? C27 Ir2 Cl1 130.8(2) . . ? C24 Ir2 Cl1 120.1(2) . . ? C25 Ir2 Cl1 91.74(17) . . ? C7 N1 C11 118.7(5) . . ? C7 N1 Ir2 118.3(4) . . ? C11 N1 Ir2 123.0(4) . . ? C3 N2 C13 122.0(5) . . ? C3 N2 C12 121.6(5) . . ? C13 N2 C12 116.4(5) . . ? C2 C1 C6 116.5(5) . . ? C2 C1 Ir2 129.0(4) . . ? C6 C1 Ir2 114.5(4) . . ? C2 C1 Ir1 67.0(3) . . ? C6 C1 Ir1 67.1(3) . . ? Ir2 C1 Ir1 138.9(3) . . ? C1 C2 C3 122.4(5) . . ? C1 C2 Ir1 77.4(3) . . ? C3 C2 Ir1 79.1(3) . . ? C1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? Ir1 C2 H2 115.0 . . ? N2 C3 C4 120.9(5) . . ? N2 C3 C2 123.8(5) . . ? C4 C3 C2 114.6(5) . . ? N2 C3 Ir1 134.2(4) . . ? C4 C3 Ir1 64.2(3) . . ? C2 C3 Ir1 64.9(3) . . ? C5 C4 C3 120.8(5) . . ? C5 C4 Ir1 69.6(3) . . ? C3 C4 Ir1 79.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? Ir1 C4 H4 121.9 . . ? C4 C5 C6 121.1(5) . . ? C4 C5 Ir1 73.4(3) . . ? C6 C5 Ir1 74.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? Ir1 C5 H5 124.8 . . ? C5 C6 C1 120.3(5) . . ? C5 C6 C7 124.0(5) . . ? C1 C6 C7 115.6(5) . . ? C5 C6 Ir1 68.3(3) . . ? C1 C6 Ir1 76.8(3) . . ? C7 C6 Ir1 127.9(4) . . ? N1 C7 C8 122.4(6) . . ? N1 C7 C6 112.1(5) . . ? C8 C7 C6 125.4(6) . . ? C9 C8 C7 118.5(6) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C8 C9 C10 119.4(6) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 119.1(7) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N1 C11 C10 121.8(7) . . ? N1 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C18 108.3(5) . . ? C15 C14 C19 125.7(7) . . ? C18 C14 C19 125.9(6) . . ? C15 C14 Ir1 71.4(4) . . ? C18 C14 Ir1 71.7(3) . . ? C19 C14 Ir1 126.1(4) . . ? C14 C15 C16 107.6(6) . . ? C14 C15 C20 127.4(7) . . ? C16 C15 C20 124.9(7) . . ? C14 C15 Ir1 70.1(4) . . ? C16 C15 Ir1 71.4(4) . . ? C20 C15 Ir1 126.0(5) . . ? C17 C16 C15 107.5(5) . . ? C17 C16 C21 127.3(6) . . ? C15 C16 C21 124.9(6) . . ? C17 C16 Ir1 71.6(3) . . ? C15 C16 Ir1 70.0(3) . . ? C21 C16 Ir1 128.4(5) . . ? C18 C17 C16 108.6(5) . . ? C18 C17 C22 127.3(6) . . ? C16 C17 C22 123.9(6) . . ? C18 C17 Ir1 70.2(3) . . ? C16 C17 Ir1 70.4(3) . . ? C22 C17 Ir1 129.2(5) . . ? C17 C18 C14 108.0(5) . . ? C17 C18 C23 126.5(6) . . ? C14 C18 C23 124.9(6) . . ? C17 C18 Ir1 72.1(3) . . ? C14 C18 Ir1 69.7(3) . . ? C23 C18 Ir1 130.6(4) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C28 108.5(6) . . ? C25 C24 C29 126.6(8) . . ? C28 C24 C29 124.8(8) . . ? C25 C24 Ir2 72.6(4) . . ? C28 C24 Ir2 67.6(4) . . ? C29 C24 Ir2 127.4(5) . . ? C24 C25 C26 107.8(6) . . ? C24 C25 C30 127.8(8) . . ? C26 C25 C30 124.4(8) . . ? C24 C25 Ir2 70.9(4) . . ? C26 C25 Ir2 68.1(3) . . ? C30 C25 Ir2 125.7(4) . . ? C27 C26 C25 108.5(6) . . ? C27 C26 C31 127.0(8) . . ? C25 C26 C31 124.2(7) . . ? C27 C26 Ir2 71.4(3) . . ? C25 C26 Ir2 73.8(3) . . ? C31 C26 Ir2 125.2(5) . . ? C26 C27 C28 106.8(6) . . ? C26 C27 C32 124.9(8) . . ? C28 C27 C32 128.3(8) . . ? C26 C27 Ir2 70.4(3) . . ? C28 C27 Ir2 69.0(3) . . ? C32 C27 Ir2 127.8(5) . . ? C27 C28 C24 108.1(6) . . ? C27 C28 C33 124.9(8) . . ? C24 C28 C33 126.2(8) . . ? C27 C28 Ir2 72.2(4) . . ? C24 C28 Ir2 74.0(4) . . ? C33 C28 Ir2 127.7(5) . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? F6 P1 F3 91.4(3) . . ? F6 P1 F2 91.4(3) . . ? F3 P1 F2 90.1(3) . . ? F6 P1 F4 90.0(3) . . ? F3 P1 F4 90.4(3) . . ? F2 P1 F4 178.6(4) . . ? F6 P1 F5 178.1(3) . . ? F3 P1 F5 89.9(3) . . ? F2 P1 F5 90.0(3) . . ? F4 P1 F5 88.6(3) . . ? F6 P1 F1 89.0(3) . . ? F3 P1 F1 179.4(3) . . ? F2 P1 F1 89.4(3) . . ? F4 P1 F1 90.1(2) . . ? F5 P1 F1 89.7(3) . . ? F9 P2 F12 93.6(5) . . ? F9 P2 F8 91.2(5) . . ? F12 P2 F8 96.1(5) . . ? F9 P2 F7 175.0(6) . . ? F12 P2 F7 90.5(5) . . ? F8 P2 F7 91.1(5) . . ? F9 P2 F10 90.8(5) . . ? F12 P2 F10 87.1(6) . . ? F8 P2 F10 176.2(6) . . ? F7 P2 F10 86.6(5) . . ? F9 P2 F11 87.1(5) . . ? F12 P2 F11 178.2(5) . . ? F8 P2 F11 85.6(5) . . ? F7 P2 F11 88.7(5) . . ? F10 P2 F11 91.3(6) . . ? O1 C34 C36 122.0(12) . . ? O1 C34 C35 120.3(12) . . ? C36 C34 C35 117.6(12) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.681 _refine_diff_density_min -2.894 _refine_diff_density_rms 0.354 ###END data_[endo-4a][PF6] _database_code_depnum_ccdc_archive 'CCDC 805115' #TrackingRef '- compilation_djukic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H43 Cl Ir N2 Ru, F6 P' _chemical_formula_sum 'C33 H43 Cl F6 Ir N2 P Ru' _chemical_formula_weight 941.38 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/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 8.671(1) _cell_length_b 13.989(1) _cell_length_c 28.862(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.194(2) _cell_angle_gamma 90.00 _cell_volume 3378.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 5834 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Plate _exptl_crystal_colour Orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 4.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4069 _exptl_absorpt_correction_T_max 0.6102 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29565 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 30.02 _reflns_number_total 9531 _reflns_number_gt 7714 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9531 _refine_ls_number_parameters 454 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.844963(12) -0.137877(7) -0.116340(5) 0.02553(4) Uani 1 1 d . . . Ru1 Ru 0.79350(3) -0.427170(16) -0.152148(10) 0.02529(6) Uani 1 1 d . . . Cl1 Cl 0.87665(9) -0.13713(5) -0.19604(3) 0.03517(18) Uani 1 1 d . . . N1 N 0.6036(3) -0.16953(19) -0.14670(10) 0.0300(6) Uani 1 1 d . A . N2 N 1.0850(3) -0.49226(17) -0.05146(11) 0.0332(6) Uani 1 1 d . . . C1 C 0.4964(4) -0.1058(2) -0.17177(13) 0.0357(8) Uani 1 1 d . . . H1 H 0.5336 -0.0461 -0.1802 0.043 Uiso 1 1 calc R A . C2 C 0.3354(4) -0.1248(3) -0.18539(15) 0.0434(9) Uani 1 1 d . A . H2 H 0.2627 -0.0792 -0.2033 0.052 Uiso 1 1 calc R . . C3 C 0.2809(4) -0.2104(3) -0.17283(15) 0.0463(10) Uani 1 1 d . . . H3 H 0.1695 -0.2232 -0.1806 0.056 Uiso 1 1 calc R A . C4 C 0.3891(4) -0.2781(2) -0.14881(15) 0.0401(9) Uani 1 1 d . A . H4 H 0.3530 -0.3384 -0.1408 0.048 Uiso 1 1 calc R . . C5 C 0.5519(3) -0.2565(2) -0.13658(12) 0.0296(7) Uani 1 1 d . . . C6 C 0.6830(3) -0.3208(2) -0.11297(12) 0.0264(6) Uani 1 1 d . A . C7 C 0.8396(3) -0.2840(2) -0.10852(11) 0.0243(6) Uani 1 1 d . A . C8 C 0.9692(3) -0.34706(19) -0.09333(12) 0.0256(6) Uani 1 1 d . A . H8 H 1.0712 -0.3275 -0.0962 0.031 Uiso 1 1 d R . . C9 C 0.9532(4) -0.4388(2) -0.07387(12) 0.0281(6) Uani 1 1 d . A . C10 C 0.7955(3) -0.4738(2) -0.07885(13) 0.0294(7) Uani 1 1 d . A . H10 H 0.7803 -0.5375 -0.0695 0.035 Uiso 1 1 d R . . C11 C 0.6610(3) -0.4151(2) -0.09771(13) 0.0311(7) Uani 1 1 d . A . H11 H 0.5564 -0.4386 -0.1001 0.037 Uiso 1 1 d R . . C12 C 1.0654(4) -0.5932(2) -0.04254(14) 0.0391(8) Uani 1 1 d . A . H12A H 0.9884 -0.6007 -0.0233 0.059 Uiso 1 1 calc R . . H12B H 1.1686 -0.6203 -0.0251 0.059 Uiso 1 1 calc R . . H12C H 1.0261 -0.6266 -0.0732 0.059 Uiso 1 1 calc R . . C13 C 1.2437(4) -0.4594(2) -0.05102(16) 0.0445(10) Uani 1 1 d . A . H13A H 1.2571 -0.4616 -0.0837 0.067 Uiso 1 1 calc R . . H13B H 1.3235 -0.5007 -0.0300 0.067 Uiso 1 1 calc R . . H13C H 1.2580 -0.3936 -0.0390 0.067 Uiso 1 1 calc R . . C14 C 0.8544(4) -0.4284(2) -0.22165(13) 0.0322(7) Uani 1 1 d . A . C15 C 0.6853(4) -0.4150(2) -0.22969(13) 0.0358(8) Uani 1 1 d . A . C16 C 0.6241(4) -0.4977(2) -0.21074(13) 0.0350(8) Uani 1 1 d . A . C17 C 0.7553(4) -0.5606(2) -0.19197(14) 0.0384(8) Uani 1 1 d . A . C18 C 0.8974(4) -0.5176(2) -0.19789(13) 0.0343(7) Uani 1 1 d . A . C19 C 0.9645(5) -0.3665(2) -0.24054(17) 0.0507(11) Uani 1 1 d . . . H19A H 1.0742 -0.3747 -0.2207 0.076 Uiso 1 1 calc R A . H19B H 0.9326 -0.2994 -0.2396 0.076 Uiso 1 1 calc R . . H19C H 0.9590 -0.3847 -0.2737 0.076 Uiso 1 1 calc R . . C20 C 0.5910(5) -0.3321(3) -0.25584(16) 0.0525(10) Uani 1 1 d . . . H20A H 0.6581 -0.2747 -0.2507 0.079 Uiso 1 1 calc R A . H20B H 0.4972 -0.3212 -0.2436 0.079 Uiso 1 1 calc R . . H20C H 0.5564 -0.3465 -0.2902 0.079 Uiso 1 1 calc R . . C21 C 0.4519(4) -0.5171(3) -0.21228(17) 0.0541(11) Uani 1 1 d . . . H21A H 0.4004 -0.5511 -0.2420 0.081 Uiso 1 1 calc R A . H21B H 0.3965 -0.4564 -0.2113 0.081 Uiso 1 1 calc R . . H21C H 0.4467 -0.5563 -0.1846 0.081 Uiso 1 1 calc R . . C22 C 0.7412(5) -0.6596(2) -0.17174(16) 0.0523(11) Uani 1 1 d . . . H22A H 0.7259 -0.7071 -0.1975 0.078 Uiso 1 1 calc R A . H22B H 0.6496 -0.6612 -0.1578 0.078 Uiso 1 1 calc R . . H22C H 0.8391 -0.6744 -0.1468 0.078 Uiso 1 1 calc R . . C23 C 1.0609(4) -0.5627(3) -0.18518(16) 0.0522(10) Uani 1 1 d . . . H23A H 1.0756 -0.5990 -0.2127 0.078 Uiso 1 1 calc R A . H23B H 1.0710 -0.6058 -0.1578 0.078 Uiso 1 1 calc R . . H23C H 1.1425 -0.5126 -0.1767 0.078 Uiso 1 1 calc R . . C24A C 0.9421(6) -0.1134(3) -0.04081(15) 0.0333(11) Uani 0.763(5) 1 d PD A 1 C25A C 1.0632(4) -0.0927(3) -0.06455(19) 0.0308(11) Uani 0.763(5) 1 d PD A 1 C26A C 1.0079(7) -0.0118(4) -0.0943(3) 0.0406(14) Uani 0.763(5) 1 d PD A 1 C27A C 0.8514(7) 0.0135(5) -0.0915(3) 0.0375(14) Uani 0.763(5) 1 d PD A 1 C28A C 0.8107(5) -0.0500(4) -0.0579(2) 0.0375(13) Uani 0.763(5) 1 d PD A 1 C29A C 0.9557(9) -0.1858(3) -0.00111(17) 0.0624(19) Uani 0.763(5) 1 d PD A 1 H29A H 0.9898 -0.1536 0.0301 0.094 Uiso 0.763(5) 1 calc PR A 1 H29B H 1.0346 -0.2345 -0.0034 0.094 Uiso 0.763(5) 1 calc PR A 1 H29C H 0.8517 -0.2162 -0.0043 0.094 Uiso 0.763(5) 1 calc PR A 1 C30A C 1.2272(5) -0.1374(4) -0.0537(3) 0.067(2) Uani 0.763(5) 1 d PD A 1 H30A H 1.3036 -0.0970 -0.0310 0.100 Uiso 0.763(5) 1 calc PR A 1 H30B H 1.2607 -0.1435 -0.0835 0.100 Uiso 0.763(5) 1 calc PR A 1 H30C H 1.2239 -0.2009 -0.0396 0.100 Uiso 0.763(5) 1 calc PR A 1 C31A C 1.0998(10) 0.0382(5) -0.1251(3) 0.076(2) Uani 0.763(5) 1 d PD A 1 H31A H 1.0266 0.0554 -0.1560 0.114 Uiso 0.763(5) 1 calc PR A 1 H31B H 1.1829 -0.0046 -0.1305 0.114 Uiso 0.763(5) 1 calc PR A 1 H31C H 1.1495 0.0962 -0.1088 0.114 Uiso 0.763(5) 1 calc PR A 1 C32A C 0.7533(10) 0.0961(4) -0.1174(3) 0.079(3) Uani 0.763(5) 1 d PD A 1 H32A H 0.7915 0.1559 -0.1006 0.118 Uiso 0.763(5) 1 calc PR A 1 H32B H 0.6408 0.0865 -0.1181 0.118 Uiso 0.763(5) 1 calc PR A 1 H32C H 0.7639 0.0996 -0.1503 0.118 Uiso 0.763(5) 1 calc PR A 1 C33A C 0.6572(6) -0.0530(5) -0.0424(3) 0.071(2) Uani 0.763(5) 1 d PD A 1 H33A H 0.6296 -0.1196 -0.0378 0.106 Uiso 0.763(5) 1 calc PR A 1 H33B H 0.5712 -0.0236 -0.0673 0.106 Uiso 0.763(5) 1 calc PR A 1 H33C H 0.6714 -0.0179 -0.0122 0.106 Uiso 0.763(5) 1 calc PR A 1 C24B C 0.8745(18) -0.0997(12) -0.0421(6) 0.0333(11) Uani 0.237(5) 1 d PD A 2 C25B C 1.0268(17) -0.1032(13) -0.0521(7) 0.0308(11) Uani 0.237(5) 1 d PD A 2 C26B C 1.029(3) -0.0371(18) -0.0895(10) 0.0406(14) Uani 0.237(5) 1 d PD A 2 C27B C 0.883(3) 0.0156(18) -0.1005(11) 0.0375(14) Uani 0.237(5) 1 d PD A 2 C28B C 0.7865(19) -0.0286(16) -0.0735(6) 0.0375(13) Uani 0.237(5) 1 d PD A 2 C29B C 0.843(3) -0.1589(13) -0.0017(6) 0.0624(19) Uani 0.237(5) 1 d PD A 2 H29D H 0.8881 -0.2230 -0.0025 0.094 Uiso 0.237(5) 1 calc PR A 2 H29E H 0.7280 -0.1636 -0.0056 0.094 Uiso 0.237(5) 1 calc PR A 2 H29F H 0.8941 -0.1284 0.0291 0.094 Uiso 0.237(5) 1 calc PR A 2 C30B C 1.1684(18) -0.1629(13) -0.0263(8) 0.067(2) Uani 0.237(5) 1 d PD A 2 H30D H 1.1355 -0.2076 -0.0046 0.100 Uiso 0.237(5) 1 calc PR A 2 H30E H 1.2529 -0.1210 -0.0078 0.100 Uiso 0.237(5) 1 calc PR A 2 H30F H 1.2088 -0.1987 -0.0499 0.100 Uiso 0.237(5) 1 calc PR A 2 C31B C 1.164(3) -0.0020(18) -0.1092(10) 0.076(2) Uani 0.237(5) 1 d PD A 2 H31D H 1.1217 0.0143 -0.1432 0.114 Uiso 0.237(5) 1 calc PR A 2 H31E H 1.2444 -0.0523 -0.1059 0.114 Uiso 0.237(5) 1 calc PR A 2 H31F H 1.2120 0.0549 -0.0914 0.114 Uiso 0.237(5) 1 calc PR A 2 C32B C 0.841(3) 0.1020(13) -0.1327(9) 0.079(3) Uani 0.237(5) 1 d PD A 2 H32D H 0.9262 0.1499 -0.1232 0.118 Uiso 0.237(5) 1 calc PR A 2 H32E H 0.7402 0.1292 -0.1297 0.118 Uiso 0.237(5) 1 calc PR A 2 H32F H 0.8304 0.0829 -0.1661 0.118 Uiso 0.237(5) 1 calc PR A 2 C33B C 0.627(2) 0.0028(18) -0.0666(10) 0.071(2) Uani 0.237(5) 1 d PD A 2 H33D H 0.5758 -0.0512 -0.0552 0.106 Uiso 0.237(5) 1 calc PR A 2 H33E H 0.5590 0.0256 -0.0973 0.106 Uiso 0.237(5) 1 calc PR A 2 H33F H 0.6442 0.0547 -0.0430 0.106 Uiso 0.237(5) 1 calc PR A 2 P1 P 0.45955(11) -0.72150(6) -0.07166(4) 0.0411(2) Uani 1 1 d . . . F1 F 0.4660(3) -0.76303(18) -0.12255(10) 0.0671(7) Uani 1 1 d . . . F2 F 0.4481(4) -0.61652(17) -0.09322(12) 0.0844(10) Uani 1 1 d . . . F3 F 0.4529(3) -0.67909(19) -0.02091(10) 0.0658(7) Uani 1 1 d . . . F4 F 0.4714(3) -0.82647(17) -0.05057(11) 0.0765(9) Uani 1 1 d . . . F5 F 0.2705(2) -0.72962(18) -0.08738(10) 0.0677(7) Uani 1 1 d . . . F6 F 0.6497(3) -0.71188(17) -0.05651(11) 0.0714(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02660(6) 0.02519(7) 0.02301(7) 0.00034(5) 0.00330(5) 0.00327(4) Ru1 0.02353(11) 0.02742(12) 0.02459(15) -0.00425(10) 0.00570(10) -0.00158(9) Cl1 0.0300(4) 0.0489(5) 0.0253(5) 0.0018(3) 0.0049(3) 0.0050(3) N1 0.0250(12) 0.0376(13) 0.0243(16) -0.0048(12) 0.0012(11) 0.0077(10) N2 0.0347(13) 0.0288(13) 0.0334(19) 0.0036(12) 0.0044(12) 0.0077(10) C1 0.0367(17) 0.0427(17) 0.027(2) 0.0030(15) 0.0067(14) 0.0141(14) C2 0.0320(17) 0.056(2) 0.038(2) -0.0027(17) 0.0012(16) 0.0184(15) C3 0.0258(15) 0.063(2) 0.046(3) -0.014(2) 0.0006(15) 0.0096(15) C4 0.0269(15) 0.0434(19) 0.047(3) -0.0108(17) 0.0052(15) 0.0010(13) C5 0.0248(14) 0.0350(16) 0.029(2) -0.0078(14) 0.0060(13) 0.0029(11) C6 0.0235(13) 0.0295(14) 0.0260(19) -0.0070(13) 0.0062(12) 0.0023(11) C7 0.0236(13) 0.0254(15) 0.0221(18) -0.0033(12) 0.0029(12) 0.0023(10) C8 0.0261(14) 0.0256(14) 0.0249(18) -0.0056(12) 0.0065(12) 0.0000(11) C9 0.0406(16) 0.0257(15) 0.0195(17) -0.0041(12) 0.0104(13) -0.0014(12) C10 0.0343(15) 0.0273(15) 0.029(2) -0.0007(13) 0.0126(14) -0.0007(12) C11 0.0275(14) 0.0362(16) 0.031(2) -0.0047(14) 0.0108(13) -0.0024(12) C12 0.052(2) 0.0312(17) 0.033(2) 0.0008(15) 0.0089(16) 0.0099(14) C13 0.0302(16) 0.0400(18) 0.059(3) 0.0066(18) 0.0039(16) 0.0115(13) C14 0.0320(15) 0.0399(17) 0.0260(19) -0.0101(14) 0.0099(13) -0.0070(12) C15 0.0351(16) 0.0423(18) 0.025(2) -0.0059(15) -0.0017(14) -0.0016(13) C16 0.0327(16) 0.0422(18) 0.030(2) -0.0149(15) 0.0073(14) -0.0107(13) C17 0.0478(19) 0.0357(17) 0.034(2) -0.0121(15) 0.0142(16) -0.0084(14) C18 0.0376(16) 0.0395(17) 0.027(2) -0.0117(14) 0.0110(14) -0.0020(13) C19 0.063(2) 0.054(2) 0.044(3) -0.0173(18) 0.030(2) -0.0247(17) C20 0.053(2) 0.057(2) 0.037(3) 0.000(2) -0.0071(19) 0.0070(18) C21 0.0383(19) 0.077(3) 0.049(3) -0.025(2) 0.0142(18) -0.0224(18) C22 0.080(3) 0.0332(18) 0.045(3) -0.0071(18) 0.020(2) -0.0119(18) C23 0.045(2) 0.067(2) 0.047(3) -0.014(2) 0.0159(19) 0.0172(18) C24A 0.040(3) 0.027(2) 0.029(2) -0.0064(17) 0.002(3) -0.003(2) C25A 0.027(2) 0.031(2) 0.032(3) -0.007(2) 0.0037(17) -0.0063(18) C26A 0.053(3) 0.026(4) 0.045(3) -0.015(3) 0.018(3) -0.016(2) C27A 0.057(4) 0.0210(16) 0.030(4) -0.005(2) 0.003(2) 0.007(2) C28A 0.045(3) 0.043(4) 0.024(4) -0.018(3) 0.007(3) -0.002(2) C29A 0.116(6) 0.039(3) 0.026(3) -0.002(2) 0.007(4) -0.012(3) C30A 0.031(3) 0.084(4) 0.074(5) -0.046(4) -0.009(2) 0.009(2) C31A 0.116(6) 0.068(5) 0.053(6) -0.010(3) 0.038(5) -0.048(4) C32A 0.110(6) 0.039(3) 0.063(6) -0.010(3) -0.021(4) 0.034(4) C33A 0.056(3) 0.088(5) 0.078(6) -0.048(4) 0.034(4) -0.010(3) C24B 0.040(3) 0.027(2) 0.029(2) -0.0064(17) 0.002(3) -0.003(2) C25B 0.027(2) 0.031(2) 0.032(3) -0.007(2) 0.0037(17) -0.0063(18) C26B 0.053(3) 0.026(4) 0.045(3) -0.015(3) 0.018(3) -0.016(2) C27B 0.057(4) 0.0210(16) 0.030(4) -0.005(2) 0.003(2) 0.007(2) C28B 0.045(3) 0.043(4) 0.024(4) -0.018(3) 0.007(3) -0.002(2) C29B 0.116(6) 0.039(3) 0.026(3) -0.002(2) 0.007(4) -0.012(3) C30B 0.031(3) 0.084(4) 0.074(5) -0.046(4) -0.009(2) 0.009(2) C31B 0.116(6) 0.068(5) 0.053(6) -0.010(3) 0.038(5) -0.048(4) C32B 0.110(6) 0.039(3) 0.063(6) -0.010(3) -0.021(4) 0.034(4) C33B 0.056(3) 0.088(5) 0.078(6) -0.048(4) 0.034(4) -0.010(3) P1 0.0410(5) 0.0385(5) 0.0447(7) 0.0014(4) 0.0131(4) 0.0069(4) F1 0.0691(16) 0.0798(16) 0.058(2) -0.0175(14) 0.0270(14) 0.0050(12) F2 0.119(2) 0.0461(13) 0.087(3) 0.0145(15) 0.026(2) 0.0047(14) F3 0.0602(14) 0.0879(16) 0.0477(19) -0.0176(14) 0.0110(12) 0.0078(12) F4 0.0901(19) 0.0496(13) 0.085(3) 0.0206(14) 0.0151(17) 0.0068(13) F5 0.0394(12) 0.0958(17) 0.065(2) -0.0177(15) 0.0073(12) 0.0139(11) F6 0.0417(12) 0.0848(17) 0.087(2) -0.0183(16) 0.0156(13) -0.0006(11) _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 C7 2.058(3) . ? Ir1 N1 2.094(2) . ? Ir1 C28B 2.11(2) . ? Ir1 C26B 2.12(3) . ? Ir1 C24A 2.149(5) . ? Ir1 C25B 2.152(19) . ? Ir1 C24B 2.157(17) . ? Ir1 C28A 2.170(6) . ? Ir1 C25A 2.176(5) . ? Ir1 C27B 2.20(3) . ? Ir1 C27A 2.232(8) . ? Ir1 C26A 2.246(7) . ? Ru1 C16 2.165(3) . ? Ru1 C17 2.172(3) . ? Ru1 C11 2.183(3) . ? Ru1 C18 2.186(3) . ? Ru1 C15 2.195(4) . ? Ru1 C14 2.204(3) . ? Ru1 C10 2.210(3) . ? Ru1 C6 2.232(3) . ? Ru1 C8 2.259(3) . ? Ru1 C9 2.325(3) . ? Ru1 C7 2.344(3) . ? N1 C1 1.353(4) . ? N1 C5 1.354(4) . ? N2 C9 1.378(4) . ? N2 C13 1.448(4) . ? N2 C12 1.453(4) . ? C1 C2 1.373(5) . ? C2 C3 1.371(5) . ? C3 C4 1.385(5) . ? C4 C5 1.395(4) . ? C5 C6 1.470(4) . ? C6 C11 1.420(4) . ? C6 C7 1.427(4) . ? C7 C8 1.405(4) . ? C8 C9 1.422(4) . ? C9 C10 1.423(4) . ? C10 C11 1.414(4) . ? C14 C18 1.426(5) . ? C14 C15 1.435(4) . ? C14 C19 1.494(4) . ? C15 C16 1.439(5) . ? C15 C20 1.503(5) . ? C16 C17 1.428(5) . ? C16 C21 1.507(4) . ? C17 C18 1.421(4) . ? C17 C22 1.521(5) . ? C18 C23 1.506(4) . ? C24A C28A 1.4254(19) . ? C24A C25A 1.4261(19) . ? C24A C29A 1.510(2) . ? C25A C26A 1.426(2) . ? C25A C30A 1.5101(19) . ? C26A C27A 1.4255(19) . ? C26A C31A 1.510(2) . ? C27A C28A 1.427(2) . ? C27A C32A 1.511(2) . ? C28A C33A 1.511(2) . ? C24B C25B 1.425(2) . ? C24B C28B 1.425(2) . ? C24B C29B 1.510(2) . ? C25B C26B 1.425(2) . ? C25B C30B 1.510(2) . ? C26B C27B 1.425(2) . ? C26B C31B 1.510(2) . ? C27B C28B 1.425(2) . ? C27B C32B 1.510(2) . ? C28B C33B 1.510(2) . ? P1 F4 1.583(2) . ? P1 F5 1.586(2) . ? P1 F2 1.588(3) . ? P1 F1 1.594(3) . ? P1 F3 1.595(3) . ? P1 F6 1.597(2) . ? 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 C7 Ir1 N1 77.71(10) . . ? C7 Ir1 C28B 129.8(5) . . ? N1 Ir1 C28B 91.8(5) . . ? C7 Ir1 C26B 131.1(5) . . ? N1 Ir1 C26B 150.3(5) . . ? C28B Ir1 C26B 64.9(8) . . ? C7 Ir1 C24A 93.51(13) . . ? N1 Ir1 C24A 122.77(14) . . ? C28B Ir1 C24A 51.7(4) . . ? C26B Ir1 C24A 57.7(6) . . ? C7 Ir1 C25B 99.3(4) . . ? N1 Ir1 C25B 146.6(4) . . ? C28B Ir1 C25B 64.3(6) . . ? C26B Ir1 C25B 39.0(3) . . ? C24A Ir1 C25B 23.9(4) . . ? C7 Ir1 C24B 97.9(4) . . ? N1 Ir1 C24B 108.3(4) . . ? C28B Ir1 C24B 39.0(2) . . ? C26B Ir1 C24B 65.8(7) . . ? C24A Ir1 C24B 16.2(3) . . ? C25B Ir1 C24B 38.6(2) . . ? C7 Ir1 C28A 117.75(15) . . ? N1 Ir1 C28A 96.87(14) . . ? C28B Ir1 C28A 14.3(4) . . ? C26B Ir1 C28A 65.3(7) . . ? C24A Ir1 C28A 38.54(8) . . ? C25B Ir1 C28A 54.6(4) . . ? C24B Ir1 C28A 24.8(4) . . ? C7 Ir1 C25A 104.71(13) . . ? N1 Ir1 C25A 160.59(14) . . ? C28B Ir1 C25A 71.7(5) . . ? C26B Ir1 C25A 28.2(5) . . ? C24A Ir1 C25A 38.51(8) . . ? C25B Ir1 C25A 14.8(4) . . ? C24B Ir1 C25A 52.4(4) . . ? C28A Ir1 C25A 64.70(15) . . ? C7 Ir1 C27B 162.2(7) . . ? N1 Ir1 C27B 111.9(6) . . ? C28B Ir1 C27B 38.5(4) . . ? C26B Ir1 C27B 38.5(4) . . ? C24A Ir1 C27B 68.6(7) . . ? C25B Ir1 C27B 64.2(8) . . ? C24B Ir1 C27B 65.2(8) . . ? C28A Ir1 C27B 47.9(6) . . ? C25A Ir1 C27B 61.2(7) . . ? C7 Ir1 C27A 155.03(17) . . ? N1 Ir1 C27A 105.86(17) . . ? C28B Ir1 C27A 27.6(6) . . ? C26B Ir1 C27A 45.4(6) . . ? C24A Ir1 C27A 63.43(19) . . ? C25B Ir1 C27A 63.8(5) . . ? C24B Ir1 C27A 57.3(4) . . ? C28A Ir1 C27A 37.80(10) . . ? C25A Ir1 C27A 63.9(2) . . ? C27B Ir1 C27A 11.0(5) . . ? C7 Ir1 C26A 141.24(14) . . ? N1 Ir1 C26A 140.40(13) . . ? C28B Ir1 C26A 59.7(6) . . ? C26B Ir1 C26A 10.1(5) . . ? C24A Ir1 C26A 62.46(19) . . ? C25B Ir1 C26A 46.7(5) . . ? C24B Ir1 C26A 67.8(4) . . ? C28A Ir1 C26A 62.58(19) . . ? C25A Ir1 C26A 37.60(10) . . ? C27B Ir1 C26A 29.1(6) . . ? C27A Ir1 C26A 37.13(10) . . ? C16 Ru1 C17 38.44(13) . . ? C16 Ru1 C11 102.72(12) . . ? C17 Ru1 C11 114.30(12) . . ? C16 Ru1 C18 64.35(12) . . ? C17 Ru1 C18 38.07(12) . . ? C11 Ru1 C18 149.04(12) . . ? C16 Ru1 C15 38.54(13) . . ? C17 Ru1 C15 64.01(13) . . ? C11 Ru1 C15 124.26(12) . . ? C18 Ru1 C15 64.08(13) . . ? C16 Ru1 C14 63.95(12) . . ? C17 Ru1 C14 63.33(12) . . ? C11 Ru1 C14 162.30(12) . . ? C18 Ru1 C14 37.89(12) . . ? C15 Ru1 C14 38.09(12) . . ? C16 Ru1 C10 116.53(12) . . ? C17 Ru1 C10 102.40(13) . . ? C11 Ru1 C10 37.55(11) . . ? C18 Ru1 C10 120.40(12) . . ? C15 Ru1 C10 153.27(12) . . ? C14 Ru1 C10 157.71(11) . . ? C16 Ru1 C6 113.97(11) . . ? C17 Ru1 C6 144.61(11) . . ? C11 Ru1 C6 37.49(11) . . ? C18 Ru1 C6 172.61(13) . . ? C15 Ru1 C6 109.84(12) . . ? C14 Ru1 C6 134.72(12) . . ? C10 Ru1 C6 66.96(11) . . ? C16 Ru1 C8 177.17(12) . . ? C17 Ru1 C8 143.47(12) . . ? C11 Ru1 C8 78.41(11) . . ? C18 Ru1 C8 115.94(11) . . ? C15 Ru1 C8 138.74(12) . . ? C14 Ru1 C8 114.38(11) . . ? C10 Ru1 C8 65.95(11) . . ? C6 Ru1 C8 65.35(10) . . ? C16 Ru1 C9 146.72(12) . . ? C17 Ru1 C9 115.05(12) . . ? C11 Ru1 C9 66.28(11) . . ? C18 Ru1 C9 108.15(12) . . ? C15 Ru1 C9 169.30(12) . . ? C14 Ru1 C9 131.30(11) . . ? C10 Ru1 C9 36.47(10) . . ? C6 Ru1 C9 77.28(11) . . ? C8 Ru1 C9 36.11(10) . . ? C16 Ru1 C7 142.59(11) . . ? C17 Ru1 C7 178.95(12) . . ? C11 Ru1 C7 66.11(11) . . ? C18 Ru1 C7 141.24(11) . . ? C15 Ru1 C7 116.65(11) . . ? C14 Ru1 C7 116.61(11) . . ? C10 Ru1 C7 77.33(11) . . ? C6 Ru1 C7 36.23(9) . . ? C8 Ru1 C7 35.49(9) . . ? C9 Ru1 C7 64.13(10) . . ? C1 N1 C5 119.2(3) . . ? C1 N1 Ir1 123.8(2) . . ? C5 N1 Ir1 116.8(2) . . ? C9 N2 C13 120.1(3) . . ? C9 N2 C12 119.3(3) . . ? C13 N2 C12 117.5(2) . . ? N1 C1 C2 122.0(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 C4 119.6(3) . . ? C3 C4 C5 119.1(3) . . ? N1 C5 C4 120.7(3) . . ? N1 C5 C6 113.0(2) . . ? C4 C5 C6 126.3(3) . . ? C11 C6 C7 120.6(3) . . ? C11 C6 C5 124.2(3) . . ? C7 C6 C5 115.0(3) . . ? C11 C6 Ru1 69.38(17) . . ? C7 C6 Ru1 76.18(16) . . ? C5 C6 Ru1 123.8(2) . . ? C8 C7 C6 117.7(3) . . ? C8 C7 Ir1 128.2(2) . . ? C6 C7 Ir1 113.38(19) . . ? C8 C7 Ru1 68.93(16) . . ? C6 C7 Ru1 67.59(16) . . ? Ir1 C7 Ru1 142.68(15) . . ? C7 C8 C9 122.5(3) . . ? C7 C8 Ru1 75.57(17) . . ? C9 C8 Ru1 74.50(17) . . ? N2 C9 C8 121.4(3) . . ? N2 C9 C10 121.2(3) . . ? C8 C9 C10 117.5(3) . . ? N2 C9 Ru1 134.7(2) . . ? C8 C9 Ru1 69.39(18) . . ? C10 C9 Ru1 67.34(19) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 Ru1 70.19(19) . . ? C9 C10 Ru1 76.20(19) . . ? C10 C11 C6 119.7(3) . . ? C10 C11 Ru1 72.26(18) . . ? C6 C11 Ru1 73.13(18) . . ? C18 C14 C15 108.7(3) . . ? C18 C14 C19 124.8(3) . . ? C15 C14 C19 126.0(3) . . ? C18 C14 Ru1 70.4(2) . . ? C15 C14 Ru1 70.6(2) . . ? C19 C14 Ru1 131.0(2) . . ? C14 C15 C16 107.2(3) . . ? C14 C15 C20 125.5(3) . . ? C16 C15 C20 127.2(3) . . ? C14 C15 Ru1 71.3(2) . . ? C16 C15 Ru1 69.6(2) . . ? C20 C15 Ru1 127.1(3) . . ? C17 C16 C15 107.7(3) . . ? C17 C16 C21 125.8(3) . . ? C15 C16 C21 126.5(3) . . ? C17 C16 Ru1 71.02(19) . . ? C15 C16 Ru1 71.83(18) . . ? C21 C16 Ru1 124.7(3) . . ? C18 C17 C16 108.9(3) . . ? C18 C17 C22 126.2(3) . . ? C16 C17 C22 124.8(3) . . ? C18 C17 Ru1 71.53(18) . . ? C16 C17 Ru1 70.55(18) . . ? C22 C17 Ru1 126.6(3) . . ? C17 C18 C14 107.6(3) . . ? C17 C18 C23 125.7(3) . . ? C14 C18 C23 126.5(3) . . ? C17 C18 Ru1 70.40(18) . . ? C14 C18 Ru1 71.73(18) . . ? C23 C18 Ru1 127.3(3) . . ? C28A C24A C25A 109.3(3) . . ? C28A C24A C29A 125.2(4) . . ? C25A C24A C29A 125.4(4) . . ? C28A C24A Ir1 71.5(3) . . ? C25A C24A Ir1 71.8(3) . . ? C29A C24A Ir1 126.5(3) . . ? C24A C25A C26A 106.1(3) . . ? C24A C25A C30A 126.0(4) . . ? C26A C25A C30A 127.1(4) . . ? C24A C25A Ir1 69.7(2) . . ? C26A C25A Ir1 73.9(3) . . ? C30A C25A Ir1 128.6(4) . . ? C27A C26A C25A 109.7(3) . . ? C27A C26A C31A 125.1(4) . . ? C25A C26A C31A 125.2(4) . . ? C27A C26A Ir1 70.9(4) . . ? C25A C26A Ir1 68.5(3) . . ? C31A C26A Ir1 125.9(6) . . ? C26A C27A C28A 107.1(3) . . ? C26A C27A C32A 125.6(5) . . ? C28A C27A C32A 127.2(5) . . ? C26A C27A Ir1 72.0(4) . . ? C28A C27A Ir1 68.8(4) . . ? C32A C27A Ir1 127.1(6) . . ? C24A C28A C27A 107.7(3) . . ? C24A C28A C33A 124.5(4) . . ? C27A C28A C33A 127.8(4) . . ? C24A C28A Ir1 69.9(3) . . ? C27A C28A Ir1 73.4(4) . . ? C33A C28A Ir1 121.6(4) . . ? C25B C24B C28B 105.4(11) . . ? C25B C24B C29B 120.0(16) . . ? C28B C24B C29B 134.4(16) . . ? C25B C24B Ir1 70.5(10) . . ? C28B C24B Ir1 68.7(11) . . ? C29B C24B Ir1 129.2(13) . . ? C24B C25B C26B 109.1(12) . . ? C24B C25B C30B 126.6(15) . . ? C26B C25B C30B 124.2(16) . . ? C24B C25B Ir1 70.9(10) . . ? C26B C25B Ir1 69.2(14) . . ? C30B C25B Ir1 128.1(14) . . ? C27B C26B C25B 108.6(14) . . ? C27B C26B C31B 118.5(17) . . ? C25B C26B C31B 131.4(18) . . ? C27B C26B Ir1 74.0(17) . . ? C25B C26B Ir1 71.8(13) . . ? C31B C26B Ir1 131(2) . . ? C26B C27B C28B 105.5(13) . . ? C26B C27B C32B 127.3(16) . . ? C28B C27B C32B 127.1(19) . . ? C26B C27B Ir1 67.5(16) . . ? C28B C27B Ir1 67.2(13) . . ? C32B C27B Ir1 131(2) . . ? C24B C28B C27B 110.9(13) . . ? C24B C28B C33B 118.4(17) . . ? C27B C28B C33B 129.3(18) . . ? C24B C28B Ir1 72.3(11) . . ? C27B C28B Ir1 74.3(15) . . ? C33B C28B Ir1 131.1(17) . . ? F4 P1 F5 90.10(15) . . ? F4 P1 F2 179.50(19) . . ? F5 P1 F2 90.02(16) . . ? F4 P1 F1 90.10(16) . . ? F5 P1 F1 89.63(14) . . ? F2 P1 F1 89.41(17) . . ? F4 P1 F3 90.35(16) . . ? F5 P1 F3 90.34(14) . . ? F2 P1 F3 90.13(16) . . ? F1 P1 F3 179.55(15) . . ? F4 P1 F6 90.82(14) . . ? F5 P1 F6 179.02(18) . . ? F2 P1 F6 89.06(16) . . ? F1 P1 F6 90.01(14) . . ? F3 P1 F6 90.01(14) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 1.624 _refine_diff_density_min -1.549 _refine_diff_density_rms 0.118 ###END data_[exo-5b]0 _database_code_depnum_ccdc_archive 'CCDC 805116' #TrackingRef '- compilation_djukic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H36 Cl Cr Ir N2 O3, C3 H6 O' _chemical_formula_sum 'C33 H42 Cl Cr Ir N2 O4' _chemical_formula_weight 810.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cr Cr 0.3209 0.6236 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/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 10.649(1) _cell_length_b 15.812(1) _cell_length_c 21.131(1) _cell_angle_alpha 90.00 _cell_angle_beta 107.397(3) _cell_angle_gamma 90.00 _cell_volume 3395.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 4521 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 4.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3193 _exptl_absorpt_correction_T_max 0.9180 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26792 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 29.95 _reflns_number_total 9667 _reflns_number_gt 6935 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0095P)^2^+4.6460P] 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 9667 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.350506(17) -0.533408(13) -0.302494(8) 0.01645(5) Uani 1 1 d . . . Cr1 Cr 0.02443(7) -0.38651(5) -0.34818(3) 0.01881(17) Uani 1 1 d . . . Cl1 Cl 0.35593(12) -0.60408(9) -0.40228(5) 0.0269(3) Uani 1 1 d . . . O1 O -0.0539(4) -0.2067(3) -0.38025(19) 0.0488(11) Uani 1 1 d . . . O2 O 0.2106(3) -0.3075(3) -0.22822(17) 0.0434(11) Uani 1 1 d . . . O3 O -0.1654(3) -0.4033(3) -0.26954(16) 0.0347(9) Uani 1 1 d . . . N1 N 0.3947(4) -0.4257(3) -0.35000(16) 0.0180(9) Uani 1 1 d . . . N2 N -0.1877(4) -0.5513(3) -0.40688(17) 0.0248(10) Uani 1 1 d . . . C1 C 0.1674(4) -0.4935(3) -0.3570(2) 0.0176(10) Uani 1 1 d . . . C2 C 0.0471(4) -0.5305(4) -0.35772(19) 0.0198(10) Uani 1 1 d . . . H2 H 0.0469 -0.5718 -0.3251 0.024 Uiso 1 1 calc R . . C3 C -0.0754(4) -0.5087(3) -0.4056(2) 0.0205(11) Uani 1 1 d . . . C4 C -0.0737(4) -0.4417(3) -0.4496(2) 0.0208(11) Uani 1 1 d . . . H4 H -0.1538 -0.4238 -0.4805 0.025 Uiso 1 1 calc R . . C5 C 0.0447(4) -0.4012(3) -0.4482(2) 0.0202(10) Uani 1 1 d . . . H5 H 0.0438 -0.3568 -0.4786 0.024 Uiso 1 1 calc R . . C6 C 0.1650(4) -0.4260(3) -0.4021(2) 0.0187(10) Uani 1 1 d . . . C7 C 0.2921(4) -0.3872(3) -0.39643(19) 0.0181(10) Uani 1 1 d . . . C8 C 0.3139(4) -0.3206(3) -0.4340(2) 0.0199(11) Uani 1 1 d . . . H8 H 0.2411 -0.2949 -0.4655 0.024 Uiso 1 1 calc R . . C9 C 0.4402(4) -0.2900(3) -0.42665(19) 0.0180(10) Uani 1 1 d . . . C10 C 0.5428(4) -0.3308(3) -0.3793(2) 0.0229(11) Uani 1 1 d . . . H10 H 0.6311 -0.3129 -0.3721 0.028 Uiso 1 1 calc R . . C11 C 0.5158(4) -0.3970(3) -0.3430(2) 0.0230(11) Uani 1 1 d . . . H11 H 0.5874 -0.4236 -0.3113 0.028 Uiso 1 1 calc R . . C12 C -0.1866(5) -0.6086(4) -0.3526(2) 0.0313(13) Uani 1 1 d . . . H12A H -0.1259 -0.6555 -0.3517 0.047 Uiso 1 1 calc R . . H12B H -0.2754 -0.6310 -0.3591 0.047 Uiso 1 1 calc R . . H12C H -0.1579 -0.5779 -0.3104 0.047 Uiso 1 1 calc R . . C13 C -0.3143(4) -0.5159(4) -0.4449(2) 0.0294(13) Uani 1 1 d . . . H13A H -0.3215 -0.4577 -0.4304 0.044 Uiso 1 1 calc R . . H13B H -0.3856 -0.5501 -0.4377 0.044 Uiso 1 1 calc R . . H13C H -0.3210 -0.5161 -0.4922 0.044 Uiso 1 1 calc R . . C14 C 0.4631(5) -0.2171(3) -0.4694(2) 0.0238(11) Uani 1 1 d . . . C15 C 0.3890(6) -0.1384(4) -0.4559(2) 0.0353(14) Uani 1 1 d . . . H15A H 0.4246 -0.1221 -0.4092 0.053 Uiso 1 1 calc R . . H15B H 0.2952 -0.1516 -0.4658 0.053 Uiso 1 1 calc R . . H15C H 0.4003 -0.0916 -0.4841 0.053 Uiso 1 1 calc R . . C16 C 0.4078(5) -0.2415(4) -0.5428(2) 0.0305(13) Uani 1 1 d . . . H16A H 0.4201 -0.1944 -0.5705 0.046 Uiso 1 1 calc R . . H16B H 0.3138 -0.2542 -0.5531 0.046 Uiso 1 1 calc R . . H16C H 0.4543 -0.2915 -0.5517 0.046 Uiso 1 1 calc R . . C17 C 0.6088(5) -0.1951(4) -0.4546(3) 0.0431(16) Uani 1 1 d . . . H17A H 0.6450 -0.1797 -0.4077 0.065 Uiso 1 1 calc R . . H17B H 0.6184 -0.1474 -0.4823 0.065 Uiso 1 1 calc R . . H17C H 0.6563 -0.2442 -0.4641 0.065 Uiso 1 1 calc R . . C18 C 0.4428(5) -0.5110(3) -0.1974(2) 0.0245(12) Uani 1 1 d . . . C19 C 0.5286(5) -0.5688(4) -0.2176(2) 0.0261(12) Uani 1 1 d . . . C20 C 0.4559(5) -0.6421(4) -0.2421(2) 0.0285(13) Uani 1 1 d . . . C21 C 0.3240(5) -0.6318(4) -0.2375(2) 0.0262(12) Uani 1 1 d . . . C22 C 0.3187(5) -0.5520(3) -0.2067(2) 0.0241(12) Uani 1 1 d . . . C23 C 0.4865(6) -0.4293(4) -0.1632(2) 0.0482(18) Uani 1 1 d . . . H23A H 0.4099 -0.3930 -0.1675 0.072 Uiso 1 1 calc R . . H23B H 0.5472 -0.4013 -0.1834 0.072 Uiso 1 1 calc R . . H23C H 0.5314 -0.4399 -0.1162 0.072 Uiso 1 1 calc R . . C24 C 0.6728(5) -0.5573(5) -0.2080(3) 0.054(2) Uani 1 1 d . . . H24A H 0.7230 -0.5797 -0.1646 0.082 Uiso 1 1 calc R . . H24B H 0.6922 -0.4970 -0.2103 0.082 Uiso 1 1 calc R . . H24C H 0.6975 -0.5878 -0.2429 0.082 Uiso 1 1 calc R . . C25 C 0.5046(7) -0.7194(4) -0.2686(3) 0.0537(19) Uani 1 1 d . . . H25A H 0.5703 -0.7028 -0.2903 0.081 Uiso 1 1 calc R . . H25B H 0.4306 -0.7474 -0.3009 0.081 Uiso 1 1 calc R . . H25C H 0.5445 -0.7583 -0.2321 0.081 Uiso 1 1 calc R . . C26 C 0.2192(6) -0.6993(4) -0.2532(3) 0.0523(19) Uani 1 1 d . . . H26A H 0.1401 -0.6777 -0.2442 0.079 Uiso 1 1 calc R . . H26B H 0.2515 -0.7492 -0.2256 0.079 Uiso 1 1 calc R . . H26C H 0.1980 -0.7149 -0.3001 0.079 Uiso 1 1 calc R . . C27 C 0.2081(6) -0.5215(4) -0.1825(2) 0.0462(18) Uani 1 1 d . . . H27A H 0.2105 -0.5511 -0.1414 0.069 Uiso 1 1 calc R . . H27B H 0.1240 -0.5329 -0.2162 0.069 Uiso 1 1 calc R . . H27C H 0.2173 -0.4605 -0.1740 0.069 Uiso 1 1 calc R . . C28 C -0.0251(5) -0.2773(4) -0.3688(2) 0.0295(12) Uani 1 1 d . . . C29 C 0.1416(5) -0.3415(4) -0.2746(2) 0.0258(12) Uani 1 1 d . . . C30 C -0.0924(4) -0.3963(3) -0.3012(2) 0.0222(11) Uani 1 1 d . . . O4 O 0.0505(5) -0.2609(4) -0.0548(3) 0.089(2) Uani 1 1 d . . . C31 C -0.0252(7) -0.3183(6) -0.0698(3) 0.058(2) Uani 1 1 d . . . C32 C -0.1581(7) -0.3141(6) -0.0630(4) 0.091(3) Uani 1 1 d . . . H32A H -0.1593 -0.3425 -0.0220 0.136 Uiso 1 1 calc R . . H32B H -0.2201 -0.3422 -0.1010 0.136 Uiso 1 1 calc R . . H32C H -0.1838 -0.2548 -0.0616 0.136 Uiso 1 1 calc R . . C33 C 0.0145(9) -0.3961(8) -0.0979(5) 0.149(5) Uani 1 1 d . . . H33A H -0.0464 -0.4063 -0.1422 0.223 Uiso 1 1 calc R . . H33B H 0.0121 -0.4443 -0.0691 0.223 Uiso 1 1 calc R . . H33C H 0.1039 -0.3892 -0.1009 0.223 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 0.01871(8) 0.01505(10) 0.01789(8) 0.00112(8) 0.00896(6) 0.00113(9) Cr1 0.0163(4) 0.0192(5) 0.0225(4) -0.0014(3) 0.0082(3) -0.0002(3) Cl1 0.0326(7) 0.0265(8) 0.0241(6) -0.0044(5) 0.0123(5) 0.0053(6) O1 0.062(3) 0.024(3) 0.064(3) 0.007(2) 0.023(2) 0.012(2) O2 0.032(2) 0.047(3) 0.044(2) -0.014(2) 0.0003(17) -0.006(2) O3 0.032(2) 0.035(3) 0.048(2) 0.0007(18) 0.0276(17) -0.0012(19) N1 0.0177(19) 0.019(3) 0.0201(19) 0.0018(15) 0.0094(15) -0.0013(17) N2 0.023(2) 0.027(3) 0.026(2) -0.0020(17) 0.0100(16) -0.0084(19) C1 0.022(2) 0.016(3) 0.017(2) -0.0036(17) 0.0096(17) 0.0005(19) C2 0.023(2) 0.016(3) 0.024(2) -0.005(2) 0.0121(17) -0.002(2) C3 0.024(2) 0.023(3) 0.018(2) -0.0057(18) 0.0115(18) -0.002(2) C4 0.018(2) 0.024(3) 0.021(2) -0.0020(18) 0.0072(17) -0.002(2) C5 0.020(2) 0.022(3) 0.020(2) -0.0024(19) 0.0089(17) 0.000(2) C6 0.019(2) 0.018(3) 0.022(2) -0.0023(18) 0.0100(18) -0.003(2) C7 0.021(2) 0.020(3) 0.017(2) 0.0001(18) 0.0116(17) 0.003(2) C8 0.016(2) 0.027(3) 0.019(2) 0.0008(19) 0.0075(17) 0.000(2) C9 0.022(2) 0.019(3) 0.015(2) -0.0022(17) 0.0091(17) -0.002(2) C10 0.018(2) 0.028(3) 0.025(2) -0.002(2) 0.0092(18) -0.007(2) C11 0.020(2) 0.026(3) 0.024(2) 0.002(2) 0.0068(18) -0.001(2) C12 0.033(3) 0.031(4) 0.031(3) -0.006(2) 0.012(2) -0.016(3) C13 0.023(3) 0.029(4) 0.038(3) -0.005(2) 0.011(2) -0.005(2) C14 0.028(3) 0.023(3) 0.021(2) -0.0006(19) 0.0077(19) -0.004(2) C15 0.057(4) 0.022(4) 0.028(3) 0.001(2) 0.016(2) -0.009(3) C16 0.041(3) 0.028(4) 0.025(3) 0.001(2) 0.015(2) -0.005(3) C17 0.040(3) 0.045(5) 0.043(3) 0.012(3) 0.010(3) -0.015(3) C18 0.034(3) 0.025(3) 0.013(2) 0.0031(18) 0.0063(19) 0.002(2) C19 0.021(3) 0.037(4) 0.021(2) 0.013(2) 0.0078(19) 0.003(2) C20 0.045(3) 0.024(3) 0.020(2) 0.007(2) 0.015(2) 0.017(3) C21 0.034(3) 0.026(3) 0.017(2) 0.007(2) 0.0049(19) -0.005(2) C22 0.032(3) 0.023(4) 0.023(2) 0.0058(19) 0.0166(19) 0.009(2) C23 0.073(5) 0.033(4) 0.025(3) -0.002(2) -0.007(3) -0.005(3) C24 0.031(3) 0.091(7) 0.039(3) 0.035(3) 0.008(2) -0.001(3) C25 0.085(5) 0.037(5) 0.049(4) 0.007(3) 0.035(3) 0.033(4) C26 0.058(4) 0.031(4) 0.055(4) 0.016(3) -0.002(3) -0.021(3) C27 0.053(4) 0.060(5) 0.038(3) 0.017(3) 0.033(3) 0.023(4) C28 0.035(3) 0.023(4) 0.033(3) 0.003(2) 0.013(2) 0.005(3) C29 0.022(3) 0.025(3) 0.033(3) 0.000(2) 0.011(2) -0.001(2) C30 0.019(2) 0.020(3) 0.026(2) -0.004(2) 0.0044(18) -0.003(2) O4 0.054(3) 0.117(6) 0.100(4) -0.053(4) 0.027(3) -0.025(4) C31 0.042(4) 0.089(7) 0.041(4) -0.030(4) 0.007(3) -0.003(4) C32 0.054(5) 0.123(10) 0.104(6) -0.020(6) 0.037(4) -0.007(5) C33 0.096(8) 0.157(13) 0.185(10) -0.119(9) 0.029(7) 0.010(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C1 2.046(4) . ? Ir1 N1 2.101(4) . ? Ir1 C21 2.150(5) . ? Ir1 C22 2.170(4) . ? Ir1 C18 2.171(4) . ? Ir1 C20 2.233(5) . ? Ir1 C19 2.257(4) . ? Ir1 Cl1 2.4024(11) . ? Cr1 C30 1.815(5) . ? Cr1 C28 1.820(6) . ? Cr1 C29 1.823(5) . ? Cr1 C5 2.201(4) . ? Cr1 C6 2.224(4) . ? Cr1 C4 2.260(4) . ? Cr1 C2 2.305(5) . ? Cr1 C1 2.321(5) . ? Cr1 C3 2.359(5) . ? O1 C28 1.163(6) . ? O2 C29 1.165(5) . ? O3 C30 1.173(5) . ? N1 C11 1.333(5) . ? N1 C7 1.373(5) . ? N2 C3 1.366(6) . ? N2 C13 1.460(6) . ? N2 C12 1.460(6) . ? C1 C2 1.404(6) . ? C1 C6 1.427(6) . ? C2 C3 1.434(6) . ? C2 H2 0.9500 . ? C3 C4 1.411(6) . ? C4 C5 1.407(6) . ? C4 H4 0.9500 . ? C5 C6 1.413(6) . ? C5 H5 0.9500 . ? C6 C7 1.457(6) . ? C7 C8 1.380(6) . ? C8 C9 1.393(6) . ? C8 H8 0.9500 . ? C9 C10 1.400(6) . ? C9 C14 1.529(6) . ? C10 C11 1.377(7) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.528(7) . ? C14 C16 1.535(6) . ? C14 C15 1.545(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C22 1.433(7) . ? C18 C19 1.444(7) . ? C18 C23 1.485(7) . ? C19 C20 1.404(7) . ? C19 C24 1.498(6) . ? C20 C21 1.446(7) . ? C20 C25 1.500(7) . ? C21 C22 1.428(7) . ? C21 C26 1.507(7) . ? C22 C27 1.498(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? O4 C31 1.192(9) . ? C31 C32 1.466(9) . ? C31 C33 1.481(11) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 N1 78.06(17) . . ? C1 Ir1 C21 107.32(19) . . ? N1 Ir1 C21 169.53(16) . . ? C1 Ir1 C22 100.29(17) . . ? N1 Ir1 C22 132.49(18) . . ? C21 Ir1 C22 38.61(19) . . ? C1 Ir1 C18 126.11(18) . . ? N1 Ir1 C18 104.97(17) . . ? C21 Ir1 C18 64.57(19) . . ? C22 Ir1 C18 38.53(18) . . ? C1 Ir1 C20 142.2(2) . . ? N1 Ir1 C20 138.69(18) . . ? C21 Ir1 C20 38.46(18) . . ? C22 Ir1 C20 63.53(17) . . ? C18 Ir1 C20 62.92(19) . . ? C1 Ir1 C19 163.17(16) . . ? N1 Ir1 C19 109.00(17) . . ? C21 Ir1 C19 63.40(18) . . ? C22 Ir1 C19 63.49(17) . . ? C18 Ir1 C19 38.00(18) . . ? C20 Ir1 C19 36.44(19) . . ? C1 Ir1 Cl1 85.31(12) . . ? N1 Ir1 Cl1 83.70(10) . . ? C21 Ir1 Cl1 105.45(15) . . ? C22 Ir1 Cl1 143.81(15) . . ? C18 Ir1 Cl1 148.31(14) . . ? C20 Ir1 Cl1 90.22(13) . . ? C19 Ir1 Cl1 110.31(14) . . ? C30 Cr1 C28 90.9(2) . . ? C30 Cr1 C29 88.5(2) . . ? C28 Cr1 C29 84.8(2) . . ? C30 Cr1 C5 142.77(18) . . ? C28 Cr1 C5 88.6(2) . . ? C29 Cr1 C5 128.48(19) . . ? C30 Cr1 C6 158.8(2) . . ? C28 Cr1 C6 109.6(2) . . ? C29 Cr1 C6 98.79(19) . . ? C5 Cr1 C6 37.24(15) . . ? C30 Cr1 C4 106.68(18) . . ? C28 Cr1 C4 97.0(2) . . ? C29 Cr1 C4 164.69(19) . . ? C5 Cr1 C4 36.75(15) . . ? C6 Cr1 C4 66.24(16) . . ? C30 Cr1 C2 94.0(2) . . ? C28 Cr1 C2 161.24(19) . . ? C29 Cr1 C2 113.4(2) . . ? C5 Cr1 C2 76.62(17) . . ? C6 Cr1 C2 64.78(17) . . ? C4 Cr1 C2 64.29(16) . . ? C30 Cr1 C1 123.7(2) . . ? C28 Cr1 C1 145.4(2) . . ? C29 Cr1 C1 93.2(2) . . ? C5 Cr1 C1 65.84(16) . . ? C6 Cr1 C1 36.52(16) . . ? C4 Cr1 C1 76.73(16) . . ? C2 Cr1 C1 35.33(15) . . ? C30 Cr1 C3 86.23(19) . . ? C28 Cr1 C3 126.9(2) . . ? C29 Cr1 C3 147.9(2) . . ? C5 Cr1 C3 65.01(17) . . ? C6 Cr1 C3 77.02(16) . . ? C4 Cr1 C3 35.51(16) . . ? C2 Cr1 C3 35.80(15) . . ? C1 Cr1 C3 64.34(16) . . ? C11 N1 C7 117.8(4) . . ? C11 N1 Ir1 124.8(3) . . ? C7 N1 Ir1 117.1(3) . . ? C3 N2 C13 118.7(4) . . ? C3 N2 C12 119.4(4) . . ? C13 N2 C12 117.4(4) . . ? C2 C1 C6 118.1(4) . . ? C2 C1 Ir1 126.2(4) . . ? C6 C1 Ir1 115.5(3) . . ? C2 C1 Cr1 71.7(3) . . ? C6 C1 Cr1 68.1(3) . . ? Ir1 C1 Cr1 135.8(2) . . ? C1 C2 C3 122.8(4) . . ? C1 C2 Cr1 72.9(3) . . ? C3 C2 Cr1 74.1(3) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? Cr1 C2 H2 126.3 . . ? N2 C3 C4 122.7(4) . . ? N2 C3 C2 120.1(4) . . ? C4 C3 C2 117.2(4) . . ? N2 C3 Cr1 132.2(3) . . ? C4 C3 Cr1 68.4(3) . . ? C2 C3 Cr1 70.1(3) . . ? C5 C4 C3 121.0(4) . . ? C5 C4 Cr1 69.3(2) . . ? C3 C4 Cr1 76.1(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? Cr1 C4 H4 127.1 . . ? C4 C5 C6 120.7(4) . . ? C4 C5 Cr1 73.9(2) . . ? C6 C5 Cr1 72.3(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? Cr1 C5 H5 126.0 . . ? C5 C6 C1 120.0(4) . . ? C5 C6 C7 124.6(4) . . ? C1 C6 C7 115.4(4) . . ? C5 C6 Cr1 70.5(2) . . ? C1 C6 Cr1 75.4(2) . . ? C7 C6 Cr1 126.2(3) . . ? N1 C7 C8 120.9(4) . . ? N1 C7 C6 113.2(4) . . ? C8 C7 C6 125.9(4) . . ? C7 C8 C9 121.6(4) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C10 116.1(4) . . ? C8 C9 C14 121.0(4) . . ? C10 C9 C14 122.8(4) . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? N1 C11 C10 123.6(4) . . ? N1 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C9 112.4(4) . . ? C17 C14 C16 108.9(4) . . ? C9 C14 C16 109.1(4) . . ? C17 C14 C15 108.8(5) . . ? C9 C14 C15 108.5(4) . . ? C16 C14 C15 109.1(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 C18 C19 108.2(5) . . ? C22 C18 C23 127.0(5) . . ? C19 C18 C23 124.1(5) . . ? C22 C18 Ir1 70.7(2) . . ? C19 C18 Ir1 74.2(3) . . ? C23 C18 Ir1 128.3(4) . . ? C20 C19 C18 107.7(4) . . ? C20 C19 C24 125.4(5) . . ? C18 C19 C24 126.6(6) . . ? C20 C19 Ir1 70.9(3) . . ? C18 C19 Ir1 67.8(2) . . ? C24 C19 Ir1 131.4(3) . . ? C19 C20 C21 108.8(5) . . ? C19 C20 C25 126.6(5) . . ? C21 C20 C25 124.6(6) . . ? C19 C20 Ir1 72.7(3) . . ? C21 C20 Ir1 67.6(3) . . ? C25 C20 Ir1 125.7(3) . . ? C22 C21 C20 107.6(4) . . ? C22 C21 C26 126.7(5) . . ? C20 C21 C26 125.1(6) . . ? C22 C21 Ir1 71.5(3) . . ? C20 C21 Ir1 73.9(3) . . ? C26 C21 Ir1 126.9(3) . . ? C21 C22 C18 107.6(4) . . ? C21 C22 C27 125.6(5) . . ? C18 C22 C27 126.5(5) . . ? C21 C22 Ir1 69.9(2) . . ? C18 C22 Ir1 70.8(2) . . ? C27 C22 Ir1 129.3(3) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O1 C28 Cr1 178.0(5) . . ? O2 C29 Cr1 175.0(5) . . ? O3 C30 Cr1 178.3(4) . . ? O4 C31 C32 122.4(8) . . ? O4 C31 C33 119.2(7) . . ? C32 C31 C33 118.4(8) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.943 _refine_diff_density_min -0.940 _refine_diff_density_rms 0.193