Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Daniel Carmona' _publ_contact_author_address ; Dept. de Coordinacion y Catalisis Homogenea Consejo Superior de Investigaciones Cientificas Zaragoza 50009 SPAIN ; _publ_contact_author_email DCARMONA@UNIZAR.ES _publ_section_title ; Pentamethylcyclopentadienyl-iridium(III) complexes with pyridylamino ligands: synthesis and applications as asymmetric catalysts for Diels-Alder reactions ; loop_ _publ_author_name 'Daniel Carmona' 'Isabel T. Dobrinovitch' 'Fernando J. Lahoz' 'M. Pilar Lamata' 'Luis Oro' ; R.Rodriguez ; 'Fernando Viguri' # Data for compound_1a (local labelling as dan23as) data_compound1a _database_code_depnum_ccdc_archive 'CCDC 631835' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H31 Cl Ir N2, F6 Sb' _chemical_formula_sum 'C24 H31 Cl F6 Ir N2 Sb' _chemical_formula_weight 810.91 _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6422(5) _cell_length_b 17.6321(11) _cell_length_c 17.8479(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2719.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7471 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.35 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.980 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 6.036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.241 _exptl_absorpt_correction_T_max 0.430 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS within SAINT+ package, v. 6.01. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 18196 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.72 _reflns_number_total 6460 _reflns_number_gt 5547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v. 5.611 (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_data_reduction 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP program, SHELXTL v6.12, Bruker2000' _computing_publication_material 'XCIF program, SHELXTLv6.12, BrukerAXS' _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. All non-hydrogen atoms were refined with anisotropic displacement parameters. The hydrogen atoms were included in calculated positions and refined with coordinates riding on carbon atoms and free isotropic displacement parameters. The maximun electron residual was of 0.93 e/\%A^3^ at 0.92\%A from the Ir atom and has no chemical sense. ; _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^)+(0.0180P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.017(7) _refine_ls_number_reflns 6460 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.001 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 Ir Ir 0.75057(3) 0.637296(10) 0.198073(8) 0.02448(5) Uani 1 1 d . . . Cl Cl 1.02004(14) 0.66124(9) 0.18262(7) 0.0370(3) Uani 1 1 d . . . N1 N 0.7254(5) 0.6648(2) 0.08563(19) 0.0251(10) Uani 1 1 d . . . N2 N 0.7998(4) 0.5329(2) 0.1392(2) 0.0252(10) Uani 1 1 d . . . H2N H 0.8985 0.5384 0.1192 0.007(11) Uiso 1 1 calc R . . C1 C 0.5361(6) 0.6163(3) 0.2574(3) 0.0311(13) Uani 1 1 d . . . C2 C 0.6627(6) 0.6072(4) 0.3089(3) 0.0356(14) Uani 1 1 d . . . C3 C 0.7449(9) 0.6749(3) 0.3142(2) 0.0387(12) Uani 1 1 d . . . C4 C 0.6752(6) 0.7304(4) 0.2655(3) 0.0339(13) Uani 1 1 d . . . C5 C 0.5425(6) 0.6938(3) 0.2326(3) 0.0287(12) Uani 1 1 d . . . C6 C 0.4111(6) 0.5623(4) 0.2408(3) 0.0429(15) Uani 1 1 d . . . H6A H 0.4524 0.5106 0.2414 0.05(2) Uiso 1 1 calc R . . H6B H 0.3680 0.5734 0.1912 0.058(19) Uiso 1 1 calc R . . H6C H 0.3297 0.5671 0.2787 0.08(2) Uiso 1 1 calc R . . C7 C 0.6897(7) 0.5390(4) 0.3572(3) 0.0470(19) Uani 1 1 d . . . H7A H 0.8011 0.5297 0.3614 0.07(3) Uiso 1 1 calc R . . H7B H 0.6394 0.4948 0.3346 0.039(17) Uiso 1 1 calc R . . H7C H 0.6462 0.5481 0.4071 0.043(16) Uiso 1 1 calc R . . C8 C 0.8875(7) 0.6897(4) 0.3619(3) 0.0528(19) Uani 1 1 d . . . H8A H 0.8556 0.7082 0.4113 0.07(2) Uiso 1 1 calc R . . H8B H 0.9524 0.7279 0.3374 0.043(17) Uiso 1 1 calc R . . H8C H 0.9463 0.6425 0.3676 0.07(2) Uiso 1 1 calc R . . C9 C 0.7206(7) 0.8111(4) 0.2585(4) 0.0476(17) Uani 1 1 d . . . H9A H 0.6920 0.8384 0.3044 0.06(2) Uiso 1 1 calc R . . H9B H 0.6672 0.8338 0.2156 0.13(4) Uiso 1 1 calc R . . H9C H 0.8327 0.8146 0.2510 0.06(2) Uiso 1 1 calc R . . C10 C 0.4273(6) 0.7294(4) 0.1800(3) 0.0407(15) Uani 1 1 d . . . H10A H 0.3965 0.6923 0.1420 0.038(16) Uiso 1 1 calc R . . H10B H 0.4746 0.7734 0.1555 0.038(16) Uiso 1 1 calc R . . H10C H 0.3360 0.7457 0.2083 0.057(19) Uiso 1 1 calc R . . C11 C 0.7261(7) 0.7363(3) 0.0585(3) 0.0315(14) Uani 1 1 d . . . H11 H 0.7551 0.7769 0.0906 0.036(12) Uiso 1 1 calc R . . C12 C 0.6862(6) 0.7519(3) -0.0142(3) 0.0380(14) Uani 1 1 d . . . H12 H 0.6843 0.8028 -0.0318 0.012(11) Uiso 1 1 calc R . . C13 C 0.6486(6) 0.6929(4) -0.0615(3) 0.0360(14) Uani 1 1 d . . . H13 H 0.6191 0.7025 -0.1119 0.040(16) Uiso 1 1 calc R . . C14 C 0.6547(6) 0.6208(3) -0.0347(3) 0.0318(13) Uani 1 1 d . . . H14 H 0.6334 0.5795 -0.0672 0.027(14) Uiso 1 1 calc R . . C15 C 0.6913(5) 0.6072(3) 0.0388(3) 0.0263(11) Uani 1 1 d . . . C16 C 0.6925(6) 0.5316(3) 0.0747(3) 0.0294(12) Uani 1 1 d . . . H16A H 0.5870 0.5183 0.0919 0.053(18) Uiso 1 1 calc R . . H16B H 0.7263 0.4927 0.0381 0.030(13) Uiso 1 1 calc R . . C17 C 0.8025(6) 0.4612(3) 0.1838(3) 0.0309(12) Uani 1 1 d . . . H17 H 0.7125 0.4621 0.2190 0.037 Uiso 1 1 calc R . . C18 C 0.9509(7) 0.4606(4) 0.2305(3) 0.0443(15) Uani 1 1 d . . . H18A H 1.0404 0.4550 0.1973 0.037(15) Uiso 1 1 calc R . . H18B H 0.9478 0.4181 0.2658 0.042(17) Uiso 1 1 calc R . . H18C H 0.9594 0.5083 0.2583 0.09(3) Uiso 1 1 calc R . . C19 C 0.7905(6) 0.3907(3) 0.1366(3) 0.0335(14) Uani 1 1 d . . . C20 C 0.6763(7) 0.3368(4) 0.1509(3) 0.0510(18) Uani 1 1 d . . . H20 H 0.6032 0.3463 0.1895 0.08(2) Uiso 1 1 calc R . . C21 C 0.6658(9) 0.2711(4) 0.1116(4) 0.066(2) Uani 1 1 d . . . H21 H 0.5885 0.2349 0.1240 0.11(3) Uiso 1 1 calc R . . C22 C 0.7662(11) 0.2569(3) 0.0540(3) 0.0503(17) Uani 1 1 d . . . H22 H 0.7572 0.2117 0.0253 0.029(11) Uiso 1 1 calc R . . C23 C 0.8792(7) 0.3082(4) 0.0386(4) 0.0445(15) Uani 1 1 d . . . H23 H 0.9496 0.2987 -0.0012 0.10(3) Uiso 1 1 calc R . . C24 C 0.8928(7) 0.3733(3) 0.0794(3) 0.0446(15) Uani 1 1 d . . . H24 H 0.9745 0.4076 0.0684 0.037(15) Uiso 1 1 calc R . . Sb Sb 0.74517(7) 0.997083(18) 0.018609(17) 0.03492(8) Uani 1 1 d . . . F1 F 0.7268(7) 0.9313(2) 0.09857(17) 0.0768(13) Uani 1 1 d . . . F2 F 0.7650(6) 1.0618(2) -0.06310(18) 0.0721(11) Uani 1 1 d . . . F3 F 0.5515(4) 0.9652(2) -0.01590(19) 0.0532(10) Uani 1 1 d . . . F4 F 0.9392(4) 1.0290(2) 0.0528(2) 0.0715(13) Uani 1 1 d . . . F5 F 0.8391(4) 0.9204(2) -0.0376(2) 0.0599(11) Uani 1 1 d . . . F6 F 0.6501(4) 1.0753(2) 0.0722(2) 0.0568(10) 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 Ir 0.02157(8) 0.02787(10) 0.02400(8) 0.00258(7) -0.00053(15) -0.00024(16) Cl 0.0246(6) 0.0461(9) 0.0402(8) 0.0040(7) 0.0020(5) -0.0070(6) N1 0.024(3) 0.028(2) 0.0229(17) 0.0033(16) -0.0026(18) 0.001(2) N2 0.023(2) 0.025(2) 0.027(2) 0.0054(19) -0.0007(14) 0.0023(16) C1 0.026(3) 0.041(4) 0.025(3) 0.001(3) 0.005(2) 0.001(2) C2 0.031(3) 0.050(4) 0.025(3) 0.007(3) 0.005(2) 0.007(3) C3 0.031(2) 0.066(4) 0.019(2) -0.002(2) 0.001(4) -0.001(5) C4 0.035(3) 0.034(3) 0.033(3) -0.009(3) 0.004(2) 0.007(3) C5 0.029(3) 0.031(3) 0.026(3) -0.003(2) 0.002(2) 0.001(2) C6 0.034(3) 0.049(5) 0.045(4) 0.001(3) 0.007(3) -0.007(3) C7 0.043(3) 0.063(5) 0.036(3) 0.026(3) 0.004(2) 0.007(3) C8 0.040(4) 0.083(6) 0.035(4) -0.002(4) -0.008(3) -0.009(4) C9 0.037(5) 0.048(4) 0.058(4) -0.020(3) 0.009(3) -0.003(3) C10 0.033(3) 0.046(4) 0.044(3) 0.003(3) -0.005(2) 0.009(3) C11 0.035(4) 0.029(3) 0.031(2) 0.002(2) -0.002(2) -0.006(3) C12 0.055(4) 0.026(3) 0.033(3) 0.010(3) 0.004(2) -0.003(3) C13 0.040(3) 0.044(4) 0.024(3) 0.009(3) 0.001(2) -0.002(3) C14 0.034(3) 0.033(4) 0.028(3) -0.002(3) 0.002(2) -0.001(2) C15 0.029(3) 0.020(3) 0.030(3) 0.001(2) 0.0024(19) 0.002(2) C16 0.033(3) 0.025(3) 0.030(3) 0.000(2) 0.000(2) 0.003(2) C17 0.033(3) 0.024(3) 0.036(3) 0.012(2) 0.004(2) 0.001(2) C18 0.047(4) 0.043(4) 0.042(3) 0.004(3) -0.009(3) 0.007(3) C19 0.035(4) 0.028(3) 0.038(3) 0.011(3) 0.000(2) 0.002(2) C20 0.051(4) 0.061(5) 0.041(4) 0.002(3) 0.008(3) -0.016(4) C21 0.089(5) 0.056(5) 0.053(4) -0.009(4) 0.007(4) -0.049(4) C22 0.073(5) 0.037(3) 0.040(3) 0.001(3) -0.022(4) 0.002(5) C23 0.042(4) 0.034(4) 0.058(4) -0.001(3) 0.006(3) 0.001(3) C24 0.034(3) 0.030(4) 0.071(4) 0.002(3) 0.011(3) -0.004(3) Sb 0.03159(17) 0.02976(18) 0.04341(17) -0.00235(14) -0.0052(3) 0.0006(3) F1 0.119(4) 0.056(2) 0.0553(19) 0.0198(17) -0.012(3) 0.002(3) F2 0.076(3) 0.072(3) 0.068(2) 0.0297(19) 0.017(3) -0.008(4) F3 0.0362(19) 0.052(3) 0.071(2) -0.004(2) -0.0121(17) -0.0054(18) F4 0.040(2) 0.057(3) 0.117(3) -0.028(3) -0.029(2) -0.004(2) F5 0.040(2) 0.053(3) 0.087(3) -0.028(2) -0.0003(18) 0.0059(18) F6 0.054(2) 0.040(2) 0.076(2) -0.015(2) 0.0102(19) 0.0056(19) _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 Ir N1 2.076(3) . ? Ir C4 2.137(5) . ? Ir C5 2.146(5) . ? Ir N2 2.161(4) . ? Ir C1 2.167(5) . ? Ir C3 2.177(4) . ? Ir C2 2.184(5) . ? Ir Cl 2.3828(13) . ? N1 C15 1.347(6) . ? N1 C11 1.352(6) . ? N2 C16 1.478(6) . ? N2 C17 1.494(6) . ? N2 H2N 0.9300 . ? C1 C5 1.437(8) . ? C1 C2 1.438(7) . ? C1 C6 1.469(7) . ? C2 C3 1.393(8) . ? C2 C7 1.497(8) . ? C3 C4 1.440(7) . ? C3 C8 1.520(8) . ? C4 C5 1.441(7) . ? C4 C9 1.483(8) . ? C5 C10 1.505(7) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.370(7) . ? C11 H11 0.9500 . ? C12 C13 1.379(8) . ? C12 H12 0.9500 . ? C13 C14 1.359(8) . ? C13 H13 0.9500 . ? C14 C15 1.372(7) . ? C14 H14 0.9500 . ? C15 C16 1.480(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C19 1.505(7) . ? C17 C18 1.529(7) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.385(7) . ? C19 C20 1.394(8) . ? C20 C21 1.356(9) . ? C20 H20 0.9500 . ? C21 C22 1.368(9) . ? C21 H21 0.9500 . ? C22 C23 1.360(9) . ? C22 H22 0.9500 . ? C23 C24 1.365(8) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? Sb F1 1.846(3) . ? Sb F2 1.860(3) . ? Sb F6 1.868(3) . ? Sb F4 1.870(3) . ? Sb F3 1.870(3) . ? Sb F5 1.869(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir C4 109.50(19) . . ? N1 Ir C5 94.68(18) . . ? C4 Ir C5 39.33(19) . . ? N1 Ir N2 75.48(15) . . ? C4 Ir N2 171.00(19) . . ? C5 Ir N2 134.40(18) . . ? N1 Ir C1 115.00(18) . . ? C4 Ir C1 66.1(2) . . ? C5 Ir C1 38.9(2) . . ? N2 Ir C1 105.10(18) . . ? N1 Ir C3 147.91(19) . . ? C4 Ir C3 39.0(2) . . ? C5 Ir C3 64.3(2) . . ? N2 Ir C3 136.60(18) . . ? C1 Ir C3 64.4(2) . . ? N1 Ir C2 153.60(19) . . ? C4 Ir C2 64.6(2) . . ? C5 Ir C2 64.00(19) . . ? N2 Ir C2 107.55(19) . . ? C1 Ir C2 38.61(18) . . ? C3 Ir C2 37.2(2) . . ? N1 Ir Cl 87.09(13) . . ? C4 Ir Cl 103.12(16) . . ? C5 Ir Cl 140.34(15) . . ? N2 Ir Cl 84.39(11) . . ? C1 Ir Cl 157.37(13) . . ? C3 Ir Cl 94.5(2) . . ? C2 Ir Cl 119.19(15) . . ? C15 N1 C11 118.8(4) . . ? C15 N1 Ir 116.5(3) . . ? C11 N1 Ir 124.3(3) . . ? C16 N2 C17 114.2(4) . . ? C16 N2 Ir 105.6(3) . . ? C17 N2 Ir 117.7(3) . . ? C16 N2 H2N 106.2 . . ? C17 N2 H2N 106.2 . . ? Ir N2 H2N 106.2 . . ? C5 C1 C2 105.9(5) . . ? C5 C1 C6 125.6(5) . . ? C2 C1 C6 128.0(5) . . ? C5 C1 Ir 69.8(3) . . ? C2 C1 Ir 71.4(3) . . ? C6 C1 Ir 129.8(4) . . ? C3 C2 C1 109.6(5) . . ? C3 C2 C7 124.7(5) . . ? C1 C2 C7 125.2(6) . . ? C3 C2 Ir 71.1(3) . . ? C1 C2 Ir 70.0(3) . . ? C7 C2 Ir 131.5(4) . . ? C2 C3 C4 109.1(5) . . ? C2 C3 C8 126.8(5) . . ? C4 C3 C8 124.1(6) . . ? C2 C3 Ir 71.6(3) . . ? C4 C3 Ir 69.0(3) . . ? C8 C3 Ir 124.5(5) . . ? C3 C4 C5 106.0(5) . . ? C3 C4 C9 126.3(5) . . ? C5 C4 C9 127.3(5) . . ? C3 C4 Ir 72.0(3) . . ? C5 C4 Ir 70.7(3) . . ? C9 C4 Ir 127.6(4) . . ? C1 C5 C4 109.3(5) . . ? C1 C5 C10 124.3(5) . . ? C4 C5 C10 126.4(5) . . ? C1 C5 Ir 71.3(3) . . ? C4 C5 Ir 70.0(3) . . ? C10 C5 Ir 124.6(4) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 121.7(5) . . ? N1 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 119.2(5) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 118.8(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? N1 C15 C14 120.8(5) . . ? N1 C15 C16 114.2(4) . . ? C14 C15 C16 125.0(5) . . ? N2 C16 C15 109.1(4) . . ? N2 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N2 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? N2 C17 C19 113.6(4) . . ? N2 C17 C18 108.0(4) . . ? C19 C17 C18 110.9(4) . . ? N2 C17 H17 108.0 . . ? C19 C17 H17 108.0 . . ? C18 C17 H17 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 115.9(6) . . ? C24 C19 C17 123.4(5) . . ? C20 C19 C17 120.7(5) . . ? C21 C20 C19 122.4(6) . . ? C21 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? C20 C21 C22 120.1(6) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 119.1(6) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 120.9(6) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C19 121.6(6) . . ? C23 C24 H24 119.2 . . ? C19 C24 H24 119.2 . . ? F1 Sb F2 178.87(18) . . ? F1 Sb F6 91.76(17) . . ? F2 Sb F6 89.36(17) . . ? F1 Sb F4 90.8(2) . . ? F2 Sb F4 89.3(2) . . ? F6 Sb F4 90.34(18) . . ? F1 Sb F3 89.4(2) . . ? F2 Sb F3 90.49(19) . . ? F6 Sb F3 89.79(16) . . ? F4 Sb F3 179.79(17) . . ? F1 Sb F5 89.84(18) . . ? F2 Sb F5 89.05(17) . . ? F6 Sb F5 178.32(17) . . ? F4 Sb F5 90.16(16) . . ? F3 Sb F5 89.71(16) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.943 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.111 #===END # ---------------------------------------------------------- # Data for compound_5a (local labelling as dan13as) data_compound5a _database_code_depnum_ccdc_archive 'CCDC 631836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H39 Cl Ir N2, F6 Sb, C3 H6 O' _chemical_formula_sum 'C29 H45 Cl F6 Ir N2 O Sb' _chemical_formula_weight 901.07 _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.6957(6) _cell_length_b 14.0751(9) _cell_length_c 24.6210(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3360.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4315 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 4.898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.459 _exptl_absorpt_correction_T_max 0.584 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS within SAINT+ package, v. 6.01. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 22478 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0943 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.69 _reflns_number_total 7930 _reflns_number_gt 6441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v. 5.611 (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_data_reduction 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP program, SHELXTL v6.12, Bruker2001' _computing_publication_material 'XCIF program, SHELXTL v6.12, BrukerAXS' _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. All non-hydrogen atoms were refined with anisotropic displacement parameters, except one C atom. It was not possible to establish a simple model for static disorder for SbF~6~^-^ anion. The acetone molecule was observed to be disordered and one C atom was refined in two positions. Occupancy factors were established for the different geometries holding the sum equal to one. The hydrogen atoms were included in calculated positions according to their geometry and refined riding on carbon atoms. The maximum electron residual was of 1.24 e/\%A^3^ close to the Ir atom and has no sensible chemical sense. ; _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^)+(0.0050P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(6) _refine_ls_number_reflns 7930 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0593 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.001 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 Ir Ir 0.23379(3) 0.482486(16) 0.887915(10) 0.02985(6) Uani 1 1 d . . . Cl Cl 0.36656(17) 0.55466(13) 0.95800(8) 0.0434(5) Uani 1 1 d . . . N1 N 0.2643(7) 0.6109(3) 0.8470(2) 0.0399(13) Uani 1 1 d . . . N2 N 0.0737(5) 0.5758(3) 0.9185(2) 0.0296(13) Uani 1 1 d . . . H2N H 0.1228 0.6066 0.9437 0.04(2) Uiso 1 1 d R . . C1 C 0.3164(7) 0.3388(5) 0.8997(3) 0.0329(19) Uani 1 1 d . . . C2 C 0.1707(7) 0.3348(5) 0.8992(3) 0.033(2) Uani 1 1 d . . . C3 C 0.1236(8) 0.3698(5) 0.8473(3) 0.037(2) Uani 1 1 d . . . C4 C 0.2397(10) 0.3949(4) 0.8170(3) 0.0458(19) Uani 1 1 d . . . C5 C 0.3594(8) 0.3795(6) 0.8496(4) 0.044(2) Uani 1 1 d . . . C6 C 0.4052(7) 0.3077(6) 0.9457(4) 0.052(2) Uani 1 1 d . . . H6A H 0.3525 0.3110 0.9796 0.079 Uiso 1 1 calc R . . H6B H 0.4858 0.3495 0.9482 0.079 Uiso 1 1 calc R . . H6C H 0.4356 0.2422 0.9396 0.079 Uiso 1 1 calc R . . C7 C 0.0810(8) 0.2881(6) 0.9417(4) 0.047(2) Uani 1 1 d . . . H7A H 0.0572 0.2236 0.9299 0.070 Uiso 1 1 calc R . . H7B H -0.0035 0.3253 0.9466 0.070 Uiso 1 1 calc R . . H7C H 0.1313 0.2850 0.9762 0.070 Uiso 1 1 calc R . . C8 C -0.0215(8) 0.3667(6) 0.8278(4) 0.063(3) Uani 1 1 d . . . H8A H -0.0342 0.4140 0.7991 0.094 Uiso 1 1 calc R . . H8B H -0.0840 0.3809 0.8581 0.094 Uiso 1 1 calc R . . H8C H -0.0419 0.3033 0.8135 0.094 Uiso 1 1 calc R . . C9 C 0.2373(11) 0.4289(4) 0.7591(2) 0.071(2) Uani 1 1 d . . . H9A H 0.2447 0.3743 0.7346 0.106 Uiso 1 1 calc R . . H9B H 0.3151 0.4720 0.7529 0.106 Uiso 1 1 calc R . . H9C H 0.1506 0.4625 0.7521 0.106 Uiso 1 1 calc R . . C10 C 0.5084(8) 0.3881(6) 0.8326(4) 0.070(3) Uani 1 1 d . . . H10A H 0.5652 0.4035 0.8644 0.104 Uiso 1 1 calc R . . H10B H 0.5176 0.4387 0.8055 0.104 Uiso 1 1 calc R . . H10C H 0.5394 0.3278 0.8170 0.104 Uiso 1 1 calc R . . C11 C 0.3889(8) 0.6395(5) 0.8273(3) 0.045(2) Uani 1 1 d . . . H11 H 0.4648 0.5919 0.8331 0.04(2) Uiso 1 1 d R . . C12 C 0.4002(9) 0.7246(6) 0.7992(3) 0.056(3) Uani 1 1 d . . . H12 H 0.4951 0.7362 0.7777 0.04(2) Uiso 1 1 d R . . C13 C 0.2868(9) 0.7811(5) 0.7941(3) 0.057(2) Uani 1 1 d . . . H13 H 0.3061 0.8304 0.7726 0.04(2) Uiso 1 1 d R . . C14 C 0.1631(8) 0.7545(5) 0.8162(3) 0.040(2) Uani 1 1 d . . . H14 H 0.0762 0.7891 0.8068 0.012(15) Uiso 1 1 d R . . C15 C 0.1561(8) 0.6686(5) 0.8427(3) 0.0348(19) Uani 1 1 d . . . C16 C 0.0282(7) 0.6328(5) 0.8709(3) 0.0367(18) Uani 1 1 d . . . H16A H -0.0295 0.6868 0.8829 0.044 Uiso 1 1 calc R . . H16B H -0.0268 0.5929 0.8458 0.044 Uiso 1 1 calc R . . C17 C -0.0410(6) 0.5359(4) 0.9522(3) 0.0298(15) Uani 1 1 d . . . H17 H -0.0940 0.4815 0.9335 0.019(14) Uiso 1 1 d R . . C18 C 0.0173(6) 0.5005(5) 1.0064(3) 0.0363(17) Uani 1 1 d . . . H18A H 0.0065 0.4308 1.0098 0.044 Uiso 1 1 calc R . . H18B H 0.1163 0.5168 1.0098 0.044 Uiso 1 1 calc R . . C19 C -0.0676(7) 0.5518(5) 1.0486(3) 0.0400(18) Uani 1 1 d . . . H19 H -0.0597 0.5261 1.0861 0.004(12) Uiso 1 1 d R . . C20 C -0.0232(8) 0.6572(5) 1.0475(3) 0.054(2) Uani 1 1 d . . . H20A H -0.0597 0.6919 1.0794 0.065 Uiso 1 1 calc R . . H20B H 0.0785 0.6633 1.0468 0.065 Uiso 1 1 calc R . . C21 C -0.0869(8) 0.6937(5) 0.9953(3) 0.049(2) Uani 1 1 d . . . H21A H -0.0150 0.7190 0.9707 0.058 Uiso 1 1 calc R . . H21B H -0.1547 0.7446 1.0029 0.058 Uiso 1 1 calc R . . C22 C -0.1579(7) 0.6071(5) 0.9700(3) 0.0360(17) Uani 1 1 d . . . C23 C -0.2113(7) 0.5559(4) 1.0230(3) 0.0340(16) Uani 1 1 d . . . C24 C -0.2698(7) 0.6267(4) 0.9278(3) 0.0503(19) Uani 1 1 d . . . H24A H -0.3526 0.6509 0.9459 0.075 Uiso 1 1 calc R . . H24B H -0.2923 0.5677 0.9086 0.075 Uiso 1 1 calc R . . H24C H -0.2364 0.6739 0.9017 0.075 Uiso 1 1 calc R . . C25 C -0.3176(7) 0.6107(5) 1.0556(3) 0.051(2) Uani 1 1 d . . . H25A H -0.4070 0.6079 1.0371 0.077 Uiso 1 1 calc R . . H25B H -0.2884 0.6771 1.0590 0.077 Uiso 1 1 calc R . . H25C H -0.3260 0.5825 1.0919 0.077 Uiso 1 1 calc R . . C26 C -0.2726(8) 0.4564(4) 1.0123(3) 0.0447(18) Uani 1 1 d . . . H26A H -0.2952 0.4261 1.0470 0.067 Uiso 1 1 calc R . . H26B H -0.2050 0.4175 0.9928 0.067 Uiso 1 1 calc R . . H26C H -0.3564 0.4626 0.9903 0.067 Uiso 1 1 calc R . . Sb Sb 0.22386(6) 0.09302(3) 0.78114(2) 0.04416(14) Uani 1 1 d . . . F1 F 0.2505(7) 0.0530(3) 0.71056(17) 0.1008(16) Uani 1 1 d . . . F2 F 0.1954(7) 0.1306(4) 0.8510(2) 0.125(3) Uani 1 1 d . . . F3 F 0.1215(6) -0.0143(4) 0.7944(3) 0.121(2) Uani 1 1 d . . . F4 F 0.3279(7) 0.1980(4) 0.7706(3) 0.160(4) Uani 1 1 d . . . F5 F 0.3783(6) 0.0251(5) 0.7978(3) 0.149(3) Uani 1 1 d . . . F6 F 0.0720(6) 0.1570(5) 0.7608(3) 0.158(3) Uani 1 1 d . . . O O 0.2456(9) 0.3100(5) 0.0781(3) 0.112(2) Uani 1 1 d . A . C27 C 0.2589(12) 0.3732(6) 0.1116(4) 0.079(3) Uani 1 1 d . . . C28A C 0.2254(19) 0.3538(10) 0.1711(6) 0.067(4) Uiso 0.55 1 d P A 1 C28B C 0.154(2) 0.3835(14) 0.1565(9) 0.066(6) Uiso 0.45 1 d P A 2 C29 C 0.3444(10) 0.4615(9) 0.1045(5) 0.136(5) Uani 1 1 d . A . H29A H 0.4252 0.4583 0.1283 0.164 Uiso 1 1 calc R . . H29B H 0.2890 0.5174 0.1139 0.164 Uiso 1 1 calc R . . H29C H 0.3745 0.4664 0.0666 0.164 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 Ir 0.03148(13) 0.02542(11) 0.03267(12) 0.00003(11) 0.00269(13) 0.00047(11) Cl 0.0348(10) 0.0436(11) 0.0518(12) -0.0074(9) -0.0037(9) -0.0033(8) N1 0.043(4) 0.036(3) 0.041(3) 0.000(2) 0.004(3) 0.010(3) N2 0.028(3) 0.023(3) 0.037(4) 0.004(3) 0.007(3) -0.002(2) C1 0.042(4) 0.020(4) 0.036(5) -0.002(3) 0.007(3) 0.005(3) C2 0.038(4) 0.017(4) 0.046(6) 0.000(3) 0.005(3) -0.001(3) C3 0.054(5) 0.017(4) 0.040(5) -0.005(4) -0.008(4) -0.006(4) C4 0.075(6) 0.027(3) 0.036(4) -0.004(3) -0.003(5) 0.012(5) C5 0.041(5) 0.038(5) 0.054(6) -0.010(4) 0.015(4) -0.001(4) C6 0.049(5) 0.047(6) 0.061(7) 0.007(4) -0.001(4) 0.011(4) C7 0.054(5) 0.028(4) 0.058(6) -0.004(4) 0.015(4) -0.004(4) C8 0.069(6) 0.041(5) 0.079(8) -0.012(5) -0.035(5) 0.009(4) C9 0.132(8) 0.046(4) 0.034(4) 0.000(3) 0.006(6) -0.001(7) C10 0.074(7) 0.045(6) 0.090(8) 0.008(5) 0.044(6) 0.020(5) C11 0.052(5) 0.028(4) 0.054(6) 0.005(4) 0.024(4) 0.002(4) C12 0.074(7) 0.038(5) 0.055(6) -0.010(4) 0.031(5) -0.008(4) C13 0.083(7) 0.036(4) 0.052(5) 0.004(4) 0.029(5) -0.016(5) C14 0.063(5) 0.027(4) 0.031(5) 0.010(3) 0.002(4) 0.006(4) C15 0.040(5) 0.031(4) 0.034(5) -0.002(3) 0.008(4) -0.003(3) C16 0.043(4) 0.034(4) 0.033(5) 0.009(3) 0.006(3) 0.002(3) C17 0.025(3) 0.028(4) 0.037(4) 0.002(3) 0.003(3) -0.005(3) C18 0.032(4) 0.039(5) 0.039(4) 0.011(3) -0.003(3) -0.001(3) C19 0.041(4) 0.046(5) 0.033(5) 0.001(3) 0.001(3) -0.003(4) C20 0.042(5) 0.064(6) 0.056(6) -0.016(4) 0.000(4) -0.022(4) C21 0.052(5) 0.033(4) 0.061(6) -0.011(4) 0.012(4) -0.006(4) C22 0.035(4) 0.029(4) 0.043(5) -0.012(3) 0.002(3) 0.000(3) C23 0.026(4) 0.034(4) 0.041(4) 0.001(3) 0.001(3) -0.005(3) C24 0.039(4) 0.053(4) 0.059(5) 0.012(3) 0.006(4) 0.009(4) C25 0.051(5) 0.046(5) 0.057(6) -0.003(4) 0.013(4) 0.003(4) C26 0.035(4) 0.048(4) 0.051(4) 0.006(3) 0.008(4) -0.015(4) Sb 0.0516(3) 0.0378(3) 0.0431(3) -0.0043(2) 0.0026(3) 0.0012(3) F1 0.132(4) 0.111(4) 0.059(3) -0.020(2) 0.019(4) 0.020(5) F2 0.214(8) 0.100(4) 0.062(4) -0.033(3) 0.045(4) -0.045(5) F3 0.156(5) 0.072(4) 0.135(6) -0.019(4) 0.056(4) -0.049(4) F4 0.190(8) 0.066(4) 0.225(8) -0.025(4) 0.124(6) -0.051(4) F5 0.117(5) 0.113(6) 0.218(9) -0.049(6) -0.096(5) 0.037(4) F6 0.134(6) 0.197(8) 0.142(7) -0.024(6) -0.029(5) 0.117(6) O 0.095(5) 0.139(6) 0.103(6) -0.036(4) 0.009(6) 0.000(6) C27 0.096(7) 0.078(6) 0.063(6) -0.008(5) -0.007(8) 0.015(7) C29 0.102(8) 0.185(13) 0.122(12) 0.010(10) -0.009(7) -0.056(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 Ir N1 2.091(5) . ? Ir C5 2.114(8) . ? Ir C4 2.139(6) . ? Ir C3 2.158(7) . ? Ir N2 2.168(5) . ? Ir C2 2.185(7) . ? Ir C1 2.194(7) . ? Ir Cl 2.3805(18) . ? N1 C15 1.330(8) . ? N1 C11 1.362(9) . ? N2 C16 1.488(8) . ? N2 C17 1.498(7) . ? N2 H2N 0.8943 . ? C1 C2 1.414(8) . ? C1 C5 1.421(11) . ? C1 C6 1.489(10) . ? C2 C3 1.442(11) . ? C2 C7 1.511(10) . ? C3 C4 1.397(11) . ? C3 C8 1.487(10) . ? C4 C5 1.429(11) . ? C4 C9 1.503(8) . ? C5 C10 1.510(10) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.388(10) . ? C11 H11 1.0056 . ? C12 C13 1.362(11) . ? C12 H12 1.0739 . ? C13 C14 1.368(10) . ? C13 H13 0.8934 . ? C14 C15 1.377(9) . ? C14 H14 0.9999 . ? C15 C16 1.507(9) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.531(8) . ? C17 C22 1.575(8) . ? C17 H17 1.0297 . ? C18 C19 1.510(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C23 1.530(9) . ? C19 C20 1.545(9) . ? C19 H19 0.9945 . ? C20 C21 1.517(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.531(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C24 1.528(9) . ? C22 C23 1.577(9) . ? C23 C25 1.518(8) . ? C23 C26 1.544(8) . ? 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 . ? Sb F6 1.797(5) . ? Sb F4 1.808(5) . ? Sb F2 1.821(5) . ? Sb F5 1.824(6) . ? Sb F3 1.837(5) . ? Sb F1 1.845(4) . ? O C27 1.221(9) . ? C27 C28B 1.51(2) . ? C27 C28A 1.526(16) . ? C27 C29 1.504(12) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 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 N1 Ir C5 107.2(3) . . ? N1 Ir C4 95.8(2) . . ? C5 Ir C4 39.2(3) . . ? N1 Ir C3 118.8(3) . . ? C5 Ir C3 64.9(3) . . ? C4 Ir C3 37.9(3) . . ? N1 Ir N2 75.2(2) . . ? C5 Ir N2 169.2(3) . . ? C4 Ir N2 130.7(3) . . ? C3 Ir N2 104.6(3) . . ? N1 Ir C2 157.4(2) . . ? C5 Ir C2 64.3(3) . . ? C4 Ir C2 64.1(3) . . ? C3 Ir C2 38.8(3) . . ? N2 Ir C2 109.4(2) . . ? N1 Ir C1 144.0(2) . . ? C5 Ir C1 38.5(3) . . ? C4 Ir C1 64.3(3) . . ? C3 Ir C1 64.2(3) . . ? N2 Ir C1 140.7(2) . . ? C2 Ir C1 37.7(2) . . ? N1 Ir Cl 84.50(16) . . ? C5 Ir Cl 107.7(2) . . ? C4 Ir Cl 145.4(3) . . ? C3 Ir Cl 156.5(2) . . ? N2 Ir Cl 82.94(16) . . ? C2 Ir Cl 117.7(2) . . ? C1 Ir Cl 95.7(2) . . ? C15 N1 C11 119.4(6) . . ? C15 N1 Ir 117.0(5) . . ? C11 N1 Ir 123.5(5) . . ? C16 N2 C17 114.8(5) . . ? C16 N2 Ir 105.4(4) . . ? C17 N2 Ir 119.8(4) . . ? C16 N2 H2N 116.3 . . ? C17 N2 H2N 101.1 . . ? Ir N2 H2N 98.8 . . ? C2 C1 C5 107.6(8) . . ? C2 C1 C6 124.9(8) . . ? C5 C1 C6 127.5(7) . . ? C2 C1 Ir 70.8(5) . . ? C5 C1 Ir 67.7(4) . . ? C6 C1 Ir 125.6(5) . . ? C1 C2 C3 108.1(8) . . ? C1 C2 C7 125.9(8) . . ? C3 C2 C7 125.4(7) . . ? C1 C2 Ir 71.5(5) . . ? C3 C2 Ir 69.6(4) . . ? C7 C2 Ir 131.5(5) . . ? C4 C3 C2 107.8(7) . . ? C4 C3 C8 126.6(8) . . ? C2 C3 C8 125.1(8) . . ? C4 C3 Ir 70.3(4) . . ? C2 C3 Ir 71.6(4) . . ? C8 C3 Ir 129.7(6) . . ? C3 C4 C5 108.3(6) . . ? C3 C4 C9 125.2(8) . . ? C5 C4 C9 126.5(8) . . ? C3 C4 Ir 71.7(4) . . ? C5 C4 Ir 69.4(4) . . ? C9 C4 Ir 126.2(4) . . ? C1 C5 C4 108.1(7) . . ? C1 C5 C10 123.6(8) . . ? C4 C5 C10 127.5(8) . . ? C1 C5 Ir 73.8(4) . . ? C4 C5 Ir 71.3(4) . . ? C10 C5 Ir 128.3(6) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 120.1(8) . . ? N1 C11 H11 113.7 . . ? C12 C11 H11 126.1 . . ? C13 C12 C11 119.1(8) . . ? C13 C12 H12 123.9 . . ? C11 C12 H12 116.3 . . ? C14 C13 C12 120.8(7) . . ? C14 C13 H13 129.1 . . ? C12 C13 H13 109.8 . . ? C13 C14 C15 118.1(7) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 119.7 . . ? N1 C15 C14 122.3(7) . . ? N1 C15 C16 114.1(6) . . ? C14 C15 C16 123.5(7) . . ? N2 C16 C15 107.4(6) . . ? N2 C16 H16A 110.2 . . ? C15 C16 H16A 110.2 . . ? N2 C16 H16B 110.2 . . ? C15 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? N2 C17 C18 109.3(5) . . ? N2 C17 C22 116.7(5) . . ? C18 C17 C22 103.4(5) . . ? N2 C17 H17 113.6 . . ? C18 C17 H17 109.4 . . ? C22 C17 H17 103.8 . . ? C19 C18 C17 104.0(5) . . ? C19 C18 H18A 111.0 . . ? C17 C18 H18A 111.0 . . ? C19 C18 H18B 111.0 . . ? C17 C18 H18B 111.0 . . ? H18A C18 H18B 109.0 . . ? C18 C19 C23 103.4(6) . . ? C18 C19 C20 107.2(6) . . ? C23 C19 C20 102.2(5) . . ? C18 C19 H19 115.0 . . ? C23 C19 H19 117.8 . . ? C20 C19 H19 110.1 . . ? C21 C20 C19 103.0(6) . . ? C21 C20 H20A 111.2 . . ? C19 C20 H20A 111.2 . . ? C21 C20 H20B 111.2 . . ? C19 C20 H20B 111.2 . . ? H20A C20 H20B 109.1 . . ? C20 C21 C22 105.0(6) . . ? C20 C21 H21A 110.7 . . ? C22 C21 H21A 110.8 . . ? C20 C21 H21B 110.8 . . ? C22 C21 H21B 110.7 . . ? H21A C21 H21B 108.8 . . ? C24 C22 C21 116.9(6) . . ? C24 C22 C17 115.9(5) . . ? C21 C22 C17 107.2(5) . . ? C24 C22 C23 114.3(5) . . ? C21 C22 C23 100.1(6) . . ? C17 C22 C23 100.1(5) . . ? C25 C23 C19 114.8(6) . . ? C25 C23 C26 106.9(5) . . ? C19 C23 C26 112.7(5) . . ? C25 C23 C22 115.4(6) . . ? C19 C23 C22 93.4(5) . . ? C26 C23 C22 113.6(5) . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? F6 Sb F4 90.4(4) . . ? F6 Sb F2 89.6(3) . . ? F4 Sb F2 89.0(3) . . ? F6 Sb F5 176.7(3) . . ? F4 Sb F5 90.2(3) . . ? F2 Sb F5 93.7(3) . . ? F6 Sb F3 91.1(3) . . ? F4 Sb F3 177.7(4) . . ? F2 Sb F3 89.3(2) . . ? F5 Sb F3 88.4(3) . . ? F6 Sb F1 90.3(3) . . ? F4 Sb F1 92.1(3) . . ? F2 Sb F1 178.9(2) . . ? F5 Sb F1 86.4(3) . . ? F3 Sb F1 89.6(3) . . ? O C27 C28B 119.6(13) . . ? O C27 C28A 119.8(10) . . ? O C27 C29 125.6(11) . . ? C28B C27 C29 112.2(10) . . ? C28A C27 C29 112.2(10) . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.589 _refine_diff_density_min -1.221 _refine_diff_density_rms 0.124 #===END # ---------------------------------------------------------- # Data for compound_6a (local labelling as fjl11as) data_compound6a _database_code_depnum_ccdc_archive 'CCDC 631837' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H33 Ir N2 O, 2(F6 Sb), H2 O' _chemical_formula_sum 'C24 H35 F12 Ir N2 O2 Sb2' _chemical_formula_weight 1047.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 _symmetry_space_group_name_Hall 'P 1' _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.6645(8) _cell_length_b 9.7425(8) _cell_length_c 10.1365(8) _cell_angle_alpha 65.4000(10) _cell_angle_beta 68.4620(10) _cell_angle_gamma 72.7420(10) _cell_volume 795.43(11) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4788 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.6 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 5.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5639 _exptl_absorpt_correction_T_max 0.6217 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS within SAINT+ package, v. 6.01. ; _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 SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 9980 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.80 _reflns_number_total 7235 _reflns_number_gt 7051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v. 5.611 (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_data_reduction 'SAINT+ v. 6.01 (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP program, SHELXTL v6.12, Bruker2000' _computing_publication_material 'XCIF program, SHELXTLv6.12, BrukerAXS' _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. All non-hydrogen atoms were refined with anisotropic displacement parameters. The aminic hydrogen atom was included from the residual density map and refined as a free atom; the rest were included in calculated positions with riding positional and thermal parameters. Water molecule hydrogens were included in calculated positions from the geometry of evident hydrogen bonds (J. Apply. Cryst. 32 (1999) 563). All electron residual peaks above 1 e/\%A^3^ were located close to the Ir or Sb atoms (distance shorter than 1.0\%A) and have no chemical sense. ; _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^)+(0.0408P)^2^+1.3071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(4) _refine_ls_number_reflns 7235 _refine_ls_number_parameters 399 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Ir Ir 0.180610(17) 0.042758(17) 0.215400(17) 0.01324(7) Uani 1 1 d . . . N1 N 0.0255(7) 0.1616(7) 0.0883(7) 0.0173(12) Uani 1 1 d . . . N2 N -0.0127(8) -0.0721(8) 0.3373(7) 0.0158(13) Uani 1 1 d . . . H2N H 0.001(9) -0.118(9) 0.270(10) 0.01(2) Uiso 1 1 d . . . O1 O 0.2374(7) -0.1202(8) 0.1045(8) 0.0236(15) Uani 1 1 d . . . H101 H 0.2005 -0.1171 0.0497 0.037(15) Uiso 1 1 d R . . H102 H 0.3033 -0.1848 0.1064 0.037(15) Uiso 1 1 d R . . C1 C 0.1830(9) 0.1974(9) 0.3120(9) 0.0170(15) Uani 1 1 d . . . C2 C 0.2513(8) 0.0498(8) 0.3942(8) 0.0186(14) Uani 1 1 d . . . C3 C 0.3788(9) -0.0063(9) 0.2919(8) 0.0180(15) Uani 1 1 d . . . C4 C 0.3961(9) 0.1161(10) 0.1433(9) 0.0181(16) Uani 1 1 d . . . C5 C 0.2788(9) 0.2390(9) 0.1583(8) 0.0202(15) Uani 1 1 d . . . C6 C 0.0470(9) 0.3004(9) 0.3757(9) 0.0240(16) Uani 1 1 d . . . H6A H -0.0233 0.2377 0.4612 0.036 Uiso 1 1 calc R . . H6B H -0.0033 0.3676 0.2972 0.036 Uiso 1 1 calc R . . H6C H 0.0796 0.3629 0.4100 0.036 Uiso 1 1 calc R . . C7 C 0.2031(9) -0.0304(9) 0.5610(8) 0.0213(15) Uani 1 1 d . . . H7A H 0.2166 -0.1407 0.5829 0.032 Uiso 1 1 calc R . . H7B H 0.0965 0.0085 0.6015 0.032 Uiso 1 1 calc R . . H7C H 0.2645 -0.0118 0.6083 0.032 Uiso 1 1 calc R . . C8 C 0.4888(9) -0.1493(9) 0.3310(9) 0.0217(15) Uani 1 1 d . . . H8A H 0.5648 -0.1309 0.3616 0.033 Uiso 1 1 calc R . . H8B H 0.5385 -0.1818 0.2428 0.033 Uiso 1 1 calc R . . H8C H 0.4360 -0.2299 0.4145 0.033 Uiso 1 1 calc R . . C9 C 0.5207(8) 0.1034(10) 0.0055(8) 0.0231(16) Uani 1 1 d . . . H9A H 0.4983 0.1871 -0.0841 0.035 Uiso 1 1 calc R . . H9B H 0.5295 0.0049 -0.0041 0.035 Uiso 1 1 calc R . . H9C H 0.6160 0.1098 0.0146 0.035 Uiso 1 1 calc R . . C10 C 0.2588(9) 0.3920(9) 0.0367(9) 0.0247(16) Uani 1 1 d . . . H10A H 0.3041 0.4639 0.0461 0.037 Uiso 1 1 calc R . . H10B H 0.1509 0.4311 0.0472 0.037 Uiso 1 1 calc R . . H10C H 0.3082 0.3809 -0.0626 0.037 Uiso 1 1 calc R . . C11 C 0.0597(9) 0.2461(9) -0.0584(9) 0.0235(16) Uani 1 1 d . . . H11 H 0.1627 0.2407 -0.1161 0.028 Uiso 1 1 calc R . . C12 C -0.0472(10) 0.3395(10) -0.1280(9) 0.0276(18) Uani 1 1 d . . . H12 H -0.0200 0.3973 -0.2330 0.033 Uiso 1 1 calc R . . C13 C -0.1979(10) 0.3488(10) -0.0425(11) 0.0277(19) Uani 1 1 d . . . H13 H -0.2747 0.4178 -0.0870 0.033 Uiso 1 1 calc R . . C14 C -0.2341(9) 0.2567(9) 0.1075(9) 0.0224(15) Uani 1 1 d . . . H14 H -0.3364 0.2591 0.1669 0.027 Uiso 1 1 calc R . . C15 C -0.1203(8) 0.1614(9) 0.1699(8) 0.0166(14) Uani 1 1 d . . . C16 C -0.1455(8) 0.0505(8) 0.3278(8) 0.0186(14) Uani 1 1 d . . . H16A H -0.1611 0.1036 0.3981 0.022 Uiso 1 1 calc R . . H16B H -0.2367 0.0062 0.3569 0.022 Uiso 1 1 calc R . . C17 C -0.0235(8) -0.1886(8) 0.4933(8) 0.0169(14) Uani 1 1 d . . . H17 H -0.0231 -0.1357 0.5591 0.020 Uiso 1 1 calc R . . C18 C 0.1160(9) -0.3128(9) 0.4890(9) 0.0234(16) Uani 1 1 d . . . H18A H 0.1147 -0.3827 0.5922 0.035 Uiso 1 1 calc R . . H18B H 0.2068 -0.2655 0.4430 0.035 Uiso 1 1 calc R . . H18C H 0.1163 -0.3701 0.4291 0.035 Uiso 1 1 calc R . . C19 C -0.1688(9) -0.2506(9) 0.5593(8) 0.0195(15) Uani 1 1 d . . . C20 C -0.2878(9) -0.2002(9) 0.6638(9) 0.0225(15) Uani 1 1 d . . . H20 H -0.2778 -0.1244 0.6941 0.027 Uiso 1 1 calc R . . C21 C -0.4220(10) -0.2568(10) 0.7260(10) 0.0277(19) Uani 1 1 d . . . H21 H -0.5039 -0.2178 0.7955 0.033 Uiso 1 1 calc R . . C22 C -0.4359(10) -0.3710(11) 0.6860(9) 0.0303(19) Uani 1 1 d . . . H22 H -0.5266 -0.4123 0.7303 0.036 Uiso 1 1 calc R . . C23 C -0.3192(10) -0.4243(10) 0.5829(11) 0.029(2) Uani 1 1 d . . . H23 H -0.3294 -0.5019 0.5552 0.035 Uiso 1 1 calc R . . C24 C -0.1862(9) -0.3651(9) 0.5189(9) 0.0233(16) Uani 1 1 d . . . H24 H -0.1059 -0.4022 0.4469 0.028 Uiso 1 1 calc R . . Sb1 Sb 0.44378(6) -0.72992(6) 0.55935(6) 0.01991(13) Uani 1 1 d . . . F1 F 0.3902(6) -0.6142(6) 0.6846(6) 0.0303(12) Uani 1 1 d . . . F2 F 0.4807(8) -0.5529(7) 0.3909(6) 0.0517(16) Uani 1 1 d . . . F3 F 0.4955(6) -0.8417(7) 0.4326(6) 0.0312(12) Uani 1 1 d . . . F4 F 0.4055(7) -0.9048(6) 0.7294(6) 0.0383(12) Uani 1 1 d . . . F5 F 0.6442(6) -0.7685(7) 0.5601(7) 0.0428(14) Uani 1 1 d . . . F6 F 0.2434(6) -0.6899(6) 0.5596(7) 0.0379(13) Uani 1 1 d . . . Sb2 Sb -0.06874(5) -0.19752(6) -0.02332(6) 0.02045(12) Uani 1 1 d . . . F7 F -0.2436(7) -0.2800(8) 0.0442(7) 0.0485(18) Uani 1 1 d . . . F8 F -0.1576(6) -0.0827(5) 0.1049(6) 0.0268(11) Uani 1 1 d . . . F9 F 0.1059(6) -0.1107(7) -0.0926(6) 0.0377(14) Uani 1 1 d . . . F10 F 0.0247(6) -0.3158(6) -0.1474(6) 0.0391(13) Uani 1 1 d . . . F11 F -0.1403(6) -0.0395(6) -0.1767(6) 0.0317(12) Uani 1 1 d . . . F12 F 0.0022(7) -0.3499(7) 0.1356(6) 0.0493(17) Uani 1 1 d . . . O2 O 0.4676(7) -0.3474(7) 0.1093(7) 0.0322(13) Uani 1 1 d . . . H201 H 0.4606 -0.4052 0.1876 0.037(15) Uiso 1 1 d R . . H202 H 0.5425 -0.3221 0.0817 0.037(15) Uiso 1 1 d 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 Ir 0.01034(13) 0.01700(13) 0.01175(12) -0.00501(10) -0.00273(10) -0.00188(10) N1 0.011(3) 0.024(3) 0.011(3) -0.005(2) 0.002(2) -0.003(2) N2 0.016(3) 0.021(3) 0.017(3) -0.010(3) -0.007(3) -0.002(3) O1 0.021(3) 0.032(4) 0.027(3) -0.017(3) -0.011(3) -0.002(3) C1 0.016(4) 0.028(4) 0.015(3) -0.012(3) -0.006(3) -0.006(3) C2 0.012(3) 0.021(4) 0.023(4) -0.007(3) 0.001(3) -0.012(3) C3 0.022(4) 0.030(4) 0.008(3) -0.006(3) -0.008(3) -0.008(3) C4 0.012(4) 0.027(4) 0.016(4) -0.004(3) -0.005(3) -0.008(3) C5 0.021(4) 0.022(4) 0.021(4) -0.009(3) -0.007(3) -0.006(3) C6 0.022(4) 0.025(4) 0.025(4) -0.016(3) -0.001(3) -0.002(3) C7 0.025(4) 0.024(4) 0.015(3) -0.005(3) -0.007(3) -0.006(3) C8 0.018(4) 0.025(4) 0.021(4) -0.011(3) -0.004(3) -0.001(3) C9 0.016(4) 0.033(4) 0.016(4) -0.008(3) 0.000(3) -0.005(3) C10 0.027(4) 0.020(4) 0.025(4) -0.007(3) -0.006(3) -0.004(3) C11 0.018(4) 0.028(4) 0.019(4) -0.004(3) -0.005(3) -0.003(3) C12 0.030(4) 0.029(4) 0.014(4) 0.000(3) -0.008(3) -0.002(3) C13 0.025(4) 0.022(4) 0.031(5) 0.000(3) -0.017(4) 0.001(3) C14 0.016(4) 0.023(4) 0.027(4) -0.011(3) -0.008(3) 0.003(3) C15 0.009(3) 0.023(4) 0.017(3) -0.010(3) 0.000(3) -0.002(3) C16 0.018(4) 0.016(3) 0.019(4) -0.005(3) -0.006(3) -0.001(3) C17 0.018(3) 0.021(3) 0.013(3) -0.006(3) -0.003(3) -0.007(3) C18 0.020(4) 0.020(4) 0.029(4) -0.003(3) -0.010(3) -0.005(3) C19 0.021(4) 0.020(4) 0.018(3) -0.003(3) -0.009(3) -0.004(3) C20 0.028(4) 0.021(4) 0.023(4) -0.007(3) -0.011(3) -0.008(3) C21 0.020(4) 0.037(5) 0.020(4) -0.006(4) -0.003(3) -0.006(4) C22 0.031(5) 0.035(5) 0.019(4) 0.006(3) -0.011(4) -0.015(4) C23 0.028(5) 0.014(4) 0.042(6) -0.003(4) -0.012(4) -0.006(3) C24 0.021(4) 0.025(4) 0.028(4) -0.014(3) -0.007(3) -0.003(3) Sb1 0.0165(3) 0.0242(3) 0.0208(3) -0.0107(2) -0.0031(2) -0.0044(2) F1 0.030(3) 0.030(3) 0.038(3) -0.024(2) -0.004(2) -0.005(2) F2 0.076(5) 0.041(3) 0.031(3) 0.002(3) -0.008(3) -0.029(3) F3 0.024(3) 0.048(3) 0.035(3) -0.031(3) -0.003(2) -0.008(2) F4 0.054(3) 0.025(3) 0.034(3) -0.005(2) -0.014(3) -0.009(2) F5 0.017(2) 0.066(4) 0.068(4) -0.049(3) -0.008(2) -0.004(2) F6 0.020(2) 0.045(3) 0.059(4) -0.028(3) -0.018(2) 0.005(2) Sb2 0.0183(3) 0.0233(3) 0.0177(2) -0.0087(2) -0.0023(2) -0.0019(2) F7 0.047(4) 0.062(4) 0.045(4) -0.034(3) 0.016(3) -0.037(3) F8 0.028(3) 0.027(3) 0.029(3) -0.018(2) -0.004(2) -0.002(2) F9 0.025(3) 0.070(4) 0.026(3) -0.019(3) -0.005(2) -0.018(3) F10 0.048(3) 0.034(3) 0.033(3) -0.023(2) -0.002(2) 0.003(2) F11 0.026(3) 0.042(3) 0.027(3) -0.011(2) -0.014(2) 0.003(2) F12 0.058(4) 0.043(3) 0.020(3) -0.003(2) -0.010(3) 0.016(3) O2 0.027(3) 0.035(3) 0.030(3) -0.010(3) -0.008(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir N1 2.096(6) . ? Ir C1 2.120(7) . ? Ir O1 2.145(6) . ? Ir C5 2.154(7) . ? Ir N2 2.160(7) . ? Ir C4 2.171(8) . ? Ir C3 2.176(7) . ? Ir C2 2.190(7) . ? N1 C11 1.334(10) . ? N1 C15 1.347(9) . ? N2 C16 1.473(9) . ? N2 C17 1.501(9) . ? N2 H2N 0.91(8) . ? O1 H101 0.7500 . ? O1 H102 0.7500 . ? C1 C2 1.429(11) . ? C1 C5 1.445(10) . ? C1 C6 1.512(10) . ? C2 C3 1.424(10) . ? C2 C7 1.491(10) . ? C3 C4 1.469(10) . ? C3 C8 1.483(11) . ? C4 C5 1.400(11) . ? C4 C9 1.495(10) . ? C5 C10 1.501(10) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.355(11) . ? C11 H11 0.9500 . ? C12 C13 1.393(12) . ? C12 H12 0.9500 . ? C13 C14 1.378(12) . ? C13 H13 0.9500 . ? C14 C15 1.374(10) . ? C14 H14 0.9500 . ? C15 C16 1.490(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C19 1.504(10) . ? C17 C18 1.522(10) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.374(11) . ? C19 C24 1.409(10) . ? C20 C21 1.385(11) . ? C20 H20 0.9500 . ? C21 C22 1.387(13) . ? C21 H21 0.9500 . ? C22 C23 1.368(13) . ? C22 H22 0.9500 . ? C23 C24 1.386(12) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? Sb1 F6 1.858(5) . ? Sb1 F3 1.860(5) . ? Sb1 F5 1.862(5) . ? Sb1 F4 1.863(5) . ? Sb1 F2 1.866(5) . ? Sb1 F1 1.874(5) . ? Sb2 F11 1.853(5) . ? Sb2 F7 1.862(6) . ? Sb2 F10 1.866(5) . ? Sb2 F12 1.867(5) . ? Sb2 F8 1.870(5) . ? Sb2 F9 1.881(5) . ? O2 H201 0.7501 . ? O2 H202 0.7500 . ? 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 N1 Ir C1 104.3(3) . . ? N1 Ir O1 85.5(2) . . ? C1 Ir O1 165.9(2) . . ? N1 Ir C5 95.4(3) . . ? C1 Ir C5 39.5(3) . . ? O1 Ir C5 130.8(3) . . ? N1 Ir N2 75.0(2) . . ? C1 Ir N2 111.8(3) . . ? O1 Ir N2 80.2(2) . . ? C5 Ir N2 147.4(3) . . ? N1 Ir C4 120.0(3) . . ? C1 Ir C4 65.3(3) . . ? O1 Ir C4 101.1(3) . . ? C5 Ir C4 37.8(3) . . ? N2 Ir C4 164.9(2) . . ? N1 Ir C3 158.9(2) . . ? C1 Ir C3 65.4(3) . . ? O1 Ir C3 101.9(3) . . ? C5 Ir C3 64.7(3) . . ? N2 Ir C3 125.4(3) . . ? C4 Ir C3 39.5(3) . . ? N1 Ir C2 140.8(3) . . ? C1 Ir C2 38.7(3) . . ? O1 Ir C2 133.4(3) . . ? C5 Ir C2 64.3(3) . . ? N2 Ir C2 103.7(2) . . ? C4 Ir C2 64.4(3) . . ? C3 Ir C2 38.1(3) . . ? C11 N1 C15 119.6(7) . . ? C11 N1 Ir 125.5(5) . . ? C15 N1 Ir 114.5(5) . . ? C16 N2 C17 113.7(6) . . ? C16 N2 Ir 105.5(5) . . ? C17 N2 Ir 120.2(5) . . ? C16 N2 H2N 108(5) . . ? C17 N2 H2N 111(5) . . ? Ir N2 H2N 97(5) . . ? Ir O1 H101 125.9 . . ? Ir O1 H102 126.1 . . ? H101 O1 H102 107.7 . . ? C2 C1 C5 107.1(7) . . ? C2 C1 C6 127.0(7) . . ? C5 C1 C6 125.6(7) . . ? C2 C1 Ir 73.3(4) . . ? C5 C1 Ir 71.5(4) . . ? C6 C1 Ir 126.0(5) . . ? C3 C2 C1 108.9(6) . . ? C3 C2 C7 124.9(7) . . ? C1 C2 C7 126.1(7) . . ? C3 C2 Ir 70.4(4) . . ? C1 C2 Ir 68.0(4) . . ? C7 C2 Ir 129.9(5) . . ? C2 C3 C4 106.9(7) . . ? C2 C3 C8 126.8(7) . . ? C4 C3 C8 125.6(7) . . ? C2 C3 Ir 71.5(4) . . ? C4 C3 Ir 70.1(4) . . ? C8 C3 Ir 131.1(5) . . ? C5 C4 C3 107.8(7) . . ? C5 C4 C9 128.8(7) . . ? C3 C4 C9 123.4(7) . . ? C5 C4 Ir 70.5(4) . . ? C3 C4 Ir 70.4(4) . . ? C9 C4 Ir 124.7(6) . . ? C4 C5 C1 109.0(7) . . ? C4 C5 C10 125.8(7) . . ? C1 C5 C10 125.1(7) . . ? C4 C5 Ir 71.8(4) . . ? C1 C5 Ir 69.0(4) . . ? C10 C5 Ir 127.3(5) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 122.3(7) . . ? N1 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C11 C12 C13 118.6(7) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 119.1(7) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 119.2(7) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? N1 C15 C14 120.9(7) . . ? N1 C15 C16 114.9(6) . . ? C14 C15 C16 124.2(6) . . ? N2 C16 C15 109.0(6) . . ? N2 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N2 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? N2 C17 C19 111.5(6) . . ? N2 C17 C18 109.3(6) . . ? C19 C17 C18 113.2(6) . . ? N2 C17 H17 107.5 . . ? C19 C17 H17 107.5 . . ? C18 C17 H17 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 117.7(7) . . ? C20 C19 C17 121.2(7) . . ? C24 C19 C17 121.0(7) . . ? C19 C20 C21 121.8(7) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.1 . . ? C20 C21 C22 119.5(8) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.2(8) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.1(8) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 120.7(8) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? F6 Sb1 F3 90.1(2) . . ? F6 Sb1 F5 179.4(2) . . ? F3 Sb1 F5 90.5(2) . . ? F6 Sb1 F4 89.2(3) . . ? F3 Sb1 F4 90.9(2) . . ? F5 Sb1 F4 90.9(3) . . ? F6 Sb1 F2 90.5(3) . . ? F3 Sb1 F2 89.9(3) . . ? F5 Sb1 F2 89.3(3) . . ? F4 Sb1 F2 179.1(3) . . ? F6 Sb1 F1 89.3(2) . . ? F3 Sb1 F1 179.0(3) . . ? F5 Sb1 F1 90.1(2) . . ? F4 Sb1 F1 89.9(2) . . ? F2 Sb1 F1 89.2(3) . . ? F11 Sb2 F7 89.8(3) . . ? F11 Sb2 F10 90.8(2) . . ? F7 Sb2 F10 90.0(3) . . ? F11 Sb2 F12 177.2(3) . . ? F7 Sb2 F12 91.2(3) . . ? F10 Sb2 F12 91.8(3) . . ? F11 Sb2 F8 90.9(2) . . ? F7 Sb2 F8 90.9(2) . . ? F10 Sb2 F8 178.0(2) . . ? F12 Sb2 F8 86.5(2) . . ? F11 Sb2 F9 89.3(2) . . ? F7 Sb2 F9 179.0(3) . . ? F10 Sb2 F9 90.6(3) . . ? F12 Sb2 F9 89.6(3) . . ? F8 Sb2 F9 88.6(2) . . ? H201 O2 H202 107.7 . . ? 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 Ir N1 C11 93.5(7) . . . . ? O1 Ir N1 C11 -76.2(7) . . . . ? C5 Ir N1 C11 54.4(7) . . . . ? N2 Ir N1 C11 -157.2(7) . . . . ? C4 Ir N1 C11 24.0(8) . . . . ? C3 Ir N1 C11 35.7(11) . . . . ? C2 Ir N1 C11 109.3(7) . . . . ? C1 Ir N1 C15 -79.5(6) . . . . ? O1 Ir N1 C15 110.7(5) . . . . ? C5 Ir N1 C15 -118.7(5) . . . . ? N2 Ir N1 C15 29.7(5) . . . . ? C4 Ir N1 C15 -149.1(5) . . . . ? C3 Ir N1 C15 -137.4(7) . . . . ? C2 Ir N1 C15 -63.8(7) . . . . ? N1 Ir N2 C16 -39.4(4) . . . . ? C1 Ir N2 C16 60.3(5) . . . . ? O1 Ir N2 C16 -127.4(5) . . . . ? C5 Ir N2 C16 36.8(7) . . . . ? C4 Ir N2 C16 136.4(11) . . . . ? C3 Ir N2 C16 134.9(5) . . . . ? C2 Ir N2 C16 100.1(5) . . . . ? N1 Ir N2 C17 -169.5(6) . . . . ? C1 Ir N2 C17 -69.8(6) . . . . ? O1 Ir N2 C17 102.5(5) . . . . ? C5 Ir N2 C17 -93.3(7) . . . . ? C4 Ir N2 C17 6.3(15) . . . . ? C3 Ir N2 C17 4.8(6) . . . . ? C2 Ir N2 C17 -30.0(6) . . . . ? N1 Ir C1 C2 164.0(4) . . . . ? O1 Ir C1 C2 -62.8(14) . . . . ? C5 Ir C1 C2 -115.0(6) . . . . ? N2 Ir C1 C2 84.7(4) . . . . ? C4 Ir C1 C2 -79.2(5) . . . . ? C3 Ir C1 C2 -35.6(4) . . . . ? N1 Ir C1 C5 -80.9(5) . . . . ? O1 Ir C1 C5 52.3(15) . . . . ? N2 Ir C1 C5 -160.3(4) . . . . ? C4 Ir C1 C5 35.8(4) . . . . ? C3 Ir C1 C5 79.5(5) . . . . ? C2 Ir C1 C5 115.0(6) . . . . ? N1 Ir C1 C6 40.1(7) . . . . ? O1 Ir C1 C6 173.3(10) . . . . ? C5 Ir C1 C6 121.0(9) . . . . ? N2 Ir C1 C6 -39.3(7) . . . . ? C4 Ir C1 C6 156.9(8) . . . . ? C3 Ir C1 C6 -159.5(8) . . . . ? C2 Ir C1 C6 -123.9(9) . . . . ? C5 C1 C2 C3 -5.4(8) . . . . ? C6 C1 C2 C3 -178.5(7) . . . . ? Ir C1 C2 C3 58.6(5) . . . . ? C5 C1 C2 C7 171.7(7) . . . . ? C6 C1 C2 C7 -1.4(12) . . . . ? Ir C1 C2 C7 -124.2(7) . . . . ? C5 C1 C2 Ir -64.0(5) . . . . ? C6 C1 C2 Ir 122.8(8) . . . . ? N1 Ir C2 C3 -145.9(4) . . . . ? C1 Ir C2 C3 -121.0(6) . . . . ? O1 Ir C2 C3 41.7(6) . . . . ? C5 Ir C2 C3 -81.2(5) . . . . ? N2 Ir C2 C3 131.1(4) . . . . ? C4 Ir C2 C3 -39.1(4) . . . . ? N1 Ir C2 C1 -24.9(6) . . . . ? O1 Ir C2 C1 162.6(4) . . . . ? C5 Ir C2 C1 39.8(4) . . . . ? N2 Ir C2 C1 -108.0(4) . . . . ? C4 Ir C2 C1 81.9(5) . . . . ? C3 Ir C2 C1 121.0(6) . . . . ? N1 Ir C2 C7 94.4(7) . . . . ? C1 Ir C2 C7 119.4(9) . . . . ? O1 Ir C2 C7 -78.0(8) . . . . ? C5 Ir C2 C7 159.1(8) . . . . ? N2 Ir C2 C7 11.4(7) . . . . ? C4 Ir C2 C7 -158.8(8) . . . . ? C3 Ir C2 C7 -119.7(9) . . . . ? C1 C2 C3 C4 4.3(8) . . . . ? C7 C2 C3 C4 -172.8(7) . . . . ? Ir C2 C3 C4 61.5(5) . . . . ? C1 C2 C3 C8 174.9(7) . . . . ? C7 C2 C3 C8 -2.3(12) . . . . ? Ir C2 C3 C8 -128.0(8) . . . . ? C1 C2 C3 Ir -57.2(5) . . . . ? C7 C2 C3 Ir 125.7(7) . . . . ? N1 Ir C3 C2 100.6(7) . . . . ? C1 Ir C3 C2 36.1(4) . . . . ? O1 Ir C3 C2 -150.4(4) . . . . ? C5 Ir C3 C2 79.9(5) . . . . ? N2 Ir C3 C2 -64.0(5) . . . . ? C4 Ir C3 C2 116.6(6) . . . . ? N1 Ir C3 C4 -16.0(9) . . . . ? C1 Ir C3 C4 -80.5(5) . . . . ? O1 Ir C3 C4 93.0(5) . . . . ? C5 Ir C3 C4 -36.7(5) . . . . ? N2 Ir C3 C4 179.4(5) . . . . ? C2 Ir C3 C4 -116.6(6) . . . . ? N1 Ir C3 C8 -136.3(7) . . . . ? C1 Ir C3 C8 159.2(8) . . . . ? O1 Ir C3 C8 -27.3(7) . . . . ? C5 Ir C3 C8 -157.0(8) . . . . ? N2 Ir C3 C8 59.1(8) . . . . ? C4 Ir C3 C8 -120.3(9) . . . . ? C2 Ir C3 C8 123.1(9) . . . . ? C2 C3 C4 C5 -1.6(8) . . . . ? C8 C3 C4 C5 -172.3(7) . . . . ? Ir C3 C4 C5 60.9(5) . . . . ? C2 C3 C4 C9 178.2(7) . . . . ? C8 C3 C4 C9 7.6(12) . . . . ? Ir C3 C4 C9 -119.3(8) . . . . ? C2 C3 C4 Ir -62.4(5) . . . . ? C8 C3 C4 Ir 126.9(7) . . . . ? N1 Ir C4 C5 55.4(5) . . . . ? C1 Ir C4 C5 -37.5(4) . . . . ? O1 Ir C4 C5 146.6(4) . . . . ? N2 Ir C4 C5 -120.0(11) . . . . ? C3 Ir C4 C5 -118.1(6) . . . . ? C2 Ir C4 C5 -80.4(5) . . . . ? N1 Ir C4 C3 173.4(4) . . . . ? C1 Ir C4 C3 80.6(5) . . . . ? O1 Ir C4 C3 -95.4(5) . . . . ? C5 Ir C4 C3 118.1(6) . . . . ? N2 Ir C4 C3 -1.9(14) . . . . ? C2 Ir C4 C3 37.7(4) . . . . ? N1 Ir C4 C9 -68.9(8) . . . . ? C1 Ir C4 C9 -161.7(8) . . . . ? O1 Ir C4 C9 22.3(7) . . . . ? C5 Ir C4 C9 -124.3(9) . . . . ? N2 Ir C4 C9 115.8(11) . . . . ? C3 Ir C4 C9 117.7(9) . . . . ? C2 Ir C4 C9 155.4(8) . . . . ? C3 C4 C5 C1 -1.7(9) . . . . ? C9 C4 C5 C1 178.5(8) . . . . ? Ir C4 C5 C1 59.1(5) . . . . ? C3 C4 C5 C10 175.8(7) . . . . ? C9 C4 C5 C10 -4.0(13) . . . . ? Ir C4 C5 C10 -123.4(7) . . . . ? C3 C4 C5 Ir -60.8(5) . . . . ? C9 C4 C5 Ir 119.4(9) . . . . ? C2 C1 C5 C4 4.4(9) . . . . ? C6 C1 C5 C4 177.7(7) . . . . ? Ir C1 C5 C4 -60.8(5) . . . . ? C2 C1 C5 C10 -173.2(7) . . . . ? C6 C1 C5 C10 0.1(12) . . . . ? Ir C1 C5 C10 121.6(7) . . . . ? C2 C1 C5 Ir 65.2(5) . . . . ? C6 C1 C5 Ir -121.5(8) . . . . ? N1 Ir C5 C4 -134.3(5) . . . . ? C1 Ir C5 C4 119.7(7) . . . . ? O1 Ir C5 C4 -45.6(6) . . . . ? N2 Ir C5 C4 155.3(4) . . . . ? C3 Ir C5 C4 38.4(4) . . . . ? C2 Ir C5 C4 80.7(5) . . . . ? N1 Ir C5 C1 106.1(5) . . . . ? O1 Ir C5 C1 -165.2(4) . . . . ? N2 Ir C5 C1 35.6(7) . . . . ? C4 Ir C5 C1 -119.7(7) . . . . ? C3 Ir C5 C1 -81.3(5) . . . . ? C2 Ir C5 C1 -39.0(4) . . . . ? N1 Ir C5 C10 -12.8(7) . . . . ? C1 Ir C5 C10 -118.8(9) . . . . ? O1 Ir C5 C10 76.0(7) . . . . ? N2 Ir C5 C10 -83.2(8) . . . . ? C4 Ir C5 C10 121.5(9) . . . . ? C3 Ir C5 C10 159.9(7) . . . . ? C2 Ir C5 C10 -157.8(8) . . . . ? C15 N1 C11 C12 3.6(12) . . . . ? Ir N1 C11 C12 -169.1(6) . . . . ? N1 C11 C12 C13 1.0(13) . . . . ? C11 C12 C13 C14 -3.7(13) . . . . ? C12 C13 C14 C15 1.9(13) . . . . ? C11 N1 C15 C14 -5.5(11) . . . . ? Ir N1 C15 C14 168.0(6) . . . . ? C11 N1 C15 C16 173.8(7) . . . . ? Ir N1 C15 C16 -12.7(8) . . . . ? C13 C14 C15 N1 2.7(12) . . . . ? C13 C14 C15 C16 -176.5(8) . . . . ? C17 N2 C16 C15 178.3(6) . . . . ? Ir N2 C16 C15 44.5(6) . . . . ? N1 C15 C16 N2 -22.5(9) . . . . ? C14 C15 C16 N2 156.7(7) . . . . ? C16 N2 C17 C19 51.8(8) . . . . ? Ir N2 C17 C19 178.2(5) . . . . ? C16 N2 C17 C18 177.8(6) . . . . ? Ir N2 C17 C18 -55.9(7) . . . . ? N2 C17 C19 C20 -101.7(8) . . . . ? C18 C17 C19 C20 134.6(7) . . . . ? N2 C17 C19 C24 79.9(9) . . . . ? C18 C17 C19 C24 -43.8(10) . . . . ? C24 C19 C20 C21 -1.2(11) . . . . ? C17 C19 C20 C21 -179.7(7) . . . . ? C19 C20 C21 C22 2.1(12) . . . . ? C20 C21 C22 C23 -1.7(13) . . . . ? C21 C22 C23 C24 0.5(13) . . . . ? C22 C23 C24 C19 0.4(13) . . . . ? C20 C19 C24 C23 -0.1(12) . . . . ? C17 C19 C24 C23 178.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.606 _refine_diff_density_min -1.057 _refine_diff_density_rms 0.143