data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Baranoff, Etienne' 'Jung, Il' 'Scopelliti, Rosario' 'Solari, Euro' 'Gratzel, Michael' 'Nazeeruddin, Mohammad' _publ_contact_author_name 'Baranoff, Etienne' _publ_contact_author_email etienne.baranoff@epfl.ch _publ_section_title ; Room-Temperature Combinatorial Screening of Cylometallated Iridium (III) Complexes for a Step Towards Molecular Control of Color Purity ; # Attachment '- eb183.cif' data_eb183b _database_code_depnum_ccdc_archive 'CCDC 803764' #TrackingRef '- eb183.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 Ir N3 O2' _chemical_formula_sum 'C28 H20 Ir N3 O2' _chemical_formula_weight 622.67 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.1602(9) _cell_length_b 14.1871(9) _cell_length_c 9.5929(10) _cell_angle_alpha 90.00 _cell_angle_beta 117.348(13) _cell_angle_gamma 90.00 _cell_volume 1107.31(18) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 7692 _cell_measurement_theta_min 2.8658 _cell_measurement_theta_max 27.2743 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 6.061 _exptl_absorpt_correction_T_min 0.66460 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction, KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2812 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9835 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4283 _reflns_number_gt 3865 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0500P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(12) _refine_ls_number_reflns 4283 _refine_ls_number_parameters 307 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.038 _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 0.78060(2) 0.53271(4) 0.64253(2) 0.01304(8) Uani 1 1 d . . . O1 O 0.7734(7) 0.6039(4) 0.4417(7) 0.0207(11) Uani 1 1 d . . . O2 O 0.6064(7) 0.6854(4) 0.2264(7) 0.0257(12) Uani 1 1 d . . . N1 N 0.7872(8) 0.4071(4) 0.5423(7) 0.0165(13) Uani 1 1 d . . . N2 N 0.7899(7) 0.6550(4) 0.7568(7) 0.0139(12) Uani 1 1 d . . . N3 N 0.5225(7) 0.5572(4) 0.4983(7) 0.0175(15) Uani 1 1 d . . . C1 C 0.6509(9) 0.3595(5) 0.4345(9) 0.0209(16) Uani 1 1 d . . . H1 H 0.5451 0.3855 0.4047 0.025 Uiso 1 1 calc R . . C2 C 0.6629(11) 0.2763(6) 0.3690(10) 0.0263(18) Uani 1 1 d . . . H2 H 0.5666 0.2458 0.2935 0.032 Uiso 1 1 calc R . . C3 C 0.8175(11) 0.2362(5) 0.4134(10) 0.0251(17) Uani 1 1 d . . . H3 H 0.8285 0.1784 0.3689 0.030 Uiso 1 1 calc R . . C4 C 0.9545(10) 0.2832(5) 0.5246(10) 0.0220(17) Uani 1 1 d . . . H4 H 1.0609 0.2568 0.5596 0.026 Uiso 1 1 calc R . . C5 C 0.9361(9) 0.3688(5) 0.5847(9) 0.0178(15) Uani 1 1 d . . . C6 C 1.0714(9) 0.4274(5) 0.6971(9) 0.0172(15) Uani 1 1 d . . . C7 C 1.2387(9) 0.4022(6) 0.7551(9) 0.0221(16) Uani 1 1 d . . . H7 H 1.2687 0.3456 0.7219 0.026 Uiso 1 1 calc R . . C8 C 1.3577(10) 0.4615(6) 0.8607(10) 0.0236(17) Uani 1 1 d . . . H8 H 1.4706 0.4468 0.8974 0.028 Uiso 1 1 calc R . . C9 C 1.3150(8) 0.5398(15) 0.9120(9) 0.030(2) Uani 1 1 d . . . H9 H 1.3988 0.5778 0.9886 0.036 Uiso 1 1 calc R . . C10 C 1.1503(10) 0.5670(5) 0.8559(9) 0.0185(15) Uani 1 1 d . . . H10 H 1.1243 0.6237 0.8921 0.022 Uiso 1 1 calc R . . C11 C 1.0236(9) 0.5105(4) 0.7462(9) 0.0159(19) Uani 1 1 d . . . C12 C 0.7757(9) 0.4798(5) 0.8331(9) 0.0166(15) Uani 1 1 d . . . C13 C 0.7748(14) 0.3856(7) 0.8761(12) 0.020(2) Uani 1 1 d . . . H13 H 0.7716 0.3373 0.8061 0.024 Uiso 1 1 calc R . . C14 C 0.7785(14) 0.3603(6) 1.0171(13) 0.022(2) Uani 1 1 d . . . H14 H 0.7758 0.2955 1.0411 0.026 Uiso 1 1 calc R . . C15 C 0.7859(9) 0.4287(6) 1.1237(9) 0.0240(18) Uani 1 1 d . . . H15 H 0.7917 0.4109 1.2216 0.029 Uiso 1 1 calc R . . C16 C 0.7849(7) 0.5234(11) 1.0862(9) 0.0187(18) Uani 1 1 d . . . H16 H 0.7870 0.5709 1.1569 0.022 Uiso 1 1 calc R . . C17 C 0.7807(8) 0.5481(6) 0.9422(8) 0.016(2) Uani 1 1 d . . . C18 C 0.7837(12) 0.6466(7) 0.8967(12) 0.017(2) Uani 1 1 d . . . C19 C 0.7818(13) 0.7271(7) 0.9793(13) 0.020(2) Uani 1 1 d . . . H19 H 0.7716 0.7212 1.0731 0.024 Uiso 1 1 calc R . . C20 C 0.7948(10) 0.8153(6) 0.9254(10) 0.0248(18) Uani 1 1 d . . . H20 H 0.7957 0.8703 0.9824 0.030 Uiso 1 1 calc R . . C21 C 0.8064(9) 0.8226(5) 0.7870(10) 0.0206(16) Uani 1 1 d . . . H21 H 0.8168 0.8824 0.7481 0.025 Uiso 1 1 calc R . . C22 C 0.8027(9) 0.7419(5) 0.7071(9) 0.0191(15) Uani 1 1 d . . . H22 H 0.8094 0.7475 0.6116 0.023 Uiso 1 1 calc R . . C23 C 0.4883(10) 0.6080(5) 0.3685(9) 0.0176(15) Uani 1 1 d . . . C24 C 0.3291(9) 0.6311(5) 0.2652(9) 0.0211(16) Uani 1 1 d . . . H24 H 0.3064 0.6675 0.1743 0.025 Uiso 1 1 calc R . . C25 C 0.2021(10) 0.6012(6) 0.2945(11) 0.0258(18) Uani 1 1 d . . . H25 H 0.0914 0.6164 0.2238 0.031 Uiso 1 1 calc R . . C26 C 0.2381(9) 0.5490(6) 0.4276(10) 0.022(2) Uani 1 1 d . . . H26 H 0.1528 0.5270 0.4494 0.027 Uiso 1 1 calc R . . C27 C 0.4000(7) 0.5293(11) 0.5281(7) 0.0180(12) Uani 1 1 d . . . H27 H 0.4256 0.4949 0.6215 0.022 Uiso 1 1 calc R . . C28 C 0.6311(9) 0.6357(5) 0.3401(9) 0.0167(15) 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 0.01096(11) 0.01502(11) 0.01061(11) -0.0001(3) 0.00279(8) 0.0003(2) O1 0.020(3) 0.025(3) 0.018(3) 0.000(2) 0.010(2) -0.003(2) O2 0.025(3) 0.028(3) 0.021(3) 0.010(2) 0.008(3) 0.000(2) N1 0.017(3) 0.016(3) 0.014(3) 0.001(2) 0.005(3) 0.002(2) N2 0.009(3) 0.015(3) 0.013(3) 0.004(2) 0.001(2) 0.003(2) N3 0.014(3) 0.022(4) 0.013(3) 0.000(2) 0.002(3) -0.002(2) C1 0.016(4) 0.027(4) 0.012(4) 0.001(3) 0.000(3) -0.002(3) C2 0.023(4) 0.034(4) 0.016(4) -0.005(3) 0.003(4) -0.007(3) C3 0.035(5) 0.021(3) 0.021(4) 0.000(3) 0.015(4) -0.005(3) C4 0.024(4) 0.018(3) 0.026(5) 0.005(3) 0.014(4) 0.008(3) C5 0.021(4) 0.021(3) 0.014(4) 0.003(3) 0.010(3) -0.001(3) C6 0.019(4) 0.021(4) 0.014(4) 0.000(3) 0.009(3) 0.000(3) C7 0.019(4) 0.031(4) 0.016(4) 0.003(3) 0.008(3) 0.005(3) C8 0.011(4) 0.038(4) 0.023(4) 0.007(4) 0.009(3) 0.004(3) C9 0.011(3) 0.059(7) 0.014(3) 0.003(7) 0.001(3) 0.000(7) C10 0.014(4) 0.025(3) 0.014(4) 0.004(3) 0.004(3) -0.001(3) C11 0.015(3) 0.020(5) 0.014(3) 0.005(3) 0.008(3) 0.001(2) C12 0.009(3) 0.024(4) 0.020(4) 0.006(3) 0.010(3) -0.003(3) C13 0.023(4) 0.020(5) 0.016(5) 0.001(4) 0.007(4) 0.000(4) C14 0.021(5) 0.015(5) 0.025(6) 0.004(4) 0.007(4) 0.000(3) C15 0.014(4) 0.034(4) 0.021(4) 0.014(3) 0.005(3) 0.002(3) C16 0.010(3) 0.025(5) 0.017(3) -0.008(5) 0.002(2) 0.000(4) C17 0.009(3) 0.023(6) 0.015(3) -0.001(3) 0.005(3) -0.001(3) C18 0.008(4) 0.024(5) 0.017(5) 0.001(4) 0.005(3) -0.001(4) C19 0.015(4) 0.027(5) 0.016(5) 0.002(4) 0.003(4) 0.000(4) C20 0.018(4) 0.026(4) 0.021(4) -0.004(3) 0.000(4) 0.000(3) C21 0.019(4) 0.016(3) 0.025(4) 0.001(3) 0.008(3) -0.004(3) C22 0.015(4) 0.027(4) 0.011(3) 0.003(3) 0.003(3) 0.005(3) C23 0.025(4) 0.013(3) 0.011(4) -0.002(3) 0.004(3) -0.001(3) C24 0.015(4) 0.023(4) 0.014(4) -0.001(3) -0.003(3) 0.002(3) C25 0.018(4) 0.029(4) 0.023(4) -0.004(4) 0.002(3) 0.002(3) C26 0.015(3) 0.022(7) 0.031(4) -0.007(3) 0.012(3) 0.000(3) C27 0.019(3) 0.017(3) 0.019(3) 0.001(7) 0.010(3) 0.005(6) C28 0.017(4) 0.019(3) 0.011(4) -0.002(3) 0.005(3) 0.000(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 Ir1 C12 1.996(7) . ? Ir1 C11 2.002(7) . ? Ir1 N2 2.033(6) . ? Ir1 N1 2.039(6) . ? Ir1 O1 2.149(5) . ? Ir1 N3 2.149(6) . ? O1 C28 1.298(9) . ? O2 C28 1.229(9) . ? N1 C5 1.346(10) . ? N1 C1 1.377(9) . ? N2 C22 1.345(9) . ? N2 C18 1.375(11) . ? N3 C27 1.339(10) . ? N3 C23 1.345(9) . ? C1 C2 1.365(11) . ? C1 H1 0.9500 . ? C2 C3 1.399(13) . ? C2 H2 0.9500 . ? C3 C4 1.389(12) . ? C3 H3 0.9500 . ? C4 C5 1.387(10) . ? C4 H4 0.9500 . ? C5 C6 1.470(10) . ? C6 C11 1.412(9) . ? C6 C7 1.415(11) . ? C7 C8 1.380(12) . ? C7 H7 0.9500 . ? C8 C9 1.34(2) . ? C8 H8 0.9500 . ? C9 C10 1.403(12) . ? C9 H9 0.9500 . ? C10 C11 1.405(10) . ? C10 H10 0.9500 . ? C12 C13 1.400(11) . ? C12 C17 1.411(11) . ? C13 C14 1.384(14) . ? C13 H13 0.9500 . ? C14 C15 1.388(13) . ? C14 H14 0.9500 . ? C15 C16 1.389(17) . ? C15 H15 0.9500 . ? C16 C17 1.409(11) . ? C16 H16 0.9500 . ? C17 C18 1.468(12) . ? C18 C19 1.394(14) . ? C19 C20 1.380(13) . ? C19 H19 0.9500 . ? C20 C21 1.383(12) . ? C20 H20 0.9500 . ? C21 C22 1.370(11) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.375(11) . ? C23 C28 1.506(11) . ? C24 C25 1.383(12) . ? C24 H24 0.9500 . ? C25 C26 1.378(13) . ? C25 H25 0.9500 . ? C26 C27 1.376(10) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 Ir1 C11 88.5(3) . . ? C12 Ir1 N2 80.8(3) . . ? C11 Ir1 N2 96.0(2) . . ? C12 Ir1 N1 97.0(3) . . ? C11 Ir1 N1 80.2(3) . . ? N2 Ir1 N1 175.7(2) . . ? C12 Ir1 O1 173.5(3) . . ? C11 Ir1 O1 95.1(2) . . ? N2 Ir1 O1 93.4(2) . . ? N1 Ir1 O1 89.0(2) . . ? C12 Ir1 N3 99.8(3) . . ? C11 Ir1 N3 171.2(3) . . ? N2 Ir1 N3 88.3(2) . . ? N1 Ir1 N3 95.7(2) . . ? O1 Ir1 N3 77.0(2) . . ? C28 O1 Ir1 116.3(5) . . ? C5 N1 C1 118.2(6) . . ? C5 N1 Ir1 117.1(5) . . ? C1 N1 Ir1 124.7(5) . . ? C22 N2 C18 118.3(7) . . ? C22 N2 Ir1 125.4(5) . . ? C18 N2 Ir1 116.2(5) . . ? C27 N3 C23 119.6(7) . . ? C27 N3 Ir1 126.6(5) . . ? C23 N3 Ir1 113.7(5) . . ? C2 C1 N1 122.2(7) . . ? C2 C1 H1 118.9 . . ? N1 C1 H1 118.9 . . ? C1 C2 C3 119.7(8) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 118.0(7) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C5 C4 C3 120.0(7) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 121.8(7) . . ? N1 C5 C6 113.0(6) . . ? C4 C5 C6 125.2(7) . . ? C11 C6 C7 121.7(7) . . ? C11 C6 C5 115.5(7) . . ? C7 C6 C5 122.8(7) . . ? C8 C7 C6 118.9(7) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C9 C8 C7 120.5(8) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 122.0(11) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C11 120.2(10) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 116.8(7) . . ? C10 C11 Ir1 129.0(5) . . ? C6 C11 Ir1 114.2(5) . . ? C13 C12 C17 116.1(7) . . ? C13 C12 Ir1 129.4(6) . . ? C17 C12 Ir1 114.4(5) . . ? C14 C13 C12 122.3(9) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 120.6(9) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.6(8) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 119.2(10) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C12 122.2(9) . . ? C16 C17 C18 122.2(9) . . ? C12 C17 C18 115.6(7) . . ? N2 C18 C19 120.0(8) . . ? N2 C18 C17 112.8(8) . . ? C19 C18 C17 127.2(9) . . ? C20 C19 C18 120.3(9) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.0(8) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 118.8(7) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? N2 C22 C21 123.5(7) . . ? N2 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? N3 C23 C24 121.0(7) . . ? N3 C23 C28 117.1(6) . . ? C24 C23 C28 121.9(7) . . ? C23 C24 C25 119.5(8) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C24 119.2(8) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C27 C26 C25 118.7(8) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? N3 C27 C26 122.0(8) . . ? N3 C27 H27 119.0 . . ? C26 C27 H27 119.0 . . ? O2 C28 O1 125.3(7) . . ? O2 C28 C23 119.3(7) . . ? O1 C28 C23 115.4(6) . . ? 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 C11 Ir1 O1 C28 -177.4(5) . . . . ? N2 Ir1 O1 C28 -81.1(5) . . . . ? N1 Ir1 O1 C28 102.5(5) . . . . ? N3 Ir1 O1 C28 6.4(5) . . . . ? C12 Ir1 N1 C5 -87.5(6) . . . . ? C11 Ir1 N1 C5 -0.3(5) . . . . ? O1 Ir1 N1 C5 95.0(5) . . . . ? N3 Ir1 N1 C5 171.9(5) . . . . ? C12 Ir1 N1 C1 92.8(6) . . . . ? C11 Ir1 N1 C1 -179.9(6) . . . . ? O1 Ir1 N1 C1 -84.6(6) . . . . ? N3 Ir1 N1 C1 -7.8(6) . . . . ? C12 Ir1 N2 C22 177.6(6) . . . . ? C11 Ir1 N2 C22 90.1(6) . . . . ? O1 Ir1 N2 C22 -5.4(6) . . . . ? N3 Ir1 N2 C22 -82.3(6) . . . . ? C12 Ir1 N2 C18 -1.9(6) . . . . ? C11 Ir1 N2 C18 -89.3(6) . . . . ? O1 Ir1 N2 C18 175.2(6) . . . . ? N3 Ir1 N2 C18 98.3(6) . . . . ? C12 Ir1 N3 C27 -8.7(8) . . . . ? N2 Ir1 N3 C27 -89.0(8) . . . . ? N1 Ir1 N3 C27 89.4(8) . . . . ? O1 Ir1 N3 C27 177.1(8) . . . . ? C12 Ir1 N3 C23 169.6(5) . . . . ? N2 Ir1 N3 C23 89.3(5) . . . . ? N1 Ir1 N3 C23 -92.3(5) . . . . ? O1 Ir1 N3 C23 -4.6(5) . . . . ? C5 N1 C1 C2 -0.8(11) . . . . ? Ir1 N1 C1 C2 178.8(6) . . . . ? N1 C1 C2 C3 1.1(13) . . . . ? C1 C2 C3 C4 0.3(12) . . . . ? C2 C3 C4 C5 -1.9(12) . . . . ? C1 N1 C5 C4 -0.9(11) . . . . ? Ir1 N1 C5 C4 179.5(6) . . . . ? C1 N1 C5 C6 178.6(6) . . . . ? Ir1 N1 C5 C6 -1.1(8) . . . . ? C3 C4 C5 N1 2.3(11) . . . . ? C3 C4 C5 C6 -177.1(7) . . . . ? N1 C5 C6 C11 2.6(9) . . . . ? C4 C5 C6 C11 -178.0(7) . . . . ? N1 C5 C6 C7 -178.4(7) . . . . ? C4 C5 C6 C7 1.0(12) . . . . ? C11 C6 C7 C8 -0.9(11) . . . . ? C5 C6 C7 C8 -179.8(7) . . . . ? C6 C7 C8 C9 2.5(13) . . . . ? C7 C8 C9 C10 -3.1(16) . . . . ? C8 C9 C10 C11 2.0(15) . . . . ? C9 C10 C11 C6 -0.3(11) . . . . ? C9 C10 C11 Ir1 -178.3(7) . . . . ? C7 C6 C11 C10 -0.2(10) . . . . ? C5 C6 C11 C10 178.8(6) . . . . ? C7 C6 C11 Ir1 178.2(6) . . . . ? C5 C6 C11 Ir1 -2.8(8) . . . . ? C12 Ir1 C11 C10 -82.9(7) . . . . ? N2 Ir1 C11 C10 -2.3(7) . . . . ? N1 Ir1 C11 C10 179.8(7) . . . . ? O1 Ir1 C11 C10 91.7(7) . . . . ? C12 Ir1 C11 C6 99.0(5) . . . . ? N2 Ir1 C11 C6 179.6(5) . . . . ? N1 Ir1 C11 C6 1.7(5) . . . . ? O1 Ir1 C11 C6 -86.4(5) . . . . ? C11 Ir1 C12 C13 -80.7(8) . . . . ? N2 Ir1 C12 C13 -177.1(9) . . . . ? N1 Ir1 C12 C13 -0.8(8) . . . . ? N3 Ir1 C12 C13 96.3(8) . . . . ? C11 Ir1 C12 C17 96.4(5) . . . . ? N2 Ir1 C12 C17 0.0(5) . . . . ? N1 Ir1 C12 C17 176.3(5) . . . . ? N3 Ir1 C12 C17 -86.6(5) . . . . ? C17 C12 C13 C14 0.0(14) . . . . ? Ir1 C12 C13 C14 177.1(8) . . . . ? C12 C13 C14 C15 -1.1(16) . . . . ? C13 C14 C15 C16 1.9(14) . . . . ? C14 C15 C16 C17 -1.7(11) . . . . ? C15 C16 C17 C12 0.7(10) . . . . ? C15 C16 C17 C18 -178.3(7) . . . . ? C13 C12 C17 C16 0.1(11) . . . . ? Ir1 C12 C17 C16 -177.4(5) . . . . ? C13 C12 C17 C18 179.2(6) . . . . ? Ir1 C12 C17 C18 1.7(9) . . . . ? C22 N2 C18 C19 3.5(13) . . . . ? Ir1 N2 C18 C19 -177.1(7) . . . . ? C22 N2 C18 C17 -176.3(7) . . . . ? Ir1 N2 C18 C17 3.2(10) . . . . ? C16 C17 C18 N2 175.9(7) . . . . ? C12 C17 C18 N2 -3.2(11) . . . . ? C16 C17 C18 C19 -3.8(14) . . . . ? C12 C17 C18 C19 177.1(9) . . . . ? N2 C18 C19 C20 -3.4(15) . . . . ? C17 C18 C19 C20 176.3(9) . . . . ? C18 C19 C20 C21 1.2(14) . . . . ? C19 C20 C21 C22 0.8(12) . . . . ? C18 N2 C22 C21 -1.4(11) . . . . ? Ir1 N2 C22 C21 179.1(6) . . . . ? C20 C21 C22 N2 -0.7(12) . . . . ? C27 N3 C23 C24 -0.5(12) . . . . ? Ir1 N3 C23 C24 -178.9(5) . . . . ? C27 N3 C23 C28 -178.9(8) . . . . ? Ir1 N3 C23 C28 2.6(8) . . . . ? N3 C23 C24 C25 -0.5(11) . . . . ? C28 C23 C24 C25 177.9(7) . . . . ? C23 C24 C25 C26 0.4(12) . . . . ? C24 C25 C26 C27 0.7(13) . . . . ? C23 N3 C27 C26 1.6(16) . . . . ? Ir1 N3 C27 C26 179.8(8) . . . . ? C25 C26 C27 N3 -1.8(16) . . . . ? Ir1 O1 C28 O2 172.9(6) . . . . ? Ir1 O1 C28 C23 -6.9(8) . . . . ? N3 C23 C28 O2 -177.0(6) . . . . ? C24 C23 C28 O2 4.5(11) . . . . ? N3 C23 C28 O1 2.8(9) . . . . ? C24 C23 C28 O1 -175.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 3.179 _refine_diff_density_min -1.080 _refine_diff_density_rms 0.187 # Attachment '- eb43.cif' data_eb43 _database_code_depnum_ccdc_archive 'CCDC 803765' #TrackingRef '- eb43.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H42 F4 Ir N8, F6 P' _chemical_formula_sum 'C40 H42 F10 Ir N8 P' _chemical_formula_weight 1047.99 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8685(3) _cell_length_b 12.1840(3) _cell_length_c 18.1833(5) _cell_angle_alpha 82.031(2) _cell_angle_beta 74.703(2) _cell_angle_gamma 82.763(2) _cell_volume 2079.33(10) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 15149 _cell_measurement_theta_min 2.9469 _cell_measurement_theta_max 27.4241 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 3.335 _exptl_absorpt_correction_T_min 0.73889 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction, KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2812 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19019 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 26.02 _reflns_number_total 8132 _reflns_number_gt 7301 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0474P)^2^+1.8605P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8132 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.244272(13) 0.306284(11) 0.294940(7) 0.02295(6) Uani 1 1 d . . . F1 F -0.1731(3) 0.0730(2) 0.47947(14) 0.0432(6) Uani 1 1 d . . . F2 F -0.0118(2) 0.34018(19) 0.58648(11) 0.0310(5) Uani 1 1 d . . . F3 F -0.1655(3) 0.3897(3) 0.15329(16) 0.0542(7) Uani 1 1 d . . . F4 F -0.0791(3) 0.6918(2) 0.26059(16) 0.0482(6) Uani 1 1 d . . . N1 N 0.2814(3) 0.4068(2) 0.36806(16) 0.0232(6) Uani 1 1 d . . . N2 N 0.3334(3) 0.6012(3) 0.52940(17) 0.0282(7) Uani 1 1 d . . . N3 N 0.4077(3) 0.1877(3) 0.32824(17) 0.0264(6) Uani 1 1 d . . . N4 N 0.7241(3) -0.0562(3) 0.3720(2) 0.0325(7) Uani 1 1 d . . . N5 N 0.3969(3) 0.3632(3) 0.19044(17) 0.0295(7) Uani 1 1 d . . . N6 N 0.7196(4) 0.4676(4) 0.0012(2) 0.0526(11) Uani 1 1 d . . . N7 N 0.1789(3) 0.2075(3) 0.23123(17) 0.0287(7) Uani 1 1 d . . . N8 N -0.0060(5) 0.0067(4) 0.1237(3) 0.0571(11) Uani 1 1 d . . . C1 C 0.1012(3) 0.2590(3) 0.3913(2) 0.0230(7) Uani 1 1 d . . . C2 C 0.0086(4) 0.1760(3) 0.4013(2) 0.0279(8) Uani 1 1 d . . . H2 H 0.0106 0.1360 0.3597 0.033 Uiso 1 1 calc R . . C3 C -0.0844(4) 0.1531(3) 0.4711(2) 0.0305(8) Uani 1 1 d . . . C4 C -0.0942(4) 0.2071(3) 0.5341(2) 0.0276(8) Uani 1 1 d . . . H4 H -0.1598 0.1896 0.5817 0.033 Uiso 1 1 calc R . . C5 C -0.0033(4) 0.2881(3) 0.52403(19) 0.0234(7) Uani 1 1 d . . . C6 C 0.0952(3) 0.3157(3) 0.45505(19) 0.0219(7) Uani 1 1 d . . . C7 C 0.1974(3) 0.3982(3) 0.44181(19) 0.0208(7) Uani 1 1 d . . . C8 C 0.2140(4) 0.4619(3) 0.49566(19) 0.0224(7) Uani 1 1 d . . . H8 H 0.1556 0.4531 0.5464 0.027 Uiso 1 1 calc R . . C9 C 0.3147(4) 0.5390(3) 0.4771(2) 0.0243(7) Uani 1 1 d . . . C10 C 0.3983(4) 0.5484(3) 0.4009(2) 0.0266(7) Uani 1 1 d . . . H10 H 0.4668 0.6007 0.3846 0.032 Uiso 1 1 calc R . . C11 C 0.3791(4) 0.4810(3) 0.3510(2) 0.0256(7) Uani 1 1 d . . . H11 H 0.4389 0.4868 0.3005 0.031 Uiso 1 1 calc R . . C12 C 0.2556(4) 0.5833(4) 0.6094(2) 0.0344(9) Uani 1 1 d . . . H12A H 0.1549 0.6041 0.6137 0.052 Uiso 1 1 calc R . . H12B H 0.2896 0.6291 0.6398 0.052 Uiso 1 1 calc R . . H12C H 0.2701 0.5046 0.6285 0.052 Uiso 1 1 calc R . . C13 C 0.4265(4) 0.6897(3) 0.5067(2) 0.0327(8) Uani 1 1 d . . . H13A H 0.5249 0.6573 0.4955 0.049 Uiso 1 1 calc R . . H13B H 0.4094 0.7366 0.5485 0.049 Uiso 1 1 calc R . . H13C H 0.4082 0.7350 0.4608 0.049 Uiso 1 1 calc R . . C14 C 0.3788(4) 0.0916(3) 0.3730(2) 0.0317(8) Uani 1 1 d . . . H14 H 0.2824 0.0787 0.3935 0.038 Uiso 1 1 calc R . . C15 C 0.4781(4) 0.0115(3) 0.3910(2) 0.0316(8) Uani 1 1 d . . . H15 H 0.4494 -0.0533 0.4243 0.038 Uiso 1 1 calc R . . C16 C 0.6234(4) 0.0241(3) 0.3606(2) 0.0286(8) Uani 1 1 d . . . C17 C 0.6535(4) 0.1282(3) 0.3177(2) 0.0288(8) Uani 1 1 d . . . H17 H 0.7485 0.1452 0.2981 0.035 Uiso 1 1 calc R . . C18 C 0.5455(4) 0.2046(3) 0.3044(2) 0.0279(8) Uani 1 1 d . . . H18 H 0.5696 0.2742 0.2765 0.033 Uiso 1 1 calc R . . C19 C 0.6866(4) -0.1615(4) 0.4160(3) 0.0439(11) Uani 1 1 d . . . H19A H 0.6190 -0.1478 0.4648 0.066 Uiso 1 1 calc R . . H19B H 0.7716 -0.2050 0.4261 0.066 Uiso 1 1 calc R . . H19C H 0.6439 -0.2030 0.3868 0.066 Uiso 1 1 calc R . . C20 C 0.8692(4) -0.0537(3) 0.3283(3) 0.0379(9) Uani 1 1 d . . . H20A H 0.8949 0.0230 0.3194 0.057 Uiso 1 1 calc R . . H20B H 0.8805 -0.0820 0.2790 0.057 Uiso 1 1 calc R . . H20C H 0.9306 -0.1004 0.3570 0.057 Uiso 1 1 calc R . . C21 C 0.4165(4) 0.4712(4) 0.1671(2) 0.0321(8) Uani 1 1 d . . . H21 H 0.3539 0.5250 0.1955 0.039 Uiso 1 1 calc R . . C22 C 0.5188(4) 0.5092(4) 0.1061(2) 0.0373(9) Uani 1 1 d . . . H22 H 0.5269 0.5869 0.0943 0.045 Uiso 1 1 calc R . . C23 C 0.6129(4) 0.4340(4) 0.0603(2) 0.0423(11) Uani 1 1 d . . . C24 C 0.5868(4) 0.3218(4) 0.0814(2) 0.0421(11) Uani 1 1 d . . . H24 H 0.6417 0.2666 0.0510 0.050 Uiso 1 1 calc R . . C25 C 0.4829(4) 0.2904(4) 0.1454(2) 0.0362(9) Uani 1 1 d . . . H25 H 0.4711 0.2134 0.1586 0.043 Uiso 1 1 calc R . . C26 C 0.7538(6) 0.5814(5) -0.0128(3) 0.0657(16) Uani 1 1 d . . . H26A H 0.6788 0.6290 -0.0309 0.099 Uiso 1 1 calc R . . H26B H 0.8433 0.5871 -0.0519 0.099 Uiso 1 1 calc R . . H26C H 0.7625 0.6055 0.0348 0.099 Uiso 1 1 calc R . . C27 C 0.8119(6) 0.3874(6) -0.0452(3) 0.0739(19) Uani 1 1 d . . . H27A H 0.8712 0.3414 -0.0150 0.111 Uiso 1 1 calc R . . H27B H 0.8720 0.4267 -0.0904 0.111 Uiso 1 1 calc R . . H27C H 0.7551 0.3398 -0.0617 0.111 Uiso 1 1 calc R . . C28 C 0.2317(4) 0.1007(3) 0.2202(2) 0.0361(9) Uani 1 1 d . . . H28 H 0.3113 0.0712 0.2391 0.043 Uiso 1 1 calc R . . C29 C 0.1770(5) 0.0333(4) 0.1836(3) 0.0420(10) Uani 1 1 d . . . H29 H 0.2205 -0.0398 0.1761 0.050 Uiso 1 1 calc R . . C30 C 0.0563(5) 0.0720(4) 0.1568(3) 0.0443(11) Uani 1 1 d . . . C31 C 0.0029(4) 0.1836(4) 0.1673(2) 0.0376(9) Uani 1 1 d . . . H31 H -0.0771 0.2144 0.1491 0.045 Uiso 1 1 calc R . . C32 C 0.0644(4) 0.2486(3) 0.2034(2) 0.0302(8) Uani 1 1 d . . . C33 C 0.0187(4) 0.3646(3) 0.2181(2) 0.0282(8) Uani 1 1 d . . . C34 C -0.0885(4) 0.4319(4) 0.1930(2) 0.0344(9) Uani 1 1 d . . . C35 C -0.1247(4) 0.5412(4) 0.2061(2) 0.0355(9) Uani 1 1 d . . . H35 H -0.1992 0.5850 0.1886 0.043 Uiso 1 1 calc R . . C36 C -0.0464(4) 0.5835(3) 0.2461(2) 0.0325(8) Uani 1 1 d . . . C37 C 0.0608(4) 0.5223(3) 0.2733(2) 0.0280(8) Uani 1 1 d . . . H37 H 0.1111 0.5556 0.3010 0.034 Uiso 1 1 calc R . . C38 C 0.0947(4) 0.4113(3) 0.26007(19) 0.0257(7) Uani 1 1 d . . . C39 C 0.0479(7) -0.1098(5) 0.1170(3) 0.0671(16) Uani 1 1 d . . . H39A H 0.1438 -0.1137 0.0835 0.101 Uiso 1 1 calc R . . H39B H -0.0134 -0.1458 0.0951 0.101 Uiso 1 1 calc R . . H39C H 0.0496 -0.1480 0.1679 0.101 Uiso 1 1 calc R . . C40 C -0.1389(6) 0.0459(5) 0.1037(4) 0.0681(16) Uani 1 1 d . . . H40A H -0.2087 0.0706 0.1491 0.102 Uiso 1 1 calc R . . H40B H -0.1734 -0.0148 0.0857 0.102 Uiso 1 1 calc R . . H40C H -0.1241 0.1082 0.0631 0.102 Uiso 1 1 calc R . . P1 P -0.47392(17) 0.80160(11) 0.21201(8) 0.0565(4) Uani 1 1 d . . . F5 F -0.5884(5) 0.7770(5) 0.1751(4) 0.142(2) Uani 1 1 d . . . F6 F -0.3548(4) 0.7771(3) 0.1360(2) 0.0931(12) Uani 1 1 d . . . F7 F -0.4448(5) 0.6769(3) 0.2419(3) 0.1149(18) Uani 1 1 d . . . F8 F -0.3493(5) 0.8344(5) 0.2443(3) 0.1292(19) Uani 1 1 d . . . F9 F -0.5857(6) 0.8266(4) 0.2870(3) 0.131(2) Uani 1 1 d . . . F10 F -0.4926(5) 0.9271(3) 0.1814(3) 0.1011(14) 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 0.01792(8) 0.02730(8) 0.02220(8) -0.00580(5) -0.00203(5) 0.00023(5) F1 0.0351(13) 0.0456(14) 0.0485(14) -0.0096(11) 0.0008(11) -0.0218(11) F2 0.0280(11) 0.0399(12) 0.0237(10) -0.0061(9) 0.0000(8) -0.0084(9) F3 0.0457(15) 0.0691(19) 0.0595(17) -0.0199(14) -0.0342(13) 0.0101(13) F4 0.0549(16) 0.0308(13) 0.0564(16) -0.0031(11) -0.0178(13) 0.0118(11) N1 0.0198(14) 0.0275(15) 0.0206(14) -0.0018(12) -0.0032(11) -0.0010(12) N2 0.0238(15) 0.0343(17) 0.0274(15) -0.0057(13) -0.0039(12) -0.0086(13) N3 0.0212(15) 0.0299(16) 0.0275(15) -0.0051(13) -0.0047(12) -0.0019(12) N4 0.0223(16) 0.0290(17) 0.0466(19) -0.0028(15) -0.0094(14) -0.0033(13) N5 0.0208(15) 0.0438(19) 0.0219(15) -0.0064(13) -0.0024(12) 0.0009(13) N6 0.0290(19) 0.094(3) 0.0260(18) 0.0048(19) 0.0016(14) -0.004(2) N7 0.0215(15) 0.0369(18) 0.0286(16) -0.0133(13) -0.0035(12) -0.0015(13) N8 0.069(3) 0.053(3) 0.062(3) -0.025(2) -0.026(2) -0.013(2) C1 0.0158(16) 0.0231(17) 0.0281(17) -0.0049(14) -0.0028(13) 0.0029(13) C2 0.0231(18) 0.0279(19) 0.0330(19) -0.0102(15) -0.0039(15) -0.0024(14) C3 0.0197(17) 0.029(2) 0.041(2) -0.0022(16) -0.0047(15) -0.0052(15) C4 0.0184(17) 0.032(2) 0.0287(18) 0.0017(15) -0.0018(14) -0.0025(14) C5 0.0187(16) 0.0266(18) 0.0237(17) -0.0039(14) -0.0046(13) 0.0021(14) C6 0.0171(16) 0.0222(17) 0.0252(17) -0.0022(13) -0.0051(13) 0.0017(13) C7 0.0169(16) 0.0227(17) 0.0219(16) -0.0021(13) -0.0054(12) 0.0021(13) C8 0.0203(16) 0.0248(17) 0.0208(16) -0.0004(13) -0.0047(13) 0.0001(13) C9 0.0195(17) 0.0247(18) 0.0278(17) 0.0002(14) -0.0072(14) 0.0005(14) C10 0.0213(17) 0.0272(18) 0.0298(18) 0.0037(15) -0.0052(14) -0.0069(14) C11 0.0213(17) 0.0319(19) 0.0214(16) -0.0006(14) -0.0024(13) -0.0033(14) C12 0.0266(19) 0.048(2) 0.0296(19) -0.0118(17) -0.0015(15) -0.0103(17) C13 0.030(2) 0.032(2) 0.039(2) -0.0068(17) -0.0101(16) -0.0061(16) C14 0.0207(18) 0.032(2) 0.038(2) -0.0043(16) 0.0001(15) -0.0030(15) C15 0.0206(18) 0.029(2) 0.043(2) -0.0015(16) -0.0039(16) -0.0038(15) C16 0.0247(18) 0.0290(19) 0.034(2) -0.0076(16) -0.0103(15) -0.0006(15) C17 0.0192(17) 0.031(2) 0.036(2) -0.0049(16) -0.0064(15) -0.0028(15) C18 0.0255(18) 0.0291(19) 0.0290(18) -0.0033(15) -0.0064(14) -0.0030(15) C19 0.028(2) 0.036(2) 0.064(3) 0.007(2) -0.014(2) 0.0019(18) C20 0.024(2) 0.030(2) 0.057(3) -0.0063(19) -0.0068(18) 0.0022(16) C21 0.0283(19) 0.043(2) 0.0236(18) -0.0009(16) -0.0065(15) -0.0004(17) C22 0.033(2) 0.052(3) 0.0258(19) 0.0037(18) -0.0100(16) -0.0058(19) C23 0.025(2) 0.078(3) 0.0208(18) 0.001(2) -0.0034(15) -0.004(2) C24 0.027(2) 0.068(3) 0.027(2) -0.011(2) -0.0020(16) 0.012(2) C25 0.026(2) 0.052(3) 0.0281(19) -0.0090(18) -0.0054(15) 0.0063(18) C26 0.044(3) 0.102(5) 0.040(3) 0.019(3) 0.001(2) -0.019(3) C27 0.044(3) 0.116(5) 0.040(3) 0.002(3) 0.016(2) 0.006(3) C28 0.030(2) 0.036(2) 0.040(2) -0.0149(18) -0.0029(17) 0.0022(17) C29 0.042(2) 0.039(2) 0.044(2) -0.0196(19) -0.0024(19) -0.0014(19) C30 0.042(2) 0.052(3) 0.041(2) -0.018(2) -0.0055(19) -0.011(2) C31 0.032(2) 0.050(3) 0.034(2) -0.0127(18) -0.0086(17) -0.0046(18) C32 0.0247(18) 0.041(2) 0.0239(17) -0.0077(16) -0.0023(14) -0.0026(16) C33 0.0220(18) 0.038(2) 0.0221(17) -0.0060(15) -0.0007(14) -0.0010(15) C34 0.0239(19) 0.052(3) 0.0280(19) -0.0058(17) -0.0078(15) -0.0024(17) C35 0.028(2) 0.045(2) 0.0285(19) 0.0020(17) -0.0053(16) 0.0059(17) C36 0.031(2) 0.033(2) 0.0270(19) 0.0011(16) -0.0017(15) 0.0039(16) C37 0.0255(18) 0.032(2) 0.0236(17) -0.0019(15) -0.0024(14) -0.0010(15) C38 0.0215(17) 0.0319(19) 0.0188(16) -0.0018(14) 0.0015(13) 0.0008(14) C39 0.091(4) 0.059(3) 0.063(3) -0.026(3) -0.023(3) -0.021(3) C40 0.076(4) 0.078(4) 0.070(4) -0.022(3) -0.038(3) -0.019(3) P1 0.0776(10) 0.0422(7) 0.0455(7) -0.0090(6) -0.0157(7) 0.0157(7) F5 0.074(3) 0.170(5) 0.212(6) -0.128(5) -0.045(3) 0.017(3) F6 0.091(3) 0.088(3) 0.080(2) -0.014(2) 0.005(2) 0.015(2) F7 0.105(3) 0.068(2) 0.125(4) 0.030(2) 0.023(3) 0.012(2) F8 0.113(4) 0.150(5) 0.151(5) -0.059(4) -0.076(4) 0.028(3) F9 0.158(5) 0.115(4) 0.089(3) -0.053(3) 0.055(3) -0.042(3) F10 0.097(3) 0.056(2) 0.141(4) -0.008(2) -0.024(3) 0.012(2) _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 C38 2.003(4) . ? Ir1 C1 2.003(3) . ? Ir1 N7 2.045(3) . ? Ir1 N1 2.055(3) . ? Ir1 N3 2.177(3) . ? Ir1 N5 2.179(3) . ? F1 C3 1.358(4) . ? F2 C5 1.355(4) . ? F3 C34 1.361(5) . ? F4 C36 1.364(5) . ? N1 C11 1.352(5) . ? N1 C7 1.376(4) . ? N2 C9 1.357(5) . ? N2 C13 1.451(5) . ? N2 C12 1.455(5) . ? N3 C14 1.346(5) . ? N3 C18 1.346(5) . ? N4 C16 1.340(5) . ? N4 C20 1.444(5) . ? N4 C19 1.450(5) . ? N5 C21 1.347(5) . ? N5 C25 1.350(5) . ? N6 C23 1.350(5) . ? N6 C26 1.440(8) . ? N6 C27 1.448(7) . ? N7 C28 1.361(5) . ? N7 C32 1.369(5) . ? N8 C30 1.350(6) . ? N8 C40 1.458(7) . ? N8 C39 1.462(7) . ? C1 C2 1.409(5) . ? C1 C6 1.414(5) . ? C2 C3 1.373(5) . ? C2 H2 0.9500 . ? C3 C4 1.374(6) . ? C4 C5 1.378(5) . ? C4 H4 0.9500 . ? C5 C6 1.398(5) . ? C6 C7 1.465(5) . ? C7 C8 1.384(5) . ? C8 C9 1.398(5) . ? C8 H8 0.9500 . ? C9 C10 1.410(5) . ? C10 C11 1.368(5) . ? 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 1.364(5) . ? C14 H14 0.9500 . ? C15 C16 1.414(5) . ? C15 H15 0.9500 . ? C16 C17 1.415(5) . ? C17 C18 1.373(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 C22 1.360(5) . ? C21 H21 0.9500 . ? C22 C23 1.409(6) . ? C22 H22 0.9500 . ? C23 C24 1.405(7) . ? C24 C25 1.377(6) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.364(6) . ? C28 H28 0.9500 . ? C29 C30 1.407(7) . ? C29 H29 0.9500 . ? C30 C31 1.415(6) . ? C31 C32 1.380(6) . ? C31 H31 0.9500 . ? C32 C33 1.467(5) . ? C33 C34 1.391(5) . ? C33 C38 1.414(5) . ? C34 C35 1.371(6) . ? C35 C36 1.376(6) . ? C35 H35 0.9500 . ? C36 C37 1.377(5) . ? C37 C38 1.390(5) . ? C37 H37 0.9500 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? P1 F5 1.536(5) . ? P1 F9 1.551(4) . ? P1 F7 1.559(4) . ? P1 F10 1.559(4) . ? P1 F6 1.597(4) . ? P1 F8 1.609(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C38 Ir1 C1 89.56(13) . . ? C38 Ir1 N7 79.81(14) . . ? C1 Ir1 N7 93.25(13) . . ? C38 Ir1 N1 96.08(13) . . ? C1 Ir1 N1 79.80(13) . . ? N7 Ir1 N1 172.01(11) . . ? C38 Ir1 N3 177.28(12) . . ? C1 Ir1 N3 91.63(12) . . ? N7 Ir1 N3 97.67(12) . . ? N1 Ir1 N3 86.54(11) . . ? C38 Ir1 N5 89.05(13) . . ? C1 Ir1 N5 178.15(12) . . ? N7 Ir1 N5 87.70(12) . . ? N1 Ir1 N5 99.14(12) . . ? N3 Ir1 N5 89.82(11) . . ? C11 N1 C7 116.7(3) . . ? C11 N1 Ir1 126.7(2) . . ? C7 N1 Ir1 116.6(2) . . ? C9 N2 C13 121.1(3) . . ? C9 N2 C12 120.5(3) . . ? C13 N2 C12 118.4(3) . . ? C14 N3 C18 115.2(3) . . ? C14 N3 Ir1 122.6(2) . . ? C18 N3 Ir1 122.3(2) . . ? C16 N4 C20 122.3(3) . . ? C16 N4 C19 120.4(3) . . ? C20 N4 C19 115.8(3) . . ? C21 N5 C25 115.1(3) . . ? C21 N5 Ir1 123.6(2) . . ? C25 N5 Ir1 121.3(3) . . ? C23 N6 C26 121.3(4) . . ? C23 N6 C27 120.4(5) . . ? C26 N6 C27 118.0(4) . . ? C28 N7 C32 117.2(3) . . ? C28 N7 Ir1 125.3(3) . . ? C32 N7 Ir1 117.2(2) . . ? C30 N8 C40 120.8(4) . . ? C30 N8 C39 120.4(5) . . ? C40 N8 C39 118.3(4) . . ? C2 C1 C6 117.9(3) . . ? C2 C1 Ir1 126.7(3) . . ? C6 C1 Ir1 115.4(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? F1 C3 C2 119.1(3) . . ? F1 C3 C4 117.2(3) . . ? C2 C3 C4 123.7(3) . . ? C3 C4 C5 116.1(3) . . ? C3 C4 H4 122.0 . . ? C5 C4 H4 122.0 . . ? F2 C5 C4 116.0(3) . . ? F2 C5 C6 120.3(3) . . ? C4 C5 C6 123.7(3) . . ? C5 C6 C1 118.6(3) . . ? C5 C6 C7 126.1(3) . . ? C1 C6 C7 115.3(3) . . ? N1 C7 C8 121.3(3) . . ? N1 C7 C6 112.8(3) . . ? C8 C7 C6 125.9(3) . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? N2 C9 C8 122.2(3) . . ? N2 C9 C10 121.1(3) . . ? C8 C9 C10 116.7(3) . . ? C11 C10 C9 119.0(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N1 C11 C10 124.9(3) . . ? N1 C11 H11 117.5 . . ? C10 C11 H11 117.5 . . ? 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 . . ? N3 C14 C15 124.6(3) . . ? N3 C14 H14 117.7 . . ? C15 C14 H14 117.7 . . ? C14 C15 C16 120.5(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N4 C16 C15 122.4(4) . . ? N4 C16 C17 122.9(3) . . ? C15 C16 C17 114.7(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? N3 C18 C17 124.6(3) . . ? N3 C18 H18 117.7 . . ? C17 C18 H18 117.7 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N5 C21 C22 125.2(4) . . ? N5 C21 H21 117.4 . . ? C22 C21 H21 117.4 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? N6 C23 C24 123.0(4) . . ? N6 C23 C22 122.3(5) . . ? C24 C23 C22 114.7(4) . . ? C25 C24 C23 121.0(4) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? N5 C25 C24 123.6(4) . . ? N5 C25 H25 118.2 . . ? C24 C25 H25 118.2 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N6 C27 H27A 109.5 . . ? N6 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N6 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N7 C28 C29 123.9(4) . . ? N7 C28 H28 118.0 . . ? C29 C28 H28 118.0 . . ? C28 C29 C30 120.1(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? N8 C30 C29 122.3(4) . . ? N8 C30 C31 121.8(4) . . ? C29 C30 C31 115.9(4) . . ? C32 C31 C30 121.4(4) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? N7 C32 C31 121.4(4) . . ? N7 C32 C33 112.0(3) . . ? C31 C32 C33 126.6(4) . . ? C34 C33 C38 118.1(4) . . ? C34 C33 C32 126.1(4) . . ? C38 C33 C32 115.8(3) . . ? F3 C34 C35 116.1(4) . . ? F3 C34 C33 119.9(4) . . ? C35 C34 C33 124.0(4) . . ? C34 C35 C36 115.8(4) . . ? C34 C35 H35 122.1 . . ? C36 C35 H35 122.1 . . ? F4 C36 C35 117.7(4) . . ? F4 C36 C37 118.4(4) . . ? C35 C36 C37 123.8(4) . . ? C36 C37 C38 119.4(4) . . ? C36 C37 H37 120.3 . . ? C38 C37 H37 120.3 . . ? C37 C38 C33 118.9(3) . . ? C37 C38 Ir1 126.4(3) . . ? C33 C38 Ir1 114.7(3) . . ? N8 C39 H39A 109.5 . . ? N8 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N8 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? N8 C40 H40A 109.5 . . ? N8 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N8 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? F5 P1 F9 91.4(3) . . ? F5 P1 F7 92.9(3) . . ? F9 P1 F7 93.2(3) . . ? F5 P1 F10 90.2(3) . . ? F9 P1 F10 88.8(3) . . ? F7 P1 F10 176.3(3) . . ? F5 P1 F6 90.6(3) . . ? F9 P1 F6 178.0(3) . . ? F7 P1 F6 86.9(2) . . ? F10 P1 F6 91.0(2) . . ? F5 P1 F8 175.2(4) . . ? F9 P1 F8 91.6(3) . . ? F7 P1 F8 90.7(3) . . ? F10 P1 F8 86.1(3) . . ? F6 P1 F8 86.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C38 Ir1 N1 C11 -92.3(3) . . . . ? C1 Ir1 N1 C11 179.3(3) . . . . ? N3 Ir1 N1 C11 87.0(3) . . . . ? N5 Ir1 N1 C11 -2.2(3) . . . . ? C38 Ir1 N1 C7 87.2(3) . . . . ? C1 Ir1 N1 C7 -1.2(2) . . . . ? N3 Ir1 N1 C7 -93.5(2) . . . . ? N5 Ir1 N1 C7 177.2(2) . . . . ? C1 Ir1 N3 C14 28.9(3) . . . . ? N7 Ir1 N3 C14 -64.6(3) . . . . ? N1 Ir1 N3 C14 108.6(3) . . . . ? N5 Ir1 N3 C14 -152.2(3) . . . . ? C1 Ir1 N3 C18 -152.2(3) . . . . ? N7 Ir1 N3 C18 114.3(3) . . . . ? N1 Ir1 N3 C18 -72.5(3) . . . . ? N5 Ir1 N3 C18 26.7(3) . . . . ? C38 Ir1 N5 C21 52.4(3) . . . . ? N7 Ir1 N5 C21 132.2(3) . . . . ? N1 Ir1 N5 C21 -43.6(3) . . . . ? N3 Ir1 N5 C21 -130.1(3) . . . . ? C38 Ir1 N5 C25 -129.9(3) . . . . ? N7 Ir1 N5 C25 -50.0(3) . . . . ? N1 Ir1 N5 C25 134.1(3) . . . . ? N3 Ir1 N5 C25 47.7(3) . . . . ? C38 Ir1 N7 C28 -180.0(3) . . . . ? C1 Ir1 N7 C28 -91.0(3) . . . . ? N3 Ir1 N7 C28 1.1(3) . . . . ? N5 Ir1 N7 C28 90.6(3) . . . . ? C38 Ir1 N7 C32 -6.4(3) . . . . ? C1 Ir1 N7 C32 82.6(3) . . . . ? N3 Ir1 N7 C32 174.7(3) . . . . ? N5 Ir1 N7 C32 -95.8(3) . . . . ? C38 Ir1 C1 C2 85.7(3) . . . . ? N7 Ir1 C1 C2 5.9(3) . . . . ? N1 Ir1 C1 C2 -178.1(3) . . . . ? N3 Ir1 C1 C2 -91.9(3) . . . . ? C38 Ir1 C1 C6 -94.6(3) . . . . ? N7 Ir1 C1 C6 -174.4(3) . . . . ? N1 Ir1 C1 C6 1.6(2) . . . . ? N3 Ir1 C1 C6 87.8(3) . . . . ? C6 C1 C2 C3 0.5(5) . . . . ? Ir1 C1 C2 C3 -179.8(3) . . . . ? C1 C2 C3 F1 179.8(3) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? F1 C3 C4 C5 -179.9(3) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 F2 -179.1(3) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? F2 C5 C6 C1 179.6(3) . . . . ? C4 C5 C6 C1 1.1(5) . . . . ? F2 C5 C6 C7 0.8(5) . . . . ? C4 C5 C6 C7 -177.8(3) . . . . ? C2 C1 C6 C5 -1.1(5) . . . . ? Ir1 C1 C6 C5 179.2(2) . . . . ? C2 C1 C6 C7 177.9(3) . . . . ? Ir1 C1 C6 C7 -1.8(4) . . . . ? C11 N1 C7 C8 -0.7(5) . . . . ? Ir1 N1 C7 C8 179.8(2) . . . . ? C11 N1 C7 C6 -179.9(3) . . . . ? Ir1 N1 C7 C6 0.6(4) . . . . ? C5 C6 C7 N1 179.6(3) . . . . ? C1 C6 C7 N1 0.7(4) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? C1 C6 C7 C8 -178.4(3) . . . . ? N1 C7 C8 C9 1.2(5) . . . . ? C6 C7 C8 C9 -179.7(3) . . . . ? C13 N2 C9 C8 -172.6(3) . . . . ? C12 N2 C9 C8 4.9(5) . . . . ? C13 N2 C9 C10 8.2(5) . . . . ? C12 N2 C9 C10 -174.2(3) . . . . ? C7 C8 C9 N2 -179.3(3) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? N2 C9 C10 C11 177.6(3) . . . . ? C8 C9 C10 C11 -1.6(5) . . . . ? C7 N1 C11 C10 -1.1(5) . . . . ? Ir1 N1 C11 C10 178.4(3) . . . . ? C9 C10 C11 N1 2.3(6) . . . . ? C18 N3 C14 C15 -3.7(6) . . . . ? Ir1 N3 C14 C15 175.3(3) . . . . ? N3 C14 C15 C16 -1.8(6) . . . . ? C20 N4 C16 C15 166.5(4) . . . . ? C19 N4 C16 C15 0.9(6) . . . . ? C20 N4 C16 C17 -13.9(6) . . . . ? C19 N4 C16 C17 -179.5(4) . . . . ? C14 C15 C16 N4 -174.8(4) . . . . ? C14 C15 C16 C17 5.6(6) . . . . ? N4 C16 C17 C18 176.3(4) . . . . ? C15 C16 C17 C18 -4.1(5) . . . . ? C14 N3 C18 C17 5.4(5) . . . . ? Ir1 N3 C18 C17 -173.6(3) . . . . ? C16 C17 C18 N3 -1.5(6) . . . . ? C25 N5 C21 C22 -3.9(6) . . . . ? Ir1 N5 C21 C22 173.9(3) . . . . ? N5 C21 C22 C23 1.6(6) . . . . ? C26 N6 C23 C24 -172.2(4) . . . . ? C27 N6 C23 C24 1.5(7) . . . . ? C26 N6 C23 C22 7.5(7) . . . . ? C27 N6 C23 C22 -178.7(4) . . . . ? C21 C22 C23 N6 -177.2(4) . . . . ? C21 C22 C23 C24 2.6(6) . . . . ? N6 C23 C24 C25 175.4(4) . . . . ? C22 C23 C24 C25 -4.4(6) . . . . ? C21 N5 C25 C24 2.0(6) . . . . ? Ir1 N5 C25 C24 -175.9(3) . . . . ? C23 C24 C25 N5 2.2(6) . . . . ? C32 N7 C28 C29 -0.1(6) . . . . ? Ir1 N7 C28 C29 173.5(3) . . . . ? N7 C28 C29 C30 -2.1(7) . . . . ? C40 N8 C30 C29 173.7(5) . . . . ? C39 N8 C30 C29 2.3(8) . . . . ? C40 N8 C30 C31 -5.7(8) . . . . ? C39 N8 C30 C31 -177.1(5) . . . . ? C28 C29 C30 N8 -176.6(5) . . . . ? C28 C29 C30 C31 2.8(6) . . . . ? N8 C30 C31 C32 177.8(4) . . . . ? C29 C30 C31 C32 -1.6(6) . . . . ? C28 N7 C32 C31 1.5(5) . . . . ? Ir1 N7 C32 C31 -172.6(3) . . . . ? C28 N7 C32 C33 -179.3(3) . . . . ? Ir1 N7 C32 C33 6.5(4) . . . . ? C30 C31 C32 N7 -0.6(6) . . . . ? C30 C31 C32 C33 -179.7(4) . . . . ? N7 C32 C33 C34 175.7(3) . . . . ? C31 C32 C33 C34 -5.1(6) . . . . ? N7 C32 C33 C38 -2.5(5) . . . . ? C31 C32 C33 C38 176.6(4) . . . . ? C38 C33 C34 F3 -179.1(3) . . . . ? C32 C33 C34 F3 2.6(6) . . . . ? C38 C33 C34 C35 0.4(6) . . . . ? C32 C33 C34 C35 -177.9(4) . . . . ? F3 C34 C35 C36 -179.9(3) . . . . ? C33 C34 C35 C36 0.6(6) . . . . ? C34 C35 C36 F4 -179.8(3) . . . . ? C34 C35 C36 C37 -1.1(6) . . . . ? F4 C36 C37 C38 179.2(3) . . . . ? C35 C36 C37 C38 0.5(6) . . . . ? C36 C37 C38 C33 0.6(5) . . . . ? C36 C37 C38 Ir1 -179.4(3) . . . . ? C34 C33 C38 C37 -1.0(5) . . . . ? C32 C33 C38 C37 177.4(3) . . . . ? C34 C33 C38 Ir1 179.0(3) . . . . ? C32 C33 C38 Ir1 -2.6(4) . . . . ? C1 Ir1 C38 C37 91.2(3) . . . . ? N7 Ir1 C38 C37 -175.4(3) . . . . ? N1 Ir1 C38 C37 11.5(3) . . . . ? N5 Ir1 C38 C37 -87.6(3) . . . . ? C1 Ir1 C38 C33 -88.8(3) . . . . ? N7 Ir1 C38 C33 4.6(2) . . . . ? N1 Ir1 C38 C33 -168.5(3) . . . . ? N5 Ir1 C38 C33 92.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.829 _refine_diff_density_min -1.178 _refine_diff_density_rms 0.094 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.000 117 17 ' ' 2 0.146 0.792 0.281 8 0 ' ' 3 0.854 0.208 0.719 8 0 ' ' _platon_squeeze_details ; ; # Attachment '- eb73.cif' data_eb73 _database_code_depnum_ccdc_archive 'CCDC 803766' #TrackingRef '- eb73.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H21 Cl4 Ir N4 O2' _chemical_formula_sum 'C30 H21 Cl4 Ir N4 O2' _chemical_formula_weight 803.51 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9283(13) _cell_length_b 11.5891(10) _cell_length_c 14.914(3) _cell_angle_alpha 88.213(10) _cell_angle_beta 78.226(13) _cell_angle_gamma 64.844(9) _cell_volume 1517.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 155 _cell_measurement_theta_min 3.486 _cell_measurement_theta_max 21.048 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 4.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6511 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS, Bruker AXS, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 33984 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6926 _reflns_number_gt 6345 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0151P)^2^+1.9906P] 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 6926 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0527 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 0.309284(14) 0.263849(11) 0.271393(8) 0.01373(4) Uani 1 1 d . . . Cl1 Cl 0.37503(10) -0.14378(8) 0.04019(6) 0.02754(19) Uani 1 1 d . . . Cl2 Cl 0.10799(10) 0.32585(8) -0.06828(6) 0.02587(18) Uani 1 1 d . . . Cl3 Cl 0.95793(9) 0.04561(8) 0.13789(7) 0.0301(2) Uani 1 1 d . . . Cl4 Cl 0.63385(10) 0.52741(8) 0.06986(7) 0.0341(2) Uani 1 1 d . . . O1 O 0.3077(2) 0.3130(2) 0.41020(15) 0.0189(5) Uani 1 1 d . . . O2 O 0.1769(3) 0.3440(2) 0.55483(15) 0.0220(5) Uani 1 1 d . . . N1 N 0.4071(3) 0.0720(2) 0.28511(19) 0.0179(6) Uani 1 1 d . . . N2 N 0.2342(3) 0.4518(2) 0.24303(18) 0.0157(5) Uani 1 1 d . . . N3 N 0.0934(3) 0.2807(2) 0.34634(18) 0.0172(6) Uani 1 1 d . . . N4 N -0.3298(3) 0.3504(3) 0.5143(2) 0.0245(6) Uani 1 1 d . . . C1 C 0.4715(4) 0.0211(3) 0.3570(2) 0.0243(8) Uani 1 1 d . . . H1 H 0.4570 0.0763 0.4075 0.029 Uiso 1 1 calc R . . C2 C 0.5581(4) -0.1091(3) 0.3596(3) 0.0303(9) Uani 1 1 d . . . H2 H 0.6021 -0.1429 0.4109 0.036 Uiso 1 1 calc R . . C3 C 0.5790(4) -0.1884(3) 0.2857(3) 0.0291(9) Uani 1 1 d . . . H3 H 0.6394 -0.2778 0.2852 0.035 Uiso 1 1 calc R . . C4 C 0.5113(4) -0.1367(3) 0.2123(3) 0.0250(8) Uani 1 1 d . . . H4 H 0.5250 -0.1913 0.1617 0.030 Uiso 1 1 calc R . . C5 C 0.4231(4) -0.0051(3) 0.2121(2) 0.0185(7) Uani 1 1 d . . . C6 C 0.3483(3) 0.0676(3) 0.1392(2) 0.0176(7) Uani 1 1 d . . . C7 C 0.3257(4) 0.0191(3) 0.0616(2) 0.0194(7) Uani 1 1 d . . . C8 C 0.2553(4) 0.0966(3) -0.0031(2) 0.0210(7) Uani 1 1 d . . . H8 H 0.2431 0.0612 -0.0557 0.025 Uiso 1 1 calc R . . C9 C 0.2031(4) 0.2274(3) 0.0112(2) 0.0190(7) Uani 1 1 d . . . C10 C 0.2202(3) 0.2814(3) 0.0870(2) 0.0171(7) Uani 1 1 d . . . H10 H 0.1831 0.3715 0.0949 0.020 Uiso 1 1 calc R . . C11 C 0.2923(3) 0.2027(3) 0.1522(2) 0.0162(6) Uani 1 1 d . . . C12 C 0.5075(3) 0.2656(3) 0.2090(2) 0.0149(6) Uani 1 1 d . . . C13 C 0.6525(4) 0.1630(3) 0.1990(2) 0.0180(7) Uani 1 1 d . . . H13 H 0.6631 0.0847 0.2252 0.022 Uiso 1 1 calc R . . C14 C 0.7795(4) 0.1757(3) 0.1513(2) 0.0201(7) Uani 1 1 d . . . C15 C 0.7714(4) 0.2875(3) 0.1116(2) 0.0202(7) Uani 1 1 d . . . H15 H 0.8604 0.2933 0.0781 0.024 Uiso 1 1 calc R . . C16 C 0.6291(4) 0.3914(3) 0.1221(2) 0.0200(7) Uani 1 1 d . . . C17 C 0.4954(3) 0.3837(3) 0.1701(2) 0.0164(6) Uani 1 1 d . . . C18 C 0.3388(4) 0.4876(3) 0.1897(2) 0.0175(7) Uani 1 1 d . . . C19 C 0.2901(4) 0.6130(3) 0.1630(2) 0.0262(8) Uani 1 1 d . . . H19 H 0.3605 0.6379 0.1242 0.031 Uiso 1 1 calc R . . C20 C 0.1408(4) 0.7013(3) 0.1923(3) 0.0301(9) Uani 1 1 d . . . H20 H 0.1082 0.7862 0.1733 0.036 Uiso 1 1 calc R . . C21 C 0.0393(4) 0.6648(3) 0.2494(2) 0.0252(8) Uani 1 1 d . . . H21 H -0.0628 0.7247 0.2725 0.030 Uiso 1 1 calc R . . C22 C 0.0897(4) 0.5394(3) 0.2722(2) 0.0194(7) Uani 1 1 d . . . H22 H 0.0194 0.5136 0.3102 0.023 Uiso 1 1 calc R . . C23 C -0.0166(4) 0.2678(3) 0.3129(2) 0.0227(7) Uani 1 1 d . . . H23 H 0.0042 0.2427 0.2497 0.027 Uiso 1 1 calc R . . C24 C -0.1572(4) 0.2891(3) 0.3656(2) 0.0224(7) Uani 1 1 d . . . H24 H -0.2305 0.2788 0.3386 0.027 Uiso 1 1 calc R . . C25 C -0.1919(4) 0.3263(3) 0.4602(2) 0.0183(7) Uani 1 1 d . . . C26 C -0.0748(4) 0.3374(3) 0.4947(2) 0.0181(7) Uani 1 1 d . . . H26 H -0.0908 0.3606 0.5578 0.022 Uiso 1 1 calc R . . C27 C 0.0622(3) 0.3147(3) 0.4369(2) 0.0155(6) Uani 1 1 d . . . C28 C 0.1899(3) 0.3257(3) 0.4722(2) 0.0154(6) Uani 1 1 d . . . C29 C -0.4399(4) 0.3214(4) 0.4809(3) 0.0295(8) Uani 1 1 d . . . H29A H -0.4531 0.3582 0.4215 0.044 Uiso 1 1 calc R . . H29B H -0.5377 0.3577 0.5250 0.044 Uiso 1 1 calc R . . H29C H -0.4035 0.2285 0.4737 0.044 Uiso 1 1 calc R . . C30 C -0.3578(4) 0.3825(5) 0.6126(3) 0.0384(10) Uani 1 1 d . . . H30A H -0.2984 0.3068 0.6426 0.058 Uiso 1 1 calc R . . H30B H -0.4664 0.4114 0.6396 0.058 Uiso 1 1 calc R . . H30C H -0.3273 0.4507 0.6214 0.058 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 0.01247(6) 0.01773(6) 0.01183(6) -0.00096(4) -0.00101(4) -0.00783(5) Cl1 0.0357(5) 0.0218(4) 0.0276(5) -0.0048(3) -0.0008(4) -0.0168(4) Cl2 0.0261(4) 0.0340(5) 0.0186(4) 0.0017(3) -0.0090(3) -0.0120(4) Cl3 0.0137(4) 0.0249(4) 0.0441(6) 0.0009(4) 0.0012(4) -0.0045(3) Cl4 0.0295(5) 0.0244(4) 0.0453(6) 0.0068(4) 0.0055(4) -0.0148(4) O1 0.0148(11) 0.0298(12) 0.0148(12) -0.0037(9) -0.0025(9) -0.0121(10) O2 0.0191(12) 0.0354(13) 0.0147(12) 0.0008(10) -0.0050(9) -0.0141(10) N1 0.0141(13) 0.0222(14) 0.0168(14) 0.0020(11) 0.0009(11) -0.0091(11) N2 0.0157(13) 0.0190(13) 0.0125(13) -0.0025(10) -0.0043(10) -0.0067(11) N3 0.0150(13) 0.0245(14) 0.0149(14) -0.0013(11) -0.0022(11) -0.0113(11) N4 0.0172(14) 0.0391(17) 0.0216(16) -0.0045(13) -0.0004(12) -0.0175(13) C1 0.0218(17) 0.0308(18) 0.0207(18) 0.0080(14) -0.0028(14) -0.0126(15) C2 0.0242(19) 0.033(2) 0.030(2) 0.0137(16) -0.0056(16) -0.0104(16) C3 0.0235(18) 0.0192(17) 0.037(2) 0.0088(15) -0.0002(16) -0.0048(14) C4 0.0254(18) 0.0203(17) 0.0260(19) 0.0000(14) 0.0016(15) -0.0097(14) C5 0.0168(16) 0.0195(16) 0.0174(17) 0.0014(13) 0.0027(13) -0.0088(13) C6 0.0143(15) 0.0210(16) 0.0163(16) -0.0013(12) 0.0027(12) -0.0089(13) C7 0.0194(16) 0.0192(16) 0.0206(17) -0.0046(13) 0.0047(13) -0.0126(13) C8 0.0226(17) 0.0275(17) 0.0162(17) -0.0064(13) 0.0022(13) -0.0162(14) C9 0.0152(15) 0.0273(17) 0.0153(16) 0.0013(13) -0.0019(13) -0.0105(13) C10 0.0156(15) 0.0214(16) 0.0139(16) -0.0021(12) -0.0001(12) -0.0087(13) C11 0.0140(15) 0.0222(16) 0.0127(16) -0.0021(12) 0.0011(12) -0.0095(13) C12 0.0144(15) 0.0214(16) 0.0111(15) -0.0008(12) -0.0017(12) -0.0100(13) C13 0.0195(16) 0.0185(15) 0.0166(16) 0.0008(12) -0.0011(13) -0.0099(13) C14 0.0151(16) 0.0200(16) 0.0220(18) -0.0048(13) -0.0032(13) -0.0045(13) C15 0.0160(16) 0.0255(17) 0.0204(17) -0.0017(13) 0.0034(13) -0.0133(14) C16 0.0228(17) 0.0190(16) 0.0195(17) 0.0000(13) -0.0003(14) -0.0121(14) C17 0.0157(15) 0.0203(16) 0.0137(16) -0.0024(12) -0.0017(12) -0.0086(13) C18 0.0171(16) 0.0189(15) 0.0177(17) -0.0013(12) -0.0027(13) -0.0090(13) C19 0.0223(18) 0.0255(18) 0.0257(19) 0.0065(14) -0.0013(15) -0.0075(15) C20 0.029(2) 0.0210(17) 0.034(2) 0.0089(15) -0.0073(16) -0.0048(15) C21 0.0186(17) 0.0268(18) 0.0226(19) 0.0015(14) -0.0052(14) -0.0022(14) C22 0.0168(16) 0.0246(17) 0.0141(16) -0.0022(13) -0.0034(13) -0.0060(13) C23 0.0233(18) 0.0339(19) 0.0159(17) -0.0044(14) -0.0026(14) -0.0171(15) C24 0.0207(17) 0.0347(19) 0.0199(18) -0.0037(14) -0.0061(14) -0.0183(15) C25 0.0156(15) 0.0243(16) 0.0180(17) 0.0010(13) -0.0035(13) -0.0113(13) C26 0.0184(16) 0.0249(17) 0.0135(16) 0.0000(13) -0.0042(13) -0.0113(13) C27 0.0146(15) 0.0191(15) 0.0151(16) 0.0015(12) -0.0056(12) -0.0082(12) C28 0.0160(15) 0.0178(15) 0.0150(16) 0.0005(12) -0.0048(12) -0.0088(12) C29 0.0176(17) 0.048(2) 0.031(2) -0.0009(17) -0.0038(15) -0.0222(17) C30 0.026(2) 0.076(3) 0.020(2) -0.0066(19) 0.0027(16) -0.032(2) _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 C11 1.998(3) . ? Ir1 C12 2.006(3) . ? Ir1 N1 2.036(3) . ? Ir1 N2 2.042(3) . ? Ir1 N3 2.135(3) . ? Ir1 O1 2.160(2) . ? Cl1 C7 1.758(3) . ? Cl2 C9 1.748(3) . ? Cl3 C14 1.748(3) . ? Cl4 C16 1.751(3) . ? O1 C28 1.291(4) . ? O2 C28 1.229(4) . ? N1 C1 1.352(4) . ? N1 C5 1.370(4) . ? N2 C22 1.346(4) . ? N2 C18 1.375(4) . ? N3 C23 1.353(4) . ? N3 C27 1.354(4) . ? N4 C25 1.357(4) . ? N4 C29 1.450(4) . ? N4 C30 1.464(5) . ? C1 C2 1.387(5) . ? C1 H1 0.9500 . ? C2 C3 1.381(6) . ? C2 H2 0.9500 . ? C3 C4 1.388(5) . ? C3 H3 0.9500 . ? C4 C5 1.400(4) . ? C4 H4 0.9500 . ? C5 C6 1.479(5) . ? C6 C7 1.400(5) . ? C6 C11 1.426(4) . ? C7 C8 1.383(5) . ? C8 C9 1.386(5) . ? C8 H8 0.9500 . ? C9 C10 1.382(5) . ? C10 C11 1.401(4) . ? C10 H10 0.9500 . ? C12 C13 1.406(4) . ? C12 C17 1.437(4) . ? C13 C14 1.380(4) . ? C13 H13 0.9500 . ? C14 C15 1.385(4) . ? C15 C16 1.395(5) . ? C15 H15 0.9500 . ? C16 C17 1.411(4) . ? C17 C18 1.483(4) . ? C18 C19 1.396(4) . ? C19 C20 1.382(5) . ? C19 H19 0.9500 . ? C20 C21 1.382(5) . ? C20 H20 0.9500 . ? C21 C22 1.378(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.377(4) . ? C23 H23 0.9500 . ? C24 C25 1.418(5) . ? C24 H24 0.9500 . ? C25 C26 1.417(4) . ? C26 C27 1.376(4) . ? C26 H26 0.9500 . ? C27 C28 1.521(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 C11 Ir1 C12 89.24(12) . . ? C11 Ir1 N1 80.47(12) . . ? C12 Ir1 N1 93.01(11) . . ? C11 Ir1 N2 95.96(12) . . ? C12 Ir1 N2 80.23(11) . . ? N1 Ir1 N2 172.44(10) . . ? C11 Ir1 N3 95.79(11) . . ? C12 Ir1 N3 173.65(11) . . ? N1 Ir1 N3 91.65(10) . . ? N2 Ir1 N3 95.35(10) . . ? C11 Ir1 O1 170.86(10) . . ? C12 Ir1 O1 98.63(11) . . ? N1 Ir1 O1 94.42(10) . . ? N2 Ir1 O1 89.98(10) . . ? N3 Ir1 O1 76.69(9) . . ? C28 O1 Ir1 116.9(2) . . ? C1 N1 C5 120.5(3) . . ? C1 N1 Ir1 122.1(2) . . ? C5 N1 Ir1 116.8(2) . . ? C22 N2 C18 119.6(3) . . ? C22 N2 Ir1 123.5(2) . . ? C18 N2 Ir1 116.8(2) . . ? C23 N3 C27 117.2(3) . . ? C23 N3 Ir1 127.6(2) . . ? C27 N3 Ir1 115.1(2) . . ? C25 N4 C29 121.0(3) . . ? C25 N4 C30 119.7(3) . . ? C29 N4 C30 118.2(3) . . ? N1 C1 C2 122.1(4) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 118.5(4) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N1 C5 C4 118.7(3) . . ? N1 C5 C6 112.8(3) . . ? C4 C5 C6 128.4(3) . . ? C7 C6 C11 117.9(3) . . ? C7 C6 C5 127.6(3) . . ? C11 C6 C5 114.5(3) . . ? C8 C7 C6 122.6(3) . . ? C8 C7 Cl1 113.9(3) . . ? C6 C7 Cl1 123.4(3) . . ? C7 C8 C9 118.1(3) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 122.1(3) . . ? C10 C9 Cl2 119.7(3) . . ? C8 C9 Cl2 118.1(3) . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 119.5(3) . . ? C10 C11 Ir1 125.3(2) . . ? C6 C11 Ir1 115.0(2) . . ? C13 C12 C17 118.6(3) . . ? C13 C12 Ir1 126.2(2) . . ? C17 C12 Ir1 115.2(2) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 122.5(3) . . ? C13 C14 Cl3 119.3(3) . . ? C15 C14 Cl3 118.1(3) . . ? C14 C15 C16 118.2(3) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C15 C16 C17 121.6(3) . . ? C15 C16 Cl4 114.0(2) . . ? C17 C16 Cl4 124.4(2) . . ? C16 C17 C12 118.7(3) . . ? C16 C17 C18 127.3(3) . . ? C12 C17 C18 114.0(3) . . ? N2 C18 C19 118.9(3) . . ? N2 C18 C17 113.2(3) . . ? C19 C18 C17 127.9(3) . . ? C20 C19 C18 120.8(3) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C22 C21 C20 118.5(3) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? N2 C22 C21 122.8(3) . . ? N2 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? N3 C23 C24 123.5(3) . . ? N3 C23 H23 118.2 . . ? C24 C23 H23 118.2 . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? N4 C25 C26 122.2(3) . . ? N4 C25 C24 121.7(3) . . ? C26 C25 C24 116.2(3) . . ? C27 C26 C25 120.2(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N3 C27 C26 123.2(3) . . ? N3 C27 C28 115.6(3) . . ? C26 C27 C28 121.2(3) . . ? O2 C28 O1 124.6(3) . . ? O2 C28 C27 120.0(3) . . ? O1 C28 C27 115.4(3) . . ? N4 C29 H29A 109.5 . . ? N4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N4 C30 H30A 109.5 . . ? N4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C12 Ir1 O1 C28 177.6(2) . . . . ? N1 Ir1 O1 C28 -88.7(2) . . . . ? N2 Ir1 O1 C28 97.5(2) . . . . ? N3 Ir1 O1 C28 2.0(2) . . . . ? C11 Ir1 N1 C1 174.6(3) . . . . ? C12 Ir1 N1 C1 85.9(3) . . . . ? N3 Ir1 N1 C1 -89.8(2) . . . . ? O1 Ir1 N1 C1 -13.0(2) . . . . ? C11 Ir1 N1 C5 3.1(2) . . . . ? C12 Ir1 N1 C5 -85.6(2) . . . . ? N3 Ir1 N1 C5 98.7(2) . . . . ? O1 Ir1 N1 C5 175.4(2) . . . . ? C11 Ir1 N2 C22 97.7(3) . . . . ? C12 Ir1 N2 C22 -174.1(3) . . . . ? N3 Ir1 N2 C22 1.3(3) . . . . ? O1 Ir1 N2 C22 -75.4(3) . . . . ? C11 Ir1 N2 C18 -81.1(2) . . . . ? C12 Ir1 N2 C18 7.1(2) . . . . ? N3 Ir1 N2 C18 -177.5(2) . . . . ? O1 Ir1 N2 C18 105.9(2) . . . . ? C11 Ir1 N3 C23 -7.3(3) . . . . ? N1 Ir1 N3 C23 -87.9(3) . . . . ? N2 Ir1 N3 C23 89.2(3) . . . . ? O1 Ir1 N3 C23 177.9(3) . . . . ? C11 Ir1 N3 C27 176.3(2) . . . . ? N1 Ir1 N3 C27 95.7(2) . . . . ? N2 Ir1 N3 C27 -87.2(2) . . . . ? O1 Ir1 N3 C27 1.5(2) . . . . ? C5 N1 C1 C2 1.3(5) . . . . ? Ir1 N1 C1 C2 -169.9(2) . . . . ? N1 C1 C2 C3 0.2(5) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C1 N1 C5 C4 -2.0(4) . . . . ? Ir1 N1 C5 C4 169.7(2) . . . . ? C1 N1 C5 C6 -178.6(3) . . . . ? Ir1 N1 C5 C6 -6.8(3) . . . . ? C3 C4 C5 N1 1.1(5) . . . . ? C3 C4 C5 C6 177.1(3) . . . . ? N1 C5 C6 C7 -171.1(3) . . . . ? C4 C5 C6 C7 12.8(5) . . . . ? N1 C5 C6 C11 8.1(4) . . . . ? C4 C5 C6 C11 -168.1(3) . . . . ? C11 C6 C7 C8 1.7(5) . . . . ? C5 C6 C7 C8 -179.2(3) . . . . ? C11 C6 C7 Cl1 -175.1(2) . . . . ? C5 C6 C7 Cl1 4.0(5) . . . . ? C6 C7 C8 C9 -1.2(5) . . . . ? Cl1 C7 C8 C9 175.8(2) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C7 C8 C9 Cl2 -177.7(2) . . . . ? C8 C9 C10 C11 0.0(5) . . . . ? Cl2 C9 C10 C11 178.1(2) . . . . ? C9 C10 C11 C6 0.4(4) . . . . ? C9 C10 C11 Ir1 -173.7(2) . . . . ? C7 C6 C11 C10 -1.2(4) . . . . ? C5 C6 C11 C10 179.6(3) . . . . ? C7 C6 C11 Ir1 173.5(2) . . . . ? C5 C6 C11 Ir1 -5.7(3) . . . . ? C12 Ir1 C11 C10 -90.8(3) . . . . ? N1 Ir1 C11 C10 176.0(3) . . . . ? N2 Ir1 C11 C10 -10.7(3) . . . . ? N3 Ir1 C11 C10 85.3(3) . . . . ? C12 Ir1 C11 C6 94.8(2) . . . . ? N1 Ir1 C11 C6 1.6(2) . . . . ? N2 Ir1 C11 C6 174.9(2) . . . . ? N3 Ir1 C11 C6 -89.1(2) . . . . ? C11 Ir1 C12 C13 -88.8(3) . . . . ? N1 Ir1 C12 C13 -8.4(3) . . . . ? N2 Ir1 C12 C13 175.0(3) . . . . ? O1 Ir1 C12 C13 86.5(3) . . . . ? C11 Ir1 C12 C17 89.9(2) . . . . ? N1 Ir1 C12 C17 170.3(2) . . . . ? N2 Ir1 C12 C17 -6.3(2) . . . . ? O1 Ir1 C12 C17 -94.8(2) . . . . ? C17 C12 C13 C14 -1.2(5) . . . . ? Ir1 C12 C13 C14 177.5(2) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C12 C13 C14 Cl3 -178.7(3) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? Cl3 C14 C15 C16 179.9(3) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C14 C15 C16 Cl4 179.4(3) . . . . ? C15 C16 C17 C12 0.1(5) . . . . ? Cl4 C16 C17 C12 179.4(2) . . . . ? C15 C16 C17 C18 177.2(3) . . . . ? Cl4 C16 C17 C18 -3.6(5) . . . . ? C13 C12 C17 C16 1.1(5) . . . . ? Ir1 C12 C17 C16 -177.8(2) . . . . ? C13 C12 C17 C18 -176.4(3) . . . . ? Ir1 C12 C17 C18 4.8(4) . . . . ? C22 N2 C18 C19 -3.4(5) . . . . ? Ir1 N2 C18 C19 175.4(3) . . . . ? C22 N2 C18 C17 174.8(3) . . . . ? Ir1 N2 C18 C17 -6.4(4) . . . . ? C16 C17 C18 N2 -176.1(3) . . . . ? C12 C17 C18 N2 1.0(4) . . . . ? C16 C17 C18 C19 1.9(6) . . . . ? C12 C17 C18 C19 179.0(3) . . . . ? N2 C18 C19 C20 2.4(5) . . . . ? C17 C18 C19 C20 -175.5(4) . . . . ? C18 C19 C20 C21 0.6(6) . . . . ? C19 C20 C21 C22 -2.6(6) . . . . ? C18 N2 C22 C21 1.4(5) . . . . ? Ir1 N2 C22 C21 -177.3(3) . . . . ? C20 C21 C22 N2 1.7(5) . . . . ? C27 N3 C23 C24 1.0(5) . . . . ? Ir1 N3 C23 C24 -175.3(3) . . . . ? N3 C23 C24 C25 -0.2(5) . . . . ? C29 N4 C25 C26 -171.3(3) . . . . ? C30 N4 C25 C26 -3.3(5) . . . . ? C29 N4 C25 C24 9.0(5) . . . . ? C30 N4 C25 C24 177.0(3) . . . . ? C23 C24 C25 N4 178.9(3) . . . . ? C23 C24 C25 C26 -0.9(5) . . . . ? N4 C25 C26 C27 -178.6(3) . . . . ? C24 C25 C26 C27 1.1(5) . . . . ? C23 N3 C27 C26 -0.7(5) . . . . ? Ir1 N3 C27 C26 176.1(2) . . . . ? C23 N3 C27 C28 178.9(3) . . . . ? Ir1 N3 C27 C28 -4.4(3) . . . . ? C25 C26 C27 N3 -0.3(5) . . . . ? C25 C26 C27 C28 -179.9(3) . . . . ? Ir1 O1 C28 O2 174.3(2) . . . . ? Ir1 O1 C28 C27 -4.8(3) . . . . ? N3 C27 C28 O2 -173.0(3) . . . . ? C26 C27 C28 O2 6.6(5) . . . . ? N3 C27 C28 O1 6.1(4) . . . . ? C26 C27 C28 O1 -174.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.724 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.112 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 162 34 ' ' 2 0.177 0.502 0.783 11 1 ' ' 3 0.823 0.498 0.217 11 1 ' ' _platon_squeeze_details ; ; # Attachment '- eb95.cif' data_eb95h _database_code_depnum_ccdc_archive 'CCDC 803767' #TrackingRef '- eb95.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H20 Cl4 Ir N3 O3' _chemical_formula_sum 'C33 H20 Cl4 Ir N3 O3' _chemical_formula_weight 840.52 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9629(3) _cell_length_b 11.1318(3) _cell_length_c 12.1713(3) _cell_angle_alpha 90.525(2) _cell_angle_beta 91.673(2) _cell_angle_gamma 102.779(2) _cell_volume 1447.75(7) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 10516 _cell_measurement_theta_min 2.9058 _cell_measurement_theta_max 27.3541 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.928 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 5.023 _exptl_absorpt_correction_T_min 0.60029 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction, KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2812 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11733 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 26.02 _reflns_number_total 5655 _reflns_number_gt 5360 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0320P)^2^+0.8354P] 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 5655 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0203 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0477 _refine_ls_wR_factor_gt 0.0472 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.154655(9) 0.324843(9) 0.271091(7) 0.01706(4) Uani 1 1 d . . . Cl1 Cl 0.44008(8) -0.03418(7) 0.19760(6) 0.03532(17) Uani 1 1 d . . . Cl2 Cl 0.51442(7) 0.21198(7) 0.57922(6) 0.02835(15) Uani 1 1 d . . . Cl3 Cl -0.19709(7) -0.13434(7) 0.32148(6) 0.03404(17) Uani 1 1 d . . . Cl4 Cl -0.12850(7) 0.18779(7) 0.65279(6) 0.03330(17) Uani 1 1 d . . . O1 O 0.00914(17) 0.40453(18) 0.20437(16) 0.0240(4) Uani 1 1 d . . . O2 O -0.03034(19) 0.5689(2) 0.11815(17) 0.0304(5) Uani 1 1 d . . . O3 O 0.3852(2) 0.7478(2) -0.05603(18) 0.0352(5) Uani 1 1 d . . . N1 N 0.1609(2) 0.2172(2) 0.13677(18) 0.0183(4) Uani 1 1 d . . . N2 N 0.1527(2) 0.4191(2) 0.41410(17) 0.0182(4) Uani 1 1 d . . . N3 N 0.2551(2) 0.4838(2) 0.17796(18) 0.0187(4) Uani 1 1 d . . . C1 C 0.0928(3) 0.2241(3) 0.0434(2) 0.0230(6) Uani 1 1 d . . . H1 H 0.0398 0.2811 0.0410 0.028 Uiso 1 1 calc R . . C2 C 0.0970(3) 0.1527(3) -0.0474(2) 0.0297(7) Uani 1 1 d . . . H2 H 0.0491 0.1604 -0.1122 0.036 Uiso 1 1 calc R . . C3 C 0.1727(3) 0.0691(3) -0.0425(3) 0.0349(7) Uani 1 1 d . . . H3 H 0.1768 0.0173 -0.1042 0.042 Uiso 1 1 calc R . . C4 C 0.2427(3) 0.0605(3) 0.0522(3) 0.0326(7) Uani 1 1 d . . . H4 H 0.2942 0.0022 0.0558 0.039 Uiso 1 1 calc R . . C5 C 0.2379(3) 0.1371(2) 0.1428(2) 0.0221(6) Uani 1 1 d . . . C6 C 0.3101(3) 0.1463(2) 0.2486(2) 0.0201(5) Uani 1 1 d . . . C7 C 0.4003(3) 0.0807(3) 0.2795(2) 0.0246(6) Uani 1 1 d . . . C8 C 0.4656(3) 0.1020(3) 0.3798(2) 0.0250(6) Uani 1 1 d . . . H8 H 0.5281 0.0583 0.3990 0.030 Uiso 1 1 calc R . . C9 C 0.4372(3) 0.1884(3) 0.4508(2) 0.0222(6) Uani 1 1 d . . . C10 C 0.3480(2) 0.2542(2) 0.4249(2) 0.0201(5) Uani 1 1 d . . . H10 H 0.3299 0.3119 0.4765 0.024 Uiso 1 1 calc R . . C11 C 0.2833(2) 0.2365(2) 0.3220(2) 0.0204(5) Uani 1 1 d . . . C12 C 0.0335(2) 0.1992(3) 0.3538(2) 0.0195(5) Uani 1 1 d . . . C13 C -0.0297(3) 0.0846(3) 0.3123(2) 0.0223(6) Uani 1 1 d . . . H13 H -0.0117 0.0582 0.2413 0.027 Uiso 1 1 calc R . . C14 C -0.1187(3) 0.0090(3) 0.3741(2) 0.0250(6) Uani 1 1 d . . . C15 C -0.1470(3) 0.0436(3) 0.4775(2) 0.0264(6) Uani 1 1 d . . . H15 H -0.2090 -0.0088 0.5186 0.032 Uiso 1 1 calc R . . C16 C -0.0833(3) 0.1561(3) 0.5204(2) 0.0238(6) Uani 1 1 d . . . C17 C 0.0076(2) 0.2370(3) 0.4614(2) 0.0210(5) Uani 1 1 d . . . C18 C 0.0804(2) 0.3590(3) 0.4959(2) 0.0198(5) Uani 1 1 d . . . C19 C 0.0838(3) 0.4175(3) 0.5984(2) 0.0248(6) Uani 1 1 d . . . H19 H 0.0363 0.3761 0.6564 0.030 Uiso 1 1 calc R . . C20 C 0.1556(3) 0.5347(3) 0.6158(2) 0.0265(6) Uani 1 1 d . . . H20 H 0.1560 0.5749 0.6850 0.032 Uiso 1 1 calc R . . C21 C 0.2268(3) 0.5935(3) 0.5326(2) 0.0265(6) Uani 1 1 d . . . H21 H 0.2769 0.6743 0.5437 0.032 Uiso 1 1 calc R . . C22 C 0.2239(3) 0.5330(3) 0.4331(2) 0.0236(6) Uani 1 1 d . . . H22 H 0.2739 0.5729 0.3759 0.028 Uiso 1 1 calc R . . C23 C 0.1784(3) 0.5423(3) 0.1241(2) 0.0207(5) Uani 1 1 d . . . C24 C 0.2160(3) 0.6334(3) 0.0472(2) 0.0248(6) Uani 1 1 d . . . H24 H 0.1563 0.6712 0.0116 0.030 Uiso 1 1 calc R . . C25 C 0.3396(3) 0.6679(3) 0.0232(2) 0.0260(6) Uani 1 1 d . . . C26 C 0.4278(3) 0.6174(3) 0.0837(2) 0.0236(6) Uani 1 1 d . . . C27 C 0.3829(2) 0.5252(3) 0.1615(2) 0.0212(5) Uani 1 1 d . . . C28 C 0.4698(3) 0.4760(3) 0.2232(2) 0.0278(6) Uani 1 1 d . . . H28 H 0.4412 0.4153 0.2766 0.033 Uiso 1 1 calc R . . C29 C 0.5950(3) 0.5146(3) 0.2074(3) 0.0348(7) Uani 1 1 d . . . H29 H 0.6524 0.4802 0.2499 0.042 Uiso 1 1 calc R . . C30 C 0.6402(3) 0.6039(3) 0.1298(3) 0.0367(8) Uani 1 1 d . . . H30 H 0.7276 0.6294 0.1194 0.044 Uiso 1 1 calc R . . C31 C 0.5586(3) 0.6544(3) 0.0690(3) 0.0318(7) Uani 1 1 d . . . H31 H 0.5896 0.7149 0.0162 0.038 Uiso 1 1 calc R . . C32 C 0.0402(3) 0.5042(3) 0.1500(2) 0.0217(6) Uani 1 1 d . . . C33 C 0.2957(3) 0.7844(3) -0.1285(3) 0.0406(8) Uani 1 1 d . . . H33A H 0.2374 0.7110 -0.1587 0.061 Uiso 1 1 calc R . . H33B H 0.3390 0.8321 -0.1886 0.061 Uiso 1 1 calc R . . H33C H 0.2491 0.8351 -0.0879 0.061 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 0.01576(6) 0.01999(6) 0.01480(6) 0.00456(4) -0.00019(4) 0.00253(4) Cl1 0.0465(5) 0.0368(4) 0.0290(4) -0.0010(3) -0.0022(3) 0.0233(4) Cl2 0.0270(3) 0.0317(4) 0.0246(3) 0.0053(3) -0.0092(3) 0.0039(3) Cl3 0.0352(4) 0.0314(4) 0.0270(4) 0.0036(3) -0.0002(3) -0.0109(3) Cl4 0.0380(4) 0.0362(4) 0.0247(4) 0.0046(3) 0.0139(3) 0.0041(3) O1 0.0184(9) 0.0314(11) 0.0235(10) 0.0087(8) 0.0016(8) 0.0076(8) O2 0.0248(10) 0.0404(12) 0.0305(11) 0.0103(9) 0.0024(9) 0.0161(9) O3 0.0337(12) 0.0338(12) 0.0352(12) 0.0202(10) 0.0049(10) 0.0003(10) N1 0.0177(11) 0.0216(11) 0.0140(10) 0.0044(9) 0.0018(8) 0.0003(9) N2 0.0165(10) 0.0250(12) 0.0138(10) 0.0017(9) 0.0001(8) 0.0058(9) N3 0.0174(11) 0.0204(11) 0.0175(11) 0.0036(9) 0.0009(8) 0.0021(9) C1 0.0239(14) 0.0258(14) 0.0182(13) 0.0052(11) -0.0033(11) 0.0033(11) C2 0.0374(17) 0.0310(16) 0.0189(14) 0.0038(12) -0.0063(12) 0.0047(13) C3 0.053(2) 0.0320(17) 0.0215(15) -0.0042(13) -0.0063(14) 0.0144(15) C4 0.0424(18) 0.0286(16) 0.0294(16) -0.0006(13) -0.0039(13) 0.0138(14) C5 0.0260(14) 0.0192(13) 0.0195(13) 0.0066(10) -0.0011(11) 0.0015(11) C6 0.0219(13) 0.0187(13) 0.0189(13) 0.0074(10) 0.0019(10) 0.0022(10) C7 0.0266(14) 0.0238(14) 0.0235(14) 0.0029(11) 0.0025(11) 0.0060(12) C8 0.0233(14) 0.0251(14) 0.0274(15) 0.0097(12) 0.0003(11) 0.0069(11) C9 0.0202(13) 0.0232(14) 0.0207(13) 0.0072(11) -0.0042(10) -0.0003(11) C10 0.0212(13) 0.0196(13) 0.0183(13) 0.0047(10) -0.0005(10) 0.0023(11) C11 0.0188(13) 0.0202(13) 0.0212(13) 0.0089(11) 0.0008(10) 0.0018(10) C12 0.0178(12) 0.0236(13) 0.0155(12) 0.0065(10) -0.0001(10) 0.0009(10) C13 0.0226(13) 0.0280(15) 0.0146(12) 0.0055(11) -0.0013(10) 0.0022(11) C14 0.0224(14) 0.0250(14) 0.0237(14) 0.0046(11) -0.0050(11) -0.0026(11) C15 0.0207(14) 0.0309(16) 0.0263(15) 0.0089(12) 0.0044(11) 0.0019(12) C16 0.0248(14) 0.0323(15) 0.0153(13) 0.0063(11) 0.0036(11) 0.0079(12) C17 0.0201(13) 0.0266(14) 0.0173(13) 0.0059(11) 0.0008(10) 0.0070(11) C18 0.0162(12) 0.0270(14) 0.0179(13) 0.0063(11) 0.0000(10) 0.0085(11) C19 0.0197(13) 0.0331(16) 0.0222(14) 0.0022(12) 0.0014(11) 0.0072(12) C20 0.0215(14) 0.0374(17) 0.0216(14) -0.0058(12) -0.0026(11) 0.0094(12) C21 0.0198(13) 0.0274(15) 0.0314(16) -0.0045(12) -0.0022(12) 0.0037(12) C22 0.0197(13) 0.0271(14) 0.0244(14) 0.0036(11) 0.0017(11) 0.0058(11) C23 0.0219(13) 0.0219(13) 0.0187(13) 0.0017(10) -0.0002(10) 0.0056(11) C24 0.0286(15) 0.0247(14) 0.0230(14) 0.0067(11) -0.0009(11) 0.0101(12) C25 0.0323(16) 0.0208(14) 0.0235(14) 0.0037(11) 0.0030(12) 0.0024(12) C26 0.0233(14) 0.0199(13) 0.0254(14) 0.0025(11) 0.0025(11) 0.0001(11) C27 0.0180(13) 0.0209(13) 0.0227(14) -0.0002(11) 0.0028(10) -0.0001(10) C28 0.0218(14) 0.0303(15) 0.0301(16) 0.0076(12) -0.0008(12) 0.0033(12) C29 0.0207(15) 0.0430(19) 0.0404(18) 0.0117(15) -0.0024(13) 0.0063(13) C30 0.0185(14) 0.0414(19) 0.046(2) 0.0056(15) 0.0041(13) -0.0025(13) C31 0.0247(15) 0.0333(16) 0.0333(16) 0.0098(13) 0.0039(12) -0.0030(13) C32 0.0214(13) 0.0296(15) 0.0154(12) 0.0035(11) 0.0010(10) 0.0083(11) C33 0.047(2) 0.0396(19) 0.0329(18) 0.0183(15) -0.0013(15) 0.0054(16) _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 C11 1.979(3) . ? Ir1 C12 2.004(3) . ? Ir1 N2 2.027(2) . ? Ir1 N1 2.030(2) . ? Ir1 O1 2.1343(19) . ? Ir1 N3 2.208(2) . ? Cl1 C7 1.752(3) . ? Cl2 C9 1.745(3) . ? Cl3 C14 1.743(3) . ? Cl4 C16 1.754(3) . ? O1 C32 1.283(3) . ? O2 C32 1.225(3) . ? O3 C25 1.348(3) . ? O3 C33 1.428(4) . ? N1 C1 1.354(3) . ? N1 C5 1.358(4) . ? N2 C22 1.348(4) . ? N2 C18 1.375(3) . ? N3 C23 1.333(3) . ? N3 C27 1.396(3) . ? C1 C2 1.363(4) . ? C1 H1 0.9500 . ? C2 C3 1.378(4) . ? C2 H2 0.9500 . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.397(4) . ? C4 H4 0.9500 . ? C5 C6 1.482(4) . ? C6 C7 1.398(4) . ? C6 C11 1.421(4) . ? C7 C8 1.389(4) . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 C10 1.377(4) . ? C10 C11 1.411(4) . ? C10 H10 0.9500 . ? C12 C13 1.393(4) . ? C12 C17 1.427(4) . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.376(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9500 . ? C16 C17 1.407(4) . ? C17 C18 1.465(4) . ? C18 C19 1.398(4) . ? C19 C20 1.378(4) . ? C19 H19 0.9500 . ? C20 C21 1.376(4) . ? C20 H20 0.9500 . ? C21 C22 1.377(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.389(4) . ? C23 C32 1.523(4) . ? C24 C25 1.365(4) . ? C24 H24 0.9500 . ? C25 C26 1.414(4) . ? C26 C27 1.419(4) . ? C26 C31 1.419(4) . ? C27 C28 1.403(4) . ? C28 C29 1.364(4) . ? C28 H28 0.9500 . ? C29 C30 1.398(5) . ? C29 H29 0.9500 . ? C30 C31 1.361(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? 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 C11 Ir1 C12 86.06(11) . . ? C11 Ir1 N2 95.42(10) . . ? C12 Ir1 N2 80.13(10) . . ? C11 Ir1 N1 79.82(10) . . ? C12 Ir1 N1 96.61(10) . . ? N2 Ir1 N1 174.45(8) . . ? C11 Ir1 O1 174.01(9) . . ? C12 Ir1 O1 92.34(9) . . ? N2 Ir1 O1 89.99(8) . . ? N1 Ir1 O1 94.65(8) . . ? C11 Ir1 N3 105.89(9) . . ? C12 Ir1 N3 167.78(10) . . ? N2 Ir1 N3 95.92(9) . . ? N1 Ir1 N3 88.17(8) . . ? O1 Ir1 N3 76.02(8) . . ? C32 O1 Ir1 118.20(17) . . ? C25 O3 C33 116.7(2) . . ? C1 N1 C5 120.2(2) . . ? C1 N1 Ir1 122.36(19) . . ? C5 N1 Ir1 117.46(17) . . ? C22 N2 C18 120.0(2) . . ? C22 N2 Ir1 122.75(18) . . ? C18 N2 Ir1 117.12(18) . . ? C23 N3 C27 116.7(2) . . ? C23 N3 Ir1 113.04(17) . . ? C27 N3 Ir1 130.10(18) . . ? N1 C1 C2 122.7(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.1(3) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 118.7(2) . . ? N1 C5 C6 113.0(2) . . ? C4 C5 C6 128.3(3) . . ? C7 C6 C11 119.3(2) . . ? C7 C6 C5 127.5(2) . . ? C11 C6 C5 113.2(2) . . ? C8 C7 C6 121.8(3) . . ? C8 C7 Cl1 114.5(2) . . ? C6 C7 Cl1 123.8(2) . . ? C9 C8 C7 118.2(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 122.2(3) . . ? C10 C9 Cl2 119.1(2) . . ? C8 C9 Cl2 118.7(2) . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 118.1(2) . . ? C10 C11 Ir1 125.4(2) . . ? C6 C11 Ir1 116.48(19) . . ? C13 C12 C17 119.5(2) . . ? C13 C12 Ir1 125.3(2) . . ? C17 C12 Ir1 115.13(19) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 121.7(3) . . ? C15 C14 Cl3 118.5(2) . . ? C13 C14 Cl3 119.8(2) . . ? C14 C15 C16 118.7(3) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 122.2(3) . . ? C15 C16 Cl4 113.7(2) . . ? C17 C16 Cl4 124.0(2) . . ? C16 C17 C12 117.7(3) . . ? C16 C17 C18 128.0(2) . . ? C12 C17 C18 114.3(2) . . ? N2 C18 C19 118.8(3) . . ? N2 C18 C17 113.1(2) . . ? C19 C18 C17 128.1(2) . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 118.7(3) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? N2 C22 C21 122.2(3) . . ? N2 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? N3 C23 C24 124.7(3) . . ? N3 C23 C32 116.4(2) . . ? C24 C23 C32 118.9(2) . . ? C25 C24 C23 119.3(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? O3 C25 C24 124.4(3) . . ? O3 C25 C26 116.5(3) . . ? C24 C25 C26 119.1(3) . . ? C25 C26 C27 118.4(3) . . ? C25 C26 C31 122.7(3) . . ? C27 C26 C31 118.9(3) . . ? N3 C27 C28 119.9(2) . . ? N3 C27 C26 121.4(2) . . ? C28 C27 C26 118.7(3) . . ? C29 C28 C27 120.6(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 121.1(3) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C31 C30 C29 119.8(3) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C26 120.7(3) . . ? C30 C31 H31 119.6 . . ? C26 C31 H31 119.6 . . ? O2 C32 O1 126.0(3) . . ? O2 C32 C23 118.8(2) . . ? O1 C32 C23 115.1(2) . . ? O3 C33 H33A 109.5 . . ? O3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 C12 Ir1 O1 C32 172.6(2) . . . . ? N2 Ir1 O1 C32 92.4(2) . . . . ? N1 Ir1 O1 C32 -90.6(2) . . . . ? N3 Ir1 O1 C32 -3.66(19) . . . . ? C11 Ir1 N1 C1 -176.7(2) . . . . ? C12 Ir1 N1 C1 98.5(2) . . . . ? O1 Ir1 N1 C1 5.6(2) . . . . ? N3 Ir1 N1 C1 -70.2(2) . . . . ? C11 Ir1 N1 C5 2.69(19) . . . . ? C12 Ir1 N1 C5 -82.1(2) . . . . ? O1 Ir1 N1 C5 -174.99(19) . . . . ? N3 Ir1 N1 C5 109.19(19) . . . . ? C11 Ir1 N2 C22 93.1(2) . . . . ? C12 Ir1 N2 C22 178.1(2) . . . . ? O1 Ir1 N2 C22 -89.5(2) . . . . ? N3 Ir1 N2 C22 -13.5(2) . . . . ? C11 Ir1 N2 C18 -82.93(19) . . . . ? C12 Ir1 N2 C18 2.11(18) . . . . ? O1 Ir1 N2 C18 94.49(18) . . . . ? N3 Ir1 N2 C18 170.44(18) . . . . ? C11 Ir1 N3 C23 170.49(19) . . . . ? C12 Ir1 N3 C23 -21.8(5) . . . . ? N2 Ir1 N3 C23 -92.14(19) . . . . ? N1 Ir1 N3 C23 91.62(19) . . . . ? O1 Ir1 N3 C23 -3.63(18) . . . . ? C11 Ir1 N3 C27 -4.5(2) . . . . ? C12 Ir1 N3 C27 163.2(4) . . . . ? N2 Ir1 N3 C27 92.9(2) . . . . ? N1 Ir1 N3 C27 -83.4(2) . . . . ? O1 Ir1 N3 C27 -178.6(2) . . . . ? C5 N1 C1 C2 0.2(4) . . . . ? Ir1 N1 C1 C2 179.6(2) . . . . ? N1 C1 C2 C3 1.0(5) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C1 N1 C5 C4 -1.6(4) . . . . ? Ir1 N1 C5 C4 179.0(2) . . . . ? C1 N1 C5 C6 177.0(2) . . . . ? Ir1 N1 C5 C6 -2.3(3) . . . . ? C3 C4 C5 N1 1.8(5) . . . . ? C3 C4 C5 C6 -176.6(3) . . . . ? N1 C5 C6 C7 -177.4(3) . . . . ? C4 C5 C6 C7 1.1(5) . . . . ? N1 C5 C6 C11 0.3(3) . . . . ? C4 C5 C6 C11 178.8(3) . . . . ? C11 C6 C7 C8 -0.6(4) . . . . ? C5 C6 C7 C8 177.0(3) . . . . ? C11 C6 C7 Cl1 179.0(2) . . . . ? C5 C6 C7 Cl1 -3.4(4) . . . . ? C6 C7 C8 C9 1.6(4) . . . . ? Cl1 C7 C8 C9 -178.0(2) . . . . ? C7 C8 C9 C10 -0.7(4) . . . . ? C7 C8 C9 Cl2 177.7(2) . . . . ? C8 C9 C10 C11 -1.2(4) . . . . ? Cl2 C9 C10 C11 -179.6(2) . . . . ? C9 C10 C11 C6 2.2(4) . . . . ? C9 C10 C11 Ir1 -179.1(2) . . . . ? C7 C6 C11 C10 -1.3(4) . . . . ? C5 C6 C11 C10 -179.2(2) . . . . ? C7 C6 C11 Ir1 179.9(2) . . . . ? C5 C6 C11 Ir1 1.9(3) . . . . ? C12 Ir1 C11 C10 -83.8(2) . . . . ? N2 Ir1 C11 C10 -4.1(2) . . . . ? N1 Ir1 C11 C10 178.8(2) . . . . ? N3 Ir1 C11 C10 93.7(2) . . . . ? C12 Ir1 C11 C6 95.0(2) . . . . ? N2 Ir1 C11 C6 174.7(2) . . . . ? N1 Ir1 C11 C6 -2.5(2) . . . . ? N3 Ir1 C11 C6 -87.6(2) . . . . ? C11 Ir1 C12 C13 -86.4(2) . . . . ? N2 Ir1 C12 C13 177.3(3) . . . . ? N1 Ir1 C12 C13 -7.2(2) . . . . ? O1 Ir1 C12 C13 87.8(2) . . . . ? N3 Ir1 C12 C13 105.4(5) . . . . ? C11 Ir1 C12 C17 97.1(2) . . . . ? N2 Ir1 C12 C17 0.93(19) . . . . ? N1 Ir1 C12 C17 176.40(19) . . . . ? O1 Ir1 C12 C17 -88.6(2) . . . . ? N3 Ir1 C12 C17 -71.0(5) . . . . ? C17 C12 C13 C14 1.3(4) . . . . ? Ir1 C12 C13 C14 -175.0(2) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C12 C13 C14 Cl3 -179.9(2) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? Cl3 C14 C15 C16 178.7(2) . . . . ? C14 C15 C16 C17 1.1(4) . . . . ? C14 C15 C16 Cl4 -179.8(2) . . . . ? C15 C16 C17 C12 -0.2(4) . . . . ? Cl4 C16 C17 C12 -179.2(2) . . . . ? C15 C16 C17 C18 179.0(3) . . . . ? Cl4 C16 C17 C18 -0.1(4) . . . . ? C13 C12 C17 C16 -1.0(4) . . . . ? Ir1 C12 C17 C16 175.6(2) . . . . ? C13 C12 C17 C18 179.8(2) . . . . ? Ir1 C12 C17 C18 -3.6(3) . . . . ? C22 N2 C18 C19 -0.8(4) . . . . ? Ir1 N2 C18 C19 175.31(19) . . . . ? C22 N2 C18 C17 179.3(2) . . . . ? Ir1 N2 C18 C17 -4.6(3) . . . . ? C16 C17 C18 N2 -173.9(3) . . . . ? C12 C17 C18 N2 5.2(3) . . . . ? C16 C17 C18 C19 6.2(5) . . . . ? C12 C17 C18 C19 -174.6(3) . . . . ? N2 C18 C19 C20 1.9(4) . . . . ? C17 C18 C19 C20 -178.3(3) . . . . ? C18 C19 C20 C21 -1.6(4) . . . . ? C19 C20 C21 C22 0.2(4) . . . . ? C18 N2 C22 C21 -0.6(4) . . . . ? Ir1 N2 C22 C21 -176.5(2) . . . . ? C20 C21 C22 N2 0.9(4) . . . . ? C27 N3 C23 C24 5.5(4) . . . . ? Ir1 N3 C23 C24 -170.2(2) . . . . ? C27 N3 C23 C32 -174.9(2) . . . . ? Ir1 N3 C23 C32 9.4(3) . . . . ? N3 C23 C24 C25 -0.2(4) . . . . ? C32 C23 C24 C25 -179.8(3) . . . . ? C33 O3 C25 C24 -9.0(4) . . . . ? C33 O3 C25 C26 170.6(3) . . . . ? C23 C24 C25 O3 174.5(3) . . . . ? C23 C24 C25 C26 -5.1(4) . . . . ? O3 C25 C26 C27 -174.7(3) . . . . ? C24 C25 C26 C27 4.9(4) . . . . ? O3 C25 C26 C31 4.6(4) . . . . ? C24 C25 C26 C31 -175.8(3) . . . . ? C23 N3 C27 C28 173.9(3) . . . . ? Ir1 N3 C27 C28 -11.3(4) . . . . ? C23 N3 C27 C26 -5.5(4) . . . . ? Ir1 N3 C27 C26 169.3(2) . . . . ? C25 C26 C27 N3 0.5(4) . . . . ? C31 C26 C27 N3 -178.9(3) . . . . ? C25 C26 C27 C28 -179.0(3) . . . . ? C31 C26 C27 C28 1.7(4) . . . . ? N3 C27 C28 C29 179.4(3) . . . . ? C26 C27 C28 C29 -1.2(5) . . . . ? C27 C28 C29 C30 0.1(5) . . . . ? C28 C29 C30 C31 0.4(5) . . . . ? C29 C30 C31 C26 0.1(5) . . . . ? C25 C26 C31 C30 179.5(3) . . . . ? C27 C26 C31 C30 -1.2(5) . . . . ? Ir1 O1 C32 O2 -170.6(2) . . . . ? Ir1 O1 C32 C23 9.5(3) . . . . ? N3 C23 C32 O2 167.3(3) . . . . ? C24 C23 C32 O2 -13.1(4) . . . . ? N3 C23 C32 O1 -12.8(4) . . . . ? C24 C23 C32 O1 166.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.846 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.086 # Attachment '- n977.cif' data_n977 _database_code_depnum_ccdc_archive 'CCDC 803768' #TrackingRef '- n977.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H31 F4 Ir N6 O2, C H4 O' _chemical_formula_sum 'C35 H35 F4 Ir N6 O3' _chemical_formula_weight 855.89 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' 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 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4762(8) _cell_length_b 13.8917(9) _cell_length_c 15.4205(14) _cell_angle_alpha 108.231(7) _cell_angle_beta 93.780(7) _cell_angle_gamma 107.916(7) _cell_volume 1804.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 2908 _cell_measurement_theta_min 2.8988 _cell_measurement_theta_max 28.9760 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 3.762 _exptl_absorpt_correction_T_min 0.97653 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'multiwire proportional' _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 9199 _diffrn_reflns_av_R_equivalents 0.1066 _diffrn_reflns_av_sigmaI/netI 0.1807 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 22.99 _reflns_number_total 4465 _reflns_number_gt 3034 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0345P)^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 4465 _refine_ls_number_parameters 442 _refine_ls_number_restraints 270 _refine_ls_R_factor_all 0.1127 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.923 _refine_ls_shift/su_max 0.000 _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 0.45926(7) 0.29655(5) 0.19922(5) 0.0219(2) Uani 1 1 d . . . F1 F -0.1351(7) 0.0960(6) 0.0860(6) 0.042(2) Uani 1 1 d . . . F2 F 0.0305(9) 0.1844(7) 0.4065(7) 0.063(3) Uani 1 1 d . . . F3 F 0.3752(8) -0.1337(5) 0.0530(5) 0.039(2) Uani 1 1 d . . . F4 F 0.6284(8) 0.0549(5) 0.3634(5) 0.035(2) Uani 1 1 d . . . O1 O 0.4658(9) 0.4609(6) 0.2200(6) 0.025(2) Uani 1 1 d U . . O2 O 0.6148(10) 0.6230(7) 0.2192(7) 0.045(3) Uani 1 1 d U . . N1 N 0.3327(11) 0.2446(7) 0.0710(8) 0.021(2) Uani 1 1 d U . . N2 N 0.0538(11) 0.1320(8) -0.1934(9) 0.030(2) Uani 1 1 d U . . N3 N 0.5771(11) 0.3406(8) 0.3283(8) 0.026(2) Uani 1 1 d U . . N4 N 0.8801(14) 0.4257(9) 0.5780(9) 0.048(3) Uani 1 1 d U . . N5 N 0.6720(11) 0.3689(8) 0.1602(8) 0.023(2) Uani 1 1 d U . . N6 N 1.0908(11) 0.5446(8) 0.1112(8) 0.032(2) Uani 1 1 d U . . C1 C 0.3902(13) 0.2582(9) -0.0068(10) 0.023(2) Uani 1 1 d U . . H1 H 0.4956 0.2937 0.0000 0.028 Uiso 1 1 calc R . . C2 C 0.3016(13) 0.2226(9) -0.0942(10) 0.023(2) Uani 1 1 d U . . H2 H 0.3475 0.2342 -0.1447 0.028 Uiso 1 1 calc R . . C3 C 0.1443(14) 0.1695(10) -0.1084(10) 0.024(2) Uani 1 1 d U . . C4 C 0.0856(13) 0.1557(9) -0.0287(9) 0.023(2) Uani 1 1 d U . . H4 H -0.0190 0.1179 -0.0350 0.028 Uiso 1 1 calc R . . C5 C 0.1766(13) 0.1960(9) 0.0577(10) 0.022(2) Uani 1 1 d U . . C6 C 0.1317(13) 0.1909(9) 0.1469(10) 0.022(2) Uani 1 1 d U . . C7 C -0.0181(14) 0.1412(10) 0.1604(11) 0.028(2) Uani 1 1 d U . . C8 C -0.0550(15) 0.1386(10) 0.2445(10) 0.030(2) Uani 1 1 d U . . H8 H -0.1556 0.1044 0.2505 0.037 Uiso 1 1 calc R . . C9 C 0.0641(16) 0.1892(11) 0.3215(11) 0.035(3) Uani 1 1 d U . . C10 C 0.2138(14) 0.2325(10) 0.3139(10) 0.031(2) Uani 1 1 d U . . H10 H 0.2909 0.2592 0.3669 0.037 Uiso 1 1 calc R . . C11 C 0.2513(14) 0.2370(9) 0.2302(10) 0.022(2) Uani 1 1 d U . . C12 C 0.4775(13) 0.1508(10) 0.1903(10) 0.024(2) Uani 1 1 d U . . C13 C 0.4216(13) 0.0527(10) 0.1136(10) 0.023(2) Uani 1 1 d U . . H13 H 0.3747 0.0490 0.0557 0.027 Uiso 1 1 calc R . . C14 C 0.4381(13) -0.0366(11) 0.1266(10) 0.024(2) Uani 1 1 d U . . C15 C 0.5027(13) -0.0404(11) 0.2080(10) 0.025(2) Uani 1 1 d U . . H15 H 0.5071 -0.1057 0.2134 0.030 Uiso 1 1 calc R . . C16 C 0.5607(13) 0.0576(11) 0.2814(10) 0.027(2) Uani 1 1 d U . . C17 C 0.5564(13) 0.1551(10) 0.2747(10) 0.026(2) Uani 1 1 d U . . C18 C 0.6194(13) 0.2606(10) 0.3513(10) 0.026(2) Uani 1 1 d U . . C19 C 0.7154(14) 0.2862(10) 0.4337(10) 0.036(2) Uani 1 1 d U . . H19 H 0.7419 0.2309 0.4468 0.043 Uiso 1 1 calc R . . C20 C 0.7749(16) 0.3942(11) 0.4990(11) 0.041(2) Uani 1 1 d U . . C21 C 0.7177(15) 0.4748(11) 0.4798(11) 0.037(3) Uani 1 1 d U . . H21 H 0.7440 0.5457 0.5239 0.045 Uiso 1 1 calc R . . C22 C 0.6251(14) 0.4436(10) 0.3959(10) 0.030(3) Uani 1 1 d U . . H22 H 0.5914 0.4963 0.3831 0.036 Uiso 1 1 calc R . . C23 C -0.1088(13) 0.0748(10) -0.2070(10) 0.037(3) Uani 1 1 d U . . H23A H -0.1265 0.0064 -0.1965 0.055 Uiso 1 1 calc R . . H23B H -0.1552 0.0603 -0.2706 0.055 Uiso 1 1 calc R . . H23C H -0.1534 0.1196 -0.1631 0.055 Uiso 1 1 calc R . . C24 C 0.1170(14) 0.1287(11) -0.2778(10) 0.042(4) Uani 1 1 d U . . H24A H 0.1697 0.2025 -0.2752 0.064 Uiso 1 1 calc R . . H24B H 0.0354 0.0917 -0.3320 0.064 Uiso 1 1 calc R . . H24C H 0.1880 0.0895 -0.2829 0.064 Uiso 1 1 calc R . . C25 C 0.9240(17) 0.3438(11) 0.6017(11) 0.058(4) Uani 1 1 d U . . H25A H 0.8390 0.2979 0.6200 0.087 Uiso 1 1 calc R . . H25B H 1.0098 0.3792 0.6534 0.087 Uiso 1 1 calc R . . H25C H 0.9528 0.2993 0.5477 0.087 Uiso 1 1 calc R . . C26 C 0.9310(18) 0.5349(11) 0.6455(11) 0.059(4) Uani 1 1 d U . . H26A H 0.9492 0.5868 0.6129 0.089 Uiso 1 1 calc R . . H26B H 1.0247 0.5482 0.6856 0.089 Uiso 1 1 calc R . . H26C H 0.8536 0.5435 0.6833 0.089 Uiso 1 1 calc R . . C27 C 0.7762(14) 0.3242(10) 0.1327(9) 0.028(2) Uani 1 1 d U . . H27 H 0.7527 0.2500 0.1244 0.033 Uiso 1 1 calc R . . C28 C 0.9156(13) 0.3776(9) 0.1151(9) 0.025(2) Uani 1 1 d U . . H28 H 0.9835 0.3407 0.0950 0.029 Uiso 1 1 calc R . . C29 C 0.9528(14) 0.4877(10) 0.1281(10) 0.026(2) Uani 1 1 d U . . C30 C 0.8405(13) 0.5352(10) 0.1563(9) 0.025(2) Uani 1 1 d U . . H30 H 0.8588 0.6085 0.1628 0.029 Uiso 1 1 calc R . . C31 C 0.7049(13) 0.4752(10) 0.1743(10) 0.025(2) Uani 1 1 d U . . C32 C 0.5881(14) 0.5248(10) 0.2055(10) 0.026(2) Uani 1 1 d U . . C33 C 1.2079(13) 0.4960(10) 0.0917(10) 0.038(4) Uani 1 1 d U . . H33A H 1.2317 0.4722 0.1426 0.057 Uiso 1 1 calc R . . H33B H 1.2988 0.5496 0.0860 0.057 Uiso 1 1 calc R . . H33C H 1.1713 0.4338 0.0336 0.057 Uiso 1 1 calc R . . C34 C 1.1361(15) 0.6651(10) 0.1325(11) 0.043(4) Uani 1 1 d U . . H34A H 1.0619 0.6798 0.0960 0.064 Uiso 1 1 calc R . . H34B H 1.2356 0.6921 0.1165 0.064 Uiso 1 1 calc R . . H34C H 1.1402 0.7015 0.1988 0.064 Uiso 1 1 calc R . . O3 O 0.4497(13) 0.7491(10) 0.2979(10) 0.093(4) Uani 1 1 d U . . H3 H 0.4674 0.6924 0.2711 0.140 Uiso 1 1 calc R . . C35 C 0.518(2) 0.7915(18) 0.3914(16) 0.109(6) Uani 1 1 d U . . H35A H 0.6272 0.8237 0.3967 0.163 Uiso 1 1 calc R . . H35B H 0.4957 0.7336 0.4173 0.163 Uiso 1 1 calc R . . H35C H 0.4785 0.8470 0.4256 0.163 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 0.0138(3) 0.0214(3) 0.0304(4) 0.0072(3) 0.0055(2) 0.0075(2) F1 0.018(4) 0.043(5) 0.063(7) 0.024(5) 0.010(4) 0.002(4) F2 0.048(6) 0.088(7) 0.060(7) 0.031(7) 0.031(5) 0.023(5) F3 0.052(5) 0.022(4) 0.031(6) -0.008(5) 0.004(4) 0.016(4) F4 0.045(5) 0.029(4) 0.032(6) 0.012(5) 0.006(4) 0.013(4) O1 0.022(4) 0.006(4) 0.046(5) 0.005(4) 0.013(4) 0.008(3) O2 0.035(5) 0.038(5) 0.064(7) 0.012(5) 0.006(5) 0.020(5) N1 0.014(4) 0.015(4) 0.040(5) 0.014(4) 0.011(4) 0.007(3) N2 0.019(4) 0.030(4) 0.038(5) 0.011(4) 0.003(4) 0.004(4) N3 0.026(4) 0.015(4) 0.038(5) 0.009(4) 0.006(4) 0.007(4) N4 0.054(5) 0.031(4) 0.040(6) -0.001(5) -0.013(4) 0.006(4) N5 0.025(4) 0.016(4) 0.038(4) 0.015(4) 0.008(4) 0.014(3) N6 0.024(4) 0.029(4) 0.047(5) 0.017(4) 0.012(4) 0.008(4) C1 0.017(4) 0.019(4) 0.036(5) 0.014(4) 0.009(4) 0.005(4) C2 0.017(4) 0.023(4) 0.033(5) 0.015(4) 0.009(4) 0.005(4) C3 0.016(4) 0.024(4) 0.034(5) 0.013(4) 0.007(3) 0.005(3) C4 0.015(4) 0.020(4) 0.036(5) 0.012(4) 0.007(4) 0.006(3) C5 0.016(3) 0.017(3) 0.037(4) 0.013(4) 0.009(3) 0.006(3) C6 0.021(4) 0.017(3) 0.036(5) 0.014(4) 0.006(3) 0.012(3) C7 0.024(4) 0.024(4) 0.038(5) 0.012(5) 0.008(4) 0.010(4) C8 0.028(5) 0.027(4) 0.037(5) 0.009(5) 0.013(4) 0.010(4) C9 0.034(5) 0.028(5) 0.038(6) 0.009(5) 0.015(4) 0.007(4) C10 0.031(4) 0.022(4) 0.037(5) 0.008(5) 0.010(4) 0.009(4) C11 0.026(4) 0.012(4) 0.036(5) 0.014(4) 0.010(4) 0.011(4) C12 0.014(4) 0.028(4) 0.024(5) 0.002(4) 0.008(4) 0.006(4) C13 0.016(4) 0.027(4) 0.021(5) 0.002(4) 0.005(4) 0.008(4) C14 0.016(4) 0.027(4) 0.023(5) 0.000(4) 0.007(4) 0.007(4) C15 0.017(4) 0.026(4) 0.026(5) 0.001(4) 0.006(4) 0.006(4) C16 0.016(4) 0.029(4) 0.028(5) 0.003(4) 0.004(4) 0.005(4) C17 0.017(4) 0.026(4) 0.028(5) 0.002(4) 0.008(3) 0.003(3) C18 0.022(4) 0.020(3) 0.031(5) 0.005(4) 0.006(3) 0.006(3) C19 0.033(4) 0.028(4) 0.034(5) 0.004(4) -0.001(4) 0.004(4) C20 0.041(4) 0.030(4) 0.038(5) 0.002(4) -0.005(4) 0.005(4) C21 0.037(5) 0.025(4) 0.038(5) 0.002(4) 0.000(4) 0.005(4) C22 0.030(4) 0.019(4) 0.037(5) 0.005(4) 0.002(4) 0.008(4) C23 0.021(6) 0.037(7) 0.049(8) 0.013(7) -0.003(6) 0.009(6) C24 0.028(7) 0.045(7) 0.046(8) 0.012(7) 0.000(6) 0.008(6) C25 0.062(8) 0.042(7) 0.049(9) 0.002(7) -0.024(7) 0.012(7) C26 0.080(8) 0.027(7) 0.044(9) -0.012(7) -0.020(8) 0.013(7) C27 0.027(4) 0.021(4) 0.037(5) 0.013(4) 0.007(4) 0.009(4) C28 0.024(4) 0.015(4) 0.036(5) 0.013(4) 0.007(4) 0.006(4) C29 0.023(4) 0.019(4) 0.039(4) 0.013(4) 0.007(4) 0.007(3) C30 0.023(4) 0.017(4) 0.039(5) 0.015(4) 0.003(4) 0.009(3) C31 0.023(4) 0.018(4) 0.040(4) 0.013(4) 0.007(3) 0.011(3) C32 0.026(4) 0.016(4) 0.044(4) 0.014(4) 0.008(4) 0.013(3) C33 0.023(6) 0.031(7) 0.055(8) 0.010(7) 0.012(6) 0.008(5) C34 0.035(7) 0.041(7) 0.052(8) 0.019(7) 0.014(6) 0.010(6) O3 0.079(9) 0.091(10) 0.120(13) 0.029(11) 0.024(9) 0.049(8) C35 0.091(12) 0.106(12) 0.124(15) 0.028(13) 0.032(11) 0.037(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N3 2.027(11) . ? Ir1 N1 2.032(11) . ? Ir1 C11 2.041(13) . ? Ir1 C12 2.048(13) . ? Ir1 N5 2.174(10) . ? Ir1 O1 2.184(7) . ? F1 C7 1.376(14) . ? F2 C9 1.387(16) . ? F3 C14 1.386(14) . ? F4 C16 1.395(14) . ? O1 C32 1.306(14) . ? O2 C32 1.252(13) . ? N1 C1 1.392(16) . ? N1 C5 1.395(14) . ? N2 C3 1.369(16) . ? N2 C24 1.462(17) . ? N2 C23 1.466(14) . ? N3 C22 1.394(16) . ? N3 C18 1.423(14) . ? N4 C20 1.381(16) . ? N4 C26 1.453(16) . ? N4 C25 1.461(16) . ? N5 C27 1.344(14) . ? N5 C31 1.354(14) . ? N6 C29 1.393(15) . ? N6 C33 1.469(14) . ? N6 C34 1.513(15) . ? C1 C2 1.395(16) . ? C1 H1 0.9500 . ? C2 C3 1.411(16) . ? C2 H2 0.9500 . ? C3 C4 1.424(17) . ? C4 C5 1.385(16) . ? C4 H4 0.9500 . ? C5 C6 1.482(18) . ? C6 C7 1.436(17) . ? C6 C11 1.480(16) . ? C7 C8 1.373(18) . ? C8 C9 1.411(18) . ? C8 H8 0.9500 . ? C9 C10 1.389(18) . ? C10 C11 1.376(18) . ? C10 H10 0.9500 . ? C12 C13 1.414(17) . ? C12 C17 1.432(18) . ? C13 C14 1.370(16) . ? C13 H13 0.9500 . ? C14 C15 1.382(17) . ? C15 C16 1.389(17) . ? C15 H15 0.9500 . ? C16 C17 1.403(17) . ? C17 C18 1.478(17) . ? C18 C19 1.390(17) . ? C19 C20 1.429(18) . ? C19 H19 0.9500 . ? C20 C21 1.483(18) . ? C21 C22 1.377(17) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C28 1.392(16) . ? C27 H27 0.9500 . ? C28 C29 1.404(15) . ? C28 H28 0.9500 . ? C29 C30 1.439(16) . ? C30 C31 1.398(16) . ? C30 H30 0.9500 . ? C31 C32 1.505(16) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O3 C35 1.40(2) . ? O3 H3 0.8400 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 N3 Ir1 N1 176.6(5) . . ? N3 Ir1 C11 96.3(5) . . ? N1 Ir1 C11 81.0(5) . . ? N3 Ir1 C12 81.4(5) . . ? N1 Ir1 C12 96.3(5) . . ? C11 Ir1 C12 85.5(5) . . ? N3 Ir1 N5 87.2(4) . . ? N1 Ir1 N5 95.6(4) . . ? C11 Ir1 N5 174.5(5) . . ? C12 Ir1 N5 99.2(4) . . ? N3 Ir1 O1 92.7(4) . . ? N1 Ir1 O1 89.8(3) . . ? C11 Ir1 O1 98.7(4) . . ? C12 Ir1 O1 173.1(5) . . ? N5 Ir1 O1 76.9(3) . . ? C32 O1 Ir1 115.9(7) . . ? C1 N1 C5 115.6(11) . . ? C1 N1 Ir1 124.3(8) . . ? C5 N1 Ir1 120.0(9) . . ? C3 N2 C24 121.6(11) . . ? C3 N2 C23 121.6(12) . . ? C24 N2 C23 115.9(11) . . ? C22 N3 C18 116.8(11) . . ? C22 N3 Ir1 125.9(8) . . ? C18 N3 Ir1 117.4(8) . . ? C20 N4 C26 121.7(12) . . ? C20 N4 C25 119.1(12) . . ? C26 N4 C25 118.5(12) . . ? C27 N5 C31 118.1(11) . . ? C27 N5 Ir1 128.4(8) . . ? C31 N5 Ir1 113.3(8) . . ? C29 N6 C33 121.2(10) . . ? C29 N6 C34 120.1(10) . . ? C33 N6 C34 117.4(10) . . ? N1 C1 C2 123.6(11) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 120.7(13) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? N2 C3 C2 122.4(13) . . ? N2 C3 C4 121.9(12) . . ? C2 C3 C4 115.7(12) . . ? C5 C4 C3 121.8(12) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 N1 122.4(13) . . ? C4 C5 C6 128.1(11) . . ? N1 C5 C6 109.5(11) . . ? C7 C6 C11 115.7(13) . . ? C7 C6 C5 126.1(12) . . ? C11 C6 C5 118.1(11) . . ? C8 C7 F1 116.6(12) . . ? C8 C7 C6 124.3(14) . . ? F1 C7 C6 119.1(13) . . ? C7 C8 C9 116.6(13) . . ? C7 C8 H8 121.7 . . ? C9 C8 H8 121.7 . . ? F2 C9 C10 118.9(13) . . ? F2 C9 C8 117.6(13) . . ? C10 C9 C8 123.1(15) . . ? C11 C10 C9 120.4(14) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C6 119.7(12) . . ? C10 C11 Ir1 128.8(10) . . ? C6 C11 Ir1 111.4(10) . . ? C13 C12 C17 120.1(12) . . ? C13 C12 Ir1 127.7(10) . . ? C17 C12 Ir1 112.2(10) . . ? C14 C13 C12 117.0(13) . . ? C14 C13 H13 121.5 . . ? C12 C13 H13 121.5 . . ? C13 C14 C15 126.2(14) . . ? C13 C14 F3 116.7(12) . . ? C15 C14 F3 117.0(12) . . ? C14 C15 C16 115.7(13) . . ? C14 C15 H15 122.2 . . ? C16 C15 H15 122.2 . . ? C15 C16 F4 116.1(12) . . ? C15 C16 C17 123.1(13) . . ? F4 C16 C17 120.8(12) . . ? C16 C17 C12 117.7(12) . . ? C16 C17 C18 124.1(13) . . ? C12 C17 C18 118.1(12) . . ? C19 C18 N3 121.5(12) . . ? C19 C18 C17 127.7(12) . . ? N3 C18 C17 110.7(12) . . ? C18 C19 C20 121.2(13) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? N4 C20 C19 123.5(13) . . ? N4 C20 C21 119.4(13) . . ? C19 C20 C21 117.1(13) . . ? C22 C21 C20 117.8(13) . . ? C22 C21 H21 121.1 . . ? C20 C21 H21 121.1 . . ? C21 C22 N3 125.1(12) . . ? C21 C22 H22 117.5 . . ? N3 C22 H22 117.5 . . ? N2 C23 H23A 109.5 . . ? N2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N2 C24 H24A 109.5 . . ? N2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 C28 125.5(11) . . ? N5 C27 H27 117.3 . . ? C28 C27 H27 117.3 . . ? C27 C28 C29 118.0(12) . . ? C27 C28 H28 121.0 . . ? C29 C28 H28 121.0 . . ? N6 C29 C28 120.1(11) . . ? N6 C29 C30 123.3(11) . . ? C28 C29 C30 116.6(12) . . ? C31 C30 C29 121.1(11) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? N5 C31 C30 120.7(11) . . ? N5 C31 C32 117.8(11) . . ? C30 C31 C32 121.4(11) . . ? O2 C32 O1 124.5(12) . . ? O2 C32 C31 119.5(12) . . ? O1 C32 C31 115.9(10) . . ? N6 C33 H33A 109.5 . . ? N6 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N6 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N6 C34 H34A 109.5 . . ? N6 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N6 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 O3 H3 109.5 . . ? O3 C35 H35A 109.5 . . ? O3 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O3 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 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 N3 Ir1 O1 C32 83.3(10) . . . . ? N1 Ir1 O1 C32 -99.1(10) . . . . ? C11 Ir1 O1 C32 -179.9(10) . . . . ? N5 Ir1 O1 C32 -3.2(9) . . . . ? C11 Ir1 N1 C1 177.0(10) . . . . ? C12 Ir1 N1 C1 -98.7(10) . . . . ? N5 Ir1 N1 C1 1.3(9) . . . . ? O1 Ir1 N1 C1 78.1(9) . . . . ? C11 Ir1 N1 C5 0.0(8) . . . . ? C12 Ir1 N1 C5 84.4(9) . . . . ? N5 Ir1 N1 C5 -175.6(8) . . . . ? O1 Ir1 N1 C5 -98.9(8) . . . . ? C11 Ir1 N3 C22 -96.0(11) . . . . ? C12 Ir1 N3 C22 179.5(11) . . . . ? N5 Ir1 N3 C22 79.7(11) . . . . ? O1 Ir1 N3 C22 3.1(11) . . . . ? C11 Ir1 N3 C18 86.3(10) . . . . ? C12 Ir1 N3 C18 1.9(10) . . . . ? N5 Ir1 N3 C18 -97.9(9) . . . . ? O1 Ir1 N3 C18 -174.6(9) . . . . ? N3 Ir1 N5 C27 84.9(11) . . . . ? N1 Ir1 N5 C27 -93.3(11) . . . . ? C12 Ir1 N5 C27 4.0(12) . . . . ? O1 Ir1 N5 C27 178.3(12) . . . . ? N3 Ir1 N5 C31 -88.9(9) . . . . ? N1 Ir1 N5 C31 92.9(9) . . . . ? C12 Ir1 N5 C31 -169.8(9) . . . . ? O1 Ir1 N5 C31 4.4(9) . . . . ? C5 N1 C1 C2 -2.5(17) . . . . ? Ir1 N1 C1 C2 -179.6(8) . . . . ? N1 C1 C2 C3 0.0(18) . . . . ? C24 N2 C3 C2 10.2(19) . . . . ? C23 N2 C3 C2 178.6(11) . . . . ? C24 N2 C3 C4 -168.8(11) . . . . ? C23 N2 C3 C4 -0.4(18) . . . . ? C1 C2 C3 N2 -179.1(11) . . . . ? C1 C2 C3 C4 0.0(17) . . . . ? N2 C3 C4 C5 -178.4(11) . . . . ? C2 C3 C4 C5 2.5(17) . . . . ? C3 C4 C5 N1 -5.3(18) . . . . ? C3 C4 C5 C6 178.2(11) . . . . ? C1 N1 C5 C4 5.1(16) . . . . ? Ir1 N1 C5 C4 -177.7(8) . . . . ? C1 N1 C5 C6 -177.8(9) . . . . ? Ir1 N1 C5 C6 -0.6(13) . . . . ? C4 C5 C6 C7 0(2) . . . . ? N1 C5 C6 C7 -176.4(11) . . . . ? C4 C5 C6 C11 178.0(11) . . . . ? N1 C5 C6 C11 1.1(15) . . . . ? C11 C6 C7 C8 2.7(19) . . . . ? C5 C6 C7 C8 -179.8(12) . . . . ? C11 C6 C7 F1 -179.6(9) . . . . ? C5 C6 C7 F1 -2.1(19) . . . . ? F1 C7 C8 C9 -177.3(10) . . . . ? C6 C7 C8 C9 0(2) . . . . ? C7 C8 C9 F2 -177.8(11) . . . . ? C7 C8 C9 C10 -5(2) . . . . ? F2 C9 C10 C11 179.0(11) . . . . ? C8 C9 C10 C11 6(2) . . . . ? C9 C10 C11 C6 -2.8(19) . . . . ? C9 C10 C11 Ir1 179.5(9) . . . . ? C7 C6 C11 C10 -1.5(17) . . . . ? C5 C6 C11 C10 -179.3(11) . . . . ? C7 C6 C11 Ir1 176.6(8) . . . . ? C5 C6 C11 Ir1 -1.2(13) . . . . ? N3 Ir1 C11 C10 0.5(12) . . . . ? N1 Ir1 C11 C10 178.5(12) . . . . ? C12 Ir1 C11 C10 81.4(12) . . . . ? O1 Ir1 C11 C10 -93.2(12) . . . . ? N3 Ir1 C11 C6 -177.3(8) . . . . ? N1 Ir1 C11 C6 0.6(8) . . . . ? C12 Ir1 C11 C6 -96.5(9) . . . . ? O1 Ir1 C11 C6 89.0(8) . . . . ? N3 Ir1 C12 C13 -179.7(12) . . . . ? N1 Ir1 C12 C13 2.9(12) . . . . ? C11 Ir1 C12 C13 83.3(12) . . . . ? N5 Ir1 C12 C13 -93.9(11) . . . . ? N3 Ir1 C12 C17 0.9(9) . . . . ? N1 Ir1 C12 C17 -176.5(9) . . . . ? C11 Ir1 C12 C17 -96.1(10) . . . . ? N5 Ir1 C12 C17 86.7(10) . . . . ? C17 C12 C13 C14 4.1(18) . . . . ? Ir1 C12 C13 C14 -175.2(10) . . . . ? C12 C13 C14 C15 1(2) . . . . ? C12 C13 C14 F3 176.3(10) . . . . ? C13 C14 C15 C16 -3(2) . . . . ? F3 C14 C15 C16 -178.1(10) . . . . ? C14 C15 C16 F4 -178.9(11) . . . . ? C14 C15 C16 C17 -0.5(19) . . . . ? C15 C16 C17 C12 5(2) . . . . ? F4 C16 C17 C12 -176.5(11) . . . . ? C15 C16 C17 C18 -179.0(12) . . . . ? F4 C16 C17 C18 -1(2) . . . . ? C13 C12 C17 C16 -7.0(19) . . . . ? Ir1 C12 C17 C16 172.5(10) . . . . ? C13 C12 C17 C18 177.0(11) . . . . ? Ir1 C12 C17 C18 -3.6(15) . . . . ? C22 N3 C18 C19 -5.7(19) . . . . ? Ir1 N3 C18 C19 172.2(10) . . . . ? C22 N3 C18 C17 178.1(11) . . . . ? Ir1 N3 C18 C17 -4.1(14) . . . . ? C16 C17 C18 C19 13(2) . . . . ? C12 C17 C18 C19 -171.0(13) . . . . ? C16 C17 C18 N3 -170.8(12) . . . . ? C12 C17 C18 N3 5.0(17) . . . . ? N3 C18 C19 C20 0(2) . . . . ? C17 C18 C19 C20 175.9(13) . . . . ? C26 N4 C20 C19 -176.3(15) . . . . ? C25 N4 C20 C19 -6(2) . . . . ? C26 N4 C20 C21 3(2) . . . . ? C25 N4 C20 C21 173.5(14) . . . . ? C18 C19 C20 N4 -174.5(14) . . . . ? C18 C19 C20 C21 6(2) . . . . ? N4 C20 C21 C22 173.3(14) . . . . ? C19 C20 C21 C22 -7(2) . . . . ? C20 C21 C22 N3 2(2) . . . . ? C18 N3 C22 C21 4(2) . . . . ? Ir1 N3 C22 C21 -173.2(11) . . . . ? C31 N5 C27 C28 -1(2) . . . . ? Ir1 N5 C27 C28 -175.0(10) . . . . ? N5 C27 C28 C29 1(2) . . . . ? C33 N6 C29 C28 -8(2) . . . . ? C34 N6 C29 C28 -175.1(12) . . . . ? C33 N6 C29 C30 173.8(12) . . . . ? C34 N6 C29 C30 7(2) . . . . ? C27 C28 C29 N6 -179.8(12) . . . . ? C27 C28 C29 C30 -1.6(19) . . . . ? N6 C29 C30 C31 -178.7(13) . . . . ? C28 C29 C30 C31 3(2) . . . . ? C27 N5 C31 C30 2.9(19) . . . . ? Ir1 N5 C31 C30 177.4(10) . . . . ? C27 N5 C31 C32 -179.7(12) . . . . ? Ir1 N5 C31 C32 -5.2(15) . . . . ? C29 C30 C31 N5 -4(2) . . . . ? C29 C30 C31 C32 178.8(12) . . . . ? Ir1 O1 C32 O2 -175.7(11) . . . . ? Ir1 O1 C32 C31 1.5(15) . . . . ? N5 C31 C32 O2 179.9(13) . . . . ? C30 C31 C32 O2 -3(2) . . . . ? N5 C31 C32 O1 2.6(19) . . . . ? C30 C31 C32 O1 179.9(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.84 2.00 2.756(16) 149 . _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 22.99 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 1.689 _refine_diff_density_min -1.845 _refine_diff_density_rms 0.172 # Attachment '- n995.cif' data_n995-b _database_code_depnum_ccdc_archive 'CCDC 803769' #TrackingRef '- n995.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H32 F4 Ir N7, C H2 Cl2' _chemical_formula_sum 'C35 H34 Cl2 F4 Ir N7' _chemical_formula_weight 891.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.753(5) _cell_length_b 12.791(6) _cell_length_c 15.288(6) _cell_angle_alpha 73.78(3) _cell_angle_beta 85.69(4) _cell_angle_gamma 69.36(3) _cell_volume 1713.2(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 90 _cell_measurement_theta_min 3.293 _cell_measurement_theta_max 15.977 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 4.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4409 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2.10, Bruker AXS, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 22003 _diffrn_reflns_av_R_equivalents 0.0981 _diffrn_reflns_av_sigmaI/netI 0.0872 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5957 _reflns_number_gt 4787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0808P)^2^+63.3081P] 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 5957 _refine_ls_number_parameters 477 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.1186 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.2299 _refine_ls_wR_factor_gt 0.2070 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.000 _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 0.13660(7) 0.32559(5) 0.29858(4) 0.0246(2) Uani 1 1 d . . . F1 F 0.5730(11) 0.0462(8) 0.1500(7) 0.044(3) Uani 1 1 d . . . F2 F 0.4944(10) -0.1229(7) 0.4546(6) 0.032(2) Uani 1 1 d . . . F3 F -0.1747(12) 0.1798(10) 0.1075(7) 0.045(3) Uani 1 1 d . . . F4 F -0.2255(11) 0.0952(9) 0.4226(7) 0.038(2) Uani 1 1 d . . . N1 N 0.2160(15) 0.3552(11) 0.1677(10) 0.033(3) Uani 1 1 d . . . N2 N 0.4513(16) 0.4180(12) -0.0698(9) 0.035(3) Uani 1 1 d . . . N3 N 0.0713(14) 0.2749(10) 0.4301(8) 0.024(3) Uani 1 1 d . . . N4 N -0.0657(15) 0.1519(11) 0.6933(9) 0.031(3) Uani 1 1 d . . . N5 N -0.1168(15) 0.5784(12) 0.2559(10) 0.034(3) Uani 1 1 d . . . N6 N 0.2874(13) 0.4004(10) 0.3322(8) 0.020(3) Uani 1 1 d . . . N7 N 0.5828(14) 0.5454(11) 0.3927(9) 0.028(3) Uani 1 1 d . . . C1 C 0.1697(18) 0.4576(15) 0.1032(11) 0.031(4) Uani 1 1 d . . . H1 H 0.0839 0.5168 0.1139 0.038 Uiso 1 1 calc R . . C2 C 0.242(2) 0.4809(14) 0.0217(11) 0.035(4) Uani 1 1 d . . . H2 H 0.2032 0.5529 -0.0231 0.042 Uiso 1 1 calc R . . C3 C 0.373(2) 0.3953(16) 0.0070(11) 0.035(4) Uani 1 1 d . . . C4 C 0.4182(17) 0.2900(13) 0.0743(10) 0.027(3) Uani 1 1 d . . . H4 H 0.5050 0.2301 0.0659 0.032 Uiso 1 1 calc R . . C5 C 0.3429(17) 0.2706(12) 0.1510(10) 0.024(3) Uani 1 1 d . . . C6 C 0.3823(17) 0.1631(14) 0.2298(10) 0.026(3) Uani 1 1 d . . . C7 C 0.4943(18) 0.0554(13) 0.2270(11) 0.032(4) Uani 1 1 d . . . C8 C 0.5339(19) -0.0386(14) 0.3009(11) 0.031(4) Uani 1 1 d . . . H8 H 0.6112 -0.1082 0.2988 0.037 Uiso 1 1 calc R . . C9 C 0.4554(17) -0.0277(13) 0.3805(11) 0.026(3) Uani 1 1 d . . . C10 C 0.3408(18) 0.0724(12) 0.3859(10) 0.024(3) Uani 1 1 d . . . H10 H 0.2893 0.0759 0.4408 0.029 Uiso 1 1 calc R . . C11 C 0.3016(18) 0.1703(13) 0.3069(10) 0.026(3) Uani 1 1 d . . . C12 C 0.399(2) 0.5271(15) -0.1412(12) 0.045(5) Uani 1 1 d . . . H12A H 0.3223 0.5259 -0.1782 0.068 Uiso 1 1 calc R . . H12B H 0.4809 0.5370 -0.1800 0.068 Uiso 1 1 calc R . . H12C H 0.3597 0.5918 -0.1134 0.068 Uiso 1 1 calc R . . C13 C 0.584(2) 0.3232(16) -0.0840(12) 0.043(5) Uani 1 1 d . . . H13A H 0.6454 0.2879 -0.0280 0.065 Uiso 1 1 calc R . . H13B H 0.6402 0.3548 -0.1338 0.065 Uiso 1 1 calc R . . H13C H 0.5559 0.2643 -0.0994 0.065 Uiso 1 1 calc R . . C14 C -0.0021(17) 0.2515(12) 0.2776(10) 0.024(3) Uani 1 1 d . . . C15 C -0.0425(18) 0.2449(14) 0.1935(12) 0.031(4) Uani 1 1 d . . . H15 H -0.0059 0.2808 0.1384 0.038 Uiso 1 1 calc R . . C16 C -0.137(2) 0.1848(16) 0.1920(12) 0.038(4) Uani 1 1 d . . . C17 C -0.202(2) 0.1366(14) 0.2681(13) 0.037(4) Uani 1 1 d . . . H17 H -0.2707 0.1007 0.2643 0.044 Uiso 1 1 calc R . . C18 C -0.1613(17) 0.1433(14) 0.3499(13) 0.034(4) Uani 1 1 d . . . C19 C -0.0658(17) 0.1981(11) 0.3585(11) 0.024(3) Uani 1 1 d . . . C20 C -0.021(2) 0.2122(13) 0.4435(12) 0.033(4) Uani 1 1 d . . . C21 C -0.0634(18) 0.1670(13) 0.5308(11) 0.029(4) Uani 1 1 d . . . H21 H -0.1211 0.1188 0.5395 0.035 Uiso 1 1 calc R . . C22 C -0.0210(17) 0.1924(14) 0.6066(11) 0.026(3) Uani 1 1 d . . . C23 C 0.0686(18) 0.2596(15) 0.5914(12) 0.033(4) Uani 1 1 d . . . H23 H 0.0993 0.2786 0.6406 0.040 Uiso 1 1 calc R . . C24 C 0.1116(18) 0.2978(13) 0.5050(11) 0.027(3) Uani 1 1 d . . . H24 H 0.1732 0.3430 0.4961 0.033 Uiso 1 1 calc R . . C25 C -0.160(2) 0.0821(15) 0.7061(12) 0.036(4) Uani 1 1 d . . . H25A H -0.2545 0.1294 0.6741 0.054 Uiso 1 1 calc R . . H25B H -0.1765 0.0548 0.7713 0.054 Uiso 1 1 calc R . . H25C H -0.1130 0.0152 0.6816 0.054 Uiso 1 1 calc R . . C26 C 0.000(2) 0.1575(16) 0.7733(11) 0.036(4) Uani 1 1 d . . . H26A H 0.0906 0.0903 0.7913 0.053 Uiso 1 1 calc R . . H26B H -0.0685 0.1568 0.8234 0.053 Uiso 1 1 calc R . . H26C H 0.0232 0.2290 0.7591 0.053 Uiso 1 1 calc R . . C27 C -0.0279(16) 0.4875(13) 0.2744(11) 0.024(3) Uani 1 1 d . . . C28 C 0.2583(18) 0.5173(13) 0.3094(11) 0.028(3) Uani 1 1 d . . . H28 H 0.1668 0.5663 0.2798 0.034 Uiso 1 1 calc R . . C29 C 0.3494(17) 0.5684(13) 0.3258(12) 0.031(4) Uani 1 1 d . . . H29 H 0.3222 0.6504 0.3057 0.037 Uiso 1 1 calc R . . C30 C 0.4914(17) 0.4982(15) 0.3748(11) 0.028(3) Uani 1 1 d . . . C31 C 0.5203(17) 0.3787(12) 0.3951(10) 0.022(3) Uani 1 1 d . . . H31 H 0.6110 0.3267 0.4242 0.027 Uiso 1 1 calc R . . C32 C 0.4221(18) 0.3346(13) 0.3743(11) 0.030(4) Uani 1 1 d . . . H32 H 0.4486 0.2526 0.3902 0.036 Uiso 1 1 calc R . . C33 C 0.556(2) 0.6686(15) 0.3599(14) 0.040(4) Uani 1 1 d . . . H33A H 0.5492 0.6922 0.2932 0.060 Uiso 1 1 calc R . . H33B H 0.6364 0.6859 0.3801 0.060 Uiso 1 1 calc R . . H33C H 0.4636 0.7112 0.3841 0.060 Uiso 1 1 calc R . . C34 C 0.7249(18) 0.4683(14) 0.4386(12) 0.032(4) Uani 1 1 d . . . H34A H 0.7158 0.3949 0.4751 0.048 Uiso 1 1 calc R . . H34B H 0.7534 0.5057 0.4785 0.048 Uiso 1 1 calc R . . H34C H 0.7997 0.4532 0.3928 0.048 Uiso 1 1 calc R . . Cl1A Cl -0.1883(10) 1.0017(7) -0.0180(5) 0.066(3) Uani 0.783(15) 1 d PDU A 1 Cl2A Cl -0.200(3) 0.7774(15) 0.0721(15) 0.112(7) Uani 0.783(15) 1 d PDU A 1 C35A C -0.265(5) 0.899(2) -0.021(2) 0.087(7) Uani 0.783(15) 1 d PDU A 1 H35A H -0.2400 0.8755 -0.0781 0.105 Uiso 0.783(15) 1 calc PR A 1 H35B H -0.3735 0.9326 -0.0188 0.105 Uiso 0.783(15) 1 calc PR A 1 Cl1B Cl -0.317(5) 1.004(3) -0.054(3) 0.098(9) Uani 0.217(15) 1 d PDU A 2 Cl2B Cl -0.235(9) 0.788(4) 0.082(4) 0.078(9) Uani 0.217(15) 1 d PDU A 2 C35B C -0.170(6) 0.890(7) 0.008(8) 0.089(8) Uani 0.217(15) 1 d PDU A 2 H35C H -0.1180 0.9197 0.0428 0.106 Uiso 0.217(15) 1 calc PR A 2 H35D H -0.0996 0.8530 -0.0344 0.106 Uiso 0.217(15) 1 calc PR A 2 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 0.0275(4) 0.0215(3) 0.0231(3) -0.0024(2) 0.0008(2) -0.0091(2) F1 0.040(6) 0.025(5) 0.049(6) 0.012(5) 0.007(5) -0.008(4) F2 0.037(5) 0.018(4) 0.035(5) -0.002(4) 0.003(4) -0.007(4) F3 0.056(7) 0.053(7) 0.030(6) -0.010(5) -0.013(5) -0.021(5) F4 0.045(6) 0.039(6) 0.040(6) -0.011(5) 0.004(5) -0.027(5) N1 0.030(7) 0.019(7) 0.039(8) -0.001(6) 0.005(6) -0.003(6) N2 0.047(9) 0.028(7) 0.018(7) 0.001(6) 0.008(6) -0.005(6) N3 0.039(8) 0.005(5) 0.018(6) -0.002(5) -0.003(5) 0.005(5) N4 0.033(8) 0.024(7) 0.029(7) 0.001(6) 0.003(6) -0.007(6) N5 0.025(7) 0.029(8) 0.040(8) -0.003(6) -0.002(6) -0.005(6) N6 0.023(6) 0.016(6) 0.021(6) -0.008(5) 0.011(5) -0.005(5) N7 0.031(7) 0.026(7) 0.032(7) -0.007(6) 0.003(6) -0.016(6) C1 0.033(9) 0.038(9) 0.023(8) -0.014(7) 0.009(7) -0.010(7) C2 0.046(10) 0.021(8) 0.024(9) 0.005(7) -0.008(7) -0.002(7) C3 0.042(10) 0.041(10) 0.024(9) -0.013(8) 0.006(7) -0.014(8) C4 0.024(8) 0.023(8) 0.022(8) -0.002(6) 0.004(6) 0.001(6) C5 0.030(8) 0.017(7) 0.027(8) -0.006(6) -0.003(6) -0.010(6) C6 0.024(8) 0.035(9) 0.021(8) -0.009(7) 0.006(6) -0.014(7) C7 0.036(9) 0.017(8) 0.027(9) 0.003(6) 0.008(7) 0.001(7) C8 0.039(10) 0.031(9) 0.023(8) -0.008(7) 0.008(7) -0.014(7) C9 0.028(8) 0.022(8) 0.025(8) -0.001(6) -0.006(6) -0.007(6) C10 0.039(9) 0.017(7) 0.013(7) 0.004(6) -0.008(6) -0.011(6) C11 0.038(9) 0.019(8) 0.018(8) 0.002(6) -0.003(6) -0.010(7) C12 0.058(12) 0.031(10) 0.021(9) 0.013(7) -0.010(8) 0.000(9) C13 0.040(10) 0.040(10) 0.022(9) 0.010(7) 0.008(7) 0.004(8) C14 0.028(8) 0.013(7) 0.023(8) 0.005(6) -0.010(6) -0.003(6) C15 0.035(9) 0.025(8) 0.033(9) -0.002(7) -0.007(7) -0.011(7) C16 0.038(9) 0.042(10) 0.033(10) -0.017(8) -0.005(8) -0.007(8) C17 0.037(10) 0.022(8) 0.053(12) -0.011(8) -0.012(8) -0.011(7) C18 0.022(8) 0.024(8) 0.053(11) -0.019(8) 0.002(7) 0.001(7) C19 0.032(8) 0.007(6) 0.031(8) -0.011(6) 0.002(7) -0.001(6) C20 0.046(10) 0.019(8) 0.033(9) -0.012(7) -0.003(8) -0.005(7) C21 0.038(9) 0.019(7) 0.028(8) -0.002(6) 0.008(7) -0.012(7) C22 0.026(8) 0.029(8) 0.027(8) -0.019(7) 0.010(6) -0.007(7) C23 0.026(9) 0.037(9) 0.029(9) -0.005(7) 0.002(7) -0.005(7) C24 0.032(9) 0.022(8) 0.031(9) -0.004(7) 0.008(7) -0.017(7) C25 0.045(10) 0.037(10) 0.032(9) -0.008(8) 0.012(8) -0.023(8) C26 0.039(10) 0.047(11) 0.029(9) -0.014(8) 0.008(7) -0.023(8) C27 0.018(7) 0.018(8) 0.028(8) 0.001(6) -0.004(6) 0.000(6) C28 0.031(9) 0.022(8) 0.027(8) -0.001(6) 0.002(7) -0.008(7) C29 0.028(9) 0.018(8) 0.039(10) -0.003(7) 0.008(7) -0.006(7) C30 0.024(8) 0.039(9) 0.028(8) -0.014(7) 0.010(6) -0.015(7) C31 0.030(8) 0.016(7) 0.017(7) -0.002(6) -0.001(6) -0.006(6) C32 0.034(9) 0.013(7) 0.037(9) -0.010(7) -0.002(7) 0.004(6) C33 0.034(10) 0.031(9) 0.056(12) -0.015(9) -0.006(8) -0.009(8) C34 0.030(9) 0.025(8) 0.039(10) -0.003(7) 0.000(7) -0.011(7) Cl1A 0.093(6) 0.060(4) 0.048(4) -0.006(3) 0.005(4) -0.037(4) Cl2A 0.160(14) 0.075(7) 0.091(8) 0.000(6) -0.048(9) -0.036(7) C35A 0.123(14) 0.064(12) 0.070(13) 0.003(11) -0.024(12) -0.037(12) Cl1B 0.113(15) 0.078(13) 0.085(14) -0.005(12) -0.001(13) -0.024(13) Cl2B 0.14(2) 0.058(13) 0.066(15) 0.001(12) -0.046(15) -0.077(14) C35B 0.125(14) 0.066(12) 0.070(12) 0.001(11) -0.023(12) -0.036(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 C14 1.992(15) . ? Ir1 C11 2.046(16) . ? Ir1 N3 2.059(12) . ? Ir1 N1 2.074(14) . ? Ir1 C27 2.078(14) . ? Ir1 N6 2.173(12) . ? F1 C7 1.366(19) . ? F2 C9 1.371(17) . ? F3 C16 1.39(2) . ? F4 C18 1.34(2) . ? N1 C1 1.35(2) . ? N1 C5 1.39(2) . ? N2 C3 1.37(2) . ? N2 C12 1.460(19) . ? N2 C13 1.48(2) . ? N3 C24 1.37(2) . ? N3 C20 1.38(2) . ? N4 C22 1.38(2) . ? N4 C26 1.45(2) . ? N4 C25 1.46(2) . ? N5 C27 1.151(19) . ? N6 C28 1.365(19) . ? N6 C32 1.38(2) . ? N7 C30 1.32(2) . ? N7 C33 1.45(2) . ? N7 C34 1.48(2) . ? C1 C2 1.39(2) . ? C1 H1 0.9500 . ? C2 C3 1.41(2) . ? C2 H2 0.9500 . ? C3 C4 1.39(2) . ? C4 C5 1.35(2) . ? C4 H4 0.9500 . ? C5 C6 1.50(2) . ? C6 C11 1.37(2) . ? C6 C7 1.43(2) . ? C7 C8 1.36(2) . ? C8 C9 1.40(2) . ? C8 H8 0.9500 . ? C9 C10 1.39(2) . ? C10 C11 1.43(2) . ? C10 H10 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 1.40(2) . ? C14 C19 1.45(2) . ? C15 C16 1.40(2) . ? C15 H15 0.9500 . ? C16 C17 1.38(3) . ? C17 C18 1.37(3) . ? C17 H17 0.9500 . ? C18 C19 1.38(2) . ? C19 C20 1.48(2) . ? C20 C21 1.39(2) . ? C21 C22 1.41(2) . ? C21 H21 0.9500 . ? C22 C23 1.39(2) . ? C23 C24 1.36(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C28 C29 1.35(2) . ? C28 H28 0.9500 . ? C29 C30 1.48(2) . ? C29 H29 0.9500 . ? C30 C31 1.40(2) . ? C31 C32 1.36(2) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? Cl1A C35A 1.74(2) . ? Cl2A C35A 1.74(2) . ? C35A H35A 0.9900 . ? C35A H35B 0.9900 . ? Cl1B C35B 1.75(2) . ? Cl2B C35B 1.75(2) . ? C35B H35C 0.9900 . ? C35B H35D 0.9900 . ? 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 C11 87.7(6) . . ? C14 Ir1 N3 80.3(6) . . ? C11 Ir1 N3 94.1(5) . . ? C14 Ir1 N1 97.3(6) . . ? C11 Ir1 N1 79.1(6) . . ? N3 Ir1 N1 173.0(5) . . ? C14 Ir1 C27 91.9(6) . . ? C11 Ir1 C27 173.6(6) . . ? N3 Ir1 C27 92.1(5) . . ? N1 Ir1 C27 94.6(6) . . ? C14 Ir1 N6 175.8(5) . . ? C11 Ir1 N6 91.6(5) . . ? N3 Ir1 N6 95.6(5) . . ? N1 Ir1 N6 86.7(5) . . ? C27 Ir1 N6 89.3(5) . . ? C1 N1 C5 117.3(14) . . ? C1 N1 Ir1 124.7(11) . . ? C5 N1 Ir1 117.0(10) . . ? C3 N2 C12 122.0(15) . . ? C3 N2 C13 118.0(14) . . ? C12 N2 C13 119.6(14) . . ? C24 N3 C20 117.4(13) . . ? C24 N3 Ir1 126.1(11) . . ? C20 N3 Ir1 116.4(10) . . ? C22 N4 C26 121.5(14) . . ? C22 N4 C25 118.8(14) . . ? C26 N4 C25 118.6(13) . . ? C28 N6 C32 114.4(13) . . ? C28 N6 Ir1 122.3(10) . . ? C32 N6 Ir1 123.2(10) . . ? C30 N7 C33 122.1(14) . . ? C30 N7 C34 118.7(13) . . ? C33 N7 C34 118.8(13) . . ? N1 C1 C2 123.2(15) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.8(15) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N2 C3 C4 122.8(15) . . ? N2 C3 C2 120.3(16) . . ? C4 C3 C2 116.9(15) . . ? C5 C4 C3 122.1(14) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 N1 121.6(14) . . ? C4 C5 C6 127.3(14) . . ? N1 C5 C6 111.0(13) . . ? C11 C6 C7 119.6(14) . . ? C11 C6 C5 116.6(14) . . ? C7 C6 C5 123.7(13) . . ? C8 C7 F1 117.0(14) . . ? C8 C7 C6 122.6(15) . . ? F1 C7 C6 120.3(13) . . ? C7 C8 C9 116.9(15) . . ? C7 C8 H8 121.6 . . ? C9 C8 H8 121.6 . . ? F2 C9 C10 120.1(14) . . ? F2 C9 C8 116.8(14) . . ? C10 C9 C8 123.1(14) . . ? C9 C10 C11 118.8(14) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C6 C11 C10 118.7(15) . . ? C6 C11 Ir1 115.5(11) . . ? C10 C11 Ir1 125.7(12) . . ? 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 C19 117.3(14) . . ? C15 C14 Ir1 127.0(12) . . ? C19 C14 Ir1 115.7(11) . . ? C16 C15 C14 119.2(16) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C17 C16 F3 118.3(16) . . ? C17 C16 C15 123.9(17) . . ? F3 C16 C15 117.7(16) . . ? C18 C17 C16 116.2(17) . . ? C18 C17 H17 121.9 . . ? C16 C17 H17 121.9 . . ? F4 C18 C17 114.8(15) . . ? F4 C18 C19 121.2(16) . . ? C17 C18 C19 124.0(17) . . ? C18 C19 C14 119.2(15) . . ? C18 C19 C20 126.9(15) . . ? C14 C19 C20 113.8(14) . . ? N3 C20 C21 120.8(15) . . ? N3 C20 C19 113.6(14) . . ? C21 C20 C19 125.7(16) . . ? C20 C21 C22 120.5(15) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? N4 C22 C23 120.7(15) . . ? N4 C22 C21 121.5(15) . . ? C23 C22 C21 117.9(15) . . ? C24 C23 C22 119.3(16) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 N3 124.0(15) . . ? C23 C24 H24 118.0 . . ? N3 C24 H24 118.0 . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 H26A 109.5 . . ? N4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N5 C27 Ir1 176.1(14) . . ? C29 C28 N6 125.0(15) . . ? C29 C28 H28 117.5 . . ? N6 C28 H28 117.5 . . ? C28 C29 C30 120.8(14) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? N7 C30 C31 124.5(15) . . ? N7 C30 C29 122.4(15) . . ? C31 C30 C29 113.0(14) . . ? C32 C31 C30 122.0(14) . . ? C32 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? C31 C32 N6 124.7(14) . . ? C31 C32 H32 117.7 . . ? N6 C32 H32 117.7 . . ? N7 C33 H33A 109.5 . . ? N7 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N7 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N7 C34 H34A 109.5 . . ? N7 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N7 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? Cl1A C35A Cl2A 109.9(14) . . ? Cl1A C35A H35A 109.7 . . ? Cl2A C35A H35A 109.7 . . ? Cl1A C35A H35B 109.7 . . ? Cl2A C35A H35B 109.7 . . ? H35A C35A H35B 108.2 . . ? Cl1B C35B Cl2B 109.1(18) . . ? Cl1B C35B H35C 109.9 . . ? Cl2B C35B H35C 109.9 . . ? Cl1B C35B H35D 109.9 . . ? Cl2B C35B H35D 109.9 . . ? H35C C35B H35D 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Ir1 N1 C1 98.9(14) . . . . ? C11 Ir1 N1 C1 -174.9(15) . . . . ? C27 Ir1 N1 C1 6.4(15) . . . . ? N6 Ir1 N1 C1 -82.6(14) . . . . ? C14 Ir1 N1 C5 -93.4(12) . . . . ? C11 Ir1 N1 C5 -7.2(12) . . . . ? C27 Ir1 N1 C5 174.1(12) . . . . ? N6 Ir1 N1 C5 85.2(12) . . . . ? C14 Ir1 N3 C24 -176.1(13) . . . . ? C11 Ir1 N3 C24 97.0(12) . . . . ? C27 Ir1 N3 C24 -84.5(12) . . . . ? N6 Ir1 N3 C24 4.9(12) . . . . ? C14 Ir1 N3 C20 3.9(11) . . . . ? C11 Ir1 N3 C20 -83.0(11) . . . . ? C27 Ir1 N3 C20 95.5(11) . . . . ? N6 Ir1 N3 C20 -175.1(10) . . . . ? C11 Ir1 N6 C28 157.6(12) . . . . ? N3 Ir1 N6 C28 -108.1(11) . . . . ? N1 Ir1 N6 C28 78.5(11) . . . . ? C27 Ir1 N6 C28 -16.1(12) . . . . ? C11 Ir1 N6 C32 -19.6(12) . . . . ? N3 Ir1 N6 C32 74.7(12) . . . . ? N1 Ir1 N6 C32 -98.7(12) . . . . ? C27 Ir1 N6 C32 166.7(12) . . . . ? C5 N1 C1 C2 1(3) . . . . ? Ir1 N1 C1 C2 168.5(13) . . . . ? N1 C1 C2 C3 -3(3) . . . . ? C12 N2 C3 C4 177.6(17) . . . . ? C13 N2 C3 C4 4(3) . . . . ? C12 N2 C3 C2 -4(3) . . . . ? C13 N2 C3 C2 -177.1(17) . . . . ? C1 C2 C3 N2 -175.9(17) . . . . ? C1 C2 C3 C4 3(3) . . . . ? N2 C3 C4 C5 177.5(17) . . . . ? C2 C3 C4 C5 -1(3) . . . . ? C3 C4 C5 N1 -1(3) . . . . ? C3 C4 C5 C6 -177.8(15) . . . . ? C1 N1 C5 C4 1(2) . . . . ? Ir1 N1 C5 C4 -167.7(12) . . . . ? C1 N1 C5 C6 178.6(14) . . . . ? Ir1 N1 C5 C6 9.9(17) . . . . ? C4 C5 C6 C11 169.6(16) . . . . ? N1 C5 C6 C11 -8(2) . . . . ? C4 C5 C6 C7 -12(3) . . . . ? N1 C5 C6 C7 170.4(15) . . . . ? C11 C6 C7 C8 -6(3) . . . . ? C5 C6 C7 C8 175.9(16) . . . . ? C11 C6 C7 F1 178.5(15) . . . . ? C5 C6 C7 F1 0(3) . . . . ? F1 C7 C8 C9 178.4(15) . . . . ? C6 C7 C8 C9 3(3) . . . . ? C7 C8 C9 F2 179.3(15) . . . . ? C7 C8 C9 C10 1(3) . . . . ? F2 C9 C10 C11 -179.5(13) . . . . ? C8 C9 C10 C11 -1(2) . . . . ? C7 C6 C11 C10 6(2) . . . . ? C5 C6 C11 C10 -176.2(13) . . . . ? C7 C6 C11 Ir1 -176.1(12) . . . . ? C5 C6 C11 Ir1 2.2(18) . . . . ? C9 C10 C11 C6 -2(2) . . . . ? C9 C10 C11 Ir1 179.5(11) . . . . ? C14 Ir1 C11 C6 100.3(13) . . . . ? N3 Ir1 C11 C6 -179.6(12) . . . . ? N1 Ir1 C11 C6 2.4(12) . . . . ? N6 Ir1 C11 C6 -83.9(12) . . . . ? C14 Ir1 C11 C10 -81.4(14) . . . . ? N3 Ir1 C11 C10 -1.3(14) . . . . ? N1 Ir1 C11 C10 -179.3(15) . . . . ? N6 Ir1 C11 C10 94.4(14) . . . . ? C11 Ir1 C14 C15 -88.0(14) . . . . ? N3 Ir1 C14 C15 177.4(14) . . . . ? N1 Ir1 C14 C15 -9.3(14) . . . . ? C27 Ir1 C14 C15 85.6(14) . . . . ? C11 Ir1 C14 C19 91.2(11) . . . . ? N3 Ir1 C14 C19 -3.4(10) . . . . ? N1 Ir1 C14 C19 169.9(10) . . . . ? C27 Ir1 C14 C19 -95.2(11) . . . . ? C19 C14 C15 C16 -2(2) . . . . ? Ir1 C14 C15 C16 177.2(12) . . . . ? C14 C15 C16 C17 4(3) . . . . ? C14 C15 C16 F3 -179.9(14) . . . . ? F3 C16 C17 C18 179.8(14) . . . . ? C15 C16 C17 C18 -4(3) . . . . ? C16 C17 C18 F4 -179.8(14) . . . . ? C16 C17 C18 C19 2(2) . . . . ? F4 C18 C19 C14 -178.3(13) . . . . ? C17 C18 C19 C14 -1(2) . . . . ? F4 C18 C19 C20 0(2) . . . . ? C17 C18 C19 C20 177.7(15) . . . . ? C15 C14 C19 C18 0(2) . . . . ? Ir1 C14 C19 C18 -179.0(11) . . . . ? C15 C14 C19 C20 -178.2(13) . . . . ? Ir1 C14 C19 C20 2.5(16) . . . . ? C24 N3 C20 C21 -5(2) . . . . ? Ir1 N3 C20 C21 175.5(12) . . . . ? C24 N3 C20 C19 176.4(13) . . . . ? Ir1 N3 C20 C19 -3.6(17) . . . . ? C18 C19 C20 N3 -177.6(14) . . . . ? C14 C19 C20 N3 0.7(19) . . . . ? C18 C19 C20 C21 3(3) . . . . ? C14 C19 C20 C21 -178.3(15) . . . . ? N3 C20 C21 C22 5(2) . . . . ? C19 C20 C21 C22 -176.1(15) . . . . ? C26 N4 C22 C23 -12(2) . . . . ? C25 N4 C22 C23 179.7(15) . . . . ? C26 N4 C22 C21 167.5(15) . . . . ? C25 N4 C22 C21 -1(2) . . . . ? C20 C21 C22 N4 177.7(15) . . . . ? C20 C21 C22 C23 -3(2) . . . . ? N4 C22 C23 C24 179.6(15) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C22 C23 C24 N3 0(2) . . . . ? C20 N3 C24 C23 2(2) . . . . ? Ir1 N3 C24 C23 -178.1(12) . . . . ? C32 N6 C28 C29 0(2) . . . . ? Ir1 N6 C28 C29 -177.8(12) . . . . ? N6 C28 C29 C30 -2(3) . . . . ? C33 N7 C30 C31 171.8(16) . . . . ? C34 N7 C30 C31 -1(2) . . . . ? C33 N7 C30 C29 -5(2) . . . . ? C34 N7 C30 C29 -177.5(14) . . . . ? C28 C29 C30 N7 -179.4(15) . . . . ? C28 C29 C30 C31 4(2) . . . . ? N7 C30 C31 C32 -179.4(15) . . . . ? C29 C30 C31 C32 -3(2) . . . . ? C30 C31 C32 N6 0(2) . . . . ? C28 N6 C32 C31 2(2) . . . . ? Ir1 N6 C32 C31 178.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 3.861 _refine_diff_density_min -2.324 _refine_diff_density_rms 0.317 # Attachment '- n995b.cif' data_n995 _database_code_depnum_ccdc_archive 'CCDC 803770' #TrackingRef '- n995b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C61 H54 F8 Ir2 N12' _chemical_formula_sum 'C61 H54 F8 Ir2 N12' _chemical_formula_weight 1491.56 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' 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' 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 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 17.450(2) _cell_length_b 18.5594(19) _cell_length_c 24.439(4) _cell_angle_alpha 80.953(10) _cell_angle_beta 76.281(12) _cell_angle_gamma 68.024(8) _cell_volume 7109.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 418 _cell_measurement_theta_min 3.144 _cell_measurement_theta_max 21.717 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2920 _exptl_absorpt_coefficient_mu 3.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6696 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2.10, G.M.Sheldrick, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 161099 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 27.50 _reflns_number_total 31819 _reflns_number_gt 24805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0409P)^2^+24.6403P] 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 31819 _refine_ls_number_parameters 1495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 1.118568(13) -0.189823(10) 0.138003(8) 0.02469(5) Uani 1 1 d . . . Ir2 Ir 0.917656(12) -0.298223(10) 0.295019(8) 0.02398(5) Uani 1 1 d . . . Ir3 Ir 0.657455(13) -0.545143(10) 0.253064(8) 0.02652(5) Uani 1 1 d . . . Ir4 Ir 0.908881(13) -0.795006(10) 0.299396(8) 0.02520(5) Uani 1 1 d . . . F1 F 1.4250(2) -0.3106(2) 0.01277(15) 0.0506(9) Uani 1 1 d . . . F2 F 1.3013(2) -0.03985(19) -0.01889(15) 0.0476(9) Uani 1 1 d . . . F3 F 1.0121(2) -0.32958(16) 0.00696(13) 0.0422(8) Uani 1 1 d . . . F4 F 0.8804(2) -0.05927(16) 0.01666(14) 0.0399(8) Uani 1 1 d . . . F5 F 0.8452(2) -0.55677(16) 0.33518(13) 0.0353(7) Uani 1 1 d . . . F6 F 0.7813(2) -0.4192(2) 0.49516(13) 0.0449(8) Uani 1 1 d . . . F7 F 1.1536(2) -0.33164(19) 0.41041(14) 0.0431(8) Uani 1 1 d . . . F8 F 1.2126(2) -0.54166(17) 0.30291(14) 0.0402(8) Uani 1 1 d . . . F9 F 0.7571(3) -0.5139(2) 0.03110(14) 0.0554(10) Uani 1 1 d . . . F10 F 0.6409(2) -0.71035(19) 0.09529(15) 0.0459(9) Uani 1 1 d . . . F11 F 0.4328(2) -0.28640(19) 0.16503(17) 0.0538(10) Uani 1 1 d . . . F12 F 0.3339(2) -0.4827(2) 0.26155(16) 0.0524(9) Uani 1 1 d . . . F13 F 1.0031(2) -1.09959(17) 0.28932(14) 0.0422(8) Uani 1 1 d . . . F14 F 1.1563(2) -1.02497(19) 0.38917(17) 0.0537(10) Uani 1 1 d . . . F15 F 0.6481(3) -0.8489(2) 0.45360(16) 0.0571(10) Uani 1 1 d . . . F16 F 0.7963(3) -0.7197(3) 0.51224(15) 0.0604(11) Uani 1 1 d . . . N1 N 0.9778(3) -0.2321(2) 0.23350(18) 0.0258(9) Uani 1 1 d . . . N2 N 0.7271(3) -0.2052(3) 0.2797(3) 0.0517(14) Uani 1 1 d . . . N3 N 1.1852(3) -0.1818(2) 0.20101(18) 0.0304(10) Uani 1 1 d . . . N4 N 1.3514(4) -0.2146(4) 0.3097(3) 0.0723(19) Uani 1 1 d . . . N5 N 1.1995(3) -0.3044(2) 0.13420(17) 0.0276(9) Uani 1 1 d . . . N6 N 1.3747(3) -0.5323(3) 0.1187(2) 0.0471(13) Uani 1 1 d . . . N7 N 1.0443(3) -0.0743(2) 0.12779(17) 0.0255(9) Uani 1 1 d . . . N8 N 0.8999(3) 0.1585(2) 0.08943(19) 0.0340(10) Uani 1 1 d . . . N9 N 0.9307(3) -0.3769(2) 0.23976(17) 0.0251(9) Uani 1 1 d . . . N10 N 0.9621(3) -0.5456(3) 0.13361(19) 0.0385(11) Uani 1 1 d . . . N11 N 0.9165(3) -0.2288(2) 0.35326(17) 0.0275(9) Uani 1 1 d . . . N12 N 0.9331(4) -0.0862(3) 0.4640(2) 0.0429(13) Uani 1 1 d . . . N13 N 0.8250(3) -0.6849(2) 0.27508(18) 0.0277(9) Uani 1 1 d . . . N14 N 1.0595(4) -0.7999(3) 0.1934(2) 0.0447(12) Uani 1 1 d . . . N15 N 0.6355(3) -0.5066(3) 0.33763(19) 0.0330(10) Uani 1 1 d . . . N16 N 0.5724(4) -0.4455(4) 0.5061(2) 0.0699(19) Uani 1 1 d . . . N17 N 0.7146(3) -0.4699(2) 0.20599(19) 0.0310(10) Uani 1 1 d . . . N18 N 0.7723(4) -0.2895(3) 0.0991(2) 0.0509(14) Uani 1 1 d . . . N19 N 0.5829(3) -0.6101(2) 0.29107(18) 0.0308(10) Uani 1 1 d . . . N20 N 0.4192(4) -0.7292(3) 0.3694(3) 0.0644(18) Uani 1 1 d . . . N21 N 0.8596(3) -0.8564(2) 0.26306(18) 0.0278(9) Uani 1 1 d . . . N22 N 0.7673(3) -0.9919(3) 0.1932(2) 0.0428(12) Uani 1 1 d . . . N23 N 0.9510(3) -0.7389(2) 0.34556(17) 0.0263(9) Uani 1 1 d . . . N24 N 1.0246(3) -0.6204(3) 0.4442(2) 0.0383(11) Uani 1 1 d . . . C1 C 1.0278(3) -0.2126(2) 0.2000(2) 0.0255(11) Uani 1 1 d . . . C2 C 0.7951(3) -0.2353(3) 0.2836(2) 0.0286(11) Uani 1 1 d . . . C3 C 1.1846(3) -0.2281(3) 0.2494(2) 0.0320(11) Uani 1 1 d . . . H3 H 1.1463 -0.2555 0.2582 0.038 Uiso 1 1 calc R . . C4 C 1.2363(4) -0.2381(4) 0.2871(2) 0.0410(14) Uani 1 1 d . . . H4 H 1.2320 -0.2707 0.3209 0.049 Uiso 1 1 calc R . . C5 C 1.2942(4) -0.2008(4) 0.2756(3) 0.0526(17) Uani 1 1 d . . . C6 C 1.2912(5) -0.1478(4) 0.2268(3) 0.0560(18) Uani 1 1 d . . . H6 H 1.3259 -0.1168 0.2185 0.067 Uiso 1 1 calc R . . C7 C 1.2377(4) -0.1414(3) 0.1916(3) 0.0395(13) Uani 1 1 d . . . H7 H 1.2379 -0.1065 0.1587 0.047 Uiso 1 1 calc R . . C8 C 1.3596(6) -0.2778(6) 0.3548(4) 0.086(3) Uani 1 1 d . . . H8A H 1.3084 -0.2644 0.3842 0.129 Uiso 1 1 calc R . . H8B H 1.4082 -0.2849 0.3713 0.129 Uiso 1 1 calc R . . H8C H 1.3677 -0.3262 0.3392 0.129 Uiso 1 1 calc R . . C9 C 1.4213(7) -0.1842(8) 0.2897(5) 0.116(4) Uani 1 1 d . . . H9A H 1.4505 -0.2007 0.2518 0.174 Uiso 1 1 calc R . . H9B H 1.4610 -0.2047 0.3156 0.174 Uiso 1 1 calc R . . H9C H 1.3987 -0.1272 0.2885 0.174 Uiso 1 1 calc R . . C10 C 1.1825(4) -0.3667(3) 0.1650(2) 0.0315(11) Uani 1 1 d . . . H10 H 1.1302 -0.3572 0.1907 0.038 Uiso 1 1 calc R . . C11 C 1.2372(4) -0.4424(3) 0.1606(2) 0.0351(12) Uani 1 1 d . . . H11 H 1.2220 -0.4837 0.1827 0.042 Uiso 1 1 calc R . . C12 C 1.3164(4) -0.4589(3) 0.1230(2) 0.0351(12) Uani 1 1 d . . . C13 C 1.3314(4) -0.3940(3) 0.0902(2) 0.0339(12) Uani 1 1 d . . . H13 H 1.3824 -0.4021 0.0633 0.041 Uiso 1 1 calc R . . C14 C 1.2738(3) -0.3187(3) 0.0961(2) 0.0296(11) Uani 1 1 d . . . C15 C 1.2854(3) -0.2481(3) 0.0641(2) 0.0294(11) Uani 1 1 d . . . C16 C 1.3569(4) -0.2443(3) 0.0252(2) 0.0362(12) Uani 1 1 d . . . C17 C 1.3640(4) -0.1761(4) -0.0033(2) 0.0398(13) Uani 1 1 d . . . H17 H 1.4134 -0.1755 -0.0299 0.048 Uiso 1 1 calc R . . C18 C 1.2957(4) -0.1086(3) 0.0089(2) 0.0359(13) Uani 1 1 d . . . C19 C 1.2230(4) -0.1072(3) 0.0468(2) 0.0323(12) Uani 1 1 d . . . H19 H 1.1776 -0.0592 0.0533 0.039 Uiso 1 1 calc R . . C20 C 1.2157(3) -0.1766(3) 0.0759(2) 0.0290(11) Uani 1 1 d . . . C21 C 1.0535(3) -0.1973(3) 0.0825(2) 0.0262(10) Uani 1 1 d . . . C22 C 1.0586(4) -0.2662(3) 0.0620(2) 0.0297(11) Uani 1 1 d . . . H22 H 1.0983 -0.3150 0.0720 0.036 Uiso 1 1 calc R . . C23 C 1.0057(4) -0.2618(3) 0.0275(2) 0.0324(12) Uani 1 1 d . . . C24 C 0.9456(4) -0.1936(3) 0.0110(2) 0.0322(12) Uani 1 1 d . . . H24 H 0.9102 -0.1927 -0.0134 0.039 Uiso 1 1 calc R . . C25 C 0.9404(4) -0.1266(3) 0.0324(2) 0.0313(12) Uani 1 1 d . . . C26 C 0.9926(3) -0.1258(3) 0.0670(2) 0.0271(11) Uani 1 1 d . . . C27 C 0.9906(3) -0.0562(3) 0.0906(2) 0.0252(10) Uani 1 1 d . . . C28 C 0.9411(3) 0.0202(3) 0.0785(2) 0.0291(11) Uani 1 1 d . . . H28 H 0.9022 0.0307 0.0543 0.035 Uiso 1 1 calc R . . C29 C 0.9474(3) 0.0831(3) 0.1014(2) 0.0278(11) Uani 1 1 d . . . C30 C 1.0057(3) 0.0627(3) 0.1380(2) 0.0291(11) Uani 1 1 d . . . H30 H 1.0140 0.1021 0.1540 0.035 Uiso 1 1 calc R . . C31 C 1.0500(3) -0.0143(3) 0.1500(2) 0.0282(11) Uani 1 1 d . . . H31 H 1.0872 -0.0266 0.1756 0.034 Uiso 1 1 calc R . . C32 C 0.8364(4) 0.1761(3) 0.0554(2) 0.0359(13) Uani 1 1 d . . . H32A H 0.8627 0.1527 0.0192 0.054 Uiso 1 1 calc R . . H32B H 0.8108 0.2327 0.0486 0.054 Uiso 1 1 calc R . . H32C H 0.7929 0.1548 0.0755 0.054 Uiso 1 1 calc R . . C33 C 0.9100(4) 0.2222(3) 0.1119(2) 0.0360(13) Uani 1 1 d . . . H33A H 0.8924 0.2191 0.1532 0.054 Uiso 1 1 calc R . . H33B H 0.8751 0.2722 0.0959 0.054 Uiso 1 1 calc R . . H33C H 0.9692 0.2180 0.1018 0.054 Uiso 1 1 calc R . . C34 C 0.9595(3) -0.3693(3) 0.1838(2) 0.0296(11) Uani 1 1 d . . . H34 H 0.9728 -0.3241 0.1686 0.036 Uiso 1 1 calc R . . C35 C 0.9708(4) -0.4230(3) 0.1476(2) 0.0319(12) Uani 1 1 d . . . H35 H 0.9912 -0.4148 0.1084 0.038 Uiso 1 1 calc R . . C36 C 0.9516(4) -0.4913(3) 0.1692(2) 0.0303(11) Uani 1 1 d . . . C37 C 0.9217(3) -0.4991(3) 0.2274(2) 0.0273(11) Uani 1 1 d . . . H37 H 0.9090 -0.5442 0.2436 0.033 Uiso 1 1 calc R . . C38 C 0.9103(3) -0.4413(3) 0.2622(2) 0.0243(10) Uani 1 1 d . . . C39 C 0.8769(3) -0.4398(3) 0.3235(2) 0.0250(10) Uani 1 1 d . . . C40 C 0.8455(3) -0.4941(3) 0.3579(2) 0.0280(11) Uani 1 1 d . . . C41 C 0.8145(3) -0.4893(3) 0.4151(2) 0.0306(11) Uani 1 1 d . . . H41 H 0.7952 -0.5280 0.4376 0.037 Uiso 1 1 calc R . . C42 C 0.8131(4) -0.4251(3) 0.4382(2) 0.0328(12) Uani 1 1 d . . . C43 C 0.8412(4) -0.3684(3) 0.4074(2) 0.0327(12) Uani 1 1 d . . . H43 H 0.8390 -0.3257 0.4254 0.039 Uiso 1 1 calc R . . C44 C 0.8736(3) -0.3734(3) 0.3487(2) 0.0279(11) Uani 1 1 d . . . C45 C 0.9802(5) -0.5295(4) 0.0723(2) 0.0533(18) Uani 1 1 d . . . H45A H 0.9359 -0.4821 0.0612 0.080 Uiso 1 1 calc R . . H45B H 0.9823 -0.5735 0.0537 0.080 Uiso 1 1 calc R . . H45C H 1.0347 -0.5220 0.0609 0.080 Uiso 1 1 calc R . . C46 C 0.9361(5) -0.6129(3) 0.1549(2) 0.0450(16) Uani 1 1 d . . . H46A H 0.9519 -0.6332 0.1917 0.067 Uiso 1 1 calc R . . H46B H 0.9640 -0.6535 0.1283 0.067 Uiso 1 1 calc R . . H46C H 0.8749 -0.5969 0.1591 0.067 Uiso 1 1 calc R . . C47 C 0.8539(4) -0.1610(3) 0.3678(2) 0.0326(12) Uani 1 1 d . . . H47 H 0.8045 -0.1464 0.3524 0.039 Uiso 1 1 calc R . . C48 C 0.8568(4) -0.1120(3) 0.4031(2) 0.0375(13) Uani 1 1 d . . . H48 H 0.8111 -0.0646 0.4111 0.045 Uiso 1 1 calc R . . C49 C 0.9279(4) -0.1328(3) 0.4274(2) 0.0354(13) Uani 1 1 d . . . C50 C 0.9946(4) -0.2034(3) 0.4126(2) 0.0332(12) Uani 1 1 d . . . H50 H 1.0438 -0.2193 0.4282 0.040 Uiso 1 1 calc R . . C51 C 0.9884(4) -0.2497(3) 0.3753(2) 0.0302(11) Uani 1 1 d . . . C52 C 1.0529(3) -0.3246(3) 0.3557(2) 0.0277(11) Uani 1 1 d . . . C53 C 1.1284(4) -0.3640(3) 0.3740(2) 0.0331(12) Uani 1 1 d . . . C54 C 1.1844(4) -0.4354(3) 0.3566(2) 0.0361(13) Uani 1 1 d . . . H54 H 1.2361 -0.4602 0.3695 0.043 Uiso 1 1 calc R . . C55 C 1.1610(4) -0.4690(3) 0.3192(2) 0.0328(12) Uani 1 1 d . . . C56 C 1.0882(3) -0.4326(3) 0.2984(2) 0.0279(11) Uani 1 1 d . . . H56 H 1.0757 -0.4568 0.2718 0.033 Uiso 1 1 calc R . . C57 C 1.0319(3) -0.3595(3) 0.3164(2) 0.0261(10) Uani 1 1 d . . . C58 C 0.8713(5) -0.0076(3) 0.4703(3) 0.0539(18) Uani 1 1 d . . . H58A H 0.8755 0.0236 0.4341 0.081 Uiso 1 1 calc R . . H58B H 0.8822 0.0165 0.4991 0.081 Uiso 1 1 calc R . . H58C H 0.8145 -0.0102 0.4817 0.081 Uiso 1 1 calc R . . C59 C 1.0065(5) -0.1100(3) 0.4897(3) 0.0468(16) Uani 1 1 d . . . H59A H 1.0178 -0.1634 0.5068 0.070 Uiso 1 1 calc R . . H59B H 0.9960 -0.0750 0.5189 0.070 Uiso 1 1 calc R . . H59C H 1.0553 -0.1076 0.4608 0.070 Uiso 1 1 calc R . . C60 C 0.7682(3) -0.6309(3) 0.2660(2) 0.0279(11) Uani 1 1 d . . . C61 C 1.0040(4) -0.7969(3) 0.2293(2) 0.0306(11) Uani 1 1 d . . . C62 C 0.6578(4) -0.5597(3) 0.3811(2) 0.0361(12) Uani 1 1 d . . . H62 H 0.6894 -0.6122 0.3728 0.043 Uiso 1 1 calc R . . C63 C 0.6375(4) -0.5421(4) 0.4366(2) 0.0436(14) Uani 1 1 d . . . H63 H 0.6537 -0.5825 0.4652 0.052 Uiso 1 1 calc R . . C64 C 0.5931(4) -0.4651(4) 0.4513(3) 0.0494(16) Uani 1 1 d . . . C65 C 0.5710(4) -0.4096(4) 0.4059(3) 0.0476(16) Uani 1 1 d . . . H65 H 0.5415 -0.3562 0.4126 0.057 Uiso 1 1 calc R . . C66 C 0.5921(4) -0.4326(3) 0.3519(3) 0.0394(13) Uani 1 1 d . . . H66 H 0.5750 -0.3938 0.3225 0.047 Uiso 1 1 calc R . . C67 C 0.6026(5) -0.5042(6) 0.5510(3) 0.082(3) Uani 1 1 d . . . H67A H 0.5821 -0.5470 0.5526 0.122 Uiso 1 1 calc R . . H67B H 0.5817 -0.4805 0.5873 0.122 Uiso 1 1 calc R . . H67C H 0.6644 -0.5243 0.5432 0.122 Uiso 1 1 calc R . . C68 C 0.5303(6) -0.3639(6) 0.5194(4) 0.096(3) Uani 1 1 d . . . H68A H 0.5714 -0.3373 0.5095 0.145 Uiso 1 1 calc R . . H68B H 0.5060 -0.3616 0.5598 0.145 Uiso 1 1 calc R . . H68C H 0.4854 -0.3382 0.4976 0.145 Uiso 1 1 calc R . . C69 C 0.7248(3) -0.4113(3) 0.2259(2) 0.0316(11) Uani 1 1 d . . . H69 H 0.7190 -0.4121 0.2657 0.038 Uiso 1 1 calc R . . C70 C 0.7430(4) -0.3503(3) 0.1933(2) 0.0366(13) Uani 1 1 d . . . H70 H 0.7470 -0.3095 0.2102 0.044 Uiso 1 1 calc R . . C71 C 0.7557(4) -0.3495(3) 0.1338(3) 0.0396(13) Uani 1 1 d . . . C72 C 0.7484(4) -0.4121(3) 0.1119(2) 0.0380(13) Uani 1 1 d . . . H72 H 0.7582 -0.4145 0.0722 0.046 Uiso 1 1 calc R . . C73 C 0.7269(3) -0.4703(3) 0.1481(2) 0.0299(11) Uani 1 1 d . . . C74 C 0.7103(4) -0.5347(3) 0.1306(2) 0.0327(12) Uani 1 1 d . . . C75 C 0.7216(4) -0.5536(3) 0.0750(2) 0.0389(13) Uani 1 1 d . . . C76 C 0.6997(4) -0.6120(3) 0.0615(2) 0.0421(14) Uani 1 1 d . . . H76 H 0.7082 -0.6237 0.0236 0.051 Uiso 1 1 calc R . . C77 C 0.6644(4) -0.6530(3) 0.1070(2) 0.0358(13) Uani 1 1 d . . . C78 C 0.6526(3) -0.6387(3) 0.1623(2) 0.0329(12) Uani 1 1 d . . . H78 H 0.6295 -0.6691 0.1916 0.039 Uiso 1 1 calc R . . C79 C 0.6749(3) -0.5790(3) 0.1755(2) 0.0291(11) Uani 1 1 d . . . C80 C 0.5429(3) -0.4693(3) 0.2393(2) 0.0310(11) Uani 1 1 d . . . C81 C 0.5256(4) -0.3959(3) 0.2084(2) 0.0348(12) Uani 1 1 d . . . H81 H 0.5688 -0.3742 0.1961 0.042 Uiso 1 1 calc R . . C82 C 0.4468(4) -0.3554(3) 0.1958(2) 0.0390(13) Uani 1 1 d . . . C83 C 0.3814(4) -0.3833(3) 0.2142(3) 0.0417(14) Uani 1 1 d . . . H83 H 0.3271 -0.3548 0.2059 0.050 Uiso 1 1 calc R . . C84 C 0.3985(4) -0.4549(3) 0.2453(2) 0.0373(13) Uani 1 1 d . . . C85 C 0.4772(3) -0.4990(3) 0.2582(2) 0.0309(11) Uani 1 1 d . . . C86 C 0.4988(3) -0.5775(3) 0.2895(2) 0.0326(12) Uani 1 1 d . . . C87 C 0.4443(4) -0.6165(3) 0.3144(3) 0.0395(13) Uani 1 1 d . . . H87 H 0.3863 -0.5925 0.3125 0.047 Uiso 1 1 calc R . . C88 C 0.4727(4) -0.6916(3) 0.3427(3) 0.0423(14) Uani 1 1 d . . . C89 C 0.5602(4) -0.7247(3) 0.3428(3) 0.0397(13) Uani 1 1 d . . . H89 H 0.5836 -0.7755 0.3602 0.048 Uiso 1 1 calc R . . C90 C 0.6103(4) -0.6825(3) 0.3176(2) 0.0338(12) Uani 1 1 d . . . H90 H 0.6686 -0.7054 0.3187 0.041 Uiso 1 1 calc R . . C91 C 0.7756(5) -0.2231(4) 0.1233(3) 0.0578(19) Uani 1 1 d . . . H91A H 0.7218 -0.1986 0.1484 0.087 Uiso 1 1 calc R . . H91B H 0.7863 -0.1849 0.0927 0.087 Uiso 1 1 calc R . . H91C H 0.8211 -0.2415 0.1448 0.087 Uiso 1 1 calc R . . C92 C 0.7822(6) -0.2892(4) 0.0387(3) 0.062(2) Uani 1 1 d . . . H92A H 0.8313 -0.3341 0.0248 0.094 Uiso 1 1 calc R . . H92B H 0.7903 -0.2410 0.0204 0.094 Uiso 1 1 calc R . . H92C H 0.7316 -0.2924 0.0300 0.094 Uiso 1 1 calc R . . C93 C 0.3285(5) -0.6918(5) 0.3718(5) 0.094(3) Uani 1 1 d . . . H93A H 0.3091 -0.6401 0.3860 0.141 Uiso 1 1 calc R . . H93B H 0.2991 -0.7238 0.3972 0.141 Uiso 1 1 calc R . . H93C H 0.3165 -0.6865 0.3339 0.141 Uiso 1 1 calc R . . C94 C 0.4508(5) -0.8061(5) 0.3989(5) 0.094(3) Uani 1 1 d . . . H94A H 0.4860 -0.8442 0.3714 0.141 Uiso 1 1 calc R . . H94B H 0.4032 -0.8212 0.4199 0.141 Uiso 1 1 calc R . . H94C H 0.4845 -0.8042 0.4252 0.141 Uiso 1 1 calc R . . C95 C 0.7946(3) -0.8242(3) 0.2359(2) 0.0291(11) Uani 1 1 d . . . H95 H 0.7697 -0.7689 0.2328 0.035 Uiso 1 1 calc R . . C96 C 0.7620(4) -0.8658(3) 0.2123(2) 0.0338(12) Uani 1 1 d . . . H96 H 0.7159 -0.8396 0.1937 0.041 Uiso 1 1 calc R . . C97 C 0.7971(4) -0.9473(3) 0.2160(2) 0.0353(12) Uani 1 1 d . . . C98 C 0.8633(3) -0.9822(3) 0.2464(2) 0.0328(12) Uani 1 1 d . . . H98 H 0.8869 -1.0374 0.2514 0.039 Uiso 1 1 calc R . . C99 C 0.8942(3) -0.9368(3) 0.2690(2) 0.0258(10) Uani 1 1 d . . . C100 C 0.9634(3) -0.9635(3) 0.3005(2) 0.0290(11) Uani 1 1 d . . . C101 C 1.0149(4) -1.0413(3) 0.3098(2) 0.0325(12) Uani 1 1 d . . . C102 C 1.0799(4) -1.0634(3) 0.3392(2) 0.0379(13) Uani 1 1 d . . . H102 H 1.1136 -1.1166 0.3454 0.046 Uiso 1 1 calc R . . C103 C 1.0932(4) -1.0044(3) 0.3593(2) 0.0388(13) Uani 1 1 d . . . C104 C 1.0459(4) -0.9265(3) 0.3513(2) 0.0339(12) Uani 1 1 d . . . H104 H 1.0572 -0.8882 0.3663 0.041 Uiso 1 1 calc R . . C105 C 0.9810(3) -0.9046(3) 0.3206(2) 0.0276(11) Uani 1 1 d . . . C106 C 0.7010(5) -0.9568(4) 0.1609(3) 0.0519(18) Uani 1 1 d . . . H10A H 0.6525 -0.9191 0.1831 0.078 Uiso 1 1 calc R . . H10B H 0.6839 -0.9974 0.1517 0.078 Uiso 1 1 calc R . . H10C H 0.7216 -0.9301 0.1259 0.078 Uiso 1 1 calc R . . C107 C 0.8093(5) -1.0765(3) 0.1923(3) 0.0517(17) Uani 1 1 d . . . H10D H 0.8628 -1.0883 0.1652 0.078 Uiso 1 1 calc R . . H10E H 0.7730 -1.0989 0.1812 0.078 Uiso 1 1 calc R . . H10F H 0.8200 -1.0989 0.2300 0.078 Uiso 1 1 calc R . . C108 C 0.8267(3) -0.7947(3) 0.3751(2) 0.0288(11) Uani 1 1 d . . . C109 C 0.7620(4) -0.8251(3) 0.3885(2) 0.0344(12) Uani 1 1 d . . . H109 H 0.7525 -0.8501 0.3609 0.041 Uiso 1 1 calc R . . C110 C 0.7125(4) -0.8191(3) 0.4409(3) 0.0413(14) Uani 1 1 d . . . C111 C 0.7227(4) -0.7841(4) 0.4834(3) 0.0475(15) Uani 1 1 d . . . H111 H 0.6875 -0.7808 0.5198 0.057 Uiso 1 1 calc R . . C112 C 0.7868(4) -0.7545(4) 0.4699(3) 0.0439(14) Uani 1 1 d . . . C113 C 0.8397(4) -0.7575(3) 0.4175(2) 0.0322(12) Uani 1 1 d . . . C114 C 0.9101(3) -0.7268(3) 0.4001(2) 0.0284(11) Uani 1 1 d . . . C115 C 0.9336(4) -0.6875(3) 0.4335(2) 0.0299(11) Uani 1 1 d . . . H115 H 0.9049 -0.6805 0.4716 0.036 Uiso 1 1 calc R . . C116 C 0.9992(3) -0.6579(3) 0.4119(2) 0.0307(11) Uani 1 1 d . . . C117 C 1.0385(4) -0.6688(3) 0.3547(2) 0.0342(12) Uani 1 1 d . . . H117 H 1.0818 -0.6484 0.3376 0.041 Uiso 1 1 calc R . . C118 C 1.0135(4) -0.7093(3) 0.3238(2) 0.0333(12) Uani 1 1 d . . . H118 H 1.0411 -0.7168 0.2856 0.040 Uiso 1 1 calc R . . C119 C 0.9817(4) -0.6064(3) 0.5020(2) 0.0423(14) Uani 1 1 d . . . H11A H 0.9239 -0.5700 0.5025 0.064 Uiso 1 1 calc R . . H11B H 1.0115 -0.5840 0.5198 0.064 Uiso 1 1 calc R . . H11C H 0.9805 -0.6557 0.5228 0.064 Uiso 1 1 calc R . . C120 C 1.0797(5) -0.5766(4) 0.4176(3) 0.0496(17) Uani 1 1 d . . . H12A H 1.1300 -0.6103 0.3937 0.074 Uiso 1 1 calc R . . H12B H 1.0966 -0.5585 0.4468 0.074 Uiso 1 1 calc R . . H12C H 1.0496 -0.5317 0.3943 0.074 Uiso 1 1 calc R . . C121 C 1.4550(5) -0.5451(4) 0.0797(3) 0.069(2) Uani 1 1 d . . . H12D H 1.4450 -0.5261 0.0414 0.104 Uiso 1 1 calc R . . H12E H 1.4883 -0.6010 0.0806 0.104 Uiso 1 1 calc R . . H12F H 1.4858 -0.5170 0.0909 0.104 Uiso 1 1 calc R . . C122 C 1.3652(5) -0.5971(4) 0.1584(3) 0.067(2) Uani 1 1 d . . . H12G H 1.3480 -0.5806 0.1970 0.101 Uiso 1 1 calc R . . H12H H 1.4190 -0.6407 0.1549 0.101 Uiso 1 1 calc R . . H12I H 1.3222 -0.6135 0.1500 0.101 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 0.03222(11) 0.01746(8) 0.02617(10) -0.00419(7) -0.00977(8) -0.00727(7) Ir2 0.03073(11) 0.01930(8) 0.02528(10) -0.00650(7) -0.00952(8) -0.00822(7) Ir3 0.02991(11) 0.02159(9) 0.02874(10) -0.00446(7) -0.01069(8) -0.00580(8) Ir4 0.03041(11) 0.01891(8) 0.02899(10) -0.00511(7) -0.01164(8) -0.00688(7) F1 0.043(2) 0.0447(19) 0.049(2) -0.0073(16) 0.0040(17) -0.0050(16) F2 0.055(2) 0.0415(19) 0.050(2) 0.0068(16) -0.0082(18) -0.0274(17) F3 0.072(2) 0.0228(14) 0.0398(18) -0.0091(13) -0.0234(17) -0.0158(15) F4 0.050(2) 0.0245(14) 0.051(2) -0.0060(13) -0.0290(17) -0.0065(14) F5 0.051(2) 0.0291(15) 0.0324(16) -0.0048(12) -0.0082(14) -0.0208(14) F6 0.062(2) 0.051(2) 0.0253(16) -0.0108(14) 0.0022(15) -0.0275(18) F7 0.046(2) 0.0483(19) 0.0430(19) -0.0126(15) -0.0230(16) -0.0136(16) F8 0.0350(18) 0.0299(16) 0.048(2) -0.0075(14) -0.0094(15) 0.0001(13) F9 0.092(3) 0.048(2) 0.0301(18) 0.0001(15) -0.0104(19) -0.031(2) F10 0.051(2) 0.0417(18) 0.054(2) -0.0226(16) -0.0155(17) -0.0156(16) F11 0.054(2) 0.0317(17) 0.069(3) 0.0093(16) -0.030(2) -0.0012(16) F12 0.0298(19) 0.059(2) 0.063(2) 0.0053(18) -0.0117(17) -0.0114(17) F13 0.054(2) 0.0245(15) 0.054(2) -0.0109(14) -0.0264(17) -0.0078(14) F14 0.060(2) 0.0343(17) 0.075(3) -0.0069(17) -0.045(2) -0.0041(16) F15 0.062(3) 0.071(3) 0.052(2) -0.0009(19) -0.0056(19) -0.044(2) F16 0.078(3) 0.091(3) 0.0326(19) -0.0226(19) 0.0000(18) -0.051(2) N1 0.032(2) 0.0181(18) 0.028(2) -0.0055(16) -0.0114(19) -0.0052(17) N2 0.043(3) 0.047(3) 0.067(4) -0.026(3) -0.016(3) -0.006(3) N3 0.034(2) 0.027(2) 0.032(2) -0.0080(17) -0.0090(19) -0.0086(18) N4 0.064(4) 0.104(5) 0.067(4) 0.002(4) -0.035(4) -0.040(4) N5 0.031(2) 0.0222(19) 0.029(2) -0.0050(16) -0.0113(18) -0.0043(17) N6 0.050(3) 0.027(2) 0.050(3) -0.008(2) -0.008(3) 0.003(2) N7 0.032(2) 0.0199(18) 0.028(2) -0.0048(16) -0.0099(18) -0.0084(17) N8 0.047(3) 0.021(2) 0.037(3) -0.0058(18) -0.015(2) -0.0107(19) N9 0.029(2) 0.0216(19) 0.027(2) -0.0071(16) -0.0084(17) -0.0080(17) N10 0.065(3) 0.032(2) 0.027(2) -0.0097(18) -0.002(2) -0.028(2) N11 0.039(3) 0.0226(19) 0.025(2) -0.0046(16) -0.0107(18) -0.0111(18) N12 0.066(4) 0.027(2) 0.042(3) -0.012(2) -0.025(3) -0.012(2) N13 0.034(2) 0.023(2) 0.031(2) -0.0053(17) -0.0080(19) -0.0125(19) N14 0.058(4) 0.037(3) 0.047(3) -0.013(2) -0.013(3) -0.020(2) N15 0.034(3) 0.036(2) 0.032(2) -0.0085(19) -0.011(2) -0.010(2) N16 0.060(4) 0.112(6) 0.037(3) -0.027(3) -0.005(3) -0.024(4) N17 0.038(3) 0.025(2) 0.033(2) -0.0022(17) -0.012(2) -0.0108(19) N18 0.078(4) 0.038(3) 0.051(3) 0.007(2) -0.027(3) -0.033(3) N19 0.033(2) 0.031(2) 0.030(2) -0.0052(18) -0.0090(19) -0.0091(19) N20 0.034(3) 0.052(3) 0.094(5) 0.016(3) -0.004(3) -0.014(3) N21 0.034(2) 0.0201(19) 0.033(2) -0.0052(16) -0.0126(19) -0.0086(17) N22 0.049(3) 0.031(2) 0.058(3) -0.011(2) -0.028(3) -0.011(2) N23 0.035(2) 0.0209(19) 0.027(2) -0.0040(16) -0.0115(18) -0.0098(17) N24 0.056(3) 0.036(2) 0.034(2) -0.004(2) -0.014(2) -0.025(2) C1 0.035(3) 0.014(2) 0.028(3) -0.0047(18) -0.014(2) -0.003(2) C2 0.032(3) 0.021(2) 0.037(3) -0.003(2) -0.018(2) -0.007(2) C3 0.030(3) 0.031(3) 0.032(3) -0.006(2) -0.008(2) -0.004(2) C4 0.040(3) 0.048(3) 0.032(3) -0.006(2) -0.012(3) -0.009(3) C5 0.048(4) 0.075(5) 0.045(4) -0.009(3) -0.017(3) -0.026(4) C6 0.060(5) 0.077(5) 0.050(4) -0.007(3) -0.016(3) -0.042(4) C7 0.041(3) 0.043(3) 0.042(3) -0.008(3) -0.008(3) -0.021(3) C8 0.084(7) 0.122(8) 0.061(5) 0.019(5) -0.047(5) -0.038(6) C9 0.106(9) 0.180(12) 0.102(8) 0.010(8) -0.063(7) -0.079(9) C10 0.040(3) 0.022(2) 0.032(3) -0.004(2) -0.010(2) -0.008(2) C11 0.046(3) 0.020(2) 0.037(3) -0.003(2) -0.009(3) -0.008(2) C12 0.034(3) 0.028(3) 0.037(3) -0.007(2) -0.009(2) -0.001(2) C13 0.034(3) 0.034(3) 0.029(3) -0.010(2) -0.007(2) -0.003(2) C14 0.033(3) 0.029(2) 0.029(3) -0.003(2) -0.015(2) -0.007(2) C15 0.034(3) 0.031(3) 0.025(2) -0.009(2) -0.008(2) -0.008(2) C16 0.037(3) 0.037(3) 0.033(3) -0.008(2) -0.006(2) -0.009(2) C17 0.037(3) 0.051(3) 0.034(3) -0.005(3) -0.001(2) -0.021(3) C18 0.052(4) 0.033(3) 0.030(3) 0.002(2) -0.013(3) -0.020(3) C19 0.045(3) 0.026(2) 0.031(3) -0.004(2) -0.012(2) -0.015(2) C20 0.040(3) 0.028(2) 0.024(2) -0.0059(19) -0.011(2) -0.013(2) C21 0.035(3) 0.021(2) 0.024(2) -0.0057(18) -0.006(2) -0.010(2) C22 0.042(3) 0.021(2) 0.028(3) -0.0022(19) -0.012(2) -0.011(2) C23 0.052(3) 0.020(2) 0.030(3) -0.006(2) -0.011(2) -0.015(2) C24 0.049(3) 0.025(2) 0.030(3) -0.006(2) -0.016(2) -0.016(2) C25 0.044(3) 0.022(2) 0.029(3) -0.002(2) -0.014(2) -0.010(2) C26 0.040(3) 0.019(2) 0.023(2) -0.0037(18) -0.007(2) -0.009(2) C27 0.032(3) 0.022(2) 0.023(2) -0.0061(18) -0.007(2) -0.009(2) C28 0.032(3) 0.025(2) 0.033(3) -0.005(2) -0.011(2) -0.010(2) C29 0.038(3) 0.020(2) 0.026(2) -0.0050(18) -0.007(2) -0.008(2) C30 0.045(3) 0.022(2) 0.028(3) -0.0033(19) -0.010(2) -0.018(2) C31 0.037(3) 0.025(2) 0.027(3) -0.0060(19) -0.012(2) -0.011(2) C32 0.049(3) 0.023(2) 0.033(3) -0.005(2) -0.015(3) -0.004(2) C33 0.057(4) 0.018(2) 0.033(3) -0.007(2) -0.013(3) -0.010(2) C34 0.043(3) 0.023(2) 0.028(3) -0.0027(19) -0.009(2) -0.016(2) C35 0.050(3) 0.027(2) 0.025(3) -0.004(2) -0.009(2) -0.018(2) C36 0.042(3) 0.023(2) 0.029(3) -0.0004(19) -0.011(2) -0.012(2) C37 0.037(3) 0.023(2) 0.028(3) -0.0024(19) -0.013(2) -0.014(2) C38 0.033(3) 0.021(2) 0.024(2) -0.0032(18) -0.010(2) -0.012(2) C39 0.032(3) 0.022(2) 0.027(2) -0.0048(18) -0.013(2) -0.010(2) C40 0.033(3) 0.024(2) 0.030(3) -0.0072(19) -0.013(2) -0.007(2) C41 0.034(3) 0.031(3) 0.031(3) 0.000(2) -0.009(2) -0.015(2) C42 0.036(3) 0.036(3) 0.025(3) -0.006(2) -0.005(2) -0.011(2) C43 0.040(3) 0.031(3) 0.031(3) -0.011(2) -0.012(2) -0.011(2) C44 0.029(3) 0.027(2) 0.031(3) -0.006(2) -0.012(2) -0.007(2) C45 0.096(6) 0.051(4) 0.025(3) -0.015(3) -0.001(3) -0.040(4) C46 0.079(5) 0.028(3) 0.036(3) -0.008(2) -0.008(3) -0.028(3) C47 0.038(3) 0.025(2) 0.036(3) -0.008(2) -0.015(2) -0.006(2) C48 0.045(3) 0.026(3) 0.040(3) -0.009(2) -0.015(3) -0.004(2) C49 0.052(4) 0.025(2) 0.033(3) -0.007(2) -0.017(3) -0.012(2) C50 0.048(3) 0.028(2) 0.031(3) -0.003(2) -0.022(2) -0.012(2) C51 0.040(3) 0.026(2) 0.028(3) -0.002(2) -0.013(2) -0.012(2) C52 0.036(3) 0.026(2) 0.026(3) -0.0008(19) -0.010(2) -0.016(2) C53 0.046(3) 0.035(3) 0.028(3) 0.000(2) -0.016(2) -0.020(2) C54 0.033(3) 0.037(3) 0.035(3) -0.003(2) -0.017(2) -0.002(2) C55 0.039(3) 0.028(3) 0.031(3) -0.002(2) -0.005(2) -0.013(2) C56 0.034(3) 0.025(2) 0.026(2) -0.0037(19) -0.008(2) -0.010(2) C57 0.034(3) 0.023(2) 0.025(2) -0.0028(18) -0.005(2) -0.013(2) C58 0.081(5) 0.030(3) 0.053(4) -0.018(3) -0.029(4) -0.008(3) C59 0.079(5) 0.033(3) 0.040(3) -0.007(2) -0.032(3) -0.017(3) C60 0.030(3) 0.023(2) 0.031(3) -0.0015(19) -0.012(2) -0.007(2) C61 0.039(3) 0.020(2) 0.030(3) -0.007(2) -0.006(2) -0.006(2) C62 0.034(3) 0.044(3) 0.030(3) -0.004(2) -0.008(2) -0.013(3) C63 0.042(4) 0.064(4) 0.030(3) 0.001(3) -0.012(3) -0.023(3) C64 0.041(4) 0.072(4) 0.036(3) -0.018(3) -0.004(3) -0.017(3) C65 0.039(3) 0.058(4) 0.047(4) -0.024(3) -0.003(3) -0.014(3) C66 0.041(3) 0.037(3) 0.042(3) -0.011(2) -0.013(3) -0.009(3) C67 0.069(6) 0.148(9) 0.031(4) -0.021(5) -0.002(4) -0.042(6) C68 0.095(7) 0.132(9) 0.061(5) -0.059(6) 0.002(5) -0.028(6) C69 0.035(3) 0.031(3) 0.033(3) -0.007(2) -0.014(2) -0.009(2) C70 0.041(3) 0.027(3) 0.046(3) -0.002(2) -0.017(3) -0.012(2) C71 0.051(4) 0.030(3) 0.043(3) 0.002(2) -0.021(3) -0.015(3) C72 0.050(4) 0.034(3) 0.036(3) 0.001(2) -0.015(3) -0.019(3) C73 0.032(3) 0.028(2) 0.029(3) -0.004(2) -0.008(2) -0.008(2) C74 0.037(3) 0.023(2) 0.035(3) -0.005(2) -0.009(2) -0.005(2) C75 0.057(4) 0.029(3) 0.030(3) -0.001(2) -0.012(3) -0.012(3) C76 0.052(4) 0.038(3) 0.036(3) -0.013(2) -0.017(3) -0.006(3) C77 0.039(3) 0.026(2) 0.045(3) -0.012(2) -0.013(3) -0.008(2) C78 0.034(3) 0.027(2) 0.036(3) -0.008(2) -0.009(2) -0.006(2) C79 0.027(3) 0.025(2) 0.034(3) -0.007(2) -0.012(2) -0.003(2) C80 0.033(3) 0.028(2) 0.031(3) -0.008(2) -0.014(2) -0.003(2) C81 0.037(3) 0.027(2) 0.041(3) -0.006(2) -0.018(3) -0.004(2) C82 0.045(4) 0.030(3) 0.038(3) -0.005(2) -0.016(3) -0.002(2) C83 0.039(3) 0.037(3) 0.043(3) -0.009(2) -0.015(3) 0.002(3) C84 0.032(3) 0.045(3) 0.035(3) -0.008(2) -0.007(2) -0.010(3) C85 0.033(3) 0.029(2) 0.029(3) -0.008(2) -0.010(2) -0.005(2) C86 0.032(3) 0.037(3) 0.030(3) -0.013(2) -0.006(2) -0.009(2) C87 0.030(3) 0.041(3) 0.044(3) -0.003(3) -0.007(3) -0.008(2) C88 0.034(3) 0.040(3) 0.050(4) -0.003(3) -0.005(3) -0.011(3) C89 0.038(3) 0.031(3) 0.043(3) 0.004(2) -0.006(3) -0.008(2) C90 0.029(3) 0.032(3) 0.038(3) -0.003(2) -0.006(2) -0.008(2) C91 0.083(6) 0.040(3) 0.065(5) 0.002(3) -0.024(4) -0.035(4) C92 0.106(7) 0.058(4) 0.043(4) 0.015(3) -0.025(4) -0.051(4) C93 0.040(4) 0.069(5) 0.155(10) 0.032(6) -0.008(5) -0.021(4) C94 0.051(5) 0.070(5) 0.144(9) 0.043(6) -0.018(5) -0.024(4) C95 0.031(3) 0.025(2) 0.032(3) -0.008(2) -0.013(2) -0.005(2) C96 0.034(3) 0.032(3) 0.038(3) -0.009(2) -0.014(2) -0.008(2) C97 0.039(3) 0.031(3) 0.039(3) -0.003(2) -0.013(3) -0.012(2) C98 0.035(3) 0.025(2) 0.042(3) -0.009(2) -0.013(2) -0.008(2) C99 0.028(3) 0.023(2) 0.025(2) -0.0083(18) -0.005(2) -0.005(2) C100 0.033(3) 0.018(2) 0.036(3) -0.0041(19) -0.009(2) -0.006(2) C101 0.039(3) 0.025(2) 0.036(3) -0.010(2) -0.010(2) -0.008(2) C102 0.042(3) 0.020(2) 0.049(3) -0.004(2) -0.023(3) 0.000(2) C103 0.043(3) 0.031(3) 0.042(3) -0.003(2) -0.022(3) -0.005(2) C104 0.038(3) 0.023(2) 0.044(3) -0.008(2) -0.016(3) -0.007(2) C105 0.029(3) 0.022(2) 0.033(3) -0.0035(19) -0.012(2) -0.007(2) C106 0.068(5) 0.044(3) 0.064(4) 0.004(3) -0.041(4) -0.030(3) C107 0.062(4) 0.030(3) 0.073(5) -0.014(3) -0.023(4) -0.017(3) C108 0.033(3) 0.016(2) 0.040(3) -0.0021(19) -0.020(2) -0.005(2) C109 0.041(3) 0.029(3) 0.034(3) 0.000(2) -0.014(2) -0.011(2) C110 0.048(4) 0.043(3) 0.044(3) 0.001(3) -0.014(3) -0.026(3) C111 0.052(4) 0.058(4) 0.038(3) -0.005(3) -0.003(3) -0.028(3) C112 0.056(4) 0.049(3) 0.035(3) -0.009(3) -0.010(3) -0.026(3) C113 0.044(3) 0.024(2) 0.028(3) -0.001(2) -0.012(2) -0.009(2) C114 0.031(3) 0.021(2) 0.032(3) -0.0002(19) -0.011(2) -0.005(2) C115 0.042(3) 0.024(2) 0.026(3) -0.0028(19) -0.012(2) -0.011(2) C116 0.038(3) 0.026(2) 0.034(3) -0.001(2) -0.016(2) -0.013(2) C117 0.038(3) 0.032(3) 0.039(3) -0.003(2) -0.012(2) -0.017(2) C118 0.040(3) 0.033(3) 0.032(3) -0.005(2) -0.011(2) -0.014(2) C119 0.066(4) 0.043(3) 0.029(3) -0.004(2) -0.018(3) -0.026(3) C120 0.070(5) 0.061(4) 0.041(3) -0.015(3) -0.012(3) -0.044(4) C121 0.057(5) 0.043(4) 0.071(5) -0.012(3) 0.008(4) 0.014(3) C122 0.078(6) 0.025(3) 0.081(6) -0.002(3) -0.012(4) 0.000(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 Ir1 C21 2.013(5) . ? Ir1 C1 2.036(6) . ? Ir1 C20 2.052(6) . ? Ir1 N7 2.060(4) . ? Ir1 N5 2.068(4) . ? Ir1 N3 2.190(4) . ? Ir2 C44 2.001(5) . ? Ir2 C57 2.037(5) . ? Ir2 N11 2.057(4) . ? Ir2 N9 2.058(4) . ? Ir2 C2 2.080(5) . ? Ir2 N1 2.121(5) . ? Ir3 C79 2.011(5) . ? Ir3 C80 2.039(5) . ? Ir3 C60 2.049(5) . ? Ir3 N19 2.063(5) . ? Ir3 N17 2.064(4) . ? Ir3 N15 2.194(4) . ? Ir4 C105 2.013(5) . ? Ir4 C108 2.053(6) . ? Ir4 N23 2.058(4) . ? Ir4 N21 2.059(4) . ? Ir4 C61 2.079(6) . ? Ir4 N13 2.113(4) . ? F1 C16 1.368(6) . ? F2 C18 1.374(6) . ? F3 C23 1.384(5) . ? F4 C25 1.365(6) . ? F5 C40 1.368(5) . ? F6 C42 1.376(6) . ? F7 C53 1.376(5) . ? F8 C55 1.370(6) . ? F9 C75 1.361(7) . ? F10 C77 1.365(6) . ? F11 C82 1.347(6) . ? F12 C84 1.361(7) . ? F13 C101 1.359(5) . ? F14 C103 1.368(6) . ? F15 C110 1.381(7) . ? F16 C112 1.374(6) . ? N1 C1 1.170(7) . ? N2 C2 1.128(7) . ? N3 C7 1.347(7) . ? N3 C3 1.349(7) . ? N4 C5 1.375(8) . ? N4 C8 1.469(10) . ? N4 C9 1.479(12) . ? N5 C10 1.366(7) . ? N5 C14 1.367(7) . ? N6 C12 1.364(7) . ? N6 C122 1.455(8) . ? N6 C121 1.456(9) . ? N7 C31 1.357(6) . ? N7 C27 1.374(6) . ? N8 C29 1.359(6) . ? N8 C32 1.450(7) . ? N8 C33 1.462(6) . ? N9 C34 1.346(6) . ? N9 C38 1.369(6) . ? N10 C36 1.365(6) . ? N10 C45 1.463(7) . ? N10 C46 1.465(7) . ? N11 C47 1.353(6) . ? N11 C51 1.379(7) . ? N12 C49 1.378(6) . ? N12 C59 1.450(8) . ? N12 C58 1.458(7) . ? N13 C60 1.152(6) . ? N14 C61 1.132(7) . ? N15 C66 1.352(7) . ? N15 C62 1.353(7) . ? N16 C64 1.370(8) . ? N16 C67 1.463(11) . ? N16 C68 1.465(11) . ? N17 C69 1.345(6) . ? N17 C73 1.381(6) . ? N18 C71 1.369(7) . ? N18 C92 1.444(8) . ? N18 C91 1.473(8) . ? N19 C90 1.358(7) . ? N19 C86 1.371(7) . ? N20 C88 1.356(8) . ? N20 C94 1.461(9) . ? N20 C93 1.462(9) . ? N21 C95 1.345(6) . ? N21 C99 1.383(6) . ? N22 C97 1.368(7) . ? N22 C106 1.447(7) . ? N22 C107 1.465(7) . ? N23 C118 1.362(7) . ? N23 C114 1.363(6) . ? N24 C116 1.368(6) . ? N24 C119 1.446(7) . ? N24 C120 1.460(8) . ? C3 C4 1.381(7) . ? C3 H3 0.9500 . ? C4 C5 1.381(9) . ? C4 H4 0.9500 . ? C5 C6 1.420(10) . ? C6 C7 1.375(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.376(7) . ? C10 H10 0.9500 . ? C11 C12 1.420(8) . ? C11 H11 0.9500 . ? C12 C13 1.412(8) . ? C13 C14 1.389(7) . ? C13 H13 0.9500 . ? C14 C15 1.472(7) . ? C15 C16 1.396(8) . ? C15 C20 1.440(7) . ? C16 C17 1.378(8) . ? C17 C18 1.383(8) . ? C17 H17 0.9500 . ? C18 C19 1.376(8) . ? C19 C20 1.405(7) . ? C19 H19 0.9500 . ? C21 C22 1.410(6) . ? C21 C26 1.419(7) . ? C22 C23 1.363(7) . ? C22 H22 0.9500 . ? C23 C24 1.382(7) . ? C24 C25 1.387(6) . ? C24 H24 0.9500 . ? C25 C26 1.389(7) . ? C26 C27 1.481(6) . ? C27 C28 1.384(7) . ? C28 C29 1.423(6) . ? C28 H28 0.9500 . ? C29 C30 1.420(7) . ? C30 C31 1.370(7) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.365(6) . ? C34 H34 0.9500 . ? C35 C36 1.421(7) . ? C35 H35 0.9500 . ? C36 C37 1.400(7) . ? C37 C38 1.399(6) . ? C37 H37 0.9500 . ? C38 C39 1.475(7) . ? C39 C40 1.395(7) . ? C39 C44 1.438(6) . ? C40 C41 1.379(7) . ? C41 C42 1.386(7) . ? C41 H41 0.9500 . ? C42 C43 1.371(8) . ? C43 C44 1.416(7) . ? C43 H43 0.9500 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 C48 1.370(7) . ? C47 H47 0.9500 . ? C48 C49 1.399(8) . ? C48 H48 0.9500 . ? C49 C50 1.418(7) . ? C50 C51 1.393(6) . ? C50 H50 0.9500 . ? C51 C52 1.488(7) . ? C52 C53 1.389(7) . ? C52 C57 1.418(6) . ? C53 C54 1.379(7) . ? C54 C55 1.393(7) . ? C54 H54 0.9500 . ? C55 C56 1.373(7) . ? C56 C57 1.410(7) . ? C56 H56 0.9500 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C62 C63 1.377(8) . ? C62 H62 0.9500 . ? C63 C64 1.406(9) . ? C63 H63 0.9500 . ? C64 C65 1.410(10) . ? C65 C66 1.374(8) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C67 H67A 0.9800 . ? C67 H67B 0.9800 . ? C67 H67C 0.9800 . ? C68 H68A 0.9800 . ? C68 H68B 0.9800 . ? C68 H68C 0.9800 . ? C69 C70 1.372(8) . ? C69 H69 0.9500 . ? C70 C71 1.415(8) . ? C70 H70 0.9500 . ? C71 C72 1.411(7) . ? C72 C73 1.391(8) . ? C72 H72 0.9500 . ? C73 C74 1.474(7) . ? C74 C75 1.407(7) . ? C74 C79 1.426(8) . ? C75 C76 1.383(8) . ? C76 C77 1.397(9) . ? C76 H76 0.9500 . ? C77 C78 1.370(7) . ? C78 C79 1.406(7) . ? C78 H78 0.9500 . ? C80 C85 1.404(8) . ? C80 C81 1.413(7) . ? C81 C82 1.381(8) . ? C81 H81 0.9500 . ? C82 C83 1.377(9) . ? C83 C84 1.388(8) . ? C83 H83 0.9500 . ? C84 C85 1.392(7) . ? C85 C86 1.491(7) . ? C86 C87 1.379(8) . ? C87 C88 1.418(8) . ? C87 H87 0.9500 . ? C88 C89 1.418(8) . ? C89 C90 1.365(8) . ? C89 H89 0.9500 . ? C90 H90 0.9500 . ? C91 H91A 0.9800 . ? C91 H91B 0.9800 . ? C91 H91C 0.9800 . ? C92 H92A 0.9800 . ? C92 H92B 0.9800 . ? C92 H92C 0.9800 . ? C93 H93A 0.9800 . ? C93 H93B 0.9800 . ? C93 H93C 0.9800 . ? C94 H94A 0.9800 . ? C94 H94B 0.9800 . ? C94 H94C 0.9800 . ? C95 C96 1.370(7) . ? C95 H95 0.9500 . ? C96 C97 1.401(7) . ? C96 H96 0.9500 . ? C97 C98 1.415(7) . ? C98 C99 1.391(7) . ? C98 H98 0.9500 . ? C99 C100 1.472(7) . ? C100 C101 1.403(7) . ? C100 C105 1.422(7) . ? C101 C102 1.385(7) . ? C102 C103 1.381(7) . ? C102 H102 0.9500 . ? C103 C104 1.379(7) . ? C104 C105 1.404(7) . ? C104 H104 0.9500 . ? C106 H10A 0.9800 . ? C106 H10B 0.9800 . ? C106 H10C 0.9800 . ? C107 H10D 0.9800 . ? C107 H10E 0.9800 . ? C107 H10F 0.9800 . ? C108 C109 1.394(8) . ? C108 C113 1.434(7) . ? C109 C110 1.360(8) . ? C109 H109 0.9500 . ? C110 C111 1.386(8) . ? C111 C112 1.374(9) . ? C111 H111 0.9500 . ? C112 C113 1.386(8) . ? C113 C114 1.488(8) . ? C114 C115 1.392(7) . ? C115 C116 1.408(8) . ? C115 H115 0.9500 . ? C116 C117 1.413(8) . ? C117 C118 1.381(7) . ? C117 H117 0.9500 . ? C118 H118 0.9500 . ? C119 H11A 0.9800 . ? C119 H11B 0.9800 . ? C119 H11C 0.9800 . ? C120 H12A 0.9800 . ? C120 H12B 0.9800 . ? C120 H12C 0.9800 . ? C121 H12D 0.9800 . ? C121 H12E 0.9800 . ? C121 H12F 0.9800 . ? C122 H12G 0.9800 . ? C122 H12H 0.9800 . ? C122 H12I 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 C21 Ir1 C1 86.8(2) . . ? C21 Ir1 C20 93.5(2) . . ? C1 Ir1 C20 175.26(18) . . ? C21 Ir1 N7 80.28(17) . . ? C1 Ir1 N7 91.93(17) . . ? C20 Ir1 N7 92.79(18) . . ? C21 Ir1 N5 94.46(17) . . ? C1 Ir1 N5 95.44(17) . . ? C20 Ir1 N5 79.82(19) . . ? N7 Ir1 N5 170.71(16) . . ? C21 Ir1 N3 177.75(19) . . ? C1 Ir1 N3 90.95(18) . . ? C20 Ir1 N3 88.75(18) . . ? N7 Ir1 N3 99.43(15) . . ? N5 Ir1 N3 86.12(15) . . ? C44 Ir2 C57 87.2(2) . . ? C44 Ir2 N11 98.23(18) . . ? C57 Ir2 N11 79.92(17) . . ? C44 Ir2 N9 80.14(18) . . ? C57 Ir2 N9 93.69(17) . . ? N11 Ir2 N9 173.50(16) . . ? C44 Ir2 C2 88.4(2) . . ? C57 Ir2 C2 173.0(2) . . ? N11 Ir2 C2 95.43(18) . . ? N9 Ir2 C2 90.82(17) . . ? C44 Ir2 N1 172.20(17) . . ? C57 Ir2 N1 87.78(18) . . ? N11 Ir2 N1 86.73(16) . . ? N9 Ir2 N1 94.25(15) . . ? C2 Ir2 N1 97.17(18) . . ? C79 Ir3 C80 86.3(2) . . ? C79 Ir3 C60 90.69(19) . . ? C80 Ir3 C60 173.7(2) . . ? C79 Ir3 N19 94.30(19) . . ? C80 Ir3 N19 79.8(2) . . ? C60 Ir3 N19 94.90(19) . . ? C79 Ir3 N17 80.31(19) . . ? C80 Ir3 N17 90.3(2) . . ? C60 Ir3 N17 94.60(19) . . ? N19 Ir3 N17 169.13(17) . . ? C79 Ir3 N15 178.70(19) . . ? C80 Ir3 N15 92.41(18) . . ? C60 Ir3 N15 90.57(18) . . ? N19 Ir3 N15 85.28(17) . . ? N17 Ir3 N15 99.90(17) . . ? C105 Ir4 C108 89.7(2) . . ? C105 Ir4 N23 97.27(17) . . ? C108 Ir4 N23 80.14(18) . . ? C105 Ir4 N21 80.14(18) . . ? C108 Ir4 N21 92.88(18) . . ? N23 Ir4 N21 172.61(17) . . ? C105 Ir4 C61 86.9(2) . . ? C108 Ir4 C61 172.2(2) . . ? N23 Ir4 C61 93.39(19) . . ? N21 Ir4 C61 93.38(19) . . ? C105 Ir4 N13 174.21(18) . . ? C108 Ir4 N13 89.11(17) . . ? N23 Ir4 N13 88.11(15) . . ? N21 Ir4 N13 94.26(15) . . ? C61 Ir4 N13 94.98(18) . . ? C1 N1 Ir2 163.3(4) . . ? C7 N3 C3 115.9(5) . . ? C7 N3 Ir1 123.9(4) . . ? C3 N3 Ir1 119.4(4) . . ? C5 N4 C8 119.7(7) . . ? C5 N4 C9 118.8(7) . . ? C8 N4 C9 118.6(7) . . ? C10 N5 C14 118.0(4) . . ? C10 N5 Ir1 125.0(4) . . ? C14 N5 Ir1 117.0(3) . . ? C12 N6 C122 121.8(6) . . ? C12 N6 C121 119.8(5) . . ? C122 N6 C121 117.6(5) . . ? C31 N7 C27 117.5(4) . . ? C31 N7 Ir1 125.6(3) . . ? C27 N7 Ir1 116.5(3) . . ? C29 N8 C32 119.8(4) . . ? C29 N8 C33 120.8(4) . . ? C32 N8 C33 119.3(4) . . ? C34 N9 C38 118.9(4) . . ? C34 N9 Ir2 123.9(3) . . ? C38 N9 Ir2 117.2(3) . . ? C36 N10 C45 120.9(4) . . ? C36 N10 C46 120.4(5) . . ? C45 N10 C46 117.1(4) . . ? C47 N11 C51 117.7(4) . . ? C47 N11 Ir2 124.9(3) . . ? C51 N11 Ir2 117.1(3) . . ? C49 N12 C59 120.2(5) . . ? C49 N12 C58 119.9(5) . . ? C59 N12 C58 119.2(4) . . ? C60 N13 Ir4 167.5(4) . . ? C66 N15 C62 115.3(5) . . ? C66 N15 Ir3 124.4(4) . . ? C62 N15 Ir3 119.9(4) . . ? C64 N16 C67 120.2(7) . . ? C64 N16 C68 120.6(7) . . ? C67 N16 C68 118.6(6) . . ? C69 N17 C73 117.3(4) . . ? C69 N17 Ir3 125.5(4) . . ? C73 N17 Ir3 115.8(3) . . ? C71 N18 C92 119.9(5) . . ? C71 N18 C91 120.2(5) . . ? C92 N18 C91 119.8(5) . . ? C90 N19 C86 117.3(5) . . ? C90 N19 Ir3 125.4(4) . . ? C86 N19 Ir3 117.2(4) . . ? C88 N20 C94 120.5(6) . . ? C88 N20 C93 120.6(6) . . ? C94 N20 C93 118.8(6) . . ? C95 N21 C99 117.9(4) . . ? C95 N21 Ir4 124.9(3) . . ? C99 N21 Ir4 117.1(3) . . ? C97 N22 C106 121.4(5) . . ? C97 N22 C107 121.8(5) . . ? C106 N22 C107 116.1(5) . . ? C118 N23 C114 118.5(4) . . ? C118 N23 Ir4 123.8(3) . . ? C114 N23 Ir4 117.5(3) . . ? C116 N24 C119 120.5(5) . . ? C116 N24 C120 120.2(5) . . ? C119 N24 C120 117.4(4) . . ? N1 C1 Ir1 173.8(4) . . ? N2 C2 Ir2 175.2(5) . . ? N3 C3 C4 124.0(5) . . ? N3 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? C3 C4 C5 120.1(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N4 C5 C4 121.6(7) . . ? N4 C5 C6 122.2(7) . . ? C4 C5 C6 116.2(6) . . ? C7 C6 C5 119.6(6) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N3 C7 C6 123.8(6) . . ? N3 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 C11 123.4(5) . . ? N5 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C10 C11 C12 119.9(5) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N6 C12 C13 121.8(5) . . ? N6 C12 C11 122.6(5) . . ? C13 C12 C11 115.7(5) . . ? C14 C13 C12 122.0(5) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? N5 C14 C13 120.8(5) . . ? N5 C14 C15 113.9(4) . . ? C13 C14 C15 125.2(5) . . ? C16 C15 C20 118.1(5) . . ? C16 C15 C14 126.6(5) . . ? C20 C15 C14 115.3(5) . . ? F1 C16 C17 116.0(5) . . ? F1 C16 C15 120.2(5) . . ? C17 C16 C15 123.8(5) . . ? C16 C17 C18 116.5(5) . . ? C16 C17 H17 121.7 . . ? C18 C17 H17 121.7 . . ? F2 C18 C19 119.0(5) . . ? F2 C18 C17 117.6(5) . . ? C19 C18 C17 123.4(5) . . ? C18 C19 C20 120.1(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 118.1(5) . . ? C19 C20 Ir1 128.0(4) . . ? C15 C20 Ir1 113.9(4) . . ? C22 C21 C26 118.6(4) . . ? C22 C21 Ir1 126.5(4) . . ? C26 C21 Ir1 114.8(3) . . ? C23 C22 C21 119.2(5) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 124.5(4) . . ? C22 C23 F3 118.6(4) . . ? C24 C23 F3 116.9(4) . . ? C23 C24 C25 115.7(5) . . ? C23 C24 H24 122.2 . . ? C25 C24 H24 122.2 . . ? F4 C25 C24 115.9(4) . . ? F4 C25 C26 120.6(4) . . ? C24 C25 C26 123.5(5) . . ? C25 C26 C21 118.6(4) . . ? C25 C26 C27 125.9(4) . . ? C21 C26 C27 115.5(4) . . ? N7 C27 C28 121.1(4) . . ? N7 C27 C26 112.8(4) . . ? C28 C27 C26 126.1(4) . . ? C27 C28 C29 121.3(5) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? N8 C29 C30 121.8(4) . . ? N8 C29 C28 122.0(5) . . ? C30 C29 C28 116.1(4) . . ? C31 C30 C29 119.3(4) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? N7 C31 C30 124.5(5) . . ? N7 C31 H31 117.8 . . ? C30 C31 H31 117.8 . . ? N8 C32 H32A 109.5 . . ? N8 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N8 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N8 C33 H33A 109.5 . . ? N8 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N8 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N9 C34 C35 123.6(5) . . ? N9 C34 H34 118.2 . . ? C35 C34 H34 118.2 . . ? C34 C35 C36 119.4(5) . . ? C34 C35 H35 120.3 . . ? C36 C35 H35 120.3 . . ? N10 C36 C37 122.9(5) . . ? N10 C36 C35 120.3(5) . . ? C37 C36 C35 116.9(4) . . ? C38 C37 C36 121.0(5) . . ? C38 C37 H37 119.5 . . ? C36 C37 H37 119.5 . . ? N9 C38 C37 120.2(4) . . ? N9 C38 C39 112.4(4) . . ? C37 C38 C39 127.4(4) . . ? C40 C39 C44 118.3(4) . . ? C40 C39 C38 126.3(4) . . ? C44 C39 C38 115.3(4) . . ? F5 C40 C41 116.3(5) . . ? F5 C40 C39 120.1(4) . . ? C41 C40 C39 123.7(4) . . ? C40 C41 C42 116.6(5) . . ? C40 C41 H41 121.7 . . ? C42 C41 H41 121.7 . . ? C43 C42 F6 119.3(4) . . ? C43 C42 C41 123.5(5) . . ? F6 C42 C41 117.1(5) . . ? C42 C43 C44 120.0(5) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C39 117.8(5) . . ? C43 C44 Ir2 127.4(4) . . ? C39 C44 Ir2 114.8(4) . . ? N10 C45 H45A 109.5 . . ? N10 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? N10 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? N10 C46 H46A 109.5 . . ? N10 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? N10 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? N11 C47 C48 124.4(5) . . ? N11 C47 H47 117.8 . . ? C48 C47 H47 117.8 . . ? C47 C48 C49 119.1(5) . . ? C47 C48 H48 120.5 . . ? C49 C48 H48 120.5 . . ? N12 C49 C48 121.2(5) . . ? N12 C49 C50 121.3(5) . . ? C48 C49 C50 117.5(4) . . ? C51 C50 C49 120.5(5) . . ? C51 C50 H50 119.7 . . ? C49 C50 H50 119.7 . . ? N11 C51 C50 120.7(5) . . ? N11 C51 C52 112.6(4) . . ? C50 C51 C52 126.7(5) . . ? C53 C52 C57 118.3(5) . . ? C53 C52 C51 126.1(4) . . ? C57 C52 C51 115.5(4) . . ? F7 C53 C54 115.2(5) . . ? F7 C53 C52 120.9(5) . . ? C54 C53 C52 123.9(5) . . ? C53 C54 C55 116.4(5) . . ? C53 C54 H54 121.8 . . ? C55 C54 H54 121.8 . . ? F8 C55 C56 118.8(5) . . ? F8 C55 C54 118.5(5) . . ? C56 C55 C54 122.7(5) . . ? C55 C56 C57 120.1(5) . . ? C55 C56 H56 119.9 . . ? C57 C56 H56 119.9 . . ? C56 C57 C52 118.5(5) . . ? C56 C57 Ir2 126.8(4) . . ? C52 C57 Ir2 114.7(4) . . ? N12 C58 H58A 109.5 . . ? N12 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? N12 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? N12 C59 H59A 109.5 . . ? N12 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? N12 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? N13 C60 Ir3 171.9(5) . . ? N14 C61 Ir4 175.6(5) . . ? N15 C62 C63 123.9(6) . . ? N15 C62 H62 118.0 . . ? C63 C62 H62 118.0 . . ? C62 C63 C64 120.7(6) . . ? C62 C63 H63 119.6 . . ? C64 C63 H63 119.6 . . ? N16 C64 C63 122.3(7) . . ? N16 C64 C65 122.5(7) . . ? C63 C64 C65 115.3(5) . . ? C66 C65 C64 120.1(6) . . ? C66 C65 H65 120.0 . . ? C64 C65 H65 120.0 . . ? N15 C66 C65 124.7(6) . . ? N15 C66 H66 117.7 . . ? C65 C66 H66 117.7 . . ? N16 C67 H67A 109.5 . . ? N16 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? N16 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? N16 C68 H68A 109.5 . . ? N16 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? N16 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? N17 C69 C70 125.0(5) . . ? N17 C69 H69 117.5 . . ? C70 C69 H69 117.5 . . ? C69 C70 C71 118.6(5) . . ? C69 C70 H70 120.7 . . ? C71 C70 H70 120.7 . . ? N18 C71 C72 121.4(5) . . ? N18 C71 C70 121.3(5) . . ? C72 C71 C70 117.3(5) . . ? C73 C72 C71 120.5(5) . . ? C73 C72 H72 119.7 . . ? C71 C72 H72 119.7 . . ? N17 C73 C72 121.3(5) . . ? N17 C73 C74 113.1(4) . . ? C72 C73 C74 125.6(5) . . ? C75 C74 C79 117.9(5) . . ? C75 C74 C73 126.9(5) . . ? C79 C74 C73 115.2(5) . . ? F9 C75 C76 116.6(5) . . ? F9 C75 C74 119.7(5) . . ? C76 C75 C74 123.7(6) . . ? C75 C76 C77 116.1(5) . . ? C75 C76 H76 122.0 . . ? C77 C76 H76 122.0 . . ? F10 C77 C78 118.7(5) . . ? F10 C77 C76 117.7(5) . . ? C78 C77 C76 123.6(5) . . ? C77 C78 C79 119.8(5) . . ? C77 C78 H78 120.1 . . ? C79 C78 H78 120.1 . . ? C78 C79 C74 118.9(5) . . ? C78 C79 Ir3 126.2(4) . . ? C74 C79 Ir3 114.8(4) . . ? C85 C80 C81 118.3(5) . . ? C85 C80 Ir3 114.2(4) . . ? C81 C80 Ir3 127.1(4) . . ? C82 C81 C80 120.7(6) . . ? C82 C81 H81 119.6 . . ? C80 C81 H81 119.6 . . ? F11 C82 C83 118.7(5) . . ? F11 C82 C81 119.4(6) . . ? C83 C82 C81 121.8(5) . . ? C82 C83 C84 117.1(5) . . ? C82 C83 H83 121.5 . . ? C84 C83 H83 121.5 . . ? F12 C84 C83 116.3(5) . . ? F12 C84 C85 120.1(5) . . ? C83 C84 C85 123.6(6) . . ? C84 C85 C80 118.4(5) . . ? C84 C85 C86 125.1(5) . . ? C80 C85 C86 116.4(5) . . ? N19 C86 C87 121.1(5) . . ? N19 C86 C85 112.1(5) . . ? C87 C86 C85 126.8(5) . . ? C86 C87 C88 121.5(5) . . ? C86 C87 H87 119.2 . . ? C88 C87 H87 119.2 . . ? N20 C88 C89 121.5(6) . . ? N20 C88 C87 122.1(6) . . ? C89 C88 C87 116.3(5) . . ? C90 C89 C88 118.9(5) . . ? C90 C89 H89 120.6 . . ? C88 C89 H89 120.6 . . ? N19 C90 C89 124.9(5) . . ? N19 C90 H90 117.6 . . ? C89 C90 H90 117.6 . . ? N18 C91 H91A 109.5 . . ? N18 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? N18 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? N18 C92 H92A 109.5 . . ? N18 C92 H92B 109.5 . . ? H92A C92 H92B 109.5 . . ? N18 C92 H92C 109.5 . . ? H92A C92 H92C 109.5 . . ? H92B C92 H92C 109.5 . . ? N20 C93 H93A 109.5 . . ? N20 C93 H93B 109.5 . . ? H93A C93 H93B 109.5 . . ? N20 C93 H93C 109.5 . . ? H93A C93 H93C 109.5 . . ? H93B C93 H93C 109.5 . . ? N20 C94 H94A 109.5 . . ? N20 C94 H94B 109.5 . . ? H94A C94 H94B 109.5 . . ? N20 C94 H94C 109.5 . . ? H94A C94 H94C 109.5 . . ? H94B C94 H94C 109.5 . . ? N21 C95 C96 124.3(5) . . ? N21 C95 H95 117.9 . . ? C96 C95 H95 117.9 . . ? C95 C96 C97 119.5(5) . . ? C95 C96 H96 120.3 . . ? C97 C96 H96 120.3 . . ? N22 C97 C96 122.1(5) . . ? N22 C97 C98 121.0(5) . . ? C96 C97 C98 116.9(5) . . ? C99 C98 C97 120.9(5) . . ? C99 C98 H98 119.5 . . ? C97 C98 H98 119.5 . . ? N21 C99 C98 120.4(4) . . ? N21 C99 C100 111.8(4) . . ? C98 C99 C100 127.9(4) . . ? C101 C100 C105 118.2(5) . . ? C101 C100 C99 125.2(4) . . ? C105 C100 C99 116.6(4) . . ? F13 C101 C102 116.3(4) . . ? F13 C101 C100 120.6(5) . . ? C102 C101 C100 123.1(5) . . ? C103 C102 C101 116.7(5) . . ? C103 C102 H102 121.7 . . ? C101 C102 H102 121.7 . . ? F14 C103 C104 118.7(5) . . ? F14 C103 C102 117.7(5) . . ? C104 C103 C102 123.7(5) . . ? C103 C104 C105 119.3(5) . . ? C103 C104 H104 120.4 . . ? C105 C104 H104 120.4 . . ? C104 C105 C100 119.1(4) . . ? C104 C105 Ir4 126.5(4) . . ? C100 C105 Ir4 114.4(3) . . ? N22 C106 H10A 109.5 . . ? N22 C106 H10B 109.5 . . ? H10A C106 H10B 109.5 . . ? N22 C106 H10C 109.5 . . ? H10A C106 H10C 109.5 . . ? H10B C106 H10C 109.5 . . ? N22 C107 H10D 109.5 . . ? N22 C107 H10E 109.5 . . ? H10D C107 H10E 109.5 . . ? N22 C107 H10F 109.5 . . ? H10D C107 H10F 109.5 . . ? H10E C107 H10F 109.5 . . ? C109 C108 C113 118.8(5) . . ? C109 C108 Ir4 127.7(4) . . ? C113 C108 Ir4 113.5(4) . . ? C110 C109 C108 120.0(5) . . ? C110 C109 H109 120.0 . . ? C108 C109 H109 120.0 . . ? C109 C110 F15 119.6(5) . . ? C109 C110 C111 123.4(6) . . ? F15 C110 C111 117.1(6) . . ? C112 C111 C110 116.2(6) . . ? C112 C111 H111 121.9 . . ? C110 C111 H111 121.9 . . ? C111 C112 F16 115.7(5) . . ? C111 C112 C113 124.3(5) . . ? F16 C112 C113 120.0(5) . . ? C112 C113 C108 117.3(5) . . ? C112 C113 C114 127.0(5) . . ? C108 C113 C114 115.7(5) . . ? N23 C114 C115 120.9(5) . . ? N23 C114 C113 113.2(4) . . ? C115 C114 C113 125.9(5) . . ? C114 C115 C116 121.2(5) . . ? C114 C115 H115 119.4 . . ? C116 C115 H115 119.4 . . ? N24 C116 C115 122.4(5) . . ? N24 C116 C117 120.8(5) . . ? C115 C116 C117 116.8(4) . . ? C118 C117 C116 119.4(5) . . ? C118 C117 H117 120.3 . . ? C116 C117 H117 120.3 . . ? N23 C118 C117 123.1(5) . . ? N23 C118 H118 118.4 . . ? C117 C118 H118 118.4 . . ? N24 C119 H11A 109.5 . . ? N24 C119 H11B 109.5 . . ? H11A C119 H11B 109.5 . . ? N24 C119 H11C 109.5 . . ? H11A C119 H11C 109.5 . . ? H11B C119 H11C 109.5 . . ? N24 C120 H12A 109.5 . . ? N24 C120 H12B 109.5 . . ? H12A C120 H12B 109.5 . . ? N24 C120 H12C 109.5 . . ? H12A C120 H12C 109.5 . . ? H12B C120 H12C 109.5 . . ? N6 C121 H12D 109.5 . . ? N6 C121 H12E 109.5 . . ? H12D C121 H12E 109.5 . . ? N6 C121 H12F 109.5 . . ? H12D C121 H12F 109.5 . . ? H12E C121 H12F 109.5 . . ? N6 C122 H12G 109.5 . . ? N6 C122 H12H 109.5 . . ? H12G C122 H12H 109.5 . . ? N6 C122 H12I 109.5 . . ? H12G C122 H12I 109.5 . . ? H12H C122 H12I 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 C57 Ir2 N1 C1 28.2(13) . . . . ? N11 Ir2 N1 C1 108.2(13) . . . . ? N9 Ir2 N1 C1 -65.3(13) . . . . ? C2 Ir2 N1 C1 -156.7(13) . . . . ? C1 Ir1 N3 C7 -155.7(4) . . . . ? C20 Ir1 N3 C7 29.0(4) . . . . ? N7 Ir1 N3 C7 -63.6(4) . . . . ? N5 Ir1 N3 C7 108.9(4) . . . . ? C1 Ir1 N3 C3 34.5(4) . . . . ? C20 Ir1 N3 C3 -140.8(4) . . . . ? N7 Ir1 N3 C3 126.6(4) . . . . ? N5 Ir1 N3 C3 -60.9(4) . . . . ? C21 Ir1 N5 C10 -84.1(4) . . . . ? C1 Ir1 N5 C10 3.1(4) . . . . ? C20 Ir1 N5 C10 -176.9(4) . . . . ? N3 Ir1 N5 C10 93.7(4) . . . . ? C21 Ir1 N5 C14 92.8(4) . . . . ? C1 Ir1 N5 C14 -179.9(3) . . . . ? C20 Ir1 N5 C14 0.1(3) . . . . ? N3 Ir1 N5 C14 -89.3(4) . . . . ? C21 Ir1 N7 C31 -174.1(5) . . . . ? C1 Ir1 N7 C31 99.4(4) . . . . ? C20 Ir1 N7 C31 -81.1(4) . . . . ? N3 Ir1 N7 C31 8.1(5) . . . . ? C21 Ir1 N7 C27 -1.2(4) . . . . ? C1 Ir1 N7 C27 -87.6(4) . . . . ? C20 Ir1 N7 C27 91.9(4) . . . . ? N3 Ir1 N7 C27 -178.9(4) . . . . ? C44 Ir2 N9 C34 178.2(4) . . . . ? C57 Ir2 N9 C34 -95.3(4) . . . . ? C2 Ir2 N9 C34 89.9(4) . . . . ? N1 Ir2 N9 C34 -7.3(4) . . . . ? C44 Ir2 N9 C38 -3.4(4) . . . . ? C57 Ir2 N9 C38 83.1(4) . . . . ? C2 Ir2 N9 C38 -91.6(4) . . . . ? N1 Ir2 N9 C38 171.1(4) . . . . ? C44 Ir2 N11 C47 -96.3(5) . . . . ? C57 Ir2 N11 C47 178.1(5) . . . . ? C2 Ir2 N11 C47 -7.1(5) . . . . ? N1 Ir2 N11 C47 89.8(4) . . . . ? C44 Ir2 N11 C51 89.6(4) . . . . ? C57 Ir2 N11 C51 4.0(4) . . . . ? C2 Ir2 N11 C51 178.8(4) . . . . ? N1 Ir2 N11 C51 -84.3(4) . . . . ? C108 Ir4 N13 C60 -43.4(18) . . . . ? N23 Ir4 N13 C60 -123.6(18) . . . . ? N21 Ir4 N13 C60 49.4(18) . . . . ? C61 Ir4 N13 C60 143.2(18) . . . . ? C80 Ir3 N15 C66 -34.8(5) . . . . ? C60 Ir3 N15 C66 150.8(5) . . . . ? N19 Ir3 N15 C66 -114.4(5) . . . . ? N17 Ir3 N15 C66 56.0(5) . . . . ? C80 Ir3 N15 C62 137.8(4) . . . . ? C60 Ir3 N15 C62 -36.6(4) . . . . ? N19 Ir3 N15 C62 58.2(4) . . . . ? N17 Ir3 N15 C62 -131.4(4) . . . . ? C79 Ir3 N17 C69 173.5(5) . . . . ? C80 Ir3 N17 C69 87.3(4) . . . . ? C60 Ir3 N17 C69 -96.6(4) . . . . ? N19 Ir3 N17 C69 112.6(9) . . . . ? N15 Ir3 N17 C69 -5.2(4) . . . . ? C79 Ir3 N17 C73 7.6(4) . . . . ? C80 Ir3 N17 C73 -78.6(4) . . . . ? C60 Ir3 N17 C73 97.5(4) . . . . ? N19 Ir3 N17 C73 -53.3(10) . . . . ? N15 Ir3 N17 C73 -171.1(4) . . . . ? C79 Ir3 N19 C90 95.7(4) . . . . ? C80 Ir3 N19 C90 -178.9(4) . . . . ? C60 Ir3 N19 C90 4.6(4) . . . . ? N17 Ir3 N19 C90 155.4(8) . . . . ? N15 Ir3 N19 C90 -85.6(4) . . . . ? C79 Ir3 N19 C86 -84.5(4) . . . . ? C80 Ir3 N19 C86 1.0(4) . . . . ? C60 Ir3 N19 C86 -175.6(4) . . . . ? N17 Ir3 N19 C86 -24.7(11) . . . . ? N15 Ir3 N19 C86 94.3(4) . . . . ? C105 Ir4 N21 C95 177.7(5) . . . . ? C108 Ir4 N21 C95 88.5(4) . . . . ? C61 Ir4 N21 C95 -96.1(5) . . . . ? N13 Ir4 N21 C95 -0.8(5) . . . . ? C105 Ir4 N21 C99 0.1(4) . . . . ? C108 Ir4 N21 C99 -89.1(4) . . . . ? N23 Ir4 N21 C99 -69.9(14) . . . . ? C61 Ir4 N21 C99 86.4(4) . . . . ? N13 Ir4 N21 C99 -178.4(4) . . . . ? C105 Ir4 N23 C118 95.3(4) . . . . ? C108 Ir4 N23 C118 -176.3(4) . . . . ? N21 Ir4 N23 C118 164.3(11) . . . . ? C61 Ir4 N23 C118 8.0(4) . . . . ? N13 Ir4 N23 C118 -86.8(4) . . . . ? C105 Ir4 N23 C114 -88.9(4) . . . . ? C108 Ir4 N23 C114 -0.4(3) . . . . ? N21 Ir4 N23 C114 -19.9(14) . . . . ? C61 Ir4 N23 C114 -176.1(4) . . . . ? N13 Ir4 N23 C114 89.0(4) . . . . ? Ir2 N1 C1 Ir1 45(5) . . . . ? C21 Ir1 C1 N1 62(4) . . . . ? C20 Ir1 C1 N1 -32(5) . . . . ? N7 Ir1 C1 N1 142(4) . . . . ? N5 Ir1 C1 N1 -32(4) . . . . ? N3 Ir1 C1 N1 -118(4) . . . . ? C44 Ir2 C2 N2 -5(6) . . . . ? C57 Ir2 C2 N2 -56(6) . . . . ? N11 Ir2 C2 N2 -104(6) . . . . ? N9 Ir2 C2 N2 75(6) . . . . ? N1 Ir2 C2 N2 169(6) . . . . ? C7 N3 C3 C4 -2.9(8) . . . . ? Ir1 N3 C3 C4 167.8(4) . . . . ? N3 C3 C4 C5 -1.3(9) . . . . ? C8 N4 C5 C4 8.5(12) . . . . ? C9 N4 C5 C4 168.9(8) . . . . ? C8 N4 C5 C6 -171.5(8) . . . . ? C9 N4 C5 C6 -11.0(13) . . . . ? C3 C4 C5 N4 -174.4(6) . . . . ? C3 C4 C5 C6 5.5(9) . . . . ? N4 C5 C6 C7 174.3(7) . . . . ? C4 C5 C6 C7 -5.6(10) . . . . ? C3 N3 C7 C6 2.7(8) . . . . ? Ir1 N3 C7 C6 -167.5(5) . . . . ? C5 C6 C7 N3 1.6(11) . . . . ? C14 N5 C10 C11 1.8(7) . . . . ? Ir1 N5 C10 C11 178.7(4) . . . . ? N5 C10 C11 C12 0.7(8) . . . . ? C122 N6 C12 C13 170.2(6) . . . . ? C121 N6 C12 C13 0.3(9) . . . . ? C122 N6 C12 C11 -9.5(9) . . . . ? C121 N6 C12 C11 -179.4(6) . . . . ? C10 C11 C12 N6 177.0(5) . . . . ? C10 C11 C12 C13 -2.7(8) . . . . ? N6 C12 C13 C14 -177.1(5) . . . . ? C11 C12 C13 C14 2.6(8) . . . . ? C10 N5 C14 C13 -2.0(7) . . . . ? Ir1 N5 C14 C13 -179.2(4) . . . . ? C10 N5 C14 C15 178.6(4) . . . . ? Ir1 N5 C14 C15 1.4(5) . . . . ? C12 C13 C14 N5 -0.2(8) . . . . ? C12 C13 C14 C15 179.2(5) . . . . ? N5 C14 C15 C16 175.6(5) . . . . ? C13 C14 C15 C16 -3.8(8) . . . . ? N5 C14 C15 C20 -2.7(6) . . . . ? C13 C14 C15 C20 177.8(5) . . . . ? C20 C15 C16 F1 179.6(4) . . . . ? C14 C15 C16 F1 1.2(8) . . . . ? C20 C15 C16 C17 -1.3(8) . . . . ? C14 C15 C16 C17 -179.6(5) . . . . ? F1 C16 C17 C18 -180.0(5) . . . . ? C15 C16 C17 C18 0.8(8) . . . . ? C16 C17 C18 F2 180.0(5) . . . . ? C16 C17 C18 C19 -0.5(8) . . . . ? F2 C18 C19 C20 -179.8(4) . . . . ? C17 C18 C19 C20 0.7(8) . . . . ? C18 C19 C20 C15 -1.1(7) . . . . ? C18 C19 C20 Ir1 175.5(4) . . . . ? C16 C15 C20 C19 1.3(7) . . . . ? C14 C15 C20 C19 179.8(4) . . . . ? C16 C15 C20 Ir1 -175.7(4) . . . . ? C14 C15 C20 Ir1 2.8(5) . . . . ? C21 Ir1 C20 C19 87.8(4) . . . . ? C1 Ir1 C20 C19 -178(100) . . . . ? N7 Ir1 C20 C19 7.4(4) . . . . ? N5 Ir1 C20 C19 -178.3(5) . . . . ? N3 Ir1 C20 C19 -92.0(4) . . . . ? C21 Ir1 C20 C15 -95.5(4) . . . . ? C1 Ir1 C20 C15 -2(2) . . . . ? N7 Ir1 C20 C15 -175.9(3) . . . . ? N5 Ir1 C20 C15 -1.6(3) . . . . ? N3 Ir1 C20 C15 84.7(4) . . . . ? C1 Ir1 C21 C22 -84.1(5) . . . . ? C20 Ir1 C21 C22 91.2(5) . . . . ? N7 Ir1 C21 C22 -176.6(5) . . . . ? N5 Ir1 C21 C22 11.2(5) . . . . ? N3 Ir1 C21 C22 -94(4) . . . . ? C1 Ir1 C21 C26 90.8(4) . . . . ? C20 Ir1 C21 C26 -93.9(4) . . . . ? N7 Ir1 C21 C26 -1.7(4) . . . . ? N5 Ir1 C21 C26 -174.0(4) . . . . ? N3 Ir1 C21 C26 81(4) . . . . ? C26 C21 C22 C23 0.7(8) . . . . ? Ir1 C21 C22 C23 175.4(4) . . . . ? C21 C22 C23 C24 -0.5(9) . . . . ? C21 C22 C23 F3 179.1(5) . . . . ? C22 C23 C24 C25 -0.6(9) . . . . ? F3 C23 C24 C25 179.8(5) . . . . ? C23 C24 C25 F4 -179.3(5) . . . . ? C23 C24 C25 C26 1.5(9) . . . . ? F4 C25 C26 C21 179.5(5) . . . . ? C24 C25 C26 C21 -1.4(8) . . . . ? F4 C25 C26 C27 0.3(9) . . . . ? C24 C25 C26 C27 179.4(5) . . . . ? C22 C21 C26 C25 0.2(8) . . . . ? Ir1 C21 C26 C25 -175.1(4) . . . . ? C22 C21 C26 C27 179.5(5) . . . . ? Ir1 C21 C26 C27 4.2(6) . . . . ? C31 N7 C27 C28 -3.2(7) . . . . ? Ir1 N7 C27 C28 -176.7(4) . . . . ? C31 N7 C27 C26 177.2(4) . . . . ? Ir1 N7 C27 C26 3.7(6) . . . . ? C25 C26 C27 N7 174.1(5) . . . . ? C21 C26 C27 N7 -5.1(7) . . . . ? C25 C26 C27 C28 -5.5(9) . . . . ? C21 C26 C27 C28 175.3(5) . . . . ? N7 C27 C28 C29 3.7(8) . . . . ? C26 C27 C28 C29 -176.7(5) . . . . ? C32 N8 C29 C30 -175.1(5) . . . . ? C33 N8 C29 C30 2.9(8) . . . . ? C32 N8 C29 C28 4.3(8) . . . . ? C33 N8 C29 C28 -177.7(5) . . . . ? C27 C28 C29 N8 179.3(5) . . . . ? C27 C28 C29 C30 -1.2(8) . . . . ? N8 C29 C30 C31 177.9(5) . . . . ? C28 C29 C30 C31 -1.6(8) . . . . ? C27 N7 C31 C30 0.3(8) . . . . ? Ir1 N7 C31 C30 173.1(4) . . . . ? C29 C30 C31 N7 2.1(8) . . . . ? C38 N9 C34 C35 -0.7(8) . . . . ? Ir2 N9 C34 C35 177.7(4) . . . . ? N9 C34 C35 C36 -0.2(9) . . . . ? C45 N10 C36 C37 169.9(6) . . . . ? C46 N10 C36 C37 4.6(9) . . . . ? C45 N10 C36 C35 -9.7(9) . . . . ? C46 N10 C36 C35 -175.0(5) . . . . ? C34 C35 C36 N10 179.7(5) . . . . ? C34 C35 C36 C37 0.1(8) . . . . ? N10 C36 C37 C38 -178.7(5) . . . . ? C35 C36 C37 C38 0.9(8) . . . . ? C34 N9 C38 C37 1.7(7) . . . . ? Ir2 N9 C38 C37 -176.8(4) . . . . ? C34 N9 C38 C39 -177.9(4) . . . . ? Ir2 N9 C38 C39 3.6(5) . . . . ? C36 C37 C38 N9 -1.8(8) . . . . ? C36 C37 C38 C39 177.7(5) . . . . ? N9 C38 C39 C40 175.5(5) . . . . ? C37 C38 C39 C40 -4.1(8) . . . . ? N9 C38 C39 C44 -1.5(6) . . . . ? C37 C38 C39 C44 178.9(5) . . . . ? C44 C39 C40 F5 178.0(4) . . . . ? C38 C39 C40 F5 1.1(8) . . . . ? C44 C39 C40 C41 -2.7(8) . . . . ? C38 C39 C40 C41 -179.7(5) . . . . ? F5 C40 C41 C42 -178.8(5) . . . . ? C39 C40 C41 C42 2.0(8) . . . . ? C40 C41 C42 C43 -0.7(8) . . . . ? C40 C41 C42 F6 179.1(5) . . . . ? F6 C42 C43 C44 -179.6(5) . . . . ? C41 C42 C43 C44 0.3(8) . . . . ? C42 C43 C44 C39 -1.0(8) . . . . ? C42 C43 C44 Ir2 179.8(4) . . . . ? C40 C39 C44 C43 2.2(7) . . . . ? C38 C39 C44 C43 179.4(4) . . . . ? C40 C39 C44 Ir2 -178.5(4) . . . . ? C38 C39 C44 Ir2 -1.3(6) . . . . ? C57 Ir2 C44 C43 87.4(5) . . . . ? N11 Ir2 C44 C43 8.0(5) . . . . ? N9 Ir2 C44 C43 -178.4(5) . . . . ? C2 Ir2 C44 C43 -87.2(5) . . . . ? N1 Ir2 C44 C43 137.2(11) . . . . ? C57 Ir2 C44 C39 -91.8(4) . . . . ? N11 Ir2 C44 C39 -171.2(4) . . . . ? N9 Ir2 C44 C39 2.4(4) . . . . ? C2 Ir2 C44 C39 93.5(4) . . . . ? N1 Ir2 C44 C39 -42.0(14) . . . . ? C51 N11 C47 C48 -0.3(8) . . . . ? Ir2 N11 C47 C48 -174.4(4) . . . . ? N11 C47 C48 C49 -1.4(9) . . . . ? C59 N12 C49 C48 178.4(6) . . . . ? C58 N12 C49 C48 -11.1(9) . . . . ? C59 N12 C49 C50 -1.9(9) . . . . ? C58 N12 C49 C50 168.6(6) . . . . ? C47 C48 C49 N12 -178.8(6) . . . . ? C47 C48 C49 C50 1.5(9) . . . . ? N12 C49 C50 C51 -179.8(5) . . . . ? C48 C49 C50 C51 -0.1(9) . . . . ? C47 N11 C51 C50 1.8(8) . . . . ? Ir2 N11 C51 C50 176.4(4) . . . . ? C47 N11 C51 C52 -179.2(5) . . . . ? Ir2 N11 C51 C52 -4.7(6) . . . . ? C49 C50 C51 N11 -1.6(8) . . . . ? C49 C50 C51 C52 179.6(5) . . . . ? N11 C51 C52 C53 -174.3(5) . . . . ? C50 C51 C52 C53 4.6(9) . . . . ? N11 C51 C52 C57 2.7(7) . . . . ? C50 C51 C52 C57 -178.5(5) . . . . ? C57 C52 C53 F7 177.5(5) . . . . ? C51 C52 C53 F7 -5.6(8) . . . . ? C57 C52 C53 C54 -0.3(8) . . . . ? C51 C52 C53 C54 176.6(5) . . . . ? F7 C53 C54 C55 -179.2(5) . . . . ? C52 C53 C54 C55 -1.3(9) . . . . ? C53 C54 C55 F8 -176.8(5) . . . . ? C53 C54 C55 C56 2.6(9) . . . . ? F8 C55 C56 C57 177.0(5) . . . . ? C54 C55 C56 C57 -2.4(8) . . . . ? C55 C56 C57 C52 0.7(8) . . . . ? C55 C56 C57 Ir2 -176.1(4) . . . . ? C53 C52 C57 C56 0.6(7) . . . . ? C51 C52 C57 C56 -176.6(5) . . . . ? C53 C52 C57 Ir2 177.8(4) . . . . ? C51 C52 C57 Ir2 0.6(6) . . . . ? C44 Ir2 C57 C56 75.7(5) . . . . ? N11 Ir2 C57 C56 174.6(5) . . . . ? N9 Ir2 C57 C56 -4.2(5) . . . . ? C2 Ir2 C57 C56 126.1(14) . . . . ? N1 Ir2 C57 C56 -98.4(5) . . . . ? C44 Ir2 C57 C52 -101.2(4) . . . . ? N11 Ir2 C57 C52 -2.3(4) . . . . ? N9 Ir2 C57 C52 178.9(4) . . . . ? C2 Ir2 C57 C52 -50.8(17) . . . . ? N1 Ir2 C57 C52 84.7(4) . . . . ? Ir4 N13 C60 Ir3 -10(5) . . . . ? C79 Ir3 C60 N13 -83(3) . . . . ? C80 Ir3 C60 N13 -22(4) . . . . ? N19 Ir3 C60 N13 11(3) . . . . ? N17 Ir3 C60 N13 -164(3) . . . . ? N15 Ir3 C60 N13 96(3) . . . . ? C105 Ir4 C61 N14 -46(6) . . . . ? C108 Ir4 C61 N14 18(7) . . . . ? N23 Ir4 C61 N14 51(6) . . . . ? N21 Ir4 C61 N14 -126(6) . . . . ? N13 Ir4 C61 N14 139(6) . . . . ? C66 N15 C62 C63 1.3(8) . . . . ? Ir3 N15 C62 C63 -171.9(5) . . . . ? N15 C62 C63 C64 -1.9(9) . . . . ? C67 N16 C64 C63 5.2(11) . . . . ? C68 N16 C64 C63 176.4(7) . . . . ? C67 N16 C64 C65 -175.1(7) . . . . ? C68 N16 C64 C65 -3.8(11) . . . . ? C62 C63 C64 N16 -179.5(6) . . . . ? C62 C63 C64 C65 0.7(9) . . . . ? N16 C64 C65 C66 -178.9(6) . . . . ? C63 C64 C65 C66 0.8(9) . . . . ? C62 N15 C66 C65 0.4(9) . . . . ? Ir3 N15 C66 C65 173.3(5) . . . . ? C64 C65 C66 N15 -1.5(10) . . . . ? C73 N17 C69 C70 2.9(8) . . . . ? Ir3 N17 C69 C70 -162.8(4) . . . . ? N17 C69 C70 C71 -2.8(9) . . . . ? C92 N18 C71 C72 0.3(10) . . . . ? C91 N18 C71 C72 177.1(6) . . . . ? C92 N18 C71 C70 -177.9(6) . . . . ? C91 N18 C71 C70 -1.2(10) . . . . ? C69 C70 C71 N18 178.6(6) . . . . ? C69 C70 C71 C72 0.2(8) . . . . ? N18 C71 C72 C73 -176.4(6) . . . . ? C70 C71 C72 C73 2.0(9) . . . . ? C69 N17 C73 C72 -0.4(8) . . . . ? Ir3 N17 C73 C72 166.7(4) . . . . ? C69 N17 C73 C74 -177.3(5) . . . . ? Ir3 N17 C73 C74 -10.2(6) . . . . ? C71 C72 C73 N17 -1.9(9) . . . . ? C71 C72 C73 C74 174.5(5) . . . . ? N17 C73 C74 C75 -176.2(5) . . . . ? C72 C73 C74 C75 7.1(9) . . . . ? N17 C73 C74 C79 7.4(7) . . . . ? C72 C73 C74 C79 -169.3(5) . . . . ? C79 C74 C75 F9 -178.4(5) . . . . ? C73 C74 C75 F9 5.3(9) . . . . ? C79 C74 C75 C76 0.5(9) . . . . ? C73 C74 C75 C76 -175.8(5) . . . . ? F9 C75 C76 C77 179.1(5) . . . . ? C74 C75 C76 C77 0.2(9) . . . . ? C75 C76 C77 F10 179.0(5) . . . . ? C75 C76 C77 C78 -1.2(9) . . . . ? F10 C77 C78 C79 -178.8(5) . . . . ? C76 C77 C78 C79 1.4(9) . . . . ? C77 C78 C79 C74 -0.6(8) . . . . ? C77 C78 C79 Ir3 176.7(4) . . . . ? C75 C74 C79 C78 -0.3(8) . . . . ? C73 C74 C79 C78 176.4(5) . . . . ? C75 C74 C79 Ir3 -177.9(4) . . . . ? C73 C74 C79 Ir3 -1.2(6) . . . . ? C80 Ir3 C79 C78 -89.7(5) . . . . ? C60 Ir3 C79 C78 84.8(5) . . . . ? N19 Ir3 C79 C78 -10.2(5) . . . . ? N17 Ir3 C79 C78 179.3(5) . . . . ? N15 Ir3 C79 C78 -81(9) . . . . ? C80 Ir3 C79 C74 87.7(4) . . . . ? C60 Ir3 C79 C74 -97.8(4) . . . . ? N19 Ir3 C79 C74 167.2(4) . . . . ? N17 Ir3 C79 C74 -3.3(4) . . . . ? N15 Ir3 C79 C74 96(9) . . . . ? C79 Ir3 C80 C85 91.8(4) . . . . ? C60 Ir3 C80 C85 30(2) . . . . ? N19 Ir3 C80 C85 -3.3(4) . . . . ? N17 Ir3 C80 C85 172.0(4) . . . . ? N15 Ir3 C80 C85 -88.0(4) . . . . ? C79 Ir3 C80 C81 -81.1(5) . . . . ? C60 Ir3 C80 C81 -142.7(18) . . . . ? N19 Ir3 C80 C81 -176.2(5) . . . . ? N17 Ir3 C80 C81 -0.8(4) . . . . ? N15 Ir3 C80 C81 99.1(4) . . . . ? C85 C80 C81 C82 -1.7(8) . . . . ? Ir3 C80 C81 C82 170.9(4) . . . . ? C80 C81 C82 F11 -178.3(5) . . . . ? C80 C81 C82 C83 2.0(8) . . . . ? F11 C82 C83 C84 179.4(5) . . . . ? C81 C82 C83 C84 -0.9(8) . . . . ? C82 C83 C84 F12 -177.9(5) . . . . ? C82 C83 C84 C85 -0.5(8) . . . . ? F12 C84 C85 C80 178.1(5) . . . . ? C83 C84 C85 C80 0.8(8) . . . . ? F12 C84 C85 C86 0.0(8) . . . . ? C83 C84 C85 C86 -177.4(5) . . . . ? C81 C80 C85 C84 0.3(7) . . . . ? Ir3 C80 C85 C84 -173.2(4) . . . . ? C81 C80 C85 C86 178.6(4) . . . . ? Ir3 C80 C85 C86 5.1(6) . . . . ? C90 N19 C86 C87 0.5(7) . . . . ? Ir3 N19 C86 C87 -179.3(4) . . . . ? C90 N19 C86 C85 -178.8(4) . . . . ? Ir3 N19 C86 C85 1.4(5) . . . . ? C84 C85 C86 N19 174.0(5) . . . . ? C80 C85 C86 N19 -4.2(6) . . . . ? C84 C85 C86 C87 -5.3(8) . . . . ? C80 C85 C86 C87 176.5(5) . . . . ? N19 C86 C87 C88 0.3(8) . . . . ? C85 C86 C87 C88 179.5(5) . . . . ? C94 N20 C88 C89 -0.6(12) . . . . ? C93 N20 C88 C89 176.0(8) . . . . ? C94 N20 C88 C87 -179.0(8) . . . . ? C93 N20 C88 C87 -2.4(12) . . . . ? C86 C87 C88 N20 177.1(6) . . . . ? C86 C87 C88 C89 -1.4(9) . . . . ? N20 C88 C89 C90 -176.8(6) . . . . ? C87 C88 C89 C90 1.7(9) . . . . ? C86 N19 C90 C89 -0.2(8) . . . . ? Ir3 N19 C90 C89 179.7(4) . . . . ? C88 C89 C90 N19 -1.0(9) . . . . ? C99 N21 C95 C96 -1.9(8) . . . . ? Ir4 N21 C95 C96 -179.4(4) . . . . ? N21 C95 C96 C97 -0.1(9) . . . . ? C106 N22 C97 C96 4.0(10) . . . . ? C107 N22 C97 C96 174.0(6) . . . . ? C106 N22 C97 C98 -178.5(6) . . . . ? C107 N22 C97 C98 -8.5(9) . . . . ? C95 C96 C97 N22 -179.9(6) . . . . ? C95 C96 C97 C98 2.5(9) . . . . ? N22 C97 C98 C99 179.3(5) . . . . ? C96 C97 C98 C99 -3.1(9) . . . . ? C95 N21 C99 C98 1.3(7) . . . . ? Ir4 N21 C99 C98 179.0(4) . . . . ? C95 N21 C99 C100 -178.8(5) . . . . ? Ir4 N21 C99 C100 -1.1(6) . . . . ? C97 C98 C99 N21 1.3(8) . . . . ? C97 C98 C99 C100 -178.6(5) . . . . ? N21 C99 C100 C101 -175.0(5) . . . . ? C98 C99 C100 C101 4.9(9) . . . . ? N21 C99 C100 C105 1.9(7) . . . . ? C98 C99 C100 C105 -178.2(5) . . . . ? C105 C100 C101 F13 -177.2(5) . . . . ? C99 C100 C101 F13 -0.3(9) . . . . ? C105 C100 C101 C102 2.4(9) . . . . ? C99 C100 C101 C102 179.3(6) . . . . ? F13 C101 C102 C103 178.9(5) . . . . ? C100 C101 C102 C103 -0.7(9) . . . . ? C101 C102 C103 F14 179.2(5) . . . . ? C101 C102 C103 C104 -0.1(10) . . . . ? F14 C103 C104 C105 179.9(5) . . . . ? C102 C103 C104 C105 -0.8(10) . . . . ? C103 C104 C105 C100 2.5(9) . . . . ? C103 C104 C105 Ir4 -175.9(5) . . . . ? C101 C100 C105 C104 -3.2(8) . . . . ? C99 C100 C105 C104 179.6(5) . . . . ? C101 C100 C105 Ir4 175.3(4) . . . . ? C99 C100 C105 Ir4 -1.9(6) . . . . ? C108 Ir4 C105 C104 -87.7(5) . . . . ? N23 Ir4 C105 C104 -7.7(5) . . . . ? N21 Ir4 C105 C104 179.3(5) . . . . ? C61 Ir4 C105 C104 85.4(5) . . . . ? N13 Ir4 C105 C104 -165.9(16) . . . . ? C108 Ir4 C105 C100 93.9(4) . . . . ? N23 Ir4 C105 C100 173.9(4) . . . . ? N21 Ir4 C105 C100 0.9(4) . . . . ? C61 Ir4 C105 C100 -93.1(4) . . . . ? N13 Ir4 C105 C100 16(2) . . . . ? C105 Ir4 C108 C109 -82.5(4) . . . . ? N23 Ir4 C108 C109 -179.9(5) . . . . ? N21 Ir4 C108 C109 -2.3(4) . . . . ? C61 Ir4 C108 C109 -146.2(12) . . . . ? N13 Ir4 C108 C109 91.9(4) . . . . ? C105 Ir4 C108 C113 98.1(4) . . . . ? N23 Ir4 C108 C113 0.6(3) . . . . ? N21 Ir4 C108 C113 178.2(3) . . . . ? C61 Ir4 C108 C113 34.4(15) . . . . ? N13 Ir4 C108 C113 -87.6(4) . . . . ? C113 C108 C109 C110 0.2(7) . . . . ? Ir4 C108 C109 C110 -179.3(4) . . . . ? C108 C109 C110 F15 179.4(5) . . . . ? C108 C109 C110 C111 -0.5(9) . . . . ? C109 C110 C111 C112 0.2(10) . . . . ? F15 C110 C111 C112 -179.6(6) . . . . ? C110 C111 C112 F16 179.8(6) . . . . ? C110 C111 C112 C113 0.3(10) . . . . ? C111 C112 C113 C108 -0.6(9) . . . . ? F16 C112 C113 C108 179.9(5) . . . . ? C111 C112 C113 C114 -179.9(6) . . . . ? F16 C112 C113 C114 0.6(9) . . . . ? C109 C108 C113 C112 0.4(7) . . . . ? Ir4 C108 C113 C112 179.9(4) . . . . ? C109 C108 C113 C114 179.7(4) . . . . ? Ir4 C108 C113 C114 -0.8(5) . . . . ? C118 N23 C114 C115 -2.3(7) . . . . ? Ir4 N23 C114 C115 -178.4(4) . . . . ? C118 N23 C114 C113 176.2(4) . . . . ? Ir4 N23 C114 C113 0.1(5) . . . . ? C112 C113 C114 N23 179.7(5) . . . . ? C108 C113 C114 N23 0.4(6) . . . . ? C112 C113 C114 C115 -1.9(9) . . . . ? C108 C113 C114 C115 178.9(5) . . . . ? N23 C114 C115 C116 1.1(7) . . . . ? C113 C114 C115 C116 -177.2(5) . . . . ? C119 N24 C116 C115 -3.0(8) . . . . ? C120 N24 C116 C115 -167.0(5) . . . . ? C119 N24 C116 C117 177.2(5) . . . . ? C120 N24 C116 C117 13.2(8) . . . . ? C114 C115 C116 N24 -178.7(5) . . . . ? C114 C115 C116 C117 1.1(7) . . . . ? N24 C116 C117 C118 177.7(5) . . . . ? C115 C116 C117 C118 -2.2(8) . . . . ? C114 N23 C118 C117 1.3(7) . . . . ? Ir4 N23 C118 C117 177.1(4) . . . . ? C116 C117 C118 N23 1.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 2.654 _refine_diff_density_min -1.413 _refine_diff_density_rms 0.138 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.151 1997 314 ' ' _platon_squeeze_details ; ;