Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Yun Chi.' 'Chau-Jiun Chang.' 'Kellen Chen' 'Pi-Tai Chou.' 'Mei-Lin Ho.' 'Ching-Fong Shu.' 'Cheng-Han Yang.' 'Yu-Shan Yeh.' _publ_contact_author_name 'Yun Chi' _publ_contact_author_address ; Department of Chemistry National Tsing Hua University Hsinchu 300 TAIWAN ; _publ_contact_author_email YCHI@MX.NTHU.EDU.TW _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Color Tuning Associated with the Heteroleptic Cyclometalated Ir(III) Complexes: Influence of the Ancillary Ligand ; data_ic12045 _database_code_depnum_ccdc_archive 'CCDC 634398' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H23 F4 Ir N8' _chemical_formula_weight 751.75 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4704(4) _cell_length_b 21.4926(8) _cell_length_c 12.0294(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.799(1) _cell_angle_gamma 90.00 _cell_volume 2706.79(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6050 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 26.12 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 4.996 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.4348 _exptl_absorpt_correction_T_max 0.6349 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _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 20650 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6207 _reflns_number_gt 5410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0311P)^2^+0.6663P] 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 6207 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.213523(14) 0.927075(8) 0.746888(15) 0.02136(6) Uani 1 1 d . . . N1 N 0.0375(4) 0.93167(18) 0.8353(3) 0.0292(9) Uani 1 1 d . . . N2 N -0.2096(4) 0.9510(2) 0.9141(4) 0.0413(11) Uani 1 1 d . . . N3 N 0.1894(3) 1.02299(17) 0.7738(3) 0.0220(8) Uani 1 1 d . . . N4 N 0.2560(3) 1.07512(17) 0.7502(3) 0.0233(8) Uani 1 1 d . . . N5 N 0.1193(3) 0.93169(17) 0.6016(3) 0.0254(8) Uani 1 1 d . . . N6 N 0.1931(3) 0.93069(17) 0.5083(3) 0.0246(8) Uani 1 1 d . . . N7 N 0.3208(3) 0.91092(18) 0.8833(3) 0.0259(9) Uani 1 1 d . . . N8 N 0.3525(4) 0.85018(18) 0.9018(3) 0.0294(9) Uani 1 1 d . . . C1 C -0.0403(5) 0.8841(2) 0.8611(4) 0.0335(12) Uani 1 1 d . . . H1A H -0.0104 0.8426 0.8533 0.040 Uiso 1 1 calc R . . C2 C -0.1626(5) 0.8942(3) 0.8988(5) 0.0402(14) Uani 1 1 d . . . H2A H -0.2150 0.8593 0.9143 0.048 Uiso 1 1 calc R . . C3 C -0.1315(5) 0.9978(2) 0.8903(4) 0.0363(12) Uani 1 1 d . . . H3A H -0.1617 1.0391 0.9005 0.044 Uiso 1 1 calc R . . C4 C -0.0074(4) 0.9899(2) 0.8512(4) 0.0265(10) Uani 1 1 d . . . C5 C 0.0773(4) 1.0393(2) 0.8215(4) 0.0269(10) Uani 1 1 d . . . C6 C 0.0711(4) 1.1040(2) 0.8284(4) 0.0312(11) Uani 1 1 d . . . H6A H 0.0041 1.1287 0.8573 0.037 Uiso 1 1 calc R . . C7 C 0.1850(4) 1.1239(2) 0.7835(4) 0.0260(10) Uani 1 1 d . A . C8 C 0.2286(4) 1.1906(2) 0.7648(4) 0.0269(11) Uani 1 1 d . . . C9 C 0.1417(11) 1.2381(5) 0.8136(12) 0.050(3) Uani 0.580(13) 1 d P A 1 H9A H 0.1276 1.2283 0.8921 0.075 Uiso 0.580(13) 1 calc PR A 1 H9B H 0.0598 1.2377 0.7732 0.075 Uiso 0.580(13) 1 calc PR A 1 H9C H 0.1807 1.2794 0.8076 0.075 Uiso 0.580(13) 1 calc PR A 1 C10 C 0.2318(13) 1.2060(4) 0.6344(9) 0.051(4) Uani 0.580(13) 1 d P A 1 H10A H 0.2828 1.1744 0.5963 0.077 Uiso 0.580(13) 1 calc PR A 1 H10B H 0.2702 1.2471 0.6233 0.077 Uiso 0.580(13) 1 calc PR A 1 H10C H 0.1446 1.2058 0.6038 0.077 Uiso 0.580(13) 1 calc PR A 1 C11 C 0.3637(14) 1.1981(8) 0.8047(16) 0.072(6) Uani 0.580(13) 1 d P A 1 H11A H 0.3681 1.1917 0.8853 0.108 Uiso 0.580(13) 1 calc PR A 1 H11B H 0.3936 1.2401 0.7870 0.108 Uiso 0.580(13) 1 calc PR A 1 H11C H 0.4179 1.1674 0.7679 0.108 Uiso 0.580(13) 1 calc PR A 1 C9' C 0.215(2) 1.2255(7) 0.8798(14) 0.058(6) Uani 0.420(13) 1 d P A 2 H9'A H 0.2517 1.1998 0.9394 0.088 Uiso 0.420(13) 1 calc PR A 2 H9'B H 0.1244 1.2330 0.8943 0.088 Uiso 0.420(13) 1 calc PR A 2 H9'C H 0.2603 1.2654 0.8768 0.088 Uiso 0.420(13) 1 calc PR A 2 C10' C 0.1407(15) 1.2176(7) 0.6809(15) 0.060(6) Uani 0.420(13) 1 d P A 2 H10D H 0.0523 1.2106 0.7035 0.091 Uiso 0.420(13) 1 calc PR A 2 H10E H 0.1548 1.1977 0.6088 0.091 Uiso 0.420(13) 1 calc PR A 2 H10F H 0.1566 1.2624 0.6747 0.091 Uiso 0.420(13) 1 calc PR A 2 C11' C 0.3652(17) 1.1968(10) 0.7333(17) 0.048(6) Uani 0.420(13) 1 d P A 2 H11D H 0.4194 1.1763 0.7893 0.072 Uiso 0.420(13) 1 calc PR A 2 H11E H 0.3878 1.2410 0.7291 0.072 Uiso 0.420(13) 1 calc PR A 2 H11F H 0.3782 1.1772 0.6607 0.072 Uiso 0.420(13) 1 calc PR A 2 C12 C 0.3621(4) 0.92848(19) 0.6434(4) 0.0234(9) Uani 1 1 d . . . C13 C 0.4926(4) 0.9259(2) 0.6680(4) 0.0276(10) Uani 1 1 d . . . H13A H 0.5222 0.9257 0.7430 0.033 Uiso 1 1 calc R . . C14 C 0.5782(4) 0.9238(2) 0.5817(4) 0.0297(11) Uani 1 1 d . . . C15 C 0.5454(4) 0.9256(2) 0.4711(4) 0.0316(11) Uani 1 1 d . . . H15A H 0.6076 0.9250 0.4143 0.038 Uiso 1 1 calc R . . C16 C 0.4161(4) 0.9285(2) 0.4478(4) 0.0278(10) Uani 1 1 d . . . C17 C 0.3272(4) 0.9295(2) 0.5305(4) 0.0232(9) Uani 1 1 d . . . C18 C 0.1184(5) 0.9247(2) 0.4166(4) 0.0338(11) Uani 1 1 d . . . H18A H 0.1466 0.9227 0.3419 0.041 Uiso 1 1 calc R . . C19 C -0.0058(5) 0.9221(2) 0.4512(5) 0.0371(12) Uani 1 1 d . . . H19A H -0.0800 0.9182 0.4054 0.045 Uiso 1 1 calc R . . C20 C -0.0017(4) 0.9264(2) 0.5664(5) 0.0341(12) Uani 1 1 d . . . H20A H -0.0741 0.9256 0.6131 0.041 Uiso 1 1 calc R . . C21 C 0.2286(4) 0.8343(2) 0.7369(4) 0.0253(10) Uani 1 1 d . . . C22 C 0.1810(4) 0.7941(2) 0.6548(4) 0.0291(11) Uani 1 1 d . . . H22A H 0.1300 0.8097 0.5951 0.035 Uiso 1 1 calc R . . C23 C 0.2090(5) 0.7314(2) 0.6614(5) 0.0357(12) Uani 1 1 d . . . C24 C 0.2786(5) 0.7048(2) 0.7452(5) 0.0399(13) Uani 1 1 d . . . H24A H 0.2952 0.6614 0.7469 0.048 Uiso 1 1 calc R . . C25 C 0.3237(5) 0.7439(2) 0.8271(5) 0.0371(12) Uani 1 1 d . . . C26 C 0.3021(4) 0.8072(2) 0.8231(4) 0.0297(11) Uani 1 1 d . . . C27 C 0.4303(5) 0.8456(3) 0.9909(4) 0.0392(13) Uani 1 1 d . . . H27A H 0.4655 0.8082 1.0202 0.047 Uiso 1 1 calc R . . C28 C 0.4503(5) 0.9037(3) 1.0318(5) 0.0385(12) Uani 1 1 d . . . H28A H 0.5017 0.9150 1.0943 0.046 Uiso 1 1 calc R . . C29 C 0.3796(5) 0.9434(2) 0.9631(4) 0.0317(11) Uani 1 1 d . . . H29A H 0.3742 0.9872 0.9719 0.038 Uiso 1 1 calc R . . F1 F 0.7057(3) 0.92166(15) 0.6078(3) 0.0488(9) Uani 1 1 d . . . F2 F 0.3779(3) 0.93076(13) 0.3397(2) 0.0379(7) Uani 1 1 d . . . F3 F 0.1645(3) 0.69327(13) 0.5784(3) 0.0434(8) Uani 1 1 d . . . F4 F 0.3930(3) 0.71969(15) 0.9129(3) 0.0567(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir 0.01777(8) 0.01891(10) 0.02761(11) -0.00253(8) 0.00838(6) -0.00156(7) N1 0.0241(18) 0.032(2) 0.031(2) -0.0051(19) 0.0120(16) -0.0050(17) N2 0.027(2) 0.045(3) 0.052(3) -0.011(2) 0.022(2) -0.0085(19) N3 0.0171(17) 0.021(2) 0.028(2) -0.0028(16) 0.0096(14) -0.0027(14) N4 0.0199(16) 0.0197(19) 0.030(2) -0.0028(17) 0.0035(15) -0.0029(14) N5 0.0183(17) 0.022(2) 0.036(2) -0.0048(18) 0.0067(15) 0.0007(15) N6 0.0250(18) 0.023(2) 0.026(2) -0.0046(17) 0.0041(15) 0.0015(16) N7 0.0221(18) 0.025(2) 0.031(2) -0.0006(17) 0.0097(16) -0.0041(15) N8 0.033(2) 0.023(2) 0.032(2) 0.0038(18) 0.0063(17) 0.0003(17) C1 0.037(3) 0.024(3) 0.040(3) -0.008(2) 0.014(2) -0.006(2) C2 0.033(3) 0.038(3) 0.051(4) -0.012(3) 0.023(2) -0.012(2) C3 0.032(3) 0.033(3) 0.045(3) -0.006(2) 0.018(2) -0.004(2) C4 0.024(2) 0.026(2) 0.030(3) -0.007(2) 0.0076(19) -0.0033(18) C5 0.020(2) 0.030(3) 0.031(3) -0.005(2) 0.0060(18) -0.0007(18) C6 0.025(2) 0.029(3) 0.039(3) -0.006(2) 0.008(2) 0.004(2) C7 0.023(2) 0.026(3) 0.029(3) -0.007(2) 0.0005(18) 0.0005(18) C8 0.030(2) 0.006(2) 0.044(3) 0.001(2) -0.002(2) 0.0044(17) C9 0.065(7) 0.020(5) 0.066(9) -0.001(5) 0.005(6) -0.006(5) C10 0.083(9) 0.017(5) 0.054(7) 0.007(4) 0.009(6) 0.002(5) C11 0.032(6) 0.036(7) 0.146(17) 0.018(12) -0.032(11) -0.008(5) C9' 0.098(14) 0.027(8) 0.051(11) -0.023(7) 0.053(10) -0.021(8) C10' 0.051(9) 0.033(8) 0.098(15) 0.039(9) 0.009(9) 0.009(7) C11' 0.024(7) 0.033(8) 0.088(15) 0.024(11) 0.014(10) 0.005(6) C12 0.0203(19) 0.015(2) 0.035(3) 0.001(2) 0.0089(18) 0.0003(17) C13 0.023(2) 0.028(2) 0.032(3) -0.002(2) 0.0036(18) -0.0029(19) C14 0.0157(19) 0.027(3) 0.046(3) 0.002(2) 0.0105(19) 0.0019(18) C15 0.030(2) 0.023(2) 0.043(3) -0.002(2) 0.021(2) -0.004(2) C16 0.033(2) 0.018(2) 0.032(3) -0.002(2) 0.010(2) -0.0045(19) C17 0.021(2) 0.020(2) 0.030(2) -0.003(2) 0.0053(17) 0.0011(17) C18 0.038(3) 0.030(3) 0.033(3) -0.009(2) 0.000(2) 0.000(2) C19 0.030(2) 0.034(3) 0.047(3) -0.012(3) -0.003(2) 0.000(2) C20 0.019(2) 0.036(3) 0.047(3) -0.009(3) 0.002(2) -0.003(2) C21 0.021(2) 0.021(2) 0.034(3) 0.001(2) 0.0143(19) -0.0052(17) C22 0.025(2) 0.024(3) 0.038(3) 0.000(2) 0.010(2) -0.0074(18) C23 0.036(3) 0.027(3) 0.044(3) -0.006(2) 0.017(2) -0.012(2) C24 0.044(3) 0.018(2) 0.058(4) 0.000(3) 0.019(3) -0.002(2) C25 0.037(3) 0.030(3) 0.045(3) 0.013(3) 0.014(2) 0.004(2) C26 0.031(2) 0.024(2) 0.035(3) 0.001(2) 0.012(2) -0.0063(19) C27 0.041(3) 0.037(3) 0.039(3) 0.011(3) -0.001(2) -0.003(2) C28 0.036(3) 0.039(3) 0.041(3) 0.007(3) -0.004(2) -0.007(2) C29 0.032(2) 0.029(3) 0.034(3) 0.000(2) 0.009(2) -0.004(2) F1 0.0177(13) 0.063(2) 0.066(2) -0.0014(18) 0.0109(13) 0.0028(14) F2 0.0459(17) 0.0381(17) 0.0302(16) -0.0091(14) 0.0107(13) -0.0096(13) F3 0.0454(17) 0.0262(16) 0.059(2) -0.0141(15) 0.0155(15) -0.0112(13) F4 0.073(2) 0.0310(17) 0.066(2) 0.0145(18) -0.0050(18) 0.0068(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir N5 1.998(4) . ? Ir C21 2.004(5) . ? Ir N7 2.005(4) . ? Ir C12 2.007(4) . ? Ir N3 2.102(4) . ? Ir N1 2.143(4) . ? N1 C1 1.346(6) . ? N1 C4 1.351(6) . ? N2 C2 1.330(7) . ? N2 C3 1.332(6) . ? N3 N4 1.352(5) . ? N3 C5 1.359(5) . ? N4 C7 1.349(6) . ? N5 C20 1.334(6) . ? N5 N6 1.371(5) . ? N6 C18 1.350(6) . ? N6 C17 1.426(5) . ? N7 C29 1.331(6) . ? N7 N8 1.365(5) . ? N8 C27 1.341(6) . ? N8 C26 1.419(6) . ? C1 C2 1.381(6) . ? C3 C4 1.398(6) . ? C4 C5 1.433(6) . ? C5 C6 1.395(7) . ? C6 C7 1.384(6) . ? C7 C8 1.522(6) . ? C8 C10' 1.475(15) . ? C8 C11' 1.491(18) . ? C8 C9 1.493(11) . ? C8 C11 1.496(14) . ? C8 C9' 1.582(14) . ? C8 C10 1.604(11) . ? C12 C13 1.395(6) . ? C12 C17 1.401(7) . ? C13 C14 1.381(7) . ? C14 F1 1.368(5) . ? C14 C15 1.370(7) . ? C15 C16 1.381(6) . ? C16 F2 1.356(6) . ? C16 C17 1.372(6) . ? C18 C19 1.372(7) . ? C19 C20 1.389(8) . ? C21 C22 1.399(6) . ? C21 C26 1.409(7) . ? C22 C23 1.380(7) . ? C23 C24 1.361(7) . ? C23 F3 1.369(6) . ? C24 C25 1.374(7) . ? C25 F4 1.357(6) . ? C25 C26 1.380(7) . ? C27 C28 1.357(8) . ? C28 C29 1.393(7) . ? 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 N5 Ir C21 92.02(17) . . ? N5 Ir N7 171.31(15) . . ? C21 Ir N7 80.40(17) . . ? N5 Ir C12 80.45(17) . . ? C21 Ir C12 85.16(16) . . ? N7 Ir C12 94.59(17) . . ? N5 Ir N3 91.54(14) . . ? C21 Ir N3 174.02(16) . . ? N7 Ir N3 96.38(15) . . ? C12 Ir N3 100.18(15) . . ? N5 Ir N1 90.81(15) . . ? C21 Ir N1 98.30(15) . . ? N7 Ir N1 94.46(15) . . ? C12 Ir N1 170.73(17) . . ? N3 Ir N1 76.83(14) . . ? C1 N1 C4 117.2(4) . . ? C1 N1 Ir 127.4(3) . . ? C4 N1 Ir 114.6(3) . . ? C2 N2 C3 115.8(4) . . ? N4 N3 C5 109.0(4) . . ? N4 N3 Ir 135.8(3) . . ? C5 N3 Ir 115.1(3) . . ? C7 N4 N3 107.0(4) . . ? C20 N5 N6 106.4(4) . . ? C20 N5 Ir 136.8(4) . . ? N6 N5 Ir 115.9(3) . . ? C18 N6 N5 110.1(4) . . ? C18 N6 C17 135.1(4) . . ? N5 N6 C17 114.3(4) . . ? C29 N7 N8 105.9(4) . . ? C29 N7 Ir 138.4(4) . . ? N8 N7 Ir 115.6(3) . . ? C27 N8 N7 110.1(4) . . ? C27 N8 C26 134.6(4) . . ? N7 N8 C26 115.2(4) . . ? N1 C1 C2 121.6(5) . . ? N2 C2 C1 122.4(5) . . ? N2 C3 C4 123.8(5) . . ? N1 C4 C3 119.2(4) . . ? N1 C4 C5 115.7(4) . . ? C3 C4 C5 125.1(4) . . ? N3 C5 C6 108.9(4) . . ? N3 C5 C4 117.1(4) . . ? C6 C5 C4 134.0(4) . . ? C7 C6 C5 104.1(4) . . ? N4 C7 C6 110.9(4) . . ? N4 C7 C8 121.4(4) . . ? C6 C7 C8 127.6(4) . . ? C10' C8 C11' 112.5(10) . . ? C10' C8 C9 67.8(8) . . ? C11' C8 C9 129.1(10) . . ? C10' C8 C11 139.0(9) . . ? C11' C8 C11 33.4(8) . . ? C9 C8 C11 112.2(9) . . ? C10' C8 C7 106.6(7) . . ? C11' C8 C7 114.4(9) . . ? C9 C8 C7 113.6(5) . . ? C11 C8 C7 109.8(7) . . ? C10' C8 C9' 110.4(11) . . ? C11' C8 C9' 106.2(11) . . ? C9 C8 C9' 43.0(7) . . ? C11 C8 C9' 76.4(10) . . ? C7 C8 C9' 106.7(6) . . ? C10' C8 C10 43.2(7) . . ? C11' C8 C10 72.5(8) . . ? C9 C8 C10 105.4(7) . . ? C11 C8 C10 105.0(9) . . ? C7 C8 C10 110.4(5) . . ? C9' C8 C10 139.5(8) . . ? C13 C12 C17 116.6(4) . . ? C13 C12 Ir 129.3(4) . . ? C17 C12 Ir 114.1(3) . . ? C14 C13 C12 119.0(5) . . ? F1 C14 C15 117.0(4) . . ? F1 C14 C13 118.0(5) . . ? C15 C14 C13 124.9(4) . . ? C14 C15 C16 115.4(4) . . ? F2 C16 C17 120.1(4) . . ? F2 C16 C15 118.1(4) . . ? C17 C16 C15 121.8(5) . . ? C16 C17 C12 122.1(4) . . ? C16 C17 N6 122.7(4) . . ? C12 C17 N6 115.1(4) . . ? N6 C18 C19 107.2(5) . . ? C18 C19 C20 106.5(5) . . ? N5 C20 C19 109.8(4) . . ? C22 C21 C26 116.7(4) . . ? C22 C21 Ir 129.1(4) . . ? C26 C21 Ir 114.2(3) . . ? C23 C22 C21 119.3(5) . . ? C24 C23 F3 117.5(5) . . ? C24 C23 C22 124.3(5) . . ? F3 C23 C22 118.2(5) . . ? C23 C24 C25 116.7(5) . . ? F4 C25 C24 119.1(5) . . ? F4 C25 C26 119.4(5) . . ? C24 C25 C26 121.5(5) . . ? C25 C26 C21 121.4(5) . . ? C25 C26 N8 124.0(5) . . ? C21 C26 N8 114.6(4) . . ? N8 C27 C28 108.2(5) . . ? C27 C28 C29 105.7(5) . . ? N7 C29 C28 110.1(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.935 _refine_diff_density_min -2.128 _refine_diff_density_rms 0.129