# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Yun Chi' _publ_contact_author_email YCHI@MX.NTHU.EDU.TW _publ_section_title ; Blue-Emitting Ir(III) Phosphors with Ancillary 4,6-Difluorobenzyl diphenylphosphine Based Cyclometalate ; loop_ _publ_author_name 'Yun Chi' 'Chung-Chia Chen' 'Yi-Ming Cheng' 'Pi-Tai Chou' 'Jui-Yi Hung' 'Gene-Hsiang Lee' ; I.-H.Pai ; 'Ken-Tsung Wong' 'Chung-Chih Wu' 'Ya-Chien Yu' # Attachment 'total-11.cif' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 725889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H27 Cl F6 Ir N2 P' _chemical_formula_sum 'C41 H27 Cl F6 Ir N2 P' _chemical_formula_weight 920.27 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' 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 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 10.9279(6) _cell_length_b 9.5832(6) _cell_length_c 34.0479(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.773(1) _cell_angle_gamma 90.00 _cell_volume 3553.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.42 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1800 _exptl_absorpt_coefficient_mu 3.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2882 _exptl_absorpt_correction_T_max 0.7978 _exptl_absorpt_process_details sadabs _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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24188 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8038 _reflns_number_gt 7208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0237P)^2^+7.0504P] 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 8038 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.693882(16) -0.064474(18) 0.620518(5) 0.01606(6) Uani 1 1 d . . . Cl1 Cl 0.72821(10) -0.20489(11) 0.68186(3) 0.0187(2) Uani 1 1 d . . . P1 P 0.78581(11) 0.13818(12) 0.65146(4) 0.0180(2) Uani 1 1 d . . . N1 N 0.8452(3) -0.1455(4) 0.59605(11) 0.0192(8) Uani 1 1 d . . . N2 N 0.5265(3) 0.0022(4) 0.63493(11) 0.0180(8) Uani 1 1 d . . . C1 C 0.6194(4) -0.2417(5) 0.59579(13) 0.0190(10) Uani 1 1 d . . . C2 C 0.5004(5) -0.2899(5) 0.59806(14) 0.0271(11) Uani 1 1 d . . . H2 H 0.4442 -0.2382 0.6122 0.033 Uiso 1 1 calc R . . C3 C 0.4642(5) -0.4127(6) 0.57977(17) 0.0336(13) Uani 1 1 d . . . C4 C 0.5407(5) -0.4914(5) 0.55831(16) 0.0334(13) Uani 1 1 d . . . H4 H 0.5125 -0.5740 0.5450 0.040 Uiso 1 1 calc R . . C5 C 0.6586(5) -0.4459(5) 0.55690(16) 0.0295(12) Uani 1 1 d . . . C6 C 0.7015(5) -0.3221(5) 0.57509(14) 0.0228(10) Uani 1 1 d . . . C7 C 0.8266(5) -0.2666(5) 0.57489(15) 0.0239(11) Uani 1 1 d . . . C8 C 0.9221(5) -0.3259(6) 0.55574(17) 0.0377(14) Uani 1 1 d . . . H8 H 0.9089 -0.4105 0.5415 0.045 Uiso 1 1 calc R . . C9 C 1.0353(6) -0.2619(7) 0.55753(19) 0.0457(16) Uani 1 1 d . . . H9 H 1.1008 -0.3025 0.5449 0.055 Uiso 1 1 calc R . . C10 C 1.0524(5) -0.1383(6) 0.57793(17) 0.0356(13) Uani 1 1 d . . . H10 H 1.1293 -0.0915 0.5792 0.043 Uiso 1 1 calc R . . C11 C 0.9569(5) -0.0844(5) 0.59630(15) 0.0254(11) Uani 1 1 d . . . H11 H 0.9695 0.0012 0.6101 0.030 Uiso 1 1 calc R . . C12 C 0.6382(4) 0.0382(4) 0.57088(13) 0.0178(9) Uani 1 1 d . . . C13 C 0.7036(4) 0.0558(5) 0.53736(14) 0.0217(10) Uani 1 1 d . . . H13 H 0.7849 0.0210 0.5370 0.026 Uiso 1 1 calc R . . C14 C 0.6483(5) 0.1240(5) 0.50502(14) 0.0239(11) Uani 1 1 d . . . C15 C 0.5312(5) 0.1750(5) 0.50311(14) 0.0235(10) Uani 1 1 d . . . H15 H 0.4952 0.2204 0.4802 0.028 Uiso 1 1 calc R . . C16 C 0.4681(4) 0.1575(5) 0.53606(14) 0.0220(10) Uani 1 1 d . . . C17 C 0.5176(4) 0.0919(4) 0.57009(13) 0.0183(9) Uani 1 1 d . . . C18 C 0.4556(4) 0.0714(5) 0.60627(13) 0.0192(9) Uani 1 1 d . . . C19 C 0.3378(5) 0.1154(5) 0.61340(15) 0.0265(11) Uani 1 1 d . . . H19 H 0.2886 0.1632 0.5934 0.032 Uiso 1 1 calc R . . C20 C 0.2924(5) 0.0900(6) 0.64918(16) 0.0317(12) Uani 1 1 d . . . H20 H 0.2119 0.1189 0.6541 0.038 Uiso 1 1 calc R . . C21 C 0.3666(5) 0.0215(6) 0.67790(16) 0.0313(12) Uani 1 1 d . . . H21 H 0.3379 0.0045 0.7031 0.038 Uiso 1 1 calc R . . C22 C 0.4808(5) -0.0215(5) 0.67005(15) 0.0259(11) Uani 1 1 d . . . H22 H 0.5301 -0.0698 0.6899 0.031 Uiso 1 1 calc R . . C23 C 0.8243(4) 0.2708(5) 0.61472(14) 0.0224(10) Uani 1 1 d . . . H23A H 0.8528 0.2211 0.5917 0.027 Uiso 1 1 calc R . . H23B H 0.7478 0.3205 0.6056 0.027 Uiso 1 1 calc R . . C24 C 0.9191(4) 0.3779(5) 0.62767(14) 0.0231(10) Uani 1 1 d . . . C25 C 1.0407(5) 0.3574(5) 0.62096(15) 0.0269(11) Uani 1 1 d . . . C26 C 1.1352(5) 0.4453(6) 0.63376(19) 0.0379(14) Uani 1 1 d . . . H26 H 1.2177 0.4274 0.6284 0.046 Uiso 1 1 calc R . . C27 C 1.1035(6) 0.5609(6) 0.65477(19) 0.0396(14) Uani 1 1 d . . . C28 C 0.9856(6) 0.5910(5) 0.66160(18) 0.0370(14) Uani 1 1 d . . . H28 H 0.9665 0.6730 0.6755 0.044 Uiso 1 1 calc R . . C29 C 0.8944(5) 0.4996(5) 0.64787(14) 0.0237(10) Uani 1 1 d . . . H29 H 0.8117 0.5205 0.6523 0.028 Uiso 1 1 calc R . . C30 C 0.6813(4) 0.2294(5) 0.68189(15) 0.0233(10) Uani 1 1 d . . . C31 C 0.5960(5) 0.3265(6) 0.66649(16) 0.0321(12) Uani 1 1 d . . . H31 H 0.5977 0.3554 0.6399 0.039 Uiso 1 1 calc R . . C32 C 0.5085(6) 0.3820(7) 0.68920(18) 0.0433(15) Uani 1 1 d . . . H32 H 0.4523 0.4501 0.6783 0.052 Uiso 1 1 calc R . . C33 C 0.5028(6) 0.3382(7) 0.72775(19) 0.0483(17) Uani 1 1 d . . . H33 H 0.4413 0.3741 0.7431 0.058 Uiso 1 1 calc R . . C34 C 0.5876(5) 0.2414(6) 0.74391(17) 0.0394(14) Uani 1 1 d . . . H34 H 0.5846 0.2120 0.7705 0.047 Uiso 1 1 calc R . . C35 C 0.6761(5) 0.1879(6) 0.72133(16) 0.0313(12) Uani 1 1 d . . . H35 H 0.7341 0.1224 0.7326 0.038 Uiso 1 1 calc R . . C36 C 0.9230(4) 0.1181(5) 0.68550(14) 0.0201(10) Uani 1 1 d . . . C37 C 0.9823(4) -0.0100(5) 0.68963(14) 0.0207(10) Uani 1 1 d . . . H37 H 0.9523 -0.0872 0.6742 0.025 Uiso 1 1 calc R . . C38 C 1.0856(5) -0.0262(5) 0.71630(14) 0.0249(11) Uani 1 1 d . . . H38 H 1.1253 -0.1143 0.7189 0.030 Uiso 1 1 calc R . . C39 C 1.1301(4) 0.0843(6) 0.73880(14) 0.0270(11) Uani 1 1 d . . . H39 H 1.1999 0.0728 0.7571 0.032 Uiso 1 1 calc R . . C40 C 1.0725(5) 0.2127(5) 0.73471(14) 0.0259(11) Uani 1 1 d . . . H40 H 1.1038 0.2898 0.7499 0.031 Uiso 1 1 calc R . . C41 C 0.9697(5) 0.2295(5) 0.70862(14) 0.0246(11) Uani 1 1 d . . . H41 H 0.9304 0.3179 0.7064 0.030 Uiso 1 1 calc R . . F1 F 0.3476(3) -0.4580(4) 0.58129(12) 0.0538(10) Uani 1 1 d . . . F2 F 0.7333(3) -0.5235(3) 0.53579(10) 0.0442(9) Uani 1 1 d . . . F3 F 0.7120(3) 0.1388(3) 0.47290(8) 0.0343(7) Uani 1 1 d . . . F4 F 0.3509(3) 0.2084(3) 0.53394(8) 0.0309(7) Uani 1 1 d . . . F5 F 1.0701(3) 0.2416(3) 0.60036(10) 0.0371(8) Uani 1 1 d . . . F6 F 1.1952(3) 0.6488(4) 0.66830(13) 0.0606(11) 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 0.01746(9) 0.01752(9) 0.01298(9) 0.00029(7) -0.00007(6) -0.00050(7) Cl1 0.0199(5) 0.0216(5) 0.0138(5) 0.0044(4) -0.0028(4) 0.0027(4) P1 0.0198(6) 0.0181(6) 0.0156(6) -0.0006(5) -0.0012(5) 0.0015(5) N1 0.020(2) 0.022(2) 0.015(2) 0.0012(16) 0.0012(16) 0.0032(16) N2 0.0177(19) 0.0192(19) 0.017(2) 0.0011(16) 0.0011(16) 0.0001(16) C1 0.028(3) 0.017(2) 0.011(2) 0.0049(17) -0.0041(19) -0.0019(19) C2 0.034(3) 0.029(3) 0.019(3) 0.002(2) 0.003(2) -0.008(2) C3 0.038(3) 0.033(3) 0.030(3) 0.005(2) -0.001(2) -0.016(2) C4 0.053(4) 0.020(2) 0.027(3) -0.002(2) 0.001(3) -0.011(2) C5 0.042(3) 0.021(2) 0.025(3) -0.004(2) 0.002(2) -0.002(2) C6 0.031(3) 0.020(2) 0.017(2) 0.0046(19) -0.004(2) -0.001(2) C7 0.027(3) 0.021(2) 0.024(3) 0.0004(19) -0.001(2) 0.007(2) C8 0.040(3) 0.030(3) 0.044(4) -0.017(3) 0.010(3) 0.002(3) C9 0.039(4) 0.048(4) 0.053(4) -0.015(3) 0.020(3) 0.008(3) C10 0.029(3) 0.040(3) 0.039(3) -0.007(3) 0.012(3) -0.002(2) C11 0.024(3) 0.025(3) 0.027(3) -0.004(2) 0.001(2) 0.000(2) C12 0.020(2) 0.017(2) 0.015(2) -0.0041(17) -0.0053(18) -0.0042(18) C13 0.022(2) 0.025(2) 0.017(2) -0.0019(19) 0.0010(19) -0.003(2) C14 0.031(3) 0.025(2) 0.016(2) 0.002(2) 0.002(2) -0.008(2) C15 0.032(3) 0.019(2) 0.019(2) 0.0019(19) -0.002(2) -0.002(2) C16 0.022(2) 0.018(2) 0.025(3) 0.0007(19) -0.005(2) 0.0025(19) C17 0.022(2) 0.017(2) 0.015(2) -0.0004(17) -0.0017(18) -0.0028(18) C18 0.021(2) 0.020(2) 0.017(2) 0.0003(18) 0.0010(18) -0.0017(19) C19 0.022(3) 0.034(3) 0.024(3) 0.006(2) 0.001(2) 0.004(2) C20 0.023(3) 0.039(3) 0.034(3) 0.003(2) 0.008(2) 0.003(2) C21 0.026(3) 0.046(3) 0.022(3) 0.006(2) 0.007(2) 0.004(2) C22 0.027(3) 0.032(3) 0.019(3) 0.002(2) 0.003(2) 0.001(2) C23 0.024(3) 0.021(2) 0.022(3) 0.0012(19) 0.001(2) -0.0015(19) C24 0.024(3) 0.022(2) 0.024(3) 0.000(2) 0.002(2) -0.002(2) C25 0.033(3) 0.021(2) 0.027(3) 0.001(2) 0.006(2) -0.001(2) C26 0.025(3) 0.037(3) 0.052(4) 0.002(3) 0.004(3) -0.005(2) C27 0.040(3) 0.029(3) 0.049(4) -0.005(3) -0.001(3) -0.014(3) C28 0.053(4) 0.019(3) 0.040(3) -0.003(2) 0.007(3) -0.001(2) C29 0.026(3) 0.018(2) 0.028(3) 0.007(2) 0.008(2) -0.001(2) C30 0.020(2) 0.024(3) 0.025(3) -0.006(2) -0.001(2) 0.0013(19) C31 0.033(3) 0.035(3) 0.028(3) -0.005(2) 0.003(2) 0.008(2) C32 0.040(3) 0.051(4) 0.038(4) -0.012(3) 0.000(3) 0.017(3) C33 0.044(4) 0.064(4) 0.038(4) -0.023(3) 0.014(3) 0.009(3) C34 0.041(3) 0.054(4) 0.024(3) -0.010(3) 0.010(3) 0.004(3) C35 0.034(3) 0.033(3) 0.027(3) -0.006(2) 0.004(2) -0.003(2) C36 0.016(2) 0.026(2) 0.019(2) 0.0012(19) -0.0002(19) -0.0029(19) C37 0.019(2) 0.024(2) 0.020(2) 0.0003(19) 0.0049(19) -0.0029(19) C38 0.024(3) 0.028(3) 0.023(3) 0.007(2) 0.003(2) -0.001(2) C39 0.019(2) 0.043(3) 0.017(2) 0.001(2) -0.0027(19) 0.003(2) C40 0.029(3) 0.030(3) 0.019(3) -0.005(2) -0.003(2) -0.002(2) C41 0.026(3) 0.025(3) 0.022(3) -0.001(2) -0.004(2) 0.001(2) F1 0.048(2) 0.054(2) 0.061(3) -0.0125(19) 0.0137(19) -0.0324(18) F2 0.057(2) 0.0258(17) 0.050(2) -0.0171(15) 0.0078(18) 0.0002(15) F3 0.0379(18) 0.0464(19) 0.0201(16) 0.0081(14) 0.0105(13) -0.0002(15) F4 0.0300(16) 0.0364(17) 0.0256(16) 0.0062(13) -0.0016(13) 0.0104(13) F5 0.0266(17) 0.0325(17) 0.053(2) -0.0092(15) 0.0085(15) 0.0033(13) F6 0.048(2) 0.046(2) 0.087(3) -0.019(2) 0.002(2) -0.0249(18) _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 C12 2.006(4) . ? Ir C1 2.035(5) . ? Ir N2 2.036(4) . ? Ir N1 2.064(4) . ? Ir P1 2.3905(12) . ? Ir Cl1 2.4865(11) . ? P1 C36 1.828(5) . ? P1 C30 1.828(5) . ? P1 C23 1.856(5) . ? N1 C11 1.353(6) . ? N1 C7 1.372(6) . ? N2 C22 1.353(6) . ? N2 C18 1.366(6) . ? C1 C2 1.388(7) . ? C1 C6 1.415(7) . ? C2 C3 1.375(7) . ? C2 H2 0.9500 . ? C3 F1 1.351(6) . ? C3 C4 1.379(8) . ? C4 C5 1.364(8) . ? C4 H4 0.9500 . ? C5 F2 1.354(6) . ? C5 C6 1.400(7) . ? C6 C7 1.468(7) . ? C7 C8 1.397(7) . ? C8 C9 1.378(8) . ? C8 H8 0.9500 . ? C9 C10 1.378(8) . ? C9 H9 0.9500 . ? C10 C11 1.362(7) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.406(6) . ? C12 C17 1.414(6) . ? C13 C14 1.376(7) . ? C13 H13 0.9500 . ? C14 F3 1.351(5) . ? C14 C15 1.367(7) . ? C15 C16 1.375(7) . ? C15 H15 0.9500 . ? C16 F4 1.367(5) . ? C16 C17 1.387(6) . ? C17 C18 1.467(6) . ? C18 C19 1.395(7) . ? C19 C20 1.375(7) . ? C19 H19 0.9500 . ? C20 C21 1.383(7) . ? C20 H20 0.9500 . ? C21 C22 1.362(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.498(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.381(7) . ? C24 C29 1.392(7) . ? C25 F5 1.366(6) . ? C25 C26 1.375(7) . ? C26 C27 1.378(8) . ? C26 H26 0.9500 . ? C27 F6 1.360(6) . ? C27 C28 1.360(8) . ? C28 C29 1.379(7) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.388(7) . ? C30 C35 1.406(7) . ? C31 C32 1.385(8) . ? C31 H31 0.9500 . ? C32 C33 1.384(9) . ? C32 H32 0.9500 . ? C33 C34 1.391(9) . ? C33 H33 0.9500 . ? C34 C35 1.384(7) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.389(7) . ? C36 C41 1.398(7) . ? C37 C38 1.397(7) . ? C37 H37 0.9500 . ? C38 C39 1.372(7) . ? C38 H38 0.9500 . ? C39 C40 1.383(7) . ? C39 H39 0.9500 . ? C40 C41 1.382(7) . ? C40 H40 0.9500 . ? C41 H41 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 Ir C1 88.72(17) . . ? C12 Ir N2 80.43(17) . . ? C1 Ir N2 91.42(18) . . ? C12 Ir N1 92.36(17) . . ? C1 Ir N1 79.96(18) . . ? N2 Ir N1 168.93(15) . . ? C12 Ir P1 93.43(12) . . ? C1 Ir P1 177.76(13) . . ? N2 Ir P1 89.54(11) . . ? N1 Ir P1 99.32(11) . . ? C12 Ir Cl1 170.80(13) . . ? C1 Ir Cl1 85.59(12) . . ? N2 Ir Cl1 92.47(11) . . ? N1 Ir Cl1 93.76(11) . . ? P1 Ir Cl1 92.35(4) . . ? C36 P1 C30 102.1(2) . . ? C36 P1 C23 106.2(2) . . ? C30 P1 C23 104.0(2) . . ? C36 P1 Ir 119.11(16) . . ? C30 P1 Ir 112.26(16) . . ? C23 P1 Ir 111.71(16) . . ? C11 N1 C7 117.6(4) . . ? C11 N1 Ir 126.0(3) . . ? C7 N1 Ir 116.2(3) . . ? C22 N2 C18 118.9(4) . . ? C22 N2 Ir 124.5(3) . . ? C18 N2 Ir 116.6(3) . . ? C2 C1 C6 118.8(4) . . ? C2 C1 Ir 126.8(4) . . ? C6 C1 Ir 114.4(3) . . ? C3 C2 C1 119.7(5) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? F1 C3 C2 119.6(5) . . ? F1 C3 C4 117.4(5) . . ? C2 C3 C4 122.9(5) . . ? C5 C4 C3 117.4(5) . . ? C5 C4 H4 121.3 . . ? C3 C4 H4 121.3 . . ? F2 C5 C4 117.1(5) . . ? F2 C5 C6 120.4(5) . . ? C4 C5 C6 122.5(5) . . ? C5 C6 C1 118.6(5) . . ? C5 C6 C7 125.6(5) . . ? C1 C6 C7 115.7(4) . . ? N1 C7 C8 120.3(5) . . ? N1 C7 C6 113.7(4) . . ? C8 C7 C6 125.9(5) . . ? C9 C8 C7 120.1(5) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.3(5) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 118.7(5) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? N1 C11 C10 123.9(5) . . ? N1 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C13 C12 C17 118.5(4) . . ? C13 C12 Ir 127.2(3) . . ? C17 C12 Ir 114.3(3) . . ? C14 C13 C12 119.2(4) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? F3 C14 C15 117.9(4) . . ? F3 C14 C13 118.4(4) . . ? C15 C14 C13 123.7(5) . . ? C14 C15 C16 116.7(4) . . ? C14 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? F4 C16 C15 116.4(4) . . ? F4 C16 C17 120.3(4) . . ? C15 C16 C17 123.3(4) . . ? C16 C17 C12 118.6(4) . . ? C16 C17 C18 125.9(4) . . ? C12 C17 C18 115.4(4) . . ? N2 C18 C19 119.9(4) . . ? N2 C18 C17 113.0(4) . . ? C19 C18 C17 127.0(4) . . ? C20 C19 C18 120.5(5) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 118.5(5) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 119.8(5) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? N2 C22 C21 122.3(5) . . ? N2 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C24 C23 P1 117.4(3) . . ? C24 C23 H23A 107.9 . . ? P1 C23 H23A 107.9 . . ? C24 C23 H23B 107.9 . . ? P1 C23 H23B 107.9 . . ? H23A C23 H23B 107.2 . . ? C25 C24 C29 115.4(4) . . ? C25 C24 C23 120.4(4) . . ? C29 C24 C23 124.2(4) . . ? F5 C25 C26 117.2(5) . . ? F5 C25 C24 118.1(4) . . ? C26 C25 C24 124.6(5) . . ? C25 C26 C27 116.3(5) . . ? C25 C26 H26 121.9 . . ? C27 C26 H26 121.9 . . ? F6 C27 C28 119.6(5) . . ? F6 C27 C26 117.6(5) . . ? C28 C27 C26 122.8(5) . . ? C27 C28 C29 118.4(5) . . ? C27 C28 H28 120.8 . . ? C29 C28 H28 120.8 . . ? C28 C29 C24 122.4(5) . . ? C28 C29 H29 118.8 . . ? C24 C29 H29 118.8 . . ? C31 C30 C35 118.1(5) . . ? C31 C30 P1 122.5(4) . . ? C35 C30 P1 118.9(4) . . ? C32 C31 C30 121.3(5) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C33 C32 C31 120.0(6) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 119.8(6) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 120.0(6) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C30 120.7(5) . . ? C34 C35 H35 119.6 . . ? C30 C35 H35 119.6 . . ? C37 C36 C41 118.2(4) . . ? C37 C36 P1 120.5(4) . . ? C41 C36 P1 121.2(4) . . ? C36 C37 C38 120.6(5) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C39 C38 C37 120.4(5) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C38 C39 C40 119.5(5) . . ? C38 C39 H39 120.2 . . ? C40 C39 H39 120.2 . . ? C41 C40 C39 120.4(5) . . ? C41 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? C40 C41 C36 120.8(5) . . ? C40 C41 H41 119.6 . . ? C36 C41 H41 119.6 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.788 _refine_diff_density_min -1.844 _refine_diff_density_rms 0.138 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 725890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H27 Cl F6 Ir N2 P' _chemical_formula_sum 'C41 H27 Cl F6 Ir N2 P' _chemical_formula_weight 920.27 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' 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.6365(14) _cell_length_b 11.3201(5) _cell_length_c 18.1593(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.152(1) _cell_angle_gamma 90.00 _cell_volume 6803.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6325 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.98 _exptl_crystal_description plate _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3600 _exptl_absorpt_coefficient_mu 4.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4140 _exptl_absorpt_correction_T_max 0.8206 _exptl_absorpt_process_details SADABS _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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25603 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7813 _reflns_number_gt 6675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0406P)^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 7813 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 Ir Ir 0.162762(5) 0.513649(14) 0.294740(9) 0.01643(6) Uani 1 1 d . . . Cl1 Cl 0.22690(3) 0.48045(9) 0.39848(6) 0.0201(2) Uani 1 1 d . . . P1 P 0.11968(3) 0.43779(10) 0.35697(6) 0.0174(2) Uani 1 1 d . . . N1 N 0.19803(11) 0.5819(3) 0.2283(2) 0.0189(8) Uani 1 1 d . . . N2 N 0.15637(11) 0.6852(3) 0.3363(2) 0.0212(8) Uani 1 1 d . . . C1 C 0.17117(13) 0.3642(4) 0.2387(2) 0.0187(9) Uani 1 1 d . . . C2 C 0.15896(14) 0.2484(4) 0.2456(2) 0.0216(10) Uani 1 1 d . . . H2 H 0.1428 0.2320 0.2785 0.026 Uiso 1 1 calc R . . C3 C 0.16997(16) 0.1579(4) 0.2058(3) 0.0273(11) Uani 1 1 d . . . C4 C 0.19298(15) 0.1729(4) 0.1556(3) 0.0271(11) Uani 1 1 d . . . H4 H 0.2006 0.1090 0.1290 0.032 Uiso 1 1 calc R . . C5 C 0.20395(15) 0.2881(5) 0.1476(3) 0.0263(11) Uani 1 1 d . . . C6 C 0.19397(13) 0.3841(4) 0.1852(2) 0.0201(9) Uani 1 1 d . . . C7 C 0.20701(14) 0.5050(4) 0.1785(3) 0.0233(10) Uani 1 1 d . . . C8 C 0.22641(15) 0.5462(5) 0.1259(3) 0.0306(11) Uani 1 1 d . . . H8 H 0.2322 0.4933 0.0900 0.037 Uiso 1 1 calc R . . C9 C 0.23702(15) 0.6634(5) 0.1264(3) 0.0305(12) Uani 1 1 d . . . H9 H 0.2500 0.6918 0.0906 0.037 Uiso 1 1 calc R . . C10 C 0.22874(14) 0.7393(4) 0.1789(3) 0.0270(11) Uani 1 1 d . . . H10 H 0.2365 0.8200 0.1807 0.032 Uiso 1 1 calc R . . C11 C 0.20891(14) 0.6959(4) 0.2288(3) 0.0235(10) Uani 1 1 d . . . H11 H 0.2027 0.7483 0.2646 0.028 Uiso 1 1 calc R . . C12 C 0.11408(13) 0.5707(4) 0.2120(2) 0.0199(9) Uani 1 1 d . . . C13 C 0.09288(14) 0.5077(4) 0.1459(3) 0.0238(10) Uani 1 1 d . . . H13 H 0.1012 0.4301 0.1376 0.029 Uiso 1 1 calc R . . C14 C 0.06028(15) 0.5580(5) 0.0933(3) 0.0279(11) Uani 1 1 d . . . C15 C 0.04600(15) 0.6681(5) 0.1021(3) 0.0329(12) Uani 1 1 d . . . H15 H 0.0229 0.7005 0.0654 0.039 Uiso 1 1 calc R . . C16 C 0.06711(16) 0.7301(5) 0.1676(3) 0.0312(12) Uani 1 1 d . . . C17 C 0.10141(14) 0.6870(4) 0.2220(3) 0.0224(10) Uani 1 1 d . . . C18 C 0.12605(15) 0.7514(4) 0.2896(3) 0.0243(10) Uani 1 1 d . . . C19 C 0.12187(16) 0.8691(5) 0.3067(3) 0.0334(12) Uani 1 1 d . . . H19 H 0.1010 0.9155 0.2735 0.040 Uiso 1 1 calc R . . C20 C 0.14795(17) 0.9195(5) 0.3721(3) 0.0356(13) Uani 1 1 d . . . H20 H 0.1449 0.9998 0.3845 0.043 Uiso 1 1 calc R . . C21 C 0.17832(16) 0.8515(4) 0.4189(3) 0.0320(12) Uani 1 1 d . . . H21 H 0.1967 0.8842 0.4639 0.038 Uiso 1 1 calc R . . C22 C 0.18156(15) 0.7353(4) 0.3992(3) 0.0261(11) Uani 1 1 d . . . H22 H 0.2026 0.6886 0.4315 0.031 Uiso 1 1 calc R . . C23 C 0.07425(13) 0.3676(4) 0.2909(2) 0.0213(10) Uani 1 1 d . . . H23A H 0.0571 0.4311 0.2605 0.026 Uiso 1 1 calc R . . H23B H 0.0832 0.3178 0.2542 0.026 Uiso 1 1 calc R . . C24 C 0.04817(14) 0.2925(4) 0.3256(2) 0.0222(10) Uani 1 1 d . . . C25 C 0.05179(17) 0.1719(4) 0.3280(3) 0.0329(12) Uani 1 1 d . . . C26 C 0.0295(2) 0.0971(5) 0.3585(4) 0.0466(15) Uani 1 1 d . . . H26 H 0.0331 0.0139 0.3590 0.056 Uiso 1 1 calc R . . C27 C 0.00129(18) 0.1496(5) 0.3886(3) 0.0415(14) Uani 1 1 d . . . C28 C -0.00431(16) 0.2675(5) 0.3886(3) 0.0324(12) Uani 1 1 d . . . H28 H -0.0239 0.3008 0.4096 0.039 Uiso 1 1 calc R . . C29 C 0.01926(14) 0.3390(5) 0.3570(3) 0.0268(11) Uani 1 1 d . . . H29 H 0.0156 0.4222 0.3569 0.032 Uiso 1 1 calc R . . C30 C 0.13723(14) 0.3273(4) 0.4323(2) 0.0201(9) Uani 1 1 d . . . C31 C 0.11487(15) 0.3020(4) 0.4831(3) 0.0253(10) Uani 1 1 d . . . H31 H 0.0920 0.3489 0.4826 0.030 Uiso 1 1 calc R . . C32 C 0.12605(16) 0.2079(5) 0.5346(3) 0.0316(12) Uani 1 1 d . . . H32 H 0.1108 0.1905 0.5691 0.038 Uiso 1 1 calc R . . C33 C 0.15940(15) 0.1400(4) 0.5353(3) 0.0297(12) Uani 1 1 d . . . H33 H 0.1667 0.0747 0.5694 0.036 Uiso 1 1 calc R . . C34 C 0.18209(15) 0.1665(4) 0.4868(3) 0.0275(11) Uani 1 1 d . . . H34 H 0.2054 0.1210 0.4887 0.033 Uiso 1 1 calc R . . C35 C 0.17094(14) 0.2597(4) 0.4350(2) 0.0194(9) Uani 1 1 d . . . H35 H 0.1866 0.2772 0.4013 0.023 Uiso 1 1 calc R . . C36 C 0.09838(14) 0.5558(4) 0.4022(3) 0.0205(9) Uani 1 1 d . . . C37 C 0.11973(15) 0.5955(4) 0.4754(3) 0.0265(11) Uani 1 1 d . . . H37 H 0.1430 0.5539 0.5048 0.032 Uiso 1 1 calc R . . C38 C 0.10711(17) 0.6955(5) 0.5056(3) 0.0321(12) Uani 1 1 d . . . H38 H 0.1218 0.7211 0.5559 0.038 Uiso 1 1 calc R . . C39 C 0.07425(17) 0.7578(4) 0.4652(3) 0.0346(13) Uani 1 1 d . . . H39 H 0.0663 0.8271 0.4865 0.041 Uiso 1 1 calc R . . C40 C 0.05224(16) 0.7191(4) 0.3920(3) 0.0320(12) Uani 1 1 d . . . H40 H 0.0290 0.7615 0.3631 0.038 Uiso 1 1 calc R . . C41 C 0.06439(14) 0.6182(4) 0.3614(3) 0.0233(10) Uani 1 1 d . . . H41 H 0.0492 0.5915 0.3117 0.028 Uiso 1 1 calc R . . F1 F 0.15827(11) 0.0459(3) 0.21550(19) 0.0410(8) Uani 1 1 d . . . F2 F 0.22662(9) 0.3033(3) 0.09775(17) 0.0366(7) Uani 1 1 d . . . F3 F 0.04074(9) 0.4972(3) 0.02912(18) 0.0384(8) Uani 1 1 d . . . F4 F 0.05282(10) 0.8395(3) 0.17668(19) 0.0454(8) Uani 1 1 d . . . F5 F 0.07902(11) 0.1220(3) 0.2974(2) 0.0539(10) Uani 1 1 d . . . F6 F -0.02099(13) 0.0774(3) 0.4198(2) 0.0719(13) 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 0.01576(9) 0.02100(10) 0.01265(9) 0.00098(7) 0.00439(7) 0.00128(7) Cl1 0.0163(5) 0.0242(5) 0.0175(5) 0.0012(4) 0.0015(4) 0.0020(4) P1 0.0161(6) 0.0241(6) 0.0121(5) 0.0004(4) 0.0044(5) 0.0025(4) N1 0.0141(19) 0.028(2) 0.0154(19) 0.0022(15) 0.0052(15) -0.0001(15) N2 0.020(2) 0.024(2) 0.021(2) 0.0038(15) 0.0076(17) 0.0002(16) C1 0.016(2) 0.026(2) 0.011(2) -0.0004(17) -0.0004(17) 0.0040(18) C2 0.018(2) 0.032(3) 0.015(2) -0.0015(18) 0.0061(19) 0.0005(19) C3 0.032(3) 0.023(2) 0.026(3) -0.0032(19) 0.008(2) -0.001(2) C4 0.029(3) 0.029(3) 0.025(3) -0.006(2) 0.011(2) 0.002(2) C5 0.023(3) 0.042(3) 0.017(2) 0.000(2) 0.010(2) 0.002(2) C6 0.019(2) 0.027(2) 0.014(2) 0.0029(18) 0.0045(19) 0.0046(18) C7 0.018(2) 0.030(3) 0.020(2) -0.0014(18) 0.0038(19) 0.0023(19) C8 0.023(3) 0.046(3) 0.026(3) 0.004(2) 0.013(2) 0.003(2) C9 0.018(3) 0.052(3) 0.022(3) 0.007(2) 0.007(2) 0.000(2) C10 0.018(2) 0.036(3) 0.025(3) 0.008(2) 0.002(2) -0.006(2) C11 0.020(2) 0.030(3) 0.018(2) 0.0019(19) 0.001(2) 0.0001(19) C12 0.014(2) 0.031(3) 0.015(2) 0.0037(18) 0.0048(18) 0.0013(18) C13 0.016(2) 0.035(3) 0.021(2) 0.0035(19) 0.0066(19) 0.0004(19) C14 0.018(2) 0.048(3) 0.017(2) 0.005(2) 0.004(2) 0.000(2) C15 0.017(3) 0.058(4) 0.020(3) 0.009(2) 0.001(2) 0.005(2) C16 0.027(3) 0.034(3) 0.032(3) 0.007(2) 0.008(2) 0.006(2) C17 0.021(2) 0.031(3) 0.016(2) 0.0043(18) 0.0074(19) 0.0033(19) C18 0.025(3) 0.028(3) 0.025(3) 0.0032(19) 0.014(2) 0.001(2) C19 0.034(3) 0.029(3) 0.037(3) 0.007(2) 0.011(3) 0.006(2) C20 0.040(3) 0.028(3) 0.041(3) -0.004(2) 0.015(3) -0.001(2) C21 0.036(3) 0.033(3) 0.031(3) -0.005(2) 0.016(2) -0.006(2) C22 0.029(3) 0.030(3) 0.021(2) -0.003(2) 0.010(2) -0.001(2) C23 0.019(2) 0.031(2) 0.013(2) -0.0038(18) 0.0042(19) -0.0008(19) C24 0.024(3) 0.029(2) 0.011(2) -0.0007(18) 0.0003(19) -0.003(2) C25 0.035(3) 0.029(3) 0.036(3) -0.001(2) 0.013(3) 0.003(2) C26 0.064(4) 0.027(3) 0.053(4) 0.003(3) 0.024(3) -0.004(3) C27 0.047(4) 0.043(3) 0.038(3) 0.006(3) 0.018(3) -0.014(3) C28 0.028(3) 0.044(3) 0.026(3) 0.001(2) 0.010(2) -0.005(2) C29 0.022(3) 0.038(3) 0.019(2) -0.003(2) 0.004(2) -0.006(2) C30 0.020(2) 0.029(2) 0.012(2) 0.0037(17) 0.0049(18) 0.0012(19) C31 0.025(3) 0.036(3) 0.017(2) 0.0012(19) 0.010(2) 0.003(2) C32 0.036(3) 0.042(3) 0.018(3) 0.005(2) 0.011(2) 0.002(2) C33 0.037(3) 0.027(3) 0.020(3) 0.0100(19) 0.001(2) 0.004(2) C34 0.028(3) 0.029(3) 0.022(3) 0.000(2) 0.002(2) 0.006(2) C35 0.019(2) 0.026(2) 0.012(2) 0.0003(17) 0.0033(18) 0.0004(18) C36 0.020(2) 0.026(2) 0.019(2) 0.0005(18) 0.0112(19) -0.0008(19) C37 0.022(3) 0.036(3) 0.023(3) -0.004(2) 0.009(2) -0.001(2) C38 0.036(3) 0.037(3) 0.028(3) -0.010(2) 0.018(2) -0.007(2) C39 0.040(3) 0.024(3) 0.048(3) -0.004(2) 0.028(3) -0.002(2) C40 0.029(3) 0.028(3) 0.043(3) 0.007(2) 0.017(3) 0.006(2) C41 0.018(2) 0.029(3) 0.025(2) 0.0040(19) 0.010(2) 0.0003(19) F1 0.058(2) 0.0268(16) 0.045(2) -0.0045(14) 0.0262(17) -0.0042(15) F2 0.0417(19) 0.0452(18) 0.0338(17) -0.0059(14) 0.0282(15) -0.0017(15) F3 0.0220(15) 0.066(2) 0.0219(16) -0.0021(14) -0.0022(13) -0.0024(14) F4 0.042(2) 0.0432(19) 0.044(2) 0.0039(15) 0.0025(16) 0.0203(16) F5 0.057(2) 0.0339(18) 0.084(3) -0.0036(18) 0.041(2) 0.0082(16) F6 0.091(3) 0.057(2) 0.087(3) 0.010(2) 0.057(3) -0.029(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 Ir C12 2.005(4) . ? Ir C1 2.039(4) . ? Ir N1 2.100(3) . ? Ir N2 2.118(4) . ? Ir P1 2.2882(11) . ? Ir Cl1 2.4814(11) . ? P1 C30 1.820(4) . ? P1 C36 1.833(5) . ? P1 C23 1.853(4) . ? N1 C11 1.344(6) . ? N1 C7 1.356(6) . ? N2 C22 1.341(6) . ? N2 C18 1.363(6) . ? C1 C2 1.393(6) . ? C1 C6 1.439(6) . ? C2 C3 1.372(6) . ? C2 H2 0.9500 . ? C3 F1 1.358(5) . ? C3 C4 1.386(6) . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 F2 1.372(5) . ? C5 C6 1.381(6) . ? C6 C7 1.458(6) . ? C7 C8 1.399(7) . ? C8 C9 1.376(7) . ? C8 H8 0.9500 . ? C9 C10 1.374(7) . ? C9 H9 0.9500 . ? C10 C11 1.379(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.403(6) . ? C12 C17 1.417(6) . ? C13 C14 1.369(7) . ? C13 H13 0.9500 . ? C14 F3 1.351(6) . ? C14 C15 1.368(7) . ? C15 C16 1.389(7) . ? C15 H15 0.9500 . ? C16 F4 1.362(6) . ? C16 C17 1.390(7) . ? C17 C18 1.466(7) . ? C18 C19 1.386(7) . ? C19 C20 1.385(7) . ? C19 H19 0.9500 . ? C20 C21 1.376(7) . ? C20 H20 0.9500 . ? C21 C22 1.377(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.507(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.370(7) . ? C24 C29 1.394(6) . ? C25 F5 1.351(6) . ? C25 C26 1.369(7) . ? C26 C27 1.386(8) . ? C26 H26 0.9500 . ? C27 C28 1.349(8) . ? C27 F6 1.356(6) . ? C28 C29 1.388(7) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C35 1.385(6) . ? C30 C31 1.399(6) . ? C31 C32 1.395(6) . ? C31 H31 0.9500 . ? C32 C33 1.385(7) . ? C32 H32 0.9500 . ? C33 C34 1.375(7) . ? C33 H33 0.9500 . ? C34 C35 1.391(6) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C41 1.386(6) . ? C36 C37 1.392(6) . ? C37 C38 1.383(7) . ? C37 H37 0.9500 . ? C38 C39 1.356(8) . ? C38 H38 0.9500 . ? C39 C40 1.394(7) . ? C39 H39 0.9500 . ? C40 C41 1.389(7) . ? C40 H40 0.9500 . ? C41 H41 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 Ir C1 96.06(18) . . ? C12 Ir N1 87.40(16) . . ? C1 Ir N1 79.98(16) . . ? C12 Ir N2 79.57(17) . . ? C1 Ir N2 169.66(15) . . ? N1 Ir N2 90.41(14) . . ? C12 Ir P1 87.93(12) . . ? C1 Ir P1 98.33(13) . . ? N1 Ir P1 174.83(10) . . ? N2 Ir P1 90.91(10) . . ? C12 Ir Cl1 169.78(14) . . ? C1 Ir Cl1 91.46(12) . . ? N1 Ir Cl1 87.11(10) . . ? N2 Ir Cl1 91.86(11) . . ? P1 Ir Cl1 97.85(4) . . ? C30 P1 C36 104.7(2) . . ? C30 P1 C23 102.9(2) . . ? C36 P1 C23 103.0(2) . . ? C30 P1 Ir 120.46(15) . . ? C36 P1 Ir 110.80(15) . . ? C23 P1 Ir 113.19(14) . . ? C11 N1 C7 120.1(4) . . ? C11 N1 Ir 124.0(3) . . ? C7 N1 Ir 115.7(3) . . ? C22 N2 C18 119.0(4) . . ? C22 N2 Ir 125.5(3) . . ? C18 N2 Ir 115.1(3) . . ? C2 C1 C6 116.8(4) . . ? C2 C1 Ir 130.0(3) . . ? C6 C1 Ir 113.2(3) . . ? C3 C2 C1 121.0(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? F1 C3 C2 119.3(4) . . ? F1 C3 C4 116.8(4) . . ? C2 C3 C4 123.9(4) . . ? C5 C4 C3 114.6(4) . . ? C5 C4 H4 122.7 . . ? C3 C4 H4 122.7 . . ? F2 C5 C4 114.7(4) . . ? F2 C5 C6 120.2(4) . . ? C4 C5 C6 125.1(4) . . ? C5 C6 C1 118.5(4) . . ? C5 C6 C7 124.7(4) . . ? C1 C6 C7 116.7(4) . . ? N1 C7 C8 119.5(4) . . ? N1 C7 C6 114.1(4) . . ? C8 C7 C6 126.3(4) . . ? C9 C8 C7 119.9(5) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 119.8(5) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 118.6(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? N1 C11 C10 122.1(4) . . ? N1 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C13 C12 C17 118.6(4) . . ? C13 C12 Ir 126.1(3) . . ? C17 C12 Ir 115.3(3) . . ? C14 C13 C12 120.1(5) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? F3 C14 C15 117.3(4) . . ? F3 C14 C13 119.4(5) . . ? C15 C14 C13 123.3(5) . . ? C14 C15 C16 116.3(5) . . ? C14 C15 H15 121.9 . . ? C16 C15 H15 121.9 . . ? F4 C16 C15 116.4(5) . . ? F4 C16 C17 119.8(5) . . ? C15 C16 C17 123.8(5) . . ? C16 C17 C12 117.8(4) . . ? C16 C17 C18 125.8(4) . . ? C12 C17 C18 116.3(4) . . ? N2 C18 C19 120.1(5) . . ? N2 C18 C17 113.5(4) . . ? C19 C18 C17 126.3(5) . . ? C20 C19 C18 120.2(5) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.1(5) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C20 C21 C22 118.6(5) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? N2 C22 C21 122.9(5) . . ? N2 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? C24 C23 P1 118.0(3) . . ? C24 C23 H23A 107.8 . . ? P1 C23 H23A 107.8 . . ? C24 C23 H23B 107.8 . . ? P1 C23 H23B 107.8 . . ? H23A C23 H23B 107.1 . . ? C25 C24 C29 115.7(4) . . ? C25 C24 C23 121.0(4) . . ? C29 C24 C23 123.4(4) . . ? F5 C25 C26 117.0(5) . . ? F5 C25 C24 118.1(5) . . ? C26 C25 C24 124.9(5) . . ? C25 C26 C27 116.2(5) . . ? C25 C26 H26 121.9 . . ? C27 C26 H26 121.9 . . ? C28 C27 F6 119.8(5) . . ? C28 C27 C26 122.8(5) . . ? F6 C27 C26 117.4(5) . . ? C27 C28 C29 118.4(5) . . ? C27 C28 H28 120.8 . . ? C29 C28 H28 120.8 . . ? C28 C29 C24 122.0(5) . . ? C28 C29 H29 119.0 . . ? C24 C29 H29 119.0 . . ? C35 C30 C31 119.2(4) . . ? C35 C30 P1 119.9(3) . . ? C31 C30 P1 120.6(4) . . ? C32 C31 C30 120.1(5) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C33 C32 C31 119.7(4) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C34 C33 C32 120.5(4) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 120.1(5) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C30 C35 C34 120.5(4) . . ? C30 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C41 C36 C37 118.4(4) . . ? C41 C36 P1 121.5(4) . . ? C37 C36 P1 119.5(4) . . ? C38 C37 C36 120.1(5) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? C39 C38 C37 121.6(5) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C38 C39 C40 119.2(5) . . ? C38 C39 H39 120.4 . . ? C40 C39 H39 120.4 . . ? C41 C40 C39 119.7(5) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? C36 C41 C40 121.0(5) . . ? C36 C41 H41 119.5 . . ? C40 C41 H41 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.886 _refine_diff_density_min -1.306 _refine_diff_density_rms 0.186 data_complex3 _database_code_depnum_ccdc_archive 'CCDC 725891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H26 F6 Ir N2 P' _chemical_formula_sum 'C42 H28 Cl2 F6 Ir N2 P' _chemical_formula_weight 968.73 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7300(5) _cell_length_b 10.1357(5) _cell_length_c 18.3439(9) _cell_angle_alpha 80.580(1) _cell_angle_beta 80.553(1) _cell_angle_gamma 80.913(1) _cell_volume 1744.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6782 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 26.56 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 4.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2912 _exptl_absorpt_correction_T_max 0.7625 _exptl_absorpt_process_details SADABS _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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22713 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7985 _reflns_number_gt 7431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0228P)^2^+1.8487P] 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 7985 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0677 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.004 _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 0.715272(13) 0.918535(13) 0.729959(7) 0.01440(5) Uani 1 1 d . . . P1 P 0.63228(9) 0.76451(9) 0.82217(5) 0.01571(18) Uani 1 1 d . . . N1 N 0.7983(3) 1.0482(3) 0.63790(16) 0.0179(6) Uani 1 1 d . . . N2 N 0.5176(3) 1.0445(3) 0.73947(16) 0.0176(6) Uani 1 1 d . . . C1 C 0.9145(4) 0.8266(4) 0.7145(2) 0.0177(7) Uani 1 1 d . . . C2 C 0.9766(4) 0.7047(4) 0.7510(2) 0.0204(8) Uani 1 1 d . . . H2 H 0.9210 0.6527 0.7890 0.024 Uiso 1 1 calc R . . C3 C 1.1167(4) 0.6594(4) 0.7325(2) 0.0256(9) Uani 1 1 d . . . C4 C 1.2065(4) 0.7263(4) 0.6783(2) 0.0262(9) Uani 1 1 d . . . H4 H 1.3029 0.6922 0.6664 0.031 Uiso 1 1 calc R . . C5 C 1.1463(4) 0.8464(4) 0.6424(2) 0.0243(8) Uani 1 1 d . . . C6 C 1.0054(4) 0.8987(4) 0.6573(2) 0.0199(8) Uani 1 1 d . . . C7 C 0.9397(4) 1.0219(4) 0.6165(2) 0.0198(7) Uani 1 1 d . . . C8 C 1.0051(4) 1.1095(4) 0.5585(2) 0.0279(9) Uani 1 1 d . . . H8 H 1.1039 1.0936 0.5440 0.033 Uiso 1 1 calc R . . C9 C 0.9266(5) 1.2185(4) 0.5223(2) 0.0302(9) Uani 1 1 d . . . H9 H 0.9710 1.2770 0.4827 0.036 Uiso 1 1 calc R . . C10 C 0.7832(4) 1.2422(4) 0.5441(2) 0.0278(9) Uani 1 1 d . . . H10 H 0.7271 1.3160 0.5195 0.033 Uiso 1 1 calc R . . C11 C 0.7236(4) 1.1556(4) 0.6027(2) 0.0251(8) Uani 1 1 d . . . H11 H 0.6254 1.1728 0.6187 0.030 Uiso 1 1 calc R . . C12 C 0.7499(4) 1.0561(3) 0.79490(19) 0.0165(7) Uani 1 1 d . . . C13 C 0.8774(4) 1.0710(4) 0.8174(2) 0.0200(8) Uani 1 1 d . . . H13 H 0.9602 1.0117 0.8040 0.024 Uiso 1 1 calc R . . C14 C 0.8825(4) 1.1707(4) 0.8587(2) 0.0226(8) Uani 1 1 d . . . C15 C 0.7678(4) 1.2595(4) 0.8817(2) 0.0247(8) Uani 1 1 d . . . H15 H 0.7738 1.3260 0.9116 0.030 Uiso 1 1 calc R . . C16 C 0.6439(4) 1.2460(4) 0.8588(2) 0.0234(8) Uani 1 1 d . . . C17 C 0.6305(4) 1.1504(4) 0.8145(2) 0.0189(7) Uani 1 1 d . . . C18 C 0.5031(4) 1.1434(4) 0.7829(2) 0.0185(7) Uani 1 1 d . . . C19 C 0.3771(4) 1.2321(4) 0.7911(2) 0.0269(9) Uani 1 1 d . . . H19 H 0.3667 1.3007 0.8219 0.032 Uiso 1 1 calc R . . C20 C 0.2681(4) 1.2190(4) 0.7540(2) 0.0304(9) Uani 1 1 d . . . H20 H 0.1826 1.2789 0.7589 0.036 Uiso 1 1 calc R . . C21 C 0.2848(4) 1.1183(4) 0.7097(2) 0.0255(9) Uani 1 1 d . . . H21 H 0.2117 1.1086 0.6832 0.031 Uiso 1 1 calc R . . C22 C 0.4092(4) 1.0325(4) 0.7046(2) 0.0227(8) Uani 1 1 d . . . H22 H 0.4194 0.9616 0.6752 0.027 Uiso 1 1 calc R . . C23 C 0.6584(4) 0.7904(4) 0.6630(2) 0.0182(7) Uani 1 1 d . . . C24 C 0.6502(4) 0.8265(4) 0.5860(2) 0.0233(8) Uani 1 1 d . . . H24 H 0.6746 0.9114 0.5614 0.028 Uiso 1 1 calc R . . C25 C 0.6073(4) 0.7409(5) 0.5460(2) 0.0291(9) Uani 1 1 d . . . C26 C 0.5725(4) 0.6151(4) 0.5773(2) 0.0290(9) Uani 1 1 d . . . H26 H 0.5443 0.5561 0.5489 0.035 Uiso 1 1 calc R . . C27 C 0.5813(4) 0.5807(4) 0.6523(2) 0.0228(8) Uani 1 1 d . . . C28 C 0.6219(4) 0.6623(4) 0.6959(2) 0.0196(7) Uani 1 1 d . . . C29 C 0.6262(4) 0.6161(4) 0.7782(2) 0.0210(8) Uani 1 1 d . . . H29A H 0.7104 0.5492 0.7855 0.025 Uiso 1 1 calc R . . H29B H 0.5416 0.5733 0.8009 0.025 Uiso 1 1 calc R . . C30 C 0.7155(4) 0.6952(4) 0.9052(2) 0.0183(7) Uani 1 1 d . . . C31 C 0.6680(4) 0.5826(4) 0.9506(2) 0.0251(8) Uani 1 1 d . . . H31 H 0.5949 0.5428 0.9375 0.030 Uiso 1 1 calc R . . C32 C 0.7268(4) 0.5284(4) 1.0145(2) 0.0304(9) Uani 1 1 d . . . H32 H 0.6959 0.4501 1.0447 0.036 Uiso 1 1 calc R . . C33 C 0.8305(4) 0.5885(5) 1.0344(2) 0.0318(10) Uani 1 1 d . . . H33 H 0.8701 0.5520 1.0786 0.038 Uiso 1 1 calc R . . C34 C 0.8766(5) 0.7008(5) 0.9905(2) 0.0325(10) Uani 1 1 d . . . H34 H 0.9476 0.7418 1.0046 0.039 Uiso 1 1 calc R . . C35 C 0.8201(4) 0.7543(4) 0.9258(2) 0.0235(8) Uani 1 1 d . . . H35 H 0.8528 0.8315 0.8954 0.028 Uiso 1 1 calc R . . C36 C 0.4536(4) 0.8136(4) 0.8657(2) 0.0183(7) Uani 1 1 d . . . C37 C 0.3370(4) 0.7803(4) 0.8417(2) 0.0274(9) Uani 1 1 d . . . H37 H 0.3494 0.7266 0.8026 0.033 Uiso 1 1 calc R . . C38 C 0.2027(4) 0.8250(5) 0.8744(2) 0.0324(10) Uani 1 1 d . . . H38 H 0.1238 0.8002 0.8581 0.039 Uiso 1 1 calc R . . C39 C 0.1821(4) 0.9042(5) 0.9295(2) 0.0335(10) Uani 1 1 d . . . H39 H 0.0895 0.9352 0.9512 0.040 Uiso 1 1 calc R . . C40 C 0.2975(4) 0.9392(4) 0.9537(2) 0.0319(10) Uani 1 1 d . . . H40 H 0.2838 0.9947 0.9920 0.038 Uiso 1 1 calc R . . C41 C 0.4322(4) 0.8936(4) 0.9225(2) 0.0265(9) Uani 1 1 d . . . H41 H 0.5107 0.9171 0.9398 0.032 Uiso 1 1 calc R . . F1 F 1.1716(2) 0.5408(2) 0.77097(14) 0.0372(6) Uani 1 1 d . . . F2 F 1.2361(2) 0.9139(3) 0.58978(13) 0.0343(6) Uani 1 1 d . . . F3 F 1.0081(2) 1.1845(2) 0.87879(14) 0.0332(6) Uani 1 1 d . . . F4 F 0.5292(2) 1.3331(2) 0.88264(14) 0.0348(6) Uani 1 1 d . . . F5 F 0.5977(3) 0.7805(3) 0.47243(13) 0.0416(6) Uani 1 1 d . . . F6 F 0.5460(3) 0.4569(2) 0.68507(14) 0.0357(6) Uani 1 1 d . . . C42 C 0.9556(4) 0.4847(4) 0.6200(2) 0.0281(9) Uani 1 1 d . . . H42A H 0.9449 0.5750 0.6359 0.034 Uiso 1 1 calc R . . H42B H 0.8926 0.4894 0.5821 0.034 Uiso 1 1 calc R . . Cl1 Cl 0.90664(11) 0.36634(11) 0.69720(6) 0.0352(2) Uani 1 1 d . . . Cl2 Cl 1.13178(11) 0.44098(12) 0.57983(6) 0.0371(2) 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 0.01335(7) 0.01494(7) 0.01447(7) -0.00250(5) -0.00187(5) -0.00022(5) P1 0.0149(4) 0.0160(4) 0.0159(4) -0.0028(4) -0.0019(3) -0.0011(3) N1 0.0203(15) 0.0169(15) 0.0160(15) -0.0035(12) 0.0001(12) -0.0030(12) N2 0.0188(15) 0.0168(15) 0.0169(15) -0.0011(12) -0.0026(12) -0.0030(12) C1 0.0165(17) 0.0203(18) 0.0186(18) -0.0090(14) -0.0061(14) 0.0008(14) C2 0.0182(18) 0.0210(19) 0.0222(19) -0.0067(15) -0.0026(15) 0.0003(15) C3 0.025(2) 0.025(2) 0.028(2) -0.0089(17) -0.0107(17) 0.0076(16) C4 0.0167(18) 0.036(2) 0.028(2) -0.0167(18) -0.0062(16) 0.0076(16) C5 0.0189(18) 0.036(2) 0.0210(19) -0.0120(17) 0.0014(15) -0.0080(16) C6 0.0163(17) 0.026(2) 0.0193(18) -0.0075(15) -0.0045(14) -0.0022(15) C7 0.0214(18) 0.0209(19) 0.0183(18) -0.0067(15) -0.0008(15) -0.0047(15) C8 0.028(2) 0.030(2) 0.026(2) -0.0077(17) 0.0036(17) -0.0086(17) C9 0.042(2) 0.028(2) 0.020(2) -0.0016(17) 0.0017(18) -0.0119(19) C10 0.037(2) 0.021(2) 0.024(2) -0.0004(16) -0.0064(17) -0.0033(17) C11 0.029(2) 0.024(2) 0.022(2) -0.0014(16) -0.0049(16) -0.0030(17) C12 0.0194(17) 0.0128(17) 0.0160(17) -0.0004(13) -0.0013(14) -0.0015(14) C13 0.0227(19) 0.0185(18) 0.0179(18) -0.0018(14) -0.0017(15) -0.0017(15) C14 0.0241(19) 0.025(2) 0.0204(19) -0.0037(16) -0.0033(15) -0.0074(16) C15 0.039(2) 0.0182(19) 0.0181(19) -0.0062(15) -0.0033(17) -0.0050(17) C16 0.029(2) 0.0165(18) 0.023(2) -0.0043(15) -0.0002(16) 0.0016(15) C17 0.0193(18) 0.0195(18) 0.0163(17) 0.0002(14) -0.0010(14) -0.0025(14) C18 0.0184(17) 0.0143(17) 0.0204(18) 0.0004(14) 0.0008(14) -0.0010(14) C19 0.024(2) 0.023(2) 0.034(2) -0.0065(17) -0.0034(17) 0.0012(16) C20 0.022(2) 0.029(2) 0.036(2) -0.0022(19) -0.0014(17) 0.0045(17) C21 0.0168(18) 0.024(2) 0.034(2) 0.0010(17) -0.0079(16) 0.0013(15) C22 0.0211(19) 0.026(2) 0.0222(19) -0.0008(16) -0.0077(15) -0.0041(16) C23 0.0127(16) 0.0213(18) 0.0206(18) -0.0081(15) -0.0014(14) 0.0017(14) C24 0.0222(19) 0.027(2) 0.0192(19) -0.0037(16) -0.0023(15) -0.0007(16) C25 0.027(2) 0.041(3) 0.020(2) -0.0114(18) -0.0079(16) 0.0040(18) C26 0.024(2) 0.038(2) 0.030(2) -0.0189(19) -0.0068(17) -0.0017(18) C27 0.0178(18) 0.023(2) 0.029(2) -0.0119(16) -0.0018(15) -0.0003(15) C28 0.0149(17) 0.0226(19) 0.0218(19) -0.0069(15) -0.0036(14) 0.0007(14) C29 0.0233(19) 0.0157(18) 0.0242(19) -0.0042(15) -0.0030(15) -0.0017(15) C30 0.0169(17) 0.0181(18) 0.0172(18) -0.0030(14) -0.0011(14) 0.0049(14) C31 0.026(2) 0.024(2) 0.023(2) 0.0022(16) -0.0035(16) -0.0026(16) C32 0.034(2) 0.023(2) 0.028(2) 0.0042(17) -0.0005(18) 0.0010(17) C33 0.031(2) 0.040(3) 0.019(2) -0.0011(18) -0.0058(17) 0.0078(19) C34 0.031(2) 0.042(3) 0.027(2) -0.0063(19) -0.0123(18) -0.0036(19) C35 0.0243(19) 0.025(2) 0.0225(19) -0.0030(16) -0.0059(16) -0.0047(16) C36 0.0159(17) 0.0193(18) 0.0162(17) 0.0017(14) 0.0027(14) -0.0014(14) C37 0.0223(19) 0.036(2) 0.023(2) -0.0038(17) -0.0023(16) -0.0035(17) C38 0.0173(19) 0.043(3) 0.035(2) 0.003(2) -0.0048(17) -0.0039(18) C39 0.021(2) 0.038(3) 0.033(2) 0.003(2) 0.0050(17) 0.0054(18) C40 0.031(2) 0.027(2) 0.032(2) -0.0065(18) 0.0101(18) 0.0000(18) C41 0.026(2) 0.025(2) 0.028(2) -0.0059(17) 0.0026(16) -0.0052(16) F1 0.0289(13) 0.0325(14) 0.0445(15) -0.0024(12) -0.0080(11) 0.0130(11) F2 0.0217(12) 0.0480(16) 0.0316(13) -0.0069(12) 0.0065(10) -0.0092(11) F3 0.0290(13) 0.0400(15) 0.0374(14) -0.0143(11) -0.0129(11) -0.0076(11) F4 0.0305(13) 0.0290(13) 0.0462(15) -0.0214(12) -0.0007(11) 0.0041(10) F5 0.0514(16) 0.0566(18) 0.0206(12) -0.0101(12) -0.0123(11) -0.0061(14) F6 0.0421(15) 0.0267(13) 0.0436(15) -0.0121(11) -0.0083(12) -0.0111(11) C42 0.034(2) 0.025(2) 0.022(2) -0.0016(17) -0.0010(17) -0.0001(17) Cl1 0.0343(6) 0.0378(6) 0.0281(5) 0.0030(5) 0.0018(4) -0.0034(5) Cl2 0.0329(6) 0.0379(6) 0.0362(6) -0.0005(5) 0.0032(5) -0.0047(5) _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 C1 2.010(3) . ? Ir C12 2.074(3) . ? Ir N1 2.096(3) . ? Ir C23 2.115(4) . ? Ir N2 2.132(3) . ? Ir P1 2.2441(9) . ? P1 C36 1.819(4) . ? P1 C30 1.829(4) . ? P1 C29 1.832(4) . ? N1 C11 1.344(5) . ? N1 C7 1.363(5) . ? N2 C22 1.352(5) . ? N2 C18 1.355(5) . ? C1 C2 1.402(5) . ? C1 C6 1.437(5) . ? C2 C3 1.372(5) . ? C2 H2 0.9500 . ? C3 F1 1.368(4) . ? C3 C4 1.377(6) . ? C4 C5 1.377(6) . ? C4 H4 0.9500 . ? C5 F2 1.363(4) . ? C5 C6 1.389(5) . ? C6 C7 1.458(5) . ? C7 C8 1.405(5) . ? C8 C9 1.379(6) . ? C8 H8 0.9500 . ? C9 C10 1.381(6) . ? C9 H9 0.9500 . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.407(5) . ? C12 C17 1.421(5) . ? C13 C14 1.369(5) . ? C13 H13 0.9500 . ? C14 F3 1.367(4) . ? C14 C15 1.373(5) . ? C15 C16 1.373(6) . ? C15 H15 0.9500 . ? C16 F4 1.368(4) . ? C16 C17 1.395(5) . ? C17 C18 1.468(5) . ? C18 C19 1.403(5) . ? C19 C20 1.384(6) . ? C19 H19 0.9500 . ? C20 C21 1.380(6) . ? C20 H20 0.9500 . ? C21 C22 1.373(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.413(5) . ? C23 C24 1.413(5) . ? C24 C25 1.374(6) . ? C24 H24 0.9500 . ? C25 F5 1.358(4) . ? C25 C26 1.380(6) . ? C26 C27 1.378(6) . ? C26 H26 0.9500 . ? C27 F6 1.370(4) . ? C27 C28 1.380(5) . ? C28 C29 1.511(5) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C35 1.389(5) . ? C30 C31 1.392(5) . ? C31 C32 1.384(5) . ? C31 H31 0.9500 . ? C32 C33 1.382(6) . ? C32 H32 0.9500 . ? C33 C34 1.374(6) . ? C33 H33 0.9500 . ? C34 C35 1.384(5) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.389(5) . ? C36 C41 1.392(5) . ? C37 C38 1.384(6) . ? C37 H37 0.9500 . ? C38 C39 1.362(6) . ? C38 H38 0.9500 . ? C39 C40 1.388(6) . ? C39 H39 0.9500 . ? C40 C41 1.382(5) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 Cl1 1.754(4) . ? C42 Cl2 1.769(4) . ? C42 H42A 0.9900 . ? C42 H42B 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 C1 Ir C12 96.74(14) . . ? C1 Ir N1 80.07(13) . . ? C12 Ir N1 86.36(12) . . ? C1 Ir C23 89.30(13) . . ? C12 Ir C23 173.84(13) . . ? N1 Ir C23 93.56(13) . . ? C1 Ir N2 171.01(13) . . ? C12 Ir N2 78.16(12) . . ? N1 Ir N2 92.13(11) . . ? C23 Ir N2 95.70(12) . . ? C1 Ir P1 97.12(11) . . ? C12 Ir P1 98.37(10) . . ? N1 Ir P1 174.79(8) . . ? C23 Ir P1 81.98(10) . . ? N2 Ir P1 90.98(8) . . ? C36 P1 C30 100.05(16) . . ? C36 P1 C29 106.04(17) . . ? C30 P1 C29 103.96(17) . . ? C36 P1 Ir 114.43(12) . . ? C30 P1 Ir 124.93(12) . . ? C29 P1 Ir 105.79(13) . . ? C11 N1 C7 119.8(3) . . ? C11 N1 Ir 124.6(3) . . ? C7 N1 Ir 115.5(2) . . ? C22 N2 C18 119.1(3) . . ? C22 N2 Ir 124.2(3) . . ? C18 N2 Ir 116.7(2) . . ? C2 C1 C6 116.1(3) . . ? C2 C1 Ir 129.8(3) . . ? C6 C1 Ir 114.0(3) . . ? C3 C2 C1 120.9(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? F1 C3 C2 118.1(4) . . ? F1 C3 C4 117.5(3) . . ? C2 C3 C4 124.3(4) . . ? C3 C4 C5 115.1(3) . . ? C3 C4 H4 122.5 . . ? C5 C4 H4 122.5 . . ? F2 C5 C4 115.0(3) . . ? F2 C5 C6 120.8(4) . . ? C4 C5 C6 124.2(4) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 C7 124.3(3) . . ? C1 C6 C7 116.3(3) . . ? N1 C7 C8 119.1(3) . . ? N1 C7 C6 113.6(3) . . ? C8 C7 C6 127.3(3) . . ? C9 C8 C7 120.4(4) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.6(4) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 118.1(4) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? N1 C11 C10 122.9(4) . . ? N1 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? C13 C12 C17 117.4(3) . . ? C13 C12 Ir 127.9(3) . . ? C17 C12 Ir 114.6(3) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? F3 C14 C13 119.1(3) . . ? F3 C14 C15 117.0(3) . . ? C13 C14 C15 123.9(4) . . ? C14 C15 C16 115.8(3) . . ? C14 C15 H15 122.1 . . ? C16 C15 H15 122.1 . . ? F4 C16 C15 115.7(3) . . ? F4 C16 C17 120.2(3) . . ? C15 C16 C17 124.1(3) . . ? C16 C17 C12 118.5(3) . . ? C16 C17 C18 124.9(3) . . ? C12 C17 C18 116.5(3) . . ? N2 C18 C19 120.2(3) . . ? N2 C18 C17 113.9(3) . . ? C19 C18 C17 125.8(3) . . ? C20 C19 C18 119.7(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 119.4(4) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C22 C21 C20 118.7(4) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? N2 C22 C21 122.9(4) . . ? N2 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? C28 C23 C24 116.6(3) . . ? C28 C23 Ir 119.6(3) . . ? C24 C23 Ir 123.7(3) . . ? C25 C24 C23 121.1(4) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? F5 C25 C24 119.3(4) . . ? F5 C25 C26 117.7(4) . . ? C24 C25 C26 123.0(4) . . ? C27 C26 C25 115.5(4) . . ? C27 C26 H26 122.3 . . ? C25 C26 H26 122.3 . . ? F6 C27 C26 116.8(3) . . ? F6 C27 C28 118.7(3) . . ? C26 C27 C28 124.6(4) . . ? C27 C28 C23 119.3(3) . . ? C27 C28 C29 120.6(3) . . ? C23 C28 C29 120.1(3) . . ? C28 C29 P1 107.9(3) . . ? C28 C29 H29A 110.1 . . ? P1 C29 H29A 110.1 . . ? C28 C29 H29B 110.1 . . ? P1 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? C35 C30 C31 119.3(3) . . ? C35 C30 P1 122.1(3) . . ? C31 C30 P1 118.5(3) . . ? C32 C31 C30 120.2(4) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C34 C33 C32 120.3(4) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 120.3(4) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C30 120.0(4) . . ? C34 C35 H35 120.0 . . ? C30 C35 H35 120.0 . . ? C37 C36 C41 118.6(3) . . ? C37 C36 P1 122.4(3) . . ? C41 C36 P1 118.9(3) . . ? C38 C37 C36 120.3(4) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C39 C38 C37 120.9(4) . . ? C39 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 C39 C40 119.5(4) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C41 C40 C39 120.3(4) . . ? C41 C40 H40 119.9 . . ? C39 C40 H40 119.9 . . ? C40 C41 C36 120.4(4) . . ? C40 C41 H41 119.8 . . ? C36 C41 H41 119.8 . . ? Cl1 C42 Cl2 111.2(2) . . ? Cl1 C42 H42A 109.4 . . ? Cl2 C42 H42A 109.4 . . ? Cl1 C42 H42B 109.4 . . ? Cl2 C42 H42B 109.4 . . ? H42A C42 H42B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.663 _refine_diff_density_min -1.318 _refine_diff_density_rms 0.125