# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- pit3i.cif' #====================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Holdt, Hans-J\"urgen Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; _publ_contact_author_phone +49-331-977-5180 _publ_contact_author_fax +49-331-977-5055 _publ_contact_author_email holdt@chem.uni-potsdam.de #====================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; 1,12-Diazaperylene and 2,11-Dialkylated-1,12-Diazaperylene Iridium(III) Complexes [Ir(C\^N)~2~(N\^N)]PF~6~: New Supramolecular Assemblies by \p-\p Stacking and CH-\p Interactions in the Solid State, and Photophysical and Electrochemical Properties and Stabilty Measurements in the Gas Phase ; loop_ _publ_author_name _publ_author_address S.Kammer ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; I.Starke ; Universit\"at Potsdam Institut f\"ur Chemie Analytische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; A.Pietrucha ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; A.Kelling ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; W.Mickler ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; U.Schilde ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; ; C.Dosche ; ; Carl von Ossietzky Universit\"at Oldenburg Institut f\"ur Reine und Angewandte Chemie Postfach 2503 D-26111 Oldenburg Germany ; E.Kleinpeter ; Universit\"at Potsdam Institut f\"ur Chemie Analytische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; 'Hans-J\"urgen Holdt' ; Universit\"at Potsdam Institut f\"ur Chemie Anorganische Chemie Karl-Liebknecht-Str. 24-25 D-14476 Potsdam Germany ; _publ_contact_author_name 'Holdt, Hans-Jurgen' #====================================================================== data_pit1i _database_code_depnum_ccdc_archive 'CCDC 827351' #TrackingRef '- pit1i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2-(2-pyridyl)phenyl)(1,12-diazaperylene)iridium(III)-hexafluorophosphate ; _chemical_melting_point 633 _chemical_formula_moiety 'C40 H26 Ir N4 1+ , F6 P 1-' _chemical_formula_sum 'C40 H26 F6 Ir N4 P' _chemical_formula_weight 899.82 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 26.8838(18) _cell_length_b 13.3700(6) _cell_length_c 22.1567(14) _cell_angle_alpha 90.00 _cell_angle_beta 117.125(5) _cell_angle_gamma 90.00 _cell_volume 7088.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 31202 _cell_measurement_theta_min 1.53 _cell_measurement_theta_max 29.53 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method ? _exptl_crystal_F_000 3520 _exptl_absorpt_coefficient_mu 3.880 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4454 _exptl_absorpt_correction_T_max 0.4566 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12x0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 100 mm ; _diffrn_reflns_number 22490 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6245 _reflns_number_gt 5332 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were found from the difference Fourier map and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _computing_publication_material SHELXL-97 _refine_special_details ; The unit cell contains disordered solvent molecules. In spite of several attempts, no reasonable solution could be received. Therefore the contribution of the disordered solvent species was subtracted from the structure factor calculation by the SQUEEZE instruction of the PLATON program suite. SQUEEZE calculated 900,8 \%A as solvent-accessible void volume and a number of electrons of 204 per cell. In consideration of Z these values correspond roughly with 0.5 molecule of methylenechlorid per asymmetric unit. ; _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^)+(0.0263P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000027(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6243 _refine_ls_number_parameters 551 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0499 _refine_ls_wR_factor_gt 0.0487 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 C1 C 0.30768(15) 0.9451(3) 0.06278(17) 0.0325(8) Uani 1 1 d . . . H1 H 0.3267(16) 0.900(3) 0.0999(18) 0.039 Uiso 1 1 d . . . C2 C 0.32972(16) 0.9773(3) 0.02184(17) 0.0347(8) Uani 1 1 d . . . H2 H 0.3629(18) 0.950(3) 0.0272(18) 0.042 Uiso 1 1 d . . . C3 C 0.32085(18) 1.0847(3) -0.07488(18) 0.0391(9) Uani 1 1 d . . . H3 H 0.3526(19) 1.056(3) -0.0713(19) 0.047 Uiso 1 1 d . . . C4 C 0.29085(17) 1.1544(3) -0.12148(17) 0.0415(9) Uani 1 1 d . . . H4 H 0.3010(18) 1.171(3) -0.151(2) 0.050 Uiso 1 1 d . . . C5 C 0.24223(17) 1.1968(3) -0.12418(17) 0.0397(9) Uani 1 1 d . . . H5 H 0.2211(17) 1.245(3) -0.161(2) 0.048 Uiso 1 1 d . . . C6 C 0.13971(17) 1.2846(3) -0.12434(17) 0.0404(8) Uani 1 1 d . . . H6 H 0.1513(17) 1.305(3) -0.1542(19) 0.049 Uiso 1 1 d . . . C7 C 0.09300(19) 1.3253(3) -0.1222(2) 0.0473(10) Uani 1 1 d . . . H7 H 0.0729(18) 1.375(3) -0.153(2) 0.057 Uiso 1 1 d . . . C8 C 0.07662(17) 1.2935(3) -0.07495(19) 0.0427(8) Uani 1 1 d . . . H8 H 0.0452(18) 1.323(3) -0.0743(19) 0.051 Uiso 1 1 d . . . C9 C 0.09316(17) 1.1793(3) 0.02142(19) 0.0413(9) Uani 1 1 d . . . H9 H 0.0641(18) 1.207(3) 0.0283(18) 0.050 Uiso 1 1 d . . . C10 C 0.12394(16) 1.1037(3) 0.06343(18) 0.0355(8) Uani 1 1 d . . . H10 H 0.1151(17) 1.074(3) 0.0947(19) 0.043 Uiso 1 1 d . . . C11 C 0.18434(13) 1.0994(2) 0.01464(14) 0.0248(6) Uani 1 1 d . . . C12 C 0.23338(14) 1.0566(2) 0.01432(15) 0.0263(7) Uani 1 1 d . . . C13 C 0.25263(14) 1.0932(2) -0.03111(15) 0.0271(7) Uani 1 1 d . . . C14 C 0.22249(15) 1.1679(2) -0.07902(15) 0.0304(7) Uani 1 1 d . . . C15 C 0.17180(14) 1.2112(3) -0.07974(15) 0.0310(7) Uani 1 1 d . . . C16 C 0.15457(14) 1.1763(2) -0.03129(15) 0.0300(7) Uani 1 1 d . . . C17 C 0.10734(15) 1.2179(3) -0.02819(16) 0.0352(8) Uani 1 1 d . . . C18 C 0.30191(15) 1.0510(2) -0.02822(16) 0.0307(7) Uani 1 1 d . . . C19 C 0.26907(16) 1.0878(3) 0.21808(17) 0.0334(8) Uani 1 1 d . . . H19 H 0.2376(17) 1.122(3) 0.1911(18) 0.040 Uiso 1 1 d . . . C20 C 0.31140(18) 1.1299(3) 0.27516(18) 0.0390(9) Uani 1 1 d . . . H20 H 0.3067(17) 1.193(3) 0.2855(19) 0.047 Uiso 1 1 d . . . C21 C 0.35827(19) 1.0747(3) 0.31178(19) 0.0470(10) Uani 1 1 d . . . H21 H 0.388(2) 1.100(3) 0.348(2) 0.056 Uiso 1 1 d . . . C22 C 0.36179(17) 0.9780(3) 0.29313(19) 0.0416(9) Uani 1 1 d . . . H22 H 0.388(2) 0.942(3) 0.314(2) 0.050 Uiso 1 1 d . . . C23 C 0.31791(15) 0.9371(3) 0.23603(15) 0.0310(7) Uani 1 1 d . . . C24 C 0.31326(14) 0.8330(2) 0.21268(16) 0.0298(7) Uani 1 1 d . . . C25 C 0.35323(18) 0.7596(3) 0.24611(19) 0.0408(9) Uani 1 1 d . . . H25 H 0.3853(18) 0.777(3) 0.282(2) 0.049 Uiso 1 1 d . . . C26 C 0.34437(19) 0.6630(3) 0.2220(2) 0.0465(10) Uani 1 1 d . . . H26 H 0.3690(19) 0.621(4) 0.242(2) 0.056 Uiso 1 1 d . . . C27 C 0.29609(19) 0.6392(3) 0.1647(2) 0.0429(9) Uani 1 1 d . . . H27 H 0.2885(19) 0.574(3) 0.146(2) 0.051 Uiso 1 1 d . . . C28 C 0.25667(17) 0.7109(3) 0.13058(17) 0.0348(8) Uani 1 1 d . . . H28 H 0.2248(17) 0.696(3) 0.0959(19) 0.042 Uiso 1 1 d . . . C29 C 0.26355(14) 0.8109(2) 0.15336(15) 0.0275(7) Uani 1 1 d . . . C30 C 0.15728(17) 0.8338(3) -0.02840(17) 0.0369(8) Uani 1 1 d . . . H30 H 0.1899(17) 0.861(3) -0.0310(18) 0.044 Uiso 1 1 d . . . C31 C 0.11660(18) 0.7802(3) -0.08006(18) 0.0447(9) Uani 1 1 d . . . H31 H 0.1204(17) 0.774(3) -0.119(2) 0.054 Uiso 1 1 d . . . C32 C 0.0726(2) 0.7426(3) -0.0720(2) 0.0540(11) Uani 1 1 d . . . H32 H 0.0421(19) 0.706(4) -0.109(2) 0.065 Uiso 1 1 d . . . C33 C 0.07072(18) 0.7602(3) -0.0113(2) 0.0483(10) Uani 1 1 d . . . H33 H 0.0429(19) 0.731(3) -0.002(2) 0.058 Uiso 1 1 d . . . C34 C 0.11208(15) 0.8141(2) 0.03963(16) 0.0331(7) Uani 1 1 d . . . C35 C 0.11531(15) 0.8369(2) 0.10598(16) 0.0320(7) Uani 1 1 d . . . C36 C 0.07447(17) 0.8082(3) 0.1248(2) 0.0431(9) Uani 1 1 d . . . H36 H 0.0428(19) 0.775(3) 0.095(2) 0.052 Uiso 1 1 d . . . C37 C 0.08054(18) 0.8321(3) 0.1886(2) 0.0470(10) Uani 1 1 d . . . H37 H 0.0516(19) 0.812(3) 0.199(2) 0.056 Uiso 1 1 d . . . C38 C 0.12671(18) 0.8845(3) 0.23282(19) 0.0416(9) Uani 1 1 d . . . H38 H 0.1326(17) 0.899(3) 0.278(2) 0.050 Uiso 1 1 d . . . C39 C 0.16750(17) 0.9131(3) 0.21454(17) 0.0326(8) Uani 1 1 d . . . H39 H 0.1945(18) 0.944(3) 0.2421(19) 0.039 Uiso 1 1 d . . . C40 C 0.16277(15) 0.8904(2) 0.15050(16) 0.0296(7) Uani 1 1 d . . . F1 F 0.02202(13) 0.5715(2) 0.06353(14) 0.0837(9) Uani 1 1 d . . . F2 F 0.03361(11) 0.40762(19) 0.04645(13) 0.0633(7) Uani 1 1 d . . . F3 F -0.05305(12) 0.4736(2) 0.01012(17) 0.0776(8) Uani 1 1 d . . . F4 F 0.06336(12) 0.4142(3) 0.30691(13) 0.0840(9) Uani 1 1 d . . . F5 F 0.01777(17) 0.4053(5) 0.19371(17) 0.173(3) Uani 1 1 d . . . F6 F 0.0000 0.2971(5) 0.2500 0.153(3) Uani 1 2 d S . . F7 F 0.0000 0.5260(4) 0.2500 0.267(7) Uani 1 2 d S . . Ir Ir 0.214291(5) 0.929964(8) 0.111126(5) 0.02413(5) Uani 1 1 d . . . N1 N 0.25890(11) 0.98228(19) 0.05825(12) 0.0265(6) Uani 1 1 d . . . N2 N 0.16888(12) 1.06207(19) 0.06025(12) 0.0272(6) Uani 1 1 d . . . N3 N 0.27265(11) 0.99418(19) 0.19789(12) 0.0270(6) Uani 1 1 d . . . N4 N 0.15566(12) 0.8515(2) 0.03078(13) 0.0284(6) Uani 1 1 d . . . P1 P 0.0000 0.5000 0.0000 0.0382(3) Uani 1 2 d S . . P2 P 0.0000 0.41553(13) 0.2500 0.0511(4) Uani 1 2 d S . . 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 C1 0.030(2) 0.0329(19) 0.0366(17) 0.0061(15) 0.0173(16) 0.0055(16) C2 0.030(2) 0.0360(19) 0.0420(18) 0.0033(16) 0.0194(16) 0.0045(17) C3 0.038(2) 0.046(2) 0.0407(18) -0.0023(18) 0.0242(17) -0.0035(19) C4 0.048(2) 0.052(2) 0.0342(18) 0.0035(17) 0.0267(18) -0.006(2) C5 0.047(2) 0.040(2) 0.0313(16) 0.0040(16) 0.0167(17) -0.0059(19) C6 0.047(2) 0.0361(19) 0.0356(17) 0.0089(17) 0.0163(17) 0.0055(19) C7 0.048(3) 0.035(2) 0.042(2) 0.0117(17) 0.0067(18) 0.0089(19) C8 0.033(2) 0.035(2) 0.053(2) 0.0040(18) 0.0140(17) 0.0081(18) C9 0.035(2) 0.041(2) 0.052(2) 0.0025(18) 0.0227(18) 0.0109(18) C10 0.034(2) 0.0370(19) 0.0432(18) 0.0028(16) 0.0241(17) 0.0048(17) C11 0.0220(17) 0.0249(16) 0.0259(14) 0.0000(13) 0.0096(13) 0.0002(14) C12 0.0269(18) 0.0244(17) 0.0247(14) -0.0005(13) 0.0093(13) 0.0003(14) C13 0.0312(19) 0.0233(16) 0.0243(14) -0.0019(12) 0.0106(14) -0.0046(14) C14 0.035(2) 0.0291(17) 0.0245(14) -0.0010(13) 0.0111(14) -0.0051(15) C15 0.0340(19) 0.0255(16) 0.0270(15) 0.0004(14) 0.0085(14) -0.0007(16) C16 0.0302(19) 0.0259(16) 0.0299(15) -0.0011(14) 0.0101(14) -0.0012(15) C17 0.0292(19) 0.0325(18) 0.0383(17) 0.0017(16) 0.0106(15) 0.0089(17) C18 0.0306(19) 0.0315(19) 0.0316(15) -0.0010(14) 0.0156(15) -0.0030(15) C19 0.037(2) 0.029(2) 0.0338(17) 0.0016(15) 0.0168(16) 0.0007(16) C20 0.052(3) 0.0286(19) 0.0359(18) -0.0055(16) 0.0200(18) -0.0090(19) C21 0.048(3) 0.045(2) 0.0354(18) -0.0036(18) 0.0079(18) -0.014(2) C22 0.031(2) 0.043(2) 0.0392(19) 0.0030(17) 0.0068(17) -0.0031(18) C23 0.0317(19) 0.0338(18) 0.0288(15) 0.0030(15) 0.0149(14) -0.0022(16) C24 0.0303(19) 0.0296(17) 0.0324(16) 0.0054(14) 0.0168(15) 0.0044(15) C25 0.040(2) 0.039(2) 0.0382(18) 0.0057(17) 0.0130(17) 0.0056(18) C26 0.048(3) 0.035(2) 0.057(2) 0.0151(19) 0.026(2) 0.017(2) C27 0.057(3) 0.0264(18) 0.050(2) 0.0003(17) 0.029(2) 0.0026(19) C28 0.042(2) 0.0256(17) 0.0383(17) 0.0020(16) 0.0200(16) 0.0014(17) C29 0.0293(18) 0.0269(17) 0.0288(15) 0.0030(13) 0.0156(14) -0.0003(14) C30 0.043(2) 0.0350(19) 0.0341(17) -0.0026(15) 0.0187(17) -0.0012(18) C31 0.052(3) 0.042(2) 0.0340(17) -0.0087(18) 0.0149(18) 0.001(2) C32 0.052(3) 0.055(3) 0.048(2) -0.019(2) 0.016(2) -0.010(2) C33 0.041(2) 0.048(2) 0.054(2) -0.0156(19) 0.020(2) -0.016(2) C34 0.031(2) 0.0273(17) 0.0386(17) -0.0024(15) 0.0139(15) -0.0030(15) C35 0.032(2) 0.0263(17) 0.0374(17) 0.0008(14) 0.0158(15) 0.0000(15) C36 0.032(2) 0.044(2) 0.054(2) -0.0039(18) 0.0206(18) -0.0114(18) C37 0.045(3) 0.050(2) 0.062(2) 0.006(2) 0.038(2) -0.001(2) C38 0.051(3) 0.042(2) 0.043(2) 0.0050(17) 0.0303(19) 0.005(2) C39 0.038(2) 0.0312(19) 0.0336(17) -0.0009(15) 0.0206(16) -0.0039(16) C40 0.0322(19) 0.0230(15) 0.0368(16) 0.0043(14) 0.0185(15) 0.0053(15) F1 0.064(2) 0.092(2) 0.0728(17) -0.0408(16) 0.0121(15) 0.0109(17) F2 0.0487(16) 0.0567(16) 0.0794(17) 0.0128(13) 0.0248(14) 0.0103(13) F3 0.0498(17) 0.0721(18) 0.132(2) 0.0137(18) 0.0600(18) 0.0033(15) F4 0.0517(18) 0.118(3) 0.0552(15) 0.0111(16) 0.0005(13) -0.0134(18) F5 0.082(3) 0.374(8) 0.0629(19) -0.033(3) 0.034(2) -0.079(4) F6 0.119(5) 0.087(4) 0.173(6) 0.000 -0.002(4) 0.000 F7 0.260(9) 0.041(3) 0.199(7) 0.000 -0.155(7) 0.000 Ir 0.02551(8) 0.02241(7) 0.02544(7) 0.00093(5) 0.01246(5) -0.00030(6) N1 0.0300(16) 0.0228(14) 0.0293(13) 0.0023(11) 0.0158(12) 0.0012(12) N2 0.0264(15) 0.0256(13) 0.0294(12) -0.0003(11) 0.0125(12) 0.0008(12) N3 0.0284(15) 0.0258(14) 0.0290(13) 0.0007(11) 0.0150(12) -0.0033(12) N4 0.0297(16) 0.0231(13) 0.0309(13) 0.0008(12) 0.0125(12) 0.0008(12) P1 0.0260(7) 0.0417(7) 0.0468(7) -0.0087(6) 0.0165(6) -0.0023(6) P2 0.0468(10) 0.0633(10) 0.0336(7) 0.000 0.0099(6) 0.000 _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 C1 C2 1.360(4) . ? C1 N1 1.363(4) . ? C1 H1 0.96(4) . ? C2 C18 1.416(5) . ? C2 H2 0.92(4) . ? C3 C4 1.351(6) . ? C3 C18 1.418(4) . ? C3 H3 0.91(4) . ? C4 C5 1.401(5) . ? C4 H4 0.84(4) . ? C5 C14 1.384(4) . ? C5 H5 0.99(4) . ? C6 C15 1.381(5) . ? C6 C7 1.388(6) . ? C6 H6 0.89(4) . ? C7 C8 1.376(5) . ? C7 H7 0.93(5) . ? C8 C17 1.413(5) . ? C8 H8 0.94(4) . ? C9 C10 1.368(5) . ? C9 C17 1.415(5) . ? C9 H9 0.94(4) . ? C10 N2 1.361(4) . ? C10 H10 0.92(4) . ? C11 N2 1.351(4) . ? C11 C16 1.411(4) . ? C11 C12 1.440(4) . ? C12 N1 1.341(4) . ? C12 C13 1.413(4) . ? C13 C14 1.413(5) . ? C13 C18 1.414(5) . ? C14 C15 1.474(5) . ? C15 C16 1.427(4) . ? C16 C17 1.416(5) . ? C19 N3 1.347(4) . ? C19 C20 1.378(5) . ? C19 H19 0.90(4) . ? C20 C21 1.363(6) . ? C20 H20 0.90(4) . ? C21 C22 1.374(6) . ? C21 H21 0.90(5) . ? C22 C23 1.389(5) . ? C22 H22 0.80(5) . ? C23 N3 1.356(4) . ? C23 C24 1.471(5) . ? C24 C25 1.393(5) . ? C24 C29 1.414(5) . ? C25 C26 1.377(6) . ? C25 H25 0.90(4) . ? C26 C27 1.376(6) . ? C26 H26 0.83(5) . ? C27 C28 1.372(5) . ? C27 H27 0.95(4) . ? C28 C29 1.410(5) . ? C28 H28 0.88(4) . ? C29 Ir 2.009(3) . ? C30 N4 1.352(4) . ? C30 C31 1.371(5) . ? C30 H30 0.97(4) . ? C31 C32 1.371(6) . ? C31 H31 0.92(4) . ? C32 C33 1.387(6) . ? C32 H32 0.99(5) . ? C33 C34 1.374(5) . ? C33 H33 0.94(4) . ? C34 N4 1.368(4) . ? C34 C35 1.465(4) . ? C35 C36 1.395(5) . ? C35 C40 1.402(5) . ? C36 C37 1.385(5) . ? C36 H36 0.91(4) . ? C37 C38 1.372(6) . ? C37 H37 0.95(4) . ? C38 C39 1.385(5) . ? C38 H38 0.95(4) . ? C39 C40 1.399(4) . ? C39 H39 0.81(4) . ? C40 Ir 2.015(3) . ? F1 P1 1.576(3) . ? F2 P1 1.598(2) . ? F3 P1 1.581(2) . ? F4 P2 1.592(3) . ? F5 P2 1.532(3) . ? F6 P2 1.583(6) . ? F7 P2 1.477(6) . ? Ir N3 2.036(3) . ? Ir N4 2.049(3) . ? Ir N1 2.140(2) . ? Ir N2 2.151(3) . ? P1 F1 1.576(3) 5_565 ? P1 F3 1.581(2) 5_565 ? P1 F2 1.598(2) 5_565 ? P2 F5 1.531(3) 2 ? P2 F4 1.592(3) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 122.2(3) . . ? C2 C1 H1 123(2) . . ? N1 C1 H1 114(2) . . ? C1 C2 C18 120.5(3) . . ? C1 C2 H2 119(2) . . ? C18 C2 H2 121(2) . . ? C4 C3 C18 119.2(4) . . ? C4 C3 H3 125(2) . . ? C18 C3 H3 116(2) . . ? C3 C4 C5 122.1(3) . . ? C3 C4 H4 119(3) . . ? C5 C4 H4 119(3) . . ? C14 C5 C4 120.9(3) . . ? C14 C5 H5 121(2) . . ? C4 C5 H5 118(2) . . ? C15 C6 C7 122.3(3) . . ? C15 C6 H6 116(3) . . ? C7 C6 H6 122(3) . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7 120(2) . . ? C6 C7 H7 119(2) . . ? C7 C8 C17 119.7(4) . . ? C7 C8 H8 119(2) . . ? C17 C8 H8 121(2) . . ? C10 C9 C17 120.3(3) . . ? C10 C9 H9 118(2) . . ? C17 C9 H9 122(2) . . ? N2 C10 C9 122.9(3) . . ? N2 C10 H10 114(3) . . ? C9 C10 H10 123(3) . . ? N2 C11 C16 122.8(3) . . ? N2 C11 C12 116.8(3) . . ? C16 C11 C12 120.4(3) . . ? N1 C12 C13 122.8(3) . . ? N1 C12 C11 117.2(2) . . ? C13 C12 C11 120.0(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 C18 121.4(3) . . ? C12 C13 C18 118.0(3) . . ? C5 C14 C13 117.6(3) . . ? C5 C14 C15 122.7(3) . . ? C13 C14 C15 119.8(3) . . ? C6 C15 C16 117.3(3) . . ? C6 C15 C14 124.0(3) . . ? C16 C15 C14 118.6(3) . . ? C11 C16 C17 118.5(3) . . ? C11 C16 C15 120.6(3) . . ? C17 C16 C15 120.9(3) . . ? C8 C17 C16 118.9(3) . . ? C8 C17 C9 123.8(3) . . ? C16 C17 C9 117.3(3) . . ? C13 C18 C2 117.5(3) . . ? C13 C18 C3 118.7(3) . . ? C2 C18 C3 123.7(3) . . ? N3 C19 C20 122.1(4) . . ? N3 C19 H19 116(2) . . ? C20 C19 H19 122(2) . . ? C21 C20 C19 118.5(3) . . ? C21 C20 H20 124(3) . . ? C19 C20 H20 118(3) . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 122(3) . . ? C22 C21 H21 118(3) . . ? C21 C22 C23 119.8(4) . . ? C21 C22 H22 123(3) . . ? C23 C22 H22 117(3) . . ? N3 C23 C22 119.6(3) . . ? N3 C23 C24 113.9(3) . . ? C22 C23 C24 126.4(3) . . ? C25 C24 C29 121.3(3) . . ? C25 C24 C23 124.0(3) . . ? C29 C24 C23 114.7(3) . . ? C26 C25 C24 120.0(4) . . ? C26 C25 H25 121(3) . . ? C24 C25 H25 119(3) . . ? C27 C26 C25 119.9(4) . . ? C27 C26 H26 122(3) . . ? C25 C26 H26 118(3) . . ? C28 C27 C26 120.9(4) . . ? C28 C27 H27 116(3) . . ? C26 C27 H27 123(3) . . ? C27 C28 C29 121.5(4) . . ? C27 C28 H28 121(3) . . ? C29 C28 H28 117(3) . . ? C28 C29 C24 116.4(3) . . ? C28 C29 Ir 129.3(3) . . ? C24 C29 Ir 114.2(2) . . ? N4 C30 C31 122.4(4) . . ? N4 C30 H30 115(2) . . ? C31 C30 H30 123(2) . . ? C32 C31 C30 119.4(3) . . ? C32 C31 H31 124(3) . . ? C30 C31 H31 116(3) . . ? C31 C32 C33 118.6(4) . . ? C31 C32 H32 121(2) . . ? C33 C32 H32 121(2) . . ? C34 C33 C32 120.8(4) . . ? C34 C33 H33 118(3) . . ? C32 C33 H33 121(3) . . ? N4 C34 C33 119.9(3) . . ? N4 C34 C35 113.9(3) . . ? C33 C34 C35 126.1(3) . . ? C36 C35 C40 121.2(3) . . ? C36 C35 C34 123.2(3) . . ? C40 C35 C34 115.5(3) . . ? C37 C36 C35 120.0(4) . . ? C37 C36 H36 119(2) . . ? C35 C36 H36 121(2) . . ? C38 C37 C36 119.6(3) . . ? C38 C37 H37 123(2) . . ? C36 C37 H37 117(2) . . ? C37 C38 C39 120.8(3) . . ? C37 C38 H38 121(3) . . ? C39 C38 H38 118(3) . . ? C38 C39 C40 121.2(4) . . ? C38 C39 H39 118(3) . . ? C40 C39 H39 121(3) . . ? C39 C40 C35 117.2(3) . . ? C39 C40 Ir 128.3(3) . . ? C35 C40 Ir 114.4(2) . . ? C29 Ir C40 91.59(12) . . ? C29 Ir N3 80.44(12) . . ? C40 Ir N3 95.03(12) . . ? C29 Ir N4 94.66(12) . . ? C40 Ir N4 80.42(12) . . ? N3 Ir N4 173.27(10) . . ? C29 Ir N1 95.69(11) . . ? C40 Ir N1 171.86(12) . . ? N3 Ir N1 89.78(10) . . ? N4 Ir N1 95.33(10) . . ? C29 Ir N2 172.42(10) . . ? C40 Ir N2 95.99(11) . . ? N3 Ir N2 99.06(10) . . ? N4 Ir N2 86.40(10) . . ? N1 Ir N2 76.73(10) . . ? C12 N1 C1 118.7(2) . . ? C12 N1 Ir 114.3(2) . . ? C1 N1 Ir 126.9(2) . . ? C11 N2 C10 118.1(3) . . ? C11 N2 Ir 113.6(2) . . ? C10 N2 Ir 127.9(2) . . ? C19 N3 C23 119.7(3) . . ? C19 N3 Ir 124.4(2) . . ? C23 N3 Ir 116.0(2) . . ? C30 N4 C34 118.9(3) . . ? C30 N4 Ir 125.5(2) . . ? C34 N4 Ir 115.6(2) . . ? F1 P1 F1 180.0 5_565 . ? F1 P1 F3 89.77(17) 5_565 . ? F1 P1 F3 90.24(17) . . ? F1 P1 F3 90.23(17) 5_565 5_565 ? F1 P1 F3 89.76(17) . 5_565 ? F3 P1 F3 180.0 . 5_565 ? F1 P1 F2 91.24(15) 5_565 5_565 ? F1 P1 F2 88.76(15) . 5_565 ? F3 P1 F2 88.96(14) . 5_565 ? F3 P1 F2 91.04(14) 5_565 5_565 ? F1 P1 F2 88.76(15) 5_565 . ? F1 P1 F2 91.24(15) . . ? F3 P1 F2 91.04(14) . . ? F3 P1 F2 88.96(14) 5_565 . ? F2 P1 F2 180.0 5_565 . ? F7 P2 F5 95.1(3) . 2 ? F7 P2 F5 95.1(3) . . ? F5 P2 F5 169.8(5) 2 . ? F7 P2 F6 180.000(2) . . ? F5 P2 F6 84.9(3) 2 . ? F5 P2 F6 84.9(3) . . ? F7 P2 F4 90.63(14) . . ? F5 P2 F4 88.41(18) 2 . ? F5 P2 F4 91.47(18) . . ? F6 P2 F4 89.37(14) . . ? F7 P2 F4 90.63(14) . 2 ? F5 P2 F4 91.47(18) 2 2 ? F5 P2 F4 88.42(18) . 2 ? F6 P2 F4 89.37(14) . 2 ? F4 P2 F4 178.7(3) . 2 ? 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 N1 C1 C2 C18 -0.7(5) . . . . ? C18 C3 C4 C5 1.8(6) . . . . ? C3 C4 C5 C14 -0.6(6) . . . . ? C15 C6 C7 C8 0.0(6) . . . . ? C6 C7 C8 C17 -0.5(6) . . . . ? C17 C9 C10 N2 0.0(6) . . . . ? N2 C11 C12 N1 1.2(4) . . . . ? C16 C11 C12 N1 -178.5(3) . . . . ? N2 C11 C12 C13 -178.8(3) . . . . ? C16 C11 C12 C13 1.4(5) . . . . ? N1 C12 C13 C14 176.4(3) . . . . ? C11 C12 C13 C14 -3.5(4) . . . . ? N1 C12 C13 C18 -2.0(5) . . . . ? C11 C12 C13 C18 178.1(3) . . . . ? C4 C5 C14 C13 -1.0(5) . . . . ? C4 C5 C14 C15 179.5(3) . . . . ? C12 C13 C14 C5 -176.9(3) . . . . ? C18 C13 C14 C5 1.4(5) . . . . ? C12 C13 C14 C15 2.6(5) . . . . ? C18 C13 C14 C15 -179.0(3) . . . . ? C7 C6 C15 C16 1.2(5) . . . . ? C7 C6 C15 C14 -178.3(3) . . . . ? C5 C14 C15 C6 -0.8(5) . . . . ? C13 C14 C15 C6 179.7(3) . . . . ? C5 C14 C15 C16 179.8(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? N2 C11 C16 C17 1.8(5) . . . . ? C12 C11 C16 C17 -178.5(3) . . . . ? N2 C11 C16 C15 -178.2(3) . . . . ? C12 C11 C16 C15 1.5(5) . . . . ? C6 C15 C16 C11 178.2(3) . . . . ? C14 C15 C16 C11 -2.3(5) . . . . ? C6 C15 C16 C17 -1.8(5) . . . . ? C14 C15 C16 C17 177.7(3) . . . . ? C7 C8 C17 C16 -0.1(6) . . . . ? C7 C8 C17 C9 -178.9(4) . . . . ? C11 C16 C17 C8 -178.7(3) . . . . ? C15 C16 C17 C8 1.3(5) . . . . ? C11 C16 C17 C9 0.1(5) . . . . ? C15 C16 C17 C9 -179.9(3) . . . . ? C10 C9 C17 C8 177.8(4) . . . . ? C10 C9 C17 C16 -1.0(6) . . . . ? C14 C13 C18 C2 179.4(3) . . . . ? C12 C13 C18 C2 -2.2(5) . . . . ? C14 C13 C18 C3 -0.3(5) . . . . ? C12 C13 C18 C3 178.1(3) . . . . ? C1 C2 C18 C13 3.5(5) . . . . ? C1 C2 C18 C3 -176.8(3) . . . . ? C4 C3 C18 C13 -1.3(5) . . . . ? C4 C3 C18 C2 179.0(4) . . . . ? N3 C19 C20 C21 0.3(5) . . . . ? C19 C20 C21 C22 -2.4(6) . . . . ? C20 C21 C22 C23 1.3(6) . . . . ? C21 C22 C23 N3 2.1(5) . . . . ? C21 C22 C23 C24 -174.7(3) . . . . ? N3 C23 C24 C25 -176.3(3) . . . . ? C22 C23 C24 C25 0.6(5) . . . . ? N3 C23 C24 C29 2.1(4) . . . . ? C22 C23 C24 C29 179.0(3) . . . . ? C29 C24 C25 C26 -0.9(5) . . . . ? C23 C24 C25 C26 177.5(3) . . . . ? C24 C25 C26 C27 0.2(6) . . . . ? C25 C26 C27 C28 0.8(6) . . . . ? C26 C27 C28 C29 -1.1(5) . . . . ? C27 C28 C29 C24 0.5(4) . . . . ? C27 C28 C29 Ir 177.2(2) . . . . ? C25 C24 C29 C28 0.5(4) . . . . ? C23 C24 C29 C28 -178.0(3) . . . . ? C25 C24 C29 Ir -176.7(2) . . . . ? C23 C24 C29 Ir 4.8(3) . . . . ? N4 C30 C31 C32 -0.1(6) . . . . ? C30 C31 C32 C33 -0.1(7) . . . . ? C31 C32 C33 C34 0.0(7) . . . . ? C32 C33 C34 N4 0.2(6) . . . . ? C32 C33 C34 C35 -179.4(4) . . . . ? N4 C34 C35 C36 178.3(3) . . . . ? C33 C34 C35 C36 -2.1(6) . . . . ? N4 C34 C35 C40 -1.7(4) . . . . ? C33 C34 C35 C40 177.9(4) . . . . ? C40 C35 C36 C37 -0.3(6) . . . . ? C34 C35 C36 C37 179.7(4) . . . . ? C35 C36 C37 C38 0.3(6) . . . . ? C36 C37 C38 C39 -0.5(6) . . . . ? C37 C38 C39 C40 0.5(6) . . . . ? C38 C39 C40 C35 -0.5(5) . . . . ? C38 C39 C40 Ir 176.6(3) . . . . ? C36 C35 C40 C39 0.4(5) . . . . ? C34 C35 C40 C39 -179.6(3) . . . . ? C36 C35 C40 Ir -177.1(3) . . . . ? C34 C35 C40 Ir 2.9(4) . . . . ? C28 C29 Ir C40 81.5(3) . . . . ? C24 C29 Ir C40 -101.8(2) . . . . ? C28 C29 Ir N3 176.3(3) . . . . ? C24 C29 Ir N3 -6.9(2) . . . . ? C28 C29 Ir N4 0.9(3) . . . . ? C24 C29 Ir N4 177.7(2) . . . . ? C28 C29 Ir N1 -94.9(3) . . . . ? C24 C29 Ir N1 81.9(2) . . . . ? C28 C29 Ir N2 -96.9(9) . . . . ? C24 C29 Ir N2 79.9(9) . . . . ? C39 C40 Ir C29 86.1(3) . . . . ? C35 C40 Ir C29 -96.7(3) . . . . ? C39 C40 Ir N3 5.6(3) . . . . ? C35 C40 Ir N3 -177.3(2) . . . . ? C39 C40 Ir N4 -179.4(3) . . . . ? C35 C40 Ir N4 -2.3(2) . . . . ? C39 C40 Ir N1 -120.5(8) . . . . ? C35 C40 Ir N1 56.7(9) . . . . ? C39 C40 Ir N2 -94.1(3) . . . . ? C35 C40 Ir N2 83.0(2) . . . . ? C13 C12 N1 C1 4.8(5) . . . . ? C11 C12 N1 C1 -175.2(3) . . . . ? C13 C12 N1 Ir -172.3(2) . . . . ? C11 C12 N1 Ir 7.7(3) . . . . ? C2 C1 N1 C12 -3.5(5) . . . . ? C2 C1 N1 Ir 173.2(3) . . . . ? C29 Ir N1 C12 170.9(2) . . . . ? C40 Ir N1 C12 17.5(9) . . . . ? N3 Ir N1 C12 -108.8(2) . . . . ? N4 Ir N1 C12 75.6(2) . . . . ? N2 Ir N1 C12 -9.4(2) . . . . ? C29 Ir N1 C1 -6.0(3) . . . . ? C40 Ir N1 C1 -159.3(7) . . . . ? N3 Ir N1 C1 74.4(3) . . . . ? N4 Ir N1 C1 -101.2(3) . . . . ? N2 Ir N1 C1 173.8(3) . . . . ? C16 C11 N2 C10 -2.7(5) . . . . ? C12 C11 N2 C10 177.6(3) . . . . ? C16 C11 N2 Ir 170.3(2) . . . . ? C12 C11 N2 Ir -9.4(4) . . . . ? C9 C10 N2 C11 1.8(5) . . . . ? C9 C10 N2 Ir -170.1(3) . . . . ? C29 Ir N2 C11 12.0(9) . . . . ? C40 Ir N2 C11 -166.3(2) . . . . ? N3 Ir N2 C11 97.6(2) . . . . ? N4 Ir N2 C11 -86.4(2) . . . . ? N1 Ir N2 C11 10.0(2) . . . . ? C29 Ir N2 C10 -175.8(8) . . . . ? C40 Ir N2 C10 5.9(3) . . . . ? N3 Ir N2 C10 -90.2(3) . . . . ? N4 Ir N2 C10 85.9(3) . . . . ? N1 Ir N2 C10 -177.8(3) . . . . ? C20 C19 N3 C23 3.1(4) . . . . ? C20 C19 N3 Ir -175.9(2) . . . . ? C22 C23 N3 C19 -4.2(4) . . . . ? C24 C23 N3 C19 172.9(3) . . . . ? C22 C23 N3 Ir 174.8(2) . . . . ? C24 C23 N3 Ir -8.0(3) . . . . ? C29 Ir N3 C19 -172.6(3) . . . . ? C40 Ir N3 C19 -81.8(2) . . . . ? N4 Ir N3 C19 -129.0(8) . . . . ? N1 Ir N3 C19 91.6(2) . . . . ? N2 Ir N3 C19 15.1(2) . . . . ? C29 Ir N3 C23 8.4(2) . . . . ? C40 Ir N3 C23 99.2(2) . . . . ? N4 Ir N3 C23 52.0(9) . . . . ? N1 Ir N3 C23 -87.4(2) . . . . ? N2 Ir N3 C23 -163.9(2) . . . . ? C31 C30 N4 C34 0.4(5) . . . . ? C31 C30 N4 Ir 179.7(3) . . . . ? C33 C34 N4 C30 -0.4(5) . . . . ? C35 C34 N4 C30 179.2(3) . . . . ? C33 C34 N4 Ir -179.8(3) . . . . ? C35 C34 N4 Ir -0.2(4) . . . . ? C29 Ir N4 C30 -87.2(3) . . . . ? C40 Ir N4 C30 -178.0(3) . . . . ? N3 Ir N4 C30 -130.2(8) . . . . ? N1 Ir N4 C30 9.0(3) . . . . ? N2 Ir N4 C30 85.3(3) . . . . ? C29 Ir N4 C34 92.2(2) . . . . ? C40 Ir N4 C34 1.4(2) . . . . ? N3 Ir N4 C34 49.2(9) . . . . ? N1 Ir N4 C34 -171.6(2) . . . . ? N2 Ir N4 C34 -95.3(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.057 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.072 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 1 0.000 0.000 -0.003 450.4 102.2 2 0.500 0.500 0.909 450.4 102.2 _chemical_name_common ;Bis(2-(2-pyridyl)phenyl)(1,12-diazaperylene)iridium(iii)- hexafluorophosphate ; data_pit2iw2 _database_code_depnum_ccdc_archive 'CCDC 827352' #TrackingRef '- pit2iw2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(benzo[h]quinoline)(1,12-diazaperylene)iridium(III)-hexafluorophosphate ; _chemical_name_common ;Bis(benzo(h)quinoline)(1,12-diazaperylene)iridium(iii)- hexafluorophosphate ; _chemical_melting_point ? _chemical_formula_moiety 'C88 H52 Ir2 N8 2+ , F12 P2 2-' _chemical_formula_sum 'C88 H52 F12 Ir2 N8 P2' _chemical_formula_weight 1895.72 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6225(7) _cell_length_b 32.6768(13) _cell_length_c 23.6264(14) _cell_angle_alpha 90.00 _cell_angle_beta 119.336(4) _cell_angle_gamma 90.00 _cell_volume 7822.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 33652 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 27.08 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method ? _exptl_crystal_F_000 3712 _exptl_absorpt_coefficient_mu 3.520 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4195 _exptl_absorpt_correction_T_max 0.4299 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12 x 0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 120 mm ; _diffrn_reflns_number 50615 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 13762 _reflns_number_gt 9927 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were calculated in their expected positions and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _computing_publication_material SHELXL-97 _refine_special_details ; The unit cell contains disordered solvent molecules. In spite of several attempts, no reasonable solution could be received. Therefore the contribution of the disordered solvent species was subtracted from the structure factor calculation by the SQUEEZE instruction of the PLATON program suite. SQUEEZE calculated 1199,8 \%A as solvent-accessible void volume and a number of electrons of 3134 per cell. In consideration of Z these values correspond roughly with two molecules of methylenechlorid per asymmetric unit. ; _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^)+(0.0368P)^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 SHELXL _refine_ls_extinction_coef 0.00016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13766 _refine_ls_number_parameters 1010 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _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 C1 C 0.1007(5) 0.79664(15) 0.2009(2) 0.0412(11) Uani 1 1 d . . . C2 C 0.1634(5) 0.74593(16) 0.1429(2) 0.0411(11) Uani 1 1 d . . . C3 C 0.2626(5) 0.76661(17) 0.0782(2) 0.0469(13) Uani 1 1 d . . . C4 C 0.2111(5) 0.77766(16) 0.1197(2) 0.0423(12) Uani 1 1 d . . . C5 C -0.1402(6) 0.62750(17) 0.1651(3) 0.0526(14) Uani 1 1 d . . . C6 C -0.3493(7) 0.6494(2) -0.0106(3) 0.0735(19) Uani 1 1 d . . . H6 H -0.4331 0.6443 -0.0452 0.088 Uiso 1 1 calc R . . C7 C 0.3377(7) 0.56936(19) 0.1772(3) 0.0617(16) Uani 1 1 d . . . C8 C 0.3392(6) 0.62587(18) 0.2448(3) 0.0534(14) Uani 1 1 d . . . C9 C 0.1560(5) 0.82830(16) 0.1809(2) 0.0482(13) Uani 1 1 d . . . C10 C 0.2533(6) 0.84790(18) 0.1106(3) 0.0560(14) Uani 1 1 d . . . H10 H 0.2524 0.8753 0.1210 0.067 Uiso 1 1 calc R . . C11 C 0.2736(6) 0.60359(17) 0.1870(3) 0.0519(14) Uani 1 1 d . . . C12 C -0.1875(6) 0.64208(17) 0.1011(3) 0.0533(14) Uani 1 1 d . . . C14 C 0.3012(6) 0.83741(19) 0.0688(3) 0.0628(16) Uani 1 1 d . . . H14 H 0.3296 0.8580 0.0514 0.075 Uiso 1 1 calc R . . C15 C -0.0088(5) 0.77155(16) 0.2579(2) 0.0478(13) Uani 1 1 d . . . H15 H -0.0499 0.7760 0.2827 0.057 Uiso 1 1 calc R . . C16 C 0.2077(5) 0.81929(16) 0.1368(2) 0.0443(12) Uani 1 1 d . . . C17 C -0.1342(6) 0.67796(18) 0.0313(3) 0.0580(15) Uani 1 1 d . . . H17 H -0.0736 0.6925 0.0243 0.070 Uiso 1 1 calc R . . C18 C 0.1579(6) 0.86683(18) 0.2047(3) 0.0585(15) Uani 1 1 d . . . H18 H 0.1931 0.8883 0.1922 0.070 Uiso 1 1 calc R . . C19 C -0.0514(9) 0.6018(2) 0.2897(4) 0.080(2) Uani 1 1 d . . . H19 H -0.0203 0.5937 0.3325 0.096 Uiso 1 1 calc R . . C20 C 0.2627(6) 0.72506(18) 0.0638(2) 0.0538(14) Uani 1 1 d . . . H20 H 0.2954 0.7169 0.0366 0.065 Uiso 1 1 calc R . . C21 C 0.0462(5) 0.80477(17) 0.2417(2) 0.0461(12) Uani 1 1 d . . . C22 C 0.1084(7) 0.8748(2) 0.2471(3) 0.0653(17) Uani 1 1 d . . . H22 H 0.1141 0.9012 0.2632 0.078 Uiso 1 1 calc R . . C23 C 0.4683(7) 0.5604(2) 0.2274(4) 0.0732(19) Uani 1 1 d . . . H23 H 0.5118 0.5382 0.2219 0.088 Uiso 1 1 calc R . . C24 C -0.2285(7) 0.60709(19) 0.1801(4) 0.0681(18) Uani 1 1 d . . . C25 C -0.2589(6) 0.6714(2) -0.0203(3) 0.0653(17) Uani 1 1 d . . . H25 H -0.2818 0.6816 -0.0613 0.078 Uiso 1 1 calc R . . C26 C -0.3151(6) 0.6350(2) 0.0507(3) 0.0643(16) Uani 1 1 d . . . C27 C -0.1785(8) 0.5947(2) 0.2449(4) 0.077(2) Uani 1 1 d . . . H27 H -0.2336 0.5814 0.2571 0.093 Uiso 1 1 calc R . . C28 C 0.2157(5) 0.69658(18) 0.0890(2) 0.0494(13) Uani 1 1 d . . . H28 H 0.2181 0.6692 0.0790 0.059 Uiso 1 1 calc R . . C29 C 0.0756(7) 0.59102(16) 0.0876(3) 0.0581(15) Uani 1 1 d . . . H29 H -0.0113 0.5971 0.0572 0.070 Uiso 1 1 calc R . . C30 C 0.4689(6) 0.61562(19) 0.2940(3) 0.0613(16) Uani 1 1 d . . . C31 C 0.0340(7) 0.62140(18) 0.2724(3) 0.0617(16) Uani 1 1 d . . . H31 H 0.1213 0.6259 0.3040 0.074 Uiso 1 1 calc R . . C32 C -0.0028(5) 0.73288(16) 0.2380(2) 0.0432(12) Uani 1 1 d . . . H32 H -0.0392 0.7115 0.2499 0.052 Uiso 1 1 calc R . . C33 C -0.4034(7) 0.6133(2) 0.0676(4) 0.084(2) Uani 1 1 d . . . H33 H -0.4899 0.6080 0.0358 0.101 Uiso 1 1 calc R . . C34 C 0.3073(6) 0.7983(2) 0.0528(3) 0.0597(15) Uani 1 1 d . . . H34 H 0.3407 0.7920 0.0252 0.072 Uiso 1 1 calc R . . C35 C 0.5315(7) 0.5822(2) 0.2821(4) 0.075(2) Uani 1 1 d . . . H35 H 0.6177 0.5754 0.3126 0.090 Uiso 1 1 calc R . . C36 C 0.1416(6) 0.61467(17) 0.1427(3) 0.0521(14) Uani 1 1 d . . . C37 C -0.0081(6) 0.63421(15) 0.2097(3) 0.0483(13) Uani 1 1 d . . . C38 C -0.0835(6) 0.95717(16) 0.3278(2) 0.0478(13) Uani 1 1 d . . . C39 C -0.3119(5) 0.84420(15) 0.1809(2) 0.0407(11) Uani 1 1 d . . . C40 C -0.2380(5) 0.84222(16) 0.1014(2) 0.0463(13) Uani 1 1 d . . . C41 C -0.3742(5) 0.82436(16) 0.2141(2) 0.0409(12) Uani 1 1 d . . . C42 C -0.4026(5) 0.78283(15) 0.2059(2) 0.0415(11) Uani 1 1 d . . . C43 C -0.0442(5) 0.91915(17) 0.3608(2) 0.0469(13) Uani 1 1 d . . . C44 C -0.4881(5) 0.79054(18) 0.2804(2) 0.0508(14) Uani 1 1 d . . . H44 H -0.5267 0.7798 0.3036 0.061 Uiso 1 1 calc R . . C45 C -0.3231(5) 0.77925(17) 0.1253(2) 0.0475(12) Uani 1 1 d . . . C46 C -0.2245(6) 0.90301(17) 0.1617(2) 0.0508(14) Uani 1 1 d . . . H46 H -0.2014 0.9304 0.1709 0.061 Uiso 1 1 calc R . . C47 C -0.2044(6) 0.88389(18) 0.1166(2) 0.0545(14) Uani 1 1 d . . . H47 H -0.1680 0.8983 0.0953 0.065 Uiso 1 1 calc R . . C48 C -0.1064(6) 0.85245(17) 0.3708(2) 0.0490(13) Uani 1 1 d . . . H48 H -0.1699 0.8320 0.3582 0.059 Uiso 1 1 calc R . . C49 C -0.3744(5) 0.75871(17) 0.1634(2) 0.0478(13) Uani 1 1 d . . . C50 C -0.5069(5) 0.94709(16) 0.2948(2) 0.0457(12) Uani 1 1 d . . . C51 C -0.4597(5) 0.76453(18) 0.2411(2) 0.0506(13) Uani 1 1 d . . . C52 C -0.3043(6) 0.75964(18) 0.0782(2) 0.0548(14) Uani 1 1 d . . . H52 H -0.3265 0.7321 0.0694 0.066 Uiso 1 1 calc R . . C54 C -0.5045(8) 0.96250(19) 0.3949(3) 0.0705(19) Uani 1 1 d . . . H54 H -0.5436 0.9732 0.4179 0.085 Uiso 1 1 calc R . . C55 C -0.5716(6) 0.96380(18) 0.3268(3) 0.0620(16) Uani 1 1 d . . . C56 C -0.2176(6) 0.8205(2) 0.0555(3) 0.0611(16) Uani 1 1 d . . . H56 H -0.1806 0.8335 0.0332 0.073 Uiso 1 1 calc R . . C57 C -0.3179(6) 0.92906(17) 0.3956(2) 0.0544(14) Uani 1 1 d . . . H57 H -0.2341 0.9178 0.4195 0.065 Uiso 1 1 calc R . . C58 C -0.2529(6) 0.7804(2) 0.0442(3) 0.0631(16) Uani 1 1 d . . . H58 H -0.2423 0.7664 0.0128 0.076 Uiso 1 1 calc R . . C59 C -0.3824(7) 0.94563(19) 0.4271(3) 0.0672(18) Uani 1 1 d . . . H59 H -0.3396 0.9450 0.4722 0.081 Uiso 1 1 calc R . . C60 C -0.2147(5) 0.96010(15) 0.2787(2) 0.0394(11) Uani 1 1 d . . . C61 C 0.1033(5) 0.75601(16) 0.1828(2) 0.0404(11) Uani 1 1 d . . . N63 N -0.4974(4) 0.93404(13) 0.1988(2) 0.0467(10) Uani 1 1 d . . . C63 C -0.5677(5) 0.95005(16) 0.2261(3) 0.0504(13) Uani 1 1 d . . . C64 C -0.2918(5) 0.82129(16) 0.1361(2) 0.0433(12) Uani 1 1 d . . . C65 C 0.3251(6) 0.6786(2) 0.3068(3) 0.0598(15) Uani 1 1 d . . . H65 H 0.2772 0.6995 0.3122 0.072 Uiso 1 1 calc R . . C66 C 0.0861(6) 0.91266(19) 0.4114(3) 0.0551(14) Uani 1 1 d . . . C67 C -0.4596(5) 0.83105(17) 0.2846(2) 0.0487(13) Uani 1 1 d . . . H67 H -0.4815 0.8477 0.3099 0.058 Uiso 1 1 calc R . . C68 C -0.3985(6) 0.71738(18) 0.1607(3) 0.0596(15) Uani 1 1 d . . . H68 H -0.3797 0.7009 0.1341 0.071 Uiso 1 1 calc R . . C69 C 0.0214(6) 0.8447(2) 0.4209(3) 0.0613(16) Uani 1 1 d . . . H69 H 0.0418 0.8192 0.4410 0.074 Uiso 1 1 calc R . . C70 C -0.2519(6) 0.99625(17) 0.2453(3) 0.0533(14) Uani 1 1 d . . . H70 H -0.3390 0.9997 0.2129 0.064 Uiso 1 1 calc R . . C71 C 0.0523(6) 0.84468(18) 0.2648(3) 0.0572(15) Uani 1 1 d . . . H71 H 0.0179 0.8505 0.2921 0.069 Uiso 1 1 calc R . . C72 C -0.5478(6) 0.93756(17) 0.1343(3) 0.0570(15) Uani 1 1 d . . . H72 H -0.5002 0.9273 0.1153 0.068 Uiso 1 1 calc R . . C73 C -0.4509(7) 0.69945(19) 0.1971(3) 0.0677(17) Uani 1 1 d . . . H73 H -0.4646 0.6713 0.1947 0.081 Uiso 1 1 calc R . . C74 C -0.4817(6) 0.7219(2) 0.2356(3) 0.0638(16) Uani 1 1 d . . . H74 H -0.5178 0.7093 0.2587 0.077 Uiso 1 1 calc R . . C75 C 0.1157(6) 0.8739(2) 0.4405(3) 0.0633(17) Uani 1 1 d . . . H75 H 0.2007 0.8682 0.4736 0.076 Uiso 1 1 calc R . . C76 C 0.0092(6) 0.98893(19) 0.3444(3) 0.0566(15) Uani 1 1 d . . . C77 C -0.6919(6) 0.96925(17) 0.1887(3) 0.0593(15) Uani 1 1 d . . . C78 C -0.0352(7) 1.02496(19) 0.3069(3) 0.0638(16) Uani 1 1 d . . . H78 H 0.0224 1.0467 0.3151 0.077 Uiso 1 1 calc R . . C79 C -0.7560(7) 0.9846(2) 0.2223(4) 0.0723(18) Uani 1 1 d . . . H79 H -0.8386 0.9968 0.1991 0.087 Uiso 1 1 calc R . . C80 C 0.4523(6) 0.6699(2) 0.3571(3) 0.0678(17) Uani 1 1 d . . . H80 H 0.4876 0.6851 0.3953 0.081 Uiso 1 1 calc R . . C81 C 0.5241(7) 0.6396(2) 0.3505(3) 0.077(2) Uani 1 1 d . . . H81 H 0.6099 0.6347 0.3834 0.092 Uiso 1 1 calc R . . C82 C 0.1410(7) 0.9817(2) 0.3968(3) 0.0721(18) Uani 1 1 d . . . H82 H 0.2032 1.0025 0.4093 0.087 Uiso 1 1 calc R . . C83 C -0.1632(7) 1.02775(18) 0.2584(3) 0.0637(17) Uani 1 1 d . . . H83 H -0.1914 1.0515 0.2336 0.076 Uiso 1 1 calc R . . C84 C 0.2655(8) 0.5471(2) 0.1198(4) 0.075(2) Uani 1 1 d . . . H84 H 0.3043 0.5249 0.1109 0.090 Uiso 1 1 calc R . . C85 C -0.6990(7) 0.9817(2) 0.2869(4) 0.0736(19) Uani 1 1 d . . . H85 H -0.7445 0.9919 0.3071 0.088 Uiso 1 1 calc R . . C86 C 0.1399(8) 0.5575(2) 0.0771(3) 0.0703(18) Uani 1 1 d . . . H86 H 0.0939 0.5422 0.0395 0.084 Uiso 1 1 calc R . . C87 C -0.7406(7) 0.97184(19) 0.1214(3) 0.0734(19) Uani 1 1 d . . . H87 H -0.8216 0.9843 0.0950 0.088 Uiso 1 1 calc R . . C88 C -0.6690(7) 0.95613(19) 0.0951(3) 0.0677(18) Uani 1 1 d . . . H88 H -0.7014 0.9578 0.0506 0.081 Uiso 1 1 calc R . . C89 C 0.1763(7) 0.9456(3) 0.4281(3) 0.074(2) Uani 1 1 d . . . H89 H 0.2623 0.9422 0.4617 0.089 Uiso 1 1 calc R . . C90 C -0.3606(8) 0.6009(2) 0.1286(4) 0.083(2) Uani 1 1 d . . . H90 H -0.4198 0.5875 0.1381 0.100 Uiso 1 1 calc R . . F1 F 0.2946(4) 0.76602(13) 0.33889(15) 0.0790(11) Uani 1 1 d . . . F2 F 0.3568(4) 0.82645(13) 0.39051(19) 0.0956(13) Uani 1 1 d . . . F3 F 0.3624(4) 0.73380(14) 0.43431(18) 0.0969(13) Uani 1 1 d . . . F4 F 0.2173(4) 0.78515(18) 0.4060(2) 0.1114(17) Uani 1 1 d . . . F5 F 0.0507(5) 0.90189(18) -0.0283(2) 0.1201(18) Uani 1 1 d . . . F6 F -0.2131(5) 0.9261(2) -0.0313(2) 0.144(2) Uani 1 1 d . . . F7 F -0.1347(8) 0.87009(19) -0.0477(4) 0.185(3) Uani 1 1 d . . . F8 F -0.1445(5) 0.9242(2) -0.10340(19) 0.129(2) Uani 1 1 d . . . F9 F -0.0297(6) 0.95905(16) -0.0139(3) 0.141(2) Uani 1 1 d . . . F10 F -0.0153(5) 0.90654(19) 0.0460(2) 0.129(2) Uani 1 1 d . . . F11 F 0.5020(3) 0.77409(12) 0.42019(16) 0.0746(10) Uani 1 1 d . . . F12 F 0.4274(4) 0.79490(16) 0.48672(16) 0.0966(14) Uani 1 1 d . . . Ir1 Ir 0.08624(2) 0.666062(6) 0.171074(9) 0.04285(7) Uani 1 1 d . . . Ir2 Ir -0.31899(2) 0.908024(6) 0.266190(9) 0.04090(6) Uani 1 1 d . . . N1 N 0.0549(4) 0.72466(13) 0.20117(18) 0.0409(10) Uani 1 1 d . . . N2 N 0.1651(4) 0.70659(13) 0.12854(18) 0.0415(10) Uani 1 1 d . . . N3 N -0.2784(4) 0.88296(13) 0.19447(19) 0.0448(10) Uani 1 1 d . . . N4 N -0.3996(4) 0.84831(13) 0.25282(18) 0.0438(10) Uani 1 1 d . . . N5 N -0.0967(4) 0.66394(14) 0.0921(2) 0.0508(11) Uani 1 1 d . . . N6 N 0.2713(4) 0.65786(14) 0.2518(2) 0.0506(11) Uani 1 1 d . . . N7 N -0.1395(4) 0.88889(14) 0.3402(2) 0.0472(11) Uani 1 1 d . . . C91 C -0.3809(6) 0.92961(16) 0.3273(2) 0.0486(13) Uani 1 1 d . . . P11 P 0.35934(17) 0.78018(6) 0.41292(7) 0.0670(5) Uani 1 1 d . . . P12 P -0.07991(18) 0.91459(6) -0.02896(8) 0.0690(5) 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 C1 0.044(3) 0.033(3) 0.046(3) 0.002(2) 0.022(2) 0.002(2) C2 0.042(3) 0.040(3) 0.042(2) 0.001(2) 0.021(2) 0.001(2) C3 0.046(3) 0.054(3) 0.043(3) 0.000(2) 0.023(2) -0.007(3) C4 0.049(3) 0.041(3) 0.038(2) 0.002(2) 0.022(2) -0.005(2) C5 0.066(4) 0.035(3) 0.073(4) 0.000(3) 0.046(3) 0.004(3) C6 0.060(4) 0.068(5) 0.073(4) -0.021(3) 0.018(3) 0.006(4) C7 0.077(4) 0.046(4) 0.090(4) 0.010(3) 0.063(4) 0.007(3) C8 0.067(4) 0.047(3) 0.061(3) 0.014(3) 0.043(3) 0.005(3) C9 0.051(3) 0.042(3) 0.047(3) -0.003(2) 0.021(2) -0.001(3) C10 0.072(4) 0.045(3) 0.058(3) 0.003(3) 0.037(3) -0.006(3) C11 0.062(4) 0.040(3) 0.073(4) 0.018(3) 0.048(3) 0.009(3) C12 0.059(4) 0.037(3) 0.073(4) -0.009(3) 0.039(3) -0.008(3) C14 0.074(4) 0.052(4) 0.066(4) 0.012(3) 0.037(3) -0.014(3) C15 0.054(3) 0.048(3) 0.049(3) -0.003(2) 0.032(3) 0.004(3) C16 0.049(3) 0.039(3) 0.044(3) 0.000(2) 0.021(2) -0.005(3) C17 0.067(4) 0.050(4) 0.057(3) -0.007(3) 0.031(3) -0.001(3) C18 0.069(4) 0.039(3) 0.073(4) -0.003(3) 0.039(3) -0.004(3) C19 0.112(6) 0.056(4) 0.106(5) 0.013(4) 0.080(5) 0.002(4) C20 0.069(4) 0.054(4) 0.054(3) -0.008(3) 0.042(3) -0.006(3) C21 0.048(3) 0.045(3) 0.048(3) -0.003(2) 0.025(2) 0.002(3) C22 0.081(4) 0.047(4) 0.076(4) -0.011(3) 0.044(4) 0.003(3) C23 0.071(5) 0.057(4) 0.118(6) 0.024(4) 0.067(5) 0.018(4) C24 0.072(5) 0.043(3) 0.112(5) -0.012(3) 0.062(4) -0.008(3) C25 0.057(4) 0.069(4) 0.064(4) -0.011(3) 0.025(3) 0.003(3) C26 0.055(4) 0.053(4) 0.083(4) -0.017(3) 0.033(3) -0.005(3) C27 0.105(6) 0.045(4) 0.124(6) 0.010(4) 0.089(5) -0.001(4) C28 0.057(3) 0.045(3) 0.054(3) -0.004(2) 0.034(3) -0.001(3) C29 0.078(4) 0.035(3) 0.073(4) 0.000(3) 0.047(3) 0.001(3) C30 0.058(4) 0.052(4) 0.084(4) 0.025(3) 0.043(3) 0.012(3) C31 0.081(4) 0.046(3) 0.084(4) 0.002(3) 0.061(4) -0.003(3) C32 0.047(3) 0.045(3) 0.045(3) 0.002(2) 0.029(2) 0.000(3) C33 0.059(4) 0.066(5) 0.126(7) -0.019(4) 0.044(4) -0.018(4) C34 0.062(4) 0.065(4) 0.061(3) 0.000(3) 0.038(3) -0.010(3) C35 0.061(4) 0.077(5) 0.100(5) 0.033(4) 0.048(4) 0.022(4) C36 0.065(4) 0.046(3) 0.060(3) 0.004(3) 0.043(3) -0.005(3) C37 0.059(4) 0.028(3) 0.066(3) -0.001(2) 0.037(3) 0.001(3) C38 0.068(4) 0.041(3) 0.054(3) -0.006(2) 0.045(3) -0.001(3) C39 0.045(3) 0.037(3) 0.044(3) 0.001(2) 0.025(2) 0.000(2) C40 0.059(3) 0.045(3) 0.043(3) -0.001(2) 0.032(3) 0.002(3) C41 0.043(3) 0.045(3) 0.037(2) 0.006(2) 0.021(2) 0.004(2) C42 0.040(3) 0.037(3) 0.047(3) 0.004(2) 0.021(2) 0.001(2) C43 0.053(3) 0.047(3) 0.052(3) -0.004(2) 0.034(3) 0.000(3) C44 0.047(3) 0.059(4) 0.049(3) 0.006(3) 0.025(3) -0.008(3) C45 0.049(3) 0.041(3) 0.053(3) -0.002(2) 0.026(3) 0.000(3) C46 0.073(4) 0.042(3) 0.052(3) -0.003(2) 0.042(3) -0.004(3) C47 0.070(4) 0.054(4) 0.056(3) 0.008(3) 0.044(3) 0.002(3) C48 0.057(3) 0.046(3) 0.048(3) 0.007(2) 0.029(3) 0.003(3) C49 0.052(3) 0.043(3) 0.046(3) 0.000(2) 0.023(2) 0.003(3) C50 0.056(3) 0.032(3) 0.057(3) 0.002(2) 0.034(3) -0.001(3) C51 0.051(3) 0.050(3) 0.052(3) 0.003(2) 0.026(3) -0.006(3) C52 0.067(4) 0.047(3) 0.056(3) -0.014(3) 0.034(3) -0.003(3) C54 0.108(6) 0.051(4) 0.093(5) 0.000(3) 0.081(5) 0.008(4) C55 0.074(4) 0.040(3) 0.102(5) -0.002(3) 0.066(4) 0.001(3) C56 0.079(4) 0.060(4) 0.062(3) 0.000(3) 0.048(3) 0.003(3) C57 0.074(4) 0.047(3) 0.050(3) -0.002(2) 0.036(3) 0.004(3) C58 0.076(4) 0.067(4) 0.058(3) -0.011(3) 0.042(3) -0.001(4) C59 0.108(6) 0.053(4) 0.065(4) 0.003(3) 0.061(4) 0.006(4) C60 0.054(3) 0.035(3) 0.041(3) 0.002(2) 0.033(2) 0.002(2) C61 0.041(3) 0.042(3) 0.038(2) 0.003(2) 0.019(2) 0.004(2) N63 0.060(3) 0.032(2) 0.055(3) 0.0009(18) 0.033(2) 0.000(2) C63 0.052(3) 0.031(3) 0.070(4) 0.002(2) 0.031(3) -0.002(3) C64 0.046(3) 0.045(3) 0.041(2) 0.000(2) 0.023(2) 0.001(2) C65 0.065(4) 0.061(4) 0.053(3) 0.003(3) 0.029(3) 0.002(3) C66 0.055(3) 0.064(4) 0.053(3) -0.003(3) 0.032(3) 0.000(3) C67 0.053(3) 0.051(3) 0.049(3) 0.003(2) 0.030(3) 0.003(3) C68 0.070(4) 0.039(3) 0.074(4) -0.004(3) 0.039(3) 0.000(3) C69 0.065(4) 0.065(4) 0.057(3) 0.012(3) 0.032(3) 0.012(4) C70 0.067(4) 0.043(3) 0.066(3) 0.000(3) 0.045(3) 0.001(3) C71 0.073(4) 0.047(3) 0.060(3) -0.008(3) 0.039(3) 0.004(3) C72 0.069(4) 0.046(3) 0.051(3) 0.006(2) 0.027(3) 0.005(3) C73 0.082(5) 0.041(3) 0.080(4) -0.003(3) 0.040(4) -0.008(3) C74 0.072(4) 0.056(4) 0.070(4) 0.008(3) 0.039(3) -0.013(3) C75 0.056(4) 0.080(5) 0.056(3) 0.010(3) 0.029(3) 0.012(4) C76 0.065(4) 0.054(4) 0.069(4) -0.018(3) 0.047(3) -0.014(3) C77 0.058(4) 0.033(3) 0.084(4) -0.001(3) 0.032(3) -0.001(3) C78 0.085(5) 0.045(4) 0.086(4) -0.012(3) 0.060(4) -0.013(3) C79 0.057(4) 0.047(4) 0.114(6) 0.006(4) 0.043(4) 0.007(3) C80 0.063(4) 0.075(5) 0.062(4) 0.007(3) 0.028(3) 0.002(4) C81 0.060(4) 0.096(6) 0.072(4) 0.026(4) 0.030(4) 0.005(4) C82 0.067(4) 0.079(5) 0.081(4) -0.016(4) 0.045(4) -0.024(4) C83 0.096(5) 0.037(3) 0.082(4) 0.000(3) 0.062(4) 0.004(3) C84 0.107(6) 0.043(4) 0.117(6) 0.008(4) 0.087(5) 0.011(4) C85 0.076(5) 0.052(4) 0.121(6) -0.003(4) 0.071(5) 0.003(4) C86 0.099(6) 0.048(4) 0.087(4) -0.002(3) 0.063(4) 0.001(4) C87 0.055(4) 0.044(4) 0.095(5) 0.008(3) 0.016(4) 0.005(3) C88 0.073(4) 0.053(4) 0.056(3) 0.012(3) 0.015(3) 0.000(4) C89 0.055(4) 0.105(6) 0.059(4) -0.005(4) 0.026(3) -0.019(4) C90 0.086(6) 0.059(5) 0.134(7) -0.004(4) 0.077(5) -0.007(4) F1 0.080(2) 0.097(3) 0.0578(19) -0.0083(18) 0.0322(18) -0.002(2) F2 0.099(3) 0.078(3) 0.084(3) 0.001(2) 0.025(2) 0.009(2) F3 0.109(3) 0.108(4) 0.082(3) 0.017(2) 0.054(2) -0.013(3) F4 0.064(2) 0.172(5) 0.105(3) -0.042(3) 0.046(2) -0.005(3) F5 0.098(3) 0.163(5) 0.118(4) 0.037(3) 0.068(3) 0.040(3) F6 0.083(3) 0.259(8) 0.098(3) -0.024(4) 0.050(3) 0.011(4) F7 0.241(8) 0.101(5) 0.250(8) -0.051(5) 0.150(7) -0.074(5) F8 0.107(4) 0.213(6) 0.067(2) 0.002(3) 0.042(2) 0.004(4) F9 0.174(5) 0.082(4) 0.142(4) -0.005(3) 0.057(4) -0.035(4) F10 0.108(4) 0.198(6) 0.080(3) 0.042(3) 0.046(3) 0.010(4) F11 0.064(2) 0.097(3) 0.070(2) 0.0025(19) 0.0385(18) 0.004(2) F12 0.081(3) 0.156(4) 0.056(2) -0.023(2) 0.0364(19) -0.011(3) Ir1 0.05176(13) 0.03470(11) 0.05089(11) 0.00198(8) 0.03197(10) 0.00132(10) Ir2 0.05316(13) 0.03387(11) 0.04346(11) 0.00188(8) 0.02973(9) 0.00272(10) N1 0.040(2) 0.044(3) 0.041(2) 0.0044(18) 0.0216(19) 0.004(2) N2 0.046(2) 0.038(2) 0.043(2) -0.0045(18) 0.0242(19) 0.002(2) N3 0.058(3) 0.039(3) 0.047(2) 0.0004(18) 0.033(2) -0.004(2) N4 0.055(3) 0.040(2) 0.043(2) 0.0053(18) 0.028(2) 0.005(2) N5 0.057(3) 0.040(3) 0.065(3) -0.006(2) 0.037(2) -0.004(2) N6 0.059(3) 0.047(3) 0.061(3) 0.011(2) 0.042(2) 0.008(2) N7 0.057(3) 0.044(3) 0.055(2) -0.001(2) 0.039(2) 0.009(2) C91 0.064(4) 0.034(3) 0.057(3) 0.000(2) 0.036(3) -0.006(3) P11 0.0574(10) 0.0906(14) 0.0553(9) -0.0059(8) 0.0295(8) 0.0002(10) P12 0.0710(11) 0.0733(13) 0.0673(10) -0.0016(8) 0.0374(9) -0.0116(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 C1 C61 1.400(7) . ? C1 C21 1.414(7) . ? C1 C9 1.416(7) . ? C2 N2 1.332(6) . ? C2 C4 1.407(7) . ? C2 C61 1.458(7) . ? C3 C20 1.400(8) . ? C3 C34 1.417(8) . ? C3 C4 1.424(7) . ? C4 C16 1.425(7) . ? C5 C37 1.389(8) . ? C5 C24 1.408(8) . ? C5 C12 1.413(8) . ? C6 C26 1.382(9) . ? C6 C25 1.383(9) . ? C6 H6 0.9300 . ? C7 C84 1.401(9) . ? C7 C11 1.424(8) . ? C7 C23 1.426(9) . ? C8 N6 1.367(7) . ? C8 C11 1.399(8) . ? C8 C30 1.421(8) . ? C9 C18 1.375(7) . ? C9 C16 1.463(7) . ? C10 C16 1.364(7) . ? C10 C14 1.394(8) . ? C10 H10 0.9300 . ? C11 C36 1.417(8) . ? C12 N5 1.375(7) . ? C12 C26 1.393(8) . ? C14 C34 1.345(8) . ? C14 H14 0.9300 . ? C15 C32 1.362(7) . ? C15 C21 1.405(7) . ? C15 H15 0.9300 . ? C17 N5 1.360(7) . ? C17 C25 1.379(8) . ? C17 H17 0.9300 . ? C18 C22 1.403(8) . ? C18 H18 0.9300 . ? C19 C27 1.351(10) . ? C19 C31 1.399(9) . ? C19 H19 0.9300 . ? C20 C28 1.356(7) . ? C20 H20 0.9300 . ? C21 C71 1.402(7) . ? C22 C71 1.357(8) . ? C22 H22 0.9300 . ? C23 C35 1.336(10) . ? C23 H23 0.9300 . ? C24 C27 1.405(9) . ? C24 C90 1.431(10) . ? C25 H25 0.9300 . ? C26 C33 1.456(9) . ? C27 H27 0.9300 . ? C28 N2 1.366(6) . ? C28 H28 0.9300 . ? C29 C36 1.380(8) . ? C29 C86 1.413(8) . ? C29 H29 0.9300 . ? C30 C81 1.405(9) . ? C30 C35 1.414(9) . ? C31 C37 1.378(7) . ? C31 H31 0.9300 . ? C32 N1 1.361(6) . ? C32 H32 0.9300 . ? C33 C90 1.336(10) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 Ir1 2.026(6) . ? C37 Ir1 2.025(5) . ? C38 C60 1.395(7) . ? C38 C76 1.407(8) . ? C38 C43 1.418(7) . ? C39 N3 1.317(6) . ? C39 C64 1.407(7) . ? C39 C41 1.455(7) . ? C40 C56 1.409(7) . ? C40 C47 1.414(8) . ? C40 C64 1.426(7) . ? C41 N4 1.341(6) . ? C41 C42 1.387(7) . ? C42 C51 1.426(7) . ? C42 C49 1.435(7) . ? C43 N7 1.383(7) . ? C43 C66 1.412(8) . ? C44 C67 1.356(7) . ? C44 C51 1.411(8) . ? C44 H44 0.9300 . ? C45 C52 1.391(7) . ? C45 C64 1.412(7) . ? C45 C49 1.463(7) . ? C46 C47 1.351(7) . ? C46 N3 1.377(6) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 N7 1.347(7) . ? C48 C69 1.395(8) . ? C48 H48 0.9300 . ? C49 C68 1.374(8) . ? C50 C91 1.400(8) . ? C50 C55 1.413(7) . ? C50 C63 1.420(7) . ? C51 C74 1.410(8) . ? C52 C58 1.390(8) . ? C52 H52 0.9300 . ? C54 C59 1.356(9) . ? C54 C55 1.403(9) . ? C54 H54 0.9300 . ? C55 C85 1.434(9) . ? C56 C58 1.361(8) . ? C56 H56 0.9300 . ? C57 C59 1.399(8) . ? C57 C91 1.407(7) . ? C57 H57 0.9300 . ? C58 H58 0.9300 . ? C59 H59 0.9300 . ? C60 C70 1.368(7) . ? C60 Ir2 2.025(5) . ? C61 N1 1.340(6) . ? N63 C72 1.344(6) . ? N63 C63 1.368(7) . ? N63 Ir2 2.079(4) . ? C63 C77 1.417(8) . ? C65 N6 1.320(7) . ? C65 C80 1.399(8) . ? C65 H65 0.9300 . ? C66 C75 1.401(8) . ? C66 C89 1.417(9) . ? C67 N4 1.372(6) . ? C67 H67 0.9300 . ? C68 C73 1.404(8) . ? C68 H68 0.9300 . ? C69 C75 1.352(9) . ? C69 H69 0.9300 . ? C70 C83 1.380(8) . ? C70 H70 0.9300 . ? C71 H71 0.9300 . ? C72 C88 1.390(8) . ? C72 H72 0.9300 . ? C73 C74 1.347(8) . ? C73 H73 0.9300 . ? C74 H74 0.9300 . ? C75 H75 0.9300 . ? C76 C78 1.411(9) . ? C76 C82 1.441(9) . ? C77 C87 1.403(9) . ? C77 C79 1.421(9) . ? C78 C83 1.365(9) . ? C78 H78 0.9300 . ? C79 C85 1.336(9) . ? C79 H79 0.9300 . ? C80 C81 1.352(9) . ? C80 H80 0.9300 . ? C81 H81 0.9300 . ? C82 C89 1.344(10) . ? C82 H82 0.9300 . ? C83 H83 0.9300 . ? C84 C86 1.350(9) . ? C84 H84 0.9300 . ? C85 H85 0.9300 . ? C86 H86 0.9300 . ? C87 C88 1.359(9) . ? C87 H87 0.9300 . ? C88 H88 0.9300 . ? C89 H89 0.9300 . ? C90 H90 0.9300 . ? F1 P11 1.597(4) . ? F2 P11 1.597(5) . ? F3 P11 1.593(5) . ? F4 P11 1.585(4) . ? F5 P12 1.566(5) . ? F6 P12 1.568(5) . ? F7 P12 1.562(6) . ? F8 P12 1.569(4) . ? F9 P12 1.541(5) . ? F10 P12 1.571(4) . ? F11 P11 1.594(4) . ? F12 P11 1.596(4) . ? Ir1 N5 2.030(5) . ? Ir1 N6 2.077(5) . ? Ir1 N2 2.123(4) . ? Ir1 N1 2.135(4) . ? Ir2 C91 2.029(5) . ? Ir2 N7 2.056(4) . ? Ir2 N4 2.120(4) . ? Ir2 N3 2.133(4) . ? 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 C61 C1 C21 118.1(5) . . ? C61 C1 C9 120.6(5) . . ? C21 C1 C9 121.3(5) . . ? N2 C2 C4 123.6(4) . . ? N2 C2 C61 117.0(4) . . ? C4 C2 C61 119.3(5) . . ? C20 C3 C34 124.1(5) . . ? C20 C3 C4 117.7(5) . . ? C34 C3 C4 118.2(5) . . ? C2 C4 C3 117.4(5) . . ? C2 C4 C16 121.5(5) . . ? C3 C4 C16 121.1(5) . . ? C37 C5 C24 123.6(6) . . ? C37 C5 C12 117.7(5) . . ? C24 C5 C12 118.7(6) . . ? C26 C6 C25 120.0(6) . . ? C26 C6 H6 120.0 . . ? C25 C6 H6 120.0 . . ? C84 C7 C11 116.9(6) . . ? C84 C7 C23 126.0(6) . . ? C11 C7 C23 117.0(6) . . ? N6 C8 C11 116.4(5) . . ? N6 C8 C30 121.7(5) . . ? C11 C8 C30 121.9(6) . . ? C18 C9 C1 116.8(5) . . ? C18 C9 C16 123.0(5) . . ? C1 C9 C16 120.1(5) . . ? C16 C10 C14 122.2(6) . . ? C16 C10 H10 118.9 . . ? C14 C10 H10 118.9 . . ? C8 C11 C36 117.6(5) . . ? C8 C11 C7 119.3(6) . . ? C36 C11 C7 123.0(6) . . ? N5 C12 C26 122.0(5) . . ? N5 C12 C5 114.5(5) . . ? C26 C12 C5 123.5(6) . . ? C34 C14 C10 121.8(6) . . ? C34 C14 H14 119.1 . . ? C10 C14 H14 119.1 . . ? C32 C15 C21 121.0(5) . . ? C32 C15 H15 119.5 . . ? C21 C15 H15 119.5 . . ? C10 C16 C4 117.0(5) . . ? C10 C16 C9 124.8(5) . . ? C4 C16 C9 118.1(5) . . ? N5 C17 C25 122.4(6) . . ? N5 C17 H17 118.8 . . ? C25 C17 H17 118.8 . . ? C9 C18 C22 122.2(6) . . ? C9 C18 H18 118.9 . . ? C22 C18 H18 118.9 . . ? C27 C19 C31 120.7(7) . . ? C27 C19 H19 119.7 . . ? C31 C19 H19 119.7 . . ? C28 C20 C3 120.7(5) . . ? C28 C20 H20 119.7 . . ? C3 C20 H20 119.7 . . ? C71 C21 C15 123.8(5) . . ? C71 C21 C1 119.1(5) . . ? C15 C21 C1 117.1(5) . . ? C71 C22 C18 120.8(6) . . ? C71 C22 H22 119.6 . . ? C18 C22 H22 119.6 . . ? C35 C23 C7 123.5(7) . . ? C35 C23 H23 118.2 . . ? C7 C23 H23 118.2 . . ? C27 C24 C5 116.6(6) . . ? C27 C24 C90 125.8(7) . . ? C5 C24 C90 117.6(7) . . ? C17 C25 C6 119.2(6) . . ? C17 C25 H25 120.4 . . ? C6 C25 H25 120.4 . . ? C6 C26 C12 118.6(6) . . ? C6 C26 C33 125.0(7) . . ? C12 C26 C33 116.4(6) . . ? C19 C27 C24 120.9(6) . . ? C19 C27 H27 119.5 . . ? C24 C27 H27 119.5 . . ? C20 C28 N2 122.5(5) . . ? C20 C28 H28 118.7 . . ? N2 C28 H28 118.7 . . ? C36 C29 C86 120.1(6) . . ? C36 C29 H29 119.9 . . ? C86 C29 H29 119.9 . . ? C81 C30 C35 125.5(7) . . ? C81 C30 C8 117.0(6) . . ? C35 C30 C8 117.6(6) . . ? C37 C31 C19 121.5(7) . . ? C37 C31 H31 119.2 . . ? C19 C31 H31 119.2 . . ? N1 C32 C15 121.9(5) . . ? N1 C32 H32 119.0 . . ? C15 C32 H32 119.0 . . ? C90 C33 C26 120.2(7) . . ? C90 C33 H33 119.9 . . ? C26 C33 H33 119.9 . . ? C14 C34 C3 119.7(5) . . ? C14 C34 H34 120.2 . . ? C3 C34 H34 120.2 . . ? C23 C35 C30 120.7(7) . . ? C23 C35 H35 119.7 . . ? C30 C35 H35 119.7 . . ? C29 C36 C11 117.0(5) . . ? C29 C36 Ir1 131.1(5) . . ? C11 C36 Ir1 111.9(4) . . ? C31 C37 C5 116.5(5) . . ? C31 C37 Ir1 130.9(4) . . ? C5 C37 Ir1 112.3(4) . . ? C60 C38 C76 123.9(5) . . ? C60 C38 C43 116.3(5) . . ? C76 C38 C43 119.8(6) . . ? N3 C39 C64 123.8(4) . . ? N3 C39 C41 117.6(4) . . ? C64 C39 C41 118.6(5) . . ? C56 C40 C47 123.5(5) . . ? C56 C40 C64 119.2(5) . . ? C47 C40 C64 117.4(4) . . ? N4 C41 C42 123.4(4) . . ? N4 C41 C39 116.2(4) . . ? C42 C41 C39 120.4(4) . . ? C41 C42 C51 118.3(5) . . ? C41 C42 C49 121.1(5) . . ? C51 C42 C49 120.6(5) . . ? N7 C43 C66 122.2(5) . . ? N7 C43 C38 116.5(5) . . ? C66 C43 C38 121.3(5) . . ? C67 C44 C51 120.6(5) . . ? C67 C44 H44 119.7 . . ? C51 C44 H44 119.7 . . ? C52 C45 C64 117.7(5) . . ? C52 C45 C49 123.5(5) . . ? C64 C45 C49 118.8(5) . . ? C47 C46 N3 121.7(5) . . ? C47 C46 H46 119.2 . . ? N3 C46 H46 119.2 . . ? C46 C47 C40 120.9(5) . . ? C46 C47 H47 119.5 . . ? C40 C47 H47 119.5 . . ? N7 C48 C69 121.4(6) . . ? N7 C48 H48 119.3 . . ? C69 C48 H48 119.3 . . ? C68 C49 C42 117.5(5) . . ? C68 C49 C45 123.8(5) . . ? C42 C49 C45 118.6(5) . . ? C91 C50 C55 123.5(5) . . ? C91 C50 C63 117.1(5) . . ? C55 C50 C63 119.2(5) . . ? C74 C51 C44 124.4(5) . . ? C74 C51 C42 118.4(5) . . ? C44 C51 C42 117.2(5) . . ? C58 C52 C45 121.3(5) . . ? C58 C52 H52 119.4 . . ? C45 C52 H52 119.4 . . ? C59 C54 C55 119.8(5) . . ? C59 C54 H54 120.1 . . ? C55 C54 H54 120.1 . . ? C54 C55 C50 117.4(6) . . ? C54 C55 C85 125.6(6) . . ? C50 C55 C85 117.0(6) . . ? C58 C56 C40 119.2(5) . . ? C58 C56 H56 120.4 . . ? C40 C56 H56 120.4 . . ? C59 C57 C91 119.4(6) . . ? C59 C57 H57 120.3 . . ? C91 C57 H57 120.3 . . ? C56 C58 C52 121.9(5) . . ? C56 C58 H58 119.0 . . ? C52 C58 H58 119.0 . . ? C54 C59 C57 123.1(6) . . ? C54 C59 H59 118.5 . . ? C57 C59 H59 118.5 . . ? C70 C60 C38 116.5(5) . . ? C70 C60 Ir2 130.1(4) . . ? C38 C60 Ir2 113.3(4) . . ? N1 C61 C1 123.4(4) . . ? N1 C61 C2 116.5(4) . . ? C1 C61 C2 120.0(5) . . ? C72 N63 C63 118.2(5) . . ? C72 N63 Ir2 128.4(4) . . ? C63 N63 Ir2 113.4(3) . . ? N63 C63 C77 122.4(5) . . ? N63 C63 C50 115.8(5) . . ? C77 C63 C50 121.8(5) . . ? C39 C64 C45 122.0(5) . . ? C39 C64 C40 117.3(5) . . ? C45 C64 C40 120.6(5) . . ? N6 C65 C80 121.8(6) . . ? N6 C65 H65 119.1 . . ? C80 C65 H65 119.1 . . ? C75 C66 C43 117.0(6) . . ? C75 C66 C89 125.4(6) . . ? C43 C66 C89 117.5(6) . . ? C44 C67 N4 122.2(5) . . ? C44 C67 H67 118.9 . . ? N4 C67 H67 118.9 . . ? C49 C68 C73 121.4(6) . . ? C49 C68 H68 119.3 . . ? C73 C68 H68 119.3 . . ? C75 C69 C48 120.7(6) . . ? C75 C69 H69 119.7 . . ? C48 C69 H69 119.7 . . ? C60 C70 C83 121.7(6) . . ? C60 C70 H70 119.2 . . ? C83 C70 H70 119.2 . . ? C22 C71 C21 119.7(5) . . ? C22 C71 H71 120.1 . . ? C21 C71 H71 120.1 . . ? N63 C72 C88 121.9(6) . . ? N63 C72 H72 119.0 . . ? C88 C72 H72 119.0 . . ? C74 C73 C68 121.7(6) . . ? C74 C73 H73 119.1 . . ? C68 C73 H73 119.1 . . ? C73 C74 C51 120.3(6) . . ? C73 C74 H74 119.9 . . ? C51 C74 H74 119.9 . . ? C69 C75 C66 120.4(6) . . ? C69 C75 H75 119.8 . . ? C66 C75 H75 119.8 . . ? C38 C76 C78 116.5(6) . . ? C38 C76 C82 117.7(6) . . ? C78 C76 C82 125.8(6) . . ? C87 C77 C63 117.1(6) . . ? C87 C77 C79 125.5(6) . . ? C63 C77 C79 117.4(6) . . ? C83 C78 C76 119.7(6) . . ? C83 C78 H78 120.1 . . ? C76 C78 H78 120.1 . . ? C85 C79 C77 120.7(6) . . ? C85 C79 H79 119.6 . . ? C77 C79 H79 119.6 . . ? C81 C80 C65 120.3(6) . . ? C81 C80 H80 119.8 . . ? C65 C80 H80 119.8 . . ? C80 C81 C30 119.9(6) . . ? C80 C81 H81 120.1 . . ? C30 C81 H81 120.1 . . ? C89 C82 C76 121.8(6) . . ? C89 C82 H82 119.1 . . ? C76 C82 H82 119.1 . . ? C78 C83 C70 121.7(6) . . ? C78 C83 H83 119.1 . . ? C70 C83 H83 119.1 . . ? C86 C84 C7 120.4(6) . . ? C86 C84 H84 119.8 . . ? C7 C84 H84 119.8 . . ? C79 C85 C55 123.7(6) . . ? C79 C85 H85 118.1 . . ? C55 C85 H85 118.1 . . ? C84 C86 C29 122.5(7) . . ? C84 C86 H86 118.7 . . ? C29 C86 H86 118.7 . . ? C88 C87 C77 119.8(6) . . ? C88 C87 H87 120.1 . . ? C77 C87 H87 120.1 . . ? C87 C88 C72 120.6(6) . . ? C87 C88 H88 119.7 . . ? C72 C88 H88 119.7 . . ? C82 C89 C66 121.9(6) . . ? C82 C89 H89 119.1 . . ? C66 C89 H89 119.1 . . ? C33 C90 C24 123.5(7) . . ? C33 C90 H90 118.3 . . ? C24 C90 H90 118.3 . . ? C37 Ir1 C36 93.0(2) . . ? C37 Ir1 N5 80.9(2) . . ? C36 Ir1 N5 91.5(2) . . ? C37 Ir1 N6 93.8(2) . . ? C36 Ir1 N6 81.0(2) . . ? N5 Ir1 N6 170.62(18) . . ? C37 Ir1 N2 171.46(18) . . ? C36 Ir1 N2 94.57(18) . . ? N5 Ir1 N2 94.98(16) . . ? N6 Ir1 N2 91.24(16) . . ? C37 Ir1 N1 95.30(18) . . ? C36 Ir1 N1 170.77(19) . . ? N5 Ir1 N1 93.67(16) . . ? N6 Ir1 N1 94.53(16) . . ? N2 Ir1 N1 77.41(15) . . ? C60 Ir2 C91 89.96(19) . . ? C60 Ir2 N7 81.15(19) . . ? C91 Ir2 N7 93.78(19) . . ? C60 Ir2 N63 93.97(18) . . ? C91 Ir2 N63 80.46(19) . . ? N7 Ir2 N63 172.50(16) . . ? C60 Ir2 N4 169.85(18) . . ? C91 Ir2 N4 98.11(18) . . ? N7 Ir2 N4 92.12(17) . . ? N63 Ir2 N4 93.44(16) . . ? C60 Ir2 N3 95.13(17) . . ? C91 Ir2 N3 172.9(2) . . ? N7 Ir2 N3 91.84(16) . . ? N63 Ir2 N3 94.28(16) . . ? N4 Ir2 N3 77.39(15) . . ? C61 N1 C32 118.3(4) . . ? C61 N1 Ir1 114.2(3) . . ? C32 N1 Ir1 127.5(3) . . ? C2 N2 C28 118.1(4) . . ? C2 N2 Ir1 114.7(3) . . ? C28 N2 Ir1 127.2(4) . . ? C39 N3 C46 118.9(4) . . ? C39 N3 Ir2 114.1(3) . . ? C46 N3 Ir2 127.0(3) . . ? C41 N4 C67 118.2(4) . . ? C41 N4 Ir2 114.2(3) . . ? C67 N4 Ir2 127.1(3) . . ? C17 N5 C12 117.8(5) . . ? C17 N5 Ir1 127.5(4) . . ? C12 N5 Ir1 114.4(4) . . ? C65 N6 C8 119.2(5) . . ? C65 N6 Ir1 128.0(4) . . ? C8 N6 Ir1 112.8(4) . . ? C48 N7 C43 118.3(5) . . ? C48 N7 Ir2 129.0(4) . . ? C43 N7 Ir2 112.7(3) . . ? C50 C91 C57 116.8(5) . . ? C50 C91 Ir2 113.0(4) . . ? C57 C91 Ir2 130.1(4) . . ? F4 P11 F3 89.5(3) . . ? F4 P11 F11 178.7(3) . . ? F3 P11 F11 89.2(2) . . ? F4 P11 F12 90.9(2) . . ? F3 P11 F12 91.0(2) . . ? F11 P11 F12 89.3(2) . . ? F4 P11 F1 90.5(2) . . ? F3 P11 F1 89.8(2) . . ? F11 P11 F1 89.3(2) . . ? F12 P11 F1 178.4(3) . . ? F4 P11 F2 91.1(3) . . ? F3 P11 F2 179.0(3) . . ? F11 P11 F2 90.2(2) . . ? F12 P11 F2 89.8(2) . . ? F1 P11 F2 89.4(2) . . ? F9 P12 F7 177.3(4) . . ? F9 P12 F5 89.5(4) . . ? F7 P12 F5 90.9(4) . . ? F9 P12 F6 92.1(4) . . ? F7 P12 F6 87.5(4) . . ? F5 P12 F6 178.1(4) . . ? F9 P12 F8 89.4(3) . . ? F7 P12 F8 87.9(4) . . ? F5 P12 F8 89.6(3) . . ? F6 P12 F8 89.5(3) . . ? F9 P12 F10 88.8(3) . . ? F7 P12 F10 93.8(4) . . ? F5 P12 F10 91.1(3) . . ? F6 P12 F10 89.9(3) . . ? F8 P12 F10 178.1(4) . . ? 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 N2 C2 C4 C3 0.6(7) . . . . ? C61 C2 C4 C3 -176.7(4) . . . . ? N2 C2 C4 C16 -179.7(5) . . . . ? C61 C2 C4 C16 3.0(7) . . . . ? C20 C3 C4 C2 -0.4(7) . . . . ? C34 C3 C4 C2 178.1(5) . . . . ? C20 C3 C4 C16 179.9(5) . . . . ? C34 C3 C4 C16 -1.7(7) . . . . ? C61 C1 C9 C18 -175.5(5) . . . . ? C21 C1 C9 C18 2.0(8) . . . . ? C61 C1 C9 C16 4.6(7) . . . . ? C21 C1 C9 C16 -177.9(5) . . . . ? N6 C8 C11 C36 -3.2(7) . . . . ? C30 C8 C11 C36 176.2(5) . . . . ? N6 C8 C11 C7 -178.7(5) . . . . ? C30 C8 C11 C7 0.7(8) . . . . ? C84 C7 C11 C8 177.3(5) . . . . ? C23 C7 C11 C8 -1.4(8) . . . . ? C84 C7 C11 C36 2.0(8) . . . . ? C23 C7 C11 C36 -176.6(5) . . . . ? C37 C5 C12 N5 -4.1(7) . . . . ? C24 C5 C12 N5 175.9(5) . . . . ? C37 C5 C12 C26 175.5(5) . . . . ? C24 C5 C12 C26 -4.5(8) . . . . ? C16 C10 C14 C34 -1.2(9) . . . . ? C14 C10 C16 C4 0.1(8) . . . . ? C14 C10 C16 C9 -179.9(5) . . . . ? C2 C4 C16 C10 -178.5(5) . . . . ? C3 C4 C16 C10 1.3(7) . . . . ? C2 C4 C16 C9 1.6(7) . . . . ? C3 C4 C16 C9 -178.7(5) . . . . ? C18 C9 C16 C10 -5.3(9) . . . . ? C1 C9 C16 C10 174.6(5) . . . . ? C18 C9 C16 C4 174.7(5) . . . . ? C1 C9 C16 C4 -5.4(7) . . . . ? C1 C9 C18 C22 0.4(9) . . . . ? C16 C9 C18 C22 -179.7(5) . . . . ? C34 C3 C20 C28 -178.6(5) . . . . ? C4 C3 C20 C28 -0.3(8) . . . . ? C32 C15 C21 C71 -174.9(5) . . . . ? C32 C15 C21 C1 3.6(8) . . . . ? C61 C1 C21 C71 174.9(5) . . . . ? C9 C1 C21 C71 -2.7(8) . . . . ? C61 C1 C21 C15 -3.7(7) . . . . ? C9 C1 C21 C15 178.8(5) . . . . ? C9 C18 C22 C71 -2.2(10) . . . . ? C84 C7 C23 C35 -178.3(6) . . . . ? C11 C7 C23 C35 0.1(9) . . . . ? C37 C5 C24 C27 2.6(9) . . . . ? C12 C5 C24 C27 -177.4(5) . . . . ? C37 C5 C24 C90 -177.5(6) . . . . ? C12 C5 C24 C90 2.5(8) . . . . ? N5 C17 C25 C6 -0.7(9) . . . . ? C26 C6 C25 C17 1.3(10) . . . . ? C25 C6 C26 C12 -2.0(9) . . . . ? C25 C6 C26 C33 176.9(6) . . . . ? N5 C12 C26 C6 2.1(9) . . . . ? C5 C12 C26 C6 -177.6(5) . . . . ? N5 C12 C26 C33 -176.9(5) . . . . ? C5 C12 C26 C33 3.4(9) . . . . ? C31 C19 C27 C24 -0.7(11) . . . . ? C5 C24 C27 C19 -0.7(9) . . . . ? C90 C24 C27 C19 179.4(7) . . . . ? C3 C20 C28 N2 0.8(8) . . . . ? N6 C8 C30 C81 0.6(8) . . . . ? C11 C8 C30 C81 -178.8(5) . . . . ? N6 C8 C30 C35 -179.5(5) . . . . ? C11 C8 C30 C35 1.1(8) . . . . ? C27 C19 C31 C37 0.4(10) . . . . ? C21 C15 C32 N1 -0.7(8) . . . . ? C6 C26 C33 C90 -179.5(7) . . . . ? C12 C26 C33 C90 -0.6(10) . . . . ? C10 C14 C34 C3 0.9(9) . . . . ? C20 C3 C34 C14 178.9(6) . . . . ? C4 C3 C34 C14 0.6(8) . . . . ? C7 C23 C35 C30 1.8(10) . . . . ? C81 C30 C35 C23 177.6(6) . . . . ? C8 C30 C35 C23 -2.3(9) . . . . ? C86 C29 C36 C11 -0.2(8) . . . . ? C86 C29 C36 Ir1 175.9(4) . . . . ? C8 C11 C36 C29 -176.5(5) . . . . ? C7 C11 C36 C29 -1.2(8) . . . . ? C8 C11 C36 Ir1 6.7(6) . . . . ? C7 C11 C36 Ir1 -178.0(4) . . . . ? C19 C31 C37 C5 1.4(8) . . . . ? C19 C31 C37 Ir1 175.6(5) . . . . ? C24 C5 C37 C31 -3.0(8) . . . . ? C12 C5 C37 C31 177.1(5) . . . . ? C24 C5 C37 Ir1 -178.2(4) . . . . ? C12 C5 C37 Ir1 1.8(6) . . . . ? N3 C39 C41 N4 4.1(7) . . . . ? C64 C39 C41 N4 -175.4(4) . . . . ? N3 C39 C41 C42 -175.0(5) . . . . ? C64 C39 C41 C42 5.5(7) . . . . ? N4 C41 C42 C51 -1.0(7) . . . . ? C39 C41 C42 C51 178.0(4) . . . . ? N4 C41 C42 C49 179.4(5) . . . . ? C39 C41 C42 C49 -1.6(7) . . . . ? C60 C38 C43 N7 1.0(6) . . . . ? C76 C38 C43 N7 -177.6(4) . . . . ? C60 C38 C43 C66 -180.0(4) . . . . ? C76 C38 C43 C66 1.4(7) . . . . ? N3 C46 C47 C40 -0.1(9) . . . . ? C56 C40 C47 C46 -179.1(6) . . . . ? C64 C40 C47 C46 -0.9(8) . . . . ? C41 C42 C49 C68 176.4(5) . . . . ? C51 C42 C49 C68 -3.1(8) . . . . ? C41 C42 C49 C45 -4.1(7) . . . . ? C51 C42 C49 C45 176.4(5) . . . . ? C52 C45 C49 C68 5.8(9) . . . . ? C64 C45 C49 C68 -174.8(5) . . . . ? C52 C45 C49 C42 -173.7(5) . . . . ? C64 C45 C49 C42 5.8(7) . . . . ? C67 C44 C51 C74 177.7(5) . . . . ? C67 C44 C51 C42 -1.0(8) . . . . ? C41 C42 C51 C74 -176.5(5) . . . . ? C49 C42 C51 C74 3.0(8) . . . . ? C41 C42 C51 C44 2.3(7) . . . . ? C49 C42 C51 C44 -178.1(5) . . . . ? C64 C45 C52 C58 1.8(8) . . . . ? C49 C45 C52 C58 -178.8(5) . . . . ? C59 C54 C55 C50 0.0(9) . . . . ? C59 C54 C55 C85 -178.1(6) . . . . ? C91 C50 C55 C54 0.0(8) . . . . ? C63 C50 C55 C54 -176.1(5) . . . . ? C91 C50 C55 C85 178.2(5) . . . . ? C63 C50 C55 C85 2.2(8) . . . . ? C47 C40 C56 C58 179.8(6) . . . . ? C64 C40 C56 C58 1.7(9) . . . . ? C40 C56 C58 C52 -2.3(10) . . . . ? C45 C52 C58 C56 0.6(9) . . . . ? C55 C54 C59 C57 0.1(10) . . . . ? C91 C57 C59 C54 0.0(9) . . . . ? C76 C38 C60 C70 0.6(7) . . . . ? C43 C38 C60 C70 -177.9(4) . . . . ? C76 C38 C60 Ir2 178.3(4) . . . . ? C43 C38 C60 Ir2 -0.3(5) . . . . ? C21 C1 C61 N1 1.1(7) . . . . ? C9 C1 C61 N1 178.7(4) . . . . ? C21 C1 C61 C2 -177.5(4) . . . . ? C9 C1 C61 C2 0.1(7) . . . . ? N2 C2 C61 N1 -0.1(6) . . . . ? C4 C2 C61 N1 177.4(4) . . . . ? N2 C2 C61 C1 178.6(4) . . . . ? C4 C2 C61 C1 -3.9(7) . . . . ? C72 N63 C63 C77 1.4(8) . . . . ? Ir2 N63 C63 C77 179.9(4) . . . . ? C72 N63 C63 C50 -177.3(5) . . . . ? Ir2 N63 C63 C50 1.3(6) . . . . ? C91 C50 C63 N63 2.2(7) . . . . ? C55 C50 C63 N63 178.5(5) . . . . ? C91 C50 C63 C77 -176.5(5) . . . . ? C55 C50 C63 C77 -0.2(8) . . . . ? N3 C39 C64 C45 176.8(5) . . . . ? C41 C39 C64 C45 -3.8(7) . . . . ? N3 C39 C64 C40 -3.2(8) . . . . ? C41 C39 C64 C40 176.2(4) . . . . ? C52 C45 C64 C39 177.7(5) . . . . ? C49 C45 C64 C39 -1.8(8) . . . . ? C52 C45 C64 C40 -2.3(8) . . . . ? C49 C45 C64 C40 178.2(5) . . . . ? C56 C40 C64 C39 -179.3(5) . . . . ? C47 C40 C64 C39 2.4(7) . . . . ? C56 C40 C64 C45 0.7(8) . . . . ? C47 C40 C64 C45 -177.6(5) . . . . ? N7 C43 C66 C75 -0.2(8) . . . . ? C38 C43 C66 C75 -179.3(5) . . . . ? N7 C43 C66 C89 179.2(5) . . . . ? C38 C43 C66 C89 0.2(8) . . . . ? C51 C44 C67 N4 -1.7(8) . . . . ? C42 C49 C68 C73 1.1(8) . . . . ? C45 C49 C68 C73 -178.4(5) . . . . ? N7 C48 C69 C75 0.4(8) . . . . ? C38 C60 C70 C83 1.6(7) . . . . ? Ir2 C60 C70 C83 -175.6(4) . . . . ? C18 C22 C71 C21 1.5(9) . . . . ? C15 C21 C71 C22 179.3(5) . . . . ? C1 C21 C71 C22 0.9(8) . . . . ? C63 N63 C72 C88 -1.2(8) . . . . ? Ir2 N63 C72 C88 -179.5(4) . . . . ? C49 C68 C73 C74 1.0(10) . . . . ? C68 C73 C74 C51 -1.1(10) . . . . ? C44 C51 C74 C73 -179.6(6) . . . . ? C42 C51 C74 C73 -0.9(9) . . . . ? C48 C69 C75 C66 0.9(9) . . . . ? C43 C66 C75 C69 -0.9(8) . . . . ? C89 C66 C75 C69 179.6(6) . . . . ? C60 C38 C76 C78 -2.1(7) . . . . ? C43 C38 C76 C78 176.4(5) . . . . ? C60 C38 C76 C82 179.2(5) . . . . ? C43 C38 C76 C82 -2.3(7) . . . . ? N63 C63 C77 C87 -0.9(8) . . . . ? C50 C63 C77 C87 177.7(5) . . . . ? N63 C63 C77 C79 179.8(5) . . . . ? C50 C63 C77 C79 -1.7(8) . . . . ? C38 C76 C78 C83 1.4(8) . . . . ? C82 C76 C78 C83 180.0(6) . . . . ? C87 C77 C79 C85 -177.8(6) . . . . ? C63 C77 C79 C85 1.5(9) . . . . ? N6 C65 C80 C81 -0.1(10) . . . . ? C65 C80 C81 C30 -2.6(10) . . . . ? C35 C30 C81 C80 -177.7(6) . . . . ? C8 C30 C81 C80 2.2(9) . . . . ? C38 C76 C82 C89 1.7(9) . . . . ? C78 C76 C82 C89 -176.9(6) . . . . ? C76 C78 C83 C70 0.7(9) . . . . ? C60 C70 C83 C78 -2.3(9) . . . . ? C11 C7 C84 C86 -1.6(9) . . . . ? C23 C7 C84 C86 176.9(6) . . . . ? C77 C79 C85 C55 0.6(10) . . . . ? C54 C55 C85 C79 175.6(6) . . . . ? C50 C55 C85 C79 -2.5(9) . . . . ? C7 C84 C86 C29 0.3(10) . . . . ? C36 C29 C86 C84 0.6(9) . . . . ? C63 C77 C87 C88 0.2(9) . . . . ? C79 C77 C87 C88 179.5(6) . . . . ? C77 C87 C88 C72 -0.1(10) . . . . ? N63 C72 C88 C87 0.6(9) . . . . ? C76 C82 C89 C66 0.0(10) . . . . ? C75 C66 C89 C82 178.5(6) . . . . ? C43 C66 C89 C82 -0.9(9) . . . . ? C26 C33 C90 C24 -1.2(11) . . . . ? C27 C24 C90 C33 -179.9(7) . . . . ? C5 C24 C90 C33 0.2(10) . . . . ? C31 C37 Ir1 C36 95.0(5) . . . . ? C5 C37 Ir1 C36 -90.6(4) . . . . ? C31 C37 Ir1 N5 -173.9(5) . . . . ? C5 C37 Ir1 N5 0.5(4) . . . . ? C31 C37 Ir1 N6 13.9(5) . . . . ? C5 C37 Ir1 N6 -171.7(4) . . . . ? C31 C37 Ir1 N2 -112.1(12) . . . . ? C5 C37 Ir1 N2 62.3(14) . . . . ? C31 C37 Ir1 N1 -81.0(5) . . . . ? C5 C37 Ir1 N1 93.4(4) . . . . ? C29 C36 Ir1 C37 84.6(5) . . . . ? C11 C36 Ir1 C37 -99.1(4) . . . . ? C29 C36 Ir1 N5 3.7(5) . . . . ? C11 C36 Ir1 N5 179.9(4) . . . . ? C29 C36 Ir1 N6 178.0(6) . . . . ? C11 C36 Ir1 N6 -5.7(4) . . . . ? C29 C36 Ir1 N2 -91.5(5) . . . . ? C11 C36 Ir1 N2 84.8(4) . . . . ? C29 C36 Ir1 N1 -120.8(11) . . . . ? C11 C36 Ir1 N1 55.5(13) . . . . ? C70 C60 Ir2 C91 -89.2(5) . . . . ? C38 C60 Ir2 C91 93.6(4) . . . . ? C70 C60 Ir2 N7 177.0(5) . . . . ? C38 C60 Ir2 N7 -0.3(3) . . . . ? C70 C60 Ir2 N63 -8.8(5) . . . . ? C38 C60 Ir2 N63 174.0(3) . . . . ? C70 C60 Ir2 N4 128.0(9) . . . . ? C38 C60 Ir2 N4 -49.2(10) . . . . ? C70 C60 Ir2 N3 85.9(5) . . . . ? C38 C60 Ir2 N3 -91.3(3) . . . . ? C72 N63 Ir2 C60 86.2(5) . . . . ? C63 N63 Ir2 C60 -92.2(4) . . . . ? C72 N63 Ir2 C91 175.5(5) . . . . ? C63 N63 Ir2 C91 -2.9(4) . . . . ? C72 N63 Ir2 N7 135.3(12) . . . . ? C63 N63 Ir2 N7 -43.0(14) . . . . ? C72 N63 Ir2 N4 -86.9(5) . . . . ? C63 N63 Ir2 N4 94.8(4) . . . . ? C72 N63 Ir2 N3 -9.3(5) . . . . ? C63 N63 Ir2 N3 172.4(3) . . . . ? C1 C61 N1 C32 1.8(7) . . . . ? C2 C61 N1 C32 -179.6(4) . . . . ? C1 C61 N1 Ir1 -175.8(4) . . . . ? C2 C61 N1 Ir1 2.8(5) . . . . ? C15 C32 N1 C61 -2.0(7) . . . . ? C15 C32 N1 Ir1 175.2(4) . . . . ? C37 Ir1 N1 C61 -178.7(3) . . . . ? C36 Ir1 N1 C61 26.8(13) . . . . ? N5 Ir1 N1 C61 -97.5(3) . . . . ? N6 Ir1 N1 C61 87.1(3) . . . . ? N2 Ir1 N1 C61 -3.2(3) . . . . ? C37 Ir1 N1 C32 4.0(4) . . . . ? C36 Ir1 N1 C32 -150.5(11) . . . . ? N5 Ir1 N1 C32 85.2(4) . . . . ? N6 Ir1 N1 C32 -90.3(4) . . . . ? N2 Ir1 N1 C32 179.5(4) . . . . ? C4 C2 N2 C28 -0.1(7) . . . . ? C61 C2 N2 C28 177.2(4) . . . . ? C4 C2 N2 Ir1 179.9(4) . . . . ? C61 C2 N2 Ir1 -2.7(5) . . . . ? C20 C28 N2 C2 -0.6(8) . . . . ? C20 C28 N2 Ir1 179.3(4) . . . . ? C37 Ir1 N2 C2 34.9(14) . . . . ? C36 Ir1 N2 C2 -172.3(4) . . . . ? N5 Ir1 N2 C2 95.8(4) . . . . ? N6 Ir1 N2 C2 -91.2(4) . . . . ? N1 Ir1 N2 C2 3.1(3) . . . . ? C37 Ir1 N2 C28 -145.0(12) . . . . ? C36 Ir1 N2 C28 7.8(4) . . . . ? N5 Ir1 N2 C28 -84.1(4) . . . . ? N6 Ir1 N2 C28 88.9(4) . . . . ? N1 Ir1 N2 C28 -176.8(4) . . . . ? C64 C39 N3 C46 2.3(8) . . . . ? C41 C39 N3 C46 -177.2(4) . . . . ? C64 C39 N3 Ir2 -178.7(4) . . . . ? C41 C39 N3 Ir2 1.8(6) . . . . ? C47 C46 N3 C39 -0.5(8) . . . . ? C47 C46 N3 Ir2 -179.4(4) . . . . ? C60 Ir2 N3 C39 168.6(4) . . . . ? C91 Ir2 N3 C39 -55.4(16) . . . . ? N7 Ir2 N3 C39 87.3(4) . . . . ? N63 Ir2 N3 C39 -97.0(4) . . . . ? N4 Ir2 N3 C39 -4.4(4) . . . . ? C60 Ir2 N3 C46 -12.5(5) . . . . ? C91 Ir2 N3 C46 123.5(15) . . . . ? N7 Ir2 N3 C46 -93.8(4) . . . . ? N63 Ir2 N3 C46 81.9(4) . . . . ? N4 Ir2 N3 C46 174.5(5) . . . . ? C42 C41 N4 C67 -1.7(7) . . . . ? C39 C41 N4 C67 179.3(4) . . . . ? C42 C41 N4 Ir2 171.2(4) . . . . ? C39 C41 N4 Ir2 -7.8(5) . . . . ? C44 C67 N4 C41 3.1(7) . . . . ? C44 C67 N4 Ir2 -168.7(4) . . . . ? C60 Ir2 N4 C41 -36.6(11) . . . . ? C91 Ir2 N4 C41 -178.9(4) . . . . ? N7 Ir2 N4 C41 -84.8(3) . . . . ? N63 Ir2 N4 C41 100.3(3) . . . . ? N3 Ir2 N4 C41 6.6(3) . . . . ? C60 Ir2 N4 C67 135.6(9) . . . . ? C91 Ir2 N4 C67 -6.8(4) . . . . ? N7 Ir2 N4 C67 87.3(4) . . . . ? N63 Ir2 N4 C67 -87.6(4) . . . . ? N3 Ir2 N4 C67 178.8(4) . . . . ? C25 C17 N5 C12 0.7(8) . . . . ? C25 C17 N5 Ir1 173.6(4) . . . . ? C26 C12 N5 C17 -1.4(8) . . . . ? C5 C12 N5 C17 178.2(5) . . . . ? C26 C12 N5 Ir1 -175.3(4) . . . . ? C5 C12 N5 Ir1 4.4(6) . . . . ? C37 Ir1 N5 C17 -175.8(5) . . . . ? C36 Ir1 N5 C17 -83.0(5) . . . . ? N6 Ir1 N5 C17 -119.6(10) . . . . ? N2 Ir1 N5 C17 11.7(5) . . . . ? N1 Ir1 N5 C17 89.4(4) . . . . ? C37 Ir1 N5 C12 -2.7(4) . . . . ? C36 Ir1 N5 C12 90.1(4) . . . . ? N6 Ir1 N5 C12 53.5(12) . . . . ? N2 Ir1 N5 C12 -175.1(4) . . . . ? N1 Ir1 N5 C12 -97.5(4) . . . . ? C80 C65 N6 C8 2.9(8) . . . . ? C80 C65 N6 Ir1 -179.3(4) . . . . ? C11 C8 N6 C65 176.3(5) . . . . ? C30 C8 N6 C65 -3.2(8) . . . . ? C11 C8 N6 Ir1 -1.8(6) . . . . ? C30 C8 N6 Ir1 178.7(4) . . . . ? C37 Ir1 N6 C65 -81.2(5) . . . . ? C36 Ir1 N6 C65 -173.7(5) . . . . ? N5 Ir1 N6 C65 -136.5(10) . . . . ? N2 Ir1 N6 C65 91.9(5) . . . . ? N1 Ir1 N6 C65 14.4(5) . . . . ? C37 Ir1 N6 C8 96.7(4) . . . . ? C36 Ir1 N6 C8 4.2(4) . . . . ? N5 Ir1 N6 C8 41.4(12) . . . . ? N2 Ir1 N6 C8 -90.2(4) . . . . ? N1 Ir1 N6 C8 -167.7(3) . . . . ? C69 C48 N7 C43 -1.6(7) . . . . ? C69 C48 N7 Ir2 -179.6(4) . . . . ? C66 C43 N7 C48 1.5(7) . . . . ? C38 C43 N7 C48 -179.5(4) . . . . ? C66 C43 N7 Ir2 179.8(4) . . . . ? C38 C43 N7 Ir2 -1.1(5) . . . . ? C60 Ir2 N7 C48 178.8(4) . . . . ? C91 Ir2 N7 C48 89.5(4) . . . . ? N63 Ir2 N7 C48 129.1(12) . . . . ? N4 Ir2 N7 C48 -8.8(4) . . . . ? N3 Ir2 N7 C48 -86.2(4) . . . . ? C60 Ir2 N7 C43 0.8(3) . . . . ? C91 Ir2 N7 C43 -88.6(3) . . . . ? N63 Ir2 N7 C43 -49.0(14) . . . . ? N4 Ir2 N7 C43 173.1(3) . . . . ? N3 Ir2 N7 C43 95.7(3) . . . . ? C55 C50 C91 C57 0.1(8) . . . . ? C63 C50 C91 C57 176.2(5) . . . . ? C55 C50 C91 Ir2 179.3(4) . . . . ? C63 C50 C91 Ir2 -4.6(6) . . . . ? C59 C57 C91 C50 0.0(8) . . . . ? C59 C57 C91 Ir2 -179.1(4) . . . . ? C60 Ir2 C91 C50 98.0(4) . . . . ? N7 Ir2 C91 C50 179.1(4) . . . . ? N63 Ir2 C91 C50 4.0(4) . . . . ? N4 Ir2 C91 C50 -88.2(4) . . . . ? N3 Ir2 C91 C50 -38.2(17) . . . . ? C60 Ir2 C91 C57 -82.9(5) . . . . ? N7 Ir2 C91 C57 -1.8(5) . . . . ? N63 Ir2 C91 C57 -176.9(5) . . . . ? N4 Ir2 C91 C57 90.9(5) . . . . ? N3 Ir2 C91 C57 140.9(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.173 _refine_diff_density_min -1.285 _refine_diff_density_rms 0.087 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 1 -0.500 0.000 0.000 599.9 156.6 2 -0.500 0.500 0.500 599.9 155.6 ; data_pit3i _database_code_depnum_ccdc_archive 'CCDC 827353' #TrackingRef '- pit3i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(1-phenylisoqinoline)(1,12-diazaperylene)iridium(III)-hexafluorophosphate ; _chemical_melting_point '> 633' _chemical_formula_moiety 'C48 H30 Ir N4 1+ , F6 P 1-' _chemical_formula_sum 'C48 H30 F6 Ir N4 P' _chemical_formula_weight 999.93 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 24.5034(4) _cell_length_b 35.5337(12) _cell_length_c 9.600(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8358.3(19) _cell_formula_units_Z 8 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 33786 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 26.92 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 1.350 _exptl_crystal_size_mid 0.580 _exptl_crystal_size_min 0.170 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method ? _exptl_crystal_F_000 3936 _exptl_absorpt_coefficient_mu 3.299 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.3357 _exptl_absorpt_correction_T_max 0.3494 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12 x 0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 120 mm ; _diffrn_reflns_number 63946 _diffrn_reflns_av_R_equivalents 0.1609 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.10 _reflns_number_total 9236 _reflns_number_gt 5673 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were calculated in their expected positions and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _refine_special_details ; The unit cell contains disordered solvent molecules. In spite of several attempts, no reasonable solution could be received. Therefore the contribution of the disordered solvent species was subtracted from the structure factor calculation by the SQUEEZE instruction of the PLATON program suite. SQUEEZE calculated 1261,8 \%A as solvent-accessible void volume and a number of electrons of 353 per cell. In consideration of Z these values correspond roughly with two molecules of methylenechlorid per asymmetric unit. The PF6 anions were refined isotropically. One of the both PF6 anions were refined with a disorder model by means of the restraint instructions SADI, SIMU and SAME. The occupancies (over two sides) were refined using free variables giving an occupation ratio of about 0.8/0.2. ; _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^)+(0.1282P)^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 SHELXL _refine_ls_extinction_coef 0.0032(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9236 _refine_ls_number_parameters 522 _refine_ls_number_restraints 279 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.2113 _refine_ls_wR_factor_gt 0.1966 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.006 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 C1 C 0.1572(3) 0.0673(2) 0.4992(8) 0.083(2) Uani 1 1 d . . . H1 H 0.1404 0.0862 0.4478 0.099 Uiso 1 1 calc R . . C2 C 0.1426(4) 0.0303(3) 0.4764(9) 0.092(2) Uani 1 1 d . . . H2 H 0.1156 0.0247 0.4116 0.111 Uiso 1 1 calc R . . C3 C 0.1571(4) -0.0372(3) 0.5317(11) 0.109(3) Uani 1 1 d . . . H3 H 0.1295 -0.0444 0.4709 0.130 Uiso 1 1 calc R . . C4 C 0.1852(5) -0.0636(3) 0.5992(12) 0.110(3) Uani 1 1 d . . . H4 H 0.1777 -0.0889 0.5835 0.132 Uiso 1 1 calc R . . C5 C 0.2250(4) -0.0534(3) 0.6918(13) 0.105(3) Uani 1 1 d . . . H5 H 0.2442 -0.0726 0.7361 0.126 Uiso 1 1 calc R . . C6 C 0.3115(4) -0.0297(3) 0.8920(10) 0.102(3) Uani 1 1 d . . . H6 H 0.3072 -0.0554 0.8759 0.122 Uiso 1 1 calc R . . C7 C 0.3521(4) -0.0174(3) 0.9919(11) 0.118(3) Uani 1 1 d . . . H7 H 0.3733 -0.0350 1.0389 0.142 Uiso 1 1 calc R . . C8 C 0.3597(4) 0.0214(3) 1.0178(10) 0.109(3) Uani 1 1 d . . . H8 H 0.3862 0.0297 1.0800 0.131 Uiso 1 1 calc R . . C9 C 0.3301(4) 0.0857(3) 0.9701(9) 0.098(2) Uani 1 1 d . . . H9 H 0.3543 0.0950 1.0364 0.118 Uiso 1 1 calc R . . C10 C 0.2984(4) 0.1105(3) 0.8955(8) 0.086(2) Uani 1 1 d . . . H10 H 0.3016 0.1361 0.9136 0.104 Uiso 1 1 calc R . . C11 C 0.2580(3) 0.0616(2) 0.7769(8) 0.0756(18) Uani 1 1 d . . . C12 C 0.2200(3) 0.0494(3) 0.6687(8) 0.081(2) Uani 1 1 d . . . C13 C 0.2089(4) 0.0107(3) 0.6478(9) 0.086(2) Uani 1 1 d . . . C14 C 0.2388(3) -0.0165(2) 0.7242(9) 0.083(2) Uani 1 1 d . . . C15 C 0.2798(3) -0.0054(3) 0.8221(10) 0.088(2) Uani 1 1 d . . . C16 C 0.2872(4) 0.0344(3) 0.8498(8) 0.087(2) Uani 1 1 d . . . C17 C 0.3266(4) 0.0468(2) 0.9480(9) 0.090(2) Uani 1 1 d . . . C18 C 0.1679(3) 0.0014(2) 0.5496(10) 0.088(2) Uani 1 1 d . . . C19 C 0.3380(3) 0.1171(2) 0.5437(9) 0.0834(19) Uani 1 1 d . . . H19 H 0.3425 0.1060 0.6306 0.100 Uiso 1 1 calc R . . C20 C 0.3810(3) 0.1201(3) 0.4590(10) 0.089(2) Uani 1 1 d . . . H20 H 0.4138 0.1086 0.4826 0.106 Uiso 1 1 calc R . . C21 C 0.3767(4) 0.1406(3) 0.3346(9) 0.089(2) Uani 1 1 d . . . C22 C 0.4230(3) 0.1484(3) 0.2482(12) 0.113(3) Uani 1 1 d . . . H22 H 0.4564 0.1379 0.2725 0.136 Uiso 1 1 calc R . . C23 C 0.4207(4) 0.1691(4) 0.1388(11) 0.120(4) Uani 1 1 d . . . H23 H 0.4514 0.1728 0.0836 0.144 Uiso 1 1 calc R . . C24 C 0.3696(4) 0.1863(3) 0.1038(10) 0.110(3) Uani 1 1 d . . . H24 H 0.3675 0.2019 0.0261 0.132 Uiso 1 1 calc R . . C25 C 0.3248(4) 0.1804(3) 0.1805(8) 0.091(2) Uani 1 1 d . . . H25 H 0.2924 0.1925 0.1567 0.109 Uiso 1 1 calc R . . C26 C 0.3260(3) 0.1560(2) 0.2982(8) 0.082(2) Uani 1 1 d . . . C27 C 0.2793(3) 0.1471(3) 0.3830(8) 0.0752(18) Uani 1 1 d . . . C28 C 0.2229(3) 0.1568(3) 0.3541(7) 0.077(2) Uani 1 1 d . . . C29 C 0.2007(4) 0.1645(2) 0.2244(8) 0.092(2) Uani 1 1 d . . . H29 H 0.2223 0.1631 0.1449 0.110 Uiso 1 1 calc R . . C30 C 0.1466(3) 0.1743(3) 0.2141(8) 0.094(2) Uani 1 1 d . . . H30 H 0.1316 0.1790 0.1268 0.113 Uiso 1 1 calc R . . C31 C 0.1143(4) 0.1772(3) 0.3300(8) 0.095(2) Uani 1 1 d . . . H31 H 0.0786 0.1856 0.3208 0.114 Uiso 1 1 calc R . . C32 C 0.1341(3) 0.1680(2) 0.4601(8) 0.083(2) Uani 1 1 d . . . H32 H 0.1114 0.1692 0.5376 0.100 Uiso 1 1 calc R . . C33 C 0.1883(3) 0.1569(2) 0.4747(7) 0.0757(18) Uani 1 1 d . . . C34 C 0.1130(3) 0.1253(2) 0.7883(8) 0.083(2) Uani 1 1 d . . . H34 H 0.1135 0.1005 0.7566 0.100 Uiso 1 1 calc R . . C35 C 0.0682(4) 0.1373(3) 0.8515(8) 0.093(3) Uani 1 1 d . . . H35 H 0.0402 0.1205 0.8720 0.112 Uiso 1 1 calc R . . C36 C 0.0631(3) 0.1746(3) 0.8866(8) 0.088(2) Uani 1 1 d . . . C37 C 0.0148(4) 0.1891(4) 0.9426(10) 0.120(3) Uani 1 1 d . . . H37 H -0.0149 0.1735 0.9609 0.144 Uiso 1 1 calc R . . C38 C 0.0124(5) 0.2292(4) 0.9715(15) 0.141(4) Uani 1 1 d . . . H38 H -0.0183 0.2391 1.0150 0.169 Uiso 1 1 calc R . . C39 C 0.0533(5) 0.2518(4) 0.9367(16) 0.143(5) Uani 1 1 d . . . H39 H 0.0494 0.2776 0.9487 0.172 Uiso 1 1 calc R . . C40 C 0.1008(4) 0.2379(3) 0.8838(11) 0.109(3) Uani 1 1 d . . . H40 H 0.1286 0.2544 0.8597 0.131 Uiso 1 1 calc R . . C41 C 0.1084(4) 0.1989(3) 0.8650(7) 0.087(2) Uani 1 1 d . . . C42 C 0.1580(3) 0.1829(2) 0.8162(7) 0.0780(18) Uani 1 1 d . . . C43 C 0.2119(3) 0.2012(2) 0.8047(8) 0.0754(18) Uani 1 1 d . . . C44 C 0.2293(4) 0.2315(3) 0.8855(10) 0.093(3) Uani 1 1 d . . . H44 H 0.2052 0.2425 0.9484 0.112 Uiso 1 1 calc R . . C45 C 0.2800(4) 0.2452(3) 0.8744(11) 0.100(3) Uani 1 1 d . . . H45 H 0.2906 0.2652 0.9309 0.121 Uiso 1 1 calc R . . C46 C 0.3167(4) 0.2303(2) 0.7816(10) 0.097(2) Uani 1 1 d . . . H46 H 0.3512 0.2409 0.7715 0.116 Uiso 1 1 calc R . . C47 C 0.3009(4) 0.1984(2) 0.7008(9) 0.085(2) Uani 1 1 d . . . H47 H 0.3250 0.1880 0.6365 0.102 Uiso 1 1 calc R . . C48 C 0.2483(3) 0.1827(2) 0.7193(7) 0.0743(17) Uani 1 1 d . . . Ir Ir 0.222996(12) 0.132807(9) 0.64382(3) 0.07313(17) Uani 1 1 d . . . N1 N 0.1956(3) 0.07677(17) 0.5946(6) 0.0772(15) Uani 1 1 d . . . N2 N 0.2630(3) 0.09920(19) 0.7978(7) 0.0769(15) Uani 1 1 d . . . N3 N 0.2872(2) 0.12998(17) 0.5060(7) 0.0751(16) Uani 1 1 d . . . N4 N 0.1588(2) 0.14685(18) 0.7667(6) 0.0754(14) Uani 1 1 d . . . P1 P 0.0000 0.03341(15) 0.7500 0.1476(17) Uiso 1 2 d SD . . F1 F 0.0587(4) 0.0329(3) 0.8154(14) 0.331(8) Uiso 1 1 d D . . F2 F 0.0186(4) 0.0652(3) 0.6465(8) 0.248(5) Uiso 1 1 d D . . F3 F 0.0189(5) 0.0023(3) 0.6436(9) 0.403(11) Uiso 1 1 d D . . P2 P 0.5000 0.16938(18) 0.7500 0.162(2) Uiso 1 2 d SD . . F4A F 0.4734(4) 0.1682(3) 0.6008(8) 0.183(4) Uiso 0.777(12) 1 d PDU A 1 F5A F 0.4595(3) 0.2004(2) 0.8007(9) 0.167(4) Uiso 0.777(12) 1 d PDU A 1 F6A F 0.4578(3) 0.1374(3) 0.7970(11) 0.243(8) Uiso 0.777(12) 1 d PD A 1 F4B F 0.4355(6) 0.1692(5) 0.783(4) 0.176(7) Uiso 0.223(12) 1 d PDU A 2 F5B F 0.4905(12) 0.2017(4) 0.6343(13) 0.45(7) Uiso 0.223(12) 1 d PD A 2 F6B F 0.4910(11) 0.1377(4) 0.6329(13) 0.186(9) Uiso 0.223(12) 1 d PDU 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 C1 0.086(5) 0.087(5) 0.075(4) -0.007(4) -0.007(4) -0.013(4) C2 0.096(5) 0.098(6) 0.083(5) -0.011(5) 0.005(4) -0.012(5) C3 0.103(7) 0.106(7) 0.116(7) -0.021(6) 0.018(6) -0.020(5) C4 0.123(8) 0.086(6) 0.122(8) -0.002(6) 0.016(7) -0.009(6) C5 0.119(8) 0.082(6) 0.113(7) 0.009(5) 0.028(6) 0.003(5) C6 0.118(7) 0.098(6) 0.088(6) 0.012(5) 0.010(5) 0.011(6) C7 0.118(7) 0.133(9) 0.104(7) 0.024(7) 0.015(6) 0.039(7) C8 0.110(7) 0.125(8) 0.091(6) -0.001(6) -0.006(5) 0.011(6) C9 0.105(6) 0.119(7) 0.071(4) -0.005(4) -0.011(4) 0.002(5) C10 0.090(5) 0.097(6) 0.072(4) 0.004(4) -0.009(4) -0.005(4) C11 0.079(4) 0.078(5) 0.070(4) 0.007(4) 0.008(4) -0.001(4) C12 0.096(5) 0.078(5) 0.068(4) 0.003(4) 0.012(4) 0.000(4) C13 0.096(5) 0.082(5) 0.080(5) 0.000(4) 0.022(4) -0.003(4) C14 0.097(5) 0.074(5) 0.078(5) 0.002(4) 0.019(4) 0.003(4) C15 0.099(6) 0.085(6) 0.080(5) 0.010(4) 0.011(4) 0.012(4) C16 0.095(6) 0.096(6) 0.069(5) 0.006(4) -0.003(4) 0.002(4) C17 0.104(6) 0.091(5) 0.076(5) 0.011(4) -0.004(4) 0.014(5) C18 0.093(5) 0.077(5) 0.094(5) -0.009(4) 0.008(5) -0.011(4) C19 0.079(5) 0.084(5) 0.087(5) -0.006(4) -0.006(4) 0.000(4) C20 0.072(4) 0.100(5) 0.095(6) -0.016(5) 0.006(4) -0.001(4) C21 0.082(5) 0.109(6) 0.077(5) -0.004(4) 0.008(4) -0.006(4) C22 0.065(5) 0.162(9) 0.112(7) 0.005(7) 0.015(5) -0.014(5) C23 0.094(7) 0.170(11) 0.096(7) 0.013(7) 0.016(5) -0.029(7) C24 0.115(7) 0.142(8) 0.071(5) 0.008(5) -0.002(5) -0.033(7) C25 0.093(5) 0.112(6) 0.069(4) -0.001(4) 0.013(4) -0.014(5) C26 0.074(4) 0.099(6) 0.071(4) -0.016(4) 0.004(4) -0.007(4) C27 0.081(5) 0.080(5) 0.065(4) -0.005(4) 0.003(3) 0.001(4) C28 0.083(5) 0.088(6) 0.061(4) -0.007(3) -0.006(3) -0.004(4) C29 0.107(6) 0.101(6) 0.068(4) -0.008(4) 0.007(4) -0.008(5) C30 0.081(5) 0.140(7) 0.060(4) 0.011(5) -0.011(4) 0.000(5) C31 0.081(5) 0.128(7) 0.077(5) 0.014(5) 0.002(4) 0.005(5) C32 0.076(4) 0.103(5) 0.070(4) 0.009(4) -0.008(4) 0.003(4) C33 0.083(4) 0.076(4) 0.068(4) 0.000(3) -0.005(3) -0.009(3) C34 0.076(4) 0.100(5) 0.074(4) 0.001(4) -0.004(4) -0.019(4) C35 0.092(6) 0.123(8) 0.064(4) 0.000(4) 0.010(4) -0.005(5) C36 0.084(5) 0.110(7) 0.070(4) 0.002(4) 0.008(4) 0.000(5) C37 0.094(6) 0.175(11) 0.091(6) 0.009(7) 0.011(5) 0.010(6) C38 0.122(9) 0.148(10) 0.152(11) 0.002(9) 0.023(8) 0.034(8) C39 0.115(8) 0.130(9) 0.184(13) 0.042(9) 0.046(8) 0.034(7) C40 0.116(7) 0.095(6) 0.116(7) 0.015(5) 0.024(6) 0.022(5) C41 0.095(5) 0.100(6) 0.066(4) 0.003(4) -0.001(4) 0.008(5) C42 0.088(5) 0.085(5) 0.061(4) 0.001(3) -0.001(3) 0.002(4) C43 0.084(5) 0.079(5) 0.064(4) 0.002(4) -0.004(4) 0.004(4) C44 0.115(7) 0.083(6) 0.081(5) -0.001(4) -0.001(5) 0.003(5) C45 0.109(8) 0.086(6) 0.106(7) -0.017(5) -0.009(5) -0.007(5) C46 0.095(6) 0.089(5) 0.107(6) 0.002(5) -0.015(5) -0.007(4) C47 0.091(5) 0.079(5) 0.084(5) -0.004(4) -0.014(4) -0.009(4) C48 0.070(4) 0.089(5) 0.064(4) 0.014(4) -0.003(3) -0.004(4) Ir 0.0776(2) 0.0783(2) 0.0635(2) 0.00149(12) -0.00158(12) -0.00322(13) N1 0.084(4) 0.076(4) 0.071(3) -0.003(3) -0.003(3) -0.007(3) N2 0.084(4) 0.080(4) 0.067(3) 0.001(3) -0.006(3) -0.001(3) N3 0.069(3) 0.092(5) 0.064(3) -0.005(3) -0.003(3) 0.000(3) N4 0.086(4) 0.084(4) 0.056(3) 0.003(3) -0.002(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 C1 N1 1.355(9) . ? C1 C2 1.381(11) . ? C1 H1 0.9300 . ? C2 C18 1.391(12) . ? C2 H2 0.9300 . ? C3 C4 1.334(14) . ? C3 C18 1.405(12) . ? C3 H3 0.9300 . ? C4 C5 1.369(15) . ? C4 H4 0.9300 . ? C5 C14 1.390(13) . ? C5 H5 0.9300 . ? C6 C15 1.341(13) . ? C6 C7 1.452(15) . ? C6 H6 0.9300 . ? C7 C8 1.412(14) . ? C7 H7 0.9300 . ? C8 C17 1.387(12) . ? C8 H8 0.9300 . ? C9 C10 1.376(12) . ? C9 C17 1.400(12) . ? C9 H9 0.9300 . ? C10 N2 1.338(11) . ? C10 H10 0.9300 . ? C11 N2 1.357(10) . ? C11 C16 1.391(12) . ? C11 C12 1.461(11) . ? C12 N1 1.345(10) . ? C12 C13 1.416(13) . ? C13 C14 1.417(12) . ? C13 C18 1.416(12) . ? C14 C15 1.432(12) . ? C15 C16 1.452(15) . ? C16 C17 1.419(12) . ? C19 C20 1.335(11) . ? C19 N3 1.374(9) . ? C19 H19 0.9300 . ? C20 C21 1.402(12) . ? C20 H20 0.9300 . ? C21 C26 1.401(12) . ? C21 C22 1.433(12) . ? C22 C23 1.283(14) . ? C22 H22 0.9300 . ? C23 C24 1.434(15) . ? C23 H23 0.9300 . ? C24 C25 1.338(12) . ? C24 H24 0.9300 . ? C25 C26 1.425(12) . ? C25 H25 0.9300 . ? C26 C27 1.442(10) . ? C27 N3 1.342(10) . ? C27 C28 1.451(10) . ? C28 C29 1.386(11) . ? C28 C33 1.434(10) . ? C29 C30 1.374(12) . ? C29 H29 0.9300 . ? C30 C31 1.369(11) . ? C30 H30 0.9300 . ? C31 C32 1.379(10) . ? C31 H31 0.9300 . ? C32 C33 1.391(10) . ? C32 H32 0.9300 . ? C33 Ir 2.024(7) . ? C34 C35 1.325(13) . ? C34 N4 1.374(9) . ? C34 H34 0.9300 . ? C35 C36 1.374(12) . ? C35 H35 0.9300 . ? C36 C41 1.420(12) . ? C36 C37 1.396(12) . ? C37 C38 1.452(16) . ? C37 H37 0.9300 . ? C38 C39 1.326(17) . ? C38 H38 0.9300 . ? C39 C40 1.363(14) . ? C39 H39 0.9300 . ? C40 C41 1.410(13) . ? C40 H40 0.9300 . ? C41 C42 1.423(11) . ? C42 N4 1.365(10) . ? C42 C43 1.477(11) . ? C43 C48 1.377(11) . ? C43 C44 1.395(13) . ? C44 C45 1.338(12) . ? C44 H44 0.9300 . ? C45 C46 1.372(13) . ? C45 H45 0.9300 . ? C46 C47 1.428(11) . ? C46 H46 0.9300 . ? C47 C48 1.416(11) . ? C47 H47 0.9300 . ? C48 Ir 2.014(8) . ? Ir N4 2.029(6) . ? Ir N3 2.058(6) . ? Ir N2 2.138(6) . ? Ir N1 2.153(6) . ? P1 F1 1.570(8) 4_556 ? P1 F1 1.570(8) . ? P1 F2 1.573(8) 4_556 ? P1 F2 1.573(9) . ? P1 F3 1.576(9) . ? P1 F3 1.576(9) 4_556 ? P2 F5A 1.560(8) 4_656 ? P2 F5A 1.560(8) . ? P2 F4A 1.574(7) . ? P2 F4A 1.574(7) 4_656 ? P2 F6B 1.606(15) . ? P2 F6B 1.606(15) 4_656 ? P2 F6A 1.602(8) . ? P2 F6A 1.602(8) 4_656 ? P2 F4B 1.613(14) 4_656 ? P2 F4B 1.613(14) . ? P2 F5B 1.614(15) 4_656 ? P2 F5B 1.614(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.5(8) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C2 C18 120.6(8) . . ? C1 C2 H2 119.7 . . ? C18 C2 H2 119.7 . . ? C4 C3 C18 122.0(10) . . ? C4 C3 H3 119.0 . . ? C18 C3 H3 119.0 . . ? C3 C4 C5 119.8(10) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C14 124.6(10) . . ? C4 C5 H5 117.7 . . ? C14 C5 H5 117.7 . . ? C15 C6 C7 122.2(10) . . ? C15 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C8 C7 C6 120.1(9) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 120.0 . . ? C17 C8 C7 118.4(10) . . ? C17 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C10 C9 C17 121.2(8) . . ? C10 C9 H9 119.4 . . ? C17 C9 H9 119.4 . . ? N2 C10 C9 122.6(9) . . ? N2 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? N2 C11 C16 124.1(8) . . ? N2 C11 C12 117.1(7) . . ? C16 C11 C12 118.7(8) . . ? N1 C12 C13 122.9(8) . . ? N1 C12 C11 116.3(8) . . ? C13 C12 C11 120.8(8) . . ? C14 C13 C12 119.3(8) . . ? C14 C13 C18 123.5(8) . . ? C12 C13 C18 117.2(8) . . ? C5 C14 C13 113.7(9) . . ? C5 C14 C15 125.2(9) . . ? C13 C14 C15 121.0(8) . . ? C6 C15 C14 123.8(10) . . ? C6 C15 C16 117.7(9) . . ? C14 C15 C16 118.5(8) . . ? C11 C16 C17 118.0(9) . . ? C11 C16 C15 121.3(8) . . ? C17 C16 C15 120.7(8) . . ? C8 C17 C9 122.3(9) . . ? C8 C17 C16 121.0(9) . . ? C9 C17 C16 116.7(8) . . ? C2 C18 C3 125.1(9) . . ? C2 C18 C13 118.6(8) . . ? C3 C18 C13 116.3(9) . . ? C20 C19 N3 121.9(8) . . ? C20 C19 H19 119.1 . . ? N3 C19 H19 119.1 . . ? C19 C20 C21 120.0(8) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C26 118.8(8) . . ? C20 C21 C22 122.3(9) . . ? C26 C21 C22 118.8(9) . . ? C23 C22 C21 123.4(10) . . ? C23 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? C22 C23 C24 118.3(9) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C25 C24 C23 121.4(9) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 120.9(9) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 117.1(7) . . ? C21 C26 C27 118.5(8) . . ? C25 C26 C27 124.4(8) . . ? N3 C27 C26 118.8(7) . . ? N3 C27 C28 114.5(7) . . ? C26 C27 C28 126.6(8) . . ? C29 C28 C33 119.5(7) . . ? C29 C28 C27 126.3(7) . . ? C33 C28 C27 114.2(6) . . ? C28 C29 C30 119.5(8) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C31 C30 C29 121.3(8) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C32 121.0(8) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C31 C32 C33 119.5(7) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C32 C33 C28 118.9(7) . . ? C32 C33 Ir 126.9(6) . . ? C28 C33 Ir 113.4(5) . . ? C35 C34 N4 124.4(8) . . ? C35 C34 H34 117.8 . . ? N4 C34 H34 117.8 . . ? C34 C35 C36 120.0(9) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C41 118.5(8) . . ? C35 C36 C37 121.8(10) . . ? C41 C36 C37 119.7(10) . . ? C36 C37 C38 117.9(10) . . ? C36 C37 H37 121.0 . . ? C38 C37 H37 121.0 . . ? C39 C38 C37 121.0(11) . . ? C39 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 C39 C40 121.2(12) . . ? C38 C39 H39 119.4 . . ? C40 C39 H39 119.4 . . ? C39 C40 C41 121.2(11) . . ? C39 C40 H40 119.4 . . ? C41 C40 H40 119.4 . . ? C40 C41 C36 118.3(9) . . ? C40 C41 C42 123.3(9) . . ? C36 C41 C42 118.3(8) . . ? N4 C42 C41 120.1(7) . . ? N4 C42 C43 112.1(7) . . ? C41 C42 C43 127.8(8) . . ? C48 C43 C44 120.1(8) . . ? C48 C43 C42 114.4(7) . . ? C44 C43 C42 124.9(8) . . ? C45 C44 C43 121.3(9) . . ? C45 C44 H44 119.4 . . ? C43 C44 H44 119.4 . . ? C44 C45 C46 121.4(10) . . ? C44 C45 H45 119.3 . . ? C46 C45 H45 119.3 . . ? C45 C46 C47 118.7(9) . . ? C45 C46 H46 120.6 . . ? C47 C46 H46 120.6 . . ? C48 C47 C46 119.4(8) . . ? C48 C47 H47 120.3 . . ? C46 C47 H47 120.3 . . ? C43 C48 C47 118.5(7) . . ? C43 C48 Ir 115.7(6) . . ? C47 C48 Ir 125.5(6) . . ? C48 Ir C33 92.6(3) . . ? C48 Ir N4 79.2(3) . . ? C33 Ir N4 92.1(3) . . ? C48 Ir N3 92.2(3) . . ? C33 Ir N3 80.0(3) . . ? N4 Ir N3 168.1(2) . . ? C48 Ir N2 95.9(3) . . ? C33 Ir N2 169.7(3) . . ? N4 Ir N2 95.2(2) . . ? N3 Ir N2 93.8(3) . . ? C48 Ir N1 171.6(3) . . ? C33 Ir N1 94.9(3) . . ? N4 Ir N1 96.5(3) . . ? N3 Ir N1 93.0(2) . . ? N2 Ir N1 77.2(2) . . ? C12 N1 C1 119.1(7) . . ? C12 N1 Ir 114.5(5) . . ? C1 N1 Ir 126.4(5) . . ? C10 N2 C11 117.3(7) . . ? C10 N2 Ir 127.8(6) . . ? C11 N2 Ir 113.9(5) . . ? C27 N3 C19 120.9(7) . . ? C27 N3 Ir 115.6(5) . . ? C19 N3 Ir 122.6(6) . . ? C42 N4 C34 117.4(7) . . ? C42 N4 Ir 116.3(5) . . ? C34 N4 Ir 125.7(6) . . ? F1 P1 F1 178.7(8) 4_556 . ? F1 P1 F2 89.7(4) 4_556 4_556 ? F1 P1 F2 91.2(4) . 4_556 ? F1 P1 F2 91.2(4) 4_556 . ? F1 P1 F2 89.7(4) . . ? F2 P1 F2 88.0(6) 4_556 . ? F1 P1 F3 90.1(5) 4_556 . ? F1 P1 F3 88.9(4) . . ? F2 P1 F3 178.6(6) 4_556 . ? F2 P1 F3 90.6(3) . . ? F1 P1 F3 88.9(4) 4_556 4_556 ? F1 P1 F3 90.1(5) . 4_556 ? F2 P1 F3 90.6(3) 4_556 4_556 ? F2 P1 F3 178.6(6) . 4_556 ? F3 P1 F3 90.8(7) . 4_556 ? F5A P2 F5A 90.2(6) 4_656 . ? F5A P2 F4A 89.8(4) 4_656 . ? F5A P2 F4A 92.3(4) . . ? F5A P2 F4A 92.3(4) 4_656 4_656 ? F5A P2 F4A 89.8(4) . 4_656 ? F4A P2 F4A 177.0(7) . 4_656 ? F5A P2 F6B 111.3(9) 4_656 . ? F5A P2 F6B 128.8(10) . . ? F4A P2 F6B 44.6(6) . . ? F4A P2 F6B 132.5(6) 4_656 . ? F5A P2 F6B 128.8(10) 4_656 4_656 ? F5A P2 F6B 111.3(9) . 4_656 ? F4A P2 F6B 132.5(6) . 4_656 ? F4A P2 F6B 44.6(6) 4_656 4_656 ? F6B P2 F6B 91.0(8) . 4_656 ? F5A P2 F6A 178.2(4) 4_656 . ? F5A P2 F6A 90.2(3) . . ? F4A P2 F6A 88.3(4) . . ? F4A P2 F6A 89.5(4) 4_656 . ? F6B P2 F6A 67.1(9) . . ? F6B P2 F6A 52.7(10) 4_656 . ? F5A P2 F6A 90.2(3) 4_656 4_656 ? F5A P2 F6A 178.2(4) . 4_656 ? F4A P2 F6A 89.5(4) . 4_656 ? F4A P2 F6A 88.3(4) 4_656 4_656 ? F6B P2 F6A 52.7(10) . 4_656 ? F6B P2 F6A 67.1(9) 4_656 4_656 ? F6A P2 F6A 89.5(6) . 4_656 ? F5A P2 F4B 47.0(6) 4_656 4_656 ? F5A P2 F4B 133.4(7) . 4_656 ? F4A P2 F4B 103.0(14) . 4_656 ? F4A P2 F4B 77.0(14) 4_656 4_656 ? F6B P2 F4B 89.6(6) . 4_656 ? F6B P2 F4B 90.1(5) 4_656 4_656 ? F6A P2 F4B 133.3(7) . 4_656 ? F6A P2 F4B 46.3(6) 4_656 4_656 ? F5A P2 F4B 133.4(7) 4_656 . ? F5A P2 F4B 47.0(6) . . ? F4A P2 F4B 77.0(14) . . ? F4A P2 F4B 103.0(14) 4_656 . ? F6B P2 F4B 90.1(5) . . ? F6B P2 F4B 89.6(6) 4_656 . ? F6A P2 F4B 46.3(6) . . ? F6A P2 F4B 133.3(7) 4_656 . ? F4B P2 F4B 179.5(11) 4_656 . ? F5A P2 F5B 67.7(9) 4_656 4_656 ? F5A P2 F5B 51.3(10) . 4_656 ? F4A P2 F5B 134.8(6) . 4_656 ? F4A P2 F5B 48.1(6) 4_656 4_656 ? F6B P2 F5B 179.0(7) . 4_656 ? F6B P2 F5B 89.8(4) 4_656 4_656 ? F6A P2 F5B 113.9(9) . 4_656 ? F6A P2 F5B 127.3(10) 4_656 4_656 ? F4B P2 F5B 89.9(5) 4_656 4_656 ? F4B P2 F5B 90.5(6) . 4_656 ? F5A P2 F5B 51.3(10) 4_656 . ? F5A P2 F5B 67.7(9) . . ? F4A P2 F5B 48.1(6) . . ? F4A P2 F5B 134.8(6) 4_656 . ? F6B P2 F5B 89.8(4) . . ? F6B P2 F5B 179.0(7) 4_656 . ? F6A P2 F5B 127.3(10) . . ? F6A P2 F5B 113.9(9) 4_656 . ? F4B P2 F5B 90.5(6) 4_656 . ? F4B P2 F5B 89.9(5) . . ? F5B P2 F5B 89.4(8) 4_656 . ? 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 N1 C1 C2 C18 -1.3(12) . . . . ? C18 C3 C4 C5 1.6(16) . . . . ? C3 C4 C5 C14 1.0(17) . . . . ? C15 C6 C7 C8 -0.3(15) . . . . ? C6 C7 C8 C17 1.4(15) . . . . ? C17 C9 C10 N2 -0.6(14) . . . . ? N2 C11 C12 N1 3.4(10) . . . . ? C16 C11 C12 N1 -175.4(7) . . . . ? N2 C11 C12 C13 -174.8(7) . . . . ? C16 C11 C12 C13 6.4(11) . . . . ? N1 C12 C13 C14 176.1(7) . . . . ? C11 C12 C13 C14 -5.8(11) . . . . ? N1 C12 C13 C18 -3.8(12) . . . . ? C11 C12 C13 C18 174.3(7) . . . . ? C4 C5 C14 C13 -2.3(14) . . . . ? C4 C5 C14 C15 179.1(9) . . . . ? C12 C13 C14 C5 -178.5(8) . . . . ? C18 C13 C14 C5 1.4(12) . . . . ? C12 C13 C14 C15 0.1(12) . . . . ? C18 C13 C14 C15 180.0(8) . . . . ? C7 C6 C15 C14 -179.2(8) . . . . ? C7 C6 C15 C16 -0.2(14) . . . . ? C5 C14 C15 C6 2.2(14) . . . . ? C13 C14 C15 C6 -176.3(8) . . . . ? C5 C14 C15 C16 -176.7(8) . . . . ? C13 C14 C15 C16 4.8(12) . . . . ? N2 C11 C16 C17 -2.8(13) . . . . ? C12 C11 C16 C17 175.9(7) . . . . ? N2 C11 C16 C15 180.0(8) . . . . ? C12 C11 C16 C15 -1.3(12) . . . . ? C6 C15 C16 C11 176.8(8) . . . . ? C14 C15 C16 C11 -4.2(13) . . . . ? C6 C15 C16 C17 -0.3(13) . . . . ? C14 C15 C16 C17 178.7(8) . . . . ? C7 C8 C17 C9 178.2(9) . . . . ? C7 C8 C17 C16 -2.0(14) . . . . ? C10 C9 C17 C8 177.3(9) . . . . ? C10 C9 C17 C16 -2.6(13) . . . . ? C11 C16 C17 C8 -175.8(8) . . . . ? C15 C16 C17 C8 1.4(13) . . . . ? C11 C16 C17 C9 4.1(12) . . . . ? C15 C16 C17 C9 -178.7(8) . . . . ? C1 C2 C18 C3 -178.2(8) . . . . ? C1 C2 C18 C13 0.0(12) . . . . ? C4 C3 C18 C2 175.8(9) . . . . ? C4 C3 C18 C13 -2.5(14) . . . . ? C14 C13 C18 C2 -177.5(8) . . . . ? C12 C13 C18 C2 2.4(12) . . . . ? C14 C13 C18 C3 0.9(12) . . . . ? C12 C13 C18 C3 -179.3(8) . . . . ? N3 C19 C20 C21 7.4(13) . . . . ? C19 C20 C21 C26 -3.2(13) . . . . ? C19 C20 C21 C22 172.6(9) . . . . ? C20 C21 C22 C23 -175.3(11) . . . . ? C26 C21 C22 C23 0.5(17) . . . . ? C21 C22 C23 C24 2.1(19) . . . . ? C22 C23 C24 C25 -1.6(17) . . . . ? C23 C24 C25 C26 -1.6(15) . . . . ? C20 C21 C26 C25 172.4(8) . . . . ? C22 C21 C26 C25 -3.6(12) . . . . ? C20 C21 C26 C27 -6.0(12) . . . . ? C22 C21 C26 C27 178.0(9) . . . . ? C24 C25 C26 C21 4.1(13) . . . . ? C24 C25 C26 C27 -177.5(9) . . . . ? C21 C26 C27 N3 11.5(12) . . . . ? C25 C26 C27 N3 -166.8(8) . . . . ? C21 C26 C27 C28 -172.8(8) . . . . ? C25 C26 C27 C28 8.8(14) . . . . ? N3 C27 C28 C29 -160.6(9) . . . . ? C26 C27 C28 C29 23.6(15) . . . . ? N3 C27 C28 C33 17.5(11) . . . . ? C26 C27 C28 C33 -158.3(8) . . . . ? C33 C28 C29 C30 3.7(13) . . . . ? C27 C28 C29 C30 -178.3(9) . . . . ? C28 C29 C30 C31 1.3(15) . . . . ? C29 C30 C31 C32 -4.5(16) . . . . ? C30 C31 C32 C33 2.6(14) . . . . ? C31 C32 C33 C28 2.3(12) . . . . ? C31 C32 C33 Ir -167.4(7) . . . . ? C29 C28 C33 C32 -5.4(12) . . . . ? C27 C28 C33 C32 176.3(8) . . . . ? C29 C28 C33 Ir 165.7(7) . . . . ? C27 C28 C33 Ir -12.6(9) . . . . ? N4 C34 C35 C36 7.1(13) . . . . ? C34 C35 C36 C41 -5.5(12) . . . . ? C34 C35 C36 C37 174.6(8) . . . . ? C35 C36 C37 C38 -177.6(10) . . . . ? C41 C36 C37 C38 2.4(14) . . . . ? C36 C37 C38 C39 4.6(19) . . . . ? C37 C38 C39 C40 -6(2) . . . . ? C38 C39 C40 C41 0(2) . . . . ? C39 C40 C41 C36 7.5(15) . . . . ? C39 C40 C41 C42 -177.0(11) . . . . ? C35 C36 C41 C40 171.8(8) . . . . ? C37 C36 C41 C40 -8.2(12) . . . . ? C35 C36 C41 C42 -3.9(11) . . . . ? C37 C36 C41 C42 176.1(8) . . . . ? C40 C41 C42 N4 -163.2(8) . . . . ? C36 C41 C42 N4 12.3(11) . . . . ? C40 C41 C42 C43 13.6(13) . . . . ? C36 C41 C42 C43 -170.9(7) . . . . ? N4 C42 C43 C48 14.4(9) . . . . ? C41 C42 C43 C48 -162.7(7) . . . . ? N4 C42 C43 C44 -156.9(8) . . . . ? C41 C42 C43 C44 26.0(13) . . . . ? C48 C43 C44 C45 5.2(15) . . . . ? C42 C43 C44 C45 176.0(9) . . . . ? C43 C44 C45 C46 1.1(17) . . . . ? C44 C45 C46 C47 -3.3(16) . . . . ? C45 C46 C47 C48 -0.6(13) . . . . ? C44 C43 C48 C47 -8.9(12) . . . . ? C42 C43 C48 C47 179.4(7) . . . . ? C44 C43 C48 Ir 166.3(7) . . . . ? C42 C43 C48 Ir -5.5(9) . . . . ? C46 C47 C48 C43 6.6(11) . . . . ? C46 C47 C48 Ir -168.0(6) . . . . ? C43 C48 Ir C33 89.0(6) . . . . ? C47 C48 Ir C33 -96.3(7) . . . . ? C43 C48 Ir N4 -2.6(5) . . . . ? C47 C48 Ir N4 172.1(7) . . . . ? C43 C48 Ir N3 169.1(6) . . . . ? C47 C48 Ir N3 -16.2(7) . . . . ? C43 C48 Ir N2 -96.9(6) . . . . ? C47 C48 Ir N2 77.9(6) . . . . ? C43 C48 Ir N1 -63(2) . . . . ? C47 C48 Ir N1 112.0(18) . . . . ? C32 C33 Ir C48 -93.9(7) . . . . ? C28 C33 Ir C48 95.9(6) . . . . ? C32 C33 Ir N4 -14.6(7) . . . . ? C28 C33 Ir N4 175.2(6) . . . . ? C32 C33 Ir N3 174.3(7) . . . . ? C28 C33 Ir N3 4.1(5) . . . . ? C32 C33 Ir N2 120.9(15) . . . . ? C28 C33 Ir N2 -49.3(18) . . . . ? C32 C33 Ir N1 82.1(7) . . . . ? C28 C33 Ir N1 -88.1(6) . . . . ? C13 C12 N1 C1 2.6(11) . . . . ? C11 C12 N1 C1 -175.6(6) . . . . ? C13 C12 N1 Ir -177.6(6) . . . . ? C11 C12 N1 Ir 4.2(8) . . . . ? C2 C1 N1 C12 0.0(11) . . . . ? C2 C1 N1 Ir -179.7(6) . . . . ? C48 Ir N1 C12 -42(2) . . . . ? C33 Ir N1 C12 166.6(5) . . . . ? N4 Ir N1 C12 -100.7(5) . . . . ? N3 Ir N1 C12 86.4(6) . . . . ? N2 Ir N1 C12 -6.8(5) . . . . ? C48 Ir N1 C1 138.1(17) . . . . ? C33 Ir N1 C1 -13.6(7) . . . . ? N4 Ir N1 C1 79.1(6) . . . . ? N3 Ir N1 C1 -93.8(6) . . . . ? N2 Ir N1 C1 173.0(7) . . . . ? C9 C10 N2 C11 2.1(13) . . . . ? C9 C10 N2 Ir -166.2(6) . . . . ? C16 C11 N2 C10 -0.3(12) . . . . ? C12 C11 N2 C10 -179.1(7) . . . . ? C16 C11 N2 Ir 169.5(6) . . . . ? C12 C11 N2 Ir -9.2(8) . . . . ? C48 Ir N2 C10 -7.8(8) . . . . ? C33 Ir N2 C10 137.3(14) . . . . ? N4 Ir N2 C10 -87.4(8) . . . . ? N3 Ir N2 C10 84.9(8) . . . . ? N1 Ir N2 C10 177.1(8) . . . . ? C48 Ir N2 C11 -176.3(5) . . . . ? C33 Ir N2 C11 -31.3(18) . . . . ? N4 Ir N2 C11 104.0(5) . . . . ? N3 Ir N2 C11 -83.7(5) . . . . ? N1 Ir N2 C11 8.5(5) . . . . ? C26 C27 N3 C19 -7.8(12) . . . . ? C28 C27 N3 C19 176.0(7) . . . . ? C26 C27 N3 Ir 162.1(6) . . . . ? C28 C27 N3 Ir -14.1(9) . . . . ? C20 C19 N3 C27 -1.7(12) . . . . ? C20 C19 N3 Ir -170.9(6) . . . . ? C48 Ir N3 C27 -86.6(6) . . . . ? C33 Ir N3 C27 5.6(6) . . . . ? N4 Ir N3 C27 -43.0(14) . . . . ? N2 Ir N3 C27 177.4(6) . . . . ? N1 Ir N3 C27 100.1(6) . . . . ? C48 Ir N3 C19 83.1(6) . . . . ? C33 Ir N3 C19 175.3(6) . . . . ? N4 Ir N3 C19 126.7(11) . . . . ? N2 Ir N3 C19 -12.9(6) . . . . ? N1 Ir N3 C19 -90.3(6) . . . . ? C41 C42 N4 C34 -10.9(10) . . . . ? C43 C42 N4 C34 171.7(6) . . . . ? C41 C42 N4 Ir 160.5(5) . . . . ? C43 C42 N4 Ir -16.9(8) . . . . ? C35 C34 N4 C42 1.3(11) . . . . ? C35 C34 N4 Ir -169.2(6) . . . . ? C48 Ir N4 C42 11.2(5) . . . . ? C33 Ir N4 C42 -81.0(5) . . . . ? N3 Ir N4 C42 -33.4(14) . . . . ? N2 Ir N4 C42 106.2(5) . . . . ? N1 Ir N4 C42 -176.2(5) . . . . ? C48 Ir N4 C34 -178.2(6) . . . . ? C33 Ir N4 C34 89.6(6) . . . . ? N3 Ir N4 C34 137.3(11) . . . . ? N2 Ir N4 C34 -83.2(6) . . . . ? N1 Ir N4 C34 -5.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.361 _refine_diff_density_min -1.247 _refine_diff_density_rms 0.167 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 1 0.500 0.000 -0.029 392.3 94.0 2 0.000 0.500 -0.028 392.3 93.5 3 0.000 0.103 0.250 119.3 42.9 4 0.500 0.603 0.250 119.3 43.8 5 0.500 0.397 0.750 119.3 40.4 6 1.000 0.897 0.750 119.3 40.7 _chemical_name_common ;Bis(1-phenylisoqinoline)(1,12-diazaperylene)iridium(iii)- hexafluorophosphate ; #====================================================================== data_pit4i _database_code_depnum_ccdc_archive 'CCDC 827354' #TrackingRef '- pit4i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2-(2-pyridyl)phenyl)(2,11-diisopropyl-1,12-diazaperylene)iridium(III)- hexafluorophosphate ; _chemical_melting_point '> 633' _chemical_formula_moiety 'C46 H38 Ir N4 1+, F6 P 1-' _chemical_formula_sum 'C46 H38 F6 Ir N4 P' _chemical_formula_weight 983.97 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2725(5) _cell_length_b 14.8955(6) _cell_length_c 25.3919(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.784(4) _cell_angle_gamma 90.00 _cell_volume 3885.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 32040 _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 29.53 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.253 _exptl_crystal_size_min 0.215 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method ? _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 3.547 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4471 _exptl_absorpt_correction_T_max 0.4582 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). The methyl groups of one isopropyl substituent are disordered over two sides with an occupation ratio of 0.8/0.2. In this moieties the C-C distances were restrained using the DFIX instruction. ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12 x 0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 100 mm ; _diffrn_reflns_number 24965 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6565 _reflns_number_gt 5690 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were found from the difference Fourier map and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0268P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00056(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6846 _refine_ls_number_parameters 638 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0461 _refine_ls_wR_factor_gt 0.0447 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _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 C1 C 0.2661(2) 0.39993(19) 0.85723(12) 0.0347(6) Uani 1 1 d . A . C2 C -0.0482(2) 0.37964(17) 0.92207(11) 0.0321(6) Uani 1 1 d . . . C3 C 0.0642(2) 0.42011(17) 0.89644(11) 0.0315(6) Uani 1 1 d . . . C4 C 0.2698(2) 0.12298(18) 0.81714(12) 0.0374(7) Uani 1 1 d . . . C5 C -0.1648(3) 0.2389(2) 0.78559(13) 0.0414(7) Uani 1 1 d . . . C6 C -0.2552(3) 0.2734(3) 0.74923(14) 0.0532(9) Uani 1 1 d . . . H6 H -0.323(4) 0.235(2) 0.7382(16) 0.064 Uiso 1 1 d . . . C7 C -0.2334(3) 0.3001(2) 0.98093(13) 0.0415(7) Uani 1 1 d . . . H7 H -0.294(3) 0.273(2) 1.0047(15) 0.050 Uiso 1 1 d . . . C8 C -0.1474(3) 0.24944(18) 0.95283(12) 0.0348(6) Uani 1 1 d . . . C9 C -0.1361(2) 0.43552(18) 0.94889(11) 0.0333(6) Uani 1 1 d . . . C10 C 0.0749(2) 0.51434(17) 0.89503(11) 0.0333(6) Uani 1 1 d . . . C12 C -0.2340(2) 0.3937(2) 0.97876(12) 0.0376(7) Uani 1 1 d . . . C13 C 0.2811(3) 0.4913(2) 0.85382(13) 0.0399(7) Uani 1 1 d . . . H13 H 0.365(3) 0.517(2) 0.8411(13) 0.048 Uiso 1 1 d . . . C14 C 0.1930(3) 0.1621(2) 0.95387(13) 0.0422(7) Uani 1 1 d . . . H14 H 0.133(3) 0.202(2) 0.9717(14) 0.051 Uiso 1 1 d . . . C15 C 0.2770(2) 0.11184(18) 0.87399(13) 0.0386(7) Uani 1 1 d . . . C16 C -0.1292(3) 0.53085(19) 0.94528(12) 0.0378(7) Uani 1 1 d . . . C17 C -0.0229(3) 0.57137(18) 0.91609(12) 0.0378(7) Uani 1 1 d . . . C18 C 0.1841(3) 0.55106(18) 0.87000(12) 0.0380(6) Uani 1 1 d . . . C19 C -0.0520(3) 0.12630(19) 0.83779(12) 0.0378(6) Uani 1 1 d . . . C20 C -0.1484(3) 0.14868(19) 0.95797(13) 0.0396(7) Uani 1 1 d . . . H20 H -0.083(3) 0.126(2) 0.9369(14) 0.048 Uiso 1 1 d . . . C21 C -0.0546(3) 0.3755(2) 0.78391(13) 0.0423(7) Uani 1 1 d . . . H21 H 0.020(3) 0.407(2) 0.7953(13) 0.051 Uiso 1 1 d . . . C22 C -0.1193(4) 0.1197(2) 1.01502(14) 0.0485(8) Uani 1 1 d . . . H22A H -0.189(3) 0.139(2) 1.0375(15) 0.058 Uiso 1 1 d . . . H22B H -0.037(3) 0.143(2) 1.0287(14) 0.058 Uiso 1 1 d . . . H22C H -0.110(3) 0.053(3) 1.0158(14) 0.058 Uiso 1 1 d . . . C23 C 0.1617(3) 0.1961(2) 0.74486(13) 0.0450(7) Uani 1 1 d . . . H23 H 0.091(4) 0.237(2) 0.7316(15) 0.054 Uiso 1 1 d . . . C24 C 0.3573(3) 0.0838(2) 0.78247(16) 0.0496(8) Uani 1 1 d . . . H24 H 0.423(3) 0.049(2) 0.7957(15) 0.059 Uiso 1 1 d . . . C25 C -0.0365(3) 0.0370(2) 0.85408(14) 0.0477(8) Uani 1 1 d . . . H25 H 0.040(3) 0.020(2) 0.8753(15) 0.057 Uiso 1 1 d . . . C26 C -0.2422(3) 0.3589(3) 0.73003(15) 0.0593(10) Uani 1 1 d . . . H26 H -0.299(4) 0.382(3) 0.7086(16) 0.071 Uiso 1 1 d . . . C27 C -0.2236(3) 0.5800(2) 0.97097(14) 0.0477(8) Uani 1 1 d . . . H27 H -0.219(3) 0.638(3) 0.9680(14) 0.057 Uiso 1 1 d . . . C28 C -0.0102(3) 0.6631(2) 0.90784(14) 0.0474(8) Uani 1 1 d . . . H28 H -0.078(3) 0.701(2) 0.9200(15) 0.057 Uiso 1 1 d . . . C29 C 0.0968(3) 0.6982(2) 0.88239(14) 0.0514(8) Uani 1 1 d . . . H29 H 0.114(4) 0.760(2) 0.8808(16) 0.062 Uiso 1 1 d . . . C30 C -0.3257(3) 0.4476(2) 1.00534(14) 0.0463(8) Uani 1 1 d . . . H30 H -0.383(3) 0.420(2) 1.0241(15) 0.056 Uiso 1 1 d . . . C31 C 0.1943(3) 0.6451(2) 0.86451(15) 0.0483(8) Uani 1 1 d . . . H31 H 0.274(3) 0.666(2) 0.8488(14) 0.058 Uiso 1 1 d . . . C32 C -0.3201(3) 0.5385(2) 1.00014(16) 0.0524(9) Uani 1 1 d . . . H32 H -0.381(4) 0.573(2) 1.0164(15) 0.063 Uiso 1 1 d . . . C33 C 0.3627(3) 0.0563(2) 0.90182(17) 0.0527(9) Uani 1 1 d . . . H33 H 0.424(4) 0.026(2) 0.8813(16) 0.063 Uiso 1 1 d . . . C34 C 0.2764(3) 0.1089(3) 0.98255(16) 0.0556(9) Uani 1 1 d . . . H34 H 0.274(4) 0.115(3) 1.0158(17) 0.067 Uiso 1 1 d . . . C35 C -0.1593(3) 0.1470(2) 0.80501(13) 0.0435(7) Uani 1 1 d . . . C36 C 0.3458(3) 0.1002(2) 0.72963(17) 0.0574(10) Uani 1 1 d . . . H36 H 0.406(4) 0.079(2) 0.7057(17) 0.069 Uiso 1 1 d . . . C37 C -0.1407(3) 0.4107(3) 0.74757(15) 0.0539(9) Uani 1 1 d . . . H37 H -0.126(4) 0.467(3) 0.7339(15) 0.065 Uiso 1 1 d . . . C38 C 0.3609(3) 0.0550(3) 0.95536(18) 0.0627(11) Uani 1 1 d . . . H38 H 0.413(4) 0.019(3) 0.9751(17) 0.075 Uiso 1 1 d . . . C39 C -0.1290(4) -0.0270(3) 0.84006(17) 0.0641(11) Uani 1 1 d . . . H39 H -0.115(4) -0.083(3) 0.8540(17) 0.077 Uiso 1 1 d . . . C40 C -0.2783(3) 0.1103(3) 0.93846(16) 0.0509(8) Uani 1 1 d . . . H40A H -0.272(3) 0.044(3) 0.9375(15) 0.061 Uiso 1 1 d . . . H40B H -0.300(3) 0.130(2) 0.9029(16) 0.061 Uiso 1 1 d . . . H40C H -0.346(4) 0.132(2) 0.9606(16) 0.061 Uiso 1 1 d . . . C41 C 0.2483(3) 0.1557(2) 0.71058(15) 0.0540(8) Uani 1 1 d . . . H41 H 0.235(3) 0.167(2) 0.6733(16) 0.065 Uiso 1 1 d . . . C42 C -0.2502(4) 0.0806(3) 0.79134(16) 0.0639(10) Uani 1 1 d . . . H42 H -0.321(4) 0.097(3) 0.7692(17) 0.077 Uiso 1 1 d . . . C43 C -0.2360(4) -0.0047(3) 0.80921(18) 0.0734(12) Uani 1 1 d . . . H43 H -0.294(4) -0.051(3) 0.7991(18) 0.088 Uiso 1 1 d . . . C47 C 0.1717(2) 0.18238(18) 0.79890(12) 0.0342(6) Uani 1 1 d . . . F1 F 0.31878(19) 0.22581(14) 1.09911(10) 0.0709(6) Uani 1 1 d . . . F2 F 0.62615(18) 0.19551(17) 1.10264(11) 0.0792(7) Uani 1 1 d . . . F3 F 0.4900(2) 0.31312(18) 1.11781(14) 0.1068(10) Uani 1 1 d . . . F4 F 0.4775(3) 0.24120(17) 1.04096(11) 0.0883(8) Uani 1 1 d . . . F5 F 0.4515(2) 0.11093(13) 1.08297(10) 0.0715(6) Uani 1 1 d . . . F6 F 0.4667(3) 0.1836(3) 1.16014(11) 0.1094(10) Uani 1 1 d . . . Ir1 Ir 0.060668(9) 0.233271(7) 0.856468(4) 0.02887(5) Uani 1 1 d . . . N1 N 0.1902(2) 0.16285(14) 0.90118(10) 0.0333(5) Uani 1 1 d . . . N2 N -0.0664(2) 0.29225(16) 0.80343(9) 0.0345(5) Uani 1 1 d . . . N4 N 0.15157(19) 0.36418(14) 0.87546(9) 0.0307(5) Uani 1 1 d . . . N5 N -0.0565(2) 0.28963(15) 0.92134(9) 0.0320(5) Uani 1 1 d . . . P1 P 0.47223(8) 0.21147(6) 1.10115(4) 0.0491(2) Uani 1 1 d . . . C11 C 0.3744(3) 0.3368(2) 0.84321(13) 0.0399(7) Uani 1 1 d D . . H11 H 0.346(3) 0.283(2) 0.8406(14) 0.048 Uiso 1 1 d . . . C441 C 0.4892(6) 0.3424(5) 0.8817(3) 0.083(2) Uani 0.80 1 d PD A 1 H44A H 0.5558 0.3012 0.8711 0.125 Uiso 0.80 1 calc PR A 1 H44B H 0.4607 0.3272 0.9165 0.125 Uiso 0.80 1 calc PR A 1 H44C H 0.5235 0.4023 0.8818 0.125 Uiso 0.80 1 calc PR A 1 C451 C 0.4195(6) 0.3492(4) 0.7866(2) 0.0660(15) Uani 0.80 1 d PD A 1 H45A H 0.4885 0.3076 0.7794 0.099 Uiso 0.80 1 calc PR A 1 H45B H 0.4504 0.4095 0.7819 0.099 Uiso 0.80 1 calc PR A 1 H45C H 0.3479 0.3383 0.7627 0.099 Uiso 0.80 1 calc PR A 1 C442 C 0.4451(16) 0.3120(13) 0.8950(10) 0.044(5) Uani 0.20 1 d PD A 2 H44D H 0.5155 0.2717 0.8877 0.066 Uiso 0.20 1 calc PR A 2 H44E H 0.3850 0.2834 0.9183 0.066 Uiso 0.20 1 calc PR A 2 H44F H 0.4788 0.3654 0.9113 0.066 Uiso 0.20 1 calc PR A 2 C452 C 0.4701(18) 0.3745(15) 0.8048(9) 0.054(5) Uani 0.20 1 d PD A 2 H45D H 0.5360 0.3305 0.7978 0.081 Uiso 0.20 1 calc PR A 2 H45E H 0.5100 0.4273 0.8195 0.081 Uiso 0.20 1 calc PR A 2 H45F H 0.4256 0.3897 0.7725 0.081 Uiso 0.20 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 C1 0.0278(12) 0.0390(16) 0.0372(18) 0.0052(11) 0.0012(11) -0.0064(11) C2 0.0284(12) 0.0334(16) 0.0344(17) 0.0002(11) -0.0019(11) -0.0036(10) C3 0.0286(12) 0.0323(15) 0.0335(17) 0.0015(11) -0.0023(11) -0.0010(10) C4 0.0315(13) 0.0304(15) 0.050(2) -0.0010(12) 0.0048(12) -0.0039(11) C5 0.0293(13) 0.0577(19) 0.0373(19) -0.0105(13) 0.0050(12) 0.0011(12) C6 0.0317(15) 0.079(3) 0.049(2) -0.0183(17) -0.0044(14) 0.0088(15) C7 0.0348(14) 0.0476(17) 0.042(2) 0.0011(14) 0.0076(12) -0.0063(13) C8 0.0296(13) 0.0387(17) 0.0362(18) 0.0019(11) 0.0038(11) -0.0056(10) C9 0.0297(13) 0.0362(16) 0.0338(17) -0.0014(11) -0.0019(11) 0.0018(10) C10 0.0343(13) 0.0288(14) 0.0366(17) 0.0007(11) -0.0057(12) -0.0033(10) C12 0.0288(13) 0.0466(18) 0.0375(18) -0.0029(12) 0.0040(11) -0.0004(11) C13 0.0331(14) 0.0399(17) 0.047(2) 0.0039(13) 0.0030(13) -0.0090(12) C14 0.0438(16) 0.0408(17) 0.042(2) 0.0055(13) -0.0060(14) -0.0095(13) C15 0.0297(13) 0.0312(16) 0.055(2) 0.0055(12) 0.0003(12) -0.0049(11) C16 0.0342(14) 0.0375(16) 0.0416(19) -0.0039(12) -0.0077(12) 0.0033(11) C17 0.0387(14) 0.0308(15) 0.0435(19) -0.0007(12) -0.0088(13) 0.0010(11) C18 0.0378(14) 0.0330(16) 0.0431(19) 0.0037(12) -0.0036(12) -0.0073(11) C19 0.0368(14) 0.0387(17) 0.0381(18) -0.0062(12) 0.0118(12) -0.0089(11) C20 0.0410(15) 0.0322(17) 0.046(2) -0.0018(12) 0.0123(13) -0.0084(12) C21 0.0405(16) 0.0475(19) 0.039(2) 0.0040(13) 0.0031(13) 0.0043(13) C22 0.0556(19) 0.045(2) 0.046(2) 0.0040(14) 0.0099(16) -0.0065(15) C23 0.0414(16) 0.0511(19) 0.043(2) 0.0005(14) 0.0080(13) -0.0014(14) C24 0.0377(16) 0.0421(19) 0.069(3) -0.0023(15) 0.0105(15) 0.0017(13) C25 0.0548(18) 0.0353(18) 0.053(2) -0.0047(14) 0.0121(15) -0.0089(14) C26 0.051(2) 0.081(3) 0.046(2) -0.0022(18) -0.0091(16) 0.0263(18) C27 0.0404(16) 0.0391(18) 0.063(2) -0.0093(15) -0.0051(15) 0.0069(13) C28 0.0530(18) 0.0342(17) 0.055(2) -0.0028(14) -0.0043(15) 0.0020(13) C29 0.064(2) 0.0311(16) 0.059(2) -0.0002(15) -0.0051(16) -0.0082(15) C30 0.0329(15) 0.057(2) 0.049(2) -0.0062(15) 0.0048(13) 0.0026(13) C31 0.0531(18) 0.0352(18) 0.057(2) 0.0048(14) 0.0007(16) -0.0113(14) C32 0.0356(16) 0.058(2) 0.063(2) -0.0138(17) 0.0014(15) 0.0129(14) C33 0.0392(16) 0.0455(19) 0.073(3) 0.0174(16) -0.0009(16) 0.0044(14) C34 0.0523(19) 0.065(2) 0.049(2) 0.0170(17) -0.0119(17) -0.0100(16) C35 0.0364(15) 0.054(2) 0.040(2) -0.0112(13) 0.0065(13) -0.0108(13) C36 0.0487(19) 0.061(2) 0.064(3) -0.0125(17) 0.0261(17) -0.0025(16) C37 0.0496(18) 0.064(2) 0.048(2) 0.0076(16) -0.0023(15) 0.0181(16) C38 0.0448(19) 0.065(2) 0.078(3) 0.030(2) -0.0167(19) -0.0014(16) C39 0.079(3) 0.046(2) 0.068(3) -0.0105(18) 0.022(2) -0.0231(19) C40 0.0481(18) 0.049(2) 0.055(2) 0.0009(16) 0.0086(16) -0.0167(15) C41 0.0530(19) 0.065(2) 0.044(2) -0.0024(16) 0.0138(16) -0.0035(16) C42 0.054(2) 0.085(3) 0.053(3) -0.0144(19) 0.0033(17) -0.0264(19) C43 0.079(3) 0.069(3) 0.073(3) -0.021(2) 0.008(2) -0.040(2) C47 0.0300(13) 0.0317(16) 0.0409(18) -0.0022(11) 0.0045(11) -0.0042(10) F1 0.0452(10) 0.0758(15) 0.0918(18) -0.0129(12) 0.0085(11) 0.0069(9) F2 0.0437(11) 0.0865(16) 0.108(2) -0.0328(14) 0.0084(11) -0.0032(10) F3 0.0823(16) 0.0689(17) 0.169(3) -0.0547(18) 0.0086(18) -0.0080(13) F4 0.0927(18) 0.0981(19) 0.0747(19) 0.0196(13) 0.0230(14) -0.0121(13) F5 0.0686(13) 0.0413(11) 0.1037(19) -0.0077(11) -0.0260(12) 0.0072(9) F6 0.0898(18) 0.190(3) 0.0488(17) 0.0088(17) -0.0026(13) -0.0131(19) Ir1 0.02640(6) 0.02872(7) 0.03153(7) 0.00152(4) 0.00247(4) -0.00171(4) N1 0.0333(11) 0.0294(12) 0.0372(15) 0.0044(9) -0.0026(10) -0.0037(9) N2 0.0279(10) 0.0421(14) 0.0335(14) -0.0014(10) 0.0019(9) 0.0031(9) N4 0.0289(11) 0.0298(12) 0.0333(14) 0.0033(9) 0.0006(9) -0.0034(8) N5 0.0295(10) 0.0319(13) 0.0346(14) 0.0018(9) 0.0031(9) -0.0034(9) P1 0.0434(4) 0.0487(5) 0.0553(6) -0.0099(4) 0.0084(4) -0.0033(3) C11 0.0321(14) 0.0390(16) 0.049(2) -0.0001(13) 0.0075(13) -0.0021(12) C441 0.055(4) 0.105(6) 0.089(6) -0.029(4) -0.021(4) 0.031(4) C451 0.060(4) 0.078(4) 0.061(4) 0.009(3) 0.027(3) 0.008(3) C442 0.014(8) 0.035(10) 0.084(16) -0.004(9) 0.009(8) 0.010(6) C452 0.035(10) 0.064(14) 0.063(15) -0.010(10) 0.000(9) 0.002(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C13 1.372(4) . ? C1 N4 1.378(3) . ? C1 C11 1.503(4) . ? C2 N5 1.343(3) . ? C2 C9 1.411(4) . ? C2 C3 1.463(4) . ? C3 N4 1.341(3) . ? C3 C10 1.408(4) . ? C4 C24 1.395(4) . ? C4 C47 1.414(4) . ? C4 C15 1.454(4) . ? C5 N2 1.358(4) . ? C5 C6 1.398(5) . ? C5 C35 1.457(4) . ? C6 C26 1.372(6) . ? C6 H6 0.93(4) . ? C7 C8 1.370(4) . ? C7 C12 1.395(4) . ? C7 H7 0.96(4) . ? C8 N5 1.375(3) . ? C8 C20 1.507(4) . ? C9 C12 1.413(4) . ? C9 C16 1.425(4) . ? C10 C18 1.408(4) . ? C10 C17 1.425(4) . ? C12 C30 1.416(4) . ? C13 C18 1.402(4) . ? C13 H13 1.00(3) . ? C14 N1 1.338(4) . ? C14 C34 1.369(5) . ? C14 H14 0.97(3) . ? C15 N1 1.366(4) . ? C15 C33 1.394(4) . ? C16 C27 1.385(4) . ? C16 C17 1.458(4) . ? C17 C28 1.389(4) . ? C18 C31 1.412(4) . ? C19 C25 1.402(4) . ? C19 C35 1.406(4) . ? C19 Ir1 2.022(3) . ? C20 C40 1.528(4) . ? C20 C22 1.537(5) . ? C20 H20 0.93(3) . ? C21 N2 1.342(4) . ? C21 C37 1.373(4) . ? C21 H21 0.95(3) . ? C22 H22A 0.96(4) . ? C22 H22B 0.97(4) . ? C22 H22C 0.99(4) . ? C23 C47 1.390(4) . ? C23 C41 1.390(5) . ? C23 H23 1.01(3) . ? C24 C36 1.367(5) . ? C24 H24 0.91(4) . ? C25 C39 1.389(5) . ? C25 H25 0.98(3) . ? C26 C37 1.367(5) . ? C26 H26 0.86(4) . ? C27 C32 1.390(5) . ? C27 H27 0.86(4) . ? C28 C29 1.385(5) . ? C28 H28 0.95(4) . ? C29 C31 1.360(5) . ? C29 H29 0.94(4) . ? C30 C32 1.362(5) . ? C30 H30 0.86(4) . ? C31 H31 0.97(4) . ? C32 H32 0.92(4) . ? C33 C38 1.360(6) . ? C33 H33 0.94(4) . ? C34 C38 1.375(6) . ? C34 H34 0.85(4) . ? C35 C42 1.400(4) . ? C36 C41 1.381(5) . ? C36 H36 0.93(4) . ? C37 H37 0.92(4) . ? C38 H38 0.91(4) . ? C39 C43 1.382(6) . ? C39 H39 0.92(4) . ? C40 H40A 0.98(4) . ? C40 H40B 0.97(4) . ? C40 H40C 0.95(4) . ? C41 H41 0.97(4) . ? C42 C43 1.357(6) . ? C42 H42 0.94(4) . ? C43 H43 0.95(4) . ? C47 Ir1 2.014(3) . ? F1 P1 1.591(2) . ? F2 P1 1.599(2) . ? F3 P1 1.582(3) . ? F4 P1 1.593(3) . ? F5 P1 1.581(2) . ? F6 P1 1.556(3) . ? Ir1 N1 2.030(2) . ? Ir1 N2 2.059(2) . ? Ir1 N4 2.212(2) . ? Ir1 N5 2.218(2) . ? C11 C452 1.50(2) . ? C11 C441 1.524(7) . ? C11 C451 1.529(6) . ? C11 C442 1.54(2) . ? C11 H11 0.85(3) . ? C441 H44A 0.9600 . ? C441 H44B 0.9600 . ? C441 H44C 0.9600 . ? C451 H45A 0.9600 . ? C451 H45B 0.9600 . ? C451 H45C 0.9600 . ? C442 H44D 0.9600 . ? C442 H44E 0.9600 . ? C442 H44F 0.9600 . ? C452 H45D 0.9600 . ? C452 H45E 0.9600 . ? C452 H45F 0.9600 . ? 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 C13 C1 N4 120.1(2) . . ? C13 C1 C11 121.5(2) . . ? N4 C1 C11 118.4(2) . . ? N5 C2 C9 123.7(2) . . ? N5 C2 C3 117.1(2) . . ? C9 C2 C3 119.1(2) . . ? N4 C3 C10 123.8(2) . . ? N4 C3 C2 117.2(2) . . ? C10 C3 C2 119.0(2) . . ? C24 C4 C47 121.2(3) . . ? C24 C4 C15 123.6(3) . . ? C47 C4 C15 115.0(2) . . ? N2 C5 C6 119.4(3) . . ? N2 C5 C35 114.3(3) . . ? C6 C5 C35 126.2(3) . . ? C26 C6 C5 120.6(3) . . ? C26 C6 H6 122(2) . . ? C5 C6 H6 117(2) . . ? C8 C7 C12 122.2(3) . . ? C8 C7 H7 122(2) . . ? C12 C7 H7 115.9(19) . . ? C7 C8 N5 120.8(3) . . ? C7 C8 C20 119.9(3) . . ? N5 C8 C20 119.3(2) . . ? C2 C9 C12 117.7(2) . . ? C2 C9 C16 121.6(3) . . ? C12 C9 C16 120.7(2) . . ? C18 C10 C3 117.5(2) . . ? C18 C10 C17 120.5(2) . . ? C3 C10 C17 121.9(2) . . ? C7 C12 C9 117.3(3) . . ? C7 C12 C30 123.4(3) . . ? C9 C12 C30 119.3(3) . . ? C1 C13 C18 122.1(3) . . ? C1 C13 H13 119.7(18) . . ? C18 C13 H13 118.2(18) . . ? N1 C14 C34 122.8(3) . . ? N1 C14 H14 117(2) . . ? C34 C14 H14 120(2) . . ? N1 C15 C33 119.1(3) . . ? N1 C15 C4 114.4(2) . . ? C33 C15 C4 126.5(3) . . ? C27 C16 C9 117.4(3) . . ? C27 C16 C17 123.7(3) . . ? C9 C16 C17 118.9(2) . . ? C28 C17 C10 117.5(3) . . ? C28 C17 C16 123.8(3) . . ? C10 C17 C16 118.7(2) . . ? C13 C18 C10 117.4(2) . . ? C13 C18 C31 123.2(3) . . ? C10 C18 C31 119.4(3) . . ? C25 C19 C35 117.9(3) . . ? C25 C19 Ir1 128.0(2) . . ? C35 C19 Ir1 114.1(2) . . ? C8 C20 C40 110.6(3) . . ? C8 C20 C22 111.1(3) . . ? C40 C20 C22 111.0(3) . . ? C8 C20 H20 108(2) . . ? C40 C20 H20 108(2) . . ? C22 C20 H20 108(2) . . ? N2 C21 C37 122.8(3) . . ? N2 C21 H21 115(2) . . ? C37 C21 H21 122(2) . . ? C20 C22 H22A 110(2) . . ? C20 C22 H22B 113(2) . . ? H22A C22 H22B 109(3) . . ? C20 C22 H22C 108(2) . . ? H22A C22 H22C 111(3) . . ? H22B C22 H22C 105(3) . . ? C47 C23 C41 121.0(3) . . ? C47 C23 H23 118(2) . . ? C41 C23 H23 121(2) . . ? C36 C24 C4 119.8(3) . . ? C36 C24 H24 121(2) . . ? C4 C24 H24 119(2) . . ? C39 C25 C19 120.1(4) . . ? C39 C25 H25 120(2) . . ? C19 C25 H25 120(2) . . ? C37 C26 C6 119.1(3) . . ? C37 C26 H26 119(3) . . ? C6 C26 H26 121(3) . . ? C16 C27 C32 121.6(3) . . ? C16 C27 H27 117(2) . . ? C32 C27 H27 122(2) . . ? C29 C28 C17 121.3(3) . . ? C29 C28 H28 121(2) . . ? C17 C28 H28 118(2) . . ? C31 C29 C28 121.9(3) . . ? C31 C29 H29 115(2) . . ? C28 C29 H29 123(2) . . ? C32 C30 C12 119.2(3) . . ? C32 C30 H30 124(2) . . ? C12 C30 H30 117(2) . . ? C29 C31 C18 119.3(3) . . ? C29 C31 H31 126(2) . . ? C18 C31 H31 115(2) . . ? C30 C32 C27 121.7(3) . . ? C30 C32 H32 119(2) . . ? C27 C32 H32 119(2) . . ? C38 C33 C15 119.8(4) . . ? C38 C33 H33 125(2) . . ? C15 C33 H33 115(2) . . ? C14 C34 C38 117.7(4) . . ? C14 C34 H34 116(3) . . ? C38 C34 H34 126(3) . . ? C42 C35 C19 120.5(3) . . ? C42 C35 C5 123.9(3) . . ? C19 C35 C5 115.6(2) . . ? C24 C36 C41 120.2(3) . . ? C24 C36 H36 122(2) . . ? C41 C36 H36 117(2) . . ? C26 C37 C21 119.0(4) . . ? C26 C37 H37 121(2) . . ? C21 C37 H37 120(2) . . ? C33 C38 C34 120.8(3) . . ? C33 C38 H38 123(3) . . ? C34 C38 H38 116(3) . . ? C43 C39 C25 121.1(4) . . ? C43 C39 H39 124(3) . . ? C25 C39 H39 115(3) . . ? C20 C40 H40A 109(2) . . ? C20 C40 H40B 112(2) . . ? H40A C40 H40B 107(3) . . ? C20 C40 H40C 109(2) . . ? H40A C40 H40C 113(3) . . ? H40B C40 H40C 107(3) . . ? C36 C41 C23 120.5(4) . . ? C36 C41 H41 123(2) . . ? C23 C41 H41 117(2) . . ? C43 C42 C35 120.7(4) . . ? C43 C42 H42 121(3) . . ? C35 C42 H42 118(3) . . ? C42 C43 C39 119.7(3) . . ? C42 C43 H43 122(3) . . ? C39 C43 H43 118(3) . . ? C23 C47 C4 117.3(3) . . ? C23 C47 Ir1 128.8(2) . . ? C4 C47 Ir1 113.9(2) . . ? C47 Ir1 C19 82.02(11) . . ? C47 Ir1 N1 80.68(11) . . ? C19 Ir1 N1 95.33(10) . . ? C47 Ir1 N2 92.63(10) . . ? C19 Ir1 N2 80.04(11) . . ? N1 Ir1 N2 172.39(9) . . ? C47 Ir1 N4 104.39(9) . . ? C19 Ir1 N4 169.81(10) . . ? N1 Ir1 N4 93.55(8) . . ? N2 Ir1 N4 91.63(9) . . ? C47 Ir1 N5 178.34(9) . . ? C19 Ir1 N5 99.08(10) . . ? N1 Ir1 N5 97.96(9) . . ? N2 Ir1 N5 88.78(9) . . ? N4 Ir1 N5 74.70(8) . . ? C14 N1 C15 119.7(3) . . ? C14 N1 Ir1 124.6(2) . . ? C15 N1 Ir1 115.6(2) . . ? C21 N2 C5 119.2(3) . . ? C21 N2 Ir1 125.21(19) . . ? C5 N2 Ir1 115.5(2) . . ? C3 N4 C1 118.2(2) . . ? C3 N4 Ir1 110.57(16) . . ? C1 N4 Ir1 128.86(19) . . ? C2 N5 C8 118.0(2) . . ? C2 N5 Ir1 110.67(17) . . ? C8 N5 Ir1 130.30(18) . . ? F6 P1 F5 91.27(18) . . ? F6 P1 F3 90.2(2) . . ? F5 P1 F3 178.11(16) . . ? F6 P1 F1 91.02(15) . . ? F5 P1 F1 89.31(12) . . ? F3 P1 F1 89.46(13) . . ? F6 P1 F4 179.30(19) . . ? F5 P1 F4 89.38(15) . . ? F3 P1 F4 89.15(17) . . ? F1 P1 F4 88.75(15) . . ? F6 P1 F2 89.25(15) . . ? F5 P1 F2 89.74(12) . . ? F3 P1 F2 91.48(13) . . ? F1 P1 F2 179.02(14) . . ? F4 P1 F2 90.99(15) . . ? C1 C11 C452 114.4(9) . . ? C1 C11 C441 112.5(4) . . ? C452 C11 C441 83.6(9) . . ? C1 C11 C451 112.5(3) . . ? C452 C11 C451 30.1(7) . . ? C441 C11 C451 110.8(4) . . ? C1 C11 C442 106.9(8) . . ? C452 C11 C442 109.8(10) . . ? C441 C11 C442 27.5(6) . . ? C451 C11 C442 133.5(7) . . ? C1 C11 H11 111(2) . . ? C452 C11 H11 122(3) . . ? C441 C11 H11 111(2) . . ? C451 C11 H11 98(2) . . ? C442 C11 H11 90(2) . . ? C11 C441 H44A 109.5 . . ? C11 C441 H44B 109.5 . . ? H44A C441 H44B 109.5 . . ? C11 C441 H44C 109.5 . . ? H44A C441 H44C 109.5 . . ? H44B C441 H44C 109.5 . . ? C11 C451 H45A 109.5 . . ? C11 C451 H45B 109.5 . . ? H45A C451 H45B 109.5 . . ? C11 C451 H45C 109.5 . . ? H45A C451 H45C 109.5 . . ? H45B C451 H45C 109.5 . . ? C11 C442 H44D 109.5 . . ? C11 C442 H44E 109.5 . . ? H44D C442 H44E 109.5 . . ? C11 C442 H44F 109.5 . . ? H44D C442 H44F 109.5 . . ? H44E C442 H44F 109.5 . . ? C11 C452 H45D 109.5 . . ? C11 C452 H45E 109.5 . . ? H45D C452 H45E 109.5 . . ? C11 C452 H45F 109.5 . . ? H45D C452 H45F 109.5 . . ? H45E C452 H45F 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 N5 C2 C3 N4 -1.7(4) . . . . ? C9 C2 C3 N4 174.2(2) . . . . ? N5 C2 C3 C10 178.3(2) . . . . ? C9 C2 C3 C10 -5.9(4) . . . . ? N2 C5 C6 C26 2.6(5) . . . . ? C35 C5 C6 C26 -173.4(3) . . . . ? C12 C7 C8 N5 0.6(5) . . . . ? C12 C7 C8 C20 178.1(3) . . . . ? N5 C2 C9 C12 3.4(4) . . . . ? C3 C2 C9 C12 -172.2(2) . . . . ? N5 C2 C9 C16 -175.2(2) . . . . ? C3 C2 C9 C16 9.2(4) . . . . ? N4 C3 C10 C18 0.1(4) . . . . ? C2 C3 C10 C18 -179.9(3) . . . . ? N4 C3 C10 C17 177.6(3) . . . . ? C2 C3 C10 C17 -2.4(4) . . . . ? C8 C7 C12 C9 -4.1(4) . . . . ? C8 C7 C12 C30 176.8(3) . . . . ? C2 C9 C12 C7 2.2(4) . . . . ? C16 C9 C12 C7 -179.2(3) . . . . ? C2 C9 C12 C30 -178.7(3) . . . . ? C16 C9 C12 C30 -0.1(4) . . . . ? N4 C1 C13 C18 2.1(5) . . . . ? C11 C1 C13 C18 -175.8(3) . . . . ? C24 C4 C15 N1 173.8(3) . . . . ? C47 C4 C15 N1 -2.0(3) . . . . ? C24 C4 C15 C33 -5.5(5) . . . . ? C47 C4 C15 C33 178.7(3) . . . . ? C2 C9 C16 C27 177.0(3) . . . . ? C12 C9 C16 C27 -1.6(4) . . . . ? C2 C9 C16 C17 -4.3(4) . . . . ? C12 C9 C16 C17 177.1(3) . . . . ? C18 C10 C17 C28 4.1(4) . . . . ? C3 C10 C17 C28 -173.3(3) . . . . ? C18 C10 C17 C16 -175.3(3) . . . . ? C3 C10 C17 C16 7.3(4) . . . . ? C27 C16 C17 C28 -4.7(5) . . . . ? C9 C16 C17 C28 176.7(3) . . . . ? C27 C16 C17 C10 174.7(3) . . . . ? C9 C16 C17 C10 -3.9(4) . . . . ? C1 C13 C18 C10 6.3(5) . . . . ? C1 C13 C18 C31 -176.8(3) . . . . ? C3 C10 C18 C13 -7.2(4) . . . . ? C17 C10 C18 C13 175.3(3) . . . . ? C3 C10 C18 C31 175.7(3) . . . . ? C17 C10 C18 C31 -1.8(4) . . . . ? C7 C8 C20 C40 63.1(4) . . . . ? N5 C8 C20 C40 -119.3(3) . . . . ? C7 C8 C20 C22 -60.6(4) . . . . ? N5 C8 C20 C22 117.0(3) . . . . ? C47 C4 C24 C36 -2.4(4) . . . . ? C15 C4 C24 C36 -177.9(3) . . . . ? C35 C19 C25 C39 -3.3(5) . . . . ? Ir1 C19 C25 C39 175.7(3) . . . . ? C5 C6 C26 C37 -1.0(5) . . . . ? C9 C16 C27 C32 1.3(5) . . . . ? C17 C16 C27 C32 -177.3(3) . . . . ? C10 C17 C28 C29 -3.1(5) . . . . ? C16 C17 C28 C29 176.3(3) . . . . ? C17 C28 C29 C31 -0.3(5) . . . . ? C7 C12 C30 C32 -178.8(3) . . . . ? C9 C12 C30 C32 2.1(5) . . . . ? C28 C29 C31 C18 2.7(5) . . . . ? C13 C18 C31 C29 -178.5(3) . . . . ? C10 C18 C31 C29 -1.6(5) . . . . ? C12 C30 C32 C27 -2.4(5) . . . . ? C16 C27 C32 C30 0.7(5) . . . . ? N1 C15 C33 C38 -1.5(5) . . . . ? C4 C15 C33 C38 177.9(3) . . . . ? N1 C14 C34 C38 0.6(5) . . . . ? C25 C19 C35 C42 2.8(5) . . . . ? Ir1 C19 C35 C42 -176.2(3) . . . . ? C25 C19 C35 C5 -175.0(3) . . . . ? Ir1 C19 C35 C5 6.0(3) . . . . ? N2 C5 C35 C42 -179.5(3) . . . . ? C6 C5 C35 C42 -3.4(5) . . . . ? N2 C5 C35 C19 -1.8(4) . . . . ? C6 C5 C35 C19 174.4(3) . . . . ? C4 C24 C36 C41 0.3(5) . . . . ? C6 C26 C37 C21 0.0(5) . . . . ? N2 C21 C37 C26 -0.5(5) . . . . ? C15 C33 C38 C34 -0.8(5) . . . . ? C14 C34 C38 C33 1.3(5) . . . . ? C19 C25 C39 C43 1.3(6) . . . . ? C24 C36 C41 C23 0.6(5) . . . . ? C47 C23 C41 C36 0.5(5) . . . . ? C19 C35 C42 C43 -0.4(5) . . . . ? C5 C35 C42 C43 177.2(4) . . . . ? C35 C42 C43 C39 -1.7(6) . . . . ? C25 C39 C43 C42 1.3(6) . . . . ? C41 C23 C47 C4 -2.5(4) . . . . ? C41 C23 C47 Ir1 179.5(2) . . . . ? C24 C4 C47 C23 3.4(4) . . . . ? C15 C4 C47 C23 179.3(2) . . . . ? C24 C4 C47 Ir1 -178.3(2) . . . . ? C15 C4 C47 Ir1 -2.4(3) . . . . ? C23 C47 Ir1 C19 85.3(3) . . . . ? C4 C47 Ir1 C19 -92.8(2) . . . . ? C23 C47 Ir1 N1 -177.9(3) . . . . ? C4 C47 Ir1 N1 4.03(18) . . . . ? C23 C47 Ir1 N2 5.8(3) . . . . ? C4 C47 Ir1 N2 -172.31(19) . . . . ? C23 C47 Ir1 N4 -86.6(3) . . . . ? C4 C47 Ir1 N4 95.33(19) . . . . ? C23 C47 Ir1 N5 -143(3) . . . . ? C4 C47 Ir1 N5 39(3) . . . . ? C25 C19 Ir1 C47 81.1(3) . . . . ? C35 C19 Ir1 C47 -100.0(2) . . . . ? C25 C19 Ir1 N1 1.3(3) . . . . ? C35 C19 Ir1 N1 -179.7(2) . . . . ? C25 C19 Ir1 N2 175.2(3) . . . . ? C35 C19 Ir1 N2 -5.8(2) . . . . ? C25 C19 Ir1 N4 -149.2(5) . . . . ? C35 C19 Ir1 N4 29.7(7) . . . . ? C25 C19 Ir1 N5 -97.7(3) . . . . ? C35 C19 Ir1 N5 81.3(2) . . . . ? C34 C14 N1 C15 -2.9(4) . . . . ? C34 C14 N1 Ir1 175.4(2) . . . . ? C33 C15 N1 C14 3.3(4) . . . . ? C4 C15 N1 C14 -176.1(2) . . . . ? C33 C15 N1 Ir1 -175.2(2) . . . . ? C4 C15 N1 Ir1 5.4(3) . . . . ? C47 Ir1 N1 C14 176.4(2) . . . . ? C19 Ir1 N1 C14 -102.6(2) . . . . ? N2 Ir1 N1 C14 -154.8(6) . . . . ? N4 Ir1 N1 C14 72.4(2) . . . . ? N5 Ir1 N1 C14 -2.7(2) . . . . ? C47 Ir1 N1 C15 -5.27(18) . . . . ? C19 Ir1 N1 C15 75.72(19) . . . . ? N2 Ir1 N1 C15 23.5(7) . . . . ? N4 Ir1 N1 C15 -109.28(18) . . . . ? N5 Ir1 N1 C15 175.69(18) . . . . ? C37 C21 N2 C5 2.1(5) . . . . ? C37 C21 N2 Ir1 178.3(3) . . . . ? C6 C5 N2 C21 -3.1(4) . . . . ? C35 C5 N2 C21 173.4(3) . . . . ? C6 C5 N2 Ir1 -179.7(2) . . . . ? C35 C5 N2 Ir1 -3.2(3) . . . . ? C47 Ir1 N2 C21 -89.9(2) . . . . ? C19 Ir1 N2 C21 -171.3(3) . . . . ? N1 Ir1 N2 C21 -118.3(6) . . . . ? N4 Ir1 N2 C21 14.6(2) . . . . ? N5 Ir1 N2 C21 89.2(2) . . . . ? C47 Ir1 N2 C5 86.5(2) . . . . ? C19 Ir1 N2 C5 5.0(2) . . . . ? N1 Ir1 N2 C5 58.1(7) . . . . ? N4 Ir1 N2 C5 -169.1(2) . . . . ? N5 Ir1 N2 C5 -94.4(2) . . . . ? C10 C3 N4 C1 8.3(4) . . . . ? C2 C3 N4 C1 -171.7(2) . . . . ? C10 C3 N4 Ir1 -155.9(2) . . . . ? C2 C3 N4 Ir1 24.0(3) . . . . ? C13 C1 N4 C3 -9.3(4) . . . . ? C11 C1 N4 C3 168.6(3) . . . . ? C13 C1 N4 Ir1 151.6(2) . . . . ? C11 C1 N4 Ir1 -30.5(4) . . . . ? C47 Ir1 N4 C3 155.29(19) . . . . ? C19 Ir1 N4 C3 27.2(7) . . . . ? N1 Ir1 N4 C3 -123.43(19) . . . . ? N2 Ir1 N4 C3 62.15(19) . . . . ? N5 Ir1 N4 C3 -26.14(18) . . . . ? C47 Ir1 N4 C1 -6.8(2) . . . . ? C19 Ir1 N4 C1 -134.9(5) . . . . ? N1 Ir1 N4 C1 74.5(2) . . . . ? N2 Ir1 N4 C1 -99.9(2) . . . . ? N5 Ir1 N4 C1 171.8(2) . . . . ? C9 C2 N5 C8 -6.9(4) . . . . ? C3 C2 N5 C8 168.7(2) . . . . ? C9 C2 N5 Ir1 162.8(2) . . . . ? C3 C2 N5 Ir1 -21.6(3) . . . . ? C7 C8 N5 C2 4.9(4) . . . . ? C20 C8 N5 C2 -172.7(3) . . . . ? C7 C8 N5 Ir1 -162.5(2) . . . . ? C20 C8 N5 Ir1 20.0(4) . . . . ? C47 Ir1 N5 C2 82(3) . . . . ? C19 Ir1 N5 C2 -146.43(18) . . . . ? N1 Ir1 N5 C2 116.83(17) . . . . ? N2 Ir1 N5 C2 -66.72(17) . . . . ? N4 Ir1 N5 C2 25.30(16) . . . . ? C47 Ir1 N5 C8 -110(3) . . . . ? C19 Ir1 N5 C8 21.6(2) . . . . ? N1 Ir1 N5 C8 -75.1(2) . . . . ? N2 Ir1 N5 C8 101.4(2) . . . . ? N4 Ir1 N5 C8 -166.6(2) . . . . ? C13 C1 C11 C452 -25.5(10) . . . . ? N4 C1 C11 C452 156.6(9) . . . . ? C13 C1 C11 C441 67.7(5) . . . . ? N4 C1 C11 C441 -110.2(4) . . . . ? C13 C1 C11 C451 -58.3(5) . . . . ? N4 C1 C11 C451 123.8(4) . . . . ? C13 C1 C11 C442 96.3(7) . . . . ? N4 C1 C11 C442 -81.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.758 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.061 _chemical_name_common ; Bis(2-(2-pyridyl)phenyl)(2,11-diisopropyl-1,12- diazaperylene)iridium(iii)-hexafluorophosphate ; #====================================================================== data_pit5i _database_code_depnum_ccdc_archive 'CCDC 827355' #TrackingRef '- pit5i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(1-phenylpyrazole)(1,12-diazaperylene)iridium(III)-hexafluorophosphate ; _chemical_melting_point '> 633' _chemical_formula_moiety 'C36 H24 N6 Ir 1+, F6 P 1-' _chemical_formula_sum 'C36 H24 F6 Ir N6 P' _chemical_formula_weight 877.78 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 27.111(2) _cell_length_b 13.1104(5) _cell_length_c 21.6429(17) _cell_angle_alpha 90.00 _cell_angle_beta 119.347(6) _cell_angle_gamma 90.00 _cell_volume 6705.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 21337 _cell_measurement_theta_min 1.37 _cell_measurement_theta_max 27.08 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.825 _exptl_crystal_size_mid 0.343 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method ? _exptl_crystal_F_000 3424 _exptl_absorpt_coefficient_mu 4.100 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4714 _exptl_absorpt_correction_T_max 0.4800 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12 x 0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 120 mm ; _diffrn_reflns_number 21315 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5896 _reflns_number_gt 4606 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were calculated in their expected positions and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; The unit cell contains disordered solvent molecules. In spite of several attempts, no reasonable solution could be received. Therefore the contribution of the disordered solvent species was subtracted from the structure factor calculation by the SQUEEZE instruction of the PLATON program suite. SQUEEZE calculated 874.8 \%A as solvent-accessible void volume and a number of electrons of 184 per cell. In consideration of Z these values correspond roughly with a half molecule of methylenechlorid per asymmetric unit. One of the both PF6 anions were refined isotropically using the restraint instruction SADI. ; _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^)+(0.08P)^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 SHELXL _refine_ls_extinction_coef 0.00016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5896 _refine_ls_number_parameters 436 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.009 _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 C1 C 0.3090(4) 0.9429(6) 0.0641(4) 0.0334(18) Uani 1 1 d . . . H1 H 0.3282 0.8913 0.0966 0.040 Uiso 1 1 calc R . . C2 C 0.3301(4) 0.9769(6) 0.0227(4) 0.0353(18) Uani 1 1 d . . . H2 H 0.3638 0.9502 0.0283 0.042 Uiso 1 1 calc R . . C3 C 0.3192(4) 1.0889(7) -0.0765(4) 0.042(2) Uani 1 1 d . . . H3 H 0.3517 1.0627 -0.0749 0.051 Uiso 1 1 calc R . . C4 C 0.2880(4) 1.1624(8) -0.1246(4) 0.046(2) Uani 1 1 d . . . H4 H 0.2997 1.1855 -0.1559 0.055 Uiso 1 1 calc R . . C5 C 0.2395(4) 1.2040(6) -0.1286(4) 0.040(2) Uani 1 1 d . . . H5 H 0.2194 1.2533 -0.1627 0.048 Uiso 1 1 calc R . . C6 C 0.1363(4) 1.2918(6) -0.1305(4) 0.041(2) Uani 1 1 d . . . H6 H 0.1462 1.3176 -0.1630 0.049 Uiso 1 1 calc R . . C7 C 0.0893(4) 1.3307(6) -0.1295(4) 0.042(2) Uani 1 1 d . . . H7 H 0.0676 1.3807 -0.1621 0.051 Uiso 1 1 calc R . . C8 C 0.0741(4) 1.2972(6) -0.0816(4) 0.0411(19) Uani 1 1 d . . . H8 H 0.0430 1.3257 -0.0807 0.049 Uiso 1 1 calc R . . C9 C 0.0927(4) 1.1793(7) 0.0182(4) 0.043(2) Uani 1 1 d . . . H9 H 0.0631 1.2066 0.0231 0.052 Uiso 1 1 calc R . . C10 C 0.1236(4) 1.1013(6) 0.0601(4) 0.0350(18) Uani 1 1 d . . . H10 H 0.1134 1.0743 0.0921 0.042 Uiso 1 1 calc R . . C11 C 0.1837(3) 1.0999(6) 0.0122(3) 0.0277(16) Uani 1 1 d . . . C12 C 0.2333(3) 1.0559(5) 0.0131(4) 0.0279(16) Uani 1 1 d . . . C13 C 0.2513(3) 1.0953(6) -0.0333(4) 0.0291(16) Uani 1 1 d . . . C14 C 0.2205(3) 1.1735(6) -0.0828(4) 0.0326(17) Uani 1 1 d . . . C15 C 0.1689(3) 1.2152(6) -0.0844(3) 0.0308(16) Uani 1 1 d . . . C16 C 0.1536(3) 1.1782(6) -0.0349(3) 0.0297(16) Uani 1 1 d . . . C17 C 0.1054(3) 1.2195(6) -0.0334(4) 0.0343(17) Uani 1 1 d . . . C18 C 0.3009(3) 1.0534(6) -0.0292(4) 0.0309(17) Uani 1 1 d . . . C19 C 0.2833(4) 1.0765(6) 0.2379(4) 0.041(2) Uani 1 1 d . . . H19 H 0.2576 1.1300 0.2245 0.049 Uiso 1 1 calc R . . C20 C 0.3369(5) 1.0773(7) 0.2958(4) 0.049(2) Uani 1 1 d . . . H20 H 0.3538 1.1299 0.3282 0.059 Uiso 1 1 calc R . . C21 C 0.3601(4) 0.9850(7) 0.2956(4) 0.044(2) Uani 1 1 d . . . H21 H 0.3964 0.9633 0.3282 0.053 Uiso 1 1 calc R . . C22 C 0.3172(4) 0.8269(6) 0.2182(4) 0.0341(18) Uani 1 1 d . . . C23 C 0.3603(4) 0.7572(7) 0.2561(4) 0.045(2) Uani 1 1 d . . . H23 H 0.3940 0.7771 0.2954 0.054 Uiso 1 1 calc R . . C24 C 0.3511(4) 0.6577(8) 0.2332(5) 0.050(2) Uani 1 1 d . . . H24 H 0.3785 0.6086 0.2581 0.060 Uiso 1 1 calc R . . C25 C 0.3016(5) 0.6302(7) 0.1735(5) 0.050(2) Uani 1 1 d . . . H25 H 0.2961 0.5628 0.1582 0.060 Uiso 1 1 calc R . . C26 C 0.2602(4) 0.7014(6) 0.1364(4) 0.0394(19) Uani 1 1 d . . . H26 H 0.2270 0.6808 0.0965 0.047 Uiso 1 1 calc R . . C27 C 0.2664(4) 0.8039(6) 0.1569(4) 0.0336(18) Uani 1 1 d . . . C28 C 0.1525(4) 0.8259(6) -0.0403(4) 0.041(2) Uani 1 1 d . . . H28 H 0.1771 0.8442 -0.0570 0.049 Uiso 1 1 calc R . . C29 C 0.1028(4) 0.7705(7) -0.0782(4) 0.049(2) Uani 1 1 d . . . H29 H 0.0876 0.7462 -0.1243 0.058 Uiso 1 1 calc R . . C30 C 0.0809(4) 0.7590(7) -0.0337(4) 0.046(2) Uani 1 1 d . . . H30 H 0.0478 0.7244 -0.0441 0.055 Uiso 1 1 calc R . . C31 C 0.1141(4) 0.8238(6) 0.0914(4) 0.0356(18) Uani 1 1 d . . . C32 C 0.0712(4) 0.7893(7) 0.1025(4) 0.0414(19) Uani 1 1 d . . . H32 H 0.0417 0.7513 0.0676 0.050 Uiso 1 1 calc R . . C33 C 0.0718(4) 0.8104(7) 0.1646(5) 0.048(2) Uani 1 1 d . . . H33 H 0.0423 0.7892 0.1718 0.058 Uiso 1 1 calc R . . C34 C 0.1169(4) 0.8638(8) 0.2165(5) 0.050(2) Uani 1 1 d . . . H34 H 0.1177 0.8781 0.2591 0.060 Uiso 1 1 calc R . . C35 C 0.1616(4) 0.8971(6) 0.2065(4) 0.0368(19) Uani 1 1 d . . . H35 H 0.1918 0.9322 0.2426 0.044 Uiso 1 1 calc R . . C36 C 0.1610(3) 0.8779(6) 0.1430(4) 0.0307(16) Uani 1 1 d . . . Ir Ir 0.215728(12) 0.92524(2) 0.110836(13) 0.02712(13) Uani 1 1 d . . . N1 N 0.2606(3) 0.9815(5) 0.0598(3) 0.0273(13) Uani 1 1 d . . . N2 N 0.1693(3) 1.0598(5) 0.0581(3) 0.0301(14) Uani 1 1 d . . . N3 N 0.2738(3) 0.9887(5) 0.2042(3) 0.0307(14) Uani 1 1 d . . . N4 N 0.3218(3) 0.9315(5) 0.2408(3) 0.0356(15) Uani 1 1 d . . . N5 N 0.1596(3) 0.8489(5) 0.0240(3) 0.0327(14) Uani 1 1 d . . . N6 N 0.1152(3) 0.8061(5) 0.0276(3) 0.0353(15) Uani 1 1 d . . . P1 P 0.0000 0.5000 0.0000 0.0318(6) Uani 1 2 d S . . F1 F 0.0283(2) 0.3936(4) 0.0358(3) 0.0495(12) Uani 1 1 d . . . F2 F 0.0227(3) 0.5494(5) 0.0758(3) 0.082(2) Uani 1 1 d . . . F3 F 0.0570(3) 0.5327(6) 0.0018(4) 0.086(2) Uani 1 1 d . . . P2 P 0.0000 0.4035(3) 0.2500 0.0545(9) Uiso 1 2 d SD . . F4 F 0.0000 0.2840(8) 0.2500 0.118(4) Uiso 1 2 d SD . . F5 F 0.0670(3) 0.4031(5) 0.2989(4) 0.089(2) Uiso 1 1 d D . . F6 F 0.0053(6) 0.3996(9) 0.1816(6) 0.189(6) Uiso 1 1 d D . . F7 F 0.0000 0.5208(11) 0.2500 0.288(14) Uiso 1 2 d SD . . 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 C1 0.037(5) 0.029(4) 0.034(4) 0.001(3) 0.017(4) 0.004(3) C2 0.038(5) 0.035(4) 0.041(4) 0.005(3) 0.026(4) 0.005(4) C3 0.041(5) 0.054(6) 0.037(4) -0.004(4) 0.023(4) -0.007(4) C4 0.050(6) 0.065(6) 0.030(4) 0.000(4) 0.025(4) -0.008(5) C5 0.052(5) 0.041(5) 0.028(4) 0.007(3) 0.019(4) 0.003(4) C6 0.052(5) 0.032(4) 0.035(4) 0.008(3) 0.019(4) 0.008(4) C7 0.043(5) 0.033(4) 0.037(4) 0.004(3) 0.008(4) 0.004(4) C8 0.037(5) 0.035(5) 0.047(4) 0.002(4) 0.017(4) 0.007(4) C9 0.036(5) 0.055(6) 0.041(4) -0.001(4) 0.021(4) 0.004(4) C10 0.043(5) 0.039(4) 0.029(4) 0.006(3) 0.022(4) 0.010(4) C11 0.027(4) 0.030(4) 0.023(3) -0.003(3) 0.010(3) -0.002(3) C12 0.034(4) 0.023(4) 0.025(3) -0.002(3) 0.013(3) -0.002(3) C13 0.033(4) 0.029(4) 0.024(3) -0.004(3) 0.013(3) -0.003(3) C14 0.036(4) 0.035(4) 0.024(3) -0.005(3) 0.012(3) -0.005(4) C15 0.034(4) 0.029(4) 0.022(3) 0.001(3) 0.009(3) 0.003(4) C16 0.026(4) 0.032(4) 0.024(3) -0.001(3) 0.007(3) 0.003(3) C17 0.033(4) 0.031(4) 0.036(4) -0.002(3) 0.016(3) 0.000(4) C18 0.034(4) 0.033(4) 0.029(4) -0.001(3) 0.018(3) 0.000(3) C19 0.057(6) 0.040(5) 0.032(4) -0.010(3) 0.028(4) -0.016(4) C20 0.063(7) 0.048(5) 0.032(4) -0.010(4) 0.019(5) -0.021(5) C21 0.040(5) 0.053(6) 0.025(4) -0.005(4) 0.006(4) -0.015(4) C22 0.038(5) 0.041(4) 0.025(3) 0.005(3) 0.017(3) 0.004(4) C23 0.045(5) 0.055(6) 0.032(4) 0.009(4) 0.015(4) 0.004(4) C24 0.042(5) 0.056(6) 0.046(5) 0.007(4) 0.017(4) 0.017(5) C25 0.073(7) 0.039(5) 0.049(5) 0.011(4) 0.039(5) 0.016(5) C26 0.054(5) 0.034(4) 0.032(4) 0.004(3) 0.023(4) 0.000(4) C27 0.044(5) 0.037(4) 0.021(3) 0.001(3) 0.016(3) -0.008(4) C28 0.054(6) 0.042(5) 0.024(4) -0.001(3) 0.017(4) 0.002(4) C29 0.056(6) 0.049(5) 0.029(4) -0.010(4) 0.013(4) -0.003(5) C30 0.037(5) 0.038(5) 0.048(5) -0.017(4) 0.009(4) -0.005(4) C31 0.042(5) 0.029(4) 0.035(4) 0.005(3) 0.019(4) 0.003(4) C32 0.038(5) 0.039(5) 0.046(4) 0.011(4) 0.020(4) 0.001(4) C33 0.038(5) 0.058(6) 0.056(5) 0.006(4) 0.029(5) -0.004(5) C34 0.058(6) 0.059(6) 0.048(5) 0.006(4) 0.036(5) 0.007(5) C35 0.039(5) 0.042(5) 0.032(4) 0.005(3) 0.019(4) 0.004(4) C36 0.034(4) 0.025(4) 0.029(4) 0.000(3) 0.012(3) -0.005(3) Ir 0.0311(2) 0.02885(18) 0.02177(18) 0.00032(11) 0.01324(14) -0.00124(14) N1 0.028(3) 0.032(3) 0.022(3) -0.005(2) 0.012(3) -0.003(3) N2 0.032(4) 0.033(4) 0.028(3) -0.001(3) 0.018(3) -0.002(3) N3 0.028(3) 0.037(4) 0.027(3) 0.003(3) 0.014(3) -0.003(3) N4 0.036(4) 0.036(4) 0.029(3) 0.000(3) 0.011(3) -0.001(3) N5 0.032(4) 0.035(4) 0.030(3) 0.001(3) 0.014(3) 0.003(3) N6 0.037(4) 0.036(4) 0.031(3) 0.001(3) 0.015(3) 0.001(3) P1 0.0299(15) 0.0327(15) 0.0330(14) 0.0023(11) 0.0156(12) 0.0027(12) F1 0.054(3) 0.038(3) 0.055(3) 0.009(2) 0.025(3) 0.011(2) F2 0.102(6) 0.076(4) 0.038(3) -0.004(3) 0.011(3) 0.041(4) F3 0.050(4) 0.075(4) 0.149(6) 0.041(5) 0.062(4) 0.009(4) _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 C1 C2 1.351(11) . ? C1 N1 1.368(10) . ? C1 H1 0.9300 . ? C2 C18 1.423(11) . ? C2 H2 0.9300 . ? C3 C4 1.365(13) . ? C3 C18 1.418(11) . ? C3 H3 0.9300 . ? C4 C5 1.387(12) . ? C4 H4 0.9300 . ? C5 C14 1.381(10) . ? C5 H5 0.9300 . ? C6 C15 1.386(11) . ? C6 C7 1.384(12) . ? C6 H6 0.9300 . ? C7 C8 1.362(12) . ? C7 H7 0.9300 . ? C8 C17 1.405(11) . ? C8 H8 0.9300 . ? C9 C10 1.351(12) . ? C9 C17 1.423(11) . ? C9 H9 0.9300 . ? C10 N2 1.373(10) . ? C10 H10 0.9300 . ? C11 N2 1.340(9) . ? C11 C16 1.394(10) . ? C11 C12 1.455(11) . ? C12 N1 1.336(9) . ? C12 C13 1.412(10) . ? C13 C14 1.422(11) . ? C13 C18 1.414(11) . ? C14 C15 1.485(11) . ? C15 C16 1.412(10) . ? C16 C17 1.431(11) . ? C19 N3 1.319(10) . ? C19 C20 1.377(14) . ? C19 H19 0.9300 . ? C20 C21 1.365(13) . ? C20 H20 0.9300 . ? C21 N4 1.331(10) . ? C21 H21 0.9300 . ? C22 C27 1.398(11) . ? C22 C23 1.390(12) . ? C22 N4 1.441(10) . ? C23 C24 1.374(13) . ? C23 H23 0.9300 . ? C24 C25 1.378(14) . ? C24 H24 0.9300 . ? C25 C26 1.377(12) . ? C25 H25 0.9300 . ? C26 C27 1.399(11) . ? C26 H26 0.9300 . ? C27 Ir 2.018(8) . ? C28 N5 1.343(9) . ? C28 C29 1.391(13) . ? C28 H28 0.9300 . ? C29 C30 1.365(13) . ? C29 H29 0.9300 . ? C30 N6 1.339(10) . ? C30 H30 0.9300 . ? C31 C32 1.373(11) . ? C31 C36 1.406(11) . ? C31 N6 1.416(9) . ? C32 C33 1.364(12) . ? C32 H32 0.9300 . ? C33 C34 1.379(13) . ? C33 H33 0.9300 . ? C34 C35 1.399(12) . ? C34 H34 0.9300 . ? C35 C36 1.389(10) . ? C35 H35 0.9300 . ? C36 Ir 2.022(8) . ? Ir N5 2.011(6) . ? Ir N3 2.033(6) . ? Ir N2 2.142(6) . ? Ir N1 2.136(6) . ? N3 N4 1.370(9) . ? N5 N6 1.365(9) . ? P1 F2 1.581(5) 5_565 ? P1 F2 1.581(5) . ? P1 F3 1.586(6) 5_565 ? P1 F3 1.586(6) . ? P1 F1 1.598(5) . ? P1 F1 1.598(5) 5_565 ? P2 F6 1.557(10) . ? P2 F6 1.557(10) 2 ? P2 F7 1.538(15) . ? P2 F4 1.566(11) . ? P2 F5 1.593(7) . ? P2 F5 1.593(7) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 122.4(7) . . ? C2 C1 H1 118.8 . . ? N1 C1 H1 118.8 . . ? C1 C2 C18 120.3(8) . . ? C1 C2 H2 119.9 . . ? C18 C2 H2 119.9 . . ? C4 C3 C18 118.4(8) . . ? C4 C3 H3 120.8 . . ? C18 C3 H3 120.8 . . ? C3 C4 C5 122.7(7) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C4 C5 C14 121.1(8) . . ? C4 C5 H5 119.4 . . ? C14 C5 H5 119.4 . . ? C15 C6 C7 121.6(7) . . ? C15 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 121.2(8) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C17 120.0(8) . . ? C7 C8 H8 120.0 . . ? C17 C8 H8 120.0 . . ? C10 C9 C17 120.0(8) . . ? C10 C9 H9 120.0 . . ? C17 C9 H9 120.0 . . ? C9 C10 N2 123.4(7) . . ? C9 C10 H10 118.3 . . ? N2 C10 H10 118.3 . . ? N2 C11 C16 123.6(7) . . ? N2 C11 C12 116.0(6) . . ? C16 C11 C12 120.5(6) . . ? N1 C12 C13 123.3(7) . . ? N1 C12 C11 117.7(6) . . ? C13 C12 C11 119.0(6) . . ? C12 C13 C14 121.3(7) . . ? C12 C13 C18 117.6(7) . . ? C14 C13 C18 121.1(7) . . ? C5 C14 C13 117.5(8) . . ? C5 C14 C15 123.6(7) . . ? C13 C14 C15 118.8(6) . . ? C6 C15 C16 118.3(7) . . ? C6 C15 C14 123.1(7) . . ? C16 C15 C14 118.6(6) . . ? C11 C16 C17 118.4(7) . . ? C11 C16 C15 121.6(7) . . ? C17 C16 C15 119.9(7) . . ? C8 C17 C16 119.0(7) . . ? C8 C17 C9 124.1(8) . . ? C16 C17 C9 116.9(7) . . ? C3 C18 C13 119.1(7) . . ? C3 C18 C2 123.1(8) . . ? C13 C18 C2 117.8(6) . . ? N3 C19 C20 110.1(9) . . ? N3 C19 H19 125.0 . . ? C20 C19 H19 125.0 . . ? C21 C20 C19 105.9(8) . . ? C21 C20 H20 127.1 . . ? C19 C20 H20 127.1 . . ? N4 C21 C20 108.1(8) . . ? N4 C21 H21 126.0 . . ? C20 C21 H21 126.0 . . ? C27 C22 C23 124.8(8) . . ? C27 C22 N4 114.1(7) . . ? C23 C22 N4 121.1(8) . . ? C24 C23 C22 117.3(9) . . ? C24 C23 H23 121.3 . . ? C22 C23 H23 121.3 . . ? C23 C24 C25 120.5(9) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 120.7(9) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 121.9(9) . . ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C22 C27 C26 114.7(8) . . ? C22 C27 Ir 114.5(6) . . ? C26 C27 Ir 130.8(6) . . ? N5 C28 C29 109.4(8) . . ? N5 C28 H28 125.3 . . ? C29 C28 H28 125.3 . . ? C30 C29 C28 105.9(7) . . ? C30 C29 H29 127.1 . . ? C28 C29 H29 127.1 . . ? N6 C30 C29 108.5(8) . . ? N6 C30 H30 125.8 . . ? C29 C30 H30 125.8 . . ? C32 C31 C36 122.7(7) . . ? C32 C31 N6 122.8(8) . . ? C36 C31 N6 114.5(7) . . ? C33 C32 C31 120.2(8) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 118.9(8) . . ? C32 C33 H33 120.5 . . ? C34 C33 H33 120.5 . . ? C33 C34 C35 121.4(8) . . ? C33 C34 H34 119.3 . . ? C35 C34 H34 119.3 . . ? C34 C35 C36 120.3(8) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C31 C36 C35 116.5(7) . . ? C31 C36 Ir 114.3(5) . . ? C35 C36 Ir 129.1(6) . . ? N5 Ir C27 95.1(3) . . ? N5 Ir C36 79.8(3) . . ? C27 Ir C36 91.5(3) . . ? N5 Ir N3 174.0(2) . . ? C27 Ir N3 79.8(3) . . ? C36 Ir N3 97.1(3) . . ? N5 Ir N2 86.2(2) . . ? C27 Ir N2 173.0(3) . . ? C36 Ir N2 95.6(3) . . ? N3 Ir N2 99.2(2) . . ? N5 Ir N1 92.9(2) . . ? C27 Ir N1 96.1(3) . . ? C36 Ir N1 170.0(3) . . ? N3 Ir N1 90.8(2) . . ? N2 Ir N1 77.0(2) . . ? C12 N1 C1 118.6(6) . . ? C12 N1 Ir 113.5(5) . . ? C1 N1 Ir 127.5(5) . . ? C11 N2 C10 117.6(6) . . ? C11 N2 Ir 114.2(5) . . ? C10 N2 Ir 127.8(5) . . ? C19 N3 N4 106.6(7) . . ? C19 N3 Ir 138.8(6) . . ? N4 N3 Ir 113.9(5) . . ? C21 N4 N3 109.4(7) . . ? C21 N4 C22 134.9(8) . . ? N3 N4 C22 115.1(6) . . ? C28 N5 N6 106.5(7) . . ? C28 N5 Ir 137.6(6) . . ? N6 N5 Ir 115.9(4) . . ? C30 N6 N5 109.7(7) . . ? C30 N6 C31 134.8(8) . . ? N5 N6 C31 115.4(6) . . ? F2 P1 F2 179.997(1) 5_565 . ? F2 P1 F3 89.2(5) 5_565 5_565 ? F2 P1 F3 90.9(5) . 5_565 ? F2 P1 F3 90.8(5) 5_565 . ? F2 P1 F3 89.2(5) . . ? F3 P1 F3 179.997(2) 5_565 . ? F2 P1 F1 89.7(3) 5_565 . ? F2 P1 F1 90.3(3) . . ? F3 P1 F1 90.4(3) 5_565 . ? F3 P1 F1 89.6(3) . . ? F2 P1 F1 90.3(3) 5_565 5_565 ? F2 P1 F1 89.7(3) . 5_565 ? F3 P1 F1 89.6(3) 5_565 5_565 ? F3 P1 F1 90.4(3) . 5_565 ? F1 P1 F1 180.0(4) . 5_565 ? F6 P2 F6 176.3(9) . 2 ? F6 P2 F7 91.9(4) . . ? F6 P2 F7 91.9(4) 2 . ? F6 P2 F4 88.1(4) . . ? F6 P2 F4 88.1(4) 2 . ? F7 P2 F4 180.000(3) . . ? F6 P2 F5 91.4(5) . . ? F6 P2 F5 88.6(5) 2 . ? F7 P2 F5 90.2(3) . . ? F4 P2 F5 89.8(3) . . ? F6 P2 F5 88.6(5) . 2 ? F6 P2 F5 91.4(5) 2 2 ? F7 P2 F5 90.2(3) . 2 ? F4 P2 F5 89.8(3) . 2 ? F5 P2 F5 179.6(6) . 2 ? 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 N1 C1 C2 C18 -2.0(12) . . . . ? C18 C3 C4 C5 0.4(14) . . . . ? C3 C4 C5 C14 0.8(14) . . . . ? C15 C6 C7 C8 1.9(13) . . . . ? C6 C7 C8 C17 -1.9(13) . . . . ? C17 C9 C10 N2 2.8(13) . . . . ? N2 C11 C12 N1 -1.1(10) . . . . ? C16 C11 C12 N1 179.6(7) . . . . ? N2 C11 C12 C13 -179.2(6) . . . . ? C16 C11 C12 C13 1.4(11) . . . . ? N1 C12 C13 C14 179.1(7) . . . . ? C11 C12 C13 C14 -2.9(11) . . . . ? N1 C12 C13 C18 -0.3(11) . . . . ? C11 C12 C13 C18 177.7(7) . . . . ? C4 C5 C14 C13 -2.3(12) . . . . ? C4 C5 C14 C15 180.0(8) . . . . ? C12 C13 C14 C5 -176.8(7) . . . . ? C18 C13 C14 C5 2.6(11) . . . . ? C12 C13 C14 C15 1.0(11) . . . . ? C18 C13 C14 C15 -179.6(7) . . . . ? C7 C6 C15 C16 -1.0(12) . . . . ? C7 C6 C15 C14 -178.3(8) . . . . ? C5 C14 C15 C6 -2.6(12) . . . . ? C13 C14 C15 C6 179.7(7) . . . . ? C5 C14 C15 C16 -180.0(7) . . . . ? C13 C14 C15 C16 2.3(10) . . . . ? N2 C11 C16 C17 1.2(11) . . . . ? C12 C11 C16 C17 -179.5(7) . . . . ? N2 C11 C16 C15 -177.3(7) . . . . ? C12 C11 C16 C15 2.0(11) . . . . ? C6 C15 C16 C11 178.7(7) . . . . ? C14 C15 C16 C11 -3.8(11) . . . . ? C6 C15 C16 C17 0.2(11) . . . . ? C14 C15 C16 C17 177.7(7) . . . . ? C7 C8 C17 C16 1.2(12) . . . . ? C7 C8 C17 C9 -179.7(8) . . . . ? C11 C16 C17 C8 -178.8(7) . . . . ? C15 C16 C17 C8 -0.3(11) . . . . ? C11 C16 C17 C9 2.0(11) . . . . ? C15 C16 C17 C9 -179.5(7) . . . . ? C10 C9 C17 C8 177.0(8) . . . . ? C10 C9 C17 C16 -3.9(12) . . . . ? C4 C3 C18 C13 -0.1(12) . . . . ? C4 C3 C18 C2 179.8(8) . . . . ? C12 C13 C18 C3 178.0(7) . . . . ? C14 C13 C18 C3 -1.4(11) . . . . ? C12 C13 C18 C2 -1.9(11) . . . . ? C14 C13 C18 C2 178.7(7) . . . . ? C1 C2 C18 C3 -176.9(8) . . . . ? C1 C2 C18 C13 3.1(12) . . . . ? N3 C19 C20 C21 0.4(10) . . . . ? C19 C20 C21 N4 -0.8(10) . . . . ? C27 C22 C23 C24 -2.8(12) . . . . ? N4 C22 C23 C24 176.4(8) . . . . ? C22 C23 C24 C25 1.9(13) . . . . ? C23 C24 C25 C26 -0.8(14) . . . . ? C24 C25 C26 C27 0.4(13) . . . . ? C23 C22 C27 C26 2.3(11) . . . . ? N4 C22 C27 C26 -176.9(6) . . . . ? C23 C22 C27 Ir -175.5(6) . . . . ? N4 C22 C27 Ir 5.3(8) . . . . ? C25 C26 C27 C22 -1.1(11) . . . . ? C25 C26 C27 Ir 176.3(6) . . . . ? N5 C28 C29 C30 -1.3(10) . . . . ? C28 C29 C30 N6 0.7(10) . . . . ? C36 C31 C32 C33 2.6(13) . . . . ? N6 C31 C32 C33 -178.6(8) . . . . ? C31 C32 C33 C34 -2.1(14) . . . . ? C32 C33 C34 C35 0.5(14) . . . . ? C33 C34 C35 C36 0.9(14) . . . . ? C32 C31 C36 C35 -1.2(12) . . . . ? N6 C31 C36 C35 179.9(7) . . . . ? C32 C31 C36 Ir -177.3(7) . . . . ? N6 C31 C36 Ir 3.9(9) . . . . ? C34 C35 C36 C31 -0.5(12) . . . . ? C34 C35 C36 Ir 174.9(7) . . . . ? C22 C27 Ir N5 172.4(5) . . . . ? C26 C27 Ir N5 -4.9(8) . . . . ? C22 C27 Ir C36 -107.7(6) . . . . ? C26 C27 Ir C36 74.9(8) . . . . ? C22 C27 Ir N3 -10.7(5) . . . . ? C26 C27 Ir N3 171.9(8) . . . . ? C22 C27 Ir N2 72(2) . . . . ? C26 C27 Ir N2 -106(2) . . . . ? C22 C27 Ir N1 79.0(6) . . . . ? C26 C27 Ir N1 -98.4(7) . . . . ? C31 C36 Ir N5 -2.4(6) . . . . ? C35 C36 Ir N5 -177.8(8) . . . . ? C31 C36 Ir C27 -97.3(6) . . . . ? C35 C36 Ir C27 87.2(8) . . . . ? C31 C36 Ir N3 -177.2(6) . . . . ? C35 C36 Ir N3 7.3(8) . . . . ? C31 C36 Ir N2 82.8(6) . . . . ? C35 C36 Ir N2 -92.7(8) . . . . ? C31 C36 Ir N1 41.1(18) . . . . ? C35 C36 Ir N1 -134.4(13) . . . . ? C13 C12 N1 C1 1.5(10) . . . . ? C11 C12 N1 C1 -176.6(7) . . . . ? C13 C12 N1 Ir -171.6(5) . . . . ? C11 C12 N1 Ir 10.4(8) . . . . ? C2 C1 N1 C12 -0.3(11) . . . . ? C2 C1 N1 Ir 171.7(6) . . . . ? N5 Ir N1 C12 74.3(5) . . . . ? C27 Ir N1 C12 169.8(5) . . . . ? C36 Ir N1 C12 31.6(17) . . . . ? N3 Ir N1 C12 -110.4(5) . . . . ? N2 Ir N1 C12 -11.1(5) . . . . ? N5 Ir N1 C1 -98.0(6) . . . . ? C27 Ir N1 C1 -2.5(6) . . . . ? C36 Ir N1 C1 -140.7(14) . . . . ? N3 Ir N1 C1 77.3(6) . . . . ? N2 Ir N1 C1 176.6(6) . . . . ? C16 C11 N2 C10 -2.5(11) . . . . ? C12 C11 N2 C10 178.2(7) . . . . ? C16 C11 N2 Ir 170.6(6) . . . . ? C12 C11 N2 Ir -8.8(8) . . . . ? C9 C10 N2 C11 0.4(12) . . . . ? C9 C10 N2 Ir -171.5(6) . . . . ? N5 Ir N2 C11 -83.1(5) . . . . ? C27 Ir N2 C11 18(2) . . . . ? C36 Ir N2 C11 -162.5(5) . . . . ? N3 Ir N2 C11 99.4(5) . . . . ? N1 Ir N2 C11 10.7(5) . . . . ? N5 Ir N2 C10 89.0(7) . . . . ? C27 Ir N2 C10 -169.6(19) . . . . ? C36 Ir N2 C10 9.7(7) . . . . ? N3 Ir N2 C10 -88.5(7) . . . . ? N1 Ir N2 C10 -177.1(7) . . . . ? C20 C19 N3 N4 0.1(9) . . . . ? C20 C19 N3 Ir -168.9(6) . . . . ? N5 Ir N3 C19 -145(2) . . . . ? C27 Ir N3 C19 -176.8(8) . . . . ? C36 Ir N3 C19 -86.6(8) . . . . ? N2 Ir N3 C19 10.2(8) . . . . ? N1 Ir N3 C19 87.2(8) . . . . ? N5 Ir N3 N4 47(3) . . . . ? C27 Ir N3 N4 14.7(5) . . . . ? C36 Ir N3 N4 104.9(5) . . . . ? N2 Ir N3 N4 -158.2(5) . . . . ? N1 Ir N3 N4 -81.3(5) . . . . ? C20 C21 N4 N3 0.9(9) . . . . ? C20 C21 N4 C22 -169.3(8) . . . . ? C19 N3 N4 C21 -0.6(8) . . . . ? Ir N3 N4 C21 171.5(5) . . . . ? C19 N3 N4 C22 171.7(6) . . . . ? Ir N3 N4 C22 -16.2(7) . . . . ? C27 C22 N4 C21 177.0(8) . . . . ? C23 C22 N4 C21 -2.3(14) . . . . ? C27 C22 N4 N3 7.3(9) . . . . ? C23 C22 N4 N3 -172.0(7) . . . . ? C29 C28 N5 N6 1.3(9) . . . . ? C29 C28 N5 Ir -178.8(6) . . . . ? C27 Ir N5 C28 -88.9(9) . . . . ? C36 Ir N5 C28 -179.4(9) . . . . ? N3 Ir N5 C28 -120(2) . . . . ? N2 Ir N5 C28 84.2(8) . . . . ? N1 Ir N5 C28 7.5(8) . . . . ? C27 Ir N5 N6 91.0(5) . . . . ? C36 Ir N5 N6 0.5(5) . . . . ? N3 Ir N5 N6 60(3) . . . . ? N2 Ir N5 N6 -95.9(5) . . . . ? N1 Ir N5 N6 -172.6(5) . . . . ? C29 C30 N6 N5 0.1(10) . . . . ? C29 C30 N6 C31 177.1(9) . . . . ? C28 N5 N6 C30 -0.9(9) . . . . ? Ir N5 N6 C30 179.2(5) . . . . ? C28 N5 N6 C31 -178.6(7) . . . . ? Ir N5 N6 C31 1.5(8) . . . . ? C32 C31 N6 C30 0.7(14) . . . . ? C36 C31 N6 C30 179.6(9) . . . . ? C32 C31 N6 N5 177.6(7) . . . . ? C36 C31 N6 N5 -3.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.206 _refine_diff_density_min -1.808 _refine_diff_density_rms 0.169 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 1 0.000 0.000 -0.002 437.4 92.0 2 0.500 0.500 0.245 437.4 92.0 _chemical_name_common ;Bis(1-phenylpyrazole)(1,12-diazaperylene)iridium(iii)- hexafluorophosphate ; #====================================================================== data_pit7iw1 _database_code_depnum_ccdc_archive 'CCDC 827356' #TrackingRef '- pit7iw1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2-(2-pyridyl)phenyl)(2,11-dimethyl-1,12-diazaperylene)iridium(III)- hexafluorophosphate ; _chemical_melting_point '> 633' _chemical_formula_moiety 'C42 H30 Ir N4 1+, F6 P 1-' _chemical_formula_sum 'C42 H30 F6 Ir N4 P' _chemical_formula_weight 927.87 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 26.3013(16) _cell_length_b 13.0436(9) _cell_length_c 24.8890(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.398(4) _cell_angle_gamma 90.00 _cell_volume 8232.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 24511 _cell_measurement_theta_min 1.56 _cell_measurement_theta_max 28.81 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method ? _exptl_crystal_F_000 3648 _exptl_absorpt_coefficient_mu 3.343 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.4033 _exptl_absorpt_correction_T_max 0.4163 _exptl_absorpt_process_details ; The value of _exptl_absorpt_correction_T_max was calculated from the crystal dimensions and absorption coefficient. The value of exptl absorpt correction T min was derived from *_T_max and the ratio of minimum to maximum apparent transmission given by X-RED32 (Stoe, 2002). ; _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source ; sealed X-ray tube, 12 x 0.4 mm long-fine focus ; _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_source_power 2.00 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 210(2) _diffrn_measurement_method 'rotation method, delta omega = 1.0 deg' _diffrn_measurement_details ; 180 frames, detector distance = 100 mm ; _diffrn_reflns_number 26183 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7231 _reflns_number_gt 5285 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All hydrogen atoms were calculated in their expected positions and refined with a riding model. ; _computing_data_collection 'X-AREA (Stoe, 2006)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-RED32 (Stoe, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997) DIAMOND (Brandenburg, 2005) ; _computing_publication_material SHELXL-97 _refine_special_details ; The unit cell contains disordered solvent molecules. In spite of several attempts, no reasonable solution could be received. Therefore the contribution of the disordered solvent species was subtracted from the structure factor calculation by the SQUEEZE instruction of the PLATON program suite. SQUEEZE calculated 1949.6 \%A as solvent-accessible void volume and a number of electrons of 485 per cell. In consideration of Z these values correspond roughly with one molecule of chloroform per asymmetric unit. The PF6 anion was refined isotropically using a disorder model by means of the restraint instructions SADI and SAME. ; _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^)+(0.0714P)^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 SHELXL _refine_ls_extinction_coef 0.00027(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7231 _refine_ls_number_parameters 469 _refine_ls_number_restraints 115 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.975 _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 C1 C 0.1863(3) 0.5111(5) 0.4394(3) 0.0512(17) Uani 1 1 d . . . C2 C 0.1713(3) 0.4892(6) 0.4865(4) 0.064(2) Uani 1 1 d . . . H2 H 0.1381 0.5102 0.4886 0.076 Uiso 1 1 calc R . . C3 C 0.1881(4) 0.4157(7) 0.5815(4) 0.077(2) Uani 1 1 d . . . H3 H 0.1559 0.4384 0.5857 0.092 Uiso 1 1 calc R . . C4 C 0.2219(5) 0.3615(7) 0.6228(4) 0.090(3) Uani 1 1 d . . . H4 H 0.2125 0.3488 0.6557 0.108 Uiso 1 1 calc R . . C5 C 0.2696(4) 0.3248(6) 0.6171(3) 0.075(2) Uani 1 1 d . . . H5 H 0.2917 0.2888 0.6464 0.090 Uiso 1 1 calc R . . C6 C 0.3685(4) 0.2371(6) 0.5994(4) 0.075(2) Uani 1 1 d . . . H6 H 0.3606 0.2212 0.6326 0.090 Uiso 1 1 calc R . . C7 C 0.4141(4) 0.1982(7) 0.5887(4) 0.084(3) Uani 1 1 d . . . H7 H 0.4366 0.1575 0.6153 0.100 Uiso 1 1 calc R . . C8 C 0.4262(4) 0.2182(6) 0.5408(4) 0.078(3) Uani 1 1 d . . . H8 H 0.4565 0.1896 0.5343 0.094 Uiso 1 1 calc R . . C9 C 0.4040(3) 0.3071(5) 0.4490(3) 0.0590(19) Uani 1 1 d . . . H9 H 0.4335 0.2792 0.4406 0.071 Uiso 1 1 calc R . . C10 C 0.3718(3) 0.3714(5) 0.4112(3) 0.0522(17) Uani 1 1 d . . . C11 C 0.3159(3) 0.3889(4) 0.4699(3) 0.0466(16) Uani 1 1 d . . . C12 C 0.2663(3) 0.4271(5) 0.4776(3) 0.0472(16) Uani 1 1 d . . . C13 C 0.2513(3) 0.4005(5) 0.5258(3) 0.0528(17) Uani 1 1 d . . . C14 C 0.2847(3) 0.3406(5) 0.5694(3) 0.0581(18) Uani 1 1 d . . . C15 C 0.3346(3) 0.3001(5) 0.5603(3) 0.0578(18) Uani 1 1 d . . . C16 C 0.3472(3) 0.3239(5) 0.5104(3) 0.0535(17) Uani 1 1 d . . . C17 C 0.3936(3) 0.2826(5) 0.4996(3) 0.0591(19) Uani 1 1 d . . . C18 C 0.2033(3) 0.4368(5) 0.5317(3) 0.0616(19) Uani 1 1 d . . . C19 C 0.1497(3) 0.5598(6) 0.3901(3) 0.065(2) Uani 1 1 d . . . H19A H 0.1385 0.6251 0.4006 0.078 Uiso 1 1 calc R . . H19B H 0.1195 0.5165 0.3766 0.078 Uiso 1 1 calc R . . H19C H 0.1674 0.5691 0.3614 0.078 Uiso 1 1 calc R . . C20 C 0.3846(3) 0.3921(6) 0.3574(3) 0.0596(19) Uani 1 1 d . . . H20A H 0.3846 0.3287 0.3377 0.072 Uiso 1 1 calc R . . H20B H 0.4188 0.4234 0.3646 0.072 Uiso 1 1 calc R . . H20C H 0.3586 0.4374 0.3351 0.072 Uiso 1 1 calc R . . C21 C 0.2387(3) 0.3879(5) 0.2967(3) 0.0547(18) Uani 1 1 d . . . H21 H 0.2620 0.3438 0.3204 0.066 Uiso 1 1 calc R . . C22 C 0.2089(3) 0.3514(6) 0.2478(3) 0.067(2) Uani 1 1 d . . . H22 H 0.2124 0.2835 0.2379 0.080 Uiso 1 1 calc R . . C23 C 0.1728(4) 0.4160(7) 0.2120(4) 0.077(2) Uani 1 1 d . . . H23 H 0.1518 0.3924 0.1781 0.092 Uiso 1 1 calc R . . C24 C 0.1695(3) 0.5143(6) 0.2284(3) 0.0601(19) Uani 1 1 d . . . H24 H 0.1450 0.5578 0.2056 0.072 Uiso 1 1 calc R . . C25 C 0.2012(3) 0.5517(5) 0.2776(3) 0.0531(16) Uani 1 1 d . . . C26 C 0.2028(3) 0.6564(5) 0.2992(3) 0.0526(16) Uani 1 1 d . . . C27 C 0.1681(3) 0.7335(6) 0.2721(3) 0.066(2) Uani 1 1 d . . . H27 H 0.1433 0.7200 0.2385 0.079 Uiso 1 1 calc R . . C28 C 0.1716(4) 0.8297(6) 0.2960(4) 0.073(2) Uani 1 1 d . . . H28 H 0.1487 0.8813 0.2785 0.088 Uiso 1 1 calc R . . C29 C 0.2086(3) 0.8497(6) 0.3453(4) 0.071(2) Uani 1 1 d . . . H29 H 0.2112 0.9154 0.3603 0.085 Uiso 1 1 calc R . . C30 C 0.2421(3) 0.7733(5) 0.3730(3) 0.0597(18) Uani 1 1 d . . . H30 H 0.2661 0.7876 0.4070 0.072 Uiso 1 1 calc R . . C31 C 0.2400(3) 0.6744(5) 0.3501(3) 0.0478(15) Uani 1 1 d . . . C32 C 0.3254(3) 0.6468(6) 0.4973(3) 0.0623(19) Uani 1 1 d . . . H32 H 0.2968 0.6150 0.5058 0.075 Uiso 1 1 calc R . . C33 C 0.3587(4) 0.7046(7) 0.5375(4) 0.082(3) Uani 1 1 d . . . H33 H 0.3535 0.7108 0.5729 0.098 Uiso 1 1 calc R . . C34 C 0.4005(4) 0.7536(8) 0.5244(5) 0.097(3) Uani 1 1 d . . . H34 H 0.4240 0.7931 0.5508 0.117 Uiso 1 1 calc R . . C35 C 0.4064(3) 0.7430(7) 0.4718(4) 0.079(3) Uani 1 1 d . . . H35 H 0.4339 0.7770 0.4623 0.094 Uiso 1 1 calc R . . C36 C 0.3725(3) 0.6826(5) 0.4325(3) 0.0582(19) Uani 1 1 d . . . C37 C 0.3746(3) 0.6671(5) 0.3756(4) 0.063(2) Uani 1 1 d . . . C38 C 0.4150(3) 0.7054(6) 0.3542(5) 0.076(2) Uani 1 1 d . . . H38 H 0.4425 0.7427 0.3771 0.091 Uiso 1 1 calc R . . C39 C 0.4143(4) 0.6882(7) 0.2999(5) 0.092(3) Uani 1 1 d . . . H39 H 0.4413 0.7133 0.2859 0.111 Uiso 1 1 calc R . . C40 C 0.3732(4) 0.6330(7) 0.2660(4) 0.078(3) Uani 1 1 d . . . H40 H 0.3724 0.6227 0.2288 0.093 Uiso 1 1 calc R . . C41 C 0.3332(3) 0.5927(6) 0.2863(3) 0.0594(18) Uani 1 1 d . . . H41 H 0.3060 0.5560 0.2627 0.071 Uiso 1 1 calc R . . C42 C 0.3334(3) 0.6070(5) 0.3422(3) 0.0581(18) Uani 1 1 d . . . Ir Ir 0.283007(10) 0.550766(17) 0.382731(10) 0.04367(12) Uani 1 1 d . . . N1 N 0.2365(2) 0.4864(4) 0.4369(2) 0.0456(13) Uani 1 1 d . . . N2 N 0.3290(2) 0.4159(4) 0.4224(2) 0.0431(12) Uani 1 1 d . . . N3 N 0.2358(2) 0.4871(4) 0.3127(2) 0.0488(13) Uani 1 1 d . . . N4 N 0.3321(2) 0.6339(4) 0.4460(3) 0.0521(14) Uani 1 1 d . . . P P 0.47298(11) 0.0516(2) 0.39862(12) 0.0874(7) Uiso 1 1 d D . . F4 F 0.4868(3) 0.1312(5) 0.4473(3) 0.125(2) Uiso 1 1 d D A . F6 F 0.4580(3) -0.0282(6) 0.3506(4) 0.176(3) Uiso 1 1 d D A . F1A F 0.5255(4) -0.0058(8) 0.4279(4) 0.135(3) Uiso 0.70 1 d PD A 1 F2A F 0.4220(3) 0.1172(5) 0.3701(3) 0.089(2) Uiso 0.70 1 d PD A 1 F3A F 0.5049(4) 0.1173(8) 0.3662(4) 0.137(4) Uiso 0.70 1 d PD A 1 F5A F 0.4415(5) -0.0094(10) 0.4328(5) 0.181(5) Uiso 0.70 1 d PD A 1 F1B F 0.4973(10) -0.0402(16) 0.4394(7) 0.208(16) Uiso 0.30 1 d PD A 2 F2B F 0.4437(8) 0.1345(10) 0.3529(7) 0.116(7) Uiso 0.30 1 d PD A 2 F3B F 0.5250(5) 0.0655(15) 0.3816(8) 0.116(7) Uiso 0.30 1 d PD A 2 F5B F 0.4172(7) 0.0290(19) 0.4102(10) 0.201(15) Uiso 0.30 1 d PD 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 C1 0.052(4) 0.038(3) 0.069(5) -0.004(3) 0.024(4) -0.003(3) C2 0.058(4) 0.054(4) 0.084(6) -0.001(4) 0.028(4) -0.003(4) C3 0.104(7) 0.059(5) 0.083(6) -0.005(5) 0.050(6) -0.001(5) C4 0.144(9) 0.064(6) 0.076(6) 0.003(5) 0.056(7) -0.010(6) C5 0.122(8) 0.049(4) 0.059(5) 0.003(4) 0.030(5) -0.001(5) C6 0.100(7) 0.054(4) 0.062(5) 0.006(4) 0.009(5) 0.004(5) C7 0.103(7) 0.068(5) 0.069(6) 0.018(4) 0.003(5) 0.020(5) C8 0.079(6) 0.061(5) 0.088(6) 0.022(4) 0.012(5) 0.023(4) C9 0.050(4) 0.049(4) 0.073(5) 0.006(4) 0.007(4) 0.006(3) C10 0.054(4) 0.036(3) 0.065(4) -0.003(3) 0.013(3) 0.004(3) C11 0.050(4) 0.031(3) 0.052(4) -0.006(3) 0.003(3) -0.005(3) C12 0.054(4) 0.034(3) 0.051(4) -0.005(3) 0.010(3) -0.007(3) C13 0.070(5) 0.031(3) 0.059(4) -0.007(3) 0.020(4) -0.010(3) C14 0.078(5) 0.037(3) 0.054(4) -0.002(3) 0.010(4) -0.003(3) C15 0.076(5) 0.038(3) 0.055(4) 0.001(3) 0.010(4) -0.002(3) C16 0.068(4) 0.032(3) 0.056(4) 0.001(3) 0.007(3) -0.005(3) C17 0.058(4) 0.044(4) 0.070(5) 0.007(3) 0.006(4) 0.009(3) C18 0.084(5) 0.041(4) 0.068(5) -0.007(3) 0.035(4) -0.015(4) C19 0.049(4) 0.069(5) 0.076(5) 0.003(4) 0.015(4) 0.004(4) C20 0.056(4) 0.053(4) 0.070(5) -0.004(4) 0.016(4) 0.007(3) C21 0.061(4) 0.038(3) 0.060(4) -0.007(3) 0.009(4) 0.000(3) C22 0.079(5) 0.050(4) 0.069(5) -0.015(4) 0.014(4) -0.004(4) C23 0.084(6) 0.078(6) 0.065(5) -0.019(4) 0.013(5) -0.018(5) C24 0.059(4) 0.069(5) 0.047(4) 0.008(4) 0.003(3) -0.001(4) C25 0.057(4) 0.048(4) 0.054(4) 0.009(3) 0.014(3) -0.005(3) C26 0.056(4) 0.041(3) 0.063(4) 0.006(3) 0.021(3) 0.005(3) C27 0.061(4) 0.067(5) 0.068(5) 0.016(4) 0.012(4) 0.010(4) C28 0.085(6) 0.050(4) 0.089(6) 0.020(4) 0.031(5) 0.021(4) C29 0.085(6) 0.039(4) 0.094(6) -0.001(4) 0.032(5) 0.012(4) C30 0.066(5) 0.041(4) 0.074(5) -0.002(3) 0.024(4) 0.003(3) C31 0.054(4) 0.033(3) 0.061(4) 0.003(3) 0.024(3) -0.004(3) C32 0.073(5) 0.051(4) 0.059(4) -0.007(4) 0.012(4) -0.013(4) C33 0.089(6) 0.073(5) 0.075(6) -0.032(5) 0.006(5) -0.022(5) C34 0.079(6) 0.099(7) 0.106(8) -0.054(6) 0.011(6) -0.028(6) C35 0.063(5) 0.060(5) 0.110(7) -0.021(5) 0.016(5) -0.016(4) C36 0.053(4) 0.039(3) 0.080(5) -0.005(3) 0.013(4) -0.005(3) C37 0.054(4) 0.046(4) 0.095(6) 0.002(4) 0.029(4) 0.002(3) C38 0.068(5) 0.057(5) 0.115(8) -0.001(5) 0.046(5) -0.006(4) C39 0.079(6) 0.072(6) 0.145(10) 0.009(6) 0.063(7) -0.005(5) C40 0.093(6) 0.064(5) 0.092(6) 0.018(5) 0.054(6) 0.025(5) C41 0.068(5) 0.052(4) 0.063(5) 0.010(4) 0.026(4) 0.011(4) C42 0.061(4) 0.039(4) 0.079(5) 0.002(3) 0.028(4) 0.011(3) Ir 0.04797(17) 0.03005(14) 0.05184(17) -0.00059(11) 0.01127(11) 0.00008(11) N1 0.051(3) 0.032(2) 0.054(3) -0.001(2) 0.015(3) -0.001(2) N2 0.046(3) 0.029(2) 0.054(3) -0.002(2) 0.011(3) 0.005(2) N3 0.051(3) 0.035(3) 0.059(3) 0.001(2) 0.013(3) 0.001(2) N4 0.052(3) 0.035(3) 0.068(4) -0.003(3) 0.013(3) -0.002(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 C1 C2 1.365(11) . ? C1 N1 1.376(9) . ? C1 C19 1.485(10) . ? C2 C18 1.392(11) . ? C2 H2 0.9300 . ? C3 C4 1.364(13) . ? C3 C18 1.424(11) . ? C3 H3 0.9300 . ? C4 C5 1.385(13) . ? C4 H4 0.9300 . ? C5 C14 1.366(11) . ? C5 H5 0.9300 . ? C6 C15 1.398(10) . ? C6 C7 1.392(13) . ? C6 H6 0.9300 . ? C7 C8 1.339(13) . ? C7 H7 0.9300 . ? C8 C17 1.422(10) . ? C8 H8 0.9300 . ? C9 C10 1.372(9) . ? C9 C17 1.394(11) . ? C9 H9 0.9300 . ? C10 N2 1.360(8) . ? C10 C20 1.491(11) . ? C11 N2 1.362(9) . ? C11 C16 1.404(9) . ? C11 C12 1.456(10) . ? C12 N1 1.348(8) . ? C12 C13 1.403(10) . ? C13 C18 1.393(11) . ? C13 C14 1.434(10) . ? C14 C15 1.485(11) . ? C15 C16 1.405(10) . ? C16 C17 1.424(10) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.347(10) . ? C21 N3 1.362(8) . ? C21 H21 0.9300 . ? C22 C23 1.398(12) . ? C22 H22 0.9300 . ? C23 C24 1.355(11) . ? C23 H23 0.9300 . ? C24 C25 1.374(10) . ? C24 H24 0.9300 . ? C25 N3 1.371(9) . ? C25 C26 1.465(10) . ? C26 C31 1.398(10) . ? C26 C27 1.405(10) . ? C27 C28 1.381(11) . ? C27 H27 0.9300 . ? C28 C29 1.375(12) . ? C28 H28 0.9300 . ? C29 C30 1.385(10) . ? C29 H29 0.9300 . ? C30 C31 1.406(9) . ? C30 H30 0.9300 . ? C31 Ir 2.013(6) . ? C32 N4 1.345(9) . ? C32 C33 1.369(10) . ? C32 H32 0.9300 . ? C33 C34 1.382(13) . ? C33 H33 0.9300 . ? C34 C35 1.365(14) . ? C34 H34 0.9300 . ? C35 C36 1.382(10) . ? C35 H35 0.9300 . ? C36 N4 1.357(9) . ? C36 C37 1.445(11) . ? C37 C38 1.401(11) . ? C37 C42 1.414(11) . ? C38 C39 1.365(14) . ? C38 H38 0.9300 . ? C39 C40 1.384(13) . ? C39 H39 0.9300 . ? C40 C41 1.386(12) . ? C40 H40 0.9300 . ? C41 C42 1.403(11) . ? C41 H41 0.9300 . ? C42 Ir 2.005(8) . ? Ir N3 2.030(6) . ? Ir N4 2.060(6) . ? Ir N2 2.213(5) . ? Ir N1 2.213(6) . ? P F3B 1.547(11) . ? P F6 1.555(8) . ? P F5A 1.555(10) . ? P F4 1.563(7) . ? P F1A 1.570(8) . ? P F3A 1.565(8) . ? P F2A 1.590(7) . ? P F1B 1.590(13) . ? P F5B 1.595(13) . ? P F2B 1.610(11) . ? 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 C2 C1 N1 119.3(7) . . ? C2 C1 C19 121.8(7) . . ? N1 C1 C19 118.9(7) . . ? C1 C2 C18 123.2(7) . . ? C1 C2 H2 118.4 . . ? C18 C2 H2 118.4 . . ? C4 C3 C18 118.7(9) . . ? C4 C3 H3 120.6 . . ? C18 C3 H3 120.6 . . ? C3 C4 C5 121.8(9) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C14 C5 C4 121.2(9) . . ? C14 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C15 C6 C7 120.3(8) . . ? C15 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 121.3(8) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C17 121.1(9) . . ? C7 C8 H8 119.5 . . ? C17 C8 H8 119.5 . . ? C10 C9 C17 121.7(7) . . ? C10 C9 H9 119.1 . . ? C17 C9 H9 119.1 . . ? C9 C10 N2 121.0(7) . . ? C9 C10 C20 118.7(7) . . ? N2 C10 C20 120.3(6) . . ? N2 C11 C16 123.0(6) . . ? N2 C11 C12 117.8(6) . . ? C16 C11 C12 119.2(7) . . ? N1 C12 C13 122.9(7) . . ? N1 C12 C11 117.5(6) . . ? C13 C12 C11 119.6(6) . . ? C18 C13 C12 118.5(7) . . ? C18 C13 C14 119.7(7) . . ? C12 C13 C14 121.7(7) . . ? C5 C14 C13 118.6(8) . . ? C5 C14 C15 123.5(7) . . ? C13 C14 C15 117.9(7) . . ? C6 C15 C16 119.2(8) . . ? C6 C15 C14 122.0(7) . . ? C16 C15 C14 118.8(6) . . ? C15 C16 C11 122.5(7) . . ? C15 C16 C17 120.0(7) . . ? C11 C16 C17 117.5(7) . . ? C9 C17 C8 124.1(8) . . ? C9 C17 C16 117.8(6) . . ? C8 C17 C16 118.1(8) . . ? C13 C18 C2 116.8(7) . . ? C13 C18 C3 119.8(8) . . ? C2 C18 C3 123.3(8) . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 N3 122.4(7) . . ? C22 C21 H21 118.8 . . ? N3 C21 H21 118.8 . . ? C21 C22 C23 119.7(7) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 117.8(7) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? C23 C24 C25 122.1(8) . . ? C23 C24 H24 118.9 . . ? C25 C24 H24 118.9 . . ? N3 C25 C24 119.5(7) . . ? N3 C25 C26 112.9(6) . . ? C24 C25 C26 127.6(7) . . ? C31 C26 C27 121.6(7) . . ? C31 C26 C25 115.8(6) . . ? C27 C26 C25 122.6(7) . . ? C28 C27 C26 118.9(8) . . ? C28 C27 H27 120.6 . . ? C26 C27 H27 120.6 . . ? C29 C28 C27 120.4(7) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C30 120.9(7) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C29 C30 C31 120.5(8) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C26 C31 C30 117.6(6) . . ? C26 C31 Ir 114.5(5) . . ? C30 C31 Ir 127.9(6) . . ? N4 C32 C33 122.8(8) . . ? N4 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C32 C33 C34 118.5(9) . . ? C32 C33 H33 120.8 . . ? C34 C33 H33 120.8 . . ? C33 C34 C35 118.7(8) . . ? C33 C34 H34 120.6 . . ? C35 C34 H34 120.6 . . ? C36 C35 C34 121.4(9) . . ? C36 C35 H35 119.3 . . ? C34 C35 H35 119.3 . . ? N4 C36 C35 119.4(8) . . ? N4 C36 C37 114.4(6) . . ? C35 C36 C37 126.1(8) . . ? C38 C37 C42 121.0(8) . . ? C38 C37 C36 123.5(8) . . ? C42 C37 C36 115.5(7) . . ? C39 C38 C37 120.4(9) . . ? C39 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C38 C39 C40 119.5(9) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C41 C40 C39 121.4(9) . . ? C41 C40 H40 119.3 . . ? C39 C40 H40 119.3 . . ? C40 C41 C42 120.5(8) . . ? C40 C41 H41 119.7 . . ? C42 C41 H41 119.7 . . ? C37 C42 C41 117.2(7) . . ? C37 C42 Ir 114.4(6) . . ? C41 C42 Ir 128.4(6) . . ? C42 Ir C31 83.1(3) . . ? C42 Ir N3 93.0(3) . . ? C31 Ir N3 80.3(2) . . ? C42 Ir N4 80.1(3) . . ? C31 Ir N4 93.3(2) . . ? N3 Ir N4 171.2(2) . . ? C42 Ir N2 99.2(2) . . ? C31 Ir N2 177.2(2) . . ? N3 Ir N2 101.25(19) . . ? N4 Ir N2 85.4(2) . . ? C42 Ir N1 172.5(3) . . ? C31 Ir N1 102.0(2) . . ? N3 Ir N1 93.2(2) . . ? N4 Ir N1 94.0(2) . . ? N2 Ir N1 75.6(2) . . ? C12 N1 C1 118.4(6) . . ? C12 N1 Ir 111.6(4) . . ? C1 N1 Ir 129.1(5) . . ? C11 N2 C10 118.7(6) . . ? C11 N2 Ir 111.1(4) . . ? C10 N2 Ir 129.2(5) . . ? C21 N3 C25 118.5(6) . . ? C21 N3 Ir 124.8(5) . . ? C25 N3 Ir 116.5(4) . . ? C32 N4 C36 119.1(6) . . ? C32 N4 Ir 125.3(5) . . ? C36 N4 Ir 115.5(5) . . ? F3B P F6 86.0(7) . . ? F3B P F5A 148.1(8) . . ? F6 P F5A 90.8(5) . . ? F3B P F4 95.4(7) . . ? F6 P F4 178.6(5) . . ? F5A P F4 87.9(6) . . ? F3B P F1A 56.7(7) . . ? F6 P F1A 92.8(5) . . ? F5A P F1A 91.9(5) . . ? F4 P F1A 87.9(4) . . ? F3B P F3A 32.9(7) . . ? F6 P F3A 91.8(5) . . ? F5A P F3A 177.3(7) . . ? F4 P F3A 89.5(5) . . ? F1A P F3A 88.6(5) . . ? F3B P F2A 121.2(8) . . ? F6 P F2A 90.3(4) . . ? F5A P F2A 90.6(5) . . ? F4 P F2A 89.0(4) . . ? F1A P F2A 176.0(5) . . ? F3A P F2A 88.8(4) . . ? F3B P F1B 91.6(7) . . ? F6 P F1B 87.9(8) . . ? F5A P F1B 56.5(9) . . ? F4 P F1B 91.9(9) . . ? F1A P F1B 35.8(9) . . ? F3A P F1B 124.2(9) . . ? F2A P F1B 147.0(9) . . ? F3B P F5B 173.5(11) . . ? F6 P F5B 87.5(8) . . ? F5A P F5B 32.6(9) . . ? F4 P F5B 91.1(9) . . ? F1A P F5B 124.4(9) . . ? F3A P F5B 147.0(9) . . ? F2A P F5B 58.2(9) . . ? F1B P F5B 88.8(7) . . ? F3B P F2B 91.2(7) . . ? F6 P F2B 86.0(7) . . ? F5A P F2B 120.4(8) . . ? F4 P F2B 94.1(7) . . ? F1A P F2B 147.8(8) . . ? F3A P F2B 59.3(7) . . ? F2A P F2B 30.1(7) . . ? F1B P F2B 173.1(10) . . ? F5B P F2B 87.8(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C18 -4.1(11) . . . . ? C19 C1 C2 C18 175.1(7) . . . . ? C18 C3 C4 C5 -1.5(14) . . . . ? C3 C4 C5 C14 -0.7(14) . . . . ? C15 C6 C7 C8 -1.2(14) . . . . ? C6 C7 C8 C17 1.8(15) . . . . ? C17 C9 C10 N2 1.7(10) . . . . ? C17 C9 C10 C20 -178.5(7) . . . . ? N2 C11 C12 N1 0.4(8) . . . . ? C16 C11 C12 N1 -177.7(5) . . . . ? N2 C11 C12 C13 179.6(5) . . . . ? C16 C11 C12 C13 1.5(9) . . . . ? N1 C12 C13 C18 0.1(9) . . . . ? C11 C12 C13 C18 -179.0(6) . . . . ? N1 C12 C13 C14 -177.7(6) . . . . ? C11 C12 C13 C14 3.2(9) . . . . ? C4 C5 C14 C13 3.1(12) . . . . ? C4 C5 C14 C15 -177.9(7) . . . . ? C18 C13 C14 C5 -3.2(10) . . . . ? C12 C13 C14 C5 174.5(6) . . . . ? C18 C13 C14 C15 177.7(6) . . . . ? C12 C13 C14 C15 -4.5(9) . . . . ? C7 C6 C15 C16 -0.3(12) . . . . ? C7 C6 C15 C14 178.1(8) . . . . ? C5 C14 C15 C6 3.9(11) . . . . ? C13 C14 C15 C6 -177.1(7) . . . . ? C5 C14 C15 C16 -177.7(7) . . . . ? C13 C14 C15 C16 1.3(9) . . . . ? C6 C15 C16 C11 -178.2(6) . . . . ? C14 C15 C16 C11 3.4(10) . . . . ? C6 C15 C16 C17 1.1(10) . . . . ? C14 C15 C16 C17 -177.3(6) . . . . ? N2 C11 C16 C15 177.2(6) . . . . ? C12 C11 C16 C15 -4.9(9) . . . . ? N2 C11 C16 C17 -2.1(9) . . . . ? C12 C11 C16 C17 175.8(6) . . . . ? C10 C9 C17 C8 -178.6(7) . . . . ? C10 C9 C17 C16 2.0(11) . . . . ? C7 C8 C17 C9 179.6(8) . . . . ? C7 C8 C17 C16 -0.9(12) . . . . ? C15 C16 C17 C9 178.9(6) . . . . ? C11 C16 C17 C9 -1.7(10) . . . . ? C15 C16 C17 C8 -0.5(10) . . . . ? C11 C16 C17 C8 178.8(6) . . . . ? C12 C13 C18 C2 6.0(10) . . . . ? C14 C13 C18 C2 -176.2(6) . . . . ? C12 C13 C18 C3 -176.7(6) . . . . ? C14 C13 C18 C3 1.1(10) . . . . ? C1 C2 C18 C13 -4.1(11) . . . . ? C1 C2 C18 C3 178.7(7) . . . . ? C4 C3 C18 C13 1.2(12) . . . . ? C4 C3 C18 C2 178.3(8) . . . . ? N3 C21 C22 C23 -1.2(13) . . . . ? C21 C22 C23 C24 0.2(13) . . . . ? C22 C23 C24 C25 1.9(13) . . . . ? C23 C24 C25 N3 -3.0(12) . . . . ? C23 C24 C25 C26 177.9(8) . . . . ? N3 C25 C26 C31 2.3(9) . . . . ? C24 C25 C26 C31 -178.5(7) . . . . ? N3 C25 C26 C27 -175.4(7) . . . . ? C24 C25 C26 C27 3.8(12) . . . . ? C31 C26 C27 C28 1.0(12) . . . . ? C25 C26 C27 C28 178.6(7) . . . . ? C26 C27 C28 C29 0.5(13) . . . . ? C27 C28 C29 C30 -2.1(13) . . . . ? C28 C29 C30 C31 2.2(12) . . . . ? C27 C26 C31 C30 -0.9(10) . . . . ? C25 C26 C31 C30 -178.6(6) . . . . ? C27 C26 C31 Ir 177.3(6) . . . . ? C25 C26 C31 Ir -0.4(8) . . . . ? C29 C30 C31 C26 -0.7(11) . . . . ? C29 C30 C31 Ir -178.6(6) . . . . ? N4 C32 C33 C34 1.4(14) . . . . ? C32 C33 C34 C35 0.4(15) . . . . ? C33 C34 C35 C36 -1.6(16) . . . . ? C34 C35 C36 N4 0.9(13) . . . . ? C34 C35 C36 C37 178.9(9) . . . . ? N4 C36 C37 C38 -175.9(7) . . . . ? C35 C36 C37 C38 5.9(12) . . . . ? N4 C36 C37 C42 2.1(9) . . . . ? C35 C36 C37 C42 -176.1(7) . . . . ? C42 C37 C38 C39 2.3(12) . . . . ? C36 C37 C38 C39 -179.8(8) . . . . ? C37 C38 C39 C40 0.3(14) . . . . ? C38 C39 C40 C41 -1.5(13) . . . . ? C39 C40 C41 C42 0.0(12) . . . . ? C38 C37 C42 C41 -3.7(10) . . . . ? C36 C37 C42 C41 178.2(6) . . . . ? C38 C37 C42 Ir 175.3(6) . . . . ? C36 C37 C42 Ir -2.8(8) . . . . ? C40 C41 C42 C37 2.6(10) . . . . ? C40 C41 C42 Ir -176.2(6) . . . . ? C37 C42 Ir C31 96.6(5) . . . . ? C41 C42 Ir C31 -84.6(6) . . . . ? C37 C42 Ir N3 176.4(5) . . . . ? C41 C42 Ir N3 -4.8(6) . . . . ? C37 C42 Ir N4 2.0(5) . . . . ? C41 C42 Ir N4 -179.2(7) . . . . ? C37 C42 Ir N2 -81.7(5) . . . . ? C41 C42 Ir N2 97.1(6) . . . . ? C37 C42 Ir N1 -36(2) . . . . ? C41 C42 Ir N1 142.4(16) . . . . ? C26 C31 Ir C42 93.3(5) . . . . ? C30 C31 Ir C42 -88.7(7) . . . . ? C26 C31 Ir N3 -1.0(5) . . . . ? C30 C31 Ir N3 177.0(7) . . . . ? C26 C31 Ir N4 172.9(5) . . . . ? C30 C31 Ir N4 -9.1(7) . . . . ? C26 C31 Ir N2 -123(4) . . . . ? C30 C31 Ir N2 55(5) . . . . ? C26 C31 Ir N1 -92.3(5) . . . . ? C30 C31 Ir N1 85.7(6) . . . . ? C13 C12 N1 C1 -8.4(9) . . . . ? C11 C12 N1 C1 170.8(5) . . . . ? C13 C12 N1 Ir 161.9(5) . . . . ? C11 C12 N1 Ir -19.0(6) . . . . ? C2 C1 N1 C12 10.2(9) . . . . ? C19 C1 N1 C12 -169.0(6) . . . . ? C2 C1 N1 Ir -158.1(5) . . . . ? C19 C1 N1 Ir 22.7(9) . . . . ? C42 Ir N1 C12 -25.2(19) . . . . ? C31 Ir N1 C12 -157.3(4) . . . . ? N3 Ir N1 C12 122.0(4) . . . . ? N4 Ir N1 C12 -63.0(4) . . . . ? N2 Ir N1 C12 21.2(4) . . . . ? C42 Ir N1 C1 143.7(17) . . . . ? C31 Ir N1 C1 11.6(6) . . . . ? N3 Ir N1 C1 -69.1(6) . . . . ? N4 Ir N1 C1 105.9(6) . . . . ? N2 Ir N1 C1 -169.9(6) . . . . ? C16 C11 N2 C10 5.8(9) . . . . ? C12 C11 N2 C10 -172.2(5) . . . . ? C16 C11 N2 Ir -163.7(5) . . . . ? C12 C11 N2 Ir 18.3(6) . . . . ? C9 C10 N2 C11 -5.5(9) . . . . ? C20 C10 N2 C11 174.7(6) . . . . ? C9 C10 N2 Ir 161.8(5) . . . . ? C20 C10 N2 Ir -18.0(9) . . . . ? C42 Ir N2 C11 153.7(4) . . . . ? C31 Ir N2 C11 11(5) . . . . ? N3 Ir N2 C11 -111.3(4) . . . . ? N4 Ir N2 C11 74.5(4) . . . . ? N1 Ir N2 C11 -20.8(4) . . . . ? C42 Ir N2 C10 -14.3(6) . . . . ? C31 Ir N2 C10 -157(4) . . . . ? N3 Ir N2 C10 80.7(6) . . . . ? N4 Ir N2 C10 -93.5(5) . . . . ? N1 Ir N2 C10 171.2(6) . . . . ? C22 C21 N3 C25 0.1(11) . . . . ? C22 C21 N3 Ir -175.1(6) . . . . ? C24 C25 N3 C21 1.9(10) . . . . ? C26 C25 N3 C21 -178.8(6) . . . . ? C24 C25 N3 Ir 177.6(6) . . . . ? C26 C25 N3 Ir -3.2(8) . . . . ? C42 Ir N3 C21 95.2(6) . . . . ? C31 Ir N3 C21 177.7(6) . . . . ? N4 Ir N3 C21 134.1(13) . . . . ? N2 Ir N3 C21 -4.8(6) . . . . ? N1 Ir N3 C21 -80.7(6) . . . . ? C42 Ir N3 C25 -80.1(5) . . . . ? C31 Ir N3 C25 2.4(5) . . . . ? N4 Ir N3 C25 -41.2(17) . . . . ? N2 Ir N3 C25 179.9(5) . . . . ? N1 Ir N3 C25 104.0(5) . . . . ? C33 C32 N4 C36 -2.2(11) . . . . ? C33 C32 N4 Ir -178.7(6) . . . . ? C35 C36 N4 C32 1.0(10) . . . . ? C37 C36 N4 C32 -177.3(6) . . . . ? C35 C36 N4 Ir 177.9(6) . . . . ? C37 C36 N4 Ir -0.4(8) . . . . ? C42 Ir N4 C32 175.8(6) . . . . ? C31 Ir N4 C32 93.4(6) . . . . ? N3 Ir N4 C32 136.3(14) . . . . ? N2 Ir N4 C32 -84.0(6) . . . . ? N1 Ir N4 C32 -8.8(6) . . . . ? C42 Ir N4 C36 -0.9(5) . . . . ? C31 Ir N4 C36 -83.3(5) . . . . ? N3 Ir N4 C36 -40.4(16) . . . . ? N2 Ir N4 C36 99.3(5) . . . . ? N1 Ir N4 C36 174.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.566 _refine_diff_density_min -1.439 _refine_diff_density_rms 0.114 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 1 0.000 -0.010 -0.001 974.8 242.6 2 0.500 0.111 0.229 974.8 242.6 #====================================================================== # end of cif _chemical_name_common ; Bis(2-(2-pyridyl)phenyl)(2,11-dimethyl-1,12- diazaperylene)iridium(iii)-hexafluorophosphate ;