# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Lo, Kenneth' _publ_contact_author_email bhkenlo@cityu.edu.hk _publ_section_title ; Luminescent cyclometallated iridium(III) bis(quinolylbenzaldehyde) diimine complexes - synthesis, photophysics, electrochemistry, protein cross-linking properties, cytotoxicity and cellular uptake ; _publ_author_name K.Lo # Attachment '- Ir qba bpy.cif' data_021810a_yuqin _database_code_depnum_ccdc_archive 'CCDC 775620' #TrackingRef '- Ir qba bpy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H33 F6 Ir N4 O2.50 P' _chemical_formula_weight 994.91 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6285(3) _cell_length_b 13.1359(3) _cell_length_c 14.5805(3) _cell_angle_alpha 93.7062(17) _cell_angle_beta 102.689(2) _cell_angle_gamma 105.697(2) _cell_volume 1895.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 31243 _cell_measurement_theta_min 3.5956 _cell_measurement_theta_max 32.1903 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 982 _exptl_absorpt_coefficient_mu 3.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.37794 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1270 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25201 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6659 _reflns_number_gt 6219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ortep-3 _computing_publication_material wingx _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6659 _refine_ls_number_parameters 523 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0193 _refine_ls_R_factor_gt 0.0170 _refine_ls_wR_factor_ref 0.0452 _refine_ls_wR_factor_gt 0.0447 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.427544(8) 0.272348(7) 0.703285(6) 0.01441(4) Uani 1 1 d . A . P1 P 0.88328(7) 0.74314(6) 0.85356(5) 0.02742(16) Uani 1 1 d . . . F1 F 1.0365(2) 0.76265(17) 0.85306(19) 0.0642(6) Uani 1 1 d . . . F2 F 0.72842(17) 0.72310(15) 0.85353(13) 0.0427(4) Uani 1 1 d . . . F3 F 0.91667(18) 0.86417(13) 0.89925(13) 0.0394(4) Uani 1 1 d . . . F4 F 0.8528(2) 0.77724(15) 0.75018(13) 0.0516(5) Uani 1 1 d . . . F5 F 0.8492(2) 0.62192(13) 0.80872(15) 0.0488(5) Uani 1 1 d . . . F6 F 0.9119(2) 0.71044(15) 0.95787(14) 0.0525(5) Uani 1 1 d . . . O2 O -0.1128(2) 0.13968(18) 0.34728(15) 0.0418(5) Uani 1 1 d . . . N1 N 0.3697(2) 0.41230(16) 0.69162(14) 0.0183(4) Uani 1 1 d . A . N2 N 0.4920(2) 0.13626(16) 0.69060(15) 0.0187(4) Uani 1 1 d . A . N3 N 0.5286(2) 0.35213(17) 0.84626(15) 0.0191(4) Uani 1 1 d . . . N4 N 0.31316(19) 0.18419(16) 0.79357(14) 0.0172(4) Uani 1 1 d . . . C1A C 0.8481(9) 0.3501(7) 0.5282(7) 0.030(3) Uiso 0.50 1 d PD A 1 O1A O 0.9471(4) 0.4073(3) 0.5075(3) 0.0413(10) Uiso 0.50 1 d PD A 1 C1B C 0.8645(8) 0.3466(6) 0.5427(6) 0.022(3) Uiso 0.50 1 d PD A 2 O1B O 0.8561(4) 0.2538(3) 0.5319(3) 0.0278(8) Uiso 0.50 1 d PD A 2 C2 C 0.7541(3) 0.3878(2) 0.56795(19) 0.0240(6) Uani 1 1 d D . . C3 C 0.7559(3) 0.4931(2) 0.56405(19) 0.0261(6) Uani 1 1 d . A . H3 H 0.8210 0.5389 0.5405 0.031 Uiso 1 1 calc R . . C4 C 0.6608(3) 0.5299(2) 0.59510(19) 0.0256(6) Uani 1 1 d . . . H4 H 0.6614 0.6006 0.5926 0.031 Uiso 1 1 calc R A . C5 C 0.5636(2) 0.4604(2) 0.63035(17) 0.0199(5) Uani 1 1 d . A . C6 C 0.5608(2) 0.35395(19) 0.63724(17) 0.0184(5) Uani 1 1 d . . . C7 C 0.6578(2) 0.3184(2) 0.60354(18) 0.0217(5) Uani 1 1 d . A . H7 H 0.6577 0.2477 0.6051 0.026 Uiso 1 1 calc R . . C8 C 0.4571(3) 0.4915(2) 0.66326(18) 0.0212(5) Uani 1 1 d . . . C9 C 0.4447(3) 0.5958(2) 0.6644(2) 0.0309(6) Uani 1 1 d . A . H9 H 0.5087 0.6493 0.6467 0.037 Uiso 1 1 calc R . . C10 C 0.2413(3) 0.5368(2) 0.7154(2) 0.0293(6) Uani 1 1 d . A . C11 C 0.2570(3) 0.4325(2) 0.71479(18) 0.0222(5) Uani 1 1 d . . . C12 C 0.1573(3) 0.3504(2) 0.73626(19) 0.0282(6) Uani 1 1 d . A . H12 H 0.1649 0.2814 0.7338 0.034 Uiso 1 1 calc R . . C13 C 0.0486(3) 0.3708(3) 0.7609(2) 0.0394(7) Uani 1 1 d . . . H13 H -0.0171 0.3156 0.7750 0.047 Uiso 1 1 calc R A . C14 C 0.0353(3) 0.4747(3) 0.7650(2) 0.0428(8) Uani 1 1 d . A . H14 H -0.0377 0.4881 0.7834 0.051 Uiso 1 1 calc R . . C15 C 0.1276(3) 0.5543(3) 0.7426(2) 0.0376(7) Uani 1 1 d . . . H15 H 0.1171 0.6224 0.7448 0.045 Uiso 1 1 calc R A . C16 C -0.0065(3) 0.1973(2) 0.39554(19) 0.0267(6) Uani 1 1 d . . . H16 H 0.0066 0.2705 0.3996 0.032 Uiso 1 1 calc R . . C17 C 0.1037(3) 0.1597(2) 0.44844(18) 0.0213(5) Uani 1 1 d . . . C18 C 0.1091(3) 0.0560(2) 0.42708(19) 0.0256(6) Uani 1 1 d . . . H18 H 0.0446 0.0100 0.3771 0.031 Uiso 1 1 calc R . . C19 C 0.2095(3) 0.0223(2) 0.47987(19) 0.0269(6) Uani 1 1 d . . . H19 H 0.2146 -0.0461 0.4649 0.032 Uiso 1 1 calc R . . C20 C 0.3054(2) 0.0910(2) 0.55688(18) 0.0198(5) Uani 1 1 d . A . C21 C 0.3015(2) 0.19550(19) 0.58117(17) 0.0168(5) Uani 1 1 d . . . C22 C 0.2000(2) 0.22819(19) 0.52352(17) 0.0180(5) Uani 1 1 d . A . H22 H 0.1967 0.2977 0.5357 0.022 Uiso 1 1 calc R . . C23 C 0.4140(3) 0.0612(2) 0.61818(18) 0.0211(5) Uani 1 1 d . . . C24 C 0.4398(3) -0.0376(2) 0.6015(2) 0.0318(6) Uani 1 1 d . A . H24 H 0.3821 -0.0889 0.5523 0.038 Uiso 1 1 calc R . . C25 C 0.5479(3) -0.0578(2) 0.6566(2) 0.0364(7) Uani 1 1 d . . . H25 H 0.5643 -0.1230 0.6458 0.044 Uiso 1 1 calc R A . C26 C 0.6356(3) 0.0202(2) 0.7304(2) 0.0297(6) Uani 1 1 d . A . C27 C 0.6054(2) 0.1178(2) 0.74667(19) 0.0216(5) Uani 1 1 d . . . C28 C 0.6950(3) 0.1961(2) 0.8184(2) 0.0291(6) Uani 1 1 d . A . H28 H 0.6784 0.2613 0.8287 0.035 Uiso 1 1 calc R . . C29 C 0.8065(3) 0.1782(3) 0.8734(2) 0.0372(7) Uani 1 1 d . . . H29 H 0.8647 0.2313 0.9209 0.045 Uiso 1 1 calc R A . C30 C 0.8347(3) 0.0812(3) 0.8596(2) 0.0382(8) Uani 1 1 d . A . H30 H 0.9096 0.0693 0.8988 0.046 Uiso 1 1 calc R . . C31 C 0.7524(3) 0.0047(3) 0.7887(2) 0.0382(7) Uani 1 1 d . . . H31 H 0.7729 -0.0589 0.7783 0.046 Uiso 1 1 calc R A . C32 C 0.6364(3) 0.4396(2) 0.86862(19) 0.0246(6) Uani 1 1 d . . . H32 H 0.6733 0.4677 0.8202 0.029 Uiso 1 1 calc R . . C33 C 0.6940(3) 0.4891(2) 0.9598(2) 0.0337(7) Uani 1 1 d . . . H33 H 0.7700 0.5482 0.9731 0.040 Uiso 1 1 calc R . . C34 C 0.6374(3) 0.4497(2) 1.0314(2) 0.0363(7) Uani 1 1 d . . . H34 H 0.6748 0.4819 1.0937 0.044 Uiso 1 1 calc R . . C35 C 0.5253(3) 0.3624(2) 1.00980(19) 0.0304(6) Uani 1 1 d . . . H35 H 0.4850 0.3359 1.0573 0.037 Uiso 1 1 calc R . . C36 C 0.4723(2) 0.3140(2) 0.91639(17) 0.0203(5) Uani 1 1 d . . . C37 C 0.3553(2) 0.21783(19) 0.88749(17) 0.0177(5) Uani 1 1 d . . . C38 C 0.2941(3) 0.1623(2) 0.95123(19) 0.0233(5) Uani 1 1 d . . . H38 H 0.3231 0.1874 1.0157 0.028 Uiso 1 1 calc R . . C39 C 0.1905(3) 0.0698(2) 0.91874(19) 0.0256(6) Uani 1 1 d . . . H39 H 0.1478 0.0323 0.9608 0.031 Uiso 1 1 calc R . . C40 C 0.1505(3) 0.0335(2) 0.8236(2) 0.0254(6) Uani 1 1 d . . . H40 H 0.0823 -0.0300 0.8004 0.031 Uiso 1 1 calc R . . C41 C 0.2133(2) 0.0929(2) 0.76304(19) 0.0219(5) Uani 1 1 d . . . H41 H 0.1852 0.0687 0.6984 0.026 Uiso 1 1 calc R . . C43 C 0.3400(3) 0.6183(2) 0.6910(2) 0.0345(7) Uani 1 1 d . . . H43 H 0.3333 0.6875 0.6932 0.041 Uiso 1 1 calc R A . O1S O 0.4953(6) 0.9981(5) 1.0179(3) 0.0372(11) Uiso 0.50 1 d P . . C1S C 0.4697(7) 0.9607(5) 0.9192(5) 0.0408(15) Uiso 0.50 1 d P . . C2S C 0.3973(6) 0.9047(5) 0.9546(5) 0.0357(14) Uiso 0.50 1 d P . . C3S C 0.3547(8) 0.8561(7) 0.8952(6) 0.0543(19) Uiso 0.50 1 d P . . C4S C 0.3826(7) 0.8670(6) 0.8523(5) 0.0429(16) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01431(6) 0.01498(6) 0.01266(6) 0.00177(4) 0.00294(4) 0.00251(4) P1 0.0306(4) 0.0207(4) 0.0329(4) 0.0066(3) 0.0124(3) 0.0064(3) F1 0.0364(11) 0.0477(12) 0.112(2) 0.0021(12) 0.0322(12) 0.0089(9) F2 0.0303(9) 0.0587(12) 0.0357(10) -0.0043(9) 0.0089(7) 0.0094(8) F3 0.0537(11) 0.0235(9) 0.0412(11) 0.0030(8) 0.0159(9) 0.0084(8) F4 0.0866(15) 0.0439(11) 0.0315(10) 0.0117(9) 0.0280(10) 0.0185(11) F5 0.0559(12) 0.0238(9) 0.0654(14) -0.0004(9) 0.0177(10) 0.0087(9) F6 0.0557(12) 0.0364(10) 0.0433(11) 0.0179(9) -0.0111(9) -0.0074(9) O2 0.0300(11) 0.0479(13) 0.0360(13) -0.0017(10) -0.0054(9) 0.0050(10) N1 0.0201(10) 0.0209(11) 0.0124(10) -0.0017(8) 0.0007(8) 0.0069(9) N2 0.0178(10) 0.0200(11) 0.0194(11) 0.0055(9) 0.0070(8) 0.0047(9) N3 0.0192(10) 0.0189(11) 0.0177(11) 0.0043(9) 0.0018(8) 0.0049(9) N4 0.0153(10) 0.0190(10) 0.0178(11) 0.0035(8) 0.0048(8) 0.0048(8) C2 0.0235(13) 0.0265(14) 0.0206(14) 0.0044(11) 0.0088(11) 0.0022(11) C3 0.0245(13) 0.0262(14) 0.0237(15) 0.0064(12) 0.0082(11) -0.0013(11) C4 0.0296(14) 0.0168(13) 0.0276(15) 0.0055(11) 0.0058(11) 0.0025(11) C5 0.0231(13) 0.0195(13) 0.0143(13) 0.0011(10) 0.0023(10) 0.0034(10) C6 0.0182(12) 0.0186(12) 0.0149(12) 0.0026(10) 0.0001(10) 0.0028(10) C7 0.0222(12) 0.0222(13) 0.0203(13) 0.0037(11) 0.0069(10) 0.0046(11) C8 0.0259(13) 0.0176(13) 0.0162(13) -0.0006(10) 0.0004(10) 0.0043(11) C9 0.0393(16) 0.0219(14) 0.0309(16) 0.0035(12) 0.0081(13) 0.0083(12) C10 0.0366(16) 0.0333(16) 0.0200(14) -0.0020(12) 0.0014(12) 0.0193(13) C11 0.0249(13) 0.0304(14) 0.0122(13) -0.0012(11) 0.0009(10) 0.0135(11) C12 0.0254(14) 0.0353(16) 0.0272(15) 0.0047(12) 0.0060(11) 0.0144(12) C13 0.0273(15) 0.055(2) 0.0416(19) 0.0087(16) 0.0116(13) 0.0184(15) C14 0.0359(17) 0.063(2) 0.0398(19) 0.0013(16) 0.0112(14) 0.0311(17) C15 0.0427(18) 0.0438(18) 0.0331(17) -0.0021(14) 0.0049(14) 0.0292(16) C16 0.0241(14) 0.0322(15) 0.0196(14) -0.0002(12) 0.0027(11) 0.0046(12) C17 0.0210(12) 0.0241(13) 0.0161(13) 0.0032(10) 0.0057(10) 0.0011(10) C18 0.0269(14) 0.0232(14) 0.0192(14) -0.0036(11) 0.0007(11) 0.0004(11) C19 0.0332(15) 0.0201(14) 0.0243(15) -0.0026(11) 0.0049(12) 0.0056(12) C20 0.0230(13) 0.0187(13) 0.0167(13) 0.0018(10) 0.0068(10) 0.0030(10) C21 0.0184(12) 0.0191(12) 0.0123(12) 0.0024(10) 0.0067(9) 0.0023(10) C22 0.0219(12) 0.0157(12) 0.0155(13) 0.0027(10) 0.0058(10) 0.0026(10) C23 0.0242(13) 0.0190(13) 0.0225(14) 0.0054(11) 0.0113(11) 0.0049(11) C24 0.0417(17) 0.0255(15) 0.0304(16) 0.0028(12) 0.0085(13) 0.0138(13) C25 0.0498(19) 0.0270(16) 0.0425(19) 0.0080(14) 0.0165(15) 0.0227(14) C26 0.0319(15) 0.0344(16) 0.0342(17) 0.0169(13) 0.0168(13) 0.0187(13) C27 0.0193(12) 0.0275(14) 0.0225(14) 0.0106(11) 0.0093(10) 0.0091(11) C28 0.0234(14) 0.0339(16) 0.0315(16) 0.0064(13) 0.0058(12) 0.0111(12) C29 0.0223(14) 0.053(2) 0.0364(18) 0.0119(15) 0.0044(12) 0.0128(14) C30 0.0260(15) 0.056(2) 0.0440(19) 0.0260(17) 0.0127(14) 0.0227(15) C31 0.0389(17) 0.0450(19) 0.046(2) 0.0202(16) 0.0175(15) 0.0276(15) C32 0.0231(13) 0.0201(13) 0.0231(14) 0.0038(11) -0.0009(11) -0.0006(11) C33 0.0364(16) 0.0258(15) 0.0268(16) 0.0038(12) -0.0030(12) -0.0022(13) C34 0.0510(19) 0.0270(15) 0.0169(14) -0.0012(12) -0.0034(13) -0.0011(14) C35 0.0439(17) 0.0275(15) 0.0155(14) 0.0024(11) 0.0047(12) 0.0053(13) C36 0.0250(13) 0.0200(13) 0.0162(13) 0.0027(10) 0.0027(10) 0.0087(11) C37 0.0182(12) 0.0200(13) 0.0161(13) 0.0029(10) 0.0038(10) 0.0080(10) C38 0.0249(13) 0.0285(14) 0.0179(13) 0.0037(11) 0.0077(10) 0.0081(11) C39 0.0245(13) 0.0312(15) 0.0250(15) 0.0102(12) 0.0130(11) 0.0075(12) C40 0.0202(13) 0.0242(14) 0.0300(16) 0.0037(12) 0.0084(11) 0.0015(11) C41 0.0188(12) 0.0246(14) 0.0188(13) 0.0010(11) 0.0049(10) 0.0011(11) C43 0.0505(19) 0.0236(15) 0.0315(17) -0.0001(12) 0.0071(14) 0.0173(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C21 1.993(2) . ? Ir1 C6 1.998(2) . ? Ir1 N2 2.091(2) . ? Ir1 N1 2.096(2) . ? Ir1 N4 2.1657(19) . ? Ir1 N3 2.173(2) . ? P1 F1 1.5798(19) . ? P1 F4 1.5903(19) . ? P1 F6 1.5943(19) . ? P1 F2 1.5949(17) . ? P1 F5 1.5950(18) . ? P1 F3 1.5972(18) . ? O2 C16 1.209(3) . ? N1 C8 1.349(3) . ? N1 C11 1.398(3) . ? N2 C23 1.347(3) . ? N2 C27 1.389(3) . ? N3 C32 1.347(3) . ? N3 C36 1.352(3) . ? N4 C41 1.341(3) . ? N4 C37 1.348(3) . ? C1A O1A 1.226(9) . ? C1A C2 1.437(9) . ? C1B O1B 1.195(8) . ? C1B C2 1.521(8) . ? C2 C3 1.384(4) . ? C2 C7 1.392(3) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C5 1.396(4) . ? C4 H4 0.9300 . ? C5 C6 1.402(3) . ? C5 C8 1.463(4) . ? C6 C7 1.407(3) . ? C7 H7 0.9300 . ? C8 C9 1.410(4) . ? C9 C43 1.352(4) . ? C9 H9 0.9300 . ? C10 C43 1.406(4) . ? C10 C15 1.420(4) . ? C10 C11 1.425(4) . ? C11 C12 1.398(4) . ? C12 C13 1.370(4) . ? C12 H12 0.9300 . ? C13 C14 1.408(5) . ? C13 H13 0.9300 . ? C14 C15 1.339(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.475(4) . ? C16 H16 0.9300 . ? C17 C22 1.392(4) . ? C17 C18 1.397(4) . ? C18 C19 1.366(4) . ? C18 H18 0.9300 . ? C19 C20 1.408(4) . ? C19 H19 0.9300 . ? C20 C21 1.409(3) . ? C20 C23 1.456(4) . ? C21 C22 1.398(3) . ? C22 H22 0.9300 . ? C23 C24 1.414(4) . ? C24 C25 1.350(4) . ? C24 H24 0.9300 . ? C25 C26 1.406(4) . ? C25 H25 0.9300 . ? C26 C31 1.415(4) . ? C26 C27 1.421(4) . ? C27 C28 1.397(4) . ? C28 C29 1.365(4) . ? C28 H28 0.9300 . ? C29 C30 1.397(5) . ? C29 H29 0.9300 . ? C30 C31 1.354(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.371(4) . ? C32 H32 0.9300 . ? C33 C34 1.376(4) . ? C33 H33 0.9300 . ? C34 C35 1.372(4) . ? C34 H34 0.9300 . ? C35 C36 1.391(4) . ? C35 H35 0.9300 . ? C36 C37 1.473(3) . ? C37 C38 1.384(3) . ? C38 C39 1.373(4) . ? C38 H38 0.9300 . ? C39 C40 1.370(4) . ? C39 H39 0.9300 . ? C40 C41 1.379(4) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C43 H43 0.9300 . ? O1S O1S 0.555(9) 2_677 ? O1S C1S 0.975(7) 2_677 ? O1S C2S 1.428(9) 2_677 ? O1S C1S 1.431(10) . ? O1S C2S 1.476(9) . ? C1S O1S 0.975(7) 2_677 ? C1S C2S 1.147(9) . ? C1S C4S 1.468(10) . ? C1S C3S 1.532(11) . ? C2S C3S 0.982(9) . ? C2S O1S 1.428(9) 2_677 ? C2S C4S 1.503(10) . ? C3S C4S 0.756(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 Ir1 C6 92.27(9) . . ? C21 Ir1 N2 79.61(9) . . ? C6 Ir1 N2 92.44(9) . . ? C21 Ir1 N1 94.42(9) . . ? C6 Ir1 N1 79.17(9) . . ? N2 Ir1 N1 169.57(7) . . ? C21 Ir1 N4 95.77(8) . . ? C6 Ir1 N4 170.19(8) . . ? N2 Ir1 N4 83.52(7) . . ? N1 Ir1 N4 105.72(8) . . ? C21 Ir1 N3 168.59(8) . . ? C6 Ir1 N3 97.63(9) . . ? N2 Ir1 N3 105.50(8) . . ? N1 Ir1 N3 81.96(8) . . ? N4 Ir1 N3 74.99(8) . . ? F1 P1 F4 90.31(13) . . ? F1 P1 F6 90.61(13) . . ? F4 P1 F6 178.75(12) . . ? F1 P1 F2 179.70(13) . . ? F4 P1 F2 89.49(11) . . ? F6 P1 F2 89.59(11) . . ? F1 P1 F5 90.52(11) . . ? F4 P1 F5 90.19(11) . . ? F6 P1 F5 90.64(11) . . ? F2 P1 F5 89.26(10) . . ? F1 P1 F3 89.83(11) . . ? F4 P1 F3 90.23(10) . . ? F6 P1 F3 88.93(10) . . ? F2 P1 F3 90.39(10) . . ? F5 P1 F3 179.45(11) . . ? C8 N1 C11 118.5(2) . . ? C8 N1 Ir1 114.29(16) . . ? C11 N1 Ir1 127.13(17) . . ? C23 N2 C27 118.5(2) . . ? C23 N2 Ir1 114.40(16) . . ? C27 N2 Ir1 127.10(17) . . ? C32 N3 C36 118.4(2) . . ? C32 N3 Ir1 124.95(17) . . ? C36 N3 Ir1 116.49(17) . . ? C41 N4 C37 118.4(2) . . ? C41 N4 Ir1 123.99(17) . . ? C37 N4 Ir1 117.18(16) . . ? O1A C1A C2 125.0(7) . . ? O1B C1B C2 122.8(6) . . ? C3 C2 C7 120.9(2) . . ? C3 C2 C1A 118.2(4) . . ? C7 C2 C1A 120.8(4) . . ? C3 C2 C1B 121.3(4) . . ? C7 C2 C1B 117.5(4) . . ? C1A C2 C1B 9.5(6) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 122.1(2) . . ? C4 C5 C8 123.6(2) . . ? C6 C5 C8 114.3(2) . . ? C5 C6 C7 116.9(2) . . ? C5 C6 Ir1 115.95(18) . . ? C7 C6 Ir1 126.93(18) . . ? C2 C7 C6 120.7(2) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N1 C8 C9 122.0(2) . . ? N1 C8 C5 114.9(2) . . ? C9 C8 C5 123.1(2) . . ? C43 C9 C8 120.3(3) . . ? C43 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C43 C10 C15 122.9(3) . . ? C43 C10 C11 118.7(3) . . ? C15 C10 C11 118.4(3) . . ? C12 C11 N1 120.6(2) . . ? C12 C11 C10 119.0(2) . . ? N1 C11 C10 120.4(2) . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.6(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 121.3(3) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? O2 C16 C17 124.7(3) . . ? O2 C16 H16 117.7 . . ? C17 C16 H16 117.7 . . ? C22 C17 C18 120.0(2) . . ? C22 C17 C16 118.7(2) . . ? C18 C17 C16 121.2(2) . . ? C19 C18 C17 119.7(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C21 121.5(2) . . ? C19 C20 C23 123.9(2) . . ? C21 C20 C23 114.6(2) . . ? C22 C21 C20 116.6(2) . . ? C22 C21 Ir1 127.45(18) . . ? C20 C21 Ir1 115.44(18) . . ? C17 C22 C21 121.9(2) . . ? C17 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? N2 C23 C24 121.9(2) . . ? N2 C23 C20 115.1(2) . . ? C24 C23 C20 122.9(2) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 119.7(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C31 122.2(3) . . ? C25 C26 C27 118.6(3) . . ? C31 C26 C27 119.1(3) . . ? N2 C27 C28 120.8(2) . . ? N2 C27 C26 120.8(2) . . ? C28 C27 C26 118.3(2) . . ? C29 C28 C27 121.0(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 121.0(3) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C31 C30 C29 119.7(3) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C26 120.9(3) . . ? C30 C31 H31 119.6 . . ? C26 C31 H31 119.6 . . ? N3 C32 C33 122.7(3) . . ? N3 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C32 C33 C34 118.8(3) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 119.4(3) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 119.5(3) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? N3 C36 C35 121.1(2) . . ? N3 C36 C37 115.8(2) . . ? C35 C36 C37 123.1(2) . . ? N4 C37 C38 121.3(2) . . ? N4 C37 C36 115.4(2) . . ? C38 C37 C36 123.3(2) . . ? C39 C38 C37 119.6(2) . . ? C39 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? C40 C39 C38 119.2(2) . . ? C40 C39 H39 120.4 . . ? C38 C39 H39 120.4 . . ? C39 C40 C41 118.8(3) . . ? C39 C40 H40 120.6 . . ? C41 C40 H40 120.6 . . ? N4 C41 C40 122.6(2) . . ? N4 C41 H41 118.7 . . ? C40 C41 H41 118.7 . . ? C9 C43 C10 119.9(3) . . ? C9 C43 H43 120.1 . . ? C10 C43 H43 120.1 . . ? O1S O1S C1S 137.0(16) 2_677 2_677 ? O1S O1S C2S 83.9(13) 2_677 2_677 ? C1S O1S C2S 53.1(6) 2_677 2_677 ? O1S O1S C1S 27.7(11) 2_677 . ? C1S O1S C1S 164.7(6) 2_677 . ? C2S O1S C1S 111.6(5) 2_677 . ? O1S O1S C2S 74.1(13) 2_677 . ? C1S O1S C2S 148.8(7) 2_677 . ? C2S O1S C2S 158.1(3) 2_677 . ? C1S O1S C2S 46.5(4) . . ? O1S C1S C2S 84.2(7) 2_677 . ? O1S C1S O1S 15.3(6) 2_677 . ? C2S C1S O1S 68.8(5) . . ? O1S C1S C4S 152.9(8) 2_677 . ? C2S C1S C4S 68.9(6) . . ? O1S C1S C4S 137.6(6) . . ? O1S C1S C3S 124.0(8) 2_677 . ? C2S C1S C3S 39.8(5) . . ? O1S C1S C3S 108.7(6) . . ? C4S C1S C3S 29.1(4) . . ? C3S C2S C1S 91.7(8) . . ? C3S C2S O1S 134.4(8) . 2_677 ? C1S C2S O1S 42.8(4) . 2_677 ? C3S C2S O1S 156.3(8) . . ? C1S C2S O1S 64.7(5) . . ? O1S C2S O1S 21.9(3) 2_677 . ? C3S C2S C4S 26.0(6) . . ? C1S C2S C4S 65.7(5) . . ? O1S C2S C4S 108.4(5) 2_677 . ? O1S C2S C4S 130.3(5) . . ? C4S C3S C2S 119.2(13) . . ? C4S C3S C1S 70.8(9) . . ? C2S C3S C1S 48.5(6) . . ? C3S C4S C1S 80.1(10) . . ? C3S C4S C2S 34.8(8) . . ? C1S C4S C2S 45.4(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.122 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.074 #============================================================================== # Formatted by publCIF data_010510a_kei _database_code_depnum_ccdc_archive 'CCDC 775621' #TrackingRef '- Ir qba phen.cif' _diffrn_ambient_pressure ? #Added by publCIF _symmetry_space_group_name_hall ? #Added by publCIF _refine_ls_abs_structure_Flack ? #Added by publCIF _refine_ls_abs_structure_details ? #Added by publCIF _audit_update_record ; 2010-01-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50.50 H42 F6 Ir N4 O4 P' _chemical_formula_weight 1106.05 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1167(3) _cell_length_b 12.1327(4) _cell_length_c 16.8271(5) _cell_angle_alpha 82.778(3) _cell_angle_beta 85.602(3) _cell_angle_gamma 78.438(3) _cell_volume 2202.76(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11103 _cell_measurement_theta_min 3.4442 _cell_measurement_theta_max 27.4942 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1102 _exptl_absorpt_coefficient_mu 3.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85734 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1270 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13448 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7729 _reflns_number_gt 6830 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics wingx _computing_publication_material 'WinGX, ORTEP-3^4^, publCIF' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0280P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7729 _refine_ls_number_parameters 646 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0476 _refine_ls_wR_factor_gt 0.0469 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.842561(10) 0.286158(9) 0.322644(7) 0.01637(4) Uani 1 1 d . . . P1 P 0.28305(8) 0.86678(7) 0.17425(5) 0.0313(2) Uani 1 1 d . . . F1 F 0.14772(19) 0.8434(2) 0.19468(16) 0.0665(7) Uani 1 1 d . . . F2 F 0.23813(19) 0.99126(17) 0.19892(13) 0.0510(6) Uani 1 1 d . . . F3 F 0.3190(2) 0.8219(2) 0.26420(13) 0.0572(6) Uani 1 1 d . . . F4 F 0.2460(2) 0.91146(18) 0.08425(12) 0.0534(6) Uani 1 1 d . . . F5 F 0.3266(2) 0.74157(17) 0.15087(14) 0.0568(6) Uani 1 1 d . . . F6 F 0.41698(19) 0.89169(19) 0.15361(14) 0.0565(6) Uani 1 1 d . . . O1 O 1.2984(2) 0.2253(2) 0.47837(15) 0.0469(6) Uani 1 1 d . . . O2 O 0.4409(2) 0.30432(18) 0.63337(13) 0.0341(5) Uani 1 1 d . . . O3 O 0.4388(3) 0.3148(3) 0.08145(19) 0.0726(9) Uani 1 1 d . . . N1 N 0.7695(2) 0.13913(19) 0.32937(13) 0.0205(5) Uani 1 1 d . . . N2 N 0.9246(2) 0.42227(19) 0.33798(14) 0.0191(5) Uani 1 1 d . . . N3 N 0.8986(2) 0.23852(19) 0.20164(14) 0.0193(5) Uani 1 1 d . . . N4 N 0.7223(2) 0.40964(19) 0.24492(14) 0.0185(5) Uani 1 1 d . . . C1 C 0.9756(3) 0.1741(2) 0.37777(16) 0.0192(6) Uani 1 1 d . . . C2 C 0.9674(3) 0.0594(2) 0.37613(17) 0.0234(7) Uani 1 1 d . . . C3 C 1.0635(3) -0.0287(3) 0.40057(19) 0.0313(8) Uani 1 1 d . . . H3 H 1.0575 -0.1050 0.3974 0.038 Uiso 1 1 calc R . . C4 C 1.1669(3) -0.0047(3) 0.42932(19) 0.0322(8) Uani 1 1 d . . . H4 H 1.2330 -0.0644 0.4451 0.039 Uiso 1 1 calc R . . C5 C 1.1748(3) 0.1067(3) 0.43532(17) 0.0257(7) Uani 1 1 d . . . C6 C 1.0798(3) 0.1948(2) 0.41013(16) 0.0228(6) Uani 1 1 d . . . H6 H 1.0860 0.2706 0.4151 0.027 Uiso 1 1 calc R . . C7 C 1.2856(3) 0.1313(3) 0.46756(18) 0.0324(8) Uani 1 1 d . . . H7 H 1.3510 0.0695 0.4806 0.039 Uiso 1 1 calc R . . C8 C 0.8518(3) 0.0433(2) 0.34918(17) 0.0228(6) Uani 1 1 d . . . C9 C 0.8217(3) -0.0641(3) 0.34755(19) 0.0319(8) Uani 1 1 d . . . H9 H 0.8817 -0.1305 0.3602 0.038 Uiso 1 1 calc R . . C10 C 0.7085(3) -0.0735(3) 0.32814(19) 0.0339(8) Uani 1 1 d . . . H10 H 0.6902 -0.1461 0.3252 0.041 Uiso 1 1 calc R . . C11 C 0.6177(3) 0.0250(3) 0.31224(18) 0.0308(8) Uani 1 1 d . . . C12 C 0.6509(3) 0.1322(3) 0.31410(17) 0.0230(7) Uani 1 1 d . . . C13 C 0.5592(3) 0.2296(3) 0.30366(18) 0.0274(7) Uani 1 1 d . . . H13 H 0.5789 0.3016 0.3063 0.033 Uiso 1 1 calc R . . C14 C 0.4413(3) 0.2224(3) 0.2897(2) 0.0364(8) Uani 1 1 d . . . H14 H 0.3801 0.2894 0.2835 0.044 Uiso 1 1 calc R . . C15 C 0.4103(3) 0.1170(3) 0.2844(2) 0.0432(10) Uani 1 1 d . . . H15 H 0.3289 0.1132 0.2730 0.052 Uiso 1 1 calc R . . C16 C 0.4960(3) 0.0208(3) 0.2955(2) 0.0380(9) Uani 1 1 d . . . H16 H 0.4743 -0.0502 0.2920 0.046 Uiso 1 1 calc R . . C17 C 0.7570(2) 0.3317(2) 0.42487(16) 0.0181(6) Uani 1 1 d . . . C18 C 0.7781(3) 0.4342(2) 0.44775(17) 0.0197(6) Uani 1 1 d . . . C19 C 0.7117(3) 0.4827(2) 0.51366(18) 0.0254(7) Uani 1 1 d . . . H19 H 0.7265 0.5521 0.5276 0.031 Uiso 1 1 calc R . . C20 C 0.6260(3) 0.4305(2) 0.55769(17) 0.0243(7) Uani 1 1 d . . . H20 H 0.5807 0.4637 0.6017 0.029 Uiso 1 1 calc R . . C21 C 0.6056(3) 0.3272(2) 0.53720(16) 0.0202(6) Uani 1 1 d . . . C22 C 0.6706(3) 0.2804(2) 0.47227(16) 0.0191(6) Uani 1 1 d . . . H22 H 0.6559 0.2104 0.4594 0.023 Uiso 1 1 calc R . . C23 C 0.5120(3) 0.2685(3) 0.58123(17) 0.0242(7) Uani 1 1 d . . . H23 H 0.5078 0.1961 0.5669 0.029 Uiso 1 1 calc R . . C24 C 0.8733(3) 0.4811(2) 0.39902(17) 0.0220(6) Uani 1 1 d . . . C25 C 0.9167(3) 0.5768(3) 0.41664(19) 0.0285(7) Uani 1 1 d . . . H25 H 0.8765 0.6192 0.4582 0.034 Uiso 1 1 calc R . . C26 C 1.0152(3) 0.6080(3) 0.3744(2) 0.0312(8) Uani 1 1 d . . . H26 H 1.0441 0.6723 0.3863 0.037 Uiso 1 1 calc R . . C27 C 1.0753(3) 0.5456(3) 0.31289(19) 0.0266(7) Uani 1 1 d . . . C28 C 1.0272(3) 0.4526(2) 0.29491(17) 0.0224(7) Uani 1 1 d . . . C29 C 1.0875(3) 0.3887(3) 0.23495(18) 0.0276(7) Uani 1 1 d . . . H29 H 1.0571 0.3253 0.2228 0.033 Uiso 1 1 calc R . . C30 C 1.1901(3) 0.4168(3) 0.1935(2) 0.0337(8) Uani 1 1 d . . . H30 H 1.2295 0.3733 0.1523 0.040 Uiso 1 1 calc R . . C31 C 1.2375(3) 0.5089(3) 0.2112(2) 0.0370(8) Uani 1 1 d . . . H31 H 1.3090 0.5275 0.1824 0.044 Uiso 1 1 calc R . . C32 C 1.1810(3) 0.5717(3) 0.2695(2) 0.0337(8) Uani 1 1 d . . . H32 H 1.2134 0.6343 0.2811 0.040 Uiso 1 1 calc R . . C33 C 0.6445(3) 0.5016(2) 0.26564(17) 0.0220(6) Uani 1 1 d . . . H33 H 0.6378 0.5160 0.3202 0.026 Uiso 1 1 calc R . . C34 C 0.5727(3) 0.5775(3) 0.21070(18) 0.0265(7) Uani 1 1 d . . . H34 H 0.5188 0.6423 0.2278 0.032 Uiso 1 1 calc R . . C35 C 0.5805(3) 0.5581(3) 0.13236(18) 0.0270(7) Uani 1 1 d . . . H35 H 0.5306 0.6083 0.0947 0.032 Uiso 1 1 calc R . . C36 C 0.6624(3) 0.4638(3) 0.10767(18) 0.0240(7) Uani 1 1 d . . . C37 C 0.7342(3) 0.3924(2) 0.16604(17) 0.0191(6) Uani 1 1 d . . . C38 C 0.8247(3) 0.2991(2) 0.14366(17) 0.0193(6) Uani 1 1 d . . . C39 C 0.8365(3) 0.2740(3) 0.06369(17) 0.0256(7) Uani 1 1 d . . . C40 C 0.9258(3) 0.1804(3) 0.04501(19) 0.0334(8) Uani 1 1 d . . . H40 H 0.9355 0.1592 -0.0079 0.040 Uiso 1 1 calc R . . C41 C 0.9991(3) 0.1194(3) 0.10356(19) 0.0333(8) Uani 1 1 d . . . H41 H 1.0601 0.0560 0.0915 0.040 Uiso 1 1 calc R . . C42 C 0.9831(3) 0.1514(2) 0.18125(18) 0.0259(7) Uani 1 1 d . . . H42 H 1.0351 0.1090 0.2212 0.031 Uiso 1 1 calc R . . C43 C 0.7597(3) 0.3455(3) 0.00580(18) 0.0318(8) Uani 1 1 d . . . H43 H 0.7661 0.3281 -0.0480 0.038 Uiso 1 1 calc R . . C44 C 0.6785(3) 0.4368(3) 0.02622(18) 0.0290(7) Uani 1 1 d . . . H44 H 0.6309 0.4843 -0.0139 0.035 Uiso 1 1 calc R . . C45 C 0.5724(4) 0.1371(4) 0.0909(3) 0.0591(11) Uani 1 1 d . . . H45A H 0.6175 0.1731 0.1248 0.089 Uiso 1 1 calc R . . H45B H 0.6239 0.1173 0.0430 0.089 Uiso 1 1 calc R . . H45C H 0.5513 0.0684 0.1210 0.089 Uiso 1 1 calc R . . C46 C 0.4576(4) 0.2172(3) 0.0666(2) 0.0464(10) Uani 1 1 d . . . C47 C 0.3709(5) 0.1740(5) 0.0225(4) 0.0945(19) Uani 1 1 d . . . H47A H 0.3107 0.2377 -0.0013 0.142 Uiso 1 1 calc R . . H47B H 0.3281 0.1238 0.0594 0.142 Uiso 1 1 calc R . . H47C H 0.4161 0.1319 -0.0201 0.142 Uiso 1 1 calc R . . O1E O 0.1265(6) 0.2718(6) 0.9089(4) 0.0583(16) Uani 0.50 1 d PU A 1 C1E C 0.0536(8) 0.4511(7) 0.9590(5) 0.062(2) Uani 0.50 1 d PU A 1 H1E1 H -0.0076 0.4225 0.9968 0.093 Uiso 0.50 1 calc PR A 1 H1E2 H 0.0228 0.5309 0.9404 0.093 Uiso 0.50 1 calc PR A 1 H1E3 H 0.1305 0.4438 0.9857 0.093 Uiso 0.50 1 calc PR A 1 C2E C 0.0767(17) 0.3833(13) 0.8882(12) 0.056(3) Uani 0.50 1 d PU A 1 H2E1 H -0.0020 0.3885 0.8628 0.068 Uiso 0.50 1 calc PR A 1 H2E2 H 0.1330 0.4167 0.8481 0.068 Uiso 0.50 1 calc PR A 1 C3E C 0.154(2) 0.2045(13) 0.8496(9) 0.125(7) Uani 0.50 1 d PU A 1 H3E1 H 0.2157 0.2344 0.8115 0.150 Uiso 0.50 1 calc PR A 1 H3E2 H 0.0793 0.2096 0.8202 0.150 Uiso 0.50 1 calc PR A 1 C4E C 0.2004(19) 0.0916(13) 0.8736(12) 0.134(9) Uani 0.50 1 d PU A 1 H4E1 H 0.2904 0.0786 0.8723 0.201 Uiso 0.50 1 calc PR A 1 H4E2 H 0.1748 0.0445 0.8373 0.201 Uiso 0.50 1 calc PR A 1 H4E3 H 0.1687 0.0715 0.9284 0.201 Uiso 0.50 1 calc PR A 1 O1A O 0.1874(8) 0.2966(7) 0.7729(5) 0.121(3) Uani 0.50 1 d PDU B 2 C1A C 0.086(2) 0.3453(15) 0.8905(14) 0.105(8) Uani 0.50 1 d PDU B 2 H1A1 H 0.0850 0.4210 0.8619 0.157 Uiso 0.50 1 calc PR B 2 H1A2 H 0.1329 0.3360 0.9385 0.157 Uiso 0.50 1 calc PR B 2 H1A3 H 0.0010 0.3365 0.9063 0.157 Uiso 0.50 1 calc PR B 2 C2A C 0.1422(9) 0.2595(11) 0.8380(7) 0.068(3) Uani 0.50 1 d PDU B 2 C3A C 0.1538(12) 0.1367(12) 0.8668(9) 0.075(4) Uani 0.50 1 d PDU B 2 H3A1 H 0.0756 0.1133 0.8618 0.113 Uiso 0.50 1 calc PR B 2 H3A2 H 0.1750 0.1233 0.9231 0.113 Uiso 0.50 1 calc PR B 2 H3A3 H 0.2186 0.0926 0.8343 0.113 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01808(6) 0.01332(6) 0.01672(6) -0.00326(4) -0.00105(4) 0.00034(4) P1 0.0265(5) 0.0267(5) 0.0416(5) -0.0096(4) -0.0094(4) -0.0008(4) F1 0.0324(13) 0.0670(17) 0.101(2) 0.0007(14) -0.0121(13) -0.0149(11) F2 0.0520(14) 0.0384(12) 0.0629(14) -0.0251(11) -0.0115(11) 0.0059(10) F3 0.0581(15) 0.0643(16) 0.0464(13) 0.0016(11) -0.0193(11) -0.0039(12) F4 0.0658(15) 0.0481(14) 0.0414(13) -0.0108(10) -0.0168(11) 0.0093(11) F5 0.0579(14) 0.0312(12) 0.0824(17) -0.0239(11) -0.0338(13) 0.0109(10) F6 0.0343(12) 0.0656(16) 0.0731(16) -0.0159(12) 0.0040(11) -0.0157(11) O1 0.0409(15) 0.0516(17) 0.0496(16) -0.0106(13) -0.0088(12) -0.0065(13) O2 0.0382(14) 0.0324(13) 0.0316(13) -0.0118(10) 0.0126(11) -0.0070(11) O3 0.078(2) 0.049(2) 0.084(2) -0.0099(17) 0.0242(18) -0.0065(17) N1 0.0281(14) 0.0193(13) 0.0152(12) -0.0060(10) 0.0008(10) -0.0054(11) N2 0.0194(13) 0.0158(12) 0.0206(13) 0.0000(10) -0.0028(10) -0.0005(10) N3 0.0219(13) 0.0165(13) 0.0189(13) -0.0032(10) 0.0002(10) -0.0022(10) N4 0.0178(13) 0.0188(13) 0.0191(13) -0.0049(10) -0.0018(10) -0.0022(10) C1 0.0255(16) 0.0175(15) 0.0132(14) -0.0033(11) 0.0010(12) -0.0008(12) C2 0.0296(17) 0.0192(16) 0.0189(15) -0.0005(12) -0.0008(13) 0.0003(13) C3 0.039(2) 0.0173(16) 0.0344(19) -0.0027(14) -0.0009(15) 0.0014(14) C4 0.0317(19) 0.0274(18) 0.0299(18) 0.0000(14) -0.0042(15) 0.0116(14) C5 0.0242(17) 0.0282(18) 0.0207(16) -0.0012(13) -0.0014(13) 0.0037(13) C6 0.0262(17) 0.0216(16) 0.0186(15) -0.0022(12) -0.0024(13) 0.0005(13) C7 0.0304(19) 0.038(2) 0.0252(18) -0.0038(15) -0.0057(14) 0.0046(15) C8 0.0305(17) 0.0177(15) 0.0189(15) -0.0041(12) 0.0003(13) -0.0009(13) C9 0.045(2) 0.0186(17) 0.0318(19) -0.0042(14) -0.0015(16) -0.0049(15) C10 0.054(2) 0.0252(18) 0.0280(18) -0.0084(14) 0.0028(16) -0.0184(17) C11 0.044(2) 0.036(2) 0.0176(16) -0.0063(14) 0.0016(14) -0.0192(16) C12 0.0271(17) 0.0266(17) 0.0164(15) -0.0015(12) 0.0027(13) -0.0093(13) C13 0.0280(18) 0.0318(18) 0.0240(17) -0.0022(14) -0.0032(13) -0.0097(14) C14 0.0277(19) 0.047(2) 0.035(2) -0.0045(16) -0.0018(15) -0.0086(16) C15 0.037(2) 0.069(3) 0.032(2) -0.0079(18) -0.0038(16) -0.028(2) C16 0.045(2) 0.048(2) 0.0296(19) -0.0092(16) 0.0004(16) -0.0273(19) C17 0.0179(15) 0.0146(14) 0.0199(15) -0.0035(11) -0.0061(12) 0.0041(11) C18 0.0219(16) 0.0158(15) 0.0202(15) -0.0029(12) -0.0048(12) 0.0015(12) C19 0.0311(18) 0.0192(16) 0.0273(17) -0.0106(13) -0.0043(14) -0.0019(13) C20 0.0265(17) 0.0242(17) 0.0212(16) -0.0084(13) 0.0025(13) 0.0000(13) C21 0.0214(16) 0.0212(16) 0.0157(14) -0.0011(12) -0.0028(12) 0.0013(12) C22 0.0240(16) 0.0135(14) 0.0189(15) -0.0031(11) -0.0043(12) 0.0007(12) C23 0.0263(17) 0.0217(16) 0.0224(16) -0.0039(13) -0.0011(14) 0.0009(13) C24 0.0248(16) 0.0181(15) 0.0220(16) -0.0020(12) -0.0056(13) 0.0000(12) C25 0.0345(19) 0.0219(17) 0.0310(18) -0.0053(13) -0.0038(15) -0.0076(14) C26 0.038(2) 0.0189(16) 0.040(2) -0.0040(14) -0.0086(16) -0.0094(14) C27 0.0270(17) 0.0205(16) 0.0320(18) 0.0039(13) -0.0074(14) -0.0059(13) C28 0.0195(16) 0.0230(16) 0.0227(16) 0.0056(13) -0.0087(13) -0.0019(12) C29 0.0223(17) 0.0292(18) 0.0314(18) -0.0050(14) -0.0041(14) -0.0028(13) C30 0.0212(17) 0.044(2) 0.0335(19) -0.0018(15) 0.0036(14) -0.0034(15) C31 0.0246(18) 0.043(2) 0.043(2) 0.0070(17) -0.0008(16) -0.0125(16) C32 0.0336(19) 0.0340(19) 0.036(2) 0.0033(15) -0.0084(16) -0.0149(16) C33 0.0248(16) 0.0181(15) 0.0218(16) -0.0050(12) -0.0006(13) 0.0007(12) C34 0.0232(17) 0.0238(17) 0.0297(18) -0.0059(13) -0.0046(14) 0.0049(13) C35 0.0239(17) 0.0277(17) 0.0273(17) 0.0007(14) -0.0072(13) -0.0005(13) C36 0.0218(16) 0.0257(17) 0.0241(16) -0.0013(13) -0.0056(13) -0.0030(13) C37 0.0189(15) 0.0180(15) 0.0211(15) -0.0036(12) -0.0024(12) -0.0041(12) C38 0.0196(15) 0.0173(15) 0.0215(15) -0.0034(12) -0.0006(12) -0.0040(12) C39 0.0288(17) 0.0284(17) 0.0210(16) -0.0082(13) -0.0009(13) -0.0054(14) C40 0.039(2) 0.037(2) 0.0229(17) -0.0132(15) 0.0014(15) -0.0010(16) C41 0.036(2) 0.0289(18) 0.0307(19) -0.0106(15) 0.0044(15) 0.0066(15) C42 0.0285(17) 0.0208(16) 0.0248(17) -0.0039(13) 0.0011(13) 0.0034(13) C43 0.0355(19) 0.042(2) 0.0184(16) -0.0075(14) -0.0060(14) -0.0049(16) C44 0.0300(18) 0.0347(19) 0.0206(16) -0.0025(14) -0.0087(14) 0.0001(15) C45 0.051(3) 0.067(3) 0.056(3) -0.012(2) 0.009(2) -0.005(2) C46 0.052(2) 0.039(2) 0.044(2) -0.0025(18) 0.0122(19) -0.0050(19) C47 0.074(4) 0.077(4) 0.134(5) 0.006(4) -0.040(4) -0.017(3) O1E 0.071(5) 0.051(4) 0.046(4) 0.010(3) -0.010(3) -0.004(3) C1E 0.056(6) 0.043(4) 0.088(6) 0.004(4) -0.001(5) -0.019(4) C2E 0.048(7) 0.057(5) 0.060(6) 0.019(4) -0.018(5) -0.012(5) C3E 0.214(19) 0.082(8) 0.056(8) -0.001(6) 0.037(10) 0.004(11) C4E 0.21(2) 0.090(7) 0.074(10) -0.019(7) 0.003(12) 0.047(11) O1A 0.129(7) 0.116(7) 0.111(6) -0.012(5) 0.042(5) -0.026(6) C1A 0.118(16) 0.109(15) 0.080(12) -0.008(12) 0.002(10) -0.007(14) C2A 0.029(5) 0.130(8) 0.043(5) -0.009(5) -0.017(4) -0.007(5) C3A 0.057(7) 0.120(9) 0.055(7) -0.026(8) 0.000(6) -0.021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C17 1.987(3) . ? Ir1 C1 1.996(3) . ? Ir1 N1 2.091(2) . ? Ir1 N2 2.091(2) . ? Ir1 N4 2.172(2) . ? Ir1 N3 2.197(2) . ? P1 F6 1.582(2) . ? P1 F5 1.588(2) . ? P1 F2 1.589(2) . ? P1 F1 1.591(2) . ? P1 F3 1.596(2) . ? P1 F4 1.599(2) . ? O1 C7 1.214(4) . ? O2 C23 1.198(4) . ? O3 C46 1.214(4) . ? N1 C8 1.350(4) . ? N1 C12 1.383(4) . ? N2 C24 1.350(4) . ? N2 C28 1.391(4) . ? N3 C42 1.327(4) . ? N3 C38 1.366(3) . ? N4 C33 1.333(4) . ? N4 C37 1.362(4) . ? C1 C6 1.395(4) . ? C1 C2 1.417(4) . ? C2 C3 1.397(4) . ? C2 C8 1.451(4) . ? C3 C4 1.377(4) . ? C3 H3 0.9500 . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 C6 1.393(4) . ? C5 C7 1.480(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.413(4) . ? C9 C10 1.355(5) . ? C9 H9 0.9500 . ? C10 C11 1.413(5) . ? C10 H10 0.9500 . ? C11 C16 1.415(5) . ? C11 C12 1.426(4) . ? C12 C13 1.399(4) . ? C13 C14 1.371(4) . ? C13 H13 0.9500 . ? C14 C15 1.404(5) . ? C14 H14 0.9500 . ? C15 C16 1.354(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.394(4) . ? C17 C18 1.414(4) . ? C18 C19 1.409(4) . ? C18 C24 1.451(4) . ? C19 C20 1.369(4) . ? C19 H19 0.9500 . ? C20 C21 1.405(4) . ? C20 H20 0.9500 . ? C21 C22 1.382(4) . ? C21 C23 1.478(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.415(4) . ? C25 C26 1.352(4) . ? C25 H25 0.9500 . ? C26 C27 1.406(5) . ? C26 H26 0.9500 . ? C27 C32 1.405(4) . ? C27 C28 1.416(4) . ? C28 C29 1.397(4) . ? C29 C30 1.371(4) . ? C29 H29 0.9500 . ? C30 C31 1.400(5) . ? C30 H30 0.9500 . ? C31 C32 1.356(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.394(4) . ? C33 H33 0.9500 . ? C34 C35 1.361(4) . ? C34 H34 0.9500 . ? C35 C36 1.398(4) . ? C35 H35 0.9500 . ? C36 C37 1.407(4) . ? C36 C44 1.438(4) . ? C37 C38 1.424(4) . ? C38 C39 1.407(4) . ? C39 C40 1.402(4) . ? C39 C43 1.431(4) . ? C40 C41 1.371(4) . ? C40 H40 0.9500 . ? C41 C42 1.399(4) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 C44 1.344(4) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.491(5) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.472(6) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? O1E C3E 1.347(16) . ? O1E C2E 1.368(16) . ? C1E C2E 1.509(18) . ? C1E H1E1 0.9800 . ? C1E H1E2 0.9800 . ? C1E H1E3 0.9800 . ? C2E H2E1 0.9900 . ? C2E H2E2 0.9900 . ? C3E C4E 1.384(18) . ? C3E H3E1 0.9900 . ? C3E H3E2 0.9900 . ? C4E H4E1 0.9800 . ? C4E H4E2 0.9800 . ? C4E H4E3 0.9800 . ? O1A C2A 1.240(11) . ? C1A C2A 1.464(16) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2A C3A 1.492(14) . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 Ir1 C1 93.50(11) . . ? C17 Ir1 N1 93.62(10) . . ? C1 Ir1 N1 79.67(10) . . ? C17 Ir1 N2 79.56(10) . . ? C1 Ir1 N2 92.38(10) . . ? N1 Ir1 N2 169.26(8) . . ? C17 Ir1 N4 95.73(10) . . ? C1 Ir1 N4 169.71(10) . . ? N1 Ir1 N4 104.22(9) . . ? N2 Ir1 N4 84.85(8) . . ? C17 Ir1 N3 168.17(9) . . ? C1 Ir1 N3 95.61(10) . . ? N1 Ir1 N3 80.64(8) . . ? N2 Ir1 N3 107.53(9) . . ? N4 Ir1 N3 75.88(9) . . ? F6 P1 F5 90.75(13) . . ? F6 P1 F2 90.00(12) . . ? F5 P1 F2 179.01(14) . . ? F6 P1 F1 179.29(14) . . ? F5 P1 F1 89.87(13) . . ? F2 P1 F1 89.39(13) . . ? F6 P1 F3 89.76(12) . . ? F5 P1 F3 89.27(13) . . ? F2 P1 F3 90.08(13) . . ? F1 P1 F3 90.61(13) . . ? F6 P1 F4 90.67(13) . . ? F5 P1 F4 90.69(12) . . ? F2 P1 F4 89.95(12) . . ? F1 P1 F4 88.97(13) . . ? F3 P1 F4 179.57(13) . . ? C8 N1 C12 119.5(2) . . ? C8 N1 Ir1 113.50(19) . . ? C12 N1 Ir1 126.94(19) . . ? C24 N2 C28 118.9(2) . . ? C24 N2 Ir1 114.33(18) . . ? C28 N2 Ir1 126.69(19) . . ? C42 N3 C38 118.0(2) . . ? C42 N3 Ir1 127.79(19) . . ? C38 N3 Ir1 113.59(19) . . ? C33 N4 C37 117.9(2) . . ? C33 N4 Ir1 127.08(19) . . ? C37 N4 Ir1 114.95(18) . . ? C6 C1 C2 117.1(3) . . ? C6 C1 Ir1 128.0(2) . . ? C2 C1 Ir1 114.6(2) . . ? C3 C2 C1 121.2(3) . . ? C3 C2 C8 124.4(3) . . ? C1 C2 C8 114.4(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.1(3) . . ? C4 C5 C7 119.6(3) . . ? C6 C5 C7 120.3(3) . . ? C5 C6 C1 121.4(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O1 C7 C5 124.2(3) . . ? O1 C7 H7 117.9 . . ? C5 C7 H7 117.9 . . ? N1 C8 C9 120.8(3) . . ? N1 C8 C2 115.5(2) . . ? C9 C8 C2 123.6(3) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C16 122.5(3) . . ? C10 C11 C12 118.1(3) . . ? C16 C11 C12 119.3(3) . . ? N1 C12 C13 121.0(3) . . ? N1 C12 C11 120.7(3) . . ? C13 C12 C11 118.3(3) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.6(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C22 C17 C18 116.5(3) . . ? C22 C17 Ir1 127.6(2) . . ? C18 C17 Ir1 115.6(2) . . ? C19 C18 C17 121.1(3) . . ? C19 C18 C24 124.6(3) . . ? C17 C18 C24 114.3(3) . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.4(3) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 119.8(3) . . ? C22 C21 C23 118.3(3) . . ? C20 C21 C23 121.8(3) . . ? C21 C22 C17 122.7(3) . . ? C21 C22 H22 118.7 . . ? C17 C22 H22 118.7 . . ? O2 C23 C21 125.6(3) . . ? O2 C23 H23 117.2 . . ? C21 C23 H23 117.2 . . ? N2 C24 C25 121.4(3) . . ? N2 C24 C18 115.2(2) . . ? C25 C24 C18 123.2(3) . . ? C26 C25 C24 120.1(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C32 C27 C26 122.6(3) . . ? C32 C27 C28 119.2(3) . . ? C26 C27 C28 118.3(3) . . ? N2 C28 C29 120.3(3) . . ? N2 C28 C27 120.9(3) . . ? C29 C28 C27 118.7(3) . . ? C30 C29 C28 120.6(3) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 120.6(3) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C32 C31 C30 119.9(3) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C27 121.0(3) . . ? C31 C32 H32 119.5 . . ? C27 C32 H32 119.5 . . ? N4 C33 C34 122.8(3) . . ? N4 C33 H33 118.6 . . ? C34 C33 H33 118.6 . . ? C35 C34 C33 119.5(3) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 119.6(3) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C35 C36 C37 117.7(3) . . ? C35 C36 C44 123.8(3) . . ? C37 C36 C44 118.5(3) . . ? N4 C37 C36 122.3(3) . . ? N4 C37 C38 117.3(2) . . ? C36 C37 C38 120.3(3) . . ? N3 C38 C39 122.7(3) . . ? N3 C38 C37 117.7(2) . . ? C39 C38 C37 119.6(3) . . ? C40 C39 C38 117.4(3) . . ? C40 C39 C43 123.5(3) . . ? C38 C39 C43 119.1(3) . . ? C41 C40 C39 119.6(3) . . ? C41 C40 H40 120.2 . . ? C39 C40 H40 120.2 . . ? C40 C41 C42 119.4(3) . . ? C40 C41 H41 120.3 . . ? C42 C41 H41 120.3 . . ? N3 C42 C41 122.8(3) . . ? N3 C42 H42 118.6 . . ? C41 C42 H42 118.6 . . ? C44 C43 C39 121.2(3) . . ? C44 C43 H43 119.4 . . ? C39 C43 H43 119.4 . . ? C43 C44 C36 121.2(3) . . ? C43 C44 H44 119.4 . . ? C36 C44 H44 119.4 . . ? C46 C45 H45A 109.5 . . ? C46 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C46 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O3 C46 C47 121.9(4) . . ? O3 C46 C45 120.7(4) . . ? C47 C46 C45 117.4(4) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C3E O1E C2E 117.6(13) . . ? O1E C2E C1E 112.8(14) . . ? O1E C2E H2E1 109.0 . . ? C1E C2E H2E1 109.0 . . ? O1E C2E H2E2 109.0 . . ? C1E C2E H2E2 109.0 . . ? H2E1 C2E H2E2 107.8 . . ? O1E C3E C4E 115.6(15) . . ? O1E C3E H3E1 108.4 . . ? C4E C3E H3E1 108.4 . . ? O1E C3E H3E2 108.4 . . ? C4E C3E H3E2 108.4 . . ? H3E1 C3E H3E2 107.4 . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? O1A C2A C1A 115.3(15) . . ? O1A C2A C3A 124.0(12) . . ? C1A C2A C3A 120.5(14) . . ? C2A C3A H3A1 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C2A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.113 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.075