# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_complex2 _database_code_depnum_ccdc_archive 'CCDC 857584' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H36 F4 Ir N5' _chemical_formula_weight 866.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.524(2) _cell_length_b 13.963(3) _cell_length_c 14.858(3) _cell_angle_alpha 73.185(3) _cell_angle_beta 74.497(3) _cell_angle_gamma 73.671(3) _cell_volume 1777.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 252 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 3.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3107 _exptl_absorpt_correction_T_max 0.3941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9323 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.07 _reflns_number_total 6124 _reflns_number_gt 5044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6124 _refine_ls_number_parameters 464 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.22297(3) 0.79931(2) 0.28967(2) 0.02029(12) Uani 1 1 d . . . F1 F -0.1946(6) 0.8691(4) 0.6038(4) 0.0470(14) Uani 1 1 d . . . F2 F -0.1431(6) 1.1470(4) 0.3432(4) 0.0498(14) Uani 1 1 d . . . F3 F 0.5295(6) 0.7045(4) 0.5622(4) 0.0545(15) Uani 1 1 d . . . F4 F 0.5879(6) 1.0086(4) 0.3372(4) 0.0499(15) Uani 1 1 d . . . N1 N 0.2477(7) 0.6715(5) 0.3962(5) 0.0257(15) Uani 1 1 d . . . N2 N 0.1963(7) 0.9387(5) 0.1969(5) 0.0228(14) Uani 1 1 d . . . N3 N 0.1006(7) 0.7461(5) 0.2192(5) 0.0238(15) Uani 1 1 d . . . N4 N 0.3447(7) 0.7114(4) 0.1812(5) 0.0212(14) Uani 1 1 d . . . N5 N 0.2167(7) 0.6432(5) 0.1026(5) 0.0294(16) Uani 1 1 d . . . C1 C 0.3709(8) 0.8280(6) 0.3481(6) 0.0234(18) Uani 1 1 d . . . C2 C 0.0609(8) 0.8809(5) 0.3721(6) 0.0222(17) Uani 1 1 d . . . C3 C 0.4038(8) 0.7556(6) 0.4316(5) 0.0235(17) Uani 1 1 d . . . C4 C 0.4976(9) 0.7722(7) 0.4803(6) 0.034(2) Uani 1 1 d . . . C5 C 0.5606(9) 0.8559(7) 0.4503(7) 0.037(2) Uani 1 1 d . . . H15 H 0.6241 0.8656 0.4850 0.044 Uiso 1 1 calc R . . C6 C 0.5278(9) 0.9248(7) 0.3683(7) 0.035(2) Uani 1 1 d . . . C7 C 0.4353(8) 0.9134(6) 0.3162(6) 0.0270(18) Uani 1 1 d . . . H17 H 0.4157 0.9631 0.2593 0.032 Uiso 1 1 calc R . . C8 C 0.3321(9) 0.6686(6) 0.4601(6) 0.033(2) Uani 1 1 d . . . C9 C 0.3453(10) 0.5871(8) 0.5380(7) 0.047(3) Uani 1 1 d . . . H19 H 0.4021 0.5853 0.5824 0.056 Uiso 1 1 calc R . . C10 C 0.2762(12) 0.5075(8) 0.5521(8) 0.062(3) Uani 1 1 d . . . H20 H 0.2851 0.4512 0.6060 0.074 Uiso 1 1 calc R . . C11 C 0.1943(10) 0.5109(7) 0.4869(7) 0.043(2) Uani 1 1 d . . . H21 H 0.1477 0.4564 0.4947 0.051 Uiso 1 1 calc R . . C12 C 0.1814(8) 0.5933(6) 0.4116(6) 0.0288(19) Uani 1 1 d . . . H22 H 0.1231 0.5958 0.3678 0.035 Uiso 1 1 calc R . . C13 C 0.0163(9) 0.9837(6) 0.3295(6) 0.0268(18) Uani 1 1 d . . . C14 C -0.0987(9) 1.0453(6) 0.3820(7) 0.031(2) Uani 1 1 d . . . C15 C -0.1713(9) 1.0092(7) 0.4726(7) 0.034(2) Uani 1 1 d . . . H4 H -0.2508 1.0524 0.5062 0.040 Uiso 1 1 calc R . . C16 C -0.1239(9) 0.9067(7) 0.5133(6) 0.032(2) Uani 1 1 d . . . C17 C -0.0115(8) 0.8420(6) 0.4668(6) 0.0262(18) Uani 1 1 d . . . H2 H 0.0177 0.7718 0.4976 0.031 Uiso 1 1 calc R . . C18 C 0.0938(8) 1.0166(6) 0.2311(6) 0.0260(18) Uani 1 1 d . . . C19 C 0.0724(10) 1.1142(6) 0.1710(7) 0.037(2) Uani 1 1 d . . . H8 H -0.0007 1.1689 0.1933 0.045 Uiso 1 1 calc R . . C20 C 0.1562(11) 1.1317(7) 0.0797(8) 0.048(3) Uani 1 1 d . . . H10 H 0.1426 1.1988 0.0393 0.058 Uiso 1 1 calc R . . C21 C 0.2597(10) 1.0525(7) 0.0465(7) 0.043(2) Uani 1 1 d . . . H9 H 0.3180 1.0635 -0.0168 0.051 Uiso 1 1 calc R . . C22 C 0.2768(9) 0.9573(6) 0.1070(6) 0.0295(19) Uani 1 1 d . . . H11 H 0.3485 0.9021 0.0846 0.035 Uiso 1 1 calc R . . C23 C 0.2219(9) 0.6986(6) 0.1672(6) 0.0250(18) Uani 1 1 d . . . C24 C -0.0520(8) 0.7652(6) 0.2027(6) 0.0254(18) Uani 1 1 d . . . H24 H -0.0468 0.7375 0.1466 0.030 Uiso 1 1 calc R . . C25 C -0.1190(10) 0.8793(6) 0.1802(7) 0.037(2) Uani 1 1 d . . . H25A H -0.1210 0.9078 0.2337 0.056 Uiso 1 1 calc R . . H25B H -0.2211 0.8911 0.1708 0.056 Uiso 1 1 calc R . . H25C H -0.0583 0.9129 0.1216 0.056 Uiso 1 1 calc R . . C26 C -0.1460(9) 0.7093(7) 0.2909(7) 0.038(2) Uani 1 1 d . . . H26A H -0.1043 0.6352 0.3007 0.057 Uiso 1 1 calc R . . H26B H -0.2488 0.7242 0.2816 0.057 Uiso 1 1 calc R . . H26C H -0.1458 0.7322 0.3472 0.057 Uiso 1 1 calc R . . C27 C 0.4923(8) 0.6486(6) 0.1521(6) 0.0276(19) Uani 1 1 d . . . H27 H 0.4820 0.5989 0.1188 0.033 Uiso 1 1 calc R . . C28 C 0.5556(10) 0.5893(7) 0.2408(7) 0.042(2) Uani 1 1 d . . . H28A H 0.5594 0.6374 0.2764 0.063 Uiso 1 1 calc R . . H28B H 0.6566 0.5495 0.2216 0.063 Uiso 1 1 calc R . . H28C H 0.4916 0.5428 0.2818 0.063 Uiso 1 1 calc R . . C29 C 0.5968(9) 0.7168(7) 0.0823(8) 0.052(3) Uani 1 1 d . . . H29A H 0.5537 0.7547 0.0257 0.077 Uiso 1 1 calc R . . H29B H 0.6948 0.6736 0.0624 0.077 Uiso 1 1 calc R . . H29C H 0.6084 0.7654 0.1146 0.077 Uiso 1 1 calc R . . C30 C 0.1554(9) 0.5535(6) 0.1425(7) 0.033(2) Uani 1 1 d . . . C31 C 0.2009(11) 0.4848(7) 0.2219(8) 0.045(2) Uani 1 1 d . . . H33 H 0.2748 0.4957 0.2476 0.054 Uiso 1 1 calc R . . C32 C 0.1387(15) 0.3989(8) 0.2649(9) 0.070(4) Uani 1 1 d . . . H39 H 0.1701 0.3516 0.3199 0.084 Uiso 1 1 calc R . . C33 C 0.0332(15) 0.3827(9) 0.2281(10) 0.076(4) Uani 1 1 d . . . H42 H -0.0109 0.3252 0.2582 0.092 Uiso 1 1 calc R . . C34 C -0.0092(13) 0.4504(10) 0.1469(9) 0.064(3) Uani 1 1 d . . . H41 H -0.0801 0.4378 0.1198 0.077 Uiso 1 1 calc R . . C35 C 0.0498(10) 0.5360(7) 0.1046(7) 0.043(2) Uani 1 1 d . . . H36 H 0.0180 0.5829 0.0495 0.052 Uiso 1 1 calc R . . C36 C 0.2659(8) 0.6781(6) 0.0034(6) 0.0282(19) Uani 1 1 d . . . C37 C 0.3330(9) 0.6112(7) -0.0566(7) 0.039(2) Uani 1 1 d . . . H34 H 0.3429 0.5394 -0.0313 0.047 Uiso 1 1 calc R . . C38 C 0.3854(11) 0.6483(8) -0.1528(8) 0.051(3) Uani 1 1 d . . . H37 H 0.4303 0.6015 -0.1933 0.062 Uiso 1 1 calc R . . C39 C 0.3743(11) 0.7508(8) -0.1912(7) 0.052(3) Uani 1 1 d . . . H40 H 0.4132 0.7752 -0.2574 0.062 Uiso 1 1 calc R . . C40 C 0.3054(11) 0.8188(8) -0.1322(7) 0.048(3) Uani 1 1 d . . . H38 H 0.2958 0.8905 -0.1581 0.057 Uiso 1 1 calc R . . C41 C 0.2509(10) 0.7827(6) -0.0363(6) 0.037(2) Uani 1 1 d . . . H35 H 0.2023 0.8299 0.0033 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01898(17) 0.02366(17) 0.01571(18) -0.00309(12) 0.00263(12) -0.00809(11) F1 0.041(3) 0.066(4) 0.031(3) -0.021(3) 0.019(3) -0.021(3) F2 0.049(3) 0.038(3) 0.050(4) -0.013(3) -0.005(3) 0.006(2) F3 0.056(4) 0.066(4) 0.045(4) -0.002(3) -0.027(3) -0.015(3) F4 0.047(3) 0.055(3) 0.060(4) -0.015(3) -0.007(3) -0.032(3) N1 0.014(3) 0.033(4) 0.024(4) -0.009(3) 0.006(3) -0.003(3) N2 0.028(4) 0.028(3) 0.013(4) 0.002(3) -0.003(3) -0.014(3) N3 0.020(3) 0.030(3) 0.024(4) -0.008(3) 0.001(3) -0.013(3) N4 0.020(3) 0.022(3) 0.018(4) -0.007(3) 0.004(3) -0.004(3) N5 0.028(4) 0.030(4) 0.031(4) -0.015(3) 0.004(3) -0.009(3) C1 0.019(4) 0.034(4) 0.022(5) -0.015(4) 0.005(3) -0.013(3) C2 0.025(4) 0.023(4) 0.019(4) -0.004(3) 0.001(3) -0.010(3) C3 0.017(4) 0.035(4) 0.012(4) -0.006(4) 0.005(3) -0.004(3) C4 0.025(5) 0.047(5) 0.025(5) -0.008(4) -0.003(4) -0.002(4) C5 0.021(4) 0.060(6) 0.038(6) -0.030(5) 0.003(4) -0.011(4) C6 0.028(5) 0.041(5) 0.036(6) -0.018(5) 0.011(4) -0.016(4) C7 0.023(4) 0.036(5) 0.024(5) -0.012(4) 0.002(4) -0.010(3) C8 0.023(4) 0.041(5) 0.028(5) 0.001(4) -0.002(4) -0.010(4) C9 0.035(5) 0.066(6) 0.035(6) 0.012(5) -0.013(5) -0.022(5) C10 0.055(7) 0.065(7) 0.058(8) 0.032(6) -0.026(6) -0.032(6) C11 0.029(5) 0.039(5) 0.052(7) 0.008(5) -0.005(5) -0.015(4) C12 0.020(4) 0.029(4) 0.032(5) -0.003(4) 0.002(4) -0.009(3) C13 0.025(4) 0.035(4) 0.023(5) -0.010(4) -0.004(4) -0.008(3) C14 0.030(5) 0.028(4) 0.039(6) -0.014(4) -0.008(4) -0.005(4) C15 0.020(4) 0.047(5) 0.037(6) -0.025(5) 0.004(4) -0.006(4) C16 0.029(5) 0.048(5) 0.027(5) -0.013(4) 0.003(4) -0.021(4) C17 0.026(4) 0.032(4) 0.018(4) -0.007(4) 0.005(4) -0.009(3) C18 0.024(4) 0.026(4) 0.027(5) -0.006(4) -0.004(4) -0.005(3) C19 0.037(5) 0.029(5) 0.035(6) 0.001(4) -0.003(4) -0.004(4) C20 0.053(6) 0.029(5) 0.045(7) 0.010(5) -0.002(5) -0.008(4) C21 0.046(6) 0.045(5) 0.029(6) 0.002(5) 0.001(5) -0.016(4) C22 0.034(5) 0.032(4) 0.019(5) 0.004(4) -0.004(4) -0.013(4) C23 0.027(4) 0.030(4) 0.018(5) -0.005(4) 0.001(4) -0.012(3) C24 0.024(4) 0.037(4) 0.014(4) -0.006(4) 0.001(3) -0.011(3) C25 0.035(5) 0.039(5) 0.039(6) -0.005(4) -0.014(4) -0.008(4) C26 0.023(5) 0.047(5) 0.039(6) 0.001(5) -0.001(4) -0.015(4) C27 0.022(4) 0.034(4) 0.023(5) -0.004(4) 0.001(4) -0.010(3) C28 0.030(5) 0.042(5) 0.052(7) -0.013(5) -0.009(5) -0.001(4) C29 0.019(5) 0.058(6) 0.057(7) 0.002(6) 0.007(5) -0.008(4) C30 0.029(5) 0.030(4) 0.036(6) -0.014(4) 0.009(4) -0.009(4) C31 0.043(6) 0.032(5) 0.053(7) -0.013(5) 0.004(5) -0.007(4) C32 0.112(11) 0.046(6) 0.048(8) -0.008(6) 0.007(7) -0.036(7) C33 0.112(11) 0.064(8) 0.065(9) -0.028(7) 0.023(8) -0.063(8) C34 0.066(8) 0.088(9) 0.061(8) -0.040(8) 0.010(6) -0.051(7) C35 0.035(5) 0.056(6) 0.043(6) -0.028(5) 0.012(5) -0.017(4) C36 0.019(4) 0.037(5) 0.028(5) -0.015(4) 0.003(4) -0.004(3) C37 0.031(5) 0.036(5) 0.046(6) -0.018(5) 0.009(5) -0.006(4) C38 0.057(7) 0.056(7) 0.036(6) -0.023(5) 0.013(5) -0.015(5) C39 0.063(7) 0.071(7) 0.015(5) -0.008(5) 0.006(5) -0.019(6) C40 0.055(7) 0.044(6) 0.033(6) -0.009(5) 0.006(5) -0.008(5) C41 0.048(6) 0.032(5) 0.022(5) -0.004(4) -0.005(4) -0.001(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 Ir1 C2 1.997(8) . ? Ir1 C1 2.018(7) . ? Ir1 N1 2.019(7) . ? Ir1 N2 2.028(6) . ? Ir1 N3 2.143(6) . ? Ir1 N4 2.190(6) . ? Ir1 C23 2.606(8) . ? F1 C16 1.357(10) . ? F2 C14 1.358(9) . ? F3 C4 1.356(10) . ? F4 C6 1.355(9) . ? N1 C12 1.345(9) . ? N1 C8 1.384(10) . ? N2 C22 1.342(10) . ? N2 C18 1.361(10) . ? N3 C23 1.328(10) . ? N3 C24 1.476(9) . ? N4 C23 1.309(9) . ? N4 C27 1.461(10) . ? N5 C36 1.404(11) . ? N5 C23 1.413(10) . ? N5 C30 1.434(10) . ? C1 C7 1.397(10) . ? C1 C3 1.401(11) . ? C2 C13 1.384(11) . ? C2 C17 1.415(11) . ? C3 C4 1.391(11) . ? C3 C8 1.461(11) . ? C4 C5 1.369(12) . ? C5 C6 1.365(13) . ? C5 H15 0.9500 . ? C6 C7 1.384(11) . ? C7 H17 0.9500 . ? C8 C9 1.373(12) . ? C9 C10 1.383(13) . ? C9 H19 0.9500 . ? C10 C11 1.380(13) . ? C10 H20 0.9500 . ? C11 C12 1.356(12) . ? C11 H21 0.9500 . ? C12 H22 0.9500 . ? C13 C14 1.397(11) . ? C13 C18 1.456(11) . ? C14 C15 1.360(12) . ? C15 C16 1.378(12) . ? C15 H4 0.9500 . ? C16 C17 1.364(11) . ? C17 H2 0.9500 . ? C18 C19 1.390(11) . ? C19 C20 1.370(13) . ? C19 H8 0.9500 . ? C20 C21 1.372(13) . ? C20 H10 0.9500 . ? C21 C22 1.366(11) . ? C21 H9 0.9500 . ? C22 H11 0.9500 . ? C24 C25 1.514(11) . ? C24 C26 1.517(11) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.517(12) . ? C27 C29 1.543(11) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.372(13) . ? C30 C35 1.381(12) . ? C31 C32 1.397(13) . ? C31 H33 0.9500 . ? C32 C33 1.360(16) . ? C32 H39 0.9500 . ? C33 C34 1.377(17) . ? C33 H42 0.9500 . ? C34 C35 1.376(14) . ? C34 H41 0.9500 . ? C35 H36 0.9500 . ? C36 C37 1.386(11) . ? C36 C41 1.389(12) . ? C37 C38 1.377(13) . ? C37 H34 0.9500 . ? C38 C39 1.364(14) . ? C38 H37 0.9500 . ? C39 C40 1.388(13) . ? C39 H40 0.9500 . ? C40 C41 1.374(13) . ? C40 H38 0.9500 . ? C41 H35 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Ir1 C1 87.8(3) . . ? C2 Ir1 N1 94.2(3) . . ? C1 Ir1 N1 80.1(3) . . ? C2 Ir1 N2 79.8(3) . . ? C1 Ir1 N2 93.9(3) . . ? N1 Ir1 N2 171.8(2) . . ? C2 Ir1 N3 102.7(3) . . ? C1 Ir1 N3 169.1(3) . . ? N1 Ir1 N3 95.7(2) . . ? N2 Ir1 N3 91.1(2) . . ? C2 Ir1 N4 162.9(3) . . ? C1 Ir1 N4 109.1(3) . . ? N1 Ir1 N4 91.2(2) . . ? N2 Ir1 N4 96.1(2) . . ? N3 Ir1 N4 60.6(2) . . ? C2 Ir1 C23 133.2(3) . . ? C1 Ir1 C23 139.0(3) . . ? N1 Ir1 C23 93.1(2) . . ? N2 Ir1 C23 95.1(2) . . ? N3 Ir1 C23 30.5(2) . . ? N4 Ir1 C23 30.1(2) . . ? C12 N1 C8 118.9(7) . . ? C12 N1 Ir1 124.4(5) . . ? C8 N1 Ir1 116.6(5) . . ? C22 N2 C18 119.9(6) . . ? C22 N2 Ir1 123.6(5) . . ? C18 N2 Ir1 116.5(5) . . ? C23 N3 C24 124.0(6) . . ? C23 N3 Ir1 94.4(4) . . ? C24 N3 Ir1 140.0(5) . . ? C23 N4 C27 123.2(6) . . ? C23 N4 Ir1 92.8(5) . . ? C27 N4 Ir1 140.1(5) . . ? C36 N5 C23 120.2(6) . . ? C36 N5 C30 122.5(7) . . ? C23 N5 C30 117.3(7) . . ? C7 C1 C3 118.8(7) . . ? C7 C1 Ir1 126.6(6) . . ? C3 C1 Ir1 114.6(5) . . ? C13 C2 C17 119.0(7) . . ? C13 C2 Ir1 115.3(6) . . ? C17 C2 Ir1 125.7(6) . . ? C4 C3 C1 118.7(7) . . ? C4 C3 C8 125.9(7) . . ? C1 C3 C8 115.3(7) . . ? F3 C4 C5 116.6(7) . . ? F3 C4 C3 120.1(7) . . ? C5 C4 C3 123.2(8) . . ? C6 C5 C4 116.9(8) . . ? C6 C5 H15 121.6 . . ? C4 C5 H15 121.6 . . ? F4 C6 C5 118.2(7) . . ? F4 C6 C7 118.7(8) . . ? C5 C6 C7 123.2(7) . . ? C6 C7 C1 119.3(8) . . ? C6 C7 H17 120.4 . . ? C1 C7 H17 120.4 . . ? C9 C8 N1 119.7(7) . . ? C9 C8 C3 127.4(8) . . ? N1 C8 C3 112.8(7) . . ? C8 C9 C10 120.3(9) . . ? C8 C9 H19 119.9 . . ? C10 C9 H19 119.9 . . ? C11 C10 C9 119.3(9) . . ? C11 C10 H20 120.4 . . ? C9 C10 H20 120.4 . . ? C12 C11 C10 119.0(8) . . ? C12 C11 H21 120.5 . . ? C10 C11 H21 120.5 . . ? N1 C12 C11 122.9(8) . . ? N1 C12 H22 118.6 . . ? C11 C12 H22 118.6 . . ? C2 C13 C14 118.6(8) . . ? C2 C13 C18 115.4(7) . . ? C14 C13 C18 126.0(7) . . ? F2 C14 C15 116.6(8) . . ? F2 C14 C13 120.1(8) . . ? C15 C14 C13 123.3(8) . . ? C14 C15 C16 116.8(8) . . ? C14 C15 H4 121.6 . . ? C16 C15 H4 121.6 . . ? F1 C16 C17 119.1(8) . . ? F1 C16 C15 117.7(8) . . ? C17 C16 C15 123.3(8) . . ? C16 C17 C2 119.0(7) . . ? C16 C17 H2 120.5 . . ? C2 C17 H2 120.5 . . ? N2 C18 C19 119.0(8) . . ? N2 C18 C13 113.0(6) . . ? C19 C18 C13 128.0(8) . . ? C20 C19 C18 120.3(8) . . ? C20 C19 H8 119.9 . . ? C18 C19 H8 119.9 . . ? C19 C20 C21 120.0(8) . . ? C19 C20 H10 120.0 . . ? C21 C20 H10 120.0 . . ? C22 C21 C20 118.2(9) . . ? C22 C21 H9 120.9 . . ? C20 C21 H9 120.9 . . ? N2 C22 C21 122.6(8) . . ? N2 C22 H11 118.7 . . ? C21 C22 H11 118.7 . . ? N4 C23 N3 112.1(7) . . ? N4 C23 N5 124.7(7) . . ? N3 C23 N5 123.2(7) . . ? N4 C23 Ir1 57.0(4) . . ? N3 C23 Ir1 55.1(4) . . ? N5 C23 Ir1 178.1(6) . . ? N3 C24 C25 110.1(6) . . ? N3 C24 C26 109.0(6) . . ? C25 C24 C26 111.3(7) . . ? N3 C24 H24 108.8 . . ? C25 C24 H24 108.8 . . ? C26 C24 H24 108.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 C28 109.0(7) . . ? N4 C27 C29 110.3(7) . . ? C28 C27 C29 110.8(7) . . ? N4 C27 H27 108.9 . . ? C28 C27 H27 108.9 . . ? C29 C27 H27 108.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C35 119.4(8) . . ? C31 C30 N5 118.7(8) . . ? C35 C30 N5 121.8(8) . . ? C30 C31 C32 120.1(10) . . ? C30 C31 H33 119.9 . . ? C32 C31 H33 119.9 . . ? C33 C32 C31 120.2(12) . . ? C33 C32 H39 119.9 . . ? C31 C32 H39 119.9 . . ? C32 C33 C34 119.5(10) . . ? C32 C33 H42 120.3 . . ? C34 C33 H42 120.3 . . ? C35 C34 C33 120.8(10) . . ? C35 C34 H41 119.6 . . ? C33 C34 H41 119.6 . . ? C34 C35 C30 119.9(10) . . ? C34 C35 H36 120.1 . . ? C30 C35 H36 120.1 . . ? C37 C36 C41 118.3(8) . . ? C37 C36 N5 122.0(8) . . ? C41 C36 N5 119.7(7) . . ? C38 C37 C36 120.3(9) . . ? C38 C37 H34 119.9 . . ? C36 C37 H34 119.9 . . ? C39 C38 C37 121.3(9) . . ? C39 C38 H37 119.3 . . ? C37 C38 H37 119.3 . . ? C38 C39 C40 119.0(9) . . ? C38 C39 H40 120.5 . . ? C40 C39 H40 120.5 . . ? C41 C40 C39 120.1(9) . . ? C41 C40 H38 119.9 . . ? C39 C40 H38 119.9 . . ? C40 C41 C36 120.9(9) . . ? C40 C41 H35 119.5 . . ? C36 C41 H35 119.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 3.478 _refine_diff_density_min -3.345 _refine_diff_density_rms 0.189 data_4 _database_code_depnum_ccdc_archive 'CCDC 857585' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H40 Ir N5' _chemical_formula_weight 843.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.378(3) _cell_length_b 10.421(3) _cell_length_c 17.146(5) _cell_angle_alpha 85.018(3) _cell_angle_beta 81.768(3) _cell_angle_gamma 79.502(4) _cell_volume 1801.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 3.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3157 _exptl_absorpt_correction_T_max 0.8348 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9120 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.08 _reflns_number_total 6074 _reflns_number_gt 5495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6074 _refine_ls_number_parameters 464 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.227442(15) 0.735940(15) 0.790185(9) 0.02032(7) Uani 1 1 d . . . N1 N 0.1172(3) 0.9178(3) 0.7742(2) 0.0237(8) Uani 1 1 d . . . N2 N 0.3350(3) 0.5591(3) 0.8205(2) 0.0242(8) Uani 1 1 d . . . N3 N 0.3198(3) 0.7283(4) 0.6679(2) 0.0282(8) Uani 1 1 d . . . N4 N 0.1329(3) 0.6533(3) 0.7055(2) 0.0240(8) Uani 1 1 d . . . N5 N 0.2302(4) 0.6287(4) 0.5692(2) 0.0288(8) Uani 1 1 d . . . C1 C 0.1053(4) 0.7401(4) 0.8929(2) 0.0249(9) Uani 1 1 d . . . C2 C 0.3612(4) 0.8003(4) 0.8439(2) 0.0223(9) Uani 1 1 d . . . C3 C 0.0948(4) 0.6473(5) 0.9564(2) 0.0295(10) Uani 1 1 d . . . H15 H 0.1531 0.5656 0.9549 0.035 Uiso 1 1 calc R . . C4 C -0.0009(5) 0.6733(5) 1.0223(3) 0.0377(12) Uani 1 1 d . . . H16 H -0.0048 0.6089 1.0649 0.045 Uiso 1 1 calc R . . C5 C -0.0882(5) 0.7878(5) 1.0272(3) 0.0376(12) Uani 1 1 d . . . H17 H -0.1522 0.8013 1.0725 0.045 Uiso 1 1 calc R . . C6 C -0.0845(4) 0.8865(5) 0.9656(3) 0.0321(11) Uani 1 1 d . . . C7 C 0.0133(4) 0.8583(4) 0.8999(2) 0.0236(9) Uani 1 1 d . . . C8 C 0.0216(4) 0.9528(4) 0.8358(2) 0.0242(9) Uani 1 1 d . . . C9 C -0.0642(4) 1.0734(5) 0.8355(3) 0.0314(11) Uani 1 1 d . . . C10 C -0.1600(5) 1.0990(5) 0.9042(3) 0.0393(12) Uani 1 1 d . . . H20 H -0.2181 1.1807 0.9064 0.047 Uiso 1 1 calc R . . C11 C -0.1689(5) 1.0097(5) 0.9653(3) 0.0395(12) Uani 1 1 d . . . H21 H -0.2336 1.0299 1.0096 0.047 Uiso 1 1 calc R . . C12 C -0.0486(5) 1.1606(5) 0.7693(3) 0.0402(12) Uani 1 1 d . . . H26 H -0.1040 1.2438 0.7670 0.048 Uiso 1 1 calc R . . C13 C 0.0473(5) 1.1244(5) 0.7079(3) 0.0395(12) Uani 1 1 d . . . H25 H 0.0577 1.1822 0.6624 0.047 Uiso 1 1 calc R . . C14 C 0.1297(5) 1.0035(4) 0.7120(3) 0.0318(11) Uani 1 1 d . . . H24 H 0.1969 0.9810 0.6692 0.038 Uiso 1 1 calc R . . C15 C 0.3838(4) 0.9245(4) 0.8528(3) 0.0294(10) Uani 1 1 d . . . H2 H 0.3254 0.9983 0.8343 0.035 Uiso 1 1 calc R . . C16 C 0.4924(5) 0.9439(5) 0.8890(3) 0.0374(12) Uani 1 1 d . . . H3 H 0.5041 1.0307 0.8949 0.045 Uiso 1 1 calc R . . C17 C 0.5811(5) 0.8418(5) 0.9158(3) 0.0378(12) Uani 1 1 d . . . H4 H 0.6532 0.8578 0.9398 0.045 Uiso 1 1 calc R . . C18 C 0.5647(5) 0.7131(5) 0.9076(3) 0.0313(10) Uani 1 1 d . . . C19 C 0.4563(4) 0.6954(4) 0.8720(2) 0.0241(9) Uani 1 1 d . . . C20 C 0.4395(4) 0.5667(4) 0.8595(2) 0.0253(9) Uani 1 1 d . . . C21 C 0.5263(5) 0.4550(5) 0.8838(3) 0.0335(11) Uani 1 1 d . . . C22 C 0.6342(5) 0.4776(5) 0.9216(3) 0.0432(13) Uani 1 1 d . . . H7 H 0.6935 0.4046 0.9402 0.052 Uiso 1 1 calc R . . C23 C 0.6544(5) 0.5992(5) 0.9318(3) 0.0419(13) Uani 1 1 d . . . H8 H 0.7290 0.6096 0.9554 0.050 Uiso 1 1 calc R . . C24 C 0.4999(5) 0.3330(5) 0.8696(3) 0.0402(12) Uani 1 1 d . . . H12 H 0.5551 0.2552 0.8860 0.048 Uiso 1 1 calc R . . C25 C 0.3936(5) 0.3264(4) 0.8316(3) 0.0374(12) Uani 1 1 d . . . H11 H 0.3752 0.2438 0.8216 0.045 Uiso 1 1 calc R . . C26 C 0.3132(4) 0.4402(4) 0.8078(3) 0.0303(10) Uani 1 1 d . . . H13 H 0.2401 0.4337 0.7816 0.036 Uiso 1 1 calc R . . C27 C 0.2282(4) 0.6715(4) 0.6469(2) 0.0264(10) Uani 1 1 d . . . C28 C 0.2361(4) 0.7199(5) 0.5027(3) 0.0294(10) Uani 1 1 d . . . C29 C 0.3070(5) 0.6821(5) 0.4310(3) 0.0356(11) Uani 1 1 d . . . H29 H 0.3512 0.5944 0.4258 0.043 Uiso 1 1 calc R . . C30 C 0.2517(6) 0.9007(5) 0.3739(3) 0.0466(14) Uani 1 1 d . . . H30 H 0.2580 0.9627 0.3301 0.056 Uiso 1 1 calc R . . C31 C 0.1811(6) 0.9376(5) 0.4446(3) 0.0457(14) Uani 1 1 d . . . H31 H 0.1370 1.0254 0.4492 0.055 Uiso 1 1 calc R . . C32 C 0.1728(5) 0.8492(5) 0.5092(3) 0.0377(12) Uani 1 1 d . . . H32 H 0.1242 0.8764 0.5580 0.045 Uiso 1 1 calc R . . C33 C 0.3132(5) 0.7730(5) 0.3672(3) 0.0438(13) Uani 1 1 d . . . H33 H 0.3607 0.7465 0.3180 0.053 Uiso 1 1 calc R . . C34 C 0.2407(4) 0.4925(4) 0.5601(2) 0.0265(10) Uani 1 1 d . . . C35 C 0.3321(5) 0.2697(5) 0.5965(3) 0.0404(12) Uani 1 1 d . . . H35 H 0.3885 0.2087 0.6264 0.049 Uiso 1 1 calc R . . C36 C 0.1787(5) 0.3152(5) 0.5032(3) 0.0371(12) Uani 1 1 d . . . H36 H 0.1285 0.2853 0.4686 0.045 Uiso 1 1 calc R . . C37 C 0.3233(5) 0.4029(5) 0.6037(3) 0.0363(11) Uani 1 1 d . . . H37 H 0.3736 0.4328 0.6383 0.044 Uiso 1 1 calc R . . C38 C 0.2599(5) 0.2257(5) 0.5466(3) 0.0398(12) Uani 1 1 d . . . H38 H 0.2657 0.1346 0.5419 0.048 Uiso 1 1 calc R . . C39 C 0.1698(5) 0.4479(5) 0.5097(3) 0.0318(10) Uani 1 1 d . . . H39 H 0.1142 0.5085 0.4792 0.038 Uiso 1 1 calc R . . C40 C 0.0019(4) 0.6316(4) 0.6937(3) 0.0285(10) Uani 1 1 d . . . H40 H 0.0030 0.6178 0.6366 0.034 Uiso 1 1 calc R . . C41 C -0.1017(5) 0.7495(5) 0.7151(3) 0.0441(13) Uani 1 1 d . . . H41A H -0.0768 0.8274 0.6849 0.066 Uiso 1 1 calc R . . H41B H -0.1080 0.7613 0.7717 0.066 Uiso 1 1 calc R . . H41C H -0.1873 0.7361 0.7026 0.066 Uiso 1 1 calc R . . C42 C -0.0312(6) 0.5101(6) 0.7420(4) 0.066(2) Uani 1 1 d . . . H42A H -0.0310 0.5212 0.7981 0.099 Uiso 1 1 calc R . . H42B H 0.0349 0.4341 0.7256 0.099 Uiso 1 1 calc R . . H42C H -0.1188 0.4963 0.7333 0.099 Uiso 1 1 calc R . . C43 C 0.5568(4) 0.6463(5) 0.6675(3) 0.0378(12) Uani 1 1 d . . . H43A H 0.5352 0.5584 0.6798 0.057 Uiso 1 1 calc R . . H43B H 0.5608 0.6861 0.7166 0.057 Uiso 1 1 calc R . . H43C H 0.6426 0.6404 0.6344 0.057 Uiso 1 1 calc R . . C44 C 0.4513(4) 0.7296(5) 0.6237(3) 0.0320(10) Uani 1 1 d . . . H44 H 0.4547 0.6947 0.5708 0.038 Uiso 1 1 calc R . . C45 C 0.4741(6) 0.8718(5) 0.6126(4) 0.0535(15) Uani 1 1 d . . . H45A H 0.4652 0.9081 0.6643 0.080 Uiso 1 1 calc R . . H45B H 0.4086 0.9235 0.5813 0.080 Uiso 1 1 calc R . . H45C H 0.5632 0.8747 0.5850 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01964(10) 0.01657(10) 0.02454(10) -0.00397(6) -0.00318(6) -0.00106(7) N1 0.0223(19) 0.0198(19) 0.0295(19) -0.0047(15) -0.0063(15) -0.0012(15) N2 0.025(2) 0.0188(19) 0.0286(19) -0.0067(14) -0.0041(15) -0.0004(15) N3 0.021(2) 0.033(2) 0.031(2) -0.0130(16) 0.0008(15) -0.0037(17) N4 0.0200(19) 0.024(2) 0.0275(19) -0.0043(15) -0.0034(15) -0.0008(15) N5 0.036(2) 0.025(2) 0.0256(19) -0.0078(15) -0.0027(16) -0.0046(17) C1 0.022(2) 0.030(3) 0.026(2) -0.0080(18) -0.0062(18) -0.0084(19) C2 0.024(2) 0.022(2) 0.021(2) -0.0072(16) -0.0008(17) -0.0019(18) C3 0.028(3) 0.033(3) 0.030(2) -0.0009(19) -0.0062(19) -0.010(2) C4 0.045(3) 0.048(3) 0.026(2) 0.002(2) -0.006(2) -0.025(3) C5 0.032(3) 0.056(4) 0.029(3) -0.011(2) 0.005(2) -0.025(3) C6 0.023(2) 0.044(3) 0.034(3) -0.019(2) 0.0006(19) -0.013(2) C7 0.021(2) 0.026(2) 0.027(2) -0.0067(17) -0.0047(17) -0.0084(19) C8 0.015(2) 0.025(2) 0.033(2) -0.0102(18) -0.0041(17) -0.0016(18) C9 0.023(2) 0.028(3) 0.047(3) -0.012(2) -0.009(2) -0.004(2) C10 0.019(2) 0.033(3) 0.066(4) -0.028(3) -0.001(2) 0.003(2) C11 0.024(3) 0.047(3) 0.050(3) -0.028(3) 0.005(2) -0.009(2) C12 0.031(3) 0.022(3) 0.066(4) -0.003(2) -0.013(3) 0.003(2) C13 0.041(3) 0.027(3) 0.048(3) 0.009(2) -0.009(2) -0.004(2) C14 0.032(3) 0.028(3) 0.034(3) 0.003(2) -0.004(2) -0.004(2) C15 0.029(3) 0.022(2) 0.038(3) -0.0061(19) -0.005(2) -0.002(2) C16 0.040(3) 0.025(3) 0.052(3) -0.010(2) -0.011(2) -0.012(2) C17 0.032(3) 0.036(3) 0.050(3) -0.010(2) -0.016(2) -0.008(2) C18 0.028(3) 0.030(3) 0.039(3) -0.007(2) -0.011(2) -0.005(2) C19 0.021(2) 0.023(2) 0.028(2) -0.0065(17) -0.0012(18) -0.0017(18) C20 0.022(2) 0.025(2) 0.030(2) -0.0042(18) -0.0070(18) -0.0023(19) C21 0.031(3) 0.026(3) 0.044(3) -0.006(2) -0.010(2) 0.002(2) C22 0.038(3) 0.033(3) 0.059(3) -0.004(2) -0.027(3) 0.007(2) C23 0.034(3) 0.037(3) 0.058(3) -0.010(2) -0.023(2) 0.000(2) C24 0.036(3) 0.023(3) 0.062(3) -0.004(2) -0.020(2) 0.005(2) C25 0.042(3) 0.014(2) 0.059(3) -0.006(2) -0.016(2) -0.002(2) C26 0.028(3) 0.025(3) 0.039(3) -0.0077(19) -0.007(2) -0.004(2) C27 0.030(3) 0.021(2) 0.027(2) -0.0051(17) -0.0029(19) 0.0017(19) C28 0.030(3) 0.031(3) 0.029(2) -0.0051(19) -0.0073(19) -0.007(2) C29 0.040(3) 0.030(3) 0.036(3) -0.005(2) -0.002(2) -0.003(2) C30 0.058(4) 0.042(3) 0.042(3) 0.008(2) -0.017(3) -0.014(3) C31 0.060(4) 0.029(3) 0.050(3) -0.001(2) -0.023(3) -0.001(3) C32 0.047(3) 0.030(3) 0.038(3) -0.008(2) -0.011(2) -0.002(2) C33 0.049(3) 0.050(4) 0.031(3) 0.003(2) -0.001(2) -0.009(3) C34 0.028(2) 0.024(2) 0.026(2) -0.0075(17) 0.0050(18) -0.0052(19) C35 0.043(3) 0.027(3) 0.049(3) -0.006(2) -0.010(2) 0.005(2) C36 0.048(3) 0.039(3) 0.030(3) -0.009(2) -0.004(2) -0.019(2) C37 0.032(3) 0.034(3) 0.043(3) -0.014(2) -0.010(2) 0.001(2) C38 0.056(3) 0.023(3) 0.039(3) -0.008(2) 0.003(2) -0.009(2) C39 0.035(3) 0.033(3) 0.028(2) -0.0017(19) -0.003(2) -0.008(2) C40 0.026(2) 0.030(3) 0.032(2) -0.0028(19) -0.0065(19) -0.008(2) C41 0.028(3) 0.040(3) 0.068(4) -0.014(3) -0.016(2) -0.003(2) C42 0.040(3) 0.045(4) 0.117(6) 0.028(4) -0.022(4) -0.022(3) C43 0.020(2) 0.051(3) 0.040(3) -0.014(2) 0.006(2) -0.002(2) C44 0.026(3) 0.038(3) 0.032(2) -0.009(2) 0.0061(19) -0.008(2) C45 0.043(3) 0.040(3) 0.073(4) -0.004(3) 0.016(3) -0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C2 2.009(4) . ? Ir1 C1 2.016(4) . ? Ir1 N2 2.040(3) . ? Ir1 N1 2.046(3) . ? Ir1 N4 2.178(3) . ? Ir1 N3 2.179(4) . ? Ir1 C27 2.600(4) . ? N1 C14 1.337(5) . ? N1 C8 1.368(5) . ? N2 C26 1.340(6) . ? N2 C20 1.371(5) . ? N3 C27 1.313(5) . ? N3 C44 1.465(6) . ? N4 C27 1.331(6) . ? N4 C40 1.463(5) . ? N5 C28 1.421(6) . ? N5 C34 1.424(6) . ? N5 C27 1.439(5) . ? C1 C3 1.398(6) . ? C1 C7 1.417(6) . ? C2 C15 1.382(6) . ? C2 C19 1.433(6) . ? C3 C4 1.403(7) . ? C4 C5 1.361(7) . ? C5 C6 1.410(7) . ? C6 C7 1.416(6) . ? C6 C11 1.416(7) . ? C7 C8 1.415(6) . ? C8 C9 1.401(6) . ? C9 C12 1.401(7) . ? C9 C10 1.439(7) . ? C10 C11 1.344(7) . ? C12 C13 1.368(7) . ? C13 C14 1.390(7) . ? C15 C16 1.415(6) . ? C16 C17 1.368(7) . ? C17 C18 1.404(7) . ? C18 C19 1.402(6) . ? C18 C23 1.438(6) . ? C19 C20 1.422(6) . ? C20 C21 1.407(6) . ? C21 C24 1.396(7) . ? C21 C22 1.436(6) . ? C22 C23 1.350(7) . ? C24 C25 1.374(6) . ? C25 C26 1.387(6) . ? C28 C29 1.387(6) . ? C28 C32 1.393(7) . ? C29 C33 1.386(7) . ? C30 C31 1.370(8) . ? C30 C33 1.374(8) . ? C31 C32 1.381(7) . ? C34 C39 1.371(6) . ? C34 C37 1.391(6) . ? C35 C38 1.372(7) . ? C35 C37 1.390(7) . ? C36 C38 1.381(7) . ? C36 C39 1.381(7) . ? C40 C41 1.510(7) . ? C40 C42 1.517(7) . ? C43 C44 1.514(6) . ? C44 C45 1.534(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Ir1 C1 89.48(16) . . ? C2 Ir1 N2 81.65(15) . . ? C1 Ir1 N2 93.32(16) . . ? C2 Ir1 N1 94.19(15) . . ? C1 Ir1 N1 80.91(16) . . ? N2 Ir1 N1 172.95(12) . . ? C2 Ir1 N4 162.98(15) . . ? C1 Ir1 N4 106.97(14) . . ? N2 Ir1 N4 92.82(13) . . ? N1 Ir1 N4 92.74(13) . . ? C2 Ir1 N3 102.87(15) . . ? C1 Ir1 N3 167.19(14) . . ? N2 Ir1 N3 91.84(14) . . ? N1 Ir1 N3 94.64(14) . . ? N4 Ir1 N3 61.04(13) . . ? C2 Ir1 C27 132.85(15) . . ? C1 Ir1 C27 137.65(15) . . ? N2 Ir1 C27 92.14(13) . . ? N1 Ir1 C27 94.85(13) . . ? N4 Ir1 C27 30.77(13) . . ? N3 Ir1 C27 30.28(13) . . ? C14 N1 C8 118.2(4) . . ? C14 N1 Ir1 127.6(3) . . ? C8 N1 Ir1 114.2(3) . . ? C26 N2 C20 118.1(4) . . ? C26 N2 Ir1 127.6(3) . . ? C20 N2 Ir1 114.2(3) . . ? C27 N3 C44 125.3(4) . . ? C27 N3 Ir1 92.9(3) . . ? C44 N3 Ir1 137.9(3) . . ? C27 N4 C40 124.0(4) . . ? C27 N4 Ir1 92.4(3) . . ? C40 N4 Ir1 139.7(3) . . ? C28 N5 C34 121.4(3) . . ? C28 N5 C27 119.7(4) . . ? C34 N5 C27 118.5(3) . . ? C3 C1 C7 115.6(4) . . ? C3 C1 Ir1 131.5(4) . . ? C7 C1 Ir1 112.9(3) . . ? C15 C2 C19 115.2(4) . . ? C15 C2 Ir1 132.2(3) . . ? C19 C2 Ir1 112.3(3) . . ? C1 C3 C4 120.7(5) . . ? C5 C4 C3 122.2(5) . . ? C4 C5 C6 120.6(4) . . ? C5 C6 C7 116.2(5) . . ? C5 C6 C11 125.2(4) . . ? C7 C6 C11 118.6(4) . . ? C8 C7 C6 119.0(4) . . ? C8 C7 C1 116.4(4) . . ? C6 C7 C1 124.6(4) . . ? N1 C8 C9 122.5(4) . . ? N1 C8 C7 115.6(4) . . ? C9 C8 C7 121.9(4) . . ? C12 C9 C8 117.8(4) . . ? C12 C9 C10 125.0(5) . . ? C8 C9 C10 117.2(4) . . ? C11 C10 C9 121.4(5) . . ? C10 C11 C6 121.9(5) . . ? C13 C12 C9 119.2(5) . . ? C12 C13 C14 120.3(4) . . ? N1 C14 C13 122.0(4) . . ? C2 C15 C16 121.3(4) . . ? C17 C16 C15 122.1(4) . . ? C16 C17 C18 119.5(4) . . ? C19 C18 C17 117.7(4) . . ? C19 C18 C23 118.5(4) . . ? C17 C18 C23 123.8(4) . . ? C18 C19 C20 119.4(4) . . ? C18 C19 C2 124.2(4) . . ? C20 C19 C2 116.4(4) . . ? N2 C20 C21 122.4(4) . . ? N2 C20 C19 115.4(4) . . ? C21 C20 C19 122.2(4) . . ? C24 C21 C20 117.6(4) . . ? C24 C21 C22 125.9(4) . . ? C20 C21 C22 116.4(4) . . ? C23 C22 C21 122.3(5) . . ? C22 C23 C18 121.1(4) . . ? C25 C24 C21 119.5(4) . . ? C24 C25 C26 120.1(4) . . ? N2 C26 C25 122.2(4) . . ? N3 C27 N4 113.6(4) . . ? N3 C27 N5 124.2(4) . . ? N4 C27 N5 122.2(4) . . ? N3 C27 Ir1 56.8(2) . . ? N4 C27 Ir1 56.8(2) . . ? N5 C27 Ir1 176.9(3) . . ? C29 C28 C32 119.2(4) . . ? C29 C28 N5 120.5(4) . . ? C32 C28 N5 120.3(4) . . ? C33 C29 C28 119.7(5) . . ? C31 C30 C33 119.2(5) . . ? C30 C31 C32 121.1(5) . . ? C31 C32 C28 119.8(5) . . ? C30 C33 C29 121.0(5) . . ? C39 C34 C37 119.4(4) . . ? C39 C34 N5 121.2(4) . . ? C37 C34 N5 119.5(4) . . ? C38 C35 C37 120.4(5) . . ? C38 C36 C39 120.7(4) . . ? C35 C37 C34 119.9(4) . . ? C35 C38 C36 119.3(5) . . ? C34 C39 C36 120.3(4) . . ? N4 C40 C41 110.7(4) . . ? N4 C40 C42 110.3(4) . . ? C41 C40 C42 110.7(5) . . ? N3 C44 C43 110.7(4) . . ? N3 C44 C45 108.0(4) . . ? C43 C44 C45 110.3(4) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.890 _refine_diff_density_min -1.402 _refine_diff_density_rms 0.121 data_5 _database_code_depnum_ccdc_archive 'CCDC 857586' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H40 Ir N5 O2' _chemical_formula_weight 875.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.130(8) _cell_length_b 17.026(14) _cell_length_c 24.47(2) _cell_angle_alpha 88.939(13) _cell_angle_beta 89.100(12) _cell_angle_gamma 87.355(12) _cell_volume 3798(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 320 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 3.560 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3301 _exptl_absorpt_correction_T_max 0.4148 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20097 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.1525 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.34 _reflns_number_total 13267 _reflns_number_gt 8584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+83.0437P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13267 _refine_ls_number_parameters 895 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1298 _refine_ls_R_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.2235 _refine_ls_wR_factor_gt 0.2130 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.29267(7) 0.70361(4) 0.09330(3) 0.0212(2) Uani 1 1 d . . . Ir2 Ir 0.73208(7) 0.21485(4) 0.40270(3) 0.0227(2) Uani 1 1 d . . . N1 N 0.3582(16) 0.5831(9) 0.0913(5) 0.027(4) Uani 1 1 d . . . N2 N 0.2384(16) 0.8207(8) 0.0832(5) 0.023(3) Uani 1 1 d . . . N3 N 0.3564(15) 0.7211(9) 0.1778(6) 0.026(3) Uani 1 1 d . . . N4 N 0.1317(14) 0.6829(8) 0.1574(6) 0.023(3) Uani 1 1 d . . . N5 N 0.1804(17) 0.7006(8) 0.2555(5) 0.029(4) Uani 1 1 d . . . N6 N 0.6794(15) 0.0981(8) 0.4165(6) 0.024(3) Uani 1 1 d . . . N7 N 0.7841(14) 0.3310(9) 0.4048(5) 0.028(4) Uani 1 1 d . . . N8 N 0.6631(15) 0.2234(8) 0.3161(6) 0.022(3) Uani 1 1 d . . . N9 N 0.8938(16) 0.1828(8) 0.3379(5) 0.024(3) Uani 1 1 d . . . N10 N 0.8341(16) 0.1905(8) 0.2421(6) 0.024(3) Uani 1 1 d . . . O1 O 0.2975(16) 0.9384(7) 0.0485(6) 0.047(4) Uani 1 1 d . . . O2 O 0.3554(14) 0.4715(7) 0.0483(5) 0.034(3) Uani 1 1 d . . . O3 O 0.6965(15) -0.0075(8) 0.4715(6) 0.042(4) Uani 1 1 d . . . O4 O 0.7254(13) 0.4522(7) 0.4344(5) 0.033(3) Uani 1 1 d . . . C1 C 0.1992(19) 0.6718(11) 0.0214(8) 0.0308(13) Uani 1 1 d . . . C2 C 0.4698(16) 0.7385(10) 0.0475(6) 0.018(4) Uani 1 1 d . . . C3 C 0.2153(19) 0.5884(10) 0.0112(7) 0.028(4) Uani 1 1 d . . . C4 C 0.1177(19) 0.7186(12) -0.0164(7) 0.0308(13) Uani 1 1 d . . . H19 H 0.1042 0.7737 -0.0115 0.037 Uiso 1 1 d R . . C5 C 0.056(2) 0.6827(13) -0.0624(7) 0.035(5) Uani 1 1 d . . . H18 H 0.0057 0.7146 -0.0891 0.042 Uiso 1 1 d R . . C6 C 0.0667(19) 0.6027(13) -0.0687(8) 0.036(5) Uani 1 1 d . . . H17 H 0.0161 0.5802 -0.0978 0.043 Uiso 1 1 d R . . C7 C 0.149(2) 0.5539(12) -0.0341(8) 0.038(5) Uani 1 1 d . . . H16 H 0.1617 0.4991 -0.0405 0.046 Uiso 1 1 d R . . C8 C 0.3049(19) 0.5480(11) 0.0516(8) 0.0308(13) Uani 1 1 d . . . C9 C 0.455(2) 0.5313(9) 0.1192(8) 0.029(4) Uani 1 1 d . . . C10 C 0.453(2) 0.4610(12) 0.0922(8) 0.035(5) Uani 1 1 d . . . C11 C 0.535(2) 0.3933(11) 0.1080(9) 0.041(5) Uani 1 1 d . . . H21 H 0.5331 0.3452 0.0891 0.049 Uiso 1 1 d R . . C12 C 0.621(2) 0.4023(12) 0.1533(9) 0.041(5) Uani 1 1 d . . . H25 H 0.6774 0.3578 0.1667 0.049 Uiso 1 1 d R . . C13 C 0.630(2) 0.4724(12) 0.1807(8) 0.037(5) Uani 1 1 d . . . H26 H 0.6936 0.4753 0.2109 0.044 Uiso 1 1 d R . . C14 C 0.5457(19) 0.5397(11) 0.1639(7) 0.030(4) Uani 1 1 d . . . H22 H 0.5498 0.5882 0.1822 0.036 Uiso 1 1 d R . . C15 C 0.4732(19) 0.8204(10) 0.0377(7) 0.025(4) Uani 1 1 d . . . C16 C 0.587(2) 0.8565(13) 0.0086(8) 0.039(5) Uani 1 1 d . . . H3 H 0.5822 0.9112 0.0003 0.047 Uiso 1 1 d R . . C17 C 0.706(2) 0.8085(14) -0.0074(8) 0.049(6) Uani 1 1 d . . . H5 H 0.7882 0.8315 -0.0243 0.058 Uiso 1 1 d R . . C18 C 0.7062(19) 0.7268(11) 0.0005(7) 0.0308(13) Uani 1 1 d . . . H4A H 0.7863 0.6946 -0.0127 0.037 Uiso 1 1 d R . . C19 C 0.589(2) 0.6924(13) 0.0289(7) 0.035(5) Uani 1 1 d . . . H6 H 0.5912 0.6370 0.0347 0.042 Uiso 1 1 d R . . C20 C 0.3377(19) 0.8612(11) 0.0565(8) 0.0308(13) Uani 1 1 d . . . C21 C 0.1150(19) 0.8711(11) 0.0922(8) 0.0308(13) Uani 1 1 d . . . C22 C 0.155(2) 0.9461(11) 0.0700(9) 0.040(5) Uani 1 1 d . . . C23 C 0.060(3) 1.0126(15) 0.0714(11) 0.070(8) Uani 1 1 d . . . H13 H 0.0870 1.0619 0.0565 0.084 Uiso 1 1 d R . . C24 C -0.077(3) 1.0028(14) 0.0953(12) 0.072(8) Uani 1 1 d . . . H12 H -0.1453 1.0465 0.0984 0.086 Uiso 1 1 d R . . C25 C -0.115(3) 0.9287(14) 0.1151(10) 0.057(7) Uani 1 1 d . . . H11 H -0.2118 0.9228 0.1292 0.069 Uiso 1 1 d R . . C26 C -0.019(2) 0.8647(11) 0.1153(8) 0.037(5) Uani 1 1 d . . . H9 H -0.0466 0.8160 0.1310 0.044 Uiso 1 1 d R . . C27 C 0.2218(19) 0.7000(11) 0.1973(7) 0.027(4) Uani 1 1 d . . . C28 C 0.0033(19) 0.6347(11) 0.1685(7) 0.028(4) Uani 1 1 d . . . H28 H -0.0621 0.6620 0.1960 0.034 Uiso 1 1 d R . . C29 C -0.0798(19) 0.6304(12) 0.1142(7) 0.034(5) Uani 1 1 d . . . H29A H -0.0981 0.6836 0.0992 0.050 Uiso 1 1 d R . . H29B H -0.1735 0.6057 0.1209 0.050 Uiso 1 1 d R . . H29C H -0.0206 0.5991 0.0880 0.050 Uiso 1 1 d R . . C30 C 0.048(2) 0.5535(13) 0.1906(10) 0.053(6) Uani 1 1 d . . . H30A H 0.1161 0.5271 0.1646 0.080 Uiso 1 1 d R . . H30B H -0.0391 0.5228 0.1956 0.080 Uiso 1 1 d R . . H30C H 0.0969 0.5580 0.2258 0.080 Uiso 1 1 d R . . C31 C 0.4645(19) 0.7648(11) 0.2087(7) 0.028(4) Uani 1 1 d . . . H31 H 0.4819 0.7377 0.2447 0.034 Uiso 1 1 d R . . C32 C 0.607(2) 0.7618(15) 0.1752(9) 0.061(8) Uani 1 1 d . . . H32A H 0.6161 0.7121 0.1555 0.092 Uiso 1 1 d R . . H32B H 0.6903 0.7655 0.1996 0.092 Uiso 1 1 d R . . H32C H 0.6055 0.8059 0.1489 0.092 Uiso 1 1 d R . . C33 C 0.410(2) 0.8497(14) 0.2184(13) 0.083(11) Uani 1 1 d . . . H33A H 0.3587 0.8703 0.1859 0.124 Uiso 1 1 d R . . H33B H 0.4938 0.8819 0.2254 0.124 Uiso 1 1 d R . . H33C H 0.3428 0.8513 0.2500 0.124 Uiso 1 1 d R . . C34 C 0.0447(19) 0.7390(12) 0.2716(7) 0.027(4) Uani 1 1 d . . . C35 C -0.0478(19) 0.6995(14) 0.3065(8) 0.040(5) Uani 1 1 d . . . H35 H -0.0202 0.6484 0.3201 0.048 Uiso 1 1 d R . . C36 C 0.008(2) 0.8156(13) 0.2538(8) 0.043(5) Uani 1 1 d . . . H36 H 0.0737 0.8423 0.2304 0.051 Uiso 1 1 d R . . C37 C -0.184(2) 0.7361(12) 0.3221(8) 0.0308(13) Uani 1 1 d . . . H37 H -0.2526 0.7079 0.3434 0.037 Uiso 1 1 d R . . C38 C -0.126(3) 0.8545(15) 0.2702(11) 0.062(7) Uani 1 1 d . . . H38 H -0.1539 0.9060 0.2574 0.075 Uiso 1 1 d R . . C39 C -0.215(3) 0.8107(17) 0.3074(10) 0.071(9) Uani 1 1 d . . . H39 H -0.3022 0.8364 0.3215 0.085 Uiso 1 1 d R . . C40 C 0.2869(19) 0.7025(11) 0.3480(7) 0.028(4) Uani 1 1 d . . . H40 H 0.2260 0.7474 0.3567 0.034 Uiso 1 1 d R . . C41 C 0.472(2) 0.6057(12) 0.3762(8) 0.041(5) Uani 1 1 d . . . H41 H 0.5380 0.5841 0.4026 0.049 Uiso 1 1 d R . . C42 C 0.2760(18) 0.6697(10) 0.2950(7) 0.023(4) Uani 1 1 d . . . C43 C 0.366(2) 0.6025(11) 0.2850(7) 0.030(4) Uani 1 1 d . . . H43 H 0.3610 0.5778 0.2507 0.036 Uiso 1 1 d R . . C44 C 0.462(2) 0.5713(10) 0.3237(8) 0.035(5) Uani 1 1 d . . . H44 H 0.5219 0.5259 0.3153 0.042 Uiso 1 1 d R . . C45 C 0.382(2) 0.6718(12) 0.3874(7) 0.033(5) Uani 1 1 d . . . H45 H 0.3853 0.6959 0.4220 0.040 Uiso 1 1 d R . . C46 C 0.8337(17) 0.1910(10) 0.4748(7) 0.024(4) Uani 1 1 d . . . C47 C 0.824(2) 0.1137(10) 0.4967(7) 0.032(5) Uani 1 1 d . . . C48 C 0.891(2) 0.0853(13) 0.5452(8) 0.044(5) Uani 1 1 d . . . H48 H 0.8839 0.0323 0.5575 0.053 Uiso 1 1 d R . . C49 C 0.969(2) 0.1406(15) 0.5745(8) 0.046(6) Uani 1 1 d . . . H49 H 1.0165 0.1244 0.6073 0.055 Uiso 1 1 d R . . C50 C 0.976(2) 0.2157(13) 0.5564(8) 0.038(5) Uani 1 1 d . . . H50 H 1.0297 0.2511 0.5769 0.045 Uiso 1 1 d R . . C51 C 0.907(2) 0.2433(11) 0.5087(7) 0.028(4) Uani 1 1 d . . . H51 H 0.9101 0.2974 0.4987 0.034 Uiso 1 1 d R . . C52 C 0.737(2) 0.0690(10) 0.4617(7) 0.031(5) Uani 1 1 d . . . C53 C 0.500(2) 0.0417(11) 0.3490(7) 0.031(5) Uani 1 1 d . . . H53 H 0.4873 0.0864 0.3254 0.038 Uiso 1 1 d R . . C54 C 0.5925(19) 0.0426(10) 0.3944(8) 0.030(4) Uani 1 1 d . . . C55 C 0.607(2) -0.0257(10) 0.4285(8) 0.032(5) Uani 1 1 d . . . C56 C 0.533(3) -0.0924(12) 0.4201(10) 0.060(7) Uani 1 1 d . . . H56 H 0.5404 -0.1365 0.4443 0.072 Uiso 1 1 d R . . C57 C 0.446(2) -0.0918(13) 0.3740(10) 0.048(6) Uani 1 1 d . . . H57 H 0.3968 -0.1381 0.3657 0.058 Uiso 1 1 d R . . C58 C 0.427(2) -0.0264(11) 0.3398(9) 0.040(5) Uani 1 1 d . . . H58 H 0.3637 -0.0284 0.3096 0.049 Uiso 1 1 d R . . C59 C 0.5523(19) 0.2603(11) 0.4425(8) 0.0308(13) Uani 1 1 d . . . C60 C 0.5544(18) 0.3460(10) 0.4511(7) 0.026(4) Uani 1 1 d . . . C61 C 0.432(2) 0.3867(13) 0.4738(9) 0.045(6) Uani 1 1 d . . . H61 H 0.4348 0.4419 0.4784 0.054 Uiso 1 1 d R . . C62 C 0.310(2) 0.3492(14) 0.4889(8) 0.046(6) Uani 1 1 d . . . H62 H 0.2282 0.3785 0.5037 0.055 Uiso 1 1 d R . . C63 C 0.303(2) 0.2665(14) 0.4834(8) 0.044(6) Uani 1 1 d . . . H63 H 0.2178 0.2404 0.4947 0.053 Uiso 1 1 d R . . C64 C 0.427(2) 0.2233(11) 0.4603(8) 0.034(5) Uani 1 1 d . . . H64 H 0.4230 0.1679 0.4570 0.041 Uiso 1 1 d R . . C65 C 0.6841(19) 0.3756(11) 0.4349(8) 0.0308(13) Uani 1 1 d . . . C66 C 0.9040(19) 0.3792(11) 0.3918(8) 0.0308(13) Uani 1 1 d . . . C67 C 1.0409(19) 0.3625(11) 0.3650(8) 0.035(5) Uani 1 1 d . . . H67 H 1.0675 0.3122 0.3507 0.042 Uiso 1 1 d R . . C68 C 1.133(2) 0.4252(13) 0.3612(9) 0.043(5) Uani 1 1 d . . . H68 H 1.2272 0.4169 0.3450 0.052 Uiso 1 1 d R . . C69 C 0.864(2) 0.4532(10) 0.4099(7) 0.031(4) Uani 1 1 d . . . C70 C 0.955(3) 0.5158(12) 0.4059(11) 0.060(7) Uani 1 1 d . . . H70 H 0.9275 0.5662 0.4197 0.072 Uiso 1 1 d R . . C71 C 1.091(3) 0.4998(14) 0.3801(10) 0.061(7) Uani 1 1 d . . . H71 H 1.1571 0.5411 0.3753 0.074 Uiso 1 1 d R . . C72 C 0.798(2) 0.1990(11) 0.2986(8) 0.0308(13) Uani 1 1 d . . . C73 C 0.5508(19) 0.2696(11) 0.2869(7) 0.028(4) Uani 1 1 d . . . H73 H 0.5691 0.2618 0.2469 0.033 Uiso 1 1 d R . . C74 C 0.4024(19) 0.2409(12) 0.3003(9) 0.042(5) Uani 1 1 d . . . H74A H 0.3866 0.1932 0.2797 0.063 Uiso 1 1 d R . . H74B H 0.3276 0.2817 0.2905 0.063 Uiso 1 1 d R . . H74C H 0.3956 0.2290 0.3395 0.063 Uiso 1 1 d R . . C75 C 0.560(2) 0.3595(10) 0.2980(8) 0.039(5) Uani 1 1 d . . . H75A H 0.5197 0.3709 0.3345 0.059 Uiso 1 1 d R . . H75B H 0.5032 0.3899 0.2706 0.059 Uiso 1 1 d R . . H75C H 0.6626 0.3739 0.2959 0.059 Uiso 1 1 d R . . C76 C 1.0284(19) 0.1322(10) 0.3328(7) 0.025(4) Uani 1 1 d . . . H76 H 1.0911 0.1538 0.3027 0.030 Uiso 1 1 d R . . C77 C 0.988(2) 0.0448(12) 0.3176(10) 0.049(6) Uani 1 1 d . . . H77A H 1.0778 0.0116 0.3141 0.074 Uiso 1 1 d R . . H77B H 0.9356 0.0460 0.2828 0.074 Uiso 1 1 d R . . H77C H 0.9249 0.0233 0.3465 0.074 Uiso 1 1 d R . . C78 C 1.1109(19) 0.1318(12) 0.3844(8) 0.035(5) Uani 1 1 d . . . H78A H 1.1343 0.1858 0.3931 0.053 Uiso 1 1 d R . . H78B H 1.2019 0.0996 0.3802 0.053 Uiso 1 1 d R . . H78C H 1.0510 0.1099 0.4140 0.053 Uiso 1 1 d R . . C79 C 1.061(2) 0.1802(13) 0.1870(8) 0.038(5) Uani 1 1 d . . . H79 H 1.0419 0.1272 0.1794 0.045 Uiso 1 1 d R . . C80 C 1.187(2) 0.2130(18) 0.1656(10) 0.064(8) Uani 1 1 d . . . H80 H 1.2547 0.1816 0.1447 0.077 Uiso 1 1 d R . . C81 C 0.962(2) 0.2235(13) 0.2189(7) 0.038(5) Uani 1 1 d . . . C82 C 1.119(3) 0.3342(13) 0.2083(9) 0.053(7) Uani 1 1 d . . . H82 H 1.1389 0.3871 0.2158 0.064 Uiso 1 1 d R . . C83 C 0.992(2) 0.3012(11) 0.2303(8) 0.033(5) Uani 1 1 d . . . H83 H 0.9271 0.3314 0.2531 0.040 Uiso 1 1 d R . . C84 C 1.212(3) 0.2901(19) 0.1753(9) 0.062(8) Uani 1 1 d . . . H84 H 1.2958 0.3128 0.1590 0.074 Uiso 1 1 d R . . C85 C 0.715(2) 0.1855(11) 0.1510(8) 0.032(4) Uani 1 1 d . . . H85 H 0.7680 0.2294 0.1388 0.038 Uiso 1 1 d R . . C86 C 0.7355(19) 0.1559(11) 0.2044(7) 0.030(4) Uani 1 1 d . . . C87 C 0.655(2) 0.0896(10) 0.2201(8) 0.033(5) Uani 1 1 d . . . H87 H 0.6689 0.0664 0.2553 0.040 Uiso 1 1 d R . . C88 C 0.618(2) 0.1518(12) 0.1157(8) 0.042(5) Uani 1 1 d . . . H88 H 0.6070 0.1729 0.0797 0.050 Uiso 1 1 d R . . C89 C 0.560(2) 0.0589(13) 0.1849(9) 0.047(6) Uani 1 1 d . . . H89 H 0.5050 0.0156 0.1971 0.057 Uiso 1 1 d R . . C90 C 0.539(2) 0.0882(13) 0.1319(9) 0.046(6) Uani 1 1 d . . . H90 H 0.4724 0.0654 0.1080 0.055 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0222(4) 0.0206(4) 0.0210(4) -0.0016(3) 0.0003(3) -0.0023(3) Ir2 0.0223(4) 0.0236(4) 0.0222(4) 0.0002(3) 0.0010(3) -0.0012(3) N1 0.028(9) 0.044(10) 0.006(7) 0.001(6) 0.006(6) 0.010(7) N2 0.035(9) 0.016(8) 0.017(7) -0.004(6) -0.005(6) 0.003(6) N3 0.024(9) 0.035(9) 0.020(8) -0.005(7) -0.010(6) 0.000(7) N4 0.013(7) 0.019(8) 0.037(9) -0.005(7) 0.003(6) -0.005(6) N5 0.045(10) 0.029(9) 0.011(7) 0.003(6) 0.010(7) 0.000(7) N6 0.020(8) 0.023(8) 0.029(9) 0.008(7) -0.001(7) -0.007(6) N7 0.010(7) 0.061(11) 0.015(8) -0.017(7) -0.002(6) 0.001(7) N8 0.020(8) 0.023(8) 0.024(8) 0.012(6) 0.000(6) -0.006(6) N9 0.035(9) 0.018(8) 0.018(8) 0.000(6) 0.009(6) 0.000(6) N10 0.031(9) 0.022(8) 0.019(8) 0.005(6) 0.010(7) -0.005(7) O1 0.053(10) 0.016(7) 0.073(11) 0.016(7) -0.006(8) -0.007(6) O2 0.044(8) 0.018(7) 0.040(8) -0.015(6) 0.003(7) 0.002(6) O3 0.047(9) 0.036(8) 0.044(9) 0.016(7) 0.003(7) -0.006(7) O4 0.034(8) 0.023(7) 0.042(8) -0.005(6) 0.011(6) -0.002(6) C1 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C2 0.005(8) 0.032(10) 0.017(9) 0.010(7) -0.003(7) -0.009(7) C3 0.026(10) 0.031(11) 0.028(10) -0.013(8) 0.014(8) -0.007(8) C4 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C5 0.023(11) 0.059(15) 0.023(10) 0.005(9) 0.007(8) -0.005(9) C6 0.018(10) 0.056(14) 0.035(12) -0.006(10) -0.007(9) -0.012(9) C7 0.022(11) 0.046(13) 0.046(13) -0.012(10) 0.015(9) -0.007(9) C8 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C9 0.032(11) 0.008(9) 0.046(12) -0.001(8) 0.002(9) 0.002(7) C10 0.018(10) 0.044(13) 0.042(12) -0.001(10) 0.006(9) 0.001(9) C11 0.028(11) 0.024(11) 0.071(16) -0.002(10) 0.019(11) 0.004(9) C12 0.034(12) 0.041(13) 0.046(13) 0.011(10) 0.002(10) 0.009(10) C13 0.035(12) 0.042(13) 0.033(11) 0.011(9) 0.004(9) 0.000(10) C14 0.030(11) 0.026(10) 0.033(11) 0.011(8) 0.006(9) -0.004(8) C15 0.030(10) 0.033(11) 0.013(9) 0.007(7) -0.004(7) -0.012(8) C16 0.037(12) 0.053(14) 0.029(11) 0.014(10) 0.000(9) -0.015(10) C17 0.026(12) 0.083(18) 0.038(13) 0.002(12) 0.016(10) -0.016(11) C18 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C19 0.025(11) 0.055(14) 0.026(11) 0.000(9) 0.001(9) -0.004(10) C20 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C21 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C22 0.025(11) 0.025(11) 0.070(15) -0.002(10) 0.015(10) -0.002(8) C23 0.07(2) 0.045(16) 0.09(2) -0.009(14) 0.015(16) 0.008(14) C24 0.055(17) 0.039(15) 0.12(2) -0.014(15) -0.013(16) 0.029(13) C25 0.045(15) 0.058(17) 0.066(17) -0.001(13) 0.009(12) 0.027(12) C26 0.039(12) 0.023(10) 0.047(13) -0.003(9) 0.010(10) 0.000(9) C27 0.028(11) 0.043(12) 0.010(9) 0.004(8) 0.004(8) 0.002(9) C28 0.026(10) 0.042(12) 0.019(9) -0.019(8) 0.003(8) -0.009(9) C29 0.023(10) 0.050(13) 0.029(11) -0.011(9) -0.007(8) -0.011(9) C30 0.031(13) 0.047(14) 0.081(18) 0.007(13) -0.001(12) 0.004(10) C31 0.024(10) 0.037(11) 0.026(10) -0.005(8) -0.003(8) -0.016(8) C32 0.020(11) 0.11(2) 0.058(16) -0.042(15) 0.005(10) -0.021(12) C33 0.020(12) 0.067(18) 0.17(3) -0.068(19) -0.012(15) -0.008(11) C34 0.020(10) 0.047(12) 0.014(9) -0.006(8) -0.007(7) -0.004(9) C35 0.018(10) 0.075(16) 0.027(11) -0.010(10) 0.002(8) 0.003(10) C36 0.044(13) 0.046(14) 0.040(12) -0.018(10) -0.003(10) -0.007(11) C37 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C38 0.056(16) 0.059(17) 0.073(18) -0.043(14) -0.011(14) 0.011(13) C39 0.048(15) 0.11(2) 0.060(17) -0.063(17) 0.005(13) 0.007(15) C40 0.028(11) 0.030(11) 0.027(10) -0.008(8) 0.002(8) -0.005(8) C41 0.036(12) 0.044(13) 0.042(13) 0.004(10) -0.005(10) -0.015(10) C42 0.024(10) 0.021(9) 0.023(9) -0.009(8) 0.003(8) 0.000(7) C43 0.036(11) 0.035(11) 0.021(10) -0.007(8) 0.005(8) -0.012(9) C44 0.056(14) 0.013(10) 0.035(11) 0.007(8) 0.000(10) -0.002(9) C45 0.034(12) 0.048(13) 0.018(10) -0.004(9) -0.001(8) -0.011(10) C46 0.014(9) 0.017(9) 0.042(11) 0.002(8) 0.004(8) -0.002(7) C47 0.048(13) 0.024(10) 0.025(10) 0.006(8) 0.011(9) -0.001(9) C48 0.041(13) 0.050(14) 0.039(13) 0.011(11) 0.007(10) 0.005(11) C49 0.040(13) 0.084(18) 0.013(10) -0.001(11) -0.005(9) 0.021(12) C50 0.030(12) 0.053(14) 0.030(11) -0.007(10) -0.002(9) -0.004(10) C51 0.035(11) 0.029(11) 0.021(10) 0.002(8) 0.008(8) -0.009(8) C52 0.049(13) 0.014(9) 0.028(11) 0.008(8) 0.016(9) 0.004(8) C53 0.039(12) 0.030(11) 0.027(10) -0.010(8) -0.002(9) -0.015(9) C54 0.020(10) 0.029(11) 0.039(11) 0.004(9) -0.005(8) 0.008(8) C55 0.045(12) 0.019(10) 0.033(11) 0.004(8) 0.005(9) -0.011(9) C56 0.09(2) 0.025(12) 0.060(16) 0.002(11) 0.040(15) 0.001(12) C57 0.055(15) 0.038(13) 0.055(15) -0.020(11) 0.014(12) -0.028(11) C58 0.028(11) 0.030(12) 0.063(15) -0.018(11) 0.007(10) 0.004(9) C59 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C60 0.012(9) 0.031(11) 0.035(11) 0.001(8) 0.001(8) -0.008(8) C61 0.033(13) 0.050(14) 0.049(14) -0.004(11) 0.005(10) 0.015(10) C62 0.028(12) 0.067(16) 0.042(13) -0.019(11) 0.015(10) 0.009(11) C63 0.020(11) 0.085(18) 0.029(11) -0.012(11) 0.008(9) -0.009(11) C64 0.032(11) 0.032(11) 0.041(12) -0.020(9) -0.001(9) -0.002(9) C65 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C66 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C67 0.016(10) 0.034(11) 0.054(13) -0.003(10) 0.007(9) -0.003(8) C68 0.032(12) 0.051(14) 0.047(13) 0.002(11) -0.003(10) -0.008(10) C69 0.035(11) 0.024(10) 0.033(11) 0.010(8) 0.008(9) 0.002(8) C70 0.067(17) 0.019(11) 0.10(2) -0.015(12) 0.030(15) -0.020(11) C71 0.050(15) 0.050(15) 0.085(19) 0.008(13) 0.030(14) -0.025(12) C72 0.020(3) 0.038(4) 0.034(3) 0.000(3) -0.001(2) -0.006(3) C73 0.025(10) 0.035(11) 0.022(10) -0.007(8) -0.003(8) 0.006(8) C74 0.018(10) 0.052(14) 0.056(14) -0.002(11) -0.011(9) 0.007(9) C75 0.043(13) 0.025(11) 0.049(13) 0.019(9) 0.007(10) 0.001(9) C76 0.024(10) 0.023(10) 0.028(10) -0.004(8) 0.002(8) -0.004(8) C77 0.030(12) 0.046(14) 0.073(16) -0.032(12) -0.013(11) 0.010(10) C78 0.013(10) 0.044(12) 0.047(13) 0.001(10) -0.007(9) 0.008(8) C79 0.031(12) 0.055(14) 0.029(11) -0.011(10) -0.005(9) -0.005(10) C80 0.023(13) 0.11(2) 0.056(16) 0.022(16) 0.010(11) 0.019(14) C81 0.030(11) 0.063(15) 0.021(10) 0.004(10) -0.003(9) 0.002(10) C82 0.070(17) 0.046(14) 0.045(14) 0.032(11) -0.020(13) -0.031(13) C83 0.040(12) 0.029(11) 0.032(11) 0.007(9) -0.012(9) -0.006(9) C84 0.035(14) 0.12(3) 0.032(13) 0.034(15) -0.012(11) -0.015(15) C85 0.032(11) 0.027(11) 0.035(11) 0.002(9) 0.004(9) -0.001(8) C86 0.024(10) 0.037(11) 0.028(10) -0.005(9) 0.012(8) 0.003(8) C87 0.043(12) 0.025(10) 0.031(11) -0.003(8) 0.001(9) -0.009(9) C88 0.056(14) 0.044(13) 0.024(11) -0.003(9) 0.004(10) 0.004(11) C89 0.039(13) 0.045(14) 0.058(15) -0.005(11) 0.005(11) -0.013(10) C90 0.044(13) 0.050(14) 0.043(13) -0.023(11) -0.006(11) 0.006(11) _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 N2 2.043(13) . ? Ir1 C2 2.058(15) . ? Ir1 C1 2.059(18) . ? Ir1 N1 2.112(15) . ? Ir1 N4 2.167(13) . ? Ir1 N3 2.185(13) . ? Ir1 C27 2.617(16) . ? Ir2 C59 2.026(18) . ? Ir2 C46 2.033(18) . ? Ir2 N7 2.057(16) . ? Ir2 N6 2.086(13) . ? Ir2 N9 2.208(13) . ? Ir2 N8 2.220(14) . ? Ir2 C72 2.623(19) . ? N1 C8 1.27(2) . ? N1 C9 1.40(2) . ? N2 C20 1.32(2) . ? N2 C21 1.40(2) . ? N3 C27 1.37(2) . ? N3 C31 1.49(2) . ? N4 C27 1.33(2) . ? N4 C28 1.48(2) . ? N5 C42 1.39(2) . ? N5 C34 1.43(2) . ? N5 C27 1.47(2) . ? N6 C52 1.31(2) . ? N6 C54 1.39(2) . ? N7 C65 1.37(2) . ? N7 C66 1.43(2) . ? N8 C72 1.34(2) . ? N8 C73 1.45(2) . ? N9 C72 1.33(2) . ? N9 C76 1.47(2) . ? N10 C72 1.42(2) . ? N10 C81 1.43(2) . ? N10 C86 1.45(2) . ? O1 C20 1.36(2) . ? O1 C22 1.40(2) . ? O2 C8 1.36(2) . ? O2 C10 1.41(2) . ? O3 C52 1.39(2) . ? O3 C55 1.39(2) . ? O4 C65 1.37(2) . ? O4 C69 1.40(2) . ? C1 C4 1.41(3) . ? C1 C3 1.45(2) . ? C2 C19 1.39(2) . ? C2 C15 1.41(2) . ? C3 C7 1.42(3) . ? C3 C8 1.44(3) . ? C4 C5 1.43(3) . ? C4 H19 0.9500 . ? C5 C6 1.37(3) . ? C5 H18 0.9500 . ? C6 C7 1.38(3) . ? C6 H17 0.9500 . ? C7 H16 0.9500 . ? C9 C10 1.38(2) . ? C9 C14 1.39(3) . ? C10 C11 1.40(3) . ? C11 C12 1.38(3) . ? C11 H21 0.9500 . ? C12 C13 1.38(3) . ? C12 H25 0.9500 . ? C13 C14 1.41(3) . ? C13 H26 0.9500 . ? C14 H22 0.9500 . ? C15 C16 1.41(2) . ? C15 C20 1.46(2) . ? C16 C17 1.38(3) . ? C16 H3 0.9500 . ? C17 C18 1.40(3) . ? C17 H5 0.9500 . ? C18 C19 1.41(2) . ? C18 H4A 0.9500 . ? C19 H6 0.9500 . ? C21 C26 1.34(2) . ? C21 C22 1.44(3) . ? C22 C23 1.40(3) . ? C23 C24 1.39(3) . ? C23 H13 0.9500 . ? C24 C25 1.40(3) . ? C24 H12 0.9500 . ? C25 C26 1.37(3) . ? C25 H11 0.9500 . ? C26 H9 0.9500 . ? C28 C30 1.52(3) . ? C28 C29 1.54(2) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.53(2) . ? C31 C33 1.53(3) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.38(3) . ? C34 C36 1.40(3) . ? C35 C37 1.41(3) . ? C35 H35 0.9500 . ? C36 C38 1.42(3) . ? C36 H36 0.9500 . ? C37 C39 1.33(3) . ? C37 H37 0.9500 . ? C38 C39 1.43(4) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C45 1.38(3) . ? C40 C42 1.43(2) . ? C40 H40 0.9500 . ? C41 C45 1.39(3) . ? C41 C44 1.43(3) . ? C41 H41 0.9500 . ? C42 C43 1.40(2) . ? C43 C44 1.38(3) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C47 1.42(2) . ? C46 C51 1.43(2) . ? C47 C48 1.41(3) . ? C47 C52 1.43(3) . ? C48 C49 1.42(3) . ? C48 H48 0.9500 . ? C49 C50 1.35(3) . ? C49 H49 0.9500 . ? C50 C51 1.40(3) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? C53 C58 1.38(2) . ? C53 C54 1.41(2) . ? C53 H53 0.9500 . ? C54 C55 1.42(2) . ? C55 C56 1.37(3) . ? C56 C57 1.39(3) . ? C56 H56 0.9500 . ? C57 C58 1.39(3) . ? C57 H57 0.9500 . ? C58 H58 0.9500 . ? C59 C64 1.39(2) . ? C59 C60 1.48(2) . ? C60 C65 1.36(2) . ? C60 C61 1.40(2) . ? C61 C62 1.36(3) . ? C61 H61 0.9500 . ? C62 C63 1.42(3) . ? C62 H62 0.9500 . ? C63 C64 1.43(3) . ? C63 H63 0.9500 . ? C64 H64 0.9500 . ? C66 C69 1.37(2) . ? C66 C67 1.42(2) . ? C67 C68 1.39(3) . ? C67 H67 0.9500 . ? C68 C71 1.39(3) . ? C68 H68 0.9500 . ? C69 C70 1.38(2) . ? C70 C71 1.40(3) . ? C70 H70 0.9500 . ? C71 H71 0.9500 . ? C73 C74 1.49(2) . ? C73 C75 1.57(2) . ? C73 H73 1.0000 . ? C74 H74A 0.9800 . ? C74 H74B 0.9800 . ? C74 H74C 0.9800 . ? C75 H75A 0.9800 . ? C75 H75B 0.9800 . ? C75 H75C 0.9800 . ? C76 C78 1.48(2) . ? C76 C77 1.60(2) . ? C76 H76 1.0000 . ? C77 H77A 0.9800 . ? C77 H77B 0.9800 . ? C77 H77C 0.9800 . ? C78 H78A 0.9800 . ? C78 H78B 0.9800 . ? C78 H78C 0.9800 . ? C79 C81 1.38(3) . ? C79 C80 1.39(3) . ? C79 H79 0.9500 . ? C80 C84 1.37(4) . ? C80 H80 0.9500 . ? C81 C83 1.40(3) . ? C82 C84 1.37(3) . ? C82 C83 1.40(3) . ? C82 H82 0.9500 . ? C83 H83 0.9500 . ? C84 H84 0.9500 . ? C85 C88 1.40(3) . ? C85 C86 1.40(3) . ? C85 H85 0.9500 . ? C86 C87 1.42(2) . ? C87 C89 1.36(3) . ? C87 H87 0.9500 . ? C88 C90 1.38(3) . ? C88 H88 0.9500 . ? C89 C90 1.39(3) . ? C89 H89 0.9500 . ? C90 H90 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ir1 C2 79.7(6) . . ? N2 Ir1 C1 94.6(7) . . ? C2 Ir1 C1 87.7(6) . . ? N2 Ir1 N1 171.4(5) . . ? C2 Ir1 N1 94.0(6) . . ? C1 Ir1 N1 79.3(7) . . ? N2 Ir1 N4 95.7(5) . . ? C2 Ir1 N4 165.7(6) . . ? C1 Ir1 N4 106.2(6) . . ? N1 Ir1 N4 91.8(5) . . ? N2 Ir1 N3 91.3(5) . . ? C2 Ir1 N3 104.2(6) . . ? C1 Ir1 N3 167.5(6) . . ? N1 Ir1 N3 95.9(5) . . ? N4 Ir1 N3 62.2(5) . . ? N2 Ir1 C27 94.4(6) . . ? C2 Ir1 C27 135.7(6) . . ? C1 Ir1 C27 136.6(6) . . ? N1 Ir1 C27 94.1(5) . . ? N4 Ir1 C27 30.5(5) . . ? N3 Ir1 C27 31.6(5) . . ? C59 Ir2 C46 90.9(7) . . ? C59 Ir2 N7 80.2(6) . . ? C46 Ir2 N7 91.7(6) . . ? C59 Ir2 N6 94.5(6) . . ? C46 Ir2 N6 79.0(6) . . ? N7 Ir2 N6 169.2(5) . . ? C59 Ir2 N9 162.5(7) . . ? C46 Ir2 N9 106.1(6) . . ? N7 Ir2 N9 95.1(5) . . ? N6 Ir2 N9 92.6(5) . . ? C59 Ir2 N8 102.0(6) . . ? C46 Ir2 N8 166.8(6) . . ? N7 Ir2 N8 93.3(5) . . ? N6 Ir2 N8 96.9(5) . . ? N9 Ir2 N8 61.2(5) . . ? C59 Ir2 C72 132.6(7) . . ? C46 Ir2 C72 136.5(6) . . ? N7 Ir2 C72 94.7(5) . . ? N6 Ir2 C72 95.7(6) . . ? N9 Ir2 C72 30.4(5) . . ? N8 Ir2 C72 30.8(5) . . ? C8 N1 C9 109.2(16) . . ? C8 N1 Ir1 112.9(13) . . ? C9 N1 Ir1 137.6(12) . . ? C20 N2 C21 107.8(15) . . ? C20 N2 Ir1 114.7(12) . . ? C21 N2 Ir1 137.1(12) . . ? C27 N3 C31 125.4(14) . . ? C27 N3 Ir1 91.8(10) . . ? C31 N3 Ir1 139.3(11) . . ? C27 N4 C28 120.9(15) . . ? C27 N4 Ir1 93.7(10) . . ? C28 N4 Ir1 139.8(10) . . ? C42 N5 C34 120.0(13) . . ? C42 N5 C27 121.0(14) . . ? C34 N5 C27 118.9(15) . . ? C52 N6 C54 108.8(15) . . ? C52 N6 Ir2 111.9(11) . . ? C54 N6 Ir2 139.1(12) . . ? C65 N7 C66 107.3(15) . . ? C65 N7 Ir2 112.3(11) . . ? C66 N7 Ir2 139.5(12) . . ? C72 N8 C73 128.8(15) . . ? C72 N8 Ir2 91.4(11) . . ? C73 N8 Ir2 134.4(11) . . ? C72 N9 C76 125.9(14) . . ? C72 N9 Ir2 92.4(11) . . ? C76 N9 Ir2 137.2(11) . . ? C72 N10 C81 121.2(15) . . ? C72 N10 C86 121.8(14) . . ? C81 N10 C86 116.6(14) . . ? C20 O1 C22 104.5(14) . . ? C8 O2 C10 104.5(13) . . ? C52 O3 C55 106.2(14) . . ? C65 O4 C69 107.1(13) . . ? C4 C1 C3 117.2(17) . . ? C4 C1 Ir1 129.2(14) . . ? C3 C1 Ir1 113.5(13) . . ? C19 C2 C15 117.3(15) . . ? C19 C2 Ir1 127.9(13) . . ? C15 C2 Ir1 114.7(12) . . ? C7 C3 C8 126.3(17) . . ? C7 C3 C1 122.1(19) . . ? C8 C3 C1 111.6(16) . . ? C1 C4 C5 119.5(18) . . ? C1 C4 H19 120.4 . . ? C5 C4 H19 120.1 . . ? C6 C5 C4 121.1(19) . . ? C6 C5 H18 119.4 . . ? C4 C5 H18 119.6 . . ? C5 C6 C7 122.0(18) . . ? C5 C6 H17 118.9 . . ? C7 C6 H17 119.1 . . ? C6 C7 C3 117.8(19) . . ? C6 C7 H16 121.2 . . ? C3 C7 H16 121.0 . . ? N1 C8 O2 112.7(17) . . ? N1 C8 C3 122.3(17) . . ? O2 C8 C3 124.6(16) . . ? C10 C9 C14 121.1(18) . . ? C10 C9 N1 105.7(17) . . ? C14 C9 N1 133.2(16) . . ? C9 C10 C11 123(2) . . ? C9 C10 O2 107.9(17) . . ? C11 C10 O2 128.7(18) . . ? C12 C11 C10 114.5(19) . . ? C12 C11 H21 122.8 . . ? C10 C11 H21 122.7 . . ? C11 C12 C13 124(2) . . ? C11 C12 H25 118.1 . . ? C13 C12 H25 117.9 . . ? C12 C13 C14 120(2) . . ? C12 C13 H26 119.9 . . ? C14 C13 H26 119.7 . . ? C9 C14 C13 116.6(17) . . ? C9 C14 H22 121.7 . . ? C13 C14 H22 121.7 . . ? C16 C15 C2 123.6(17) . . ? C16 C15 C20 124.7(17) . . ? C2 C15 C20 111.5(15) . . ? C17 C16 C15 116.9(19) . . ? C17 C16 H3 121.8 . . ? C15 C16 H3 121.3 . . ? C16 C17 C18 121.3(18) . . ? C16 C17 H5 119.1 . . ? C18 C17 H5 119.5 . . ? C17 C18 C19 120.0(18) . . ? C17 C18 H4A 120.0 . . ? C19 C18 H4A 120.0 . . ? C2 C19 C18 120.6(19) . . ? C2 C19 H6 120.0 . . ? C18 C19 H6 119.4 . . ? N2 C20 O1 113.9(16) . . ? N2 C20 C15 119.0(17) . . ? O1 C20 C15 127.1(16) . . ? C26 C21 N2 136.1(18) . . ? C26 C21 C22 118.9(18) . . ? N2 C21 C22 105.0(15) . . ? C23 C22 O1 128.8(19) . . ? C23 C22 C21 122.6(19) . . ? O1 C22 C21 108.6(16) . . ? C24 C23 C22 116(2) . . ? C24 C23 H13 121.8 . . ? C22 C23 H13 121.9 . . ? C23 C24 C25 120(2) . . ? C23 C24 H12 120.0 . . ? C25 C24 H12 119.9 . . ? C26 C25 C24 123(2) . . ? C26 C25 H11 119.0 . . ? C24 C25 H11 118.4 . . ? C21 C26 C25 119(2) . . ? C21 C26 H9 120.4 . . ? C25 C26 H9 120.2 . . ? N4 C27 N3 112.3(14) . . ? N4 C27 N5 124.2(15) . . ? N3 C27 N5 123.4(15) . . ? N4 C27 Ir1 55.7(8) . . ? N3 C27 Ir1 56.6(8) . . ? N5 C27 Ir1 178.2(13) . . ? N4 C28 C30 111.8(15) . . ? N4 C28 C29 106.9(14) . . ? C30 C28 C29 111.6(16) . . ? N4 C28 H28 108.8 . . ? C30 C28 H28 108.8 . . ? C29 C28 H28 108.9 . . ? C28 C29 H29A 109.3 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.6 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.6 . . ? C28 C30 H30B 109.1 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.8 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N3 C31 C32 106.8(14) . . ? N3 C31 C33 111.6(15) . . ? C32 C31 C33 111.1(17) . . ? N3 C31 H31 109.0 . . ? C32 C31 H31 109.0 . . ? C33 C31 H31 109.2 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.6 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.3 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.4 . . ? C31 C33 H33B 109.6 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C36 120.5(18) . . ? C35 C34 N5 118.5(18) . . ? C36 C34 N5 121.0(17) . . ? C34 C35 C37 119(2) . . ? C34 C35 H35 120.4 . . ? C37 C35 H35 120.3 . . ? C34 C36 C38 121(2) . . ? C34 C36 H36 119.3 . . ? C38 C36 H36 119.4 . . ? C39 C37 C35 120(2) . . ? C39 C37 H37 119.9 . . ? C35 C37 H37 120.2 . . ? C36 C38 C39 115(2) . . ? C36 C38 H38 121.8 . . ? C39 C38 H38 123.0 . . ? C37 C39 C38 123(2) . . ? C37 C39 H39 119.0 . . ? C38 C39 H39 117.5 . . ? C45 C40 C42 123.1(17) . . ? C45 C40 H40 118.4 . . ? C42 C40 H40 118.5 . . ? C45 C41 C44 118.1(19) . . ? C45 C41 H41 121.0 . . ? C44 C41 H41 121.0 . . ? N5 C42 C43 121.1(15) . . ? N5 C42 C40 123.0(15) . . ? C43 C42 C40 115.9(17) . . ? C44 C43 C42 121.8(16) . . ? C44 C43 H43 119.1 . . ? C42 C43 H43 119.1 . . ? C43 C44 C41 121.2(18) . . ? C43 C44 H44 119.4 . . ? C41 C44 H44 119.5 . . ? C40 C45 C41 119.9(17) . . ? C40 C45 H45 120.0 . . ? C41 C45 H45 120.0 . . ? C47 C46 C51 114.6(17) . . ? C47 C46 Ir2 116.8(13) . . ? C51 C46 Ir2 128.5(13) . . ? C48 C47 C46 125.1(18) . . ? C48 C47 C52 125.5(18) . . ? C46 C47 C52 109.4(16) . . ? C47 C48 C49 116(2) . . ? C47 C48 H48 121.9 . . ? C49 C48 H48 122.1 . . ? C50 C49 C48 121.0(19) . . ? C50 C49 H49 119.6 . . ? C48 C49 H49 119.4 . . ? C49 C50 C51 122.5(18) . . ? C49 C50 H50 118.7 . . ? C51 C50 H50 118.8 . . ? C50 C51 C46 120.5(18) . . ? C50 C51 H51 119.7 . . ? C46 C51 H51 119.8 . . ? N6 C52 O3 111.3(16) . . ? N6 C52 C47 122.8(16) . . ? O3 C52 C47 125.8(17) . . ? C58 C53 C54 117.9(19) . . ? C58 C53 H53 121.1 . . ? C54 C53 H53 121.0 . . ? N6 C54 C53 134.5(17) . . ? N6 C54 C55 106.7(16) . . ? C53 C54 C55 118.7(17) . . ? C56 C55 O3 129.6(19) . . ? C56 C55 C54 123(2) . . ? O3 C55 C54 106.9(14) . . ? C55 C56 C57 116(2) . . ? C55 C56 H56 122.0 . . ? C57 C56 H56 121.8 . . ? C58 C57 C56 122.5(19) . . ? C58 C57 H57 118.8 . . ? C56 C57 H57 118.7 . . ? C53 C58 C57 121(2) . . ? C53 C58 H58 119.5 . . ? C57 C58 H58 119.3 . . ? C64 C59 C60 116.6(16) . . ? C64 C59 Ir2 129.3(14) . . ? C60 C59 Ir2 114.0(12) . . ? C65 C60 C61 127.6(18) . . ? C65 C60 C59 111.9(16) . . ? C61 C60 C59 120.4(16) . . ? C62 C61 C60 121(2) . . ? C62 C61 H61 119.3 . . ? C60 C61 H61 119.4 . . ? C61 C62 C63 120.9(18) . . ? C61 C62 H62 119.5 . . ? C63 C62 H62 119.6 . . ? C62 C63 C64 119.0(18) . . ? C62 C63 H63 120.4 . . ? C64 C63 H63 120.6 . . ? C59 C64 C63 121.7(18) . . ? C59 C64 H64 119.1 . . ? C63 C64 H64 119.2 . . ? C60 C65 N7 120.6(17) . . ? C60 C65 O4 129.0(17) . . ? N7 C65 O4 109.1(14) . . ? C69 C66 C67 121.8(16) . . ? C69 C66 N7 106.4(15) . . ? C67 C66 N7 131.8(17) . . ? C68 C67 C66 114.9(18) . . ? C68 C67 H67 122.6 . . ? C66 C67 H67 122.5 . . ? C67 C68 C71 122.6(19) . . ? C67 C68 H68 118.6 . . ? C71 C68 H68 118.8 . . ? C66 C69 C70 123.3(18) . . ? C66 C69 O4 109.2(15) . . ? C70 C69 O4 127.4(17) . . ? C69 C70 C71 115.4(19) . . ? C69 C70 H70 122.3 . . ? C71 C70 H70 122.3 . . ? C68 C71 C70 121.9(19) . . ? C68 C71 H71 119.0 . . ? C70 C71 H71 119.1 . . ? N9 C72 N8 115.0(16) . . ? N9 C72 N10 122.5(16) . . ? N8 C72 N10 122.5(17) . . ? N9 C72 Ir2 57.2(9) . . ? N8 C72 Ir2 57.8(9) . . ? N10 C72 Ir2 179.6(13) . . ? N8 C73 C74 110.6(15) . . ? N8 C73 C75 111.5(14) . . ? C74 C73 C75 111.8(15) . . ? N8 C73 H73 107.5 . . ? C74 C73 H73 107.5 . . ? C75 C73 H73 107.7 . . ? C73 C74 H74A 109.7 . . ? C73 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C73 C74 H74C 109.3 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C73 C75 H75A 109.5 . . ? C73 C75 H75B 109.5 . . ? H75A C75 H75B 109.5 . . ? C73 C75 H75C 109.4 . . ? H75A C75 H75C 109.5 . . ? H75B C75 H75C 109.5 . . ? N9 C76 C78 110.0(14) . . ? N9 C76 C77 110.0(14) . . ? C78 C76 C77 110.7(16) . . ? N9 C76 H76 108.7 . . ? C78 C76 H76 108.8 . . ? C77 C76 H76 108.7 . . ? C76 C77 H77A 109.5 . . ? C76 C77 H77B 109.5 . . ? H77A C77 H77B 109.5 . . ? C76 C77 H77C 109.4 . . ? H77A C77 H77C 109.5 . . ? H77B C77 H77C 109.5 . . ? C76 C78 H78A 109.5 . . ? C76 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C76 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C81 C79 C80 121(2) . . ? C81 C79 H79 119.1 . . ? C80 C79 H79 119.7 . . ? C84 C80 C79 120(2) . . ? C84 C80 H80 120.5 . . ? C79 C80 H80 119.7 . . ? C79 C81 C83 118.6(19) . . ? C79 C81 N10 122.1(19) . . ? C83 C81 N10 119.3(17) . . ? C84 C82 C83 120(2) . . ? C84 C82 H82 120.1 . . ? C83 C82 H82 120.1 . . ? C81 C83 C82 120(2) . . ? C81 C83 H83 119.7 . . ? C82 C83 H83 120.3 . . ? C80 C84 C82 121(2) . . ? C80 C84 H84 119.2 . . ? C82 C84 H84 120.2 . . ? C88 C85 C86 121.2(18) . . ? C88 C85 H85 119.4 . . ? C86 C85 H85 119.4 . . ? C85 C86 C87 116.8(17) . . ? C85 C86 N10 122.3(16) . . ? C87 C86 N10 120.9(16) . . ? C89 C87 C86 120.5(19) . . ? C89 C87 H87 119.8 . . ? C86 C87 H87 119.6 . . ? C90 C88 C85 121.3(19) . . ? C90 C88 H88 119.3 . . ? C85 C88 H88 119.3 . . ? C87 C89 C90 123(2) . . ? C87 C89 H89 118.6 . . ? C90 C89 H89 118.6 . . ? C88 C90 C89 117.2(19) . . ? C88 C90 H90 121.4 . . ? C89 C90 H90 121.4 . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 3.956 _refine_diff_density_min -2.947 _refine_diff_density_rms 0.227 data_6 _database_code_depnum_ccdc_archive 'CCDC 857587' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H40 Ir N5 S2' _chemical_formula_weight 907.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.311(6) _cell_length_b 16.719(11) _cell_length_c 24.391(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.481(12) _cell_angle_gamma 90.00 _cell_volume 3797(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 258 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 3.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5276 _exptl_absorpt_correction_T_max 0.7106 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19580 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.1670 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.08 _reflns_number_total 6694 _reflns_number_gt 3887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6694 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 0.655 _refine_ls_restrained_S_all 0.655 _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 0.74936(3) 0.214057(18) 0.592920(13) 0.02054(8) Uani 1 1 d . . . S1 S 0.7637(2) 0.47483(11) 0.55044(9) 0.0372(6) Uani 1 1 d . . . S2 S 0.7978(2) -0.03149(11) 0.52037(9) 0.0367(6) Uani 1 1 d . . . N1 N 0.7070(6) 0.3344(3) 0.5872(2) 0.0223(15) Uani 1 1 d . . . N2 N 0.8006(5) 0.0957(3) 0.5807(2) 0.0205(15) Uani 1 1 d . . . N3 N 0.5983(6) 0.1844(3) 0.6574(2) 0.0228(15) Uani 1 1 d . . . N4 N 0.8144(5) 0.2248(3) 0.6783(2) 0.0234(14) Uani 1 1 d . . . N5 N 0.6545(5) 0.1964(3) 0.7537(2) 0.0269(16) Uani 1 1 d . . . C1 C 0.9217(7) 0.2497(4) 0.5523(3) 0.0241(19) Uani 1 1 d . . . C2 C 0.6498(7) 0.1943(4) 0.5217(3) 0.0235(19) Uani 1 1 d . . . C3 C 0.9317(7) 0.3334(4) 0.5435(3) 0.0224(18) Uani 1 1 d . . . C4 C 1.0513(7) 0.3712(4) 0.5213(3) 0.029(2) Uani 1 1 d . . . H4 H 1.0540 0.4278 0.5178 0.035 Uiso 1 1 d R . . C5 C 1.1651(8) 0.3258(5) 0.5048(3) 0.036(2) Uani 1 1 d . . . H5 H 1.2473 0.3500 0.4891 0.043 Uiso 1 1 d R . . C6 C 1.1588(7) 0.2437(4) 0.5110(3) 0.034(2) Uani 1 1 d . . . H6 H 1.2366 0.2114 0.4994 0.040 Uiso 1 1 d R . . C7 C 1.0398(7) 0.2085(5) 0.5343(3) 0.0268(18) Uani 1 1 d . . . H7 H 1.0394 0.1520 0.5381 0.032 Uiso 1 1 d R . . C8 C 0.8048(7) 0.3752(4) 0.5621(3) 0.0215(18) Uani 1 1 d . . . C9 C 0.5857(7) 0.3811(4) 0.5997(3) 0.0222(18) Uani 1 1 d . . . C10 C 0.5983(7) 0.4602(4) 0.5817(3) 0.031(2) Uani 1 1 d . . . C11 C 0.4894(8) 0.5158(4) 0.5874(3) 0.037(2) Uani 1 1 d . . . H11 H 0.5004 0.5692 0.5747 0.044 Uiso 1 1 d R . . C12 C 0.3652(8) 0.4917(5) 0.6118(3) 0.042(2) Uani 1 1 d . . . H12 H 0.2878 0.5282 0.6159 0.050 Uiso 1 1 d R . . C13 C 0.3517(7) 0.4130(5) 0.6311(3) 0.038(2) Uani 1 1 d . . . H13 H 0.2661 0.3980 0.6494 0.045 Uiso 1 1 d R . . C14 C 0.4591(7) 0.3562(4) 0.6243(3) 0.0287(19) Uani 1 1 d . . . H14 H 0.4466 0.3024 0.6359 0.034 Uiso 1 1 d R . . C15 C 0.6585(7) 0.1166(4) 0.5009(3) 0.0240(18) Uani 1 1 d . . . C16 C 0.5927(7) 0.0907(4) 0.4519(3) 0.030(2) Uani 1 1 d . . . H16 H 0.6029 0.0370 0.4397 0.036 Uiso 1 1 d R . . C17 C 0.5137(7) 0.1441(5) 0.4222(3) 0.034(2) Uani 1 1 d . . . H17 H 0.4671 0.1280 0.3892 0.041 Uiso 1 1 d R . . C18 C 0.5016(6) 0.2230(5) 0.4406(3) 0.0257(18) Uani 1 1 d . . . H18 H 0.4470 0.2604 0.4199 0.031 Uiso 1 1 d R . . C19 C 0.5686(7) 0.2476(4) 0.4891(3) 0.0251(19) Uani 1 1 d . . . H19 H 0.5592 0.3016 0.5005 0.030 Uiso 1 1 d R . . C20 C 0.7468(7) 0.0662(4) 0.5344(3) 0.0233(19) Uani 1 1 d . . . C21 C 0.8964(7) 0.0422(4) 0.6058(3) 0.0255(19) Uani 1 1 d . . . C22 C 0.9056(8) -0.0312(4) 0.5784(3) 0.033(2) Uani 1 1 d . . . C23 C 0.9999(8) -0.0898(5) 0.5982(4) 0.042(2) Uani 1 1 d . . . H23 H 1.0077 -0.1400 0.5802 0.051 Uiso 1 1 d R . . C24 C 1.0801(8) -0.0736(5) 0.6441(4) 0.042(2) Uani 1 1 d . . . H24 H 1.1438 -0.1134 0.6578 0.051 Uiso 1 1 d R . . C25 C 1.0718(8) -0.0011(4) 0.6712(3) 0.035(2) Uani 1 1 d . . . H25 H 1.1290 0.0083 0.7030 0.042 Uiso 1 1 d R . . C26 C 0.9798(7) 0.0577(4) 0.6516(3) 0.0289(19) Uani 1 1 d . . . H26 H 0.9741 0.1080 0.6696 0.035 Uiso 1 1 d R . . C27 C 0.6897(7) 0.2027(4) 0.6979(3) 0.0217(17) Uani 1 1 d . . . C28 C 0.9148(7) 0.2762(5) 0.7093(3) 0.034(2) Uani 1 1 d . . . H28 H 0.9154 0.2584 0.7485 0.040 Uiso 1 1 d R . . C29 C 0.8769(9) 0.3622(5) 0.7075(4) 0.075(3) Uani 1 1 d . . . H29A H 0.7840 0.3702 0.7254 0.113 Uiso 1 1 d R . . H29B H 0.9508 0.3934 0.7268 0.113 Uiso 1 1 d R . . H29C H 0.8703 0.3800 0.6693 0.113 Uiso 1 1 d R . . C30 C 1.0672(7) 0.2653(5) 0.6864(4) 0.068(3) Uani 1 1 d . . . H30A H 1.0659 0.2754 0.6468 0.102 Uiso 1 1 d R . . H30B H 1.1332 0.3030 0.7044 0.102 Uiso 1 1 d R . . H30C H 1.0996 0.2104 0.6934 0.102 Uiso 1 1 d R . . C31 C 0.4739(7) 0.1304(4) 0.6640(3) 0.0277(19) Uani 1 1 d . . . H31 H 0.4129 0.1513 0.6943 0.033 Uiso 1 1 d R . . C32 C 0.5244(7) 0.0450(4) 0.6795(3) 0.047(2) Uani 1 1 d . . . H32A H 0.5790 0.0471 0.7140 0.071 Uiso 1 1 d R . . H32B H 0.4406 0.0102 0.6840 0.071 Uiso 1 1 d R . . H32C H 0.5856 0.0238 0.6505 0.071 Uiso 1 1 d R . . C33 C 0.3851(7) 0.1302(4) 0.6115(3) 0.038(2) Uani 1 1 d . . . H33A H 0.4433 0.1102 0.5811 0.057 Uiso 1 1 d R . . H33B H 0.3011 0.0955 0.6161 0.057 Uiso 1 1 d R . . H33C H 0.3532 0.1848 0.6034 0.057 Uiso 1 1 d R . . C34 C 0.5196(7) 0.2259(5) 0.7729(3) 0.037(2) Uani 1 1 d . . . C35 C 0.4734(4) 0.3013(2) 0.76151(16) 0.052(3) Uani 1 1 d . . . H35 H 0.5304 0.3356 0.7396 0.062 Uiso 1 1 d R . . C39 C 0.4353(4) 0.1743(2) 0.80410(16) 0.058(3) Uani 1 1 d R . . H39 H 0.4661 0.1213 0.8119 0.070 Uiso 1 1 d R . . C40 C 0.7560(4) 0.1687(2) 0.79413(16) 0.0244(19) Uani 1 1 d R . . C41 C 0.7639(4) 0.2051(2) 0.84440(16) 0.0275(18) Uani 1 1 d R . . H41 H 0.7021 0.2486 0.8527 0.033 Uiso 1 1 d R . . C36 C 0.3420(9) 0.3301(5) 0.7817(4) 0.065 Uani 1 1 d . . . H36 H 0.3108 0.3832 0.7743 0.079 Uiso 1 1 d R . . C37 C 0.2652(8) 0.2790(6) 0.8116(3) 0.063 Uani 1 1 d . . . H37 H 0.1758 0.2974 0.8253 0.075 Uiso 1 1 d R . . C38 C 0.3027(8) 0.2026(6) 0.8237(3) 0.063 Uani 1 1 d . . . H38 H 0.2433 0.1687 0.8449 0.075 Uiso 1 1 d R . . C42 C 0.8631(7) 0.1783(4) 0.8834(3) 0.034(2) Uani 1 1 d . . . H42 H 0.8667 0.2023 0.9187 0.040 Uiso 1 1 d R . . C43 C 0.9566(8) 0.1160(5) 0.8709(3) 0.036(2) Uani 1 1 d . . . H43 H 1.0266 0.0987 0.8968 0.043 Uiso 1 1 d R . . C44 C 0.9463(8) 0.0801(5) 0.8202(3) 0.035(2) Uani 1 1 d . . . H44 H 1.0092 0.0373 0.8116 0.042 Uiso 1 1 d R . . C45 C 0.8462(7) 0.1052(4) 0.7815(3) 0.030(2) Uani 1 1 d . . . H45 H 0.8393 0.0793 0.7469 0.036 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02260(15) 0.01830(15) 0.02069(16) 0.00043(18) -0.00029(11) -0.00036(18) S1 0.0394(13) 0.0219(12) 0.0505(16) 0.0074(11) 0.0100(11) 0.0025(10) S2 0.0449(14) 0.0224(12) 0.0427(15) -0.0079(10) -0.0041(11) 0.0030(10) N1 0.024(4) 0.025(4) 0.018(4) -0.003(3) -0.003(3) 0.001(3) N2 0.016(3) 0.013(3) 0.032(4) 0.005(3) 0.000(3) 0.004(3) N3 0.026(4) 0.017(3) 0.025(4) -0.005(3) -0.007(3) -0.008(3) N4 0.022(3) 0.031(4) 0.017(3) 0.002(3) -0.002(3) -0.007(3) N5 0.022(3) 0.033(4) 0.025(4) 0.008(3) 0.001(3) -0.001(3) C1 0.027(5) 0.021(4) 0.024(5) -0.008(4) -0.003(4) 0.003(4) C2 0.020(4) 0.021(5) 0.029(5) 0.002(4) 0.005(4) -0.008(3) C3 0.021(4) 0.030(5) 0.017(5) 0.004(4) 0.005(4) 0.001(4) C4 0.039(5) 0.026(5) 0.022(5) 0.001(4) 0.004(4) 0.001(4) C5 0.035(5) 0.033(5) 0.039(6) 0.006(4) 0.017(4) 0.005(4) C6 0.023(5) 0.024(5) 0.054(6) 0.001(4) 0.002(4) 0.013(4) C7 0.029(4) 0.016(4) 0.036(5) 0.003(4) 0.004(4) -0.005(4) C8 0.025(4) 0.023(4) 0.017(5) 0.001(3) 0.011(4) -0.007(4) C9 0.031(5) 0.017(4) 0.018(5) -0.004(3) -0.004(4) -0.003(4) C10 0.028(5) 0.026(5) 0.039(6) 0.000(4) 0.004(4) 0.001(4) C11 0.040(5) 0.025(5) 0.046(6) 0.006(4) 0.006(4) 0.005(4) C12 0.043(6) 0.035(6) 0.048(6) 0.006(5) -0.004(5) 0.016(4) C13 0.026(5) 0.045(6) 0.043(6) 0.001(5) 0.011(4) 0.000(4) C14 0.031(5) 0.024(5) 0.032(5) -0.002(4) 0.007(4) 0.001(4) C15 0.026(4) 0.030(5) 0.016(5) 0.000(4) 0.000(4) -0.006(4) C16 0.034(5) 0.032(5) 0.025(5) -0.001(4) 0.000(4) -0.006(4) C17 0.040(5) 0.039(5) 0.024(5) -0.002(4) -0.009(4) -0.010(4) C18 0.018(4) 0.038(5) 0.021(4) 0.006(4) -0.005(3) 0.007(4) C19 0.024(4) 0.021(4) 0.030(5) -0.005(4) 0.001(4) -0.004(3) C20 0.023(4) 0.022(5) 0.025(5) -0.008(4) 0.000(4) -0.007(4) C21 0.024(4) 0.017(4) 0.035(5) 0.005(4) 0.006(4) -0.004(4) C22 0.036(5) 0.024(5) 0.040(6) 0.010(4) 0.013(4) 0.002(4) C23 0.037(5) 0.039(6) 0.051(7) 0.000(5) 0.001(5) 0.015(4) C24 0.042(6) 0.039(6) 0.046(7) 0.011(5) 0.008(5) 0.013(5) C25 0.040(5) 0.037(5) 0.028(5) 0.010(4) -0.005(4) 0.015(4) C26 0.031(5) 0.021(5) 0.035(5) 0.002(4) 0.002(4) -0.001(4) C27 0.036(5) 0.010(4) 0.020(4) 0.003(3) 0.003(4) 0.001(4) C28 0.035(5) 0.033(5) 0.034(5) -0.002(4) -0.004(4) -0.013(4) C29 0.094(8) 0.047(7) 0.085(9) -0.013(6) -0.021(6) -0.014(6) C30 0.036(5) 0.094(8) 0.074(8) -0.021(6) -0.004(5) -0.029(5) C31 0.023(4) 0.033(5) 0.027(5) 0.005(4) -0.003(4) -0.007(4) C32 0.043(5) 0.031(5) 0.067(7) 0.007(5) -0.009(5) -0.008(4) C33 0.031(5) 0.056(6) 0.028(5) -0.004(4) -0.007(4) -0.016(4) C34 0.028(5) 0.060(6) 0.023(5) -0.021(5) -0.004(4) -0.002(5) C35 0.045(6) 0.076(8) 0.035(6) -0.022(5) -0.010(4) 0.024(5) C39 0.038(6) 0.101(8) 0.036(6) -0.008(5) 0.001(5) -0.014(5) C40 0.030(5) 0.021(4) 0.022(5) 0.006(4) 0.007(4) -0.010(4) C41 0.023(4) 0.033(5) 0.026(5) 0.004(4) 0.001(3) -0.001(4) C36 0.062 0.066 0.068 -0.030 -0.016 0.017 C37 0.044 0.100 0.045 -0.023 -0.004 0.007 C38 0.052 0.098 0.038 -0.012 -0.002 -0.024 C42 0.043(5) 0.038(5) 0.020(5) -0.001(4) -0.003(4) -0.012(4) C43 0.028(5) 0.045(6) 0.035(6) 0.017(5) 0.004(4) -0.001(4) C44 0.029(5) 0.037(5) 0.040(6) 0.014(5) 0.003(4) 0.007(4) C45 0.028(5) 0.035(5) 0.026(5) -0.006(4) 0.006(4) -0.008(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 Ir1 C1 1.984(7) . ? Ir1 C2 1.991(7) . ? Ir1 N1 2.056(5) . ? Ir1 N2 2.058(5) . ? Ir1 N4 2.171(6) . ? Ir1 N3 2.176(6) . ? S1 C8 1.732(7) . ? S1 C10 1.741(7) . ? S2 C22 1.729(8) . ? S2 C20 1.736(7) . ? N1 C8 1.295(7) . ? N1 C9 1.408(8) . ? N2 C20 1.326(8) . ? N2 C21 1.400(8) . ? N3 C27 1.333(8) . ? N3 C31 1.479(7) . ? N4 C27 1.312(7) . ? N4 C28 1.475(8) . ? N5 C27 1.407(8) . ? N5 C34 1.433(8) . ? N5 C40 1.437(6) . ? C1 C7 1.373(8) . ? C1 C3 1.420(8) . ? C2 C15 1.397(9) . ? C2 C19 1.410(9) . ? C3 C4 1.394(8) . ? C3 C8 1.448(8) . ? C4 C5 1.367(8) . ? C4 H4 0.9500 . ? C5 C6 1.381(8) . ? C5 H5 0.9500 . ? C6 C7 1.381(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C9 C14 1.390(8) . ? C9 C10 1.399(9) . ? C10 C11 1.384(9) . ? C11 C12 1.366(9) . ? C11 H11 0.9500 . ? C12 C13 1.403(9) . ? C12 H12 0.9500 . ? C13 C14 1.391(9) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.407(9) . ? C15 C20 1.429(9) . ? C16 C17 1.362(9) . ? C16 H16 0.9500 . ? C17 C18 1.398(9) . ? C17 H17 0.9500 . ? C18 C19 1.393(9) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C21 C26 1.381(9) . ? C21 C22 1.401(9) . ? C22 C23 1.399(9) . ? C23 C24 1.367(11) . ? C23 H23 0.9500 . ? C24 C25 1.384(10) . ? C24 H24 0.9500 . ? C25 C26 1.386(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C28 C29 1.482(10) . ? C28 C30 1.540(8) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C33 1.518(9) . ? C31 C32 1.549(9) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.360(9) . ? C34 C39 1.396(8) . ? C35 C36 1.408(9) . ? C35 H35 0.9500 . ? C39 C38 1.409(8) . ? C39 H39 0.9500 . ? C40 C41 1.3708 . ? C40 C45 1.390(7) . ? C41 C42 1.396(8) . ? C41 H41 0.9500 . ? C36 C37 1.335(11) . ? C36 H36 0.9500 . ? C37 C38 1.356(12) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C42 C43 1.394(9) . ? C42 H42 0.9500 . ? C43 C44 1.376(10) . ? C43 H43 0.9500 . ? C44 C45 1.386(9) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 C2 89.2(3) . . ? C1 Ir1 N1 80.1(2) . . ? C2 Ir1 N1 90.9(2) . . ? C1 Ir1 N2 91.5(2) . . ? C2 Ir1 N2 79.7(3) . . ? N1 Ir1 N2 167.5(2) . . ? C1 Ir1 N4 103.5(2) . . ? C2 Ir1 N4 167.2(2) . . ? N1 Ir1 N4 92.1(2) . . ? N2 Ir1 N4 98.9(2) . . ? C1 Ir1 N3 163.6(3) . . ? C2 Ir1 N3 107.1(2) . . ? N1 Ir1 N3 98.5(2) . . ? N2 Ir1 N3 92.2(2) . . ? N4 Ir1 N3 60.1(2) . . ? C8 S1 C10 89.3(3) . . ? C22 S2 C20 89.7(4) . . ? C8 N1 C9 112.3(6) . . ? C8 N1 Ir1 114.3(4) . . ? C9 N1 Ir1 133.0(4) . . ? C20 N2 C21 111.7(6) . . ? C20 N2 Ir1 113.2(5) . . ? C21 N2 Ir1 134.3(5) . . ? C27 N3 C31 123.8(6) . . ? C27 N3 Ir1 94.0(4) . . ? C31 N3 Ir1 136.8(4) . . ? C27 N4 C28 122.5(6) . . ? C27 N4 Ir1 94.9(4) . . ? C28 N4 Ir1 135.3(4) . . ? C27 N5 C34 120.3(6) . . ? C27 N5 C40 122.1(5) . . ? C34 N5 C40 117.3(5) . . ? C7 C1 C3 113.1(7) . . ? C7 C1 Ir1 131.5(6) . . ? C3 C1 Ir1 115.2(5) . . ? C15 C2 C19 114.5(7) . . ? C15 C2 Ir1 116.3(5) . . ? C19 C2 Ir1 129.2(5) . . ? C4 C3 C1 124.0(7) . . ? C4 C3 C8 124.1(7) . . ? C1 C3 C8 111.9(6) . . ? C5 C4 C3 119.1(7) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 119.1(7) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.2(7) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.9 . . ? C1 C7 C6 124.4(7) . . ? C1 C7 H7 117.6 . . ? C6 C7 H7 117.9 . . ? N1 C8 C3 118.3(6) . . ? N1 C8 S1 115.3(5) . . ? C3 C8 S1 126.3(5) . . ? C14 C9 C10 119.5(6) . . ? C14 C9 N1 127.7(6) . . ? C10 C9 N1 112.7(6) . . ? C11 C10 C9 122.7(7) . . ? C11 C10 S1 127.0(6) . . ? C9 C10 S1 110.3(5) . . ? C12 C11 C10 118.0(7) . . ? C12 C11 H11 120.9 . . ? C10 C11 H11 121.1 . . ? C11 C12 C13 120.1(7) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 122.2(7) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.8 . . ? C9 C14 C13 117.4(7) . . ? C9 C14 H14 121.2 . . ? C13 C14 H14 121.4 . . ? C2 C15 C16 124.6(7) . . ? C2 C15 C20 112.0(7) . . ? C16 C15 C20 123.3(7) . . ? C17 C16 C15 118.7(7) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.8 . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 121.0(7) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.5 . . ? C18 C19 C2 121.7(7) . . ? C18 C19 H19 119.2 . . ? C2 C19 H19 119.1 . . ? N2 C20 C15 118.7(6) . . ? N2 C20 S2 114.5(5) . . ? C15 C20 S2 126.8(6) . . ? C26 C21 N2 125.9(7) . . ? C26 C21 C22 120.9(7) . . ? N2 C21 C22 113.1(7) . . ? C23 C22 C21 119.3(8) . . ? C23 C22 S2 129.8(6) . . ? C21 C22 S2 110.8(6) . . ? C24 C23 C22 118.8(8) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.5 . . ? C23 C24 C25 122.1(8) . . ? C23 C24 H24 118.9 . . ? C25 C24 H24 118.9 . . ? C24 C25 C26 119.6(8) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.3 . . ? C21 C26 C25 119.2(7) . . ? C21 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? N4 C27 N3 110.9(6) . . ? N4 C27 N5 126.0(6) . . ? N3 C27 N5 123.1(6) . . ? N4 C28 C29 113.6(6) . . ? N4 C28 C30 109.1(6) . . ? C29 C28 C30 108.9(7) . . ? N4 C28 H28 108.4 . . ? C29 C28 H28 108.4 . . ? C30 C28 H28 108.3 . . ? C28 C29 H29A 109.2 . . ? C28 C29 H29B 109.6 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.6 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.4 . . ? C28 C30 H30B 109.7 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.3 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N3 C31 C33 109.4(6) . . ? N3 C31 C32 110.7(5) . . ? C33 C31 C32 111.5(6) . . ? N3 C31 H31 108.5 . . ? C33 C31 H31 108.4 . . ? C32 C31 H31 108.3 . . ? C31 C32 H32A 109.4 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.7 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.3 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C39 120.4(6) . . ? C35 C34 N5 121.9(6) . . ? C39 C34 N5 117.6(6) . . ? C34 C35 C36 121.3(6) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 118.8 . . ? C34 C39 C38 118.3(6) . . ? C34 C39 H39 121.1 . . ? C38 C39 H39 120.6 . . ? C41 C40 C45 120.7(4) . . ? C41 C40 N5 120.0(3) . . ? C45 C40 N5 119.2(5) . . ? C40 C41 C42 119.8(4) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.0 . . ? C37 C36 C35 116.4(8) . . ? C37 C36 H36 122.5 . . ? C35 C36 H36 121.2 . . ? C36 C37 C38 125.6(9) . . ? C36 C37 H37 117.3 . . ? C38 C37 H37 117.1 . . ? C37 C38 C39 117.9(8) . . ? C37 C38 H38 122.1 . . ? C39 C38 H38 120.0 . . ? C43 C42 C41 120.1(7) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 120.0 . . ? C44 C43 C42 119.0(8) . . ? C44 C43 H43 120.6 . . ? C42 C43 H43 120.4 . . ? C43 C44 C45 121.5(7) . . ? C43 C44 H44 119.2 . . ? C45 C44 H44 119.3 . . ? C44 C45 C40 118.9(7) . . ? C44 C45 H45 120.5 . . ? C40 C45 H45 120.6 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.432 _refine_diff_density_min -1.274 _refine_diff_density_rms 0.131 data_7 _database_code_depnum_ccdc_archive 'CCDC 857588' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H48 Ir N5 S2' _chemical_formula_sum 'C52 H48 Ir N5 S2' _chemical_formula_weight 999.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.335(5) _cell_length_b 13.420(7) _cell_length_c 17.234(9) _cell_angle_alpha 80.228(7) _cell_angle_beta 77.838(7) _cell_angle_gamma 72.643(7) _cell_volume 2216(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 230 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 3.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3656 _exptl_absorpt_correction_T_max 0.6494 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11639 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.20 _reflns_number_total 7659 _reflns_number_gt 6081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7659 _refine_ls_number_parameters 511 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.010 _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 0.79957(3) 0.69822(2) 0.743857(15) 0.02082(8) Uani 1 1 d . . . S1 S 1.04948(19) 0.42604(13) 0.60631(10) 0.0361(5) Uani 1 1 d . . . S2 S 0.81202(17) 0.54415(13) 0.99781(9) 0.0300(4) Uani 1 1 d . . . N1 N 0.9064(5) 0.7470(4) 0.8104(3) 0.0202(12) Uani 1 1 d . . . N2 N 0.6989(5) 0.6435(4) 0.6766(3) 0.0251(12) Uani 1 1 d . . . N3 N 0.7916(5) 0.8343(4) 0.6532(3) 0.0197(12) Uani 1 1 d . . . N4 N 0.6327(5) 0.8394(4) 0.7613(3) 0.0237(12) Uani 1 1 d . . . N5 N 0.6018(6) 0.9939(4) 0.6625(3) 0.0320(14) Uani 1 1 d . . . C1 C 0.7767(6) 0.6013(5) 0.8471(3) 0.0201(14) Uani 1 1 d . . . C2 C 0.9565(6) 0.5802(4) 0.6994(3) 0.0185(14) Uani 1 1 d . . . C3 C 0.8356(6) 0.6211(4) 0.9050(3) 0.0229(15) Uani 1 1 d . . . C4 C 0.7084(6) 0.5195(5) 0.8778(3) 0.0229(15) Uani 1 1 d . . . C5 C 0.7203(6) 0.4809(5) 0.9580(4) 0.0266(15) Uani 1 1 d . . . C6 C 0.6628(6) 0.4019(5) 0.9984(4) 0.0315(17) Uani 1 1 d . . . H18 H 0.6707 0.3778 1.0527 0.038 Uiso 1 1 calc R . . C7 C 0.5944(7) 0.3588(5) 0.9592(4) 0.0374(18) Uani 1 1 d . . . H19 H 0.5538 0.3051 0.9869 0.045 Uiso 1 1 calc R . . C8 C 0.5835(7) 0.3930(5) 0.8785(4) 0.0366(18) Uani 1 1 d . . . H20 H 0.5373 0.3615 0.8516 0.044 Uiso 1 1 calc R . . C9 C 0.6401(6) 0.4725(5) 0.8383(4) 0.0306(16) Uani 1 1 d . . . H21 H 0.6327 0.4954 0.7838 0.037 Uiso 1 1 calc R . . C10 C 0.9110(6) 0.6984(5) 0.8865(3) 0.0224(15) Uani 1 1 d . . . C11 C 0.9862(6) 0.7234(5) 0.9352(4) 0.0254(15) Uani 1 1 d . . . H23 H 0.9898 0.6884 0.9878 0.031 Uiso 1 1 calc R . . C12 C 1.0555(7) 0.7998(5) 0.9066(4) 0.0318(17) Uani 1 1 d . . . H24 H 1.1065 0.8180 0.9392 0.038 Uiso 1 1 calc R . . C13 C 1.0491(7) 0.8489(5) 0.8295(3) 0.0302(16) Uani 1 1 d . . . H25 H 1.0958 0.9014 0.8087 0.036 Uiso 1 1 calc R . . C14 C 0.9745(6) 0.8213(5) 0.7831(4) 0.0265(15) Uani 1 1 d . . . H26 H 0.9709 0.8556 0.7303 0.032 Uiso 1 1 calc R . . C15 C 0.9179(7) 0.5287(4) 0.6479(3) 0.0252(15) Uani 1 1 d . . . C16 C 1.0995(7) 0.5338(5) 0.7051(3) 0.0264(15) Uani 1 1 d . . . C17 C 1.1638(7) 0.4498(5) 0.6566(3) 0.0301(16) Uani 1 1 d . . . C18 C 1.3023(7) 0.3946(5) 0.6551(4) 0.0378(18) Uani 1 1 d . . . H5 H 1.3436 0.3386 0.6230 0.045 Uiso 1 1 calc R . . C19 C 1.3777(7) 0.4219(6) 0.7004(4) 0.044(2) Uani 1 1 d . . . H6 H 1.4720 0.3849 0.6993 0.052 Uiso 1 1 calc R . . C20 C 1.3178(7) 0.5028(5) 0.7479(4) 0.0394(18) Uani 1 1 d . . . H7 H 1.3712 0.5201 0.7795 0.047 Uiso 1 1 calc R . . C21 C 1.1821(7) 0.5585(5) 0.7497(4) 0.0309(16) Uani 1 1 d . . . H8 H 1.1437 0.6147 0.7818 0.037 Uiso 1 1 calc R . . C22 C 0.7794(7) 0.5630(5) 0.6332(4) 0.0293(16) Uani 1 1 d . . . C23 C 0.7243(8) 0.5267(5) 0.5793(4) 0.0356(17) Uani 1 1 d . . . H10 H 0.7802 0.4716 0.5490 0.043 Uiso 1 1 calc R . . C24 C 0.5902(8) 0.5706(6) 0.5707(4) 0.043(2) Uani 1 1 d . . . H11 H 0.5526 0.5470 0.5337 0.052 Uiso 1 1 calc R . . C25 C 0.5099(8) 0.6492(6) 0.6158(4) 0.0422(19) Uani 1 1 d . . . H13 H 0.4159 0.6793 0.6110 0.051 Uiso 1 1 calc R . . C26 C 0.5663(7) 0.6838(5) 0.6679(4) 0.0332(17) Uani 1 1 d . . . H12 H 0.5098 0.7380 0.6988 0.040 Uiso 1 1 calc R . . C27 C 0.6763(6) 0.8902(5) 0.6933(4) 0.0254(15) Uani 1 1 d . . . C28 C 0.8491(7) 0.8600(5) 0.5692(3) 0.0300(16) Uani 1 1 d . . . H28 H 0.7915 0.9296 0.5485 0.036 Uiso 1 1 calc R . . C29 C 0.9955(8) 0.8669(6) 0.5630(4) 0.058(2) Uani 1 1 d . . . H29A H 1.0517 0.8001 0.5857 0.087 Uiso 1 1 calc R . . H29B H 0.9944 0.9236 0.5925 0.087 Uiso 1 1 calc R . . H29C H 1.0346 0.8816 0.5067 0.087 Uiso 1 1 calc R . . C30 C 0.8490(8) 0.7776(5) 0.5192(4) 0.047(2) Uani 1 1 d . . . H30A H 0.7542 0.7765 0.5208 0.070 Uiso 1 1 calc R . . H30B H 0.9018 0.7085 0.5406 0.070 Uiso 1 1 calc R . . H30C H 0.8911 0.7946 0.4639 0.070 Uiso 1 1 calc R . . C31 C 0.4129(7) 0.8324(6) 0.8446(4) 0.049(2) Uani 1 1 d . . . H31A H 0.4532 0.7562 0.8527 0.073 Uiso 1 1 calc R . . H31B H 0.3607 0.8497 0.8005 0.073 Uiso 1 1 calc R . . H31C H 0.3512 0.8559 0.8936 0.073 Uiso 1 1 calc R . . C32 C 0.5902(7) 0.8818(6) 0.8990(3) 0.047(2) Uani 1 1 d . . . H32A H 0.6607 0.9200 0.8859 0.070 Uiso 1 1 calc R . . H32B H 0.6319 0.8081 0.9172 0.070 Uiso 1 1 calc R . . H32C H 0.5177 0.9134 0.9414 0.070 Uiso 1 1 calc R . . C33 C 0.5278(6) 0.8879(5) 0.8244(3) 0.0301(16) Uani 1 1 d . . . H33 H 0.4882 0.9634 0.8052 0.036 Uiso 1 1 calc R . . C34 C 0.6605(7) 1.0792(5) 0.6562(4) 0.0349(17) Uani 1 1 d . . . C35 C 0.6278(7) 1.1661(5) 0.5990(4) 0.0359(17) Uani 1 1 d . . . H35 H 0.5643 1.1699 0.5652 0.043 Uiso 1 1 calc R . . C36 C 0.7508(7) 1.0762(6) 0.7071(4) 0.046(2) Uani 1 1 d . . . H36 H 0.7721 1.0177 0.7464 0.055 Uiso 1 1 calc R . . C37 C 0.7785(8) 1.2442(6) 0.6419(5) 0.054(2) Uani 1 1 d . . . H37 H 0.8188 1.3005 0.6366 0.065 Uiso 1 1 calc R . . C38 C 0.6889(8) 1.2455(5) 0.5924(5) 0.049(2) Uani 1 1 d . . . H38 H 0.6688 1.3034 0.5524 0.059 Uiso 1 1 calc R . . C39 C 0.8087(8) 1.1579(6) 0.7002(5) 0.053(2) Uani 1 1 d . . . H39 H 0.8695 1.1559 0.7352 0.064 Uiso 1 1 calc R . . C40 C 0.4620(7) 1.0114(5) 0.6534(4) 0.0318(17) Uani 1 1 d . . . C41 C 0.4295(7) 0.9441(5) 0.6123(4) 0.0387(18) Uani 1 1 d . . . H41 H 0.5010 0.8921 0.5856 0.046 Uiso 1 1 calc R . . C42 C 0.3570(7) 1.0937(5) 0.6867(4) 0.0338(17) Uani 1 1 d . . . H42 H 0.3785 1.1439 0.7110 0.041 Uiso 1 1 calc R . . C43 C 0.2230(7) 1.1007(5) 0.6838(4) 0.0403(19) Uani 1 1 d . . . H43 H 0.1514 1.1551 0.7079 0.048 Uiso 1 1 calc R . . C44 C 0.2933(7) 0.9522(5) 0.6101(4) 0.0410(19) Uani 1 1 d . . . H44 H 0.2713 0.9044 0.5835 0.049 Uiso 1 1 calc R . . C45 C 0.1898(7) 1.0303(6) 0.6466(4) 0.0427(19) Uani 1 1 d . . . H45 H 0.0962 1.0355 0.6462 0.051 Uiso 1 1 calc R . . C46 C 0.0370(9) 0.1166(7) 0.9000(5) 0.072(3) Uiso 1 1 d . . . H46 H 0.0023 0.0570 0.9172 0.086 Uiso 1 1 calc R . . C47 C 0.1722(8) 0.1108(6) 0.9047(4) 0.058(2) Uiso 1 1 d . . . H47 H 0.2289 0.0471 0.9266 0.069 Uiso 1 1 calc R . . C48 C 0.2249(8) 0.1959(6) 0.8780(4) 0.050(2) Uiso 1 1 d . . . C49 C 0.1372(8) 0.2864(6) 0.8484(4) 0.052(2) Uiso 1 1 d . . . H49 H 0.1692 0.3471 0.8302 0.062 Uiso 1 1 calc R . . C50 C 0.3716(10) 0.1926(7) 0.8826(5) 0.094(3) Uiso 1 1 d . . . H50A H 0.3700 0.2468 0.9146 0.141 Uiso 1 1 calc R . . H50B H 0.4218 0.2054 0.8286 0.141 Uiso 1 1 calc R . . H50C H 0.4174 0.1233 0.9075 0.141 Uiso 1 1 calc R . . C51 C 0.0085(9) 0.2907(7) 0.8449(5) 0.061(2) Uiso 1 1 d . . . H51 H -0.0487 0.3543 0.8231 0.074 Uiso 1 1 calc R . . C52 C -0.0433(10) 0.2081(7) 0.8709(5) 0.081(3) Uiso 1 1 d . . . H52 H -0.1365 0.2142 0.8688 0.097 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02352(15) 0.01867(14) 0.02009(14) -0.00010(9) -0.00557(10) -0.00536(10) S1 0.0449(12) 0.0278(10) 0.0332(10) -0.0109(8) -0.0028(9) -0.0049(9) S2 0.0334(11) 0.0333(10) 0.0224(9) 0.0056(7) -0.0064(8) -0.0117(8) N1 0.014(3) 0.020(3) 0.025(3) -0.004(2) -0.002(2) -0.004(2) N2 0.029(3) 0.020(3) 0.027(3) 0.004(2) -0.006(3) -0.011(3) N3 0.022(3) 0.020(3) 0.015(3) 0.001(2) -0.003(2) -0.005(2) N4 0.020(3) 0.028(3) 0.021(3) -0.001(2) -0.004(2) -0.004(2) N5 0.033(4) 0.023(3) 0.041(3) 0.001(3) -0.012(3) -0.007(3) C1 0.009(3) 0.026(4) 0.023(3) -0.002(3) -0.001(3) -0.003(3) C2 0.022(4) 0.016(3) 0.019(3) 0.009(3) -0.007(3) -0.011(3) C3 0.026(4) 0.018(3) 0.020(3) 0.004(3) -0.004(3) -0.002(3) C4 0.018(4) 0.020(3) 0.027(4) -0.005(3) -0.003(3) 0.001(3) C5 0.018(4) 0.023(4) 0.032(4) 0.001(3) -0.004(3) 0.000(3) C6 0.027(4) 0.031(4) 0.030(4) 0.008(3) -0.004(3) -0.006(3) C7 0.032(4) 0.029(4) 0.048(5) 0.006(3) -0.006(4) -0.009(3) C8 0.040(5) 0.036(4) 0.042(4) 0.003(3) -0.013(4) -0.023(4) C9 0.028(4) 0.038(4) 0.028(4) 0.008(3) -0.010(3) -0.016(3) C10 0.023(4) 0.025(4) 0.018(3) -0.004(3) -0.005(3) -0.002(3) C11 0.022(4) 0.029(4) 0.024(4) -0.003(3) -0.005(3) -0.004(3) C12 0.032(4) 0.039(4) 0.031(4) -0.007(3) -0.010(3) -0.015(3) C13 0.039(4) 0.028(4) 0.030(4) -0.003(3) -0.006(3) -0.018(3) C14 0.029(4) 0.023(4) 0.025(4) -0.001(3) -0.002(3) -0.006(3) C15 0.034(4) 0.017(3) 0.023(3) 0.004(3) -0.003(3) -0.009(3) C16 0.032(4) 0.019(4) 0.022(3) 0.005(3) 0.000(3) -0.005(3) C17 0.032(4) 0.025(4) 0.027(4) -0.001(3) -0.001(3) -0.003(3) C18 0.038(5) 0.028(4) 0.036(4) -0.008(3) 0.005(4) 0.002(3) C19 0.025(4) 0.048(5) 0.041(4) 0.003(4) 0.003(4) 0.005(4) C20 0.024(4) 0.048(5) 0.044(4) -0.005(4) -0.011(3) -0.004(4) C21 0.034(4) 0.026(4) 0.030(4) -0.001(3) -0.005(3) -0.005(3) C22 0.043(5) 0.021(4) 0.027(4) 0.005(3) -0.005(3) -0.017(3) C23 0.052(5) 0.029(4) 0.032(4) -0.005(3) -0.011(4) -0.017(4) C24 0.060(6) 0.047(5) 0.040(4) 0.004(4) -0.025(4) -0.034(4) C25 0.044(5) 0.042(5) 0.050(5) 0.005(4) -0.024(4) -0.020(4) C26 0.032(4) 0.033(4) 0.036(4) 0.001(3) -0.012(3) -0.008(3) C27 0.024(4) 0.023(4) 0.033(4) 0.000(3) -0.014(3) -0.008(3) C28 0.046(5) 0.023(4) 0.019(3) 0.008(3) -0.010(3) -0.009(3) C29 0.056(6) 0.084(6) 0.031(4) -0.002(4) 0.008(4) -0.027(5) C30 0.083(6) 0.040(4) 0.021(4) -0.003(3) -0.001(4) -0.030(4) C31 0.037(5) 0.057(5) 0.046(5) -0.010(4) 0.006(4) -0.010(4) C32 0.044(5) 0.058(5) 0.023(4) -0.008(4) -0.004(3) 0.010(4) C33 0.028(4) 0.031(4) 0.023(4) -0.001(3) -0.002(3) 0.001(3) C34 0.036(5) 0.027(4) 0.041(4) -0.006(3) -0.008(4) -0.004(3) C35 0.031(4) 0.029(4) 0.046(4) -0.001(3) -0.005(3) -0.008(3) C36 0.046(5) 0.036(4) 0.059(5) -0.005(4) -0.023(4) -0.007(4) C37 0.039(5) 0.021(4) 0.097(7) -0.007(4) 0.000(5) -0.010(4) C38 0.044(5) 0.025(4) 0.068(6) 0.002(4) -0.003(4) -0.003(4) C39 0.037(5) 0.055(6) 0.077(6) -0.025(5) -0.016(4) -0.013(4) C40 0.038(5) 0.029(4) 0.033(4) 0.009(3) -0.014(3) -0.017(3) C41 0.037(5) 0.039(4) 0.042(4) -0.012(4) -0.008(4) -0.009(4) C42 0.034(4) 0.027(4) 0.037(4) -0.004(3) -0.011(3) 0.001(3) C43 0.038(5) 0.040(5) 0.036(4) -0.011(4) -0.007(4) 0.004(4) C44 0.046(5) 0.034(4) 0.048(5) -0.003(4) -0.019(4) -0.013(4) C45 0.031(5) 0.047(5) 0.051(5) 0.003(4) -0.007(4) -0.015(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 Ir1 C2 2.021(6) . ? Ir1 C1 2.034(6) . ? Ir1 N1 2.044(5) . ? Ir1 N2 2.053(5) . ? Ir1 N4 2.163(5) . ? Ir1 N3 2.186(4) . ? Ir1 C27 2.601(6) . ? S1 C17 1.732(7) . ? S1 C15 1.751(6) . ? S2 C5 1.744(7) . ? S2 C3 1.763(6) . ? N1 C14 1.354(7) . ? N1 C10 1.366(7) . ? N2 C26 1.345(8) . ? N2 C22 1.377(7) . ? N3 C27 1.325(7) . ? N3 C28 1.468(7) . ? N4 C27 1.316(7) . ? N4 C33 1.450(7) . ? N5 C40 1.431(8) . ? N5 C34 1.428(8) . ? N5 C27 1.447(7) . ? C1 C3 1.372(8) . ? C1 C4 1.445(8) . ? C2 C15 1.395(8) . ? C2 C16 1.439(8) . ? C3 C10 1.431(8) . ? C4 C9 1.405(8) . ? C4 C5 1.408(8) . ? C5 C6 1.384(8) . ? C6 C7 1.366(9) . ? C6 H18 0.9500 . ? C7 C8 1.407(9) . ? C7 H19 0.9500 . ? C8 C9 1.382(8) . ? C8 H20 0.9500 . ? C9 H21 0.9500 . ? C10 C11 1.396(8) . ? C11 C12 1.387(9) . ? C11 H23 0.9500 . ? C12 C13 1.384(8) . ? C12 H24 0.9500 . ? C13 C14 1.378(8) . ? C13 H25 0.9500 . ? C14 H26 0.9500 . ? C15 C22 1.430(9) . ? C16 C21 1.401(8) . ? C16 C17 1.431(8) . ? C17 C18 1.399(9) . ? C18 C19 1.369(9) . ? C18 H5 0.9500 . ? C19 C20 1.385(9) . ? C19 H6 0.9500 . ? C20 C21 1.375(8) . ? C20 H7 0.9500 . ? C21 H8 0.9500 . ? C22 C23 1.402(8) . ? C23 C24 1.364(9) . ? C23 H10 0.9500 . ? C24 C25 1.375(9) . ? C24 H11 0.9500 . ? C25 C26 1.373(9) . ? C25 H13 0.9500 . ? C26 H12 0.9500 . ? C28 C30 1.513(8) . ? C28 C29 1.523(9) . ? C28 H28 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C33 1.533(9) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.536(8) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33 1.0000 . ? C34 C35 1.400(8) . ? C34 C36 1.397(9) . ? C35 C38 1.370(9) . ? C35 H35 0.9500 . ? C36 C39 1.376(10) . ? C36 H36 0.9500 . ? C37 C38 1.380(10) . ? C37 C39 1.404(10) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 C41 1.389(9) . ? C40 C42 1.401(8) . ? C41 C44 1.388(9) . ? C41 H41 0.9500 . ? C42 C43 1.371(9) . ? C42 H42 0.9500 . ? C43 C45 1.384(9) . ? C43 H43 0.9500 . ? C44 C45 1.382(9) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C52 1.343(10) . ? C46 C47 1.394(11) . ? C46 H46 0.9500 . ? C47 C48 1.378(10) . ? C47 H47 0.9500 . ? C48 C49 1.372(9) . ? C48 C50 1.521(11) . ? C49 C51 1.328(10) . ? C49 H49 0.9500 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 C52 1.342(11) . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Ir1 C1 88.1(2) . . ? C2 Ir1 N1 97.1(2) . . ? C1 Ir1 N1 79.6(2) . . ? C2 Ir1 N2 80.6(2) . . ? C1 Ir1 N2 99.7(2) . . ? N1 Ir1 N2 177.6(2) . . ? C2 Ir1 N4 166.12(19) . . ? C1 Ir1 N4 105.0(2) . . ? N1 Ir1 N4 89.70(18) . . ? N2 Ir1 N4 92.70(19) . . ? C2 Ir1 N3 106.37(19) . . ? C1 Ir1 N3 164.80(19) . . ? N1 Ir1 N3 93.87(18) . . ? N2 Ir1 N3 87.40(18) . . ? N4 Ir1 N3 60.92(18) . . ? C2 Ir1 C27 136.7(2) . . ? C1 Ir1 C27 135.2(2) . . ? N1 Ir1 C27 92.44(19) . . ? N2 Ir1 C27 89.69(19) . . ? N4 Ir1 C27 30.33(17) . . ? N3 Ir1 C27 30.59(17) . . ? C17 S1 C15 90.3(3) . . ? C5 S2 C3 89.4(3) . . ? C14 N1 C10 118.8(5) . . ? C14 N1 Ir1 124.3(4) . . ? C10 N1 Ir1 116.8(4) . . ? C26 N2 C22 118.6(6) . . ? C26 N2 Ir1 125.8(4) . . ? C22 N2 Ir1 115.4(4) . . ? C27 N3 C28 125.6(5) . . ? C27 N3 Ir1 92.3(4) . . ? C28 N3 Ir1 139.6(4) . . ? C27 N4 C33 124.7(5) . . ? C27 N4 Ir1 93.6(4) . . ? C33 N4 Ir1 139.9(4) . . ? C40 N5 C34 121.4(5) . . ? C40 N5 C27 118.8(5) . . ? C34 N5 C27 118.8(5) . . ? C3 C1 C4 110.4(5) . . ? C3 C1 Ir1 112.5(4) . . ? C4 C1 Ir1 137.0(5) . . ? C15 C2 C16 109.8(5) . . ? C15 C2 Ir1 112.3(4) . . ? C16 C2 Ir1 137.9(5) . . ? C1 C3 C10 119.5(5) . . ? C1 C3 S2 114.9(5) . . ? C10 C3 S2 125.7(5) . . ? C9 C4 C5 117.9(6) . . ? C9 C4 C1 129.3(6) . . ? C5 C4 C1 112.7(6) . . ? C6 C5 C4 121.8(6) . . ? C6 C5 S2 125.7(5) . . ? C4 C5 S2 112.6(5) . . ? C7 C6 C5 119.3(6) . . ? C7 C6 H18 120.3 . . ? C5 C6 H18 120.3 . . ? C6 C7 C8 120.7(6) . . ? C6 C7 H19 119.6 . . ? C8 C7 H19 119.6 . . ? C9 C8 C7 120.0(7) . . ? C9 C8 H20 120.0 . . ? C7 C8 H20 120.0 . . ? C8 C9 C4 120.3(6) . . ? C8 C9 H21 119.8 . . ? C4 C9 H21 119.8 . . ? N1 C10 C11 120.9(6) . . ? N1 C10 C3 111.5(5) . . ? C11 C10 C3 127.6(6) . . ? C12 C11 C10 119.7(6) . . ? C12 C11 H23 120.2 . . ? C10 C11 H23 120.2 . . ? C13 C12 C11 118.8(6) . . ? C13 C12 H24 120.6 . . ? C11 C12 H24 120.6 . . ? C14 C13 C12 119.7(6) . . ? C14 C13 H25 120.2 . . ? C12 C13 H25 120.2 . . ? N1 C14 C13 122.1(6) . . ? N1 C14 H26 118.9 . . ? C13 C14 H26 118.9 . . ? C2 C15 C22 119.0(5) . . ? C2 C15 S1 114.9(5) . . ? C22 C15 S1 126.1(5) . . ? C21 C16 C17 116.9(6) . . ? C21 C16 C2 130.1(6) . . ? C17 C16 C2 113.0(6) . . ? C18 C17 C16 121.1(6) . . ? C18 C17 S1 126.8(5) . . ? C16 C17 S1 112.0(5) . . ? C19 C18 C17 119.4(6) . . ? C19 C18 H5 120.3 . . ? C17 C18 H5 120.3 . . ? C18 C19 C20 120.6(7) . . ? C18 C19 H6 119.7 . . ? C20 C19 H6 119.7 . . ? C21 C20 C19 120.9(7) . . ? C21 C20 H7 119.5 . . ? C19 C20 H7 119.5 . . ? C20 C21 C16 121.1(6) . . ? C20 C21 H8 119.5 . . ? C16 C21 H8 119.5 . . ? N2 C22 C23 120.2(6) . . ? N2 C22 C15 112.5(6) . . ? C23 C22 C15 127.3(6) . . ? C24 C23 C22 119.8(7) . . ? C24 C23 H10 120.1 . . ? C22 C23 H10 120.1 . . ? C23 C24 C25 119.5(7) . . ? C23 C24 H11 120.2 . . ? C25 C24 H11 120.2 . . ? C24 C25 C26 119.6(7) . . ? C24 C25 H13 120.2 . . ? C26 C25 H13 120.2 . . ? N2 C26 C25 122.3(6) . . ? N2 C26 H12 118.9 . . ? C25 C26 H12 118.9 . . ? N4 C27 N3 113.2(5) . . ? N4 C27 N5 123.7(6) . . ? N3 C27 N5 123.0(6) . . ? N4 C27 Ir1 56.1(3) . . ? N3 C27 Ir1 57.1(3) . . ? N5 C27 Ir1 175.9(4) . . ? N3 C28 C30 110.7(5) . . ? N3 C28 C29 109.7(5) . . ? C30 C28 C29 109.7(6) . . ? N3 C28 H28 108.9 . . ? C30 C28 H28 108.9 . . ? C29 C28 H28 108.9 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C33 C31 H31A 109.5 . . ? C33 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C33 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C33 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N4 C33 C31 109.5(5) . . ? N4 C33 C32 110.5(5) . . ? C31 C33 C32 110.2(6) . . ? N4 C33 H33 108.9 . . ? C31 C33 H33 108.9 . . ? C32 C33 H33 108.9 . . ? C35 C34 C36 119.9(7) . . ? C35 C34 N5 120.1(6) . . ? C36 C34 N5 120.0(6) . . ? C38 C35 C34 119.0(7) . . ? C38 C35 H35 120.5 . . ? C34 C35 H35 120.5 . . ? C39 C36 C34 120.0(7) . . ? C39 C36 H36 120.0 . . ? C34 C36 H36 120.0 . . ? C38 C37 C39 118.6(7) . . ? C38 C37 H37 120.7 . . ? C39 C37 H37 120.7 . . ? C35 C38 C37 122.1(7) . . ? C35 C38 H38 118.9 . . ? C37 C38 H38 118.9 . . ? C36 C39 C37 120.4(7) . . ? C36 C39 H39 119.8 . . ? C37 C39 H39 119.8 . . ? C41 C40 C42 119.5(6) . . ? C41 C40 N5 119.2(6) . . ? C42 C40 N5 121.2(6) . . ? C44 C41 C40 120.4(7) . . ? C44 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C43 C42 C40 119.2(7) . . ? C43 C42 H42 120.4 . . ? C40 C42 H42 120.4 . . ? C42 C43 C45 121.3(7) . . ? C42 C43 H43 119.3 . . ? C45 C43 H43 119.3 . . ? C41 C44 C45 119.6(7) . . ? C41 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C43 C45 C44 119.7(7) . . ? C43 C45 H45 120.1 . . ? C44 C45 H45 120.1 . . ? C52 C46 C47 118.8(10) . . ? C52 C46 H46 120.6 . . ? C47 C46 H46 120.6 . . ? C48 C47 C46 121.2(8) . . ? C48 C47 H47 119.4 . . ? C46 C47 H47 119.4 . . ? C49 C48 C47 116.7(8) . . ? C49 C48 C50 120.7(8) . . ? C47 C48 C50 122.6(8) . . ? C51 C49 C48 121.3(8) . . ? C51 C49 H49 119.4 . . ? C48 C49 H49 119.4 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C49 C51 C52 122.2(9) . . ? C49 C51 H51 118.9 . . ? C52 C51 H51 118.9 . . ? C46 C52 C51 119.8(10) . . ? C46 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.688 _refine_diff_density_min -1.158 _refine_diff_density_rms 0.130 data_8 _database_code_depnum_ccdc_archive 'CCDC 864457' #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[(Piq)2Ir{iPrN)2C(NPh2)}]' _chemical_melting_point ? _chemical_formula_moiety 'C49 H44 Ir N5, C7 H8' _chemical_formula_sum 'C56 H52 Ir N5' _chemical_formula_weight 987.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.992(7) _cell_length_b 29.691(14) _cell_length_c 10.583(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.707(7) _cell_angle_gamma 90.00 _cell_volume 4512(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 215 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 3.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3796 _exptl_absorpt_correction_T_max 0.4661 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11814 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0949 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3972 _reflns_number_gt 3048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0184P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3972 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.0000 0.176586(10) 0.2500 0.02867(10) Uani 1 2 d S . . N1 N -0.1087(3) 0.17837(13) 0.3295(3) 0.0307(9) Uani 1 1 d . . . N2 N -0.0426(3) 0.11272(12) 0.1466(3) 0.0302(10) Uani 1 1 d . . . N3 N 0.0000 0.03997(17) 0.2500 0.0345(15) Uani 1 2 d S . . C1 C 0.0419(4) 0.22582(15) 0.3829(4) 0.0302(13) Uani 1 1 d . . . C2 C 0.1187(4) 0.25335(16) 0.4008(5) 0.0398(14) Uani 1 1 d . . . H2 H 0.1610 0.2476 0.3513 0.058 Uiso 1 1 d R . . C3 C 0.1361(4) 0.28920(17) 0.4890(5) 0.0482(15) Uani 1 1 d . . . H3 H 0.1909 0.3067 0.5012 0.056 Uiso 1 1 d R . . C4 C 0.0741(4) 0.29917(17) 0.5579(5) 0.0466(15) Uani 1 1 d . . . C5 C -0.0026(4) 0.27254(16) 0.5449(5) 0.0400(14) Uani 1 1 d . . . H4 H 0.0845 0.3246 0.6146 0.048 Uiso 1 1 d R . . C6 C -0.0190(3) 0.23468(15) 0.4612(4) 0.0288(12) Uani 1 1 d . . . H5 H -0.0455 0.2797 0.5931 0.035 Uiso 1 1 d R . . C7 C -0.1831(4) 0.15118(16) 0.2866(5) 0.0348(13) Uani 1 1 d . . . H7 H -0.1892 0.1342 0.2084 0.042 Uiso 1 1 d R . . C8 C -0.2499(4) 0.14678(16) 0.3493(5) 0.0383(13) Uani 1 1 d . . . H8 H -0.3035 0.1289 0.3116 0.046 Uiso 1 1 d R . . C9 C -0.2395(4) 0.16922(16) 0.4722(4) 0.0351(13) Uani 1 1 d . . . C10 C -0.1618(4) 0.19740(16) 0.5175(5) 0.0339(13) Uani 1 1 d . . . C11 C -0.0983(3) 0.20456(15) 0.4385(4) 0.0297(12) Uani 1 1 d . . . C12 C -0.1455(4) 0.21578(16) 0.6485(5) 0.0427(14) Uani 1 1 d . . . H12 H -0.0924 0.2341 0.6850 0.051 Uiso 1 1 d R . . C13 C -0.2060(4) 0.20704(19) 0.7202(5) 0.0520(16) Uani 1 1 d . . . H13 H -0.1938 0.2193 0.8064 0.062 Uiso 1 1 d R . . C14 C -0.2845(4) 0.1808(2) 0.6706(5) 0.0502(15) Uani 1 1 d . . . H14 H -0.3270 0.1762 0.7209 0.060 Uiso 1 1 d R . . C15 C -0.3007(4) 0.16153(16) 0.5483(5) 0.0456(15) Uani 1 1 d . . . H15 H -0.3538 0.1429 0.5149 0.055 Uiso 1 1 d R . . C16 C 0.0000 0.0880(2) 0.2500 0.0319(18) Uani 1 2 d S . . C17 C -0.0805(4) 0.09514(16) 0.0121(4) 0.0367(13) Uani 1 1 d . . . H17 H -0.0674 0.0621 0.0134 0.044 Uiso 1 1 d R . . C18 C -0.1847(4) 0.10188(19) -0.0351(5) 0.0578(17) Uani 1 1 d . . . H18A H -0.2141 0.0847 0.0213 0.087 Uiso 1 1 d R . . H18B H -0.2086 0.0914 -0.1264 0.087 Uiso 1 1 d R . . H18C H -0.1991 0.1339 -0.0307 0.087 Uiso 1 1 d R . . C19 C -0.0337(4) 0.11781(15) -0.0817(4) 0.0448(15) Uani 1 1 d . . . H19A H -0.0484 0.1500 -0.0875 0.067 Uiso 1 1 d R . . H19B H -0.0565 0.1042 -0.1694 0.067 Uiso 1 1 d R . . H19C H 0.0339 0.1138 -0.0484 0.067 Uiso 1 1 d R . . C20 C -0.0856(4) 0.01717(16) 0.2251(4) 0.0332(13) Uani 1 1 d . . . C21 C -0.1538(4) 0.03187(17) 0.2785(5) 0.0460(15) Uani 1 1 d . . . H21 H -0.1418 0.0574 0.3349 0.055 Uiso 1 1 d R . . C22 C -0.2389(4) 0.0108(2) 0.2533(6) 0.0605(17) Uani 1 1 d . . . H22 H -0.2848 0.0219 0.2914 0.073 Uiso 1 1 d R . . C23 C -0.2571(4) -0.0265(2) 0.1721(6) 0.0610(18) Uani 1 1 d . . . H23 H -0.3158 -0.0412 0.1525 0.073 Uiso 1 1 d R . . C24 C -0.1887(5) -0.04217(19) 0.1198(5) 0.0542(16) Uani 1 1 d . . . H24 H -0.2004 -0.0682 0.0653 0.065 Uiso 1 1 d R . . C25 C -0.1038(4) -0.02089(16) 0.1449(5) 0.0441(15) Uani 1 1 d . . . H25 H -0.0578 -0.0321 0.1075 0.053 Uiso 1 1 d R . . C26 C 0.5000 -0.0380(5) 0.7500 0.190(6) Uiso 1 2 d S . . H26A H 0.4380 -0.0490 0.7014 0.285 Uiso 0.50 1 d PR . . H26B H 0.5161 -0.0490 0.8411 0.285 Uiso 0.50 1 d PR . . H26C H 0.5459 -0.0490 0.7076 0.285 Uiso 0.50 1 d PR . . C27 C 0.5000 0.0119(4) 0.7500 0.123(4) Uiso 1 2 d S . . C28 C 0.5469(6) 0.0350(3) 0.8585(8) 0.118(3) Uiso 1 1 d . . . H28 H 0.5796 0.0193 0.9362 0.142 Uiso 1 1 d R . . C29 C 0.5474(7) 0.0808(3) 0.8572(10) 0.145(4) Uiso 1 1 d . . . H29 H 0.5822 0.0965 0.9338 0.174 Uiso 1 1 d R . . C30 C 0.5000 0.1047(5) 0.7500 0.170(6) Uiso 1 2 d S . . H30 H 0.5000 0.1367 0.7500 0.204 Uiso 1 2 d SR . . 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 0.03573(19) 0.03052(16) 0.02142(15) 0.000 0.01085(12) 0.000 N1 0.033(2) 0.033(2) 0.026(2) 0.001(2) 0.0066(19) 0.002(2) N2 0.039(3) 0.031(2) 0.020(2) -0.0017(17) 0.006(2) 0.001(2) N3 0.040(4) 0.027(3) 0.035(3) 0.000 0.008(3) 0.000 C1 0.032(3) 0.025(3) 0.030(3) 0.006(2) 0.003(3) -0.001(3) C2 0.048(4) 0.038(3) 0.035(3) 0.001(2) 0.014(3) 0.000(3) C3 0.052(4) 0.043(3) 0.049(4) -0.006(3) 0.013(3) -0.014(3) C4 0.056(4) 0.035(3) 0.044(3) -0.009(3) 0.008(3) -0.008(3) C5 0.045(4) 0.038(3) 0.035(3) 0.000(2) 0.010(3) 0.008(3) C6 0.035(3) 0.028(3) 0.022(3) 0.002(2) 0.005(2) 0.004(3) C7 0.038(4) 0.039(3) 0.028(3) -0.008(2) 0.009(3) -0.006(3) C8 0.031(3) 0.043(3) 0.039(3) -0.002(3) 0.007(3) -0.009(3) C9 0.034(3) 0.045(3) 0.027(3) 0.002(2) 0.009(2) 0.003(3) C10 0.037(3) 0.036(3) 0.031(3) 0.002(2) 0.013(3) 0.009(3) C11 0.034(3) 0.027(3) 0.027(3) 0.003(2) 0.007(3) 0.011(3) C12 0.050(4) 0.052(3) 0.030(3) -0.005(2) 0.016(3) -0.001(3) C13 0.062(5) 0.067(4) 0.033(3) 0.000(3) 0.024(3) 0.008(4) C14 0.050(4) 0.069(4) 0.042(3) 0.003(3) 0.030(3) 0.006(4) C15 0.040(4) 0.050(4) 0.050(4) 0.008(3) 0.018(3) 0.008(3) C16 0.036(5) 0.035(4) 0.028(4) 0.000 0.015(4) 0.000 C17 0.048(4) 0.036(3) 0.025(3) -0.003(2) 0.008(3) 0.002(3) C18 0.054(4) 0.084(4) 0.029(3) -0.011(3) 0.002(3) 0.000(4) C19 0.067(4) 0.044(3) 0.027(3) -0.007(2) 0.019(3) -0.006(3) C20 0.038(4) 0.033(3) 0.029(3) 0.006(2) 0.009(3) -0.002(3) C21 0.051(4) 0.042(3) 0.047(3) 0.000(3) 0.018(3) -0.004(3) C22 0.054(5) 0.066(4) 0.072(5) 0.003(4) 0.035(4) -0.002(4) C23 0.048(4) 0.067(4) 0.064(4) 0.015(4) 0.009(4) -0.015(4) C24 0.063(5) 0.055(4) 0.042(4) -0.003(3) 0.010(3) -0.011(4) C25 0.047(4) 0.046(3) 0.039(3) -0.007(3) 0.012(3) -0.008(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 Ir1 2.000(5) . ? Ir1 C1 2.000(5) 2 ? Ir1 N1 2.038(4) 2 ? Ir1 N1 2.038(4) . ? Ir1 N2 2.191(4) . ? Ir1 N2 2.191(4) 2 ? N1 C7 1.346(5) . ? N1 C11 1.363(5) . ? N2 C16 1.320(5) . ? N2 C17 1.469(5) . ? N3 C20 1.408(5) . ? N3 C20 1.408(5) 2 ? N3 C16 1.427(8) . ? C2 C1 1.381(6) . ? C2 H2 0.9468 . ? C3 C2 1.390(6) . ? C3 H3 0.9498 . ? C4 C3 1.369(7) . ? C4 H4 0.9479 . ? C5 C4 1.369(7) . ? C5 H5 0.9536 . ? C6 C5 1.408(6) . ? C6 C1 1.422(6) . ? C6 C11 1.452(6) . ? C7 C8 1.357(6) . ? C7 H7 0.9500 . ? C8 C9 1.430(6) . ? C8 H8 0.9500 . ? C9 C10 1.402(6) . ? C9 C15 1.403(6) . ? C10 C12 1.444(6) . ? C10 C11 1.452(6) . ? C12 C13 1.363(7) . ? C12 H12 0.9500 . ? C13 C14 1.384(7) . ? C13 H13 0.9500 . ? C14 C15 1.371(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N2 1.320(5) 2 ? C17 C18 1.510(7) . ? C17 C19 1.527(6) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.374(7) . ? C20 C25 1.392(6) . ? C21 C22 1.376(7) . ? C21 H21 0.9500 . ? C22 C23 1.381(7) . ? C22 H22 0.9500 . ? C23 C24 1.378(8) . ? C23 H23 0.9500 . ? C24 C25 1.376(7) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.482(15) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.350(9) . ? C27 C28 1.350(9) 2_656 ? C28 C29 1.358(9) . ? C28 H28 0.9500 . ? C29 C30 1.354(10) . ? C29 H29 0.9500 . ? C30 C29 1.354(10) 2_656 ? C30 H30 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ir1 C1 86.1(2) . 2 ? C1 Ir1 N1 98.32(18) . 2 ? C1 Ir1 N1 79.47(19) 2 2 ? C1 Ir1 N1 79.47(19) . . ? C1 Ir1 N1 98.32(18) 2 . ? N1 Ir1 N1 177.0(2) 2 . ? C1 Ir1 N2 166.21(15) . . ? C1 Ir1 N2 107.08(16) 2 . ? N1 Ir1 N2 88.26(15) 2 . ? N1 Ir1 N2 94.33(15) . . ? C1 Ir1 N2 107.08(16) . 2 ? C1 Ir1 N2 166.21(15) 2 2 ? N1 Ir1 N2 94.33(15) 2 2 ? N1 Ir1 N2 88.26(15) . 2 ? N2 Ir1 N2 60.10(19) . 2 ? C7 N1 C11 120.7(4) . . ? C7 N1 Ir1 121.9(3) . . ? C11 N1 Ir1 117.0(3) . . ? C16 N2 C17 124.5(4) . . ? C16 N2 Ir1 93.7(3) . . ? C17 N2 Ir1 140.1(3) . . ? C20 N3 C20 122.5(6) . 2 ? C20 N3 C16 118.8(3) . . ? C20 N3 C16 118.8(3) 2 . ? C2 C1 C6 117.4(4) . . ? C2 C1 Ir1 127.6(4) . . ? C6 C1 Ir1 114.9(4) . . ? C1 C2 C3 122.2(5) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.9(5) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.3(5) . . ? C5 C6 C11 125.6(5) . . ? C1 C6 C11 114.9(4) . . ? N1 C7 C8 123.3(4) . . ? N1 C7 H7 118.4 . . ? C8 C7 H7 118.3 . . ? C7 C8 C9 119.8(5) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C15 121.1(5) . . ? C10 C9 C8 116.9(5) . . ? C15 C9 C8 121.9(5) . . ? C9 C10 C12 116.6(5) . . ? C9 C10 C11 120.5(4) . . ? C12 C10 C11 122.7(5) . . ? N1 C11 C10 118.0(4) . . ? N1 C11 C6 112.4(4) . . ? C10 C11 C6 129.5(4) . . ? C13 C12 C10 120.4(5) . . ? C13 C12 H12 119.8 . . ? C10 C12 H12 119.8 . . ? C12 C13 C14 121.7(5) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 119.6(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C9 120.4(5) . . ? C14 C15 H15 119.8 . . ? C9 C15 H15 119.8 . . ? N2 C16 N2 112.5(6) 2 . ? N2 C16 N3 123.8(3) 2 . ? N2 C16 N3 123.8(3) . . ? N2 C17 C18 110.4(4) . . ? N2 C17 C19 110.6(4) . . ? C18 C17 C19 110.6(4) . . ? N2 C17 H17 108.4 . . ? C18 C17 H17 108.4 . . ? C19 C17 H17 108.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 118.0(5) . . ? C21 C20 N3 121.1(4) . . ? C25 C20 N3 120.9(5) . . ? C20 C21 C22 122.2(5) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C21 C22 C23 119.5(6) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 119.0(6) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C25 C24 C23 121.4(6) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C20 119.9(6) . . ? C24 C25 H25 120.0 . . ? C20 C25 H25 120.0 . . ? C27 C26 H26A 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C27 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C28 118.8(13) . 2_656 ? C28 C27 C26 120.6(6) . . ? C28 C27 C26 120.6(6) 2_656 . ? C27 C28 C29 120.3(11) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 122.0(12) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C29 116.8(15) . 2_656 ? C29 C30 H30 121.6 . . ? C29 C30 H30 121.6 2_656 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.112 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.098