_publ_requested_journal Crystal Growth & Design. _publ_contact_author_name 'Chuluo Yang' _publ_contact_author_address 'Department of Chemistry, Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Wuhan University, Wuhan 430072, China' _publ_contact_author_email clyang@whu.edu.cn _publ_contact_author_phone +86-27-68756757 _publ_contact_author_fax +86-27-68756757 loop_ _publ_author_name _publ_author_address 'Lianqing Chen' 'Department of Chemistry, Wuhan University, Wuhan 430072, China' 'Chuluo Yang' 'Department of Chemistry, Wuhan University, Wuhan 430072, China' 'Ming Li' 'Department of Chemistry, Wuhan University, Wuhan 430072, China' 'Jingui Qin' 'Department of Chemistry, Wuhan University, Wuhan 430072, China' 'Han,You' 'State Key Laboratory of Polymer Chemistry and Physics, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China' 'Dongge Ma' 'State Key Laboratory of Polymer Chemistry and Physics, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China' data_dimer _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrakis[2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole-C~2~,N](u-dichloro) diiridium (III) dichloromethane solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C66 H56 Cl6 Ir2 N8 O12' _chemical_formula_sum 'C66 H56 Cl6 Ir2 N8 O12' _chemical_formula_weight 1750.29 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' 'Cl' 'Cl' 0.1484 0.1585 '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 _symmetry_space_group_name_Hall -C2yc 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 11.5352(10) _cell_length_b 23.390(2) _cell_length_c 25.239(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.423(2) _cell_angle_gamma 90.00 _cell_volume 6736.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 3335 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 20.42 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3440 _exptl_absorpt_coefficient_mu 4.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3823 _exptl_absorpt_correction_T_max 0.8483 _exptl_absorpt_process_details 'SADABS,Sheldric, 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(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 17436 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6526 _reflns_number_gt 4696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6526 _refine_ls_number_parameters 437 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _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 1.0000 0.059116(16) 0.2500 0.03952(14) Uani 1 2 d S . . Ir2 Ir 1.0000 0.217624(15) 0.2500 0.03821(14) Uani 1 2 d S . . N1 N 0.7310(6) 0.0695(3) 0.1952(3) 0.0527(18) Uani 1 1 d . A . N2 N 0.8471(5) 0.0495(2) 0.1986(3) 0.0451(15) Uani 1 1 d . A . N3 N 0.7632(6) 0.2033(2) 0.1674(2) 0.0477(16) Uani 1 1 d . . . N4 N 0.8321(5) 0.2262(2) 0.2119(2) 0.0424(15) Uani 1 1 d . . . Cl1 Cl 0.6639(3) 0.40657(17) 0.94598(16) 0.1370(14) Uani 1 1 d . . . Cl2 Cl 0.5944(4) 0.30336(17) 0.99093(17) 0.1555(15) Uani 1 1 d . . . O1 O 0.1878(8) 0.0521(5) 0.0861(5) 0.088(3) Uani 0.623(9) 1 d PD A 1 O2 O 0.7436(5) 0.0006(2) 0.1354(2) 0.0607(15) Uani 1 1 d . A . O3 O 1.2747(6) -0.1028(3) 0.1722(3) 0.0795(19) Uani 1 1 d . A . O4 O 0.2343(6) 0.1865(3) 0.0355(3) 0.088(2) Uani 1 1 d . . . O5 O 0.6579(4) 0.2637(2) 0.2094(2) 0.0509(13) Uani 1 1 d . . . O6 O 1.0094(6) 0.3657(2) 0.0812(2) 0.0652(16) Uani 1 1 d . . . O1' O 0.2224(13) 0.0328(9) 0.0464(7) 0.088(3) Uani 0.377(9) 1 d PD A 2 Cl3 Cl 1.06422(17) 0.13871(7) 0.19509(8) 0.0442(4) Uani 1 1 d . . . C1 C 0.1390(15) 0.0175(10) 0.0404(8) 0.118(8) Uani 0.623(9) 1 d PD A 1 H1A H 0.1801 0.0254 0.0107 0.176 Uiso 0.623(9) 1 calc PR A 1 H1B H 0.0575 0.0265 0.0306 0.176 Uiso 0.623(9) 1 calc PR A 1 H1C H 0.1472 -0.0222 0.0496 0.176 Uiso 0.623(9) 1 calc PR A 1 C2 C 0.3150(11) 0.0428(5) 0.0939(6) 0.106(4) Uani 1 1 d DU . . C3 C 0.3867(11) 0.0122(5) 0.0673(6) 0.113(4) Uani 1 1 d U A . H3 H 0.3585 -0.0073 0.0359 0.136 Uiso 1 1 calc R . . C4 C 0.5075(10) 0.0111(4) 0.0892(5) 0.097(3) Uani 1 1 d U . . H4 H 0.5596 -0.0099 0.0721 0.117 Uiso 1 1 calc R A . C5 C 0.5493(8) 0.0411(3) 0.1363(4) 0.068(3) Uani 1 1 d . A . C6 C 0.4716(8) 0.0711(4) 0.1606(5) 0.088(4) Uani 1 1 d . . . H6 H 0.4982 0.0916 0.1915 0.106 Uiso 1 1 calc R A . C7 C 0.3517(10) 0.0719(5) 0.1400(6) 0.101(4) Uani 1 1 d U A . H7 H 0.2986 0.0919 0.1575 0.122 Uiso 1 1 calc R . . C8 C 0.6732(7) 0.0395(3) 0.1576(4) 0.060(2) Uani 1 1 d . . . C9 C 0.8505(7) 0.0093(3) 0.1630(3) 0.052(2) Uani 1 1 d . . . C10 C 0.9567(7) -0.0216(3) 0.1621(3) 0.051(2) Uani 1 1 d . A . C11 C 0.9737(8) -0.0665(4) 0.1277(4) 0.070(3) Uani 1 1 d . . . H11 H 0.9130 -0.0778 0.1014 0.084 Uiso 1 1 calc R A . C12 C 1.0804(8) -0.0940(4) 0.1325(4) 0.075(3) Uani 1 1 d . A . H12 H 1.0919 -0.1249 0.1106 0.090 Uiso 1 1 calc R . . C13 C 1.1702(8) -0.0744(4) 0.1709(4) 0.064(2) Uani 1 1 d . . . C14 C 1.1545(7) -0.0300(3) 0.2051(3) 0.055(2) Uani 1 1 d . A . H14 H 1.2164 -0.0182 0.2306 0.067 Uiso 1 1 calc R . . C15 C 1.0458(6) -0.0027(3) 0.2018(3) 0.0409(17) Uani 1 1 d . . . C16 C 1.3720(8) -0.0816(4) 0.2070(4) 0.081(3) Uani 1 1 d . . . H16A H 1.3874 -0.0429 0.1973 0.121 Uiso 1 1 calc R A . H16B H 1.4393 -0.1048 0.2042 0.121 Uiso 1 1 calc R . . H16C H 1.3554 -0.0825 0.2432 0.121 Uiso 1 1 calc R . . C17 C 0.2299(10) 0.1626(5) -0.0150(4) 0.106(4) Uani 1 1 d . . . H17A H 0.2705 0.1869 -0.0368 0.158 Uiso 1 1 calc R . . H17B H 0.1497 0.1586 -0.0312 0.158 Uiso 1 1 calc R . . H17C H 0.2665 0.1256 -0.0119 0.158 Uiso 1 1 calc R . . C18 C 0.3448(8) 0.1953(4) 0.0659(4) 0.062(2) Uani 1 1 d . . . C19 C 0.3415(9) 0.2224(4) 0.1135(4) 0.074(3) Uani 1 1 d . . . H19 H 0.2706 0.2330 0.1240 0.089 Uiso 1 1 calc R . . C20 C 0.4455(8) 0.2336(4) 0.1451(4) 0.067(3) Uani 1 1 d . . . H20 H 0.4448 0.2538 0.1768 0.081 Uiso 1 1 calc R . . C21 C 0.5524(7) 0.2158(3) 0.1316(3) 0.053(2) Uani 1 1 d . . . C22 C 0.5507(8) 0.1880(4) 0.0836(4) 0.063(2) Uani 1 1 d . . . H22 H 0.6209 0.1757 0.0735 0.076 Uiso 1 1 calc R . . C23 C 0.4477(8) 0.1780(4) 0.0502(3) 0.063(2) Uani 1 1 d . . . H23 H 0.4478 0.1597 0.0175 0.075 Uiso 1 1 calc R . . C24 C 0.6622(7) 0.2255(3) 0.1675(3) 0.050(2) Uani 1 1 d . . . C25 C 0.7693(6) 0.2618(3) 0.2347(3) 0.0437(18) Uani 1 1 d . . . C26 C 0.8901(9) 0.3539(4) 0.0615(4) 0.072(3) Uani 1 1 d . . . H26A H 0.8802 0.3135 0.0555 0.108 Uiso 1 1 calc R . . H26B H 0.8677 0.3739 0.0284 0.108 Uiso 1 1 calc R . . H26C H 0.8419 0.3662 0.0873 0.108 Uiso 1 1 calc R . . C27 C 1.0621(8) 0.3397(3) 0.1275(3) 0.052(2) Uani 1 1 d . . . C28 C 1.0031(7) 0.3005(3) 0.1561(3) 0.0454(18) Uani 1 1 d . . . H28 H 0.9256 0.2908 0.1439 0.054 Uiso 1 1 calc R . . C29 C 1.0622(6) 0.2758(3) 0.2033(3) 0.0397(17) Uani 1 1 d . . . C30 C 1.1810(6) 0.2919(3) 0.2187(3) 0.0441(18) Uani 1 1 d . . . C31 C 1.2351(7) 0.3323(3) 0.1902(3) 0.054(2) Uani 1 1 d . . . H31 H 1.3122 0.3430 0.2021 0.064 Uiso 1 1 calc R . . C32 C 1.1758(8) 0.3563(3) 0.1449(4) 0.060(2) Uani 1 1 d . . . H32 H 1.2118 0.3836 0.1260 0.073 Uiso 1 1 calc R . . C33 C 0.5878(15) 0.3418(7) 0.9344(5) 0.153(6) Uani 1 1 d . . . H33A H 0.5065 0.3496 0.9204 0.183 Uiso 1 1 calc R . . H33B H 0.6213 0.3199 0.9078 0.183 Uiso 1 1 calc R . . C1' C 0.128(2) 0.0545(18) 0.0716(14) 0.118(8) Uani 0.377(9) 1 d PD A 2 H1F H 0.1089 0.0276 0.0978 0.176 Uiso 0.377(9) 1 calc PR A 2 H1E H 0.0600 0.0604 0.0450 0.176 Uiso 0.377(9) 1 calc PR A 2 H1D H 0.1503 0.0902 0.0888 0.176 Uiso 0.377(9) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0377(2) 0.0362(2) 0.0443(3) 0.000 0.00478(19) 0.000 Ir2 0.0423(3) 0.0350(2) 0.0379(3) 0.000 0.00792(19) 0.000 N1 0.040(4) 0.050(4) 0.065(5) 0.014(3) 0.000(4) 0.004(3) N2 0.036(3) 0.047(4) 0.051(4) 0.004(3) -0.001(3) -0.001(3) N3 0.057(4) 0.045(4) 0.040(4) -0.004(3) 0.001(3) 0.002(3) N4 0.043(4) 0.038(3) 0.047(4) -0.004(3) 0.008(3) -0.003(3) Cl1 0.126(3) 0.137(3) 0.143(3) 0.054(3) 0.004(3) -0.006(2) Cl2 0.209(4) 0.110(3) 0.140(4) 0.014(2) 0.001(3) -0.013(3) O1 0.033(5) 0.106(8) 0.116(11) 0.004(7) -0.016(6) 0.005(5) O2 0.056(3) 0.055(3) 0.066(4) -0.003(3) -0.012(3) -0.012(3) O3 0.074(4) 0.072(4) 0.092(5) -0.038(4) 0.013(4) 0.013(3) O4 0.084(5) 0.105(5) 0.065(5) -0.017(4) -0.018(4) -0.012(4) O5 0.051(3) 0.054(3) 0.046(3) -0.009(3) 0.003(3) 0.009(3) O6 0.083(5) 0.066(4) 0.048(4) 0.015(3) 0.014(3) 0.001(3) O1' 0.033(5) 0.106(8) 0.116(11) 0.004(7) -0.016(6) 0.005(5) Cl3 0.0490(11) 0.0407(9) 0.0453(11) -0.0021(8) 0.0148(9) -0.0001(8) C1 0.042(8) 0.19(2) 0.109(19) 0.007(13) -0.035(11) -0.025(12) C2 0.091(7) 0.090(7) 0.130(8) 0.035(6) -0.010(7) -0.019(6) C3 0.102(7) 0.089(7) 0.133(8) -0.002(6) -0.034(7) -0.016(6) C4 0.083(6) 0.071(6) 0.125(7) 0.002(6) -0.030(6) -0.008(5) C5 0.052(5) 0.047(5) 0.095(8) 0.023(5) -0.019(5) -0.011(4) C6 0.042(5) 0.079(7) 0.138(11) 0.035(7) -0.004(6) 0.007(5) C7 0.073(6) 0.105(7) 0.125(8) 0.038(6) 0.009(6) 0.001(5) C8 0.045(5) 0.042(4) 0.087(7) 0.008(4) -0.010(5) -0.007(4) C9 0.053(5) 0.046(4) 0.051(5) -0.002(4) -0.005(4) -0.018(4) C10 0.045(5) 0.045(4) 0.060(5) -0.003(4) -0.005(4) -0.004(3) C11 0.068(6) 0.070(6) 0.069(7) -0.029(5) 0.006(5) -0.024(5) C12 0.060(6) 0.070(6) 0.096(8) -0.038(6) 0.016(6) -0.005(5) C13 0.066(6) 0.055(5) 0.074(7) -0.023(5) 0.024(5) -0.003(4) C14 0.057(5) 0.042(4) 0.069(6) -0.015(4) 0.015(4) -0.007(4) C15 0.043(4) 0.037(4) 0.044(4) -0.004(3) 0.011(3) -0.007(3) C16 0.065(6) 0.073(6) 0.107(9) -0.016(6) 0.023(6) 0.007(5) C17 0.105(9) 0.119(9) 0.083(8) -0.020(7) -0.018(7) -0.009(8) C18 0.057(6) 0.074(6) 0.052(6) -0.008(5) 0.000(5) 0.000(5) C19 0.059(6) 0.089(7) 0.068(7) -0.024(5) -0.009(5) 0.012(5) C20 0.053(6) 0.076(6) 0.069(7) -0.017(5) -0.004(5) 0.013(5) C21 0.057(5) 0.049(5) 0.054(6) 0.000(4) 0.008(4) -0.003(4) C22 0.059(6) 0.073(6) 0.057(6) -0.008(5) 0.005(5) -0.002(5) C23 0.078(7) 0.067(6) 0.042(5) -0.008(4) 0.007(5) -0.005(5) C24 0.050(5) 0.052(5) 0.048(5) 0.003(4) 0.009(4) 0.009(4) C25 0.048(5) 0.034(4) 0.049(5) -0.006(3) 0.007(4) 0.002(3) C26 0.072(7) 0.081(7) 0.060(6) 0.010(5) 0.001(5) 0.017(5) C27 0.072(6) 0.043(4) 0.043(5) 0.007(4) 0.018(4) 0.012(4) C28 0.058(5) 0.038(4) 0.042(5) -0.002(3) 0.012(4) -0.001(3) C29 0.039(4) 0.036(4) 0.045(5) -0.008(3) 0.010(3) -0.002(3) C30 0.050(5) 0.033(4) 0.050(5) 0.000(3) 0.009(4) 0.000(3) C31 0.058(5) 0.040(4) 0.065(6) 0.003(4) 0.016(5) -0.002(4) C32 0.066(6) 0.050(5) 0.069(6) 0.007(4) 0.021(5) -0.005(4) C33 0.187(16) 0.200(16) 0.075(9) -0.034(10) 0.030(10) -0.074(13) C1' 0.042(8) 0.19(2) 0.109(19) 0.007(13) -0.035(11) -0.025(12) _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 C15 2.010(7) . ? Ir1 C15 2.010(7) 2_755 ? Ir1 N2 2.043(6) . ? Ir1 N2 2.043(6) 2_755 ? Ir1 Cl3 2.4973(18) 2_755 ? Ir1 Cl3 2.4973(18) . ? Ir2 C29 2.001(7) 2_755 ? Ir2 C29 2.001(7) . ? Ir2 N4 2.042(6) . ? Ir2 N4 2.042(6) 2_755 ? Ir2 Cl3 2.4854(17) . ? Ir2 Cl3 2.4855(17) 2_755 ? N1 C8 1.285(10) . ? N1 N2 1.409(8) . ? N2 C9 1.306(9) . ? N3 C24 1.276(9) . ? N3 N4 1.385(8) . ? N4 C25 1.292(8) . ? Cl1 C33 1.753(14) . ? Cl2 C33 1.679(14) . ? O1 C1 1.454(16) . ? O1 C2 1.468(14) . ? O2 C9 1.339(8) . ? O2 C8 1.389(10) . ? O3 C13 1.372(10) . ? O3 C16 1.410(10) . ? O4 C17 1.388(12) . ? O4 C18 1.404(10) . ? O5 C25 1.349(8) . ? O5 C24 1.389(9) . ? O6 C27 1.376(9) . ? O6 C26 1.419(11) . ? O1' C1' 1.44(2) . ? O1' C2 1.504(17) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.344(17) . ? C2 C7 1.363(17) . ? C3 C4 1.423(14) . ? C3 H3 0.9300 . ? C4 C5 1.404(14) . ? C4 H4 0.9300 . ? C5 C6 1.353(14) . ? C5 C8 1.453(11) . ? C6 C7 1.404(14) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.425(10) . ? C10 C11 1.395(11) . ? C10 C15 1.397(10) . ? C11 C12 1.379(12) . ? C11 H11 0.9300 . ? C12 C13 1.390(12) . ? C12 H12 0.9300 . ? C13 C14 1.378(11) . ? C14 C15 1.398(10) . ? C14 H14 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.363(12) . ? C18 C23 1.367(11) . ? C19 C20 1.366(12) . ? C19 H19 0.9300 . ? C20 C21 1.390(11) . ? C20 H20 0.9300 . ? C21 C22 1.373(11) . ? C21 C24 1.464(11) . ? C22 C23 1.373(11) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C25 C30 1.419(10) 2_755 ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C32 1.377(12) . ? C27 C28 1.405(10) . ? C28 C29 1.406(10) . ? C28 H28 0.9300 . ? C29 C30 1.419(9) . ? C30 C31 1.390(10) . ? C30 C25 1.419(10) 2_755 ? C31 C32 1.364(11) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C1' H1F 0.9600 . ? C1' H1E 0.9600 . ? C1' H1D 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 Ir1 C15 87.9(4) . 2_755 ? C15 Ir1 N2 79.4(3) . . ? C15 Ir1 N2 91.5(3) 2_755 . ? C15 Ir1 N2 91.5(3) . 2_755 ? C15 Ir1 N2 79.4(3) 2_755 2_755 ? N2 Ir1 N2 167.4(3) . 2_755 ? C15 Ir1 Cl3 176.4(2) . 2_755 ? C15 Ir1 Cl3 94.3(2) 2_755 2_755 ? N2 Ir1 Cl3 97.80(18) . 2_755 ? N2 Ir1 Cl3 91.60(17) 2_755 2_755 ? C15 Ir1 Cl3 94.3(2) . . ? C15 Ir1 Cl3 176.4(2) 2_755 . ? N2 Ir1 Cl3 91.61(17) . . ? N2 Ir1 Cl3 97.80(18) 2_755 . ? Cl3 Ir1 Cl3 83.59(8) 2_755 . ? C29 Ir2 C29 94.3(4) 2_755 . ? C29 Ir2 N4 79.2(3) 2_755 . ? C29 Ir2 N4 93.0(3) . . ? C29 Ir2 N4 93.0(3) 2_755 2_755 ? C29 Ir2 N4 79.2(3) . 2_755 ? N4 Ir2 N4 168.7(3) . 2_755 ? C29 Ir2 Cl3 174.54(19) 2_755 . ? C29 Ir2 Cl3 90.86(19) . . ? N4 Ir2 Cl3 98.63(17) . . ? N4 Ir2 Cl3 89.76(16) 2_755 . ? C29 Ir2 Cl3 90.86(19) 2_755 2_755 ? C29 Ir2 Cl3 174.54(19) . 2_755 ? N4 Ir2 Cl3 89.76(16) . 2_755 ? N4 Ir2 Cl3 98.63(17) 2_755 2_755 ? Cl3 Ir2 Cl3 84.08(8) . 2_755 ? C8 N1 N2 104.5(7) . . ? C9 N2 N1 108.7(6) . . ? C9 N2 Ir1 114.0(5) . . ? N1 N2 Ir1 136.6(5) . . ? C24 N3 N4 104.8(6) . . ? C25 N4 N3 108.5(6) . . ? C25 N4 Ir2 114.2(5) . . ? N3 N4 Ir2 137.4(5) . . ? C1 O1 C2 106.7(12) . . ? C9 O2 C8 103.8(6) . . ? C13 O3 C16 117.4(7) . . ? C17 O4 C18 118.0(8) . . ? C25 O5 C24 101.6(6) . . ? C27 O6 C26 119.8(7) . . ? C1' O1' C2 95.1(17) . . ? Ir2 Cl3 Ir1 96.16(6) . . ? C3 C2 C7 123.9(13) . . ? C3 C2 O1 133.4(13) . . ? C7 C2 O1 102.6(13) . . ? C3 C2 O1' 86.3(12) . . ? C7 C2 O1' 148.8(14) . . ? O1 C2 O1' 48.4(9) . . ? C2 C3 C4 117.0(12) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? C5 C4 C3 121.0(12) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 118.4(9) . . ? C6 C5 C8 121.9(10) . . ? C4 C5 C8 119.8(10) . . ? C5 C6 C7 121.5(12) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C2 C7 C6 118.3(13) . . ? C2 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? N1 C8 O2 112.6(7) . . ? N1 C8 C5 129.4(9) . . ? O2 C8 C5 118.0(8) . . ? N2 C9 O2 110.4(7) . . ? N2 C9 C10 119.2(7) . . ? O2 C9 C10 130.0(7) . . ? C11 C10 C15 121.9(7) . . ? C11 C10 C9 126.2(7) . . ? C15 C10 C9 111.9(7) . . ? C12 C11 C10 120.1(8) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 118.1(8) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? O3 C13 C14 123.1(8) . . ? O3 C13 C12 114.7(7) . . ? C14 C13 C12 122.2(8) . . ? C13 C14 C15 120.3(8) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 117.2(7) . . ? C10 C15 Ir1 115.5(5) . . ? C14 C15 Ir1 127.2(6) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 122.2(9) . . ? C19 C18 O4 114.1(8) . . ? C23 C18 O4 123.7(8) . . ? C18 C19 C20 117.9(9) . . ? C18 C19 H19 121.1 . . ? C20 C19 H19 121.1 . . ? C19 C20 C21 122.3(9) . . ? C19 C20 H20 118.9 . . ? C21 C20 H20 118.9 . . ? C22 C21 C20 117.4(8) . . ? C22 C21 C24 121.2(8) . . ? C20 C21 C24 121.4(8) . . ? C23 C22 C21 121.4(8) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C18 C23 C22 118.8(8) . . ? C18 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? N3 C24 O5 113.5(7) . . ? N3 C24 C21 130.0(8) . . ? O5 C24 C21 116.5(7) . . ? N4 C25 O5 111.6(6) . . ? N4 C25 C30 120.2(7) . 2_755 ? O5 C25 C30 128.1(6) . 2_755 ? O6 C26 H26A 109.5 . . ? O6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O6 C27 C32 115.4(7) . . ? O6 C27 C28 122.6(8) . . ? C32 C27 C28 122.0(8) . . ? C27 C28 C29 119.5(7) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C28 C29 C30 116.9(7) . . ? C28 C29 Ir2 127.3(5) . . ? C30 C29 Ir2 115.7(5) . . ? C31 C30 C29 121.8(7) . . ? C31 C30 C25 127.5(7) . 2_755 ? C29 C30 C25 110.7(6) . 2_755 ? C32 C31 C30 120.4(8) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C27 119.3(8) . . ? C31 C32 H32 120.3 . . ? C27 C32 H32 120.3 . . ? Cl2 C33 Cl1 111.3(7) . . ? Cl2 C33 H33A 109.4 . . ? Cl1 C33 H33A 109.4 . . ? Cl2 C33 H33B 109.4 . . ? Cl1 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? O1' C1' H1F 109.5 . . ? O1' C1' H1E 109.5 . . ? H1F C1' H1E 109.5 . . ? O1' C1' H1D 109.5 . . ? H1F C1' H1D 109.5 . . ? H1E C1' H1D 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 0.0(8) . . . . ? C8 N1 N2 Ir1 -169.3(6) . . . . ? C15 Ir1 N2 C9 2.4(5) . . . . ? C15 Ir1 N2 C9 -85.2(6) 2_755 . . . ? Cl3 Ir1 N2 C9 -179.8(5) 2_755 . . . ? Cl3 Ir1 N2 C9 96.5(5) . . . . ? C15 Ir1 N2 N1 171.3(7) . . . . ? C15 Ir1 N2 N1 83.7(7) 2_755 . . . ? N2 Ir1 N2 N1 127.0(6) 2_755 . . . ? Cl3 Ir1 N2 N1 -10.9(7) 2_755 . . . ? Cl3 Ir1 N2 N1 -94.6(6) . . . . ? C24 N3 N4 C25 -1.9(8) . . . . ? C24 N3 N4 Ir2 176.9(6) . . . . ? C29 Ir2 N4 C25 -0.9(5) 2_755 . . . ? C29 Ir2 N4 C25 -94.7(5) . . . . ? Cl3 Ir2 N4 C25 174.0(5) . . . . ? Cl3 Ir2 N4 C25 90.0(5) 2_755 . . . ? C29 Ir2 N4 N3 -179.6(7) 2_755 . . . ? C29 Ir2 N4 N3 86.6(7) . . . . ? N4 Ir2 N4 N3 133.0(7) 2_755 . . . ? Cl3 Ir2 N4 N3 -4.7(7) . . . . ? Cl3 Ir2 N4 N3 -88.7(6) 2_755 . . . ? C29 Ir2 Cl3 Ir1 177.9(2) . . . . ? N4 Ir2 Cl3 Ir1 -88.85(17) . . . . ? N4 Ir2 Cl3 Ir1 98.70(17) 2_755 . . . ? Cl3 Ir2 Cl3 Ir1 0.0 2_755 . . . ? C15 Ir1 Cl3 Ir2 177.1(2) . . . . ? N2 Ir1 Cl3 Ir2 97.67(18) . . . . ? N2 Ir1 Cl3 Ir2 -90.75(17) 2_755 . . . ? Cl3 Ir1 Cl3 Ir2 0.0 2_755 . . . ? C1 O1 C2 C3 3(2) . . . . ? C1 O1 C2 C7 -174.3(13) . . . . ? C1 O1 C2 O1' 19.1(16) . . . . ? C1' O1' C2 C3 170(2) . . . . ? C1' O1' C2 C7 -24(4) . . . . ? C1' O1' C2 O1 2(2) . . . . ? C7 C2 C3 C4 0(2) . . . . ? O1 C2 C3 C4 -176.5(12) . . . . ? O1' C2 C3 C4 171.1(13) . . . . ? C2 C3 C4 C5 -0.6(17) . . . . ? C3 C4 C5 C6 0.3(15) . . . . ? C3 C4 C5 C8 -179.6(9) . . . . ? C4 C5 C6 C7 0.8(14) . . . . ? C8 C5 C6 C7 -179.3(9) . . . . ? C3 C2 C7 C6 1.3(19) . . . . ? O1 C2 C7 C6 178.6(10) . . . . ? O1' C2 C7 C6 -162(2) . . . . ? C5 C6 C7 C2 -1.6(16) . . . . ? N2 N1 C8 O2 -0.1(9) . . . . ? N2 N1 C8 C5 -180.0(8) . . . . ? C9 O2 C8 N1 0.2(9) . . . . ? C9 O2 C8 C5 -179.9(7) . . . . ? C6 C5 C8 N1 -10.4(15) . . . . ? C4 C5 C8 N1 169.6(9) . . . . ? C6 C5 C8 O2 169.7(8) . . . . ? C4 C5 C8 O2 -10.3(12) . . . . ? N1 N2 C9 O2 0.1(8) . . . . ? Ir1 N2 C9 O2 172.0(5) . . . . ? N1 N2 C9 C10 -173.9(7) . . . . ? Ir1 N2 C9 C10 -2.0(9) . . . . ? C8 O2 C9 N2 -0.1(8) . . . . ? C8 O2 C9 C10 173.0(8) . . . . ? N2 C9 C10 C11 178.4(8) . . . . ? O2 C9 C10 C11 5.7(14) . . . . ? N2 C9 C10 C15 -0.1(11) . . . . ? O2 C9 C10 C15 -172.8(7) . . . . ? C15 C10 C11 C12 0.7(14) . . . . ? C9 C10 C11 C12 -177.7(9) . . . . ? C10 C11 C12 C13 -2.4(15) . . . . ? C16 O3 C13 C14 -5.9(13) . . . . ? C16 O3 C13 C12 174.4(9) . . . . ? C11 C12 C13 O3 -178.0(9) . . . . ? C11 C12 C13 C14 2.3(15) . . . . ? O3 C13 C14 C15 179.9(8) . . . . ? C12 C13 C14 C15 -0.5(14) . . . . ? C11 C10 C15 C14 1.1(12) . . . . ? C9 C10 C15 C14 179.7(7) . . . . ? C11 C10 C15 Ir1 -176.4(7) . . . . ? C9 C10 C15 Ir1 2.2(9) . . . . ? C13 C14 C15 C10 -1.3(12) . . . . ? C13 C14 C15 Ir1 175.9(6) . . . . ? C15 Ir1 C15 C10 89.4(6) 2_755 . . . ? N2 Ir1 C15 C10 -2.5(5) . . . . ? N2 Ir1 C15 C10 168.7(6) 2_755 . . . ? Cl3 Ir1 C15 C10 -93.3(5) . . . . ? C15 Ir1 C15 C14 -87.8(7) 2_755 . . . ? N2 Ir1 C15 C14 -179.7(7) . . . . ? N2 Ir1 C15 C14 -8.5(7) 2_755 . . . ? Cl3 Ir1 C15 C14 89.4(6) . . . . ? C17 O4 C18 C19 175.9(10) . . . . ? C17 O4 C18 C23 -4.8(14) . . . . ? C23 C18 C19 C20 1.8(15) . . . . ? O4 C18 C19 C20 -178.8(8) . . . . ? C18 C19 C20 C21 -3.3(15) . . . . ? C19 C20 C21 C22 2.4(14) . . . . ? C19 C20 C21 C24 -176.6(8) . . . . ? C20 C21 C22 C23 -0.1(13) . . . . ? C24 C21 C22 C23 178.9(8) . . . . ? C19 C18 C23 C22 0.3(14) . . . . ? O4 C18 C23 C22 -179.0(8) . . . . ? C21 C22 C23 C18 -1.2(13) . . . . ? N4 N3 C24 O5 1.1(8) . . . . ? N4 N3 C24 C21 -177.2(8) . . . . ? C25 O5 C24 N3 0.1(8) . . . . ? C25 O5 C24 C21 178.6(7) . . . . ? C22 C21 C24 N3 -14.4(13) . . . . ? C20 C21 C24 N3 164.6(9) . . . . ? C22 C21 C24 O5 167.4(7) . . . . ? C20 C21 C24 O5 -13.7(11) . . . . ? N3 N4 C25 O5 2.1(8) . . . . ? Ir2 N4 C25 O5 -177.0(4) . . . . ? N3 N4 C25 C30 -179.5(6) . . . 2_755 ? Ir2 N4 C25 C30 1.4(9) . . . 2_755 ? C24 O5 C25 N4 -1.4(8) . . . . ? C24 O5 C25 C30 -179.6(7) . . . 2_755 ? C26 O6 C27 C32 -176.5(7) . . . . ? C26 O6 C27 C28 1.5(11) . . . . ? O6 C27 C28 C29 -179.6(6) . . . . ? C32 C27 C28 C29 -1.7(11) . . . . ? C27 C28 C29 C30 -1.2(10) . . . . ? C27 C28 C29 Ir2 -178.2(5) . . . . ? C29 Ir2 C29 C28 -90.3(6) 2_755 . . . ? N4 Ir2 C29 C28 -10.9(6) . . . . ? N4 Ir2 C29 C28 177.4(6) 2_755 . . . ? Cl3 Ir2 C29 C28 87.8(6) . . . . ? C29 Ir2 C29 C30 92.7(5) 2_755 . . . ? N4 Ir2 C29 C30 172.1(5) . . . . ? N4 Ir2 C29 C30 0.4(5) 2_755 . . . ? Cl3 Ir2 C29 C30 -89.2(5) . . . . ? C28 C29 C30 C31 3.3(10) . . . . ? Ir2 C29 C30 C31 -179.4(6) . . . . ? C28 C29 C30 C25 -177.2(6) . . . 2_755 ? Ir2 C29 C30 C25 0.2(8) . . . 2_755 ? C29 C30 C31 C32 -2.5(11) . . . . ? C25 C30 C31 C32 178.0(8) 2_755 . . . ? C30 C31 C32 C27 -0.6(12) . . . . ? O6 C27 C32 C31 -179.3(7) . . . . ? C28 C27 C32 C31 2.7(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C33 H33B N3 0.97 2.53 3.460(16) 159.9 7_656 C26 H26C O3 0.96 2.49 3.420(12) 162.6 3_455 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.843 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.137 end data_complex 2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2, 5-di-p-tolyl-1, 3, 4-oxadiazolyl-C2,N)iridium (acetylacetonate) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H35 Cl2 Ir N4 O4' _chemical_formula_weight 874.80 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ir' 'Ir' -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2710(8) _cell_length_b 13.3034(10) _cell_length_c 14.1672(11) _cell_angle_alpha 92.3960(10) _cell_angle_beta 108.3660(10) _cell_angle_gamma 98.2710(10) _cell_volume 1810.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4761 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 25.25 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 3.881 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.4438 _exptl_absorpt_correction_T_max 0.6531 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 11845 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8077 _reflns_number_gt 6669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00083(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8077 _refine_ls_number_parameters 449 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.555 _refine_ls_shift/su_mean 0.015 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7636(5) 0.3667(4) 0.3289(3) 0.0441(12) Uani 1 1 d . . . C2 C 0.7295(5) 0.3264(4) 0.2260(3) 0.0399(11) Uani 1 1 d . . . C3 C 0.8419(5) 0.3482(4) 0.1901(3) 0.0423(12) Uani 1 1 d . . . H3 H 0.8281 0.3255 0.1241 0.051 Uiso 1 1 calc R . . C4 C 0.9703(6) 0.4002(4) 0.2446(4) 0.0497(13) Uani 1 1 d . . . C5 C 0.9969(6) 0.4349(5) 0.3458(4) 0.0609(16) Uani 1 1 d . . . H5 H 1.0842 0.4694 0.3844 0.073 Uiso 1 1 calc R . . C6 C 0.8914(6) 0.4167(5) 0.3858(4) 0.0611(17) Uani 1 1 d . . . H6 H 0.9072 0.4386 0.4522 0.073 Uiso 1 1 calc R . . C7 C 1.0843(6) 0.4205(5) 0.1986(4) 0.0748(19) Uani 1 1 d . . . H7A H 1.1650 0.3951 0.2385 0.112 Uiso 1 1 calc R . . H7B H 1.1075 0.4926 0.1959 0.112 Uiso 1 1 calc R . . H7C H 1.0531 0.3868 0.1323 0.112 Uiso 1 1 calc R . . C8 C 0.6429(5) 0.3488(4) 0.3585(3) 0.0442(12) Uani 1 1 d . . . C9 C 0.4894(6) 0.3413(4) 0.4316(3) 0.0466(13) Uani 1 1 d . . . C10 C 0.4346(6) 0.3566(4) 0.5143(3) 0.0475(13) Uani 1 1 d . . . C11 C 0.3016(6) 0.3173(5) 0.5046(4) 0.0648(17) Uani 1 1 d . . . H11 H 0.2438 0.2820 0.4446 0.078 Uiso 1 1 calc R . . C12 C 0.2507(7) 0.3293(5) 0.5836(4) 0.0692(18) Uani 1 1 d . . . H12 H 0.1581 0.3036 0.5745 0.083 Uiso 1 1 calc R . . C13 C 0.3321(8) 0.3772(5) 0.6733(4) 0.0625(17) Uani 1 1 d . . . C14 C 0.2778(8) 0.3849(6) 0.7593(4) 0.086(2) Uani 1 1 d . . . H14A H 0.3419 0.3638 0.8175 0.129 Uiso 1 1 calc R . . H14B H 0.1891 0.3416 0.7432 0.129 Uiso 1 1 calc R . . H14C H 0.2677 0.4543 0.7724 0.129 Uiso 1 1 calc R . . C15 C 0.4649(7) 0.4198(5) 0.6820(4) 0.074(2) Uani 1 1 d . . . H15 H 0.5208 0.4569 0.7416 0.089 Uiso 1 1 calc R . . C16 C 0.5192(6) 0.4095(5) 0.6046(4) 0.0672(18) Uani 1 1 d . . . H16 H 0.6109 0.4376 0.6130 0.081 Uiso 1 1 calc R . . C17 C 0.3448(6) 0.3898(4) 0.0474(3) 0.0456(13) Uani 1 1 d . . . C18 C 0.2362(6) 0.3084(5) 0.0125(4) 0.0537(14) Uani 1 1 d . . . H18 H 0.1557 0.3227 -0.0338 0.064 Uiso 1 1 calc R . . C19 C 0.2316(5) 0.2087(4) 0.0373(3) 0.0446(12) Uani 1 1 d . . . C20 C 0.3179(7) 0.4940(5) 0.0179(4) 0.0629(16) Uani 1 1 d . . . H20A H 0.3034 0.5318 0.0718 0.094 Uiso 1 1 calc R . . H20B H 0.2367 0.4874 -0.0402 0.094 Uiso 1 1 calc R . . H20C H 0.3966 0.5293 0.0032 0.094 Uiso 1 1 calc R . . C21 C 0.0998(6) 0.1346(5) -0.0081(4) 0.0682(17) Uani 1 1 d . . . H21A H 0.1129 0.0686 0.0146 0.102 Uiso 1 1 calc R . . H21B H 0.0750 0.1302 -0.0795 0.102 Uiso 1 1 calc R . . H21C H 0.0267 0.1573 0.0116 0.102 Uiso 1 1 calc R . . C22 C 0.6536(6) -0.0792(5) 0.2447(4) 0.0630(16) Uani 1 1 d . . . H22 H 0.6745 -0.1441 0.2571 0.076 Uiso 1 1 calc R . . C23 C 0.6589(6) -0.0387(4) 0.1577(4) 0.0590(16) Uani 1 1 d . . . H23 H 0.6836 -0.0764 0.1111 0.071 Uiso 1 1 calc R . . C24 C 0.6278(5) 0.0571(4) 0.1399(4) 0.0468(12) Uani 1 1 d . . . C25 C 0.5895(5) 0.1217(4) 0.2084(3) 0.0412(12) Uani 1 1 d . . . C26 C 0.5867(5) 0.0746(4) 0.2941(3) 0.0477(13) Uani 1 1 d . . . H26 H 0.5629 0.1111 0.3419 0.057 Uiso 1 1 calc R . . C27 C 0.6166(6) -0.0222(5) 0.3136(4) 0.0550(14) Uani 1 1 d . . . C28 C 0.6055(8) -0.0675(5) 0.4077(4) 0.081(2) Uani 1 1 d . . . H28A H 0.5479 -0.1334 0.3903 0.121 Uiso 1 1 calc R . . H28B H 0.5651 -0.0235 0.4418 0.121 Uiso 1 1 calc R . . H28C H 0.6966 -0.0742 0.4505 0.121 Uiso 1 1 calc R . . C29 C 0.6281(5) 0.1113(4) 0.0533(3) 0.0437(12) Uani 1 1 d . . . C30 C 0.6653(5) 0.1709(4) -0.0743(3) 0.0453(13) Uani 1 1 d . . . C31 C 0.7155(6) 0.1738(4) -0.1598(4) 0.0496(14) Uani 1 1 d . . . C32 C 0.7373(6) 0.0857(5) -0.2045(4) 0.0562(15) Uani 1 1 d . . . H32 H 0.7200 0.0228 -0.1806 0.067 Uiso 1 1 calc R . . C33 C 0.7855(7) 0.0934(5) -0.2854(4) 0.0650(18) Uani 1 1 d . . . H33 H 0.7999 0.0343 -0.3154 0.078 Uiso 1 1 calc R . . C34 C 0.8124(7) 0.1829(6) -0.3224(4) 0.0694(19) Uani 1 1 d . . . C35 C 0.7909(9) 0.2698(6) -0.2764(5) 0.104(3) Uani 1 1 d . . . H35 H 0.8087 0.3326 -0.3004 0.124 Uiso 1 1 calc R . . C36 C 0.7436(8) 0.2651(5) -0.1959(5) 0.086(2) Uani 1 1 d . . . H36 H 0.7307 0.3246 -0.1657 0.104 Uiso 1 1 calc R . . C37 C 0.8653(9) 0.1906(6) -0.4115(5) 0.106(3) Uani 1 1 d . . . H37A H 0.9133 0.2585 -0.4096 0.159 Uiso 1 1 calc R . . H37B H 0.7881 0.1752 -0.4723 0.159 Uiso 1 1 calc R . . H37C H 0.9279 0.1428 -0.4086 0.159 Uiso 1 1 calc R . . C38 C 0.9592(8) 0.1379(7) 0.3117(5) 0.102(3) Uani 1 1 d . . . H38A H 0.9501 0.2070 0.3298 0.123 Uiso 1 1 calc R . . H38B H 0.8669 0.1015 0.2748 0.123 Uiso 1 1 calc R . . Cl2 Cl 1.0577(4) 0.1423(2) 0.23566(19) 0.1680(15) Uani 1 1 d . . . Cl1 Cl 1.0220(2) 0.0816(2) 0.41688(14) 0.1093(7) Uani 1 1 d . . . Ir1 Ir 0.53668(2) 0.252725(15) 0.161884(13) 0.03764(7) Uani 1 1 d . . . N1 N 0.5244(4) 0.3028(3) 0.2957(3) 0.0397(9) Uani 1 1 d . . . N2 N 0.4233(4) 0.2973(3) 0.3433(3) 0.0440(10) Uani 1 1 d . . . N3 N 0.5860(4) 0.1981(3) 0.0439(3) 0.0424(10) Uani 1 1 d . . . N4 N 0.6109(4) 0.2396(3) -0.0396(3) 0.0452(10) Uani 1 1 d . . . O1 O 0.4664(4) 0.3864(3) 0.1038(2) 0.0458(9) Uani 1 1 d . . . O2 O 0.3309(4) 0.1723(3) 0.0978(2) 0.0480(9) Uani 1 1 d . . . O3 O 0.6275(4) 0.3751(3) 0.4472(2) 0.0486(9) Uani 1 1 d . . . O4 O 0.6791(4) 0.0882(3) -0.0204(2) 0.0476(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(3) 0.049(3) 0.043(3) -0.006(2) 0.019(2) 0.005(3) C2 0.042(3) 0.034(3) 0.050(3) -0.004(2) 0.025(2) 0.008(2) C3 0.047(3) 0.037(3) 0.040(3) -0.007(2) 0.014(2) 0.004(2) C4 0.044(3) 0.050(3) 0.058(3) -0.007(3) 0.023(3) 0.004(3) C5 0.041(3) 0.070(4) 0.062(3) -0.016(3) 0.015(3) -0.012(3) C6 0.041(3) 0.085(5) 0.050(3) -0.029(3) 0.018(3) -0.012(3) C7 0.063(4) 0.082(5) 0.086(4) -0.013(4) 0.046(4) -0.009(4) C8 0.041(3) 0.051(3) 0.040(3) -0.009(2) 0.015(2) 0.003(3) C9 0.045(3) 0.049(3) 0.046(3) -0.006(2) 0.020(3) 0.001(3) C10 0.053(4) 0.055(4) 0.042(3) 0.000(2) 0.024(3) 0.012(3) C11 0.059(4) 0.077(5) 0.057(3) -0.020(3) 0.031(3) -0.011(3) C12 0.065(4) 0.078(5) 0.073(4) -0.004(3) 0.039(4) 0.002(4) C13 0.091(5) 0.058(4) 0.053(3) 0.003(3) 0.040(4) 0.020(4) C14 0.119(7) 0.088(6) 0.077(4) 0.004(4) 0.068(4) 0.018(5) C15 0.086(5) 0.090(5) 0.049(3) -0.016(3) 0.030(3) 0.006(4) C16 0.053(4) 0.091(5) 0.054(3) -0.013(3) 0.021(3) -0.003(4) C17 0.058(4) 0.046(3) 0.040(3) -0.003(2) 0.024(3) 0.016(3) C18 0.043(4) 0.070(4) 0.048(3) 0.005(3) 0.014(3) 0.016(3) C19 0.037(3) 0.057(4) 0.041(3) -0.006(2) 0.018(2) 0.004(3) C20 0.072(5) 0.059(4) 0.064(3) 0.010(3) 0.025(3) 0.024(3) C21 0.047(4) 0.074(5) 0.072(4) -0.002(3) 0.012(3) -0.007(3) C22 0.068(4) 0.047(4) 0.073(4) 0.013(3) 0.018(3) 0.016(3) C23 0.062(4) 0.045(4) 0.066(3) -0.007(3) 0.012(3) 0.019(3) C24 0.043(3) 0.039(3) 0.054(3) -0.002(2) 0.012(2) 0.003(2) C25 0.034(3) 0.052(3) 0.032(2) -0.011(2) 0.008(2) 0.001(2) C26 0.045(3) 0.049(3) 0.045(3) -0.002(2) 0.011(2) 0.004(3) C27 0.047(4) 0.053(4) 0.060(3) 0.008(3) 0.011(3) 0.003(3) C28 0.089(6) 0.073(5) 0.079(4) 0.024(4) 0.023(4) 0.015(4) C29 0.047(3) 0.038(3) 0.041(3) -0.009(2) 0.010(2) 0.006(2) C30 0.046(3) 0.043(3) 0.045(3) -0.008(2) 0.015(2) 0.005(3) C31 0.050(4) 0.051(4) 0.049(3) -0.005(3) 0.019(3) 0.009(3) C32 0.058(4) 0.054(4) 0.057(3) -0.007(3) 0.019(3) 0.013(3) C33 0.078(5) 0.065(5) 0.063(4) -0.005(3) 0.034(3) 0.024(4) C34 0.078(5) 0.074(5) 0.068(4) -0.005(4) 0.040(4) 0.019(4) C35 0.175(9) 0.069(5) 0.115(6) 0.026(4) 0.103(6) 0.042(6) C36 0.129(7) 0.063(5) 0.097(5) -0.005(4) 0.076(5) 0.025(5) C37 0.147(8) 0.110(7) 0.095(5) 0.008(5) 0.085(6) 0.028(6) C38 0.070(6) 0.110(7) 0.119(6) 0.040(5) 0.017(4) 0.013(5) Cl2 0.288(4) 0.146(3) 0.162(2) 0.070(2) 0.159(3) 0.119(3) Cl1 0.1149(19) 0.133(2) 0.0912(12) 0.0225(12) 0.0406(12) 0.0380(16) Ir1 0.03689(12) 0.03474(11) 0.03878(11) -0.00692(8) 0.01157(8) 0.00251(8) N1 0.036(2) 0.038(2) 0.043(2) -0.0092(18) 0.0143(19) -0.0015(19) N2 0.040(3) 0.048(3) 0.046(2) -0.007(2) 0.021(2) 0.002(2) N3 0.043(3) 0.038(3) 0.039(2) -0.0103(18) 0.0070(19) 0.003(2) N4 0.050(3) 0.044(3) 0.042(2) -0.0077(19) 0.017(2) 0.004(2) O1 0.049(2) 0.043(2) 0.0447(18) -0.0046(15) 0.0139(17) 0.0086(18) O2 0.044(2) 0.044(2) 0.0526(19) -0.0057(16) 0.0145(17) 0.0034(18) O3 0.042(2) 0.062(3) 0.0407(18) -0.0135(16) 0.0173(16) -0.0016(18) O4 0.053(2) 0.043(2) 0.0494(19) -0.0092(17) 0.0218(17) 0.0098(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.360(7) . ? C1 C8 1.422(7) . ? C1 C2 1.447(6) . ? C2 C3 1.401(6) . ? C2 Ir1 1.986(5) . ? C3 C4 1.366(7) . ? C4 C5 1.417(6) . ? C4 C7 1.507(7) . ? C5 C6 1.370(7) . ? C8 N1 1.306(6) . ? C8 O3 1.353(5) . ? C9 N2 1.288(6) . ? C9 O3 1.369(6) . ? C9 C10 1.469(6) . ? C10 C11 1.352(8) . ? C10 C16 1.391(7) . ? C11 C12 1.388(6) . ? C12 C13 1.354(9) . ? C13 C15 1.365(9) . ? C13 C14 1.496(6) . ? C15 C16 1.387(7) . ? C17 O1 1.261(6) . ? C17 C18 1.387(8) . ? C17 C20 1.502(7) . ? C18 C19 1.384(7) . ? C19 O2 1.280(6) . ? C19 C21 1.495(8) . ? C22 C27 1.388(7) . ? C22 C23 1.379(7) . ? C23 C24 1.373(7) . ? C24 C29 1.450(7) . ? C24 C25 1.450(6) . ? C25 C26 1.396(7) . ? C25 Ir1 1.978(5) . ? C26 C27 1.386(7) . ? C27 C28 1.514(7) . ? C29 N3 1.287(6) . ? C29 O4 1.350(5) . ? C30 N4 1.293(5) . ? C30 O4 1.364(6) . ? C30 C31 1.458(6) . ? C31 C36 1.365(8) . ? C31 C32 1.389(7) . ? C32 C33 1.387(7) . ? C33 C34 1.348(9) . ? C34 C35 1.383(8) . ? C34 C37 1.525(7) . ? C35 C36 1.374(7) . ? C38 Cl1 1.680(7) . ? C38 Cl2 1.692(7) . ? Ir1 N3 2.029(4) . ? Ir1 N1 2.031(3) . ? Ir1 O1 2.116(3) . ? Ir1 O2 2.120(4) . ? N1 N2 1.401(5) . ? N3 N4 1.405(5) . ? 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 C6 C1 C8 126.3(4) . . ? C6 C1 C2 124.2(5) . . ? C8 C1 C2 109.5(5) . . ? C3 C2 C1 112.2(5) . . ? C3 C2 Ir1 132.0(3) . . ? C1 C2 Ir1 115.8(3) . . ? C4 C3 C2 125.0(4) . . ? C3 C4 C5 119.5(5) . . ? C3 C4 C7 120.9(5) . . ? C5 C4 C7 119.6(5) . . ? C6 C5 C4 118.6(5) . . ? C1 C6 C5 120.4(5) . . ? N1 C8 O3 110.2(4) . . ? N1 C8 C1 120.6(4) . . ? O3 C8 C1 129.2(4) . . ? N2 C9 O3 113.6(4) . . ? N2 C9 C10 127.9(5) . . ? O3 C9 C10 118.6(4) . . ? C11 C10 C16 118.8(5) . . ? C11 C10 C9 120.5(5) . . ? C16 C10 C9 120.8(5) . . ? C10 C11 C12 120.6(5) . . ? C13 C12 C11 121.9(6) . . ? C15 C13 C12 117.5(5) . . ? C15 C13 C14 121.3(6) . . ? C12 C13 C14 121.3(7) . . ? C13 C15 C16 122.1(6) . . ? C10 C16 C15 119.1(6) . . ? O1 C17 C18 126.5(5) . . ? O1 C17 C20 115.2(5) . . ? C18 C17 C20 118.3(5) . . ? C19 C18 C17 128.8(5) . . ? O2 C19 C18 126.0(5) . . ? O2 C19 C21 115.0(5) . . ? C18 C19 C21 118.9(5) . . ? C27 C22 C23 119.4(5) . . ? C24 C23 C22 120.1(5) . . ? C23 C24 C29 127.5(5) . . ? C23 C24 C25 123.9(5) . . ? C29 C24 C25 108.6(4) . . ? C26 C25 C24 112.1(5) . . ? C26 C25 Ir1 131.3(4) . . ? C24 C25 Ir1 116.4(3) . . ? C27 C26 C25 125.1(5) . . ? C22 C27 C26 119.5(5) . . ? C22 C27 C28 119.8(5) . . ? C26 C27 C28 120.7(5) . . ? N3 C29 O4 110.9(4) . . ? N3 C29 C24 120.1(4) . . ? O4 C29 C24 128.7(4) . . ? N4 C30 O4 113.7(4) . . ? N4 C30 C31 128.0(5) . . ? O4 C30 C31 118.2(4) . . ? C36 C31 C32 119.2(5) . . ? C36 C31 C30 119.5(5) . . ? C32 C31 C30 121.3(5) . . ? C33 C32 C31 118.6(6) . . ? C34 C33 C32 122.8(5) . . ? C33 C34 C35 117.6(6) . . ? C33 C34 C37 122.4(6) . . ? C35 C34 C37 119.9(7) . . ? C36 C35 C34 121.1(7) . . ? C31 C36 C35 120.6(6) . . ? Cl1 C38 Cl2 114.7(4) . . ? C25 Ir1 C2 92.06(19) . . ? C25 Ir1 N3 79.92(17) . . ? C2 Ir1 N3 91.40(16) . . ? C25 Ir1 N1 93.47(16) . . ? C2 Ir1 N1 79.96(17) . . ? N3 Ir1 N1 168.97(15) . . ? C25 Ir1 O1 175.60(16) . . ? C2 Ir1 O1 92.09(16) . . ? N3 Ir1 O1 98.51(14) . . ? N1 Ir1 O1 88.71(13) . . ? C25 Ir1 O2 86.83(17) . . ? C2 Ir1 O2 178.17(16) . . ? N3 Ir1 O2 89.85(14) . . ? N1 Ir1 O2 98.64(14) . . ? O1 Ir1 O2 89.06(14) . . ? C8 N1 N2 108.7(4) . . ? C8 N1 Ir1 113.8(3) . . ? N2 N1 Ir1 137.4(3) . . ? C9 N2 N1 104.2(4) . . ? C29 N3 N4 108.8(4) . . ? C29 N3 Ir1 114.8(3) . . ? N4 N3 Ir1 135.1(3) . . ? C30 N4 N3 103.5(4) . . ? C17 O1 Ir1 124.7(4) . . ? C19 O2 Ir1 124.1(3) . . ? C8 O3 C9 103.4(4) . . ? C29 O4 C30 102.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.3(7) . . . . ? C8 C1 C2 C3 175.7(4) . . . . ? C6 C1 C2 Ir1 178.1(5) . . . . ? C8 C1 C2 Ir1 -4.0(5) . . . . ? C1 C2 C3 C4 0.7(7) . . . . ? Ir1 C2 C3 C4 -179.7(4) . . . . ? C2 C3 C4 C5 0.9(8) . . . . ? C2 C3 C4 C7 -179.5(5) . . . . ? C3 C4 C5 C6 -1.2(8) . . . . ? C7 C4 C5 C6 179.3(5) . . . . ? C8 C1 C6 C5 -175.4(5) . . . . ? C2 C1 C6 C5 2.2(9) . . . . ? C4 C5 C6 C1 -0.4(9) . . . . ? C6 C1 C8 N1 177.5(6) . . . . ? C2 C1 C8 N1 -0.4(7) . . . . ? C6 C1 C8 O3 -0.9(9) . . . . ? C2 C1 C8 O3 -178.9(5) . . . . ? N2 C9 C10 C11 3.9(8) . . . . ? O3 C9 C10 C11 -174.8(5) . . . . ? N2 C9 C10 C16 -177.6(6) . . . . ? O3 C9 C10 C16 3.8(7) . . . . ? C16 C10 C11 C12 -0.3(9) . . . . ? C9 C10 C11 C12 178.3(5) . . . . ? C10 C11 C12 C13 -2.1(9) . . . . ? C11 C12 C13 C15 4.2(9) . . . . ? C11 C12 C13 C14 -176.9(6) . . . . ? C12 C13 C15 C16 -4.1(9) . . . . ? C14 C13 C15 C16 177.0(6) . . . . ? C11 C10 C16 C15 0.4(9) . . . . ? C9 C10 C16 C15 -178.2(5) . . . . ? C13 C15 C16 C10 1.9(9) . . . . ? O1 C17 C18 C19 6.1(9) . . . . ? C20 C17 C18 C19 -172.8(4) . . . . ? C17 C18 C19 O2 -1.1(8) . . . . ? C17 C18 C19 C21 177.9(5) . . . . ? C27 C22 C23 C24 0.0(9) . . . . ? C22 C23 C24 C29 180.0(6) . . . . ? C22 C23 C24 C25 0.6(9) . . . . ? C23 C24 C25 C26 -0.6(7) . . . . ? C29 C24 C25 C26 179.9(4) . . . . ? C23 C24 C25 Ir1 -175.9(4) . . . . ? C29 C24 C25 Ir1 4.6(5) . . . . ? C24 C25 C26 C27 0.1(7) . . . . ? Ir1 C25 C26 C27 174.5(4) . . . . ? C23 C22 C27 C26 -0.5(9) . . . . ? C23 C22 C27 C28 177.8(6) . . . . ? C25 C26 C27 C22 0.4(8) . . . . ? C25 C26 C27 C28 -177.9(5) . . . . ? C23 C24 C29 N3 174.6(5) . . . . ? C25 C24 C29 N3 -5.9(7) . . . . ? C23 C24 C29 O4 -11.7(9) . . . . ? C25 C24 C29 O4 167.8(5) . . . . ? N4 C30 C31 C36 18.2(9) . . . . ? O4 C30 C31 C36 -159.8(6) . . . . ? N4 C30 C31 C32 -162.8(5) . . . . ? O4 C30 C31 C32 19.2(7) . . . . ? C36 C31 C32 C33 -0.8(9) . . . . ? C30 C31 C32 C33 -179.8(5) . . . . ? C31 C32 C33 C34 0.2(9) . . . . ? C32 C33 C34 C35 0.3(11) . . . . ? C32 C33 C34 C37 180.0(6) . . . . ? C33 C34 C35 C36 -0.1(12) . . . . ? C37 C34 C35 C36 -179.8(7) . . . . ? C32 C31 C36 C35 1.0(11) . . . . ? C30 C31 C36 C35 -180.0(6) . . . . ? C34 C35 C36 C31 -0.6(12) . . . . ? C26 C25 Ir1 C2 92.6(5) . . . . ? C24 C25 Ir1 C2 -93.2(4) . . . . ? C26 C25 Ir1 N3 -176.3(5) . . . . ? C24 C25 Ir1 N3 -2.2(4) . . . . ? C26 C25 Ir1 N1 12.6(5) . . . . ? C24 C25 Ir1 N1 -173.3(4) . . . . ? C26 C25 Ir1 O1 -106.9(19) . . . . ? C24 C25 Ir1 O1 67(2) . . . . ? C26 C25 Ir1 O2 -85.9(5) . . . . ? C24 C25 Ir1 O2 88.3(4) . . . . ? C3 C2 Ir1 C25 92.2(5) . . . . ? C1 C2 Ir1 C25 -88.3(4) . . . . ? C3 C2 Ir1 N3 12.2(5) . . . . ? C1 C2 Ir1 N3 -168.2(4) . . . . ? C3 C2 Ir1 N1 -174.7(5) . . . . ? C1 C2 Ir1 N1 4.9(3) . . . . ? C3 C2 Ir1 O1 -86.3(4) . . . . ? C1 C2 Ir1 O1 93.2(3) . . . . ? C3 C2 Ir1 O2 145(5) . . . . ? C1 C2 Ir1 O2 -35(5) . . . . ? O3 C8 N1 N2 0.0(5) . . . . ? C1 C8 N1 N2 -178.7(4) . . . . ? O3 C8 N1 Ir1 -176.9(3) . . . . ? C1 C8 N1 Ir1 4.4(6) . . . . ? C25 Ir1 N1 C8 86.5(4) . . . . ? C2 Ir1 N1 C8 -5.0(4) . . . . ? N3 Ir1 N1 C8 33.8(11) . . . . ? O1 Ir1 N1 C8 -97.3(4) . . . . ? O2 Ir1 N1 C8 173.8(4) . . . . ? C25 Ir1 N1 N2 -89.1(4) . . . . ? C2 Ir1 N1 N2 179.4(5) . . . . ? N3 Ir1 N1 N2 -141.8(8) . . . . ? O1 Ir1 N1 N2 87.1(4) . . . . ? O2 Ir1 N1 N2 -1.8(4) . . . . ? O3 C9 N2 N1 -0.6(6) . . . . ? C10 C9 N2 N1 -179.4(5) . . . . ? C8 N1 N2 C9 0.4(5) . . . . ? Ir1 N1 N2 C9 176.1(4) . . . . ? O4 C29 N3 N4 -1.2(5) . . . . ? C24 C29 N3 N4 173.6(4) . . . . ? O4 C29 N3 Ir1 -170.3(3) . . . . ? C24 C29 N3 Ir1 4.4(6) . . . . ? C25 Ir1 N3 C29 -1.2(4) . . . . ? C2 Ir1 N3 C29 90.7(4) . . . . ? N1 Ir1 N3 C29 52.6(10) . . . . ? O1 Ir1 N3 C29 -177.0(4) . . . . ? O2 Ir1 N3 C29 -88.0(4) . . . . ? C25 Ir1 N3 N4 -166.5(5) . . . . ? C2 Ir1 N3 N4 -74.7(4) . . . . ? N1 Ir1 N3 N4 -112.8(9) . . . . ? O1 Ir1 N3 N4 17.6(5) . . . . ? O2 Ir1 N3 N4 106.7(4) . . . . ? O4 C30 N4 N3 -0.4(5) . . . . ? C31 C30 N4 N3 -178.4(5) . . . . ? C29 N3 N4 C30 0.9(5) . . . . ? Ir1 N3 N4 C30 166.9(4) . . . . ? C18 C17 O1 Ir1 -0.6(7) . . . . ? C20 C17 O1 Ir1 178.3(3) . . . . ? C25 Ir1 O1 C17 16(2) . . . . ? C2 Ir1 O1 C17 176.2(4) . . . . ? N3 Ir1 O1 C17 84.5(4) . . . . ? N1 Ir1 O1 C17 -103.9(4) . . . . ? O2 Ir1 O1 C17 -5.2(3) . . . . ? C18 C19 O2 Ir1 -7.9(6) . . . . ? C21 C19 O2 Ir1 173.0(3) . . . . ? C25 Ir1 O2 C19 -169.2(3) . . . . ? C2 Ir1 O2 C19 138(5) . . . . ? N3 Ir1 O2 C19 -89.3(3) . . . . ? N1 Ir1 O2 C19 97.8(3) . . . . ? O1 Ir1 O2 C19 9.2(3) . . . . ? N1 C8 O3 C9 -0.4(5) . . . . ? C1 C8 O3 C9 178.3(5) . . . . ? N2 C9 O3 C8 0.6(6) . . . . ? C10 C9 O3 C8 179.5(4) . . . . ? N3 C29 O4 C30 0.9(5) . . . . ? C24 C29 O4 C30 -173.3(5) . . . . ? N4 C30 O4 C29 -0.3(5) . . . . ? C31 C30 O4 C29 178.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.515 _refine_diff_density_min -1.722 _refine_diff_density_rms 0.112 end data_complex 3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2,5-di-p-tolyl-1,3,4-oxadiazolyl-C2,N)iridium(O,O¡¯ -diethyldithiophosphate) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H36 Ir N4 O4 P S2' _chemical_formula_weight 875.98 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' 'P' 'P' 0.1023 0.0942 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.943(2) _cell_length_b 11.978(2) _cell_length_c 13.793(3) _cell_angle_alpha 70.35(3) _cell_angle_beta 75.84(3) _cell_angle_gamma 89.60(3) _cell_volume 1795.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 3.923 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6504 _exptl_absorpt_correction_T_max 0.7443 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8129 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8129 _reflns_number_gt 7082 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0523P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8129 _refine_ls_number_parameters 448 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0752 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3374(3) 1.0090(4) 0.0611(3) 0.0387(8) Uani 1 1 d . . . C2 C 0.3213(3) 1.0526(4) 0.1469(3) 0.0388(8) Uani 1 1 d . . . C3 C 0.3603(4) 1.1723(4) 0.1190(4) 0.0517(11) Uani 1 1 d . . . H3 H 0.3508 1.2055 0.1722 0.062 Uiso 1 1 calc R . . C4 C 0.4121(4) 1.2419(4) 0.0156(4) 0.0554(11) Uani 1 1 d . . . C5 C 0.4255(4) 1.1956(4) -0.0662(4) 0.0543(11) Uani 1 1 d . . . H5 H 0.4592 1.2436 -0.1362 0.065 Uiso 1 1 calc R . . C6 C 0.3891(4) 1.0787(4) -0.0435(3) 0.0442(9) Uani 1 1 d . . . H6 H 0.3990 1.0469 -0.0977 0.053 Uiso 1 1 calc R . . C7 C 0.4547(6) 1.3699(5) -0.0099(6) 0.086(2) Uani 1 1 d . . . H7A H 0.4380 1.3885 0.0544 0.130 Uiso 1 1 calc R . . H7B H 0.4162 1.4216 -0.0591 0.130 Uiso 1 1 calc R . . H7C H 0.5368 1.3807 -0.0412 0.130 Uiso 1 1 calc R . . C8 C 0.2989(3) 0.8861(3) 0.1001(3) 0.0381(8) Uani 1 1 d . . . C9 C 0.2353(4) 0.7093(4) 0.1267(3) 0.0437(9) Uani 1 1 d . . . C10 C 0.2033(4) 0.6075(4) 0.1002(4) 0.0494(10) Uani 1 1 d . . . C11 C 0.2066(6) 0.6189(4) -0.0030(4) 0.0654(14) Uani 1 1 d . . . H11 H 0.2314 0.6912 -0.0581 0.078 Uiso 1 1 calc R . . C12 C 0.1721(6) 0.5204(5) -0.0235(4) 0.0724(16) Uani 1 1 d . . . H12 H 0.1737 0.5279 -0.0932 0.087 Uiso 1 1 calc R . . C13 C 0.1357(5) 0.4123(4) 0.0557(4) 0.0601(12) Uani 1 1 d . . . C14 C 0.1310(6) 0.4035(5) 0.1584(5) 0.0716(15) Uani 1 1 d . . . H14 H 0.1045 0.3316 0.2135 0.086 Uiso 1 1 calc R . . C15 C 0.1653(5) 0.5000(4) 0.1811(4) 0.0665(14) Uani 1 1 d . . . H15 H 0.1626 0.4924 0.2510 0.080 Uiso 1 1 calc R . . C16 C 0.0983(6) 0.3058(5) 0.0329(5) 0.0834(19) Uani 1 1 d . . . H16A H 0.0765 0.3320 -0.0332 0.125 Uiso 1 1 calc R . . H16B H 0.0334 0.2615 0.0894 0.125 Uiso 1 1 calc R . . H16C H 0.1613 0.2560 0.0281 0.125 Uiso 1 1 calc R . . C17 C 0.0357(3) 1.0509(3) 0.3203(3) 0.0372(8) Uani 1 1 d . . . C18 C 0.0906(3) 0.9718(3) 0.2714(3) 0.0342(8) Uani 1 1 d . . . C19 C 0.0293(4) 0.9372(4) 0.2100(3) 0.0426(9) Uani 1 1 d . . . H19 H 0.0606 0.8838 0.1770 0.051 Uiso 1 1 calc R . . C20 C -0.0752(4) 0.9791(4) 0.1967(3) 0.0488(10) Uani 1 1 d . . . C21 C -0.1268(4) 1.0539(5) 0.2487(4) 0.0572(12) Uani 1 1 d . . . H21 H -0.1993 1.0791 0.2421 0.069 Uiso 1 1 calc R . . C22 C -0.0712(4) 1.0914(4) 0.3105(4) 0.0502(10) Uani 1 1 d . . . H22 H -0.1050 1.1427 0.3449 0.060 Uiso 1 1 calc R . . C23 C -0.1352(5) 0.9417(6) 0.1264(5) 0.0723(16) Uani 1 1 d . . . H23A H -0.1353 1.0090 0.0642 0.108 Uiso 1 1 calc R . . H23B H -0.2136 0.9117 0.1651 0.108 Uiso 1 1 calc R . . H23C H -0.0948 0.8806 0.1053 0.108 Uiso 1 1 calc R . . C24 C 0.1086(3) 1.0867(3) 0.3743(3) 0.0373(8) Uani 1 1 d . . . C25 C 0.1846(3) 1.1630(4) 0.4642(3) 0.0412(9) Uani 1 1 d . . . C26 C 0.1881(4) 1.2350(4) 0.5297(3) 0.0471(10) Uani 1 1 d . . . C27 C 0.1004(4) 1.3089(4) 0.5457(4) 0.0598(12) Uani 1 1 d . . . H27 H 0.0396 1.3137 0.5136 0.072 Uiso 1 1 calc R . . C28 C 0.1046(5) 1.3755(5) 0.6103(5) 0.0699(15) Uani 1 1 d . . . H28 H 0.0451 1.4234 0.6224 0.084 Uiso 1 1 calc R . . C29 C 0.1942(5) 1.3719(5) 0.6561(4) 0.0654(14) Uani 1 1 d . . . C30 C 0.2793(5) 1.2982(5) 0.6410(4) 0.0666(14) Uani 1 1 d . . . H30 H 0.3396 1.2944 0.6735 0.080 Uiso 1 1 calc R . . C31 C 0.2780(4) 1.2286(5) 0.5782(4) 0.0571(12) Uani 1 1 d . . . H31 H 0.3366 1.1786 0.5689 0.068 Uiso 1 1 calc R . . C32 C 0.1981(6) 1.4484(6) 0.7247(5) 0.095(2) Uani 1 1 d . . . H32A H 0.2309 1.5271 0.6797 0.142 Uiso 1 1 calc R . . H32B H 0.2449 1.4137 0.7730 0.142 Uiso 1 1 calc R . . H32C H 0.1209 1.4522 0.7645 0.142 Uiso 1 1 calc R . . C33 C 0.4042(6) 0.8322(5) 0.5972(4) 0.0741(16) Uani 1 1 d . . . H33A H 0.4647 0.8942 0.5515 0.089 Uiso 1 1 calc R . . H33B H 0.3302 0.8665 0.6004 0.089 Uiso 1 1 calc R . . C34 C 0.4223(8) 0.7850(8) 0.7029(5) 0.106(3) Uani 1 1 d . . . H34A H 0.3567 0.7319 0.7502 0.159 Uiso 1 1 calc R . . H34B H 0.4314 0.8492 0.7280 0.159 Uiso 1 1 calc R . . H34C H 0.4908 0.7425 0.7007 0.159 Uiso 1 1 calc R . . C35 C 0.3652(7) 0.5687(7) 0.3928(8) 0.110(3) Uani 1 1 d . . . H35A H 0.3486 0.6329 0.3342 0.132 Uiso 1 1 calc R A 1 H35B H 0.2928 0.5206 0.4320 0.132 Uiso 1 1 calc R A 1 C36 C 0.4401(7) 0.4979(6) 0.3482(5) 0.091(2) Uani 1 1 d . B . H36A H 0.5139 0.5419 0.3108 0.137 Uiso 1 1 calc R . . H36B H 0.4076 0.4758 0.2995 0.137 Uiso 1 1 calc R . . H36C H 0.4501 0.4276 0.4038 0.137 Uiso 1 1 calc R . . Ir1 Ir 0.249843(12) 0.931877(13) 0.293806(11) 0.03637(6) Uani 1 1 d . . . N1 N 0.2628(3) 0.8300(3) 0.2019(3) 0.0411(7) Uani 1 1 d . . . N2 N 0.2210(3) 0.7148(3) 0.2206(3) 0.0477(9) Uani 1 1 d . . . N3 N 0.2108(3) 1.0488(3) 0.3722(3) 0.0402(7) Uani 1 1 d . . . N4 N 0.2614(3) 1.0985(3) 0.4319(3) 0.0457(8) Uani 1 1 d . . . O1 O 0.2851(3) 0.8138(2) 0.0462(2) 0.0428(6) Uani 1 1 d . . . O2 O 0.0863(2) 1.1606(2) 0.4306(2) 0.0418(6) Uani 1 1 d . . . O3 O 0.4060(3) 0.7368(3) 0.5540(3) 0.0622(9) Uani 1 1 d . B . O4 O 0.3953(6) 0.6177(6) 0.4569(5) 0.0498(15) Uani 0.60 1 d P B 1 O4' O 0.4235(9) 0.6677(10) 0.3957(11) 0.070(3) Uani 0.40 1 d P B 2 P1 P 0.36412(12) 0.75390(12) 0.45071(11) 0.0557(3) Uani 1 1 d . . . S1 S 0.19473(10) 0.76547(11) 0.46995(9) 0.0499(3) Uani 1 1 d . B . S2 S 0.44338(11) 0.89424(16) 0.32844(10) 0.0680(4) Uani 1 1 d . B . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(2) 0.048(2) 0.0392(19) -0.0186(17) -0.0140(16) 0.0080(16) C2 0.034(2) 0.045(2) 0.044(2) -0.0197(17) -0.0170(16) 0.0050(16) C3 0.045(2) 0.059(3) 0.061(3) -0.032(2) -0.017(2) 0.003(2) C4 0.044(2) 0.051(3) 0.068(3) -0.020(2) -0.010(2) -0.004(2) C5 0.043(2) 0.064(3) 0.050(2) -0.015(2) -0.009(2) -0.002(2) C6 0.041(2) 0.055(2) 0.041(2) -0.0189(19) -0.0144(17) 0.0054(18) C7 0.078(4) 0.063(4) 0.109(5) -0.034(3) -0.001(4) -0.019(3) C8 0.040(2) 0.046(2) 0.0367(19) -0.0213(17) -0.0170(16) 0.0131(17) C9 0.054(3) 0.041(2) 0.040(2) -0.0171(17) -0.0143(18) 0.0143(18) C10 0.060(3) 0.046(2) 0.049(2) -0.024(2) -0.014(2) 0.012(2) C11 0.104(4) 0.045(3) 0.049(3) -0.020(2) -0.017(3) -0.003(3) C12 0.103(5) 0.070(4) 0.057(3) -0.034(3) -0.025(3) -0.004(3) C13 0.069(3) 0.049(3) 0.069(3) -0.027(2) -0.020(3) 0.000(2) C14 0.099(5) 0.051(3) 0.062(3) -0.015(2) -0.021(3) -0.006(3) C15 0.100(4) 0.052(3) 0.050(3) -0.021(2) -0.019(3) 0.003(3) C16 0.107(5) 0.065(4) 0.092(4) -0.040(3) -0.032(4) -0.008(3) C17 0.035(2) 0.043(2) 0.041(2) -0.0196(17) -0.0161(16) 0.0062(15) C18 0.0350(19) 0.0371(19) 0.0347(18) -0.0163(15) -0.0109(15) 0.0019(15) C19 0.042(2) 0.054(2) 0.041(2) -0.0237(19) -0.0193(17) 0.0054(18) C20 0.045(2) 0.061(3) 0.045(2) -0.019(2) -0.0191(19) -0.001(2) C21 0.039(2) 0.077(3) 0.067(3) -0.029(3) -0.028(2) 0.016(2) C22 0.042(2) 0.060(3) 0.056(3) -0.027(2) -0.017(2) 0.015(2) C23 0.062(3) 0.104(5) 0.074(3) -0.045(3) -0.039(3) 0.005(3) C24 0.038(2) 0.042(2) 0.0372(19) -0.0200(16) -0.0097(16) 0.0050(16) C25 0.038(2) 0.051(2) 0.040(2) -0.0233(18) -0.0098(17) -0.0016(17) C26 0.043(2) 0.057(3) 0.047(2) -0.029(2) -0.0049(19) -0.0037(19) C27 0.055(3) 0.067(3) 0.074(3) -0.045(3) -0.018(2) 0.006(2) C28 0.066(3) 0.075(4) 0.086(4) -0.056(3) -0.011(3) 0.008(3) C29 0.069(3) 0.081(4) 0.057(3) -0.046(3) -0.002(2) -0.015(3) C30 0.064(3) 0.090(4) 0.062(3) -0.045(3) -0.018(3) -0.007(3) C31 0.053(3) 0.074(3) 0.059(3) -0.040(3) -0.017(2) 0.004(2) C32 0.113(5) 0.106(5) 0.086(4) -0.074(4) -0.005(4) -0.020(4) C33 0.103(5) 0.072(4) 0.065(3) -0.036(3) -0.036(3) 0.016(3) C34 0.139(7) 0.131(7) 0.073(4) -0.050(4) -0.051(5) 0.028(5) C35 0.095(5) 0.085(5) 0.185(9) -0.086(6) -0.045(6) 0.027(4) C36 0.135(6) 0.071(4) 0.085(4) -0.044(4) -0.036(4) 0.028(4) Ir1 0.03720(10) 0.04649(10) 0.03531(9) -0.02166(7) -0.01668(6) 0.01256(6) N1 0.050(2) 0.0422(18) 0.0379(17) -0.0171(14) -0.0186(15) 0.0141(15) N2 0.066(2) 0.0418(19) 0.0404(18) -0.0186(15) -0.0173(17) 0.0153(17) N3 0.0368(18) 0.055(2) 0.0414(17) -0.0281(16) -0.0166(14) 0.0086(15) N4 0.0406(19) 0.063(2) 0.0474(19) -0.0337(18) -0.0148(16) 0.0027(16) O1 0.0527(17) 0.0473(16) 0.0358(13) -0.0218(12) -0.0141(12) 0.0084(13) O2 0.0392(15) 0.0489(16) 0.0502(16) -0.0305(13) -0.0157(12) 0.0068(12) O3 0.082(2) 0.0563(19) 0.068(2) -0.0254(17) -0.0498(19) 0.0221(17) O4 0.065(4) 0.045(3) 0.045(3) -0.013(3) -0.029(3) 0.023(3) O4' 0.057(6) 0.061(7) 0.118(10) -0.062(7) -0.027(7) 0.016(5) P1 0.0587(7) 0.0705(8) 0.0645(7) -0.0426(7) -0.0374(6) 0.0325(6) S1 0.0508(6) 0.0592(7) 0.0429(5) -0.0189(5) -0.0162(5) 0.0159(5) S2 0.0401(6) 0.1197(12) 0.0455(6) -0.0267(7) -0.0165(5) 0.0269(7) _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 C6 1.386(6) . ? C1 C2 1.419(5) . ? C1 C8 1.422(6) . ? C2 C3 1.403(6) . ? C2 Ir1 2.032(4) . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C4 C5 1.392(7) . ? C4 C7 1.514(7) . ? C5 C6 1.377(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.296(5) . ? C8 O1 1.351(4) . ? C9 N2 1.288(5) . ? C9 O1 1.380(5) . ? C9 C10 1.463(6) . ? C10 C11 1.375(6) . ? C10 C15 1.379(7) . ? C11 C12 1.390(7) . ? C11 H11 0.9300 . ? C12 C13 1.372(8) . ? C12 H12 0.9300 . ? C13 C14 1.371(7) . ? C13 C16 1.508(7) . ? C14 C15 1.384(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.384(6) . ? C17 C18 1.410(5) . ? C17 C24 1.426(5) . ? C18 C19 1.403(5) . ? C18 Ir1 2.029(4) . ? C19 C20 1.372(6) . ? C19 H19 0.9300 . ? C20 C21 1.380(6) . ? C20 C23 1.514(6) . ? C21 C22 1.382(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N3 1.296(5) . ? C24 O2 1.348(4) . ? C25 N4 1.287(5) . ? C25 O2 1.367(5) . ? C25 C26 1.450(5) . ? C26 C31 1.387(7) . ? C26 C27 1.391(6) . ? C27 C28 1.390(6) . ? C27 H27 0.9300 . ? C28 C29 1.363(8) . ? C28 H28 0.9300 . ? C29 C30 1.365(8) . ? C29 C32 1.530(6) . ? C30 C31 1.393(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.445(8) . ? C33 O3 1.453(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 O4 1.328(9) . ? C35 O4' 1.396(12) . ? C35 C36 1.403(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? Ir1 N1 2.015(3) . ? Ir1 N3 2.028(3) . ? Ir1 S2 2.4809(13) . ? Ir1 S1 2.5076(16) . ? N1 N2 1.389(5) . ? N3 N4 1.406(4) . ? O3 P1 1.573(3) . ? O4 P1 1.650(6) . ? O4' P1 1.548(9) . ? P1 S2 1.975(2) . ? P1 S1 1.9851(18) . ? 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 C6 C1 C2 122.7(4) . . ? C6 C1 C8 127.1(4) . . ? C2 C1 C8 110.1(3) . . ? C3 C2 C1 115.6(4) . . ? C3 C2 Ir1 128.9(3) . . ? C1 C2 Ir1 115.5(3) . . ? C4 C3 C2 122.2(4) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 C7 120.0(5) . . ? C5 C4 C7 119.6(5) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.1(4) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 O1 110.3(4) . . ? N1 C8 C1 119.8(3) . . ? O1 C8 C1 129.7(3) . . ? N2 C9 O1 113.3(4) . . ? N2 C9 C10 126.9(4) . . ? O1 C9 C10 119.8(3) . . ? C11 C10 C15 119.9(4) . . ? C11 C10 C9 121.0(4) . . ? C15 C10 C9 119.1(4) . . ? C10 C11 C12 118.7(5) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 122.1(5) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C14 C13 C12 118.2(4) . . ? C14 C13 C16 119.9(5) . . ? C12 C13 C16 121.8(5) . . ? C13 C14 C15 120.9(5) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 120.1(5) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 123.3(4) . . ? C22 C17 C24 126.1(4) . . ? C18 C17 C24 110.4(3) . . ? C19 C18 C17 115.0(3) . . ? C19 C18 Ir1 129.7(3) . . ? C17 C18 Ir1 115.3(3) . . ? C20 C19 C18 122.6(4) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C21 120.2(4) . . ? C19 C20 C23 120.1(4) . . ? C21 C20 C23 119.8(4) . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 118.6(4) . . ? C21 C22 H22 120.7 . . ? C17 C22 H22 120.7 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 O2 111.2(3) . . ? N3 C24 C17 120.8(3) . . ? O2 C24 C17 128.0(3) . . ? N4 C25 O2 113.2(3) . . ? N4 C25 C26 129.6(4) . . ? O2 C25 C26 117.2(4) . . ? C31 C26 C27 119.8(4) . . ? C31 C26 C25 120.0(4) . . ? C27 C26 C25 120.2(4) . . ? C28 C27 C26 119.1(5) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C29 C28 C27 121.4(5) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C28 C29 C30 119.1(4) . . ? C28 C29 C32 120.3(6) . . ? C30 C29 C32 120.6(5) . . ? C29 C30 C31 121.6(5) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C26 C31 C30 118.9(5) . . ? C26 C31 H31 120.5 . . ? C30 C31 H31 120.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 O3 109.2(5) . . ? C34 C33 H33A 109.8 . . ? O3 C33 H33A 109.8 . . ? C34 C33 H33B 109.8 . . ? O3 C33 H33B 109.8 . . ? H33A C33 H33B 108.3 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O4 C35 O4' 35.9(5) . . ? O4 C35 C36 120.7(7) . . ? O4' C35 C36 112.8(8) . . ? O4 C35 H35A 107.1 . . ? O4' C35 H35A 77.6 . . ? C36 C35 H35A 107.1 . . ? O4 C35 H35B 107.1 . . ? O4' C35 H35B 136.5 . . ? C36 C35 H35B 107.1 . . ? H35A C35 H35B 106.8 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N1 Ir1 N3 168.32(13) . . ? N1 Ir1 C18 89.54(14) . . ? N3 Ir1 C18 79.34(14) . . ? N1 Ir1 C2 78.67(14) . . ? N3 Ir1 C2 97.42(15) . . ? C18 Ir1 C2 88.88(15) . . ? N1 Ir1 S2 94.82(11) . . ? N3 Ir1 S2 96.28(10) . . ? C18 Ir1 S2 175.62(10) . . ? C2 Ir1 S2 91.52(12) . . ? N1 Ir1 S1 96.79(10) . . ? N3 Ir1 S1 88.75(11) . . ? C18 Ir1 S1 100.31(12) . . ? C2 Ir1 S1 169.78(11) . . ? S2 Ir1 S1 79.66(6) . . ? C8 N1 N2 109.5(3) . . ? C8 N1 Ir1 115.6(3) . . ? N2 N1 Ir1 133.6(3) . . ? C9 N2 N1 104.0(3) . . ? C24 N3 N4 107.8(3) . . ? C24 N3 Ir1 114.1(2) . . ? N4 N3 Ir1 138.0(3) . . ? C25 N4 N3 104.6(3) . . ? C8 O1 C9 102.8(3) . . ? C24 O2 C25 103.1(3) . . ? C33 O3 P1 121.1(3) . . ? C35 O4 P1 121.0(5) . . ? C35 O4' P1 123.7(8) . . ? O4' P1 O3 109.4(5) . . ? O4' P1 O4 30.3(5) . . ? O3 P1 O4 90.2(2) . . ? O4' P1 S2 91.8(5) . . ? O3 P1 S2 113.21(16) . . ? O4 P1 S2 121.5(2) . . ? O4' P1 S1 118.5(4) . . ? O3 P1 S1 114.28(17) . . ? O4 P1 S1 109.5(3) . . ? S2 P1 S1 107.58(8) . . ? P1 S1 Ir1 85.19(7) . . ? P1 S2 Ir1 86.13(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.6(6) . . . . ? C8 C1 C2 C3 177.6(4) . . . . ? C6 C1 C2 Ir1 -177.5(3) . . . . ? C8 C1 C2 Ir1 -0.4(4) . . . . ? C1 C2 C3 C4 -0.9(6) . . . . ? Ir1 C2 C3 C4 176.9(3) . . . . ? C2 C3 C4 C5 1.3(7) . . . . ? C2 C3 C4 C7 -178.8(5) . . . . ? C3 C4 C5 C6 -1.4(7) . . . . ? C7 C4 C5 C6 178.8(5) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C2 C1 C6 C5 -0.7(6) . . . . ? C8 C1 C6 C5 -177.2(4) . . . . ? C6 C1 C8 N1 173.0(4) . . . . ? C2 C1 C8 N1 -3.9(5) . . . . ? C6 C1 C8 O1 -12.2(7) . . . . ? C2 C1 C8 O1 170.9(4) . . . . ? N2 C9 C10 C11 169.7(5) . . . . ? O1 C9 C10 C11 -9.3(7) . . . . ? N2 C9 C10 C15 -7.8(7) . . . . ? O1 C9 C10 C15 173.1(4) . . . . ? C15 C10 C11 C12 -0.6(9) . . . . ? C9 C10 C11 C12 -178.1(5) . . . . ? C10 C11 C12 C13 -0.4(10) . . . . ? C11 C12 C13 C14 1.6(10) . . . . ? C11 C12 C13 C16 180.0(6) . . . . ? C12 C13 C14 C15 -1.8(9) . . . . ? C16 C13 C14 C15 179.8(6) . . . . ? C11 C10 C15 C14 0.3(9) . . . . ? C9 C10 C15 C14 178.0(5) . . . . ? C13 C14 C15 C10 0.9(9) . . . . ? C22 C17 C18 C19 0.8(6) . . . . ? C24 C17 C18 C19 -176.0(4) . . . . ? C22 C17 C18 Ir1 177.7(3) . . . . ? C24 C17 C18 Ir1 0.9(4) . . . . ? C17 C18 C19 C20 1.2(6) . . . . ? Ir1 C18 C19 C20 -175.1(3) . . . . ? C18 C19 C20 C21 -3.1(7) . . . . ? C18 C19 C20 C23 177.9(4) . . . . ? C19 C20 C21 C22 3.0(7) . . . . ? C23 C20 C21 C22 -178.1(5) . . . . ? C20 C21 C22 C17 -1.0(7) . . . . ? C18 C17 C22 C21 -0.9(7) . . . . ? C24 C17 C22 C21 175.3(4) . . . . ? C22 C17 C24 N3 -175.3(4) . . . . ? C18 C17 C24 N3 1.4(6) . . . . ? C22 C17 C24 O2 3.8(7) . . . . ? C18 C17 C24 O2 -179.5(4) . . . . ? N4 C25 C26 C31 -8.4(7) . . . . ? O2 C25 C26 C31 171.2(4) . . . . ? N4 C25 C26 C27 172.8(5) . . . . ? O2 C25 C26 C27 -7.6(6) . . . . ? C31 C26 C27 C28 0.1(8) . . . . ? C25 C26 C27 C28 178.9(5) . . . . ? C26 C27 C28 C29 1.5(9) . . . . ? C27 C28 C29 C30 -2.3(9) . . . . ? C27 C28 C29 C32 178.6(6) . . . . ? C28 C29 C30 C31 1.4(9) . . . . ? C32 C29 C30 C31 -179.5(5) . . . . ? C27 C26 C31 C30 -1.0(8) . . . . ? C25 C26 C31 C30 -179.8(5) . . . . ? C29 C30 C31 C26 0.2(8) . . . . ? C19 C18 Ir1 N1 -1.9(4) . . . . ? C17 C18 Ir1 N1 -178.3(3) . . . . ? C19 C18 Ir1 N3 174.5(4) . . . . ? C17 C18 Ir1 N3 -1.8(3) . . . . ? C19 C18 Ir1 C2 76.7(4) . . . . ? C17 C18 Ir1 C2 -99.6(3) . . . . ? C19 C18 Ir1 S2 172.0(12) . . . . ? C17 C18 Ir1 S2 -4.3(16) . . . . ? C19 C18 Ir1 S1 -98.8(4) . . . . ? C17 C18 Ir1 S1 84.9(3) . . . . ? C3 C2 Ir1 N1 -175.0(4) . . . . ? C1 C2 Ir1 N1 2.7(3) . . . . ? C3 C2 Ir1 N3 16.1(4) . . . . ? C1 C2 Ir1 N3 -166.1(3) . . . . ? C3 C2 Ir1 C18 95.2(4) . . . . ? C1 C2 Ir1 C18 -87.0(3) . . . . ? C3 C2 Ir1 S2 -80.4(4) . . . . ? C1 C2 Ir1 S2 97.3(3) . . . . ? C3 C2 Ir1 S1 -110.6(6) . . . . ? C1 C2 Ir1 S1 67.2(7) . . . . ? O1 C8 N1 N2 -0.7(5) . . . . ? C1 C8 N1 N2 175.1(3) . . . . ? O1 C8 N1 Ir1 -169.4(2) . . . . ? C1 C8 N1 Ir1 6.4(5) . . . . ? N3 Ir1 N1 C8 66.6(8) . . . . ? C18 Ir1 N1 C8 84.1(3) . . . . ? C2 Ir1 N1 C8 -4.8(3) . . . . ? S2 Ir1 N1 C8 -95.4(3) . . . . ? S1 Ir1 N1 C8 -175.6(3) . . . . ? N3 Ir1 N1 N2 -98.7(7) . . . . ? C18 Ir1 N1 N2 -81.1(4) . . . . ? C2 Ir1 N1 N2 -170.1(4) . . . . ? S2 Ir1 N1 N2 99.3(4) . . . . ? S1 Ir1 N1 N2 19.2(4) . . . . ? O1 C9 N2 N1 0.5(5) . . . . ? C10 C9 N2 N1 -178.6(4) . . . . ? C8 N1 N2 C9 0.1(5) . . . . ? Ir1 N1 N2 C9 166.0(3) . . . . ? O2 C24 N3 N4 0.8(5) . . . . ? C17 C24 N3 N4 -180.0(4) . . . . ? O2 C24 N3 Ir1 177.8(2) . . . . ? C17 C24 N3 Ir1 -2.9(5) . . . . ? N1 Ir1 N3 C24 20.4(8) . . . . ? C18 Ir1 N3 C24 2.5(3) . . . . ? C2 Ir1 N3 C24 90.0(3) . . . . ? S2 Ir1 N3 C24 -177.7(3) . . . . ? S1 Ir1 N3 C24 -98.2(3) . . . . ? N1 Ir1 N3 N4 -163.8(6) . . . . ? C18 Ir1 N3 N4 178.3(4) . . . . ? C2 Ir1 N3 N4 -94.3(4) . . . . ? S2 Ir1 N3 N4 -1.9(4) . . . . ? S1 Ir1 N3 N4 77.6(4) . . . . ? O2 C25 N4 N3 -0.1(5) . . . . ? C26 C25 N4 N3 179.5(4) . . . . ? C24 N3 N4 C25 -0.4(5) . . . . ? Ir1 N3 N4 C25 -176.4(3) . . . . ? N1 C8 O1 C9 0.9(4) . . . . ? C1 C8 O1 C9 -174.3(4) . . . . ? N2 C9 O1 C8 -0.9(5) . . . . ? C10 C9 O1 C8 178.3(4) . . . . ? N3 C24 O2 C25 -0.8(4) . . . . ? C17 C24 O2 C25 -180.0(4) . . . . ? N4 C25 O2 C24 0.6(5) . . . . ? C26 C25 O2 C24 -179.1(4) . . . . ? C34 C33 O3 P1 167.5(5) . . . . ? O4' C35 O4 P1 53.7(8) . . . . ? C36 C35 O4 P1 140.6(7) . . . . ? O4 C35 O4' P1 -62.2(11) . . . . ? C36 C35 O4' P1 -173.7(9) . . . . ? C35 O4' P1 O3 109.5(11) . . . . ? C35 O4' P1 O4 55.8(11) . . . . ? C35 O4' P1 S2 -135.1(12) . . . . ? C35 O4' P1 S1 -24.0(14) . . . . ? C33 O3 P1 O4' 154.9(6) . . . . ? C33 O3 P1 O4 178.9(5) . . . . ? C33 O3 P1 S2 54.2(4) . . . . ? C33 O3 P1 S1 -69.5(4) . . . . ? C35 O4 P1 O4' -57.6(10) . . . . ? C35 O4 P1 O3 171.8(7) . . . . ? C35 O4 P1 S2 -70.5(7) . . . . ? C35 O4 P1 S1 55.9(7) . . . . ? O4' P1 S1 Ir1 -91.8(6) . . . . ? O3 P1 S1 Ir1 136.91(15) . . . . ? O4 P1 S1 Ir1 -123.6(2) . . . . ? S2 P1 S1 Ir1 10.29(7) . . . . ? N1 Ir1 S1 P1 85.77(11) . . . . ? N3 Ir1 S1 P1 -104.54(10) . . . . ? C18 Ir1 S1 P1 176.53(11) . . . . ? C2 Ir1 S1 P1 22.8(6) . . . . ? S2 Ir1 S1 P1 -7.92(6) . . . . ? O4' P1 S2 Ir1 110.4(4) . . . . ? O3 P1 S2 Ir1 -137.64(15) . . . . ? O4 P1 S2 Ir1 116.8(3) . . . . ? S1 P1 S2 Ir1 -10.39(7) . . . . ? N1 Ir1 S2 P1 -88.09(11) . . . . ? N3 Ir1 S2 P1 95.52(12) . . . . ? C18 Ir1 S2 P1 98.0(14) . . . . ? C2 Ir1 S2 P1 -166.85(12) . . . . ? S1 Ir1 S2 P1 7.95(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.625 _refine_diff_density_min -1.824 _refine_diff_density_rms 0.253 end data_Complex 4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2,5-di-p-tolyl-1,3,4-oxadiazolyl-C2,N)iridium(N,N¡¯ -diethyldithiocarbamate) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H36 Ir N5 O2 S2' _chemical_formula_weight 847.03 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' '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 13.2095(18) _cell_length_b 16.274(2) _cell_length_c 19.153(3) _cell_angle_alpha 96.262(2) _cell_angle_beta 99.371(2) _cell_angle_gamma 102.316(2) _cell_volume 3924.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 5199 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 22.89 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 3.546 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.4159 _exptl_absorpt_correction_T_max 0.8712 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(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 27902 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 13664 _reflns_number_gt 10908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+137.1310P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13664 _refine_ls_number_parameters 877 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1037 _refine_ls_R_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.2555 _refine_ls_wR_factor_gt 0.2481 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.189 _refine_ls_shift/su_max 0.029 _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 0.37611(5) 0.23266(4) 0.04641(3) 0.0369(2) Uani 1 1 d . . . S1 S 0.4560(4) 0.3830(3) 0.0933(2) 0.0470(11) Uani 1 1 d . . . S2 S 0.3173(4) 0.3171(3) -0.0428(2) 0.0468(11) Uani 1 1 d . . . O1 O 0.1795(9) 0.2138(8) 0.1896(6) 0.048(3) Uani 1 1 d . . . O2 O 0.5549(10) 0.1089(8) -0.0595(7) 0.052(3) Uani 1 1 d . . . O3 O 0.5973(9) 0.9334(8) 0.5774(6) 0.042(3) Uani 1 1 d . . . O4 O 0.9475(10) 0.6089(8) 0.5881(7) 0.052(3) Uani 1 1 d . . . N1 N 0.1663(12) 0.2739(10) 0.0904(8) 0.048(4) Uani 1 1 d . . . N2 N 0.2554(11) 0.2386(8) 0.0988(7) 0.039(3) Uani 1 1 d . . . N3 N 0.4945(11) 0.2031(9) -0.0001(7) 0.041(3) Uani 1 1 d . . . N4 N 0.5977(12) 0.2421(10) -0.0039(8) 0.048(4) Uani 1 1 d . . . N5 N 0.3594(13) 0.4827(10) 0.0144(8) 0.051(4) Uani 1 1 d . . . N6 N 0.5425(11) 0.8193(10) 0.4931(9) 0.047(4) Uani 1 1 d . . . N7 N 0.6487(10) 0.8283(9) 0.5222(7) 0.037(3) Uani 1 1 d . . . N8 N 0.9633(11) 0.6913(9) 0.5023(9) 0.046(4) Uani 1 1 d . . . N9 N 0.8728(11) 0.6944(9) 0.5284(8) 0.041(3) Uani 1 1 d . . . N10 N 0.7007(14) 0.7151(10) 0.2863(8) 0.058(4) Uani 1 1 d . . . C1 C -0.248(2) 0.3439(17) 0.2241(16) 0.088(8) Uani 1 1 d . . . H1A H -0.2308 0.4023 0.2460 0.132 Uiso 1 1 calc R . . H1B H -0.2736 0.3082 0.2574 0.132 Uiso 1 1 calc R . . H1C H -0.3022 0.3358 0.1821 0.132 Uiso 1 1 calc R . . C2 C -0.1506(18) 0.3205(15) 0.2033(14) 0.068(6) Uani 1 1 d . . . C3 C -0.0866(17) 0.2827(15) 0.2469(13) 0.068(6) Uani 1 1 d . . . H3 H -0.1041 0.2706 0.2904 0.082 Uiso 1 1 calc R . . C4 C -0.127(3) 0.331(2) 0.1367(19) 0.112(12) Uani 1 1 d . . . H4 H -0.1710 0.3511 0.1036 0.135 Uiso 1 1 calc R . . C5 C 0.0018(16) 0.2622(15) 0.2288(10) 0.058(5) Uani 1 1 d . . . H5 H 0.0430 0.2368 0.2598 0.070 Uiso 1 1 calc R . . C6 C -0.035(3) 0.309(2) 0.1191(17) 0.120(13) Uani 1 1 d . . . H6 H -0.0186 0.3169 0.0744 0.144 Uiso 1 1 calc R . . C7 C 0.0295(15) 0.2789(13) 0.1659(11) 0.053(5) Uani 1 1 d . . . C8 C 0.1251(14) 0.2576(11) 0.1447(10) 0.042(4) Uani 1 1 d . . . C9 C 0.2603(14) 0.2052(11) 0.1564(9) 0.043(4) Uani 1 1 d . . . C10 C 0.3472(15) 0.1705(13) 0.1815(10) 0.050(5) Uani 1 1 d . . . C11 C 0.3632(19) 0.1364(16) 0.2442(11) 0.069(6) Uani 1 1 d . . . H11 H 0.3117 0.1278 0.2722 0.083 Uiso 1 1 calc R . . C12 C 0.4239(13) 0.1812(10) 0.1356(8) 0.036(4) Uani 1 1 d . . . C13 C 0.457(2) 0.1159(17) 0.2632(13) 0.080(8) Uani 1 1 d . . . H13 H 0.4694 0.0945 0.3061 0.096 Uiso 1 1 calc R . . C14 C 0.5144(15) 0.1573(12) 0.1588(10) 0.047(4) Uani 1 1 d . . . H14 H 0.5653 0.1629 0.1302 0.057 Uiso 1 1 calc R . . C15 C 0.537(2) 0.1246(16) 0.2231(12) 0.071(7) Uani 1 1 d . . . C16 C 0.641(2) 0.107(2) 0.2510(13) 0.102(10) Uani 1 1 d . . . H16A H 0.6635 0.1306 0.3006 0.153 Uiso 1 1 calc R . . H16B H 0.6922 0.1317 0.2244 0.153 Uiso 1 1 calc R . . H16C H 0.6343 0.0463 0.2458 0.153 Uiso 1 1 calc R . . C17 C 1.032(2) 0.201(2) -0.1238(19) 0.119(12) Uani 1 1 d . . . H17A H 1.0698 0.1647 -0.1000 0.178 Uiso 1 1 calc R . . H17B H 1.0722 0.2593 -0.1105 0.178 Uiso 1 1 calc R . . H17C H 1.0226 0.1857 -0.1747 0.178 Uiso 1 1 calc R . . C18 C 0.9286(19) 0.193(2) -0.1028(13) 0.081(8) Uani 1 1 d . . . C19 C 0.901(2) 0.266(2) -0.0748(18) 0.109(11) Uani 1 1 d . . . H19 H 0.9483 0.3189 -0.0702 0.131 Uiso 1 1 calc R . . C20 C 0.8547(19) 0.1197(19) -0.1090(15) 0.088(8) Uani 1 1 d . . . H20 H 0.8711 0.0697 -0.1267 0.105 Uiso 1 1 calc R . . C21 C 0.805(2) 0.263(2) -0.0539(17) 0.100(10) Uani 1 1 d . . . H21 H 0.7898 0.3127 -0.0350 0.120 Uiso 1 1 calc R . . C22 C 0.7560(17) 0.1135(16) -0.0907(13) 0.071(6) Uani 1 1 d . . . H22 H 0.7070 0.0614 -0.0988 0.085 Uiso 1 1 calc R . . C23 C 0.7324(16) 0.1864(15) -0.0603(13) 0.069(6) Uani 1 1 d . . . C24 C 0.6319(14) 0.1854(12) -0.0403(10) 0.047(4) Uani 1 1 d . . . C25 C 0.4736(13) 0.1257(12) -0.0324(9) 0.041(4) Uani 1 1 d . . . C26 C 0.3718(15) 0.0713(11) -0.0385(9) 0.043(4) Uani 1 1 d . . . C27 C 0.339(2) -0.0107(13) -0.0761(11) 0.066(6) Uani 1 1 d . . . H27 H 0.3869 -0.0372 -0.0938 0.079 Uiso 1 1 calc R . . C28 C 0.3055(14) 0.1130(10) -0.0080(9) 0.039(4) Uani 1 1 d . . . C29 C 0.234(2) -0.0525(16) -0.0869(13) 0.081(8) Uani 1 1 d . . . H29 H 0.2108 -0.1070 -0.1128 0.097 Uiso 1 1 calc R . . C30 C 0.1990(16) 0.0704(14) -0.0193(10) 0.061(6) Uani 1 1 d . . . H30 H 0.1514 0.0970 -0.0007 0.073 Uiso 1 1 calc R . . C31 C 0.1625(17) -0.0125(13) -0.0585(12) 0.063(6) Uani 1 1 d . . . C32 C 0.0482(18) -0.0551(18) -0.0735(17) 0.106(12) Uani 1 1 d . . . H32A H 0.0253 -0.0754 -0.1238 0.158 Uiso 1 1 calc R . . H32B H 0.0086 -0.0152 -0.0591 0.158 Uiso 1 1 calc R . . H32C H 0.0367 -0.1021 -0.0473 0.158 Uiso 1 1 calc R . . C33 C 0.3779(17) 0.4061(13) 0.0224(11) 0.057(6) Uani 1 1 d . . . C34 C 0.2846(18) 0.4972(14) -0.0426(12) 0.064(6) Uani 1 1 d . . . H34A H 0.2905 0.4647 -0.0868 0.077 Uiso 1 1 calc R . . H34B H 0.3025 0.5570 -0.0478 0.077 Uiso 1 1 calc R . . C35 C 0.170(2) 0.4736(19) -0.0327(19) 0.107(10) Uani 1 1 d . . . H35A H 0.1688 0.4641 0.0158 0.160 Uiso 1 1 calc R . . H35B H 0.1334 0.4227 -0.0648 0.160 Uiso 1 1 calc R . . H35C H 0.1370 0.5191 -0.0428 0.160 Uiso 1 1 calc R . . C36 C 0.4141(19) 0.5552(12) 0.0715(12) 0.064(6) Uani 1 1 d . . . H36A H 0.4817 0.5462 0.0934 0.077 Uiso 1 1 calc R . . H36B H 0.4270 0.6074 0.0509 0.077 Uiso 1 1 calc R . . C37 C 0.348(2) 0.5627(18) 0.1265(15) 0.096(9) Uani 1 1 d . . . H37A H 0.2782 0.5635 0.1037 0.145 Uiso 1 1 calc R . . H37B H 0.3787 0.6144 0.1592 0.145 Uiso 1 1 calc R . . H37C H 0.3452 0.5150 0.1521 0.145 Uiso 1 1 calc R . . C38 C 0.1009(15) 0.9481(16) 0.5010(13) 0.070(7) Uani 1 1 d . . . H38A H 0.0903 0.9742 0.5458 0.105 Uiso 1 1 calc R . . H38B H 0.0508 0.8944 0.4862 0.105 Uiso 1 1 calc R . . H38C H 0.0912 0.9846 0.4655 0.105 Uiso 1 1 calc R . . C39 C 0.2125(16) 0.9344(14) 0.5097(13) 0.059(5) Uani 1 1 d . . . C40 C 0.2930(16) 0.9837(14) 0.5586(11) 0.057(5) Uani 1 1 d . . . H40 H 0.2817 1.0283 0.5888 0.068 Uiso 1 1 calc R . . C41 C 0.2329(18) 0.8707(16) 0.469(2) 0.115(13) Uani 1 1 d . . . H41 H 0.1758 0.8333 0.4379 0.138 Uiso 1 1 calc R . . C42 C 0.3964(14) 0.9677(11) 0.5644(10) 0.042(4) Uani 1 1 d . . . H42 H 0.4526 1.0024 0.5977 0.051 Uiso 1 1 calc R . . C43 C 0.3322(17) 0.8554(15) 0.4677(15) 0.078(8) Uani 1 1 d . . . H43 H 0.3431 0.8159 0.4325 0.094 Uiso 1 1 calc R . . C44 C 0.4122(14) 0.9001(12) 0.5201(10) 0.045(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0424(4) 0.0343(4) 0.0349(4) 0.0042(3) 0.0135(3) 0.0065(3) Ir2 0.0364(4) 0.0420(4) 0.0360(4) 0.0078(3) 0.0118(3) 0.0165(3) S1 0.054(3) 0.039(2) 0.042(2) 0.0030(19) 0.006(2) 0.004(2) S2 0.056(3) 0.045(3) 0.035(2) 0.0061(19) 0.005(2) 0.005(2) S3 0.050(3) 0.044(2) 0.040(2) 0.0065(19) 0.013(2) 0.014(2) S4 0.052(3) 0.042(2) 0.043(2) 0.004(2) 0.012(2) 0.010(2) O1 0.043(7) 0.064(8) 0.045(7) 0.013(6) 0.017(6) 0.022(6) O2 0.049(8) 0.052(8) 0.061(8) 0.010(6) 0.024(6) 0.015(6) O3 0.035(6) 0.049(7) 0.044(7) -0.002(6) 0.007(5) 0.019(5) O4 0.051(8) 0.058(8) 0.061(8) 0.030(7) 0.015(6) 0.029(6) N1 0.050(9) 0.054(9) 0.043(9) 0.004(7) 0.019(7) 0.015(7) N2 0.053(9) 0.030(7) 0.036(7) -0.001(6) 0.017(6) 0.013(6) N3 0.049(9) 0.038(8) 0.038(8) 0.003(6) 0.020(7) 0.006(7) N4 0.046(9) 0.046(9) 0.054(9) 0.009(7) 0.014(7) 0.010(7) N5 0.069(11) 0.042(9) 0.049(9) 0.013(7) 0.014(8) 0.019(8) N6 0.035(8) 0.045(9) 0.064(10) 0.006(7) 0.016(7) 0.012(7) N7 0.034(7) 0.042(8) 0.039(8) 0.009(6) 0.002(6) 0.017(6) N8 0.039(8) 0.044(9) 0.063(10) 0.013(7) 0.018(7) 0.021(7) N9 0.042(8) 0.037(8) 0.050(9) 0.010(7) 0.014(7) 0.018(6) N10 0.073(12) 0.050(10) 0.040(9) -0.004(7) 0.010(8) -0.002(8) C1 0.071(17) 0.083(18) 0.11(2) -0.007(16) 0.027(15) 0.026(14) C2 0.058(14) 0.064(14) 0.086(17) 0.000(12) 0.019(12) 0.022(11) C3 0.058(13) 0.083(16) 0.063(14) 0.005(12) 0.025(11) 0.011(12) C4 0.11(2) 0.14(3) 0.13(3) 0.07(2) 0.06(2) 0.09(2) C5 0.056(12) 0.085(16) 0.044(11) 0.017(10) 0.021(9) 0.028(11) C6 0.13(3) 0.19(3) 0.11(2) 0.08(2) 0.09(2) 0.12(3) C7 0.050(11) 0.054(12) 0.063(13) 0.009(10) 0.018(10) 0.026(9) C8 0.042(10) 0.036(9) 0.046(10) 0.002(8) 0.012(8) 0.004(8) C9 0.052(11) 0.046(10) 0.043(10) 0.013(8) 0.025(8) 0.025(9) C10 0.056(12) 0.063(12) 0.040(10) 0.019(9) 0.020(9) 0.022(10) C11 0.078(16) 0.100(18) 0.049(12) 0.032(12) 0.032(11) 0.037(14) C12 0.048(10) 0.034(9) 0.031(8) 0.002(7) 0.017(7) 0.012(7) C13 0.102(19) 0.11(2) 0.063(14) 0.053(14) 0.042(14) 0.067(17) C14 0.052(11) 0.057(12) 0.043(10) 0.016(9) 0.025(9) 0.019(9) C15 0.086(17) 0.091(17) 0.053(13) 0.023(12) 0.016(12) 0.052(14) C16 0.10(2) 0.18(3) 0.054(14) 0.035(18) 0.025(14) 0.08(2) C17 0.064(18) 0.16(3) 0.13(3) 0.01(2) 0.044(18) 0.02(2) C18 0.053(14) 0.12(2) 0.060(14) 0.008(15) 0.014(11) 0.007(15) C19 0.070(18) 0.12(3) 0.13(3) 0.00(2) 0.053(18) 0.000(18) C20 0.051(14) 0.10(2) 0.10(2) -0.017(17) 0.025(13) 0.016(14) C21 0.063(16) 0.10(2) 0.13(3) -0.018(19) 0.051(17) 0.007(15) C22 0.043(12) 0.086(17) 0.089(17) 0.006(14) 0.030(11) 0.019(11) C23 0.036(11) 0.078(16) 0.091(17) 0.002(13) 0.034(11) 0.002(10) C24 0.037(10) 0.053(11) 0.057(11) 0.011(9) 0.019(8) 0.016(8) C25 0.037(9) 0.057(11) 0.036(9) 0.008(8) 0.013(7) 0.019(8) C26 0.057(11) 0.044(10) 0.035(9) 0.011(8) 0.016(8) 0.017(9) C27 0.102(19) 0.040(11) 0.055(13) 0.003(9) 0.018(12) 0.014(12) C28 0.046(10) 0.035(9) 0.032(8) -0.001(7) 0.009(7) 0.002(7) C29 0.10(2) 0.059(14) 0.068(15) -0.015(12) 0.030(14) 0.001(14) C30 0.050(12) 0.076(15) 0.046(11) -0.017(10) 0.011(9) 0.003(10) C31 0.064(13) 0.046(11) 0.073(14) -0.007(10) 0.030(11) -0.004(10) C32 0.053(14) 0.10(2) 0.13(3) -0.058(19) 0.037(15) -0.028(14) C33 0.075(14) 0.070(13) 0.058(12) 0.043(11) 0.046(11) 0.045(11) C34 0.074(15) 0.054(12) 0.071(14) 0.033(11) 0.014(12) 0.017(11) C35 0.08(2) 0.09(2) 0.14(3) 0.020(19) -0.001(19) 0.012(17) C36 0.082(16) 0.032(10) 0.079(15) 0.004(10) 0.028(13) 0.007(10) C37 0.12(2) 0.083(19) 0.09(2) -0.017(15) 0.041(18) 0.028(17) C38 0.040(11) 0.100(18) 0.094(17) 0.041(15) 0.031(11) 0.038(12) C39 0.044(11) 0.071(14) 0.077(15) 0.028(12) 0.026(11) 0.022(10) C40 0.062(13) 0.071(14) 0.055(12) 0.024(11) 0.015(10) 0.041(11) C41 0.040(13) 0.060(15) 0.24(4) -0.03(2) 0.056(18) 0.006(11) C42 0.041(10) 0.050(10) 0.047(10) 0.012(8) 0.009(8) 0.031(8) C43 0.049(13) 0.067(15) 0.11(2) -0.024(14) 0.004(13) 0.028(11) C44 0.047(10) 0.051(11) 0.047(10) 0.011(9) 0.013(8) 0.028(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N2 2.030(14) . ? Ir1 N3 2.038(14) . ? Ir1 C12 2.050(16) . ? Ir1 C28 2.052(16) . ? Ir1 S2 2.438(5) . ? Ir1 S1 2.453(5) . ? Ir2 N7 2.012(13) . ? Ir2 N9 2.034(13) . ? Ir2 C64 2.048(17) . ? Ir2 C49 2.052(19) . ? Ir2 S4 2.446(5) . ? Ir2 S3 2.452(4) . ? S1 C33 1.690(2) . ? S2 C33 1.706(2) . ? S3 C70 1.703(19) . ? S4 C70 1.711(18) . ? O1 C9 1.353(19) . ? O1 C8 1.38(2) . ? O2 C25 1.33(2) . ? O2 C24 1.40(2) . ? O3 C45 1.36(2) . ? O3 C46 1.376(18) . ? O4 C62 1.351(19) . ? O4 C61 1.38(2) . ? N1 C8 1.28(2) . ? N1 N2 1.41(2) . ? N2 C9 1.28(2) . ? N3 C25 1.29(2) . ? N3 N4 1.39(2) . ? N4 C24 1.30(2) . ? N5 C33 1.34(2) . ? N5 C34 1.42(3) . ? N5 C36 1.49(3) . ? N6 C45 1.31(2) . ? N6 N7 1.392(19) . ? N7 C46 1.34(2) . ? N8 C61 1.29(2) . ? N8 N9 1.377(19) . ? N9 C62 1.31(2) . ? N10 C70 1.36(2) . ? N10 C71 1.46(3) . ? N10 C73 1.49(3) . ? C1 C2 1.52(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.38(3) . ? C2 C4 1.38(4) . ? C3 C5 1.37(3) . ? C3 H3 0.9300 . ? C4 C6 1.41(3) . ? C4 H4 0.9300 . ? C5 C7 1.35(3) . ? C5 H5 0.9300 . ? C6 C7 1.34(3) . ? C6 H6 0.9300 . ? C7 C8 1.48(2) . ? C9 C10 1.42(2) . ? C10 C11 1.38(3) . ? C10 C12 1.44(2) . ? C11 C13 1.36(3) . ? C11 H11 0.9300 . ? C12 C14 1.36(2) . ? C13 C15 1.39(3) . ? C13 H13 0.9300 . ? C14 C15 1.41(3) . ? C14 H14 0.9300 . ? C15 C16 1.49(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.47(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C20 1.35(4) . ? C18 C19 1.40(4) . ? C19 C21 1.38(3) . ? C19 H19 0.9300 . ? C20 C22 1.39(3) . ? C20 H20 0.9300 . ? C21 C23 1.38(3) . ? C21 H21 0.9300 . ? C22 C23 1.38(3) . ? C22 H22 0.9300 . ? C23 C24 1.44(2) . ? C25 C26 1.42(2) . ? C26 C28 1.38(2) . ? C26 C27 1.39(3) . ? C27 C29 1.38(3) . ? C27 H27 0.9300 . ? C28 C30 1.40(3) . ? C29 C31 1.40(3) . ? C29 H29 0.9300 . ? C30 C31 1.41(3) . ? C30 H30 0.9300 . ? C31 C32 1.49(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C34 C35 1.52(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C37 1.48(3) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 C39 1.52(3) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 C41 1.33(3) . ? C39 C40 1.34(3) . ? C40 C42 1.43(2) . ? C40 H40 0.9300 . ? C41 C43 1.39(3) . ? C41 H41 0.9300 . ? C42 C44 1.39(2) . ? C42 H42 0.9300 . ? C43 C44 1.35(3) . ? C43 H43 0.9300 . ? C44 C45 1.45(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ir1 N3 168.5(5) . . ? N2 Ir1 C12 79.7(6) . . ? N3 Ir1 C12 91.7(6) . . ? N2 Ir1 C28 93.9(6) . . ? N3 Ir1 C28 78.3(6) . . ? C12 Ir1 C28 90.1(7) . . ? N2 Ir1 S2 93.6(4) . . ? N3 Ir1 S2 96.1(4) . . ? C12 Ir1 S2 168.8(4) . . ? C28 Ir1 S2 99.4(5) . . ? N2 Ir1 S1 89.4(4) . . ? N3 Ir1 S1 99.5(4) . . ? C12 Ir1 S1 98.6(5) . . ? C28 Ir1 S1 171.1(5) . . ? S2 Ir1 S1 72.17(16) . . ? N7 Ir2 N9 168.9(6) . . ? N7 Ir2 C64 92.4(6) . . ? N9 Ir2 C64 79.1(6) . . ? N7 Ir2 C49 79.4(6) . . ? N9 Ir2 C49 93.2(6) . . ? C64 Ir2 C49 89.0(6) . . ? N7 Ir2 S4 95.6(4) . . ? N9 Ir2 S4 92.9(4) . . ? C64 Ir2 S4 99.8(5) . . ? C49 Ir2 S4 170.0(4) . . ? N7 Ir2 S3 93.3(4) . . ? N9 Ir2 S3 96.2(4) . . ? C64 Ir2 S3 170.1(5) . . ? C49 Ir2 S3 100.0(4) . . ? S4 Ir2 S3 71.54(15) . . ? C33 S1 Ir1 86.9(8) . . ? C33 S2 Ir1 86.0(6) . . ? C70 S3 Ir2 87.2(6) . . ? C70 S4 Ir2 87.2(6) . . ? C9 O1 C8 102.1(13) . . ? C25 O2 C24 103.6(14) . . ? C45 O3 C46 104.3(13) . . ? C62 O4 C61 102.1(14) . . ? C8 N1 N2 104.0(15) . . ? C9 N2 N1 108.6(13) . . ? C9 N2 Ir1 114.7(12) . . ? N1 N2 Ir1 136.6(11) . . ? C25 N3 N4 108.1(14) . . ? C25 N3 Ir1 114.2(11) . . ? N4 N3 Ir1 137.6(11) . . ? C24 N4 N3 105.7(14) . . ? C33 N5 C34 123.9(18) . . ? C33 N5 C36 117.7(18) . . ? C34 N5 C36 118.2(17) . . ? C45 N6 N7 104.4(14) . . ? C46 N7 N6 109.3(13) . . ? C46 N7 Ir2 113.7(10) . . ? N6 N7 Ir2 136.8(11) . . ? C61 N8 N9 104.2(15) . . ? C62 N9 N8 109.2(14) . . ? C62 N9 Ir2 113.9(11) . . ? N8 N9 Ir2 136.7(11) . . ? C70 N10 C71 122.2(17) . . ? C70 N10 C73 119.9(16) . . ? C71 N10 C73 117.8(17) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C4 117(2) . . ? C3 C2 C1 122(2) . . ? C4 C2 C1 121(2) . . ? C5 C3 C2 123(2) . . ? C5 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C2 C4 C6 120(3) . . ? C2 C4 H4 120.1 . . ? C6 C4 H4 120.1 . . ? C7 C5 C3 120(2) . . ? C7 C5 H5 119.9 . . ? C3 C5 H5 119.9 . . ? C7 C6 C4 121(3) . . ? C7 C6 H6 119.5 . . ? C4 C6 H6 119.5 . . ? C6 C7 C5 119(2) . . ? C6 C7 C8 118.8(19) . . ? C5 C7 C8 121.5(18) . . ? N1 C8 O1 113.7(15) . . ? N1 C8 C7 129.6(18) . . ? O1 C8 C7 116.7(15) . . ? N2 C9 O1 111.5(15) . . ? N2 C9 C10 121.0(16) . . ? O1 C9 C10 127.3(16) . . ? C11 C10 C9 126.1(18) . . ? C11 C10 C12 122.4(18) . . ? C9 C10 C12 111.3(15) . . ? C13 C11 C10 117(2) . . ? C13 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? C14 C12 C10 115.6(15) . . ? C14 C12 Ir1 131.5(12) . . ? C10 C12 Ir1 113.0(12) . . ? C11 C13 C15 125(2) . . ? C11 C13 H13 117.7 . . ? C15 C13 H13 117.7 . . ? C12 C14 C15 124.6(17) . . ? C12 C14 H14 117.7 . . ? C15 C14 H14 117.7 . . ? C13 C15 C14 115.5(19) . . ? C13 C15 C16 121(2) . . ? C14 C15 C16 124(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C20 C18 C19 115(2) . . ? C20 C18 C17 126(3) . . ? C19 C18 C17 119(3) . . ? C21 C19 C18 122(3) . . ? C21 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C18 C20 C22 125(3) . . ? C18 C20 H20 117.5 . . ? C22 C20 H20 117.5 . . ? C19 C21 C23 121(3) . . ? C19 C21 H21 119.4 . . ? C23 C21 H21 119.4 . . ? C23 C22 C20 118(2) . . ? C23 C22 H22 120.8 . . ? C20 C22 H22 120.8 . . ? C21 C23 C22 118(2) . . ? C21 C23 C24 120(2) . . ? C22 C23 C24 122(2) . . ? N4 C24 O2 110.8(15) . . ? N4 C24 C23 132.2(19) . . ? O2 C24 C23 116.9(17) . . ? N3 C25 O2 111.7(16) . . ? N3 C25 C26 120.3(15) . . ? O2 C25 C26 127.9(17) . . ? C28 C26 C27 123.2(19) . . ? C28 C26 C25 111.4(15) . . ? C27 C26 C25 125.2(18) . . ? C29 C27 C26 120(2) . . ? C29 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C26 C28 C30 116.8(16) . . ? C26 C28 Ir1 115.1(13) . . ? C30 C28 Ir1 128.1(14) . . ? C27 C29 C31 120(2) . . ? C27 C29 H29 120.2 . . ? C31 C29 H29 120.2 . . ? C28 C30 C31 121.2(19) . . ? C28 C30 H30 119.4 . . ? C31 C30 H30 119.4 . . ? C29 C31 C30 119(2) . . ? C29 C31 C32 120(2) . . ? C30 C31 C32 121(2) . . ? C31 C32 H32A 109.5 . . ? 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 . . ? N5 C33 S1 126.0(18) . . ? N5 C33 S2 120.8(16) . . ? S1 C33 S2 113.2(11) . . ? N5 C34 C35 114(2) . . ? N5 C34 H34A 108.7 . . ? C35 C34 H34A 108.7 . . ? N5 C34 H34B 108.6 . . ? C35 C34 H34B 108.6 . . ? H34A C34 H34B 107.6 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 N5 109.9(19) . . ? C37 C36 H36A 109.7 . . ? N5 C36 H36A 109.7 . . ? C37 C36 H36B 109.7 . . ? N5 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 H38A 109.5 . . ? C39 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C39 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C41 C39 C40 117(2) . . ? C41 C39 C38 120(2) . . ? C40 C39 C38 122(2) . . ? C39 C40 C42 120(2) . . ? C39 C40 H40 120.0 . . ? C42 C40 H40 120.0 . . ? C39 C41 C43 125(3) . . ? C39 C41 H41 117.3 . . ? C43 C41 H41 117.3 . . ? C44 C42 C40 119.6(18) . . ? C44 C42 H42 120.2 . . ? C40 C42 H42 120.2 . . ? C44 C43 C41 117(2) . . ? C44 C43 H43 121.3 . . ? C41 C43 H43 121.3 . . ? C43 C44 C42 119.3(17) . . ? C43 C44 C45 121.4(17) . . ? C42 C44 C45 119.1(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ir1 S1 C33 -85.6(7) . . . . ? N3 Ir1 S1 C33 101.7(7) . . . . ? C12 Ir1 S1 C33 -165.2(8) . . . . ? C28 Ir1 S1 C33 27(3) . . . . ? S2 Ir1 S1 C33 8.3(6) . . . . ? N2 Ir1 S2 C33 80.2(7) . . . . ? N3 Ir1 S2 C33 -106.0(7) . . . . ? C12 Ir1 S2 C33 27(3) . . . . ? C28 Ir1 S2 C33 174.8(8) . . . . ? S1 Ir1 S2 C33 -8.0(6) . . . . ? N7 Ir2 S3 C70 -95.2(7) . . . . ? N9 Ir2 S3 C70 90.6(7) . . . . ? C64 Ir2 S3 C70 30(3) . . . . ? C49 Ir2 S3 C70 -175.0(8) . . . . ? S4 Ir2 S3 C70 -0.4(6) . . . . ? N7 Ir2 S4 C70 92.0(7) . . . . ? N9 Ir2 S4 C70 -95.2(7) . . . . ? C64 Ir2 S4 C70 -174.7(8) . . . . ? C49 Ir2 S4 C70 33(3) . . . . ? S3 Ir2 S4 C70 0.4(6) . . . . ? C8 N1 N2 C9 -0.2(19) . . . . ? C8 N1 N2 Ir1 -177.1(13) . . . . ? N3 Ir1 N2 C9 38(3) . . . . ? C12 Ir1 N2 C9 -4.1(13) . . . . ? C28 Ir1 N2 C9 85.3(14) . . . . ? S2 Ir1 N2 C9 -175.0(12) . . . . ? S1 Ir1 N2 C9 -102.9(13) . . . . ? N3 Ir1 N2 N1 -145(3) . . . . ? C12 Ir1 N2 N1 172.6(16) . . . . ? C28 Ir1 N2 N1 -98.0(16) . . . . ? S2 Ir1 N2 N1 1.7(15) . . . . ? S1 Ir1 N2 N1 73.8(15) . . . . ? N2 Ir1 N3 C25 42(3) . . . . ? C12 Ir1 N3 C25 83.0(13) . . . . ? C28 Ir1 N3 C25 -6.8(13) . . . . ? S2 Ir1 N3 C25 -105.2(12) . . . . ? S1 Ir1 N3 C25 -178.1(12) . . . . ? N2 Ir1 N3 N4 -134(3) . . . . ? C12 Ir1 N3 N4 -92.1(17) . . . . ? C28 Ir1 N3 N4 178.1(18) . . . . ? S2 Ir1 N3 N4 79.7(17) . . . . ? S1 Ir1 N3 N4 6.8(17) . . . . ? C25 N3 N4 C24 1.5(19) . . . . ? Ir1 N3 N4 C24 176.8(14) . . . . ? C45 N6 N7 C46 -2.3(18) . . . . ? C45 N6 N7 Ir2 172.0(13) . . . . ? N9 Ir2 N7 C46 48(3) . . . . ? C64 Ir2 N7 C46 88.1(12) . . . . ? C49 Ir2 N7 C46 -0.5(12) . . . . ? S4 Ir2 N7 C46 -171.8(11) . . . . ? S3 Ir2 N7 C46 -100.0(11) . . . . ? N9 Ir2 N7 N6 -126(3) . . . . ? C64 Ir2 N7 N6 -86.0(16) . . . . ? C49 Ir2 N7 N6 -174.6(17) . . . . ? S4 Ir2 N7 N6 14.1(16) . . . . ? S3 Ir2 N7 N6 85.9(16) . . . . ? C61 N8 N9 C62 0(2) . . . . ? C61 N8 N9 Ir2 174.4(15) . . . . ? N7 Ir2 N9 C62 39(4) . . . . ? C64 Ir2 N9 C62 -1.6(14) . . . . ? C49 Ir2 N9 C62 86.8(14) . . . . ? S4 Ir2 N9 C62 -101.0(14) . . . . ? S3 Ir2 N9 C62 -172.8(14) . . . . ? N7 Ir2 N9 N8 -135(3) . . . . ? C64 Ir2 N9 N8 -175.9(18) . . . . ? C49 Ir2 N9 N8 -87.5(17) . . . . ? S4 Ir2 N9 N8 84.7(17) . . . . ? S3 Ir2 N9 N8 12.9(17) . . . . ? C4 C2 C3 C5 5(4) . . . . ? C1 C2 C3 C5 -179(2) . . . . ? C3 C2 C4 C6 -6(5) . . . . ? C1 C2 C4 C6 179(3) . . . . ? C2 C3 C5 C7 0(4) . . . . ? C2 C4 C6 C7 1(6) . . . . ? C4 C6 C7 C5 5(5) . . . . ? C4 C6 C7 C8 180(3) . . . . ? C3 C5 C7 C6 -5(4) . . . . ? C3 C5 C7 C8 180(2) . . . . ? N2 N1 C8 O1 0.0(19) . . . . ? N2 N1 C8 C7 179.7(18) . . . . ? C9 O1 C8 N1 0(2) . . . . ? C9 O1 C8 C7 -179.5(16) . . . . ? C6 C7 C8 N1 10(4) . . . . ? C5 C7 C8 N1 -175(2) . . . . ? C6 C7 C8 O1 -170(2) . . . . ? C5 C7 C8 O1 5(3) . . . . ? N1 N2 C9 O1 0(2) . . . . ? Ir1 N2 C9 O1 178.0(11) . . . . ? N1 N2 C9 C10 -175.1(17) . . . . ? Ir1 N2 C9 C10 3(2) . . . . ? C8 O1 C9 N2 -0.4(19) . . . . ? C8 O1 C9 C10 174.7(19) . . . . ? N2 C9 C10 C11 177(2) . . . . ? O1 C9 C10 C11 2(4) . . . . ? N2 C9 C10 C12 2(3) . . . . ? O1 C9 C10 C12 -173.0(17) . . . . ? C9 C10 C11 C13 -172(2) . . . . ? C12 C10 C11 C13 3(4) . . . . ? C11 C10 C12 C14 -1(3) . . . . ? C9 C10 C12 C14 174.1(17) . . . . ? C11 C10 C12 Ir1 179.6(18) . . . . ? C9 C10 C12 Ir1 -5(2) . . . . ? N2 Ir1 C12 C14 -174.0(18) . . . . ? N3 Ir1 C12 C14 13.7(18) . . . . ? C28 Ir1 C12 C14 92.1(18) . . . . ? S2 Ir1 C12 C14 -120(2) . . . . ? S1 Ir1 C12 C14 -86.1(17) . . . . ? N2 Ir1 C12 C10 4.9(13) . . . . ? N3 Ir1 C12 C10 -167.4(13) . . . . ? C28 Ir1 C12 C10 -89.1(13) . . . . ? S2 Ir1 C12 C10 59(3) . . . . ? S1 Ir1 C12 C10 92.8(13) . . . . ? C10 C11 C13 C15 -2(4) . . . . ? C10 C12 C14 C15 -1(3) . . . . ? Ir1 C12 C14 C15 178.2(17) . . . . ? C11 C13 C15 C14 0(4) . . . . ? C11 C13 C15 C16 175(3) . . . . ? C12 C14 C15 C13 1(4) . . . . ? C12 C14 C15 C16 -174(2) . . . . ? C20 C18 C19 C21 1(5) . . . . ? C17 C18 C19 C21 -180(3) . . . . ? C19 C18 C20 C22 1(4) . . . . ? C17 C18 C20 C22 -178(3) . . . . ? C18 C19 C21 C23 -1(5) . . . . ? C18 C20 C22 C23 -4(4) . . . . ? C19 C21 C23 C22 -2(5) . . . . ? C19 C21 C23 C24 -178(3) . . . . ? C20 C22 C23 C21 4(4) . . . . ? C20 C22 C23 C24 180(2) . . . . ? N3 N4 C24 O2 -1(2) . . . . ? N3 N4 C24 C23 -178(2) . . . . ? C25 O2 C24 N4 1(2) . . . . ? C25 O2 C24 C23 177.9(18) . . . . ? C21 C23 C24 N4 -14(4) . . . . ? C22 C23 C24 N4 170(2) . . . . ? C21 C23 C24 O2 169(2) . . . . ? C22 C23 C24 O2 -6(3) . . . . ? N4 N3 C25 O2 -1(2) . . . . ? Ir1 N3 C25 O2 -177.7(11) . . . . ? N4 N3 C25 C26 -178.2(15) . . . . ? Ir1 N3 C25 C26 5(2) . . . . ? C24 O2 C25 N3 0.3(19) . . . . ? C24 O2 C25 C26 177.1(17) . . . . ? N3 C25 C26 C28 1(2) . . . . ? O2 C25 C26 C28 -175.3(17) . . . . ? N3 C25 C26 C27 175.4(18) . . . . ? O2 C25 C26 C27 -1(3) . . . . ? C28 C26 C27 C29 3(3) . . . . ? C25 C26 C27 C29 -171(2) . . . . ? C27 C26 C28 C30 -3(3) . . . . ? C25 C26 C28 C30 171.3(17) . . . . ? C27 C26 C28 Ir1 178.6(15) . . . . ? C25 C26 C28 Ir1 -7.1(19) . . . . ? N2 Ir1 C28 C26 -163.8(13) . . . . ? N3 Ir1 C28 C26 7.6(13) . . . . ? C12 Ir1 C28 C26 -84.1(13) . . . . ? S2 Ir1 C28 C26 101.9(13) . . . . ? S1 Ir1 C28 C26 84(4) . . . . ? N2 Ir1 C28 C30 18.1(18) . . . . ? N3 Ir1 C28 C30 -170.5(18) . . . . ? C12 Ir1 C28 C30 97.8(18) . . . . ? S2 Ir1 C28 C30 -76.2(17) . . . . ? S1 Ir1 C28 C30 -94(3) . . . . ? C26 C27 C29 C31 -1(4) . . . . ? C26 C28 C30 C31 2(3) . . . . ? Ir1 C28 C30 C31 179.8(16) . . . . ? C27 C29 C31 C30 0(4) . . . . ? C27 C29 C31 C32 176(3) . . . . ? C28 C30 C31 C29 0(4) . . . . ? C28 C30 C31 C32 -177(2) . . . . ? C34 N5 C33 S1 -173.3(16) . . . . ? C36 N5 C33 S1 2(3) . . . . ? C34 N5 C33 S2 6(3) . . . . ? C36 N5 C33 S2 -179.5(14) . . . . ? Ir1 S1 C33 N5 166.9(17) . . . . ? Ir1 S1 C33 S2 -12.0(9) . . . . ? Ir1 S2 C33 N5 -166.9(15) . . . . ? Ir1 S2 C33 S1 12.1(9) . . . . ? C33 N5 C34 C35 79(3) . . . . ? C36 N5 C34 C35 -96(2) . . . . ? C33 N5 C36 C37 -90(2) . . . . ? C34 N5 C36 C37 85(2) . . . . ? C41 C39 C40 C42 1(3) . . . . ? C38 C39 C40 C42 179.9(18) . . . . ? C40 C39 C41 C43 -6(5) . . . . ? C38 C39 C41 C43 175(3) . . . . ? C39 C40 C42 C44 -1(3) . . . . ? C39 C41 C43 C44 11(5) . . . . ? C41 C43 C44 C42 -10(4) . . . . ? C41 C43 C44 C45 173(2) . . . . ? C40 C42 C44 C43 6(3) . . . . ? C40 C42 C44 C45 -177.6(17) . . . . ? N7 N6 C45 O3 1(2) . . . . ? N7 N6 C45 C44 -177.6(17) . . . . ? C46 O3 C45 N6 0.4(19) . . . . ? C46 O3 C45 C44 179.2(15) . . . . ? C43 C44 C45 N6 -7(3) . . . . ? C42 C44 C45 N6 176.6(18) . . . . ? C43 C44 C45 O3 174(2) . . . . ? C42 C44 C45 O3 -2(3) . . . . ? N6 N7 C46 O3 2.6(18) . . . . ? Ir2 N7 C46 O3 -173.1(10) . . . . ? N6 N7 C46 C47 174.5(15) . . . . ? Ir2 N7 C46 C47 -1(2) . . . . ? C45 O3 C46 N7 -1.8(17) . . . . ? C45 O3 C46 C47 -172.7(18) . . . . ? N7 C46 C47 C48 178.9(17) . . . . ? O3 C46 C47 C48 -11(3) . . . . ? N7 C46 C47 C49 3(2) . . . . ? O3 C46 C47 C49 172.9(16) . . . . ? C49 C47 C48 C50 -1(3) . . . . ? C46 C47 C48 C50 -176.2(18) . . . . ? C48 C47 C49 C51 3(2) . . . . ? C46 C47 C49 C51 179.3(15) . . . . ? C48 C47 C49 Ir2 -179.3(14) . . . . ? C46 C47 C49 Ir2 -3.2(18) . . . . ? N7 Ir2 C49 C47 2.1(12) . . . . ? N9 Ir2 C49 C47 -169.5(12) . . . . ? C64 Ir2 C49 C47 -90.4(12) . . . . ? S4 Ir2 C49 C47 63(3) . . . . ? S3 Ir2 C49 C47 93.6(12) . . . . ? N7 Ir2 C49 C51 179.1(16) . . . . ? N9 Ir2 C49 C51 7.5(16) . . . . ? C64 Ir2 C49 C51 86.5(16) . . . . ? S4 Ir2 C49 C51 -120(3) . . . . ? S3 Ir2 C49 C51 -89.4(15) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 3.184 _refine_diff_density_min -1.759 _refine_diff_density_rms 0.236 end