data_dc08m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H33 Cl2 Ir N2 O2' _chemical_formula_weight 812.76 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n

loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0499(6) _cell_length_b 14.3738(6) _cell_length_c 17.4301(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.893(1) _cell_angle_gamma 90.00 _cell_volume 3267.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6778 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 4.287 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.61558 _exptl_absorpt_correction_T_max 0.98253 _exptl_absorpt_process_details ? _exptl_special_details ;

? ; _diffrn_ambient_temperature 294(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 17393 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.07 _reflns_number_total 5793 _reflns_number_gt 4880 _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^)+(0.0265P)^2^+3.4289P] 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 5793 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.274 _refine_ls_restrained_S_all 1.274 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label

_atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir -0.38683(2) 0.705598(18) 0.613576(15) 0.03369(9) Uani 1 1 d . . . Cl1 Cl 0.0460(2) 0.77744(19) 0.51017(16) 0.0939(8) Uani 1 1 d . . . Cl2 Cl -0.0841(3) 0.7137(3) 0.38387(17) 0.1293(13) Uani 1 1 d . . . O1 O -0.4973(4) 0.8111(3) 0.6415(3) 0.0470(13) Uani 1 1 d . . . O2 O -0.4860(3) 0.6047(3) 0.6659(3) 0.0448(12) Uani 1 1 d . . . N1 N -0.4503(4) 0.6965(4) 0.5056(3) 0.0370(13) Uani 1 1 d . . . N2 N -0.3089(4) 0.7070(4) 0.7174(3) 0.0396(13) Uani 1 1 d . . . C1 C -0.5220(5) 0.6308(5) 0.4864(4) 0.0433(18) Uani 1 1 d . . . H1A H -0.5484 0.5938 0.5249 0.052 Uiso 1 1 calc R . . C2 C -0.5557(6) 0.6182(5) 0.4138(4) 0.0487(19) Uani 1 1 d . . . H2A H -0.6068 0.5745 0.4032 0.058 Uiso 1 1 calc R . . C3 C -0.5156(5) 0.6690(5) 0.3538(4) 0.0429(18) Uani 1 1 d . . . C4 C -0.5487(6) 0.6564(6) 0.2764(4) 0.054(2) Uani 1 1 d . . . H4A H -0.6012 0.6144 0.2650 0.065 Uiso 1 1 calc R . . C5 C -0.5059(6) 0.7041(6) 0.2185(5) 0.064(2) Uani 1 1 d . . . H5A H -0.5313 0.6975 0.1683 0.077 Uiso 1 1 calc R . . C6 C -0.4240(7) 0.7626(6) 0.2350(5) 0.066(2) Uani 1 1 d . . . H6A H -0.3915 0.7924 0.1951 0.080 Uiso 1 1 calc R . . C7 C -0.3900(6) 0.7774(6) 0.3090(4) 0.062(2) Uani 1 1 d . . . H7A H -0.3343 0.8167 0.3182 0.075 Uiso 1 1 calc R . . C8 C -0.4368(5) 0.7350(5) 0.3719(4) 0.0391(17) Uani 1 1 d . . . C9 C -0.4079(5) 0.7501(5) 0.4506(4) 0.0354(16) Uani 1 1 d . . . C10 C -0.3333(5) 0.8176(4) 0.4830(4) 0.0371(17) Uani 1 1 d . . . C11 C -0.2909(6) 0.8938(5) 0.4454(4) 0.0481(19) Uani 1 1 d . . . H11A H -0.3127 0.9076 0.3953 0.058 Uiso 1 1 calc R . .

C12 C -0.2171(6) 0.9489(5) 0.4817(5) 0.054(2) Uani 1 1 d . . . H12A H -0.1873 0.9971 0.4546 0.064 Uiso 1 1 calc R . . C13 C -0.1868(5) 0.9337(5) 0.5571(4) 0.0429(18) Uani 1 1 d . . . C14 C -0.2329(5) 0.8621(5) 0.5963(4) 0.0395(17) Uani 1 1 d . . . H14A H -0.2147 0.8529 0.6477 0.047 Uiso 1 1 calc R . . C15 C -0.3063(5) 0.8026(5) 0.5611(4) 0.0358(15) Uani 1 1 d . . . C16 C -0.1070(6) 0.9949(5) 0.5958(5) 0.057(2) Uani 1 1 d . . . H16A H -0.0954 0.9748 0.6479 0.085 Uiso 1 1 calc R . . H16B H -0.1305 1.0582 0.5954 0.085 Uiso 1 1 calc R . . H16C H -0.0442 0.9907 0.5689 0.085 Uiso 1 1 calc R . . C17 C -0.3329(5) 0.7661(5) 0.7755(4) 0.0416(18) Uani 1 1 d . . . H17A H -0.3827 0.8113 0.7661 0.050 Uiso 1 1 calc R . . C18 C -0.2876(5) 0.7613(5) 0.8453(4) 0.0442(18) Uani 1 1 d . . . H18A H -0.3028 0.8052 0.8824 0.053 Uiso 1 1 calc R . . C19 C -0.2166(5) 0.6895(5) 0.8627(4) 0.0423(18) Uani 1 1 d . . . C20 C -0.1745(6) 0.6779(6) 0.9377(4) 0.051(2) Uani 1 1 d . . . H20A H -0.1924 0.7192 0.9760 0.061 Uiso 1 1 calc R . . C21 C -0.1090(6) 0.6081(6) 0.9547(4) 0.055(2) Uani 1 1 d . . . H21A H -0.0781 0.6043 1.0034 0.066 Uiso 1 1 calc R . . C22 C -0.0874(6) 0.5415(6) 0.8994(5) 0.059(2) Uani 1 1 d . . . H22A H -0.0453 0.4913 0.9120 0.071 Uiso 1 1 calc R . . C23 C -0.1289(5) 0.5503(5) 0.8252(4) 0.0455(19) Uani 1 1 d . . . H23A H -0.1152 0.5049 0.7889 0.055 Uiso 1 1 calc R . . C24 C -0.1915(5) 0.6269(5) 0.8036(4) 0.0381(17) Uani 1 1 d . . . C25 C -0.2353(5) 0.6419(4) 0.7280(4) 0.0345(16) Uani 1 1 d . . . C26 C -0.2113(5) 0.5917(4) 0.6572(4) 0.0348(16) Uani 1 1 d . . . C27 C -0.1271(5) 0.5344(5) 0.6452(4) 0.0479(19) Uani 1 1 d . . . H27A H -0.0784 0.5260 0.6848 0.058 Uiso 1 1 calc R . . C28 C -0.1142(6) 0.4898(5) 0.5762(4) 0.052(2) Uani 1 1 d . . . H28A H -0.0578 0.4513 0.5701 0.062 Uiso 1 1 calc R . . C29 C -0.1854(6) 0.5019(5) 0.5154(4) 0.0451(18) Uani 1 1 d . . . C30 C -0.2645(5) 0.5628(5) 0.5253(4) 0.0389(17) Uani 1 1 d . . . H30A H -0.3099 0.5737 0.4840 0.047 Uiso 1 1 calc R . . C31 C -0.2807(5) 0.6095(4) 0.5940(4) 0.0321(15) Uani 1 1 d . . . C32 C -0.1740(6) 0.4509(6) 0.4395(5) 0.067(2) Uani 1 1 d . . . H32A H -0.2298 0.4673 0.4049 0.100 Uiso 1 1 calc R . . H32B H -0.1746 0.3850 0.4483 0.100 Uiso 1 1 calc R . .

H32C H -0.1103 0.4683 0.4174 0.100 Uiso 1 1 calc R . . C33 C -0.5833(6) 0.7941(6) 0.6711(4) 0.0502(19) Uani 1 1 d . . . C34 C -0.6199(6) 0.7105(6) 0.6959(4) 0.057(2) Uani 1 1 d . . . H34A H -0.6854 0.7115 0.7155 0.068 Uiso 1 1 calc R . . C35 C -0.5713(5) 0.6237(5) 0.6956(4) 0.0429(18) Uani 1 1 d . . . C36 C -0.6484(7) 0.8817(6) 0.6825(5) 0.081(3) Uani 1 1 d . . . H36A H -0.6136 0.9348 0.6625 0.121 Uiso 1 1 calc R . . H36B H -0.6588 0.8907 0.7363 0.121 Uiso 1 1 calc R . . H36D H -0.7135 0.8745 0.6560 0.121 Uiso 1 1 calc R . . C37 C -0.6230(6) 0.5436(6) 0.7336(5) 0.068(2) Uani 1 1 d . . . H37A H -0.5817 0.4887 0.7292 0.101 Uiso 1 1 calc R . . H37B H -0.6890 0.5331 0.7091 0.101 Uiso 1 1 calc R . . H37C H -0.6315 0.5577 0.7869 0.101 Uiso 1 1 calc R . . C38 C -0.0687(7) 0.7286(7) 0.4814(5) 0.081(3) Uani 1 1 d . . . H38B H -0.1238 0.7677 0.4989 0.098 Uiso 1 1 calc R . . H38C H -0.0749 0.6685 0.5061 0.098 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.03231(14) 0.03583(15) 0.03302(15) 0.00516(14) 0.00237(10) 0.00633(14) Cl1 0.097(2) 0.094(2) 0.0927(19) 0.0032(15) 0.0285(16) -0.0017(15) Cl2 0.119(3) 0.191(4) 0.0775(19) -0.007(2) 0.0028(18) 0.056(2) O1 0.043(3) 0.045(3) 0.053(3) 0.003(2) 0.011(2) 0.012(2) O2 0.043(3) 0.049(3) 0.043(3) 0.008(2) 0.008(2) 0.001(2) N1 0.036(3) 0.036(3) 0.039(3) 0.008(3) -0.006(3) 0.008(3) N2 0.042(3) 0.039(3) 0.038(3) 0.006(3) 0.004(3) 0.009(3) C1 0.047(4) 0.038(4) 0.046(5) 0.007(3) 0.000(3) -0.001(3) C2 0.053(5) 0.049(5) 0.044(5) -0.002(4) 0.001(4) -0.005(4) C3 0.042(4) 0.049(4) 0.037(4) -0.002(3) -0.004(3) 0.013(3) C4 0.047(5) 0.071(6) 0.044(5) -0.014(4) -0.007(4) 0.004(4) C5 0.063(5) 0.089(7) 0.041(5) -0.005(5) -0.002(4) 0.009(5)

C6 0.069(6) 0.095(7) 0.036(5) 0.005(4) 0.012(4) -0.016(5) C7 0.059(5) 0.088(7) 0.041(5) 0.011(4) 0.008(4) -0.016(5) C8 0.032(4) 0.047(4) 0.038(4) 0.004(3) 0.001(3) 0.009(3) C9 0.029(4) 0.043(4) 0.034(4) 0.002(3) -0.001(3) 0.013(3) C10 0.035(4) 0.038(4) 0.038(4) 0.008(3) 0.003(3) 0.008(3) C11 0.058(5) 0.048(5) 0.038(4) 0.016(4) 0.000(4) 0.006(4) C12 0.060(5) 0.042(5) 0.060(5) 0.015(4) 0.010(4) -0.008(4) C13 0.041(4) 0.035(4) 0.054(5) 0.001(4) 0.007(4) 0.006(3) C14 0.038(4) 0.038(4) 0.043(4) 0.006(3) 0.001(3) 0.004(3) C15 0.035(4) 0.036(4) 0.037(4) -0.003(3) 0.006(3) 0.008(3) C16 0.063(5) 0.042(5) 0.065(6) 0.008(4) -0.002(4) -0.005(4) C17 0.039(4) 0.037(4) 0.048(5) -0.002(3) 0.008(4) 0.011(3) C18 0.048(5) 0.050(5) 0.034(4) -0.002(3) -0.003(4) -0.004(4) C19 0.041(4) 0.049(5) 0.036(4) 0.009(3) -0.003(3) -0.017(3) C20 0.054(5) 0.061(5) 0.038(4) 0.005(4) 0.001(4) -0.015(4) C21 0.059(5) 0.064(6) 0.041(5) 0.014(4) -0.013(4) -0.015(4) C22 0.053(5) 0.063(6) 0.061(6) 0.025(5) -0.018(4) -0.003(4) C23 0.057(5) 0.040(4) 0.039(4) 0.011(3) -0.007(4) 0.004(4) C24 0.033(4) 0.040(4) 0.041(4) 0.012(3) -0.001(3) -0.008(3) C25 0.032(4) 0.036(4) 0.035(4) 0.010(3) -0.002(3) -0.003(3) C26 0.032(4) 0.035(4) 0.038(4) 0.010(3) 0.003(3) 0.004(3) C27 0.040(4) 0.053(5) 0.050(5) 0.005(4) -0.001(4) 0.012(4) C28 0.043(5) 0.049(5) 0.064(6) -0.004(4) 0.009(4) 0.017(4) C29 0.049(5) 0.039(4) 0.049(5) 0.002(4) 0.012(4) 0.002(3) C30 0.033(4) 0.042(4) 0.042(4) -0.003(3) 0.004(3) 0.002(3) C31 0.033(4) 0.027(3) 0.037(4) 0.002(3) 0.007(3) -0.003(3) C32 0.070(6) 0.063(6) 0.067(6) -0.028(5) 0.006(5) 0.021(4) C33 0.047(5) 0.058(5) 0.046(4) 0.006(4) 0.002(4) 0.019(4) C34 0.042(4) 0.071(6) 0.057(5) 0.015(5) 0.014(4) 0.005(4) C35 0.037(4) 0.053(5) 0.038(4) 0.011(4) 0.004(3) 0.007(4) C36 0.072(6) 0.076(7) 0.096(7) 0.026(6) 0.036(5) 0.035(5) C37 0.056(5) 0.073(6) 0.074(6) 0.018(5) 0.017(5) -0.003(4) C38 0.090(7) 0.077(7) 0.078(7) -0.003(5) 0.026(6) 0.010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C15 1.987(7) . ? Ir1 C31 1.994(6) . ? Ir1 N1 2.035(5) . ? Ir1 N2 2.046(5) . ? Ir1 O1 2.159(5) . ? Ir1 O2 2.166(5) . ? Cl1 C38 1.713(10) . ? Cl2 C38 1.718(9) . ? O1 C33 1.274(9) . ? O2 C35 1.272(8) . ? N1 C9 1.361(8) . ? N1 C1 1.364(8) . ? N2 C25 1.349(8) . ? N2 C17 1.366(8) . ? C1 C2 1.338(9) . ? C2 C3 1.391(10) . ? C3 C4 1.414(9) . ? C3 C8 1.427(10) . ? C4 C5 1.356(11) . ? C5 C6 1.384(11) . ? C6 C7 1.366(10) . ? C7 C8 1.411(10) . ? C8 C9 1.429(9) . ? C9 C10 1.473(9) . ?

C10 C11 1.400(9) . ? C10 C15 1.411(9) . ? C11 C12 1.384(10) . ? C12 C13 1.378(10) . ? C13 C14 1.383(9) . ? C13 C16 1.506(10) . ? C14 C15 1.409(9) . ? C17 C18 1.337(9) . ? C18 C19 1.414(10) . ? C19 C20 1.411(9) . ? C19 C24 1.413(10) . ? C20 C21 1.344(10) . ? C21 C22 1.394(11) . ? C22 C23 1.391(10) . ? C23 C24 1.414(9) . ? C24 C25 1.435(9) . ? C25 C26 1.473(9) . ? C26 C27 1.395(9) . ? C26 C31 1.427(8) . ? C27 C28 1.378(10) . ? C28 C29 1.396(10) . ? C29 C30 1.370(9) . ? C29 C32 1.525(10) . ? C30 C31 1.395(9) . ? C33 C34 1.370(11) . ? C33 C36 1.536(10) . ? C34 C35 1.400(10) . ? C35 C37 1.500(10) . ? 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 C31 91.5(3) . . ? C15 Ir1 N1 79.9(2) . . ? C31 Ir1 N1 93.5(2) . . ? C15 Ir1 N2 98.3(2) . . ? C31 Ir1 N2 80.2(2) . . ? N1 Ir1 N2 173.5(2) . . ? C15 Ir1 O1 88.8(2) . . ? C31 Ir1 O1 176.5(2) . . ? N1 Ir1 O1 89.96(19) . . ? N2 Ir1 O1 96.3(2) . . ? C15 Ir1 O2 175.2(2) . . ? C31 Ir1 O2 92.1(2) . . ? N1 Ir1 O2 96.7(2) . . ? N2 Ir1 O2 85.5(2) . . ? O1 Ir1 O2 87.86(18) . . ? C33 O1 Ir1 124.1(5) . . ? C35 O2 Ir1 124.7(5) . . ? C9 N1 C1 120.7(6) . . ? C9 N1 Ir1 116.9(4) . . ? C1 N1 Ir1 121.8(5) . . ? C25 N2 C17 120.6(6) . . ? C25 N2 Ir1 116.5(4) . . ? C17 N2 Ir1 122.8(4) . . ? C2 C1 N1 121.8(7) . . ? C1 C2 C3 121.3(7) . . ? C2 C3 C4 122.6(7) . . ? C2 C3 C8 118.0(6) . . ? C4 C3 C8 119.3(7) . . ? C5 C4 C3 121.7(8) . . ? C4 C5 C6 119.1(7) . . ? C7 C6 C5 121.0(8) . . ? C6 C7 C8 122.1(8) . . ? C7 C8 C3 116.3(7) . . ? C7 C8 C9 125.0(7) . . ? C3 C8 C9 118.6(7) . . ? N1 C9 C8 119.4(6) . . ? N1 C9 C10 112.4(6) . . ?

C8 C9 C10 128.2(7) . . ? C11 C10 C15 118.8(6) . . ? C11 C10 C9 127.0(6) . . ? C15 C10 C9 114.2(6) . . ? C12 C11 C10 120.9(7) . . ? C13 C12 C11 121.2(7) . . ? C12 C13 C14 118.3(7) . . ? C12 C13 C16 120.5(7) . . ? C14 C13 C16 121.3(7) . . ? C13 C14 C15 122.5(7) . . ? C14 C15 C10 118.1(6) . . ? C14 C15 Ir1 126.0(5) . . ? C10 C15 Ir1 115.6(5) . . ? C18 C17 N2 122.5(6) . . ? C17 C18 C19 120.0(7) . . ? C20 C19 C24 120.5(7) . . ? C20 C19 C18 121.2(7) . . ? C24 C19 C18 118.3(6) . . ? C21 C20 C19 121.2(8) . . ? C20 C21 C22 120.1(7) . . ? C23 C22 C21 119.9(7) . . ? C22 C23 C24 121.4(7) . . ? C19 C24 C23 116.6(6) . . ? C19 C24 C25 118.6(6) . . ? C23 C24 C25 124.7(7) . . ? N2 C25 C24 119.4(6) . . ? N2 C25 C26 113.3(5) . . ? C24 C25 C26 127.3(6) . . ? C27 C26 C31 118.3(6) . . ? C27 C26 C25 127.3(6) . . ? C31 C26 C25 114.3(5) . . ? C28 C27 C26 121.7(7) . . ? C27 C28 C29 120.5(7) . . ? C30 C29 C28 118.0(7) . . ? C30 C29 C32 120.8(7) . . ? C28 C29 C32 121.1(7) . . ? C29 C30 C31 123.4(6) . . ?

C30 C31 C26 117.9(6) . . ? C30 C31 Ir1 127.3(5) . . ? C26 C31 Ir1 114.8(5) . . ? O1 C33 C34 128.1(7) . . ? O1 C33 C36 113.2(7) . . ? C34 C33 C36 118.5(7) . . ? C33 C34 C35 128.1(7) . . ? O2 C35 C34 126.6(7) . . ? O2 C35 C37 115.2(7) . . ? C34 C35 C37 118.1(7) . . ? Cl1 C38 Cl2 114.4(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.932 _refine_diff_density_min -1.719 _refine_diff_density_rms 0.105

data_mr36m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H33 Cl2 Ir N2 O4' _chemical_formula_weight 844.76 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c

loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9546(7) _cell_length_b 12.1572(7) _cell_length_c 23.4973(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.620(1) _cell_angle_gamma 90.00 _cell_volume 3408.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3809 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Tabular _exptl_crystal_colour Red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 4.118 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.73005 _exptl_absorpt_correction_T_max 0.98063 _exptl_absorpt_process_details ? _exptl_special_details ;

? ; _diffrn_ambient_temperature 294(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 24861 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.1081 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.33 _reflns_number_total 8471 _reflns_number_gt 4770 _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^)+(0.0358P)^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 8471 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 0.808 _refine_ls_restrained_S_all 0.808 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label

_atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.327691(19) 0.688038(18) 0.089206(10) 0.03998(8) Uani 1 1 d . . . Cl1 Cl 0.6960(2) 0.2103(2) 0.18097(12) 0.1235(9) Uani 1 1 d . . . Cl2 Cl 0.9129(2) 0.2710(3) 0.23281(13) 0.1348(10) Uani 1 1 d . . . O1 O 0.2473(3) 0.5625(3) 0.03695(17) 0.0537(11) Uani 1 1 d . . . O2 O 0.2527(3) 0.6136(4) 0.16102(17) 0.0525(11) Uani 1 1 d . . . O3 O 0.6038(4) 0.7348(4) 0.26349(19) 0.0671(13) Uani 1 1 d . . . O4 O 0.2804(4) 0.9856(4) -0.06922(19) 0.0656(13) Uani 1 1 d . . . N1 N 0.4676(4) 0.5992(3) 0.11123(19) 0.0393(11) Uani 1 1 d . . . N2 N 0.1935(4) 0.7805(4) 0.0620(2) 0.0419(12) Uani 1 1 d . . . C1 C 0.4936(5) 0.5056(5) 0.0833(3) 0.0527(16) Uani 1 1 d . . . H1A H 0.4391 0.4734 0.0587 0.063 Uiso 1 1 calc R . . C2 C 0.5953(6) 0.4576(5) 0.0900(3) 0.0588(18) Uani 1 1 d . . . H2A H 0.6084 0.3911 0.0719 0.071 Uiso 1 1 calc R . . C3 C 0.6804(5) 0.5071(6) 0.1236(3) 0.0569(17) Uani 1 1 d . . . C4 C 0.7924(6) 0.4692(7) 0.1263(3) 0.080(2) Uani 1 1 d . . . H4A H 0.8088 0.4027 0.1090 0.097 Uiso 1 1 calc R . . C5 C 0.8757(7) 0.5270(9) 0.1532(4) 0.103(3) Uani 1 1 d . . . H5A H 0.9489 0.5009 0.1542 0.123 Uiso 1 1 calc R . . C6 C 0.8516(6) 0.6267(8) 0.1797(4) 0.088(3) Uani 1 1 d . . . H6A H 0.9102 0.6669 0.1974 0.105 Uiso 1 1 calc R . . C7 C 0.7474(6) 0.6658(6) 0.1804(3) 0.065(2) Uani 1 1 d . . . H7A H 0.7343 0.7320 0.1986 0.078 Uiso 1 1 calc R . . C8 C 0.6558(5) 0.6065(5) 0.1531(3) 0.0495(16) Uani 1 1 d . . . C9 C 0.5423(5) 0.6469(5) 0.1492(2) 0.0396(14) Uani 1 1 d . . . C10 C 0.4984(5) 0.7476(5) 0.1750(2) 0.0428(14) Uani 1 1 d . . .

C11 C 0.4044(5) 0.7932(5) 0.1429(2) 0.0413(14) Uani 1 1 d . . . C12 C 0.3696(5) 0.8982(5) 0.1579(3) 0.0514(16) Uani 1 1 d . . . H12A H 0.3129 0.9330 0.1358 0.062 Uiso 1 1 calc R . . C13 C 0.4181(6) 0.9511(5) 0.2053(3) 0.0631(19) Uani 1 1 d . . . H13A H 0.3968 1.0230 0.2129 0.076 Uiso 1 1 calc R . . C14 C 0.4966(6) 0.9008(5) 0.2414(3) 0.0591(18) Uani 1 1 d . . . H14A H 0.5241 0.9359 0.2745 0.071 Uiso 1 1 calc R . . C15 C 0.5350(5) 0.7962(5) 0.2277(3) 0.0511(16) Uani 1 1 d . . . C16 C 0.6137(7) 0.7635(7) 0.3223(3) 0.087(3) Uani 1 1 d . . . H16A H 0.6646 0.7138 0.3424 0.131 Uiso 1 1 calc R . . H16B H 0.5415 0.7587 0.3378 0.131 Uiso 1 1 calc R . . H16C H 0.6415 0.8373 0.3264 0.131 Uiso 1 1 calc R . . C17 C 0.0952(5) 0.7805(5) 0.0889(3) 0.0518(17) Uani 1 1 d . . . H17A H 0.0946 0.7500 0.1252 0.062 Uiso 1 1 calc R . . C18 C 0.0001(5) 0.8224(5) 0.0652(3) 0.0559(17) Uani 1 1 d . . . H18A H -0.0620 0.8302 0.0868 0.067 Uiso 1 1 calc R . . C19 C -0.0063(5) 0.8550(5) 0.0075(3) 0.0481(16) Uani 1 1 d . . . C20 C -0.1086(5) 0.8850(5) -0.0219(4) 0.063(2) Uani 1 1 d . . . H20A H -0.1729 0.8932 -0.0021 0.075 Uiso 1 1 calc R . . C21 C -0.1129(6) 0.9015(5) -0.0781(4) 0.074(2) Uani 1 1 d . . . H21A H -0.1808 0.9210 -0.0970 0.089 Uiso 1 1 calc R . . C22 C -0.0181(6) 0.8901(5) -0.1093(3) 0.069(2) Uani 1 1 d . . . H22A H -0.0238 0.8990 -0.1487 0.083 Uiso 1 1 calc R . . C23 C 0.0836(6) 0.8659(5) -0.0818(3) 0.0619(18) Uani 1 1 d . . . H23A H 0.1469 0.8588 -0.1026 0.074 Uiso 1 1 calc R . . C24 C 0.0923(5) 0.8515(4) -0.0213(3) 0.0455(15) Uani 1 1 d . . . C25 C 0.1968(5) 0.8244(4) 0.0097(2) 0.0408(13) Uani 1 1 d . . . C26 C 0.3121(5) 0.8315(4) -0.0086(2) 0.0411(14) Uani 1 1 d . . . C27 C 0.3909(5) 0.7625(5) 0.0237(2) 0.0425(14) Uani 1 1 d . . . C28 C 0.5014(5) 0.7618(5) 0.0082(3) 0.0481(15) Uani 1 1 d . . . H28A H 0.5528 0.7146 0.0268 0.058 Uiso 1 1 calc R . . C29 C 0.5354(5) 0.8287(6) -0.0337(3) 0.0621(19) Uani 1 1 d . . . H29A H 0.6090 0.8241 -0.0442 0.075 Uiso 1 1 calc R . . C30 C 0.4636(5) 0.9031(6) -0.0610(3) 0.0582(18) Uani 1 1 d . . . H30A H 0.4898 0.9508 -0.0881 0.070 Uiso 1 1 calc R . . C31 C 0.3532(5) 0.9066(5) -0.0481(3) 0.0515(16) Uani 1 1 d . . . C32 C 0.3170(6) 1.0620(6) -0.1098(3) 0.081(2) Uani 1 1 d . . .

H32A H 0.2569 1.1115 -0.1208 0.122 Uiso 1 1 calc R . . H32B H 0.3394 1.0231 -0.1427 0.122 Uiso 1 1 calc R . . H32C H 0.3795 1.1031 -0.0932 0.122 Uiso 1 1 calc R . . C33 C 0.1925(6) 0.4833(5) 0.0549(3) 0.0584(18) Uani 1 1 d . . . C34 C 0.1722(5) 0.4611(5) 0.1115(3) 0.0625(19) Uani 1 1 d . . . H34A H 0.1327 0.3967 0.1177 0.075 Uiso 1 1 calc R . . C35 C 0.2026(5) 0.5216(6) 0.1595(3) 0.0541(17) Uani 1 1 d . . . C36 C 0.1453(7) 0.4071(6) 0.0097(3) 0.099(3) Uani 1 1 d . . . H36A H 0.1661 0.4322 -0.0269 0.149 Uiso 1 1 calc R . . H36B H 0.0651 0.4057 0.0102 0.149 Uiso 1 1 calc R . . H36C H 0.1744 0.3344 0.0166 0.149 Uiso 1 1 calc R . . C37 C 0.1728(6) 0.4783(6) 0.2173(3) 0.077(2) Uani 1 1 d . . . H37A H 0.1992 0.5287 0.2466 0.116 Uiso 1 1 calc R . . H37B H 0.2074 0.4078 0.2240 0.116 Uiso 1 1 calc R . . H37C H 0.0929 0.4709 0.2178 0.116 Uiso 1 1 calc R . . C38 C 0.7668(7) 0.2830(8) 0.2364(4) 0.101(3) Uani 1 1 d . . . H38A H 0.7451 0.2547 0.2727 0.121 Uiso 1 1 calc R . . H38B H 0.7456 0.3600 0.2340 0.121 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.04098(13) 0.03863(13) 0.03992(13) 0.00070(13) -0.00071(9) -0.00340(12) Cl1 0.1100(19) 0.154(3) 0.107(2) -0.0221(18) 0.0117(16) 0.0114(17) Cl2 0.0994(19) 0.163(3) 0.141(2) 0.037(2) 0.0025(18) 0.0192(17) O1 0.061(3) 0.046(3) 0.053(3) -0.002(2) -0.009(2) -0.014(2) O2 0.050(3) 0.060(3) 0.047(3) 0.009(2) 0.001(2) -0.008(2) O3 0.092(4) 0.062(3) 0.045(3) -0.001(2) -0.017(3) -0.002(3) O4 0.071(3) 0.062(3) 0.064(3) 0.027(3) 0.009(2) 0.001(2) N1 0.049(3) 0.032(3) 0.037(3) -0.003(2) -0.002(2) 0.002(2) N2 0.044(3) 0.042(3) 0.039(3) 0.001(2) 0.001(2) -0.005(2) C1 0.057(4) 0.050(4) 0.050(4) -0.007(3) -0.007(3) 0.005(3)

C2 0.074(5) 0.048(4) 0.052(4) -0.007(3) -0.006(4) 0.016(4) C3 0.055(4) 0.069(5) 0.047(4) 0.004(4) 0.003(3) 0.011(3) C4 0.068(5) 0.099(7) 0.073(6) 0.005(5) 0.001(5) 0.034(5) C5 0.049(5) 0.157(10) 0.100(8) 0.016(7) -0.011(5) 0.025(6) C6 0.051(5) 0.120(8) 0.089(7) 0.006(6) -0.019(5) -0.005(5) C7 0.053(4) 0.076(5) 0.066(5) 0.009(4) -0.004(4) -0.007(4) C8 0.045(4) 0.060(4) 0.042(4) 0.014(3) -0.004(3) -0.005(3) C9 0.047(4) 0.044(3) 0.028(3) 0.006(3) 0.002(3) -0.005(3) C10 0.054(4) 0.039(4) 0.035(3) -0.002(3) -0.001(3) -0.017(3) C11 0.042(3) 0.042(4) 0.040(3) 0.002(3) 0.004(3) -0.002(3) C12 0.060(4) 0.047(4) 0.047(4) 0.002(3) 0.003(3) 0.001(3) C13 0.090(5) 0.036(4) 0.063(5) -0.011(3) -0.001(4) 0.004(4) C14 0.085(5) 0.042(4) 0.050(4) -0.013(3) -0.001(4) -0.013(4) C15 0.053(4) 0.054(5) 0.045(4) 0.004(3) -0.006(3) -0.012(3) C16 0.115(7) 0.096(6) 0.046(5) -0.002(4) -0.026(5) -0.019(5) C17 0.049(4) 0.055(4) 0.051(4) 0.005(3) 0.005(3) -0.006(3) C18 0.047(4) 0.052(4) 0.070(5) -0.003(4) 0.008(3) -0.002(3) C19 0.040(4) 0.038(3) 0.065(5) -0.004(3) -0.003(3) -0.010(3) C20 0.044(4) 0.044(4) 0.099(6) -0.001(4) -0.009(4) -0.003(3) C21 0.064(5) 0.051(5) 0.102(7) 0.002(4) -0.029(5) 0.007(4) C22 0.081(6) 0.062(5) 0.062(5) 0.000(4) -0.025(4) 0.008(4) C23 0.066(5) 0.055(4) 0.064(5) 0.000(4) -0.007(4) 0.000(3) C24 0.050(4) 0.033(3) 0.052(4) -0.001(3) -0.007(3) -0.007(3) C25 0.044(3) 0.034(3) 0.044(4) -0.003(3) 0.003(3) -0.004(3) C26 0.048(3) 0.037(4) 0.038(3) -0.001(3) 0.000(3) -0.007(3) C27 0.049(4) 0.046(4) 0.032(3) -0.015(3) 0.001(3) -0.010(3) C28 0.040(4) 0.063(4) 0.041(4) -0.007(3) 0.002(3) 0.000(3) C29 0.049(4) 0.088(6) 0.051(4) -0.005(4) 0.010(3) -0.008(4) C30 0.055(4) 0.074(5) 0.046(4) 0.004(4) 0.011(3) -0.011(4) C31 0.058(4) 0.053(4) 0.043(4) 0.000(3) 0.000(3) -0.005(3) C32 0.095(6) 0.071(5) 0.079(6) 0.038(4) 0.012(5) 0.003(4) C33 0.063(4) 0.045(4) 0.065(5) 0.003(4) -0.014(4) -0.008(3) C34 0.067(5) 0.043(4) 0.077(6) 0.012(4) -0.002(4) -0.010(3) C35 0.040(4) 0.064(5) 0.059(5) 0.016(4) 0.003(3) 0.003(3) C36 0.144(8) 0.059(5) 0.093(7) 0.000(5) -0.017(6) -0.039(5) C37 0.068(5) 0.083(6) 0.081(6) 0.029(5) 0.009(4) -0.004(4) C38 0.102(7) 0.130(8) 0.074(6) 0.000(6) 0.021(5) 0.023(6)

_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 C27 1.976(6) . ? Ir1 C11 1.980(6) . ? Ir1 N2 2.029(5) . ? Ir1 N1 2.031(4) . ? Ir1 O1 2.147(4) . ? Ir1 O2 2.159(4) . ? Cl1 C38 1.747(9) . ? Cl2 C38 1.760(8) . ? O1 C33 1.253(7) . ? O2 C35 1.268(7) . ? O3 C15 1.362(7) . ? O3 C16 1.423(7) . ? O4 C31 1.368(7) . ? O4 C32 1.419(7) . ? N1 C9 1.352(7) . ? N1 C1 1.358(7) . ? N2 C25 1.342(7) . ? N2 C17 1.370(7) . ? C1 C2 1.349(8) . ? C1 H1A 0.9300 . ?

C2 C3 1.386(9) . ? C2 H2A 0.9300 . ? C3 C4 1.415(9) . ? C3 C8 1.433(8) . ? C4 C5 1.343(11) . ? C4 H4A 0.9300 . ? C5 C6 1.401(11) . ? C5 H5A 0.9300 . ? C6 C7 1.335(9) . ? C6 H6A 0.9300 . ? C7 C8 1.427(8) . ? C7 H7A 0.9300 . ? C8 C9 1.441(8) . ? C9 C10 1.478(8) . ? C10 C15 1.416(8) . ? C10 C11 1.425(8) . ? C11 C12 1.395(8) . ? C12 C13 1.382(8) . ? C12 H12A 0.9300 . ? C13 C14 1.368(8) . ? C13 H13A 0.9300 . ? C14 C15 1.396(8) . ? C14 H14A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.334(8) . ? C17 H17A 0.9300 . ? C18 C19 1.411(9) . ? C18 H18A 0.9300 . ? C19 C24 1.397(8) . ? C19 C20 1.414(8) . ? C20 C21 1.332(10) . ? C20 H20A 0.9300 . ? C21 C22 1.395(10) . ? C21 H21A 0.9300 . ? C22 C23 1.371(9) . ?

C22 H22A 0.9300 . ? C23 C24 1.430(9) . ? C23 H23A 0.9300 . ? C24 C25 1.444(8) . ? C25 C26 1.472(7) . ? C26 C31 1.413(8) . ? C26 C27 1.441(8) . ? C27 C28 1.393(8) . ? C28 C29 1.359(8) . ? C28 H28A 0.9300 . ? C29 C30 1.378(9) . ? C29 H29A 0.9300 . ? C30 C31 1.373(8) . ? C30 H30A 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.393(9) . ? C33 C36 1.494(9) . ? C34 C35 1.377(9) . ? C34 H34A 0.9300 . ? C35 C37 1.519(8) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? 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 C27 Ir1 C11 90.9(2) . . ? C27 Ir1 N2 80.4(2) . . ? C11 Ir1 N2 99.7(2) . . ? C27 Ir1 N1 95.3(2) . . ? C11 Ir1 N1 80.8(2) . . ? N2 Ir1 N1 175.74(18) . . ? C27 Ir1 O1 93.43(19) . . ? C11 Ir1 O1 174.66(19) . . ? N2 Ir1 O1 84.07(17) . . ? N1 Ir1 O1 95.71(17) . . ? C27 Ir1 O2 177.1(2) . . ? C11 Ir1 O2 88.32(19) . . ? N2 Ir1 O2 96.88(17) . . ? N1 Ir1 O2 87.36(16) . . ? O1 Ir1 O2 87.48(16) . . ? C33 O1 Ir1 125.3(4) . . ? C35 O2 Ir1 124.5(4) . . ? C15 O3 C16 118.3(6) . . ? C31 O4 C32 119.1(5) . . ? C9 N1 C1 121.1(5) . . ? C9 N1 Ir1 116.0(4) . . ? C1 N1 Ir1 122.1(4) . . ? C25 N2 C17 119.9(5) . . ? C25 N2 Ir1 116.2(4) . . ? C17 N2 Ir1 122.6(4) . . ? C2 C1 N1 122.6(6) . . ? C2 C1 H1A 118.7 . . ? N1 C1 H1A 118.7 . . ? C1 C2 C3 120.1(6) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C2 C3 C4 122.9(7) . . ? C2 C3 C8 118.5(6) . . ? C4 C3 C8 118.4(7) . . ? C5 C4 C3 121.5(8) . . ?

C5 C4 H4A 119.3 . . ? C3 C4 H4A 119.3 . . ? C4 C5 C6 119.7(8) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 122.1(8) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C8 120.3(8) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C7 C8 C3 117.9(6) . . ? C7 C8 C9 123.3(6) . . ? C3 C8 C9 118.4(6) . . ? N1 C9 C8 118.5(5) . . ? N1 C9 C10 112.9(5) . . ? C8 C9 C10 127.8(5) . . ? C15 C10 C11 119.4(6) . . ? C15 C10 C9 127.3(6) . . ? C11 C10 C9 113.1(5) . . ? C12 C11 C10 117.4(5) . . ? C12 C11 Ir1 128.2(4) . . ? C10 C11 Ir1 113.8(4) . . ? C13 C12 C11 120.9(6) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C14 C13 C12 121.8(6) . . ? C14 C13 H13A 119.1 . . ? C12 C13 H13A 119.1 . . ? C13 C14 C15 119.2(6) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? O3 C15 C14 123.5(6) . . ? O3 C15 C10 116.9(6) . . ? C14 C15 C10 119.5(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 . . ? C18 C17 N2 122.7(6) . . ? C18 C17 H17A 118.7 . . ? N2 C17 H17A 118.7 . . ? C17 C18 C19 120.1(6) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C24 C19 C18 117.4(6) . . ? C24 C19 C20 120.1(7) . . ? C18 C19 C20 122.4(6) . . ? C21 C20 C19 120.1(7) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C20 C21 C22 121.5(7) . . ? C20 C21 H21A 119.2 . . ? C22 C21 H21A 119.2 . . ? C23 C22 C21 120.0(7) . . ? C23 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? C22 C23 C24 120.0(7) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C19 C24 C23 117.9(6) . . ? C19 C24 C25 119.5(6) . . ? C23 C24 C25 122.4(6) . . ? N2 C25 C24 118.6(5) . . ? N2 C25 C26 111.9(5) . . ? C24 C25 C26 129.5(5) . . ? C31 C26 C27 118.7(5) . . ? C31 C26 C25 126.9(5) . . ? C27 C26 C25 113.9(5) . . ? C28 C27 C26 117.6(5) . . ? C28 C27 Ir1 128.1(5) . . ? C26 C27 Ir1 114.1(4) . . ?

C29 C28 C27 121.3(6) . . ? C29 C28 H28A 119.4 . . ? C27 C28 H28A 119.4 . . ? C28 C29 C30 121.6(6) . . ? C28 C29 H29A 119.2 . . ? C30 C29 H29A 119.2 . . ? C31 C30 C29 119.8(6) . . ? C31 C30 H30A 120.1 . . ? C29 C30 H30A 120.1 . . ? O4 C31 C30 122.7(6) . . ? O4 C31 C26 116.9(5) . . ? C30 C31 C26 120.3(6) . . ? O4 C32 H32A 109.5 . . ? O4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O1 C33 C34 126.7(6) . . ? O1 C33 C36 114.8(6) . . ? C34 C33 C36 118.6(6) . . ? C35 C34 C33 128.7(6) . . ? C35 C34 H34A 115.6 . . ? C33 C34 H34A 115.6 . . ? O2 C35 C34 126.4(6) . . ? O2 C35 C37 114.7(6) . . ? C34 C35 C37 118.9(6) . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ?

H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? Cl1 C38 Cl2 111.0(5) . . ? Cl1 C38 H38A 109.4 . . ? Cl2 C38 H38A 109.4 . . ? Cl1 C38 H38B 109.4 . . ? Cl2 C38 H38B 109.4 . . ? H38A C38 H38B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.698 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.118