# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Fritz Kuhn' _publ_contact_author_email FRITZ.KUEHN@CH.TUM.DE _publ_section_title ; N-Heterocyclic Carbenes of Iridium(I): Ligand Effects on the Catalytic Activity in Transfer Hydrogenation ; loop_ _publ_author_name 'Fritz Kuhn' 'Eberhardt Herdtweck' 'Wolfgang Anton Herrmann' 'Christoph F. Rentzsch' 'Sandra C. Zinner' # Attachment 'Compound_1-Cl1.cif' # CIF-file generated for RENA 1082-153 # Compound 1-Cl #=================================================================== data_RENA-1082-153 _database_code_depnum_ccdc_archive 'CCDC 726759' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C13 H22 Cl Ir N2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H22 Cl Ir N2' _chemical_formula_weight 434.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 7.2573(1) _cell_length_b 12.3428(1) _cell_length_c 15.7279(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1408.83(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(1) _cell_measurement_reflns_used 47286 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.34 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method none _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 9.648 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0226 _exptl_absorpt_correction_T_max 0.1400 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; Diffractometer operator S. D. Hoffmann exposure_time 10 s per image dx 50 1552 films measured in 10 data sets set 1 to 8: omega-scans with delta_omega = 1.0 set 9 to 10: phi-scan with delta_phi = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Straight forward after integration (Oxford, 2005). Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were calculated in ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 153(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'sealed tube, Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Xcalibur \k-CCD diffractometer' _diffrn_measurement_method 'phi- and omega-rotation' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0 _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 34211 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0092 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2576 _reflns_number_gt 2559 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrysAlis (Oxford, 2005)' _computing_cell_refinement 'CrysAlis (Oxford, 2005)' _computing_data_reduction 'CrysAlis (Oxford, 2005)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'PLATON (Spek, 2007)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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^)+(0.0191P)^2^+2.3014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00164(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(8) _chemical_absolute_configuration ad _refine_ls_number_reflns 2576 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0151 _refine_ls_R_factor_gt 0.0149 _refine_ls_wR_factor_ref 0.0374 _refine_ls_wR_factor_gt 0.0373 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.150 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.091 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir Ir Uani 0.19769(2) 0.51338(1) 0.07177(1) 1.000 0.0169(1) . . Cl Cl Uani 0.34464(14) 0.40132(9) 0.17197(7) 1.000 0.0263(3) . . N1 N Uani 0.1644(5) 0.6870(3) 0.2038(2) 1.000 0.0228(11) . . N2 N Uani -0.0789(5) 0.5858(3) 0.2036(2) 1.000 0.0239(11) . . C1 C Uani 0.0860(6) 0.6012(3) 0.1669(3) 1.000 0.0185(11) . . C2 C Uani 0.0477(6) 0.7373(4) 0.2687(3) 1.000 0.0247(12) . . C3 C Uani -0.1226(6) 0.6658(4) 0.2684(3) 1.000 0.0270(12) . . C4 C Uani 0.3419(6) 0.7310(4) 0.1827(3) 1.000 0.0283(12) . . C5 C Uani -0.2156(5) 0.5069(4) 0.1775(3) 1.000 0.0298(11) . . C6 C Uani -0.0071(6) 0.5693(4) -0.0118(3) 1.000 0.0237(12) . . C7 C Uani 0.1494(6) 0.6376(4) -0.0176(3) 1.000 0.0237(14) . . C8 C Uani 0.2821(7) 0.6378(4) -0.0912(3) 1.000 0.0317(14) . . C9 C Uani 0.4393(8) 0.5593(5) -0.0813(4) 1.000 0.0450(17) . . C10 C Uani 0.3952(7) 0.4622(4) -0.0251(3) 1.000 0.0307(14) . . C11 C Uani 0.2415(7) 0.3970(4) -0.0321(3) 1.000 0.0310(14) . . C12 C Uani 0.1004(9) 0.4110(5) -0.1018(4) 1.000 0.0460(17) . . C13 C Uani -0.0574(7) 0.4833(4) -0.0761(3) 1.000 0.0360(14) . . H21 H Uiso 0.01670 0.81300 0.25340 1.000 0.0300 calc R H22 H Uiso 0.10860 0.73670 0.32510 1.000 0.0300 calc R H31 H Uiso -0.14180 0.63120 0.32450 1.000 0.0330 calc R H32 H Uiso -0.23400 0.70770 0.25300 1.000 0.0330 calc R H41 H Uiso 0.41490 0.73980 0.23470 1.000 0.0420 calc R H42 H Uiso 0.32610 0.80160 0.15520 1.000 0.0420 calc R H43 H Uiso 0.40590 0.68160 0.14390 1.000 0.0420 calc R H51 H Uiso -0.25760 0.46600 0.22720 1.000 0.0450 calc R H52 H Uiso -0.16100 0.45710 0.13600 1.000 0.0450 calc R H53 H Uiso -0.32060 0.54430 0.15160 1.000 0.0450 calc R H61 H Uiso -0.08590 0.57820 0.03600 1.000 0.0280 calc R H71 H Uiso 0.17200 0.68650 0.02790 1.000 0.0280 calc R H81 H Uiso 0.21390 0.61990 -0.14380 1.000 0.0380 calc R H82 H Uiso 0.33300 0.71180 -0.09790 1.000 0.0380 calc R H91 H Uiso 0.54610 0.59820 -0.05680 1.000 0.0540 calc R H92 H Uiso 0.47570 0.53280 -0.13830 1.000 0.0540 calc R H101 H Uiso 0.48100 0.44490 0.01850 1.000 0.0370 calc R H111 H Uiso 0.22360 0.34110 0.00860 1.000 0.0370 calc R H121 H Uiso 0.16150 0.44220 -0.15250 1.000 0.0550 calc R H122 H Uiso 0.05130 0.33900 -0.11780 1.000 0.0550 calc R H131 H Uiso -0.15700 0.43780 -0.05220 1.000 0.0430 calc R H132 H Uiso -0.10660 0.51930 -0.12760 1.000 0.0430 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 Ir 0.0167(1) 0.0180(1) 0.0159(1) 0.0001(1) -0.0001(1) 0.0004(1) Cl 0.0251(6) 0.0277(5) 0.0262(5) 0.0117(4) -0.0028(4) -0.0001(4) N1 0.0244(19) 0.0234(18) 0.0205(18) -0.0072(14) 0.0036(14) -0.0038(15) N2 0.0209(18) 0.0254(19) 0.0253(19) -0.0024(15) 0.0061(15) -0.0053(15) C1 0.020(2) 0.017(2) 0.0185(19) 0.0090(16) -0.0039(17) 0.0006(18) C2 0.031(2) 0.024(2) 0.019(2) -0.0025(17) 0.0010(17) 0.0045(18) C3 0.032(2) 0.025(2) 0.024(2) 0.0010(18) 0.0089(19) 0.0036(19) C4 0.026(2) 0.031(2) 0.028(2) -0.0056(18) 0.0014(19) -0.0079(18) C5 0.0245(19) 0.027(2) 0.038(2) 0.0030(18) 0.0033(19) -0.004(3) C6 0.024(2) 0.027(2) 0.020(2) -0.0020(17) -0.0010(18) 0.0075(18) C7 0.035(3) 0.021(2) 0.015(2) 0.0007(16) -0.0032(17) 0.0059(18) C8 0.039(3) 0.032(2) 0.024(2) 0.0032(17) 0.003(2) -0.001(2) C9 0.051(3) 0.044(3) 0.040(3) 0.006(3) 0.023(3) 0.010(3) C10 0.029(2) 0.035(3) 0.028(2) -0.003(2) 0.0095(19) 0.009(2) C11 0.038(3) 0.027(2) 0.028(2) -0.0115(19) -0.0010(19) 0.007(2) C12 0.053(3) 0.045(3) 0.040(3) -0.019(2) -0.013(3) 0.008(3) C13 0.038(2) 0.039(3) 0.031(2) -0.005(3) -0.0106(19) 0.001(2) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir Cl 2.3524(11) . . yes Ir C1 2.018(4) . . yes Ir C6 2.101(5) . . yes Ir C7 2.109(5) . . yes Ir C10 2.185(5) . . yes Ir C11 2.199(5) . . yes N1 C1 1.335(5) . . yes N1 C2 1.465(6) . . yes N1 C4 1.437(6) . . yes N2 C1 1.342(6) . . yes N2 C3 1.454(6) . . yes N2 C5 1.450(6) . . yes C2 C3 1.519(6) . . no C6 C7 1.417(6) . . no C6 C13 1.511(7) . . no C7 C8 1.506(7) . . no C8 C9 1.505(8) . . no C9 C10 1.523(8) . . no C10 C11 1.380(7) . . no C11 C12 1.510(8) . . no C12 C13 1.507(8) . . no C2 H21 0.9900 . . no C2 H22 0.9900 . . no C3 H31 0.9900 . . no C3 H32 0.9900 . . no C4 H41 0.9800 . . no C4 H42 0.9800 . . no C4 H43 0.9800 . . no C5 H51 0.9800 . . no C5 H52 0.9800 . . no C5 H53 0.9800 . . no C6 H61 0.9500 . . no C7 H71 0.9500 . . no C8 H81 0.9900 . . no C8 H82 0.9900 . . no C9 H91 0.9900 . . no C9 H92 0.9900 . . no C10 H101 0.9500 . . no C11 H111 0.9500 . . no C12 H121 0.9900 . . no C12 H122 0.9900 . . no C13 H131 0.9900 . . no C13 H132 0.9900 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl Ir C1 90.07(13) . . . yes Cl Ir C6 158.92(13) . . . yes Cl Ir C7 161.64(12) . . . yes Cl Ir C10 89.99(13) . . . yes Cl Ir C11 92.76(13) . . . yes C1 Ir C6 90.19(18) . . . yes C1 Ir C7 92.12(17) . . . yes C1 Ir C10 159.38(18) . . . yes C1 Ir C11 163.78(18) . . . yes C6 Ir C7 39.35(18) . . . yes C6 Ir C10 97.06(18) . . . yes C6 Ir C11 81.49(18) . . . yes C7 Ir C10 81.63(18) . . . yes C7 Ir C11 90.22(18) . . . yes C10 Ir C11 36.69(19) . . . yes C1 N1 C2 113.1(4) . . . yes C1 N1 C4 125.6(4) . . . yes C2 N1 C4 121.3(4) . . . yes C1 N2 C3 113.6(4) . . . yes C1 N2 C5 125.7(4) . . . yes C3 N2 C5 120.4(3) . . . yes Ir C1 N1 125.3(3) . . . yes Ir C1 N2 127.0(3) . . . yes N1 C1 N2 107.8(4) . . . yes N1 C2 C3 102.8(4) . . . yes N2 C3 C2 102.7(4) . . . yes Ir C6 C7 70.7(3) . . . yes Ir C6 C13 111.0(3) . . . yes C7 C6 C13 124.6(4) . . . no Ir C7 C6 70.0(3) . . . yes Ir C7 C8 114.0(3) . . . yes C6 C7 C8 124.3(4) . . . no C7 C8 C9 113.8(4) . . . no C8 C9 C10 114.0(5) . . . no Ir C10 C9 108.4(3) . . . yes Ir C10 C11 72.2(3) . . . yes C9 C10 C11 125.6(5) . . . no Ir C11 C10 71.1(3) . . . yes Ir C11 C12 111.5(4) . . . yes C10 C11 C12 122.6(5) . . . no C11 C12 C13 112.9(5) . . . no C6 C13 C12 114.3(4) . . . no N1 C2 H21 111.00 . . . no N1 C2 H22 111.00 . . . no C3 C2 H21 111.00 . . . no C3 C2 H22 111.00 . . . no H21 C2 H22 109.00 . . . no N2 C3 H31 111.00 . . . no N2 C3 H32 111.00 . . . no C2 C3 H31 111.00 . . . no C2 C3 H32 111.00 . . . no H31 C3 H32 109.00 . . . no N1 C4 H41 109.00 . . . no N1 C4 H42 109.00 . . . no N1 C4 H43 109.00 . . . no H41 C4 H42 109.00 . . . no H41 C4 H43 109.00 . . . no H42 C4 H43 110.00 . . . no N2 C5 H51 109.00 . . . no N2 C5 H52 109.00 . . . no N2 C5 H53 109.00 . . . no H51 C5 H52 110.00 . . . no H51 C5 H53 109.00 . . . no H52 C5 H53 109.00 . . . no Ir C6 H61 88.00 . . . no C7 C6 H61 118.00 . . . no C13 C6 H61 118.00 . . . no Ir C7 H71 86.00 . . . no C6 C7 H71 118.00 . . . no C8 C7 H71 118.00 . . . no C7 C8 H81 109.00 . . . no C7 C8 H82 109.00 . . . no C9 C8 H81 109.00 . . . no C9 C8 H82 109.00 . . . no H81 C8 H82 108.00 . . . no C8 C9 H91 109.00 . . . no C8 C9 H92 109.00 . . . no C10 C9 H91 109.00 . . . no C10 C9 H92 109.00 . . . no H91 C9 H92 108.00 . . . no Ir C10 H101 90.00 . . . no C9 C10 H101 117.00 . . . no C11 C10 H101 117.00 . . . no Ir C11 H111 87.00 . . . no C10 C11 H111 119.00 . . . no C12 C11 H111 119.00 . . . no C11 C12 H121 109.00 . . . no C11 C12 H122 109.00 . . . no C13 C12 H121 109.00 . . . no C13 C12 H122 109.00 . . . no H121 C12 H122 108.00 . . . no C6 C13 H131 109.00 . . . no C6 C13 H132 109.00 . . . no C12 C13 H131 109.00 . . . no C12 C13 H132 109.00 . . . no H131 C13 H132 108.00 . . . no # End of Crystallographic Information File # Attachment 'Compound_5-Cl1.cif' # CIF-file generated for ZINA 7007-173 # Compound 5-Cl #=================================================================== data_ZINA-7007-173 _database_code_depnum_ccdc_archive 'CCDC 726760' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C19 H32 Cl Ir N2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H32 Cl Ir N2' _chemical_formula_weight 516.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 11.1962(4) _cell_length_b 19.4417(6) _cell_length_c 17.7586(6) _cell_angle_alpha 90 _cell_angle_beta 91.4342(15) _cell_angle_gamma 90 _cell_volume 3864.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 9670 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 67.04 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method none _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 14.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000472 _exptl_absorpt_correction_T_max 0.004662 _exptl_absorpt_process_details 'SHX_ABS procedure, Spek, A. L. (2007)' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10s per film dx 40 5620 films measured in 17 data sets phi-scan with delta_phi = 1.0 omega-scans with delta_omega = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed on a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were calculated in ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 47684 _diffrn_reflns_av_R_equivalents 0.1273 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 67.04 _reflns_number_total 6727 _reflns_number_gt 6636 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'PLATON (Spek, 2007)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+21.0899P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00057(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6727 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 67.04 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 2.419 _refine_diff_density_min -2.052 _refine_diff_density_rms 0.233 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir1 Ir Uani 0.51263(2) 0.19914(1) 0.02567(1) 1.000 0.0115(1) . . Cl1 Cl Uani 0.42640(13) 0.31023(8) 0.00867(9) 1.000 0.0219(4) . . N1 N Uani 0.3806(4) 0.1684(3) 0.1725(3) 1.000 0.0157(16) . . N2 N Uani 0.2740(4) 0.1328(3) 0.0766(3) 1.000 0.0140(16) . . C1 C Uani 0.3768(5) 0.1684(3) 0.0950(3) 1.000 0.0131(17) . . C2 C Uani 0.2852(6) 0.1313(3) 0.1997(4) 1.000 0.0216(19) . . C3 C Uani 0.2201(5) 0.1090(3) 0.1409(4) 1.000 0.0209(19) . . C4 C Uani 0.4649(6) 0.2027(3) 0.2279(4) 1.000 0.0174(19) . . C5 C Uani 0.2102(5) 0.1220(3) 0.0021(3) 1.000 0.0158(17) . . C6 C Uani 0.5461(7) 0.2541(5) 0.1911(4) 1.000 0.035(3) . . C7 C Uani 0.5381(7) 0.1461(4) 0.2670(5) 1.000 0.038(3) . . C8 C Uani 0.3912(6) 0.2412(4) 0.2855(4) 1.000 0.026(2) . . C9 C Uani 0.2667(6) 0.1629(4) -0.0609(4) 1.000 0.0262(19) . . C10 C Uani 0.2105(7) 0.0453(4) -0.0164(4) 1.000 0.028(2) . . C11 C Uani 0.0826(6) 0.1475(4) 0.0090(4) 1.000 0.030(2) . . C12 C Uani 0.6845(5) 0.2423(3) 0.0047(4) 1.000 0.0197(17) . . C13 C Uani 0.6352(6) 0.2192(4) -0.0642(4) 1.000 0.0220(19) . . C14 C Uani 0.6751(7) 0.1544(4) -0.1038(4) 1.000 0.027(2) . . C15 C Uani 0.5968(6) 0.0931(4) -0.0842(4) 1.000 0.026(2) . . C16 C Uani 0.5492(5) 0.0974(3) -0.0051(4) 1.000 0.0164(17) . . C17 C Uani 0.6192(6) 0.1142(3) 0.0594(4) 1.000 0.0170(17) . . C18 C Uani 0.7539(5) 0.1282(4) 0.0590(4) 1.000 0.022(2) . . C19 C Uani 0.7822(6) 0.2044(4) 0.0481(4) 1.000 0.026(2) . . Ir2 Ir Uani 1.04839(2) 0.46117(1) 0.19553(1) 1.000 0.0138(1) . . Cl2 Cl Uani 0.97617(15) 0.46498(9) 0.32066(9) 1.000 0.0265(5) . . N11 N Uani 0.9351(4) 0.5996(3) 0.1461(3) 1.000 0.0157(17) . . N12 N Uani 0.8078(5) 0.5160(3) 0.1282(3) 1.000 0.0170(16) . . C21 C Uani 0.9219(6) 0.5307(3) 0.1569(4) 1.000 0.0156(17) . . C22 C Uani 0.8352(6) 0.6259(3) 0.1085(4) 1.000 0.0187(17) . . C23 C Uani 0.7571(6) 0.5754(3) 0.0983(4) 1.000 0.0204(19) . . C24 C Uani 1.0359(6) 0.6475(3) 0.1707(4) 1.000 0.0203(19) . . C25 C Uani 0.7312(6) 0.4537(3) 0.1420(4) 1.000 0.0197(17) . . C26 C Uani 1.1080(8) 0.6171(4) 0.2349(5) 1.000 0.041(3) . . C27 C Uani 1.1112(8) 0.6637(5) 0.1032(5) 1.000 0.047(3) . . C28 C Uani 0.9801(8) 0.7134(5) 0.1980(6) 1.000 0.049(3) . . C29 C Uani 0.8007(7) 0.3864(4) 0.1367(5) 1.000 0.038(3) . . C30 C Uani 0.6308(8) 0.4511(5) 0.0812(5) 1.000 0.046(3) . . C31 C Uani 0.6801(7) 0.4602(4) 0.2200(5) 1.000 0.033(3) . . C32 C Uani 1.2183(6) 0.4236(4) 0.2411(4) 1.000 0.028(2) . . C33 C Uani 1.1476(7) 0.3674(4) 0.2235(4) 1.000 0.026(2) . . C34 C Uani 1.1716(9) 0.3241(4) 0.1546(5) 1.000 0.043(3) . . C35 C Uani 1.1001(7) 0.3458(4) 0.0858(4) 1.000 0.028(2) . . C36 C Uani 1.0707(6) 0.4222(3) 0.0863(4) 1.000 0.0210(19) . . C37 C Uani 1.1520(6) 0.4754(4) 0.0992(4) 1.000 0.023(2) . . C38 C Uani 1.2861(6) 0.4649(4) 0.1137(5) 1.000 0.032(2) . . C39 C Uani 1.3198(8) 0.4504(5) 0.1949(6) 1.000 0.048(3) . . H21 H Uiso 0.26910 0.12310 0.25120 1.000 0.0260 calc R H31 H Uiso 0.14970 0.08190 0.14270 1.000 0.0250 calc R H61 H Uiso 0.49780 0.28960 0.16570 1.000 0.0530 calc R H62 H Uiso 0.59510 0.23040 0.15420 1.000 0.0530 calc R H63 H Uiso 0.59800 0.27550 0.22970 1.000 0.0530 calc R H71 H Uiso 0.48440 0.11490 0.29330 1.000 0.0570 calc R H72 H Uiso 0.59460 0.16680 0.30350 1.000 0.0570 calc R H73 H Uiso 0.58230 0.12020 0.22940 1.000 0.0570 calc R H81 H Uiso 0.35190 0.20800 0.31820 1.000 0.0400 calc R H82 H Uiso 0.33060 0.26930 0.25930 1.000 0.0400 calc R H83 H Uiso 0.44380 0.27090 0.31610 1.000 0.0400 calc R H91 H Uiso 0.34850 0.14670 -0.06810 1.000 0.0390 calc R H92 H Uiso 0.26820 0.21180 -0.04760 1.000 0.0390 calc R H93 H Uiso 0.21970 0.15660 -0.10770 1.000 0.0390 calc R H101 H Uiso 0.29290 0.02990 -0.02340 1.000 0.0420 calc R H102 H Uiso 0.16340 0.03720 -0.06280 1.000 0.0420 calc R H103 H Uiso 0.17560 0.01950 0.02510 1.000 0.0420 calc R H111 H Uiso 0.04250 0.12120 0.04800 1.000 0.0440 calc R H112 H Uiso 0.03960 0.14150 -0.03930 1.000 0.0440 calc R H113 H Uiso 0.08340 0.19640 0.02260 1.000 0.0440 calc R H121 H Uiso 0.65500 0.28390 0.02520 1.000 0.0230 calc R H131 H Uiso 0.57330 0.24570 -0.08740 1.000 0.0260 calc R H141 H Uiso 0.75910 0.14420 -0.08890 1.000 0.0330 calc R H142 H Uiso 0.67150 0.16190 -0.15890 1.000 0.0330 calc R H151 H Uiso 0.52870 0.09060 -0.12070 1.000 0.0310 calc R H152 H Uiso 0.64390 0.05030 -0.08900 1.000 0.0310 calc R H161 H Uiso 0.46680 0.08820 0.00140 1.000 0.0200 calc R H171 H Uiso 0.58030 0.11690 0.10620 1.000 0.0210 calc R H181 H Uiso 0.79060 0.11240 0.10720 1.000 0.0270 calc R H182 H Uiso 0.78990 0.10140 0.01790 1.000 0.0270 calc R H191 H Uiso 0.79410 0.22620 0.09800 1.000 0.0310 calc R H192 H Uiso 0.85790 0.20860 0.02070 1.000 0.0310 calc R H221 H Uiso 0.82460 0.67220 0.09280 1.000 0.0230 calc R H231 H Uiso 0.68030 0.57920 0.07480 1.000 0.0240 calc R H261 H Uiso 1.05630 0.60970 0.27790 1.000 0.0620 calc R H262 H Uiso 1.17260 0.64880 0.24950 1.000 0.0620 calc R H263 H Uiso 1.14200 0.57310 0.21930 1.000 0.0620 calc R H271 H Uiso 1.16120 0.62390 0.09170 1.000 0.0710 calc R H272 H Uiso 1.16230 0.70350 0.11470 1.000 0.0710 calc R H273 H Uiso 1.05890 0.67420 0.05970 1.000 0.0710 calc R H281 H Uiso 0.92900 0.70340 0.24060 1.000 0.0740 calc R H282 H Uiso 0.93190 0.73400 0.15700 1.000 0.0740 calc R H283 H Uiso 1.04320 0.74560 0.21390 1.000 0.0740 calc R H291 H Uiso 0.83480 0.38250 0.08660 1.000 0.0570 calc R H292 H Uiso 0.74680 0.34760 0.14500 1.000 0.0570 calc R H293 H Uiso 0.86520 0.38590 0.17500 1.000 0.0570 calc R H301 H Uiso 0.66560 0.45360 0.03120 1.000 0.0690 calc R H302 H Uiso 0.57650 0.49000 0.08790 1.000 0.0690 calc R H303 H Uiso 0.58630 0.40790 0.08580 1.000 0.0690 calc R H311 H Uiso 0.63670 0.50380 0.22380 1.000 0.0500 calc R H312 H Uiso 0.74520 0.45910 0.25790 1.000 0.0500 calc R H313 H Uiso 0.62530 0.42180 0.22880 1.000 0.0500 calc R H321 H Uiso 1.20170 0.44750 0.28630 1.000 0.0340 calc R H331 H Uiso 1.08310 0.35580 0.25480 1.000 0.0320 calc R H341 H Uiso 1.25770 0.32690 0.14350 1.000 0.0520 calc R H342 H Uiso 1.15300 0.27540 0.16600 1.000 0.0520 calc R H351 H Uiso 1.02480 0.31910 0.08310 1.000 0.0340 calc R H352 H Uiso 1.14580 0.33500 0.04030 1.000 0.0340 calc R H361 H Uiso 0.98960 0.43470 0.07710 1.000 0.0250 calc R H371 H Uiso 1.12220 0.52110 0.09890 1.000 0.0280 calc R H381 H Uiso 1.31340 0.42620 0.08240 1.000 0.0380 calc R H382 H Uiso 1.32890 0.50680 0.09750 1.000 0.0380 calc R H391 H Uiso 1.35060 0.49330 0.21830 1.000 0.0580 calc R H392 H Uiso 1.38540 0.41620 0.19650 1.000 0.0580 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 0.0062(2) 0.0125(2) 0.0157(2) 0.0006(1) 0.0003(1) 0.0012(1) Cl1 0.0147(7) 0.0167(7) 0.0343(9) 0.0018(6) -0.0011(6) 0.0050(5) N1 0.009(2) 0.021(3) 0.017(3) 0.002(2) 0.000(2) -0.002(2) N2 0.009(2) 0.016(3) 0.017(3) 0.0019(19) 0.000(2) 0.0004(19) C1 0.012(3) 0.008(3) 0.019(3) 0.001(2) -0.003(2) 0.004(2) C2 0.018(3) 0.028(4) 0.019(3) 0.003(3) 0.005(3) -0.003(3) C3 0.012(3) 0.026(4) 0.025(3) 0.004(3) 0.005(3) -0.006(2) C4 0.008(3) 0.026(4) 0.018(3) -0.005(2) -0.004(2) 0.001(2) C5 0.011(3) 0.016(3) 0.020(3) -0.006(2) -0.005(2) 0.002(2) C6 0.034(4) 0.047(5) 0.025(4) -0.013(3) 0.002(3) -0.025(4) C7 0.030(4) 0.046(5) 0.037(4) -0.015(3) -0.023(3) 0.018(4) C8 0.025(4) 0.029(4) 0.025(4) -0.012(3) -0.001(3) 0.003(3) C9 0.017(3) 0.039(4) 0.022(3) 0.005(3) -0.012(3) -0.004(3) C10 0.025(4) 0.025(4) 0.033(4) -0.005(3) -0.011(3) -0.002(3) C11 0.012(3) 0.041(4) 0.036(4) -0.004(3) -0.005(3) 0.007(3) C12 0.009(3) 0.022(3) 0.028(3) 0.001(3) 0.001(2) 0.002(2) C13 0.011(3) 0.029(4) 0.026(3) 0.006(3) 0.001(3) 0.006(3) C14 0.027(4) 0.033(4) 0.022(3) 0.001(3) 0.003(3) 0.006(3) C15 0.024(4) 0.031(4) 0.023(3) -0.010(3) 0.000(3) 0.009(3) C16 0.011(3) 0.012(3) 0.026(3) -0.004(2) -0.006(2) 0.008(2) C17 0.015(3) 0.018(3) 0.018(3) -0.002(2) 0.001(2) 0.006(2) C18 0.007(3) 0.029(4) 0.031(4) -0.005(3) -0.004(3) 0.009(2) C19 0.008(3) 0.034(4) 0.035(4) -0.007(3) -0.005(3) 0.005(3) Ir2 0.0096(2) 0.0159(2) 0.0159(2) 0.0021(1) -0.0005(1) 0.0031(1) Cl2 0.0229(8) 0.0391(10) 0.0177(7) 0.0019(6) 0.0030(6) 0.0109(6) N11 0.012(3) 0.019(3) 0.016(3) 0.001(2) 0.001(2) 0.004(2) N12 0.010(2) 0.025(3) 0.016(3) 0.004(2) -0.002(2) 0.000(2) C21 0.012(3) 0.016(3) 0.019(3) -0.001(2) 0.002(2) 0.002(2) C22 0.017(3) 0.021(3) 0.018(3) 0.007(2) 0.001(2) 0.006(2) C23 0.012(3) 0.027(4) 0.022(3) 0.002(3) -0.001(2) 0.010(2) C24 0.014(3) 0.015(3) 0.032(4) 0.001(3) 0.003(3) -0.004(2) C25 0.014(3) 0.024(3) 0.021(3) 0.000(2) -0.002(3) -0.008(2) C26 0.041(5) 0.029(4) 0.053(5) 0.003(4) -0.021(4) -0.012(3) C27 0.041(5) 0.052(6) 0.049(5) -0.001(4) 0.015(4) -0.035(4) C28 0.029(4) 0.032(5) 0.087(7) -0.015(5) 0.003(5) -0.004(4) C29 0.018(4) 0.026(4) 0.070(6) -0.011(4) 0.007(4) -0.007(3) C30 0.031(4) 0.056(6) 0.050(5) 0.020(4) -0.020(4) -0.019(4) C31 0.028(4) 0.028(4) 0.044(5) 0.005(3) 0.011(3) -0.006(3) C32 0.010(3) 0.039(4) 0.035(4) 0.013(3) -0.005(3) 0.009(3) C33 0.031(4) 0.026(4) 0.022(3) 0.005(3) -0.004(3) 0.015(3) C34 0.071(6) 0.024(4) 0.034(4) 0.007(3) -0.002(4) 0.014(4) C35 0.028(4) 0.029(4) 0.027(4) -0.005(3) 0.000(3) 0.005(3) C36 0.014(3) 0.028(4) 0.021(3) 0.003(3) 0.002(2) 0.010(3) C37 0.017(3) 0.028(4) 0.025(4) 0.010(3) 0.006(3) 0.008(3) C38 0.013(3) 0.033(4) 0.049(5) 0.006(3) 0.005(3) 0.001(3) C39 0.020(4) 0.066(6) 0.059(6) 0.014(5) 0.001(4) 0.003(4) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 Cl1 2.3819(16) . . yes Ir1 C1 2.069(6) . . yes Ir1 C12 2.141(6) . . yes Ir1 C13 2.166(7) . . yes Ir1 C16 2.095(6) . . yes Ir1 C17 2.115(6) . . yes Ir2 Cl2 2.3848(16) . . yes Ir2 C21 2.063(6) . . yes Ir2 C32 2.175(7) . . yes Ir2 C33 2.186(8) . . yes Ir2 C36 2.103(7) . . yes Ir2 C37 2.109(7) . . yes N1 C4 1.502(8) . . yes N1 C1 1.376(8) . . yes N1 C2 1.386(8) . . yes N2 C5 1.503(7) . . yes N2 C1 1.375(7) . . yes N2 C3 1.384(8) . . yes N11 C21 1.362(8) . . yes N11 C22 1.386(8) . . yes N11 C24 1.519(8) . . yes N12 C21 1.393(9) . . yes N12 C23 1.387(8) . . yes N12 C25 1.508(8) . . yes C2 C3 1.331(10) . . no C4 C6 1.511(11) . . no C4 C7 1.529(10) . . no C4 C8 1.526(10) . . no C5 C10 1.527(10) . . no C5 C11 1.520(9) . . no C5 C9 1.523(9) . . no C12 C13 1.404(10) . . no C12 C19 1.514(9) . . no C13 C14 1.516(11) . . no C14 C15 1.525(11) . . no C15 C16 1.517(10) . . no C16 C17 1.410(10) . . no C17 C18 1.533(9) . . no C18 C19 1.528(11) . . no C2 H21 0.9500 . . no C3 H31 0.9500 . . no C6 H63 0.9800 . . no C6 H61 0.9800 . . no C6 H62 0.9800 . . no C7 H71 0.9800 . . no C7 H72 0.9800 . . no C7 H73 0.9800 . . no C8 H83 0.9800 . . no C8 H81 0.9800 . . no C8 H82 0.9800 . . no C9 H93 0.9800 . . no C9 H92 0.9800 . . no C9 H91 0.9800 . . no C10 H102 0.9800 . . no C10 H103 0.9800 . . no C10 H101 0.9800 . . no C11 H111 0.9800 . . no C11 H112 0.9800 . . no C11 H113 0.9800 . . no C12 H121 0.9500 . . no C13 H131 0.9500 . . no C14 H141 0.9900 . . no C14 H142 0.9900 . . no C15 H151 0.9900 . . no C15 H152 0.9900 . . no C16 H161 0.9500 . . no C17 H171 0.9500 . . no C18 H181 0.9900 . . no C18 H182 0.9900 . . no C19 H192 0.9900 . . no C19 H191 0.9900 . . no C22 C23 1.324(9) . . no C24 C26 1.502(11) . . no C24 C27 1.516(11) . . no C24 C28 1.511(11) . . no C25 C29 1.526(10) . . no C25 C30 1.540(11) . . no C25 C31 1.517(11) . . no C32 C33 1.381(11) . . no C32 C39 1.511(12) . . no C33 C34 1.515(11) . . no C34 C35 1.504(12) . . no C35 C36 1.522(10) . . no C36 C37 1.393(10) . . no C37 C38 1.531(10) . . no C38 C39 1.508(14) . . no C22 H221 0.9500 . . no C23 H231 0.9500 . . no C26 H261 0.9800 . . no C26 H262 0.9800 . . no C26 H263 0.9800 . . no C27 H271 0.9800 . . no C27 H272 0.9800 . . no C27 H273 0.9800 . . no C28 H281 0.9800 . . no C28 H282 0.9800 . . no C28 H283 0.9800 . . no C29 H291 0.9800 . . no C29 H292 0.9800 . . no C29 H293 0.9800 . . no C30 H301 0.9800 . . no C30 H302 0.9800 . . no C30 H303 0.9800 . . no C31 H311 0.9800 . . no C31 H312 0.9800 . . no C31 H313 0.9800 . . no C32 H321 0.9500 . . no C33 H331 0.9500 . . no C34 H341 0.9900 . . no C34 H342 0.9900 . . no C35 H351 0.9900 . . no C35 H352 0.9900 . . no C36 H361 0.9500 . . no C37 H371 0.9500 . . no C38 H381 0.9900 . . no C38 H382 0.9900 . . no C39 H391 0.9900 . . no C39 H392 0.9900 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ir1 C1 92.05(16) . . . yes Cl1 Ir1 C12 89.19(16) . . . yes Cl1 Ir1 C13 90.3(2) . . . yes Cl1 Ir1 C16 154.72(19) . . . yes Cl1 Ir1 C17 165.43(18) . . . yes C1 Ir1 C12 153.4(2) . . . yes C1 Ir1 C13 168.3(2) . . . yes C1 Ir1 C16 91.9(2) . . . yes C1 Ir1 C17 91.4(2) . . . yes C12 Ir1 C13 38.0(3) . . . yes C12 Ir1 C16 98.2(2) . . . yes C12 Ir1 C17 81.5(2) . . . yes C13 Ir1 C16 81.2(3) . . . yes C13 Ir1 C17 89.2(3) . . . yes C16 Ir1 C17 39.1(3) . . . yes C36 Ir2 C37 38.6(3) . . . yes C21 Ir2 C33 164.4(3) . . . yes Cl2 Ir2 C21 92.5(2) . . . yes Cl2 Ir2 C32 88.71(19) . . . yes Cl2 Ir2 C33 89.79(19) . . . yes Cl2 Ir2 C36 157.14(17) . . . yes Cl2 Ir2 C37 163.3(2) . . . yes C21 Ir2 C32 158.5(3) . . . yes C33 Ir2 C37 90.4(3) . . . yes C21 Ir2 C36 91.5(3) . . . yes C21 Ir2 C37 91.8(3) . . . yes C32 Ir2 C33 36.9(3) . . . yes C32 Ir2 C36 95.7(3) . . . yes C32 Ir2 C37 81.5(3) . . . yes C33 Ir2 C36 80.7(3) . . . yes C1 N1 C4 131.2(5) . . . yes C1 N1 C2 110.1(5) . . . yes C2 N1 C4 118.7(5) . . . yes C1 N2 C3 110.6(5) . . . yes C1 N2 C5 131.0(5) . . . yes C3 N2 C5 118.2(5) . . . yes C22 N11 C24 119.8(5) . . . yes C21 N11 C22 110.0(5) . . . yes C21 N11 C24 130.2(5) . . . yes C23 N12 C25 120.2(5) . . . yes C21 N12 C25 128.7(5) . . . yes C21 N12 C23 109.4(5) . . . yes N1 C1 N2 104.0(5) . . . yes Ir1 C1 N1 126.2(4) . . . yes Ir1 C1 N2 128.9(4) . . . yes N1 C2 C3 107.9(6) . . . yes N2 C3 C2 107.3(5) . . . yes C7 C4 C8 110.0(6) . . . no N1 C4 C6 112.7(6) . . . yes N1 C4 C7 107.4(5) . . . yes N1 C4 C8 108.4(5) . . . yes C6 C4 C7 110.6(6) . . . no C6 C4 C8 107.9(6) . . . no C10 C5 C11 110.1(5) . . . no N2 C5 C10 108.8(5) . . . yes N2 C5 C11 108.1(5) . . . yes N2 C5 C9 112.1(5) . . . yes C9 C5 C11 107.3(5) . . . no C9 C5 C10 110.4(5) . . . no Ir1 C12 C19 111.2(4) . . . yes Ir1 C12 C13 72.0(4) . . . yes C13 C12 C19 123.5(6) . . . no Ir1 C13 C12 70.0(4) . . . yes Ir1 C13 C14 113.1(5) . . . yes C12 C13 C14 123.8(6) . . . no C13 C14 C15 111.5(6) . . . no C14 C15 C16 112.7(6) . . . no Ir1 C16 C15 111.7(4) . . . yes Ir1 C16 C17 71.2(4) . . . yes C15 C16 C17 124.3(5) . . . no Ir1 C17 C16 69.7(4) . . . yes C16 C17 C18 124.4(6) . . . no Ir1 C17 C18 114.1(4) . . . yes C17 C18 C19 112.3(5) . . . no C12 C19 C18 112.8(5) . . . no C3 C2 H21 126.00 . . . no N1 C2 H21 126.00 . . . no N2 C3 H31 126.00 . . . no C2 C3 H31 126.00 . . . no H61 C6 H63 109.00 . . . no C4 C6 H61 110.00 . . . no C4 C6 H62 109.00 . . . no C4 C6 H63 109.00 . . . no H61 C6 H62 110.00 . . . no H62 C6 H63 110.00 . . . no H71 C7 H72 109.00 . . . no H72 C7 H73 109.00 . . . no C4 C7 H72 110.00 . . . no H71 C7 H73 109.00 . . . no C4 C7 H71 109.00 . . . no C4 C7 H73 110.00 . . . no C4 C8 H81 109.00 . . . no H82 C8 H83 110.00 . . . no C4 C8 H83 109.00 . . . no H81 C8 H82 109.00 . . . no C4 C8 H82 110.00 . . . no H81 C8 H83 109.00 . . . no C5 C9 H91 110.00 . . . no C5 C9 H92 110.00 . . . no H92 C9 H93 109.00 . . . no C5 C9 H93 109.00 . . . no H91 C9 H92 109.00 . . . no H91 C9 H93 109.00 . . . no H101 C10 H102 109.00 . . . no H101 C10 H103 109.00 . . . no H102 C10 H103 109.00 . . . no C5 C10 H103 110.00 . . . no C5 C10 H101 109.00 . . . no C5 C10 H102 110.00 . . . no C5 C11 H113 109.00 . . . no C5 C11 H111 110.00 . . . no C5 C11 H112 109.00 . . . no H112 C11 H113 109.00 . . . no H111 C11 H112 109.00 . . . no H111 C11 H113 109.00 . . . no Ir1 C12 H121 87.00 . . . no C13 C12 H121 118.00 . . . no C19 C12 H121 118.00 . . . no Ir1 C13 H131 87.00 . . . no C14 C13 H131 118.00 . . . no C12 C13 H131 118.00 . . . no C13 C14 H142 109.00 . . . no C15 C14 H141 109.00 . . . no C13 C14 H141 109.00 . . . no H141 C14 H142 108.00 . . . no C15 C14 H142 109.00 . . . no H151 C15 H152 108.00 . . . no C16 C15 H152 109.00 . . . no C14 C15 H151 109.00 . . . no C14 C15 H152 109.00 . . . no C16 C15 H151 109.00 . . . no Ir1 C16 H161 87.00 . . . no C15 C16 H161 118.00 . . . no C17 C16 H161 118.00 . . . no C18 C17 H171 118.00 . . . no C16 C17 H171 118.00 . . . no Ir1 C17 H171 86.00 . . . no C19 C18 H181 109.00 . . . no C17 C18 H182 109.00 . . . no C17 C18 H181 109.00 . . . no C19 C18 H182 109.00 . . . no H181 C18 H182 108.00 . . . no H191 C19 H192 108.00 . . . no C12 C19 H191 109.00 . . . no C12 C19 H192 109.00 . . . no C18 C19 H191 109.00 . . . no C18 C19 H192 109.00 . . . no Ir2 C21 N11 128.0(5) . . . yes Ir2 C21 N12 127.1(4) . . . yes N11 C21 N12 104.6(5) . . . yes N11 C22 C23 108.3(5) . . . yes N12 C23 C22 107.6(6) . . . yes N11 C24 C26 111.0(5) . . . yes N11 C24 C27 108.9(6) . . . yes N11 C24 C28 107.6(6) . . . yes C26 C24 C27 112.5(6) . . . no C26 C24 C28 108.0(7) . . . no C27 C24 C28 108.7(6) . . . no N12 C25 C29 112.7(6) . . . yes N12 C25 C30 108.7(6) . . . yes N12 C25 C31 108.1(5) . . . yes C29 C25 C30 107.0(6) . . . no C29 C25 C31 109.4(6) . . . no C30 C25 C31 111.0(6) . . . no Ir2 C32 C33 72.0(4) . . . yes Ir2 C32 C39 110.2(5) . . . yes C33 C32 C39 125.8(7) . . . no Ir2 C33 C32 71.1(4) . . . yes Ir2 C33 C34 112.3(5) . . . yes C32 C33 C34 120.7(7) . . . no C33 C34 C35 113.5(7) . . . no C34 C35 C36 112.3(6) . . . no Ir2 C36 C35 112.8(5) . . . yes Ir2 C36 C37 70.9(4) . . . yes C35 C36 C37 125.8(6) . . . no Ir2 C37 C36 70.5(4) . . . yes Ir2 C37 C38 113.8(5) . . . yes C36 C37 C38 124.3(7) . . . no C37 C38 C39 114.0(7) . . . no C32 C39 C38 114.2(7) . . . no N11 C22 H221 126.00 . . . no C23 C22 H221 126.00 . . . no N12 C23 H231 126.00 . . . no C22 C23 H231 126.00 . . . no C24 C26 H261 109.00 . . . no C24 C26 H262 109.00 . . . no C24 C26 H263 110.00 . . . no H261 C26 H262 109.00 . . . no H261 C26 H263 109.00 . . . no H262 C26 H263 110.00 . . . no C24 C27 H271 109.00 . . . no C24 C27 H272 109.00 . . . no C24 C27 H273 109.00 . . . no H271 C27 H272 109.00 . . . no H271 C27 H273 110.00 . . . no H272 C27 H273 110.00 . . . no C24 C28 H281 110.00 . . . no C24 C28 H282 109.00 . . . no C24 C28 H283 109.00 . . . no H281 C28 H282 109.00 . . . no H281 C28 H283 110.00 . . . no H282 C28 H283 109.00 . . . no C25 C29 H291 109.00 . . . no C25 C29 H292 110.00 . . . no C25 C29 H293 109.00 . . . no H291 C29 H292 109.00 . . . no H291 C29 H293 109.00 . . . no H292 C29 H293 110.00 . . . no C25 C30 H301 110.00 . . . no C25 C30 H302 110.00 . . . no C25 C30 H303 109.00 . . . no H301 C30 H302 110.00 . . . no H301 C30 H303 109.00 . . . no H302 C30 H303 109.00 . . . no C25 C31 H311 110.00 . . . no C25 C31 H312 110.00 . . . no C25 C31 H313 109.00 . . . no H311 C31 H312 109.00 . . . no H311 C31 H313 110.00 . . . no H312 C31 H313 109.00 . . . no Ir2 C32 H321 88.00 . . . no C33 C32 H321 117.00 . . . no C39 C32 H321 117.00 . . . no Ir2 C33 H331 87.00 . . . no C32 C33 H331 120.00 . . . no C34 C33 H331 120.00 . . . no C33 C34 H341 109.00 . . . no C33 C34 H342 109.00 . . . no C35 C34 H341 109.00 . . . no C35 C34 H342 109.00 . . . no H341 C34 H342 108.00 . . . no C34 C35 H351 109.00 . . . no C34 C35 H352 109.00 . . . no C36 C35 H351 109.00 . . . no C36 C35 H352 109.00 . . . no H351 C35 H352 108.00 . . . no Ir2 C36 H361 86.00 . . . no C35 C36 H361 117.00 . . . no C37 C36 H361 117.00 . . . no Ir2 C37 H371 86.00 . . . no C36 C37 H371 118.00 . . . no C38 C37 H371 118.00 . . . no C37 C38 H381 109.00 . . . no C37 C38 H382 109.00 . . . no C39 C38 H381 109.00 . . . no C39 C38 H382 109.00 . . . no H381 C38 H382 108.00 . . . no C32 C39 H391 109.00 . . . no C32 C39 H392 109.00 . . . no C38 C39 H391 109.00 . . . no C38 C39 H392 109.00 . . . no H391 C39 H392 108.00 . . . no # End of Crystallographic Information File