# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pro5-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H33 Ir N4 O2, 2(C H2 Cl2)' _chemical_formula_sum 'C45 H37 Cl4 Ir N4 O2' _chemical_formula_weight 999.79 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 25.083(5) _cell_length_b 9.7633(17) _cell_length_c 16.902(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.130(2) _cell_angle_gamma 90.00 _cell_volume 4061.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8117 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 28.0 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 3.595 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6817 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'DATABS (Rigaku)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn724+' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12750 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4856 _reflns_number_gt 4736 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0500P)^2^+5.0000P] 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 SHELXL _refine_ls_extinction_coef 0.00107(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4856 _refine_ls_number_parameters 257 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.408 _refine_ls_restrained_S_all 1.410 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL PRO5-3 in C2/c CELL 0.71073 25.0826 9.7633 16.9019 90.000 101.130 90.000 ZERR 4.00 0.0048 0.0017 0.0032 0.000 0.002 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O Cl Ir UNIT 180 148 16 8 16 4 OMIT -2 56 OMIT 1 1 0 OMIT 2 0 0 OMIT 0 0 2 OMIT -1 1 1 OMIT 1 1 1 L.S. 4 ACTA BOND $H FMAP 2 PLAN 10 DFIX 2.77 0.05 CL1 CL2 DFIX 1.70 0.01 C23 CL1 C23 CL2 WGHT 0.050000 5.000000 EXTI 0.001072 FVAR 0.15492 IR1 6 0.500000 0.431785 0.250000 10.50000 0.01792 0.02331 = 0.01712 0.00000 0.00373 0.00000 CL1 5 0.648645 1.005949 0.483544 11.00000 0.14886 0.10389 = 0.17122 0.02028 0.09433 0.01014 CL2 5 0.667865 0.811974 0.367467 11.00000 0.58120 0.23090 = 0.15646 -0.10103 0.14418 -0.22800 O1 4 0.515174 0.268329 0.169151 11.00000 0.03215 0.02641 = 0.02063 -0.00178 0.00339 0.00374 N1 3 0.430729 0.444981 0.161584 11.00000 0.01962 0.03079 = 0.01570 -0.00263 0.00213 0.00240 N2 3 0.342912 0.466638 0.030303 11.00000 0.02659 0.05677 = 0.02785 -0.00525 0.00024 0.01172 C1 1 0.500000 0.075889 0.250000 10.50000 0.05818 0.03082 = 0.03253 0.00000 0.00252 0.00000 AFIX 43 H1 2 0.500000 -0.019366 0.250000 10.50000 -1.20000 AFIX 0 C2 1 0.510725 0.141519 0.180967 11.00000 0.04587 0.03292 = 0.02680 -0.00647 0.00191 0.01032 C3 1 0.519125 0.050917 0.111652 11.00000 0.09237 0.03415 = 0.03797 -0.00837 0.01401 0.01613 AFIX 137 H3A 2 0.512021 0.102588 0.062413 11.00000 -1.50000 H3B 2 0.494740 -0.025697 0.107245 11.00000 -1.50000 H3C 2 0.555939 0.018442 0.121370 11.00000 -1.50000 AFIX 0 C4 1 0.382058 0.379286 0.163786 11.00000 0.01959 0.03223 = 0.02806 -0.00796 0.00436 0.00247 C5 1 0.374971 0.303852 0.230579 11.00000 0.02353 0.04214 = 0.02787 -0.00644 0.00022 -0.00696 AFIX 43 H5 2 0.402476 0.301436 0.276163 11.00000 -1.20000 AFIX 0 C6 1 0.326398 0.230886 0.229837 11.00000 0.02919 0.04716 = 0.03779 -0.00639 0.00701 -0.00846 C7 1 0.319289 0.148125 0.296080 11.00000 0.03559 0.07263 = 0.05113 0.00109 0.00918 -0.02356 AFIX 43 H7 2 0.346872 0.143003 0.341474 11.00000 -1.20000 AFIX 0 C8 1 0.272333 0.075871 0.293870 11.00000 0.04763 0.07349 = 0.06758 0.00130 0.01905 -0.03109 AFIX 43 H8 2 0.268084 0.022518 0.337813 11.00000 -1.20000 AFIX 0 C9 1 0.230349 0.081935 0.225255 11.00000 0.03536 0.08775 = 0.07644 -0.01489 0.01887 -0.03582 AFIX 43 H9 2 0.198657 0.032070 0.224445 11.00000 -1.20000 AFIX 0 C10 1 0.235285 0.158567 0.160892 11.00000 0.02589 0.07308 = 0.06054 -0.01939 0.00441 -0.01180 AFIX 43 H10 2 0.207172 0.160999 0.116097 11.00000 -1.20000 AFIX 0 C11 1 0.283512 0.236059 0.161192 11.00000 0.02667 0.05463 = 0.03943 -0.01966 0.00549 -0.00632 C12 1 0.290362 0.318202 0.097027 11.00000 0.01762 0.06694 = 0.04041 -0.01195 -0.00153 -0.00261 AFIX 43 H12 2 0.261838 0.327261 0.053147 11.00000 -1.20000 AFIX 0 C13 1 0.339090 0.387938 0.096494 11.00000 0.01936 0.05102 = 0.02853 -0.01424 0.00310 0.00102 C14 1 0.388627 0.530782 0.029870 11.00000 0.03066 0.04237 = 0.02280 -0.00425 0.00138 0.01171 C15 1 0.435270 0.518811 0.096435 11.00000 0.02555 0.02790 = 0.02075 -0.00081 0.00261 0.00726 C16 1 0.388691 0.617412 -0.043368 11.00000 0.04518 0.06471 = 0.02594 0.00855 -0.00354 0.01327 AFIX 137 H16A 2 0.414777 0.581874 -0.072799 11.00000 -1.50000 H16B 2 0.398130 0.709877 -0.027089 11.00000 -1.50000 H16C 2 0.353206 0.615947 -0.077105 11.00000 -1.50000 AFIX 0 C17 1 0.488156 0.587202 0.102571 11.00000 0.02903 0.02592 = 0.01720 0.00083 0.00649 0.00518 C18 1 0.522495 0.570591 0.178346 11.00000 0.02269 0.02407 = 0.02069 -0.00001 0.00885 0.00294 C19 1 0.571817 0.641195 0.192786 11.00000 0.02899 0.02901 = 0.02988 0.00433 0.00845 -0.00033 AFIX 43 H19 2 0.594084 0.635413 0.243495 11.00000 -1.20000 AFIX 0 C20 1 0.588532 0.719493 0.133875 11.00000 0.03359 0.03428 = 0.03980 0.00710 0.01421 -0.00198 AFIX 43 H20 2 0.621052 0.767871 0.145277 11.00000 -1.20000 AFIX 0 C21 1 0.555790 0.724876 0.056825 11.00000 0.04264 0.02932 = 0.03517 0.00794 0.02047 0.00546 AFIX 43 H21 2 0.567965 0.771508 0.015729 11.00000 -1.20000 AFIX 0 C22 1 0.506016 0.662172 0.041352 11.00000 0.04120 0.02838 = 0.02502 0.00483 0.01077 0.00828 AFIX 43 H22 2 0.484021 0.669063 -0.009513 11.00000 -1.20000 AFIX 0 C23 1 0.693249 0.894614 0.452544 11.00000 0.65966 0.24933 = 0.46565 -0.23407 0.45805 -0.26814 AFIX 23 H23A 2 0.725160 0.945255 0.444989 11.00000 -1.20000 H23B 2 0.704810 0.827812 0.494858 11.00000 -1.20000 HKLF 4 REM PRO5-3 in C2/c REM R1 = 0.0448 for 4736 Fo > 4sig(Fo) and 0.0459 for all 4856 data REM 257 parameters refined using 3 restraints END ; 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 0.5000 0.43179(2) 0.2500 0.01941(12) Uani 1 2 d S . . Cl1 Cl 0.64865(17) 1.0059(4) 0.4835(3) 0.1328(13) Uani 1 1 d D . . Cl2 Cl 0.6679(4) 0.8120(8) 0.3675(3) 0.313(6) Uani 1 1 d D . . O1 O 0.51517(14) 0.2683(3) 0.1692(2) 0.0266(7) Uani 1 1 d . . . N1 N 0.43073(17) 0.4450(4) 0.1616(2) 0.0222(8) Uani 1 1 d . . . N2 N 0.34291(19) 0.4666(6) 0.0303(3) 0.0377(10) Uani 1 1 d . . . C1 C 0.5000 0.0759(7) 0.2500 0.041(2) Uani 1 2 d S . . H1 H 0.5000 -0.0194 0.2500 0.050 Uiso 1 2 calc SR . . C2 C 0.5107(2) 0.1415(5) 0.1810(3) 0.0359(12) Uani 1 1 d . . . C3 C 0.5191(4) 0.0509(6) 0.1117(4) 0.055(2) Uani 1 1 d . . . H3A H 0.5120 0.1026 0.0624 0.082 Uiso 1 1 calc R . . H3B H 0.4947 -0.0257 0.1072 0.082 Uiso 1 1 calc R . . H3C H 0.5559 0.0184 0.1214 0.082 Uiso 1 1 calc R . . C4 C 0.38206(19) 0.3793(5) 0.1638(3) 0.0267(9) Uani 1 1 d . . . C5 C 0.3750(2) 0.3039(5) 0.2306(3) 0.0318(10) Uani 1 1 d . . . H5 H 0.4025 0.3014 0.2762 0.038 Uiso 1 1 calc R . . C6 C 0.3264(2) 0.2309(6) 0.2298(3) 0.0380(12) Uani 1 1 d . . . C7 C 0.3193(3) 0.1481(8) 0.2961(4) 0.0530(16) Uani 1 1 d . . . H7 H 0.3469 0.1430 0.3415 0.064 Uiso 1 1 calc R . . C8 C 0.2723(3) 0.0759(7) 0.2939(6) 0.062(2) Uani 1 1 d . . . H8 H 0.2681 0.0225 0.3378 0.074 Uiso 1 1 calc R . . C9 C 0.2303(3) 0.0819(8) 0.2253(6) 0.065(2) Uani 1 1 d . . . H9 H 0.1987 0.0321 0.2244 0.079 Uiso 1 1 calc R . . C10 C 0.2353(2) 0.1586(8) 0.1609(4) 0.0537(17) Uani 1 1 d . . . H10 H 0.2072 0.1610 0.1161 0.064 Uiso 1 1 calc R . . C11 C 0.2835(2) 0.2361(6) 0.1612(4) 0.0404(13) Uani 1 1 d . . . C12 C 0.2904(2) 0.3182(7) 0.0970(4) 0.0426(14) Uani 1 1 d . . . H12 H 0.2618 0.3273 0.0531 0.051 Uiso 1 1 calc R . . C13 C 0.3391(2) 0.3879(6) 0.0965(3) 0.0332(11) Uani 1 1 d . . . C14 C 0.3886(2) 0.5308(6) 0.0299(3) 0.0324(11) Uani 1 1 d . . . C15 C 0.43527(19) 0.5188(5) 0.0964(3) 0.0250(9) Uani 1 1 d . . . C16 C 0.3887(3) 0.6174(7) -0.0434(3) 0.0467(14) Uani 1 1 d . . . H16A H 0.4148 0.5819 -0.0728 0.070 Uiso 1 1 calc R . . H16B H 0.3981 0.7099 -0.0271 0.070 Uiso 1 1 calc R . . H16C H 0.3532 0.6159 -0.0771 0.070 Uiso 1 1 calc R . . C17 C 0.4882(2) 0.5872(5) 0.1026(3) 0.0238(9) Uani 1 1 d . . . C18 C 0.5225(2) 0.5706(4) 0.1783(3) 0.0219(10) Uani 1 1 d . . . C19 C 0.5718(2) 0.6412(5) 0.1928(3) 0.0289(10) Uani 1 1 d . . . H19 H 0.5941 0.6354 0.2435 0.035 Uiso 1 1 calc R . . C20 C 0.5885(2) 0.7195(5) 0.1339(3) 0.0349(11) Uani 1 1 d . . . H20 H 0.6211 0.7679 0.1453 0.042 Uiso 1 1 calc R . . C21 C 0.5558(2) 0.7249(5) 0.0568(3) 0.0340(11) Uani 1 1 d . . . H21 H 0.5680 0.7715 0.0157 0.041 Uiso 1 1 calc R . . C22 C 0.5060(2) 0.6622(5) 0.0414(3) 0.0309(10) Uani 1 1 d . . . H22 H 0.4840 0.6691 -0.0095 0.037 Uiso 1 1 calc R . . C23 C 0.6932(6) 0.895(2) 0.4525(10) 0.41(3) Uani 1 1 d D . . H23A H 0.7252 0.9453 0.4450 0.494 Uiso 1 1 calc R . . H23B H 0.7048 0.8278 0.4949 0.494 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 0.01792(15) 0.02331(16) 0.01712(16) 0.000 0.00373(10) 0.000 Cl1 0.149(3) 0.104(2) 0.171(3) 0.020(2) 0.094(3) 0.010(2) Cl2 0.581(16) 0.231(7) 0.156(4) -0.101(5) 0.144(7) -0.228(9) O1 0.0321(18) 0.0264(17) 0.0206(16) -0.0018(13) 0.0034(14) 0.0037(13) N1 0.0196(19) 0.031(2) 0.0157(19) -0.0026(13) 0.0021(15) 0.0024(13) N2 0.027(2) 0.057(3) 0.028(2) -0.005(2) 0.0002(18) 0.012(2) C1 0.058(6) 0.031(4) 0.033(5) 0.000 0.003(4) 0.000 C2 0.046(3) 0.033(3) 0.027(2) -0.006(2) 0.002(2) 0.010(2) C3 0.092(6) 0.034(3) 0.038(4) -0.008(2) 0.014(4) 0.016(3) C4 0.020(2) 0.032(2) 0.028(2) -0.0080(19) 0.0044(18) 0.0025(17) C5 0.024(2) 0.042(3) 0.028(2) -0.006(2) 0.0002(19) -0.007(2) C6 0.029(3) 0.047(3) 0.038(3) -0.006(2) 0.007(2) -0.008(2) C7 0.036(3) 0.073(4) 0.051(4) 0.001(3) 0.009(3) -0.024(3) C8 0.048(4) 0.073(5) 0.068(5) 0.001(3) 0.019(4) -0.031(3) C9 0.035(4) 0.088(6) 0.076(6) -0.015(4) 0.019(4) -0.036(3) C10 0.026(3) 0.073(4) 0.061(4) -0.019(4) 0.004(3) -0.012(3) C11 0.027(3) 0.055(3) 0.039(3) -0.020(3) 0.005(2) -0.006(2) C12 0.018(2) 0.067(4) 0.040(3) -0.012(3) -0.002(2) -0.003(2) C13 0.019(2) 0.051(3) 0.029(3) -0.014(2) 0.0031(19) 0.001(2) C14 0.031(3) 0.042(3) 0.023(2) -0.004(2) 0.001(2) 0.012(2) C15 0.026(2) 0.028(2) 0.021(2) -0.0008(18) 0.0026(17) 0.0073(18) C16 0.045(3) 0.065(4) 0.026(3) 0.009(3) -0.004(2) 0.013(3) C17 0.029(2) 0.026(2) 0.017(2) 0.0008(16) 0.0065(19) 0.0052(17) C18 0.023(2) 0.024(2) 0.021(2) 0.0000(15) 0.0088(19) 0.0029(15) C19 0.029(2) 0.029(2) 0.030(2) 0.0043(19) 0.008(2) -0.0003(18) C20 0.034(3) 0.034(3) 0.040(3) 0.007(2) 0.014(2) -0.002(2) C21 0.043(3) 0.029(2) 0.035(3) 0.008(2) 0.020(2) 0.005(2) C22 0.041(3) 0.028(2) 0.025(2) 0.0048(19) 0.011(2) 0.008(2) C23 0.66(7) 0.25(3) 0.47(5) -0.23(3) 0.46(5) -0.27(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C18 1.971(5) . ? Ir1 C18 1.971(5) 2_655 ? Ir1 N1 2.065(4) 2_655 ? Ir1 N1 2.066(4) . ? Ir1 O1 2.182(3) . ? Ir1 O1 2.182(3) 2_655 ? Cl1 C23 1.713(10) . ? Cl2 C23 1.665(10) . ? O1 C2 1.262(6) . ? N1 C15 1.339(6) . ? N1 C4 1.386(6) . ? N2 C14 1.308(8) . ? N2 C13 1.376(8) . ? C1 C2 1.402(6) . ? C1 C2 1.402(6) 2_655 ? C1 H1 0.9300 . ? C2 C3 1.515(8) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.388(7) . ? C4 C13 1.410(7) . ? C5 C6 1.409(7) . ? C5 H5 0.9300 . ? C6 C7 1.420(9) . ? C6 C11 1.423(8) . ? C7 C8 1.367(9) . ? C7 H7 0.9300 . ? C8 C9 1.409(13) . ? C8 H8 0.9300 . ? C9 C10 1.346(11) . ? C9 H9 0.9300 . ? C10 C11 1.426(8) . ? C10 H10 0.9300 . ? C11 C12 1.386(9) . ? C12 C13 1.401(7) . ? C12 H12 0.9300 . ? C14 C15 1.463(7) . ? C14 C16 1.499(8) . ? C15 C17 1.471(7) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.408(7) . ? C17 C22 1.409(7) . ? C18 C19 1.396(7) . ? C19 C20 1.383(7) . ? C19 H19 0.9300 . ? C20 C21 1.400(8) . ? C20 H20 0.9300 . ? C21 C22 1.370(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9700 . ? C23 H23B 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 C18 Ir1 C18 93.1(3) . 2_655 ? C18 Ir1 N1 95.80(19) . 2_655 ? C18 Ir1 N1 79.23(19) 2_655 2_655 ? C18 Ir1 N1 79.23(19) . . ? C18 Ir1 N1 95.80(19) 2_655 . ? N1 Ir1 N1 172.8(2) 2_655 . ? C18 Ir1 O1 90.74(17) . . ? C18 Ir1 O1 173.20(16) 2_655 . ? N1 Ir1 O1 105.94(14) 2_655 . ? N1 Ir1 O1 79.43(14) . . ? C18 Ir1 O1 173.20(16) . 2_655 ? C18 Ir1 O1 90.74(17) 2_655 2_655 ? N1 Ir1 O1 79.43(14) 2_655 2_655 ? N1 Ir1 O1 105.95(14) . 2_655 ? O1 Ir1 O1 85.98(18) . 2_655 ? C2 O1 Ir1 125.9(3) . . ? C15 N1 C4 119.1(4) . . ? C15 N1 Ir1 115.8(3) . . ? C4 N1 Ir1 125.0(3) . . ? C14 N2 C13 118.1(5) . . ? C2 C1 C2 125.6(7) . 2_655 ? C2 C1 H1 117.2 . . ? C2 C1 H1 117.2 2_655 . ? O1 C2 C1 128.1(5) . . ? O1 C2 C3 114.9(5) . . ? C1 C2 C3 117.0(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C5 121.3(4) . . ? N1 C4 C13 119.4(5) . . ? C5 C4 C13 119.3(5) . . ? C4 C5 C6 120.5(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 121.4(5) . . ? C5 C6 C11 120.4(5) . . ? C7 C6 C11 118.2(5) . . ? C8 C7 C6 120.7(7) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.2(8) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 121.2(6) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.2(6) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C6 118.1(5) . . ? C12 C11 C10 122.5(6) . . ? C6 C11 C10 119.4(6) . . ? C11 C12 C13 121.8(5) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? N2 C13 C12 118.3(5) . . ? N2 C13 C4 121.8(5) . . ? C12 C13 C4 119.8(5) . . ? N2 C14 C15 122.0(5) . . ? N2 C14 C16 114.5(5) . . ? C15 C14 C16 123.5(5) . . ? N1 C15 C14 119.5(5) . . ? N1 C15 C17 113.9(4) . . ? C14 C15 C17 126.5(5) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 120.2(5) . . ? C18 C17 C15 113.4(4) . . ? C22 C17 C15 126.5(5) . . ? C19 C18 C17 117.9(4) . . ? C19 C18 Ir1 125.5(4) . . ? C17 C18 Ir1 116.1(4) . . ? C20 C19 C18 121.9(5) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C19 C20 C21 119.0(5) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 120.7(5) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C17 119.9(5) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? Cl2 C23 Cl1 114.1(9) . . ? Cl2 C23 H23A 108.7 . . ? Cl1 C23 H23A 108.7 . . ? Cl2 C23 H23B 108.7 . . ? Cl1 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.304 _refine_diff_density_min -1.755 _refine_diff_density_rms 0.173 _database_code_depnum_ccdc_archive 'CCDC 938240'