# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mohammad Nazeeruddin' _publ_contact_author_email MDKHAJA.NAZEERUDDIN@EPFL.CH _publ_section_title ; Panchromatic Phosphorescence Emission from a Single Molecule: Application to OLED ; loop_ _publ_author_name 'Mohammad Nazeeruddin' 'Etienne Baranoff' 'Henk J. Bolink' 'Eugenio Coronado' 'Filippo De Angelis' ; S.Fantacci ; 'Michael Gratzel' 'Kuppuswamy Kalyanasundaram' 'Cedric Klein' 'Michele Sessolo' # Attachment 'N966.CIF' data_n966 _database_code_depnum_ccdc_archive 'CCDC 730761' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 Ir N4 O2, C H2 Cl2' _chemical_formula_sum 'C26 H27 Cl2 Ir N4 O2' _chemical_formula_weight 690.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5352(5) _cell_length_b 9.6023(6) _cell_length_c 15.1243(12) _cell_angle_alpha 105.916(6) _cell_angle_beta 90.915(6) _cell_angle_gamma 93.309(5) _cell_volume 1328.75(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 87 _cell_measurement_theta_min 4.262 _cell_measurement_theta_max 21.414 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 5.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5399 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX II CCD' _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 29244 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6046 _reflns_number_gt 5670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _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^)+(0.0090P)^2^+1.2766P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00233(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6046 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0387 _refine_ls_wR_factor_gt 0.0371 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.433161(9) 0.187006(9) 0.263993(6) 0.01144(4) Uani 1 1 d . . . O1 O 0.36027(18) -0.03904(17) 0.22239(12) 0.0178(4) Uani 1 1 d . . . O2 O 0.24850(18) 0.23033(18) 0.34572(12) 0.0186(4) Uani 1 1 d . . . N1 N 0.3441(2) 0.2131(2) 0.14695(13) 0.0150(4) Uani 1 1 d . . . N2 N 0.3655(2) 0.2458(2) 0.00939(14) 0.0205(5) Uani 1 1 d . . . N3 N 0.5444(2) 0.1801(2) 0.37834(13) 0.0137(4) Uani 1 1 d . . . N4 N 0.6905(2) 0.2835(2) 0.49507(14) 0.0160(4) Uani 1 1 d . . . C1 C 0.2187(3) 0.2583(3) 0.12286(18) 0.0218(5) Uani 1 1 d . . . H1 H 0.1377 0.2729 0.1592 0.026 Uiso 1 1 calc R . . C2 C 0.2311(3) 0.2785(3) 0.03756(19) 0.0268(6) Uani 1 1 d . . . H2 H 0.1604 0.3094 0.0036 0.032 Uiso 1 1 calc R . . C3 C 0.4318(3) 0.2051(2) 0.07755(16) 0.0154(5) Uani 1 1 d . . . C4 C 0.4231(3) 0.2592(3) -0.07747(19) 0.0305(7) Uani 1 1 d . . . H4A H 0.5045 0.3296 -0.0645 0.046 Uiso 1 1 calc R . . H4B H 0.3510 0.2922 -0.1126 0.046 Uiso 1 1 calc R . . H4C H 0.4522 0.1646 -0.1134 0.046 Uiso 1 1 calc R . . C5 C 0.5734(3) 0.1613(2) 0.08987(17) 0.0157(5) Uani 1 1 d . . . C6 C 0.5963(2) 0.1456(2) 0.18023(16) 0.0141(5) Uani 1 1 d . . . C7 C 0.7285(3) 0.1010(3) 0.19904(18) 0.0190(5) Uani 1 1 d . . . H7 H 0.7480 0.0883 0.2580 0.023 Uiso 1 1 calc R . . C8 C 0.8320(3) 0.0749(3) 0.13321(19) 0.0246(6) Uani 1 1 d . . . H8 H 0.9208 0.0457 0.1483 0.029 Uiso 1 1 calc R . . C9 C 0.8067(3) 0.0910(3) 0.04583(19) 0.0244(6) Uani 1 1 d . . . H9 H 0.8779 0.0735 0.0017 0.029 Uiso 1 1 calc R . . C10 C 0.6763(3) 0.1329(3) 0.02338(18) 0.0202(5) Uani 1 1 d . . . H10 H 0.6575 0.1422 -0.0365 0.024 Uiso 1 1 calc R . . C11 C 0.5075(2) 0.3955(2) 0.30862(16) 0.0143(5) Uani 1 1 d . . . C12 C 0.4833(3) 0.5095(3) 0.26998(17) 0.0170(5) Uani 1 1 d . . . H12 H 0.4269 0.4905 0.2151 0.020 Uiso 1 1 calc R . . C13 C 0.5406(3) 0.6509(3) 0.31071(18) 0.0195(5) Uani 1 1 d . . . H13 H 0.5227 0.7260 0.2830 0.023 Uiso 1 1 calc R . . C14 C 0.6232(3) 0.6826(3) 0.39111(18) 0.0201(5) Uani 1 1 d . . . H14 H 0.6617 0.7788 0.4179 0.024 Uiso 1 1 calc R . . C15 C 0.6494(3) 0.5734(3) 0.43223(17) 0.0175(5) Uani 1 1 d . . . H15 H 0.7045 0.5948 0.4877 0.021 Uiso 1 1 calc R . . C16 C 0.5937(2) 0.4313(2) 0.39106(16) 0.0138(5) Uani 1 1 d . . . C17 C 0.6127(2) 0.3057(2) 0.42472(16) 0.0138(5) Uani 1 1 d . . . C18 C 0.6692(3) 0.1391(3) 0.49273(18) 0.0195(5) Uani 1 1 d . . . H18 H 0.7100 0.0924 0.5337 0.023 Uiso 1 1 calc R . . C19 C 0.5782(3) 0.0762(3) 0.42023(17) 0.0185(5) Uani 1 1 d . . . H19 H 0.5441 -0.0228 0.4019 0.022 Uiso 1 1 calc R . . C20 C 0.7817(3) 0.3901(3) 0.56257(18) 0.0220(6) Uani 1 1 d . . . H20A H 0.8553 0.4307 0.5307 0.033 Uiso 1 1 calc R . . H20B H 0.8249 0.3428 0.6050 0.033 Uiso 1 1 calc R . . H20C H 0.7258 0.4682 0.5972 0.033 Uiso 1 1 calc R . . C21 C 0.2084(3) -0.2495(3) 0.1970(2) 0.0279(6) Uani 1 1 d . . . H21A H 0.1876 -0.2630 0.1314 0.042 Uiso 1 1 calc R . . H21B H 0.1263 -0.2835 0.2253 0.042 Uiso 1 1 calc R . . H21C H 0.2888 -0.3051 0.2042 0.042 Uiso 1 1 calc R . . C22 C 0.2434(3) -0.0896(3) 0.24376(17) 0.0184(5) Uani 1 1 d . . . C23 C 0.1467(3) -0.0142(3) 0.30464(18) 0.0220(5) Uani 1 1 d . . . H23 H 0.0670 -0.0701 0.3158 0.026 Uiso 1 1 calc R . . C24 C 0.1538(3) 0.1350(3) 0.35132(17) 0.0196(5) Uani 1 1 d . . . C25 C 0.0363(3) 0.1919(3) 0.4152(2) 0.0314(7) Uani 1 1 d . . . H25A H 0.0760 0.2387 0.4771 0.047 Uiso 1 1 calc R . . H25B H -0.0300 0.1111 0.4173 0.047 Uiso 1 1 calc R . . H25C H -0.0129 0.2627 0.3924 0.047 Uiso 1 1 calc R . . Cl1 Cl 1.04027(8) 0.53364(11) 0.71695(6) 0.0462(2) Uani 1 1 d . . . Cl2 Cl 1.09903(9) 0.51232(9) 0.90340(6) 0.0434(2) Uani 1 1 d . . . C26 C 1.1709(3) 0.5405(3) 0.8013(2) 0.0315(7) Uani 1 1 d . . . H26A H 1.2238 0.6362 0.8164 0.038 Uiso 1 1 calc R . . H26B H 1.2377 0.4652 0.7765 0.038 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 0.01212(5) 0.00946(5) 0.01273(5) 0.00321(3) 0.00212(3) -0.00074(3) O1 0.0188(9) 0.0122(8) 0.0208(9) 0.0028(7) 0.0025(7) -0.0038(7) O2 0.0177(9) 0.0177(8) 0.0196(9) 0.0039(7) 0.0068(7) 0.0007(7) N1 0.0151(10) 0.0139(9) 0.0156(10) 0.0034(8) 0.0009(8) 0.0010(8) N2 0.0260(12) 0.0212(11) 0.0157(10) 0.0065(9) 0.0024(9) 0.0058(9) N3 0.0156(10) 0.0115(9) 0.0149(10) 0.0051(8) 0.0030(8) -0.0005(8) N4 0.0162(10) 0.0170(10) 0.0150(10) 0.0049(8) 0.0023(8) 0.0012(8) C1 0.0183(13) 0.0237(13) 0.0237(13) 0.0061(11) 0.0016(10) 0.0066(10) C2 0.0256(14) 0.0308(15) 0.0265(14) 0.0098(12) -0.0011(11) 0.0121(12) C3 0.0187(12) 0.0112(10) 0.0155(12) 0.0024(9) 0.0004(9) -0.0004(9) C4 0.0420(18) 0.0343(16) 0.0204(14) 0.0143(12) 0.0075(12) 0.0111(13) C5 0.0164(12) 0.0123(11) 0.0175(12) 0.0030(9) 0.0013(9) -0.0011(9) C6 0.0146(11) 0.0088(10) 0.0181(12) 0.0028(9) 0.0016(9) -0.0015(9) C7 0.0164(12) 0.0190(12) 0.0220(13) 0.0066(10) -0.0008(10) 0.0012(10) C8 0.0144(12) 0.0268(14) 0.0323(15) 0.0074(12) 0.0029(11) 0.0040(10) C9 0.0181(13) 0.0255(14) 0.0279(14) 0.0037(11) 0.0116(11) 0.0022(10) C10 0.0216(13) 0.0193(12) 0.0180(12) 0.0027(10) 0.0040(10) -0.0020(10) C11 0.0153(11) 0.0135(11) 0.0138(11) 0.0031(9) 0.0056(9) 0.0021(9) C12 0.0192(12) 0.0162(11) 0.0171(12) 0.0062(10) 0.0034(10) 0.0040(9) C13 0.0238(13) 0.0129(11) 0.0252(13) 0.0097(10) 0.0094(11) 0.0042(10) C14 0.0218(13) 0.0098(11) 0.0263(14) 0.0009(10) 0.0050(10) -0.0006(9) C15 0.0202(12) 0.0138(11) 0.0169(12) 0.0015(9) 0.0035(10) -0.0008(9) C16 0.0128(11) 0.0120(11) 0.0169(12) 0.0041(9) 0.0059(9) 0.0006(9) C17 0.0133(11) 0.0125(11) 0.0159(12) 0.0042(9) 0.0048(9) 0.0008(9) C18 0.0209(13) 0.0191(12) 0.0213(13) 0.0097(10) 0.0035(10) 0.0049(10) C19 0.0237(13) 0.0131(11) 0.0208(13) 0.0084(10) 0.0036(10) 0.0003(10) C20 0.0199(13) 0.0233(13) 0.0204(13) 0.0025(11) -0.0033(10) -0.0003(10) C21 0.0278(15) 0.0186(13) 0.0340(16) 0.0041(12) 0.0001(12) -0.0096(11) C22 0.0196(12) 0.0186(12) 0.0179(12) 0.0077(10) -0.0026(10) -0.0046(10) C23 0.0177(12) 0.0243(13) 0.0235(13) 0.0073(11) 0.0047(10) -0.0072(10) C24 0.0156(12) 0.0257(13) 0.0189(13) 0.0089(11) 0.0028(10) -0.0013(10) C25 0.0236(15) 0.0347(16) 0.0339(16) 0.0059(13) 0.0139(12) -0.0006(12) Cl1 0.0275(4) 0.0699(6) 0.0345(4) 0.0052(4) -0.0032(3) -0.0056(4) Cl2 0.0435(5) 0.0421(4) 0.0529(5) 0.0285(4) -0.0001(4) -0.0034(4) C26 0.0164(13) 0.0324(15) 0.0462(18) 0.0121(14) 0.0015(12) -0.0013(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C6 2.010(2) . ? Ir1 C11 2.011(2) . ? Ir1 N3 2.033(2) . ? Ir1 N1 2.034(2) . ? Ir1 O1 2.1572(16) . ? Ir1 O2 2.1618(17) . ? O1 C22 1.271(3) . ? O2 C24 1.269(3) . ? N1 C3 1.341(3) . ? N1 C1 1.372(3) . ? N2 C3 1.358(3) . ? N2 C2 1.383(3) . ? N2 C4 1.467(3) . ? N3 C17 1.342(3) . ? N3 C19 1.370(3) . ? N4 C17 1.359(3) . ? N4 C18 1.380(3) . ? N4 C20 1.464(3) . ? C1 C2 1.362(4) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C5 1.461(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C10 1.401(3) . ? C5 C6 1.430(3) . ? C6 C7 1.404(3) . ? C7 C8 1.397(4) . ? C7 H7 0.9500 . ? C8 C9 1.391(4) . ? C8 H8 0.9500 . ? C9 C10 1.393(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.403(3) . ? C11 C16 1.431(3) . ? C12 C13 1.402(3) . ? C12 H12 0.9500 . ? C13 C14 1.389(4) . ? C13 H13 0.9500 . ? C14 C15 1.390(3) . ? C14 H14 0.9500 . ? C15 C16 1.404(3) . ? C15 H15 0.9500 . ? C16 C17 1.451(3) . ? C18 C19 1.366(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.519(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.400(4) . ? C23 C24 1.410(4) . ? C23 H23 0.9500 . ? C24 C25 1.517(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Cl1 C26 1.754(3) . ? Cl2 C26 1.780(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 Ir1 C11 89.22(9) . . ? C6 Ir1 N3 94.79(9) . . ? C11 Ir1 N3 80.16(9) . . ? C6 Ir1 N1 80.13(9) . . ? C11 Ir1 N1 93.55(9) . . ? N3 Ir1 N1 172.03(8) . . ? C6 Ir1 O1 90.84(8) . . ? C11 Ir1 O1 176.75(8) . . ? N3 Ir1 O1 96.59(7) . . ? N1 Ir1 O1 89.66(7) . . ? C6 Ir1 O2 176.01(8) . . ? C11 Ir1 O2 91.91(8) . . ? N3 Ir1 O2 89.17(7) . . ? N1 Ir1 O2 95.98(7) . . ? O1 Ir1 O2 88.24(6) . . ? C22 O1 Ir1 124.84(16) . . ? C24 O2 Ir1 124.75(16) . . ? C3 N1 C1 108.2(2) . . ? C3 N1 Ir1 115.10(16) . . ? C1 N1 Ir1 135.91(17) . . ? C3 N2 C2 107.3(2) . . ? C3 N2 C4 127.9(2) . . ? C2 N2 C4 124.7(2) . . ? C17 N3 C19 107.8(2) . . ? C17 N3 Ir1 115.25(16) . . ? C19 N3 Ir1 136.81(16) . . ? C17 N4 C18 107.7(2) . . ? C17 N4 C20 127.6(2) . . ? C18 N4 C20 124.7(2) . . ? C2 C1 N1 107.8(2) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 N2 107.5(2) . . ? C1 C2 H2 126.2 . . ? N2 C2 H2 126.2 . . ? N1 C3 N2 109.1(2) . . ? N1 C3 C5 117.2(2) . . ? N2 C3 C5 133.7(2) . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C6 122.1(2) . . ? C10 C5 C3 126.4(2) . . ? C6 C5 C3 111.5(2) . . ? C7 C6 C5 116.3(2) . . ? C7 C6 Ir1 128.03(19) . . ? C5 C6 Ir1 115.69(17) . . ? C8 C7 C6 121.7(2) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.7(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C5 119.5(2) . . ? C9 C10 H10 120.3 . . ? C5 C10 H10 120.3 . . ? C12 C11 C16 116.5(2) . . ? C12 C11 Ir1 128.13(18) . . ? C16 C11 Ir1 115.35(17) . . ? C13 C12 C11 121.4(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C11 121.9(2) . . ? C15 C16 C17 126.1(2) . . ? C11 C16 C17 112.0(2) . . ? N3 C17 N4 109.2(2) . . ? N3 C17 C16 117.2(2) . . ? N4 C17 C16 133.6(2) . . ? C19 C18 N4 106.9(2) . . ? C19 C18 H18 126.5 . . ? N4 C18 H18 126.5 . . ? C18 C19 N3 108.4(2) . . ? C18 C19 H19 125.8 . . ? N3 C19 H19 125.8 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C22 C23 127.1(2) . . ? O1 C22 C21 114.9(2) . . ? C23 C22 C21 118.1(2) . . ? C22 C23 C24 127.7(2) . . ? C22 C23 H23 116.2 . . ? C24 C23 H23 116.2 . . ? O2 C24 C23 127.1(2) . . ? O2 C24 C25 114.8(2) . . ? C23 C24 C25 118.1(2) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Cl1 C26 Cl2 112.01(16) . . ? Cl1 C26 H26A 109.2 . . ? Cl2 C26 H26A 109.2 . . ? Cl1 C26 H26B 109.2 . . ? Cl2 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 Ir1 O1 C22 -171.4(2) . . . . ? N3 Ir1 O1 C22 93.6(2) . . . . ? N1 Ir1 O1 C22 -91.3(2) . . . . ? O2 Ir1 O1 C22 4.69(19) . . . . ? C11 Ir1 O2 C24 -177.2(2) . . . . ? N3 Ir1 O2 C24 -97.0(2) . . . . ? N1 Ir1 O2 C24 89.1(2) . . . . ? O1 Ir1 O2 C24 -0.4(2) . . . . ? C6 Ir1 N1 C3 -5.69(16) . . . . ? C11 Ir1 N1 C3 82.90(17) . . . . ? O1 Ir1 N1 C3 -96.60(16) . . . . ? O2 Ir1 N1 C3 175.20(16) . . . . ? C6 Ir1 N1 C1 -173.9(2) . . . . ? C11 Ir1 N1 C1 -85.3(2) . . . . ? O1 Ir1 N1 C1 95.2(2) . . . . ? O2 Ir1 N1 C1 7.0(2) . . . . ? C6 Ir1 N3 C17 86.72(17) . . . . ? C11 Ir1 N3 C17 -1.66(17) . . . . ? O1 Ir1 N3 C17 178.12(16) . . . . ? O2 Ir1 N3 C17 -93.74(17) . . . . ? C6 Ir1 N3 C19 -87.8(2) . . . . ? C11 Ir1 N3 C19 -176.1(3) . . . . ? O1 Ir1 N3 C19 3.6(2) . . . . ? O2 Ir1 N3 C19 91.8(2) . . . . ? C3 N1 C1 C2 -0.2(3) . . . . ? Ir1 N1 C1 C2 168.56(19) . . . . ? N1 C1 C2 N2 -0.2(3) . . . . ? C3 N2 C2 C1 0.6(3) . . . . ? C4 N2 C2 C1 -177.5(2) . . . . ? C1 N1 C3 N2 0.6(3) . . . . ? Ir1 N1 C3 N2 -170.80(15) . . . . ? C1 N1 C3 C5 178.8(2) . . . . ? Ir1 N1 C3 C5 7.4(3) . . . . ? C2 N2 C3 N1 -0.7(3) . . . . ? C4 N2 C3 N1 177.3(2) . . . . ? C2 N2 C3 C5 -178.6(3) . . . . ? C4 N2 C3 C5 -0.5(4) . . . . ? N1 C3 C5 C10 173.5(2) . . . . ? N2 C3 C5 C10 -8.8(4) . . . . ? N1 C3 C5 C6 -4.8(3) . . . . ? N2 C3 C5 C6 172.9(2) . . . . ? C10 C5 C6 C7 0.4(3) . . . . ? C3 C5 C6 C7 178.8(2) . . . . ? C10 C5 C6 Ir1 -178.55(18) . . . . ? C3 C5 C6 Ir1 -0.1(2) . . . . ? C11 Ir1 C6 C7 90.4(2) . . . . ? N3 Ir1 C6 C7 10.4(2) . . . . ? N1 Ir1 C6 C7 -175.8(2) . . . . ? O1 Ir1 C6 C7 -86.3(2) . . . . ? C11 Ir1 C6 C5 -90.74(18) . . . . ? N3 Ir1 C6 C5 -170.81(17) . . . . ? N1 Ir1 C6 C5 3.00(16) . . . . ? O1 Ir1 C6 C5 92.51(17) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? Ir1 C6 C7 C8 179.39(19) . . . . ? C6 C7 C8 C9 -0.6(4) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C8 C9 C10 C5 1.3(4) . . . . ? C6 C5 C10 C9 -1.4(4) . . . . ? C3 C5 C10 C9 -179.5(2) . . . . ? C6 Ir1 C11 C12 86.2(2) . . . . ? N3 Ir1 C11 C12 -178.8(2) . . . . ? N1 Ir1 C11 C12 6.2(2) . . . . ? O2 Ir1 C11 C12 -89.9(2) . . . . ? C6 Ir1 C11 C16 -94.97(18) . . . . ? N3 Ir1 C11 C16 0.03(17) . . . . ? N1 Ir1 C11 C16 -175.03(17) . . . . ? O2 Ir1 C11 C16 88.85(17) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? Ir1 C11 C12 C13 178.55(18) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 1.0(4) . . . . ? C14 C15 C16 C11 -1.5(4) . . . . ? C14 C15 C16 C17 179.3(2) . . . . ? C12 C11 C16 C15 1.1(3) . . . . ? Ir1 C11 C16 C15 -177.87(18) . . . . ? C12 C11 C16 C17 -179.6(2) . . . . ? Ir1 C11 C16 C17 1.4(3) . . . . ? C19 N3 C17 N4 0.5(3) . . . . ? Ir1 N3 C17 N4 -175.53(15) . . . . ? C19 N3 C17 C16 179.0(2) . . . . ? Ir1 N3 C17 C16 3.0(3) . . . . ? C18 N4 C17 N3 -0.4(3) . . . . ? C20 N4 C17 N3 179.6(2) . . . . ? C18 N4 C17 C16 -178.6(3) . . . . ? C20 N4 C17 C16 1.4(4) . . . . ? C15 C16 C17 N3 176.4(2) . . . . ? C11 C16 C17 N3 -2.9(3) . . . . ? C15 C16 C17 N4 -5.5(4) . . . . ? C11 C16 C17 N4 175.2(2) . . . . ? C17 N4 C18 C19 0.1(3) . . . . ? C20 N4 C18 C19 -179.9(2) . . . . ? N4 C18 C19 N3 0.2(3) . . . . ? C17 N3 C19 C18 -0.4(3) . . . . ? Ir1 N3 C19 C18 174.31(18) . . . . ? Ir1 O1 C22 C23 -7.0(4) . . . . ? Ir1 O1 C22 C21 173.14(16) . . . . ? O1 C22 C23 C24 3.9(5) . . . . ? C21 C22 C23 C24 -176.2(3) . . . . ? Ir1 O2 C24 C23 -2.1(4) . . . . ? Ir1 O2 C24 C25 178.49(17) . . . . ? C22 C23 C24 O2 1.4(5) . . . . ? C22 C23 C24 C25 -179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.707 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.092