# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fuyou Li' _publ_contact_author_email fyli@fudan.edu.cn _publ_section_title ; A Cyclometalated Iridium(III) Complex with Enhanced Phosphorescence Emission in the Solid State (EPESS): Synthesis, Characterization, and its Application in Bioimaging ; loop_ _publ_author_name 'Fuyou Li' 'Huazhou Wu' 'Qiang Zhao' 'Tianshe Yang' ; Jing''Li ; 'Chunyan Zhou' # Attachment '- Ir(ppy)2(L2).cif' data_f81112b _database_code_depnum_ccdc_archive 'CCDC 709614' #TrackingRef '- Ir(ppy)2(L2).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H31 Ir N4 O2' _chemical_formula_sum 'C40 H31 Ir N4 O2' _chemical_formula_weight 791.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_HALL '-P 2ybc' 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 18.466(9) _cell_length_b 10.009(5) _cell_length_c 18.204(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.668(13) _cell_angle_gamma 90.00 _cell_volume 3240(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 784 _cell_measurement_theta_min 2.098 _cell_measurement_theta_max 25.241 _exptl_crystal_description column _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 4.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5739 _exptl_absorpt_correction_T_max 0.7318 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11216 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5557 _reflns_number_gt 3587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0323P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5557 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _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 0.289154(14) 0.82294(3) 0.161277(15) 0.03964(10) Uani 1 1 d . . . O1 O 0.1915(2) 0.9029(4) 0.1906(3) 0.0462(12) Uani 1 1 d . . . O2 O 0.2361(2) 0.8941(5) 0.0467(2) 0.0481(12) Uani 1 1 d . . . N1 N 0.2367(3) 0.6426(5) 0.1454(3) 0.0461(15) Uani 1 1 d . . . N2 N 0.3508(3) 0.9951(5) 0.1788(3) 0.0446(15) Uani 1 1 d . . . N3 N 0.0817(3) 1.0245(5) 0.1658(3) 0.0436(14) Uani 1 1 d . . . N4 N 0.0383(3) 1.1063(5) 0.1080(3) 0.0477(15) Uani 1 1 d . . . C1 C 0.1961(4) 0.5955(8) 0.0778(4) 0.058(2) Uani 1 1 d . . . H1A H 0.1892 0.6495 0.0348 0.069 Uiso 1 1 calc R . . C2 C 0.1653(4) 0.4729(9) 0.0699(6) 0.077(3) Uani 1 1 d . . . H2A H 0.1375 0.4428 0.0223 0.092 Uiso 1 1 calc R . . C3 C 0.1752(5) 0.3931(9) 0.1325(7) 0.084(3) Uani 1 1 d . . . H3A H 0.1541 0.3081 0.1279 0.101 Uiso 1 1 calc R . . C4 C 0.2163(5) 0.4391(8) 0.2020(5) 0.071(2) Uani 1 1 d . . . H4A H 0.2224 0.3855 0.2450 0.085 Uiso 1 1 calc R . . C5 C 0.2492(4) 0.5659(7) 0.2090(4) 0.0435(18) Uani 1 1 d . . . C6 C 0.2974(4) 0.6261(7) 0.2777(4) 0.0455(18) Uani 1 1 d . . . C7 C 0.3166(4) 0.5648(8) 0.3493(5) 0.062(2) Uani 1 1 d . . . H7A H 0.2995 0.4791 0.3551 0.075 Uiso 1 1 calc R . . C8 C 0.3609(5) 0.6317(10) 0.4113(5) 0.073(3) Uani 1 1 d . . . H8A H 0.3724 0.5922 0.4593 0.088 Uiso 1 1 calc R . . C9 C 0.3885(5) 0.7571(10) 0.4026(5) 0.072(2) Uani 1 1 d . . . H9A H 0.4178 0.8024 0.4448 0.087 Uiso 1 1 calc R . . C10 C 0.3726(4) 0.8157(7) 0.3309(4) 0.057(2) Uani 1 1 d . . . H10A H 0.3930 0.8990 0.3260 0.068 Uiso 1 1 calc R . . C11 C 0.3272(4) 0.7546(6) 0.2660(4) 0.0444(18) Uani 1 1 d . . . C12 C 0.3314(4) 1.1106(8) 0.2038(4) 0.056(2) Uani 1 1 d . . . H12A H 0.2860 1.1146 0.2166 0.068 Uiso 1 1 calc R . . C13 C 0.3741(5) 1.2246(8) 0.2122(4) 0.063(2) Uani 1 1 d . . . H13A H 0.3580 1.3034 0.2297 0.076 Uiso 1 1 calc R . . C14 C 0.4397(5) 1.2185(8) 0.1942(5) 0.076(3) Uani 1 1 d . . . H14A H 0.4704 1.2936 0.1999 0.091 Uiso 1 1 calc R . . C15 C 0.4617(4) 1.1016(8) 0.1674(5) 0.068(2) Uani 1 1 d . . . H15A H 0.5068 1.0980 0.1540 0.082 Uiso 1 1 calc R . . C16 C 0.4167(4) 0.9887(7) 0.1604(4) 0.0442(18) Uani 1 1 d . . . C17 C 0.4350(4) 0.8569(7) 0.1361(4) 0.052(2) Uani 1 1 d . . . C18 C 0.5011(4) 0.8282(9) 0.1148(4) 0.065(2) Uani 1 1 d . . . H18A H 0.5352 0.8954 0.1127 0.078 Uiso 1 1 calc R . . C19 C 0.5141(5) 0.6990(11) 0.0972(5) 0.074(3) Uani 1 1 d . . . H19A H 0.5579 0.6785 0.0837 0.089 Uiso 1 1 calc R . . C20 C 0.4644(4) 0.6003(9) 0.0991(4) 0.065(2) Uani 1 1 d . . . H20A H 0.4751 0.5131 0.0879 0.078 Uiso 1 1 calc R . . C21 C 0.3973(4) 0.6278(8) 0.1174(4) 0.056(2) Uani 1 1 d . . . H21A H 0.3636 0.5588 0.1174 0.067 Uiso 1 1 calc R . . C22 C 0.3799(4) 0.7586(7) 0.1359(4) 0.0457(18) Uani 1 1 d . . . C23 C 0.0601(4) 1.0059(7) 0.2341(4) 0.0440(18) Uani 1 1 d . . . C24 C 0.0909(4) 0.9087(7) 0.2858(4) 0.058(2) Uani 1 1 d . . . H24A H 0.1270 0.8507 0.2770 0.070 Uiso 1 1 calc R . . C25 C 0.0671(5) 0.8982(8) 0.3518(5) 0.075(3) Uani 1 1 d . . . H25A H 0.0881 0.8324 0.3872 0.090 Uiso 1 1 calc R . . C26 C 0.0141(5) 0.9810(10) 0.3662(5) 0.078(3) Uani 1 1 d . . . H26A H -0.0007 0.9720 0.4109 0.093 Uiso 1 1 calc R . . C27 C -0.0173(5) 1.0780(10) 0.3139(5) 0.084(3) Uani 1 1 d . . . H27A H -0.0538 1.1352 0.3226 0.100 Uiso 1 1 calc R . . C28 C 0.0061(5) 1.0897(9) 0.2477(5) 0.071(2) Uani 1 1 d . . . H28A H -0.0150 1.1552 0.2121 0.086 Uiso 1 1 calc R . . C29 C 0.0360(4) 1.1851(7) -0.0174(4) 0.0530(19) Uani 1 1 d . . . H29A H -0.0075 1.2304 -0.0104 0.079 Uiso 1 1 calc R . . H29B H 0.0214 1.1285 -0.0615 0.079 Uiso 1 1 calc R . . H29C H 0.0720 1.2496 -0.0245 0.079 Uiso 1 1 calc R . . C30 C 0.0706(4) 1.1018(6) 0.0518(4) 0.0413(17) Uani 1 1 d . . . C31 C 0.1352(3) 1.0173(7) 0.0683(4) 0.0389(16) Uani 1 1 d . . . C32 C 0.1424(4) 0.9734(7) 0.1447(4) 0.0418(17) Uani 1 1 d . . . C33 C 0.1822(4) 0.9746(7) 0.0238(4) 0.0431(17) Uani 1 1 d . . . C34 C 0.1707(4) 1.0231(7) -0.0580(4) 0.059(2) Uani 1 1 d . . . H34A H 0.1889 0.9557 -0.0869 0.071 Uiso 1 1 calc R . . H34B H 0.1173 1.0355 -0.0816 0.071 Uiso 1 1 calc R . . C35 C 0.2116(4) 1.1535(7) -0.0610(4) 0.0509(19) Uani 1 1 d . . . C36 C 0.1840(5) 1.2383(10) -0.1213(5) 0.081(3) Uani 1 1 d . . . H36 H 0.1397 1.2173 -0.1580 0.097 Uiso 1 1 calc R . . C37 C 0.2219(7) 1.3542(12) -0.1275(7) 0.114(4) Uani 1 1 d . . . H37A H 0.2032 1.4106 -0.1689 0.137 Uiso 1 1 calc R . . C38 C 0.2879(7) 1.3885(10) -0.0725(8) 0.105(4) Uani 1 1 d . . . H38A H 0.3136 1.4669 -0.0766 0.127 Uiso 1 1 calc R . . C39 C 0.3140(6) 1.3030(9) -0.0122(6) 0.088(3) Uani 1 1 d . . . H39A H 0.3578 1.3234 0.0253 0.106 Uiso 1 1 calc R . . C40 C 0.2753(5) 1.1868(8) -0.0071(5) 0.071(2) Uani 1 1 d . . . H40A H 0.2934 1.1302 0.0343 0.085 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 0.03683(15) 0.04450(16) 0.03769(16) 0.00049(16) 0.01025(11) -0.00099(16) O1 0.041(3) 0.057(3) 0.047(3) 0.003(2) 0.023(2) 0.005(2) O2 0.050(3) 0.059(3) 0.033(3) 0.003(2) 0.008(2) 0.010(3) N1 0.030(3) 0.051(4) 0.061(4) -0.006(3) 0.017(3) -0.005(3) N2 0.046(4) 0.042(4) 0.045(4) 0.009(3) 0.009(3) 0.000(3) N3 0.037(3) 0.053(4) 0.042(4) -0.005(3) 0.014(3) 0.001(3) N4 0.047(4) 0.045(3) 0.049(4) -0.002(3) 0.010(3) 0.001(3) C1 0.045(4) 0.074(6) 0.048(5) -0.012(4) 0.002(4) -0.010(4) C2 0.063(6) 0.061(6) 0.099(8) -0.024(6) 0.007(5) -0.018(5) C3 0.066(6) 0.051(5) 0.135(10) -0.011(6) 0.026(6) -0.015(5) C4 0.072(6) 0.056(5) 0.091(7) 0.007(5) 0.032(5) -0.013(5) C5 0.043(4) 0.043(4) 0.052(5) 0.007(4) 0.026(4) 0.002(3) C6 0.038(4) 0.062(5) 0.045(5) 0.003(4) 0.025(4) 0.014(4) C7 0.073(6) 0.070(5) 0.059(6) 0.027(5) 0.042(5) 0.013(5) C8 0.071(6) 0.116(8) 0.040(5) 0.014(5) 0.029(5) 0.018(6) C9 0.077(6) 0.089(7) 0.044(5) -0.006(5) 0.005(5) 0.017(5) C10 0.063(5) 0.055(5) 0.050(5) 0.004(4) 0.011(4) 0.021(4) C11 0.057(5) 0.034(4) 0.034(4) -0.007(3) -0.001(4) 0.007(4) C12 0.047(5) 0.064(5) 0.056(5) -0.006(4) 0.010(4) -0.002(4) C13 0.060(5) 0.053(5) 0.070(6) -0.007(4) 0.005(5) -0.008(4) C14 0.071(6) 0.068(6) 0.077(7) 0.008(5) 0.001(5) -0.031(5) C15 0.062(5) 0.067(6) 0.072(6) 0.001(5) 0.011(5) -0.016(5) C16 0.038(4) 0.050(5) 0.044(4) 0.010(4) 0.010(3) -0.005(4) C17 0.053(5) 0.063(5) 0.035(4) 0.009(4) 0.003(4) 0.001(4) C18 0.042(4) 0.093(7) 0.063(5) 0.004(5) 0.021(4) -0.008(5) C19 0.046(5) 0.121(8) 0.061(6) -0.001(6) 0.024(4) 0.019(6) C20 0.055(5) 0.088(6) 0.055(5) 0.001(5) 0.019(4) 0.019(5) C21 0.052(5) 0.062(5) 0.053(5) 0.003(4) 0.013(4) 0.003(4) C22 0.049(4) 0.049(4) 0.038(4) 0.001(4) 0.010(4) -0.011(4) C23 0.039(4) 0.055(5) 0.042(4) -0.013(4) 0.020(4) -0.012(4) C24 0.067(5) 0.066(5) 0.054(5) 0.004(4) 0.038(4) 0.001(4) C25 0.105(7) 0.062(5) 0.062(6) 0.003(5) 0.029(6) -0.011(5) C26 0.081(7) 0.102(7) 0.067(6) -0.014(6) 0.050(6) -0.011(6) C27 0.077(6) 0.116(8) 0.073(7) -0.012(6) 0.047(6) 0.024(6) C28 0.069(6) 0.095(7) 0.053(5) 0.001(5) 0.022(5) 0.015(5) C29 0.051(4) 0.052(4) 0.053(5) 0.001(4) 0.009(4) 0.000(4) C30 0.042(4) 0.042(4) 0.039(4) -0.005(3) 0.010(4) -0.009(3) C31 0.033(4) 0.052(4) 0.034(4) -0.003(3) 0.013(3) -0.010(3) C32 0.036(4) 0.043(4) 0.046(5) -0.005(4) 0.010(4) -0.004(3) C33 0.039(4) 0.042(4) 0.045(4) 0.000(4) 0.005(4) -0.011(3) C34 0.058(5) 0.078(6) 0.040(5) 0.000(4) 0.013(4) 0.007(4) C35 0.058(5) 0.056(5) 0.050(5) 0.014(4) 0.033(4) 0.015(4) C36 0.068(6) 0.105(7) 0.083(7) 0.044(6) 0.044(5) 0.033(6) C37 0.126(10) 0.125(10) 0.116(10) 0.082(8) 0.072(8) 0.063(8) C38 0.116(9) 0.069(7) 0.169(13) 0.040(8) 0.103(9) 0.030(7) C39 0.101(7) 0.081(7) 0.099(8) 0.007(6) 0.054(6) -0.013(6) C40 0.092(7) 0.071(6) 0.058(5) 0.013(5) 0.033(5) -0.006(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 C22 1.962(7) . ? Ir1 C11 1.968(6) . ? Ir1 N1 2.032(5) . ? Ir1 N2 2.042(5) . ? Ir1 O1 2.167(4) . ? Ir1 O2 2.171(4) . ? O1 C32 1.269(7) . ? O2 C33 1.262(7) . ? N1 C1 1.343(8) . ? N1 C5 1.356(8) . ? N2 C12 1.327(8) . ? N2 C16 1.350(8) . ? N3 C32 1.379(8) . ? N3 N4 1.401(7) . ? N3 C23 1.417(8) . ? N4 C30 1.317(8) . ? C1 C2 1.344(9) . ? C1 H1A 0.9300 . ? C2 C3 1.362(11) . ? C2 H2A 0.9300 . ? C3 C4 1.368(11) . ? C3 H3A 0.9300 . ? C4 C5 1.399(9) . ? C4 H4A 0.9300 . ? C5 C6 1.456(9) . ? C6 C7 1.397(9) . ? C6 C11 1.437(9) . ? C7 C8 1.375(10) . ? C7 H7A 0.9300 . ? C8 C9 1.380(11) . ? C8 H8A 0.9300 . ? C9 C10 1.388(10) . ? C9 H9A 0.9300 . ? C10 C11 1.392(9) . ? C10 H10A 0.9300 . ? C12 C13 1.371(9) . ? C12 H12A 0.9300 . ? C13 C14 1.339(10) . ? C13 H13A 0.9300 . ? C14 C15 1.370(11) . ? C14 H14A 0.9300 . ? C15 C16 1.387(9) . ? C15 H15A 0.9300 . ? C16 C17 1.460(9) . ? C17 C18 1.407(10) . ? C17 C22 1.416(9) . ? C18 C19 1.368(10) . ? C18 H18A 0.9300 . ? C19 C20 1.355(11) . ? C19 H19A 0.9300 . ? C20 C21 1.395(9) . ? C20 H20A 0.9300 . ? C21 C22 1.411(9) . ? C21 H21A 0.9300 . ? C23 C24 1.366(9) . ? C23 C28 1.375(9) . ? C24 C25 1.390(10) . ? C24 H24A 0.9300 . ? C25 C26 1.362(10) . ? C25 H25A 0.9300 . ? C26 C27 1.374(11) . ? C26 H26A 0.9300 . ? C27 C28 1.391(11) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 C30 1.501(9) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.426(9) . ? C31 C33 1.404(9) . ? C31 C32 1.429(9) . ? C33 C34 1.525(9) . ? C34 C35 1.516(9) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C40 1.355(10) . ? C35 C36 1.371(10) . ? C36 C37 1.375(13) . ? C36 H36 0.9300 . ? C37 C38 1.396(14) . ? C37 H37A 0.9300 . ? C38 C39 1.372(12) . ? C38 H38A 0.9300 . ? C39 C40 1.381(10) . ? C39 H39A 0.9300 . ? C40 H40A 0.9300 . ? 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 C22 Ir1 C11 90.6(3) . . ? C22 Ir1 N1 94.6(2) . . ? C11 Ir1 N1 82.0(3) . . ? C22 Ir1 N2 80.7(3) . . ? C11 Ir1 N2 96.0(2) . . ? N1 Ir1 N2 174.9(2) . . ? C22 Ir1 O1 177.3(2) . . ? C11 Ir1 O1 89.5(2) . . ? N1 Ir1 O1 88.06(19) . . ? N2 Ir1 O1 96.6(2) . . ? C22 Ir1 O2 94.2(2) . . ? C11 Ir1 O2 174.3(2) . . ? N1 Ir1 O2 94.6(2) . . ? N2 Ir1 O2 87.77(18) . . ? O1 Ir1 O2 85.80(17) . . ? C32 O1 Ir1 122.4(4) . . ? C33 O2 Ir1 129.6(4) . . ? C1 N1 C5 120.6(6) . . ? C1 N1 Ir1 124.7(5) . . ? C5 N1 Ir1 114.6(5) . . ? C12 N2 C16 118.1(6) . . ? C12 N2 Ir1 126.8(5) . . ? C16 N2 Ir1 115.1(5) . . ? C32 N3 N4 110.5(5) . . ? C32 N3 C23 129.8(6) . . ? N4 N3 C23 119.8(6) . . ? C30 N4 N3 106.1(5) . . ? N1 C1 C2 122.2(8) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C1 C2 C3 119.3(9) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C2 C3 C4 119.5(8) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 120.5(8) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? N1 C5 C4 117.8(7) . . ? N1 C5 C6 115.0(6) . . ? C4 C5 C6 127.1(7) . . ? C7 C6 C11 121.4(7) . . ? C7 C6 C5 124.2(7) . . ? C11 C6 C5 114.4(6) . . ? C8 C7 C6 119.8(8) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C7 C8 C9 120.4(8) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C8 C9 C10 120.0(8) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 122.6(8) . . ? C9 C10 H10A 118.7 . . ? C11 C10 H10A 118.7 . . ? C10 C11 C6 115.7(6) . . ? C10 C11 Ir1 130.2(5) . . ? C6 C11 Ir1 113.8(5) . . ? N2 C12 C13 124.3(7) . . ? N2 C12 H12A 117.8 . . ? C13 C12 H12A 117.8 . . ? C14 C13 C12 117.8(8) . . ? C14 C13 H13A 121.1 . . ? C12 C13 H13A 121.1 . . ? C13 C14 C15 120.0(8) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 C16 120.1(8) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? N2 C16 C15 119.8(7) . . ? N2 C16 C17 114.6(6) . . ? C15 C16 C17 125.7(7) . . ? C18 C17 C22 122.3(7) . . ? C18 C17 C16 123.8(7) . . ? C22 C17 C16 113.8(7) . . ? C19 C18 C17 118.5(8) . . ? C19 C18 H18A 120.7 . . ? C17 C18 H18A 120.7 . . ? C20 C19 C18 121.4(8) . . ? C20 C19 H19A 119.3 . . ? C18 C19 H19A 119.3 . . ? C19 C20 C21 120.9(8) . . ? C19 C20 H20A 119.5 . . ? C21 C20 H20A 119.5 . . ? C20 C21 C22 121.0(7) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C21 C22 C17 115.8(7) . . ? C21 C22 Ir1 128.7(5) . . ? C17 C22 Ir1 115.5(5) . . ? C24 C23 C28 119.9(7) . . ? C24 C23 N3 122.3(7) . . ? C28 C23 N3 117.9(7) . . ? C23 C24 C25 118.6(8) . . ? C23 C24 H24A 120.7 . . ? C25 C24 H24A 120.7 . . ? C26 C25 C24 122.2(8) . . ? C26 C25 H25A 118.9 . . ? C24 C25 H25A 118.9 . . ? C25 C26 C27 119.1(8) . . ? C25 C26 H26A 120.4 . . ? C27 C26 H26A 120.4 . . ? C26 C27 C28 119.2(8) . . ? C26 C27 H27A 120.4 . . ? C28 C27 H27A 120.4 . . ? C23 C28 C27 121.0(8) . . ? C23 C28 H28A 119.5 . . ? C27 C28 H28A 119.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N4 C30 C31 112.6(6) . . ? N4 C30 C29 117.0(6) . . ? C31 C30 C29 130.5(6) . . ? C33 C31 C30 132.1(6) . . ? C33 C31 C32 123.9(6) . . ? C30 C31 C32 104.0(6) . . ? O1 C32 N3 120.8(6) . . ? O1 C32 C31 132.5(7) . . ? N3 C32 C31 106.7(6) . . ? O2 C33 C31 124.0(6) . . ? O2 C33 C34 114.5(6) . . ? C31 C33 C34 121.4(6) . . ? C35 C34 C33 111.7(6) . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? C40 C35 C36 119.3(8) . . ? C40 C35 C34 121.9(7) . . ? C36 C35 C34 118.7(8) . . ? C35 C36 C37 120.1(9) . . ? C35 C36 H36 120.0 . . ? C37 C36 H36 120.0 . . ? C36 C37 C38 120.9(9) . . ? C36 C37 H37A 119.6 . . ? C38 C37 H37A 119.6 . . ? C39 C38 C37 118.1(10) . . ? C39 C38 H38A 121.0 . . ? C37 C38 H38A 121.0 . . ? C38 C39 C40 120.2(10) . . ? C38 C39 H39A 119.9 . . ? C40 C39 H39A 119.9 . . ? C35 C40 C39 121.5(8) . . ? C35 C40 H40A 119.3 . . ? C39 C40 H40A 119.3 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.965 _refine_diff_density_min -1.066 _refine_diff_density_rms 0.126 # Attachment '- Ir(ppy)2(L1).cif' data_s _database_code_depnum_ccdc_archive 'CCDC 737812' #TrackingRef '- Ir(ppy)2(L1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H29 Ir N4 O2, 2(C H2 Cl2)' _chemical_formula_sum 'C41 H33 Cl4 Ir N4 O2' _chemical_formula_weight 947.71 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 'P 21/c' _symmetry_space_group_name_HALL '-P 2ybc' 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 12.577(3) _cell_length_b 11.248(2) _cell_length_c 27.694(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.95(3) _cell_angle_gamma 90.00 _cell_volume 3896.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 3.741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4548 _exptl_absorpt_correction_T_max 0.6038 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 18657 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6849 _reflns_number_gt 4691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6849 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 0.775020(18) 0.45461(2) 0.391078(8) 0.03909(8) Uani 1 1 d . . . Cl1 Cl 0.6749(3) 0.9778(2) 0.43457(11) 0.1622(12) Uani 1 1 d . . . Cl2 Cl 0.6689(4) 1.0387(3) 0.53334(12) 0.229(2) Uani 1 1 d . . . Cl3 Cl 0.0730(3) 0.1730(4) 0.28494(17) 0.242(2) Uani 1 1 d . . . Cl4 Cl 0.2413(3) 0.0879(4) 0.3441(2) 0.265(3) Uani 1 1 d . . . O1 O 0.9184(3) 0.5298(3) 0.36612(14) 0.0475(10) Uani 1 1 d . . . O2 O 0.6880(3) 0.5984(3) 0.35225(14) 0.0477(10) Uani 1 1 d . . . N1 N 0.8010(3) 0.5429(5) 0.45524(16) 0.0439(11) Uani 1 1 d . . . N2 N 0.7459(4) 0.3500(4) 0.33177(16) 0.0450(12) Uani 1 1 d . . . N3 N 1.0114(4) 0.6958(4) 0.34584(17) 0.0453(12) Uani 1 1 d . . . N4 N 0.9921(4) 0.8153(4) 0.33291(19) 0.0561(14) Uani 1 1 d . . . C1 C 0.7656(5) 0.6540(5) 0.4635(2) 0.0509(16) Uani 1 1 d . . . H1 H 0.7294 0.6961 0.4380 0.061 Uiso 1 1 calc R . . C2 C 0.7815(5) 0.7060(6) 0.5083(3) 0.0624(19) Uani 1 1 d . . . H2 H 0.7559 0.7822 0.5131 0.075 Uiso 1 1 calc R . . C3 C 0.8359(6) 0.6447(7) 0.5460(3) 0.069(2) Uani 1 1 d . . . H3 H 0.8476 0.6788 0.5767 0.083 Uiso 1 1 calc R . . C4 C 0.8726(5) 0.5334(7) 0.5379(2) 0.0596(18) Uani 1 1 d . . . H4 H 0.9108 0.4921 0.5632 0.072 Uiso 1 1 calc R . . C5 C 0.8537(5) 0.4807(5) 0.4926(2) 0.0447(15) Uani 1 1 d . . . C6 C 0.8853(5) 0.3619(6) 0.4787(2) 0.0500(16) Uani 1 1 d . . . C7 C 0.9417(5) 0.2831(7) 0.5111(2) 0.065(2) Uani 1 1 d . . . H7 H 0.9587 0.3046 0.5434 0.078 Uiso 1 1 calc R . . C8 C 0.9721(6) 0.1736(7) 0.4950(3) 0.075(2) Uani 1 1 d . . . H8 H 1.0094 0.1207 0.5163 0.090 Uiso 1 1 calc R . . C9 C 0.9471(6) 0.1433(6) 0.4476(3) 0.074(2) Uani 1 1 d . . . H9 H 0.9690 0.0699 0.4368 0.089 Uiso 1 1 calc R . . C10 C 0.8901(5) 0.2190(5) 0.4152(2) 0.0599(18) Uani 1 1 d . . . H10 H 0.8732 0.1952 0.3832 0.072 Uiso 1 1 calc R . . C11 C 0.8577(4) 0.3308(5) 0.4301(2) 0.0425(15) Uani 1 1 d . . . C12 C 0.8073(5) 0.3450(6) 0.2951(2) 0.0611(18) Uani 1 1 d . . . H12 H 0.8649 0.3970 0.2953 0.073 Uiso 1 1 calc R . . C13 C 0.7888(6) 0.2663(7) 0.2570(3) 0.074(2) Uani 1 1 d . . . H13 H 0.8334 0.2639 0.2322 0.088 Uiso 1 1 calc R . . C14 C 0.7030(7) 0.1919(7) 0.2566(3) 0.080(2) Uani 1 1 d . . . H14 H 0.6878 0.1384 0.2312 0.096 Uiso 1 1 calc R . . C15 C 0.6401(6) 0.1963(6) 0.2933(3) 0.064(2) Uani 1 1 d . . . H15 H 0.5825 0.1444 0.2932 0.077 Uiso 1 1 calc R . . C16 C 0.6596(5) 0.2765(5) 0.3312(2) 0.0476(16) Uani 1 1 d . . . C17 C 0.5980(4) 0.2948(5) 0.3721(2) 0.0446(15) Uani 1 1 d . . . C18 C 0.5033(5) 0.2347(6) 0.3776(3) 0.068(2) Uani 1 1 d . . . H18 H 0.4759 0.1798 0.3545 0.081 Uiso 1 1 calc R . . C19 C 0.4501(5) 0.2581(7) 0.4182(3) 0.078(2) Uani 1 1 d . . . H19 H 0.3867 0.2184 0.4222 0.093 Uiso 1 1 calc R . . C20 C 0.4899(5) 0.3383(6) 0.4522(3) 0.071(2) Uani 1 1 d . . . H20 H 0.4537 0.3531 0.4792 0.085 Uiso 1 1 calc R . . C21 C 0.5835(5) 0.3975(5) 0.4467(2) 0.0561(18) Uani 1 1 d . . . H21 H 0.6093 0.4522 0.4702 0.067 Uiso 1 1 calc R . . C22 C 0.6410(4) 0.3784(5) 0.4071(2) 0.0433(15) Uani 1 1 d . . . C23 C 1.1164(5) 0.6521(6) 0.3546(2) 0.0494(16) Uani 1 1 d . . . C24 C 1.1402(5) 0.5387(6) 0.3393(2) 0.0562(17) Uani 1 1 d . . . H24 H 1.0875 0.4926 0.3223 0.067 Uiso 1 1 calc R . . C25 C 1.2427(6) 0.4944(7) 0.3494(3) 0.069(2) Uani 1 1 d . . . H25 H 1.2583 0.4176 0.3398 0.083 Uiso 1 1 calc R . . C26 C 1.3215(6) 0.5631(8) 0.3734(3) 0.079(2) Uani 1 1 d . . . H26 H 1.3904 0.5333 0.3802 0.095 Uiso 1 1 calc R . . C27 C 1.2975(6) 0.6759(8) 0.3873(3) 0.075(2) Uani 1 1 d . . . H27 H 1.3513 0.7228 0.4031 0.090 Uiso 1 1 calc R . . C28 C 1.1946(5) 0.7223(6) 0.3783(2) 0.0601(18) Uani 1 1 d . . . H28 H 1.1792 0.7989 0.3882 0.072 Uiso 1 1 calc R . . C29 C 0.9187(5) 0.6364(5) 0.3510(2) 0.0430(14) Uani 1 1 d . . . C30 C 0.8327(5) 0.7196(5) 0.3374(2) 0.0447(15) Uani 1 1 d . . . C31 C 0.8879(5) 0.8286(5) 0.3275(2) 0.0526(17) Uani 1 1 d . . . C32 C 0.8434(5) 0.9504(6) 0.3157(3) 0.078(2) Uani 1 1 d . . . H32A H 0.8989 1.0086 0.3223 0.117 Uiso 1 1 calc R . . H32B H 0.7864 0.9666 0.3353 0.117 Uiso 1 1 calc R . . H32C H 0.8166 0.9538 0.2820 0.117 Uiso 1 1 calc R . . C33 C 0.7241(5) 0.6910(5) 0.3347(2) 0.0448(15) Uani 1 1 d . . . C34 C 0.6404(5) 0.7739(5) 0.3111(2) 0.0468(15) Uani 1 1 d . . . C35 C 0.6433(5) 0.8139(6) 0.2644(2) 0.0607(19) Uani 1 1 d . . . H35 H 0.6990 0.7903 0.2470 0.073 Uiso 1 1 calc R . . C36 C 0.5651(6) 0.8882(6) 0.2430(3) 0.069(2) Uani 1 1 d . . . H36 H 0.5682 0.9146 0.2113 0.083 Uiso 1 1 calc R . . C37 C 0.4830(6) 0.9229(6) 0.2685(3) 0.075(2) Uani 1 1 d . . . H37 H 0.4307 0.9743 0.2545 0.090 Uiso 1 1 calc R . . C38 C 0.4777(5) 0.8818(7) 0.3150(3) 0.077(2) Uani 1 1 d . . . H38 H 0.4218 0.9052 0.3324 0.092 Uiso 1 1 calc R . . C39 C 0.5557(5) 0.8057(6) 0.3359(2) 0.0592(18) Uani 1 1 d . . . H39 H 0.5508 0.7759 0.3669 0.071 Uiso 1 1 calc R . . C40 C 0.6771(7) 1.0870(7) 0.4774(3) 0.109(3) Uani 1 1 d . . . H40A H 0.7428 1.1321 0.4770 0.131 Uiso 1 1 calc R . . H40B H 0.6180 1.1409 0.4686 0.131 Uiso 1 1 calc R . . C41 C 0.1315(9) 0.0775(11) 0.3217(7) 0.312(12) Uani 1 1 d . . . H41A H 0.0872 0.0695 0.3481 0.375 Uiso 1 1 calc R . . H41B H 0.1274 0.0020 0.3046 0.375 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 0.04348(14) 0.03552(13) 0.03944(13) 0.00403(13) 0.00983(10) -0.00161(14) Cl1 0.270(4) 0.097(2) 0.118(2) -0.0129(17) 0.011(2) -0.005(2) Cl2 0.471(7) 0.111(2) 0.114(2) -0.006(2) 0.076(3) -0.066(3) Cl3 0.137(3) 0.285(5) 0.299(5) 0.165(4) -0.010(3) -0.017(3) Cl4 0.136(3) 0.217(5) 0.415(7) 0.051(4) -0.097(4) -0.010(3) O1 0.046(2) 0.039(3) 0.059(3) 0.015(2) 0.016(2) -0.0016(19) O2 0.044(2) 0.044(2) 0.055(3) 0.013(2) 0.005(2) 0.0010(19) N1 0.041(3) 0.050(3) 0.042(3) 0.002(3) 0.010(2) -0.008(3) N2 0.053(3) 0.045(3) 0.038(3) 0.003(2) 0.009(3) 0.003(3) N3 0.039(3) 0.042(3) 0.056(3) 0.011(3) 0.007(3) -0.004(2) N4 0.053(4) 0.045(3) 0.069(4) 0.012(3) 0.002(3) -0.010(3) C1 0.059(4) 0.045(4) 0.051(4) 0.003(3) 0.012(3) 0.008(3) C2 0.076(5) 0.052(4) 0.063(5) -0.012(4) 0.025(4) -0.011(4) C3 0.091(6) 0.069(5) 0.050(5) -0.013(4) 0.024(4) -0.018(5) C4 0.063(4) 0.077(5) 0.039(4) 0.013(4) 0.008(3) -0.008(4) C5 0.045(4) 0.051(4) 0.039(4) 0.006(3) 0.010(3) -0.007(3) C6 0.053(4) 0.051(4) 0.048(4) 0.017(3) 0.019(3) -0.005(3) C7 0.073(5) 0.068(5) 0.054(5) 0.020(4) 0.011(4) -0.005(4) C8 0.070(5) 0.067(6) 0.087(6) 0.041(5) 0.001(5) 0.017(4) C9 0.086(6) 0.041(4) 0.097(6) 0.017(4) 0.012(5) 0.008(4) C10 0.070(5) 0.039(4) 0.071(5) 0.004(4) 0.008(4) 0.004(3) C11 0.040(4) 0.040(4) 0.049(4) 0.007(3) 0.011(3) -0.001(3) C12 0.078(5) 0.060(5) 0.048(4) 0.001(4) 0.018(4) 0.004(4) C13 0.089(6) 0.084(6) 0.050(5) -0.009(4) 0.018(4) 0.024(5) C14 0.109(7) 0.075(6) 0.053(5) -0.022(4) -0.009(5) 0.023(5) C15 0.070(5) 0.054(5) 0.065(5) -0.010(4) -0.009(4) -0.004(4) C16 0.056(4) 0.039(4) 0.045(4) 0.000(3) -0.006(3) 0.001(3) C17 0.041(4) 0.039(4) 0.055(4) 0.003(3) 0.008(3) -0.005(3) C18 0.058(5) 0.054(5) 0.089(6) -0.001(4) 0.002(4) -0.010(4) C19 0.056(5) 0.068(5) 0.113(7) 0.012(5) 0.024(5) -0.017(4) C20 0.068(5) 0.062(5) 0.090(6) 0.001(4) 0.036(4) -0.007(4) C21 0.056(4) 0.050(4) 0.066(5) -0.003(3) 0.021(4) -0.011(3) C22 0.039(3) 0.039(4) 0.053(4) 0.010(3) 0.012(3) 0.000(3) C23 0.043(4) 0.059(5) 0.048(4) 0.018(3) 0.012(3) -0.001(3) C24 0.059(4) 0.061(5) 0.051(4) 0.008(4) 0.018(3) 0.005(4) C25 0.064(5) 0.078(5) 0.069(5) 0.014(4) 0.030(4) 0.013(4) C26 0.058(5) 0.097(7) 0.083(6) 0.021(5) 0.015(4) 0.017(5) C27 0.054(5) 0.095(7) 0.077(5) 0.015(5) 0.010(4) -0.007(4) C28 0.057(5) 0.058(5) 0.066(5) 0.009(4) 0.011(4) -0.002(4) C29 0.047(4) 0.043(4) 0.039(4) 0.003(3) 0.005(3) -0.006(3) C30 0.052(4) 0.038(4) 0.044(4) 0.005(3) 0.004(3) -0.004(3) C31 0.049(4) 0.042(4) 0.066(5) 0.010(3) 0.005(4) -0.002(3) C32 0.064(5) 0.047(4) 0.121(6) 0.009(5) -0.004(4) 0.000(4) C33 0.048(4) 0.044(4) 0.044(4) -0.002(3) 0.012(3) -0.005(3) C34 0.051(4) 0.042(4) 0.047(4) 0.003(3) 0.003(3) -0.003(3) C35 0.056(5) 0.061(5) 0.063(5) 0.008(4) -0.002(4) -0.003(4) C36 0.064(5) 0.069(5) 0.069(5) 0.016(4) -0.016(4) -0.011(4) C37 0.054(5) 0.054(5) 0.112(7) 0.010(5) -0.023(5) -0.001(4) C38 0.053(5) 0.079(6) 0.099(7) -0.003(5) 0.007(5) 0.010(4) C39 0.047(4) 0.064(5) 0.066(5) 0.009(4) -0.001(4) -0.003(4) C40 0.143(8) 0.070(6) 0.116(8) 0.016(5) 0.025(6) -0.013(5) C41 0.129(11) 0.165(14) 0.60(3) 0.154(17) -0.174(16) -0.074(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C22 1.981(5) . ? Ir1 C11 1.988(6) . ? Ir1 N2 2.023(5) . ? Ir1 N1 2.032(5) . ? Ir1 O1 2.169(3) . ? Ir1 O2 2.174(4) . ? Cl1 C40 1.706(8) . ? Cl2 C40 1.655(8) . ? Cl3 C41 1.605(12) . ? Cl4 C41 1.458(10) . ? O1 C29 1.271(6) . ? O2 C33 1.255(6) . ? N1 C1 1.354(7) . ? N1 C5 1.363(7) . ? N2 C12 1.339(7) . ? N2 C16 1.364(7) . ? N3 C29 1.364(7) . ? N3 N4 1.405(6) . ? N3 C23 1.407(7) . ? N4 C31 1.311(7) . ? C1 C2 1.366(8) . ? C1 H1 0.9300 . ? C2 C3 1.375(9) . ? C2 H2 0.9300 . ? C3 C4 1.360(9) . ? C3 H3 0.9300 . ? C4 C5 1.387(8) . ? C4 H4 0.9300 . ? C5 C6 1.456(8) . ? C6 C7 1.401(8) . ? C6 C11 1.400(8) . ? C7 C8 1.377(9) . ? C7 H7 0.9300 . ? C8 C9 1.358(9) . ? C8 H8 0.9300 . ? C9 C10 1.382(8) . ? C9 H9 0.9300 . ? C10 C11 1.397(8) . ? C10 H10 0.9300 . ? C12 C13 1.379(9) . ? C12 H12 0.9300 . ? C13 C14 1.365(10) . ? C13 H13 0.9300 . ? C14 C15 1.352(9) . ? C14 H14 0.9300 . ? C15 C16 1.387(8) . ? C15 H15 0.9300 . ? C16 C17 1.451(8) . ? C17 C18 1.392(8) . ? C17 C22 1.416(8) . ? C18 C19 1.392(9) . ? C18 H18 0.9300 . ? C19 C20 1.360(9) . ? C19 H19 0.9300 . ? C20 C21 1.375(8) . ? C20 H20 0.9300 . ? C21 C22 1.392(7) . ? C21 H21 0.9300 . ? C23 C28 1.374(8) . ? C23 C24 1.387(8) . ? C24 C25 1.383(8) . ? C24 H24 0.9300 . ? C25 C26 1.374(9) . ? C25 H25 0.9300 . ? C26 C27 1.368(9) . ? C26 H26 0.9300 . ? C27 C28 1.394(8) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.450(8) . ? C30 C33 1.398(7) . ? C30 C31 1.449(8) . ? C31 C32 1.503(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.504(8) . ? C34 C39 1.372(8) . ? C34 C35 1.372(8) . ? C35 C36 1.377(8) . ? C35 H35 0.9300 . ? C36 C37 1.368(9) . ? C36 H36 0.9300 . ? C37 C38 1.376(9) . ? C37 H37 0.9300 . ? C38 C39 1.382(8) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 H41A 0.9700 . ? C41 H41B 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 C22 Ir1 C11 89.1(2) . . ? C22 Ir1 N2 81.0(2) . . ? C11 Ir1 N2 94.3(2) . . ? C22 Ir1 N1 94.5(2) . . ? C11 Ir1 N1 80.8(2) . . ? N2 Ir1 N1 173.41(19) . . ? C22 Ir1 O1 174.0(2) . . ? C11 Ir1 O1 92.34(18) . . ? N2 Ir1 O1 93.12(17) . . ? N1 Ir1 O1 91.41(16) . . ? C22 Ir1 O2 92.04(18) . . ? C11 Ir1 O2 176.2(2) . . ? N2 Ir1 O2 89.51(17) . . ? N1 Ir1 O2 95.51(18) . . ? O1 Ir1 O2 86.87(14) . . ? C29 O1 Ir1 120.2(3) . . ? C33 O2 Ir1 128.7(4) . . ? C1 N1 C5 119.2(5) . . ? C1 N1 Ir1 125.0(4) . . ? C5 N1 Ir1 115.7(4) . . ? C12 N2 C16 119.2(5) . . ? C12 N2 Ir1 124.8(4) . . ? C16 N2 Ir1 116.0(4) . . ? C29 N3 N4 111.6(5) . . ? C29 N3 C23 127.4(5) . . ? N4 N3 C23 120.8(5) . . ? C31 N4 N3 106.4(5) . . ? N1 C1 C2 122.0(6) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 119.3(7) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.1(6) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 119.5(6) . . ? N1 C5 C6 113.3(5) . . ? C4 C5 C6 127.2(6) . . ? C7 C6 C11 121.0(6) . . ? C7 C6 C5 123.1(6) . . ? C11 C6 C5 115.8(6) . . ? C8 C7 C6 119.9(7) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 119.5(7) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 121.6(7) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C11 120.7(7) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 117.2(6) . . ? C10 C11 Ir1 128.5(5) . . ? C6 C11 Ir1 114.3(4) . . ? N2 C12 C13 122.9(7) . . ? N2 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C14 C13 C12 118.0(7) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C15 C14 C13 119.7(7) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 121.5(7) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N2 C16 C15 118.7(6) . . ? N2 C16 C17 113.2(5) . . ? C15 C16 C17 128.0(6) . . ? C18 C17 C22 121.3(6) . . ? C18 C17 C16 123.2(6) . . ? C22 C17 C16 115.5(5) . . ? C19 C18 C17 119.0(7) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C20 C19 C18 120.7(7) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.2(7) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C22 122.2(6) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C21 C22 C17 116.6(5) . . ? C21 C22 Ir1 129.3(5) . . ? C17 C22 Ir1 114.1(4) . . ? C28 C23 C24 120.6(6) . . ? C28 C23 N3 119.6(6) . . ? C24 C23 N3 119.8(6) . . ? C25 C24 C23 119.7(7) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 120.4(7) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 119.3(7) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C26 C27 C28 121.7(7) . . ? C26 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? C23 C28 C27 118.4(7) . . ? C23 C28 H28 120.8 . . ? C27 C28 H28 120.8 . . ? O1 C29 N3 121.9(5) . . ? O1 C29 C30 131.9(5) . . ? N3 C29 C30 106.2(5) . . ? C33 C30 C31 132.0(6) . . ? C33 C30 C29 124.3(5) . . ? C31 C30 C29 103.6(5) . . ? N4 C31 C30 112.0(5) . . ? N4 C31 C32 118.3(5) . . ? C30 C31 C32 129.6(6) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O2 C33 C30 124.2(6) . . ? O2 C33 C34 114.7(5) . . ? C30 C33 C34 121.1(5) . . ? C39 C34 C35 118.9(6) . . ? C39 C34 C33 119.2(6) . . ? C35 C34 C33 121.7(6) . . ? C34 C35 C36 121.2(7) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C37 C36 C35 119.5(7) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 C38 120.0(7) . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C37 C38 C39 119.8(7) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C34 C39 C38 120.4(7) . . ? C34 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? Cl2 C40 Cl1 114.6(5) . . ? Cl2 C40 H40A 108.6 . . ? Cl1 C40 H40A 108.6 . . ? Cl2 C40 H40B 108.6 . . ? Cl1 C40 H40B 108.6 . . ? H40A C40 H40B 107.6 . . ? Cl4 C41 Cl3 124.6(8) . . ? Cl4 C41 H41A 106.2 . . ? Cl3 C41 H41A 106.2 . . ? Cl4 C41 H41B 106.2 . . ? Cl3 C41 H41B 106.2 . . ? H41A C41 H41B 106.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.860 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.094