# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Fuyou Li' _publ_contact_author_address ; Institute of Advanced Materials Fudan University Handan Road 220 Shanghai 200433 CHINA ; _publ_contact_author_email FYLI@FUDAN.EDU.CN _publ_section_title ; Aggregation-Induced Phosphorescent Emission (AIPE) of Iridium(III) Complexes ; loop_ _publ_author_name 'Fuyou Li.' 'Chunhui Huang.' 'Lei Li.' 'Zhi-Pan Liu.' 'Tao Yi.' 'Mengxiao Yu.' ; Qiang Zhao ; # Attachment 'Ir(ppy)2DBM-2R.cif' data_51017a _database_code_depnum_ccdc_archive 'CCDC 610633' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37.50 H27 Cl Ir N2 O2' _chemical_formula_weight 765.26 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' Cl Cl 0.1484 0.1585 '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 10.877(5) _cell_length_b 11.769(5) _cell_length_c 12.418(6) _cell_angle_alpha 92.106(5) _cell_angle_beta 94.577(6) _cell_angle_gamma 104.907(5) _cell_volume 1528.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2433 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 21.33 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 4.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6147 _exptl_absorpt_correction_T_max 0.7152 _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 6866 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0962 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5303 _reflns_number_gt 4266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^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 5303 _refine_ls_number_parameters 406 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.003 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 0.24203(3) 1.00224(2) 0.73328(2) 0.03748(14) Uani 1 1 d . . . N1 N 0.2064(7) 1.0105(6) 0.8916(5) 0.0443(17) Uani 1 1 d . . . N2 N 0.2844(7) 1.0153(6) 0.5757(5) 0.0435(17) Uani 1 1 d . . . O1 O 0.3401(6) 0.8661(5) 0.7534(5) 0.0506(15) Uani 1 1 d . . . O2 O 0.0679(6) 0.8664(5) 0.6934(4) 0.0483(14) Uani 1 1 d . . . C1 C 0.2873(9) 0.7551(7) 0.7477(7) 0.046(2) Uani 1 1 d . . . C2 C 0.4841(9) 0.7299(8) 0.8452(8) 0.057(2) Uani 1 1 d . . . H2A H 0.5058 0.8103 0.8637 0.069 Uiso 1 1 calc R . . C3 C 0.5641(10) 0.6627(10) 0.8844(10) 0.080(3) Uani 1 1 d . . . H3A H 0.6372 0.6973 0.9301 0.096 Uiso 1 1 calc R . . C4 C 0.5337(11) 0.5459(10) 0.8548(10) 0.087(4) Uani 1 1 d . . . H4A H 0.5873 0.5006 0.8800 0.105 Uiso 1 1 calc R . . C5 C 0.4245(12) 0.4931(9) 0.7879(11) 0.092(4) Uani 1 1 d . . . H5A H 0.4041 0.4127 0.7694 0.110 Uiso 1 1 calc R . . C6 C 0.3456(10) 0.5605(8) 0.7488(9) 0.070(3) Uani 1 1 d . . . H6A H 0.2737 0.5261 0.7016 0.084 Uiso 1 1 calc R . . C7 C 0.3741(8) 0.6804(7) 0.7800(7) 0.045(2) Uani 1 1 d . . . C8 C 0.1582(9) 0.7028(8) 0.7186(8) 0.059(2) Uani 1 1 d . . . H8A H 0.1337 0.6211 0.7197 0.070 Uiso 1 1 calc R . . C9 C 0.0587(8) 0.7558(7) 0.6875(6) 0.045(2) Uani 1 1 d . . . C10 C -0.0687(8) 0.6757(7) 0.6484(6) 0.0401(19) Uani 1 1 d . . . C11 C -0.1760(9) 0.7173(8) 0.6487(8) 0.059(3) Uani 1 1 d . . . H11A H -0.1681 0.7943 0.6747 0.071 Uiso 1 1 calc R . . C12 C -0.2950(10) 0.6468(10) 0.6113(10) 0.078(3) Uani 1 1 d . . . H12A H -0.3672 0.6745 0.6162 0.094 Uiso 1 1 calc R . . C13 C -0.3066(11) 0.5343(10) 0.5662(10) 0.076(3) Uani 1 1 d . . . H13A H -0.3859 0.4876 0.5375 0.091 Uiso 1 1 calc R . . C14 C -0.2000(9) 0.4933(8) 0.5645(8) 0.060(3) Uani 1 1 d . . . H14A H -0.2070 0.4176 0.5357 0.072 Uiso 1 1 calc R . . C15 C -0.0838(9) 0.5625(7) 0.6046(7) 0.052(2) Uani 1 1 d . . . H15A H -0.0125 0.5330 0.6026 0.062 Uiso 1 1 calc R . . C16 C 0.2400(10) 0.9451(8) 0.9686(7) 0.056(2) Uani 1 1 d . . . H16A H 0.2783 0.8864 0.9485 0.067 Uiso 1 1 calc R . . C17 C 0.2213(11) 0.9593(9) 1.0753(7) 0.065(3) Uani 1 1 d . . . H17A H 0.2472 0.9122 1.1263 0.078 Uiso 1 1 calc R . . C18 C 0.1632(11) 1.0447(9) 1.1053(7) 0.065(3) Uani 1 1 d . . . H18A H 0.1482 1.0561 1.1771 0.079 Uiso 1 1 calc R . . C19 C 0.1278(9) 1.1129(8) 1.0278(7) 0.057(2) Uani 1 1 d . . . H19A H 0.0892 1.1715 1.0475 0.069 Uiso 1 1 calc R . . C20 C 0.1486(8) 1.0959(7) 0.9204(6) 0.044(2) Uani 1 1 d . . . C21 C 0.1149(8) 1.1613(7) 0.8299(6) 0.045(2) Uani 1 1 d . . . C22 C 0.1524(8) 1.1292(7) 0.7299(7) 0.044(2) Uani 1 1 d . . . C23 C 0.1234(9) 1.1918(7) 0.6401(7) 0.050(2) Uani 1 1 d . . . H23A H 0.1476 1.1742 0.5726 0.060 Uiso 1 1 calc R . . C24 C 0.0597(10) 1.2785(7) 0.6512(8) 0.055(2) Uani 1 1 d . . . H24A H 0.0415 1.3184 0.5911 0.065 Uiso 1 1 calc R . . C25 C 0.0228(10) 1.3068(8) 0.7507(8) 0.062(3) Uani 1 1 d . . . H25A H -0.0203 1.3651 0.7573 0.074 Uiso 1 1 calc R . . C26 C 0.0501(9) 1.2483(8) 0.8397(8) 0.060(3) Uani 1 1 d . . . H26A H 0.0252 1.2670 0.9066 0.071 Uiso 1 1 calc R . . C27 C 0.2088(10) 0.9538(8) 0.4912(7) 0.054(2) Uani 1 1 d . . . H27A H 0.1321 0.9009 0.5032 0.065 Uiso 1 1 calc R . . C28 C 0.2430(11) 0.9679(9) 0.3869(7) 0.061(3) Uani 1 1 d . . . H28A H 0.1893 0.9256 0.3289 0.073 Uiso 1 1 calc R . . C29 C 0.3552(11) 1.0437(9) 0.3697(8) 0.065(3) Uani 1 1 d . . . H29A H 0.3796 1.0524 0.2998 0.077 Uiso 1 1 calc R . . C30 C 0.4329(9) 1.1076(8) 0.4547(8) 0.058(2) Uani 1 1 d . . . H30A H 0.5095 1.1603 0.4419 0.069 Uiso 1 1 calc R . . C31 C 0.3988(8) 1.0948(7) 0.5605(7) 0.044(2) Uani 1 1 d . . . C32 C 0.4666(8) 1.1528(7) 0.6586(7) 0.050(2) Uani 1 1 d . . . C33 C 0.5866(9) 1.2346(8) 0.6625(9) 0.063(3) Uani 1 1 d . . . H33A H 0.6245 1.2549 0.5989 0.076 Uiso 1 1 calc R . . C34 C 0.6479(10) 1.2846(9) 0.7605(10) 0.070(3) Uani 1 1 d . . . H34A H 0.7280 1.3377 0.7628 0.084 Uiso 1 1 calc R . . C35 C 0.5934(10) 1.2576(8) 0.8545(9) 0.062(3) Uani 1 1 d . . . H35A H 0.6358 1.2930 0.9201 0.075 Uiso 1 1 calc R . . C36 C 0.4750(9) 1.1775(8) 0.8524(8) 0.058(2) Uani 1 1 d . . . H36A H 0.4385 1.1610 0.9172 0.070 Uiso 1 1 calc R . . C37 C 0.4077(8) 1.1201(7) 0.7550(6) 0.0376(18) Uani 1 1 d . . . Cl1 Cl 0.9137(18) 0.5439(11) 0.9164(8) 0.137(6) Uani 0.50 1 d PD . . Cl2 Cl 1.088(2) 0.492(3) 1.057(3) 0.34(2) Uani 0.50 1 d PD . . C38 C 0.912(3) 0.457(3) 1.0420(19) 0.22(4) Uani 0.50 1 d PD . . 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 0.0401(2) 0.03186(19) 0.03951(19) 0.00374(12) 0.00206(13) 0.00788(13) N1 0.058(5) 0.029(4) 0.045(4) 0.006(3) 0.002(3) 0.009(3) N2 0.054(5) 0.040(4) 0.041(4) -0.001(3) 0.001(3) 0.020(3) O1 0.039(3) 0.051(4) 0.064(4) 0.008(3) 0.001(3) 0.016(3) O2 0.050(4) 0.047(4) 0.049(3) 0.010(3) 0.002(3) 0.014(3) C1 0.058(6) 0.029(4) 0.047(5) 0.006(3) 0.000(4) 0.008(4) C2 0.056(6) 0.047(6) 0.069(6) -0.002(4) -0.010(5) 0.017(5) C3 0.070(8) 0.067(8) 0.104(9) -0.004(6) -0.027(7) 0.029(6) C4 0.083(9) 0.069(8) 0.116(10) 0.008(7) -0.026(8) 0.042(7) C5 0.090(9) 0.041(6) 0.149(12) -0.005(6) -0.014(8) 0.034(6) C6 0.066(7) 0.038(5) 0.101(8) -0.007(5) -0.013(6) 0.013(5) C7 0.048(5) 0.034(5) 0.052(5) 0.004(4) 0.004(4) 0.007(4) C8 0.060(6) 0.038(5) 0.076(6) 0.002(4) -0.010(5) 0.014(4) C9 0.050(5) 0.041(5) 0.040(4) 0.012(4) 0.000(4) 0.005(4) C10 0.043(5) 0.026(4) 0.048(5) 0.004(3) 0.005(4) 0.003(3) C11 0.057(6) 0.042(5) 0.080(7) -0.001(5) 0.003(5) 0.017(5) C12 0.044(6) 0.083(8) 0.110(9) 0.005(7) -0.013(6) 0.028(6) C13 0.054(7) 0.065(7) 0.100(9) 0.009(6) -0.015(6) 0.006(6) C14 0.052(6) 0.039(5) 0.080(7) -0.002(4) -0.010(5) -0.003(4) C15 0.047(5) 0.044(5) 0.062(6) 0.004(4) 0.006(4) 0.007(4) C16 0.076(7) 0.051(6) 0.047(5) 0.005(4) 0.001(5) 0.030(5) C17 0.089(8) 0.063(7) 0.045(5) 0.019(5) 0.003(5) 0.023(6) C18 0.085(8) 0.074(7) 0.034(5) 0.000(4) -0.001(5) 0.018(6) C19 0.067(7) 0.062(6) 0.048(5) -0.005(4) 0.005(5) 0.028(5) C20 0.047(5) 0.042(5) 0.039(4) 0.008(4) -0.001(4) 0.003(4) C21 0.050(5) 0.039(5) 0.046(5) -0.001(4) 0.007(4) 0.011(4) C22 0.036(5) 0.040(5) 0.051(5) 0.003(4) 0.013(4) -0.001(4) C23 0.072(7) 0.039(5) 0.044(5) 0.013(4) 0.006(4) 0.019(4) C24 0.072(7) 0.032(5) 0.063(6) 0.016(4) 0.011(5) 0.017(5) C25 0.067(7) 0.053(6) 0.075(7) 0.010(5) 0.014(6) 0.031(5) C26 0.078(7) 0.054(6) 0.058(6) 0.008(4) 0.019(5) 0.032(5) C27 0.067(7) 0.046(5) 0.053(5) 0.007(4) 0.011(5) 0.019(5) C28 0.078(8) 0.065(7) 0.043(5) 0.001(4) 0.009(5) 0.022(6) C29 0.088(9) 0.072(7) 0.048(6) 0.011(5) 0.022(6) 0.041(7) C30 0.054(6) 0.060(6) 0.065(6) 0.021(5) 0.021(5) 0.020(5) C31 0.044(5) 0.032(4) 0.063(5) 0.014(4) 0.017(4) 0.018(4) C32 0.045(5) 0.037(5) 0.069(6) 0.005(4) 0.014(5) 0.011(4) C33 0.044(6) 0.048(6) 0.099(8) 0.022(5) 0.018(6) 0.009(5) C34 0.044(6) 0.052(6) 0.108(9) 0.005(6) -0.001(6) 0.003(5) C35 0.053(6) 0.044(6) 0.085(7) -0.001(5) -0.011(6) 0.011(5) C36 0.045(6) 0.061(6) 0.064(6) 0.019(5) -0.005(5) 0.009(5) C37 0.046(5) 0.038(4) 0.037(4) 0.014(3) -0.005(4) 0.025(4) Cl1 0.246(18) 0.090(6) 0.059(4) -0.011(5) -0.005(6) 0.021(8) Cl2 0.143(16) 0.42(4) 0.43(4) -0.32(3) -0.030(18) 0.077(19) C38 0.24(6) 0.24(5) 0.08(2) -0.10(3) 0.08(3) -0.13(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 C37 1.963(9) . ? Ir1 C22 1.983(9) . ? Ir1 N1 2.037(7) . ? Ir1 N2 2.047(7) . ? Ir1 O2 2.150(6) . ? Ir1 O1 2.153(6) . ? N1 C16 1.336(11) . ? N1 C20 1.366(10) . ? N2 C27 1.342(11) . ? N2 C31 1.382(11) . ? O1 C1 1.281(9) . ? O2 C9 1.279(9) . ? C1 C8 1.392(12) . ? C1 C7 1.489(12) . ? C2 C7 1.371(13) . ? C2 C3 1.390(13) . ? C3 C4 1.358(14) . ? C4 C5 1.383(16) . ? C5 C6 1.383(14) . ? C6 C7 1.397(11) . ? C8 C9 1.417(12) . ? C9 C10 1.494(11) . ? C10 C11 1.377(12) . ? C10 C15 1.385(11) . ? C11 C12 1.379(13) . ? C12 C13 1.390(15) . ? C13 C14 1.368(13) . ? C14 C15 1.360(12) . ? C16 C17 1.367(12) . ? C17 C18 1.373(13) . ? C18 C19 1.370(13) . ? C19 C20 1.387(11) . ? C20 C21 1.461(11) . ? C21 C26 1.391(11) . ? C21 C22 1.406(11) . ? C22 C23 1.418(12) . ? C23 C24 1.381(12) . ? C24 C25 1.384(13) . ? C25 C26 1.376(13) . ? C27 C28 1.380(12) . ? C28 C29 1.351(14) . ? C29 C30 1.365(14) . ? C30 C31 1.397(12) . ? C31 C32 1.425(12) . ? C32 C33 1.405(12) . ? C32 C37 1.422(11) . ? C33 C34 1.375(14) . ? C34 C35 1.361(14) . ? C35 C36 1.384(13) . ? C36 C37 1.413(12) . ? Cl1 Cl2 0.54(5) 2_767 ? Cl1 C38 1.93(4) 2_767 ? Cl1 C38 1.89(3) . ? Cl2 Cl1 0.54(5) 2_767 ? Cl2 C38 1.39(5) 2_767 ? Cl2 C38 1.84(3) . ? Cl2 Cl2 2.34(6) 2_767 ? C38 Cl2 1.39(5) 2_767 ? C38 Cl1 1.93(4) 2_767 ? 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 C37 Ir1 C22 90.4(3) . . ? C37 Ir1 N1 94.5(3) . . ? C22 Ir1 N1 80.6(3) . . ? C37 Ir1 N2 80.7(3) . . ? C22 Ir1 N2 94.5(3) . . ? N1 Ir1 N2 173.2(2) . . ? C37 Ir1 O2 173.6(3) . . ? C22 Ir1 O2 92.9(3) . . ? N1 Ir1 O2 91.4(2) . . ? N2 Ir1 O2 93.6(3) . . ? C37 Ir1 O1 89.0(3) . . ? C22 Ir1 O1 174.6(3) . . ? N1 Ir1 O1 94.0(2) . . ? N2 Ir1 O1 90.7(2) . . ? O2 Ir1 O1 88.3(2) . . ? C16 N1 C20 118.4(7) . . ? C16 N1 Ir1 126.1(6) . . ? C20 N1 Ir1 115.5(5) . . ? C27 N2 C31 120.7(7) . . ? C27 N2 Ir1 124.2(6) . . ? C31 N2 Ir1 115.0(5) . . ? C1 O1 Ir1 125.7(5) . . ? C9 O2 Ir1 125.3(6) . . ? O1 C1 C8 125.3(8) . . ? O1 C1 C7 115.0(8) . . ? C8 C1 C7 119.7(7) . . ? C7 C2 C3 121.6(9) . . ? C4 C3 C2 118.9(10) . . ? C3 C4 C5 121.1(10) . . ? C4 C5 C6 119.6(10) . . ? C5 C6 C7 120.0(10) . . ? C2 C7 C6 118.6(9) . . ? C2 C7 C1 119.0(8) . . ? C6 C7 C1 122.3(8) . . ? C1 C8 C9 129.4(8) . . ? O2 C9 C8 125.4(8) . . ? O2 C9 C10 117.3(8) . . ? C8 C9 C10 117.3(8) . . ? C11 C10 C15 117.6(8) . . ? C11 C10 C9 119.4(7) . . ? C15 C10 C9 122.9(8) . . ? C10 C11 C12 121.1(9) . . ? C11 C12 C13 119.8(10) . . ? C14 C13 C12 119.1(10) . . ? C15 C14 C13 120.4(9) . . ? C14 C15 C10 121.9(9) . . ? N1 C16 C17 123.8(9) . . ? C16 C17 C18 118.4(9) . . ? C19 C18 C17 118.9(8) . . ? C18 C19 C20 121.0(9) . . ? N1 C20 C19 119.5(7) . . ? N1 C20 C21 113.8(7) . . ? C19 C20 C21 126.6(8) . . ? C26 C21 C22 121.7(8) . . ? C26 C21 C20 123.7(8) . . ? C22 C21 C20 114.7(8) . . ? C21 C22 C23 116.6(8) . . ? C21 C22 Ir1 115.3(6) . . ? C23 C22 Ir1 128.2(6) . . ? C24 C23 C22 121.1(8) . . ? C23 C24 C25 120.7(8) . . ? C26 C25 C24 119.7(9) . . ? C25 C26 C21 120.2(8) . . ? N2 C27 C28 121.1(9) . . ? C29 C28 C27 119.5(10) . . ? C28 C29 C30 120.3(9) . . ? C29 C30 C31 120.7(9) . . ? N2 C31 C30 117.7(9) . . ? N2 C31 C32 113.4(7) . . ? C30 C31 C32 128.9(9) . . ? C33 C32 C37 120.9(9) . . ? C33 C32 C31 123.1(9) . . ? C37 C32 C31 116.0(8) . . ? C34 C33 C32 119.8(10) . . ? C35 C34 C33 121.1(10) . . ? C34 C35 C36 120.0(10) . . ? C35 C36 C37 122.2(9) . . ? C36 C37 C32 116.0(8) . . ? C36 C37 Ir1 129.1(6) . . ? C32 C37 Ir1 114.8(6) . . ? Cl2 Cl1 C38 73(4) 2_767 2_767 ? Cl2 Cl1 C38 18(3) 2_767 . ? C38 Cl1 C38 73.1(13) 2_767 . ? Cl1 Cl2 C38 155(4) 2_767 2_767 ? Cl1 Cl2 C38 91(5) 2_767 . ? C38 Cl2 C38 88(2) 2_767 . ? Cl1 Cl2 Cl2 123(5) 2_767 2_767 ? C38 Cl2 Cl2 52(2) 2_767 2_767 ? C38 Cl2 Cl2 36.4(10) . 2_767 ? Cl2 C38 Cl2 92(2) 2_767 . ? Cl2 C38 Cl1 106(2) 2_767 2_767 ? Cl2 C38 Cl1 16.2(15) . 2_767 ? Cl2 C38 Cl1 6.8(14) 2_767 . ? Cl2 C38 Cl1 91.5(18) . . ? Cl1 C38 Cl1 106.9(13) 2_767 . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.130 _refine_diff_density_min -2.332 _refine_diff_density_rms 0.164 # Attachment 'Ir(ppy)2(SB)-2R.cif' data_51229b _database_code_depnum_ccdc_archive 'CCDC 611152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H31 Ir N4 O' _chemical_formula_weight 787.90 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4964(13) _cell_length_b 19.529(3) _cell_length_c 15.908(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.259(2) _cell_angle_gamma 90.00 _cell_volume 3227.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 4.177 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2292 _exptl_absorpt_correction_T_max 0.6801 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18633 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.01 _reflns_number_total 6315 _reflns_number_gt 4897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0497P)^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 6315 _refine_ls_number_parameters 427 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.461039(17) 0.300086(9) 0.553039(10) 0.03513(8) Uani 1 1 d . . . O1 O 0.2842(3) 0.35471(17) 0.5143(2) 0.0471(8) Uani 1 1 d . . . N1 N 0.3659(4) 0.25560(19) 0.6516(2) 0.0395(9) Uani 1 1 d . . . N2 N 0.5275(4) 0.38620(18) 0.6195(2) 0.0379(9) Uani 1 1 d . . . N3 N 0.4101(4) 0.2169(2) 0.4790(2) 0.0428(10) Uani 1 1 d . . . C1 C 0.4155(5) 0.1928(2) 0.6913(3) 0.0428(12) Uani 1 1 d . . . C2 C 0.5235(6) 0.1936(3) 0.7507(3) 0.0532(14) Uani 1 1 d . . . H2A H 0.5630 0.2351 0.7671 0.064 Uiso 1 1 calc R . . C3 C 0.5755(6) 0.1323(3) 0.7873(4) 0.0676(17) Uani 1 1 d . . . H3A H 0.6492 0.1332 0.8274 0.081 Uiso 1 1 calc R . . C4 C 0.5181(7) 0.0724(3) 0.7639(4) 0.0738(19) Uani 1 1 d . . . H4A H 0.5533 0.0322 0.7885 0.089 Uiso 1 1 calc R . . C5 C 0.4061(6) 0.0686(3) 0.7032(4) 0.0595(15) Uani 1 1 d . . . C6 C 0.3529(5) 0.1310(3) 0.6661(3) 0.0479(12) Uani 1 1 d . . . C7 C 0.2392(6) 0.1272(3) 0.6064(4) 0.0613(15) Uani 1 1 d . . . H7A H 0.2029 0.1671 0.5814 0.074 Uiso 1 1 calc R . . C8 C 0.1819(7) 0.0649(3) 0.5851(4) 0.0783(19) Uani 1 1 d . . . H8A H 0.1075 0.0630 0.5456 0.094 Uiso 1 1 calc R . . C9 C 0.2344(8) 0.0049(3) 0.6221(5) 0.083(2) Uani 1 1 d . . . H9A H 0.1947 -0.0368 0.6073 0.100 Uiso 1 1 calc R . . C10 C 0.3435(8) 0.0065(3) 0.6800(5) 0.081(2) Uani 1 1 d . . . H10A H 0.3770 -0.0341 0.7044 0.097 Uiso 1 1 calc R . . C11 C 0.2613(5) 0.2784(3) 0.6741(3) 0.0450(12) Uani 1 1 d . . . H11A H 0.2348 0.2567 0.7207 0.054 Uiso 1 1 calc R . . C12 C 0.1802(5) 0.3322(2) 0.6377(3) 0.0434(11) Uani 1 1 d . . . C13 C 0.0724(5) 0.3479(3) 0.6784(4) 0.0576(14) Uani 1 1 d . . . H13A H 0.0662 0.3273 0.7304 0.069 Uiso 1 1 calc R . . C14 C -0.0223(5) 0.3916(3) 0.6452(5) 0.0660(17) Uani 1 1 d . . . H14A H -0.0910 0.4016 0.6741 0.079 Uiso 1 1 calc R . . C15 C -0.0133(5) 0.4208(3) 0.5669(4) 0.0632(17) Uani 1 1 d . . . H15A H -0.0783 0.4499 0.5423 0.076 Uiso 1 1 calc R . . C16 C 0.0887(5) 0.4079(3) 0.5253(4) 0.0546(13) Uani 1 1 d . . . H16A H 0.0914 0.4289 0.4732 0.066 Uiso 1 1 calc R . . C17 C 0.1911(5) 0.3636(2) 0.5581(3) 0.0428(11) Uani 1 1 d . . . C18 C 0.5452(4) 0.3486(3) 0.4644(3) 0.0417(11) Uani 1 1 d . . . C19 C 0.5516(6) 0.3284(3) 0.3806(3) 0.0564(14) Uani 1 1 d . . . H19A H 0.5139 0.2872 0.3610 0.068 Uiso 1 1 calc R . . C20 C 0.6122(6) 0.3679(4) 0.3262(4) 0.0695(18) Uani 1 1 d . . . H20A H 0.6133 0.3536 0.2705 0.083 Uiso 1 1 calc R . . C21 C 0.6710(6) 0.4285(3) 0.3540(4) 0.0674(17) Uani 1 1 d . . . H21A H 0.7147 0.4540 0.3179 0.081 Uiso 1 1 calc R . . C22 C 0.6649(5) 0.4510(3) 0.4351(4) 0.0562(14) Uani 1 1 d . . . H22A H 0.7011 0.4928 0.4535 0.067 Uiso 1 1 calc R . . C23 C 0.6040(4) 0.4107(2) 0.4894(3) 0.0420(11) Uani 1 1 d . . . C24 C 0.5936(4) 0.4315(2) 0.5771(3) 0.0402(11) Uani 1 1 d . . . C25 C 0.6425(5) 0.4912(3) 0.6168(3) 0.0512(13) Uani 1 1 d . . . H25A H 0.6870 0.5221 0.5872 0.061 Uiso 1 1 calc R . . C26 C 0.6261(5) 0.5051(3) 0.6984(4) 0.0569(14) Uani 1 1 d . . . H26A H 0.6600 0.5448 0.7250 0.068 Uiso 1 1 calc R . . C27 C 0.5582(5) 0.4591(3) 0.7412(3) 0.0551(14) Uani 1 1 d . . . H27A H 0.5447 0.4679 0.7967 0.066 Uiso 1 1 calc R . . C28 C 0.5108(5) 0.4001(3) 0.7004(3) 0.0452(11) Uani 1 1 d . . . H28A H 0.4661 0.3689 0.7294 0.054 Uiso 1 1 calc R . . C29 C 0.3003(6) 0.2115(3) 0.4247(3) 0.0587(15) Uani 1 1 d . . . H29A H 0.2432 0.2482 0.4201 0.070 Uiso 1 1 calc R . . C30 C 0.2681(7) 0.1548(3) 0.3758(4) 0.0770(19) Uani 1 1 d . . . H30A H 0.1908 0.1525 0.3392 0.092 Uiso 1 1 calc R . . C31 C 0.3548(7) 0.1010(4) 0.3828(4) 0.082(2) Uani 1 1 d . . . H31A H 0.3364 0.0619 0.3500 0.098 Uiso 1 1 calc R . . C32 C 0.4677(7) 0.1052(3) 0.4377(4) 0.0685(16) Uani 1 1 d . . . H32A H 0.5253 0.0687 0.4427 0.082 Uiso 1 1 calc R . . C33 C 0.4960(5) 0.1642(3) 0.4862(3) 0.0473(12) Uani 1 1 d . . . C34 C 0.6127(5) 0.1772(3) 0.5455(3) 0.0451(12) Uani 1 1 d . . . C35 C 0.7113(6) 0.1294(3) 0.5638(4) 0.0580(14) Uani 1 1 d . . . H35A H 0.7045 0.0865 0.5383 0.070 Uiso 1 1 calc R . . C36 C 0.8190(6) 0.1464(3) 0.6202(4) 0.0708(17) Uani 1 1 d . . . H36A H 0.8853 0.1149 0.6334 0.085 Uiso 1 1 calc R . . C37 C 0.8275(6) 0.2113(3) 0.6571(4) 0.0648(16) Uani 1 1 d . . . H37A H 0.9005 0.2230 0.6947 0.078 Uiso 1 1 calc R . . C38 C 0.7307(5) 0.2579(3) 0.6391(3) 0.0512(13) Uani 1 1 d . . . H38A H 0.7388 0.3008 0.6647 0.061 Uiso 1 1 calc R . . C39 C 0.6194(4) 0.2425(2) 0.5828(3) 0.0382(10) Uani 1 1 d . . . C40 C -0.1151(9) 0.2704(4) 0.4493(5) 0.085(2) Uani 1 1 d D . . H40C H -0.2036 0.2738 0.4580 0.23(6) Uiso 1 1 calc RD . . H40B H -0.0960 0.3060 0.4114 0.18(5) Uiso 1 1 calc RD . . H40A H -0.0605 0.2754 0.5028 0.19(5) Uiso 1 1 calc RD . . C41 C -0.0934(8) 0.2057(4) 0.4137(5) 0.086(2) Uani 1 1 d . . . N4 N -0.0753(11) 0.1555(4) 0.3841(6) 0.175(5) Uani 1 1 d . . . 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 0.03765(12) 0.03528(12) 0.03201(11) 0.00332(8) 0.00344(7) -0.00021(8) O1 0.044(2) 0.047(2) 0.0492(19) 0.0075(16) 0.0024(16) 0.0063(16) N1 0.044(2) 0.034(2) 0.041(2) 0.0020(17) 0.0091(18) -0.0017(18) N2 0.037(2) 0.037(2) 0.037(2) 0.0050(17) 0.0003(16) 0.0004(16) N3 0.047(3) 0.045(2) 0.036(2) -0.0014(17) 0.0074(18) -0.0036(18) C1 0.053(3) 0.036(3) 0.043(3) 0.011(2) 0.022(2) 0.006(2) C2 0.061(4) 0.051(3) 0.048(3) 0.012(2) 0.011(3) 0.006(3) C3 0.076(4) 0.068(4) 0.058(4) 0.018(3) 0.010(3) 0.020(3) C4 0.097(5) 0.062(4) 0.066(4) 0.024(3) 0.023(4) 0.029(4) C5 0.088(5) 0.037(3) 0.064(3) 0.009(3) 0.044(3) 0.009(3) C6 0.060(4) 0.041(3) 0.048(3) 0.005(2) 0.027(3) 0.000(2) C7 0.077(4) 0.047(3) 0.067(4) -0.004(3) 0.032(3) -0.007(3) C8 0.086(5) 0.068(4) 0.086(5) -0.020(4) 0.029(4) -0.020(4) C9 0.122(6) 0.043(4) 0.095(5) -0.012(4) 0.052(5) -0.016(4) C10 0.119(6) 0.048(4) 0.086(5) 0.004(3) 0.050(5) 0.011(4) C11 0.051(3) 0.043(3) 0.043(3) 0.003(2) 0.015(2) -0.002(2) C12 0.039(3) 0.035(3) 0.056(3) -0.004(2) 0.007(2) -0.002(2) C13 0.053(3) 0.045(3) 0.078(4) -0.004(3) 0.020(3) -0.006(3) C14 0.048(3) 0.046(3) 0.107(5) -0.011(3) 0.021(3) 0.001(3) C15 0.041(3) 0.042(3) 0.101(5) -0.005(3) -0.010(3) 0.004(2) C16 0.049(3) 0.042(3) 0.068(3) -0.001(3) -0.008(3) 0.001(2) C17 0.040(3) 0.032(3) 0.055(3) -0.006(2) 0.000(2) -0.002(2) C18 0.036(3) 0.050(3) 0.039(3) 0.010(2) 0.007(2) 0.005(2) C19 0.071(4) 0.058(3) 0.043(3) 0.010(3) 0.018(3) 0.003(3) C20 0.071(4) 0.093(5) 0.048(3) 0.020(3) 0.025(3) 0.018(4) C21 0.054(4) 0.078(4) 0.074(4) 0.037(4) 0.024(3) 0.009(3) C22 0.043(3) 0.062(4) 0.065(4) 0.023(3) 0.010(3) 0.000(3) C23 0.033(3) 0.045(3) 0.048(3) 0.014(2) 0.005(2) 0.003(2) C24 0.033(3) 0.036(3) 0.049(3) 0.010(2) 0.000(2) 0.003(2) C25 0.042(3) 0.039(3) 0.071(4) 0.006(3) 0.005(3) -0.006(2) C26 0.052(3) 0.041(3) 0.074(4) -0.013(3) -0.003(3) -0.003(3) C27 0.061(4) 0.052(3) 0.051(3) -0.009(3) 0.000(3) 0.002(3) C28 0.051(3) 0.043(3) 0.041(3) 0.004(2) 0.004(2) 0.001(2) C29 0.062(4) 0.061(4) 0.049(3) -0.005(3) -0.008(3) -0.001(3) C30 0.091(5) 0.075(5) 0.058(4) -0.018(3) -0.013(3) -0.013(4) C31 0.105(6) 0.074(5) 0.062(4) -0.031(4) 0.001(4) -0.012(4) C32 0.091(5) 0.049(3) 0.067(4) -0.017(3) 0.015(3) 0.004(3) C33 0.060(3) 0.044(3) 0.040(3) -0.004(2) 0.014(2) 0.005(3) C34 0.048(3) 0.046(3) 0.044(3) 0.003(2) 0.014(2) 0.007(2) C35 0.062(4) 0.053(3) 0.062(3) 0.001(3) 0.016(3) 0.015(3) C36 0.061(4) 0.077(5) 0.076(4) 0.021(4) 0.012(3) 0.025(3) C37 0.048(4) 0.081(5) 0.063(4) 0.015(3) -0.001(3) 0.004(3) C38 0.046(3) 0.057(3) 0.049(3) 0.006(3) 0.004(2) 0.001(3) C39 0.042(3) 0.043(3) 0.032(2) 0.007(2) 0.011(2) 0.001(2) C40 0.099(6) 0.073(5) 0.089(5) -0.007(4) 0.030(5) -0.002(4) C41 0.124(7) 0.072(5) 0.069(4) -0.013(4) 0.039(4) -0.028(4) N4 0.307(13) 0.099(6) 0.150(7) -0.034(6) 0.136(8) -0.053(7) _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 2.007(5) . ? Ir1 C39 2.007(5) . ? Ir1 N3 2.032(4) . ? Ir1 N2 2.054(4) . ? Ir1 O1 2.153(3) . ? Ir1 N1 2.158(4) . ? O1 C17 1.290(6) . ? N1 C11 1.283(6) . ? N1 C1 1.443(6) . ? N2 C28 1.351(6) . ? N2 C24 1.361(6) . ? N3 C29 1.341(6) . ? N3 C33 1.363(6) . ? C1 C2 1.368(8) . ? C1 C6 1.404(7) . ? C2 C3 1.408(7) . ? C3 C4 1.342(9) . ? C4 C5 1.413(9) . ? C5 C10 1.402(9) . ? C5 C6 1.432(7) . ? C6 C7 1.416(8) . ? C7 C8 1.379(8) . ? C8 C9 1.389(9) . ? C9 C10 1.362(9) . ? C11 C12 1.422(7) . ? C12 C13 1.415(7) . ? C12 C17 1.427(7) . ? C13 C14 1.358(7) . ? C14 C15 1.386(8) . ? C15 C16 1.361(7) . ? C16 C17 1.418(6) . ? C18 C23 1.392(7) . ? C18 C19 1.401(6) . ? C19 C20 1.381(7) . ? C20 C21 1.377(9) . ? C21 C22 1.373(8) . ? C22 C23 1.391(6) . ? C23 C24 1.473(7) . ? C24 C25 1.389(7) . ? C25 C26 1.362(7) . ? C26 C27 1.384(8) . ? C27 C28 1.382(7) . ? C29 C30 1.368(7) . ? C30 C31 1.384(9) . ? C31 C32 1.370(9) . ? C32 C33 1.395(7) . ? C33 C34 1.457(7) . ? C34 C35 1.393(7) . ? C34 C39 1.403(7) . ? C35 C36 1.379(8) . ? C36 C37 1.394(8) . ? C37 C38 1.365(7) . ? C38 C39 1.399(6) . ? C40 C41 1.418(9) . ? C41 N4 1.115(9) . ? 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 C39 89.82(18) . . ? C18 Ir1 N3 94.32(18) . . ? C39 Ir1 N3 80.14(18) . . ? C18 Ir1 N2 79.86(18) . . ? C39 Ir1 N2 97.43(17) . . ? N3 Ir1 N2 173.74(15) . . ? C18 Ir1 O1 90.80(15) . . ? C39 Ir1 O1 175.06(16) . . ? N3 Ir1 O1 94.93(15) . . ? N2 Ir1 O1 87.51(13) . . ? C18 Ir1 N1 175.56(17) . . ? C39 Ir1 N1 93.26(16) . . ? N3 Ir1 N1 89.37(15) . . ? N2 Ir1 N1 96.55(14) . . ? O1 Ir1 N1 86.41(14) . . ? C17 O1 Ir1 127.0(3) . . ? C11 N1 C1 116.3(4) . . ? C11 N1 Ir1 124.5(3) . . ? C1 N1 Ir1 119.0(3) . . ? C28 N2 C24 119.1(4) . . ? C28 N2 Ir1 125.0(3) . . ? C24 N2 Ir1 115.9(3) . . ? C29 N3 C33 119.4(4) . . ? C29 N3 Ir1 124.5(4) . . ? C33 N3 Ir1 116.1(3) . . ? C2 C1 C6 121.0(5) . . ? C2 C1 N1 120.2(4) . . ? C6 C1 N1 118.8(5) . . ? C1 C2 C3 120.6(5) . . ? C4 C3 C2 119.7(6) . . ? C3 C4 C5 122.1(5) . . ? C10 C5 C4 122.6(6) . . ? C10 C5 C6 119.1(6) . . ? C4 C5 C6 118.3(5) . . ? C1 C6 C7 123.4(5) . . ? C1 C6 C5 118.3(5) . . ? C7 C6 C5 118.2(5) . . ? C8 C7 C6 120.5(6) . . ? C7 C8 C9 120.5(7) . . ? C10 C9 C8 120.8(6) . . ? C9 C10 C5 120.9(6) . . ? N1 C11 C12 129.0(5) . . ? C13 C12 C11 116.4(5) . . ? C13 C12 C17 119.0(5) . . ? C11 C12 C17 124.0(4) . . ? C14 C13 C12 123.2(6) . . ? C13 C14 C15 117.9(6) . . ? C16 C15 C14 121.4(5) . . ? C15 C16 C17 122.8(5) . . ? O1 C17 C16 118.4(5) . . ? O1 C17 C12 125.8(4) . . ? C16 C17 C12 115.8(5) . . ? C23 C18 C19 115.9(5) . . ? C23 C18 Ir1 115.6(3) . . ? C19 C18 Ir1 128.5(4) . . ? C20 C19 C18 121.9(6) . . ? C21 C20 C19 120.2(6) . . ? C22 C21 C20 119.9(5) . . ? C21 C22 C23 119.3(5) . . ? C22 C23 C18 122.7(5) . . ? C22 C23 C24 122.4(5) . . ? C18 C23 C24 114.9(4) . . ? N2 C24 C25 120.2(4) . . ? N2 C24 C23 113.7(4) . . ? C25 C24 C23 126.1(4) . . ? C26 C25 C24 120.7(5) . . ? C25 C26 C27 119.0(5) . . ? C28 C27 C26 119.1(5) . . ? N2 C28 C27 121.9(5) . . ? N3 C29 C30 123.3(6) . . ? C29 C30 C31 117.6(6) . . ? C32 C31 C30 120.3(6) . . ? C31 C32 C33 119.9(6) . . ? N3 C33 C32 119.5(5) . . ? N3 C33 C34 114.0(4) . . ? C32 C33 C34 126.5(5) . . ? C35 C34 C39 122.0(5) . . ? C35 C34 C33 123.2(5) . . ? C39 C34 C33 114.8(4) . . ? C36 C35 C34 119.3(5) . . ? C35 C36 C37 119.3(5) . . ? C38 C37 C36 121.2(6) . . ? C37 C38 C39 121.2(5) . . ? C38 C39 C34 117.0(4) . . ? C38 C39 Ir1 128.1(4) . . ? C34 C39 Ir1 114.8(3) . . ? N4 C41 C40 178.4(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.640 _refine_diff_density_min -1.005 _refine_diff_density_rms 0.105