# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' #TrackingRef '- compound_1.cif' # "Unsaturated iridium pyridinedicarboxylate pincer complexes # with catalytic activity in borylation of arenes" # # by Duc H. Nguyen, Jesus J. Perez-Torrente, Laura Lomba, # M. Victoria Jimenez, Fernando J. Lahoz and Luis A. Oro # # # Submitted to 'Chemical Communications' # Manuscript number ........... # ----------------------------------------------------------- # _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_section_title ; Unsaturated iridium pyridinedicarboxylate pincer complexes with catalytic activity in borylation of arenes ; # Person for contact _publ_contact_author_name 'Dr. Fernando J. Lahoz' _publ_contact_author_address ; Dr. Fernando J. Lahoz Departamento de Qu\'imica Inorg\'anica - I.C.M.A. Facultad de Ciencias Universidad de Zaragoza - C.S.I.C. 50009 Zaragoza, Spain ; _publ_contact_author_phone '+34 976 761147' _publ_contact_author_fax '+34 976 761187' _publ_contact_author_email lahoz@unizar.es loop_ _publ_author_name M.V.Jimenez F.J.Lahoz Lomba,L. D.H.Nguyen L.A.Oro ; J.J.Perez-Torrente ; # ---------------------------------------------------------- # Data for compound_1 (local labelling as fjl9as) data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 819913' #TrackingRef '- compound_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H20 Ir N O5, C H4 O' _chemical_formula_sum 'C17 H24 Ir N O6' _chemical_formula_weight 530.57 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 P21/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 12.5949(7) _cell_length_b 13.7791(8) _cell_length_c 11.4521(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.4180(10) _cell_angle_gamma 90.00 _cell_volume 1779.92(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4797 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.47 _exptl_crystal_description primatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.980 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 7.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3425 _exptl_absorpt_correction_T_max 0.3998 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS within SAINT+ package, v. 6.45. ; _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 SMART APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 11737 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4273 _reflns_number_gt 3785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v. 5.611 (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT+ v. 6.45 (Bruker AXS, 2003)' _computing_data_reduction 'SAINT+ v. 6.45 (Bruker AXS, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP program, SHELXTL v6.12, Bruker2000' _computing_publication_material 'XCIF program, SHELXTLv6.12, BrukerAXS' _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. All non-hydrogen atom were refined with anisotropic displacement parameters. Hydrogen atoms were included from calculated positions and refined with only riding displacement parameters, except for hydrogens bonded to C12 which were refined also with riding positional parameters. All residuals above 1 e/A3 were found in close proximity of the metal centre and have no chemical sense. ; _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^)+(0.0257P)^2^+3.7013P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4273 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.003 _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 0.217809(12) 0.420636(11) 0.961832(13) 0.01282(6) Uani 1 1 d . . . O1 O 0.3070(2) 0.4853(2) 1.1433(3) 0.0149(6) Uani 1 1 d . . . O2 O 0.4612(3) 0.4628(2) 1.3390(3) 0.0192(6) Uani 1 1 d . . . O3 O 0.1728(2) 0.3123(2) 0.8223(3) 0.0186(6) Uani 1 1 d . . . O4 O 0.2247(3) 0.1628(2) 0.7903(3) 0.0238(7) Uani 1 1 d . . . N1 N 0.3383(3) 0.3207(2) 1.0562(3) 0.0139(7) Uani 1 1 d . . . C1 C 0.3971(4) 0.4358(3) 1.2293(4) 0.0156(8) Uani 1 1 d . . . C2 C 0.4174(3) 0.3387(3) 1.1805(4) 0.0139(8) Uani 1 1 d . . . C3 C 0.5026(4) 0.2706(3) 1.2493(4) 0.0176(8) Uani 1 1 d . . . H3 H 0.557(4) 0.283(3) 1.336(5) 0.021 Uiso 1 1 d . . . C4 C 0.5059(4) 0.1845(3) 1.1883(4) 0.0190(8) Uani 1 1 d . . . H4 H 0.567(4) 0.134(4) 1.234(4) 0.023 Uiso 1 1 d . . . C5 C 0.4217(4) 0.1667(3) 1.0592(4) 0.0180(8) Uani 1 1 d . . . H5 H 0.422(4) 0.113(4) 1.018(5) 0.022 Uiso 1 1 d . . . C6 C 0.3389(3) 0.2380(3) 0.9958(4) 0.0157(8) Uani 1 1 d . . . C7 C 0.2387(3) 0.2355(3) 0.8581(4) 0.0180(8) Uani 1 1 d . . . C11 C 0.3253(4) 0.4937(4) 0.8973(5) 0.0251(10) Uani 1 1 d . . . H11 H 0.397(5) 0.472(4) 0.937(5) 0.030 Uiso 1 1 d . . . C12 C 0.3354(4) 0.6008(4) 0.9438(5) 0.0292(11) Uani 1 1 d . . . H12A H 0.3625 0.6418 0.8913 0.035 Uiso 1 1 calc R . . H12B H 0.3953 0.6052 1.0361 0.035 Uiso 1 1 calc R . . C13 C 0.2107(5) 0.6404(3) 0.9299(5) 0.0288(11) Uani 1 1 d . . . H13A H 0.225(4) 0.676(4) 1.011(5) 0.035 Uiso 1 1 d . . . H13B H 0.180(5) 0.679(4) 0.865(5) 0.035 Uiso 1 1 d . . . C14 C 0.1266(4) 0.5594(3) 0.9208(5) 0.0227(9) Uani 1 1 d . . . H14 H 0.091(5) 0.562(3) 0.977(5) 0.027 Uiso 1 1 d . . . C15 C 0.0670(4) 0.4992(3) 0.8152(4) 0.0243(10) Uani 1 1 d . . . H15 H 0.001(4) 0.460(4) 0.817(5) 0.029 Uiso 1 1 d . . . C16 C 0.0647(5) 0.5027(4) 0.6826(4) 0.0313(11) Uani 1 1 d . . . H16A H 0.052(5) 0.439(4) 0.643(5) 0.038 Uiso 1 1 d . . . H16B H -0.007(5) 0.549(4) 0.623(5) 0.038 Uiso 1 1 d . . . C17 C 0.1698(5) 0.5407(4) 0.6693(5) 0.0367(12) Uani 1 1 d . . . H17A H 0.177(5) 0.616(5) 0.690(5) 0.044 Uiso 1 1 d . . . H17B H 0.146(5) 0.536(4) 0.564(6) 0.044 Uiso 1 1 d . . . C18 C 0.2836(5) 0.4862(4) 0.7507(5) 0.0306(11) Uani 1 1 d . . . H18A H 0.257(5) 0.421(4) 0.716(5) 0.037 Uiso 1 1 d . . . H18B H 0.360(5) 0.521(4) 0.728(5) 0.037 Uiso 1 1 d . . . O5 O 0.0954(3) 0.3517(2) 1.0348(3) 0.0167(6) Uani 1 1 d . . . H5M H 0.125(4) 0.348(4) 1.108(5) 0.020 Uiso 1 1 d . . . C19 C 0.0336(4) 0.2623(3) 0.9819(4) 0.0238(9) Uani 1 1 d . . . H19A H -0.012(5) 0.243(4) 1.025(5) 0.036 Uiso 1 1 d . . . H19B H 0.084(5) 0.211(4) 0.995(5) 0.036 Uiso 1 1 d . . . H19C H -0.025(4) 0.277(4) 0.886(5) 0.036 Uiso 1 1 d . . . C1S C 0.2468(5) 0.5896(4) 0.3896(5) 0.0292(11) Uani 1 1 d . . . H2S H 0.211(5) 0.627(5) 0.420(6) 0.044 Uiso 1 1 d . . . H3S H 0.217(5) 0.518(4) 0.396(6) 0.044 Uiso 1 1 d . . . H4S H 0.331(6) 0.592(4) 0.434(6) 0.044 Uiso 1 1 d . . . O1S O 0.2085(3) 0.6202(3) 0.2592(3) 0.0286(8) Uani 1 1 d . . . H1S H 0.230(6) 0.588(5) 0.238(7) 0.043 Uiso 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 0.01163(8) 0.01368(9) 0.01349(8) 0.00363(6) 0.00588(6) 0.00366(6) O1 0.0139(13) 0.0135(14) 0.0151(13) -0.0007(11) 0.0044(11) 0.0008(11) O2 0.0215(15) 0.0177(15) 0.0168(13) -0.0044(12) 0.0072(12) -0.0055(12) O3 0.0157(14) 0.0231(16) 0.0152(13) 0.0011(11) 0.0054(12) 0.0052(12) O4 0.0234(16) 0.0261(17) 0.0178(14) -0.0070(12) 0.0055(13) 0.0050(13) N1 0.0142(16) 0.0145(17) 0.0131(15) 0.0018(13) 0.0063(13) 0.0018(13) C1 0.0156(19) 0.014(2) 0.0216(19) 0.0007(15) 0.0125(17) -0.0025(15) C2 0.0131(18) 0.0137(19) 0.0161(18) 0.0027(15) 0.0075(15) 0.0024(15) C3 0.0151(19) 0.019(2) 0.0167(18) -0.0003(16) 0.0055(16) -0.0003(16) C4 0.019(2) 0.017(2) 0.020(2) 0.0044(16) 0.0080(17) 0.0055(17) C5 0.020(2) 0.014(2) 0.0192(19) -0.0012(16) 0.0086(17) 0.0041(16) C6 0.0164(19) 0.017(2) 0.0139(17) -0.0002(15) 0.0074(15) 0.0001(16) C7 0.0162(19) 0.024(2) 0.0139(17) -0.0001(16) 0.0068(16) 0.0033(17) C11 0.015(2) 0.033(3) 0.029(2) 0.010(2) 0.0105(19) 0.0048(19) C12 0.027(2) 0.030(3) 0.025(2) 0.0028(19) 0.007(2) -0.012(2) C13 0.047(3) 0.014(2) 0.025(2) 0.0023(18) 0.015(2) 0.003(2) C14 0.025(2) 0.016(2) 0.033(2) 0.0123(18) 0.018(2) 0.0112(17) C15 0.014(2) 0.024(2) 0.031(2) 0.0163(19) 0.0055(18) 0.0052(18) C16 0.036(3) 0.026(3) 0.019(2) 0.0009(19) 0.001(2) -0.004(2) C17 0.042(3) 0.046(3) 0.021(2) 0.004(2) 0.013(2) 0.000(3) C18 0.040(3) 0.031(3) 0.028(2) 0.004(2) 0.022(2) 0.005(2) O5 0.0175(15) 0.0171(15) 0.0143(13) 0.0020(11) 0.0060(12) -0.0005(12) C19 0.023(2) 0.019(2) 0.025(2) -0.0011(18) 0.0080(19) -0.0055(19) C1S 0.028(3) 0.033(3) 0.028(2) -0.004(2) 0.013(2) 0.001(2) O1S 0.0272(18) 0.034(2) 0.0252(16) -0.0044(15) 0.0117(14) 0.0083(15) _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 N1 1.977(3) . ? Ir1 C11 2.069(4) . ? Ir1 O3 2.073(3) . ? Ir1 O1 2.073(3) . ? Ir1 C14 2.171(4) . ? Ir1 C15 2.181(4) . ? Ir1 O5 2.263(3) . ? O1 C1 1.315(5) . ? O2 C1 1.211(5) . ? O3 C7 1.294(5) . ? O4 C7 1.231(5) . ? N1 C6 1.334(5) . ? N1 C2 1.349(5) . ? C1 C2 1.515(5) . ? C2 C3 1.378(5) . ? C3 C4 1.387(6) . ? C3 H3 0.94(5) . ? C4 C5 1.405(6) . ? C4 H4 1.00(5) . ? C5 C6 1.382(6) . ? C5 H5 0.88(5) . ? C6 C7 1.519(5) . ? C11 C18 1.523(6) . ? C11 C12 1.555(7) . ? C11 H11 0.86(5) . ? C12 C13 1.602(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.510(7) . ? C13 H13A 1.00(5) . ? C13 H13B 0.85(5) . ? C14 C15 1.381(7) . ? C14 H14 0.93(5) . ? C15 C16 1.507(7) . ? C15 H15 1.00(5) . ? C16 C17 1.493(8) . ? C16 H16A 0.96(6) . ? C16 H16B 1.07(6) . ? C17 C18 1.515(7) . ? C17 H17A 1.06(6) . ? C17 H17B 1.10(6) . ? C18 H18A 0.98(5) . ? C18 H18B 1.20(5) . ? O5 C19 1.439(5) . ? O5 H5M 0.75(5) . ? C19 H19A 0.95(5) . ? C19 H19B 0.92(6) . ? C19 H19C 1.03(5) . ? C1S O1S 1.414(6) . ? C1S H2S 0.86(6) . ? C1S H3S 1.07(6) . ? C1S H4S 0.96(6) . ? O1S H1S 0.63(6) . ? 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 N1 Ir1 C11 93.95(16) . . ? N1 Ir1 O3 78.45(12) . . ? C11 Ir1 O3 94.16(16) . . ? N1 Ir1 O1 79.02(12) . . ? C11 Ir1 O1 90.03(16) . . ? O3 Ir1 O1 157.31(11) . . ? N1 Ir1 C14 159.26(17) . . ? C11 Ir1 C14 82.05(18) . . ? O3 Ir1 C14 122.02(15) . . ? O1 Ir1 C14 80.64(15) . . ? N1 Ir1 C15 163.72(17) . . ? C11 Ir1 C15 88.13(17) . . ? O3 Ir1 C15 85.30(15) . . ? O1 Ir1 C15 117.16(16) . . ? C14 Ir1 C15 36.98(18) . . ? N1 Ir1 O5 89.39(12) . . ? C11 Ir1 O5 175.71(16) . . ? O3 Ir1 O5 89.14(11) . . ? O1 Ir1 O5 87.96(11) . . ? C14 Ir1 O5 93.88(14) . . ? C15 Ir1 O5 89.41(14) . . ? C1 O1 Ir1 115.5(2) . . ? C7 O3 Ir1 115.3(2) . . ? C6 N1 C2 122.2(3) . . ? C6 N1 Ir1 119.4(3) . . ? C2 N1 Ir1 118.4(3) . . ? O2 C1 O1 124.9(4) . . ? O2 C1 C2 120.7(4) . . ? O1 C1 C2 114.4(3) . . ? N1 C2 C3 120.0(4) . . ? N1 C2 C1 112.6(3) . . ? C3 C2 C1 127.3(4) . . ? C2 C3 C4 119.0(4) . . ? C2 C3 H3 120(3) . . ? C4 C3 H3 121(3) . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 122(3) . . ? C5 C4 H4 118(3) . . ? C6 C5 C4 117.9(4) . . ? C6 C5 H5 120(3) . . ? C4 C5 H5 122(3) . . ? N1 C6 C5 120.8(4) . . ? N1 C6 C7 111.3(3) . . ? C5 C6 C7 127.8(4) . . ? O4 C7 O3 125.0(4) . . ? O4 C7 C6 119.5(4) . . ? O3 C7 C6 115.4(3) . . ? C18 C11 C12 112.2(4) . . ? C18 C11 Ir1 113.7(3) . . ? C12 C11 Ir1 107.8(3) . . ? C18 C11 H11 109(3) . . ? C12 C11 H11 104(4) . . ? Ir1 C11 H11 110(3) . . ? C11 C12 C13 111.2(4) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 112.4(4) . . ? C14 C13 H13A 105(3) . . ? C12 C13 H13A 108(3) . . ? C14 C13 H13B 112(4) . . ? C12 C13 H13B 110(4) . . ? H13A C13 H13B 109(5) . . ? C15 C14 C13 126.6(4) . . ? C15 C14 Ir1 71.9(2) . . ? C13 C14 Ir1 110.4(3) . . ? C15 C14 H14 113(3) . . ? C13 C14 H14 117(3) . . ? Ir1 C14 H14 105(3) . . ? C14 C15 C16 128.5(4) . . ? C14 C15 Ir1 71.1(2) . . ? C16 C15 Ir1 114.3(3) . . ? C14 C15 H15 116(3) . . ? C16 C15 H15 113(3) . . ? Ir1 C15 H15 100(3) . . ? C17 C16 C15 119.6(4) . . ? C17 C16 H16A 104(3) . . ? C15 C16 H16A 111(3) . . ? C17 C16 H16B 105(3) . . ? C15 C16 H16B 107(3) . . ? H16A C16 H16B 109(4) . . ? C16 C17 C18 113.7(4) . . ? C16 C17 H17A 109(3) . . ? C18 C17 H17A 113(3) . . ? C16 C17 H17B 106(3) . . ? C18 C17 H17B 111(3) . . ? H17A C17 H17B 105(4) . . ? C17 C18 C11 114.3(4) . . ? C17 C18 H18A 98(3) . . ? C11 C18 H18A 114(3) . . ? C17 C18 H18B 107(3) . . ? C11 C18 H18B 107(3) . . ? H18A C18 H18B 116(4) . . ? C19 O5 Ir1 122.3(3) . . ? C19 O5 H5M 109(4) . . ? Ir1 O5 H5M 111(4) . . ? O5 C19 H19A 111(3) . . ? O5 C19 H19B 113(3) . . ? H19A C19 H19B 104(5) . . ? O5 C19 H19C 106(3) . . ? H19A C19 H19C 107(4) . . ? H19B C19 H19C 116(4) . . ? O1S C1S H2S 105(4) . . ? O1S C1S H3S 112(3) . . ? H2S C1S H3S 105(5) . . ? O1S C1S H4S 109(4) . . ? H2S C1S H4S 115(5) . . ? H3S C1S H4S 110(4) . . ? C1S O1S H1S 102(7) . . ? 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 N1 Ir1 O1 C1 1.7(3) . . . . ? C11 Ir1 O1 C1 -92.3(3) . . . . ? O3 Ir1 O1 C1 8.6(4) . . . . ? C14 Ir1 O1 C1 -174.2(3) . . . . ? C15 Ir1 O1 C1 179.8(3) . . . . ? O5 Ir1 O1 C1 91.5(3) . . . . ? N1 Ir1 O3 C7 0.1(3) . . . . ? C11 Ir1 O3 C7 93.2(3) . . . . ? O1 Ir1 O3 C7 -6.9(5) . . . . ? C14 Ir1 O3 C7 176.5(3) . . . . ? C15 Ir1 O3 C7 -179.0(3) . . . . ? O5 Ir1 O3 C7 -89.5(3) . . . . ? C11 Ir1 N1 C6 -92.7(3) . . . . ? O3 Ir1 N1 C6 0.7(3) . . . . ? O1 Ir1 N1 C6 178.0(3) . . . . ? C14 Ir1 N1 C6 -170.6(4) . . . . ? C15 Ir1 N1 C6 4.2(7) . . . . ? O5 Ir1 N1 C6 90.0(3) . . . . ? C11 Ir1 N1 C2 87.5(3) . . . . ? O3 Ir1 N1 C2 -179.0(3) . . . . ? O1 Ir1 N1 C2 -1.7(3) . . . . ? C14 Ir1 N1 C2 9.6(6) . . . . ? C15 Ir1 N1 C2 -175.6(5) . . . . ? O5 Ir1 N1 C2 -89.8(3) . . . . ? Ir1 O1 C1 O2 178.1(3) . . . . ? Ir1 O1 C1 C2 -1.4(4) . . . . ? C6 N1 C2 C3 0.2(6) . . . . ? Ir1 N1 C2 C3 179.9(3) . . . . ? C6 N1 C2 C1 -178.3(3) . . . . ? Ir1 N1 C2 C1 1.5(4) . . . . ? O2 C1 C2 N1 -179.5(4) . . . . ? O1 C1 C2 N1 0.0(5) . . . . ? O2 C1 C2 C3 2.1(6) . . . . ? O1 C1 C2 C3 -178.3(4) . . . . ? N1 C2 C3 C4 0.5(6) . . . . ? C1 C2 C3 C4 178.7(4) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? C3 C4 C5 C6 1.4(6) . . . . ? C2 N1 C6 C5 -0.1(6) . . . . ? Ir1 N1 C6 C5 -179.8(3) . . . . ? C2 N1 C6 C7 178.5(3) . . . . ? Ir1 N1 C6 C7 -1.3(4) . . . . ? C4 C5 C6 N1 -0.7(6) . . . . ? C4 C5 C6 C7 -179.0(4) . . . . ? Ir1 O3 C7 O4 178.5(3) . . . . ? Ir1 O3 C7 C6 -0.7(4) . . . . ? N1 C6 C7 O4 -178.0(4) . . . . ? C5 C6 C7 O4 0.5(7) . . . . ? N1 C6 C7 O3 1.3(5) . . . . ? C5 C6 C7 O3 179.7(4) . . . . ? N1 Ir1 C11 C18 111.3(3) . . . . ? O3 Ir1 C11 C18 32.6(3) . . . . ? O1 Ir1 C11 C18 -169.7(3) . . . . ? C14 Ir1 C11 C18 -89.2(4) . . . . ? C15 Ir1 C11 C18 -52.5(4) . . . . ? N1 Ir1 C11 C12 -123.7(3) . . . . ? O3 Ir1 C11 C12 157.6(3) . . . . ? O1 Ir1 C11 C12 -44.7(3) . . . . ? C14 Ir1 C11 C12 35.9(3) . . . . ? C15 Ir1 C11 C12 72.5(3) . . . . ? C18 C11 C12 C13 85.7(5) . . . . ? Ir1 C11 C12 C13 -40.2(4) . . . . ? C11 C12 C13 C14 19.7(5) . . . . ? C12 C13 C14 C15 -72.9(6) . . . . ? C12 C13 C14 Ir1 9.2(5) . . . . ? N1 Ir1 C14 C15 177.6(4) . . . . ? C11 Ir1 C14 C15 97.5(3) . . . . ? O3 Ir1 C14 C15 7.6(3) . . . . ? O1 Ir1 C14 C15 -171.1(3) . . . . ? O5 Ir1 C14 C15 -83.8(3) . . . . ? N1 Ir1 C14 C13 54.4(6) . . . . ? C11 Ir1 C14 C13 -25.7(3) . . . . ? O3 Ir1 C14 C13 -115.6(3) . . . . ? O1 Ir1 C14 C13 65.7(3) . . . . ? C15 Ir1 C14 C13 -123.2(5) . . . . ? O5 Ir1 C14 C13 153.0(3) . . . . ? C13 C14 C15 C16 -4.1(8) . . . . ? Ir1 C14 C15 C16 -106.5(5) . . . . ? C13 C14 C15 Ir1 102.4(4) . . . . ? N1 Ir1 C15 C14 -176.9(5) . . . . ? C11 Ir1 C15 C14 -79.2(3) . . . . ? O3 Ir1 C15 C14 -173.6(3) . . . . ? O1 Ir1 C15 C14 9.9(3) . . . . ? O5 Ir1 C15 C14 97.3(3) . . . . ? N1 Ir1 C15 C16 -52.3(7) . . . . ? C11 Ir1 C15 C16 45.4(4) . . . . ? O3 Ir1 C15 C16 -49.0(3) . . . . ? O1 Ir1 C15 C16 134.5(3) . . . . ? C14 Ir1 C15 C16 124.6(5) . . . . ? O5 Ir1 C15 C16 -138.1(3) . . . . ? C14 C15 C16 C17 29.9(8) . . . . ? Ir1 C15 C16 C17 -54.7(6) . . . . ? C15 C16 C17 C18 57.9(7) . . . . ? C16 C17 C18 C11 -63.9(6) . . . . ? C12 C11 C18 C17 -53.3(6) . . . . ? Ir1 C11 C18 C17 69.4(5) . . . . ? N1 Ir1 O5 C19 -74.9(3) . . . . ? O3 Ir1 O5 C19 3.6(3) . . . . ? O1 Ir1 O5 C19 -153.9(3) . . . . ? C14 Ir1 O5 C19 125.6(3) . . . . ? C15 Ir1 O5 C19 88.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.370 _refine_diff_density_min -1.514 _refine_diff_density_rms 0.150