# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jianliang Xiao' _publ_contact_author_email j.xiao@liv.ac.uk loop_ _publ_author_name 'Chao Wang' 'Jianliang Xiao' data_twin4 _database_code_depnum_ccdc_archive 'CCDC 888574' #TrackingRef '- Complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CWG61 _chemical_melting_point ? _chemical_formula_moiety '(Ir 3+), (Cl 1-), (C16 H16 O2 N 1-),(C10 H15 1-)' _chemical_formula_sum 'C26 H31 Cl Ir N O2' _chemical_formula_weight 617.17 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' 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8489(12) _cell_length_b 10.6037(13) _cell_length_c 11.3906(14) _cell_angle_alpha 90.6560(10) _cell_angle_beta 98.1770(10) _cell_angle_gamma 95.502(2) _cell_volume 1171.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6752 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.20 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 5.835 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2568 _exptl_absorpt_correction_T_max 0.4748 _exptl_absorpt_process_details 'TWINABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7159 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _reflns_number_total 5144 _reflns_number_gt 4903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0436P)^2^+0.2198P] 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 5144 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir1 Ir Uani 0.77795(1) 0.69185(1) 0.22666(1) 1.000 0.0125(1) . . Cl1 Cl Uani 1.02087(9) 0.67307(8) 0.27410(8) 1.000 0.0175(2) . . O1 O Uani 0.8486(3) 0.9083(3) -0.2014(2) 1.000 0.0264(8) . . O2 O Uani 0.5754(3) 0.1349(3) 0.4729(3) 1.000 0.0284(9) . . N1 N Uani 0.7638(3) 0.5013(3) 0.1719(3) 1.000 0.0159(8) . . C1 C Uani 0.7945(4) 0.4755(3) 0.0688(3) 1.000 0.0160(10) . . C2 C Uani 0.8160(4) 0.5854(3) -0.0040(3) 1.000 0.0158(10) . . C3 C Uani 0.8055(4) 0.7024(3) 0.0538(3) 1.000 0.0155(10) . . C4 C Uani 0.8197(4) 0.8120(3) -0.0121(3) 1.000 0.0173(10) . . C5 C Uani 0.8385(4) 0.8047(4) -0.1308(3) 1.000 0.0197(10) . . C6 C Uani 0.8467(4) 1.0309(4) -0.1474(4) 1.000 0.0255(11) . . C7 C Uani 0.8491(4) 0.6892(4) -0.1857(3) 1.000 0.0224(11) . . C8 C Uani 0.8391(4) 0.5802(4) -0.1222(3) 1.000 0.0207(11) . . C9 C Uani 0.8096(4) 0.3433(3) 0.0265(3) 1.000 0.0202(10) . . C10 C Uani 0.7222(4) 0.4037(3) 0.2492(3) 1.000 0.0155(10) . . C11 C Uani 0.5946(4) 0.3336(3) 0.2193(3) 1.000 0.0192(10) . . C12 C Uani 0.5484(4) 0.2441(3) 0.2960(4) 1.000 0.0214(11) . . C13 C Uani 0.6303(4) 0.2243(3) 0.4035(3) 1.000 0.0197(11) . . C14 C Uani 0.6612(5) 0.1030(4) 0.5777(4) 1.000 0.0287(11) . . C15 C Uani 0.7571(4) 0.2934(3) 0.4332(3) 1.000 0.0187(10) . . C16 C Uani 0.8025(4) 0.3836(3) 0.3554(3) 1.000 0.0170(10) . . C17 C Uani 0.6242(4) 0.8215(3) 0.2241(3) 1.000 0.0202(11) . . C18 C Uani 0.5807(4) 0.7079(3) 0.2835(4) 1.000 0.0197(10) . . C19 C Uani 0.6744(4) 0.6991(3) 0.3922(3) 1.000 0.0175(10) . . C20 C Uani 0.7767(4) 0.8025(3) 0.3960(3) 1.000 0.0170(10) . . C21 C Uani 0.7509(4) 0.8793(3) 0.2917(3) 1.000 0.0168(10) . . C22 C Uani 0.8251(4) 1.0034(3) 0.2695(4) 1.000 0.0230(11) . . C23 C Uani 0.8982(4) 0.8285(4) 0.4914(3) 1.000 0.0215(11) . . C24 C Uani 0.6608(4) 0.6053(4) 0.4868(4) 1.000 0.0238(11) . . C25 C Uani 0.4521(4) 0.6204(4) 0.2464(4) 1.000 0.0282(14) . . C26 C Uani 0.5436(4) 0.8763(4) 0.1176(4) 1.000 0.0283(12) . . H1 H Uiso 0.75740 1.03660 -0.12020 1.000 0.0380 calc R H2 H Uiso 0.86110 1.09650 -0.20550 1.000 0.0380 calc R H3 H Uiso 0.92040 1.04320 -0.07950 1.000 0.0380 calc R H4 H Uiso 0.84780 0.50090 -0.15870 1.000 0.0250 calc R H5 H Uiso 0.86320 0.68560 -0.26640 1.000 0.0270 calc R H6 H Uiso 0.81650 0.89240 0.02450 1.000 0.0210 calc R H7 H Uiso 0.83200 0.29020 0.09510 1.000 0.0300 calc R H8 H Uiso 0.88380 0.34590 -0.02260 1.000 0.0300 calc R H9 H Uiso 0.72300 0.30780 -0.02050 1.000 0.0300 calc R H10 H Uiso 0.74490 0.07150 0.55620 1.000 0.0430 calc R H11 H Uiso 0.61140 0.03720 0.61930 1.000 0.0430 calc R H12 H Uiso 0.68620 0.17850 0.62960 1.000 0.0430 calc R H13 H Uiso 0.88950 0.43140 0.37580 1.000 0.0200 calc R H14 H Uiso 0.81300 0.27970 0.50610 1.000 0.0220 calc R H15 H Uiso 0.46140 0.19640 0.27560 1.000 0.0260 calc R H16 H Uiso 0.53910 0.34720 0.14610 1.000 0.0230 calc R H17 H Uiso 0.80170 1.02440 0.18600 1.000 0.0350 calc R H18 H Uiso 0.92470 0.99840 0.28780 1.000 0.0350 calc R H19 H Uiso 0.79790 1.06910 0.32010 1.000 0.0350 calc R H20 H Uiso 0.87020 0.87260 0.55870 1.000 0.0320 calc R H21 H Uiso 0.97120 0.88170 0.46020 1.000 0.0320 calc R H22 H Uiso 0.93260 0.74820 0.51750 1.000 0.0320 calc R H23 H Uiso 0.75240 0.58330 0.52060 1.000 0.0360 calc R H24 H Uiso 0.60440 0.52880 0.45290 1.000 0.0360 calc R H25 H Uiso 0.61660 0.64200 0.54920 1.000 0.0360 calc R H26 H Uiso 0.37380 0.65520 0.27500 1.000 0.0430 calc R H27 H Uiso 0.46380 0.53700 0.28040 1.000 0.0430 calc R H28 H Uiso 0.43490 0.61200 0.15970 1.000 0.0430 calc R H29 H Uiso 0.49780 0.80730 0.06390 1.000 0.0420 calc R H30 H Uiso 0.60640 0.93070 0.07610 1.000 0.0420 calc R H31 H Uiso 0.47430 0.92640 0.14360 1.000 0.0420 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 0.0107(1) 0.0147(1) 0.0118(1) -0.0013(1) 0.0010(1) 0.0008(1) Cl1 0.0126(4) 0.0224(4) 0.0172(4) -0.0028(3) 0.0010(3) 0.0022(3) O1 0.0298(16) 0.0298(14) 0.0188(14) 0.0090(11) 0.0034(12) -0.0016(12) O2 0.0258(16) 0.0284(14) 0.0286(16) 0.0133(12) -0.0003(13) -0.0051(12) N1 0.0137(15) 0.0170(13) 0.0160(15) -0.0014(11) -0.0004(12) 0.0003(12) C1 0.0134(17) 0.0185(16) 0.0141(17) -0.0036(13) -0.0036(14) 0.0004(13) C2 0.0136(17) 0.0177(16) 0.0147(17) -0.0027(13) -0.0006(14) -0.0015(13) C3 0.0117(17) 0.0184(16) 0.0157(17) -0.0015(13) 0.0016(14) -0.0007(13) C4 0.0144(18) 0.0219(17) 0.0152(17) -0.0015(14) -0.0001(14) 0.0030(14) C5 0.0150(18) 0.0268(18) 0.0159(18) 0.0033(14) 0.0005(14) -0.0034(15) C6 0.022(2) 0.0260(18) 0.027(2) 0.0083(16) -0.0010(17) 0.0009(16) C7 0.019(2) 0.034(2) 0.0127(17) -0.0016(15) 0.0014(15) -0.0038(16) C8 0.0178(19) 0.0257(18) 0.0174(19) -0.0053(15) 0.0018(15) -0.0017(15) C9 0.0198(19) 0.0203(16) 0.0190(19) -0.0059(14) 0.0001(15) -0.0001(14) C10 0.0131(17) 0.0159(15) 0.0181(18) -0.0003(13) 0.0037(14) 0.0022(13) C11 0.0168(19) 0.0203(16) 0.0191(18) -0.0010(14) -0.0016(15) 0.0009(14) C12 0.0148(18) 0.0224(17) 0.025(2) 0.0024(15) -0.0006(15) -0.0037(14) C13 0.021(2) 0.0163(16) 0.0224(19) 0.0025(14) 0.0042(15) 0.0029(14) C14 0.032(2) 0.0269(19) 0.026(2) 0.0085(17) 0.0015(18) -0.0005(17) C15 0.0186(19) 0.0201(16) 0.0167(18) -0.0008(14) -0.0006(15) 0.0028(14) C16 0.0135(17) 0.0163(15) 0.0200(18) -0.0022(13) -0.0005(14) 0.0004(13) C17 0.0164(19) 0.0231(17) 0.0219(19) -0.0046(15) 0.0031(15) 0.0063(15) C18 0.0100(17) 0.0210(16) 0.029(2) -0.0020(15) 0.0045(15) 0.0039(14) C19 0.0119(17) 0.0224(17) 0.0183(18) -0.0020(14) 0.0040(14) 0.0003(14) C20 0.0157(18) 0.0167(15) 0.0204(19) -0.0041(14) 0.0071(15) 0.0043(13) C21 0.0092(17) 0.0203(16) 0.0215(19) -0.0031(14) 0.0071(14) -0.0021(13) C22 0.029(2) 0.0171(16) 0.024(2) -0.0002(15) 0.0075(17) 0.0020(15) C23 0.021(2) 0.0237(17) 0.0196(19) -0.0071(15) 0.0027(16) 0.0019(15) C24 0.028(2) 0.0242(18) 0.022(2) -0.0014(15) 0.0139(17) 0.0018(16) C25 0.015(2) 0.030(2) 0.039(3) -0.0059(18) 0.0047(18) -0.0009(16) C26 0.019(2) 0.034(2) 0.032(2) 0.0044(18) -0.0014(17) 0.0098(17) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 Cl1 2.4046(10) . . yes Ir1 N1 2.094(3) . . yes Ir1 C3 2.028(3) . . yes Ir1 C17 2.138(4) . . yes Ir1 C18 2.154(4) . . yes Ir1 C19 2.272(4) . . yes Ir1 C20 2.248(3) . . yes Ir1 C21 2.167(3) . . yes O1 C5 1.373(5) . . yes O1 C6 1.435(5) . . yes O2 C13 1.363(5) . . yes O2 C14 1.425(6) . . yes N1 C1 1.286(5) . . yes N1 C10 1.434(5) . . yes C1 C2 1.454(5) . . no C1 C9 1.505(5) . . no C2 C3 1.417(5) . . no C2 C8 1.398(5) . . no C3 C4 1.397(5) . . no C4 C5 1.393(5) . . no C5 C7 1.388(6) . . no C7 C8 1.373(6) . . no C10 C11 1.393(5) . . no C10 C16 1.379(5) . . no C11 C12 1.386(5) . . no C12 C13 1.397(6) . . no C13 C15 1.382(5) . . no C15 C16 1.397(5) . . no C17 C18 1.447(5) . . no C17 C21 1.447(5) . . no C17 C26 1.507(6) . . no C18 C19 1.445(6) . . no C18 C25 1.502(6) . . no C19 C20 1.412(5) . . no C19 C24 1.486(5) . . no C20 C21 1.454(5) . . no C20 C23 1.500(5) . . no C21 C22 1.485(5) . . no C4 H6 0.9500 . . no C6 H1 0.9800 . . no C6 H2 0.9800 . . no C6 H3 0.9800 . . no C7 H5 0.9500 . . no C8 H4 0.9500 . . no C9 H7 0.9800 . . no C9 H8 0.9800 . . no C9 H9 0.9800 . . no C11 H16 0.9500 . . no C12 H15 0.9500 . . no C14 H10 0.9800 . . no C14 H11 0.9800 . . no C14 H12 0.9800 . . no C15 H14 0.9500 . . no C16 H13 0.9500 . . no C22 H17 0.9800 . . no C22 H18 0.9800 . . no C22 H19 0.9800 . . no C23 H20 0.9800 . . no C23 H21 0.9800 . . no C23 H22 0.9800 . . no C24 H23 0.9800 . . no C24 H24 0.9800 . . no C24 H25 0.9800 . . no C25 H26 0.9800 . . no C25 H27 0.9800 . . no C25 H28 0.9800 . . no C26 H29 0.9800 . . no C26 H30 0.9800 . . no C26 H31 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ir1 N1 85.14(9) . . . yes Cl1 Ir1 C3 87.81(11) . . . yes Cl1 Ir1 C17 143.62(10) . . . yes Cl1 Ir1 C18 149.84(12) . . . yes Cl1 Ir1 C19 111.85(10) . . . yes Cl1 Ir1 C20 91.57(10) . . . yes Cl1 Ir1 C21 104.86(11) . . . yes N1 Ir1 C3 76.95(13) . . . yes N1 Ir1 C17 131.21(13) . . . yes N1 Ir1 C18 102.74(12) . . . yes N1 Ir1 C19 107.06(12) . . . yes N1 Ir1 C20 137.47(12) . . . yes N1 Ir1 C21 168.41(13) . . . yes C3 Ir1 C17 98.10(14) . . . yes C3 Ir1 C18 122.26(16) . . . yes C3 Ir1 C19 160.05(15) . . . yes C3 Ir1 C20 145.41(12) . . . yes C3 Ir1 C21 108.81(13) . . . yes C17 Ir1 C18 39.41(13) . . . yes C17 Ir1 C19 64.22(13) . . . yes C17 Ir1 C20 63.66(13) . . . yes C17 Ir1 C21 39.29(14) . . . yes C18 Ir1 C19 37.99(15) . . . yes C18 Ir1 C20 62.82(15) . . . yes C18 Ir1 C21 65.67(13) . . . yes C19 Ir1 C20 36.40(13) . . . yes C19 Ir1 C21 64.06(12) . . . yes C20 Ir1 C21 38.41(12) . . . yes C5 O1 C6 117.7(3) . . . yes C13 O2 C14 116.9(3) . . . yes Ir1 N1 C1 118.2(2) . . . yes Ir1 N1 C10 120.0(2) . . . yes C1 N1 C10 121.8(3) . . . yes N1 C1 C2 114.5(3) . . . yes N1 C1 C9 123.4(3) . . . yes C2 C1 C9 122.2(3) . . . no C1 C2 C3 113.9(3) . . . no C1 C2 C8 124.8(3) . . . no C3 C2 C8 121.2(3) . . . no Ir1 C3 C2 115.6(2) . . . yes Ir1 C3 C4 127.1(2) . . . yes C2 C3 C4 117.2(3) . . . no C3 C4 C5 120.8(3) . . . no O1 C5 C4 123.6(3) . . . yes O1 C5 C7 115.3(3) . . . yes C4 C5 C7 121.1(3) . . . no C5 C7 C8 119.4(3) . . . no C2 C8 C7 120.3(4) . . . no N1 C10 C11 119.1(3) . . . yes N1 C10 C16 121.1(3) . . . yes C11 C10 C16 119.7(3) . . . no C10 C11 C12 120.2(3) . . . no C11 C12 C13 119.8(3) . . . no O2 C13 C12 115.3(3) . . . yes O2 C13 C15 124.6(3) . . . yes C12 C13 C15 120.2(3) . . . no C13 C15 C16 119.6(3) . . . no C10 C16 C15 120.5(3) . . . no Ir1 C17 C18 70.9(2) . . . yes Ir1 C17 C21 71.4(2) . . . yes Ir1 C17 C26 127.9(3) . . . yes C18 C17 C21 108.1(3) . . . no C18 C17 C26 125.5(3) . . . no C21 C17 C26 126.1(3) . . . no Ir1 C18 C17 69.7(2) . . . yes Ir1 C18 C19 75.4(2) . . . yes Ir1 C18 C25 125.6(3) . . . yes C17 C18 C19 108.5(3) . . . no C17 C18 C25 126.3(4) . . . no C19 C18 C25 125.0(3) . . . no Ir1 C19 C18 66.6(2) . . . yes Ir1 C19 C20 70.9(2) . . . yes Ir1 C19 C24 130.9(3) . . . yes C18 C19 C20 106.9(3) . . . no C18 C19 C24 126.9(3) . . . no C20 C19 C24 126.1(3) . . . no Ir1 C20 C19 72.70(19) . . . yes Ir1 C20 C21 67.76(18) . . . yes Ir1 C20 C23 124.8(3) . . . yes C19 C20 C21 110.5(3) . . . no C19 C20 C23 125.4(3) . . . no C21 C20 C23 124.1(3) . . . no Ir1 C21 C17 69.29(19) . . . yes Ir1 C21 C20 73.83(18) . . . yes Ir1 C21 C22 129.3(3) . . . yes C17 C21 C20 105.9(3) . . . no C17 C21 C22 126.5(3) . . . no C20 C21 C22 126.9(3) . . . no C3 C4 H6 120.00 . . . no C5 C4 H6 120.00 . . . no O1 C6 H1 109.00 . . . no O1 C6 H2 109.00 . . . no O1 C6 H3 109.00 . . . no H1 C6 H2 110.00 . . . no H1 C6 H3 109.00 . . . no H2 C6 H3 109.00 . . . no C5 C7 H5 120.00 . . . no C8 C7 H5 120.00 . . . no C2 C8 H4 120.00 . . . no C7 C8 H4 120.00 . . . no C1 C9 H7 109.00 . . . no C1 C9 H8 109.00 . . . no C1 C9 H9 109.00 . . . no H7 C9 H8 109.00 . . . no H7 C9 H9 110.00 . . . no H8 C9 H9 109.00 . . . no C10 C11 H16 120.00 . . . no C12 C11 H16 120.00 . . . no C11 C12 H15 120.00 . . . no C13 C12 H15 120.00 . . . no O2 C14 H10 109.00 . . . no O2 C14 H11 109.00 . . . no O2 C14 H12 109.00 . . . no H10 C14 H11 110.00 . . . no H10 C14 H12 110.00 . . . no H11 C14 H12 109.00 . . . no C13 C15 H14 120.00 . . . no C16 C15 H14 120.00 . . . no C10 C16 H13 120.00 . . . no C15 C16 H13 120.00 . . . no C21 C22 H17 109.00 . . . no C21 C22 H18 109.00 . . . no C21 C22 H19 109.00 . . . no H17 C22 H18 109.00 . . . no H17 C22 H19 110.00 . . . no H18 C22 H19 109.00 . . . no C20 C23 H20 109.00 . . . no C20 C23 H21 109.00 . . . no C20 C23 H22 109.00 . . . no H20 C23 H21 109.00 . . . no H20 C23 H22 110.00 . . . no H21 C23 H22 109.00 . . . no C19 C24 H23 109.00 . . . no C19 C24 H24 109.00 . . . no C19 C24 H25 109.00 . . . no H23 C24 H24 109.00 . . . no H23 C24 H25 109.00 . . . no H24 C24 H25 110.00 . . . no C18 C25 H26 109.00 . . . no C18 C25 H27 109.00 . . . no C18 C25 H28 109.00 . . . no H26 C25 H27 109.00 . . . no H26 C25 H28 110.00 . . . no H27 C25 H28 110.00 . . . no C17 C26 H29 109.00 . . . no C17 C26 H30 109.00 . . . no C17 C26 H31 109.00 . . . no H29 C26 H30 109.00 . . . no H29 C26 H31 110.00 . . . no H30 C26 H31 110.00 . . . no 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 Cl1 Ir1 N1 C1 -80.2(3) . . . . no Cl1 Ir1 N1 C10 99.2(3) . . . . no C3 Ir1 N1 C1 8.7(3) . . . . no C3 Ir1 N1 C10 -172.0(3) . . . . no C17 Ir1 N1 C1 98.1(3) . . . . no C17 Ir1 N1 C10 -82.6(3) . . . . no C18 Ir1 N1 C1 129.3(3) . . . . no C18 Ir1 N1 C10 -51.3(3) . . . . no C19 Ir1 N1 C1 168.4(3) . . . . no C19 Ir1 N1 C10 -12.2(3) . . . . no C20 Ir1 N1 C1 -167.2(3) . . . . no C20 Ir1 N1 C10 12.2(4) . . . . no Cl1 Ir1 C3 C2 78.9(3) . . . . no Cl1 Ir1 C3 C4 -98.8(4) . . . . no N1 Ir1 C3 C2 -6.6(3) . . . . no N1 Ir1 C3 C4 175.7(4) . . . . no C17 Ir1 C3 C2 -137.2(3) . . . . no C17 Ir1 C3 C4 45.2(4) . . . . no C18 Ir1 C3 C2 -103.6(3) . . . . no C18 Ir1 C3 C4 78.8(4) . . . . no C20 Ir1 C3 C2 168.5(3) . . . . no C20 Ir1 C3 C4 -9.2(5) . . . . no C21 Ir1 C3 C2 -176.2(3) . . . . no C21 Ir1 C3 C4 6.2(4) . . . . no Cl1 Ir1 C17 C18 -130.1(2) . . . . no Cl1 Ir1 C17 C21 -12.5(3) . . . . no Cl1 Ir1 C17 C26 109.2(3) . . . . no N1 Ir1 C17 C18 52.8(3) . . . . no N1 Ir1 C17 C21 170.39(19) . . . . no N1 Ir1 C17 C26 -67.8(4) . . . . no C3 Ir1 C17 C18 132.5(2) . . . . no C3 Ir1 C17 C21 -109.9(2) . . . . no C3 Ir1 C17 C26 11.9(3) . . . . no C18 Ir1 C17 C21 117.6(3) . . . . no C18 Ir1 C17 C26 -120.7(4) . . . . no C19 Ir1 C17 C18 -37.7(2) . . . . no C19 Ir1 C17 C21 79.8(2) . . . . no C19 Ir1 C17 C26 -158.4(4) . . . . no C20 Ir1 C17 C18 -78.4(2) . . . . no C20 Ir1 C17 C21 39.13(19) . . . . no C20 Ir1 C17 C26 160.9(4) . . . . no C21 Ir1 C17 C18 -117.6(3) . . . . no C21 Ir1 C17 C26 121.8(4) . . . . no Cl1 Ir1 C18 C17 115.4(2) . . . . no Cl1 Ir1 C18 C19 -1.0(3) . . . . no Cl1 Ir1 C18 C25 -123.8(3) . . . . no N1 Ir1 C18 C17 -142.1(2) . . . . no N1 Ir1 C18 C19 101.48(19) . . . . no N1 Ir1 C18 C25 -21.3(4) . . . . no C3 Ir1 C18 C17 -59.6(2) . . . . no C3 Ir1 C18 C19 -176.05(18) . . . . no C3 Ir1 C18 C25 61.2(4) . . . . no C17 Ir1 C18 C19 -116.4(3) . . . . no C17 Ir1 C18 C25 120.8(5) . . . . no C19 Ir1 C18 C17 116.4(3) . . . . no C19 Ir1 C18 C25 -122.8(4) . . . . no C20 Ir1 C18 C17 80.8(2) . . . . no C20 Ir1 C18 C19 -35.67(18) . . . . no C20 Ir1 C18 C25 -158.5(4) . . . . no C21 Ir1 C18 C17 38.0(2) . . . . no C21 Ir1 C18 C19 -78.4(2) . . . . no C21 Ir1 C18 C25 158.8(4) . . . . no Cl1 Ir1 C19 C18 179.47(16) . . . . no Cl1 Ir1 C19 C20 60.4(2) . . . . no Cl1 Ir1 C19 C24 -61.2(4) . . . . no N1 Ir1 C19 C18 -89.0(2) . . . . no N1 Ir1 C19 C20 152.0(2) . . . . no N1 Ir1 C19 C24 30.4(4) . . . . no C17 Ir1 C19 C18 39.15(19) . . . . no C17 Ir1 C19 C20 -79.9(2) . . . . no C17 Ir1 C19 C24 158.5(4) . . . . no C18 Ir1 C19 C20 -119.1(3) . . . . no C18 Ir1 C19 C24 119.3(4) . . . . no C20 Ir1 C19 C18 119.1(3) . . . . no C20 Ir1 C19 C24 -121.6(4) . . . . no C21 Ir1 C19 C18 83.0(2) . . . . no C21 Ir1 C19 C20 -36.0(2) . . . . no C21 Ir1 C19 C24 -157.7(4) . . . . no Cl1 Ir1 C20 C19 -126.2(2) . . . . no Cl1 Ir1 C20 C21 112.2(2) . . . . no Cl1 Ir1 C20 C23 -4.7(3) . . . . no N1 Ir1 C20 C19 -41.7(3) . . . . no N1 Ir1 C20 C21 -163.3(2) . . . . no N1 Ir1 C20 C23 79.8(3) . . . . no C3 Ir1 C20 C19 145.4(3) . . . . no C3 Ir1 C20 C21 23.8(4) . . . . no C3 Ir1 C20 C23 -93.1(4) . . . . no C17 Ir1 C20 C19 81.6(2) . . . . no C17 Ir1 C20 C21 -40.0(2) . . . . no C17 Ir1 C20 C23 -157.0(3) . . . . no C18 Ir1 C20 C19 37.2(2) . . . . no C18 Ir1 C20 C21 -84.4(2) . . . . no C18 Ir1 C20 C23 158.7(3) . . . . no C19 Ir1 C20 C21 -121.6(3) . . . . no C19 Ir1 C20 C23 121.5(4) . . . . no C21 Ir1 C20 C19 121.6(3) . . . . no C21 Ir1 C20 C23 -116.9(4) . . . . no Cl1 Ir1 C21 C17 172.35(17) . . . . no Cl1 Ir1 C21 C20 -73.2(2) . . . . no Cl1 Ir1 C21 C22 51.5(3) . . . . no C3 Ir1 C21 C17 79.6(2) . . . . no C3 Ir1 C21 C20 -166.0(2) . . . . no C3 Ir1 C21 C22 -41.3(4) . . . . no C17 Ir1 C21 C20 114.5(3) . . . . no C17 Ir1 C21 C22 -120.8(4) . . . . no C18 Ir1 C21 C17 -38.1(2) . . . . no C18 Ir1 C21 C20 76.3(2) . . . . no C18 Ir1 C21 C22 -159.0(4) . . . . no C19 Ir1 C21 C17 -80.3(2) . . . . no C19 Ir1 C21 C20 34.2(2) . . . . no C19 Ir1 C21 C22 158.9(4) . . . . no C20 Ir1 C21 C17 -114.5(3) . . . . no C20 Ir1 C21 C22 124.7(4) . . . . no C6 O1 C5 C4 3.3(5) . . . . no C6 O1 C5 C7 -176.3(3) . . . . no C14 O2 C13 C12 174.0(3) . . . . no C14 O2 C13 C15 -6.2(5) . . . . no Ir1 N1 C1 C2 -8.7(4) . . . . no Ir1 N1 C1 C9 170.3(3) . . . . no C10 N1 C1 C2 172.0(3) . . . . no C10 N1 C1 C9 -9.0(6) . . . . no Ir1 N1 C10 C11 111.1(3) . . . . no Ir1 N1 C10 C16 -65.0(4) . . . . no C1 N1 C10 C11 -69.5(5) . . . . no C1 N1 C10 C16 114.4(4) . . . . no N1 C1 C2 C3 2.8(5) . . . . no N1 C1 C2 C8 -174.5(4) . . . . no C9 C1 C2 C3 -176.3(4) . . . . no C9 C1 C2 C8 6.4(6) . . . . no C1 C2 C3 Ir1 4.5(4) . . . . no C1 C2 C3 C4 -177.6(4) . . . . no C8 C2 C3 Ir1 -178.1(3) . . . . no C8 C2 C3 C4 -0.2(6) . . . . no C1 C2 C8 C7 175.7(4) . . . . no C3 C2 C8 C7 -1.4(6) . . . . no Ir1 C3 C4 C5 179.8(3) . . . . no C2 C3 C4 C5 2.2(6) . . . . no C3 C4 C5 O1 177.8(4) . . . . no C3 C4 C5 C7 -2.6(6) . . . . no O1 C5 C7 C8 -179.5(4) . . . . no C4 C5 C7 C8 0.8(6) . . . . no C5 C7 C8 C2 1.1(6) . . . . no N1 C10 C11 C12 -176.1(3) . . . . no C16 C10 C11 C12 0.1(5) . . . . no N1 C10 C16 C15 176.2(3) . . . . no C11 C10 C16 C15 0.1(5) . . . . no C10 C11 C12 C13 0.0(5) . . . . no C11 C12 C13 O2 179.6(3) . . . . no C11 C12 C13 C15 -0.2(5) . . . . no O2 C13 C15 C16 -179.4(3) . . . . no C12 C13 C15 C16 0.4(5) . . . . no C13 C15 C16 C10 -0.3(5) . . . . no Ir1 C17 C18 C19 66.0(3) . . . . no Ir1 C17 C18 C25 -119.9(4) . . . . no C21 C17 C18 Ir1 -62.1(3) . . . . no C21 C17 C18 C19 3.9(4) . . . . no C21 C17 C18 C25 178.0(4) . . . . no C26 C17 C18 Ir1 123.5(4) . . . . no C26 C17 C18 C19 -170.5(3) . . . . no C26 C17 C18 C25 3.6(6) . . . . no Ir1 C17 C21 C20 -65.4(2) . . . . no Ir1 C17 C21 C22 124.2(4) . . . . no C18 C17 C21 Ir1 61.8(3) . . . . no C18 C17 C21 C20 -3.6(4) . . . . no C18 C17 C21 C22 -174.0(4) . . . . no C26 C17 C21 Ir1 -123.9(4) . . . . no C26 C17 C21 C20 170.8(4) . . . . no C26 C17 C21 C22 0.3(6) . . . . no Ir1 C18 C19 C20 59.7(3) . . . . no Ir1 C18 C19 C24 -124.5(4) . . . . no C17 C18 C19 Ir1 -62.3(3) . . . . no C17 C18 C19 C20 -2.6(4) . . . . no C17 C18 C19 C24 173.2(4) . . . . no C25 C18 C19 Ir1 123.5(4) . . . . no C25 C18 C19 C20 -176.8(4) . . . . no C25 C18 C19 C24 -1.0(6) . . . . no Ir1 C19 C20 C21 57.3(3) . . . . no Ir1 C19 C20 C23 -120.8(4) . . . . no C18 C19 C20 Ir1 -57.0(3) . . . . no C18 C19 C20 C21 0.3(4) . . . . no C18 C19 C20 C23 -177.8(3) . . . . no C24 C19 C20 Ir1 127.2(4) . . . . no C24 C19 C20 C21 -175.5(4) . . . . no C24 C19 C20 C23 6.4(6) . . . . no Ir1 C20 C21 C17 62.3(2) . . . . no Ir1 C20 C21 C22 -127.3(4) . . . . no C19 C20 C21 Ir1 -60.3(3) . . . . no C19 C20 C21 C17 2.0(4) . . . . no C19 C20 C21 C22 172.4(4) . . . . no C23 C20 C21 Ir1 117.9(4) . . . . no C23 C20 C21 C17 -179.9(3) . . . . no C23 C20 C21 C22 -9.4(6) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C6 H2 Cl1 0.9800 2.7700 3.673(4) 153.00 2_775 yes C8 H4 Cl1 0.9500 2.7700 3.659(4) 156.00 2_765 yes C14 H11 O2 0.9800 2.5700 3.253(6) 127.00 2_656 yes C15 H14 Cl1 0.9500 2.8000 3.711(4) 161.00 2_766 yes _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 2.112 _refine_diff_density_min -1.903 _refine_diff_density_rms 0.153 # Attachment '- Complex 3.cif' data_cwf611m _database_code_depnum_ccdc_archive 'CCDC 888575' #TrackingRef '- Complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CWF61 _chemical_melting_point ? _chemical_formula_moiety '(Ir 3+), (Cl 1-), (C14 H18 N2 1-), (C10 H15 1-)' _chemical_formula_sum 'C24 H33 Cl Ir N' _chemical_formula_weight 563.17 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' 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 11.2929(18) _cell_length_b 13.525(2) _cell_length_c 14.951(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.771(2) _cell_angle_gamma 90.00 _cell_volume 2162.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1464 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.10 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 6.308 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1770 _exptl_absorpt_correction_T_max 0.3016 _exptl_absorpt_process_details 'SADABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; The faces of the crystal were indexed, and the distances of the faces from the centre of the crystal were measured for a numerical absorption correction. SADABS-2008/1 (Bruker,2008) was used for the absorption correction. Linear absorption coefficient set to 6.31 mm-1, giving Rint = 0.0892 wR(int) was 0.0996 before and 0.0389 after correction. Minimum and maximum transmission coefficients = 0.09166 and 0.27966 Minimum and maximum t-bar = 0.1626 and 0.3040 mm The Ratio of minimum to maximum transmission is 0.37. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 5.0 cm. ; _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 D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16589 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5344 _reflns_number_gt 4945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0208P)^2^+3.3162P] 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 5344 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0522 _refine_ls_wR_factor_gt 0.0514 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir1 Ir Uani 0.23693(1) 0.09180(1) 0.26189(1) 1.000 0.0099(1) . . Cl1 Cl Uani 0.33390(6) 0.22446(5) 0.36635(4) 1.000 0.0164(2) . . N1 N Uani 0.4120(2) 0.01954(17) 0.29733(15) 1.000 0.0113(6) . . C1 C Uani 0.4332(2) -0.0485(2) 0.36230(18) 1.000 0.0125(7) . . C2 C Uani 0.3368(2) -0.0586(2) 0.40714(18) 1.000 0.0125(7) . . C3 C Uani 0.2385(2) 0.0111(2) 0.37561(18) 1.000 0.0128(7) . . C4 C Uani 0.1530(3) 0.0158(2) 0.42554(19) 1.000 0.0175(8) . . C5 C Uani 0.1584(3) -0.0508(2) 0.49782(19) 1.000 0.0185(8) . . C6 C Uani 0.2509(3) -0.1226(2) 0.5236(2) 1.000 0.0183(8) . . C7 C Uani 0.3418(3) -0.1257(2) 0.48006(19) 1.000 0.0166(8) . . C8 C Uani 0.5497(3) -0.1103(2) 0.3933(2) 1.000 0.0159(8) . . C9 C Uani 0.5123(2) 0.0414(2) 0.25597(18) 1.000 0.0137(8) . . C10 C Uani 0.4953(3) -0.0188(2) 0.16610(19) 1.000 0.0164(8) . . C11 C Uani 0.6046(3) 0.0002(2) 0.1287(2) 1.000 0.0207(9) . . C12 C Uani 0.6221(3) 0.1096(3) 0.1131(2) 1.000 0.0223(9) . . C13 C Uani 0.6341(3) 0.1691(2) 0.2029(2) 1.000 0.0186(8) . . C14 C Uani 0.5234(3) 0.1510(2) 0.2385(2) 1.000 0.0157(8) . . C15 C Uani 0.1267(2) 0.1975(2) 0.14526(19) 1.000 0.0149(7) . . C16 C Uani 0.0538(2) 0.1563(2) 0.20036(19) 1.000 0.0140(7) . . C17 C Uani 0.0471(2) 0.0517(2) 0.18421(19) 1.000 0.0138(7) . . C18 C Uani 0.1269(3) 0.0276(2) 0.12928(18) 1.000 0.0153(7) . . C19 C Uani 0.1694(3) 0.1207(2) 0.10038(19) 1.000 0.0164(8) . . C20 C Uani 0.2306(3) 0.1336(3) 0.0261(2) 1.000 0.0232(9) . . C21 C Uani 0.1403(3) -0.0728(2) 0.0912(2) 1.000 0.0219(9) . . C22 C Uani -0.0332(3) -0.0192(2) 0.2147(2) 1.000 0.0188(8) . . C23 C Uani -0.0167(3) 0.2149(2) 0.2512(2) 1.000 0.0196(8) . . C24 C Uani 0.1493(3) 0.3057(2) 0.1380(2) 1.000 0.0205(8) . . H4 H Uiso 0.09020 0.06550 0.40990 1.000 0.0210 calc R H5 H Uiso 0.09810 -0.04700 0.52970 1.000 0.0220 calc R H6 H Uiso 0.25180 -0.16950 0.57110 1.000 0.0220 calc R H7 H Uiso 0.40740 -0.17290 0.49930 1.000 0.0200 calc R H8A H Uiso 0.56800 -0.13520 0.33760 1.000 0.0240 calc R H8B H Uiso 0.53740 -0.16610 0.43110 1.000 0.0240 calc R H8C H Uiso 0.61990 -0.06980 0.43130 1.000 0.0240 calc R H9 H Uiso 0.59320 0.02010 0.30320 1.000 0.0160 calc R H10A H Uiso 0.41570 0.00000 0.11750 1.000 0.0200 calc R H10B H Uiso 0.49130 -0.09010 0.17990 1.000 0.0200 calc R H11A H Uiso 0.68230 -0.02630 0.17430 1.000 0.0250 calc R H11B H Uiso 0.58930 -0.03550 0.06820 1.000 0.0250 calc R H12A H Uiso 0.54970 0.13420 0.06080 1.000 0.0270 calc R H12B H Uiso 0.69830 0.11890 0.09500 1.000 0.0270 calc R H13A H Uiso 0.71250 0.15030 0.25270 1.000 0.0220 calc R H13B H Uiso 0.63890 0.24040 0.18950 1.000 0.0220 calc R H14A H Uiso 0.53560 0.18820 0.29780 1.000 0.0190 calc R H14B H Uiso 0.44540 0.17480 0.19110 1.000 0.0190 calc R H20A H Uiso 0.17120 0.16390 -0.03000 1.000 0.0350 calc R H20B H Uiso 0.25670 0.06900 0.00940 1.000 0.0350 calc R H20C H Uiso 0.30400 0.17650 0.05030 1.000 0.0350 calc R H21A H Uiso 0.12540 -0.12360 0.13310 1.000 0.0330 calc R H21B H Uiso 0.22500 -0.08030 0.08770 1.000 0.0330 calc R H21C H Uiso 0.07930 -0.08020 0.02790 1.000 0.0330 calc R H22A H Uiso -0.10520 -0.03760 0.16020 1.000 0.0280 calc R H22B H Uiso -0.06260 0.01180 0.26290 1.000 0.0280 calc R H22C H Uiso 0.01530 -0.07860 0.24090 1.000 0.0280 calc R H23A H Uiso -0.08590 0.24980 0.20520 1.000 0.0300 calc R H23B H Uiso 0.03950 0.26310 0.29280 1.000 0.0300 calc R H23C H Uiso -0.05000 0.17040 0.28900 1.000 0.0300 calc R H24A H Uiso 0.19710 0.31630 0.09460 1.000 0.0310 calc R H24B H Uiso 0.19650 0.33160 0.20060 1.000 0.0310 calc R H24C H Uiso 0.06890 0.34020 0.11420 1.000 0.0310 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 0.0077(1) 0.0119(1) 0.0105(1) 0.0002(1) 0.0032(1) 0.0006(1) Cl1 0.0166(3) 0.0159(3) 0.0162(3) -0.0038(2) 0.0045(2) -0.0002(3) N1 0.0093(10) 0.0138(11) 0.0121(10) -0.0021(8) 0.0052(8) -0.0015(8) C1 0.0116(12) 0.0131(13) 0.0120(11) -0.0019(10) 0.0027(9) 0.0011(10) C2 0.0132(12) 0.0132(13) 0.0119(11) -0.0012(10) 0.0051(9) -0.0015(10) C3 0.0103(12) 0.0160(14) 0.0116(11) -0.0012(10) 0.0028(9) -0.0018(10) C4 0.0126(13) 0.0242(16) 0.0158(12) 0.0015(11) 0.0049(10) 0.0012(11) C5 0.0138(13) 0.0281(17) 0.0159(12) 0.0000(12) 0.0081(10) -0.0020(12) C6 0.0177(14) 0.0215(15) 0.0158(13) 0.0037(11) 0.0056(10) -0.0031(12) C7 0.0170(13) 0.0164(14) 0.0150(12) 0.0021(11) 0.0034(10) 0.0005(11) C8 0.0160(13) 0.0166(14) 0.0154(12) 0.0019(10) 0.0056(10) 0.0022(11) C9 0.0101(12) 0.0179(15) 0.0145(12) 0.0014(11) 0.0059(9) 0.0016(10) C10 0.0142(13) 0.0196(15) 0.0178(13) -0.0009(11) 0.0084(10) 0.0010(11) C11 0.0208(15) 0.0249(16) 0.0202(14) -0.0005(12) 0.0120(11) 0.0028(12) C12 0.0202(15) 0.0299(18) 0.0213(14) 0.0040(12) 0.0128(12) 0.0015(13) C13 0.0131(13) 0.0233(16) 0.0208(13) 0.0033(12) 0.0073(10) -0.0010(11) C14 0.0131(12) 0.0168(15) 0.0182(13) 0.0017(11) 0.0064(10) -0.0001(11) C15 0.0093(12) 0.0169(14) 0.0162(12) 0.0041(10) 0.0010(10) 0.0008(10) C16 0.0066(11) 0.0181(14) 0.0171(12) 0.0018(11) 0.0035(9) 0.0017(10) C17 0.0083(12) 0.0160(14) 0.0151(12) 0.0022(10) 0.0008(9) -0.0006(10) C18 0.0117(12) 0.0191(15) 0.0121(11) 0.0000(10) -0.0005(9) 0.0005(11) C19 0.0113(12) 0.0234(15) 0.0120(12) 0.0019(11) 0.0004(10) 0.0008(11) C20 0.0174(14) 0.038(2) 0.0133(13) 0.0027(13) 0.0036(10) -0.0013(13) C21 0.0204(15) 0.0218(16) 0.0216(14) -0.0085(12) 0.0040(12) 0.0011(12) C22 0.0161(13) 0.0178(15) 0.0230(14) -0.0010(11) 0.0068(11) -0.0043(11) C23 0.0142(13) 0.0193(16) 0.0275(14) 0.0004(12) 0.0096(11) 0.0044(11) C24 0.0165(14) 0.0164(15) 0.0280(15) 0.0083(12) 0.0062(11) 0.0007(11) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 Cl1 2.3994(7) . . yes Ir1 N1 2.114(2) . . yes Ir1 C3 2.016(3) . . yes Ir1 C15 2.288(3) . . yes Ir1 C16 2.159(3) . . yes Ir1 C17 2.153(3) . . yes Ir1 C18 2.155(3) . . yes Ir1 C19 2.320(3) . . yes N1 C1 1.303(3) . . yes N1 C9 1.484(3) . . yes C1 C2 1.457(3) . . no C1 C8 1.501(4) . . no C2 C3 1.417(4) . . no C2 C7 1.406(4) . . no C3 C4 1.399(4) . . no C4 C5 1.393(4) . . no C5 C6 1.387(4) . . no C6 C7 1.382(5) . . no C9 C10 1.529(4) . . no C9 C14 1.517(4) . . no C10 C11 1.532(5) . . no C11 C12 1.521(5) . . no C12 C13 1.533(4) . . no C13 C14 1.528(5) . . no C15 C16 1.450(4) . . no C15 C19 1.404(4) . . no C15 C24 1.495(4) . . no C16 C17 1.433(4) . . no C16 C23 1.493(4) . . no C17 C18 1.438(4) . . no C17 C22 1.489(4) . . no C18 C19 1.462(4) . . no C18 C21 1.499(4) . . no C19 C20 1.495(4) . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8A 0.9800 . . no C8 H8B 0.9800 . . no C8 H8C 0.9800 . . no C9 H9 1.0000 . . no C10 H10A 0.9900 . . no C10 H10B 0.9900 . . no C11 H11A 0.9900 . . no C11 H11B 0.9900 . . no C12 H12A 0.9900 . . no C12 H12B 0.9900 . . no C13 H13A 0.9900 . . no C13 H13B 0.9900 . . no C14 H14A 0.9900 . . no C14 H14B 0.9900 . . no C20 H20A 0.9800 . . no C20 H20B 0.9800 . . no C20 H20C 0.9800 . . no C21 H21A 0.9800 . . no C21 H21B 0.9800 . . no C21 H21C 0.9800 . . no C22 H22A 0.9800 . . no C22 H22B 0.9800 . . no C22 H22C 0.9800 . . no C23 H23A 0.9800 . . no C23 H23B 0.9800 . . no C23 H23C 0.9800 . . no C24 H24A 0.9800 . . no C24 H24B 0.9800 . . no C24 H24C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ir1 N1 89.34(6) . . . yes Cl1 Ir1 C3 88.71(8) . . . yes Cl1 Ir1 C15 92.94(7) . . . yes Cl1 Ir1 C16 98.58(7) . . . yes Cl1 Ir1 C17 134.92(7) . . . yes Cl1 Ir1 C18 155.16(7) . . . yes Cl1 Ir1 C19 118.68(7) . . . yes N1 Ir1 C3 77.56(9) . . . yes N1 Ir1 C15 135.66(9) . . . yes N1 Ir1 C16 169.72(9) . . . yes N1 Ir1 C17 135.00(9) . . . yes N1 Ir1 C18 105.08(10) . . . yes N1 Ir1 C19 107.85(10) . . . yes C3 Ir1 C15 146.72(9) . . . yes C3 Ir1 C16 108.99(10) . . . yes C3 Ir1 C17 93.19(10) . . . yes C3 Ir1 C18 113.82(11) . . . yes C3 Ir1 C19 151.66(10) . . . yes C15 Ir1 C16 37.93(9) . . . yes C15 Ir1 C17 62.83(10) . . . yes C15 Ir1 C18 62.58(10) . . . yes C15 Ir1 C19 35.46(10) . . . yes C16 Ir1 C17 38.82(10) . . . yes C16 Ir1 C18 65.23(11) . . . yes C16 Ir1 C19 62.57(11) . . . yes C17 Ir1 C18 39.01(11) . . . yes C17 Ir1 C19 62.88(11) . . . yes C18 Ir1 C19 37.91(10) . . . yes Ir1 N1 C1 116.48(18) . . . yes Ir1 N1 C9 125.51(16) . . . yes C1 N1 C9 118.0(2) . . . yes N1 C1 C2 115.1(2) . . . yes N1 C1 C8 123.8(2) . . . yes C2 C1 C8 121.1(2) . . . no C1 C2 C3 114.0(2) . . . no C1 C2 C7 124.6(2) . . . no C3 C2 C7 121.3(2) . . . no Ir1 C3 C2 115.74(18) . . . yes Ir1 C3 C4 127.2(2) . . . yes C2 C3 C4 117.0(2) . . . no C3 C4 C5 121.3(3) . . . no C4 C5 C6 120.6(3) . . . no C5 C6 C7 119.8(3) . . . no C2 C7 C6 119.7(3) . . . no N1 C9 C10 111.3(2) . . . yes N1 C9 C14 112.5(2) . . . yes C10 C9 C14 111.3(2) . . . no C9 C10 C11 110.1(2) . . . no C10 C11 C12 112.3(3) . . . no C11 C12 C13 110.8(2) . . . no C12 C13 C14 111.7(3) . . . no C9 C14 C13 109.8(2) . . . no Ir1 C15 C16 66.18(14) . . . yes Ir1 C15 C19 73.48(16) . . . yes Ir1 C15 C24 127.08(19) . . . yes C16 C15 C19 109.4(2) . . . no C16 C15 C24 124.0(2) . . . no C19 C15 C24 126.6(3) . . . no Ir1 C16 C15 75.89(14) . . . yes Ir1 C16 C17 70.38(14) . . . yes Ir1 C16 C23 126.32(19) . . . yes C15 C16 C17 107.0(2) . . . no C15 C16 C23 125.3(2) . . . no C17 C16 C23 127.0(2) . . . no Ir1 C17 C16 70.80(14) . . . yes Ir1 C17 C18 70.56(15) . . . yes Ir1 C17 C22 126.6(2) . . . yes C16 C17 C18 108.1(2) . . . no C16 C17 C22 126.1(2) . . . no C18 C17 C22 125.8(2) . . . no Ir1 C18 C17 70.43(15) . . . yes Ir1 C18 C19 77.17(16) . . . yes Ir1 C18 C21 128.0(2) . . . yes C17 C18 C19 107.4(2) . . . no C17 C18 C21 125.5(3) . . . no C19 C18 C21 125.8(3) . . . no Ir1 C19 C15 71.06(15) . . . yes Ir1 C19 C18 64.93(14) . . . yes Ir1 C19 C20 135.8(2) . . . yes C15 C19 C18 107.5(3) . . . no C15 C19 C20 125.5(3) . . . no C18 C19 C20 126.5(3) . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 119.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C2 C7 H7 120.00 . . . no C6 C7 H7 120.00 . . . no C1 C8 H8A 109.00 . . . no C1 C8 H8B 110.00 . . . no C1 C8 H8C 109.00 . . . no H8A C8 H8B 109.00 . . . no H8A C8 H8C 109.00 . . . no H8B C8 H8C 110.00 . . . no N1 C9 H9 107.00 . . . no C10 C9 H9 107.00 . . . no C14 C9 H9 107.00 . . . no C9 C10 H10A 110.00 . . . no C9 C10 H10B 110.00 . . . no C11 C10 H10A 110.00 . . . no C11 C10 H10B 110.00 . . . no H10A C10 H10B 108.00 . . . no C10 C11 H11A 109.00 . . . no C10 C11 H11B 109.00 . . . no C12 C11 H11A 109.00 . . . no C12 C11 H11B 109.00 . . . no H11A C11 H11B 108.00 . . . no C11 C12 H12A 109.00 . . . no C11 C12 H12B 109.00 . . . no C13 C12 H12A 109.00 . . . no C13 C12 H12B 109.00 . . . no H12A C12 H12B 108.00 . . . no C12 C13 H13A 109.00 . . . no C12 C13 H13B 109.00 . . . no C14 C13 H13A 109.00 . . . no C14 C13 H13B 109.00 . . . no H13A C13 H13B 108.00 . . . no C9 C14 H14A 110.00 . . . no C9 C14 H14B 110.00 . . . no C13 C14 H14A 110.00 . . . no C13 C14 H14B 110.00 . . . no H14A C14 H14B 108.00 . . . no C19 C20 H20A 109.00 . . . no C19 C20 H20B 110.00 . . . no C19 C20 H20C 109.00 . . . no H20A C20 H20B 110.00 . . . no H20A C20 H20C 109.00 . . . no H20B C20 H20C 109.00 . . . no C18 C21 H21A 109.00 . . . no C18 C21 H21B 109.00 . . . no C18 C21 H21C 109.00 . . . no H21A C21 H21B 109.00 . . . no H21A C21 H21C 109.00 . . . no H21B C21 H21C 109.00 . . . no C17 C22 H22A 109.00 . . . no C17 C22 H22B 109.00 . . . no C17 C22 H22C 109.00 . . . no H22A C22 H22B 109.00 . . . no H22A C22 H22C 109.00 . . . no H22B C22 H22C 110.00 . . . no C16 C23 H23A 109.00 . . . no C16 C23 H23B 109.00 . . . no C16 C23 H23C 110.00 . . . no H23A C23 H23B 109.00 . . . no H23A C23 H23C 109.00 . . . no H23B C23 H23C 109.00 . . . no C15 C24 H24A 110.00 . . . no C15 C24 H24B 109.00 . . . no C15 C24 H24C 109.00 . . . no H24A C24 H24B 110.00 . . . no H24A C24 H24C 109.00 . . . no H24B C24 H24C 109.00 . . . no 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 Cl1 Ir1 N1 C1 97.20(19) . . . . no Cl1 Ir1 N1 C9 -81.48(19) . . . . no C3 Ir1 N1 C1 8.4(2) . . . . no C3 Ir1 N1 C9 -170.3(2) . . . . no C15 Ir1 N1 C1 -169.28(18) . . . . no C15 Ir1 N1 C9 12.1(3) . . . . no C17 Ir1 N1 C1 -73.6(2) . . . . no C17 Ir1 N1 C9 107.8(2) . . . . no C18 Ir1 N1 C1 -103.3(2) . . . . no C18 Ir1 N1 C9 78.1(2) . . . . no C19 Ir1 N1 C1 -142.77(19) . . . . no C19 Ir1 N1 C9 38.6(2) . . . . no Cl1 Ir1 C3 C2 -99.34(19) . . . . no Cl1 Ir1 C3 C4 81.4(2) . . . . no N1 Ir1 C3 C2 -9.74(19) . . . . no N1 Ir1 C3 C4 171.0(3) . . . . no C15 Ir1 C3 C2 167.27(18) . . . . no C15 Ir1 C3 C4 -12.0(4) . . . . no C16 Ir1 C3 C2 162.03(19) . . . . no C16 Ir1 C3 C4 -17.2(3) . . . . no C17 Ir1 C3 C2 125.7(2) . . . . no C17 Ir1 C3 C4 -53.5(3) . . . . no C18 Ir1 C3 C2 91.4(2) . . . . no C18 Ir1 C3 C4 -87.8(3) . . . . no C19 Ir1 C3 C2 94.9(3) . . . . no C19 Ir1 C3 C4 -84.4(3) . . . . no Cl1 Ir1 C15 C16 -100.20(15) . . . . no Cl1 Ir1 C15 C19 139.14(17) . . . . no Cl1 Ir1 C15 C24 15.4(2) . . . . no N1 Ir1 C15 C16 167.74(15) . . . . no N1 Ir1 C15 C19 47.1(2) . . . . no N1 Ir1 C15 C24 -76.7(3) . . . . no C3 Ir1 C15 C16 -8.1(3) . . . . no C3 Ir1 C15 C19 -128.7(2) . . . . no C3 Ir1 C15 C24 107.5(3) . . . . no C16 Ir1 C15 C19 -120.7(2) . . . . no C16 Ir1 C15 C24 115.6(3) . . . . no C17 Ir1 C15 C16 40.00(15) . . . . no C17 Ir1 C15 C19 -80.65(19) . . . . no C17 Ir1 C15 C24 155.6(3) . . . . no C18 Ir1 C15 C16 84.15(18) . . . . no C18 Ir1 C15 C19 -36.51(19) . . . . no C18 Ir1 C15 C24 -160.3(3) . . . . no C19 Ir1 C15 C16 120.7(2) . . . . no C19 Ir1 C15 C24 -123.8(3) . . . . no Cl1 Ir1 C16 C15 83.73(15) . . . . no Cl1 Ir1 C16 C17 -162.09(14) . . . . no Cl1 Ir1 C16 C23 -40.0(2) . . . . no C3 Ir1 C16 C15 175.32(15) . . . . no C3 Ir1 C16 C17 -70.49(17) . . . . no C3 Ir1 C16 C23 51.6(3) . . . . no C15 Ir1 C16 C17 114.2(2) . . . . no C15 Ir1 C16 C23 -123.7(3) . . . . no C17 Ir1 C16 C15 -114.2(2) . . . . no C17 Ir1 C16 C23 122.1(3) . . . . no C18 Ir1 C16 C15 -76.52(17) . . . . no C18 Ir1 C16 C17 37.67(16) . . . . no C18 Ir1 C16 C23 159.7(3) . . . . no C19 Ir1 C16 C15 -34.21(15) . . . . no C19 Ir1 C16 C17 79.97(16) . . . . no C19 Ir1 C16 C23 -158.0(3) . . . . no Cl1 Ir1 C17 C16 25.43(19) . . . . no Cl1 Ir1 C17 C18 143.62(13) . . . . no Cl1 Ir1 C17 C22 -95.8(2) . . . . no N1 Ir1 C17 C16 -167.65(14) . . . . no N1 Ir1 C17 C18 -49.5(2) . . . . no N1 Ir1 C17 C22 71.2(3) . . . . no C3 Ir1 C17 C16 116.79(16) . . . . no C3 Ir1 C17 C18 -125.02(16) . . . . no C3 Ir1 C17 C22 -4.4(2) . . . . no C15 Ir1 C17 C16 -39.07(15) . . . . no C15 Ir1 C17 C18 79.12(16) . . . . no C15 Ir1 C17 C22 -160.3(3) . . . . no C16 Ir1 C17 C18 118.2(2) . . . . no C16 Ir1 C17 C22 -121.2(3) . . . . no C18 Ir1 C17 C16 -118.2(2) . . . . no C18 Ir1 C17 C22 120.6(3) . . . . no C19 Ir1 C17 C16 -79.09(16) . . . . no C19 Ir1 C17 C18 39.09(15) . . . . no C19 Ir1 C17 C22 159.7(3) . . . . no Cl1 Ir1 C18 C17 -90.2(2) . . . . no Cl1 Ir1 C18 C19 23.8(3) . . . . no Cl1 Ir1 C18 C21 149.52(19) . . . . no N1 Ir1 C18 C17 146.18(15) . . . . no N1 Ir1 C18 C19 -99.82(18) . . . . no N1 Ir1 C18 C21 25.9(3) . . . . no C3 Ir1 C18 C17 63.36(18) . . . . no C3 Ir1 C18 C19 177.35(17) . . . . no C3 Ir1 C18 C21 -56.9(3) . . . . no C15 Ir1 C18 C17 -79.82(16) . . . . no C15 Ir1 C18 C19 34.18(17) . . . . no C15 Ir1 C18 C21 159.9(3) . . . . no C16 Ir1 C18 C17 -37.49(15) . . . . no C16 Ir1 C18 C19 76.51(19) . . . . no C16 Ir1 C18 C21 -157.8(3) . . . . no C17 Ir1 C18 C19 114.0(2) . . . . no C17 Ir1 C18 C21 -120.3(3) . . . . no C19 Ir1 C18 C17 -114.0(2) . . . . no C19 Ir1 C18 C21 125.7(4) . . . . no Cl1 Ir1 C19 C15 -48.14(19) . . . . no Cl1 Ir1 C19 C18 -168.86(16) . . . . no Cl1 Ir1 C19 C20 73.7(3) . . . . no N1 Ir1 C19 C15 -147.47(16) . . . . no N1 Ir1 C19 C18 91.80(19) . . . . no N1 Ir1 C19 C20 -25.6(3) . . . . no C3 Ir1 C19 C15 115.6(2) . . . . no C3 Ir1 C19 C18 -5.1(3) . . . . no C3 Ir1 C19 C20 -122.5(3) . . . . no C15 Ir1 C19 C18 -120.7(3) . . . . no C15 Ir1 C19 C20 121.9(4) . . . . no C16 Ir1 C19 C15 36.56(16) . . . . no C16 Ir1 C19 C18 -84.2(2) . . . . no C16 Ir1 C19 C20 158.4(3) . . . . no C17 Ir1 C19 C15 80.48(18) . . . . no C17 Ir1 C19 C18 -40.25(18) . . . . no C17 Ir1 C19 C20 -157.7(3) . . . . no C18 Ir1 C19 C15 120.7(3) . . . . no C18 Ir1 C19 C20 -117.4(4) . . . . no Ir1 N1 C1 C2 -5.3(3) . . . . no Ir1 N1 C1 C8 177.2(2) . . . . no C9 N1 C1 C2 173.5(2) . . . . no C9 N1 C1 C8 -4.0(4) . . . . no Ir1 N1 C9 C10 -87.9(2) . . . . no Ir1 N1 C9 C14 37.8(3) . . . . no C1 N1 C9 C10 93.5(3) . . . . no C1 N1 C9 C14 -140.9(2) . . . . no N1 C1 C2 C3 -3.0(3) . . . . no N1 C1 C2 C7 -178.6(3) . . . . no C8 C1 C2 C3 174.6(2) . . . . no C8 C1 C2 C7 -1.1(4) . . . . no C1 C2 C3 Ir1 10.2(3) . . . . no C1 C2 C3 C4 -170.5(2) . . . . no C7 C2 C3 Ir1 -174.0(2) . . . . no C7 C2 C3 C4 5.3(4) . . . . no C1 C2 C7 C6 173.9(3) . . . . no C3 C2 C7 C6 -1.5(4) . . . . no Ir1 C3 C4 C5 174.0(2) . . . . no C2 C3 C4 C5 -5.3(4) . . . . no C3 C4 C5 C6 1.4(4) . . . . no C4 C5 C6 C7 2.7(4) . . . . no C5 C6 C7 C2 -2.7(4) . . . . no N1 C9 C10 C11 -176.3(2) . . . . no C14 C9 C10 C11 57.4(3) . . . . no N1 C9 C14 C13 175.9(2) . . . . no C10 C9 C14 C13 -58.5(3) . . . . no C9 C10 C11 C12 -55.0(3) . . . . no C10 C11 C12 C13 53.7(3) . . . . no C11 C12 C13 C14 -54.7(3) . . . . no C12 C13 C14 C9 57.0(3) . . . . no Ir1 C15 C16 C17 -63.97(17) . . . . no Ir1 C15 C16 C23 124.8(3) . . . . no C19 C15 C16 Ir1 61.0(2) . . . . no C19 C15 C16 C17 -3.0(3) . . . . no C19 C15 C16 C23 -174.2(3) . . . . no C24 C15 C16 Ir1 -119.8(3) . . . . no C24 C15 C16 C17 176.2(2) . . . . no C24 C15 C16 C23 5.0(4) . . . . no Ir1 C15 C19 C18 54.71(19) . . . . no Ir1 C15 C19 C20 -133.4(3) . . . . no C16 C15 C19 Ir1 -56.56(19) . . . . no C16 C15 C19 C18 -1.8(3) . . . . no C16 C15 C19 C20 170.1(3) . . . . no C24 C15 C19 Ir1 124.3(3) . . . . no C24 C15 C19 C18 179.0(3) . . . . no C24 C15 C19 C20 -9.1(5) . . . . no Ir1 C16 C17 C18 -60.99(19) . . . . no Ir1 C16 C17 C22 121.8(3) . . . . no C15 C16 C17 Ir1 67.69(18) . . . . no C15 C16 C17 C18 6.7(3) . . . . no C15 C16 C17 C22 -170.5(3) . . . . no C23 C16 C17 Ir1 -121.2(3) . . . . no C23 C16 C17 C18 177.8(3) . . . . no C23 C16 C17 C22 0.6(4) . . . . no Ir1 C17 C18 C19 -69.0(2) . . . . no Ir1 C17 C18 C21 123.3(3) . . . . no C16 C17 C18 Ir1 61.14(18) . . . . no C16 C17 C18 C19 -7.9(3) . . . . no C16 C17 C18 C21 -175.6(3) . . . . no C22 C17 C18 Ir1 -121.6(3) . . . . no C22 C17 C18 C19 169.4(3) . . . . no C22 C17 C18 C21 1.7(4) . . . . no Ir1 C18 C19 C15 -58.5(2) . . . . no Ir1 C18 C19 C20 129.7(3) . . . . no C17 C18 C19 Ir1 64.44(18) . . . . no C17 C18 C19 C15 6.0(3) . . . . no C17 C18 C19 C20 -165.9(3) . . . . no C21 C18 C19 Ir1 -127.9(3) . . . . no C21 C18 C19 C15 173.6(3) . . . . no C21 C18 C19 C20 1.8(5) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C14 H14A Cl1 0.9900 2.8300 3.443(3) 121.00 . yes _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.602 _refine_diff_density_min -1.281 _refine_diff_density_rms 0.121 # Attachment '- Complex 4.cif' data_cwg42 _database_code_depnum_ccdc_archive 'CCDC 888576' #TrackingRef '- Complex 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common cwg42 _chemical_melting_point ? _chemical_formula_moiety '(Ir 3+), (H 1-),(C16 H13 O N2 1-),(C10 H15 1-)' _chemical_formula_sum 'C26 H29 Ir N2 O' _chemical_formula_weight 577.71 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' Ir Ir -1.4442 7.9887 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.885(10) _cell_length_b 9.215(3) _cell_length_c 16.691(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.318(7) _cell_angle_gamma 90.00 _cell_volume 4700(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5081 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.41 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 5.700 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2089 _exptl_absorpt_correction_T_max 0.5995 _exptl_absorpt_process_details 'SADABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10502 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4560 _reflns_number_gt 3717 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0930P)^2^+46.9455P] 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 4560 _refine_ls_number_parameters 250 _refine_ls_number_restraints 131 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir1 Ir Uani 0.37875(1) 0.13876(4) 0.57721(2) 1.000 0.0249(1) . . O3 O Uani 0.3593(3) -0.4476(8) 0.8180(4) 1.000 0.0331(19) . . N1 N Uani 0.3299(3) 0.0778(10) 0.6449(5) 1.000 0.027(2) . . N2 N Uani 0.3078(4) 0.7524(12) 0.4013(6) 1.000 0.052(4) . . C3 C Uani 0.3337(3) 0.3015(11) 0.5551(6) 1.000 0.0267(14) . . C4 C Uani 0.3353(3) 0.4222(11) 0.5039(6) 1.000 0.0267(14) . . C5 C Uani 0.3010(3) 0.5255(11) 0.4934(6) 1.000 0.029(3) . . C6 C Uani 0.2630(4) 0.5076(12) 0.5296(6) 1.000 0.033(3) . . C7 C Uani 0.2601(4) 0.3885(11) 0.5800(7) 1.000 0.035(3) . . C8 C Uani 0.2953(3) 0.2876(11) 0.5932(6) 1.000 0.0267(14) . . C9 C Uani 0.2947(4) 0.1571(10) 0.6432(6) 1.000 0.0267(14) . . C10 C Uani 0.2568(4) 0.1210(11) 0.6877(7) 1.000 0.035(3) . . C11 C Uani 0.3043(4) 0.6514(12) 0.4421(7) 1.000 0.035(3) . . C12 C Uani 0.3348(3) -0.0580(11) 0.6888(6) 1.000 0.028(3) . . C13 C Uani 0.3422(4) -0.0620(11) 0.7752(6) 1.000 0.029(3) . . C14 C Uani 0.3487(3) -0.1923(11) 0.8162(6) 1.000 0.029(3) . . C15 C Uani 0.3500(4) -0.3214(11) 0.7727(6) 1.000 0.029(3) . . C16 C Uani 0.3418(4) -0.3210(11) 0.6878(6) 1.000 0.030(3) . . C17 C Uani 0.3344(4) -0.1882(12) 0.6470(6) 1.000 0.0331(19) . . C18 C Uiso 0.3578(4) -0.5789(11) 0.7760(6) 1.000 0.029(2) . . C19 C Uani 0.4395(3) 0.0383(12) 0.5395(6) 1.000 0.030(2) . . C20 C Uani 0.4402(4) 0.1951(13) 0.5311(6) 1.000 0.032(3) . . C21 C Uani 0.4429(3) 0.2575(12) 0.6119(6) 1.000 0.030(3) . . C22 C Uani 0.4412(4) 0.1407(12) 0.6675(7) 1.000 0.038(3) . . C23 C Uani 0.4395(3) 0.0031(11) 0.6230(6) 1.000 0.027(2) . . C24 C Uani 0.4383(4) -0.0705(15) 0.4693(7) 1.000 0.046(4) . . C25 C Uani 0.4476(4) 0.2782(15) 0.4550(7) 1.000 0.044(3) . . C26 C Uani 0.4495(4) 0.4181(13) 0.6298(8) 1.000 0.039(3) . . C27 C Uani 0.4448(4) 0.1488(13) 0.7596(6) 1.000 0.039(4) . . C28 C Uani 0.4431(4) -0.1461(11) 0.6609(7) 1.000 0.038(3) . . H1 H Uiso 0.34590 0.03860 0.50320 1.000 0.02(3) . R H4 H Uiso 0.35980 0.43460 0.47590 1.000 0.0320 calc R H6 H Uiso 0.23970 0.57560 0.51990 1.000 0.0390 calc R H7 H Uiso 0.23470 0.37480 0.60540 1.000 0.0420 calc R H10A H Uiso 0.25660 0.01660 0.69870 1.000 0.0530 calc R H10B H Uiso 0.22920 0.14860 0.65420 1.000 0.0530 calc R H10C H Uiso 0.25980 0.17460 0.73890 1.000 0.0530 calc R H13 H Uiso 0.34270 0.02610 0.80490 1.000 0.0350 calc R H14 H Uiso 0.35220 -0.19410 0.87370 1.000 0.0340 calc R H16 H Uiso 0.34130 -0.40940 0.65840 1.000 0.0360 calc R H17 H Uiso 0.32890 -0.18750 0.58950 1.000 0.0400 calc R H18A H Uiso 0.36660 -0.65800 0.81420 1.000 0.0440 calc R H18B H Uiso 0.37790 -0.57480 0.73570 1.000 0.0440 calc R H18C H Uiso 0.32800 -0.59610 0.74880 1.000 0.0440 calc R H24A H Uiso 0.42860 -0.16530 0.48640 1.000 0.0690 calc R H24B H Uiso 0.46770 -0.07960 0.45400 1.000 0.0690 calc R H24C H Uiso 0.41790 -0.03590 0.42270 1.000 0.0690 calc R H25A H Uiso 0.43550 0.37640 0.45690 1.000 0.0660 calc R H25B H Uiso 0.43280 0.22760 0.40700 1.000 0.0660 calc R H25C H Uiso 0.47900 0.28410 0.45230 1.000 0.0660 calc R H26A H Uiso 0.44470 0.43790 0.68550 1.000 0.0590 calc R H26B H Uiso 0.42870 0.47450 0.59210 1.000 0.0590 calc R H26C H Uiso 0.47950 0.44560 0.62320 1.000 0.0590 calc R H27A H Uiso 0.41930 0.10160 0.77700 1.000 0.0580 calc R H27B H Uiso 0.44590 0.25070 0.77660 1.000 0.0580 calc R H27C H Uiso 0.47160 0.09940 0.78420 1.000 0.0580 calc R H28A H Uiso 0.42840 -0.21700 0.62240 1.000 0.0580 calc R H28B H Uiso 0.47410 -0.17230 0.67470 1.000 0.0580 calc R H28C H Uiso 0.42920 -0.14580 0.71000 1.000 0.0580 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 0.0212(3) 0.0316(2) 0.0212(2) 0.0002(2) 0.0011(2) 0.0030(2) O3 0.034(4) 0.036(3) 0.029(3) 0.001(2) 0.004(3) -0.003(3) N1 0.019(4) 0.033(4) 0.028(4) -0.004(3) 0.004(3) -0.006(3) N2 0.072(9) 0.049(6) 0.035(5) 0.008(4) 0.012(5) 0.020(6) C3 0.020(3) 0.033(2) 0.026(2) -0.0076(19) 0.000(2) -0.0019(19) C4 0.020(3) 0.033(2) 0.026(2) -0.0076(19) 0.000(2) -0.0019(19) C5 0.020(5) 0.039(5) 0.024(5) -0.007(3) -0.008(4) 0.004(4) C6 0.029(6) 0.039(5) 0.028(5) -0.006(4) -0.002(4) 0.010(4) C7 0.027(6) 0.042(6) 0.036(6) -0.004(4) 0.002(5) 0.005(4) C8 0.020(3) 0.033(2) 0.026(2) -0.0076(19) 0.000(2) -0.0019(19) C9 0.020(3) 0.033(2) 0.026(2) -0.0076(19) 0.000(2) -0.0019(19) C10 0.037(6) 0.041(6) 0.029(5) -0.007(4) 0.007(5) -0.002(5) C11 0.033(7) 0.042(6) 0.028(5) -0.003(4) 0.001(5) 0.014(5) C12 0.016(5) 0.039(5) 0.028(4) 0.003(4) 0.001(4) 0.002(4) C13 0.031(5) 0.032(4) 0.024(4) -0.003(3) 0.006(4) -0.003(4) C14 0.028(5) 0.035(4) 0.025(4) 0.003(3) 0.010(4) -0.004(4) C15 0.027(5) 0.031(4) 0.030(4) 0.004(3) 0.007(4) -0.005(4) C16 0.030(5) 0.031(4) 0.029(4) -0.003(3) 0.007(4) -0.005(4) C17 0.034(4) 0.036(3) 0.029(3) 0.001(2) 0.004(3) -0.003(3) C19 0.021(4) 0.044(4) 0.026(4) 0.000(3) 0.006(4) 0.012(4) C20 0.020(5) 0.047(4) 0.030(4) 0.006(3) 0.005(4) 0.010(4) C21 0.012(5) 0.042(4) 0.034(4) 0.001(4) 0.000(4) -0.005(4) C22 0.049(8) 0.044(5) 0.023(4) 0.001(4) 0.011(5) 0.003(5) C23 0.011(4) 0.041(4) 0.029(4) 0.003(3) 0.006(4) 0.013(4) C24 0.038(7) 0.063(7) 0.036(5) -0.010(5) 0.003(5) 0.014(6) C25 0.020(6) 0.068(7) 0.044(5) 0.021(5) 0.007(5) 0.000(5) C26 0.023(6) 0.040(5) 0.054(7) -0.004(5) 0.002(5) -0.008(5) C27 0.030(7) 0.063(8) 0.022(4) 0.002(4) 0.000(5) -0.005(5) C28 0.023(6) 0.043(5) 0.047(7) 0.009(5) -0.001(5) 0.005(5) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N1 2.088(9) . . yes Ir1 C3 2.043(10) . . yes Ir1 C19 2.262(10) . . yes Ir1 C20 2.211(12) . . yes Ir1 C21 2.264(10) . . yes Ir1 C22 2.270(12) . . yes Ir1 C23 2.292(10) . . yes Ir1 H1 1.7400 . . no O3 C18 1.396(12) . . yes O3 C15 1.394(12) . . yes N1 C12 1.447(14) . . yes N1 C9 1.307(15) . . yes N2 C11 1.168(16) . . yes C3 C8 1.430(13) . . no C3 C4 1.408(14) . . no C4 C5 1.416(14) . . no C5 C11 1.454(15) . . no C5 C6 1.405(15) . . no C6 C7 1.394(15) . . no C7 C8 1.423(15) . . no C8 C9 1.465(14) . . no C9 C10 1.511(17) . . no C12 C13 1.428(14) . . no C12 C17 1.387(15) . . no C13 C14 1.382(14) . . no C14 C15 1.397(14) . . no C15 C16 1.403(14) . . no C16 C17 1.403(15) . . no C19 C23 1.431(14) . . no C19 C24 1.539(16) . . no C19 C20 1.452(16) . . no C20 C25 1.528(16) . . no C20 C21 1.457(14) . . no C21 C22 1.427(15) . . no C21 C26 1.518(16) . . no C22 C27 1.527(15) . . no C22 C23 1.467(15) . . no C23 C28 1.511(15) . . no C4 H4 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C10 H10A 0.9800 . . no C10 H10B 0.9800 . . no C10 H10C 0.9800 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 H18A 0.9800 . . no C18 H18B 0.9800 . . no C18 H18C 0.9800 . . no C24 H24A 0.9800 . . no C24 H24B 0.9800 . . no C24 H24C 0.9800 . . no C25 H25A 0.9800 . . no C25 H25B 0.9800 . . no C25 H25C 0.9800 . . no C26 H26A 0.9800 . . no C26 H26B 0.9800 . . no C26 H26C 0.9800 . . no C27 H27A 0.9800 . . no C27 H27B 0.9800 . . no C27 H27C 0.9800 . . no C28 H28A 0.9800 . . no C28 H28B 0.9800 . . no C28 H28C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C3 76.6(4) . . . yes N1 Ir1 C19 137.2(4) . . . yes N1 Ir1 C20 167.3(4) . . . yes N1 Ir1 C21 131.7(3) . . . yes N1 Ir1 C22 104.7(4) . . . yes N1 Ir1 C23 107.1(3) . . . yes C3 Ir1 C19 145.2(4) . . . yes C3 Ir1 C20 111.2(4) . . . yes C3 Ir1 C21 103.9(4) . . . yes C3 Ir1 C22 127.3(4) . . . yes C3 Ir1 C23 164.6(4) . . . yes C19 Ir1 C20 37.9(4) . . . yes C19 Ir1 C21 62.5(4) . . . yes C19 Ir1 C22 61.9(4) . . . yes C19 Ir1 C23 36.6(4) . . . yes C20 Ir1 C21 38.0(4) . . . yes C20 Ir1 C22 62.6(4) . . . yes C20 Ir1 C23 62.7(4) . . . yes C21 Ir1 C22 36.7(4) . . . yes C21 Ir1 C23 62.3(4) . . . yes C22 Ir1 C23 37.5(4) . . . yes C20 Ir1 H1 109.00 . . . no C21 Ir1 H1 147.00 . . . no C22 Ir1 H1 146.00 . . . no C23 Ir1 H1 108.00 . . . no N1 Ir1 H1 81.00 . . . no C3 Ir1 H1 87.00 . . . no C19 Ir1 H1 90.00 . . . no C15 O3 C18 117.5(7) . . . yes Ir1 N1 C12 118.4(7) . . . yes C9 N1 C12 121.4(9) . . . yes Ir1 N1 C9 120.1(7) . . . yes C4 C3 C8 116.4(9) . . . no Ir1 C3 C8 116.2(7) . . . yes Ir1 C3 C4 127.4(7) . . . yes C3 C4 C5 121.0(9) . . . no C4 C5 C6 121.6(9) . . . no C4 C5 C11 119.6(9) . . . no C6 C5 C11 118.7(9) . . . no C5 C6 C7 118.9(11) . . . no C6 C7 C8 119.6(11) . . . no C3 C8 C7 122.5(9) . . . no C3 C8 C9 114.0(9) . . . no C7 C8 C9 123.5(9) . . . no N1 C9 C8 113.1(10) . . . yes N1 C9 C10 124.6(9) . . . yes C8 C9 C10 122.4(9) . . . no N2 C11 C5 178.7(12) . . . yes N1 C12 C17 120.1(9) . . . yes N1 C12 C13 121.6(9) . . . yes C13 C12 C17 118.3(9) . . . no C12 C13 C14 120.9(9) . . . no C13 C14 C15 119.7(9) . . . no O3 C15 C14 116.6(9) . . . yes O3 C15 C16 122.9(9) . . . yes C14 C15 C16 120.5(9) . . . no C15 C16 C17 119.0(9) . . . no C12 C17 C16 121.4(9) . . . no C23 C19 C24 126.2(10) . . . no Ir1 C19 C23 72.8(5) . . . yes Ir1 C19 C20 69.2(6) . . . yes C20 C19 C24 125.0(9) . . . no Ir1 C19 C24 123.3(7) . . . yes C20 C19 C23 108.8(9) . . . no Ir1 C20 C21 73.0(6) . . . yes Ir1 C20 C19 73.0(6) . . . yes Ir1 C20 C25 130.3(8) . . . yes C19 C20 C21 107.6(9) . . . no C19 C20 C25 125.8(10) . . . no C21 C20 C25 125.2(10) . . . no Ir1 C21 C20 69.0(6) . . . yes Ir1 C21 C22 71.9(6) . . . yes Ir1 C21 C26 127.5(7) . . . yes C22 C21 C26 128.6(10) . . . no C20 C21 C22 107.6(10) . . . no C20 C21 C26 123.7(10) . . . no C21 C22 C27 127.9(10) . . . no Ir1 C22 C21 71.5(6) . . . yes Ir1 C22 C23 72.1(6) . . . yes Ir1 C22 C27 126.9(8) . . . yes C21 C22 C23 109.0(9) . . . no C23 C22 C27 123.0(10) . . . no Ir1 C23 C19 70.5(6) . . . yes Ir1 C23 C22 70.4(6) . . . yes Ir1 C23 C28 130.0(7) . . . yes C19 C23 C22 107.0(9) . . . no C19 C23 C28 127.1(9) . . . no C22 C23 C28 125.4(9) . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 119.00 . . . no C5 C6 H6 121.00 . . . no C7 C6 H6 121.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C9 C10 H10A 110.00 . . . no C9 C10 H10B 109.00 . . . no C9 C10 H10C 110.00 . . . no H10A C10 H10B 109.00 . . . no H10A C10 H10C 110.00 . . . no H10B C10 H10C 109.00 . . . no C12 C13 H13 120.00 . . . no C14 C13 H13 120.00 . . . no C13 C14 H14 120.00 . . . no C15 C14 H14 120.00 . . . no C15 C16 H16 120.00 . . . no C17 C16 H16 121.00 . . . no C12 C17 H17 119.00 . . . no C16 C17 H17 119.00 . . . no O3 C18 H18A 109.00 . . . no O3 C18 H18B 109.00 . . . no O3 C18 H18C 110.00 . . . no H18A C18 H18B 109.00 . . . no H18A C18 H18C 110.00 . . . no H18B C18 H18C 110.00 . . . no C19 C24 H24A 110.00 . . . no C19 C24 H24B 109.00 . . . no C19 C24 H24C 110.00 . . . no H24A C24 H24B 109.00 . . . no H24A C24 H24C 109.00 . . . no H24B C24 H24C 109.00 . . . no C20 C25 H25A 109.00 . . . no C20 C25 H25B 109.00 . . . no C20 C25 H25C 110.00 . . . no H25A C25 H25B 109.00 . . . no H25A C25 H25C 110.00 . . . no H25B C25 H25C 110.00 . . . no C21 C26 H26A 110.00 . . . no C21 C26 H26B 109.00 . . . no C21 C26 H26C 109.00 . . . no H26A C26 H26B 110.00 . . . no H26A C26 H26C 109.00 . . . no H26B C26 H26C 109.00 . . . no C22 C27 H27A 109.00 . . . no C22 C27 H27B 109.00 . . . no C22 C27 H27C 109.00 . . . no H27A C27 H27B 110.00 . . . no H27A C27 H27C 110.00 . . . no H27B C27 H27C 109.00 . . . no C23 C28 H28A 109.00 . . . no C23 C28 H28B 109.00 . . . no C23 C28 H28C 109.00 . . . no H28A C28 H28B 109.00 . . . no H28A C28 H28C 109.00 . . . no H28B C28 H28C 110.00 . . . no 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 C3 Ir1 N1 C9 1.8(8) . . . . no C3 Ir1 N1 C12 177.8(8) . . . . no C19 Ir1 N1 C9 -168.4(7) . . . . no C19 Ir1 N1 C12 7.6(10) . . . . no C21 Ir1 N1 C9 98.5(9) . . . . no C21 Ir1 N1 C12 -85.5(8) . . . . no C22 Ir1 N1 C9 127.3(8) . . . . no C22 Ir1 N1 C12 -56.7(8) . . . . no C23 Ir1 N1 C9 166.3(8) . . . . no C23 Ir1 N1 C12 -17.7(8) . . . . no N1 Ir1 C3 C4 -178.0(10) . . . . no N1 Ir1 C3 C8 -1.1(7) . . . . no C19 Ir1 C3 C4 -9.7(13) . . . . no C19 Ir1 C3 C8 167.3(7) . . . . no C20 Ir1 C3 C4 12.5(10) . . . . no C20 Ir1 C3 C8 -170.5(7) . . . . no C21 Ir1 C3 C4 51.7(10) . . . . no C21 Ir1 C3 C8 -131.3(7) . . . . no C22 Ir1 C3 C4 83.5(10) . . . . no C22 Ir1 C3 C8 -99.5(8) . . . . no N1 Ir1 C19 C20 -161.8(6) . . . . no N1 Ir1 C19 C23 -43.2(8) . . . . no N1 Ir1 C19 C24 79.3(10) . . . . no C3 Ir1 C19 C20 35.1(9) . . . . no C3 Ir1 C19 C23 153.6(7) . . . . no C3 Ir1 C19 C24 -83.9(11) . . . . no C20 Ir1 C19 C23 118.6(8) . . . . no C20 Ir1 C19 C24 -119.0(11) . . . . no C21 Ir1 C19 C20 -38.9(6) . . . . no C21 Ir1 C19 C23 79.6(6) . . . . no C21 Ir1 C19 C24 -157.9(10) . . . . no C22 Ir1 C19 C20 -80.6(6) . . . . no C22 Ir1 C19 C23 38.0(6) . . . . no C22 Ir1 C19 C24 160.4(10) . . . . no C23 Ir1 C19 C20 -118.6(8) . . . . no C23 Ir1 C19 C24 122.5(12) . . . . no C3 Ir1 C20 C19 -159.4(6) . . . . no C3 Ir1 C20 C21 85.5(7) . . . . no C3 Ir1 C20 C25 -36.6(12) . . . . no C19 Ir1 C20 C21 -115.2(9) . . . . no C19 Ir1 C20 C25 122.8(13) . . . . no C21 Ir1 C20 C19 115.2(9) . . . . no C21 Ir1 C20 C25 -122.0(14) . . . . no C22 Ir1 C20 C19 78.6(6) . . . . no C22 Ir1 C20 C21 -36.6(6) . . . . no C22 Ir1 C20 C25 -158.6(12) . . . . no C23 Ir1 C20 C19 36.1(6) . . . . no C23 Ir1 C20 C21 -79.0(6) . . . . no C23 Ir1 C20 C25 159.0(12) . . . . no N1 Ir1 C21 C20 168.9(6) . . . . no N1 Ir1 C21 C22 51.2(8) . . . . no N1 Ir1 C21 C26 -74.0(11) . . . . no C3 Ir1 C21 C20 -106.8(7) . . . . no C3 Ir1 C21 C22 135.5(6) . . . . no C3 Ir1 C21 C26 10.3(10) . . . . no C19 Ir1 C21 C20 38.8(6) . . . . no C19 Ir1 C21 C22 -79.0(7) . . . . no C19 Ir1 C21 C26 155.9(10) . . . . no C20 Ir1 C21 C22 -117.8(9) . . . . no C20 Ir1 C21 C26 117.1(12) . . . . no C22 Ir1 C21 C20 117.8(9) . . . . no C22 Ir1 C21 C26 -125.2(12) . . . . no C23 Ir1 C21 C20 80.3(7) . . . . no C23 Ir1 C21 C22 -37.4(6) . . . . no C23 Ir1 C21 C26 -162.6(10) . . . . no N1 Ir1 C22 C21 -143.1(6) . . . . no N1 Ir1 C22 C23 99.0(6) . . . . no N1 Ir1 C22 C27 -19.2(10) . . . . no C3 Ir1 C22 C21 -58.8(8) . . . . no C3 Ir1 C22 C23 -176.8(6) . . . . no C3 Ir1 C22 C27 65.0(11) . . . . no C19 Ir1 C22 C21 80.9(7) . . . . no C19 Ir1 C22 C23 -37.1(6) . . . . no C19 Ir1 C22 C27 -155.2(11) . . . . no C20 Ir1 C22 C21 37.9(6) . . . . no C20 Ir1 C22 C23 -80.1(7) . . . . no C20 Ir1 C22 C27 161.7(11) . . . . no C21 Ir1 C22 C23 -117.9(9) . . . . no C21 Ir1 C22 C27 123.9(12) . . . . no C23 Ir1 C22 C21 117.9(9) . . . . no C23 Ir1 C22 C27 -118.2(12) . . . . no N1 Ir1 C23 C19 150.9(6) . . . . no N1 Ir1 C23 C22 -92.1(6) . . . . no N1 Ir1 C23 C28 28.2(10) . . . . no C19 Ir1 C23 C22 117.0(9) . . . . no C19 Ir1 C23 C28 -122.7(12) . . . . no C20 Ir1 C23 C19 -37.4(6) . . . . no C20 Ir1 C23 C22 79.7(7) . . . . no C20 Ir1 C23 C28 -160.0(10) . . . . no C21 Ir1 C23 C19 -80.4(6) . . . . no C21 Ir1 C23 C22 36.6(6) . . . . no C21 Ir1 C23 C28 156.9(10) . . . . no C22 Ir1 C23 C19 -117.0(9) . . . . no C22 Ir1 C23 C28 120.3(12) . . . . no C18 O3 C15 C14 175.7(10) . . . . no C18 O3 C15 C16 -3.7(17) . . . . no C9 N1 C12 C13 -72.0(13) . . . . no Ir1 N1 C12 C17 -64.9(11) . . . . no Ir1 N1 C9 C8 -2.0(12) . . . . no C12 N1 C9 C8 -177.9(9) . . . . no Ir1 N1 C9 C10 178.1(8) . . . . no C12 N1 C9 C10 2.3(15) . . . . no Ir1 N1 C12 C13 112.1(10) . . . . no C9 N1 C12 C17 111.0(12) . . . . no Ir1 C3 C4 C5 178.8(7) . . . . no C8 C3 C4 C5 1.9(14) . . . . no Ir1 C3 C8 C7 -176.6(8) . . . . no Ir1 C3 C8 C9 0.4(11) . . . . no C4 C3 C8 C7 0.7(15) . . . . no C4 C3 C8 C9 177.7(9) . . . . no C3 C4 C5 C6 -3.8(15) . . . . no C3 C4 C5 C11 178.1(10) . . . . no C4 C5 C6 C7 3.0(15) . . . . no C11 C5 C6 C7 -178.8(10) . . . . no C5 C6 C7 C8 -0.5(16) . . . . no C6 C7 C8 C9 -178.2(10) . . . . no C6 C7 C8 C3 -1.4(16) . . . . no C3 C8 C9 N1 1.0(13) . . . . no C7 C8 C9 N1 178.0(10) . . . . no C7 C8 C9 C10 -2.1(16) . . . . no C3 C8 C9 C10 -179.1(9) . . . . no N1 C12 C13 C14 -177.2(10) . . . . no C17 C12 C13 C14 -0.2(16) . . . . no N1 C12 C17 C16 176.0(10) . . . . no C13 C12 C17 C16 -1.1(17) . . . . no C12 C13 C14 C15 2.9(17) . . . . no C13 C14 C15 O3 176.2(10) . . . . no C13 C14 C15 C16 -4.4(17) . . . . no O3 C15 C16 C17 -177.5(11) . . . . no C14 C15 C16 C17 3.1(18) . . . . no C15 C16 C17 C12 -0.4(18) . . . . no Ir1 C19 C20 C21 65.3(8) . . . . no Ir1 C19 C20 C25 -127.8(12) . . . . no C23 C19 C20 Ir1 -62.4(7) . . . . no C23 C19 C20 C21 2.9(12) . . . . no C23 C19 C20 C25 169.8(11) . . . . no C24 C19 C20 Ir1 116.8(10) . . . . no C24 C19 C20 C21 -177.9(9) . . . . no C24 C19 C20 C25 -11.0(18) . . . . no Ir1 C19 C23 C22 -61.3(7) . . . . no Ir1 C19 C23 C28 126.0(10) . . . . no C20 C19 C23 Ir1 60.1(7) . . . . no C20 C19 C23 C22 -1.2(11) . . . . no C20 C19 C23 C28 -173.9(10) . . . . no C24 C19 C23 Ir1 -119.1(10) . . . . no C24 C19 C23 C22 179.6(10) . . . . no C24 C19 C23 C28 6.9(16) . . . . no Ir1 C20 C21 C22 61.9(8) . . . . no Ir1 C20 C21 C26 -121.9(10) . . . . no C19 C20 C21 Ir1 -65.3(8) . . . . no C19 C20 C21 C22 -3.4(12) . . . . no C19 C20 C21 C26 172.8(10) . . . . no C25 C20 C21 Ir1 127.7(12) . . . . no C25 C20 C21 C22 -170.4(11) . . . . no C25 C20 C21 C26 5.8(17) . . . . no Ir1 C21 C22 C23 62.7(8) . . . . no Ir1 C21 C22 C27 -122.7(13) . . . . no C20 C21 C22 Ir1 -60.1(7) . . . . no C20 C21 C22 C23 2.6(12) . . . . no C20 C21 C22 C27 177.2(12) . . . . no C26 C21 C22 Ir1 124.0(11) . . . . no C26 C21 C22 C23 -173.3(10) . . . . no C26 C21 C22 C27 1.2(19) . . . . no Ir1 C22 C23 C19 61.4(7) . . . . no Ir1 C22 C23 C28 -125.8(10) . . . . no C21 C22 C23 Ir1 -62.3(8) . . . . no C21 C22 C23 C19 -0.9(12) . . . . no C21 C22 C23 C28 171.9(10) . . . . no C27 C22 C23 Ir1 122.8(11) . . . . no C27 C22 C23 C19 -175.8(10) . . . . no C27 C22 C23 C28 -3.0(17) . . . . no _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 3.643 _refine_diff_density_min -2.575 _refine_diff_density_rms 0.247 # Attachment '- Complex 5.cif' data_cwi29bm _database_code_depnum_ccdc_archive 'CCDC 888577' #TrackingRef '- Complex 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common CWG29B _chemical_melting_point ? _chemical_formula_moiety '(Ir 3+), (H 1-), (C16 H16 O2 N 1-), (C10 H15 1-)' _chemical_formula_sum 'C26 H32 Ir N O2' _chemical_formula_weight 582.73 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' Ir Ir -1.4442 7.9887 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 7.1562(7) _cell_length_b 31.863(3) _cell_length_c 9.9929(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.2420(10) _cell_angle_gamma 90.00 _cell_volume 2242.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5280 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 5.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2672 _exptl_absorpt_correction_T_max 0.7543 _exptl_absorpt_process_details 'SADABS V2008-1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 diffractometer with APEX detector' _diffrn_measurement_method '\w scans with a narrow frame width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12832 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.21 _reflns_number_total 4905 _reflns_number_gt 4237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v.5.632 (Bruker, 2005)' _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0107P)^2^+15.7378P] 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 4905 _refine_ls_number_parameters 281 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.212 _refine_ls_shift/su_max 0.004 _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 0.66991(3) 0.139500(7) -0.02174(2) 0.01182(7) Uani 1 1 d D . . O1 O 0.7033(7) 0.30075(14) -0.2192(4) 0.0218(10) Uani 1 1 d . . . O2 O 0.7592(6) 0.02043(14) 0.5556(5) 0.0228(10) Uani 1 1 d . . . N1 N 0.6966(7) 0.15301(15) 0.1796(5) 0.0131(10) Uani 1 1 d D . . C14 C 0.9161(10) 0.0184(2) 0.6666(7) 0.0234(15) Uani 1 1 d . . . H14A H 1.0335 0.0135 0.6313 0.035 Uiso 1 1 calc R . . H14B H 0.8959 -0.0045 0.7277 0.035 Uiso 1 1 calc R . . H14C H 0.9261 0.0450 0.7166 0.035 Uiso 1 1 calc R . . C3 C 0.6887(8) 0.20363(17) -0.0201(6) 0.0128(12) Uani 1 1 d D . . C13 C 0.7567(9) 0.0538(2) 0.4662(6) 0.0182(13) Uani 1 1 d . . . C25 C 1.0133(9) 0.1543(2) -0.2053(7) 0.0184(13) Uani 1 1 d . . . H25A H 0.9576 0.1824 -0.2155 0.028 Uiso 1 1 calc R . . H25B H 1.0406 0.1447 -0.2930 0.028 Uiso 1 1 calc R . . H25C H 1.1314 0.1551 -0.1384 0.028 Uiso 1 1 calc R . . C8 C 0.7182(8) 0.2654(2) 0.1255(6) 0.0160(13) Uani 1 1 d . . . H8 H 0.7304 0.2775 0.2135 0.019 Uiso 1 1 calc R . . C9 C 0.7083(9) 0.2068(2) 0.3631(6) 0.0197(14) Uani 1 1 d . . . H9A H 0.6716 0.1834 0.4167 0.030 Uiso 1 1 calc R . . H9B H 0.6182 0.2300 0.3629 0.030 Uiso 1 1 calc R . . H9C H 0.8362 0.2163 0.4031 0.030 Uiso 1 1 calc R . . C17 C 0.6826(9) 0.11768(19) -0.2254(6) 0.0152(13) Uani 1 1 d . . . C2 C 0.7016(8) 0.22163(19) 0.1096(6) 0.0123(12) Uani 1 1 d . . . C11 C 0.8909(9) 0.1125(2) 0.3681(6) 0.0168(13) Uani 1 1 d . . . H11 H 0.9970 0.1300 0.3631 0.020 Uiso 1 1 calc R . . C19 C 0.9155(8) 0.09711(19) -0.0444(6) 0.0143(12) Uani 1 1 d . . . C26 C 0.5889(10) 0.1371(2) -0.3561(6) 0.0241(14) Uani 1 1 d . . . H26A H 0.6294 0.1224 -0.4323 0.036 Uiso 1 1 calc R . . H26B H 0.6250 0.1667 -0.3576 0.036 Uiso 1 1 calc R . . H26C H 0.4507 0.1348 -0.3644 0.036 Uiso 1 1 calc R . . C24 C 1.0982(9) 0.0918(2) 0.0543(7) 0.0196(14) Uani 1 1 d . . . H24A H 1.1834 0.1152 0.0444 0.029 Uiso 1 1 calc R . . H24B H 1.1584 0.0653 0.0358 0.029 Uiso 1 1 calc R . . H24C H 1.0719 0.0914 0.1473 0.029 Uiso 1 1 calc R . . C10 C 0.7200(8) 0.11988(19) 0.2817(6) 0.0142(12) Uani 1 1 d . . . C1 C 0.7064(8) 0.1926(2) 0.2206(6) 0.0160(13) Uani 1 1 d . . . C16 C 0.5670(9) 0.0930(2) 0.2860(6) 0.0167(13) Uani 1 1 d . . . H16 H 0.4497 0.0973 0.2260 0.020 Uiso 1 1 calc R . . C23 C 0.7363(9) 0.0352(2) 0.0513(6) 0.0195(14) Uani 1 1 d . . . H23A H 0.6027 0.0285 0.0515 0.029 Uiso 1 1 calc R . . H23B H 0.7984 0.0430 0.1434 0.029 Uiso 1 1 calc R . . H23C H 0.8001 0.0107 0.0210 0.029 Uiso 1 1 calc R . . C22 C 0.4201(9) 0.0631(2) -0.2029(7) 0.0214(14) Uani 1 1 d . . . H22A H 0.4299 0.0419 -0.2725 0.032 Uiso 1 1 calc R . . H22B H 0.3280 0.0846 -0.2409 0.032 Uiso 1 1 calc R . . H22C H 0.3781 0.0497 -0.1251 0.032 Uiso 1 1 calc R . . C7 C 0.7168(8) 0.2906(2) 0.0134(7) 0.0186(14) Uani 1 1 d . . . H7 H 0.7266 0.3202 0.0237 0.022 Uiso 1 1 calc R . . C4 C 0.6807(8) 0.22940(19) -0.1318(6) 0.0154(13) Uani 1 1 d . . . H4 H 0.6614 0.2175 -0.2204 0.018 Uiso 1 1 calc R . . C18 C 0.8765(9) 0.12463(19) -0.1579(6) 0.0143(12) Uani 1 1 d . . . C15 C 0.5868(9) 0.0600(2) 0.3783(6) 0.0191(14) Uani 1 1 d . . . H15 H 0.4830 0.0417 0.3810 0.023 Uiso 1 1 calc R . . C21 C 0.6092(8) 0.08293(18) -0.1574(6) 0.0156(12) Uani 1 1 d D . . C12 C 0.9095(9) 0.0796(2) 0.4629(6) 0.0179(13) Uani 1 1 d . . . H12 H 1.0258 0.0753 0.5239 0.021 Uiso 1 1 calc R . . C5 C 0.7007(8) 0.27238(19) -0.1162(6) 0.0160(13) Uani 1 1 d . . . C20 C 0.7480(8) 0.07123(19) -0.0435(6) 0.0135(12) Uani 1 1 d . . . C6 C 0.7036(9) 0.28333(18) -0.3457(6) 0.0225(14) Uani 1 1 d . . . H6A H 0.8347 0.2775 -0.3564 0.034 Uiso 1 1 calc R . . H6B H 0.6456 0.3030 -0.4164 0.034 Uiso 1 1 calc R . . H6C H 0.6310 0.2571 -0.3540 0.034 Uiso 1 1 calc R . . H1 H 0.4294 0.1463 -0.0372 0.027(19) Uiso 1 1 d RD . . 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 0.01270(11) 0.01209(11) 0.01089(11) 0.00003(11) 0.00273(7) -0.00014(11) O1 0.030(3) 0.014(2) 0.021(2) 0.0063(19) 0.003(2) 0.0003(19) O2 0.025(3) 0.023(3) 0.020(2) 0.006(2) 0.001(2) -0.001(2) N1 0.013(2) 0.014(3) 0.014(3) 0.002(2) 0.006(2) -0.0015(19) C14 0.028(4) 0.024(4) 0.017(3) 0.007(3) 0.001(3) 0.005(3) C3 0.009(3) 0.019(3) 0.012(3) -0.001(3) 0.008(2) 0.005(2) C13 0.022(3) 0.018(3) 0.013(3) 0.003(3) 0.000(3) 0.002(3) C25 0.017(3) 0.016(3) 0.024(3) 0.001(3) 0.009(3) 0.001(2) C8 0.010(3) 0.022(3) 0.015(3) -0.004(3) 0.001(2) -0.002(2) C9 0.024(3) 0.021(3) 0.013(3) -0.004(3) 0.002(3) -0.001(3) C17 0.020(3) 0.013(3) 0.013(3) -0.002(2) 0.004(2) 0.006(2) C2 0.007(3) 0.018(3) 0.012(3) 0.002(2) 0.003(2) 0.004(2) C11 0.013(3) 0.023(3) 0.014(3) -0.004(3) 0.002(2) -0.001(2) C19 0.015(3) 0.015(3) 0.013(3) -0.002(2) 0.004(2) 0.004(2) C26 0.032(4) 0.022(4) 0.018(3) 0.009(3) 0.003(3) 0.008(3) C24 0.014(3) 0.022(4) 0.023(3) 0.001(3) 0.002(3) 0.005(3) C10 0.016(3) 0.016(3) 0.011(3) -0.001(2) 0.003(2) 0.001(2) C1 0.012(3) 0.018(3) 0.019(3) 0.001(3) 0.005(2) -0.001(2) C16 0.015(3) 0.021(3) 0.013(3) 0.000(3) 0.001(2) -0.001(2) C23 0.023(3) 0.018(3) 0.017(3) -0.001(3) 0.004(3) -0.001(3) C22 0.018(3) 0.021(3) 0.025(4) -0.006(3) 0.001(3) -0.001(3) C7 0.011(3) 0.015(3) 0.028(4) 0.000(3) 0.000(3) 0.002(2) C4 0.012(3) 0.019(3) 0.015(3) -0.001(3) 0.001(2) 0.001(2) C18 0.017(3) 0.015(3) 0.013(3) -0.004(2) 0.007(2) 0.001(2) C15 0.017(3) 0.021(3) 0.018(3) 0.001(3) 0.000(3) -0.006(3) C21 0.018(3) 0.013(3) 0.015(3) -0.003(3) 0.003(2) 0.005(2) C12 0.015(3) 0.022(3) 0.015(3) -0.001(3) -0.001(2) 0.002(3) C5 0.010(3) 0.015(3) 0.021(3) 0.005(3) -0.002(2) 0.004(2) C20 0.014(3) 0.016(3) 0.010(3) 0.001(2) 0.004(2) 0.000(2) C6 0.021(3) 0.021(4) 0.026(4) 0.008(3) 0.005(3) -0.002(3) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 2.033(5) . ? Ir1 C3 2.048(5) . ? Ir1 C17 2.167(6) . ? Ir1 C18 2.231(6) . ? Ir1 C21 2.251(5) . ? Ir1 C19 2.259(6) . ? Ir1 C20 2.266(6) . ? Ir1 H1 1.7141 . ? O1 C5 1.372(7) . ? O1 C6 1.381(7) . ? O2 C13 1.386(7) . ? O2 C14 1.432(8) . ? N1 C1 1.324(8) . ? N1 C10 1.457(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C3 C4 1.379(8) . ? C3 C2 1.406(8) . ? C13 C12 1.374(9) . ? C13 C15 1.382(9) . ? C25 C18 1.497(8) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C8 C7 1.377(9) . ? C8 C2 1.405(8) . ? C8 H8 0.9500 . ? C9 C1 1.491(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C17 C21 1.446(9) . ? C17 C18 1.448(9) . ? C17 C26 1.493(8) . ? C2 C1 1.441(8) . ? C11 C10 1.386(8) . ? C11 C12 1.403(9) . ? C11 H11 0.9500 . ? C19 C18 1.421(8) . ? C19 C20 1.456(8) . ? C19 C24 1.501(8) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C10 C16 1.396(8) . ? C16 C15 1.390(9) . ? C16 H16 0.9500 . ? C23 C20 1.499(8) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C22 C21 1.489(8) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C7 C5 1.405(9) . ? C7 H7 0.9500 . ? C4 C5 1.383(8) . ? C4 H4 0.9500 . ? C15 H15 0.9500 . ? C21 C20 1.421(8) . ? C12 H12 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 C3 77.7(2) . . ? N1 Ir1 C17 170.0(2) . . ? C3 Ir1 C17 108.3(2) . . ? N1 Ir1 C18 133.8(2) . . ? C3 Ir1 C18 99.6(2) . . ? C17 Ir1 C18 38.4(2) . . ? N1 Ir1 C21 137.7(2) . . ? C3 Ir1 C21 144.0(2) . . ? C17 Ir1 C21 38.2(2) . . ? C18 Ir1 C21 62.7(2) . . ? N1 Ir1 C19 106.7(2) . . ? C3 Ir1 C19 123.1(2) . . ? C17 Ir1 C19 63.3(2) . . ? C18 Ir1 C19 36.9(2) . . ? C21 Ir1 C19 62.0(2) . . ? N1 Ir1 C20 108.5(2) . . ? C3 Ir1 C20 160.3(2) . . ? C17 Ir1 C20 63.2(2) . . ? C18 Ir1 C20 62.3(2) . . ? C21 Ir1 C20 36.7(2) . . ? C19 Ir1 C20 37.5(2) . . ? N1 Ir1 H1 88.8 . . ? C3 Ir1 H1 86.4 . . ? C17 Ir1 H1 99.5 . . ? C18 Ir1 H1 137.4 . . ? C21 Ir1 H1 88.0 . . ? C19 Ir1 H1 148.6 . . ? C20 Ir1 H1 112.0 . . ? C5 O1 C6 115.1(5) . . ? C13 O2 C14 116.8(5) . . ? C1 N1 C10 118.7(5) . . ? C1 N1 Ir1 119.9(4) . . ? C10 N1 Ir1 121.2(4) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C4 C3 C2 119.4(5) . . ? C4 C3 Ir1 126.5(4) . . ? C2 C3 Ir1 114.1(4) . . ? C12 C13 C15 120.8(6) . . ? C12 C13 O2 123.8(6) . . ? C15 C13 O2 115.4(6) . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C7 C8 C2 119.9(6) . . ? C7 C8 H8 120.1 . . ? C2 C8 H8 120.1 . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C21 C17 C18 107.2(5) . . ? C21 C17 C26 125.7(6) . . ? C18 C17 C26 126.1(6) . . ? C21 C17 Ir1 74.0(3) . . ? C18 C17 Ir1 73.2(3) . . ? C26 C17 Ir1 127.0(4) . . ? C3 C2 C8 120.0(5) . . ? C3 C2 C1 115.9(5) . . ? C8 C2 C1 124.1(6) . . ? C10 C11 C12 121.0(6) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C18 C19 C20 108.0(5) . . ? C18 C19 C24 128.2(6) . . ? C20 C19 C24 123.7(5) . . ? C18 C19 Ir1 70.4(3) . . ? C20 C19 Ir1 71.5(3) . . ? C24 C19 Ir1 127.1(4) . . ? C17 C26 H26A 109.5 . . ? C17 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C17 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 C10 C16 119.2(6) . . ? C11 C10 N1 122.5(5) . . ? C16 C10 N1 118.2(5) . . ? N1 C1 C2 112.4(5) . . ? N1 C1 C9 125.2(6) . . ? C2 C1 C9 122.3(6) . . ? C15 C16 C10 119.7(6) . . ? C15 C16 H16 120.1 . . ? C10 C16 H16 120.1 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C8 C7 C5 119.8(6) . . ? C8 C7 H7 120.1 . . ? C5 C7 H7 120.1 . . ? C3 C4 C5 120.6(6) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C19 C18 C17 108.3(5) . . ? C19 C18 C25 126.5(6) . . ? C17 C18 C25 125.1(6) . . ? C19 C18 Ir1 72.7(3) . . ? C17 C18 Ir1 68.4(3) . . ? C25 C18 Ir1 126.9(4) . . ? C13 C15 C16 120.4(6) . . ? C13 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C20 C21 C17 108.4(5) . . ? C20 C21 C22 127.0(6) . . ? C17 C21 C22 124.6(6) . . ? C20 C21 Ir1 72.3(3) . . ? C17 C21 Ir1 67.8(3) . . ? C22 C21 Ir1 126.3(4) . . ? C13 C12 C11 118.9(6) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? O1 C5 C4 125.6(6) . . ? O1 C5 C7 114.2(5) . . ? C4 C5 C7 120.2(6) . . ? C21 C20 C19 107.8(5) . . ? C21 C20 C23 126.7(6) . . ? C19 C20 C23 125.1(5) . . ? C21 C20 Ir1 71.1(3) . . ? C19 C20 Ir1 71.0(3) . . ? C23 C20 Ir1 129.1(4) . . ? O1 C6 H6A 109.5 . . ? O1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 C3 Ir1 N1 C1 2.3(4) . . . . ? C17 Ir1 N1 C1 129.8(12) . . . . ? C18 Ir1 N1 C1 93.8(5) . . . . ? C21 Ir1 N1 C1 -169.9(4) . . . . ? C19 Ir1 N1 C1 123.5(4) . . . . ? C20 Ir1 N1 C1 162.9(4) . . . . ? C3 Ir1 N1 C10 -173.0(4) . . . . ? C17 Ir1 N1 C10 -45.5(14) . . . . ? C18 Ir1 N1 C10 -81.4(5) . . . . ? C21 Ir1 N1 C10 14.8(6) . . . . ? C19 Ir1 N1 C10 -51.8(4) . . . . ? C20 Ir1 N1 C10 -12.4(5) . . . . ? N1 Ir1 C3 C4 -179.0(5) . . . . ? C17 Ir1 C3 C4 9.4(6) . . . . ? C18 Ir1 C3 C4 48.0(5) . . . . ? C21 Ir1 C3 C4 -7.9(7) . . . . ? C19 Ir1 C3 C4 79.0(6) . . . . ? C20 Ir1 C3 C4 70.4(9) . . . . ? N1 Ir1 C3 C2 -2.2(4) . . . . ? C17 Ir1 C3 C2 -173.9(4) . . . . ? C18 Ir1 C3 C2 -135.2(4) . . . . ? C21 Ir1 C3 C2 168.8(4) . . . . ? C19 Ir1 C3 C2 -104.3(4) . . . . ? C20 Ir1 C3 C2 -112.8(7) . . . . ? C14 O2 C13 C12 12.8(9) . . . . ? C14 O2 C13 C15 -166.8(6) . . . . ? N1 Ir1 C17 C21 71.2(13) . . . . ? C3 Ir1 C17 C21 -163.6(3) . . . . ? C18 Ir1 C17 C21 114.1(5) . . . . ? C19 Ir1 C17 C21 77.9(4) . . . . ? C20 Ir1 C17 C21 35.7(3) . . . . ? N1 Ir1 C17 C18 -43.0(14) . . . . ? C3 Ir1 C17 C18 82.3(4) . . . . ? C21 Ir1 C17 C18 -114.1(5) . . . . ? C19 Ir1 C17 C18 -36.2(3) . . . . ? C20 Ir1 C17 C18 -78.4(4) . . . . ? N1 Ir1 C17 C26 -165.8(10) . . . . ? C3 Ir1 C17 C26 -40.5(6) . . . . ? C18 Ir1 C17 C26 -122.8(7) . . . . ? C21 Ir1 C17 C26 123.0(7) . . . . ? C19 Ir1 C17 C26 -159.1(6) . . . . ? C20 Ir1 C17 C26 158.7(6) . . . . ? C4 C3 C2 C8 -4.0(8) . . . . ? Ir1 C3 C2 C8 179.0(4) . . . . ? C4 C3 C2 C1 179.1(5) . . . . ? Ir1 C3 C2 C1 2.1(6) . . . . ? C7 C8 C2 C3 1.7(8) . . . . ? C7 C8 C2 C1 178.4(6) . . . . ? N1 Ir1 C19 C18 -143.5(3) . . . . ? C3 Ir1 C19 C18 -57.6(4) . . . . ? C17 Ir1 C19 C18 37.7(3) . . . . ? C21 Ir1 C19 C18 80.8(4) . . . . ? C20 Ir1 C19 C18 117.7(5) . . . . ? N1 Ir1 C19 C20 98.8(3) . . . . ? C3 Ir1 C19 C20 -175.3(3) . . . . ? C17 Ir1 C19 C20 -80.0(4) . . . . ? C18 Ir1 C19 C20 -117.7(5) . . . . ? C21 Ir1 C19 C20 -36.9(3) . . . . ? N1 Ir1 C19 C24 -19.9(6) . . . . ? C3 Ir1 C19 C24 66.0(6) . . . . ? C17 Ir1 C19 C24 161.3(6) . . . . ? C18 Ir1 C19 C24 123.6(7) . . . . ? C21 Ir1 C19 C24 -155.5(6) . . . . ? C20 Ir1 C19 C24 -118.7(7) . . . . ? C12 C11 C10 C16 -2.6(9) . . . . ? C12 C11 C10 N1 -178.4(5) . . . . ? C1 N1 C10 C11 -67.6(8) . . . . ? Ir1 N1 C10 C11 107.7(6) . . . . ? C1 N1 C10 C16 116.5(6) . . . . ? Ir1 N1 C10 C16 -68.1(6) . . . . ? C10 N1 C1 C2 173.6(5) . . . . ? Ir1 N1 C1 C2 -1.8(7) . . . . ? C10 N1 C1 C9 -10.5(9) . . . . ? Ir1 N1 C1 C9 174.1(5) . . . . ? C3 C2 C1 N1 -0.3(7) . . . . ? C8 C2 C1 N1 -177.1(5) . . . . ? C3 C2 C1 C9 -176.3(5) . . . . ? C8 C2 C1 C9 6.9(9) . . . . ? C11 C10 C16 C15 1.4(9) . . . . ? N1 C10 C16 C15 177.3(5) . . . . ? C2 C8 C7 C5 -0.6(9) . . . . ? C2 C3 C4 C5 5.2(8) . . . . ? Ir1 C3 C4 C5 -178.2(4) . . . . ? C20 C19 C18 C17 2.5(7) . . . . ? C24 C19 C18 C17 178.2(6) . . . . ? Ir1 C19 C18 C17 -59.4(4) . . . . ? C20 C19 C18 C25 -174.5(6) . . . . ? C24 C19 C18 C25 1.1(10) . . . . ? Ir1 C19 C18 C25 123.5(6) . . . . ? C20 C19 C18 Ir1 62.0(4) . . . . ? C24 C19 C18 Ir1 -122.4(6) . . . . ? C21 C17 C18 C19 -4.7(6) . . . . ? C26 C17 C18 C19 -174.0(6) . . . . ? Ir1 C17 C18 C19 62.1(4) . . . . ? C21 C17 C18 C25 172.5(5) . . . . ? C26 C17 C18 C25 3.1(10) . . . . ? Ir1 C17 C18 C25 -120.8(6) . . . . ? C21 C17 C18 Ir1 -66.8(4) . . . . ? C26 C17 C18 Ir1 123.9(6) . . . . ? N1 Ir1 C18 C19 52.1(4) . . . . ? C3 Ir1 C18 C19 134.2(4) . . . . ? C17 Ir1 C18 C19 -118.4(5) . . . . ? C21 Ir1 C18 C19 -79.0(4) . . . . ? C20 Ir1 C18 C19 -37.5(3) . . . . ? N1 Ir1 C18 C17 170.5(3) . . . . ? C3 Ir1 C18 C17 -107.4(4) . . . . ? C21 Ir1 C18 C17 39.4(3) . . . . ? C19 Ir1 C18 C17 118.4(5) . . . . ? C20 Ir1 C18 C17 80.9(4) . . . . ? N1 Ir1 C18 C25 -71.0(6) . . . . ? C3 Ir1 C18 C25 11.1(6) . . . . ? C17 Ir1 C18 C25 118.5(7) . . . . ? C21 Ir1 C18 C25 157.9(6) . . . . ? C19 Ir1 C18 C25 -123.1(7) . . . . ? C20 Ir1 C18 C25 -160.6(6) . . . . ? C12 C13 C15 C16 -0.8(10) . . . . ? O2 C13 C15 C16 178.8(6) . . . . ? C10 C16 C15 C13 0.3(9) . . . . ? C18 C17 C21 C20 5.0(6) . . . . ? C26 C17 C21 C20 174.5(6) . . . . ? Ir1 C17 C21 C20 -61.1(4) . . . . ? C18 C17 C21 C22 -174.2(5) . . . . ? C26 C17 C21 C22 -4.8(9) . . . . ? Ir1 C17 C21 C22 119.6(5) . . . . ? C18 C17 C21 Ir1 66.2(4) . . . . ? C26 C17 C21 Ir1 -124.4(6) . . . . ? N1 Ir1 C21 C20 -46.5(5) . . . . ? C3 Ir1 C21 C20 146.5(4) . . . . ? C17 Ir1 C21 C20 119.3(5) . . . . ? C18 Ir1 C21 C20 79.6(4) . . . . ? C19 Ir1 C21 C20 37.8(3) . . . . ? N1 Ir1 C21 C17 -165.8(3) . . . . ? C3 Ir1 C21 C17 27.2(5) . . . . ? C18 Ir1 C21 C17 -39.7(3) . . . . ? C19 Ir1 C21 C17 -81.5(4) . . . . ? C20 Ir1 C21 C17 -119.3(5) . . . . ? N1 Ir1 C21 C22 76.7(6) . . . . ? C3 Ir1 C21 C22 -90.3(6) . . . . ? C17 Ir1 C21 C22 -117.5(7) . . . . ? C18 Ir1 C21 C22 -157.1(6) . . . . ? C19 Ir1 C21 C22 161.0(6) . . . . ? C20 Ir1 C21 C22 123.2(7) . . . . ? C15 C13 C12 C11 -0.4(10) . . . . ? O2 C13 C12 C11 -179.9(6) . . . . ? C10 C11 C12 C13 2.1(9) . . . . ? C6 O1 C5 C4 -6.3(8) . . . . ? C6 O1 C5 C7 174.8(5) . . . . ? C3 C4 C5 O1 177.0(5) . . . . ? C3 C4 C5 C7 -4.2(9) . . . . ? C8 C7 C5 O1 -179.2(5) . . . . ? C8 C7 C5 C4 1.9(9) . . . . ? C17 C21 C20 C19 -3.5(6) . . . . ? C22 C21 C20 C19 175.7(5) . . . . ? Ir1 C21 C20 C19 -61.8(4) . . . . ? C17 C21 C20 C23 -176.5(6) . . . . ? C22 C21 C20 C23 2.7(9) . . . . ? Ir1 C21 C20 C23 125.2(6) . . . . ? C17 C21 C20 Ir1 58.4(4) . . . . ? C22 C21 C20 Ir1 -122.4(5) . . . . ? C18 C19 C20 C21 0.6(6) . . . . ? C24 C19 C20 C21 -175.3(5) . . . . ? Ir1 C19 C20 C21 61.9(4) . . . . ? C18 C19 C20 C23 173.7(6) . . . . ? C24 C19 C20 C23 -2.2(9) . . . . ? Ir1 C19 C20 C23 -125.0(6) . . . . ? C18 C19 C20 Ir1 -61.3(4) . . . . ? C24 C19 C20 Ir1 122.8(6) . . . . ? N1 Ir1 C20 C21 149.0(3) . . . . ? C3 Ir1 C20 C21 -105.6(7) . . . . ? C17 Ir1 C20 C21 -37.1(3) . . . . ? C18 Ir1 C20 C21 -80.5(4) . . . . ? C19 Ir1 C20 C21 -117.4(5) . . . . ? N1 Ir1 C20 C19 -93.6(3) . . . . ? C3 Ir1 C20 C19 11.8(8) . . . . ? C17 Ir1 C20 C19 80.3(4) . . . . ? C18 Ir1 C20 C19 36.9(3) . . . . ? C21 Ir1 C20 C19 117.4(5) . . . . ? N1 Ir1 C20 C23 26.7(6) . . . . ? C3 Ir1 C20 C23 132.1(7) . . . . ? C17 Ir1 C20 C23 -159.4(6) . . . . ? C18 Ir1 C20 C23 157.2(6) . . . . ? C21 Ir1 C20 C23 -122.3(7) . . . . ? C19 Ir1 C20 C23 120.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 2.217 _refine_diff_density_min -4.010 _refine_diff_density_rms 0.175