# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Rupasree Das' _publ_contact_author_email RD.RUPASREE@SAMSUNG.COM _publ_section_title ; Syntheses, Crystal Structure, Electrochemical, Photophysical, Electroluminescence and Density Functional Theory Calculations of a Set of bis-Cyclometalated Ir(III) Complexes with a Common Ancillary Ligand ; loop_ _publ_author_name 'Rupasree Das' 'Younghun Byun.' 'Seok Chang.' 'Eunsil Han' 'Woo Sung Jeon.' ; Heekyung Kim ; 'Myeongsuk Kim.' 'Ohyun Kwon.' 'Tae-Woo Lee.' 'Yi-Yeol Lyu.' # Attachment 'Refined-FCZN-o4_78mo.cif' data_o4_78mo _database_code_depnum_ccdc_archive 'CCDC 670853' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H18 F4 Ir N7 O' _chemical_formula_sum 'C30 H18 F4 Ir N7 O' _chemical_formula_weight 760.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 21.982(11) _cell_length_b 30.270(15) _cell_length_c 14.317(7) _cell_angle_alpha 90.00 _cell_angle_beta 127.848(7) _cell_angle_gamma 90.00 _cell_volume 7523(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5666 _cell_measurement_theta_min 2.249 _cell_measurement_theta_max 28.068 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 3.598 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4666 _exptl_absorpt_correction_T_max 0.8997 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2.0 _diffrn_reflns_number 17507 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.1269 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6487 _reflns_number_gt 4176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics ORTEP3 _computing_publication_material WinGX _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^)+(0.1232P)^2^+94.3432P] 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 6487 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2401 _refine_ls_wR_factor_gt 0.2241 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.73949(3) 0.41774(2) 0.83120(5) 0.0266(2) Uani 1 1 d . . . F1 F 0.8291(7) 0.2801(4) 1.1134(10) 0.065(3) Uani 1 1 d . . . F2 F 0.8095(9) 0.2543(4) 0.7738(12) 0.084(4) Uani 1 1 d . . . F3 F 0.9612(5) 0.4448(4) 0.7979(8) 0.045(3) Uani 1 1 d . . . F4 F 1.0428(5) 0.4417(4) 1.1827(7) 0.050(3) Uani 1 1 d . . . O1 O 0.6069(6) 0.5329(4) 0.7196(11) 0.044(3) Uani 1 1 d . . . N1 N 0.6167(7) 0.4159(5) 0.7337(11) 0.032(3) Uani 1 1 d . . . N2 N 0.5849(6) 0.4583(5) 0.7031(11) 0.030(3) Uani 1 1 d . . . N3 N 0.7086(7) 0.4838(5) 0.8055(11) 0.031(3) Uani 1 1 d . . . H3 H 0.7437 0.5038 0.8361 0.037 Uiso 1 1 calc R . . N4 N 0.7533(7) 0.4102(4) 0.9855(11) 0.028(3) Uani 1 1 d . . . N5 N 0.8763(9) 0.1894(6) 1.0238(18) 0.073(6) Uani 1 1 d . . . N6 N 0.7339(7) 0.4214(5) 0.6824(11) 0.031(3) Uani 1 1 d . . . N7 N 1.1416(8) 0.4549(5) 1.0635(13) 0.046(4) Uani 1 1 d . . . C1 C 0.5067(8) 0.4551(6) 0.6313(14) 0.031(4) Uani 1 1 d . . . C2 C 0.4889(9) 0.4118(6) 0.6162(15) 0.042(5) Uani 1 1 d . . . H2 H 0.4397 0.3996 0.5709 0.050 Uiso 1 1 calc R . . C3 C 0.5586(9) 0.3888(5) 0.6816(15) 0.031(4) Uani 1 1 d . . . C4 C 0.4552(9) 0.4949(7) 0.5809(16) 0.047(5) Uani 1 1 d . . . H4A H 0.4042 0.4862 0.5149 0.070 Uiso 1 1 calc R . . H4B H 0.4748 0.5160 0.5552 0.070 Uiso 1 1 calc R . . H4C H 0.4537 0.5081 0.6405 0.070 Uiso 1 1 calc R . . C5 C 0.5719(10) 0.3412(7) 0.6933(18) 0.055(5) Uani 1 1 d . . . H5A H 0.6157 0.3347 0.6960 0.083 Uiso 1 1 calc R . . H5B H 0.5272 0.3265 0.6268 0.083 Uiso 1 1 calc R . . H5C H 0.5815 0.3311 0.7649 0.083 Uiso 1 1 calc R . . C6 C 0.6357(9) 0.4954(6) 0.7428(13) 0.029(4) Uani 1 1 d . . . C7 C 0.7418(8) 0.4443(6) 1.0363(14) 0.035(4) Uani 1 1 d . . . H7 H 0.7276 0.4719 1.0002 0.042 Uiso 1 1 calc R . . C8 C 0.7507(11) 0.4387(10) 1.1387(16) 0.065(7) Uani 1 1 d . . . H8 H 0.7436 0.4625 1.1722 0.078 Uiso 1 1 calc R . . C9 C 0.7692(9) 0.4002(7) 1.1895(16) 0.037(4) Uani 1 1 d . . . H9 H 0.7732 0.3963 1.2575 0.045 Uiso 1 1 calc R . . C10 C 0.7827(9) 0.3656(6) 1.1444(15) 0.040(4) Uani 1 1 d . . . H10 H 0.7970 0.3383 1.1823 0.048 Uiso 1 1 calc R . . C11 C 0.7748(9) 0.3712(6) 1.0360(14) 0.039(4) Uani 1 1 d . . . C12 C 0.7826(8) 0.3396(6) 0.9705(15) 0.036(4) Uani 1 1 d . . . C13 C 0.8097(10) 0.2953(7) 1.0085(16) 0.051(5) Uani 1 1 d . . . C14 C 0.8214(10) 0.2678(6) 0.9464(17) 0.042(5) Uani 1 1 d . . . C15 C 0.8010(11) 0.2829(7) 0.8393(18) 0.051(5) Uani 1 1 d . . . C16 C 0.7761(9) 0.3250(6) 0.7989(16) 0.040(4) Uani 1 1 d . . . H16 H 0.7645 0.3338 0.7274 0.048 Uiso 1 1 calc R . . C17 C 0.7681(8) 0.3545(5) 0.8649(14) 0.029(4) Uani 1 1 d . . . C18 C 0.8512(11) 0.2245(8) 0.990(2) 0.057(6) Uani 1 1 d . . . C19 C 0.6702(9) 0.4150(6) 0.5753(14) 0.037(4) Uani 1 1 d . . . H19 H 0.6250 0.4094 0.5655 0.044 Uiso 1 1 calc R . . C20 C 0.6675(9) 0.4164(6) 0.4774(15) 0.038(4) Uani 1 1 d . . . H20 H 0.6212 0.4124 0.4021 0.046 Uiso 1 1 calc R . . C21 C 0.7373(9) 0.4239(6) 0.4942(15) 0.038(5) Uani 1 1 d . . . H21 H 0.7380 0.4244 0.4299 0.046 Uiso 1 1 calc R . . C22 C 0.8004(10) 0.4302(6) 0.6012(15) 0.038(4) Uani 1 1 d . . . H22 H 0.8458 0.4362 0.6119 0.046 Uiso 1 1 calc R . . C23 C 0.8024(9) 0.4281(5) 0.7019(13) 0.026(4) Uani 1 1 d . . . C24 C 0.8673(9) 0.4326(5) 0.8261(14) 0.028(4) Uani 1 1 d . . . C25 C 0.9406(9) 0.4385(6) 0.8698(14) 0.030(4) Uani 1 1 d . . . C26 C 1.0038(8) 0.4441(5) 0.9940(13) 0.029(4) Uani 1 1 d . . . C27 C 0.9846(9) 0.4384(6) 1.0682(13) 0.033(4) Uani 1 1 d . . . C28 C 0.9110(8) 0.4305(5) 1.0287(13) 0.027(4) Uani 1 1 d . . . H28 H 0.9013 0.4270 1.0830 0.032 Uiso 1 1 calc R . . C29 C 0.8502(8) 0.4277(5) 0.9077(13) 0.022(3) Uani 1 1 d . . . C30 C 1.0802(9) 0.4509(6) 1.0315(14) 0.034(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0180(3) 0.0356(4) 0.0239(3) 0.0004(3) 0.0117(3) 0.0005(3) F1 0.070(8) 0.066(8) 0.059(7) 0.023(6) 0.040(6) 0.002(7) F2 0.121(11) 0.055(8) 0.092(10) 0.001(8) 0.074(9) 0.018(8) F3 0.032(5) 0.068(8) 0.040(6) -0.001(5) 0.025(5) -0.010(5) F4 0.020(5) 0.099(9) 0.019(5) 0.001(5) 0.005(4) 0.000(5) O1 0.033(6) 0.028(7) 0.051(8) 0.003(6) 0.017(6) 0.000(6) N1 0.031(7) 0.034(8) 0.038(7) 0.000(7) 0.025(6) -0.001(7) N2 0.010(6) 0.043(9) 0.030(7) -0.001(7) 0.009(5) -0.003(6) N3 0.020(6) 0.041(9) 0.037(7) -0.001(7) 0.019(6) 0.002(6) N4 0.023(6) 0.029(9) 0.037(7) 0.014(7) 0.021(6) 0.007(6) N5 0.036(9) 0.052(13) 0.087(14) 0.006(11) 0.015(9) 0.012(9) N6 0.023(6) 0.042(9) 0.023(6) 0.001(7) 0.011(6) 0.015(7) N7 0.026(8) 0.060(12) 0.048(9) -0.018(8) 0.020(7) -0.014(7) C1 0.014(7) 0.037(11) 0.031(8) 0.007(8) 0.009(7) 0.005(7) C2 0.023(8) 0.052(14) 0.046(10) 0.011(9) 0.019(8) -0.015(9) C3 0.023(8) 0.026(10) 0.045(10) -0.014(8) 0.022(8) -0.011(7) C4 0.025(9) 0.060(14) 0.047(11) 0.010(10) 0.018(8) 0.008(9) C5 0.036(10) 0.063(15) 0.058(12) 0.004(11) 0.025(10) -0.011(10) C6 0.034(9) 0.027(10) 0.024(8) -0.012(7) 0.017(7) -0.007(8) C7 0.026(8) 0.038(11) 0.042(10) 0.008(8) 0.021(8) 0.007(8) C8 0.040(11) 0.13(2) 0.033(11) -0.015(13) 0.028(10) -0.005(13) C9 0.023(9) 0.056(12) 0.037(10) 0.000(9) 0.020(8) 0.004(8) C10 0.034(9) 0.041(12) 0.039(10) 0.008(9) 0.020(8) 0.000(9) C11 0.028(8) 0.052(13) 0.028(9) 0.007(9) 0.012(7) 0.007(8) C12 0.010(7) 0.056(13) 0.043(10) 0.003(9) 0.017(7) 0.002(8) C13 0.029(9) 0.073(16) 0.033(10) 0.011(10) 0.009(8) 0.007(10) C14 0.041(10) 0.035(12) 0.059(12) 0.006(10) 0.035(10) 0.001(9) C15 0.045(11) 0.050(14) 0.058(13) -0.023(11) 0.032(10) -0.012(10) C16 0.037(9) 0.019(10) 0.048(10) 0.001(8) 0.019(8) -0.005(8) C17 0.023(8) 0.028(10) 0.030(8) 0.003(7) 0.013(7) 0.011(7) C18 0.031(10) 0.054(15) 0.076(15) -0.003(13) 0.027(11) -0.007(11) C19 0.025(8) 0.037(11) 0.032(9) -0.008(9) 0.009(7) -0.005(8) C20 0.026(8) 0.045(11) 0.033(9) 0.007(9) 0.012(7) 0.013(9) C21 0.037(9) 0.058(13) 0.039(9) -0.005(9) 0.033(8) 0.018(9) C22 0.034(9) 0.041(12) 0.044(10) 0.016(8) 0.026(9) 0.015(8) C23 0.036(9) 0.025(10) 0.023(8) 0.006(7) 0.021(7) 0.009(7) C24 0.034(9) 0.019(9) 0.030(8) 0.007(7) 0.020(7) 0.015(7) C25 0.035(9) 0.032(10) 0.032(8) 0.003(8) 0.026(8) 0.008(8) C26 0.016(7) 0.028(10) 0.026(8) 0.005(7) 0.004(6) -0.001(7) C27 0.028(8) 0.037(10) 0.025(8) 0.010(8) 0.013(7) 0.008(8) C28 0.022(8) 0.032(10) 0.026(8) 0.007(7) 0.015(7) 0.011(7) C29 0.025(8) 0.019(9) 0.034(8) 0.015(7) 0.024(7) 0.014(6) C30 0.032(9) 0.027(10) 0.037(9) 0.004(8) 0.018(8) -0.003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C17 1.979(16) . ? Ir1 C29 1.986(14) . ? Ir1 N4 2.050(13) . ? Ir1 N6 2.060(13) . ? Ir1 N3 2.071(14) . ? Ir1 N1 2.148(12) . ? F1 C13 1.36(2) . ? F2 C15 1.37(2) . ? F3 C25 1.369(16) . ? F4 C27 1.327(17) . ? O1 C6 1.242(19) . ? N1 C3 1.300(19) . ? N1 N2 1.397(18) . ? N2 C1 1.361(17) . ? N2 C6 1.43(2) . ? N3 C6 1.316(19) . ? N4 C11 1.31(2) . ? N4 C7 1.37(2) . ? N5 C18 1.16(3) . ? N6 C19 1.310(19) . ? N6 C23 1.37(2) . ? N7 C30 1.135(19) . ? C1 C2 1.35(2) . ? C1 C4 1.50(2) . ? C2 C3 1.40(2) . ? C3 C5 1.46(3) . ? C7 C8 1.37(2) . ? C8 C9 1.30(3) . ? C9 C10 1.36(2) . ? C10 C11 1.46(2) . ? C11 C12 1.42(2) . ? C12 C17 1.42(2) . ? C12 C13 1.43(3) . ? C13 C14 1.35(3) . ? C14 C15 1.38(3) . ? C14 C18 1.43(3) . ? C15 C16 1.37(3) . ? C16 C17 1.39(2) . ? C19 C20 1.37(2) . ? C20 C21 1.42(2) . ? C21 C22 1.30(2) . ? C22 C23 1.42(2) . ? C23 C24 1.45(2) . ? C24 C25 1.34(2) . ? C24 C29 1.44(2) . ? C25 C26 1.45(2) . ? C26 C27 1.37(2) . ? C26 C30 1.43(2) . ? C27 C28 1.37(2) . ? C28 C29 1.40(2) . ? 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 C17 Ir1 C29 85.0(6) . . ? C17 Ir1 N4 79.3(6) . . ? C29 Ir1 N4 95.8(5) . . ? C17 Ir1 N6 96.4(6) . . ? C29 Ir1 N6 80.6(5) . . ? N4 Ir1 N6 174.8(5) . . ? C17 Ir1 N3 175.9(6) . . ? C29 Ir1 N3 96.2(5) . . ? N4 Ir1 N3 96.6(5) . . ? N6 Ir1 N3 87.7(5) . . ? C17 Ir1 N1 102.6(6) . . ? C29 Ir1 N1 171.4(5) . . ? N4 Ir1 N1 89.6(5) . . ? N6 Ir1 N1 94.3(5) . . ? N3 Ir1 N1 76.5(5) . . ? C3 N1 N2 105.8(12) . . ? C3 N1 Ir1 142.2(12) . . ? N2 N1 Ir1 111.5(9) . . ? C1 N2 N1 109.3(13) . . ? C1 N2 C6 132.0(15) . . ? N1 N2 C6 118.5(12) . . ? C6 N3 Ir1 120.5(11) . . ? C11 N4 C7 120.4(14) . . ? C11 N4 Ir1 117.4(11) . . ? C7 N4 Ir1 122.2(11) . . ? C19 N6 C23 120.9(14) . . ? C19 N6 Ir1 123.0(12) . . ? C23 N6 Ir1 115.9(10) . . ? C2 C1 N2 107.2(14) . . ? C2 C1 C4 130.2(15) . . ? N2 C1 C4 122.6(15) . . ? C1 C2 C3 106.7(14) . . ? N1 C3 C2 111.0(15) . . ? N1 C3 C5 120.0(15) . . ? C2 C3 C5 129.0(15) . . ? O1 C6 N3 129.4(15) . . ? O1 C6 N2 117.7(14) . . ? N3 C6 N2 112.8(14) . . ? C8 C7 N4 121.6(19) . . ? C9 C8 C7 120(2) . . ? C8 C9 C10 120.7(18) . . ? C9 C10 C11 119.8(17) . . ? N4 C11 C12 113.0(15) . . ? N4 C11 C10 117.4(16) . . ? C12 C11 C10 129.5(17) . . ? C17 C12 C11 116.7(16) . . ? C17 C12 C13 118.3(16) . . ? C11 C12 C13 124.7(16) . . ? C14 C13 F1 117.4(18) . . ? C14 C13 C12 121.8(17) . . ? F1 C13 C12 120.7(18) . . ? C13 C14 C15 117.6(18) . . ? C13 C14 C18 120.0(19) . . ? C15 C14 C18 122.3(19) . . ? C16 C15 F2 119.1(19) . . ? C16 C15 C14 123.2(18) . . ? F2 C15 C14 117.6(19) . . ? C15 C16 C17 119.9(18) . . ? C16 C17 C12 118.8(16) . . ? C16 C17 Ir1 127.7(13) . . ? C12 C17 Ir1 113.5(12) . . ? N5 C18 C14 178(2) . . ? N6 C19 C20 122.6(16) . . ? C19 C20 C21 118.0(15) . . ? C22 C21 C20 118.8(15) . . ? C21 C22 C23 122.4(16) . . ? N6 C23 C22 117.1(14) . . ? N6 C23 C24 113.3(13) . . ? C22 C23 C24 129.6(15) . . ? C25 C24 C29 118.3(14) . . ? C25 C24 C23 125.7(14) . . ? C29 C24 C23 115.9(14) . . ? C24 C25 F3 121.9(14) . . ? C24 C25 C26 124.4(14) . . ? F3 C25 C26 113.3(13) . . ? C27 C26 C30 125.1(14) . . ? C27 C26 C25 114.6(13) . . ? C30 C26 C25 120.1(14) . . ? F4 C27 C28 121.6(14) . . ? F4 C27 C26 115.1(14) . . ? C28 C27 C26 123.3(14) . . ? C27 C28 C29 120.8(14) . . ? C28 C29 C24 118.3(13) . . ? C28 C29 Ir1 127.5(10) . . ? C24 C29 Ir1 114.2(11) . . ? N7 C30 C26 177.5(19) . . ? 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 N3 H3 N7 0.86 2.35 3.198(19) 167.3 5_767 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 2.223 _refine_diff_density_min -3.387 _refine_diff_density_rms 0.283 # Attachment 'FZN-CIF.cif' data_o4_77mo _database_code_depnum_ccdc_archive 'CCDC 670854' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 F4 Ir N5 O' _chemical_formula_weight 710.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.572(2) _cell_length_b 9.523(2) _cell_length_c 22.409(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.012(4) _cell_angle_gamma 90.00 _cell_volume 2455.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5004 _cell_measurement_theta_min 2.326 _cell_measurement_theta_max 28.251 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 5.500 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2290 _exptl_absorpt_correction_T_max 0.4925 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2.0 _diffrn_reflns_number 14916 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5851 _reflns_number_gt 5131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics ORTEP3 _computing_publication_material WinGX _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^)+(0.0209P)^2^+2.2776P] 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 5851 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0517 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.280150(9) 0.762096(10) 0.574649(5) 0.01943(4) Uani 1 1 d . . . F1 F -0.0033(2) 0.3658(2) 0.65520(10) 0.0534(6) Uani 1 1 d . . . F2 F 0.00600(18) 0.8044(2) 0.74811(8) 0.0376(5) Uani 1 1 d . . . F3 F 0.6428(2) 0.7603(2) 0.74753(10) 0.0521(6) Uani 1 1 d . . . F4 F 0.58256(19) 0.3574(2) 0.62878(9) 0.0446(5) Uani 1 1 d . . . O1 O 0.39126(19) 1.0002(2) 0.43254(9) 0.0282(5) Uani 1 1 d . . . N1 N 0.1630(2) 0.8445(2) 0.50278(10) 0.0218(5) Uani 1 1 d . . . N2 N 0.2203(2) 0.9085(2) 0.45909(10) 0.0213(5) Uani 1 1 d . . . N3 N 0.3871(2) 0.8737(2) 0.52081(11) 0.0231(5) Uani 1 1 d . . . H3 H 0.4601 0.8816 0.5322 0.028 Uiso 1 1 calc R . . N4 N 0.2517(2) 0.9299(2) 0.62836(10) 0.0220(5) Uani 1 1 d . . . N5 N 0.3062(2) 0.5808(2) 0.52951(11) 0.0234(5) Uani 1 1 d . . . C1 C 0.1452(3) 0.9399(3) 0.41010(13) 0.0275(6) Uani 1 1 d . . . C2 C 0.0383(3) 0.8954(3) 0.42268(14) 0.0309(7) Uani 1 1 d . . . H2 H -0.0308 0.9028 0.3976 0.037 Uiso 1 1 calc R . . C3 C 0.0515(3) 0.8363(3) 0.48027(13) 0.0249(6) Uani 1 1 d . . . C4 C 0.3444(3) 0.9310(3) 0.47032(12) 0.0214(6) Uani 1 1 d . . . C5 C 0.1798(3) 1.0092(4) 0.35466(15) 0.0418(9) Uani 1 1 d . . . H5A H 0.2418 0.9570 0.3399 0.063 Uiso 1 1 calc R . . H5B H 0.2054 1.1032 0.3640 0.063 Uiso 1 1 calc R . . H5C H 0.1143 1.0116 0.3246 0.063 Uiso 1 1 calc R . . C6 C -0.0381(3) 0.7675(3) 0.51329(17) 0.0343(7) Uani 1 1 d . . . H6A H -0.0226 0.7872 0.5554 0.052 Uiso 1 1 calc R . . H6B H -0.0361 0.6678 0.5070 0.052 Uiso 1 1 calc R . . H6C H -0.1136 0.8029 0.4988 0.052 Uiso 1 1 calc R . . C7 C 0.3024(3) 1.0568(3) 0.62373(13) 0.0282(7) Uani 1 1 d . . . H7 H 0.3530 1.0697 0.5946 0.034 Uiso 1 1 calc R . . C8 C 0.2817(3) 1.1675(3) 0.66056(15) 0.0324(7) Uani 1 1 d . . . H8 H 0.3160 1.2545 0.6556 0.039 Uiso 1 1 calc R . . C9 C 0.2085(3) 1.1473(3) 0.70531(14) 0.0327(7) Uani 1 1 d . . . H9 H 0.1938 1.2204 0.7310 0.039 Uiso 1 1 calc R . . C10 C 0.1581(3) 1.0175(3) 0.71112(13) 0.0282(7) Uani 1 1 d . . . H10 H 0.1103 1.0023 0.7414 0.034 Uiso 1 1 calc R . . C11 C 0.1785(3) 0.9086(3) 0.67171(12) 0.0232(6) Uani 1 1 d . . . C12 C 0.1278(3) 0.7672(3) 0.66976(13) 0.0223(6) Uani 1 1 d . . . C13 C 0.1671(3) 0.6746(3) 0.62638(12) 0.0224(6) Uani 1 1 d . . . C14 C 0.1224(3) 0.5378(3) 0.62329(14) 0.0293(7) Uani 1 1 d . . . H14 H 0.1480 0.4739 0.5962 0.035 Uiso 1 1 calc R . . C15 C 0.0409(3) 0.4980(3) 0.66021(15) 0.0339(7) Uani 1 1 d . . . C16 C -0.0005(3) 0.5851(4) 0.70230(14) 0.0335(7) Uani 1 1 d . . . H16 H -0.0558 0.5553 0.7268 0.040 Uiso 1 1 calc R . . C17 C 0.0449(3) 0.7189(3) 0.70599(13) 0.0275(6) Uani 1 1 d . . . C18 C 0.2465(3) 0.5452(3) 0.47682(13) 0.0267(6) Uani 1 1 d . . . H18 H 0.1916 0.6076 0.4589 0.032 Uiso 1 1 calc R . . C19 C 0.2640(3) 0.4192(3) 0.44850(15) 0.0305(7) Uani 1 1 d . . . H19 H 0.2216 0.3976 0.4121 0.037 Uiso 1 1 calc R . . C20 C 0.3452(3) 0.3257(3) 0.47483(16) 0.0355(8) Uani 1 1 d . . . H20 H 0.3581 0.2402 0.4566 0.043 Uiso 1 1 calc R . . C21 C 0.4069(3) 0.3617(3) 0.52892(15) 0.0323(7) Uani 1 1 d . . . H21 H 0.4614 0.2995 0.5473 0.039 Uiso 1 1 calc R . . C22 C 0.3879(3) 0.4909(3) 0.55615(13) 0.0254(6) Uani 1 1 d . . . C23 C 0.4498(3) 0.5480(3) 0.61085(13) 0.0256(6) Uani 1 1 d . . . C24 C 0.4143(3) 0.6832(3) 0.62811(13) 0.0240(6) Uani 1 1 d . . . C25 C 0.4798(3) 0.7525(3) 0.67524(13) 0.0292(7) Uani 1 1 d . . . H25 H 0.4579 0.8411 0.6874 0.035 Uiso 1 1 calc R . . C26 C 0.5771(3) 0.6876(4) 0.70330(14) 0.0343(7) Uani 1 1 d . . . C27 C 0.6117(3) 0.5548(4) 0.68929(15) 0.0374(8) Uani 1 1 d . . . H27 H 0.6762 0.5123 0.7101 0.045 Uiso 1 1 calc R . . C28 C 0.5472(3) 0.4883(3) 0.64351(14) 0.0315(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01876(6) 0.01958(6) 0.02005(6) 0.00042(4) 0.00250(4) -0.00086(4) F1 0.0646(16) 0.0320(11) 0.0689(15) -0.0048(10) 0.0315(13) -0.0200(10) F2 0.0433(12) 0.0417(11) 0.0306(10) -0.0039(8) 0.0165(9) 0.0027(9) F3 0.0401(13) 0.0748(17) 0.0374(12) -0.0044(10) -0.0139(10) 0.0074(11) F4 0.0453(13) 0.0425(12) 0.0470(12) 0.0104(9) 0.0100(10) 0.0214(10) O1 0.0307(13) 0.0319(11) 0.0220(11) 0.0026(8) 0.0026(9) -0.0093(9) N1 0.0200(13) 0.0225(12) 0.0230(12) -0.0015(9) 0.0026(10) -0.0030(9) N2 0.0199(13) 0.0245(12) 0.0194(12) -0.0008(9) 0.0010(10) -0.0021(9) N3 0.0180(13) 0.0259(12) 0.0251(13) 0.0027(10) 0.0005(10) 0.0004(10) N4 0.0225(13) 0.0220(12) 0.0208(12) -0.0013(9) -0.0011(10) -0.0005(9) N5 0.0244(14) 0.0218(12) 0.0254(12) 0.0000(9) 0.0098(10) -0.0015(10) C1 0.0305(18) 0.0299(15) 0.0203(14) -0.0023(11) -0.0048(12) 0.0030(13) C2 0.0267(18) 0.0336(17) 0.0300(16) -0.0038(13) -0.0081(13) -0.0004(13) C3 0.0185(15) 0.0245(14) 0.0311(16) -0.0071(12) 0.0004(12) -0.0010(11) C4 0.0213(15) 0.0196(13) 0.0234(14) -0.0036(10) 0.0026(11) -0.0006(11) C5 0.041(2) 0.058(2) 0.0239(17) 0.0087(15) -0.0077(15) -0.0036(17) C6 0.0226(16) 0.0370(18) 0.0432(19) -0.0022(14) 0.0027(14) -0.0056(13) C7 0.0294(18) 0.0294(15) 0.0249(15) 0.0001(12) -0.0009(13) -0.0059(13) C8 0.0362(19) 0.0242(15) 0.0352(17) -0.0047(13) -0.0032(14) -0.0041(13) C9 0.037(2) 0.0323(17) 0.0276(16) -0.0103(13) -0.0037(14) 0.0033(14) C10 0.0304(18) 0.0330(16) 0.0203(15) -0.0039(12) -0.0017(12) 0.0025(13) C11 0.0220(16) 0.0268(14) 0.0197(14) -0.0001(11) -0.0022(11) 0.0030(11) C12 0.0213(15) 0.0266(14) 0.0185(13) 0.0012(10) 0.0001(11) 0.0016(11) C13 0.0233(16) 0.0226(14) 0.0210(14) 0.0027(11) 0.0006(11) 0.0026(11) C14 0.0306(18) 0.0269(15) 0.0317(16) -0.0016(12) 0.0089(14) -0.0035(12) C15 0.037(2) 0.0263(16) 0.0392(18) 0.0033(13) 0.0095(15) -0.0066(13) C16 0.0300(18) 0.0400(18) 0.0318(17) 0.0073(14) 0.0102(14) -0.0034(14) C17 0.0287(17) 0.0331(16) 0.0213(14) 0.0000(12) 0.0056(12) 0.0045(13) C18 0.0268(17) 0.0270(15) 0.0271(16) -0.0012(12) 0.0061(13) -0.0024(12) C19 0.0292(18) 0.0307(16) 0.0337(17) -0.0080(13) 0.0126(14) -0.0079(13) C20 0.038(2) 0.0243(16) 0.047(2) -0.0076(14) 0.0201(16) -0.0038(13) C21 0.0303(18) 0.0262(15) 0.0428(19) 0.0036(13) 0.0158(15) 0.0025(13) C22 0.0250(16) 0.0234(14) 0.0297(16) 0.0056(11) 0.0118(13) 0.0003(11) C23 0.0248(16) 0.0280(15) 0.0254(15) 0.0079(11) 0.0092(12) 0.0024(12) C24 0.0230(16) 0.0277(15) 0.0218(14) 0.0066(11) 0.0050(12) -0.0011(12) C25 0.0257(17) 0.0356(17) 0.0257(16) 0.0038(11) -0.0003(13) 0.0030(12) C26 0.0308(19) 0.052(2) 0.0192(15) 0.0043(14) -0.0016(13) -0.0008(15) C27 0.0291(19) 0.056(2) 0.0278(17) 0.0157(15) 0.0046(14) 0.0138(16) C28 0.0322(18) 0.0347(17) 0.0296(17) 0.0116(13) 0.0123(14) 0.0106(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C24 2.005(3) . ? Ir1 C13 2.016(3) . ? Ir1 N5 2.039(2) . ? Ir1 N4 2.048(2) . ? Ir1 N3 2.104(2) . ? Ir1 N1 2.142(2) . ? F1 C15 1.359(4) . ? F2 C17 1.358(3) . ? F3 C26 1.372(4) . ? F4 C28 1.364(4) . ? O1 C4 1.241(3) . ? N1 C3 1.338(4) . ? N1 N2 1.380(3) . ? N2 C1 1.360(4) . ? N2 C4 1.447(4) . ? N3 C4 1.306(4) . ? N4 C7 1.352(4) . ? N4 C11 1.370(4) . ? N5 C18 1.347(4) . ? N5 C22 1.366(4) . ? C1 C2 1.365(5) . ? C1 C5 1.498(4) . ? C2 C3 1.401(4) . ? C3 C6 1.488(4) . ? C7 C8 1.376(4) . ? C8 C9 1.392(5) . ? C9 C10 1.379(5) . ? C10 C11 1.398(4) . ? C11 C12 1.468(4) . ? C12 C17 1.398(4) . ? C12 C13 1.422(4) . ? C13 C14 1.401(4) . ? C14 C15 1.371(4) . ? C15 C16 1.379(5) . ? C16 C17 1.377(4) . ? C18 C19 1.382(4) . ? C19 C20 1.381(5) . ? C20 C21 1.384(5) . ? C21 C22 1.401(4) . ? C22 C23 1.459(4) . ? C23 C28 1.398(4) . ? C23 C24 1.418(4) . ? C24 C25 1.399(4) . ? C25 C26 1.377(5) . ? C26 C27 1.374(5) . ? C27 C28 1.360(5) . ? 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 C24 Ir1 C13 90.56(11) . . ? C24 Ir1 N5 80.43(11) . . ? C13 Ir1 N5 94.24(10) . . ? C24 Ir1 N4 95.91(11) . . ? C13 Ir1 N4 80.25(11) . . ? N5 Ir1 N4 173.41(9) . . ? C24 Ir1 N3 93.84(11) . . ? C13 Ir1 N3 173.68(10) . . ? N5 Ir1 N3 90.96(9) . . ? N4 Ir1 N3 94.78(9) . . ? C24 Ir1 N1 167.36(10) . . ? C13 Ir1 N1 100.73(10) . . ? N5 Ir1 N1 92.99(9) . . ? N4 Ir1 N1 91.61(9) . . ? N3 Ir1 N1 75.38(9) . . ? C3 N1 N2 105.9(2) . . ? C3 N1 Ir1 140.5(2) . . ? N2 N1 Ir1 112.45(17) . . ? C1 N2 N1 110.8(2) . . ? C1 N2 C4 130.3(2) . . ? N1 N2 C4 118.9(2) . . ? C4 N3 Ir1 121.1(2) . . ? C7 N4 C11 119.5(2) . . ? C7 N4 Ir1 123.7(2) . . ? C11 N4 Ir1 116.81(19) . . ? C18 N5 C22 119.6(3) . . ? C18 N5 Ir1 124.0(2) . . ? C22 N5 Ir1 116.5(2) . . ? N2 C1 C2 106.4(3) . . ? N2 C1 C5 124.2(3) . . ? C2 C1 C5 129.4(3) . . ? C1 C2 C3 107.5(3) . . ? N1 C3 C2 109.4(3) . . ? N1 C3 C6 122.2(3) . . ? C2 C3 C6 128.3(3) . . ? O1 C4 N3 131.3(3) . . ? O1 C4 N2 117.2(3) . . ? N3 C4 N2 111.5(2) . . ? N4 C7 C8 122.4(3) . . ? C7 C8 C9 118.9(3) . . ? C10 C9 C8 119.2(3) . . ? C9 C10 C11 120.3(3) . . ? N4 C11 C10 119.8(3) . . ? N4 C11 C12 112.9(2) . . ? C10 C11 C12 127.3(3) . . ? C17 C12 C13 118.8(3) . . ? C17 C12 C11 125.5(3) . . ? C13 C12 C11 115.7(3) . . ? C14 C13 C12 117.9(3) . . ? C14 C13 Ir1 127.9(2) . . ? C12 C13 Ir1 114.2(2) . . ? C15 C14 C13 120.1(3) . . ? F1 C15 C14 118.8(3) . . ? F1 C15 C16 117.3(3) . . ? C14 C15 C16 123.8(3) . . ? C17 C16 C15 116.1(3) . . ? F2 C17 C16 116.4(3) . . ? F2 C17 C12 120.2(3) . . ? C16 C17 C12 123.4(3) . . ? N5 C18 C19 122.3(3) . . ? C20 C19 C18 119.3(3) . . ? C19 C20 C21 118.7(3) . . ? C20 C21 C22 120.6(3) . . ? N5 C22 C21 119.5(3) . . ? N5 C22 C23 113.0(3) . . ? C21 C22 C23 127.5(3) . . ? C28 C23 C24 117.9(3) . . ? C28 C23 C22 125.9(3) . . ? C24 C23 C22 115.9(3) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 Ir1 126.8(2) . . ? C23 C24 Ir1 113.9(2) . . ? C26 C25 C24 119.1(3) . . ? F3 C26 C27 118.5(3) . . ? F3 C26 C25 118.0(3) . . ? C27 C26 C25 123.6(3) . . ? C28 C27 C26 116.8(3) . . ? C27 C28 F4 116.9(3) . . ? C27 C28 C23 123.7(3) . . ? F4 C28 C23 119.4(3) . . ? 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 N3 H3 O1 0.86 2.14 2.925(3) 152.1 3_676 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.561 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.097 # Attachment 'MeOFZN-CIF.CIF' data_o5_01tr _database_code_depnum_ccdc_archive 'CCDC 670855' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 F4 Ir N5 O3' _chemical_formula_weight 770.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6643(10) _cell_length_b 11.5990(10) _cell_length_c 12.6823(11) _cell_angle_alpha 63.5710(10) _cell_angle_beta 89.299(2) _cell_angle_gamma 89.267(2) _cell_volume 1404.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7580 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.25 _exptl_crystal_description rhomboid _exptl_crystal_colour yellow _exptl_crystal_size_max 1.13 _exptl_crystal_size_mid 0.75 _exptl_crystal_size_min 0.70 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 4.821 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0737 _exptl_absorpt_correction_T_max 0.1333 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2.0 _diffrn_reflns_number 8479 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.25 _reflns_number_total 6208 _reflns_number_gt 5799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics ORTEP3 _computing_publication_material WinGX _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^)+(0.0609P)^2^+2.3876P] 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 6208 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.241780(16) 0.294318(16) 0.378928(15) 0.02359(8) Uani 1 1 d . . . F1 F 0.1208(4) 0.7619(4) 0.0549(4) 0.0590(11) Uani 1 1 d . . . F2 F 0.5306(4) 0.7249(4) 0.1938(4) 0.0552(10) Uani 1 1 d . . . F3 F 0.6110(3) 0.0877(4) 0.2378(4) 0.0524(10) Uani 1 1 d . . . F4 F 0.2550(4) 0.1935(5) 0.0030(4) 0.0606(11) Uani 1 1 d . . . O1 O 0.1108(4) -0.0269(4) 0.6775(4) 0.0411(9) Uani 1 1 d . . . O2 O 0.7756(3) 0.1167(4) 0.5677(4) 0.0355(8) Uani 1 1 d . . . O3 O -0.2190(4) 0.5067(4) 0.0629(4) 0.0454(10) Uani 1 1 d . . . N1 N 0.1707(4) 0.3064(4) 0.5341(4) 0.0268(8) Uani 1 1 d . . . N2 N 0.1492(4) 0.1866(4) 0.6242(4) 0.0283(8) Uani 1 1 d . . . N3 N 0.1744(4) 0.1081(4) 0.4886(4) 0.0278(9) Uani 1 1 d . . . H3 H 0.1670 0.0517 0.4603 0.033 Uiso 1 1 calc R . . N4 N 0.0779(4) 0.3598(4) 0.2891(4) 0.0257(8) Uani 1 1 d . . . N5 N 0.4156(4) 0.2356(4) 0.4505(4) 0.0253(8) Uani 1 1 d . . . C1 C 0.1662(5) 0.3874(5) 0.5823(5) 0.0346(11) Uani 1 1 d . . . C2 C 0.1455(6) 0.3182(6) 0.7036(6) 0.0419(13) Uani 1 1 d . . . H2 H 0.1400 0.3534 0.7584 0.050 Uiso 1 1 calc R . . C3 C 0.1346(5) 0.1910(6) 0.7294(5) 0.0357(12) Uani 1 1 d . . . C4 C 0.1839(7) 0.5290(6) 0.5108(7) 0.0511(16) Uani 1 1 d . . . H4A H 0.2721 0.5504 0.5134 0.077 Uiso 1 1 calc R . . H4B H 0.1311 0.5756 0.5430 0.077 Uiso 1 1 calc R . . H4C H 0.1602 0.5540 0.4290 0.077 Uiso 1 1 calc R . . C5 C 0.1143(7) 0.0772(7) 0.8439(5) 0.0511(17) Uani 1 1 d . . . H5A H 0.0338 0.0379 0.8430 0.077 Uiso 1 1 calc R . . H5B H 0.1137 0.1040 0.9071 0.077 Uiso 1 1 calc R . . H5C H 0.1821 0.0145 0.8573 0.077 Uiso 1 1 calc R . . C6 C 0.1436(5) 0.0759(5) 0.5979(5) 0.0297(10) Uani 1 1 d . . . C7 C -0.0210(5) 0.2863(5) 0.3011(5) 0.0320(11) Uani 1 1 d . . . H7 H -0.0203 0.2009 0.3626 0.038 Uiso 1 1 calc R . . C8 C -0.1249(5) 0.3271(5) 0.2291(5) 0.0323(11) Uani 1 1 d . . . H8 H -0.1932 0.2709 0.2403 0.039 Uiso 1 1 calc R . . C9 C -0.1266(5) 0.4525(5) 0.1399(5) 0.0320(11) Uani 1 1 d . . . C10 C -0.0236(5) 0.5303(5) 0.1273(5) 0.0318(11) Uani 1 1 d . . . H10 H -0.0229 0.6161 0.0664 0.038 Uiso 1 1 calc R . . C11 C 0.0772(5) 0.4851(5) 0.2016(4) 0.0282(10) Uani 1 1 d . . . C12 C 0.1931(5) 0.5537(5) 0.1982(4) 0.0293(10) Uani 1 1 d . . . C13 C 0.2133(6) 0.6837(6) 0.1278(6) 0.0401(13) Uani 1 1 d . . . C14 C 0.3253(6) 0.7451(6) 0.1242(6) 0.0431(14) Uani 1 1 d . . . H14 H 0.3364 0.8346 0.0757 0.052 Uiso 1 1 calc R . . C15 C 0.4193(6) 0.6681(6) 0.1954(6) 0.0390(13) Uani 1 1 d . . . C16 C 0.4043(5) 0.5379(5) 0.2706(5) 0.0332(11) Uani 1 1 d . . . H16 H 0.4718 0.4893 0.3187 0.040 Uiso 1 1 calc R . . C17 C 0.2898(5) 0.4791(5) 0.2752(5) 0.0291(10) Uani 1 1 d . . . C18 C -0.3296(6) 0.4323(8) 0.0762(7) 0.0521(17) Uani 1 1 d . . . H18A H -0.3059 0.3481 0.0812 0.078 Uiso 1 1 calc R . . H18B H -0.3843 0.4776 0.0083 0.078 Uiso 1 1 calc R . . H18C H -0.3743 0.4202 0.1484 0.078 Uiso 1 1 calc R . . C19 C 0.4553(5) 0.2403(5) 0.5487(5) 0.0313(11) Uani 1 1 d . . . H19 H 0.3989 0.2713 0.5891 0.038 Uiso 1 1 calc R . . C20 C 0.5744(5) 0.2021(6) 0.5937(5) 0.0315(11) Uani 1 1 d . . . H20 H 0.5997 0.2070 0.6631 0.038 Uiso 1 1 calc R . . C21 C 0.6561(5) 0.1564(5) 0.5345(5) 0.0281(10) Uani 1 1 d . . . C22 C 0.6147(5) 0.1487(5) 0.4336(5) 0.0292(10) Uani 1 1 d . . . H22 H 0.6692 0.1163 0.3931 0.035 Uiso 1 1 calc R . . C23 C 0.4952(5) 0.1881(5) 0.3929(4) 0.0254(9) Uani 1 1 d . . . C24 C 0.4382(5) 0.1884(5) 0.2879(4) 0.0278(10) Uani 1 1 d . . . C25 C 0.4930(5) 0.1392(6) 0.2162(5) 0.0346(11) Uani 1 1 d . . . C26 C 0.4342(6) 0.1409(6) 0.1192(5) 0.0418(14) Uani 1 1 d . . . H26 H 0.4739 0.1081 0.0706 0.050 Uiso 1 1 calc R . . C27 C 0.3160(6) 0.1923(6) 0.0967(5) 0.0392(13) Uani 1 1 d . . . C28 C 0.2546(6) 0.2421(5) 0.1632(5) 0.0333(11) Uani 1 1 d . . . H28 H 0.1724 0.2768 0.1429 0.040 Uiso 1 1 calc R . . C29 C 0.3148(5) 0.2412(5) 0.2621(4) 0.0281(10) Uani 1 1 d . . . C30 C 0.8179(5) 0.1089(6) 0.6774(5) 0.0374(12) Uani 1 1 d . . . H30A H 0.8184 0.1953 0.6734 0.056 Uiso 1 1 calc R . . H30B H 0.9029 0.0725 0.6931 0.056 Uiso 1 1 calc R . . H30C H 0.7614 0.0537 0.7409 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02121(11) 0.02357(11) 0.02813(11) -0.01334(8) 0.00133(7) -0.00480(7) F1 0.048(2) 0.040(2) 0.068(3) -0.0051(18) -0.0049(19) -0.0054(17) F2 0.044(2) 0.061(2) 0.066(2) -0.032(2) 0.0169(18) -0.0318(19) F3 0.0358(19) 0.078(3) 0.058(2) -0.043(2) -0.0011(16) 0.0033(19) F4 0.066(3) 0.089(3) 0.045(2) -0.045(2) -0.0090(19) -0.006(2) O1 0.054(3) 0.0303(19) 0.036(2) -0.0112(16) 0.0052(18) -0.0118(18) O2 0.0221(17) 0.046(2) 0.048(2) -0.0297(19) -0.0028(15) -0.0003(16) O3 0.029(2) 0.047(2) 0.045(2) -0.0075(19) -0.0081(17) -0.0038(18) N1 0.0226(19) 0.026(2) 0.036(2) -0.0166(17) 0.0023(16) -0.0059(16) N2 0.024(2) 0.030(2) 0.032(2) -0.0145(17) 0.0004(16) -0.0050(16) N3 0.034(2) 0.0191(18) 0.032(2) -0.0138(16) 0.0027(17) -0.0083(16) N4 0.0199(19) 0.025(2) 0.033(2) -0.0136(17) 0.0023(15) -0.0073(15) N5 0.0197(18) 0.030(2) 0.031(2) -0.0172(17) 0.0035(15) -0.0052(16) C1 0.027(3) 0.036(3) 0.052(3) -0.030(3) 0.004(2) -0.005(2) C2 0.043(3) 0.053(4) 0.044(3) -0.034(3) 0.010(2) -0.012(3) C3 0.033(3) 0.050(3) 0.032(3) -0.025(2) 0.003(2) -0.009(2) C4 0.055(4) 0.038(3) 0.070(4) -0.033(3) 0.017(3) -0.008(3) C5 0.058(4) 0.066(4) 0.028(3) -0.021(3) 0.002(3) -0.017(3) C6 0.027(2) 0.031(2) 0.032(2) -0.014(2) -0.0005(19) -0.005(2) C7 0.031(3) 0.027(2) 0.035(3) -0.011(2) 0.000(2) -0.011(2) C8 0.026(2) 0.033(3) 0.037(3) -0.015(2) 0.001(2) -0.008(2) C9 0.026(2) 0.036(3) 0.033(3) -0.014(2) 0.0013(19) 0.002(2) C10 0.031(3) 0.030(2) 0.032(3) -0.011(2) 0.002(2) -0.001(2) C11 0.026(2) 0.024(2) 0.033(2) -0.0117(19) 0.0070(19) -0.0042(19) C12 0.029(2) 0.029(2) 0.032(2) -0.016(2) 0.0084(19) -0.008(2) C13 0.036(3) 0.032(3) 0.046(3) -0.012(2) 0.008(2) -0.008(2) C14 0.046(3) 0.032(3) 0.050(3) -0.018(3) 0.016(3) -0.019(3) C15 0.034(3) 0.046(3) 0.046(3) -0.029(3) 0.016(2) -0.024(3) C16 0.031(3) 0.033(3) 0.037(3) -0.017(2) 0.006(2) -0.010(2) C17 0.029(2) 0.027(2) 0.035(3) -0.016(2) 0.005(2) -0.0046(19) C18 0.028(3) 0.062(4) 0.055(4) -0.015(3) -0.007(3) -0.008(3) C19 0.025(2) 0.043(3) 0.036(3) -0.026(2) 0.000(2) -0.003(2) C20 0.026(2) 0.041(3) 0.036(3) -0.024(2) 0.001(2) -0.004(2) C21 0.021(2) 0.027(2) 0.037(3) -0.016(2) 0.0019(19) -0.0051(18) C22 0.024(2) 0.033(3) 0.037(3) -0.021(2) 0.0064(19) -0.005(2) C23 0.025(2) 0.024(2) 0.029(2) -0.0137(18) 0.0055(18) -0.0096(18) C24 0.025(2) 0.030(2) 0.028(2) -0.0126(19) 0.0050(18) -0.0081(19) C25 0.028(3) 0.044(3) 0.036(3) -0.022(2) 0.008(2) -0.009(2) C26 0.042(3) 0.057(4) 0.041(3) -0.035(3) 0.014(2) -0.014(3) C27 0.045(3) 0.050(3) 0.026(3) -0.020(2) 0.001(2) -0.015(3) C28 0.037(3) 0.035(3) 0.027(2) -0.013(2) -0.002(2) -0.010(2) C29 0.030(2) 0.027(2) 0.026(2) -0.0102(19) 0.0031(19) -0.0089(19) C30 0.027(3) 0.046(3) 0.044(3) -0.024(3) -0.007(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C29 1.989(5) . ? Ir1 C17 2.022(5) . ? Ir1 N4 2.043(4) . ? Ir1 N5 2.046(4) . ? Ir1 N3 2.112(4) . ? Ir1 N1 2.161(4) . ? F1 C13 1.380(8) . ? F2 C15 1.360(6) . ? F3 C25 1.363(7) . ? F4 C27 1.357(6) . ? O1 C6 1.222(6) . ? O2 C21 1.355(6) . ? O2 C30 1.432(7) . ? O3 C9 1.334(7) . ? O3 C18 1.434(8) . ? N1 C1 1.330(7) . ? N1 N2 1.370(6) . ? N2 C3 1.364(7) . ? N2 C6 1.465(7) . ? N3 C6 1.304(7) . ? N4 C7 1.329(6) . ? N4 C11 1.381(6) . ? N5 C19 1.344(6) . ? N5 C23 1.375(6) . ? C1 C2 1.399(9) . ? C1 C4 1.495(9) . ? C2 C3 1.369(9) . ? C3 C5 1.480(9) . ? C7 C8 1.382(7) . ? C8 C9 1.390(8) . ? C9 C10 1.393(8) . ? C10 C11 1.374(7) . ? C11 C12 1.469(7) . ? C12 C13 1.387(8) . ? C12 C17 1.419(8) . ? C13 C14 1.388(9) . ? C14 C15 1.379(10) . ? C15 C16 1.392(8) . ? C16 C17 1.395(7) . ? C19 C20 1.383(7) . ? C20 C21 1.390(7) . ? C21 C22 1.399(7) . ? C22 C23 1.375(7) . ? C23 C24 1.469(7) . ? C24 C25 1.391(7) . ? C24 C29 1.423(7) . ? C25 C26 1.379(8) . ? C26 C27 1.365(9) . ? C27 C28 1.373(9) . ? C28 C29 1.411(7) . ? 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 C29 Ir1 C17 90.5(2) . . ? C29 Ir1 N4 94.09(19) . . ? C17 Ir1 N4 80.54(19) . . ? C29 Ir1 N5 80.50(19) . . ? C17 Ir1 N5 95.8(2) . . ? N4 Ir1 N5 173.49(15) . . ? C29 Ir1 N3 93.20(18) . . ? C17 Ir1 N3 174.49(18) . . ? N4 Ir1 N3 95.08(17) . . ? N5 Ir1 N3 88.87(17) . . ? C29 Ir1 N1 166.78(18) . . ? C17 Ir1 N1 101.56(18) . . ? N4 Ir1 N1 93.33(16) . . ? N5 Ir1 N1 92.68(16) . . ? N3 Ir1 N1 75.24(16) . . ? C21 O2 C30 118.3(4) . . ? C9 O3 C18 117.7(5) . . ? C1 N1 N2 105.9(4) . . ? C1 N1 Ir1 140.4(4) . . ? N2 N1 Ir1 111.4(3) . . ? C3 N2 N1 111.6(4) . . ? C3 N2 C6 129.4(5) . . ? N1 N2 C6 119.0(4) . . ? C6 N3 Ir1 120.6(3) . . ? C7 N4 C11 118.8(4) . . ? C7 N4 Ir1 124.2(4) . . ? C11 N4 Ir1 116.5(3) . . ? C19 N5 C23 119.1(4) . . ? C19 N5 Ir1 124.4(3) . . ? C23 N5 Ir1 116.5(3) . . ? N1 C1 C2 109.4(5) . . ? N1 C1 C4 121.9(6) . . ? C2 C1 C4 128.7(5) . . ? C3 C2 C1 107.9(5) . . ? N2 C3 C2 105.2(5) . . ? N2 C3 C5 124.7(5) . . ? C2 C3 C5 130.1(5) . . ? O1 C6 N3 131.3(5) . . ? O1 C6 N2 117.4(5) . . ? N3 C6 N2 111.3(4) . . ? N4 C7 C8 123.8(5) . . ? C7 C8 C9 118.1(5) . . ? O3 C9 C8 125.8(5) . . ? O3 C9 C10 115.9(5) . . ? C8 C9 C10 118.4(5) . . ? C11 C10 C9 121.1(5) . . ? C10 C11 N4 119.8(5) . . ? C10 C11 C12 127.6(5) . . ? N4 C11 C12 112.6(4) . . ? C13 C12 C17 118.8(5) . . ? C13 C12 C11 125.1(5) . . ? C17 C12 C11 116.1(4) . . ? F1 C13 C12 121.3(5) . . ? F1 C13 C14 115.0(6) . . ? C12 C13 C14 123.7(6) . . ? C15 C14 C13 115.8(6) . . ? F2 C15 C14 117.5(5) . . ? F2 C15 C16 119.1(6) . . ? C14 C15 C16 123.4(5) . . ? C15 C16 C17 119.7(5) . . ? C16 C17 C12 118.4(5) . . ? C16 C17 Ir1 127.8(4) . . ? C12 C17 Ir1 113.9(4) . . ? N5 C19 C20 123.0(5) . . ? C19 C20 C21 118.2(5) . . ? O2 C21 C20 124.7(5) . . ? O2 C21 C22 116.2(4) . . ? C20 C21 C22 119.1(5) . . ? C23 C22 C21 120.1(5) . . ? C22 C23 N5 120.5(4) . . ? C22 C23 C24 126.9(4) . . ? N5 C23 C24 112.6(4) . . ? C25 C24 C29 119.0(5) . . ? C25 C24 C23 125.7(5) . . ? C29 C24 C23 115.3(4) . . ? F3 C25 C26 116.0(5) . . ? F3 C25 C24 120.9(5) . . ? C26 C25 C24 123.1(5) . . ? C27 C26 C25 116.5(5) . . ? F4 C27 C26 117.9(5) . . ? F4 C27 C28 117.8(6) . . ? C26 C27 C28 124.2(5) . . ? C27 C28 C29 119.4(5) . . ? C28 C29 C24 117.7(5) . . ? C28 C29 Ir1 127.1(4) . . ? C24 C29 Ir1 115.0(4) . . ? 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 N3 H3 O2 0.88 2.21 3.034(6) 155.2 2_656 _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 3.230 _refine_diff_density_min -2.014 _refine_diff_density_rms 0.157