# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'William Goddard III' _publ_contact_author_email SHIRLEY@WAG.CALTECH.EDU loop_ _publ_author_name W.GoddardIII D.H.Ess S.K.Meier J.Oxgaard R.Periana T.Stewart ; K.J.H.Young ; # Attachment 'irnncm_697907.cif' data_irnncm_1-TFA_697907 _database_code_depnum_ccdc_archive 'CCDC 697907' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H30 F3 Ir N2 O2' _chemical_formula_weight 735.79 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 19.9643(16) _cell_length_b 13.8063(11) _cell_length_c 21.8966(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.1910(10) _cell_angle_gamma 90.00 _cell_volume 6034.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 6816 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 1.618 _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2896 _exptl_absorpt_coefficient_mu 4.475 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5935 _exptl_absorpt_correction_T_max 0.8773 _exptl_absorpt_process_details Blessing,R.H.,Acta_Crystallogr.1995,A51,33 _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17914 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0739 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6816 _reflns_number_gt 4857 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+42.1662P] 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 6816 _refine_ls_number_parameters 389 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.017 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 0.192663(13) 0.12834(2) 0.295571(12) 0.02825(10) Uani 1 1 d . . . F1 F 0.4251(3) 0.1305(6) 0.2465(4) 0.109(3) Uani 1 1 d . . . F2 F 0.4036(3) 0.1642(5) 0.1550(3) 0.0829(19) Uani 1 1 d . . . F3 F 0.4220(3) 0.2785(5) 0.2171(4) 0.106(3) Uani 1 1 d . . . N1 N 0.1741(3) 0.0339(4) 0.2181(3) 0.0273(13) Uani 1 1 d . . . N2 N 0.1487(3) 0.2169(4) 0.2333(3) 0.0269(13) Uani 1 1 d . . . O1 O 0.2972(3) 0.1473(4) 0.2664(3) 0.0499(15) Uani 1 1 d . . . O2 O 0.2860(3) 0.2581(5) 0.1943(3) 0.071(2) Uani 1 1 d . . . C1 C 0.1825(3) -0.0619(5) 0.2142(3) 0.0310(16) Uani 1 1 d . . . H1 H 0.2081 -0.0934 0.2454 0.037 Uiso 1 1 calc R . . C2 C 0.1562(4) -0.1172(5) 0.1676(3) 0.0338(16) Uani 1 1 d . . . H2 H 0.1641 -0.1850 0.1676 0.041 Uiso 1 1 calc R . . C3 C 0.1181(4) -0.0761(5) 0.1205(3) 0.0317(16) Uani 1 1 d . . . C4 C 0.1130(3) 0.0247(5) 0.1229(3) 0.0288(16) Uani 1 1 d . . . H4 H 0.0903 0.0579 0.0906 0.035 Uiso 1 1 calc R . . C5 C 0.1401(3) 0.0771(5) 0.1709(3) 0.0295(16) Uani 1 1 d . . . C6 C 0.1305(3) 0.1821(5) 0.1774(3) 0.0279(15) Uani 1 1 d . . . C7 C 0.1025(4) 0.2422(6) 0.1339(3) 0.0367(18) Uani 1 1 d . . . H7 H 0.0906 0.2171 0.0948 0.044 Uiso 1 1 calc R . . C8 C 0.0913(4) 0.3401(5) 0.1466(3) 0.0337(17) Uani 1 1 d . . . C9 C 0.1107(4) 0.3722(6) 0.2043(3) 0.0359(16) Uani 1 1 d . . . H9 H 0.1038 0.4383 0.2147 0.043 Uiso 1 1 calc R . . C10 C 0.1398(3) 0.3114(5) 0.2471(3) 0.0295(16) Uani 1 1 d . . . C11 C 0.1627(4) 0.3341(5) 0.3089(3) 0.0315(16) Uani 1 1 d . . . C12 C 0.1585(4) 0.4284(6) 0.3325(4) 0.0399(19) Uani 1 1 d . . . H12 H 0.1423 0.4796 0.3073 0.048 Uiso 1 1 calc R . . C13 C 0.1777(4) 0.4469(6) 0.3922(4) 0.044(2) Uani 1 1 d . . . H13 H 0.1748 0.5106 0.4083 0.053 Uiso 1 1 calc R . . C14 C 0.2011(4) 0.3725(7) 0.4281(4) 0.045(2) Uani 1 1 d . . . H14 H 0.2139 0.3848 0.4694 0.055 Uiso 1 1 calc R . . C15 C 0.2064(4) 0.2795(6) 0.4049(4) 0.044(2) Uani 1 1 d . . . H15 H 0.2224 0.2291 0.4309 0.053 Uiso 1 1 calc R . . C16 C 0.1890(4) 0.2576(5) 0.3440(3) 0.0323(17) Uani 1 1 d . . . C17 C 0.0816(4) -0.1342(5) 0.0708(3) 0.0378(18) Uani 1 1 d . . . C18 C 0.0953(7) -0.2412(6) 0.0769(5) 0.086(4) Uani 1 1 d . . . H18A H 0.1437 -0.2526 0.0759 0.129 Uiso 1 1 calc R . . H18B H 0.0732 -0.2759 0.0431 0.129 Uiso 1 1 calc R . . H18C H 0.0780 -0.2646 0.1158 0.129 Uiso 1 1 calc R . . C19 C 0.1059(5) -0.1017(7) 0.0099(4) 0.059(3) Uani 1 1 d . . . H19A H 0.0970 -0.0323 0.0047 0.089 Uiso 1 1 calc R . . H19B H 0.0826 -0.1380 -0.0226 0.089 Uiso 1 1 calc R . . H19C H 0.1542 -0.1134 0.0076 0.089 Uiso 1 1 calc R . . C20 C 0.0067(5) -0.1176(8) 0.0753(5) 0.071(3) Uani 1 1 d . . . H20A H -0.0080 -0.1363 0.1160 0.107 Uiso 1 1 calc R . . H20B H -0.0170 -0.1568 0.0444 0.107 Uiso 1 1 calc R . . H20C H -0.0033 -0.0489 0.0683 0.107 Uiso 1 1 calc R . . C21 C 0.0607(4) 0.4063(6) 0.0974(4) 0.042(2) Uani 1 1 d . . . C22 C 0.1109(6) 0.4182(8) 0.0480(5) 0.075(3) Uani 1 1 d . . . H22A H 0.1513 0.4494 0.0649 0.112 Uiso 1 1 calc R . . H22B H 0.0917 0.4586 0.0152 0.112 Uiso 1 1 calc R . . H22C H 0.1225 0.3545 0.0315 0.112 Uiso 1 1 calc R . . C23 C -0.0032(5) 0.3595(7) 0.0706(5) 0.068(3) Uani 1 1 d . . . H23A H 0.0085 0.2998 0.0491 0.102 Uiso 1 1 calc R . . H23B H -0.0251 0.4045 0.0420 0.102 Uiso 1 1 calc R . . H23C H -0.0338 0.3442 0.1037 0.102 Uiso 1 1 calc R . . C24 C 0.0401(7) 0.5045(7) 0.1234(5) 0.086(4) Uani 1 1 d . . . H24A H 0.0136 0.4944 0.1601 0.129 Uiso 1 1 calc R . . H24B H 0.0131 0.5397 0.0928 0.129 Uiso 1 1 calc R . . H24C H 0.0803 0.5422 0.1340 0.129 Uiso 1 1 calc R . . C25 C 0.3164(5) 0.1970(6) 0.2260(4) 0.050(2) Uani 1 1 d . . . C26 C 0.3909(5) 0.1966(7) 0.2103(5) 0.059(3) Uani 1 1 d . . . C27 C 0.2359(5) 0.0000(6) 0.3376(4) 0.049(2) Uani 1 1 d . . . C28 C 0.2411(5) 0.0778(6) 0.3793(4) 0.051(2) Uani 1 1 d . . . C29 C 0.0997(6) 0.0904(9) 0.3296(5) 0.089(6) Uani 1.00(3) 1 d D . . C30 C 0.0569(9) 0.0299(14) 0.2970(8) 0.051(6) Uani 0.461(19) 1 d PD . . C30A C 0.0482(8) 0.1546(12) 0.3366(10) 0.060(6) Uani 0.539(19) 1 d PD . . C31 C 0.2824(4) 0.6641(5) 0.4956(4) 0.048(2) Uani 1 1 d D . . H31 H 0.3065 0.6051 0.4922 0.057 Uiso 1 1 calc R . . C32 C 0.2474(6) 0.6991(7) 0.4477(4) 0.162(10) Uani 1 1 d D . . H32 H 0.2438 0.6625 0.4110 0.195 Uiso 1 1 calc R . . C33 C 0.2169(6) 0.7869(7) 0.4514(4) 0.103(5) Uani 1 1 d D . . H33 H 0.1950 0.8136 0.4164 0.124 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 0.03015(15) 0.02859(15) 0.02603(15) -0.00011(14) 0.00083(10) -0.00567(14) F1 0.049(3) 0.128(7) 0.149(7) 0.059(6) 0.006(4) 0.009(4) F2 0.080(4) 0.080(4) 0.090(5) -0.011(4) 0.036(4) 0.012(4) F3 0.072(4) 0.062(4) 0.185(8) -0.032(5) 0.055(5) -0.035(3) N1 0.030(3) 0.031(3) 0.021(3) -0.001(2) -0.001(2) 0.000(3) N2 0.028(3) 0.023(3) 0.030(3) -0.005(2) 0.010(2) -0.002(2) O1 0.041(3) 0.047(4) 0.062(4) -0.007(3) 0.005(3) -0.005(3) O2 0.061(4) 0.069(5) 0.083(5) 0.023(4) 0.010(4) 0.008(4) C1 0.033(4) 0.030(4) 0.030(4) 0.003(3) 0.000(3) 0.011(3) C2 0.043(4) 0.027(4) 0.031(4) -0.002(3) 0.003(3) 0.007(3) C3 0.035(4) 0.031(4) 0.029(4) -0.007(3) 0.003(3) 0.003(3) C4 0.035(4) 0.027(4) 0.024(4) -0.004(3) 0.003(3) 0.008(3) C5 0.028(4) 0.032(4) 0.028(4) 0.000(3) 0.005(3) 0.008(3) C6 0.028(4) 0.028(4) 0.029(4) -0.006(3) 0.003(3) 0.004(3) C7 0.044(4) 0.037(4) 0.029(4) -0.009(3) -0.006(3) 0.010(4) C8 0.040(4) 0.027(4) 0.034(4) -0.010(3) -0.001(3) 0.010(3) C9 0.044(4) 0.024(4) 0.039(4) -0.006(4) 0.003(3) 0.005(4) C10 0.032(4) 0.028(4) 0.029(4) 0.002(3) 0.010(3) -0.005(3) C11 0.034(4) 0.027(4) 0.033(4) -0.006(3) 0.006(3) -0.010(3) C12 0.047(5) 0.034(4) 0.039(5) -0.009(4) 0.007(4) -0.004(4) C13 0.053(5) 0.036(5) 0.044(5) -0.015(4) 0.003(4) -0.008(4) C14 0.051(5) 0.055(5) 0.030(4) -0.010(4) 0.001(3) -0.014(5) C15 0.048(5) 0.044(5) 0.041(5) -0.005(4) 0.004(4) -0.019(4) C16 0.041(4) 0.025(4) 0.031(4) -0.002(3) 0.007(3) -0.010(3) C17 0.049(4) 0.027(4) 0.037(4) -0.002(4) -0.012(3) 0.007(4) C18 0.147(11) 0.025(5) 0.083(8) -0.012(5) -0.063(8) 0.011(6) C19 0.088(7) 0.051(6) 0.040(5) -0.006(4) -0.005(5) -0.004(5) C20 0.055(6) 0.073(8) 0.085(8) -0.008(6) -0.010(5) -0.002(6) C21 0.056(5) 0.029(4) 0.040(5) -0.004(3) -0.007(4) 0.015(4) C22 0.087(8) 0.063(7) 0.075(8) 0.023(6) -0.008(6) 0.012(6) C23 0.076(7) 0.047(6) 0.079(7) 0.003(5) -0.032(6) 0.012(5) C24 0.148(11) 0.040(6) 0.067(7) -0.018(5) -0.037(7) 0.046(7) C25 0.067(6) 0.032(5) 0.050(5) 0.016(4) 0.003(5) -0.008(4) C26 0.044(5) 0.045(6) 0.090(8) -0.004(5) 0.020(5) -0.003(4) C27 0.073(6) 0.035(5) 0.038(5) 0.011(4) -0.030(4) -0.002(4) C28 0.081(7) 0.036(5) 0.035(5) 0.002(4) -0.027(4) -0.012(4) C29 0.079(9) 0.127(13) 0.061(8) -0.018(7) 0.024(6) -0.061(9) C30 0.055(12) 0.063(14) 0.035(11) -0.007(9) 0.022(9) -0.018(10) C30A 0.027(8) 0.052(11) 0.102(16) -0.010(10) 0.025(9) 0.000(7) C31 0.068(6) 0.053(5) 0.023(4) 0.002(4) 0.023(4) -0.015(5) C32 0.198(19) 0.121(14) 0.173(18) -0.099(14) 0.137(17) -0.108(14) C33 0.123(12) 0.103(11) 0.084(10) 0.009(8) 0.000(8) -0.047(10) _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 N2 2.019(6) . ? Ir1 C16 2.078(7) . ? Ir1 C29 2.081(10) . ? Ir1 N1 2.166(6) . ? Ir1 C27 2.168(8) . ? Ir1 C28 2.170(8) . ? Ir1 O1 2.210(6) . ? F1 C26 1.380(12) . ? F2 C26 1.322(12) . ? F3 C26 1.296(10) . ? N1 C1 1.336(9) . ? N1 C5 1.362(9) . ? N2 C10 1.352(9) . ? N2 C6 1.356(9) . ? O1 C25 1.190(9) . ? O2 C25 1.242(10) . ? C1 C2 1.369(10) . ? C2 C3 1.389(10) . ? C3 C4 1.397(10) . ? C3 C17 1.526(10) . ? C4 C5 1.377(10) . ? C5 C6 1.470(10) . ? C6 C7 1.375(10) . ? C7 C8 1.399(10) . ? C8 C9 1.387(10) . ? C8 C21 1.530(11) . ? C9 C10 1.377(10) . ? C10 C11 1.455(10) . ? C11 C16 1.401(10) . ? C11 C12 1.404(10) . ? C12 C13 1.379(11) . ? C13 C14 1.369(12) . ? C14 C15 1.387(11) . ? C15 C16 1.404(10) . ? C17 C19 1.498(12) . ? C17 C18 1.508(11) . ? C17 C20 1.518(12) . ? C21 C22 1.499(13) . ? C21 C24 1.530(11) . ? C21 C23 1.535(12) . ? C25 C26 1.532(12) . ? C27 C28 1.412(12) . ? C29 C30A 1.369(15) . ? C29 C30 1.385(15) . ? C31 C32 1.338(8) . ? C31 C33 1.343(8) 7_566 ? C32 C33 1.359(8) . ? C33 C31 1.343(8) 7_566 ? 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 N2 Ir1 C16 78.8(3) . . ? N2 Ir1 C29 90.9(4) . . ? C16 Ir1 C29 89.5(4) . . ? N2 Ir1 N1 76.7(2) . . ? C16 Ir1 N1 155.4(3) . . ? C29 Ir1 N1 89.5(3) . . ? N2 Ir1 C27 161.0(3) . . ? C16 Ir1 C27 120.2(3) . . ? C29 Ir1 C27 89.6(5) . . ? N1 Ir1 C27 84.3(3) . . ? N2 Ir1 C28 161.0(3) . . ? C16 Ir1 C28 82.2(3) . . ? C29 Ir1 C28 90.1(4) . . ? N1 Ir1 C28 122.3(3) . . ? C27 Ir1 C28 38.0(3) . . ? N2 Ir1 O1 97.6(2) . . ? C16 Ir1 O1 95.1(2) . . ? C29 Ir1 O1 170.9(4) . . ? N1 Ir1 O1 89.5(2) . . ? C27 Ir1 O1 81.3(3) . . ? C28 Ir1 O1 82.9(3) . . ? C1 N1 C5 116.5(6) . . ? C1 N1 Ir1 128.8(5) . . ? C5 N1 Ir1 113.9(5) . . ? C10 N2 C6 120.6(6) . . ? C10 N2 Ir1 119.4(5) . . ? C6 N2 Ir1 120.0(5) . . ? C25 O1 Ir1 127.2(6) . . ? N1 C1 C2 123.6(7) . . ? C1 C2 C3 121.4(7) . . ? C2 C3 C4 114.7(7) . . ? C2 C3 C17 124.2(7) . . ? C4 C3 C17 121.1(7) . . ? C5 C4 C3 121.6(7) . . ? N1 C5 C4 122.1(7) . . ? N1 C5 C6 115.0(6) . . ? C4 C5 C6 122.9(7) . . ? N2 C6 C7 120.6(7) . . ? N2 C6 C5 113.8(6) . . ? C7 C6 C5 125.5(7) . . ? C6 C7 C8 120.6(7) . . ? C9 C8 C7 116.6(7) . . ? C9 C8 C21 123.4(7) . . ? C7 C8 C21 119.9(7) . . ? C10 C9 C8 122.0(7) . . ? N2 C10 C9 119.5(7) . . ? N2 C10 C11 112.1(6) . . ? C9 C10 C11 128.4(7) . . ? C16 C11 C12 121.5(7) . . ? C16 C11 C10 117.0(6) . . ? C12 C11 C10 121.5(7) . . ? C13 C12 C11 120.2(8) . . ? C14 C13 C12 119.4(8) . . ? C13 C14 C15 120.8(8) . . ? C14 C15 C16 121.9(8) . . ? C11 C16 C15 116.2(7) . . ? C11 C16 Ir1 112.6(5) . . ? C15 C16 Ir1 131.2(6) . . ? C19 C17 C18 108.1(8) . . ? C19 C17 C20 110.5(8) . . ? C18 C17 C20 108.7(8) . . ? C19 C17 C3 108.6(7) . . ? C18 C17 C3 111.6(6) . . ? C20 C17 C3 109.3(7) . . ? C22 C21 C24 111.1(9) . . ? C22 C21 C8 108.1(7) . . ? C24 C21 C8 111.9(7) . . ? C22 C21 C23 109.4(8) . . ? C24 C21 C23 106.7(8) . . ? C8 C21 C23 109.5(7) . . ? O1 C25 O2 130.1(10) . . ? O1 C25 C26 119.6(9) . . ? O2 C25 C26 110.1(8) . . ? F3 C26 F2 107.4(9) . . ? F3 C26 F1 106.4(9) . . ? F2 C26 F1 101.5(8) . . ? F3 C26 C25 115.8(8) . . ? F2 C26 C25 114.3(9) . . ? F1 C26 C25 110.2(8) . . ? C28 C27 Ir1 71.1(5) . . ? C27 C28 Ir1 70.9(4) . . ? C30A C29 C30 89.4(14) . . ? C30A C29 Ir1 123.7(11) . . ? C30 C29 Ir1 120.9(10) . . ? C32 C31 C33 119.4(4) . 7_566 ? C31 C32 C33 120.2(4) . . ? C31 C33 C32 120.3(4) 7_566 . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.374 _refine_diff_density_min -1.220 _refine_diff_density_rms 0.155 # Attachment 'tj5m_697908.cif' data_tj5m_1-cl _database_code_depnum_ccdc_archive 'CCDC 697908' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H66 Cl4 Ir2 N4' _chemical_formula_weight 1333.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.9695(11) _cell_length_b 29.356(3) _cell_length_c 16.8671(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.947(2) _cell_angle_gamma 90.00 _cell_volume 6204.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 13971 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 27.54 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 1.425 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2632 _exptl_absorpt_coefficient_mu 4.493 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.634 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_process_details 'Blessing,R.H. Acta_Crystallogr.1995,A51,33' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36987 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0891 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.54 _reflns_number_total 13971 _reflns_number_gt 9719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+53.6893P] 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 SHELXL _refine_ls_extinction_coef 0.00085(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13971 _refine_ls_number_parameters 619 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.002 _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 0.49755(3) 0.915748(13) 0.67901(3) 0.02520(13) Uani 1 1 d . . . Ir2 Ir 0.01737(3) 0.184167(14) 0.41649(3) 0.02771(13) Uani 1 1 d . . . Cl1 Cl 0.4272(2) 0.85185(10) 0.58349(19) 0.0400(7) Uani 1 1 d . . . Cl2 Cl 0.0074(2) 0.24422(10) 0.5181(2) 0.0434(7) Uani 1 1 d . . . Cl3 Cl 0.0810(5) 0.2557(2) 0.7702(4) 0.121(2) Uani 1 1 d . . . Cl4 Cl 0.1856(6) 0.1690(2) 0.7866(3) 0.131(3) Uani 1 1 d . . . N1 N 0.4175(6) 0.8939(3) 0.7584(5) 0.0249(18) Uani 1 1 d . . . N2 N 0.6086(6) 0.8691(3) 0.7564(5) 0.0242(18) Uani 1 1 d . . . N3 N -0.0473(6) 0.1384(3) 0.4920(6) 0.0280(19) Uani 1 1 d . . . N4 N 0.1494(6) 0.1593(3) 0.4964(5) 0.0246(18) Uani 1 1 d . . . C1 C 0.3555(8) 0.9516(3) 0.6386(7) 0.027(2) Uani 1 1 d . . . C2 C 0.3196(9) 0.9820(4) 0.5726(7) 0.034(3) Uani 1 1 d . . . H2 H 0.3650 0.9896 0.5384 0.041 Uiso 1 1 calc R . . C3 C 0.2187(9) 1.0009(4) 0.5572(7) 0.035(3) Uani 1 1 d . . . H3 H 0.1973 1.0215 0.5126 0.041 Uiso 1 1 calc R . . C4 C 0.1476(9) 0.9913(4) 0.6030(7) 0.036(3) Uani 1 1 d . . . H4 H 0.0782 1.0044 0.5898 0.043 Uiso 1 1 calc R . . C5 C 0.1809(9) 0.9619(4) 0.6692(7) 0.035(3) Uani 1 1 d . . . H5 H 0.1339 0.9548 0.7023 0.042 Uiso 1 1 calc R . . C6 C 0.2844(8) 0.9423(3) 0.6879(6) 0.025(2) Uani 1 1 d . . . C7 C 0.3198(8) 0.9106(3) 0.7562(6) 0.026(2) Uani 1 1 d . . . C8 C 0.2666(8) 0.8973(4) 0.8135(7) 0.032(2) Uani 1 1 d . . . H8 H 0.1975 0.9093 0.8099 0.039 Uiso 1 1 calc R . . C9 C 0.3105(9) 0.8675(4) 0.8752(8) 0.039(3) Uani 1 1 d . . . C10 C 0.4118(9) 0.8500(4) 0.8766(8) 0.037(3) Uani 1 1 d . . . H10 H 0.4450 0.8288 0.9179 0.044 Uiso 1 1 calc R . . C11 C 0.4633(8) 0.8635(4) 0.8181(7) 0.030(2) Uani 1 1 d . . . C12 C 0.5720(8) 0.8493(4) 0.8170(7) 0.033(2) Uani 1 1 d . . . C13 C 0.6320(8) 0.8186(3) 0.8703(6) 0.027(2) Uani 1 1 d . . . H13 H 0.6027 0.8050 0.9108 0.032 Uiso 1 1 calc R . . C14 C 0.7350(8) 0.8067(4) 0.8672(7) 0.030(2) Uani 1 1 d . . . C15 C 0.7706(9) 0.8276(4) 0.8058(7) 0.037(3) Uani 1 1 d . . . H15 H 0.8408 0.8215 0.8012 0.044 Uiso 1 1 calc R . . C16 C 0.7066(8) 0.8571(4) 0.7511(7) 0.031(2) Uani 1 1 d . . . H16 H 0.7327 0.8694 0.7080 0.038 Uiso 1 1 calc R . . C17 C 0.2541(9) 0.8516(5) 0.9406(8) 0.045(3) Uani 1 1 d . . . C18 C 0.1513(12) 0.8795(6) 0.9335(11) 0.083(6) Uani 1 1 d . . . H18A H 0.1111 0.8665 0.9699 0.124 Uiso 1 1 calc R . . H18B H 0.1074 0.8786 0.8767 0.124 Uiso 1 1 calc R . . H18C H 0.1701 0.9112 0.9494 0.124 Uiso 1 1 calc R . . C19 C 0.2253(10) 0.8026(5) 0.9279(10) 0.061(4) Uani 1 1 d . . . H19A H 0.1859 0.7931 0.9675 0.091 Uiso 1 1 calc R . . H19B H 0.2904 0.7843 0.9359 0.091 Uiso 1 1 calc R . . H19C H 0.1805 0.7981 0.8721 0.091 Uiso 1 1 calc R . . C20 C 0.3286(13) 0.8587(6) 1.0251(9) 0.068(4) Uani 1 1 d . . . H20A H 0.3908 0.8387 1.0318 0.101 Uiso 1 1 calc R . . H20B H 0.2911 0.8514 1.0670 0.101 Uiso 1 1 calc R . . H20C H 0.3522 0.8905 1.0310 0.101 Uiso 1 1 calc R . . C21 C 0.8008(9) 0.7724(4) 0.9288(7) 0.038(3) Uani 1 1 d . . . C22 C 0.7482(11) 0.7261(4) 0.9153(9) 0.052(4) Uani 1 1 d . . . H22A H 0.6753 0.7284 0.9214 0.078 Uiso 1 1 calc R . . H22B H 0.7890 0.7046 0.9559 0.078 Uiso 1 1 calc R . . H22C H 0.7463 0.7154 0.8600 0.078 Uiso 1 1 calc R . . C23 C 0.8055(11) 0.7885(5) 1.0160(8) 0.053(3) Uani 1 1 d . . . H23A H 0.8460 0.7664 1.0557 0.079 Uiso 1 1 calc R . . H23B H 0.7329 0.7910 1.0228 0.079 Uiso 1 1 calc R . . H23C H 0.8407 0.8183 1.0255 0.079 Uiso 1 1 calc R . . C24 C 0.9142(10) 0.7678(5) 0.9175(9) 0.052(4) Uani 1 1 d . . . H24A H 0.9102 0.7578 0.8614 0.079 Uiso 1 1 calc R . . H24B H 0.9542 0.7453 0.9565 0.079 Uiso 1 1 calc R . . H24C H 0.9504 0.7973 0.9274 0.079 Uiso 1 1 calc R . . C25 C 0.6196(8) 0.9260(4) 0.6135(7) 0.036(3) Uani 1 1 d . . . C26 C 0.5321(9) 0.9526(4) 0.5752(8) 0.040(3) Uani 1 1 d . . . C27 C 0.5650(9) 0.9695(4) 0.7587(7) 0.035(3) Uani 1 1 d . . . H27A H 0.6434 0.9653 0.7738 0.043 Uiso 1 1 calc R . . H27B H 0.5498 0.9982 0.7270 0.043 Uiso 1 1 calc R . . C28 C 0.5325(12) 0.9759(5) 0.8344(9) 0.059(4) Uani 1 1 d . . . H28A H 0.5494 0.9485 0.8683 0.088 Uiso 1 1 calc R . . H28B H 0.4555 0.9816 0.8213 0.088 Uiso 1 1 calc R . . H28C H 0.5707 1.0020 0.8645 0.088 Uiso 1 1 calc R . . C29 C -0.1496(8) 0.1294(3) 0.4898(7) 0.030(2) Uani 1 1 d . . . H29 H -0.2038 0.1388 0.4433 0.036 Uiso 1 1 calc R . . C30 C -0.1791(8) 0.1067(4) 0.5534(7) 0.030(2) Uani 1 1 d . . . H30 H -0.2525 0.1012 0.5494 0.036 Uiso 1 1 calc R . . C31 C -0.1043(8) 0.0923(3) 0.6209(7) 0.031(2) Uani 1 1 d . . . C32 C 0.0024(9) 0.0995(4) 0.6221(7) 0.032(2) Uani 1 1 d . . . H32 H 0.0575 0.0889 0.6671 0.038 Uiso 1 1 calc R . . C33 C 0.0278(8) 0.1220(3) 0.5581(7) 0.026(2) Uani 1 1 d . . . C34 C 0.1390(8) 0.1318(3) 0.5574(6) 0.025(2) Uani 1 1 d . . . C35 C 0.2264(8) 0.1161(3) 0.6138(7) 0.029(2) Uani 1 1 d . . . H35 H 0.2175 0.0960 0.6557 0.035 Uiso 1 1 calc R . . C36 C 0.3288(8) 0.1290(3) 0.6112(6) 0.028(2) Uani 1 1 d . . . C37 C 0.3354(8) 0.1580(3) 0.5467(7) 0.030(2) Uani 1 1 d . . . H37 H 0.4036 0.1677 0.5424 0.036 Uiso 1 1 calc R . . C38 C 0.2473(8) 0.1724(3) 0.4902(7) 0.027(2) Uani 1 1 d . . . C39 C 0.2407(8) 0.2046(3) 0.4242(7) 0.028(2) Uani 1 1 d . . . C40 C 0.3334(9) 0.2228(4) 0.4074(7) 0.034(2) Uani 1 1 d . . . H40 H 0.4018 0.2114 0.4350 0.041 Uiso 1 1 calc R . . C41 C 0.3236(10) 0.2575(4) 0.3498(7) 0.040(3) Uani 1 1 d . . . H41 H 0.3855 0.2704 0.3387 0.048 Uiso 1 1 calc R . . C42 C 0.2228(10) 0.2731(4) 0.3085(8) 0.042(3) Uani 1 1 d . . . H42 H 0.2160 0.2976 0.2707 0.051 Uiso 1 1 calc R . . C43 C 0.1320(9) 0.2530(4) 0.3226(7) 0.037(3) Uani 1 1 d . . . H43 H 0.0642 0.2635 0.2916 0.045 Uiso 1 1 calc R . . C44 C 0.1350(8) 0.2184(3) 0.3798(7) 0.028(2) Uani 1 1 d . . . C45 C -0.1363(9) 0.0715(4) 0.6946(8) 0.040(3) Uani 1 1 d . . . C46 C -0.2199(12) 0.0325(5) 0.6642(10) 0.062(4) Uani 1 1 d . . . H46A H -0.1832 0.0052 0.6522 0.093 Uiso 1 1 calc R . . H46B H -0.2726 0.0424 0.6144 0.093 Uiso 1 1 calc R . . H46C H -0.2561 0.0255 0.7071 0.093 Uiso 1 1 calc R . . C47 C -0.1881(12) 0.1086(5) 0.7343(9) 0.055(4) Uani 1 1 d . . . H47A H -0.2472 0.1223 0.6929 0.082 Uiso 1 1 calc R . . H47B H -0.1351 0.1321 0.7573 0.082 Uiso 1 1 calc R . . H47C H -0.2153 0.0953 0.7782 0.082 Uiso 1 1 calc R . . C48 C -0.0389(11) 0.0535(6) 0.7611(9) 0.075(5) Uani 1 1 d . . . H48A H 0.0065 0.0353 0.7349 0.112 Uiso 1 1 calc R . . H48B H -0.0637 0.0345 0.8002 0.112 Uiso 1 1 calc R . . H48C H 0.0021 0.0793 0.7901 0.112 Uiso 1 1 calc R . . C49 C 0.4310(8) 0.1139(4) 0.6759(7) 0.033(2) Uani 1 1 d . . . C50 C 0.4048(9) 0.0803(4) 0.7365(8) 0.042(3) Uani 1 1 d . . . H50A H 0.3726 0.0529 0.7072 0.063 Uiso 1 1 calc R . . H50B H 0.3544 0.0944 0.7637 0.063 Uiso 1 1 calc R . . H50C H 0.4704 0.0721 0.7777 0.063 Uiso 1 1 calc R . . C51 C 0.4859(11) 0.1570(4) 0.7190(8) 0.052(4) Uani 1 1 d . . . H51A H 0.5486 0.1483 0.7626 0.079 Uiso 1 1 calc R . . H51B H 0.4359 0.1739 0.7428 0.079 Uiso 1 1 calc R . . H51C H 0.5082 0.1763 0.6790 0.079 Uiso 1 1 calc R . . C52 C 0.5040(9) 0.0888(4) 0.6312(8) 0.041(3) Uani 1 1 d . . . H52A H 0.4655 0.0628 0.6009 0.062 Uiso 1 1 calc R . . H52B H 0.5678 0.0779 0.6716 0.062 Uiso 1 1 calc R . . H52C H 0.5250 0.1097 0.5929 0.062 Uiso 1 1 calc R . . C53 C -0.1507(10) 0.1984(4) 0.3576(8) 0.046(3) Uani 1 1 d . . . C54 C -0.0839(9) 0.2258(5) 0.3215(8) 0.050(3) Uani 1 1 d . . . C55 C 0.0206(10) 0.1334(4) 0.3301(7) 0.042(3) Uani 1 1 d . . . H55A H -0.0543 0.1250 0.3035 0.050 Uiso 1 1 calc R . . H55B H 0.0503 0.1472 0.2872 0.050 Uiso 1 1 calc R . . C56 C 0.0762(9) 0.0933(5) 0.3551(9) 0.053(4) Uani 1 1 d . . . H56A H 0.0440 0.0772 0.3936 0.079 Uiso 1 1 calc R . . H56B H 0.1508 0.1004 0.3821 0.079 Uiso 1 1 calc R . . H56C H 0.0731 0.0739 0.3072 0.079 Uiso 1 1 calc R . . C57 C 0.144(2) 0.2165(6) 0.7246(11) 0.103(7) Uani 1 1 d . . . H57A H 0.2065 0.2309 0.7116 0.123 Uiso 1 1 calc R . . H57B H 0.0946 0.2066 0.6723 0.123 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 0.0219(2) 0.0216(2) 0.0340(2) 0.00398(16) 0.01083(16) 0.00083(16) Ir2 0.0206(2) 0.0263(2) 0.0360(3) 0.00421(17) 0.00689(17) -0.00056(16) Cl1 0.0294(14) 0.0362(15) 0.0512(18) -0.0076(13) 0.0049(13) 0.0038(12) Cl2 0.0374(16) 0.0389(16) 0.058(2) -0.0066(14) 0.0206(14) 0.0019(12) Cl3 0.132(5) 0.131(5) 0.113(4) 0.051(4) 0.053(4) 0.067(4) Cl4 0.219(8) 0.096(4) 0.072(3) -0.010(3) 0.025(4) 0.069(4) N1 0.014(4) 0.021(4) 0.040(5) 0.005(4) 0.007(4) 0.002(3) N2 0.024(4) 0.022(4) 0.028(5) 0.009(3) 0.009(4) -0.003(3) N3 0.020(4) 0.023(4) 0.043(5) 0.001(4) 0.012(4) -0.005(3) N4 0.020(4) 0.023(4) 0.033(5) -0.003(4) 0.011(4) -0.001(3) C1 0.024(5) 0.023(5) 0.036(6) -0.004(4) 0.009(4) 0.000(4) C2 0.030(6) 0.032(6) 0.036(6) 0.005(5) 0.003(5) -0.004(5) C3 0.038(6) 0.022(5) 0.038(7) 0.000(5) 0.001(5) 0.008(5) C4 0.030(6) 0.027(6) 0.046(7) 0.002(5) 0.004(5) 0.011(5) C5 0.025(6) 0.031(6) 0.047(7) 0.002(5) 0.008(5) -0.004(5) C6 0.025(5) 0.017(5) 0.034(6) -0.002(4) 0.006(4) 0.001(4) C7 0.025(5) 0.021(5) 0.035(6) 0.001(4) 0.014(4) 0.001(4) C8 0.024(5) 0.032(6) 0.044(7) 0.006(5) 0.015(5) 0.003(4) C9 0.034(6) 0.045(7) 0.047(7) 0.007(6) 0.026(6) 0.000(5) C10 0.038(6) 0.025(5) 0.052(7) 0.016(5) 0.021(6) 0.009(5) C11 0.028(5) 0.027(5) 0.036(6) 0.008(4) 0.008(5) 0.001(4) C12 0.026(5) 0.029(6) 0.048(7) -0.003(5) 0.014(5) -0.002(4) C13 0.031(6) 0.022(5) 0.031(6) 0.008(4) 0.012(5) 0.001(4) C14 0.021(5) 0.030(6) 0.038(6) 0.002(5) 0.005(5) 0.005(4) C15 0.027(6) 0.034(6) 0.053(8) 0.006(5) 0.018(5) 0.007(5) C16 0.023(5) 0.034(6) 0.039(6) 0.006(5) 0.011(5) 0.004(4) C17 0.030(6) 0.057(8) 0.055(8) 0.012(6) 0.023(6) 0.013(6) C18 0.059(10) 0.104(14) 0.106(14) 0.058(11) 0.059(10) 0.036(9) C19 0.033(7) 0.078(11) 0.082(11) 0.030(8) 0.033(7) 0.006(7) C20 0.068(10) 0.081(11) 0.059(10) 0.014(8) 0.026(8) 0.011(9) C21 0.028(6) 0.048(7) 0.040(7) 0.010(5) 0.014(5) 0.001(5) C22 0.054(8) 0.041(7) 0.064(9) 0.028(7) 0.022(7) 0.017(6) C23 0.046(8) 0.053(8) 0.058(9) 0.012(7) 0.012(7) 0.008(6) C24 0.033(7) 0.058(8) 0.067(9) 0.026(7) 0.012(6) 0.024(6) C25 0.019(5) 0.048(7) 0.049(7) 0.004(5) 0.025(5) 0.000(5) C26 0.036(6) 0.042(7) 0.053(8) 0.024(6) 0.031(6) 0.014(5) C27 0.032(6) 0.030(6) 0.049(7) 0.015(5) 0.021(5) -0.001(5) C28 0.062(9) 0.044(8) 0.066(10) -0.007(7) 0.010(8) -0.011(7) C29 0.023(5) 0.028(5) 0.040(7) -0.006(5) 0.009(5) -0.001(4) C30 0.019(5) 0.029(6) 0.045(7) 0.004(5) 0.011(5) -0.001(4) C31 0.028(6) 0.025(5) 0.045(7) -0.002(5) 0.019(5) -0.004(4) C32 0.028(6) 0.031(6) 0.038(6) 0.000(5) 0.010(5) -0.004(4) C33 0.024(5) 0.014(4) 0.040(6) 0.001(4) 0.008(5) -0.003(4) C34 0.023(5) 0.022(5) 0.034(6) 0.002(4) 0.014(4) -0.003(4) C35 0.025(5) 0.025(5) 0.042(7) -0.001(5) 0.017(5) -0.001(4) C36 0.027(5) 0.023(5) 0.031(6) -0.004(4) 0.005(4) 0.000(4) C37 0.020(5) 0.028(6) 0.041(7) -0.005(5) 0.004(5) -0.005(4) C38 0.020(5) 0.021(5) 0.040(6) 0.001(4) 0.011(4) 0.003(4) C39 0.033(6) 0.014(5) 0.040(6) -0.004(4) 0.015(5) 0.000(4) C40 0.031(6) 0.033(6) 0.040(7) -0.003(5) 0.012(5) -0.003(5) C41 0.037(7) 0.042(7) 0.046(7) 0.001(6) 0.020(6) -0.007(5) C42 0.041(7) 0.045(7) 0.045(7) 0.015(6) 0.018(6) -0.001(6) C43 0.028(6) 0.038(6) 0.048(7) 0.009(5) 0.014(5) 0.003(5) C44 0.030(6) 0.022(5) 0.036(6) 0.005(4) 0.015(5) 0.003(4) C45 0.027(6) 0.036(6) 0.062(9) 0.003(6) 0.020(6) 0.002(5) C46 0.069(10) 0.048(8) 0.081(11) 0.004(7) 0.043(9) -0.022(7) C47 0.060(9) 0.055(9) 0.059(9) -0.008(7) 0.032(7) 0.003(7) C48 0.044(8) 0.117(14) 0.062(10) 0.052(10) 0.013(7) 0.000(9) C49 0.025(5) 0.034(6) 0.035(6) 0.001(5) 0.000(5) -0.003(5) C50 0.034(6) 0.044(7) 0.044(7) 0.012(6) 0.003(5) -0.001(5) C51 0.057(9) 0.043(7) 0.050(8) -0.012(6) 0.000(7) -0.013(6) C52 0.024(6) 0.043(7) 0.058(8) 0.011(6) 0.012(5) 0.010(5) C53 0.030(6) 0.046(7) 0.057(8) 0.020(6) 0.000(6) 0.003(5) C54 0.025(6) 0.068(9) 0.045(8) 0.021(7) -0.010(5) 0.006(6) C55 0.045(7) 0.040(7) 0.040(7) 0.000(5) 0.010(6) -0.023(6) C56 0.019(6) 0.073(10) 0.067(9) -0.044(8) 0.013(6) -0.007(6) C57 0.18(2) 0.077(13) 0.062(11) 0.017(10) 0.050(13) 0.049(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 N1 2.001(8) . ? Ir1 C1 2.078(10) . ? Ir1 C27 2.110(12) . ? Ir1 N2 2.165(8) . ? Ir1 C25 2.172(10) . ? Ir1 C26 2.200(11) . ? Ir1 Cl1 2.488(3) . ? Ir2 N4 2.024(8) . ? Ir2 C44 2.052(10) . ? Ir2 C55 2.092(12) . ? Ir2 N3 2.163(8) . ? Ir2 C54 2.167(11) . ? Ir2 C53 2.190(12) . ? Ir2 Cl2 2.485(3) . ? Cl3 C57 1.704(18) . ? Cl4 C57 1.745(17) . ? N1 C7 1.350(12) . ? N1 C11 1.362(13) . ? N2 C16 1.344(13) . ? N2 C12 1.362(14) . ? N3 C29 1.343(12) . ? N3 C33 1.365(13) . ? N4 C34 1.340(13) . ? N4 C38 1.356(12) . ? C1 C2 1.410(15) . ? C1 C6 1.418(14) . ? C2 C3 1.383(15) . ? C3 C4 1.375(16) . ? C4 C5 1.390(15) . ? C5 C6 1.418(14) . ? C6 C7 1.461(14) . ? C7 C8 1.380(14) . ? C8 C9 1.367(15) . ? C9 C10 1.405(15) . ? C9 C17 1.546(16) . ? C10 C11 1.386(15) . ? C11 C12 1.474(15) . ? C12 C13 1.366(15) . ? C13 C14 1.395(14) . ? C14 C15 1.383(16) . ? C14 C21 1.537(15) . ? C15 C16 1.376(15) . ? C17 C19 1.49(2) . ? C17 C20 1.52(2) . ? C17 C18 1.543(17) . ? C21 C22 1.510(18) . ? C21 C23 1.531(18) . ? C21 C24 1.537(16) . ? C25 C26 1.393(15) . ? C27 C28 1.457(18) . ? C29 C30 1.399(15) . ? C30 C31 1.359(15) . ? C31 C32 1.395(14) . ? C31 C45 1.535(16) . ? C32 C33 1.377(15) . ? C33 C34 1.474(13) . ? C34 C35 1.359(14) . ? C35 C36 1.393(14) . ? C36 C37 1.401(15) . ? C36 C49 1.548(14) . ? C37 C38 1.354(14) . ? C38 C39 1.445(14) . ? C39 C40 1.410(14) . ? C39 C44 1.440(15) . ? C40 C41 1.390(16) . ? C41 C42 1.391(17) . ? C42 C43 1.392(15) . ? C43 C44 1.394(15) . ? C45 C47 1.522(17) . ? C45 C48 1.550(18) . ? C45 C46 1.570(17) . ? C49 C50 1.521(16) . ? C49 C51 1.540(15) . ? C49 C52 1.541(16) . ? C53 C54 1.428(18) . ? C55 C56 1.389(18) . ? 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 C1 79.2(4) . . ? N1 Ir1 C27 90.8(4) . . ? C1 Ir1 C27 91.0(4) . . ? N1 Ir1 N2 76.8(3) . . ? C1 Ir1 N2 156.0(4) . . ? C27 Ir1 N2 89.3(4) . . ? N1 Ir1 C25 163.1(4) . . ? C1 Ir1 C25 117.7(4) . . ? C27 Ir1 C25 89.1(4) . . ? N2 Ir1 C25 86.3(4) . . ? N1 Ir1 C26 159.7(4) . . ? C1 Ir1 C26 80.5(4) . . ? C27 Ir1 C26 90.2(5) . . ? N2 Ir1 C26 123.4(4) . . ? C25 Ir1 C26 37.1(4) . . ? N1 Ir1 Cl1 91.4(3) . . ? C1 Ir1 Cl1 91.4(3) . . ? C27 Ir1 Cl1 177.0(3) . . ? N2 Ir1 Cl1 89.4(2) . . ? C25 Ir1 Cl1 88.2(3) . . ? C26 Ir1 Cl1 88.4(4) . . ? N4 Ir2 C44 79.1(4) . . ? N4 Ir2 C55 92.4(4) . . ? C44 Ir2 C55 89.4(4) . . ? N4 Ir2 N3 76.9(3) . . ? C44 Ir2 N3 156.0(4) . . ? C55 Ir2 N3 92.8(4) . . ? N4 Ir2 C54 160.7(4) . . ? C44 Ir2 C54 81.8(5) . . ? C55 Ir2 C54 90.2(5) . . ? N3 Ir2 C54 122.1(4) . . ? N4 Ir2 C53 160.6(4) . . ? C44 Ir2 C53 120.1(4) . . ? C55 Ir2 C53 90.9(5) . . ? N3 Ir2 C53 83.9(4) . . ? C54 Ir2 C53 38.3(5) . . ? N4 Ir2 Cl2 89.0(2) . . ? C44 Ir2 Cl2 92.0(3) . . ? C55 Ir2 Cl2 178.2(3) . . ? N3 Ir2 Cl2 86.4(2) . . ? C54 Ir2 Cl2 88.9(4) . . ? C53 Ir2 Cl2 87.4(4) . . ? C7 N1 C11 119.1(9) . . ? C7 N1 Ir1 120.7(7) . . ? C11 N1 Ir1 120.1(7) . . ? C16 N2 C12 117.2(9) . . ? C16 N2 Ir1 128.2(7) . . ? C12 N2 Ir1 114.6(7) . . ? C29 N3 C33 116.4(9) . . ? C29 N3 Ir2 129.5(7) . . ? C33 N3 Ir2 113.3(6) . . ? C34 N4 C38 120.8(9) . . ? C34 N4 Ir2 119.5(7) . . ? C38 N4 Ir2 119.6(7) . . ? C2 C1 C6 116.9(9) . . ? C2 C1 Ir1 131.6(8) . . ? C6 C1 Ir1 111.5(7) . . ? C3 C2 C1 120.4(11) . . ? C4 C3 C2 123.5(11) . . ? C3 C4 C5 117.6(10) . . ? C4 C5 C6 120.7(11) . . ? C1 C6 C5 120.8(10) . . ? C1 C6 C7 117.7(9) . . ? C5 C6 C7 121.4(10) . . ? N1 C7 C8 120.8(9) . . ? N1 C7 C6 110.8(9) . . ? C8 C7 C6 128.3(9) . . ? C9 C8 C7 121.9(10) . . ? C8 C9 C10 116.9(10) . . ? C8 C9 C17 123.8(10) . . ? C10 C9 C17 119.3(10) . . ? C11 C10 C9 120.2(10) . . ? N1 C11 C10 121.0(10) . . ? N1 C11 C12 114.3(9) . . ? C10 C11 C12 124.6(10) . . ? N2 C12 C13 121.7(10) . . ? N2 C12 C11 114.1(10) . . ? C13 C12 C11 124.2(10) . . ? C12 C13 C14 122.0(10) . . ? C15 C14 C13 115.1(10) . . ? C15 C14 C21 124.3(9) . . ? C13 C14 C21 120.6(10) . . ? C16 C15 C14 121.4(10) . . ? N2 C16 C15 122.5(10) . . ? C19 C17 C20 110.1(12) . . ? C19 C17 C18 108.8(12) . . ? C20 C17 C18 109.2(13) . . ? C19 C17 C9 109.7(11) . . ? C20 C17 C9 109.0(11) . . ? C18 C17 C9 110.1(11) . . ? C22 C21 C23 109.1(10) . . ? C22 C21 C24 108.2(11) . . ? C23 C21 C24 110.1(11) . . ? C22 C21 C14 109.7(10) . . ? C23 C21 C14 109.0(10) . . ? C24 C21 C14 110.8(9) . . ? C26 C25 Ir1 72.5(6) . . ? C25 C26 Ir1 70.3(6) . . ? C28 C27 Ir1 119.3(8) . . ? N3 C29 C30 122.5(10) . . ? C31 C30 C29 120.8(10) . . ? C30 C31 C32 117.2(10) . . ? C30 C31 C45 121.2(9) . . ? C32 C31 C45 121.5(10) . . ? C33 C32 C31 119.9(10) . . ? N3 C33 C32 123.0(9) . . ? N3 C33 C34 114.7(9) . . ? C32 C33 C34 122.2(10) . . ? N4 C34 C35 120.7(9) . . ? N4 C34 C33 114.6(9) . . ? C35 C34 C33 124.6(9) . . ? C34 C35 C36 121.0(10) . . ? C35 C36 C37 116.1(10) . . ? C35 C36 C49 123.3(10) . . ? C37 C36 C49 120.5(9) . . ? C38 C37 C36 121.8(10) . . ? C37 C38 N4 119.6(10) . . ? C37 C38 C39 128.2(10) . . ? N4 C38 C39 112.0(9) . . ? C40 C39 C44 122.4(10) . . ? C40 C39 C38 121.2(10) . . ? C44 C39 C38 116.4(9) . . ? C41 C40 C39 119.2(11) . . ? C40 C41 C42 119.8(11) . . ? C41 C42 C43 120.1(11) . . ? C42 C43 C44 123.6(11) . . ? C43 C44 C39 114.7(9) . . ? C43 C44 Ir2 132.5(8) . . ? C39 C44 Ir2 112.8(7) . . ? C47 C45 C31 108.3(10) . . ? C47 C45 C48 107.2(12) . . ? C31 C45 C48 112.4(10) . . ? C47 C45 C46 108.7(10) . . ? C31 C45 C46 109.5(11) . . ? C48 C45 C46 110.6(12) . . ? C50 C49 C51 111.8(10) . . ? C50 C49 C52 106.9(9) . . ? C51 C49 C52 110.9(10) . . ? C50 C49 C36 111.1(9) . . ? C51 C49 C36 107.8(9) . . ? C52 C49 C36 108.4(9) . . ? C54 C53 Ir2 70.0(6) . . ? C53 C54 Ir2 71.7(7) . . ? C56 C55 Ir2 119.7(9) . . ? Cl3 C57 Cl4 112.3(10) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 3.663 _refine_diff_density_min -2.400 _refine_diff_density_rms 0.243 data_irx2xm_697909 _database_code_depnum_ccdc_archive 'CCDC 697909' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H31 F6 Ir N2 O5' _chemical_formula_weight 817.78 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 11.8262(9) _cell_length_b 12.8751(10) _cell_length_c 13.0574(10) _cell_angle_alpha 60.8400(10) _cell_angle_beta 70.9100(10) _cell_angle_gamma 67.3880(10) _cell_volume 1578.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7307 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 24.54 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.720 _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 4.306 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.646 _exptl_absorpt_correction_T_max 0.806 _exptl_absorpt_process_details Blessing,R.H.,Acta_Crystallogr.1995,A51,33 _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6926 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 24.54 _reflns_number_total 4844 _reflns_number_gt 4004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4844 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.011 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 0.28567(3) 0.13838(3) 0.21950(3) 0.03715(14) Uani 1 1 d . . . N1 N 0.2708(7) 0.2105(7) 0.0331(7) 0.0374(17) Uani 1 1 d . . . N2 N 0.0983(7) 0.2000(7) 0.2228(7) 0.0366(17) Uani 1 1 d . . . O1 O 0.3088(6) 0.3005(6) 0.1923(7) 0.0426(16) Uani 1 1 d . . . O2 O 0.1289(7) 0.4394(7) 0.1435(9) 0.062(2) Uani 1 1 d . . . O3 O 0.2768(8) -0.0347(7) 0.2644(8) 0.057(2) Uani 1 1 d . . . F1 F 0.3905(6) 0.5004(7) 0.1115(9) 0.078(2) Uani 1 1 d . . . F2 F 0.2033(6) 0.6083(6) 0.1403(6) 0.0524(15) Uani 1 1 d . . . F3 F 0.2903(10) 0.4613(8) 0.2867(7) 0.089(3) Uani 1 1 d . . . F4 F 0.3188(16) -0.2781(9) 0.3721(10) 0.137(5) Uani 1 1 d . . . F5 F 0.3665(9) -0.2788(12) 0.2021(11) 0.113(4) Uani 1 1 d . . . F6 F 0.1849(7) -0.2348(11) 0.2788(10) 0.099(3) Uani 1 1 d . . . C13 C -0.1035(9) 0.2208(9) 0.3320(9) 0.041(2) Uani 1 1 d . . . H13 H -0.1567 0.2059 0.4073 0.049 Uiso 1 1 calc R . . C14 C 0.0232(9) 0.1831(8) 0.3268(9) 0.038(2) Uani 1 1 d . . . C25 C 0.4675(8) 0.0545(10) 0.2756(10) 0.046(2) Uani 1 1 d . . . H25A H 0.4934 0.1016 0.3012 0.055 Uiso 1 1 calc R . . H25B H 0.4889 -0.0357 0.3254 0.055 Uiso 1 1 calc R . . C11 C -0.0731(8) 0.2975(9) 0.1221(10) 0.042(2) Uani 1 1 d . . . H11 H -0.1049 0.3390 0.0499 0.050 Uiso 1 1 calc R . . C26 C 0.4836(9) 0.0903(10) 0.1568(10) 0.047(2) Uani 1 1 d . . . H26A H 0.5165 0.0232 0.1292 0.056 Uiso 1 1 calc R . . H26B H 0.5209 0.1602 0.1051 0.056 Uiso 1 1 calc R . . C1 C 0.3598(9) 0.2080(9) -0.0610(10) 0.045(2) Uani 1 1 d . . . H1 H 0.4437 0.1730 -0.0489 0.054 Uiso 1 1 calc R . . C12 C -0.1556(9) 0.2805(9) 0.2292(10) 0.042(2) Uani 1 1 d . . . C10 C 0.0549(8) 0.2551(9) 0.1180(9) 0.038(2) Uani 1 1 d . . . C15 C -0.2968(9) 0.3301(9) 0.2301(9) 0.042(2) Uani 1 1 d . . . C5 C 0.1501(8) 0.2640(8) 0.0110(9) 0.037(2) Uani 1 1 d . . . C27 C 0.2300(9) 0.4023(9) 0.1709(9) 0.042(2) Uani 1 1 d . . . C19 C 0.0911(9) 0.1268(9) 0.4269(8) 0.039(2) Uani 1 1 d . . . C30 C 0.2855(11) -0.2199(10) 0.2693(10) 0.051(3) Uani 1 1 d . . . C17 C -0.3300(10) 0.2720(10) 0.1686(10) 0.050(3) Uani 1 1 d . . . H17A H -0.2949 0.1821 0.2040 0.074 Uiso 1 1 calc R . . H17B H -0.2955 0.3053 0.0834 0.074 Uiso 1 1 calc R . . H17C H -0.4206 0.2916 0.1793 0.074 Uiso 1 1 calc R . . C18 C -0.3255(10) 0.4703(10) 0.1609(12) 0.054(3) Uani 1 1 d . . . H18A H -0.4110 0.5038 0.1459 0.082 Uiso 1 1 calc R . . H18B H -0.2678 0.4907 0.0849 0.082 Uiso 1 1 calc R . . H18C H -0.3159 0.5064 0.2075 0.082 Uiso 1 1 calc R . . C23 C 0.2830(10) 0.0652(10) 0.4897(10) 0.047(2) Uani 1 1 d . . . H23 H 0.3709 0.0496 0.4741 0.056 Uiso 1 1 calc R . . C4 C 0.1226(9) 0.3151(9) -0.1002(9) 0.040(2) Uani 1 1 d . . . H4 H 0.0384 0.3538 -0.1111 0.049 Uiso 1 1 calc R . . C16 C -0.3716(11) 0.2992(13) 0.3544(11) 0.056(3) Uani 1 1 d . . . H16A H -0.3579 0.3430 0.3911 0.085 Uiso 1 1 calc R . . H16B H -0.3455 0.2098 0.4021 0.085 Uiso 1 1 calc R . . H16C H -0.4602 0.3245 0.3506 0.085 Uiso 1 1 calc R . . C6 C 0.1854(11) 0.3690(11) -0.3217(10) 0.051(2) Uani 1 1 d . . . C9 C 0.0801(13) 0.3234(15) -0.3187(12) 0.069(4) Uani 1 1 d . . . H9A H 0.0879 0.2379 -0.2590 0.104 Uiso 1 1 calc R . . H9B H 0.0867 0.3272 -0.3972 0.104 Uiso 1 1 calc R . . H9C H -0.0008 0.3763 -0.2981 0.104 Uiso 1 1 calc R . . C8 C 0.1378(17) 0.5110(14) -0.3649(14) 0.077(4) Uani 1 1 d . . . H8A H 0.0613 0.5322 -0.3115 0.116 Uiso 1 1 calc R . . H8B H 0.1205 0.5486 -0.4458 0.116 Uiso 1 1 calc R . . H8C H 0.2012 0.5423 -0.3646 0.116 Uiso 1 1 calc R . . C7 C 0.2996(15) 0.337(2) -0.4137(14) 0.112(8) Uani 1 1 d . . . H7A H 0.2824 0.3931 -0.4945 0.168 Uiso 1 1 calc R . . H7B H 0.3152 0.2517 -0.4007 0.168 Uiso 1 1 calc R . . H7C H 0.3729 0.3472 -0.4037 0.168 Uiso 1 1 calc R . . C24 C 0.2212(9) 0.1044(9) 0.3968(9) 0.039(2) Uani 1 1 d . . . C2 C 0.3379(10) 0.2524(10) -0.1731(9) 0.044(2) Uani 1 1 d . . . H2 H 0.4056 0.2433 -0.2348 0.053 Uiso 1 1 calc R . . C21 C 0.0923(12) 0.0685(11) 0.6295(11) 0.056(3) Uani 1 1 d . . . H21 H 0.0495 0.0537 0.7087 0.067 Uiso 1 1 calc R . . C22 C 0.2181(11) 0.0485(11) 0.6051(10) 0.052(3) Uani 1 1 d . . . H22 H 0.2618 0.0232 0.6665 0.062 Uiso 1 1 calc R . . C28 C 0.2797(10) 0.4947(10) 0.1767(10) 0.048(2) Uani 1 1 d . . . C20 C 0.0269(11) 0.1094(11) 0.5421(10) 0.051(2) Uani 1 1 d . . . H20 H -0.0611 0.1257 0.5594 0.061 Uiso 1 1 calc R . . C3 C 0.2162(9) 0.3116(9) -0.1987(9) 0.043(2) Uani 1 1 d . . . O4 O 0.3654(15) -0.0584(13) 0.1024(12) 0.113(5) Uani 1 1 d . . . O5 O 0.1524(14) 0.9933(10) 0.9555(12) 0.113(5) Uani 1 1 d . . . C35 C 0.077(3) 0.9375(19) 0.971(2) 0.149(12) Uani 1 1 d . . . C29 C 0.285(3) -0.082(2) 0.2133(15) 0.161(14) 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 0.0318(2) 0.0275(2) 0.0540(3) -0.01369(17) -0.02416(15) -0.00036(14) N1 0.032(4) 0.029(4) 0.049(5) -0.009(4) -0.018(3) -0.006(3) N2 0.035(4) 0.030(4) 0.048(5) -0.015(4) -0.022(3) -0.001(3) O1 0.034(3) 0.032(4) 0.063(5) -0.016(3) -0.028(3) 0.001(3) O2 0.045(4) 0.037(4) 0.106(7) -0.019(5) -0.043(4) -0.003(4) O3 0.069(5) 0.039(4) 0.070(5) -0.017(4) -0.030(4) -0.014(4) F1 0.047(4) 0.045(4) 0.147(8) -0.031(5) -0.045(4) -0.007(3) F2 0.054(4) 0.036(3) 0.071(4) -0.023(3) -0.027(3) -0.003(3) F3 0.166(9) 0.057(5) 0.067(5) -0.006(4) -0.072(5) -0.034(6) F4 0.270(18) 0.043(5) 0.102(8) -0.001(6) -0.083(9) -0.043(8) F5 0.073(6) 0.156(10) 0.158(10) -0.124(9) 0.036(6) -0.045(7) F6 0.058(5) 0.147(9) 0.139(8) -0.098(8) 0.027(5) -0.057(6) C13 0.043(5) 0.034(5) 0.042(5) -0.011(5) -0.015(4) -0.007(4) C14 0.046(5) 0.024(4) 0.046(5) -0.009(4) -0.024(4) -0.005(4) C25 0.024(4) 0.042(6) 0.067(7) -0.020(5) -0.029(4) 0.009(4) C11 0.035(5) 0.032(5) 0.063(6) -0.017(5) -0.024(4) -0.003(4) C26 0.040(5) 0.041(6) 0.062(7) -0.018(5) -0.021(5) -0.007(5) C1 0.037(5) 0.031(5) 0.062(7) -0.012(5) -0.015(5) -0.008(4) C12 0.037(5) 0.029(5) 0.066(7) -0.019(5) -0.025(5) -0.003(4) C10 0.038(5) 0.032(5) 0.050(5) -0.015(5) -0.024(4) -0.004(4) C15 0.036(5) 0.035(5) 0.051(6) -0.009(5) -0.019(4) -0.009(4) C5 0.034(5) 0.027(5) 0.051(6) -0.013(4) -0.022(4) -0.001(4) C27 0.051(6) 0.033(5) 0.043(5) -0.008(5) -0.022(4) -0.013(5) C19 0.041(5) 0.032(5) 0.043(5) -0.008(4) -0.020(4) -0.008(4) C30 0.067(7) 0.038(6) 0.049(6) -0.014(5) -0.015(5) -0.017(5) C17 0.048(6) 0.045(6) 0.061(7) -0.014(5) -0.026(5) -0.015(5) C18 0.046(6) 0.039(6) 0.083(8) -0.019(6) -0.031(6) -0.009(5) C23 0.046(6) 0.043(6) 0.050(6) -0.013(5) -0.024(5) -0.008(5) C4 0.036(5) 0.030(5) 0.056(6) -0.012(5) -0.022(4) -0.006(4) C16 0.038(6) 0.059(7) 0.067(7) -0.026(7) -0.009(5) -0.008(5) C6 0.052(6) 0.054(7) 0.045(6) -0.017(6) -0.014(5) -0.014(6) C9 0.073(9) 0.084(10) 0.070(8) -0.036(8) -0.024(7) -0.023(8) C8 0.110(12) 0.059(9) 0.065(8) -0.011(7) -0.049(8) -0.016(9) C7 0.065(10) 0.22(3) 0.065(9) -0.081(14) 0.007(8) -0.032(14) C24 0.045(5) 0.029(5) 0.044(5) -0.007(4) -0.019(4) -0.012(4) C2 0.042(5) 0.032(5) 0.045(6) -0.005(5) -0.012(4) -0.007(4) C21 0.068(8) 0.054(7) 0.052(7) -0.023(6) -0.017(5) -0.017(6) C22 0.063(7) 0.047(6) 0.045(6) -0.013(5) -0.024(5) -0.012(6) C28 0.057(6) 0.036(5) 0.055(6) -0.010(5) -0.034(5) -0.008(5) C20 0.052(6) 0.049(6) 0.059(7) -0.024(6) -0.017(5) -0.012(5) C3 0.046(5) 0.031(5) 0.053(6) -0.013(5) -0.016(5) -0.009(4) O4 0.157(14) 0.084(9) 0.095(9) -0.045(8) 0.003(9) -0.039(10) O5 0.185(13) 0.044(5) 0.144(10) -0.001(6) -0.127(10) -0.033(7) C35 0.27(3) 0.059(11) 0.120(17) -0.013(12) -0.14(2) 0.015(17) C29 0.38(4) 0.094(15) 0.051(9) 0.003(10) -0.049(16) -0.14(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 N2 2.039(7) . ? Ir1 O3 2.047(7) . ? Ir1 O1 2.053(6) . ? Ir1 C24 2.060(10) . ? Ir1 C26 2.158(10) . ? Ir1 N1 2.184(8) . ? Ir1 C25 2.191(8) . ? N1 C1 1.337(13) . ? N1 C5 1.384(11) . ? N2 C14 1.324(13) . ? N2 C10 1.368(12) . ? O1 C27 1.240(12) . ? O2 C27 1.207(12) . ? O3 C29 1.065(18) . ? F1 C28 1.316(14) . ? F2 C28 1.330(13) . ? F3 C28 1.319(13) . ? F4 C30 1.287(15) . ? F5 C30 1.343(14) . ? F6 C30 1.235(13) . ? C13 C14 1.375(13) . ? C13 C12 1.394(14) . ? C14 C19 1.481(12) . ? C25 C26 1.354(16) . ? C11 C12 1.389(15) . ? C11 C10 1.391(12) . ? C1 C2 1.361(15) . ? C12 C15 1.539(12) . ? C10 C5 1.465(14) . ? C15 C16 1.509(16) . ? C15 C18 1.526(14) . ? C15 C17 1.542(12) . ? C5 C4 1.363(13) . ? C27 C28 1.556(11) . ? C19 C20 1.395(15) . ? C19 C24 1.407(14) . ? C30 C29 1.55(2) . ? C23 C24 1.400(13) . ? C23 C22 1.401(16) . ? C4 C3 1.403(14) . ? C6 C3 1.509(15) . ? C6 C8 1.55(2) . ? C6 C9 1.551(15) . ? C6 C7 1.557(19) . ? C2 C3 1.411(14) . ? C21 C22 1.362(17) . ? C21 C20 1.362(15) . ? O4 C29 1.41(3) . ? O5 C35 1.26(3) . ? 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 N2 Ir1 O3 88.5(3) . . ? N2 Ir1 O1 96.8(3) . . ? O3 Ir1 O1 172.2(3) . . ? N2 Ir1 C24 79.3(3) . . ? O3 Ir1 C24 87.0(3) . . ? O1 Ir1 C24 88.3(3) . . ? N2 Ir1 C26 161.5(4) . . ? O3 Ir1 C26 91.8(4) . . ? O1 Ir1 C26 85.0(3) . . ? C24 Ir1 C26 119.2(4) . . ? N2 Ir1 N1 76.8(3) . . ? O3 Ir1 N1 95.2(3) . . ? O1 Ir1 N1 91.6(3) . . ? C24 Ir1 N1 155.9(3) . . ? C26 Ir1 N1 84.8(3) . . ? N2 Ir1 C25 162.2(4) . . ? O3 Ir1 C25 88.8(4) . . ? O1 Ir1 C25 84.5(3) . . ? C24 Ir1 C25 82.9(4) . . ? C26 Ir1 C25 36.3(4) . . ? N1 Ir1 C25 121.0(4) . . ? C1 N1 C5 115.9(8) . . ? C1 N1 Ir1 129.8(7) . . ? C5 N1 Ir1 114.3(6) . . ? C14 N2 C10 122.4(8) . . ? C14 N2 Ir1 118.6(6) . . ? C10 N2 Ir1 119.0(6) . . ? C27 O1 Ir1 127.2(5) . . ? C29 O3 Ir1 133.2(11) . . ? C14 C13 C12 121.4(9) . . ? N2 C14 C13 119.8(8) . . ? N2 C14 C19 112.7(8) . . ? C13 C14 C19 127.4(9) . . ? C26 C25 Ir1 70.5(6) . . ? C12 C11 C10 121.6(9) . . ? C25 C26 Ir1 73.2(6) . . ? N1 C1 C2 124.2(9) . . ? C11 C12 C13 116.6(9) . . ? C11 C12 C15 120.1(9) . . ? C13 C12 C15 123.2(9) . . ? N2 C10 C11 118.0(9) . . ? N2 C10 C5 115.8(8) . . ? C11 C10 C5 126.2(9) . . ? C16 C15 C18 109.3(9) . . ? C16 C15 C12 112.7(9) . . ? C18 C15 C12 107.0(7) . . ? C16 C15 C17 108.9(8) . . ? C18 C15 C17 110.9(8) . . ? C12 C15 C17 108.0(8) . . ? C4 C5 N1 122.6(9) . . ? C4 C5 C10 123.2(8) . . ? N1 C5 C10 114.1(8) . . ? O2 C27 O1 131.5(8) . . ? O2 C27 C28 118.2(9) . . ? O1 C27 C28 110.2(8) . . ? C20 C19 C24 122.6(8) . . ? C20 C19 C14 120.8(9) . . ? C24 C19 C14 116.3(8) . . ? F6 C30 F4 109.2(12) . . ? F6 C30 F5 104.3(8) . . ? F4 C30 F5 106.5(13) . . ? F6 C30 C29 114.0(17) . . ? F4 C30 C29 110.8(10) . . ? F5 C30 C29 111.6(13) . . ? C24 C23 C22 121.4(9) . . ? C5 C4 C3 121.3(9) . . ? C3 C6 C8 109.4(9) . . ? C3 C6 C9 110.2(9) . . ? C8 C6 C9 107.6(11) . . ? C3 C6 C7 112.5(11) . . ? C8 C6 C7 108.8(13) . . ? C9 C6 C7 108.2(10) . . ? C23 C24 C19 115.8(9) . . ? C23 C24 Ir1 131.7(8) . . ? C19 C24 Ir1 112.5(6) . . ? C1 C2 C3 120.9(10) . . ? C22 C21 C20 121.1(11) . . ? C21 C22 C23 120.0(10) . . ? F1 C28 F3 106.4(9) . . ? F1 C28 F2 107.8(9) . . ? F3 C28 F2 107.5(9) . . ? F1 C28 C27 112.6(9) . . ? F3 C28 C27 110.8(9) . . ? F2 C28 C27 111.4(7) . . ? C21 C20 C19 119.0(10) . . ? C4 C3 C2 114.9(9) . . ? C4 C3 C6 121.2(9) . . ? C2 C3 C6 123.9(9) . . ? O3 C29 O4 119.6(18) . . ? O3 C29 C30 123.4(15) . . ? O4 C29 C30 107.6(17) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 24.54 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 3.420 _refine_diff_density_min -1.342 _refine_diff_density_rms 0.158