# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_irppacac _audit_update_record ; 2012-07-24 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H23 Ir N2 O2, C H2 Cl2' _chemical_formula_sum 'C28 H25 Cl2 Ir N2 O2' _chemical_formula_weight 684.60 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7074(7) _cell_length_b 9.7515(8) _cell_length_c 14.0169(11) _cell_angle_alpha 77.481(7) _cell_angle_beta 81.220(6) _cell_angle_gamma 80.021(7) _cell_volume 1266.54(18) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 8714 _cell_measurement_theta_min 2.8533 _cell_measurement_theta_max 27.2862 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 5.511 _exptl_absorpt_correction_T_min 0.27720 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 140(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 'Oxford Diffraction, KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2812 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11232 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 27.42 _reflns_number_total 5167 _reflns_number_gt 4885 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _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^)+(0.0345P)^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 5167 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0496 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 0.532448(9) 0.203918(10) 0.232191(6) 0.01313(4) Uani 1 1 d . . . O1 O 0.7312(2) 0.1028(2) 0.28317(14) 0.0186(4) Uani 1 1 d . . . O2 O 0.6121(2) 0.1383(2) 0.09417(14) 0.0214(4) Uani 1 1 d . . . N1 N 0.6011(2) 0.3945(2) 0.18173(16) 0.0160(5) Uani 1 1 d . . . N2 N 0.4461(2) 0.0227(2) 0.29178(16) 0.0161(5) Uani 1 1 d . . . C1 C 0.7250(3) 0.4243(3) 0.1993(2) 0.0199(6) Uani 1 1 d . . . H1 H 0.7868 0.3509 0.2344 0.024 Uiso 1 1 calc R . . C2 C 0.7643(3) 0.5567(3) 0.1680(2) 0.0250(6) Uani 1 1 d . . . H2 H 0.8499 0.5758 0.1840 0.030 Uiso 1 1 calc R . . C3 C 0.6776(3) 0.6624(3) 0.1130(2) 0.0248(6) Uani 1 1 d . . . H3 H 0.7048 0.7538 0.0884 0.030 Uiso 1 1 calc R . . C4 C 0.5508(3) 0.6330(3) 0.0942(2) 0.0209(6) Uani 1 1 d . . . H4 H 0.4908 0.7040 0.0558 0.025 Uiso 1 1 calc R . . C5 C 0.5114(3) 0.4990(3) 0.13200(19) 0.0164(5) Uani 1 1 d . . . C6 C 0.3775(3) 0.4548(3) 0.12635(19) 0.0168(5) Uani 1 1 d . . . C7 C 0.2688(3) 0.5444(3) 0.0787(2) 0.0220(6) Uani 1 1 d . . . H7 H 0.2811 0.6387 0.0470 0.026 Uiso 1 1 calc R . . C8 C 0.1441(3) 0.4954(3) 0.0781(2) 0.0264(7) Uani 1 1 d . . . H8 H 0.0695 0.5567 0.0472 0.032 Uiso 1 1 calc R . . C9 C 0.1272(3) 0.3561(3) 0.1225(2) 0.0249(6) Uani 1 1 d . . . H9 H 0.0416 0.3224 0.1209 0.030 Uiso 1 1 calc R . . C10 C 0.2349(3) 0.2658(3) 0.1692(2) 0.0206(6) Uani 1 1 d . . . H10 H 0.2221 0.1709 0.1991 0.025 Uiso 1 1 calc R . . C11 C 0.3625(3) 0.3132(3) 0.17284(18) 0.0146(5) Uani 1 1 d . . . C12 C 0.4513(3) 0.2475(3) 0.36323(19) 0.0151(5) Uani 1 1 d . . . C13 C 0.4477(3) 0.3723(3) 0.3999(2) 0.0177(5) Uani 1 1 d . . . H13 H 0.4881 0.4499 0.3588 0.021 Uiso 1 1 calc R . . C14 C 0.3865(3) 0.3843(3) 0.4946(2) 0.0208(6) Uani 1 1 d . . . H14 H 0.3839 0.4704 0.5166 0.025 Uiso 1 1 calc R . . C15 C 0.3291(3) 0.2719(3) 0.5577(2) 0.0214(6) Uani 1 1 d . . . H15 H 0.2906 0.2796 0.6231 0.026 Uiso 1 1 calc R . . C16 C 0.3287(3) 0.1491(3) 0.5240(2) 0.0192(6) Uani 1 1 d . . . H16 H 0.2893 0.0718 0.5664 0.023 Uiso 1 1 calc R . . C17 C 0.3860(3) 0.1381(3) 0.42796(19) 0.0163(5) Uani 1 1 d . . . C18 C 0.3810(3) 0.0152(3) 0.38571(19) 0.0158(5) Uani 1 1 d . . . C19 C 0.3153(3) -0.1023(3) 0.4327(2) 0.0212(6) Uani 1 1 d . . . H19 H 0.2720 -0.1080 0.4987 0.025 Uiso 1 1 calc R . . C20 C 0.3130(3) -0.2096(3) 0.3838(2) 0.0247(6) Uani 1 1 d . . . H20 H 0.2674 -0.2892 0.4150 0.030 Uiso 1 1 calc R . . C21 C 0.3786(3) -0.1996(3) 0.2879(2) 0.0242(6) Uani 1 1 d . . . H21 H 0.3781 -0.2722 0.2524 0.029 Uiso 1 1 calc R . . C22 C 0.4443(3) -0.0841(3) 0.2447(2) 0.0209(6) Uani 1 1 d . . . H22 H 0.4902 -0.0789 0.1794 0.025 Uiso 1 1 calc R . . C23 C 0.8318(3) 0.0360(3) 0.2348(2) 0.0209(6) Uani 1 1 d . . . C24 C 0.8333(3) 0.0129(3) 0.1387(2) 0.0253(6) Uani 1 1 d . . . H24 H 0.9148 -0.0442 0.1141 0.030 Uiso 1 1 calc R . . C25 C 0.7307(3) 0.0629(3) 0.0757(2) 0.0213(6) Uani 1 1 d . . . C26 C 0.9615(3) -0.0210(4) 0.2863(2) 0.0299(7) Uani 1 1 d . . . H26A H 0.9935 0.0565 0.3074 0.045 Uiso 1 1 calc R . . H26B H 1.0363 -0.0623 0.2411 0.045 Uiso 1 1 calc R . . H26C H 0.9390 -0.0942 0.3440 0.045 Uiso 1 1 calc R . . C27 C 0.7564(4) 0.0264(4) -0.0256(2) 0.0299(7) Uani 1 1 d . . . H27A H 0.6744 -0.0106 -0.0377 0.045 Uiso 1 1 calc R . . H27B H 0.8399 -0.0457 -0.0296 0.045 Uiso 1 1 calc R . . H27C H 0.7716 0.1119 -0.0753 0.045 Uiso 1 1 calc R . . C28 C -0.0874(3) -0.4082(4) 0.6180(3) 0.0373(8) Uani 1 1 d . . . H28A H -0.1274 -0.3923 0.5549 0.045 Uiso 1 1 calc R . . H28B H -0.1608 -0.3696 0.6664 0.045 Uiso 1 1 calc R . . Cl1 Cl -0.04122(12) -0.59115(11) 0.66004(8) 0.0528(3) Uani 1 1 d . . . Cl2 Cl 0.05822(11) -0.31763(13) 0.60071(7) 0.0558(3) 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 0.01223(6) 0.01475(6) 0.01126(6) -0.00030(4) -0.00132(4) -0.00176(4) O1 0.0148(9) 0.0213(10) 0.0169(10) 0.0005(8) -0.0025(7) 0.0002(8) O2 0.0208(10) 0.0251(11) 0.0158(10) -0.0017(8) -0.0003(8) -0.0009(8) N1 0.0153(11) 0.0190(12) 0.0127(11) -0.0020(9) 0.0003(8) -0.0026(9) N2 0.0156(11) 0.0165(11) 0.0148(11) -0.0002(9) -0.0022(8) -0.0023(9) C1 0.0137(13) 0.0242(15) 0.0206(14) -0.0024(11) -0.0016(10) -0.0018(11) C2 0.0191(15) 0.0292(16) 0.0274(16) -0.0055(13) 0.0018(11) -0.0096(12) C3 0.0282(16) 0.0191(15) 0.0248(15) -0.0036(12) 0.0064(12) -0.0065(12) C4 0.0237(15) 0.0177(14) 0.0182(14) -0.0021(11) 0.0013(11) 0.0000(11) C5 0.0189(13) 0.0179(13) 0.0107(12) -0.0029(10) -0.0009(10) 0.0011(10) C6 0.0187(13) 0.0186(13) 0.0116(12) -0.0047(10) -0.0005(10) 0.0024(10) C7 0.0228(15) 0.0220(15) 0.0198(14) -0.0040(11) -0.0054(11) 0.0030(11) C8 0.0227(15) 0.0340(17) 0.0203(15) -0.0049(12) -0.0082(11) 0.0063(13) C9 0.0160(14) 0.0371(18) 0.0231(15) -0.0085(13) -0.0058(11) -0.0013(12) C10 0.0169(14) 0.0268(15) 0.0194(14) -0.0052(11) -0.0033(10) -0.0050(11) C11 0.0135(13) 0.0203(13) 0.0095(12) -0.0029(10) -0.0029(9) 0.0005(10) C12 0.0086(12) 0.0212(14) 0.0140(13) 0.0007(10) -0.0045(9) -0.0004(10) C13 0.0162(13) 0.0192(14) 0.0187(13) -0.0043(11) -0.0028(10) -0.0040(11) C14 0.0183(14) 0.0238(15) 0.0233(15) -0.0100(12) -0.0052(11) -0.0019(11) C15 0.0206(14) 0.0302(16) 0.0135(13) -0.0068(11) -0.0004(10) -0.0023(12) C16 0.0173(13) 0.0211(14) 0.0164(13) 0.0003(11) 0.0002(10) -0.0023(11) C17 0.0128(12) 0.0200(13) 0.0141(13) -0.0002(10) -0.0035(10) 0.0005(10) C18 0.0133(12) 0.0162(13) 0.0162(13) -0.0011(10) -0.0021(10) 0.0005(10) C19 0.0214(14) 0.0201(14) 0.0196(14) 0.0016(11) 0.0004(11) -0.0051(11) C20 0.0241(15) 0.0178(14) 0.0314(16) -0.0008(12) -0.0021(12) -0.0067(12) C21 0.0276(16) 0.0197(15) 0.0268(16) -0.0075(12) -0.0024(12) -0.0043(12) C22 0.0218(15) 0.0198(14) 0.0218(14) -0.0070(11) -0.0019(11) -0.0018(11) C23 0.0187(14) 0.0184(14) 0.0215(14) 0.0047(11) -0.0006(11) -0.0040(11) C24 0.0192(15) 0.0271(16) 0.0256(16) -0.0047(12) 0.0033(11) 0.0015(12) C25 0.0239(15) 0.0172(14) 0.0200(14) -0.0001(11) 0.0038(11) -0.0051(11) C26 0.0193(15) 0.0349(18) 0.0319(17) -0.0009(14) -0.0038(12) -0.0008(13) C27 0.0355(18) 0.0299(17) 0.0210(15) -0.0055(13) 0.0019(13) 0.0005(14) C28 0.0236(17) 0.046(2) 0.046(2) -0.0167(17) -0.0069(14) -0.0027(15) Cl1 0.0568(6) 0.0422(5) 0.0642(7) -0.0157(5) -0.0224(5) -0.0008(5) Cl2 0.0520(6) 0.0800(8) 0.0424(5) -0.0061(5) -0.0048(4) -0.0368(6) _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 C12 1.989(3) . ? Ir1 C11 1.993(3) . ? Ir1 N1 2.029(2) . ? Ir1 N2 2.045(2) . ? Ir1 O2 2.159(2) . ? Ir1 O1 2.1593(19) . ? O1 C23 1.267(3) . ? O2 C25 1.277(3) . ? N1 C1 1.354(4) . ? N1 C5 1.360(4) . ? N2 C22 1.352(4) . ? N2 C18 1.363(3) . ? C1 C2 1.371(4) . ? C1 H1 0.9500 . ? C2 C3 1.385(4) . ? C2 H2 0.9500 . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.395(4) . ? C4 H4 0.9500 . ? C5 C6 1.457(4) . ? C6 C7 1.402(4) . ? C6 C11 1.416(4) . ? C7 C8 1.379(4) . ? C7 H7 0.9500 . ? C8 C9 1.393(4) . ? C8 H8 0.9500 . ? C9 C10 1.392(4) . ? C9 H9 0.9500 . ? C10 C11 1.406(4) . ? C10 H10 0.9500 . ? C12 C13 1.413(4) . ? C12 C17 1.415(4) . ? C13 C14 1.390(4) . ? C13 H13 0.9500 . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 C17 1.396(4) . ? C16 H16 0.9500 . ? C17 C18 1.459(4) . ? C18 C19 1.396(4) . ? C19 C20 1.375(4) . ? C19 H19 0.9500 . ? C20 C21 1.388(4) . ? C20 H20 0.9500 . ? C21 C22 1.369(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.410(4) . ? C23 C26 1.509(4) . ? C24 C25 1.387(4) . ? C24 H24 0.9500 . ? C25 C27 1.512(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 Cl2 1.753(3) . ? C28 Cl1 1.755(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 C12 Ir1 C11 90.83(10) . . ? C12 Ir1 N1 94.15(10) . . ? C11 Ir1 N1 80.66(10) . . ? C12 Ir1 N2 80.65(10) . . ? C11 Ir1 N2 96.15(10) . . ? N1 Ir1 N2 173.90(8) . . ? C12 Ir1 O2 174.62(9) . . ? C11 Ir1 O2 89.54(9) . . ? N1 Ir1 O2 91.21(8) . . ? N2 Ir1 O2 93.98(8) . . ? C12 Ir1 O1 92.97(9) . . ? C11 Ir1 O1 172.98(8) . . ? N1 Ir1 O1 93.17(8) . . ? N2 Ir1 O1 90.30(8) . . ? O2 Ir1 O1 87.24(8) . . ? C23 O1 Ir1 125.98(19) . . ? C25 O2 Ir1 125.74(19) . . ? C1 N1 C5 119.4(2) . . ? C1 N1 Ir1 124.04(19) . . ? C5 N1 Ir1 116.46(18) . . ? C22 N2 C18 119.0(2) . . ? C22 N2 Ir1 125.55(19) . . ? C18 N2 Ir1 115.43(18) . . ? N1 C1 C2 122.2(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 120.2(3) . . ? N1 C5 C6 113.2(2) . . ? C4 C5 C6 126.6(3) . . ? C7 C6 C11 121.1(3) . . ? C7 C6 C5 123.4(2) . . ? C11 C6 C5 115.6(2) . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 117.6(2) . . ? C10 C11 Ir1 128.3(2) . . ? C6 C11 Ir1 114.08(19) . . ? C13 C12 C17 115.8(2) . . ? C13 C12 Ir1 129.3(2) . . ? C17 C12 Ir1 114.9(2) . . ? C14 C13 C12 121.6(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 120.8(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.2(3) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 122.3(3) . . ? C16 C17 C18 123.0(2) . . ? C12 C17 C18 114.8(2) . . ? N2 C18 C19 120.2(3) . . ? N2 C18 C17 114.2(2) . . ? C19 C18 C17 125.6(2) . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 118.7(3) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 119.4(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? N2 C22 C21 122.4(3) . . ? N2 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? O1 C23 C24 126.2(3) . . ? O1 C23 C26 115.5(3) . . ? C24 C23 C26 118.3(3) . . ? C25 C24 C23 128.2(3) . . ? C25 C24 H24 115.9 . . ? C23 C24 H24 115.9 . . ? O2 C25 C24 126.5(3) . . ? O2 C25 C27 114.5(3) . . ? C24 C25 C27 119.0(3) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Cl2 C28 Cl1 111.7(2) . . ? Cl2 C28 H28A 109.3 . . ? Cl1 C28 H28A 109.3 . . ? Cl2 C28 H28B 109.3 . . ? Cl1 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 Ir1 O1 C23 172.8(2) . . . . ? N1 Ir1 O1 C23 -92.9(2) . . . . ? N2 Ir1 O1 C23 92.1(2) . . . . ? O2 Ir1 O1 C23 -1.8(2) . . . . ? C11 Ir1 O2 C25 177.2(2) . . . . ? N1 Ir1 O2 C25 96.5(2) . . . . ? N2 Ir1 O2 C25 -86.7(2) . . . . ? O1 Ir1 O2 C25 3.4(2) . . . . ? C12 Ir1 N1 C1 84.1(2) . . . . ? C11 Ir1 N1 C1 174.2(2) . . . . ? O2 Ir1 N1 C1 -96.5(2) . . . . ? O1 Ir1 N1 C1 -9.2(2) . . . . ? C12 Ir1 N1 C5 -92.29(19) . . . . ? C11 Ir1 N1 C5 -2.14(19) . . . . ? O2 Ir1 N1 C5 87.20(19) . . . . ? O1 Ir1 N1 C5 174.50(18) . . . . ? C12 Ir1 N2 C22 176.3(2) . . . . ? C11 Ir1 N2 C22 86.5(2) . . . . ? O2 Ir1 N2 C22 -3.5(2) . . . . ? O1 Ir1 N2 C22 -90.7(2) . . . . ? C12 Ir1 N2 C18 -1.01(19) . . . . ? C11 Ir1 N2 C18 -90.8(2) . . . . ? O2 Ir1 N2 C18 179.19(19) . . . . ? O1 Ir1 N2 C18 91.94(19) . . . . ? C5 N1 C1 C2 -0.4(4) . . . . ? Ir1 N1 C1 C2 -176.6(2) . . . . ? N1 C1 C2 C3 -2.9(4) . . . . ? C1 C2 C3 C4 2.5(4) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C1 N1 C5 C4 3.9(4) . . . . ? Ir1 N1 C5 C4 -179.56(19) . . . . ? C1 N1 C5 C6 -174.8(2) . . . . ? Ir1 N1 C5 C6 1.7(3) . . . . ? C3 C4 C5 N1 -4.2(4) . . . . ? C3 C4 C5 C6 174.4(3) . . . . ? N1 C5 C6 C7 -180.0(2) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? N1 C5 C6 C11 0.1(3) . . . . ? C4 C5 C6 C11 -178.5(3) . . . . ? C11 C6 C7 C8 1.0(4) . . . . ? C5 C6 C7 C8 -178.9(3) . . . . ? C6 C7 C8 C9 -1.6(4) . . . . ? C7 C8 C9 C10 1.0(4) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C9 C10 C11 C6 -0.7(4) . . . . ? C9 C10 C11 Ir1 -178.5(2) . . . . ? C7 C6 C11 C10 0.1(4) . . . . ? C5 C6 C11 C10 -180.0(2) . . . . ? C7 C6 C11 Ir1 178.2(2) . . . . ? C5 C6 C11 Ir1 -1.9(3) . . . . ? C12 Ir1 C11 C10 -86.0(2) . . . . ? N1 Ir1 C11 C10 180.0(3) . . . . ? N2 Ir1 C11 C10 -5.3(3) . . . . ? O2 Ir1 C11 C10 88.7(2) . . . . ? C12 Ir1 C11 C6 96.2(2) . . . . ? N1 Ir1 C11 C6 2.11(18) . . . . ? N2 Ir1 C11 C6 176.86(19) . . . . ? O2 Ir1 C11 C6 -89.19(19) . . . . ? C11 Ir1 C12 C13 -80.2(3) . . . . ? N1 Ir1 C12 C13 0.5(3) . . . . ? N2 Ir1 C12 C13 -176.3(3) . . . . ? O1 Ir1 C12 C13 93.9(2) . . . . ? C11 Ir1 C12 C17 98.7(2) . . . . ? N1 Ir1 C12 C17 179.4(2) . . . . ? N2 Ir1 C12 C17 2.61(19) . . . . ? O1 Ir1 C12 C17 -87.2(2) . . . . ? C17 C12 C13 C14 1.5(4) . . . . ? Ir1 C12 C13 C14 -179.7(2) . . . . ? C12 C13 C14 C15 1.4(4) . . . . ? C13 C14 C15 C16 -2.4(4) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? C15 C16 C17 C12 2.7(4) . . . . ? C15 C16 C17 C18 -176.0(3) . . . . ? C13 C12 C17 C16 -3.5(4) . . . . ? Ir1 C12 C17 C16 177.4(2) . . . . ? C13 C12 C17 C18 175.3(2) . . . . ? Ir1 C12 C17 C18 -3.8(3) . . . . ? C22 N2 C18 C19 0.8(4) . . . . ? Ir1 N2 C18 C19 178.4(2) . . . . ? C22 N2 C18 C17 -178.2(2) . . . . ? Ir1 N2 C18 C17 -0.7(3) . . . . ? C16 C17 C18 N2 -178.3(2) . . . . ? C12 C17 C18 N2 2.9(3) . . . . ? C16 C17 C18 C19 2.7(4) . . . . ? C12 C17 C18 C19 -176.1(3) . . . . ? N2 C18 C19 C20 -1.5(4) . . . . ? C17 C18 C19 C20 177.5(3) . . . . ? C18 C19 C20 C21 0.8(5) . . . . ? C19 C20 C21 C22 0.4(5) . . . . ? C18 N2 C22 C21 0.4(4) . . . . ? Ir1 N2 C22 C21 -176.9(2) . . . . ? C20 C21 C22 N2 -1.0(5) . . . . ? Ir1 O1 C23 C24 -0.9(4) . . . . ? Ir1 O1 C23 C26 178.17(18) . . . . ? O1 C23 C24 C25 3.6(5) . . . . ? C26 C23 C24 C25 -175.5(3) . . . . ? Ir1 O2 C25 C24 -2.4(4) . . . . ? Ir1 O2 C25 C27 176.98(18) . . . . ? C23 C24 C25 O2 -1.7(5) . . . . ? C23 C24 C25 C27 178.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.176 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.104 _iucr_refine_instructions_details ; TITL IRPPACAC in P-1 CELL 0.71073 9.707393 9.751465 14.016866 77.4814 81.2203 80.0211 ZERR 2.00 0.000726 0.000821 0.001123 0.0070 0.0064 0.0066 LATT 1 SFAC C H N O CL IR UNIT 56 50 4 4 4 2 REM ---------------------------------------------------------------------- REM Data collection: KUMA CCD REM Absorption correction: ABSPACK REM Crystal habit: prismatic; Crystal colour: yellow REM Mole 1 is the Ir(III) complex REM Mole 2 is a DCM solvent molecule REM ---------------------------------------------------------------------- L.S. 10 OMIT -6 5 1 OMIT -7 4 0 ACTA 50 CONF SIZE 0.28 0.18 0.15 WPDB -2 BOND $H FMAP 2 PLAN 10 TEMP -133 WGHT 0.034500 FVAR 1.46126 MOLE 1 IR1 6 0.532448 0.203918 0.232191 11.00000 0.01223 0.01475 = 0.01126 -0.00030 -0.00132 -0.00176 O1 4 0.731219 0.102754 0.283171 11.00000 0.01482 0.02126 = 0.01694 0.00054 -0.00253 0.00024 O2 4 0.612144 0.138278 0.094169 11.00000 0.02077 0.02505 = 0.01582 -0.00173 -0.00026 -0.00090 N1 3 0.601079 0.394545 0.181730 11.00000 0.01529 0.01897 = 0.01274 -0.00198 0.00028 -0.00262 N2 3 0.446098 0.022731 0.291777 11.00000 0.01561 0.01655 = 0.01484 -0.00021 -0.00217 -0.00227 C1 1 0.725006 0.424299 0.199260 11.00000 0.01366 0.02416 = 0.02057 -0.00235 -0.00165 -0.00177 AFIX 43 H1 2 0.786791 0.350939 0.234374 11.00000 -1.20000 AFIX 0 C2 1 0.764296 0.556725 0.168036 11.00000 0.01905 0.02924 = 0.02742 -0.00550 0.00185 -0.00964 AFIX 43 H2 2 0.849874 0.575762 0.183967 11.00000 -1.20000 AFIX 0 C3 1 0.677633 0.662431 0.112960 11.00000 0.02820 0.01911 = 0.02475 -0.00358 0.00640 -0.00650 AFIX 43 H3 2 0.704768 0.753799 0.088376 11.00000 -1.20000 AFIX 0 C4 1 0.550771 0.633040 0.094216 11.00000 0.02372 0.01773 = 0.01823 -0.00210 0.00131 0.00001 AFIX 43 H4 2 0.490792 0.703963 0.055761 11.00000 -1.20000 AFIX 0 C5 1 0.511450 0.498970 0.132004 11.00000 0.01891 0.01795 = 0.01071 -0.00289 -0.00092 0.00110 C6 1 0.377529 0.454834 0.126354 11.00000 0.01873 0.01858 = 0.01158 -0.00466 -0.00050 0.00239 C7 1 0.268831 0.544396 0.078746 11.00000 0.02285 0.02199 = 0.01979 -0.00397 -0.00542 0.00300 AFIX 43 H7 2 0.281083 0.638718 0.046994 11.00000 -1.20000 AFIX 0 C8 1 0.144098 0.495377 0.078074 11.00000 0.02268 0.03399 = 0.02033 -0.00487 -0.00823 0.00626 AFIX 43 H8 2 0.069519 0.556750 0.047224 11.00000 -1.20000 AFIX 0 C9 1 0.127209 0.356076 0.122527 11.00000 0.01596 0.03714 = 0.02308 -0.00848 -0.00576 -0.00126 AFIX 43 H9 2 0.041570 0.322434 0.120950 11.00000 -1.20000 AFIX 0 C10 1 0.234908 0.265803 0.169246 11.00000 0.01691 0.02676 = 0.01941 -0.00516 -0.00333 -0.00505 AFIX 43 H10 2 0.222058 0.170947 0.199098 11.00000 -1.20000 AFIX 0 C11 1 0.362522 0.313179 0.172841 11.00000 0.01354 0.02028 = 0.00955 -0.00292 -0.00295 0.00052 C12 1 0.451282 0.247508 0.363235 11.00000 0.00859 0.02120 = 0.01404 0.00068 -0.00447 -0.00042 C13 1 0.447731 0.372312 0.399864 11.00000 0.01616 0.01922 = 0.01866 -0.00427 -0.00280 -0.00399 AFIX 43 H13 2 0.488130 0.449859 0.358760 11.00000 -1.20000 AFIX 0 C14 1 0.386546 0.384338 0.494592 11.00000 0.01827 0.02377 = 0.02333 -0.00996 -0.00524 -0.00185 AFIX 43 H14 2 0.383921 0.470433 0.516555 11.00000 -1.20000 AFIX 0 C15 1 0.329084 0.271870 0.557669 11.00000 0.02060 0.03022 = 0.01346 -0.00675 -0.00036 -0.00226 AFIX 43 H15 2 0.290584 0.279569 0.623123 11.00000 -1.20000 AFIX 0 C16 1 0.328687 0.149085 0.524036 11.00000 0.01731 0.02105 = 0.01644 0.00028 0.00016 -0.00228 AFIX 43 H16 2 0.289310 0.071824 0.566360 11.00000 -1.20000 AFIX 0 C17 1 0.386018 0.138127 0.427956 11.00000 0.01281 0.02000 = 0.01414 -0.00017 -0.00350 0.00051 C18 1 0.380997 0.015179 0.385705 11.00000 0.01330 0.01616 = 0.01623 -0.00107 -0.00213 0.00047 C19 1 0.315277 -0.102256 0.432667 11.00000 0.02141 0.02008 = 0.01957 0.00157 0.00039 -0.00507 AFIX 43 H19 2 0.271967 -0.107977 0.498657 11.00000 -1.20000 AFIX 0 C20 1 0.313004 -0.209647 0.383766 11.00000 0.02411 0.01777 = 0.03135 -0.00076 -0.00210 -0.00675 AFIX 43 H20 2 0.267380 -0.289202 0.415033 11.00000 -1.20000 AFIX 0 C21 1 0.378649 -0.199571 0.287851 11.00000 0.02760 0.01969 = 0.02678 -0.00748 -0.00240 -0.00432 AFIX 43 H21 2 0.378055 -0.272152 0.252408 11.00000 -1.20000 AFIX 0 C22 1 0.444286 -0.084090 0.244745 11.00000 0.02182 0.01983 = 0.02176 -0.00702 -0.00187 -0.00177 AFIX 43 H22 2 0.490206 -0.078857 0.179431 11.00000 -1.20000 AFIX 0 C23 1 0.831822 0.036005 0.234772 11.00000 0.01870 0.01845 = 0.02145 0.00465 -0.00063 -0.00396 C24 1 0.833304 0.012884 0.138735 11.00000 0.01920 0.02710 = 0.02558 -0.00470 0.00328 0.00154 AFIX 43 H24 2 0.914833 -0.044191 0.114109 11.00000 -1.20000 AFIX 0 C25 1 0.730748 0.062949 0.075658 11.00000 0.02385 0.01717 = 0.02003 -0.00015 0.00384 -0.00512 C26 1 0.961513 -0.021015 0.286340 11.00000 0.01926 0.03491 = 0.03189 -0.00087 -0.00381 -0.00084 AFIX 33 H26A 2 0.993501 0.056460 0.307409 11.00000 -1.50000 H26B 2 1.036278 -0.062348 0.241091 11.00000 -1.50000 H26C 2 0.938978 -0.094182 0.344008 11.00000 -1.50000 AFIX 0 C27 1 0.756427 0.026414 -0.025619 11.00000 0.03549 0.02987 = 0.02101 -0.00551 0.00189 0.00054 AFIX 33 H27A 2 0.674371 -0.010586 -0.037679 11.00000 -1.50000 H27B 2 0.839922 -0.045721 -0.029567 11.00000 -1.50000 H27C 2 0.771637 0.111863 -0.075275 11.00000 -1.50000 AFIX 0 MOLE 2 C28 1 -0.087413 -0.408187 0.617965 11.00000 0.02357 0.04560 = 0.04624 -0.01669 -0.00691 -0.00271 AFIX 23 H28A 2 -0.127410 -0.392274 0.554922 11.00000 -1.20000 H28B 2 -0.160843 -0.369565 0.666354 11.00000 -1.20000 AFIX 0 CL1 5 -0.041217 -0.591147 0.660038 11.00000 0.05683 0.04224 = 0.06423 -0.01571 -0.02243 -0.00081 CL2 5 0.058224 -0.317635 0.600714 11.00000 0.05198 0.07996 = 0.04240 -0.00613 -0.00483 -0.03683 MOLE 0 HKLF 4 REM IRPPACAC in P-1 REM R1 = 0.0196 for 4885 Fo > 4sig(Fo) and 0.0213 for all 5167 data REM 316 parameters refined using 0 restraints END WGHT 0.0344 0.0178 REM Highest difference peak 1.176, deepest hole -0.562, 1-sigma level 0.104 Q1 1 0.5392 0.1407 0.2848 11.00000 0.05 1.18 Q2 1 0.4852 0.2623 0.2749 11.00000 0.05 1.11 Q3 1 0.5185 0.2698 0.1771 11.00000 0.05 0.96 Q4 1 0.5784 0.1395 0.1962 11.00000 0.05 0.83 Q5 1 0.5785 0.2569 0.2532 11.00000 0.05 0.82 Q6 1 0.4710 0.1523 0.2179 11.00000 0.05 0.76 Q7 1 0.0202 -0.5480 0.6285 11.00000 0.05 0.76 Q8 1 0.4384 0.2620 0.1880 11.00000 0.05 0.63 Q9 1 0.4364 0.1823 0.4043 11.00000 0.05 0.58 Q10 1 0.5414 0.4395 0.1728 11.00000 0.05 0.52 ; _database_code_depnum_ccdc_archive 'CCDC 964310' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eb70b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H19 F4 Ir N2 O2' _chemical_formula_sum 'C27 H19 F4 Ir N2 O2' _chemical_formula_weight 671.64 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2843(12) _cell_length_b 20.156(3) _cell_length_c 17.0651(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.041(7) _cell_angle_gamma 90.00 _cell_volume 4644.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 193 _cell_measurement_theta_min 4.074 _cell_measurement_theta_max 22.404 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 5.810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3163 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS, Bruker AXS, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 149363 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.50 _reflns_number_total 10600 _reflns_number_gt 8276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0414P)^2^+60.6415P] 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 10600 _refine_ls_number_parameters 656 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Ir1A Ir 0.37087(2) 0.72299(1) 0.16995(1) 0.00839(7) Uani 0.9441(5) 1 d P . . Ir1B Ir 0.3962(3) 0.7229(2) 0.2313(3) 0.00839(7) Uani 0.0559(5) 1 d P . . F1 F 0.2533(4) 0.5582(2) 0.3569(3) 0.0350(11) Uani 1 1 d . . . F2 F 0.0667(3) 0.5497(2) 0.0745(3) 0.0313(10) Uani 1 1 d . . . F3 F 0.6456(3) 0.5309(2) 0.2049(3) 0.0245(9) Uani 1 1 d . . . F4 F 0.4670(3) 0.5993(2) -0.0650(2) 0.0227(9) Uani 1 1 d . . . O1 O 0.4737(3) 0.8007(2) 0.1705(3) 0.0167(9) Uani 1 1 d . . . O2 O 0.2751(3) 0.7958(2) 0.1960(3) 0.0159(9) Uani 1 1 d . . . N1 N 0.4294(4) 0.7071(3) 0.2939(3) 0.0165(11) Uani 1 1 d . . . N2 N 0.3101(4) 0.7327(3) 0.0437(3) 0.0117(10) Uani 1 1 d . . . C1 C 0.5082(5) 0.7401(4) 0.3456(4) 0.0179(13) Uani 1 1 d . . . H1 H 0.5409 0.7718 0.3224 0.021 Uiso 1 1 calc R . . C2 C 0.5430(5) 0.7301(4) 0.4294(4) 0.0196(14) Uani 1 1 d . . . H2 H 0.5987 0.7542 0.4632 0.024 Uiso 1 1 calc R . . C3 C 0.4959(5) 0.6842(4) 0.4647(4) 0.0192(14) Uani 1 1 d . . . H3 H 0.5174 0.6775 0.5230 0.023 Uiso 1 1 calc R . . C4 C 0.4169(5) 0.6481(4) 0.4128(4) 0.0206(14) Uani 1 1 d . . . H4 H 0.3853 0.6154 0.4355 0.025 Uiso 1 1 calc R . . C5 C 0.3836(5) 0.6599(3) 0.3270(4) 0.0145(12) Uani 1 1 d . . . C6 C 0.3005(5) 0.6282(3) 0.2640(4) 0.0165(13) Uani 1 1 d . . . C7 C 0.2377(6) 0.5798(4) 0.2782(4) 0.0261(16) Uani 1 1 d . . . C8 C 0.1597(6) 0.5521(4) 0.2163(5) 0.0244(15) Uani 1 1 d . . . H8 H 0.1182 0.5192 0.2278 0.029 Uiso 1 1 calc R . . C9 C 0.1451(5) 0.5747(4) 0.1371(4) 0.0231(15) Uani 1 1 d . . . C10 C 0.2032(5) 0.6224(3) 0.1179(4) 0.0173(13) Uani 1 1 d . . . H10 H 0.1899 0.6361 0.0620 0.021 Uiso 1 1 calc R . . C11 C 0.2820(4) 0.6506(3) 0.1808(4) 0.0145(13) Uani 1 1 d . . . C12 C 0.4525(5) 0.6551(3) 0.1354(4) 0.0151(12) Uani 1 1 d . . . C13 C 0.5237(5) 0.6137(3) 0.1885(4) 0.0150(13) Uani 1 1 d . . . H13 H 0.5372 0.6155 0.2468 0.018 Uiso 1 1 calc R . . C14 C 0.5742(5) 0.5701(3) 0.1539(4) 0.0176(13) Uani 1 1 d . . . C15 C 0.5562(5) 0.5645(3) 0.0687(4) 0.0186(13) Uani 1 1 d . . . H15 H 0.5917 0.5339 0.0468 0.022 Uiso 1 1 calc R . . C16 C 0.4857(5) 0.6049(3) 0.0186(4) 0.0179(13) Uani 1 1 d . . . C17 C 0.4310(5) 0.6505(3) 0.0487(4) 0.0140(12) Uani 1 1 d . . . C18 C 0.3508(5) 0.6933(3) -0.0020(4) 0.0118(12) Uani 1 1 d . . . C19 C 0.3123(5) 0.6960(3) -0.0893(4) 0.0163(13) Uani 1 1 d . . . H19 H 0.3392 0.6685 -0.1218 0.020 Uiso 1 1 calc R . . C20 C 0.2350(5) 0.7391(3) -0.1274(4) 0.0166(13) Uani 1 1 d . . . H20 H 0.2092 0.7417 -0.1861 0.020 Uiso 1 1 calc R . . C21 C 0.1958(5) 0.7784(3) -0.0792(4) 0.0184(14) Uani 1 1 d . . . H21 H 0.1427 0.8079 -0.1045 0.022 Uiso 1 1 calc R . . C22 C 0.2349(5) 0.7740(3) 0.0058(4) 0.0174(13) Uani 1 1 d . . . H22 H 0.2079 0.8011 0.0387 0.021 Uiso 1 1 calc R . . C23 C 0.4613(5) 0.8617(3) 0.1869(4) 0.0169(13) Uani 1 1 d . . . C24 C 0.3801(5) 0.8892(3) 0.2029(4) 0.0172(13) Uani 1 1 d . . . H24 H 0.3841 0.9355 0.2141 0.021 Uiso 1 1 calc R . . C25 C 0.2933(5) 0.8581(3) 0.2048(4) 0.0129(12) Uani 1 1 d . . . C26 C 0.5468(5) 0.9056(4) 0.1870(5) 0.0235(15) Uani 1 1 d . . . H26A H 0.6091 0.8853 0.2211 0.035 Uiso 1 1 calc R . . H26B H 0.5394 0.9492 0.2097 0.035 Uiso 1 1 calc R . . H26C H 0.5475 0.9108 0.1301 0.035 Uiso 1 1 calc R . . C27 C 0.2122(5) 0.9001(4) 0.2182(4) 0.0188(14) Uani 1 1 d . . . H27A H 0.1524 0.8732 0.2085 0.028 Uiso 1 1 calc R . . H27B H 0.1978 0.9376 0.1796 0.028 Uiso 1 1 calc R . . H27C H 0.2339 0.9168 0.2753 0.028 Uiso 1 1 calc R . . Ir2A Ir -0.13472(2) 0.78065(1) -0.07242(1) 0.00834(7) Uani 0.9441(5) 1 d P . . Ir2B Ir -0.0989(3) 0.7195(2) -0.0266(2) 0.00834(7) Uani 0.0559(5) 1 d P . . F5 F -0.2320(3) 0.9070(2) 0.1606(2) 0.0230(9) Uani 1 1 d . . . F6 F -0.4152(3) 0.9695(2) -0.1106(3) 0.0253(9) Uani 1 1 d . . . F7 F 0.1422(3) 0.9745(3) 0.0247(3) 0.0360(11) Uani 1 1 d . . . F8 F -0.0546(4) 0.9693(2) -0.2550(3) 0.0341(11) Uani 1 1 d . . . O3 O -0.0350(3) 0.7098(2) -0.0966(3) 0.0166(9) Uani 1 1 d . . . O4 O -0.2337(3) 0.7001(2) -0.0706(3) 0.0171(9) Uani 1 1 d . . . N3 N -0.0758(4) 0.7719(3) 0.0532(3) 0.0160(11) Uani 1 1 d . . . N4 N -0.1945(4) 0.7962(3) -0.1971(3) 0.0133(11) Uani 1 1 d . . . C28 C -0.0009(5) 0.7297(3) 0.0922(4) 0.0185(14) Uani 1 1 d . . . H28 H 0.0271 0.7029 0.0598 0.022 Uiso 1 1 calc R . . C29 C 0.0356(5) 0.7245(3) 0.1769(4) 0.0192(14) Uani 1 1 d . . . H29 H 0.0886 0.6950 0.2024 0.023 Uiso 1 1 calc R . . C30 C -0.0059(5) 0.7631(3) 0.2257(4) 0.0147(13) Uani 1 1 d . . . H30 H 0.0180 0.7597 0.2844 0.018 Uiso 1 1 calc R . . C31 C -0.0827(5) 0.8062(3) 0.1863(4) 0.0166(13) Uani 1 1 d . . . H31 H -0.1115 0.8331 0.2181 0.020 Uiso 1 1 calc R . . C32 C -0.1178(5) 0.8102(3) 0.0994(4) 0.0138(12) Uani 1 1 d . . . C33 C -0.1976(4) 0.8529(3) 0.0475(4) 0.0134(12) Uani 1 1 d . . . C34 C -0.2518(5) 0.8987(3) 0.0767(4) 0.0164(13) Uani 1 1 d . . . C35 C -0.3249(5) 0.9382(3) 0.0263(4) 0.0173(13) Uani 1 1 d . . . H35 H -0.3616 0.9685 0.0475 0.021 Uiso 1 1 calc R . . C36 C -0.3418(5) 0.9307(3) -0.0587(4) 0.0176(13) Uani 1 1 d . . . C37 C -0.2912(5) 0.8879(3) -0.0917(4) 0.0169(13) Uani 1 1 d . . . H37 H -0.3054 0.8857 -0.1501 0.020 Uiso 1 1 calc R . . C38 C -0.2173(5) 0.8468(3) -0.0387(4) 0.0145(12) Uani 1 1 d . . . C39 C -0.0512(5) 0.8570(3) -0.0837(4) 0.0166(13) Uani 1 1 d . . . C40 C 0.0234(5) 0.8889(4) -0.0195(4) 0.0180(14) Uani 1 1 d . . . H40 H 0.0417 0.8726 0.0357 0.022 Uiso 1 1 calc R . . C41 C 0.0694(5) 0.9438(4) -0.0376(4) 0.0238(15) Uani 1 1 d . . . C42 C 0.0454(6) 0.9731(4) -0.1158(5) 0.0285(17) Uani 1 1 d . . . H42 H 0.0769 1.0122 -0.1258 0.034 Uiso 1 1 calc R . . C43 C -0.0282(5) 0.9406(4) -0.1779(4) 0.0226(15) Uani 1 1 d . . . C44 C -0.0759(5) 0.8837(3) -0.1657(4) 0.0179(13) Uani 1 1 d . . . C45 C -0.1530(5) 0.8465(4) -0.2295(4) 0.0194(14) Uani 1 1 d . . . C46 C -0.1860(5) 0.8572(4) -0.3159(4) 0.0208(14) Uani 1 1 d . . . H46 H -0.1570 0.8914 -0.3387 0.025 Uiso 1 1 calc R . . C47 C -0.2605(5) 0.8183(4) -0.3673(4) 0.0215(15) Uani 1 1 d . . . H47 H -0.2817 0.8248 -0.4256 0.026 Uiso 1 1 calc R . . C48 C -0.3045(5) 0.7692(4) -0.3328(4) 0.0212(14) Uani 1 1 d . . . H48 H -0.3575 0.7430 -0.3668 0.025 Uiso 1 1 calc R . . C49 C -0.2689(5) 0.7600(3) -0.2481(4) 0.0168(13) Uani 1 1 d . . . H49 H -0.2983 0.7265 -0.2245 0.020 Uiso 1 1 calc R . . C50 C -0.0498(5) 0.6473(3) -0.1033(4) 0.0172(13) Uani 1 1 d . . . C51 C -0.1333(5) 0.6130(4) -0.0979(5) 0.0243(15) Uani 1 1 d . . . H51 H -0.1333 0.5663 -0.1054 0.029 Uiso 1 1 calc R . . C52 C -0.2160(5) 0.6392(3) -0.0829(4) 0.0181(13) Uani 1 1 d . . . C53 C 0.0317(5) 0.6065(4) -0.1191(5) 0.0230(15) Uani 1 1 d . . . H53A H 0.0128 0.5956 -0.1782 0.035 Uiso 1 1 calc R . . H53B H 0.0416 0.5654 -0.0867 0.035 Uiso 1 1 calc R . . H53C H 0.0934 0.6321 -0.1027 0.035 Uiso 1 1 calc R . . C54 C -0.2956(6) 0.5908(4) -0.0778(5) 0.0319(18) Uani 1 1 d . . . H54A H -0.2798 0.5747 -0.0208 0.048 Uiso 1 1 calc R . . H54B H -0.2985 0.5532 -0.1149 0.048 Uiso 1 1 calc R . . H54C H -0.3599 0.6134 -0.0945 0.048 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 Ir1A 0.00789(12) 0.01007(13) 0.00679(12) -0.00023(9) 0.00182(9) 0.00014(8) Ir1B 0.00789(12) 0.01007(13) 0.00679(12) -0.00023(9) 0.00182(9) 0.00014(8) F1 0.048(3) 0.034(3) 0.023(2) 0.010(2) 0.012(2) -0.013(2) F2 0.031(2) 0.032(3) 0.024(2) -0.0006(19) -0.0013(19) -0.016(2) F3 0.024(2) 0.023(2) 0.024(2) 0.0072(17) 0.0053(17) 0.0097(17) F4 0.029(2) 0.025(2) 0.0154(19) -0.0035(16) 0.0080(17) 0.0051(17) O1 0.016(2) 0.016(2) 0.021(2) -0.0039(19) 0.0091(19) -0.0042(18) O2 0.018(2) 0.014(2) 0.018(2) 0.0019(18) 0.0099(19) 0.0035(18) N1 0.019(3) 0.014(3) 0.020(3) -0.007(2) 0.011(2) -0.003(2) N2 0.014(3) 0.010(3) 0.010(2) 0.0034(19) 0.003(2) -0.003(2) C1 0.015(3) 0.022(3) 0.015(3) -0.001(3) 0.003(3) 0.002(3) C2 0.016(3) 0.024(4) 0.018(3) -0.007(3) 0.005(3) 0.004(3) C3 0.020(3) 0.023(4) 0.013(3) 0.003(3) 0.004(3) 0.007(3) C4 0.020(3) 0.029(4) 0.011(3) 0.003(3) 0.003(3) 0.002(3) C5 0.015(3) 0.019(3) 0.008(3) 0.000(2) 0.001(2) 0.003(2) C6 0.018(3) 0.022(4) 0.009(3) 0.003(2) 0.004(2) 0.003(3) C7 0.038(4) 0.023(4) 0.019(3) 0.007(3) 0.011(3) -0.002(3) C8 0.028(4) 0.020(4) 0.027(4) 0.008(3) 0.012(3) 0.005(3) C9 0.020(3) 0.023(4) 0.020(3) 0.002(3) -0.002(3) -0.004(3) C10 0.017(3) 0.018(3) 0.017(3) 0.000(3) 0.006(3) -0.003(3) C11 0.009(3) 0.021(3) 0.013(3) -0.002(2) 0.002(2) 0.002(2) C12 0.013(3) 0.015(3) 0.017(3) 0.000(2) 0.005(2) -0.001(2) C13 0.015(3) 0.013(3) 0.016(3) 0.000(2) 0.004(2) -0.003(2) C14 0.020(3) 0.009(3) 0.025(3) 0.000(3) 0.009(3) -0.003(2) C15 0.023(3) 0.015(3) 0.022(3) -0.001(3) 0.012(3) 0.001(3) C16 0.020(3) 0.019(3) 0.015(3) -0.004(3) 0.006(3) -0.006(3) C17 0.017(3) 0.013(3) 0.010(3) -0.003(2) 0.001(2) -0.003(2) C18 0.016(3) 0.011(3) 0.009(3) -0.002(2) 0.004(2) -0.001(2) C19 0.014(3) 0.021(3) 0.013(3) -0.001(3) 0.003(2) -0.001(3) C20 0.017(3) 0.018(3) 0.014(3) 0.002(2) 0.005(3) -0.001(3) C21 0.011(3) 0.022(4) 0.021(3) 0.000(3) 0.004(3) 0.004(2) C22 0.018(3) 0.017(3) 0.018(3) 0.001(3) 0.007(3) 0.006(3) C23 0.018(3) 0.018(3) 0.014(3) -0.003(2) 0.004(3) -0.002(3) C24 0.026(3) 0.007(3) 0.022(3) 0.001(2) 0.013(3) 0.001(3) C25 0.020(3) 0.010(3) 0.008(3) 0.000(2) 0.004(2) 0.004(2) C26 0.022(4) 0.016(3) 0.036(4) 0.001(3) 0.014(3) -0.002(3) C27 0.021(3) 0.020(4) 0.016(3) -0.001(3) 0.007(3) 0.004(3) Ir2A 0.00792(12) 0.00991(13) 0.00675(12) -0.00069(8) 0.00177(9) -0.00036(8) Ir2B 0.00792(12) 0.00991(13) 0.00675(12) -0.00069(8) 0.00177(9) -0.00036(8) F5 0.025(2) 0.026(2) 0.0175(19) -0.0018(17) 0.0068(17) 0.0091(17) F6 0.023(2) 0.026(2) 0.023(2) 0.0051(17) 0.0031(17) 0.0130(17) F7 0.034(3) 0.039(3) 0.030(2) -0.005(2) 0.004(2) -0.022(2) F8 0.041(3) 0.034(3) 0.025(2) 0.009(2) 0.008(2) -0.010(2) O3 0.017(2) 0.017(2) 0.015(2) -0.0029(18) 0.0043(18) 0.0009(18) O4 0.016(2) 0.019(2) 0.017(2) -0.0014(19) 0.0061(18) -0.0023(18) N3 0.016(3) 0.018(3) 0.014(3) 0.001(2) 0.005(2) 0.003(2) N4 0.011(2) 0.019(3) 0.009(2) -0.004(2) 0.002(2) 0.001(2) C28 0.016(3) 0.021(4) 0.017(3) -0.002(3) 0.002(3) 0.008(3) C29 0.014(3) 0.022(4) 0.018(3) -0.001(3) 0.000(3) 0.005(3) C30 0.014(3) 0.021(3) 0.009(3) -0.003(2) 0.003(2) -0.003(3) C31 0.019(3) 0.015(3) 0.016(3) 0.000(2) 0.006(3) 0.002(3) C32 0.016(3) 0.011(3) 0.015(3) 0.001(2) 0.007(2) -0.003(2) C33 0.009(3) 0.017(3) 0.016(3) -0.001(2) 0.007(2) -0.003(2) C34 0.018(3) 0.018(3) 0.016(3) -0.004(3) 0.008(3) -0.003(3) C35 0.016(3) 0.015(3) 0.019(3) -0.002(3) 0.005(3) 0.002(3) C36 0.011(3) 0.017(3) 0.022(3) 0.000(3) 0.001(3) 0.002(2) C37 0.018(3) 0.015(3) 0.016(3) -0.001(2) 0.002(3) -0.001(3) C38 0.011(3) 0.014(3) 0.018(3) 0.002(2) 0.004(2) -0.003(2) C39 0.016(3) 0.020(3) 0.014(3) -0.005(3) 0.004(2) -0.002(3) C40 0.018(3) 0.026(4) 0.010(3) -0.003(3) 0.004(2) 0.001(3) C41 0.016(3) 0.032(4) 0.020(3) -0.008(3) 0.001(3) -0.011(3) C42 0.031(4) 0.028(4) 0.028(4) -0.002(3) 0.012(3) -0.012(3) C43 0.021(3) 0.028(4) 0.016(3) 0.002(3) 0.002(3) -0.006(3) C44 0.014(3) 0.020(3) 0.020(3) 0.003(3) 0.006(3) -0.004(3) C45 0.018(3) 0.026(4) 0.014(3) 0.003(3) 0.004(3) 0.000(3) C46 0.024(4) 0.024(4) 0.015(3) 0.003(3) 0.007(3) 0.003(3) C47 0.020(3) 0.028(4) 0.014(3) 0.003(3) 0.003(3) 0.005(3) C48 0.017(3) 0.023(4) 0.018(3) -0.006(3) -0.001(3) -0.004(3) C49 0.013(3) 0.017(3) 0.017(3) -0.006(3) 0.001(3) -0.002(2) C50 0.021(3) 0.011(3) 0.018(3) 0.002(2) 0.005(3) 0.004(3) C51 0.023(4) 0.023(4) 0.031(4) -0.003(3) 0.015(3) -0.001(3) C52 0.022(3) 0.014(3) 0.019(3) -0.002(3) 0.007(3) 0.000(3) C53 0.027(4) 0.016(3) 0.030(4) -0.004(3) 0.014(3) 0.002(3) C54 0.031(4) 0.030(4) 0.044(5) -0.013(4) 0.025(4) -0.011(3) _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 Ir1A C11 1.982(7) . ? Ir1A C12 2.008(7) . ? Ir1A N1 2.030(6) . ? Ir1A N2 2.052(5) . ? Ir1A O1 2.146(5) . ? Ir1A O2 2.149(4) . ? F1 C7 1.360(8) . ? F2 C9 1.366(8) . ? F3 C14 1.358(8) . ? F4 C16 1.367(7) . ? O1 C23 1.285(8) . ? O2 C25 1.282(8) . ? N1 C1 1.356(9) . ? N1 C5 1.375(8) . ? N2 C22 1.347(8) . ? N2 C18 1.370(8) . ? C1 C2 1.368(9) . ? C1 H1 0.9500 . ? C2 C3 1.391(10) . ? C2 H2 0.9500 . ? C3 C4 1.390(10) . ? C3 H3 0.9500 . ? C4 C5 1.406(8) . ? C4 H4 0.9500 . ? C5 C6 1.463(9) . ? C6 C7 1.399(10) . ? C6 C11 1.430(9) . ? C7 C8 1.379(11) . ? C8 C9 1.377(10) . ? C8 H8 0.9500 . ? C9 C10 1.379(10) . ? C10 C11 1.397(9) . ? C10 H10 0.9500 . ? C12 C13 1.396(9) . ? C12 C17 1.412(9) . ? C13 C14 1.386(9) . ? C13 H13 0.9500 . ? C14 C15 1.396(10) . ? C15 C16 1.360(10) . ? C15 H15 0.9500 . ? C16 C17 1.407(9) . ? C17 C18 1.468(9) . ? C18 C19 1.410(8) . ? C19 C20 1.389(9) . ? C19 H19 0.9500 . ? C20 C21 1.383(9) . ? C20 H20 0.9500 . ? C21 C22 1.377(9) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.391(9) . ? C23 C26 1.509(9) . ? C24 C25 1.398(9) . ? C24 H24 0.9500 . ? C25 C27 1.511(9) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? Ir2A C38 1.985(7) . ? Ir2A C39 1.994(7) . ? Ir2A N3 2.039(5) . ? Ir2A N4 2.042(5) . ? Ir2A O3 2.150(5) . ? Ir2A O4 2.161(5) . ? F5 C34 1.375(7) . ? F6 C36 1.374(7) . ? F7 C41 1.368(8) . ? F8 C43 1.373(8) . ? O3 C50 1.278(8) . ? O4 C52 1.283(8) . ? N3 C28 1.360(8) . ? N3 C32 1.372(8) . ? N4 C49 1.347(8) . ? N4 C45 1.378(9) . ? C28 C29 1.370(9) . ? C28 H28 0.9500 . ? C29 C30 1.404(9) . ? C29 H29 0.9500 . ? C30 C31 1.389(9) . ? C30 H30 0.9500 . ? C31 C32 1.404(9) . ? C31 H31 0.9500 . ? C32 C33 1.472(9) . ? C33 C34 1.398(9) . ? C33 C38 1.410(9) . ? C34 C35 1.371(9) . ? C35 C36 1.398(9) . ? C35 H35 0.9500 . ? C36 C37 1.361(9) . ? C37 C38 1.413(9) . ? C37 H37 0.9500 . ? C39 C40 1.411(9) . ? C39 C44 1.432(9) . ? C40 C41 1.372(10) . ? C40 H40 0.9500 . ? C41 C42 1.397(11) . ? C42 C43 1.389(10) . ? C42 H42 0.9500 . ? C43 C44 1.384(10) . ? C44 C45 1.477(9) . ? C45 C46 1.410(9) . ? C46 C47 1.382(10) . ? C46 H46 0.9500 . ? C47 C48 1.401(10) . ? C47 H47 0.9500 . ? C48 C49 1.380(10) . ? C48 H48 0.9500 . ? C49 H49 0.9500 . ? C50 C51 1.407(10) . ? C50 C53 1.520(9) . ? C51 C52 1.391(10) . ? C51 H51 0.9500 . ? C52 C54 1.523(10) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Ir1A C12 88.7(3) . . ? C11 Ir1A N1 81.1(2) . . ? C12 Ir1A N1 96.8(2) . . ? C11 Ir1A N2 95.9(2) . . ? C12 Ir1A N2 81.0(2) . . ? N1 Ir1A N2 176.4(2) . . ? C11 Ir1A O1 174.7(2) . . ? C12 Ir1A O1 92.1(2) . . ? N1 Ir1A O1 93.6(2) . . ? N2 Ir1A O1 89.41(19) . . ? C11 Ir1A O2 90.7(2) . . ? C12 Ir1A O2 175.0(2) . . ? N1 Ir1A O2 88.0(2) . . ? N2 Ir1A O2 94.13(19) . . ? O1 Ir1A O2 88.92(18) . . ? C23 O1 Ir1A 123.7(4) . . ? C25 O2 Ir1A 125.1(4) . . ? C1 N1 C5 118.5(6) . . ? C1 N1 Ir1A 124.9(5) . . ? C5 N1 Ir1A 116.5(4) . . ? C22 N2 C18 120.3(5) . . ? C22 N2 Ir1A 124.2(4) . . ? C18 N2 Ir1A 115.5(4) . . ? N1 C1 C2 123.2(7) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 119.3(7) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 118.6(6) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 120.2(7) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 120.0(6) . . ? N1 C5 C6 112.4(5) . . ? C4 C5 C6 127.5(6) . . ? C7 C6 C11 118.1(6) . . ? C7 C6 C5 126.2(6) . . ? C11 C6 C5 115.7(6) . . ? F1 C7 C8 117.2(7) . . ? F1 C7 C6 119.1(7) . . ? C8 C7 C6 123.7(6) . . ? C9 C8 C7 116.3(7) . . ? C9 C8 H8 121.9 . . ? C7 C8 H8 121.9 . . ? F2 C9 C8 117.9(7) . . ? F2 C9 C10 118.4(6) . . ? C8 C9 C10 123.7(7) . . ? C9 C10 C11 119.8(6) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 118.5(6) . . ? C10 C11 Ir1A 127.4(5) . . ? C6 C11 Ir1A 114.1(5) . . ? C13 C12 C17 120.3(6) . . ? C13 C12 Ir1A 125.9(5) . . ? C17 C12 Ir1A 113.8(5) . . ? C14 C13 C12 118.2(6) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? F3 C14 C13 118.9(6) . . ? F3 C14 C15 117.7(6) . . ? C13 C14 C15 123.3(6) . . ? C16 C15 C14 117.1(6) . . ? C16 C15 H15 121.5 . . ? C14 C15 H15 121.5 . . ? C15 C16 F4 117.3(6) . . ? C15 C16 C17 123.1(6) . . ? F4 C16 C17 119.5(6) . . ? C16 C17 C12 117.9(6) . . ? C16 C17 C18 125.9(6) . . ? C12 C17 C18 116.1(6) . . ? N2 C18 C19 119.2(6) . . ? N2 C18 C17 113.5(5) . . ? C19 C18 C17 127.3(6) . . ? C20 C19 C18 119.7(6) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 119.6(6) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 119.1(6) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? N2 C22 C21 122.1(6) . . ? N2 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? O1 C23 C24 127.5(6) . . ? O1 C23 C26 113.0(6) . . ? C24 C23 C26 119.5(6) . . ? C23 C24 C25 128.9(6) . . ? C23 C24 H24 115.6 . . ? C25 C24 H24 115.6 . . ? O2 C25 C24 125.7(6) . . ? O2 C25 C27 115.5(6) . . ? C24 C25 C27 118.8(6) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C38 Ir2A C39 86.6(3) . . ? C38 Ir2A N3 80.4(2) . . ? C39 Ir2A N3 96.5(2) . . ? C38 Ir2A N4 96.5(2) . . ? C39 Ir2A N4 80.9(2) . . ? N3 Ir2A N4 176.1(2) . . ? C38 Ir2A O3 174.3(2) . . ? C39 Ir2A O3 92.3(2) . . ? N3 Ir2A O3 94.1(2) . . ? N4 Ir2A O3 88.82(19) . . ? C38 Ir2A O4 92.7(2) . . ? C39 Ir2A O4 175.1(2) . . ? N3 Ir2A O4 88.1(2) . . ? N4 Ir2A O4 94.4(2) . . ? O3 Ir2A O4 88.95(18) . . ? C50 O3 Ir2A 124.8(4) . . ? C52 O4 Ir2A 123.4(4) . . ? C28 N3 C32 119.5(6) . . ? C28 N3 Ir2A 123.9(4) . . ? C32 N3 Ir2A 116.5(4) . . ? C49 N4 C45 119.5(6) . . ? C49 N4 Ir2A 124.3(5) . . ? C45 N4 Ir2A 116.2(4) . . ? N3 C28 C29 122.1(6) . . ? N3 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? C28 C29 C30 119.6(6) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C31 C30 C29 118.6(6) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C30 C31 C32 120.0(6) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? N3 C32 C31 120.1(6) . . ? N3 C32 C33 112.4(5) . . ? C31 C32 C33 127.4(6) . . ? C34 C33 C38 119.0(6) . . ? C34 C33 C32 125.6(6) . . ? C38 C33 C32 115.3(6) . . ? C35 C34 F5 116.1(6) . . ? C35 C34 C33 123.8(6) . . ? F5 C34 C33 120.1(6) . . ? C34 C35 C36 115.3(6) . . ? C34 C35 H35 122.3 . . ? C36 C35 H35 122.3 . . ? C37 C36 F6 119.4(6) . . ? C37 C36 C35 124.2(6) . . ? F6 C36 C35 116.4(6) . . ? C36 C37 C38 119.6(6) . . ? C36 C37 H37 120.2 . . ? C38 C37 H37 120.2 . . ? C33 C38 C37 118.0(6) . . ? C33 C38 Ir2A 115.2(5) . . ? C37 C38 Ir2A 126.8(5) . . ? C40 C39 C44 118.0(6) . . ? C40 C39 Ir2A 127.0(5) . . ? C44 C39 Ir2A 114.8(5) . . ? C41 C40 C39 119.3(6) . . ? C41 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? F7 C41 C40 119.2(6) . . ? F7 C41 C42 116.0(7) . . ? C40 C41 C42 124.8(6) . . ? C43 C42 C41 114.7(7) . . ? C43 C42 H42 122.7 . . ? C41 C42 H42 122.7 . . ? F8 C43 C44 119.9(6) . . ? F8 C43 C42 115.8(6) . . ? C44 C43 C42 124.3(7) . . ? C43 C44 C39 118.9(6) . . ? C43 C44 C45 126.6(6) . . ? C39 C44 C45 114.6(6) . . ? N4 C45 C46 119.4(6) . . ? N4 C45 C44 113.2(5) . . ? C46 C45 C44 127.4(6) . . ? C47 C46 C45 120.2(7) . . ? C47 C46 H46 119.9 . . ? C45 C46 H46 119.9 . . ? C46 C47 C48 119.5(6) . . ? C46 C47 H47 120.3 . . ? C48 C47 H47 120.3 . . ? C49 C48 C47 118.2(6) . . ? C49 C48 H48 120.9 . . ? C47 C48 H48 120.9 . . ? N4 C49 C48 123.1(6) . . ? N4 C49 H49 118.4 . . ? C48 C49 H49 118.4 . . ? O3 C50 C51 126.8(6) . . ? O3 C50 C53 115.8(6) . . ? C51 C50 C53 117.5(6) . . ? C52 C51 C50 127.9(7) . . ? C52 C51 H51 116.1 . . ? C50 C51 H51 116.1 . . ? O4 C52 C51 128.2(7) . . ? O4 C52 C54 114.3(6) . . ? C51 C52 C54 117.5(6) . . ? C50 C53 H53A 109.5 . . ? C50 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C50 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C52 C54 H54A 109.5 . . ? C52 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C52 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 Ir1A O1 C23 178.1(5) . . . . ? N1 Ir1A O1 C23 -85.0(5) . . . . ? N2 Ir1A O1 C23 97.1(5) . . . . ? O2 Ir1A O1 C23 3.0(5) . . . . ? C11 Ir1A O2 C25 174.8(5) . . . . ? N1 Ir1A O2 C25 93.7(5) . . . . ? N2 Ir1A O2 C25 -89.2(5) . . . . ? O1 Ir1A O2 C25 0.1(5) . . . . ? C11 Ir1A N1 C1 178.9(6) . . . . ? C12 Ir1A N1 C1 91.3(6) . . . . ? O1 Ir1A N1 C1 -1.2(5) . . . . ? O2 Ir1A N1 C1 -90.0(5) . . . . ? C11 Ir1A N1 C5 -2.1(5) . . . . ? C12 Ir1A N1 C5 -89.7(5) . . . . ? O1 Ir1A N1 C5 177.7(5) . . . . ? O2 Ir1A N1 C5 88.9(5) . . . . ? C11 Ir1A N2 C22 90.5(5) . . . . ? C12 Ir1A N2 C22 178.3(6) . . . . ? O1 Ir1A N2 C22 -89.5(5) . . . . ? O2 Ir1A N2 C22 -0.6(5) . . . . ? C11 Ir1A N2 C18 -89.1(5) . . . . ? C12 Ir1A N2 C18 -1.4(4) . . . . ? O1 Ir1A N2 C18 90.8(4) . . . . ? O2 Ir1A N2 C18 179.7(4) . . . . ? C5 N1 C1 C2 -1.8(10) . . . . ? Ir1A N1 C1 C2 177.1(5) . . . . ? N1 C1 C2 C3 -0.3(10) . . . . ? C1 C2 C3 C4 2.3(10) . . . . ? C2 C3 C4 C5 -2.2(10) . . . . ? C1 N1 C5 C4 1.8(9) . . . . ? Ir1A N1 C5 C4 -177.2(5) . . . . ? C1 N1 C5 C6 -179.6(6) . . . . ? Ir1A N1 C5 C6 1.4(7) . . . . ? C3 C4 C5 N1 0.2(10) . . . . ? C3 C4 C5 C6 -178.2(7) . . . . ? N1 C5 C6 C7 -178.2(7) . . . . ? C4 C5 C6 C7 0.3(12) . . . . ? N1 C5 C6 C11 0.6(8) . . . . ? C4 C5 C6 C11 179.1(7) . . . . ? C11 C6 C7 F1 -179.3(6) . . . . ? C5 C6 C7 F1 -0.5(12) . . . . ? C11 C6 C7 C8 0.5(11) . . . . ? C5 C6 C7 C8 179.3(7) . . . . ? F1 C7 C8 C9 179.8(7) . . . . ? C6 C7 C8 C9 0.0(12) . . . . ? C7 C8 C9 F2 -178.2(7) . . . . ? C7 C8 C9 C10 -0.1(12) . . . . ? F2 C9 C10 C11 177.9(6) . . . . ? C8 C9 C10 C11 -0.2(12) . . . . ? C9 C10 C11 C6 0.7(10) . . . . ? C9 C10 C11 Ir1A -176.3(5) . . . . ? C7 C6 C11 C10 -0.8(10) . . . . ? C5 C6 C11 C10 -179.7(6) . . . . ? C7 C6 C11 Ir1A 176.6(5) . . . . ? C5 C6 C11 Ir1A -2.3(7) . . . . ? C12 Ir1A C11 C10 -83.5(6) . . . . ? N1 Ir1A C11 C10 179.5(6) . . . . ? N2 Ir1A C11 C10 -2.6(6) . . . . ? O2 Ir1A C11 C10 91.6(6) . . . . ? C12 Ir1A C11 C6 99.4(5) . . . . ? N1 Ir1A C11 C6 2.4(5) . . . . ? N2 Ir1A C11 C6 -179.8(5) . . . . ? O2 Ir1A C11 C6 -85.5(5) . . . . ? C11 Ir1A C12 C13 -80.6(6) . . . . ? N1 Ir1A C12 C13 0.3(6) . . . . ? N2 Ir1A C12 C13 -176.8(6) . . . . ? O1 Ir1A C12 C13 94.2(6) . . . . ? C11 Ir1A C12 C17 98.3(5) . . . . ? N1 Ir1A C12 C17 179.2(5) . . . . ? N2 Ir1A C12 C17 2.1(5) . . . . ? O1 Ir1A C12 C17 -87.0(5) . . . . ? C17 C12 C13 C14 2.0(9) . . . . ? Ir1A C12 C13 C14 -179.2(5) . . . . ? C12 C13 C14 F3 178.2(6) . . . . ? C12 C13 C14 C15 -1.2(10) . . . . ? F3 C14 C15 C16 -178.9(6) . . . . ? C13 C14 C15 C16 0.5(10) . . . . ? C14 C15 C16 F4 -179.4(6) . . . . ? C14 C15 C16 C17 -0.6(10) . . . . ? C15 C16 C17 C12 1.4(10) . . . . ? F4 C16 C17 C12 -179.9(6) . . . . ? C15 C16 C17 C18 -176.9(6) . . . . ? F4 C16 C17 C18 1.8(10) . . . . ? C13 C12 C17 C16 -2.1(9) . . . . ? Ir1A C12 C17 C16 179.0(5) . . . . ? C13 C12 C17 C18 176.4(6) . . . . ? Ir1A C12 C17 C18 -2.5(7) . . . . ? C22 N2 C18 C19 -0.7(9) . . . . ? Ir1A N2 C18 C19 179.0(5) . . . . ? C22 N2 C18 C17 -179.2(6) . . . . ? Ir1A N2 C18 C17 0.4(7) . . . . ? C16 C17 C18 N2 179.7(6) . . . . ? C12 C17 C18 N2 1.4(8) . . . . ? C16 C17 C18 C19 1.3(11) . . . . ? C12 C17 C18 C19 -177.1(6) . . . . ? N2 C18 C19 C20 0.9(9) . . . . ? C17 C18 C19 C20 179.3(6) . . . . ? C18 C19 C20 C21 -0.7(10) . . . . ? C19 C20 C21 C22 0.3(10) . . . . ? C18 N2 C22 C21 0.3(10) . . . . ? Ir1A N2 C22 C21 -179.4(5) . . . . ? C20 C21 C22 N2 -0.1(10) . . . . ? Ir1A O1 C23 C24 -3.4(9) . . . . ? Ir1A O1 C23 C26 177.3(4) . . . . ? O1 C23 C24 C25 -0.2(12) . . . . ? C26 C23 C24 C25 179.1(7) . . . . ? Ir1A O2 C25 C24 -3.1(9) . . . . ? Ir1A O2 C25 C27 176.8(4) . . . . ? C23 C24 C25 O2 3.9(11) . . . . ? C23 C24 C25 C27 -176.0(6) . . . . ? C39 Ir2A O3 C50 -175.6(5) . . . . ? N3 Ir2A O3 C50 87.7(5) . . . . ? N4 Ir2A O3 C50 -94.8(5) . . . . ? O4 Ir2A O3 C50 -0.4(5) . . . . ? C38 Ir2A O4 C52 -175.3(5) . . . . ? N3 Ir2A O4 C52 -94.9(5) . . . . ? N4 Ir2A O4 C52 88.0(5) . . . . ? O3 Ir2A O4 C52 -0.7(5) . . . . ? C38 Ir2A N3 C28 179.9(6) . . . . ? C39 Ir2A N3 C28 -94.7(6) . . . . ? O3 Ir2A N3 C28 -1.9(6) . . . . ? O4 Ir2A N3 C28 86.9(6) . . . . ? C38 Ir2A N3 C32 1.9(5) . . . . ? C39 Ir2A N3 C32 87.3(5) . . . . ? O3 Ir2A N3 C32 -180.0(5) . . . . ? O4 Ir2A N3 C32 -91.2(5) . . . . ? C38 Ir2A N4 C49 -94.8(5) . . . . ? C39 Ir2A N4 C49 179.8(6) . . . . ? O3 Ir2A N4 C49 87.3(5) . . . . ? O4 Ir2A N4 C49 -1.5(5) . . . . ? C38 Ir2A N4 C45 86.5(5) . . . . ? C39 Ir2A N4 C45 1.1(5) . . . . ? O3 Ir2A N4 C45 -91.4(5) . . . . ? O4 Ir2A N4 C45 179.7(5) . . . . ? C32 N3 C28 C29 -0.9(10) . . . . ? Ir2A N3 C28 C29 -178.9(5) . . . . ? N3 C28 C29 C30 0.9(11) . . . . ? C28 C29 C30 C31 -0.7(10) . . . . ? C29 C30 C31 C32 0.5(10) . . . . ? C28 N3 C32 C31 0.7(9) . . . . ? Ir2A N3 C32 C31 178.9(5) . . . . ? C28 N3 C32 C33 -179.9(6) . . . . ? Ir2A N3 C32 C33 -1.8(7) . . . . ? C30 C31 C32 N3 -0.6(10) . . . . ? C30 C31 C32 C33 -179.8(6) . . . . ? N3 C32 C33 C34 -177.8(6) . . . . ? C31 C32 C33 C34 1.4(11) . . . . ? N3 C32 C33 C38 0.5(8) . . . . ? C31 C32 C33 C38 179.8(6) . . . . ? C38 C33 C34 C35 0.9(10) . . . . ? C32 C33 C34 C35 179.2(6) . . . . ? C38 C33 C34 F5 -178.0(6) . . . . ? C32 C33 C34 F5 0.3(10) . . . . ? F5 C34 C35 C36 177.9(6) . . . . ? C33 C34 C35 C36 -1.0(10) . . . . ? C34 C35 C36 C37 0.1(10) . . . . ? C34 C35 C36 F6 179.6(6) . . . . ? F6 C36 C37 C38 -178.5(6) . . . . ? C35 C36 C37 C38 1.1(11) . . . . ? C34 C33 C38 C37 0.3(9) . . . . ? C32 C33 C38 C37 -178.2(6) . . . . ? C34 C33 C38 Ir2A 179.5(5) . . . . ? C32 C33 C38 Ir2A 1.0(7) . . . . ? C36 C37 C38 C33 -1.2(9) . . . . ? C36 C37 C38 Ir2A 179.7(5) . . . . ? C39 Ir2A C38 C33 -98.7(5) . . . . ? N3 Ir2A C38 C33 -1.5(5) . . . . ? N4 Ir2A C38 C33 -179.1(5) . . . . ? O4 Ir2A C38 C33 86.1(5) . . . . ? C39 Ir2A C38 C37 80.4(6) . . . . ? N3 Ir2A C38 C37 177.6(6) . . . . ? N4 Ir2A C38 C37 0.0(6) . . . . ? O4 Ir2A C38 C37 -94.8(6) . . . . ? C38 Ir2A C39 C40 81.0(6) . . . . ? N3 Ir2A C39 C40 1.0(6) . . . . ? N4 Ir2A C39 C40 178.1(6) . . . . ? O3 Ir2A C39 C40 -93.4(6) . . . . ? C38 Ir2A C39 C44 -94.8(5) . . . . ? N3 Ir2A C39 C44 -174.7(5) . . . . ? N4 Ir2A C39 C44 2.4(5) . . . . ? O3 Ir2A C39 C44 90.8(5) . . . . ? C44 C39 C40 C41 -0.1(10) . . . . ? Ir2A C39 C40 C41 -175.7(5) . . . . ? C39 C40 C41 F7 -179.7(6) . . . . ? C39 C40 C41 C42 2.6(12) . . . . ? F7 C41 C42 C43 179.6(7) . . . . ? C40 C41 C42 C43 -2.6(12) . . . . ? C41 C42 C43 F8 178.6(7) . . . . ? C41 C42 C43 C44 0.2(12) . . . . ? F8 C43 C44 C39 -176.3(6) . . . . ? C42 C43 C44 C39 2.1(12) . . . . ? F8 C43 C44 C45 2.9(12) . . . . ? C42 C43 C44 C45 -178.7(7) . . . . ? C40 C39 C44 C43 -2.1(10) . . . . ? Ir2A C39 C44 C43 174.0(5) . . . . ? C40 C39 C44 C45 178.6(6) . . . . ? Ir2A C39 C44 C45 -5.3(8) . . . . ? C49 N4 C45 C46 -2.9(10) . . . . ? Ir2A N4 C45 C46 175.9(5) . . . . ? C49 N4 C45 C44 177.1(6) . . . . ? Ir2A N4 C45 C44 -4.1(7) . . . . ? C43 C44 C45 N4 -173.2(7) . . . . ? C39 C44 C45 N4 6.1(9) . . . . ? C43 C44 C45 C46 6.8(12) . . . . ? C39 C44 C45 C46 -173.9(7) . . . . ? N4 C45 C46 C47 1.0(10) . . . . ? C44 C45 C46 C47 -179.0(7) . . . . ? C45 C46 C47 C48 1.6(11) . . . . ? C46 C47 C48 C49 -2.3(10) . . . . ? C45 N4 C49 C48 2.2(10) . . . . ? Ir2A N4 C49 C48 -176.5(5) . . . . ? C47 C48 C49 N4 0.5(11) . . . . ? Ir2A O3 C50 C51 1.3(10) . . . . ? Ir2A O3 C50 C53 -179.0(4) . . . . ? O3 C50 C51 C52 -1.2(13) . . . . ? C53 C50 C51 C52 179.1(7) . . . . ? Ir2A O4 C52 C51 1.1(10) . . . . ? Ir2A O4 C52 C54 179.4(5) . . . . ? C50 C51 C52 O4 -0.2(13) . . . . ? C50 C51 C52 C54 -178.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 3.228 _refine_diff_density_min -2.384 _refine_diff_density_rms 0.226 _database_code_depnum_ccdc_archive 'CCDC 964311' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eb200 _audit_update_record ; 2012-07-13 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H31 Ir N2 O6, C H2 Cl2' _chemical_formula_sum 'C32 H33 Cl2 Ir N2 O6' _chemical_formula_weight 804.70 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' 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 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 23.041(3) _cell_length_b 10.8791(15) _cell_length_c 26.008(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.362(9) _cell_angle_gamma 90.00 _cell_volume 6315.6(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 227 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3184 _exptl_absorpt_coefficient_mu 4.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5785 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS 2008, Bruker AXS, 2008' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 71890 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7224 _reflns_number_gt 6224 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _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^)+(0.0212P)^2^+22.6613P] 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 7224 _refine_ls_number_parameters 416 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0568 _refine_ls_wR_factor_gt 0.0512 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.122 _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 0.009318(5) 0.202511(10) 0.125396(4) 0.01178(4) Uani 1 1 d . . . O1 O 0.11054(11) 0.5690(2) 0.04911(9) 0.0213(5) Uani 1 1 d . . . O2 O 0.16133(11) 0.5495(2) 0.23734(9) 0.0217(5) Uani 1 1 d . . . O3 O 0.20286(10) -0.0620(2) 0.10002(9) 0.0183(5) Uani 1 1 d . . . O4 O 0.14654(10) -0.0930(2) 0.26394(8) 0.0172(5) Uani 1 1 d . . . O5 O -0.05257(10) 0.0520(2) 0.10661(9) 0.0170(5) Uani 1 1 d . . . O6 O -0.06625(11) 0.3262(2) 0.10962(9) 0.0191(5) Uani 1 1 d . . . N1 N 0.01407(12) 0.2357(2) 0.04945(10) 0.0140(5) Uani 1 1 d . . . N2 N 0.00957(12) 0.1684(2) 0.20262(10) 0.0127(5) Uani 1 1 d . . . C1 C -0.00959(15) 0.1600(3) 0.00827(12) 0.0179(6) Uani 1 1 d . . . H1 H -0.0315 0.0899 0.0146 0.021 Uiso 1 1 calc R . . C2 C -0.00331(16) 0.1803(3) -0.04238(13) 0.0222(7) Uani 1 1 d . . . H2 H -0.0190 0.1238 -0.0702 0.027 Uiso 1 1 calc R . . C3 C 0.02664(18) 0.2858(3) -0.05155(13) 0.0270(8) Uani 1 1 d . . . H3 H 0.0310 0.3031 -0.0862 0.032 Uiso 1 1 calc R . . C4 C 0.05028(17) 0.3658(3) -0.01006(13) 0.0233(7) Uani 1 1 d . . . H4 H 0.0702 0.4385 -0.0165 0.028 Uiso 1 1 calc R . . C5 C 0.04475(14) 0.3395(3) 0.04142(12) 0.0153(6) Uani 1 1 d . . . C6 C 0.07205(13) 0.4040(3) 0.09093(11) 0.0131(6) Uani 1 1 d . . . C7 C 0.10667(14) 0.5132(3) 0.09527(12) 0.0154(6) Uani 1 1 d . . . C8 C 0.13526(15) 0.5591(3) 0.14503(13) 0.0182(7) Uani 1 1 d . . . H8 H 0.1583 0.6324 0.1480 0.022 Uiso 1 1 calc R . . C9 C 0.12996(15) 0.4968(3) 0.19082(12) 0.0168(6) Uani 1 1 d . . . C10 C 0.09467(14) 0.3923(3) 0.18786(12) 0.0158(6) Uani 1 1 d . . . H10 H 0.0910 0.3525 0.2194 0.019 Uiso 1 1 calc R . . C11 C 0.06419(13) 0.3456(3) 0.13779(12) 0.0124(6) Uani 1 1 d . . . C12 C 0.14507(18) 0.6794(3) 0.05363(14) 0.0257(8) Uani 1 1 d . . . H12A H 0.1288 0.7404 0.0740 0.039 Uiso 1 1 calc R . . H12B H 0.1433 0.7119 0.0181 0.039 Uiso 1 1 calc R . . H12C H 0.1868 0.6616 0.0718 0.039 Uiso 1 1 calc R . . C13 C 0.15615(17) 0.4933(3) 0.28604(13) 0.0252(8) Uani 1 1 d . . . H13A H 0.1142 0.4951 0.2879 0.038 Uiso 1 1 calc R . . H13B H 0.1808 0.5386 0.3162 0.038 Uiso 1 1 calc R . . H13C H 0.1699 0.4079 0.2872 0.038 Uiso 1 1 calc R . . C14 C 0.07865(14) 0.0881(3) 0.14439(12) 0.0140(6) Uani 1 1 d . . . C15 C 0.11640(14) 0.0548(3) 0.11116(12) 0.0136(6) Uani 1 1 d . . . H15 H 0.1095 0.0880 0.0764 0.016 Uiso 1 1 calc R . . C16 C 0.16328(14) -0.0258(3) 0.12935(12) 0.0140(6) Uani 1 1 d . . . C17 C 0.17489(14) -0.0770(3) 0.18029(12) 0.0145(6) Uani 1 1 d . . . H17 H 0.2073 -0.1326 0.1920 0.017 Uiso 1 1 calc R . . C18 C 0.13835(14) -0.0453(3) 0.21360(12) 0.0127(6) Uani 1 1 d . . . C19 C 0.08975(13) 0.0378(3) 0.19648(12) 0.0123(6) Uani 1 1 d . . . C20 C 0.05055(14) 0.0837(3) 0.22882(12) 0.0131(6) Uani 1 1 d . . . C21 C 0.05041(15) 0.0509(3) 0.28108(12) 0.0175(6) Uani 1 1 d . . . H21 H 0.0785 -0.0076 0.2997 0.021 Uiso 1 1 calc R . . C22 C 0.00938(15) 0.1036(3) 0.30565(12) 0.0191(7) Uani 1 1 d . . . H22 H 0.0084 0.0794 0.3405 0.023 Uiso 1 1 calc R . . C23 C -0.03010(16) 0.1916(3) 0.27892(13) 0.0204(7) Uani 1 1 d . . . H23 H -0.0575 0.2308 0.2956 0.025 Uiso 1 1 calc R . . C24 C -0.02899(15) 0.2214(3) 0.22755(13) 0.0172(6) Uani 1 1 d . . . H24 H -0.0563 0.2813 0.2091 0.021 Uiso 1 1 calc R . . C25 C 0.18889(15) -0.0252(3) 0.04547(12) 0.0205(7) Uani 1 1 d . . . H25A H 0.1474 -0.0480 0.0284 0.031 Uiso 1 1 calc R . . H25B H 0.2161 -0.0664 0.0274 0.031 Uiso 1 1 calc R . . H25C H 0.1936 0.0641 0.0433 0.031 Uiso 1 1 calc R . . C26 C 0.19835(16) -0.1680(3) 0.28370(13) 0.0201(7) Uani 1 1 d . . . H26A H 0.1958 -0.2418 0.2616 0.030 Uiso 1 1 calc R . . H26B H 0.2002 -0.1921 0.3204 0.030 Uiso 1 1 calc R . . H26C H 0.2345 -0.1215 0.2826 0.030 Uiso 1 1 calc R . . C27 C -0.10956(16) 0.0624(3) 0.09639(12) 0.0185(7) Uani 1 1 d . . . C28 C -0.14296(15) 0.1724(3) 0.09048(13) 0.0191(7) Uani 1 1 d . . . H28 H -0.1853 0.1639 0.0823 0.023 Uiso 1 1 calc R . . C29 C -0.12056(14) 0.2935(3) 0.09538(12) 0.0167(6) Uani 1 1 d . . . C30 C -0.14270(16) -0.0590(3) 0.08892(14) 0.0235(7) Uani 1 1 d . . . H30A H -0.1382 -0.0983 0.0562 0.035 Uiso 1 1 calc R . . H30B H -0.1853 -0.0445 0.0865 0.035 Uiso 1 1 calc R . . H30C H -0.1261 -0.1127 0.1192 0.035 Uiso 1 1 calc R . . C31 C -0.16469(16) 0.3993(3) 0.08307(14) 0.0247(7) Uani 1 1 d . . . H31A H -0.1596 0.4521 0.1144 0.037 Uiso 1 1 calc R . . H31B H -0.2056 0.3668 0.0734 0.037 Uiso 1 1 calc R . . H31C H -0.1574 0.4473 0.0534 0.037 Uiso 1 1 calc R . . C32A C 0.2728(3) 0.2175(6) 0.3644(3) 0.0345(15) Uani 0.721(6) 1 d PU A 1 H32A H 0.2701 0.3078 0.3599 0.041 Uiso 0.721(6) 1 calc PR A 1 H32B H 0.3109 0.1901 0.3569 0.041 Uiso 0.721(6) 1 calc PR A 1 Cl1A Cl 0.27355(12) 0.18000(17) 0.43115(12) 0.0531(7) Uani 0.721(6) 1 d PU A 1 Cl2A Cl 0.21260(11) 0.14834(17) 0.31899(14) 0.0641(9) Uani 0.721(6) 1 d PU A 1 C32B C 0.2721(10) 0.2327(19) 0.3376(10) 0.050(4) Uani 0.279(6) 1 d PU A 2 H32C H 0.3136 0.2052 0.3397 0.059 Uiso 0.279(6) 1 calc PR A 2 H32D H 0.2710 0.3231 0.3332 0.059 Uiso 0.279(6) 1 calc PR A 2 Cl1B Cl 0.2541(4) 0.1966(9) 0.3967(6) 0.100(3) Uani 0.279(6) 1 d PU A 2 Cl2B Cl 0.2241(3) 0.1658(5) 0.2812(5) 0.082(3) Uani 0.279(6) 1 d PU A 2 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 0.01081(7) 0.01176(6) 0.01281(6) -0.00031(4) 0.00302(4) -0.00044(5) O1 0.0310(14) 0.0170(11) 0.0164(11) 0.0016(9) 0.0066(10) -0.0092(10) O2 0.0265(14) 0.0221(12) 0.0149(11) -0.0021(9) 0.0024(10) -0.0085(10) O3 0.0157(12) 0.0239(11) 0.0167(11) -0.0006(9) 0.0067(9) 0.0040(9) O4 0.0173(12) 0.0188(11) 0.0160(11) 0.0041(9) 0.0051(9) 0.0044(9) O5 0.0119(12) 0.0197(11) 0.0186(11) -0.0014(9) 0.0021(9) -0.0026(9) O6 0.0184(13) 0.0198(11) 0.0187(11) 0.0017(9) 0.0037(10) 0.0026(9) N1 0.0122(13) 0.0168(12) 0.0116(12) -0.0003(10) 0.0000(10) 0.0008(10) N2 0.0106(13) 0.0138(12) 0.0147(12) -0.0028(9) 0.0046(10) -0.0037(9) C1 0.0153(17) 0.0173(14) 0.0183(16) -0.0019(12) -0.0011(13) -0.0016(12) C2 0.0268(19) 0.0194(16) 0.0167(15) -0.0045(12) -0.0017(14) -0.0022(13) C3 0.037(2) 0.0291(18) 0.0136(15) 0.0029(14) 0.0050(15) -0.0018(15) C4 0.031(2) 0.0196(17) 0.0188(16) 0.0035(13) 0.0051(15) -0.0030(14) C5 0.0156(16) 0.0148(14) 0.0149(14) 0.0009(11) 0.0027(12) 0.0004(12) C6 0.0109(15) 0.0138(14) 0.0135(14) -0.0001(11) 0.0011(11) 0.0018(11) C7 0.0161(16) 0.0161(14) 0.0149(14) 0.0018(12) 0.0053(12) -0.0009(12) C8 0.0181(17) 0.0135(14) 0.0226(16) -0.0016(12) 0.0043(13) -0.0064(12) C9 0.0173(17) 0.0198(15) 0.0125(14) -0.0041(12) 0.0022(12) -0.0013(12) C10 0.0202(17) 0.0150(14) 0.0136(14) -0.0016(12) 0.0066(12) -0.0008(12) C11 0.0062(14) 0.0122(13) 0.0188(15) 0.0017(11) 0.0033(12) 0.0046(10) C12 0.034(2) 0.0222(17) 0.0218(17) 0.0036(13) 0.0078(15) -0.0102(15) C13 0.032(2) 0.0249(17) 0.0170(16) -0.0005(13) 0.0038(15) -0.0065(15) C14 0.0171(16) 0.0094(13) 0.0142(14) -0.0023(11) 0.0014(12) -0.0010(11) C15 0.0109(15) 0.0174(14) 0.0112(14) -0.0004(11) 0.0004(11) -0.0042(11) C16 0.0119(15) 0.0150(14) 0.0157(14) -0.0040(11) 0.0046(12) -0.0040(11) C17 0.0124(15) 0.0137(14) 0.0173(15) 0.0000(11) 0.0039(12) -0.0004(11) C18 0.0116(15) 0.0122(13) 0.0145(14) -0.0007(11) 0.0038(12) -0.0037(11) C19 0.0091(15) 0.0106(13) 0.0174(14) -0.0006(11) 0.0040(12) -0.0035(11) C20 0.0123(15) 0.0120(13) 0.0151(14) -0.0028(11) 0.0035(12) -0.0016(11) C21 0.0214(18) 0.0153(14) 0.0170(15) -0.0008(12) 0.0069(13) -0.0016(12) C22 0.0242(18) 0.0193(15) 0.0150(15) -0.0021(12) 0.0072(13) -0.0022(13) C23 0.0194(18) 0.0212(16) 0.0242(17) -0.0044(13) 0.0121(14) -0.0006(13) C24 0.0163(17) 0.0159(15) 0.0206(16) -0.0002(12) 0.0066(13) 0.0009(11) C25 0.0189(18) 0.0304(18) 0.0155(15) -0.0008(13) 0.0107(13) 0.0003(14) C26 0.0208(18) 0.0227(16) 0.0162(15) 0.0021(12) 0.0033(13) 0.0067(13) C27 0.0229(18) 0.0243(16) 0.0080(14) -0.0008(12) 0.0028(13) -0.0078(13) C28 0.0115(16) 0.0270(17) 0.0177(15) -0.0005(13) 0.0016(13) -0.0021(12) C29 0.0125(16) 0.0253(16) 0.0122(14) 0.0006(12) 0.0028(12) 0.0010(13) C30 0.0186(18) 0.0271(17) 0.0248(18) -0.0018(14) 0.0056(14) -0.0076(14) C31 0.0192(18) 0.0283(18) 0.0255(17) 0.0031(15) 0.0033(14) 0.0080(14) C32A 0.032(3) 0.027(3) 0.043(4) -0.001(3) 0.005(4) -0.008(2) Cl1A 0.0544(14) 0.0413(9) 0.0691(16) -0.0101(9) 0.0256(12) -0.0075(8) Cl2A 0.0510(12) 0.0307(8) 0.092(2) -0.0047(10) -0.0182(12) -0.0135(8) C32B 0.040(7) 0.029(6) 0.074(9) -0.011(8) 0.005(8) -0.005(6) Cl1B 0.071(5) 0.094(5) 0.133(8) -0.059(6) 0.021(5) -0.009(4) Cl2B 0.042(3) 0.033(2) 0.149(8) -0.019(4) -0.016(4) -0.004(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 C11 1.981(3) . ? Ir1 C14 1.988(3) . ? Ir1 N1 2.038(3) . ? Ir1 N2 2.041(3) . ? Ir1 O5 2.147(2) . ? Ir1 O6 2.158(2) . ? O1 C7 1.368(4) . ? O1 C12 1.429(4) . ? O2 C9 1.371(4) . ? O2 C13 1.438(4) . ? O3 C16 1.383(4) . ? O3 C25 1.432(4) . ? O4 C18 1.377(3) . ? O4 C26 1.432(4) . ? O5 C27 1.278(4) . ? O6 C29 1.265(4) . ? N1 C1 1.354(4) . ? N1 C5 1.375(4) . ? N2 C24 1.352(4) . ? N2 C20 1.373(4) . ? C1 C2 1.378(5) . ? C1 H1 0.9500 . ? C2 C3 1.390(5) . ? C2 H2 0.9500 . ? C3 C4 1.388(5) . ? C3 H3 0.9500 . ? C4 C5 1.406(4) . ? C4 H4 0.9500 . ? C5 C6 1.464(4) . ? C6 C7 1.420(4) . ? C6 C11 1.425(4) . ? C7 C8 1.392(4) . ? C8 C9 1.401(4) . ? C8 H8 0.9500 . ? C9 C10 1.389(4) . ? C10 C11 1.412(4) . ? C10 H10 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.417(4) . ? C14 C19 1.424(4) . ? C15 C16 1.381(4) . ? C15 H15 0.9500 . ? C16 C17 1.400(4) . ? C17 C18 1.393(4) . ? C17 H17 0.9500 . ? C18 C19 1.422(4) . ? C19 C20 1.466(4) . ? C20 C21 1.406(4) . ? C21 C22 1.389(4) . ? C21 H21 0.9500 . ? C22 C23 1.383(5) . ? C22 H22 0.9500 . ? C23 C24 1.381(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.410(5) . ? C27 C30 1.514(4) . ? C28 C29 1.410(4) . ? C28 H28 0.9500 . ? C29 C31 1.516(4) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32A Cl2A 1.754(7) . ? C32A Cl1A 1.779(7) . ? C32A H32A 0.9900 . ? C32A H32B 0.9900 . ? C32B Cl1B 1.74(2) . ? C32B Cl2B 1.76(2) . ? C32B H32C 0.9900 . ? C32B H32D 0.9900 . ? 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 C11 Ir1 C14 90.60(12) . . ? C11 Ir1 N1 80.38(11) . . ? C14 Ir1 N1 96.82(11) . . ? C11 Ir1 N2 97.86(11) . . ? C14 Ir1 N2 80.54(11) . . ? N1 Ir1 N2 176.85(10) . . ? C11 Ir1 O5 176.12(10) . . ? C14 Ir1 O5 91.51(10) . . ? N1 Ir1 O5 96.14(9) . . ? N2 Ir1 O5 85.70(9) . . ? C11 Ir1 O6 89.62(10) . . ? C14 Ir1 O6 176.60(10) . . ? N1 Ir1 O6 86.56(9) . . ? N2 Ir1 O6 96.06(9) . . ? O5 Ir1 O6 88.46(9) . . ? C7 O1 C12 117.2(2) . . ? C9 O2 C13 117.3(2) . . ? C16 O3 C25 116.7(2) . . ? C18 O4 C26 117.5(2) . . ? C27 O5 Ir1 124.7(2) . . ? C29 O6 Ir1 125.0(2) . . ? C1 N1 C5 120.0(3) . . ? C1 N1 Ir1 123.4(2) . . ? C5 N1 Ir1 116.5(2) . . ? C24 N2 C20 120.0(3) . . ? C24 N2 Ir1 123.6(2) . . ? C20 N2 Ir1 116.36(19) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.1(3) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 118.9(3) . . ? N1 C5 C6 112.6(3) . . ? C4 C5 C6 128.3(3) . . ? C7 C6 C11 119.5(3) . . ? C7 C6 C5 125.5(3) . . ? C11 C6 C5 114.9(3) . . ? O1 C7 C8 122.5(3) . . ? O1 C7 C6 117.4(3) . . ? C8 C7 C6 120.1(3) . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? O2 C9 C10 124.3(3) . . ? O2 C9 C8 114.2(3) . . ? C10 C9 C8 121.5(3) . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C6 119.2(3) . . ? C10 C11 Ir1 125.8(2) . . ? C6 C11 Ir1 115.0(2) . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.3(3) . . ? C15 C14 Ir1 125.8(2) . . ? C19 C14 Ir1 114.9(2) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 O3 124.0(3) . . ? C15 C16 C17 121.7(3) . . ? O3 C16 C17 114.3(3) . . ? C18 C17 C16 119.1(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? O4 C18 C17 122.4(3) . . ? O4 C18 C19 116.7(3) . . ? C17 C18 C19 120.9(3) . . ? C18 C19 C14 118.9(3) . . ? C18 C19 C20 125.9(3) . . ? C14 C19 C20 115.1(3) . . ? N2 C20 C21 118.9(3) . . ? N2 C20 C19 112.9(3) . . ? C21 C20 C19 128.1(3) . . ? C22 C21 C20 120.3(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 119.5(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 118.7(3) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? N2 C24 C23 122.4(3) . . ? N2 C24 H24 118.8 . . ? C23 C24 H24 118.8 . . ? O3 C25 H25A 109.5 . . ? O3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O4 C26 H26A 109.5 . . ? O4 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O4 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O5 C27 C28 127.0(3) . . ? O5 C27 C30 114.1(3) . . ? C28 C27 C30 118.8(3) . . ? C29 C28 C27 127.3(3) . . ? C29 C28 H28 116.4 . . ? C27 C28 H28 116.4 . . ? O6 C29 C28 127.0(3) . . ? O6 C29 C31 114.3(3) . . ? C28 C29 C31 118.6(3) . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? Cl2A C32A Cl1A 111.9(4) . . ? Cl2A C32A H32A 109.2 . . ? Cl1A C32A H32A 109.2 . . ? Cl2A C32A H32B 109.2 . . ? Cl1A C32A H32B 109.2 . . ? H32A C32A H32B 107.9 . . ? Cl1B C32B Cl2B 113.9(13) . . ? Cl1B C32B H32C 108.8 . . ? Cl2B C32B H32C 108.8 . . ? Cl1B C32B H32D 108.8 . . ? Cl2B C32B H32D 108.8 . . ? H32C C32B H32D 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Ir1 O5 C27 171.5(2) . . . . ? N1 Ir1 O5 C27 -91.5(2) . . . . ? N2 Ir1 O5 C27 91.1(2) . . . . ? O6 Ir1 O5 C27 -5.1(2) . . . . ? C11 Ir1 O6 C29 176.5(2) . . . . ? N1 Ir1 O6 C29 96.1(2) . . . . ? N2 Ir1 O6 C29 -85.6(2) . . . . ? O5 Ir1 O6 C29 -0.1(2) . . . . ? C11 Ir1 N1 C1 171.9(3) . . . . ? C14 Ir1 N1 C1 82.5(3) . . . . ? O5 Ir1 N1 C1 -9.8(3) . . . . ? O6 Ir1 N1 C1 -97.9(3) . . . . ? C11 Ir1 N1 C5 -6.2(2) . . . . ? C14 Ir1 N1 C5 -95.6(2) . . . . ? O5 Ir1 N1 C5 172.1(2) . . . . ? O6 Ir1 N1 C5 84.0(2) . . . . ? C11 Ir1 N2 C24 88.6(2) . . . . ? C14 Ir1 N2 C24 177.9(3) . . . . ? O5 Ir1 N2 C24 -89.8(2) . . . . ? O6 Ir1 N2 C24 -1.8(2) . . . . ? C11 Ir1 N2 C20 -93.4(2) . . . . ? C14 Ir1 N2 C20 -4.1(2) . . . . ? O5 Ir1 N2 C20 88.1(2) . . . . ? O6 Ir1 N2 C20 176.1(2) . . . . ? C5 N1 C1 C2 1.5(5) . . . . ? Ir1 N1 C1 C2 -176.5(3) . . . . ? N1 C1 C2 C3 -2.6(5) . . . . ? C1 C2 C3 C4 1.3(6) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C1 N1 C5 C4 0.8(5) . . . . ? Ir1 N1 C5 C4 179.0(2) . . . . ? C1 N1 C5 C6 -174.5(3) . . . . ? Ir1 N1 C5 C6 3.6(3) . . . . ? C3 C4 C5 N1 -2.0(5) . . . . ? C3 C4 C5 C6 172.5(3) . . . . ? N1 C5 C6 C7 179.6(3) . . . . ? C4 C5 C6 C7 4.8(5) . . . . ? N1 C5 C6 C11 2.6(4) . . . . ? C4 C5 C6 C11 -172.2(3) . . . . ? C12 O1 C7 C8 -0.8(5) . . . . ? C12 O1 C7 C6 179.6(3) . . . . ? C11 C6 C7 O1 -177.0(3) . . . . ? C5 C6 C7 O1 6.1(5) . . . . ? C11 C6 C7 C8 3.3(5) . . . . ? C5 C6 C7 C8 -173.6(3) . . . . ? O1 C7 C8 C9 -179.4(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C13 O2 C9 C10 -1.2(5) . . . . ? C13 O2 C9 C8 177.7(3) . . . . ? C7 C8 C9 O2 178.5(3) . . . . ? C7 C8 C9 C10 -2.7(5) . . . . ? O2 C9 C10 C11 -180.0(3) . . . . ? C8 C9 C10 C11 1.3(5) . . . . ? C9 C10 C11 C6 2.4(4) . . . . ? C9 C10 C11 Ir1 -177.3(2) . . . . ? C7 C6 C11 C10 -4.7(4) . . . . ? C5 C6 C11 C10 172.6(3) . . . . ? C7 C6 C11 Ir1 175.0(2) . . . . ? C5 C6 C11 Ir1 -7.7(3) . . . . ? C14 Ir1 C11 C10 -76.1(3) . . . . ? N1 Ir1 C11 C10 -172.9(3) . . . . ? N2 Ir1 C11 C10 4.4(3) . . . . ? O6 Ir1 C11 C10 100.5(3) . . . . ? C14 Ir1 C11 C6 104.2(2) . . . . ? N1 Ir1 C11 C6 7.4(2) . . . . ? N2 Ir1 C11 C6 -175.3(2) . . . . ? O6 Ir1 C11 C6 -79.2(2) . . . . ? C11 Ir1 C14 C15 -77.9(3) . . . . ? N1 Ir1 C14 C15 2.5(3) . . . . ? N2 Ir1 C14 C15 -175.8(3) . . . . ? O5 Ir1 C14 C15 98.8(3) . . . . ? C11 Ir1 C14 C19 101.8(2) . . . . ? N1 Ir1 C14 C19 -177.8(2) . . . . ? N2 Ir1 C14 C19 4.0(2) . . . . ? O5 Ir1 C14 C19 -81.4(2) . . . . ? C19 C14 C15 C16 0.2(4) . . . . ? Ir1 C14 C15 C16 179.9(2) . . . . ? C14 C15 C16 O3 -179.0(3) . . . . ? C14 C15 C16 C17 0.2(4) . . . . ? C25 O3 C16 C15 -8.4(4) . . . . ? C25 O3 C16 C17 172.4(3) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? O3 C16 C17 C18 179.0(3) . . . . ? C26 O4 C18 C17 6.3(4) . . . . ? C26 O4 C18 C19 -174.5(3) . . . . ? C16 C17 C18 O4 179.2(3) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? O4 C18 C19 C14 -178.9(3) . . . . ? C17 C18 C19 C14 0.3(4) . . . . ? O4 C18 C19 C20 4.7(4) . . . . ? C17 C18 C19 C20 -176.1(3) . . . . ? C15 C14 C19 C18 -0.4(4) . . . . ? Ir1 C14 C19 C18 179.9(2) . . . . ? C15 C14 C19 C20 176.4(3) . . . . ? Ir1 C14 C19 C20 -3.4(3) . . . . ? C24 N2 C20 C21 1.8(4) . . . . ? Ir1 N2 C20 C21 -176.2(2) . . . . ? C24 N2 C20 C19 -178.6(3) . . . . ? Ir1 N2 C20 C19 3.4(3) . . . . ? C18 C19 C20 N2 176.5(3) . . . . ? C14 C19 C20 N2 0.0(4) . . . . ? C18 C19 C20 C21 -4.0(5) . . . . ? C14 C19 C20 C21 179.5(3) . . . . ? N2 C20 C21 C22 0.0(4) . . . . ? C19 C20 C21 C22 -179.5(3) . . . . ? C20 C21 C22 C23 -2.1(5) . . . . ? C21 C22 C23 C24 2.3(5) . . . . ? C20 N2 C24 C23 -1.6(5) . . . . ? Ir1 N2 C24 C23 176.3(2) . . . . ? C22 C23 C24 N2 -0.5(5) . . . . ? Ir1 O5 C27 C28 6.4(4) . . . . ? Ir1 O5 C27 C30 -175.14(19) . . . . ? O5 C27 C28 C29 -1.0(5) . . . . ? C30 C27 C28 C29 -179.4(3) . . . . ? Ir1 O6 C29 C28 4.7(4) . . . . ? Ir1 O6 C29 C31 -175.8(2) . . . . ? C27 C28 C29 O6 -5.3(5) . . . . ? C27 C28 C29 C31 175.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.733 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.117 _iucr_refine_instructions_details ; TITL EB200 in I2/a CELL 0.71073 23.0408 10.8791 26.0085 90.000 104.362 90.000 ZERR 8.00 0.0029 0.0015 0.0050 0.000 0.009 0.000 LATT 2 SYMM 0.5-X, Y, -Z SFAC C H N O CL IR UNIT 256 264 16 48 16 8 REM ---------------------------------------------------------- REM Data collection: Bruker APEX II CCD REM Absorption correction: SADABS REM Crystal habit: prismatic; Crystal colour: yellow REM ---------------------------------------------------------- TEMP -173 L.S. 10 ACTA CONF SIZE 0.500 0.461 0.203 WPDB -2 BOND $H FMAP 2 PLAN 10 SIMU 0.01 C32A > CL2B WGHT 0.021200 22.661299 FVAR 0.09752 0.72068 MOLE 1 IR1 6 0.009318 0.202511 0.125396 11.00000 0.01081 0.01176 = 0.01281 -0.00031 0.00302 -0.00044 O1 4 0.110542 0.568974 0.049108 11.00000 0.03100 0.01695 = 0.01644 0.00158 0.00661 -0.00919 O2 4 0.161326 0.549462 0.237335 11.00000 0.02650 0.02214 = 0.01487 -0.00213 0.00239 -0.00851 O3 4 0.202855 -0.062012 0.100017 11.00000 0.01566 0.02390 = 0.01673 -0.00057 0.00672 0.00401 O4 4 0.146543 -0.093013 0.263939 11.00000 0.01730 0.01884 = 0.01597 0.00413 0.00512 0.00443 O5 4 -0.052570 0.051989 0.106612 11.00000 0.01188 0.01967 = 0.01864 -0.00141 0.00212 -0.00255 O6 4 -0.066253 0.326173 0.109622 11.00000 0.01836 0.01981 = 0.01872 0.00170 0.00373 0.00259 N1 3 0.014072 0.235706 0.049445 11.00000 0.01216 0.01685 = 0.01161 -0.00028 0.00004 0.00078 N2 3 0.009572 0.168429 0.202617 11.00000 0.01057 0.01376 = 0.01466 -0.00282 0.00463 -0.00367 C1 1 -0.009591 0.160022 0.008271 11.00000 0.01528 0.01729 = 0.01825 -0.00190 -0.00107 -0.00164 AFIX 43 H1 2 -0.031455 0.089949 0.014556 11.00000 -1.20000 AFIX 0 C2 1 -0.003313 0.180300 -0.042385 11.00000 0.02683 0.01941 = 0.01668 -0.00454 -0.00172 -0.00223 AFIX 43 H2 2 -0.019008 0.123830 -0.070222 11.00000 -1.20000 AFIX 0 C3 1 0.026644 0.285754 -0.051546 11.00000 0.03744 0.02913 = 0.01362 0.00288 0.00499 -0.00180 AFIX 43 H3 2 0.030953 0.303085 -0.086207 11.00000 -1.20000 AFIX 0 C4 1 0.050281 0.365803 -0.010056 11.00000 0.03105 0.01957 = 0.01883 0.00350 0.00507 -0.00304 AFIX 43 H4 2 0.070227 0.438494 -0.016473 11.00000 -1.20000 AFIX 0 C5 1 0.044749 0.339468 0.041421 11.00000 0.01563 0.01483 = 0.01495 0.00089 0.00267 0.00041 C6 1 0.072052 0.403959 0.090933 11.00000 0.01087 0.01378 = 0.01350 -0.00007 0.00106 0.00181 C7 1 0.106670 0.513157 0.095265 11.00000 0.01606 0.01608 = 0.01495 0.00176 0.00528 -0.00085 C8 1 0.135265 0.559118 0.145032 11.00000 0.01814 0.01346 = 0.02261 -0.00163 0.00435 -0.00643 AFIX 43 H8 2 0.158280 0.632397 0.147960 11.00000 -1.20000 AFIX 0 C9 1 0.129962 0.496834 0.190815 11.00000 0.01728 0.01976 = 0.01246 -0.00413 0.00224 -0.00130 C10 1 0.094668 0.392348 0.187858 11.00000 0.02018 0.01496 = 0.01361 -0.00155 0.00664 -0.00082 AFIX 43 H10 2 0.091039 0.352466 0.219406 11.00000 -1.20000 AFIX 0 C11 1 0.064191 0.345595 0.137792 11.00000 0.00621 0.01220 = 0.01882 0.00174 0.00327 0.00460 C12 1 0.145072 0.679387 0.053625 11.00000 0.03370 0.02219 = 0.02179 0.00360 0.00784 -0.01015 AFIX 33 H12A 2 0.128789 0.740364 0.074004 11.00000 -1.50000 H12B 2 0.143298 0.711875 0.018124 11.00000 -1.50000 H12C 2 0.186804 0.661620 0.071844 11.00000 -1.50000 AFIX 0 C13 1 0.156154 0.493286 0.286043 11.00000 0.03236 0.02487 = 0.01700 -0.00052 0.00381 -0.00646 AFIX 33 H13A 2 0.114197 0.495077 0.287900 11.00000 -1.50000 H13B 2 0.180801 0.538619 0.316213 11.00000 -1.50000 H13C 2 0.169936 0.407874 0.287213 11.00000 -1.50000 AFIX 0 C14 1 0.078650 0.088093 0.144395 11.00000 0.01706 0.00943 = 0.01424 -0.00233 0.00145 -0.00099 C15 1 0.116404 0.054843 0.111162 11.00000 0.01094 0.01738 = 0.01115 -0.00044 0.00038 -0.00424 AFIX 43 H15 2 0.109470 0.088034 0.076381 11.00000 -1.20000 AFIX 0 C16 1 0.163285 -0.025828 0.129347 11.00000 0.01191 0.01503 = 0.01573 -0.00401 0.00460 -0.00397 C17 1 0.174885 -0.077009 0.180290 11.00000 0.01242 0.01372 = 0.01734 -0.00005 0.00389 -0.00035 AFIX 43 H17 2 0.207253 -0.132648 0.191978 11.00000 -1.20000 AFIX 0 C18 1 0.138353 -0.045279 0.213596 11.00000 0.01159 0.01224 = 0.01449 -0.00073 0.00377 -0.00368 C19 1 0.089747 0.037770 0.196481 11.00000 0.00910 0.01063 = 0.01745 -0.00064 0.00395 -0.00355 C20 1 0.050555 0.083739 0.228820 11.00000 0.01232 0.01200 = 0.01509 -0.00282 0.00346 -0.00157 C21 1 0.050407 0.050913 0.281083 11.00000 0.02140 0.01533 = 0.01701 -0.00080 0.00690 -0.00161 AFIX 43 H21 2 0.078502 -0.007572 0.299680 11.00000 -1.20000 AFIX 0 C22 1 0.009378 0.103586 0.305655 11.00000 0.02425 0.01931 = 0.01502 -0.00209 0.00721 -0.00218 AFIX 43 H22 2 0.008442 0.079364 0.340533 11.00000 -1.20000 AFIX 0 C23 1 -0.030102 0.191591 0.278922 11.00000 0.01943 0.02120 = 0.02423 -0.00442 0.01207 -0.00056 AFIX 43 H23 2 -0.057462 0.230789 0.295581 11.00000 -1.20000 AFIX 0 C24 1 -0.028988 0.221393 0.227548 11.00000 0.01625 0.01586 = 0.02056 -0.00017 0.00663 0.00086 AFIX 43 H24 2 -0.056322 0.281305 0.209058 11.00000 -1.20000 AFIX 0 C25 1 0.188886 -0.025165 0.045474 11.00000 0.01894 0.03036 = 0.01552 -0.00080 0.01069 0.00031 AFIX 33 H25A 2 0.147448 -0.047970 0.028361 11.00000 -1.50000 H25B 2 0.216087 -0.066384 0.027418 11.00000 -1.50000 H25C 2 0.193562 0.064078 0.043311 11.00000 -1.50000 AFIX 0 C26 1 0.198352 -0.168031 0.283704 11.00000 0.02084 0.02266 = 0.01618 0.00206 0.00332 0.00668 AFIX 33 H26A 2 0.195839 -0.241772 0.261618 11.00000 -1.50000 H26B 2 0.200214 -0.192149 0.320382 11.00000 -1.50000 H26C 2 0.234456 -0.121507 0.282636 11.00000 -1.50000 AFIX 0 C27 1 -0.109556 0.062397 0.096392 11.00000 0.02285 0.02431 = 0.00795 -0.00080 0.00284 -0.00779 C28 1 -0.142958 0.172379 0.090483 11.00000 0.01153 0.02700 = 0.01775 -0.00050 0.00161 -0.00206 AFIX 43 H28 2 -0.185297 0.163862 0.082281 11.00000 -1.20000 AFIX 0 C29 1 -0.120562 0.293547 0.095383 11.00000 0.01246 0.02531 = 0.01217 0.00061 0.00283 0.00104 C30 1 -0.142704 -0.058993 0.088925 11.00000 0.01859 0.02714 = 0.02481 -0.00182 0.00560 -0.00759 AFIX 33 H30A 2 -0.138194 -0.098305 0.056235 11.00000 -1.50000 H30B 2 -0.185288 -0.044522 0.086463 11.00000 -1.50000 H30C 2 -0.126090 -0.112740 0.119241 11.00000 -1.50000 AFIX 0 C31 1 -0.164685 0.399286 0.083066 11.00000 0.01919 0.02829 = 0.02550 0.00308 0.00325 0.00795 AFIX 33 H31A 2 -0.159586 0.452091 0.114398 11.00000 -1.50000 H31B 2 -0.205635 0.366831 0.073418 11.00000 -1.50000 H31C 2 -0.157360 0.447294 0.053419 11.00000 -1.50000 AFIX 0 MOLE 2 PART 1 C32A 1 0.272836 0.217466 0.364432 21.00000 0.03160 0.02662 = 0.04321 -0.00078 0.00515 -0.00810 AFIX 23 H32A 2 0.270131 0.307802 0.359878 21.00000 -1.20000 H32B 2 0.310875 0.190087 0.356916 21.00000 -1.20000 AFIX 0 CL1A 5 0.273548 0.179998 0.431153 21.00000 0.05439 0.04131 = 0.06909 -0.01014 0.02563 -0.00754 CL2A 5 0.212603 0.148336 0.318989 21.00000 0.05095 0.03073 = 0.09158 -0.00469 -0.01819 -0.01349 PART 2 C32B 1 0.272138 0.232682 0.337554 -21.00000 0.03985 0.02925 = 0.07446 -0.01054 0.00458 -0.00535 AFIX 23 H32C 2 0.313637 0.205190 0.339728 -21.00000 -1.20000 H32D 2 0.271047 0.323113 0.333168 -21.00000 -1.20000 AFIX 0 CL1B 5 0.254070 0.196649 0.396712 -21.00000 0.07129 0.09393 = 0.13291 -0.05872 0.02062 -0.00910 CL2B 5 0.224075 0.165827 0.281175 -21.00000 0.04171 0.03336 = 0.14941 -0.01852 -0.01555 -0.00388 PART 0 MOLE 0 HKLF 4 1 0 0 -1 0 1 0 1 0 1 REM EB200 in I2/a REM R1 = 0.0238 for 6224 Fo > 4sig(Fo) and 0.0333 for all 7224 data REM 416 parameters refined using 30 restraints END WGHT 0.0212 22.6646 REM Highest difference peak 0.733, deepest hole -0.791, 1-sigma level 0.117 Q1 1 0.0103 0.3977 0.1252 11.00000 0.05 0.73 Q2 1 -0.0189 0.2189 0.1030 11.00000 0.05 0.73 Q3 1 0.0093 0.2987 0.1450 11.00000 0.05 0.58 Q4 1 -0.0316 0.1031 0.1082 11.00000 0.05 0.55 Q5 1 0.2431 0.2563 0.3699 11.00000 0.05 0.55 Q6 1 0.0731 0.0560 0.1680 11.00000 0.05 0.54 Q7 1 0.1395 -0.0835 0.1835 11.00000 0.05 0.53 Q8 1 0.1933 0.1788 0.3496 11.00000 0.05 0.53 Q9 1 0.0493 0.1187 0.1296 11.00000 0.05 0.52 Q10 1 0.0469 0.1848 0.1544 11.00000 0.05 0.51 ; _database_code_depnum_ccdc_archive 'CCDC 964312' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jf360 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H31 Ir N2 O4' _chemical_formula_sum 'C31 H31 Ir N2 O4' _chemical_formula_weight 687.78 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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0818(16) _cell_length_b 10.4988(19) _cell_length_c 13.2307(9) _cell_angle_alpha 99.755(10) _cell_angle_beta 92.785(7) _cell_angle_gamma 103.058(16) _cell_volume 1339.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 114 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 5.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4169 _exptl_absorpt_correction_T_max 0.7467 _exptl_absorpt_process_details 'SADABS 2008, Bruker AXS, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 36079 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 34.00 _reflns_number_total 10808 _reflns_number_gt 9863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _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^)+(0.0168P)^2^+0.6623P] 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 10808 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0468 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 0.205781(6) 0.460864(6) 0.236601(5) 0.01220(2) Uani 1 1 d . . . O1 O -0.18839(14) 0.02174(14) 0.04864(11) 0.0197(3) Uani 1 1 d . . . O2 O 0.51039(16) 0.14354(15) 0.36690(12) 0.0242(3) Uani 1 1 d . . . O3 O 0.38659(13) 0.62051(13) 0.26011(11) 0.0172(2) Uani 1 1 d . . . O4 O 0.08732(14) 0.61043(13) 0.24300(11) 0.0182(2) Uani 1 1 d . . . N1 N 0.18150(15) 0.46247(15) 0.38856(12) 0.0152(3) Uani 1 1 d . . . N2 N 0.23519(15) 0.44742(15) 0.08435(12) 0.0140(3) Uani 1 1 d . . . C1 C 0.2592(2) 0.5567(2) 0.46422(15) 0.0203(3) Uani 1 1 d . . . H1 H 0.3274 0.6250 0.4454 0.024 Uiso 1 1 calc R . . C2 C 0.2439(2) 0.5582(2) 0.56777(15) 0.0228(4) Uani 1 1 d . . . H2 H 0.3009 0.6249 0.6192 0.027 Uiso 1 1 calc R . . C3 C 0.1420(2) 0.4585(2) 0.59401(15) 0.0222(4) Uani 1 1 d . . . H3 H 0.1275 0.4569 0.6642 0.027 Uiso 1 1 calc R . . C4 C 0.0618(2) 0.36152(19) 0.51682(14) 0.0186(3) Uani 1 1 d . . . H4 H -0.0078 0.2938 0.5348 0.022 Uiso 1 1 calc R . . C5 C 0.08220(18) 0.36211(17) 0.41237(14) 0.0148(3) Uani 1 1 d . . . C6 C 0.00724(17) 0.26839(17) 0.32106(14) 0.0144(3) Uani 1 1 d . . . C7 C -0.09314(18) 0.14908(18) 0.32177(14) 0.0163(3) Uani 1 1 d . . . C8 C -0.15396(18) 0.07144(18) 0.22789(15) 0.0169(3) Uani 1 1 d . . . H8 H -0.2204 -0.0089 0.2274 0.020 Uiso 1 1 calc R . . C9 C -0.11933(18) 0.10906(18) 0.13424(14) 0.0154(3) Uani 1 1 d . . . C10 C -0.01926(17) 0.22427(17) 0.13261(14) 0.0145(3) Uani 1 1 d . . . H10 H 0.0044 0.2486 0.0687 0.017 Uiso 1 1 calc R . . C11 C 0.04704(17) 0.30492(17) 0.22590(13) 0.0134(3) Uani 1 1 d . . . C12 C -0.1376(2) 0.0959(2) 0.41747(16) 0.0250(4) Uani 1 1 d . . . H12A H -0.1880 0.1544 0.4564 0.037 Uiso 1 1 calc R . . H12B H -0.0568 0.0928 0.4604 0.037 Uiso 1 1 calc R . . H12C H -0.1967 0.0061 0.3974 0.037 Uiso 1 1 calc R . . C13 C -0.1567(2) 0.0528(2) -0.05027(15) 0.0207(3) Uani 1 1 d . . . H13A H -0.1807 0.1365 -0.0571 0.031 Uiso 1 1 calc R . . H13B H -0.2090 -0.0188 -0.1045 0.031 Uiso 1 1 calc R . . H13C H -0.0587 0.0620 -0.0567 0.031 Uiso 1 1 calc R . . C14 C 0.32619(17) 0.33437(17) 0.22293(14) 0.0138(3) Uani 1 1 d . . . C15 C 0.36551(19) 0.27559(18) 0.30392(14) 0.0166(3) Uani 1 1 d . . . H15 H 0.3272 0.2887 0.3679 0.020 Uiso 1 1 calc R . . C16 C 0.46017(19) 0.19863(18) 0.29002(15) 0.0174(3) Uani 1 1 d . . . C17 C 0.51353(19) 0.17392(19) 0.19469(15) 0.0185(3) Uani 1 1 d . . . H17 H 0.5784 0.1208 0.1867 0.022 Uiso 1 1 calc R . . C18 C 0.47301(18) 0.22598(18) 0.11146(14) 0.0161(3) Uani 1 1 d . . . C19 C 0.37890(17) 0.30882(17) 0.12573(13) 0.0143(3) Uani 1 1 d . . . C20 C 0.32696(18) 0.37570(17) 0.04853(14) 0.0146(3) Uani 1 1 d . . . C21 C 0.3620(2) 0.3767(2) -0.05333(15) 0.0224(4) Uani 1 1 d . . . H21 H 0.4279 0.3304 -0.0787 0.027 Uiso 1 1 calc R . . C22 C 0.3018(2) 0.4440(2) -0.11702(15) 0.0233(4) Uani 1 1 d . . . H22 H 0.3260 0.4436 -0.1856 0.028 Uiso 1 1 calc R . . C23 C 0.2055(2) 0.5123(2) -0.07974(15) 0.0215(4) Uani 1 1 d . . . H23 H 0.1610 0.5571 -0.1224 0.026 Uiso 1 1 calc R . . C24 C 0.17674(18) 0.51258(18) 0.02162(14) 0.0171(3) Uani 1 1 d . . . H24 H 0.1130 0.5608 0.0483 0.021 Uiso 1 1 calc R . . C25 C 0.4481(3) 0.1546(2) 0.46123(17) 0.0293(5) Uani 1 1 d . . . H25A H 0.4567 0.2487 0.4901 0.044 Uiso 1 1 calc R . . H25B H 0.4936 0.1141 0.5100 0.044 Uiso 1 1 calc R . . H25C H 0.3512 0.1086 0.4485 0.044 Uiso 1 1 calc R . . C26 C 0.5303(2) 0.1851(2) 0.01050(16) 0.0222(4) Uani 1 1 d . . . H26A H 0.5832 0.2644 -0.0116 0.033 Uiso 1 1 calc R . . H26B H 0.4550 0.1393 -0.0420 0.033 Uiso 1 1 calc R . . H26C H 0.5898 0.1251 0.0198 0.033 Uiso 1 1 calc R . . C27 C 0.3896(2) 0.74392(18) 0.26857(14) 0.0176(3) Uani 1 1 d . . . C28 C 0.2769(2) 0.80220(19) 0.27058(15) 0.0209(4) Uani 1 1 d . . . H28 H 0.2970 0.8966 0.2816 0.025 Uiso 1 1 calc R . . C29 C 0.1374(2) 0.73589(19) 0.25805(14) 0.0187(3) Uani 1 1 d . . . C30 C 0.5316(2) 0.8340(2) 0.27792(16) 0.0233(4) Uani 1 1 d . . . H30A H 0.5966 0.7938 0.3110 0.035 Uiso 1 1 calc R . . H30B H 0.5320 0.9207 0.3196 0.035 Uiso 1 1 calc R . . H30C H 0.5580 0.8460 0.2092 0.035 Uiso 1 1 calc R . . C31 C 0.0322(2) 0.8194(2) 0.26062(17) 0.0256(4) Uani 1 1 d . . . H31A H -0.0268 0.7931 0.1958 0.038 Uiso 1 1 calc R . . H31B H 0.0790 0.9136 0.2695 0.038 Uiso 1 1 calc R . . H31C H -0.0236 0.8052 0.3182 0.038 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 0.01087(3) 0.01256(3) 0.01337(3) 0.00320(2) 0.00275(2) 0.00225(2) O1 0.0192(6) 0.0197(6) 0.0164(6) 0.0026(5) -0.0012(5) -0.0021(5) O2 0.0307(8) 0.0247(7) 0.0216(7) 0.0084(5) -0.0002(6) 0.0131(6) O3 0.0134(5) 0.0146(6) 0.0221(6) 0.0027(5) 0.0031(5) 0.0008(5) O4 0.0178(6) 0.0184(6) 0.0205(6) 0.0052(5) 0.0053(5) 0.0068(5) N1 0.0135(6) 0.0172(7) 0.0150(7) 0.0028(5) 0.0032(5) 0.0035(5) N2 0.0115(6) 0.0142(6) 0.0162(7) 0.0042(5) 0.0014(5) 0.0018(5) C1 0.0172(8) 0.0215(9) 0.0192(9) 0.0021(7) 0.0021(7) -0.0004(7) C2 0.0222(9) 0.0257(9) 0.0170(9) 0.0002(7) 0.0003(7) 0.0014(7) C3 0.0230(9) 0.0288(10) 0.0147(8) 0.0043(7) 0.0028(7) 0.0058(8) C4 0.0190(8) 0.0215(8) 0.0156(8) 0.0056(6) 0.0049(6) 0.0033(7) C5 0.0141(7) 0.0164(7) 0.0154(7) 0.0056(6) 0.0033(6) 0.0041(6) C6 0.0128(7) 0.0156(7) 0.0156(7) 0.0043(6) 0.0026(6) 0.0039(6) C7 0.0143(7) 0.0186(8) 0.0172(8) 0.0071(6) 0.0031(6) 0.0031(6) C8 0.0137(7) 0.0165(8) 0.0209(8) 0.0072(6) 0.0025(6) 0.0013(6) C9 0.0134(7) 0.0164(7) 0.0171(8) 0.0038(6) 0.0011(6) 0.0047(6) C10 0.0132(7) 0.0157(7) 0.0159(8) 0.0051(6) 0.0034(6) 0.0039(6) C11 0.0110(7) 0.0160(7) 0.0145(7) 0.0044(6) 0.0015(6) 0.0046(6) C12 0.0263(10) 0.0261(10) 0.0203(9) 0.0102(7) 0.0034(8) -0.0029(8) C13 0.0218(9) 0.0224(9) 0.0161(8) 0.0036(7) -0.0002(7) 0.0021(7) C14 0.0109(7) 0.0137(7) 0.0162(7) 0.0034(6) 0.0001(6) 0.0014(5) C15 0.0175(8) 0.0179(8) 0.0148(8) 0.0039(6) 0.0015(6) 0.0040(6) C16 0.0168(8) 0.0166(8) 0.0193(8) 0.0055(6) -0.0017(6) 0.0040(6) C17 0.0160(8) 0.0185(8) 0.0228(9) 0.0049(6) 0.0017(7) 0.0069(6) C18 0.0138(7) 0.0159(7) 0.0184(8) 0.0029(6) 0.0029(6) 0.0035(6) C19 0.0129(7) 0.0153(7) 0.0150(7) 0.0035(6) 0.0018(6) 0.0030(6) C20 0.0139(7) 0.0154(7) 0.0145(7) 0.0029(6) 0.0016(6) 0.0033(6) C21 0.0272(10) 0.0285(10) 0.0158(8) 0.0053(7) 0.0065(7) 0.0139(8) C22 0.0295(10) 0.0283(10) 0.0148(8) 0.0056(7) 0.0036(7) 0.0105(8) C23 0.0240(9) 0.0251(9) 0.0180(8) 0.0072(7) 0.0004(7) 0.0092(7) C24 0.0152(7) 0.0188(8) 0.0184(8) 0.0047(6) 0.0009(6) 0.0055(6) C25 0.0439(13) 0.0271(10) 0.0206(10) 0.0086(8) -0.0005(9) 0.0135(9) C26 0.0219(9) 0.0251(9) 0.0232(9) 0.0053(7) 0.0085(7) 0.0109(7) C27 0.0215(8) 0.0167(8) 0.0122(7) 0.0020(6) 0.0037(6) -0.0005(6) C28 0.0277(9) 0.0149(8) 0.0192(9) 0.0028(6) 0.0038(7) 0.0033(7) C29 0.0246(9) 0.0196(8) 0.0148(8) 0.0053(6) 0.0057(7) 0.0091(7) C30 0.0249(9) 0.0205(9) 0.0194(9) 0.0005(7) 0.0057(7) -0.0036(7) C31 0.0327(11) 0.0247(9) 0.0264(10) 0.0095(8) 0.0094(8) 0.0166(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 C14 1.9846(17) . ? Ir1 C11 1.9944(18) . ? Ir1 N1 2.0348(15) . ? Ir1 N2 2.0363(15) . ? Ir1 O3 2.1487(14) . ? Ir1 O4 2.1705(13) . ? O1 C9 1.375(2) . ? O1 C13 1.435(2) . ? O2 C16 1.381(2) . ? O2 C25 1.423(3) . ? O3 C27 1.275(2) . ? O4 C29 1.277(2) . ? N1 C1 1.354(2) . ? N1 C5 1.370(2) . ? N2 C24 1.353(2) . ? N2 C20 1.373(2) . ? C1 C2 1.384(3) . ? C1 H1 0.9500 . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.408(2) . ? C4 H4 0.9500 . ? C5 C6 1.474(3) . ? C6 C7 1.423(2) . ? C6 C11 1.427(2) . ? C7 C8 1.393(3) . ? C7 C12 1.516(3) . ? C8 C9 1.399(3) . ? C8 H8 0.9500 . ? C9 C10 1.393(2) . ? C10 C11 1.413(3) . ? C10 H10 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.407(2) . ? C14 C19 1.422(2) . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.402(3) . ? C17 C18 1.393(3) . ? C17 H17 0.9500 . ? C18 C19 1.424(2) . ? C18 C26 1.515(3) . ? C19 C20 1.472(2) . ? C20 C21 1.411(3) . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 C24 1.385(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.406(3) . ? C27 C30 1.514(3) . ? C28 C29 1.409(3) . ? C28 H28 0.9500 . ? C29 C31 1.519(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 Ir1 C11 88.00(7) . . ? C14 Ir1 N1 96.10(7) . . ? C11 Ir1 N1 79.96(7) . . ? C14 Ir1 N2 79.98(7) . . ? C11 Ir1 N2 98.73(7) . . ? N1 Ir1 N2 175.93(6) . . ? C14 Ir1 O3 88.16(6) . . ? C11 Ir1 O3 174.05(6) . . ? N1 Ir1 O3 95.95(6) . . ? N2 Ir1 O3 85.06(6) . . ? C14 Ir1 O4 174.50(6) . . ? C11 Ir1 O4 96.45(6) . . ? N1 Ir1 O4 87.88(6) . . ? N2 Ir1 O4 96.10(6) . . ? O3 Ir1 O4 87.66(5) . . ? C9 O1 C13 117.47(15) . . ? C16 O2 C25 116.99(16) . . ? C27 O3 Ir1 125.89(12) . . ? C29 O4 Ir1 125.16(12) . . ? C1 N1 C5 120.39(16) . . ? C1 N1 Ir1 122.62(13) . . ? C5 N1 Ir1 116.99(12) . . ? C24 N2 C20 120.32(15) . . ? C24 N2 Ir1 123.08(12) . . ? C20 N2 Ir1 116.43(12) . . ? N1 C1 C2 123.01(18) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 117.75(19) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 119.57(18) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.97(17) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 118.30(17) . . ? N1 C5 C6 113.34(15) . . ? C4 C5 C6 128.34(16) . . ? C7 C6 C11 120.38(16) . . ? C7 C6 C5 126.02(16) . . ? C11 C6 C5 113.57(15) . . ? C8 C7 C6 118.53(16) . . ? C8 C7 C12 116.28(16) . . ? C6 C7 C12 125.17(17) . . ? C7 C8 C9 121.49(16) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? O1 C9 C10 125.19(16) . . ? O1 C9 C8 114.34(16) . . ? C10 C9 C8 120.44(17) . . ? C9 C10 C11 120.07(16) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 119.03(16) . . ? C10 C11 Ir1 124.94(13) . . ? C6 C11 Ir1 115.83(13) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.74(16) . . ? C15 C14 Ir1 123.91(13) . . ? C19 C14 Ir1 116.29(12) . . ? C16 C15 C14 119.79(17) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O2 C16 C15 123.69(17) . . ? O2 C16 C17 115.55(16) . . ? C15 C16 C17 120.75(17) . . ? C18 C17 C16 121.12(16) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 118.64(16) . . ? C17 C18 C26 116.37(16) . . ? C19 C18 C26 124.96(17) . . ? C14 C19 C18 119.87(16) . . ? C14 C19 C20 113.39(15) . . ? C18 C19 C20 126.74(16) . . ? N2 C20 C21 118.14(16) . . ? N2 C20 C19 113.48(15) . . ? C21 C20 C19 128.36(16) . . ? C22 C21 C20 121.10(17) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 119.51(18) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 117.80(18) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? N2 C24 C23 123.07(17) . . ? N2 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C18 C26 H26A 109.5 . . ? C18 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C18 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O3 C27 C28 127.01(17) . . ? O3 C27 C30 114.63(17) . . ? C28 C27 C30 118.36(17) . . ? C27 C28 C29 127.12(17) . . ? C27 C28 H28 116.4 . . ? C29 C28 H28 116.4 . . ? O4 C29 C28 127.04(17) . . ? O4 C29 C31 114.79(18) . . ? C28 C29 C31 118.16(18) . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Ir1 O3 C27 174.75(15) . . . . ? N1 Ir1 O3 C27 -89.30(15) . . . . ? N2 Ir1 O3 C27 94.65(15) . . . . ? O4 Ir1 O3 C27 -1.68(15) . . . . ? C11 Ir1 O4 C29 174.55(15) . . . . ? N1 Ir1 O4 C29 94.91(15) . . . . ? N2 Ir1 O4 C29 -85.91(15) . . . . ? O3 Ir1 O4 C29 -1.13(15) . . . . ? C14 Ir1 N1 C1 95.69(15) . . . . ? C11 Ir1 N1 C1 -177.44(16) . . . . ? O3 Ir1 N1 C1 6.91(15) . . . . ? O4 Ir1 N1 C1 -80.51(15) . . . . ? C14 Ir1 N1 C5 -83.85(13) . . . . ? C11 Ir1 N1 C5 3.02(13) . . . . ? O3 Ir1 N1 C5 -172.63(12) . . . . ? O4 Ir1 N1 C5 99.94(13) . . . . ? C14 Ir1 N2 C24 178.67(15) . . . . ? C11 Ir1 N2 C24 92.28(15) . . . . ? O3 Ir1 N2 C24 -92.34(14) . . . . ? O4 Ir1 N2 C24 -5.23(15) . . . . ? C14 Ir1 N2 C20 -6.12(13) . . . . ? C11 Ir1 N2 C20 -92.51(13) . . . . ? O3 Ir1 N2 C20 82.88(13) . . . . ? O4 Ir1 N2 C20 169.98(12) . . . . ? C5 N1 C1 C2 -0.1(3) . . . . ? Ir1 N1 C1 C2 -179.65(15) . . . . ? N1 C1 C2 C3 -1.0(3) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C1 N1 C5 C4 1.2(3) . . . . ? Ir1 N1 C5 C4 -179.21(13) . . . . ? C1 N1 C5 C6 179.92(16) . . . . ? Ir1 N1 C5 C6 -0.53(19) . . . . ? C3 C4 C5 N1 -1.3(3) . . . . ? C3 C4 C5 C6 -179.75(18) . . . . ? N1 C5 C6 C7 174.52(16) . . . . ? C4 C5 C6 C7 -7.0(3) . . . . ? N1 C5 C6 C11 -3.6(2) . . . . ? C4 C5 C6 C11 174.96(17) . . . . ? C11 C6 C7 C8 -1.8(2) . . . . ? C5 C6 C7 C8 -179.80(17) . . . . ? C11 C6 C7 C12 176.22(17) . . . . ? C5 C6 C7 C12 -1.8(3) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? C12 C7 C8 C9 -178.83(17) . . . . ? C13 O1 C9 C10 -1.1(3) . . . . ? C13 O1 C9 C8 -179.09(16) . . . . ? C7 C8 C9 O1 179.97(16) . . . . ? C7 C8 C9 C10 1.9(3) . . . . ? O1 C9 C10 C11 -178.55(16) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C6 -1.7(2) . . . . ? C9 C10 C11 Ir1 172.85(13) . . . . ? C7 C6 C11 C10 3.0(2) . . . . ? C5 C6 C11 C10 -178.82(15) . . . . ? C7 C6 C11 Ir1 -172.06(13) . . . . ? C5 C6 C11 Ir1 6.15(19) . . . . ? C14 Ir1 C11 C10 -83.12(15) . . . . ? N1 Ir1 C11 C10 -179.68(15) . . . . ? N2 Ir1 C11 C10 -3.58(15) . . . . ? O4 Ir1 C11 C10 93.63(15) . . . . ? C14 Ir1 C11 C6 91.57(13) . . . . ? N1 Ir1 C11 C6 -4.98(12) . . . . ? N2 Ir1 C11 C6 171.12(12) . . . . ? O4 Ir1 C11 C6 -91.67(13) . . . . ? C11 Ir1 C14 C15 -78.57(16) . . . . ? N1 Ir1 C14 C15 1.11(16) . . . . ? N2 Ir1 C14 C15 -177.79(16) . . . . ? O3 Ir1 C14 C15 96.90(15) . . . . ? C11 Ir1 C14 C19 104.43(14) . . . . ? N1 Ir1 C14 C19 -175.90(13) . . . . ? N2 Ir1 C14 C19 5.20(13) . . . . ? O3 Ir1 C14 C19 -80.11(13) . . . . ? C19 C14 C15 C16 3.1(3) . . . . ? Ir1 C14 C15 C16 -173.79(14) . . . . ? C25 O2 C16 C15 7.7(3) . . . . ? C25 O2 C16 C17 -173.51(18) . . . . ? C14 C15 C16 O2 176.17(17) . . . . ? C14 C15 C16 C17 -2.6(3) . . . . ? O2 C16 C17 C18 -178.83(17) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 1.9(3) . . . . ? C16 C17 C18 C26 -176.05(18) . . . . ? C15 C14 C19 C18 -1.2(3) . . . . ? Ir1 C14 C19 C18 175.99(13) . . . . ? C15 C14 C19 C20 179.20(16) . . . . ? Ir1 C14 C19 C20 -3.7(2) . . . . ? C17 C18 C19 C14 -1.4(3) . . . . ? C26 C18 C19 C14 176.45(17) . . . . ? C17 C18 C19 C20 178.25(17) . . . . ? C26 C18 C19 C20 -4.0(3) . . . . ? C24 N2 C20 C21 2.5(3) . . . . ? Ir1 N2 C20 C21 -172.86(14) . . . . ? C24 N2 C20 C19 -178.86(16) . . . . ? Ir1 N2 C20 C19 5.79(19) . . . . ? C14 C19 C20 N2 -1.4(2) . . . . ? C18 C19 C20 N2 178.95(17) . . . . ? C14 C19 C20 C21 177.05(19) . . . . ? C18 C19 C20 C21 -2.6(3) . . . . ? N2 C20 C21 C22 -2.4(3) . . . . ? C19 C20 C21 C22 179.22(19) . . . . ? C20 C21 C22 C23 0.2(3) . . . . ? C21 C22 C23 C24 1.7(3) . . . . ? C20 N2 C24 C23 -0.5(3) . . . . ? Ir1 N2 C24 C23 174.50(15) . . . . ? C22 C23 C24 N2 -1.6(3) . . . . ? Ir1 O3 C27 C28 4.1(3) . . . . ? Ir1 O3 C27 C30 -176.29(12) . . . . ? O3 C27 C28 C29 -3.8(3) . . . . ? C30 C27 C28 C29 176.67(18) . . . . ? Ir1 O4 C29 C28 1.8(3) . . . . ? Ir1 O4 C29 C31 -179.16(12) . . . . ? C27 C28 C29 O4 0.4(3) . . . . ? C27 C28 C29 C31 -178.61(19) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 34.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.564 _refine_diff_density_min -1.084 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 964313' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jf362 _audit_update_record ; 2012-08-03 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H29 Ir N4 O6, C H2 Cl2' _chemical_formula_sum 'C30 H31 Cl2 Ir N4 O6' _chemical_formula_weight 806.69 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 30.259(8) _cell_length_b 10.1335(11) _cell_length_c 39.920(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 12241(5) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 735 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6368 _exptl_absorpt_coefficient_mu 4.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5461 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2008, Bruker AXS, 2008' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 215711 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 13983 _reflns_number_gt 11828 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _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^)+(0.0063P)^2^+25.9011P] 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 13983 _refine_ls_number_parameters 803 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0503 _refine_ls_wR_factor_gt 0.0471 _refine_ls_goodness_of_fit_ref 1.231 _refine_ls_restrained_S_all 1.231 _refine_ls_shift/su_max 0.009 _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 0.373685(4) 0.665169(11) 0.576271(3) 0.00986(3) Uani 1 1 d . . . O1 O 0.48126(7) 0.3378(2) 0.63775(6) 0.0188(5) Uani 1 1 d . . . O2 O 0.34363(8) 0.3691(2) 0.68639(6) 0.0237(6) Uani 1 1 d . . . O3 O 0.38630(7) 0.3106(2) 0.47677(5) 0.0163(5) Uani 1 1 d . . . O4 O 0.24686(7) 0.3986(2) 0.51727(5) 0.0196(5) Uani 1 1 d . . . O5 O 0.36785(7) 0.8075(2) 0.53677(5) 0.0142(5) Uani 1 1 d . . . O6 O 0.38894(7) 0.8250(2) 0.60996(5) 0.0148(5) Uani 1 1 d . . . N1 N 0.43939(8) 0.6319(3) 0.56835(6) 0.0128(5) Uani 1 1 d . . . N2 N 0.41258(9) 0.3539(3) 0.66225(6) 0.0153(6) Uani 1 1 d . . . N3 N 0.31607(8) 0.3532(3) 0.49717(6) 0.0137(6) Uani 1 1 d . . . N4 N 0.30693(8) 0.6817(3) 0.58266(6) 0.0120(5) Uani 1 1 d . . . C1 C 0.46346(10) 0.6975(3) 0.54528(9) 0.0195(7) Uani 1 1 d . . . H1 H 0.4498 0.7663 0.5328 0.023 Uiso 1 1 calc R . . C2 C 0.50716(11) 0.6678(4) 0.53919(10) 0.0266(9) Uani 1 1 d . . . H2 H 0.5236 0.7160 0.5230 0.032 Uiso 1 1 calc R . . C3 C 0.52672(11) 0.5658(4) 0.55720(9) 0.0251(8) Uani 1 1 d . . . H3 H 0.5566 0.5424 0.5532 0.030 Uiso 1 1 calc R . . C4 C 0.50239(10) 0.4989(3) 0.58098(8) 0.0185(7) Uani 1 1 d . . . H4 H 0.5157 0.4295 0.5934 0.022 Uiso 1 1 calc R . . C5 C 0.45824(10) 0.5327(3) 0.58687(8) 0.0132(6) Uani 1 1 d . . . C6 C 0.42826(10) 0.4775(3) 0.61182(8) 0.0126(6) Uani 1 1 d . . . C7 C 0.43940(10) 0.3900(3) 0.63758(8) 0.0141(7) Uani 1 1 d . . . C8 C 0.37204(10) 0.4048(3) 0.66165(7) 0.0153(7) Uani 1 1 d . . . C9 C 0.35642(10) 0.4922(3) 0.63739(8) 0.0150(7) Uani 1 1 d . . . H9 H 0.3269 0.5243 0.6383 0.018 Uiso 1 1 calc R . . C10 C 0.38452(10) 0.5314(3) 0.61196(7) 0.0127(6) Uani 1 1 d . . . C11 C 0.49390(12) 0.2606(4) 0.66657(9) 0.0239(8) Uani 1 1 d . . . H11A H 0.4918 0.3151 0.6868 0.036 Uiso 1 1 calc R . . H11B H 0.5244 0.2297 0.6638 0.036 Uiso 1 1 calc R . . H11C H 0.4741 0.1844 0.6687 0.036 Uiso 1 1 calc R . . C12 C 0.35936(12) 0.2792(4) 0.71176(9) 0.0268(9) Uani 1 1 d . . . H12A H 0.3703 0.1986 0.7011 0.040 Uiso 1 1 calc R . . H12B H 0.3351 0.2571 0.7270 0.040 Uiso 1 1 calc R . . H12C H 0.3833 0.3210 0.7244 0.040 Uiso 1 1 calc R . . C13 C 0.35415(10) 0.5257(3) 0.54484(7) 0.0113(6) Uani 1 1 d . . . C14 C 0.38035(10) 0.4503(3) 0.52327(8) 0.0123(6) Uani 1 1 d . . . H14 H 0.4117 0.4529 0.5248 0.015 Uiso 1 1 calc R . . C15 C 0.35970(10) 0.3716(3) 0.49959(8) 0.0124(6) Uani 1 1 d . . . C16 C 0.29134(10) 0.4203(3) 0.51872(8) 0.0142(7) Uani 1 1 d . . . C17 C 0.30746(10) 0.5104(3) 0.54237(7) 0.0128(6) Uani 1 1 d . . . C18 C 0.28136(10) 0.5977(3) 0.56394(8) 0.0134(7) Uani 1 1 d . . . C19 C 0.23527(10) 0.6061(3) 0.56638(8) 0.0173(7) Uani 1 1 d . . . H19 H 0.2172 0.5467 0.5540 0.021 Uiso 1 1 calc R . . C20 C 0.21600(10) 0.7000(3) 0.58663(9) 0.0194(7) Uani 1 1 d . . . H20 H 0.1847 0.7065 0.5879 0.023 Uiso 1 1 calc R . . C21 C 0.24242(11) 0.7851(4) 0.60506(8) 0.0199(7) Uani 1 1 d . . . H21 H 0.2296 0.8507 0.6190 0.024 Uiso 1 1 calc R . . C22 C 0.28764(10) 0.7722(3) 0.60270(8) 0.0148(7) Uani 1 1 d . . . H22 H 0.3059 0.8291 0.6156 0.018 Uiso 1 1 calc R . . C23 C 0.36508(11) 0.2513(3) 0.44821(8) 0.0192(7) Uani 1 1 d . . . H23A H 0.3454 0.1804 0.4558 0.029 Uiso 1 1 calc R . . H23B H 0.3876 0.2147 0.4332 0.029 Uiso 1 1 calc R . . H23C H 0.3478 0.3182 0.4363 0.029 Uiso 1 1 calc R . . C24 C 0.23147(11) 0.3028(4) 0.49333(8) 0.0224(8) Uani 1 1 d . . . H24A H 0.2353 0.3376 0.4706 0.034 Uiso 1 1 calc R . . H24B H 0.2001 0.2845 0.4973 0.034 Uiso 1 1 calc R . . H24C H 0.2485 0.2211 0.4958 0.034 Uiso 1 1 calc R . . C25 C 0.37401(10) 0.9320(3) 0.53990(8) 0.0155(7) Uani 1 1 d . . . C26 C 0.38517(11) 0.9990(3) 0.56926(8) 0.0181(7) Uani 1 1 d . . . H26 H 0.3892 1.0916 0.5671 0.022 Uiso 1 1 calc R . . C27 C 0.39116(10) 0.9470(3) 0.60147(8) 0.0174(7) Uani 1 1 d . . . C28 C 0.36913(12) 1.0111(4) 0.50827(9) 0.0245(8) Uani 1 1 d . . . H28A H 0.3835 0.9645 0.4897 0.037 Uiso 1 1 calc R . . H28B H 0.3830 1.0977 0.5113 0.037 Uiso 1 1 calc R . . H28C H 0.3377 1.0227 0.5032 0.037 Uiso 1 1 calc R . . C29 C 0.40020(12) 1.0413(4) 0.62980(9) 0.0254(8) Uani 1 1 d . . . H29A H 0.3733 1.0528 0.6432 0.038 Uiso 1 1 calc R . . H29B H 0.4094 1.1268 0.6207 0.038 Uiso 1 1 calc R . . H29C H 0.4238 1.0058 0.6440 0.038 Uiso 1 1 calc R . . Ir2 Ir 0.374298(4) 0.268464(11) 0.328207(3) 0.00962(3) Uani 1 1 d . . . O7 O 0.25057(7) 0.5526(2) 0.38535(5) 0.0189(5) Uani 1 1 d . . . O8 O 0.39058(7) 0.6270(2) 0.42688(5) 0.0178(5) Uani 1 1 d . . . O9 O 0.34911(7) 0.6152(2) 0.22738(6) 0.0201(5) Uani 1 1 d . . . O10 O 0.49278(7) 0.5359(2) 0.26074(6) 0.0180(5) Uani 1 1 d . . . O11 O 0.38866(7) 0.1068(2) 0.29504(5) 0.0164(5) Uani 1 1 d . . . O12 O 0.36348(7) 0.1273(2) 0.36731(5) 0.0149(5) Uani 1 1 d . . . N5 N 0.30773(8) 0.2642(3) 0.32053(6) 0.0122(5) Uani 1 1 d . . . N6 N 0.32036(8) 0.5898(3) 0.40605(6) 0.0142(6) Uani 1 1 d . . . N7 N 0.42115(8) 0.5742(3) 0.24355(6) 0.0134(6) Uani 1 1 d . . . N8 N 0.44062(8) 0.2823(3) 0.33605(6) 0.0110(5) Uani 1 1 d . . . C30 C 0.28776(10) 0.1781(3) 0.29976(8) 0.0154(7) Uani 1 1 d . . . H30 H 0.3055 0.1189 0.2871 0.019 Uiso 1 1 calc R . . C31 C 0.24251(10) 0.1726(3) 0.29616(8) 0.0178(7) Uani 1 1 d . . . H31 H 0.2291 0.1095 0.2818 0.021 Uiso 1 1 calc R . . C32 C 0.21706(11) 0.2615(3) 0.31408(9) 0.0194(7) Uani 1 1 d . . . H32 H 0.1858 0.2605 0.3118 0.023 Uiso 1 1 calc R . . C33 C 0.23698(10) 0.3518(3) 0.33521(8) 0.0167(7) Uani 1 1 d . . . H33 H 0.2195 0.4135 0.3473 0.020 Uiso 1 1 calc R . . C34 C 0.28310(10) 0.3521(3) 0.33874(7) 0.0126(6) Uani 1 1 d . . . C35 C 0.30991(10) 0.4339(3) 0.36086(7) 0.0121(6) Uani 1 1 d . . . C36 C 0.29467(10) 0.5260(3) 0.38424(8) 0.0135(7) Uani 1 1 d . . . C37 C 0.36354(10) 0.5669(3) 0.40401(8) 0.0136(7) Uani 1 1 d . . . C38 C 0.38341(10) 0.4844(3) 0.38055(7) 0.0137(6) Uani 1 1 d . . . H38 H 0.4147 0.4777 0.3792 0.016 Uiso 1 1 calc R . . C39 C 0.35650(10) 0.4120(3) 0.35914(7) 0.0121(6) Uani 1 1 d . . . C40 C 0.23615(11) 0.6503(4) 0.40936(8) 0.0220(8) Uani 1 1 d . . . H40A H 0.2406 0.6165 0.4321 0.033 Uiso 1 1 calc R . . H40B H 0.2047 0.6693 0.4059 0.033 Uiso 1 1 calc R . . H40C H 0.2534 0.7314 0.4064 0.033 Uiso 1 1 calc R . . C41 C 0.36937(12) 0.6836(4) 0.45577(8) 0.0228(8) Uani 1 1 d . . . H41A H 0.3516 0.7598 0.4489 0.034 Uiso 1 1 calc R . . H41B H 0.3919 0.7122 0.4719 0.034 Uiso 1 1 calc R . . H41C H 0.3502 0.6175 0.4662 0.034 Uiso 1 1 calc R . . C42 C 0.38923(10) 0.3988(3) 0.29297(7) 0.0112(6) Uani 1 1 d . . . C43 C 0.36050(10) 0.4645(3) 0.27119(8) 0.0129(7) Uani 1 1 d . . . H43 H 0.3295 0.4505 0.2724 0.016 Uiso 1 1 calc R . . C44 C 0.37846(11) 0.5508(3) 0.24772(7) 0.0145(7) Uani 1 1 d . . . C45 C 0.44855(10) 0.5130(3) 0.26460(8) 0.0133(7) Uani 1 1 d . . . C46 C 0.43522(10) 0.4275(3) 0.29009(7) 0.0121(6) Uani 1 1 d . . . C47 C 0.46384(10) 0.3618(3) 0.31442(8) 0.0125(6) Uani 1 1 d . . . C48 C 0.50980(10) 0.3711(3) 0.31771(8) 0.0145(7) Uani 1 1 d . . . H48 H 0.5261 0.4271 0.3032 0.017 Uiso 1 1 calc R . . C49 C 0.53143(10) 0.2987(3) 0.34211(8) 0.0164(7) Uani 1 1 d . . . H49 H 0.5627 0.3031 0.3440 0.020 Uiso 1 1 calc R . . C50 C 0.50745(10) 0.2198(3) 0.36377(8) 0.0165(7) Uani 1 1 d . . . H50 H 0.5219 0.1706 0.3808 0.020 Uiso 1 1 calc R . . C51 C 0.46213(10) 0.2141(3) 0.36006(8) 0.0150(7) Uani 1 1 d . . . H51 H 0.4455 0.1604 0.3749 0.018 Uiso 1 1 calc R . . C52 C 0.36673(11) 0.6978(4) 0.20120(8) 0.0223(8) Uani 1 1 d . . . H52A H 0.3848 0.7679 0.2111 0.033 Uiso 1 1 calc R . . H52B H 0.3424 0.7373 0.1885 0.033 Uiso 1 1 calc R . . H52C H 0.3850 0.6445 0.1861 0.033 Uiso 1 1 calc R . . C53 C 0.50529(11) 0.6356(4) 0.23666(9) 0.0212(8) Uani 1 1 d . . . H53A H 0.4957 0.6084 0.2142 0.032 Uiso 1 1 calc R . . H53B H 0.5375 0.6466 0.2369 0.032 Uiso 1 1 calc R . . H53C H 0.4911 0.7195 0.2425 0.032 Uiso 1 1 calc R . . C54 C 0.39155(10) -0.0140(3) 0.30413(9) 0.0170(7) Uani 1 1 d . . . C55 C 0.38401(10) -0.0652(3) 0.33612(9) 0.0196(7) Uani 1 1 d . . . H55 H 0.3892 -0.1570 0.3388 0.024 Uiso 1 1 calc R . . C56 C 0.36974(10) 0.0028(3) 0.36464(8) 0.0164(7) Uani 1 1 d . . . C57 C 0.40310(13) -0.1088(4) 0.27630(10) 0.0311(9) Uani 1 1 d . . . H57A H 0.3796 -0.1082 0.2594 0.047 Uiso 1 1 calc R . . H57B H 0.4062 -0.1980 0.2855 0.047 Uiso 1 1 calc R . . H57C H 0.4310 -0.0818 0.2659 0.047 Uiso 1 1 calc R . . C58 C 0.36013(12) -0.0757(4) 0.39573(9) 0.0247(8) Uani 1 1 d . . . H58A H 0.3725 -0.0300 0.4152 0.037 Uiso 1 1 calc R . . H58B H 0.3735 -0.1634 0.3938 0.037 Uiso 1 1 calc R . . H58C H 0.3281 -0.0847 0.3985 0.037 Uiso 1 1 calc R . . C59 C 0.25266(12) 0.5208(4) 0.20366(9) 0.0264(8) Uani 1 1 d . . . H59A H 0.2282 0.5816 0.1978 0.032 Uiso 1 1 calc R . . H59B H 0.2770 0.5739 0.2132 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.27131(4) 0.44022(12) 0.16706(3) 0.0418(3) Uani 1 1 d . . . Cl2 Cl 0.23403(4) 0.40596(11) 0.23392(3) 0.0400(2) Uani 1 1 d . . . C60A C 0.4863(4) 0.8546(9) 0.4270(2) 0.047(2) Uani 0.464(2) 1 d PDU A 1 H60A H 0.5030 0.8562 0.4056 0.057 Uiso 0.464(2) 1 calc PR A 1 H60B H 0.4603 0.7965 0.4238 0.057 Uiso 0.464(2) 1 calc PR A 1 Cl3A Cl 0.46792(9) 1.0120(3) 0.43549(6) 0.0481(7) Uani 0.464(2) 1 d PDU A 1 Cl4A Cl 0.51955(13) 0.7875(3) 0.45765(8) 0.0739(11) Uani 0.464(2) 1 d PDU A 1 C60B C 0.4980(4) 0.8480(9) 0.44367(19) 0.056(2) Uani 0.536(2) 1 d PDU A 2 H60C H 0.5292 0.8223 0.4402 0.067 Uiso 0.536(2) 1 calc PR A 2 H60D H 0.4809 0.7662 0.4477 0.067 Uiso 0.536(2) 1 calc PR A 2 Cl3B Cl 0.47892(10) 0.9204(3) 0.40788(6) 0.0640(8) Uani 0.536(2) 1 d PDU A 2 Cl4B Cl 0.49475(10) 0.9463(2) 0.47923(6) 0.0661(9) Uani 0.536(2) 1 d PD . 2 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 0.00802(5) 0.01012(6) 0.01146(6) -0.00007(4) -0.00132(5) -0.00030(5) O1 0.0154(11) 0.0207(13) 0.0205(12) 0.0043(10) -0.0027(10) 0.0074(10) O2 0.0226(12) 0.0284(15) 0.0200(12) 0.0123(11) 0.0050(10) 0.0038(11) O3 0.0138(11) 0.0185(13) 0.0165(11) -0.0074(10) 0.0027(9) -0.0020(9) O4 0.0109(10) 0.0266(14) 0.0212(12) -0.0115(11) -0.0012(10) -0.0036(10) O5 0.0139(11) 0.0139(12) 0.0148(11) 0.0015(9) -0.0019(9) 0.0003(9) O6 0.0121(10) 0.0150(12) 0.0172(11) -0.0029(10) -0.0032(9) -0.0001(9) N1 0.0123(13) 0.0117(14) 0.0145(13) 0.0009(11) -0.0029(11) -0.0006(11) N2 0.0182(14) 0.0136(15) 0.0142(13) -0.0009(11) -0.0016(11) 0.0001(11) N3 0.0137(13) 0.0119(14) 0.0155(13) -0.0012(11) 0.0009(11) -0.0030(11) N4 0.0111(12) 0.0110(14) 0.0140(13) 0.0015(11) -0.0013(10) 0.0017(10) C1 0.0157(16) 0.0190(19) 0.0237(18) 0.0065(15) 0.0022(14) 0.0009(14) C2 0.0169(17) 0.029(2) 0.034(2) 0.0136(17) 0.0071(16) 0.0016(15) C3 0.0113(16) 0.031(2) 0.033(2) 0.0069(17) 0.0029(15) 0.0034(15) C4 0.0133(15) 0.0186(18) 0.0237(18) 0.0037(15) -0.0010(14) 0.0024(13) C5 0.0134(15) 0.0114(17) 0.0149(15) -0.0021(13) -0.0035(13) -0.0022(13) C6 0.0118(14) 0.0124(17) 0.0137(15) -0.0016(13) -0.0023(12) -0.0010(12) C7 0.0142(15) 0.0119(17) 0.0162(15) -0.0033(13) -0.0045(13) 0.0003(13) C8 0.0157(15) 0.0164(17) 0.0138(15) -0.0003(13) -0.0001(13) -0.0023(14) C9 0.0133(15) 0.0164(18) 0.0154(15) -0.0004(13) -0.0025(13) -0.0004(13) C10 0.0169(16) 0.0088(16) 0.0124(14) -0.0022(12) -0.0044(13) -0.0021(12) C11 0.0245(18) 0.024(2) 0.0233(18) 0.0053(15) -0.0076(15) 0.0078(15) C12 0.0270(19) 0.034(2) 0.0195(18) 0.0137(17) 0.0026(15) 0.0048(17) C13 0.0135(14) 0.0117(16) 0.0088(14) 0.0032(12) -0.0019(12) 0.0012(13) C14 0.0073(14) 0.0099(16) 0.0198(15) 0.0037(13) 0.0000(13) 0.0007(12) C15 0.0153(15) 0.0096(16) 0.0125(15) 0.0016(12) 0.0023(12) 0.0020(12) C16 0.0116(14) 0.0164(18) 0.0146(15) 0.0016(13) -0.0023(13) -0.0013(13) C17 0.0141(15) 0.0131(17) 0.0110(14) -0.0004(13) 0.0001(12) 0.0012(13) C18 0.0130(15) 0.0124(17) 0.0149(15) -0.0001(13) -0.0005(13) -0.0018(13) C19 0.0131(15) 0.0187(19) 0.0202(16) -0.0028(14) -0.0020(13) -0.0020(14) C20 0.0103(15) 0.022(2) 0.0255(18) -0.0020(15) 0.0024(14) 0.0015(14) C21 0.0176(17) 0.0213(19) 0.0207(17) -0.0036(15) 0.0038(14) 0.0033(15) C22 0.0150(15) 0.0146(17) 0.0150(15) -0.0027(13) -0.0013(13) -0.0016(13) C23 0.0238(18) 0.022(2) 0.0115(15) -0.0054(13) 0.0022(14) -0.0021(14) C24 0.0149(16) 0.030(2) 0.0219(17) -0.0114(16) -0.0017(14) -0.0075(15) C25 0.0107(14) 0.0172(17) 0.0187(15) 0.0023(13) 0.0005(13) 0.0024(14) C26 0.0203(17) 0.0095(17) 0.0246(17) 0.0019(14) 0.0043(14) 0.0002(13) C27 0.0102(14) 0.0200(19) 0.0220(17) -0.0040(15) 0.0014(13) -0.0016(13) C28 0.0296(19) 0.0179(19) 0.0260(18) 0.0063(15) 0.0004(16) 0.0012(16) C29 0.0288(19) 0.020(2) 0.0277(19) -0.0089(16) -0.0016(16) -0.0051(16) Ir2 0.00818(5) 0.01010(6) 0.01056(5) -0.00137(4) 0.00097(5) 0.00019(5) O7 0.0110(10) 0.0233(14) 0.0226(12) -0.0094(10) 0.0006(10) 0.0038(10) O8 0.0202(12) 0.0175(13) 0.0157(11) -0.0080(10) -0.0046(9) 0.0055(10) O9 0.0153(11) 0.0275(14) 0.0175(12) 0.0107(11) -0.0027(9) 0.0004(10) O10 0.0109(11) 0.0218(13) 0.0212(12) 0.0084(10) 0.0020(9) -0.0024(9) O11 0.0140(11) 0.0164(13) 0.0187(11) -0.0055(10) 0.0012(9) 0.0003(9) O12 0.0159(11) 0.0122(12) 0.0168(11) 0.0016(9) 0.0009(9) 0.0011(9) N5 0.0108(12) 0.0140(14) 0.0117(12) -0.0003(11) 0.0001(10) -0.0008(11) N6 0.0169(13) 0.0123(14) 0.0132(13) -0.0023(11) -0.0006(11) 0.0033(11) N7 0.0135(13) 0.0148(15) 0.0118(12) 0.0000(11) 0.0002(11) -0.0004(11) N8 0.0105(12) 0.0116(14) 0.0110(12) -0.0027(11) 0.0010(10) 0.0007(11) C30 0.0151(15) 0.0153(18) 0.0160(16) -0.0031(13) 0.0027(13) -0.0003(13) C31 0.0159(16) 0.0174(18) 0.0201(16) -0.0048(14) -0.0020(14) -0.0034(14) C32 0.0116(15) 0.022(2) 0.0245(18) 0.0000(15) -0.0005(14) -0.0023(14) C33 0.0120(15) 0.0208(19) 0.0174(16) -0.0015(14) 0.0024(13) 0.0025(13) C34 0.0128(15) 0.0127(17) 0.0122(15) 0.0009(13) 0.0027(12) 0.0018(13) C35 0.0137(15) 0.0106(16) 0.0121(14) 0.0011(13) -0.0007(12) -0.0008(12) C36 0.0124(15) 0.0143(17) 0.0139(15) 0.0030(13) 0.0024(13) 0.0028(13) C37 0.0155(15) 0.0121(17) 0.0131(15) 0.0021(13) -0.0012(12) -0.0002(13) C38 0.0133(15) 0.0135(17) 0.0144(15) -0.0002(13) 0.0008(12) 0.0020(13) C39 0.0138(14) 0.0130(17) 0.0095(14) 0.0014(12) 0.0013(12) 0.0003(13) C40 0.0175(17) 0.027(2) 0.0215(17) -0.0126(15) 0.0037(14) 0.0082(15) C41 0.034(2) 0.0207(19) 0.0140(15) -0.0026(14) -0.0026(15) 0.0035(16) C42 0.0121(14) 0.0141(17) 0.0074(13) -0.0040(12) 0.0005(12) 0.0006(12) C43 0.0069(13) 0.0153(17) 0.0167(15) -0.0011(13) 0.0025(12) -0.0001(12) C44 0.0172(16) 0.0131(17) 0.0133(14) -0.0005(12) -0.0008(13) 0.0041(14) C45 0.0111(14) 0.0143(17) 0.0145(15) -0.0037(13) 0.0024(12) -0.0001(12) C46 0.0129(15) 0.0110(16) 0.0122(14) -0.0029(13) -0.0011(12) 0.0002(12) C47 0.0139(15) 0.0100(16) 0.0135(15) -0.0040(12) 0.0026(12) -0.0003(12) C48 0.0122(15) 0.0149(17) 0.0164(15) -0.0042(13) 0.0010(13) -0.0018(13) C49 0.0113(15) 0.0191(19) 0.0189(16) -0.0077(14) -0.0027(13) 0.0021(13) C50 0.0158(16) 0.0171(18) 0.0167(16) -0.0025(14) -0.0037(13) 0.0050(14) C51 0.0172(16) 0.0152(17) 0.0126(15) -0.0015(13) 0.0003(13) 0.0000(14) C52 0.0246(18) 0.027(2) 0.0149(16) 0.0087(15) -0.0026(14) 0.0009(15) C53 0.0179(17) 0.023(2) 0.0227(18) 0.0082(15) 0.0041(14) -0.0022(14) C54 0.0090(14) 0.0162(18) 0.0259(18) -0.0088(15) -0.0028(13) -0.0001(13) C55 0.0145(16) 0.0126(17) 0.0318(19) -0.0023(15) -0.0023(15) 0.0019(13) C56 0.0107(15) 0.0150(18) 0.0236(17) 0.0046(14) -0.0025(14) -0.0017(13) C57 0.036(2) 0.025(2) 0.033(2) -0.0134(18) 0.0075(18) 0.0033(17) C58 0.0291(19) 0.019(2) 0.0261(19) 0.0070(16) -0.0041(16) -0.0032(16) C59 0.0234(18) 0.030(2) 0.0256(19) -0.0001(17) -0.0032(16) 0.0008(16) Cl1 0.0445(6) 0.0549(7) 0.0260(5) -0.0027(5) 0.0004(5) 0.0151(5) Cl2 0.0471(6) 0.0411(6) 0.0317(5) -0.0013(5) 0.0027(5) -0.0122(5) C60A 0.069(6) 0.048(5) 0.024(5) 0.018(5) -0.020(5) 0.023(5) Cl3A 0.0621(17) 0.0397(15) 0.0424(14) -0.0023(11) -0.0115(12) 0.0071(12) Cl4A 0.119(3) 0.0371(17) 0.065(2) -0.0066(14) -0.043(2) 0.0114(18) C60B 0.079(6) 0.048(5) 0.041(5) 0.020(5) -0.018(5) 0.034(5) Cl3B 0.0847(19) 0.0586(17) 0.0488(15) -0.0042(13) -0.0151(13) 0.0182(14) Cl4B 0.118(2) 0.0440(15) 0.0366(12) 0.0058(10) 0.0045(13) -0.0071(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C13 1.980(3) . ? Ir1 C10 1.994(3) . ? Ir1 N1 2.041(3) . ? Ir1 N4 2.043(3) . ? Ir1 O5 2.144(2) . ? Ir1 O6 2.156(2) . ? O1 C7 1.373(4) . ? O1 C11 1.443(4) . ? O2 C8 1.358(4) . ? O2 C12 1.443(4) . ? O3 C15 1.364(4) . ? O3 C23 1.440(4) . ? O4 C16 1.365(4) . ? O4 C24 1.439(4) . ? O5 C25 1.281(4) . ? O6 C27 1.283(4) . ? N1 C1 1.349(4) . ? N1 C5 1.372(4) . ? N2 C7 1.328(4) . ? N2 C8 1.331(4) . ? N3 C16 1.327(4) . ? N3 C15 1.337(4) . ? N4 C22 1.350(4) . ? N4 C18 1.372(4) . ? C1 C2 1.378(5) . ? C1 H1 0.9500 . ? C2 C3 1.391(5) . ? C2 H2 0.9500 . ? C3 C4 1.380(5) . ? C3 H3 0.9500 . ? C4 C5 1.399(4) . ? C4 H4 0.9500 . ? C5 C6 1.459(4) . ? C6 C7 1.399(4) . ? C6 C10 1.432(4) . ? C8 C9 1.395(4) . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.398(4) . ? C13 C17 1.425(4) . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C16 C17 1.401(4) . ? C17 C18 1.465(4) . ? C18 C19 1.401(4) . ? C19 C20 1.378(5) . ? C19 H19 0.9500 . ? C20 C21 1.387(5) . ? C20 H20 0.9500 . ? C21 C22 1.378(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.396(5) . ? C25 C28 1.503(4) . ? C26 C27 1.401(5) . ? C26 H26 0.9500 . ? C27 C29 1.506(5) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? Ir2 C42 1.982(3) . ? Ir2 C39 1.982(3) . ? Ir2 N8 2.036(2) . ? Ir2 N5 2.038(3) . ? Ir2 O12 2.142(2) . ? Ir2 O11 2.151(2) . ? O7 C36 1.362(4) . ? O7 C40 1.446(4) . ? O8 C37 1.369(4) . ? O8 C41 1.439(4) . ? O9 C44 1.369(4) . ? O9 C52 1.441(4) . ? O10 C45 1.367(4) . ? O10 C53 1.445(4) . ? O11 C54 1.280(4) . ? O12 C56 1.281(4) . ? N5 C30 1.347(4) . ? N5 C34 1.370(4) . ? N6 C37 1.330(4) . ? N6 C36 1.335(4) . ? N7 C44 1.324(4) . ? N7 C45 1.333(4) . ? N8 C51 1.349(4) . ? N8 C47 1.374(4) . ? C30 C31 1.378(4) . ? C30 H30 0.9500 . ? C31 C32 1.384(5) . ? C31 H31 0.9500 . ? C32 C33 1.383(5) . ? C32 H32 0.9500 . ? C33 C34 1.403(4) . ? C33 H33 0.9500 . ? C34 C35 1.458(4) . ? C35 C36 1.398(4) . ? C35 C39 1.429(4) . ? C37 C38 1.392(4) . ? C38 C39 1.390(4) . ? C38 H38 0.9500 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.398(4) . ? C42 C46 1.426(4) . ? C43 C44 1.392(4) . ? C43 H43 0.9500 . ? C45 C46 1.396(4) . ? C46 C47 1.462(4) . ? C47 C48 1.400(4) . ? C48 C49 1.384(5) . ? C48 H48 0.9500 . ? C49 C50 1.383(5) . ? C49 H49 0.9500 . ? C50 C51 1.380(4) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 C55 1.397(5) . ? C54 C57 1.510(5) . ? C55 C56 1.398(5) . ? C55 H55 0.9500 . ? C56 C58 1.502(5) . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C59 Cl1 1.766(4) . ? C59 Cl2 1.770(4) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60A Cl3A 1.722(9) . ? C60A Cl4A 1.725(8) . ? C60A H60A 0.9900 . ? C60A H60B 0.9900 . ? C60B Cl3B 1.707(8) . ? C60B Cl4B 1.737(8) . ? C60B H60C 0.9900 . ? C60B H60D 0.9900 . ? Cl4B Cl4B 2.008(5) 5_676 ? 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 C13 Ir1 C10 90.97(12) . . ? C13 Ir1 N1 94.29(11) . . ? C10 Ir1 N1 80.69(11) . . ? C13 Ir1 N4 80.94(11) . . ? C10 Ir1 N4 97.43(11) . . ? N1 Ir1 N4 174.87(11) . . ? C13 Ir1 O5 89.39(10) . . ? C10 Ir1 O5 175.13(10) . . ? N1 Ir1 O5 94.44(9) . . ? N4 Ir1 O5 87.43(9) . . ? C13 Ir1 O6 174.67(10) . . ? C10 Ir1 O6 91.71(10) . . ? N1 Ir1 O6 90.69(9) . . ? N4 Ir1 O6 94.14(9) . . ? O5 Ir1 O6 88.33(8) . . ? C7 O1 C11 117.2(3) . . ? C8 O2 C12 118.0(3) . . ? C15 O3 C23 117.1(2) . . ? C16 O4 C24 117.1(2) . . ? C25 O5 Ir1 125.35(19) . . ? C27 O6 Ir1 124.8(2) . . ? C1 N1 C5 120.3(3) . . ? C1 N1 Ir1 123.4(2) . . ? C5 N1 Ir1 116.3(2) . . ? C7 N2 C8 116.3(3) . . ? C16 N3 C15 116.0(3) . . ? C22 N4 C18 120.1(3) . . ? C22 N4 Ir1 123.9(2) . . ? C18 N4 Ir1 116.0(2) . . ? N1 C1 C2 122.1(3) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 119.1(3) . . ? N1 C5 C6 113.0(3) . . ? C4 C5 C6 127.9(3) . . ? C7 C6 C10 117.5(3) . . ? C7 C6 C5 126.5(3) . . ? C10 C6 C5 115.5(3) . . ? N2 C7 O1 117.0(3) . . ? N2 C7 C6 124.9(3) . . ? O1 C7 C6 118.1(3) . . ? N2 C8 O2 117.8(3) . . ? N2 C8 C9 124.8(3) . . ? O2 C8 C9 117.3(3) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C6 117.5(3) . . ? C9 C10 Ir1 128.2(2) . . ? C6 C10 Ir1 114.1(2) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C17 117.4(3) . . ? C14 C13 Ir1 127.7(2) . . ? C17 C13 Ir1 114.7(2) . . ? C15 C14 C13 118.6(3) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N3 C15 O3 118.1(3) . . ? N3 C15 C14 125.1(3) . . ? O3 C15 C14 116.8(3) . . ? N3 C16 O4 116.5(3) . . ? N3 C16 C17 125.0(3) . . ? O4 C16 C17 118.5(3) . . ? C16 C17 C13 117.6(3) . . ? C16 C17 C18 127.0(3) . . ? C13 C17 C18 115.3(3) . . ? N4 C18 C19 119.1(3) . . ? N4 C18 C17 113.0(3) . . ? C19 C18 C17 127.9(3) . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 118.5(3) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? N4 C22 C21 122.3(3) . . ? N4 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 C26 126.6(3) . . ? O5 C25 C28 115.4(3) . . ? C26 C25 C28 118.0(3) . . ? C25 C26 C27 128.2(3) . . ? C25 C26 H26 115.9 . . ? C27 C26 H26 115.9 . . ? O6 C27 C26 126.7(3) . . ? O6 C27 C29 115.0(3) . . ? C26 C27 C29 118.3(3) . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C42 Ir2 C39 90.87(12) . . ? C42 Ir2 N8 80.71(11) . . ? C39 Ir2 N8 96.98(11) . . ? C42 Ir2 N5 97.62(11) . . ? C39 Ir2 N5 80.82(11) . . ? N8 Ir2 N5 177.25(11) . . ? C42 Ir2 O12 175.56(10) . . ? C39 Ir2 O12 89.68(11) . . ? N8 Ir2 O12 94.85(9) . . ? N5 Ir2 O12 86.82(9) . . ? C42 Ir2 O11 91.42(11) . . ? C39 Ir2 O11 175.67(10) . . ? N8 Ir2 O11 87.01(9) . . ? N5 Ir2 O11 95.23(9) . . ? O12 Ir2 O11 88.32(9) . . ? C36 O7 C40 117.0(2) . . ? C37 O8 C41 116.5(3) . . ? C44 O9 C52 117.8(2) . . ? C45 O10 C53 116.8(2) . . ? C54 O11 Ir2 124.6(2) . . ? C56 O12 Ir2 125.1(2) . . ? C30 N5 C34 120.3(3) . . ? C30 N5 Ir2 123.3(2) . . ? C34 N5 Ir2 116.4(2) . . ? C37 N6 C36 116.6(3) . . ? C44 N7 C45 116.4(3) . . ? C51 N8 C47 120.0(3) . . ? C51 N8 Ir2 123.4(2) . . ? C47 N8 Ir2 116.6(2) . . ? N5 C30 C31 122.4(3) . . ? N5 C30 H30 118.8 . . ? C31 C30 H30 118.8 . . ? C30 C31 C32 118.2(3) . . ? C30 C31 H31 120.9 . . ? C32 C31 H31 120.9 . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 119.7(3) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? N5 C34 C33 119.1(3) . . ? N5 C34 C35 112.9(3) . . ? C33 C34 C35 128.0(3) . . ? C36 C35 C39 117.5(3) . . ? C36 C35 C34 126.9(3) . . ? C39 C35 C34 115.6(3) . . ? N6 C36 O7 117.0(3) . . ? N6 C36 C35 124.5(3) . . ? O7 C36 C35 118.5(3) . . ? N6 C37 O8 117.9(3) . . ? N6 C37 C38 124.8(3) . . ? O8 C37 C38 117.3(3) . . ? C39 C38 C37 118.5(3) . . ? C39 C38 H38 120.7 . . ? C37 C38 H38 120.7 . . ? C38 C39 C35 117.8(3) . . ? C38 C39 Ir2 127.7(2) . . ? C35 C39 Ir2 114.3(2) . . ? O7 C40 H40A 109.5 . . ? O7 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O7 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O8 C41 H41A 109.5 . . ? O8 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? O8 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C46 117.4(3) . . ? C43 C42 Ir2 128.1(2) . . ? C46 C42 Ir2 114.5(2) . . ? C44 C43 C42 118.3(3) . . ? C44 C43 H43 120.8 . . ? C42 C43 H43 120.8 . . ? N7 C44 O9 118.3(3) . . ? N7 C44 C43 125.3(3) . . ? O9 C44 C43 116.4(3) . . ? N7 C45 O10 117.3(3) . . ? N7 C45 C46 124.6(3) . . ? O10 C45 C46 118.1(3) . . ? C45 C46 C42 117.8(3) . . ? C45 C46 C47 126.6(3) . . ? C42 C46 C47 115.6(3) . . ? N8 C47 C48 119.2(3) . . ? N8 C47 C46 112.4(3) . . ? C48 C47 C46 128.3(3) . . ? C49 C48 C47 120.0(3) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C50 C49 C48 119.9(3) . . ? C50 C49 H49 120.1 . . ? C48 C49 H49 120.1 . . ? C51 C50 C49 118.6(3) . . ? C51 C50 H50 120.7 . . ? C49 C50 H50 120.7 . . ? N8 C51 C50 122.3(3) . . ? N8 C51 H51 118.9 . . ? C50 C51 H51 118.9 . . ? O9 C52 H52A 109.5 . . ? O9 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O9 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O10 C53 H53A 109.5 . . ? O10 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? O10 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? O11 C54 C55 127.1(3) . . ? O11 C54 C57 114.6(3) . . ? C55 C54 C57 118.3(3) . . ? C54 C55 C56 127.7(3) . . ? C54 C55 H55 116.1 . . ? C56 C55 H55 116.1 . . ? O12 C56 C55 126.8(3) . . ? O12 C56 C58 115.1(3) . . ? C55 C56 C58 118.2(3) . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C56 C58 H58A 109.5 . . ? C56 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C56 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? Cl1 C59 Cl2 111.2(2) . . ? Cl1 C59 H59A 109.4 . . ? Cl2 C59 H59A 109.4 . . ? Cl1 C59 H59B 109.4 . . ? Cl2 C59 H59B 109.4 . . ? H59A C59 H59B 108.0 . . ? Cl3A C60A Cl4A 114.4(6) . . ? Cl3A C60A H60A 108.7 . . ? Cl4A C60A H60A 108.7 . . ? Cl3A C60A H60B 108.7 . . ? Cl4A C60A H60B 108.7 . . ? H60A C60A H60B 107.6 . . ? Cl3B C60B Cl4B 114.7(5) . . ? Cl3B C60B H60C 108.6 . . ? Cl4B C60B H60C 108.6 . . ? Cl3B C60B H60D 108.6 . . ? Cl4B C60B H60D 108.6 . . ? H60C C60B H60D 107.6 . . ? C60B Cl4B Cl4B 167.6(5) . 5_676 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 Ir1 O5 C25 176.4(2) . . . . ? N1 Ir1 O5 C25 -89.4(2) . . . . ? N4 Ir1 O5 C25 95.4(2) . . . . ? O6 Ir1 O5 C25 1.2(2) . . . . ? C10 Ir1 O6 C27 174.9(2) . . . . ? N1 Ir1 O6 C27 94.2(2) . . . . ? N4 Ir1 O6 C27 -87.5(2) . . . . ? O5 Ir1 O6 C27 -0.2(2) . . . . ? C13 Ir1 N1 C1 92.7(3) . . . . ? C10 Ir1 N1 C1 -177.1(3) . . . . ? O5 Ir1 N1 C1 2.9(3) . . . . ? O6 Ir1 N1 C1 -85.4(3) . . . . ? C13 Ir1 N1 C5 -84.2(2) . . . . ? C10 Ir1 N1 C5 6.1(2) . . . . ? O5 Ir1 N1 C5 -173.9(2) . . . . ? O6 Ir1 N1 C5 97.7(2) . . . . ? C13 Ir1 N4 C22 -177.6(3) . . . . ? C10 Ir1 N4 C22 92.6(3) . . . . ? O5 Ir1 N4 C22 -87.8(3) . . . . ? O6 Ir1 N4 C22 0.3(3) . . . . ? C13 Ir1 N4 C18 -0.4(2) . . . . ? C10 Ir1 N4 C18 -90.2(2) . . . . ? O5 Ir1 N4 C18 89.4(2) . . . . ? O6 Ir1 N4 C18 177.5(2) . . . . ? C5 N1 C1 C2 0.5(5) . . . . ? Ir1 N1 C1 C2 -176.3(3) . . . . ? N1 C1 C2 C3 0.8(6) . . . . ? C1 C2 C3 C4 -1.2(6) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? C1 N1 C5 C4 -1.3(5) . . . . ? Ir1 N1 C5 C4 175.6(2) . . . . ? C1 N1 C5 C6 176.9(3) . . . . ? Ir1 N1 C5 C6 -6.1(3) . . . . ? C3 C4 C5 N1 0.9(5) . . . . ? C3 C4 C5 C6 -177.0(3) . . . . ? N1 C5 C6 C7 -169.8(3) . . . . ? C4 C5 C6 C7 8.2(5) . . . . ? N1 C5 C6 C10 2.2(4) . . . . ? C4 C5 C6 C10 -179.7(3) . . . . ? C8 N2 C7 O1 -179.7(3) . . . . ? C8 N2 C7 C6 0.9(5) . . . . ? C11 O1 C7 N2 -6.7(4) . . . . ? C11 O1 C7 C6 172.8(3) . . . . ? C10 C6 C7 N2 -0.4(5) . . . . ? C5 C6 C7 N2 171.4(3) . . . . ? C10 C6 C7 O1 -179.9(3) . . . . ? C5 C6 C7 O1 -8.0(5) . . . . ? C7 N2 C8 O2 179.5(3) . . . . ? C7 N2 C8 C9 -0.4(5) . . . . ? C12 O2 C8 N2 0.4(4) . . . . ? C12 O2 C8 C9 -179.7(3) . . . . ? N2 C8 C9 C10 -0.6(5) . . . . ? O2 C8 C9 C10 179.5(3) . . . . ? C8 C9 C10 C6 1.0(4) . . . . ? C8 C9 C10 Ir1 -174.4(2) . . . . ? C7 C6 C10 C9 -0.5(4) . . . . ? C5 C6 C10 C9 -173.3(3) . . . . ? C7 C6 C10 Ir1 175.5(2) . . . . ? C5 C6 C10 Ir1 2.7(3) . . . . ? C13 Ir1 C10 C9 -94.8(3) . . . . ? N1 Ir1 C10 C9 171.0(3) . . . . ? N4 Ir1 C10 C9 -13.8(3) . . . . ? O6 Ir1 C10 C9 80.6(3) . . . . ? C13 Ir1 C10 C6 89.6(2) . . . . ? N1 Ir1 C10 C6 -4.6(2) . . . . ? N4 Ir1 C10 C6 170.6(2) . . . . ? O6 Ir1 C10 C6 -95.0(2) . . . . ? C10 Ir1 C13 C14 -87.4(3) . . . . ? N1 Ir1 C13 C14 -6.7(3) . . . . ? N4 Ir1 C13 C14 175.2(3) . . . . ? O5 Ir1 C13 C14 87.7(3) . . . . ? C10 Ir1 C13 C17 98.3(2) . . . . ? N1 Ir1 C13 C17 179.0(2) . . . . ? N4 Ir1 C13 C17 0.9(2) . . . . ? O5 Ir1 C13 C17 -86.6(2) . . . . ? C17 C13 C14 C15 3.8(4) . . . . ? Ir1 C13 C14 C15 -170.3(2) . . . . ? C16 N3 C15 O3 -176.4(3) . . . . ? C16 N3 C15 C14 2.4(5) . . . . ? C23 O3 C15 N3 11.2(4) . . . . ? C23 O3 C15 C14 -167.7(3) . . . . ? C13 C14 C15 N3 -5.6(5) . . . . ? C13 C14 C15 O3 173.2(3) . . . . ? C15 N3 C16 O4 -177.7(3) . . . . ? C15 N3 C16 C17 2.5(5) . . . . ? C24 O4 C16 N3 1.8(4) . . . . ? C24 O4 C16 C17 -178.4(3) . . . . ? N3 C16 C17 C13 -3.8(5) . . . . ? O4 C16 C17 C13 176.4(3) . . . . ? N3 C16 C17 C18 172.4(3) . . . . ? O4 C16 C17 C18 -7.4(5) . . . . ? C14 C13 C17 C16 0.4(4) . . . . ? Ir1 C13 C17 C16 175.3(2) . . . . ? C14 C13 C17 C18 -176.2(3) . . . . ? Ir1 C13 C17 C18 -1.3(4) . . . . ? C22 N4 C18 C19 -1.0(5) . . . . ? Ir1 N4 C18 C19 -178.3(2) . . . . ? C22 N4 C18 C17 177.1(3) . . . . ? Ir1 N4 C18 C17 -0.2(3) . . . . ? C16 C17 C18 N4 -175.3(3) . . . . ? C13 C17 C18 N4 1.0(4) . . . . ? C16 C17 C18 C19 2.6(6) . . . . ? C13 C17 C18 C19 178.9(3) . . . . ? N4 C18 C19 C20 1.8(5) . . . . ? C17 C18 C19 C20 -176.0(3) . . . . ? C18 C19 C20 C21 -1.1(5) . . . . ? C19 C20 C21 C22 -0.4(5) . . . . ? C18 N4 C22 C21 -0.5(5) . . . . ? Ir1 N4 C22 C21 176.5(2) . . . . ? C20 C21 C22 N4 1.2(5) . . . . ? Ir1 O5 C25 C26 -0.7(4) . . . . ? Ir1 O5 C25 C28 178.5(2) . . . . ? O5 C25 C26 C27 -1.4(6) . . . . ? C28 C25 C26 C27 179.5(3) . . . . ? Ir1 O6 C27 C26 -1.4(4) . . . . ? Ir1 O6 C27 C29 177.2(2) . . . . ? C25 C26 C27 O6 2.6(6) . . . . ? C25 C26 C27 C29 -175.9(3) . . . . ? C42 Ir2 O11 C54 169.5(2) . . . . ? N8 Ir2 O11 C54 88.9(2) . . . . ? N5 Ir2 O11 C54 -92.7(2) . . . . ? O12 Ir2 O11 C54 -6.0(2) . . . . ? C39 Ir2 O12 C56 -179.0(2) . . . . ? N8 Ir2 O12 C56 -82.0(2) . . . . ? N5 Ir2 O12 C56 100.2(2) . . . . ? O11 Ir2 O12 C56 4.9(2) . . . . ? C42 Ir2 N5 C30 91.7(3) . . . . ? C39 Ir2 N5 C30 -178.7(3) . . . . ? O12 Ir2 N5 C30 -88.5(3) . . . . ? O11 Ir2 N5 C30 -0.4(3) . . . . ? C42 Ir2 N5 C34 -90.5(2) . . . . ? C39 Ir2 N5 C34 -0.9(2) . . . . ? O12 Ir2 N5 C34 89.3(2) . . . . ? O11 Ir2 N5 C34 177.3(2) . . . . ? C42 Ir2 N8 C51 179.5(3) . . . . ? C39 Ir2 N8 C51 89.8(3) . . . . ? O12 Ir2 N8 C51 -0.5(3) . . . . ? O11 Ir2 N8 C51 -88.5(2) . . . . ? C42 Ir2 N8 C47 -3.2(2) . . . . ? C39 Ir2 N8 C47 -93.0(2) . . . . ? O12 Ir2 N8 C47 176.8(2) . . . . ? O11 Ir2 N8 C47 88.7(2) . . . . ? C34 N5 C30 C31 -0.9(5) . . . . ? Ir2 N5 C30 C31 176.8(2) . . . . ? N5 C30 C31 C32 1.6(5) . . . . ? C30 C31 C32 C33 -0.7(5) . . . . ? C31 C32 C33 C34 -0.7(5) . . . . ? C30 N5 C34 C33 -0.6(4) . . . . ? Ir2 N5 C34 C33 -178.4(2) . . . . ? C30 N5 C34 C35 177.6(3) . . . . ? Ir2 N5 C34 C35 -0.2(3) . . . . ? C32 C33 C34 N5 1.4(5) . . . . ? C32 C33 C34 C35 -176.5(3) . . . . ? N5 C34 C35 C36 -175.2(3) . . . . ? C33 C34 C35 C36 2.8(5) . . . . ? N5 C34 C35 C39 1.8(4) . . . . ? C33 C34 C35 C39 179.8(3) . . . . ? C37 N6 C36 O7 -177.7(3) . . . . ? C37 N6 C36 C35 2.9(5) . . . . ? C40 O7 C36 N6 1.8(4) . . . . ? C40 O7 C36 C35 -178.7(3) . . . . ? C39 C35 C36 N6 -3.3(5) . . . . ? C34 C35 C36 N6 173.6(3) . . . . ? C39 C35 C36 O7 177.3(3) . . . . ? C34 C35 C36 O7 -5.8(5) . . . . ? C36 N6 C37 O8 -177.5(3) . . . . ? C36 N6 C37 C38 1.5(5) . . . . ? C41 O8 C37 N6 14.5(4) . . . . ? C41 O8 C37 C38 -164.6(3) . . . . ? N6 C37 C38 C39 -5.2(5) . . . . ? O8 C37 C38 C39 173.8(3) . . . . ? C37 C38 C39 C35 4.5(4) . . . . ? C37 C38 C39 Ir2 -170.2(2) . . . . ? C36 C35 C39 C38 -0.6(4) . . . . ? C34 C35 C39 C38 -177.9(3) . . . . ? C36 C35 C39 Ir2 174.7(2) . . . . ? C34 C35 C39 Ir2 -2.5(4) . . . . ? C42 Ir2 C39 C38 -85.8(3) . . . . ? N8 Ir2 C39 C38 -5.0(3) . . . . ? N5 Ir2 C39 C38 176.6(3) . . . . ? O12 Ir2 C39 C38 89.8(3) . . . . ? C42 Ir2 C39 C35 99.4(2) . . . . ? N8 Ir2 C39 C35 -179.8(2) . . . . ? N5 Ir2 C39 C35 1.8(2) . . . . ? O12 Ir2 C39 C35 -85.0(2) . . . . ? C39 Ir2 C42 C43 -79.8(3) . . . . ? N8 Ir2 C42 C43 -176.7(3) . . . . ? N5 Ir2 C42 C43 1.1(3) . . . . ? O11 Ir2 C42 C43 96.6(3) . . . . ? C39 Ir2 C42 C46 100.1(2) . . . . ? N8 Ir2 C42 C46 3.2(2) . . . . ? N5 Ir2 C42 C46 -179.0(2) . . . . ? O11 Ir2 C42 C46 -83.6(2) . . . . ? C46 C42 C43 C44 1.4(4) . . . . ? Ir2 C42 C43 C44 -178.7(2) . . . . ? C45 N7 C44 O9 177.8(3) . . . . ? C45 N7 C44 C43 -2.7(5) . . . . ? C52 O9 C44 N7 4.1(4) . . . . ? C52 O9 C44 C43 -175.5(3) . . . . ? C42 C43 C44 N7 1.8(5) . . . . ? C42 C43 C44 O9 -178.6(3) . . . . ? C44 N7 C45 O10 -179.9(3) . . . . ? C44 N7 C45 C46 0.2(5) . . . . ? C53 O10 C45 N7 6.7(4) . . . . ? C53 O10 C45 C46 -173.4(3) . . . . ? N7 C45 C46 C42 2.8(5) . . . . ? O10 C45 C46 C42 -177.0(3) . . . . ? N7 C45 C46 C47 -177.8(3) . . . . ? O10 C45 C46 C47 2.4(5) . . . . ? C43 C42 C46 C45 -3.5(4) . . . . ? Ir2 C42 C46 C45 176.6(2) . . . . ? C43 C42 C46 C47 177.0(3) . . . . ? Ir2 C42 C46 C47 -2.8(4) . . . . ? C51 N8 C47 C48 -0.1(4) . . . . ? Ir2 N8 C47 C48 -177.5(2) . . . . ? C51 N8 C47 C46 179.8(3) . . . . ? Ir2 N8 C47 C46 2.5(3) . . . . ? C45 C46 C47 N8 -179.2(3) . . . . ? C42 C46 C47 N8 0.2(4) . . . . ? C45 C46 C47 C48 0.8(5) . . . . ? C42 C46 C47 C48 -179.8(3) . . . . ? N8 C47 C48 C49 1.3(5) . . . . ? C46 C47 C48 C49 -178.7(3) . . . . ? C47 C48 C49 C50 -1.7(5) . . . . ? C48 C49 C50 C51 0.9(5) . . . . ? C47 N8 C51 C50 -0.6(5) . . . . ? Ir2 N8 C51 C50 176.5(2) . . . . ? C49 C50 C51 N8 0.2(5) . . . . ? Ir2 O11 C54 C55 3.4(4) . . . . ? Ir2 O11 C54 C57 -178.5(2) . . . . ? O11 C54 C55 C56 3.3(5) . . . . ? C57 C54 C55 C56 -174.7(3) . . . . ? Ir2 O12 C56 C55 -1.0(4) . . . . ? Ir2 O12 C56 C58 179.5(2) . . . . ? C54 C55 C56 O12 -4.7(5) . . . . ? C54 C55 C56 C58 174.8(3) . . . . ? Cl3B C60B Cl4B Cl4B -121.9(14) . . . 5_676 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.785 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.110 _iucr_refine_instructions_details ; TITL JF362 in Pbca CELL 0.71073 30.2590 10.1335 39.9204 90.0000 90.0000 90.0000 ZERR 16.00 0.0083 0.0011 0.0101 0.0000 0.0000 0.0000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O CL IR UNIT 480 496 64 96 32 16 REM ---------------------------------------------------------- REM Data collection: Bruker APEX II CCD REM Absorption correction: SADABS REM Crystal habit: prismatic; Crystal colour: yellow REM Mole 1 and 2 are two Ir(III) neutral complexes REM Mole 3 and 4 are two DCM solvent molecules REM ---------------------------------------------------------- L.S. 10 OMIT 3 1 2 ACTA CONF WPDB -2 SIZE 0.456 0.265 0.164 BOND $H FMAP 2 PLAN 10 TEMP -173 SIMU 0.01 C60A > CL4B SADI C60A CL3A C60A CL4A C60B CL3B C60B CL4B SADI CL3A CL4A CL3B CL4B WGHT 0.006300 25.901098 FVAR 0.04493 0.46371 MOLE 1 IR1 6 0.373685 0.665169 0.576271 11.00000 0.00802 0.01012 = 0.01146 -0.00007 -0.00132 -0.00030 O1 4 0.481258 0.337797 0.637755 11.00000 0.01536 0.02067 = 0.02050 0.00430 -0.00275 0.00737 O2 4 0.343633 0.369137 0.686391 11.00000 0.02258 0.02844 = 0.02005 0.01226 0.00497 0.00385 O3 4 0.386299 0.310648 0.476774 11.00000 0.01383 0.01847 = 0.01651 -0.00739 0.00273 -0.00196 O4 4 0.246861 0.398599 0.517266 11.00000 0.01094 0.02659 = 0.02116 -0.01152 -0.00124 -0.00363 O5 4 0.367851 0.807506 0.536769 11.00000 0.01386 0.01387 = 0.01479 0.00146 -0.00188 0.00030 O6 4 0.388944 0.825039 0.609960 11.00000 0.01213 0.01499 = 0.01722 -0.00286 -0.00325 -0.00005 N1 3 0.439390 0.631905 0.568353 11.00000 0.01228 0.01169 = 0.01448 0.00094 -0.00289 -0.00064 N2 3 0.412579 0.353937 0.662251 11.00000 0.01820 0.01358 = 0.01417 -0.00094 -0.00164 0.00011 N3 3 0.316073 0.353212 0.497173 11.00000 0.01366 0.01190 = 0.01548 -0.00121 0.00089 -0.00300 N4 3 0.306927 0.681729 0.582662 11.00000 0.01113 0.01100 = 0.01397 0.00145 -0.00132 0.00167 C1 1 0.463456 0.697462 0.545279 11.00000 0.01575 0.01901 = 0.02369 0.00648 0.00221 0.00089 AFIX 43 H1 2 0.449838 0.766254 0.532836 11.00000 -1.20000 AFIX 0 C2 1 0.507158 0.667800 0.539190 11.00000 0.01692 0.02900 = 0.03402 0.01358 0.00706 0.00157 AFIX 43 H2 2 0.523597 0.715996 0.523023 11.00000 -1.20000 AFIX 0 C3 1 0.526720 0.565814 0.557204 11.00000 0.01134 0.03081 = 0.03314 0.00688 0.00292 0.00338 AFIX 43 H3 2 0.556648 0.542402 0.553155 11.00000 -1.20000 AFIX 0 C4 1 0.502386 0.498897 0.580983 11.00000 0.01327 0.01857 = 0.02374 0.00365 -0.00098 0.00240 AFIX 43 H4 2 0.515668 0.429503 0.593419 11.00000 -1.20000 AFIX 0 C5 1 0.458243 0.532746 0.586869 11.00000 0.01342 0.01140 = 0.01486 -0.00207 -0.00347 -0.00223 C6 1 0.428265 0.477453 0.611819 11.00000 0.01177 0.01236 = 0.01373 -0.00160 -0.00234 -0.00100 C7 1 0.439401 0.390014 0.637576 11.00000 0.01415 0.01185 = 0.01622 -0.00335 -0.00454 0.00026 C8 1 0.372042 0.404793 0.661647 11.00000 0.01571 0.01641 = 0.01384 -0.00028 -0.00013 -0.00226 C9 1 0.356420 0.492192 0.637394 11.00000 0.01328 0.01637 = 0.01540 -0.00043 -0.00247 -0.00045 AFIX 43 H9 2 0.326945 0.524261 0.638333 11.00000 -1.20000 AFIX 0 C10 1 0.384522 0.531412 0.611961 11.00000 0.01687 0.00883 = 0.01239 -0.00222 -0.00437 -0.00214 C11 1 0.493899 0.260550 0.666568 11.00000 0.02447 0.02401 = 0.02332 0.00527 -0.00761 0.00781 AFIX 33 H11A 2 0.491799 0.315072 0.686781 11.00000 -1.50000 H11B 2 0.524375 0.229667 0.663817 11.00000 -1.50000 H11C 2 0.474108 0.184449 0.668675 11.00000 -1.50000 AFIX 0 C12 1 0.359361 0.279245 0.711763 11.00000 0.02699 0.03405 = 0.01948 0.01372 0.00260 0.00481 AFIX 33 H12A 2 0.370343 0.198563 0.701091 11.00000 -1.50000 H12B 2 0.335088 0.257118 0.727014 11.00000 -1.50000 H12C 2 0.383334 0.321004 0.724416 11.00000 -1.50000 AFIX 0 C13 1 0.354151 0.525750 0.544837 11.00000 0.01348 0.01173 = 0.00881 0.00325 -0.00193 0.00118 C14 1 0.380346 0.450272 0.523273 11.00000 0.00726 0.00991 = 0.01981 0.00365 -0.00002 0.00072 AFIX 43 H14 2 0.411663 0.452858 0.524826 11.00000 -1.20000 AFIX 0 C15 1 0.359700 0.371637 0.499595 11.00000 0.01525 0.00959 = 0.01250 0.00158 0.00230 0.00197 C16 1 0.291343 0.420262 0.518724 11.00000 0.01164 0.01638 = 0.01463 0.00159 -0.00225 -0.00126 C17 1 0.307463 0.510383 0.542371 11.00000 0.01415 0.01310 = 0.01101 -0.00040 0.00011 0.00124 C18 1 0.281363 0.597684 0.563937 11.00000 0.01304 0.01239 = 0.01489 -0.00011 -0.00050 -0.00179 C19 1 0.235267 0.606060 0.566379 11.00000 0.01311 0.01871 = 0.02015 -0.00282 -0.00204 -0.00201 AFIX 43 H19 2 0.217215 0.546745 0.554035 11.00000 -1.20000 AFIX 0 C20 1 0.216000 0.700040 0.586626 11.00000 0.01030 0.02232 = 0.02551 -0.00196 0.00240 0.00150 AFIX 43 H20 2 0.184728 0.706548 0.587943 11.00000 -1.20000 AFIX 0 C21 1 0.242421 0.785052 0.605064 11.00000 0.01764 0.02127 = 0.02070 -0.00357 0.00380 0.00328 AFIX 43 H21 2 0.229621 0.850673 0.619017 11.00000 -1.20000 AFIX 0 C22 1 0.287636 0.772248 0.602700 11.00000 0.01495 0.01459 = 0.01496 -0.00266 -0.00133 -0.00163 AFIX 43 H22 2 0.305874 0.829099 0.615621 11.00000 -1.20000 AFIX 0 C23 1 0.365079 0.251262 0.448214 11.00000 0.02378 0.02246 = 0.01147 -0.00544 0.00223 -0.00212 AFIX 33 H23A 2 0.345413 0.180415 0.455764 11.00000 -1.50000 H23B 2 0.387564 0.214739 0.433173 11.00000 -1.50000 H23C 2 0.347823 0.318225 0.436272 11.00000 -1.50000 AFIX 0 C24 1 0.231470 0.302804 0.493333 11.00000 0.01494 0.03033 = 0.02190 -0.01137 -0.00173 -0.00747 AFIX 33 H24A 2 0.235329 0.337568 0.470612 11.00000 -1.50000 H24B 2 0.200103 0.284515 0.497310 11.00000 -1.50000 H24C 2 0.248500 0.221111 0.495782 11.00000 -1.50000 AFIX 0 C25 1 0.374014 0.931992 0.539896 11.00000 0.01069 0.01717 = 0.01867 0.00232 0.00048 0.00242 C26 1 0.385174 0.998983 0.569262 11.00000 0.02034 0.00948 = 0.02457 0.00191 0.00431 0.00022 AFIX 43 H26 2 0.389225 1.091572 0.567142 11.00000 -1.20000 AFIX 0 C27 1 0.391156 0.946961 0.601466 11.00000 0.01023 0.01999 = 0.02196 -0.00398 0.00138 -0.00164 C28 1 0.369128 1.011086 0.508273 11.00000 0.02958 0.01791 = 0.02605 0.00632 0.00037 0.00120 AFIX 33 H28A 2 0.383538 0.964479 0.489742 11.00000 -1.50000 H28B 2 0.382979 1.097707 0.511264 11.00000 -1.50000 H28C 2 0.337681 1.022654 0.503189 11.00000 -1.50000 AFIX 0 C29 1 0.400196 1.041307 0.629797 11.00000 0.02882 0.01968 = 0.02766 -0.00887 -0.00160 -0.00508 AFIX 33 H29A 2 0.373302 1.052785 0.643161 11.00000 -1.50000 H29B 2 0.409391 1.126777 0.620667 11.00000 -1.50000 H29C 2 0.423779 1.005754 0.643999 11.00000 -1.50000 AFIX 0 MOLE 2 IR2 6 0.374298 0.268464 0.328207 11.00000 0.00818 0.01010 = 0.01056 -0.00137 0.00097 0.00019 O7 4 0.250571 0.552599 0.385354 11.00000 0.01101 0.02327 = 0.02255 -0.00939 0.00062 0.00379 O8 4 0.390580 0.626999 0.426879 11.00000 0.02025 0.01746 = 0.01569 -0.00803 -0.00457 0.00549 O9 4 0.349110 0.615221 0.227378 11.00000 0.01527 0.02747 = 0.01746 0.01069 -0.00267 0.00044 O10 4 0.492785 0.535931 0.260741 11.00000 0.01087 0.02180 = 0.02119 0.00842 0.00202 -0.00238 O11 4 0.388661 0.106782 0.295045 11.00000 0.01403 0.01641 = 0.01868 -0.00548 0.00120 0.00026 O12 4 0.363481 0.127319 0.367309 11.00000 0.01591 0.01218 = 0.01676 0.00157 0.00093 0.00107 N5 3 0.307727 0.264237 0.320533 11.00000 0.01082 0.01398 = 0.01168 -0.00028 0.00007 -0.00077 N6 3 0.320359 0.589805 0.406048 11.00000 0.01691 0.01234 = 0.01323 -0.00229 -0.00056 0.00330 N7 3 0.421154 0.574164 0.243554 11.00000 0.01353 0.01478 = 0.01177 -0.00004 0.00024 -0.00040 N8 3 0.440619 0.282287 0.336051 11.00000 0.01049 0.01160 = 0.01097 -0.00271 0.00103 0.00067 C30 1 0.287755 0.178057 0.299758 11.00000 0.01506 0.01531 = 0.01596 -0.00315 0.00267 -0.00033 AFIX 43 H30 2 0.305523 0.118907 0.287129 11.00000 -1.20000 AFIX 0 C31 1 0.242505 0.172591 0.296164 11.00000 0.01585 0.01735 = 0.02006 -0.00480 -0.00196 -0.00342 AFIX 43 H31 2 0.229127 0.109487 0.281780 11.00000 -1.20000 AFIX 0 C32 1 0.217059 0.261538 0.314078 11.00000 0.01159 0.02209 = 0.02448 0.00000 -0.00051 -0.00231 AFIX 43 H32 2 0.185803 0.260527 0.311847 11.00000 -1.20000 AFIX 0 C33 1 0.236977 0.351842 0.335207 11.00000 0.01200 0.02083 = 0.01738 -0.00152 0.00242 0.00252 AFIX 43 H33 2 0.219493 0.413478 0.347285 11.00000 -1.20000 AFIX 0 C34 1 0.283100 0.352082 0.338736 11.00000 0.01282 0.01268 = 0.01219 0.00093 0.00269 0.00181 C35 1 0.309910 0.433930 0.360856 11.00000 0.01372 0.01063 = 0.01207 0.00109 -0.00071 -0.00082 C36 1 0.294666 0.525965 0.384237 11.00000 0.01236 0.01433 = 0.01391 0.00303 0.00237 0.00280 C37 1 0.363544 0.566885 0.404006 11.00000 0.01552 0.01209 = 0.01306 0.00207 -0.00119 -0.00022 C38 1 0.383411 0.484387 0.380551 11.00000 0.01330 0.01348 = 0.01441 -0.00015 0.00082 0.00203 AFIX 43 H38 2 0.414676 0.477715 0.379203 11.00000 -1.20000 AFIX 0 C39 1 0.356498 0.411969 0.359141 11.00000 0.01381 0.01296 = 0.00946 0.00138 0.00133 0.00031 C40 1 0.236148 0.650338 0.409356 11.00000 0.01752 0.02685 = 0.02149 -0.01263 0.00368 0.00819 AFIX 33 H40A 2 0.240587 0.616519 0.432108 11.00000 -1.50000 H40B 2 0.204727 0.669335 0.405869 11.00000 -1.50000 H40C 2 0.253352 0.731423 0.406365 11.00000 -1.50000 AFIX 0 C41 1 0.369374 0.683629 0.455771 11.00000 0.03364 0.02066 = 0.01401 -0.00259 -0.00263 0.00346 AFIX 33 H41A 2 0.351601 0.759768 0.448871 11.00000 -1.50000 H41B 2 0.391881 0.712169 0.471868 11.00000 -1.50000 H41C 2 0.350201 0.617511 0.466247 11.00000 -1.50000 AFIX 0 C42 1 0.389230 0.398838 0.292968 11.00000 0.01214 0.01412 = 0.00744 -0.00403 0.00053 0.00064 C43 1 0.360502 0.464483 0.271188 11.00000 0.00691 0.01526 = 0.01667 -0.00110 0.00255 -0.00008 AFIX 43 H43 2 0.329495 0.450546 0.272373 11.00000 -1.20000 AFIX 0 C44 1 0.378465 0.550802 0.247716 11.00000 0.01717 0.01312 = 0.01326 -0.00051 -0.00076 0.00408 C45 1 0.448551 0.513006 0.264602 11.00000 0.01108 0.01428 = 0.01453 -0.00366 0.00242 -0.00010 C46 1 0.435216 0.427466 0.290087 11.00000 0.01291 0.01103 = 0.01222 -0.00285 -0.00111 0.00023 C47 1 0.463844 0.361802 0.314415 11.00000 0.01388 0.00997 = 0.01351 -0.00403 0.00259 -0.00025 C48 1 0.509803 0.371105 0.317711 11.00000 0.01222 0.01493 = 0.01640 -0.00420 0.00097 -0.00179 AFIX 43 H48 2 0.526144 0.427136 0.303199 11.00000 -1.20000 AFIX 0 C49 1 0.531433 0.298682 0.342108 11.00000 0.01134 0.01913 = 0.01887 -0.00766 -0.00272 0.00208 AFIX 43 H49 2 0.562696 0.303132 0.343971 11.00000 -1.20000 AFIX 0 C50 1 0.507452 0.219810 0.363773 11.00000 0.01584 0.01710 = 0.01667 -0.00248 -0.00370 0.00498 AFIX 43 H50 2 0.521858 0.170612 0.380835 11.00000 -1.20000 AFIX 0 C51 1 0.462134 0.214134 0.360063 11.00000 0.01724 0.01523 = 0.01264 -0.00152 0.00035 -0.00003 AFIX 43 H51 2 0.445519 0.160353 0.374940 11.00000 -1.20000 AFIX 0 C52 1 0.366733 0.697836 0.201202 11.00000 0.02457 0.02739 = 0.01491 0.00874 -0.00264 0.00091 AFIX 33 H52A 2 0.384803 0.767875 0.211149 11.00000 -1.50000 H52B 2 0.342360 0.737342 0.188522 11.00000 -1.50000 H52C 2 0.385020 0.644467 0.186135 11.00000 -1.50000 AFIX 0 C53 1 0.505292 0.635648 0.236658 11.00000 0.01789 0.02303 = 0.02271 0.00822 0.00413 -0.00220 AFIX 33 H53A 2 0.495744 0.608414 0.214242 11.00000 -1.50000 H53B 2 0.537469 0.646620 0.236886 11.00000 -1.50000 H53C 2 0.491146 0.719527 0.242515 11.00000 -1.50000 AFIX 0 C54 1 0.391549 -0.014040 0.304132 11.00000 0.00897 0.01623 = 0.02593 -0.00880 -0.00283 -0.00008 C55 1 0.384007 -0.065185 0.336124 11.00000 0.01454 0.01256 = 0.03181 -0.00232 -0.00226 0.00194 AFIX 43 H55 2 0.389183 -0.157033 0.338832 11.00000 -1.20000 AFIX 0 C56 1 0.369745 0.002753 0.364637 11.00000 0.01071 0.01502 = 0.02356 0.00460 -0.00245 -0.00168 C57 1 0.403099 -0.108814 0.276303 11.00000 0.03552 0.02473 = 0.03308 -0.01335 0.00750 0.00334 AFIX 33 H57A 2 0.379573 -0.108169 0.259433 11.00000 -1.50000 H57B 2 0.406211 -0.198002 0.285497 11.00000 -1.50000 H57C 2 0.431013 -0.081800 0.265912 11.00000 -1.50000 AFIX 0 C58 1 0.360130 -0.075656 0.395729 11.00000 0.02913 0.01885 = 0.02610 0.00697 -0.00413 -0.00316 AFIX 33 H58A 2 0.372497 -0.030046 0.415241 11.00000 -1.50000 H58B 2 0.373532 -0.163355 0.393763 11.00000 -1.50000 H58C 2 0.328088 -0.084720 0.398467 11.00000 -1.50000 AFIX 0 MOLE 3 C59 1 0.252656 0.520841 0.203659 11.00000 0.02337 0.03010 = 0.02564 -0.00013 -0.00320 0.00077 AFIX 23 H59A 2 0.228225 0.581629 0.197829 11.00000 -1.20000 H59B 2 0.277050 0.573949 0.213219 11.00000 -1.20000 AFIX 0 CL1 5 0.271310 0.440222 0.167065 11.00000 0.04449 0.05485 = 0.02605 -0.00273 0.00041 0.01506 CL2 5 0.234030 0.405955 0.233915 11.00000 0.04709 0.04113 = 0.03166 -0.00134 0.00268 -0.01218 MOLE 4 PART 1 C60A 1 0.486293 0.854646 0.426978 21.00000 0.06912 0.04782 = 0.02440 0.01808 -0.02029 0.02345 AFIX 23 H60A 2 0.502954 0.856151 0.405638 21.00000 -1.20000 H60B 2 0.460333 0.796536 0.423781 21.00000 -1.20000 AFIX 0 CL3A 5 0.467920 1.011984 0.435493 21.00000 0.06209 0.03975 = 0.04239 -0.00225 -0.01146 0.00710 CL4A 5 0.519549 0.787533 0.457655 21.00000 0.11937 0.03709 = 0.06513 -0.00661 -0.04287 0.01141 PART 2 C60B 1 0.497974 0.847966 0.443672 -21.00000 0.07901 0.04797 = 0.04085 0.01989 -0.01811 0.03392 AFIX 23 H60C 2 0.529206 0.822262 0.440207 -21.00000 -1.20000 H60D 2 0.480864 0.766207 0.447684 -21.00000 -1.20000 AFIX 0 CL3B 5 0.478921 0.920397 0.407884 -21.00000 0.08472 0.05859 = 0.04884 -0.00417 -0.01510 0.01817 CL4B 5 0.494754 0.946339 0.479231 -21.00000 0.11789 0.04397 = 0.03657 0.00575 0.00446 -0.00705 PART 0 MOLE 0 HKLF 4 1 0 1 0 1 0 0 0 0 -1 REM JF362 in Pbca REM R1 = 0.0276 for 11828 Fo > 4sig(Fo) and 0.0378 for all 13983 data REM 803 parameters refined using 31 restraints END WGHT 0.0063 25.9136 REM Highest difference peak 0.785, deepest hole -0.824, 1-sigma level 0.110 Q1 1 0.4572 0.8938 0.4235 11.00000 0.05 0.79 Q2 1 0.4887 0.7774 0.4670 11.00000 0.05 0.71 Q3 1 0.3722 0.2674 0.3088 11.00000 0.05 0.70 Q4 1 0.3718 0.6640 0.5524 11.00000 0.05 0.65 Q5 1 0.3698 0.6602 0.5990 11.00000 0.05 0.64 Q6 1 0.3726 0.2713 0.3530 11.00000 0.05 0.54 Q7 1 0.3681 0.5125 0.5764 11.00000 0.05 0.49 Q8 1 0.2090 0.4342 0.2304 11.00000 0.05 0.47 Q9 1 0.3707 0.3167 0.6326 11.00000 0.05 0.47 Q10 1 0.3301 0.5212 0.5424 11.00000 0.05 0.46 ; _database_code_depnum_ccdc_archive 'CCDC 964314' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_eb370 _audit_update_record ; 2012-07-30 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H29 Ir N4 O4' _chemical_formula_sum 'C29 H29 Ir N4 O4' _chemical_formula_weight 689.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 11.1180(13) _cell_length_b 22.472(3) _cell_length_c 12.1117(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.716(11) _cell_angle_gamma 90.00 _cell_volume 3025.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 207 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description prismatic _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 4.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4144 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS 2008, Bruker AXS, 2008' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD' _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 34322 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 30.70 _reflns_number_total 4681 _reflns_number_gt 4263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs, 1990-2000)' _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^)+(0.0140P)^2^+9.1879P] 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 4681 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0560 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 0.0000 0.252852(6) 0.2500 0.01853(4) Uani 1 2 d S . . O1 O 0.32062(18) 0.10068(8) 0.07717(15) 0.0257(4) Uani 1 1 d . . . O2 O 0.13384(18) 0.32162(8) 0.23342(15) 0.0270(4) Uani 1 1 d . . . N1 N 0.03844(19) 0.24739(8) 0.41498(16) 0.0189(4) Uani 1 1 d . . . N2 N 0.2957(2) 0.09715(10) 0.26743(18) 0.0231(4) Uani 1 1 d . . . C1 C -0.0100(2) 0.28396(11) 0.49139(19) 0.0225(5) Uani 1 1 d . . . H1 H -0.0666 0.3131 0.4679 0.027 Uiso 1 1 calc R . . C2 C 0.0199(3) 0.28042(12) 0.6025(2) 0.0244(5) Uani 1 1 d . . . H2 H -0.0153 0.3067 0.6543 0.029 Uiso 1 1 calc R . . C3 C 0.1025(3) 0.23751(12) 0.6367(2) 0.0264(5) Uani 1 1 d . . . H3 H 0.1257 0.2345 0.7123 0.032 Uiso 1 1 calc R . . C4 C 0.1505(2) 0.19924(12) 0.55941(19) 0.0239(5) Uani 1 1 d . . . H4 H 0.2064 0.1696 0.5825 0.029 Uiso 1 1 calc R . . C5 C 0.1177(2) 0.20345(11) 0.44679(19) 0.0194(4) Uani 1 1 d . . . C6 C 0.1643(2) 0.16868(11) 0.35352(19) 0.0198(4) Uani 1 1 d . . . C7 C 0.2439(2) 0.12042(11) 0.3594(2) 0.0222(5) Uani 1 1 d . . . C8 C 0.2652(2) 0.12093(11) 0.1702(2) 0.0224(5) Uani 1 1 d . . . C9 C 0.1785(2) 0.16515(11) 0.1541(2) 0.0222(5) Uani 1 1 d . . . H9 H 0.1564 0.1780 0.0819 0.027 Uiso 1 1 calc R . . C10 C 0.1250(2) 0.19009(10) 0.24741(19) 0.0194(4) Uani 1 1 d . . . C11 C 0.2778(3) 0.08733(13) 0.4641(2) 0.0296(6) Uani 1 1 d . . . H11A H 0.3079 0.0477 0.4452 0.044 Uiso 1 1 calc R . . H11B H 0.2069 0.0835 0.5108 0.044 Uiso 1 1 calc R . . H11C H 0.3406 0.1094 0.5041 0.044 Uiso 1 1 calc R . . C12 C 0.4073(3) 0.05388(12) 0.0907(2) 0.0282(5) Uani 1 1 d . . . H12A H 0.4705 0.0667 0.1426 0.042 Uiso 1 1 calc R . . H12B H 0.4431 0.0447 0.0192 0.042 Uiso 1 1 calc R . . H12C H 0.3675 0.0183 0.1196 0.042 Uiso 1 1 calc R . . C13 C 0.1124(3) 0.37679(12) 0.2327(2) 0.0311(6) Uani 1 1 d . . . C14 C 0.0000 0.40447(18) 0.2500 0.0344(9) Uani 1 2 d S . . H14 H 0.0000 0.4467 0.2500 0.041 Uiso 1 2 calc SR . . C15 C 0.2201(3) 0.41575(14) 0.2095(3) 0.0411(8) Uani 1 1 d . . . H15A H 0.2846 0.4068 0.2629 0.062 Uiso 1 1 calc R . . H15B H 0.1971 0.4577 0.2162 0.062 Uiso 1 1 calc R . . H15C H 0.2484 0.4080 0.1346 0.062 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 0.02317(7) 0.02197(6) 0.01034(6) 0.000 -0.00419(4) 0.000 O1 0.0305(10) 0.0306(9) 0.0161(8) -0.0014(7) 0.0028(7) 0.0081(8) O2 0.0347(11) 0.0307(9) 0.0156(8) 0.0036(7) -0.0067(7) -0.0047(8) N1 0.0239(10) 0.0208(9) 0.0120(8) -0.0002(7) -0.0041(7) -0.0034(8) N2 0.0248(11) 0.0272(10) 0.0175(10) 0.0027(8) -0.0002(8) 0.0015(8) C1 0.0294(13) 0.0244(11) 0.0137(10) -0.0011(8) -0.0015(9) -0.0001(9) C2 0.0315(14) 0.0290(12) 0.0127(10) -0.0010(9) -0.0014(9) -0.0005(10) C3 0.0324(14) 0.0358(13) 0.0108(9) 0.0005(9) -0.0037(9) -0.0002(11) C4 0.0267(13) 0.0327(12) 0.0124(10) 0.0037(9) -0.0026(9) 0.0025(10) C5 0.0214(11) 0.0256(11) 0.0112(9) 0.0023(8) -0.0016(8) -0.0030(9) C6 0.0237(12) 0.0245(11) 0.0112(9) 0.0018(8) -0.0015(8) -0.0012(9) C7 0.0258(13) 0.0271(11) 0.0138(10) 0.0029(8) -0.0020(9) 0.0002(9) C8 0.0256(13) 0.0261(11) 0.0156(10) -0.0010(8) 0.0013(9) 0.0005(9) C9 0.0272(13) 0.0263(11) 0.0131(10) 0.0019(8) -0.0025(9) 0.0007(10) C10 0.0222(12) 0.0214(10) 0.0144(10) 0.0009(8) -0.0036(9) 0.0012(9) C11 0.0372(16) 0.0333(13) 0.0183(11) 0.0061(10) -0.0012(11) 0.0078(11) C12 0.0312(14) 0.0299(13) 0.0234(12) -0.0045(10) -0.0007(11) 0.0066(11) C13 0.0500(18) 0.0298(13) 0.0134(11) 0.0018(9) -0.0086(11) -0.0082(12) C14 0.056(3) 0.0244(17) 0.0226(18) 0.000 -0.0095(18) 0.000 C15 0.063(2) 0.0361(15) 0.0244(14) 0.0043(11) -0.0065(14) -0.0143(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C10 1.980(2) . ? Ir1 C10 1.981(2) 2 ? Ir1 N1 2.0418(19) 2 ? Ir1 N1 2.0419(19) . ? Ir1 O2 2.1565(19) 2 ? Ir1 O2 2.1565(19) . ? O1 C8 1.368(3) . ? O1 C12 1.434(3) . ? O2 C13 1.263(3) . ? N1 C1 1.355(3) . ? N1 C5 1.375(3) . ? N2 C8 1.334(3) . ? N2 C7 1.365(3) . ? C1 C2 1.385(3) . ? C1 H1 0.9500 . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.383(4) . ? C3 H3 0.9500 . ? C4 C5 1.411(3) . ? C4 H4 0.9500 . ? C5 C6 1.473(3) . ? C6 C7 1.402(3) . ? C6 C10 1.435(3) . ? C7 C11 1.513(3) . ? C8 C9 1.397(4) . ? C9 C10 1.401(3) . ? C9 H9 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.414(4) . ? C13 C15 1.513(4) . ? C14 C13 1.414(4) 2 ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Ir1 C10 89.17(14) . 2 ? C10 Ir1 N1 94.59(9) . 2 ? C10 Ir1 N1 80.47(9) 2 2 ? C10 Ir1 N1 80.47(9) . . ? C10 Ir1 N1 94.59(9) 2 . ? N1 Ir1 N1 173.10(11) 2 . ? C10 Ir1 O2 175.52(8) . 2 ? C10 Ir1 O2 91.37(9) 2 2 ? N1 Ir1 O2 89.88(7) 2 2 ? N1 Ir1 O2 95.06(8) . 2 ? C10 Ir1 O2 91.37(9) . . ? C10 Ir1 O2 175.52(8) 2 . ? N1 Ir1 O2 95.06(8) 2 . ? N1 Ir1 O2 89.89(7) . . ? O2 Ir1 O2 88.44(11) 2 . ? C8 O1 C12 117.3(2) . . ? C13 O2 Ir1 125.0(2) . . ? C1 N1 C5 120.2(2) . . ? C1 N1 Ir1 123.50(16) . . ? C5 N1 Ir1 116.29(15) . . ? C8 N2 C7 117.6(2) . . ? N1 C1 C2 122.4(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.6(2) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 118.4(2) . . ? N1 C5 C6 113.3(2) . . ? C4 C5 C6 128.1(2) . . ? C7 C6 C10 119.4(2) . . ? C7 C6 C5 126.8(2) . . ? C10 C6 C5 113.8(2) . . ? N2 C7 C6 121.8(2) . . ? N2 C7 C11 113.1(2) . . ? C6 C7 C11 125.0(2) . . ? N2 C8 O1 118.8(2) . . ? N2 C8 C9 125.1(2) . . ? O1 C8 C9 116.0(2) . . ? C8 C9 C10 118.1(2) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C9 C10 C6 117.4(2) . . ? C9 C10 Ir1 127.07(18) . . ? C6 C10 Ir1 115.48(17) . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 C14 126.7(3) . . ? O2 C13 C15 114.8(3) . . ? C14 C13 C15 118.4(3) . . ? C13 C14 C13 127.8(4) . 2 ? C13 C14 H14 116.1 . . ? C13 C14 H14 116.1 2 . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 Ir1 O2 C13 -177.8(2) . . . . ? N1 Ir1 O2 C13 87.5(2) 2 . . . ? N1 Ir1 O2 C13 -97.3(2) . . . . ? O2 Ir1 O2 C13 -2.23(16) 2 . . . ? C10 Ir1 N1 C1 175.3(2) . . . . ? C10 Ir1 N1 C1 -96.4(2) 2 . . . ? O2 Ir1 N1 C1 -4.6(2) 2 . . . ? O2 Ir1 N1 C1 83.8(2) . . . . ? C10 Ir1 N1 C5 -5.08(17) . . . . ? C10 Ir1 N1 C5 83.31(18) 2 . . . ? O2 Ir1 N1 C5 175.09(17) 2 . . . ? O2 Ir1 N1 C5 -96.48(18) . . . . ? C5 N1 C1 C2 2.1(4) . . . . ? Ir1 N1 C1 C2 -178.2(2) . . . . ? N1 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C1 N1 C5 C4 -2.6(3) . . . . ? Ir1 N1 C5 C4 177.74(18) . . . . ? C1 N1 C5 C6 -178.5(2) . . . . ? Ir1 N1 C5 C6 1.8(3) . . . . ? C3 C4 C5 N1 1.3(4) . . . . ? C3 C4 C5 C6 176.6(3) . . . . ? N1 C5 C6 C7 -178.5(2) . . . . ? C4 C5 C6 C7 6.0(4) . . . . ? N1 C5 C6 C10 4.3(3) . . . . ? C4 C5 C6 C10 -171.2(2) . . . . ? C8 N2 C7 C6 -1.8(4) . . . . ? C8 N2 C7 C11 175.8(2) . . . . ? C10 C6 C7 N2 7.2(4) . . . . ? C5 C6 C7 N2 -169.8(2) . . . . ? C5 C6 C7 C11 12.8(4) . . . . ? C7 N2 C8 O1 176.5(2) . . . . ? C7 N2 C8 C9 -4.5(4) . . . . ? C12 O1 C8 N2 1.1(3) . . . . ? C12 O1 C8 C9 -178.0(2) . . . . ? N2 C8 C9 C10 5.1(4) . . . . ? O1 C8 C9 C10 -175.9(2) . . . . ? C8 C9 C10 C6 0.6(4) . . . . ? C8 C9 C10 Ir1 -179.80(19) . . . . ? C7 C6 C10 C9 -6.4(4) . . . . ? C5 C6 C10 C9 171.0(2) . . . . ? C7 C6 C10 Ir1 173.98(19) . . . . ? C5 C6 C10 Ir1 -8.6(3) . . . . ? C10 Ir1 C10 C9 93.0(2) 2 . . . ? N1 Ir1 C10 C9 12.6(2) 2 . . . ? N1 Ir1 C10 C9 -172.2(2) . . . . ? O2 Ir1 C10 C9 -82.6(2) . . . . ? C10 Ir1 C10 C6 -87.41(19) 2 . . . ? N1 Ir1 C10 C6 -167.78(18) 2 . . . ? N1 Ir1 C10 C6 7.38(18) . . . . ? O2 Ir1 C10 C6 97.04(19) . . . . ? Ir1 O2 C13 C14 4.7(3) . . . . ? Ir1 O2 C13 C15 -174.65(17) . . . . ? O2 C13 C14 C13 -2.7(2) . . . 2 ? C15 C13 C14 C13 176.6(3) . . . 2 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.70 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.388 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.111 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.008 276 45 ' ' 2 0.500 0.500 0.368 276 45 ' ' _platon_squeeze_details ; ; _iucr_refine_instructions_details ; TITL EB370 in C2/c CELL 0.71073 11.1180 22.4725 12.1117 90.0000 90.7160 90.0000 ZERR 4.00 0.0013 0.0032 0.0014 0.0000 0.0110 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O IR UNIT 116 116 16 16 4 REM ---------------------------------------------------------- REM Data collection: Bruker APEX II CCD REM Absorption correction: SADABS REM Crystal habit: prismatic; Crystal colour: amber REM About half DCM molecule has been squeezed REM ---------------------------------------------------------- L.S. 10 ACTA WPDB -2 CONF SIZE 0.478 0.135 0.120 BOND $H FMAP 2 PLAN 10 TEMP -173 TWIN 1 0 0 0 -1 0 0 0 -1 WGHT 0.014000 9.187901 BASF 0.00314 FVAR 1.51639 IR1 5 0.000000 0.252852 0.250000 10.50000 0.02317 0.02197 = 0.01034 0.00000 -0.00419 0.00000 O1 4 0.320622 0.100677 0.077171 11.00000 0.03047 0.03059 = 0.01611 -0.00142 0.00280 0.00811 O2 4 0.133838 0.321623 0.233419 11.00000 0.03470 0.03068 = 0.01555 0.00362 -0.00667 -0.00467 N1 3 0.038439 0.247386 0.414982 11.00000 0.02391 0.02077 = 0.01200 -0.00019 -0.00406 -0.00335 N2 3 0.295694 0.097148 0.267431 11.00000 0.02475 0.02715 = 0.01751 0.00272 -0.00018 0.00150 C1 1 -0.010025 0.283964 0.491386 11.00000 0.02938 0.02439 = 0.01365 -0.00108 -0.00150 -0.00014 AFIX 43 H1 2 -0.066642 0.313129 0.467856 11.00000 -1.20000 AFIX 0 C2 1 0.019896 0.280424 0.602522 11.00000 0.03147 0.02897 = 0.01266 -0.00096 -0.00139 -0.00051 AFIX 43 H2 2 -0.015260 0.306747 0.654324 11.00000 -1.20000 AFIX 0 C3 1 0.102527 0.237509 0.636749 11.00000 0.03244 0.03581 = 0.01081 0.00054 -0.00371 -0.00017 AFIX 43 H3 2 0.125738 0.234531 0.712300 11.00000 -1.20000 AFIX 0 C4 1 0.150458 0.199236 0.559407 11.00000 0.02669 0.03269 = 0.01235 0.00368 -0.00256 0.00249 AFIX 43 H4 2 0.206354 0.169641 0.582510 11.00000 -1.20000 AFIX 0 C5 1 0.117675 0.203445 0.446793 11.00000 0.02137 0.02559 = 0.01125 0.00226 -0.00156 -0.00305 C6 1 0.164277 0.168684 0.353518 11.00000 0.02373 0.02446 = 0.01124 0.00181 -0.00153 -0.00123 C7 1 0.243948 0.120422 0.359440 11.00000 0.02577 0.02708 = 0.01381 0.00289 -0.00201 0.00018 C8 1 0.265237 0.120932 0.170158 11.00000 0.02564 0.02611 = 0.01559 -0.00100 0.00133 0.00048 C9 1 0.178477 0.165148 0.154089 11.00000 0.02720 0.02630 = 0.01312 0.00189 -0.00246 0.00066 AFIX 43 H9 2 0.156371 0.177951 0.081889 11.00000 -1.20000 AFIX 0 C10 1 0.124975 0.190086 0.247406 11.00000 0.02224 0.02143 = 0.01442 0.00093 -0.00364 0.00119 C11 1 0.277831 0.087328 0.464114 11.00000 0.03720 0.03334 = 0.01826 0.00612 -0.00123 0.00778 AFIX 33 H11A 2 0.307879 0.047665 0.445217 11.00000 -1.50000 H11B 2 0.206904 0.083466 0.510811 11.00000 -1.50000 H11C 2 0.340649 0.109425 0.504095 11.00000 -1.50000 AFIX 0 C12 1 0.407285 0.053877 0.090716 11.00000 0.03125 0.02988 = 0.02341 -0.00450 -0.00068 0.00660 AFIX 33 H12A 2 0.470486 0.066678 0.142603 11.00000 -1.50000 H12B 2 0.443058 0.044658 0.019180 11.00000 -1.50000 H12C 2 0.367521 0.018318 0.119620 11.00000 -1.50000 AFIX 0 C13 1 0.112401 0.376794 0.232709 11.00000 0.04999 0.02980 = 0.01342 0.00180 -0.00858 -0.00821 C14 1 0.000000 0.404469 0.250000 10.50000 0.05595 0.02443 = 0.02255 0.00000 -0.00952 0.00000 AFIX 43 H14 2 -0.000001 0.446742 0.250003 10.50000 -1.20000 AFIX 0 C15 1 0.220139 0.415750 0.209545 11.00000 0.06256 0.03609 = 0.02436 0.00430 -0.00645 -0.01430 AFIX 33 H15A 2 0.284636 0.406783 0.262873 11.00000 -1.50000 H15B 2 0.197142 0.457685 0.216162 11.00000 -1.50000 H15C 2 0.248437 0.408019 0.134593 11.00000 -1.50000 HKLF 4 REM EB370 in C2/c REM R1 = 0.0254 for 4263 Fo > 4sig(Fo) and 0.0301 for all 4681 data REM 174 parameters refined using 0 restraints END WGHT 0.0140 9.1793 REM Highest difference peak 1.388, deepest hole -1.079, 1-sigma level 0.111 Q1 1 0.0000 0.2862 0.2500 10.50000 0.05 1.39 Q2 1 0.0562 0.2546 0.3450 11.00000 0.05 0.92 Q3 1 0.0381 0.2078 0.2334 11.00000 0.05 0.88 Q4 1 0.0430 0.2534 0.2080 11.00000 0.05 0.67 Q5 1 -0.0459 0.2169 0.1938 11.00000 0.05 0.67 Q6 1 0.0959 0.2339 0.2632 11.00000 0.05 0.58 Q7 1 -0.0356 0.2927 0.1823 11.00000 0.05 0.57 Q8 1 0.1321 0.1792 0.4038 11.00000 0.05 0.56 Q9 1 0.0000 0.3161 0.2500 10.50000 0.05 0.55 Q10 1 0.1144 0.2794 0.2841 11.00000 0.05 0.55 ; _database_code_depnum_ccdc_archive 'CCDC 964315'