# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # 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_fro5098 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H19 B F7 Ir N6' _chemical_formula_weight 799.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6660(3) _cell_length_b 23.6037(8) _cell_length_c 12.8285(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.336(2) _cell_angle_gamma 90.00 _cell_volume 2869.77(16) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4872 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 9.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1587 _exptl_absorpt_correction_T_max 0.4434 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20569 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.98 _diffrn_reflns_theta_max 68.00 _reflns_number_total 5092 _reflns_number_gt 4894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0425P)^2^+7.7991P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5092 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Ir Ir 0.441405(17) 0.136585(7) 0.688413(13) 0.02577(8) Uani 1 1 d . . . N1 N 0.4005(4) 0.11995(15) 0.8454(3) 0.0283(7) Uani 1 1 d . . . C2 C 0.2837(5) 0.13647(18) 0.8803(4) 0.0336(10) Uani 1 1 d . . . H2 H 0.2149 0.1577 0.8347 0.040 Uiso 1 1 calc R . . C3 C 0.2619(6) 0.1232(2) 0.9806(4) 0.0438(12) Uani 1 1 d . . . H3 H 0.1800 0.1355 1.0030 0.053 Uiso 1 1 calc R . . C4 C 0.3617(6) 0.0917(2) 1.0472(4) 0.0445(12) Uani 1 1 d . . . H4 H 0.3474 0.0816 1.1152 0.053 Uiso 1 1 calc R . . C5 C 0.4828(5) 0.0752(2) 1.0142(4) 0.0381(10) Uani 1 1 d . . . H5 H 0.5525 0.0541 1.0593 0.046 Uiso 1 1 calc R . . C6 C 0.4997(5) 0.09023(18) 0.9123(3) 0.0308(9) Uani 1 1 d . . . C7 C 0.6241(5) 0.07740(17) 0.8692(3) 0.0294(9) Uani 1 1 d . . . N8 N 0.6249(4) 0.09337(15) 0.7675(3) 0.0298(7) Uani 1 1 d . . . N9 N 0.7483(4) 0.08273(15) 0.7422(3) 0.0321(8) Uani 1 1 d . . . N10 N 0.8263(4) 0.06006(15) 0.8300(3) 0.0329(8) Uani 1 1 d . . . C11 C 0.7552(5) 0.0555(2) 0.9089(4) 0.0374(10) Uani 1 1 d . . . H11 H 0.7881 0.0405 0.9772 0.045 Uiso 1 1 calc R . . C12 C 0.9735(5) 0.0429(2) 0.8315(4) 0.0421(11) Uani 1 1 d . . . H12A H 1.0330 0.0569 0.8972 0.050 Uiso 1 1 calc R . . H12B H 1.0053 0.0612 0.7717 0.050 Uiso 1 1 calc R . . B13 B 0.9965(6) -0.0242(3) 0.8241(4) 0.0394(12) Uani 1 1 d . . . F14 F 0.9393(3) -0.05351(14) 0.9003(3) 0.0588(8) Uani 1 1 d . . . F15 F 0.9385(4) -0.04479(15) 0.7235(3) 0.0622(9) Uani 1 1 d . . . F16 F 1.1435(3) -0.03499(14) 0.8441(2) 0.0501(7) Uani 1 1 d . . . N21 N 0.5132(4) 0.21552(16) 0.7378(3) 0.0336(8) Uani 1 1 d . . . C22 C 0.6440(5) 0.2259(2) 0.7945(4) 0.0442(12) Uani 1 1 d . . . H22 H 0.7045 0.1952 0.8168 0.053 Uiso 1 1 calc R . . C23 C 0.6915(7) 0.2799(2) 0.8209(5) 0.0596(15) Uani 1 1 d . . . H23 H 0.7828 0.2861 0.8609 0.071 Uiso 1 1 calc R . . C24 C 0.6037(7) 0.3246(3) 0.7879(5) 0.0653(17) Uani 1 1 d . . . H24 H 0.6346 0.3618 0.8052 0.078 Uiso 1 1 calc R . . C25 C 0.4702(7) 0.3152(2) 0.7295(5) 0.0572(14) Uani 1 1 d . . . H25 H 0.4104 0.3460 0.7059 0.069 Uiso 1 1 calc R . . C26 C 0.4240(5) 0.2596(2) 0.7053(4) 0.0374(10) Uani 1 1 d . . . C27 C 0.2861(5) 0.2411(2) 0.6464(4) 0.0396(11) Uani 1 1 d . . . C28 C 0.1715(6) 0.2755(2) 0.6063(4) 0.0492(13) Uani 1 1 d . . . F28 F 0.1874(4) 0.33328(14) 0.6156(3) 0.0683(10) Uani 1 1 d . . . C29 C 0.0431(6) 0.2562(3) 0.5570(5) 0.0608(16) Uani 1 1 d . . . H29 H -0.0321 0.2809 0.5311 0.073 Uiso 1 1 calc R . . C30 C 0.0291(5) 0.1983(3) 0.5471(5) 0.0586(16) Uani 1 1 d . . . F30 F -0.0982(4) 0.1769(2) 0.4988(4) 0.0948(15) Uani 1 1 d . . . C31 C 0.1356(5) 0.1606(2) 0.5818(4) 0.0450(12) Uani 1 1 d . . . H31 H 0.1214 0.1214 0.5716 0.054 Uiso 1 1 calc R . . C32 C 0.2661(5) 0.1821(2) 0.6327(3) 0.0345(10) Uani 1 1 d . . . N41 N 0.3572(4) 0.06238(15) 0.6200(3) 0.0288(7) Uani 1 1 d . . . C42 C 0.2879(5) 0.0238(2) 0.6673(4) 0.0361(10) Uani 1 1 d . . . H42 H 0.2832 0.0293 0.7391 0.043 Uiso 1 1 calc R . . C43 C 0.2239(5) -0.0230(2) 0.6168(4) 0.0436(11) Uani 1 1 d . . . H43 H 0.1759 -0.0489 0.6526 0.052 Uiso 1 1 calc R . . C44 C 0.2322(6) -0.0311(2) 0.5114(4) 0.0467(12) Uani 1 1 d . . . H44 H 0.1894 -0.0628 0.4740 0.056 Uiso 1 1 calc R . . C45 C 0.3036(5) 0.0076(2) 0.4617(4) 0.0417(11) Uani 1 1 d . . . H45 H 0.3101 0.0021 0.3903 0.050 Uiso 1 1 calc R . . C46 C 0.3656(4) 0.05445(19) 0.5157(3) 0.0305(9) Uani 1 1 d . . . C47 C 0.4417(5) 0.1003(2) 0.4728(3) 0.0333(10) Uani 1 1 d . . . C48 C 0.4714(5) 0.1022(2) 0.3720(4) 0.0414(11) Uani 1 1 d . . . F48 F 0.4312(4) 0.05895(15) 0.3026(2) 0.0599(8) Uani 1 1 d . . . C49 C 0.5423(6) 0.1466(3) 0.3354(4) 0.0485(13) Uani 1 1 d . . . H49 H 0.5594 0.1473 0.2658 0.058 Uiso 1 1 calc R . . C50 C 0.5860(5) 0.1895(2) 0.4063(4) 0.0460(12) Uani 1 1 d . . . F50 F 0.6550(4) 0.23395(16) 0.3727(3) 0.0641(9) Uani 1 1 d . . . C51 C 0.5635(5) 0.1900(2) 0.5080(4) 0.0374(10) Uani 1 1 d . . . H51 H 0.5969 0.2202 0.5538 0.045 Uiso 1 1 calc R . . C52 C 0.4899(4) 0.14495(18) 0.5438(4) 0.0294(9) 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 Ir 0.02140(12) 0.02909(12) 0.02597(12) 0.00283(6) 0.00254(7) 0.00176(6) N1 0.0272(18) 0.0302(18) 0.0273(17) -0.0030(14) 0.0050(14) -0.0027(15) C2 0.027(2) 0.039(2) 0.037(2) -0.0052(18) 0.0101(19) -0.0036(18) C3 0.038(3) 0.054(3) 0.042(3) -0.012(2) 0.016(2) -0.018(2) C4 0.054(3) 0.051(3) 0.031(2) -0.004(2) 0.013(2) -0.019(2) C5 0.043(3) 0.039(2) 0.030(2) 0.0000(18) 0.0003(19) -0.009(2) C6 0.034(2) 0.027(2) 0.030(2) -0.0017(17) 0.0017(17) -0.0042(18) C7 0.034(2) 0.027(2) 0.0242(19) 0.0034(16) -0.0018(17) -0.0009(17) N8 0.0255(17) 0.0315(18) 0.0300(18) -0.0004(14) -0.0004(14) 0.0021(15) N9 0.0258(17) 0.0302(19) 0.0391(19) -0.0023(15) 0.0032(15) 0.0010(15) N10 0.0238(17) 0.0328(19) 0.039(2) 0.0013(15) -0.0013(15) 0.0039(15) C11 0.036(2) 0.037(2) 0.035(2) 0.0066(19) -0.0055(19) 0.001(2) C12 0.024(2) 0.040(3) 0.059(3) 0.006(2) 0.002(2) -0.001(2) B13 0.031(3) 0.047(3) 0.040(3) 0.004(2) 0.007(2) 0.006(2) F14 0.0547(19) 0.0529(18) 0.076(2) 0.0202(16) 0.0311(16) 0.0090(15) F15 0.063(2) 0.058(2) 0.0584(19) -0.0111(16) -0.0029(16) 0.0032(16) F16 0.0382(15) 0.067(2) 0.0465(16) 0.0126(14) 0.0124(13) 0.0205(14) N21 0.0327(19) 0.0312(19) 0.0367(19) 0.0000(15) 0.0065(16) 0.0013(16) C22 0.037(3) 0.041(3) 0.051(3) -0.001(2) -0.001(2) -0.008(2) C23 0.054(3) 0.045(3) 0.074(4) -0.005(3) 0.000(3) -0.013(3) C24 0.071(4) 0.037(3) 0.082(4) -0.012(3) 0.000(3) -0.007(3) C25 0.064(4) 0.035(3) 0.073(4) 0.005(3) 0.011(3) 0.004(3) C26 0.041(3) 0.034(2) 0.038(2) 0.0035(19) 0.010(2) 0.005(2) C27 0.039(3) 0.043(3) 0.039(2) 0.008(2) 0.012(2) 0.012(2) C28 0.047(3) 0.050(3) 0.053(3) 0.012(2) 0.014(2) 0.024(2) F28 0.073(2) 0.0463(18) 0.086(2) 0.0109(17) 0.0163(19) 0.0286(17) C29 0.039(3) 0.072(4) 0.071(4) 0.024(3) 0.009(3) 0.030(3) C30 0.024(2) 0.076(4) 0.071(4) 0.015(3) -0.001(2) 0.009(3) F30 0.0289(17) 0.109(3) 0.134(4) 0.023(3) -0.015(2) 0.0033(19) C31 0.027(2) 0.054(3) 0.051(3) 0.013(2) 0.000(2) 0.005(2) C32 0.028(2) 0.045(3) 0.032(2) 0.0061(19) 0.0074(17) 0.0060(19) N41 0.0235(17) 0.0328(19) 0.0296(18) 0.0006(14) 0.0038(14) 0.0014(15) C42 0.036(2) 0.041(3) 0.032(2) -0.0017(19) 0.0082(19) -0.004(2) C43 0.038(3) 0.043(3) 0.052(3) -0.003(2) 0.012(2) -0.011(2) C44 0.045(3) 0.048(3) 0.046(3) -0.012(2) 0.006(2) -0.011(2) C45 0.039(3) 0.050(3) 0.034(2) -0.005(2) 0.005(2) 0.002(2) C46 0.025(2) 0.039(2) 0.026(2) -0.0006(17) 0.0018(16) 0.0045(18) C47 0.029(2) 0.044(3) 0.026(2) 0.0026(18) 0.0027(17) 0.0046(19) C48 0.039(3) 0.054(3) 0.031(2) 0.005(2) 0.0057(19) 0.004(2) F48 0.076(2) 0.074(2) 0.0320(15) -0.0080(14) 0.0162(15) -0.0075(18) C49 0.047(3) 0.067(4) 0.033(2) 0.013(2) 0.013(2) 0.006(3) C50 0.035(3) 0.055(3) 0.048(3) 0.020(2) 0.009(2) 0.003(2) F50 0.060(2) 0.074(2) 0.062(2) 0.0255(17) 0.0220(16) -0.0135(17) C51 0.029(2) 0.045(3) 0.038(2) 0.010(2) 0.0048(18) 0.000(2) C52 0.020(2) 0.035(2) 0.032(2) 0.0072(17) 0.0036(17) 0.0056(17) _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 Ir C52 2.011(4) . ? Ir C32 2.015(4) . ? Ir N21 2.045(4) . ? Ir N41 2.054(4) . ? Ir N8 2.123(3) . ? Ir N1 2.163(3) . ? N1 C6 1.351(6) . ? N1 C2 1.351(6) . ? C2 C3 1.379(7) . ? C2 H2 0.9400 . ? C3 C4 1.374(8) . ? C3 H3 0.9400 . ? C4 C5 1.377(7) . ? C4 H4 0.9400 . ? C5 C6 1.394(6) . ? C5 H5 0.9400 . ? C6 C7 1.451(6) . ? C7 N8 1.360(5) . ? C7 C11 1.370(6) . ? N8 N9 1.320(5) . ? N9 N10 1.338(5) . ? N10 C11 1.334(6) . ? N10 C12 1.476(6) . ? C11 H11 0.9400 . ? C12 B13 1.604(8) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? B13 F15 1.389(7) . ? B13 F14 1.397(6) . ? B13 F16 1.417(6) . ? N21 C22 1.352(6) . ? N21 C26 1.363(6) . ? C22 C23 1.375(7) . ? C22 H22 0.9400 . ? C23 C24 1.367(9) . ? C23 H23 0.9400 . ? C24 C25 1.377(9) . ? C24 H24 0.9400 . ? C25 C26 1.403(7) . ? C25 H25 0.9400 . ? C26 C27 1.463(7) . ? C27 C28 1.388(7) . ? C27 C32 1.414(7) . ? C28 C29 1.357(9) . ? C28 F28 1.374(7) . ? C29 C30 1.375(9) . ? C29 H29 0.9400 . ? C30 F30 1.361(7) . ? C30 C31 1.368(7) . ? C31 C32 1.397(7) . ? C31 H31 0.9400 . ? N41 C42 1.344(6) . ? N41 C46 1.368(5) . ? C42 C43 1.366(7) . ? C42 H42 0.9400 . ? C43 C44 1.384(7) . ? C43 H43 0.9400 . ? C44 C45 1.374(7) . ? C44 H44 0.9400 . ? C45 C46 1.378(7) . ? C45 H45 0.9400 . ? C46 C47 1.474(6) . ? C47 C48 1.380(6) . ? C47 C52 1.411(6) . ? C48 F48 1.360(6) . ? C48 C49 1.384(8) . ? C49 C50 1.370(8) . ? C49 H49 0.9400 . ? C50 F50 1.359(6) . ? C50 C51 1.364(7) . ? C51 C52 1.405(6) . ? C51 H51 0.9400 . ? 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 C52 Ir C32 87.29(17) . . ? C52 Ir N21 93.99(16) . . ? C32 Ir N21 80.51(17) . . ? C52 Ir N41 80.43(16) . . ? C32 Ir N41 93.89(17) . . ? N21 Ir N41 172.33(14) . . ? C52 Ir N8 99.43(15) . . ? C32 Ir N8 172.25(16) . . ? N21 Ir N8 95.10(14) . . ? N41 Ir N8 91.04(13) . . ? C52 Ir N1 174.45(15) . . ? C32 Ir N1 97.59(16) . . ? N21 Ir N1 89.44(14) . . ? N41 Ir N1 96.53(13) . . ? N8 Ir N1 75.89(13) . . ? C6 N1 C2 118.3(4) . . ? C6 N1 Ir 116.7(3) . . ? C2 N1 Ir 125.0(3) . . ? N1 C2 C3 122.3(5) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 119.1(5) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 118.6(5) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? N1 C6 C5 121.9(4) . . ? N1 C6 C7 113.8(4) . . ? C5 C6 C7 124.3(4) . . ? N8 C7 C11 106.4(4) . . ? N8 C7 C6 118.0(4) . . ? C11 C7 C6 135.4(4) . . ? N9 N8 C7 111.0(3) . . ? N9 N8 Ir 133.2(3) . . ? C7 N8 Ir 115.5(3) . . ? N8 N9 N10 104.8(3) . . ? C11 N10 N9 112.4(4) . . ? C11 N10 C12 127.4(4) . . ? N9 N10 C12 120.2(4) . . ? N10 C11 C7 105.3(4) . . ? N10 C11 H11 127.3 . . ? C7 C11 H11 127.3 . . ? N10 C12 B13 114.5(4) . . ? N10 C12 H12A 108.6 . . ? B13 C12 H12A 108.6 . . ? N10 C12 H12B 108.6 . . ? B13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? F15 B13 F14 109.5(5) . . ? F15 B13 F16 108.2(4) . . ? F14 B13 F16 107.7(4) . . ? F15 B13 C12 111.4(4) . . ? F14 B13 C12 111.7(4) . . ? F16 B13 C12 108.2(4) . . ? C22 N21 C26 119.7(4) . . ? C22 N21 Ir 123.9(3) . . ? C26 N21 Ir 116.4(3) . . ? N21 C22 C23 122.2(5) . . ? N21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C24 C23 C22 118.8(5) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 120.2(5) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 119.6(5) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? N21 C26 C25 119.5(5) . . ? N21 C26 C27 112.9(4) . . ? C25 C26 C27 127.6(5) . . ? C28 C27 C32 116.8(5) . . ? C28 C27 C26 126.7(5) . . ? C32 C27 C26 116.5(4) . . ? C29 C28 F28 116.8(5) . . ? C29 C28 C27 124.5(6) . . ? F28 C28 C27 118.7(5) . . ? C28 C29 C30 116.2(5) . . ? C28 C29 H29 121.9 . . ? C30 C29 H29 121.9 . . ? F30 C30 C31 117.5(6) . . ? F30 C30 C29 118.3(5) . . ? C31 C30 C29 124.2(5) . . ? C30 C31 C32 117.9(5) . . ? C30 C31 H31 121.0 . . ? C32 C31 H31 121.0 . . ? C31 C32 C27 120.3(4) . . ? C31 C32 Ir 126.3(4) . . ? C27 C32 Ir 113.3(3) . . ? C42 N41 C46 118.6(4) . . ? C42 N41 Ir 125.1(3) . . ? C46 N41 Ir 116.1(3) . . ? N41 C42 C43 123.6(4) . . ? N41 C42 H42 118.2 . . ? C43 C42 H42 118.2 . . ? C42 C43 C44 117.8(5) . . ? C42 C43 H43 121.1 . . ? C44 C43 H43 121.1 . . ? C45 C44 C43 119.6(5) . . ? C45 C44 H44 120.2 . . ? C43 C44 H44 120.2 . . ? C44 C45 C46 120.5(4) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? N41 C46 C45 119.9(4) . . ? N41 C46 C47 113.2(4) . . ? C45 C46 C47 126.9(4) . . ? C48 C47 C52 118.5(4) . . ? C48 C47 C46 125.8(4) . . ? C52 C47 C46 115.7(4) . . ? F48 C48 C47 120.2(5) . . ? F48 C48 C49 116.3(4) . . ? C47 C48 C49 123.4(5) . . ? C50 C49 C48 116.3(5) . . ? C50 C49 H49 121.9 . . ? C48 C49 H49 121.9 . . ? F50 C50 C51 118.5(5) . . ? F50 C50 C49 117.8(5) . . ? C51 C50 C49 123.7(5) . . ? C50 C51 C52 119.5(5) . . ? C50 C51 H51 120.3 . . ? C52 C51 H51 120.3 . . ? C51 C52 C47 118.6(4) . . ? C51 C52 Ir 126.9(4) . . ? C47 C52 Ir 114.5(3) . . ? 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 C52 Ir N1 C6 30.2(16) . . . . ? C32 Ir N1 C6 -178.4(3) . . . . ? N21 Ir N1 C6 -98.1(3) . . . . ? N41 Ir N1 C6 86.8(3) . . . . ? N8 Ir N1 C6 -2.7(3) . . . . ? C52 Ir N1 C2 -149.1(14) . . . . ? C32 Ir N1 C2 2.3(4) . . . . ? N21 Ir N1 C2 82.7(3) . . . . ? N41 Ir N1 C2 -92.5(3) . . . . ? N8 Ir N1 C2 178.0(4) . . . . ? C6 N1 C2 C3 -1.1(6) . . . . ? Ir N1 C2 C3 178.2(3) . . . . ? N1 C2 C3 C4 -0.5(7) . . . . ? C2 C3 C4 C5 1.5(7) . . . . ? C3 C4 C5 C6 -0.9(7) . . . . ? C2 N1 C6 C5 1.7(6) . . . . ? Ir N1 C6 C5 -177.6(3) . . . . ? C2 N1 C6 C7 -176.7(4) . . . . ? Ir N1 C6 C7 4.0(5) . . . . ? C4 C5 C6 N1 -0.7(7) . . . . ? C4 C5 C6 C7 177.5(4) . . . . ? N1 C6 C7 N8 -3.3(6) . . . . ? C5 C6 C7 N8 178.3(4) . . . . ? N1 C6 C7 C11 170.3(5) . . . . ? C5 C6 C7 C11 -8.0(8) . . . . ? C11 C7 N8 N9 0.0(5) . . . . ? C6 C7 N8 N9 175.3(4) . . . . ? C11 C7 N8 Ir -174.3(3) . . . . ? C6 C7 N8 Ir 1.1(5) . . . . ? C52 Ir N8 N9 11.2(4) . . . . ? C32 Ir N8 N9 -138.8(11) . . . . ? N21 Ir N8 N9 -83.7(4) . . . . ? N41 Ir N8 N9 91.7(4) . . . . ? N1 Ir N8 N9 -171.9(4) . . . . ? C52 Ir N8 C7 -176.2(3) . . . . ? C32 Ir N8 C7 33.9(13) . . . . ? N21 Ir N8 C7 88.9(3) . . . . ? N41 Ir N8 C7 -95.7(3) . . . . ? N1 Ir N8 C7 0.8(3) . . . . ? C7 N8 N9 N10 -0.4(4) . . . . ? Ir N8 N9 N10 172.4(3) . . . . ? N8 N9 N10 C11 0.8(5) . . . . ? N8 N9 N10 C12 -179.6(4) . . . . ? N9 N10 C11 C7 -0.8(5) . . . . ? C12 N10 C11 C7 179.6(4) . . . . ? N8 C7 C11 N10 0.5(5) . . . . ? C6 C7 C11 N10 -173.7(5) . . . . ? C11 N10 C12 B13 74.9(6) . . . . ? N9 N10 C12 B13 -104.6(5) . . . . ? N10 C12 B13 F15 70.8(6) . . . . ? N10 C12 B13 F14 -52.0(6) . . . . ? N10 C12 B13 F16 -170.3(4) . . . . ? C52 Ir N21 C22 -95.4(4) . . . . ? C32 Ir N21 C22 178.0(4) . . . . ? N41 Ir N21 C22 -138.5(10) . . . . ? N8 Ir N21 C22 4.5(4) . . . . ? N1 Ir N21 C22 80.2(4) . . . . ? C52 Ir N21 C26 81.0(3) . . . . ? C32 Ir N21 C26 -5.5(3) . . . . ? N41 Ir N21 C26 37.9(12) . . . . ? N8 Ir N21 C26 -179.1(3) . . . . ? N1 Ir N21 C26 -103.3(3) . . . . ? C26 N21 C22 C23 -0.3(8) . . . . ? Ir N21 C22 C23 176.0(4) . . . . ? N21 C22 C23 C24 -0.4(10) . . . . ? C22 C23 C24 C25 0.1(11) . . . . ? C23 C24 C25 C26 1.0(11) . . . . ? C22 N21 C26 C25 1.3(7) . . . . ? Ir N21 C26 C25 -175.3(4) . . . . ? C22 N21 C26 C27 -179.1(4) . . . . ? Ir N21 C26 C27 4.3(5) . . . . ? C24 C25 C26 N21 -1.7(9) . . . . ? C24 C25 C26 C27 178.8(6) . . . . ? N21 C26 C27 C28 177.6(5) . . . . ? C25 C26 C27 C28 -2.8(9) . . . . ? N21 C26 C27 C32 0.4(6) . . . . ? C25 C26 C27 C32 179.9(5) . . . . ? C32 C27 C28 C29 1.0(8) . . . . ? C26 C27 C28 C29 -176.2(5) . . . . ? C32 C27 C28 F28 -178.5(4) . . . . ? C26 C27 C28 F28 4.2(8) . . . . ? F28 C28 C29 C30 179.3(5) . . . . ? C27 C28 C29 C30 -0.2(9) . . . . ? C28 C29 C30 F30 179.6(6) . . . . ? C28 C29 C30 C31 -1.1(10) . . . . ? F30 C30 C31 C32 -179.2(5) . . . . ? C29 C30 C31 C32 1.6(10) . . . . ? C30 C31 C32 C27 -0.6(8) . . . . ? C30 C31 C32 Ir -178.5(4) . . . . ? C28 C27 C32 C31 -0.6(7) . . . . ? C26 C27 C32 C31 177.0(4) . . . . ? C28 C27 C32 Ir 177.6(4) . . . . ? C26 C27 C32 Ir -4.9(5) . . . . ? C52 Ir C32 C31 88.9(4) . . . . ? N21 Ir C32 C31 -176.6(4) . . . . ? N41 Ir C32 C31 8.7(4) . . . . ? N8 Ir C32 C31 -120.7(12) . . . . ? N1 Ir C32 C31 -88.4(4) . . . . ? C52 Ir C32 C27 -89.1(3) . . . . ? N21 Ir C32 C27 5.4(3) . . . . ? N41 Ir C32 C27 -169.3(3) . . . . ? N8 Ir C32 C27 61.3(13) . . . . ? N1 Ir C32 C27 93.6(3) . . . . ? C52 Ir N41 C42 -178.2(4) . . . . ? C32 Ir N41 C42 -91.6(4) . . . . ? N21 Ir N41 C42 -134.4(10) . . . . ? N8 Ir N41 C42 82.4(4) . . . . ? N1 Ir N41 C42 6.5(4) . . . . ? C52 Ir N41 C46 -2.8(3) . . . . ? C32 Ir N41 C46 83.8(3) . . . . ? N21 Ir N41 C46 41.0(12) . . . . ? N8 Ir N41 C46 -102.2(3) . . . . ? N1 Ir N41 C46 -178.1(3) . . . . ? C46 N41 C42 C43 -0.5(7) . . . . ? Ir N41 C42 C43 174.8(4) . . . . ? N41 C42 C43 C44 0.4(8) . . . . ? C42 C43 C44 C45 0.1(8) . . . . ? C43 C44 C45 C46 -0.6(8) . . . . ? C42 N41 C46 C45 0.0(6) . . . . ? Ir N41 C46 C45 -175.7(3) . . . . ? C42 N41 C46 C47 178.8(4) . . . . ? Ir N41 C46 C47 3.1(4) . . . . ? C44 C45 C46 N41 0.5(7) . . . . ? C44 C45 C46 C47 -178.1(5) . . . . ? N41 C46 C47 C48 176.9(4) . . . . ? C45 C46 C47 C48 -4.3(7) . . . . ? N41 C46 C47 C52 -1.5(5) . . . . ? C45 C46 C47 C52 177.2(4) . . . . ? C52 C47 C48 F48 177.7(4) . . . . ? C46 C47 C48 F48 -0.8(7) . . . . ? C52 C47 C48 C49 -2.2(7) . . . . ? C46 C47 C48 C49 179.4(5) . . . . ? F48 C48 C49 C50 -178.4(4) . . . . ? C47 C48 C49 C50 1.5(8) . . . . ? C48 C49 C50 F50 -179.5(4) . . . . ? C48 C49 C50 C51 0.1(8) . . . . ? F50 C50 C51 C52 178.7(4) . . . . ? C49 C50 C51 C52 -0.9(8) . . . . ? C50 C51 C52 C47 0.2(6) . . . . ? C50 C51 C52 Ir -179.1(3) . . . . ? C48 C47 C52 C51 1.3(6) . . . . ? C46 C47 C52 C51 179.9(4) . . . . ? C48 C47 C52 Ir -179.4(3) . . . . ? C46 C47 C52 Ir -0.7(5) . . . . ? C32 Ir C52 C51 86.7(4) . . . . ? N21 Ir C52 C51 6.4(4) . . . . ? N41 Ir C52 C51 -178.9(4) . . . . ? N8 Ir C52 C51 -89.4(4) . . . . ? N1 Ir C52 C51 -121.6(15) . . . . ? C32 Ir C52 C47 -92.6(3) . . . . ? N21 Ir C52 C47 -172.9(3) . . . . ? N41 Ir C52 C47 1.8(3) . . . . ? N8 Ir C52 C47 91.3(3) . . . . ? N1 Ir C52 C47 59.1(16) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.980 _refine_diff_density_min -0.990 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 963444' ####################################################################### # # 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_fro5492 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 F4 Ir N7 O3 S' _chemical_formula_weight 880.88 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 22.5873(5) _cell_length_b 16.4337(4) _cell_length_c 8.5110(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.541(1) _cell_angle_gamma 90.00 _cell_volume 3131.90(13) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6997 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 4.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3517 _exptl_absorpt_correction_T_max 0.7480 _exptl_absorpt_process_details 'Denzo (Otwinowski, Boerk, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28704 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 27.78 _reflns_number_total 7307 _reflns_number_gt 5975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0460P)^2^+4.4798P] 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 7307 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Ir Ir 1.293440(5) 0.499924(7) 1.076984(15) 0.02453(6) Uani 1 1 d . . . N11 N 1.24059(12) 0.60377(17) 0.9811(3) 0.0273(6) Uani 1 1 d . . . C12 C 1.25875(17) 0.6628(2) 0.8898(5) 0.0365(8) Uani 1 1 d . . . H12 H 1.2981 0.6610 0.8655 0.044 Uiso 1 1 calc R . . C13 C 1.22253(18) 0.7258(2) 0.8300(5) 0.0401(9) Uani 1 1 d . . . H13 H 1.2368 0.7655 0.7649 0.048 Uiso 1 1 calc R . . C14 C 1.16464(17) 0.7300(2) 0.8672(5) 0.0407(9) Uani 1 1 d . . . H14 H 1.1388 0.7719 0.8262 0.049 Uiso 1 1 calc R . . C15 C 1.14559(16) 0.6713(2) 0.9655(5) 0.0353(8) Uani 1 1 d . . . H15 H 1.1071 0.6739 0.9956 0.042 Uiso 1 1 calc R . . C16 C 1.18416(14) 0.6083(2) 1.0195(4) 0.0290(7) Uani 1 1 d . . . C17 C 1.16778(14) 0.5412(2) 1.1154(4) 0.0296(7) Uani 1 1 d . . . C18 C 1.11457(17) 0.5135(2) 1.1551(5) 0.0332(8) Uani 1 1 d . . . H18 H 1.0770 0.5387 1.1349 0.040 Uiso 1 1 calc R . . N19 N 1.12802(12) 0.44256(18) 1.2294(4) 0.0311(6) Uani 1 1 d . . . N20 N 1.18646(12) 0.42370(17) 1.2361(3) 0.0305(6) Uani 1 1 d . . . N21 N 1.21022(13) 0.48547(17) 1.1675(4) 0.0271(6) Uani 1 1 d . . . C22 C 1.08523(15) 0.3813(2) 1.2723(4) 0.0356(8) Uani 1 1 d . . . H22A H 1.0655 0.4013 1.3607 0.043 Uiso 1 1 calc R . . H22B H 1.1064 0.3309 1.3058 0.043 Uiso 1 1 calc R . . C23 C 1.03866(15) 0.3647(2) 1.1287(4) 0.0347(8) Uani 1 1 d . . . H23A H 1.0106 0.3235 1.1571 0.042 Uiso 1 1 calc R . . H23B H 1.0160 0.4147 1.1008 0.042 Uiso 1 1 calc R . . C24 C 1.06637(15) 0.3353(2) 0.9844(4) 0.0350(8) Uani 1 1 d . . . H24A H 1.0726 0.2764 0.9925 0.042 Uiso 1 1 calc R . . H24B H 1.1055 0.3611 0.9846 0.042 Uiso 1 1 calc R . . S1 S 1.02147(4) 0.35747(6) 0.80324(11) 0.03452(19) Uani 1 1 d . . . O1 O 1.01541(12) 0.44569(17) 0.7994(3) 0.0448(6) Uani 1 1 d . . . O2 O 1.05370(12) 0.32665(18) 0.6788(3) 0.0469(7) Uani 1 1 d . . . O3 O 0.96418(11) 0.31697(19) 0.8099(4) 0.0478(7) Uani 1 1 d . . . N31 N 1.25785(12) 0.41538(18) 0.9162(4) 0.0302(6) Uani 1 1 d . . . C32 C 1.21955(16) 0.4333(2) 0.7867(4) 0.0371(8) Uani 1 1 d . . . H32 H 1.2129 0.4883 0.7594 0.045 Uiso 1 1 calc R . . C33 C 1.18958(17) 0.3747(3) 0.6923(5) 0.0426(9) Uani 1 1 d . . . H33 H 1.1628 0.3893 0.6027 0.051 Uiso 1 1 calc R . . C34 C 1.19957(17) 0.2942(3) 0.7317(5) 0.0417(9) Uani 1 1 d . . . H34 H 1.1790 0.2531 0.6702 0.050 Uiso 1 1 calc R . . C35 C 1.24011(17) 0.2741(2) 0.8624(5) 0.0378(8) Uani 1 1 d . . . H35 H 1.2475 0.2192 0.8894 0.045 Uiso 1 1 calc R . . C36 C 1.26981(15) 0.3358(2) 0.9538(4) 0.0303(7) Uani 1 1 d . . . C37 C 1.31548(15) 0.3265(2) 1.0919(4) 0.0309(7) Uani 1 1 d . . . C38 C 1.34161(16) 0.2539(2) 1.1482(5) 0.0367(8) Uani 1 1 d . . . F38 F 1.32211(11) 0.18200(13) 1.0822(3) 0.0478(6) Uani 1 1 d . . . C39 C 1.38770(16) 0.2501(2) 1.2724(5) 0.0402(9) Uani 1 1 d . . . H39 H 1.4053 0.2004 1.3076 0.048 Uiso 1 1 calc R . . C40 C 1.40614(16) 0.3223(3) 1.3407(5) 0.0395(9) Uani 1 1 d . . . F40 F 1.45108(10) 0.32078(16) 1.4633(3) 0.0541(6) Uani 1 1 d . . . C41 C 1.38148(15) 0.3967(2) 1.2948(4) 0.0332(7) Uani 1 1 d . . . H41 H 1.3954 0.4446 1.3478 0.040 Uiso 1 1 calc R . . C42 C 1.33569(14) 0.3998(2) 1.1689(4) 0.0277(7) Uani 1 1 d . . . N51 N 1.33468(12) 0.57621(17) 1.2456(4) 0.0295(6) Uani 1 1 d . . . C52 C 1.31334(17) 0.5933(2) 1.3818(4) 0.0388(8) Uani 1 1 d . . . H52 H 1.2768 0.5704 1.4007 0.047 Uiso 1 1 calc R . . C53 C 1.3437(2) 0.6437(3) 1.4951(5) 0.0502(10) Uani 1 1 d . . . H53 H 1.3278 0.6555 1.5893 0.060 Uiso 1 1 calc R . . C54 C 1.3978(2) 0.6764(3) 1.4673(5) 0.0527(11) Uani 1 1 d . . . H54 H 1.4193 0.7104 1.5432 0.063 Uiso 1 1 calc R . . C55 C 1.41989(19) 0.6591(3) 1.3295(5) 0.0464(10) Uani 1 1 d . . . H55 H 1.4566 0.6815 1.3105 0.056 Uiso 1 1 calc R . . C56 C 1.38835(15) 0.6083(2) 1.2162(4) 0.0335(8) Uani 1 1 d . . . C57 C 1.40560(14) 0.5821(2) 1.0651(4) 0.0328(7) Uani 1 1 d . . . C58 C 1.45705(16) 0.6056(2) 1.0007(5) 0.0434(9) Uani 1 1 d . . . F58 F 1.49477(11) 0.65963(17) 1.0820(4) 0.0654(8) Uani 1 1 d . . . C59 C 1.47146(18) 0.5769(3) 0.8602(6) 0.0497(10) Uani 1 1 d . . . H59 H 1.5062 0.5938 0.8198 0.060 Uiso 1 1 calc R . . C60 C 1.4326(2) 0.5220(3) 0.7808(6) 0.0470(10) Uani 1 1 d . . . F60 F 1.44703(17) 0.49256(18) 0.6418(4) 0.0706(10) Uani 1 1 d . . . C61 C 1.3814(2) 0.4966(2) 0.8339(6) 0.0378(9) Uani 1 1 d . . . H61 H 1.3563 0.4590 0.7747 0.045 Uiso 1 1 calc R . . C62 C 1.36657(15) 0.5266(2) 0.9761(5) 0.0321(7) Uani 1 1 d . . . N101 N 1.17537(19) 0.5790(3) 0.5234(5) 0.0636(11) Uani 1 1 d . . . C102 C 1.1281(2) 0.5861(3) 0.5500(5) 0.0482(10) Uani 1 1 d . . . C103 C 1.0670(2) 0.5950(4) 0.5842(6) 0.0650(14) Uani 1 1 d . . . H10A H 1.0395 0.5803 0.4913 0.097 Uiso 1 1 calc R . . H10B H 1.0601 0.6511 0.6126 0.097 Uiso 1 1 calc R . . H10C H 1.0607 0.5596 0.6717 0.097 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 Ir 0.01567(9) 0.02779(9) 0.02982(9) 0.00081(5) 0.00180(6) -0.00057(4) N11 0.0211(13) 0.0294(14) 0.0311(14) 0.0015(12) 0.0019(11) -0.0013(11) C12 0.0323(19) 0.0350(19) 0.042(2) 0.0049(16) 0.0030(15) -0.0022(15) C13 0.039(2) 0.0364(19) 0.045(2) 0.0109(17) 0.0050(17) -0.0016(16) C14 0.039(2) 0.0353(19) 0.046(2) 0.0022(16) -0.0042(17) 0.0062(15) C15 0.0243(16) 0.0349(18) 0.046(2) 0.0001(16) 0.0004(14) 0.0036(14) C16 0.0224(15) 0.0302(16) 0.0339(17) -0.0029(14) 0.0017(13) 0.0013(12) C17 0.0163(14) 0.0322(18) 0.0399(19) -0.0024(14) 0.0018(13) 0.0018(12) C18 0.0220(17) 0.0380(19) 0.039(2) 0.0006(15) 0.0024(15) 0.0025(13) N19 0.0200(13) 0.0366(15) 0.0368(15) 0.0013(13) 0.0041(11) -0.0001(11) N20 0.0190(13) 0.0350(15) 0.0376(15) 0.0036(12) 0.0041(11) 0.0003(11) N21 0.0128(13) 0.0335(14) 0.0351(16) 0.0028(12) 0.0036(11) -0.0014(10) C22 0.0255(17) 0.043(2) 0.0399(19) 0.0027(16) 0.0094(14) -0.0065(15) C23 0.0228(16) 0.0385(19) 0.043(2) -0.0021(16) 0.0068(14) -0.0040(14) C24 0.0229(16) 0.0393(19) 0.043(2) -0.0046(16) 0.0058(14) 0.0027(14) S1 0.0225(4) 0.0397(5) 0.0417(5) -0.0030(4) 0.0055(3) 0.0007(3) O1 0.0387(15) 0.0415(14) 0.0554(17) 0.0048(13) 0.0101(12) 0.0072(12) O2 0.0379(15) 0.0597(18) 0.0453(16) -0.0120(14) 0.0139(12) 0.0027(13) O3 0.0245(13) 0.0608(18) 0.0577(18) -0.0045(15) 0.0040(12) -0.0073(12) N31 0.0204(13) 0.0337(15) 0.0360(15) -0.0011(12) 0.0021(11) -0.0005(11) C32 0.0293(18) 0.043(2) 0.0373(19) -0.0009(16) -0.0024(14) -0.0001(15) C33 0.034(2) 0.054(2) 0.038(2) -0.0033(18) -0.0032(15) -0.0004(17) C34 0.0290(18) 0.052(2) 0.044(2) -0.0120(18) 0.0023(16) -0.0087(16) C35 0.0335(19) 0.0380(19) 0.043(2) -0.0049(16) 0.0078(16) -0.0050(15) C36 0.0226(15) 0.0339(18) 0.0349(18) -0.0002(14) 0.0056(13) -0.0017(13) C37 0.0240(16) 0.0363(17) 0.0328(17) 0.0022(14) 0.0058(13) 0.0022(13) C38 0.0289(17) 0.0342(18) 0.048(2) 0.0000(16) 0.0088(15) 0.0027(14) F38 0.0459(13) 0.0349(11) 0.0630(15) -0.0013(11) 0.0085(11) 0.0033(10) C39 0.0310(19) 0.0381(19) 0.052(2) 0.0091(17) 0.0086(16) 0.0103(15) C40 0.0204(16) 0.052(2) 0.045(2) 0.0094(19) 0.0003(14) 0.0057(16) F40 0.0351(12) 0.0606(15) 0.0602(15) 0.0105(12) -0.0174(11) 0.0068(11) C41 0.0216(16) 0.0385(19) 0.0388(19) 0.0034(16) 0.0016(14) 0.0011(14) C42 0.0193(15) 0.0320(17) 0.0325(17) 0.0070(14) 0.0056(13) 0.0000(12) N51 0.0228(14) 0.0298(14) 0.0353(15) -0.0026(12) 0.0010(11) 0.0000(11) C52 0.0354(19) 0.046(2) 0.0356(19) 0.0011(16) 0.0050(15) 0.0043(16) C53 0.059(3) 0.053(2) 0.037(2) -0.0101(19) 0.0013(19) 0.006(2) C54 0.057(3) 0.049(2) 0.047(2) -0.013(2) -0.014(2) -0.007(2) C55 0.034(2) 0.047(2) 0.055(3) -0.002(2) -0.0065(18) -0.0098(17) C56 0.0241(16) 0.0318(17) 0.042(2) -0.0013(15) -0.0044(14) -0.0063(13) C57 0.0182(15) 0.0363(18) 0.044(2) 0.0043(15) 0.0038(13) -0.0024(13) C58 0.0239(17) 0.045(2) 0.060(3) 0.0054(19) 0.0016(16) -0.0047(15) F58 0.0310(13) 0.0716(18) 0.094(2) -0.0041(16) 0.0088(13) -0.0238(12) C59 0.0289(19) 0.060(3) 0.063(3) 0.010(2) 0.0187(18) -0.0024(18) C60 0.038(2) 0.057(2) 0.050(2) 0.002(2) 0.0195(19) 0.006(2) F60 0.064(2) 0.095(3) 0.061(2) -0.0096(14) 0.0384(17) -0.0015(14) C61 0.034(2) 0.040(2) 0.042(2) -0.0007(15) 0.0130(18) -0.0004(14) C62 0.0215(16) 0.0340(17) 0.041(2) 0.0057(16) 0.0052(14) 0.0011(14) N101 0.055(3) 0.076(3) 0.061(3) 0.010(2) 0.015(2) 0.011(2) C102 0.054(3) 0.054(2) 0.036(2) 0.0044(18) 0.0025(18) 0.000(2) C103 0.044(3) 0.097(4) 0.054(3) 0.010(3) 0.003(2) -0.006(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 Ir C62 2.008(3) . ? Ir C42 2.009(3) . ? Ir N51 2.037(3) . ? Ir N31 2.040(3) . ? Ir N21 2.136(3) . ? Ir N11 2.179(3) . ? N11 C12 1.340(5) . ? N11 C16 1.359(4) . ? C12 C13 1.375(5) . ? C12 H12 0.9400 . ? C13 C14 1.387(6) . ? C13 H13 0.9400 . ? C14 C15 1.382(5) . ? C14 H14 0.9400 . ? C15 C16 1.391(5) . ? C15 H15 0.9400 . ? C16 C17 1.449(5) . ? C17 N21 1.357(4) . ? C17 C18 1.368(5) . ? C18 N19 1.342(5) . ? C18 H18 0.9400 . ? N19 N20 1.350(4) . ? N19 C22 1.474(4) . ? N20 N21 1.320(4) . ? C22 C23 1.529(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.528(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 S1 1.769(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? S1 O2 1.453(3) . ? S1 O1 1.456(3) . ? S1 O3 1.463(3) . ? N31 C32 1.341(4) . ? N31 C36 1.365(5) . ? C32 C33 1.374(5) . ? C32 H32 0.9400 . ? C33 C34 1.376(6) . ? C33 H33 0.9400 . ? C34 C35 1.385(5) . ? C34 H34 0.9400 . ? C35 C36 1.395(5) . ? C35 H35 0.9400 . ? C36 C37 1.467(5) . ? C37 C38 1.389(5) . ? C37 C42 1.417(5) . ? C38 F38 1.356(4) . ? C38 C39 1.384(5) . ? C39 C40 1.362(6) . ? C39 H39 0.9400 . ? C40 F40 1.357(4) . ? C40 C41 1.380(5) . ? C41 C42 1.389(5) . ? C41 H41 0.9400 . ? N51 C52 1.342(5) . ? N51 C56 1.375(4) . ? C52 C53 1.383(6) . ? C52 H52 0.9400 . ? C53 C54 1.384(7) . ? C53 H53 0.9400 . ? C54 C55 1.364(7) . ? C54 H54 0.9400 . ? C55 C56 1.397(5) . ? C55 H55 0.9400 . ? C56 C57 1.457(5) . ? C57 C58 1.402(5) . ? C57 C62 1.417(5) . ? C58 F58 1.356(5) . ? C58 C59 1.364(6) . ? C59 C60 1.373(7) . ? C59 H59 0.9400 . ? C60 F60 1.356(5) . ? C60 C61 1.362(6) . ? C61 C62 1.388(6) . ? C61 H61 0.9400 . ? N101 C102 1.126(6) . ? C102 C103 1.455(6) . ? C103 H10A 0.9700 . ? C103 H10B 0.9700 . ? C103 H10C 0.9700 . ? 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 C62 Ir C42 88.29(14) . . ? C62 Ir N51 80.85(14) . . ? C42 Ir N51 94.59(12) . . ? C62 Ir N31 97.81(14) . . ? C42 Ir N31 80.12(13) . . ? N51 Ir N31 174.60(11) . . ? C62 Ir N21 172.24(12) . . ? C42 Ir N21 99.44(12) . . ? N51 Ir N21 99.03(12) . . ? N31 Ir N21 83.01(12) . . ? C62 Ir N11 96.30(13) . . ? C42 Ir N11 175.17(11) . . ? N51 Ir N11 87.66(11) . . ? N31 Ir N11 97.70(11) . . ? N21 Ir N11 75.96(11) . . ? C12 N11 C16 117.9(3) . . ? C12 N11 Ir 126.1(2) . . ? C16 N11 Ir 116.0(2) . . ? N11 C12 C13 123.2(4) . . ? N11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C12 C13 C14 119.0(4) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 118.8(3) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 119.2(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 121.9(3) . . ? N11 C16 C17 114.2(3) . . ? C15 C16 C17 123.9(3) . . ? N21 C17 C18 107.5(3) . . ? N21 C17 C16 118.4(3) . . ? C18 C17 C16 133.6(3) . . ? N19 C18 C17 104.7(3) . . ? N19 C18 H18 127.7 . . ? C17 C18 H18 127.7 . . ? C18 N19 N20 112.3(3) . . ? C18 N19 C22 126.5(3) . . ? N20 N19 C22 120.1(3) . . ? N21 N20 N19 104.9(3) . . ? N20 N21 C17 110.6(3) . . ? N20 N21 Ir 132.3(2) . . ? C17 N21 Ir 115.1(2) . . ? N19 C22 C23 109.2(3) . . ? N19 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? N19 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? C24 C23 C22 112.8(3) . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? C22 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C23 C24 S1 112.8(2) . . ? C23 C24 H24A 109.0 . . ? S1 C24 H24A 109.0 . . ? C23 C24 H24B 109.0 . . ? S1 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? O2 S1 O1 112.67(18) . . ? O2 S1 O3 113.58(18) . . ? O1 S1 O3 111.88(17) . . ? O2 S1 C24 106.19(17) . . ? O1 S1 C24 105.43(17) . . ? O3 S1 C24 106.35(18) . . ? C32 N31 C36 119.3(3) . . ? C32 N31 Ir 123.8(2) . . ? C36 N31 Ir 116.6(2) . . ? N31 C32 C33 122.8(4) . . ? N31 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C32 C33 C34 118.6(4) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C33 C34 C35 119.7(4) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 119.5(4) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? N31 C36 C35 120.0(3) . . ? N31 C36 C37 112.6(3) . . ? C35 C36 C37 127.4(3) . . ? C38 C37 C42 118.3(3) . . ? C38 C37 C36 126.0(3) . . ? C42 C37 C36 115.6(3) . . ? F38 C38 C39 116.7(3) . . ? F38 C38 C37 120.3(3) . . ? C39 C38 C37 123.0(3) . . ? C40 C39 C38 116.4(3) . . ? C40 C39 H39 121.8 . . ? C38 C39 H39 121.8 . . ? F40 C40 C39 118.0(3) . . ? F40 C40 C41 117.8(4) . . ? C39 C40 C41 124.2(4) . . ? C40 C41 C42 118.8(4) . . ? C40 C41 H41 120.6 . . ? C42 C41 H41 120.6 . . ? C41 C42 C37 119.2(3) . . ? C41 C42 Ir 126.7(3) . . ? C37 C42 Ir 114.1(2) . . ? C52 N51 C56 120.1(3) . . ? C52 N51 Ir 123.7(2) . . ? C56 N51 Ir 116.1(2) . . ? N51 C52 C53 121.8(4) . . ? N51 C52 H52 119.1 . . ? C53 C52 H52 119.1 . . ? C52 C53 C54 118.7(4) . . ? C52 C53 H53 120.6 . . ? C54 C53 H53 120.6 . . ? C55 C54 C53 119.9(4) . . ? C55 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? C54 C55 C56 120.4(4) . . ? C54 C55 H55 119.8 . . ? C56 C55 H55 119.8 . . ? N51 C56 C55 119.1(4) . . ? N51 C56 C57 113.0(3) . . ? C55 C56 C57 127.9(3) . . ? C58 C57 C62 117.2(3) . . ? C58 C57 C56 126.5(3) . . ? C62 C57 C56 116.2(3) . . ? F58 C58 C59 117.9(3) . . ? F58 C58 C57 118.5(4) . . ? C59 C58 C57 123.6(4) . . ? C58 C59 C60 116.6(4) . . ? C58 C59 H59 121.7 . . ? C60 C59 H59 121.7 . . ? F60 C60 C61 119.5(4) . . ? F60 C60 C59 116.9(4) . . ? C61 C60 C59 123.6(4) . . ? C60 C61 C62 119.6(4) . . ? C60 C61 H61 120.2 . . ? C62 C61 H61 120.2 . . ? C61 C62 C57 119.4(3) . . ? C61 C62 Ir 127.0(3) . . ? C57 C62 Ir 113.7(3) . . ? N101 C102 C103 179.8(6) . . ? C102 C103 H10A 109.5 . . ? C102 C103 H10B 109.5 . . ? H10A C103 H10B 109.5 . . ? C102 C103 H10C 109.5 . . ? H10A C103 H10C 109.5 . . ? H10B C103 H10C 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 C62 Ir N11 C12 -1.9(3) . . . . ? C42 Ir N11 C12 -163.5(13) . . . . ? N51 Ir N11 C12 78.6(3) . . . . ? N31 Ir N11 C12 -100.7(3) . . . . ? N21 Ir N11 C12 178.5(3) . . . . ? C62 Ir N11 C16 178.5(2) . . . . ? C42 Ir N11 C16 16.9(15) . . . . ? N51 Ir N11 C16 -101.0(2) . . . . ? N31 Ir N11 C16 79.7(2) . . . . ? N21 Ir N11 C16 -1.1(2) . . . . ? C16 N11 C12 C13 -2.0(5) . . . . ? Ir N11 C12 C13 178.4(3) . . . . ? N11 C12 C13 C14 1.1(6) . . . . ? C12 C13 C14 C15 1.1(6) . . . . ? C13 C14 C15 C16 -2.3(6) . . . . ? C12 N11 C16 C15 0.7(5) . . . . ? Ir N11 C16 C15 -179.7(3) . . . . ? C12 N11 C16 C17 178.7(3) . . . . ? Ir N11 C16 C17 -1.7(4) . . . . ? C14 C15 C16 N11 1.5(5) . . . . ? C14 C15 C16 C17 -176.3(3) . . . . ? N11 C16 C17 N21 5.3(5) . . . . ? C15 C16 C17 N21 -176.8(3) . . . . ? N11 C16 C17 C18 -165.8(4) . . . . ? C15 C16 C17 C18 12.1(6) . . . . ? N21 C17 C18 N19 0.1(4) . . . . ? C16 C17 C18 N19 171.9(4) . . . . ? C17 C18 N19 N20 -0.9(4) . . . . ? C17 C18 N19 C22 -168.9(3) . . . . ? C18 N19 N20 N21 1.4(4) . . . . ? C22 N19 N20 N21 170.3(3) . . . . ? N19 N20 N21 C17 -1.4(4) . . . . ? N19 N20 N21 Ir -164.4(3) . . . . ? C18 C17 N21 N20 0.8(4) . . . . ? C16 C17 N21 N20 -172.4(3) . . . . ? C18 C17 N21 Ir 167.0(3) . . . . ? C16 C17 N21 Ir -6.3(4) . . . . ? C62 Ir N21 N20 163.1(9) . . . . ? C42 Ir N21 N20 -12.2(3) . . . . ? N51 Ir N21 N20 -108.4(3) . . . . ? N31 Ir N21 N20 66.5(3) . . . . ? N11 Ir N21 N20 166.3(3) . . . . ? C62 Ir N21 C17 0.7(11) . . . . ? C42 Ir N21 C17 -174.6(3) . . . . ? N51 Ir N21 C17 89.2(3) . . . . ? N31 Ir N21 C17 -95.9(3) . . . . ? N11 Ir N21 C17 3.9(2) . . . . ? C18 N19 C22 C23 48.2(5) . . . . ? N20 N19 C22 C23 -118.9(3) . . . . ? N19 C22 C23 C24 58.0(4) . . . . ? C22 C23 C24 S1 -154.3(3) . . . . ? C23 C24 S1 O2 179.6(3) . . . . ? C23 C24 S1 O1 59.8(3) . . . . ? C23 C24 S1 O3 -59.1(3) . . . . ? C62 Ir N31 C32 -90.2(3) . . . . ? C42 Ir N31 C32 -177.1(3) . . . . ? N51 Ir N31 C32 -165.5(11) . . . . ? N21 Ir N31 C32 82.0(3) . . . . ? N11 Ir N31 C32 7.3(3) . . . . ? C62 Ir N31 C36 96.5(3) . . . . ? C42 Ir N31 C36 9.6(2) . . . . ? N51 Ir N31 C36 21.2(13) . . . . ? N21 Ir N31 C36 -91.3(3) . . . . ? N11 Ir N31 C36 -166.0(2) . . . . ? C36 N31 C32 C33 2.7(6) . . . . ? Ir N31 C32 C33 -170.4(3) . . . . ? N31 C32 C33 C34 -0.5(6) . . . . ? C32 C33 C34 C35 -1.3(6) . . . . ? C33 C34 C35 C36 0.8(6) . . . . ? C32 N31 C36 C35 -3.2(5) . . . . ? Ir N31 C36 C35 170.4(3) . . . . ? C32 N31 C36 C37 176.1(3) . . . . ? Ir N31 C36 C37 -10.3(4) . . . . ? C34 C35 C36 N31 1.5(5) . . . . ? C34 C35 C36 C37 -177.6(3) . . . . ? N31 C36 C37 C38 -172.7(3) . . . . ? C35 C36 C37 C38 6.5(6) . . . . ? N31 C36 C37 C42 4.6(4) . . . . ? C35 C36 C37 C42 -176.2(3) . . . . ? C42 C37 C38 F38 177.5(3) . . . . ? C36 C37 C38 F38 -5.3(5) . . . . ? C42 C37 C38 C39 -2.2(5) . . . . ? C36 C37 C38 C39 175.0(3) . . . . ? F38 C38 C39 C40 -178.5(3) . . . . ? C37 C38 C39 C40 1.2(6) . . . . ? C38 C39 C40 F40 179.7(3) . . . . ? C38 C39 C40 C41 0.7(6) . . . . ? F40 C40 C41 C42 179.6(3) . . . . ? C39 C40 C41 C42 -1.4(6) . . . . ? C40 C41 C42 C37 0.3(5) . . . . ? C40 C41 C42 Ir -178.9(3) . . . . ? C38 C37 C42 C41 1.4(5) . . . . ? C36 C37 C42 C41 -176.1(3) . . . . ? C38 C37 C42 Ir -179.3(3) . . . . ? C36 C37 C42 Ir 3.2(4) . . . . ? C62 Ir C42 C41 74.4(3) . . . . ? N51 Ir C42 C41 -6.2(3) . . . . ? N31 Ir C42 C41 172.7(3) . . . . ? N21 Ir C42 C41 -106.2(3) . . . . ? N11 Ir C42 C41 -123.9(13) . . . . ? C62 Ir C42 C37 -104.8(3) . . . . ? N51 Ir C42 C37 174.5(2) . . . . ? N31 Ir C42 C37 -6.6(2) . . . . ? N21 Ir C42 C37 74.5(3) . . . . ? N11 Ir C42 C37 56.8(15) . . . . ? C62 Ir N51 C52 -177.3(3) . . . . ? C42 Ir N51 C52 -89.8(3) . . . . ? N31 Ir N51 C52 -101.3(12) . . . . ? N21 Ir N51 C52 10.5(3) . . . . ? N11 Ir N51 C52 85.9(3) . . . . ? C62 Ir N51 C56 0.2(3) . . . . ? C42 Ir N51 C56 87.7(2) . . . . ? N31 Ir N51 C56 76.3(12) . . . . ? N21 Ir N51 C56 -171.9(2) . . . . ? N11 Ir N51 C56 -96.5(2) . . . . ? C56 N51 C52 C53 0.7(5) . . . . ? Ir N51 C52 C53 178.2(3) . . . . ? N51 C52 C53 C54 -0.8(6) . . . . ? C52 C53 C54 C55 0.5(7) . . . . ? C53 C54 C55 C56 -0.3(7) . . . . ? C52 N51 C56 C55 -0.4(5) . . . . ? Ir N51 C56 C55 -178.0(3) . . . . ? C52 N51 C56 C57 178.6(3) . . . . ? Ir N51 C56 C57 1.0(4) . . . . ? C54 C55 C56 N51 0.2(6) . . . . ? C54 C55 C56 C57 -178.6(4) . . . . ? N51 C56 C57 C58 178.7(3) . . . . ? C55 C56 C57 C58 -2.5(6) . . . . ? N51 C56 C57 C62 -2.2(5) . . . . ? C55 C56 C57 C62 176.7(4) . . . . ? C62 C57 C58 F58 179.0(3) . . . . ? C56 C57 C58 F58 -1.9(6) . . . . ? C62 C57 C58 C59 -1.2(6) . . . . ? C56 C57 C58 C59 178.0(4) . . . . ? F58 C58 C59 C60 179.7(4) . . . . ? C57 C58 C59 C60 -0.1(6) . . . . ? C58 C59 C60 F60 -179.3(4) . . . . ? C58 C59 C60 C61 0.9(7) . . . . ? F60 C60 C61 C62 180.0(4) . . . . ? C59 C60 C61 C62 -0.2(7) . . . . ? C60 C61 C62 C57 -1.2(6) . . . . ? C60 C61 C62 Ir 179.0(3) . . . . ? C58 C57 C62 C61 1.8(5) . . . . ? C56 C57 C62 C61 -177.4(3) . . . . ? C58 C57 C62 Ir -178.4(3) . . . . ? C56 C57 C62 Ir 2.4(4) . . . . ? C42 Ir C62 C61 83.5(4) . . . . ? N51 Ir C62 C61 178.4(4) . . . . ? N31 Ir C62 C61 3.7(4) . . . . ? N21 Ir C62 C61 -91.9(10) . . . . ? N11 Ir C62 C61 -95.0(4) . . . . ? C42 Ir C62 C57 -96.3(3) . . . . ? N51 Ir C62 C57 -1.4(3) . . . . ? N31 Ir C62 C57 -176.1(3) . . . . ? N21 Ir C62 C57 88.3(10) . . . . ? N11 Ir C62 C57 85.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.098 _refine_diff_density_min -2.232 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 963445' ####################################################################### # # 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_fro5493 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H23 B F7 Ir N10' _chemical_formula_weight 883.61 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6423(1) _cell_length_b 13.1265(2) _cell_length_c 14.9287(2) _cell_angle_alpha 75.465(1) _cell_angle_beta 79.891(1) _cell_angle_gamma 88.149(1) _cell_volume 1613.78(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3622 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.818 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 4.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2831 _exptl_absorpt_correction_T_max 0.6777 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13509 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 27.90 _reflns_number_total 7432 _reflns_number_gt 7166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0542P)^2^+2.6034P] 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 7432 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.440900(13) 1.307128(9) 0.311811(8) 0.02499(6) Uani 1 1 d . . . N11 N 0.5585(4) 1.3569(3) 0.1670(2) 0.0297(6) Uani 1 1 d . . . C12 C 0.6406(5) 1.4468(3) 0.1280(3) 0.0360(8) Uani 1 1 d . . . H12 H 0.6549 1.4915 0.1664 0.043 Uiso 1 1 calc R . . C13 C 0.7055(6) 1.4764(4) 0.0329(3) 0.0471(10) Uani 1 1 d . . . H13 H 0.7635 1.5395 0.0075 0.056 Uiso 1 1 calc R . . C14 C 0.6834(6) 1.4117(4) -0.0231(3) 0.0519(12) Uani 1 1 d . . . H14 H 0.7263 1.4302 -0.0875 0.062 Uiso 1 1 calc R . . C15 C 0.5978(6) 1.3190(4) 0.0154(3) 0.0432(9) Uani 1 1 d . . . H15 H 0.5814 1.2741 -0.0223 0.052 Uiso 1 1 calc R . . C16 C 0.5371(4) 1.2940(3) 0.1101(3) 0.0308(7) Uani 1 1 d . . . C17 C 0.4441(4) 1.1991(3) 0.1583(3) 0.0298(7) Uani 1 1 d . . . C18 C 0.4095(5) 1.1097(3) 0.1345(3) 0.0354(8) Uani 1 1 d . . . H18 H 0.4416 1.0926 0.0766 0.042 Uiso 1 1 calc R . . N19 N 0.3193(4) 1.0517(3) 0.2119(2) 0.0339(7) Uani 1 1 d . . . N20 N 0.2971(4) 1.0998(2) 0.2824(2) 0.0318(6) Uani 1 1 d . . . N21 N 0.3745(4) 1.1901(2) 0.2487(2) 0.0261(6) Uani 1 1 d . . . C22 C 0.2510(7) 0.9460(3) 0.2268(3) 0.0469(11) Uani 1 1 d . . . H22A H 0.1424 0.9452 0.2598 0.056 Uiso 1 1 calc R . . H22B H 0.3098 0.8950 0.2676 0.056 Uiso 1 1 calc R . . B1 B 0.2514(7) 0.9085(4) 0.1313(4) 0.0443(11) Uani 1 1 d . . . F1 F 0.4030(5) 0.8951(3) 0.0852(3) 0.0782(11) Uani 1 1 d . . . F2 F 0.1812(5) 0.9842(3) 0.0681(3) 0.0764(11) Uani 1 1 d . . . F3 F 0.1689(5) 0.8136(2) 0.1530(3) 0.0713(10) Uani 1 1 d . . . N31 N 0.6071(4) 1.2059(3) 0.3651(3) 0.0371(7) Uani 1 1 d . . . C32 C 0.7524(5) 1.1990(4) 0.3172(4) 0.0505(11) Uani 1 1 d . . . H32 H 0.7762 1.2353 0.2535 0.061 Uiso 1 1 calc R . . C33 C 0.8676(7) 1.1400(6) 0.3588(6) 0.077(2) Uani 1 1 d . . . H33 H 0.9688 1.1356 0.3246 0.092 Uiso 1 1 calc R . . C34 C 0.8293(10) 1.0879(7) 0.4523(7) 0.092(3) Uani 1 1 d . . . H34 H 0.9061 1.0480 0.4826 0.110 Uiso 1 1 calc R . . C35 C 0.6808(9) 1.0933(5) 0.5020(5) 0.0711(18) Uani 1 1 d . . . H35 H 0.6554 1.0566 0.5655 0.085 Uiso 1 1 calc R . . C36 C 0.5698(6) 1.1534(3) 0.4573(3) 0.0451(10) Uani 1 1 d . . . C37 C 0.4097(6) 1.1724(3) 0.4988(3) 0.0422(9) Uani 1 1 d . . . C38 C 0.3310(8) 1.1258(4) 0.5891(3) 0.0575(14) Uani 1 1 d . . . F38 F 0.4085(6) 1.0537(3) 0.6478(2) 0.0858(13) Uani 1 1 d . . . N39 N 0.1866(7) 1.1426(4) 0.6257(3) 0.0633(13) Uani 1 1 d . . . C40 C 0.1123(7) 1.2124(4) 0.5694(3) 0.0525(12) Uani 1 1 d . . . F40 F -0.0370(5) 1.2291(3) 0.6065(3) 0.0770(11) Uani 1 1 d . . . C41 C 0.1699(5) 1.2658(3) 0.4785(3) 0.0397(9) Uani 1 1 d . . . H41 H 0.1078 1.3143 0.4429 0.048 Uiso 1 1 calc R . . C42 C 0.3238(5) 1.2455(3) 0.4411(3) 0.0319(7) Uani 1 1 d . . . N51 N 0.2733(4) 1.4172(2) 0.2792(2) 0.0295(6) Uani 1 1 d . . . C52 C 0.1471(4) 1.4002(3) 0.2439(3) 0.0359(8) Uani 1 1 d . . . H52 H 0.1366 1.3352 0.2296 0.043 Uiso 1 1 calc R . . C53 C 0.0316(6) 1.4748(4) 0.2277(4) 0.0488(11) Uani 1 1 d . . . H53 H -0.0561 1.4609 0.2031 0.059 Uiso 1 1 calc R . . C54 C 0.0482(6) 1.5694(4) 0.2486(4) 0.0541(12) Uani 1 1 d . . . H54 H -0.0293 1.6210 0.2388 0.065 Uiso 1 1 calc R . . C55 C 0.1782(6) 1.5892(4) 0.2837(3) 0.0479(10) Uani 1 1 d . . . H55 H 0.1903 1.6544 0.2971 0.057 Uiso 1 1 calc R . . C56 C 0.2919(5) 1.5116(3) 0.2994(3) 0.0350(8) Uani 1 1 d . . . C57 C 0.4324(5) 1.5174(3) 0.3385(3) 0.0361(8) Uani 1 1 d . . . C58 C 0.4897(7) 1.6045(4) 0.3614(3) 0.0493(11) Uani 1 1 d . . . F58 F 0.4107(5) 1.6949(2) 0.3466(3) 0.0742(10) Uani 1 1 d . . . N59 N 0.6158(6) 1.6080(3) 0.3969(3) 0.0527(10) Uani 1 1 d . . . C60 C 0.6930(6) 1.5203(4) 0.4124(3) 0.0496(11) Uani 1 1 d . . . F60 F 0.8221(4) 1.5227(3) 0.4510(3) 0.0681(9) Uani 1 1 d . . . C61 C 0.6561(5) 1.4272(4) 0.3932(3) 0.0420(9) Uani 1 1 d . . . H61 H 0.7199 1.3676 0.4055 0.050 Uiso 1 1 calc R . . C62 C 0.5216(5) 1.4250(3) 0.3552(3) 0.0318(7) Uani 1 1 d . . . N101 N 0.7175(12) 0.6780(6) 0.1403(7) 0.122(3) Uani 1 1 d . . . C102 C 0.7281(8) 0.7598(5) 0.1436(4) 0.0642(14) Uani 1 1 d . . . C103 C 0.7464(10) 0.8661(6) 0.1486(5) 0.080(2) Uani 1 1 d . . . H10A H 0.6648 0.8817 0.1966 0.120 Uiso 1 1 calc R . . H10B H 0.7382 0.9136 0.0883 0.120 Uiso 1 1 calc R . . H10C H 0.8486 0.8750 0.1641 0.120 Uiso 1 1 calc R . . N111 N 0.9616(13) 0.7220(10) 0.8925(7) 0.151(4) Uani 1 1 d . . . C112 C 1.0188(9) 0.7847(7) 0.9102(5) 0.082(2) Uani 1 1 d . . . C113 C 1.0984(12) 0.8627(10) 0.9338(12) 0.170(7) Uani 1 1 d . . . H11A H 1.1524 0.8307 0.9855 0.255 Uiso 1 1 calc R . . H11B H 1.0236 0.9135 0.9524 0.255 Uiso 1 1 calc R . . H11C H 1.1744 0.8980 0.8799 0.255 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 Ir 0.02758(8) 0.01995(8) 0.02653(8) -0.00434(5) -0.00405(5) -0.00140(5) N11 0.0285(14) 0.0251(14) 0.0338(15) -0.0053(12) -0.0033(12) -0.0026(11) C12 0.0386(19) 0.0279(18) 0.0378(19) -0.0048(15) -0.0005(15) -0.0079(15) C13 0.053(3) 0.036(2) 0.043(2) -0.0018(18) 0.0062(19) -0.0150(19) C14 0.062(3) 0.048(3) 0.035(2) -0.0019(19) 0.010(2) -0.016(2) C15 0.053(2) 0.040(2) 0.0327(19) -0.0101(16) 0.0039(17) -0.0084(19) C16 0.0310(17) 0.0265(16) 0.0319(17) -0.0053(13) 0.0006(13) -0.0029(13) C17 0.0319(17) 0.0251(16) 0.0310(16) -0.0051(13) -0.0040(13) -0.0022(13) C18 0.043(2) 0.0285(17) 0.0343(18) -0.0090(14) -0.0042(15) -0.0057(15) N19 0.0432(18) 0.0247(15) 0.0325(15) -0.0052(12) -0.0045(13) -0.0074(13) N20 0.0366(16) 0.0242(14) 0.0323(15) -0.0032(11) -0.0052(12) -0.0038(12) N21 0.0280(14) 0.0206(13) 0.0289(14) -0.0047(11) -0.0045(11) -0.0031(11) C22 0.072(3) 0.0253(19) 0.040(2) -0.0030(16) -0.006(2) -0.0175(19) B1 0.063(3) 0.023(2) 0.050(3) -0.0087(18) -0.019(2) -0.006(2) F1 0.079(2) 0.071(2) 0.093(3) -0.048(2) 0.002(2) -0.0024(19) F2 0.118(3) 0.0453(17) 0.078(2) -0.0096(16) -0.058(2) -0.0008(18) F3 0.111(3) 0.0365(15) 0.069(2) -0.0100(14) -0.022(2) -0.0303(17) N31 0.0366(17) 0.0305(16) 0.0476(19) -0.0092(14) -0.0188(15) 0.0071(13) C32 0.037(2) 0.043(2) 0.077(3) -0.020(2) -0.017(2) 0.0103(18) C33 0.046(3) 0.068(4) 0.124(6) -0.031(4) -0.030(4) 0.023(3) C34 0.090(5) 0.077(5) 0.125(7) -0.025(5) -0.067(5) 0.041(4) C35 0.090(5) 0.055(3) 0.077(4) -0.008(3) -0.051(4) 0.023(3) C36 0.063(3) 0.0304(19) 0.048(2) -0.0085(17) -0.029(2) 0.0070(18) C37 0.070(3) 0.0266(18) 0.0280(17) -0.0011(14) -0.0112(18) -0.0040(18) C38 0.102(4) 0.035(2) 0.033(2) -0.0003(17) -0.018(2) 0.002(3) F38 0.145(4) 0.063(2) 0.0393(16) 0.0111(15) -0.026(2) 0.015(2) N39 0.108(4) 0.041(2) 0.0331(19) -0.0042(17) 0.006(2) -0.010(2) C40 0.073(3) 0.038(2) 0.039(2) -0.0114(18) 0.016(2) -0.016(2) F40 0.084(2) 0.061(2) 0.066(2) -0.0144(16) 0.0422(18) -0.0139(18) C41 0.049(2) 0.0305(19) 0.0359(19) -0.0091(15) 0.0058(17) -0.0100(16) C42 0.045(2) 0.0245(16) 0.0255(15) -0.0075(13) -0.0022(14) -0.0055(14) N51 0.0304(14) 0.0204(13) 0.0326(15) -0.0001(11) -0.0015(12) 0.0010(11) C52 0.0276(17) 0.0337(19) 0.042(2) 0.0005(16) -0.0082(15) 0.0000(14) C53 0.038(2) 0.046(3) 0.054(3) 0.003(2) -0.0083(19) 0.0082(19) C54 0.047(3) 0.050(3) 0.054(3) -0.002(2) 0.001(2) 0.023(2) C55 0.060(3) 0.029(2) 0.048(2) -0.0053(17) -0.002(2) 0.0152(19) C56 0.047(2) 0.0228(16) 0.0305(17) -0.0032(13) 0.0010(15) 0.0015(15) C57 0.047(2) 0.0269(17) 0.0323(17) -0.0093(14) 0.0026(15) -0.0041(15) C58 0.071(3) 0.029(2) 0.049(2) -0.0152(18) -0.002(2) -0.007(2) F58 0.104(3) 0.0307(15) 0.097(3) -0.0290(16) -0.026(2) 0.0074(16) N59 0.065(3) 0.043(2) 0.054(2) -0.0238(19) 0.000(2) -0.017(2) C60 0.047(2) 0.061(3) 0.047(2) -0.028(2) -0.0007(19) -0.019(2) F60 0.0574(18) 0.087(2) 0.076(2) -0.0435(19) -0.0155(16) -0.0226(17) C61 0.039(2) 0.045(2) 0.047(2) -0.0198(19) -0.0052(17) -0.0080(17) C62 0.0372(18) 0.0280(17) 0.0319(17) -0.0116(14) -0.0029(14) -0.0075(14) N101 0.161(8) 0.054(4) 0.159(8) -0.029(4) -0.045(7) -0.015(4) C102 0.072(4) 0.057(3) 0.060(3) -0.008(3) -0.011(3) -0.011(3) C103 0.107(6) 0.063(4) 0.078(4) -0.020(3) -0.029(4) -0.008(4) N111 0.151(8) 0.184(11) 0.146(8) -0.094(8) -0.014(7) -0.067(8) C112 0.074(4) 0.113(6) 0.083(5) -0.063(5) -0.018(3) 0.003(4) C113 0.103(7) 0.169(11) 0.340(19) -0.204(13) -0.115(10) 0.059(7) _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 Ir C42 1.996(4) . ? Ir C62 2.009(4) . ? Ir N51 2.045(3) . ? Ir N31 2.051(3) . ? Ir N21 2.132(3) . ? Ir N11 2.167(3) . ? N11 C12 1.342(5) . ? N11 C16 1.360(5) . ? C12 C13 1.394(6) . ? C12 H12 0.9400 . ? C13 C14 1.371(7) . ? C13 H13 0.9400 . ? C14 C15 1.384(6) . ? C14 H14 0.9400 . ? C15 C16 1.379(5) . ? C15 H15 0.9400 . ? C16 C17 1.459(5) . ? C17 N21 1.356(5) . ? C17 C18 1.364(5) . ? C18 N19 1.343(5) . ? C18 H18 0.9400 . ? N19 N20 1.341(4) . ? N19 C22 1.475(5) . ? N20 N21 1.319(4) . ? C22 B1 1.621(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? B1 F2 1.392(6) . ? B1 F3 1.392(5) . ? B1 F1 1.396(7) . ? N31 C32 1.344(6) . ? N31 C36 1.364(6) . ? C32 C33 1.380(8) . ? C32 H32 0.9400 . ? C33 C34 1.377(12) . ? C33 H33 0.9400 . ? C34 C35 1.374(12) . ? C34 H34 0.9400 . ? C35 C36 1.378(7) . ? C35 H35 0.9400 . ? C36 C37 1.454(7) . ? C37 C38 1.394(6) . ? C37 C42 1.407(6) . ? C38 N39 1.307(9) . ? C38 F38 1.364(6) . ? N39 C40 1.312(8) . ? C40 F40 1.346(6) . ? C40 C41 1.375(6) . ? C41 C42 1.394(6) . ? C41 H41 0.9400 . ? N51 C52 1.339(5) . ? N51 C56 1.368(5) . ? C52 C53 1.384(6) . ? C52 H52 0.9400 . ? C53 C54 1.372(8) . ? C53 H53 0.9400 . ? C54 C55 1.378(8) . ? C54 H54 0.9400 . ? C55 C56 1.397(6) . ? C55 H55 0.9400 . ? C56 C57 1.448(6) . ? C57 C58 1.402(6) . ? C57 C62 1.407(6) . ? C58 N59 1.299(7) . ? C58 F58 1.339(6) . ? N59 C60 1.302(8) . ? C60 F60 1.347(6) . ? C60 C61 1.382(6) . ? C61 C62 1.384(6) . ? C61 H61 0.9400 . ? N101 C102 1.095(9) . ? C102 C103 1.431(9) . ? C103 H10A 0.9700 . ? C103 H10B 0.9700 . ? C103 H10C 0.9700 . ? N111 C112 1.083(11) . ? C112 C113 1.399(10) . ? C113 H11A 0.9700 . ? C113 H11B 0.9700 . ? C113 H11C 0.9700 . ? 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 C42 Ir C62 90.54(15) . . ? C42 Ir N51 93.63(15) . . ? C62 Ir N51 80.32(15) . . ? C42 Ir N31 80.14(17) . . ? C62 Ir N31 91.98(16) . . ? N51 Ir N31 170.10(13) . . ? C42 Ir N21 96.84(13) . . ? C62 Ir N21 172.58(13) . . ? N51 Ir N21 99.89(13) . . ? N31 Ir N21 88.56(13) . . ? C42 Ir N11 172.84(12) . . ? C62 Ir N11 96.59(14) . . ? N51 Ir N11 88.18(12) . . ? N31 Ir N11 98.95(14) . . ? N21 Ir N11 76.02(12) . . ? C12 N11 C16 118.0(3) . . ? C12 N11 Ir 125.6(3) . . ? C16 N11 Ir 116.3(2) . . ? N11 C12 C13 122.3(4) . . ? N11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C12 118.8(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 119.9(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 118.6(4) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N11 C16 C15 122.5(4) . . ? N11 C16 C17 114.0(3) . . ? C15 C16 C17 123.5(4) . . ? N21 C17 C18 107.6(3) . . ? N21 C17 C16 117.7(3) . . ? C18 C17 C16 134.8(4) . . ? N19 C18 C17 104.8(3) . . ? N19 C18 H18 127.6 . . ? C17 C18 H18 127.6 . . ? N20 N19 C18 112.0(3) . . ? N20 N19 C22 119.7(3) . . ? C18 N19 C22 128.3(3) . . ? N21 N20 N19 105.4(3) . . ? N20 N21 C17 110.2(3) . . ? N20 N21 Ir 133.4(2) . . ? C17 N21 Ir 115.4(2) . . ? N19 C22 B1 114.5(3) . . ? N19 C22 H22A 108.6 . . ? B1 C22 H22A 108.6 . . ? N19 C22 H22B 108.6 . . ? B1 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? F2 B1 F3 109.6(4) . . ? F2 B1 F1 106.4(5) . . ? F3 B1 F1 108.8(4) . . ? F2 B1 C22 110.1(4) . . ? F3 B1 C22 109.2(4) . . ? F1 B1 C22 112.6(4) . . ? C32 N31 C36 120.0(4) . . ? C32 N31 Ir 123.3(3) . . ? C36 N31 Ir 116.2(3) . . ? N31 C32 C33 121.9(6) . . ? N31 C32 H32 119.1 . . ? C33 C32 H32 119.1 . . ? C34 C33 C32 117.7(6) . . ? C34 C33 H33 121.1 . . ? C32 C33 H33 121.1 . . ? C35 C34 C33 121.2(6) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C34 C35 C36 119.0(6) . . ? C34 C35 H35 120.5 . . ? C36 C35 H35 120.5 . . ? N31 C36 C35 120.2(5) . . ? N31 C36 C37 112.7(4) . . ? C35 C36 C37 127.0(5) . . ? C38 C37 C42 116.2(5) . . ? C38 C37 C36 127.5(5) . . ? C42 C37 C36 116.3(4) . . ? N39 C38 F38 114.3(5) . . ? N39 C38 C37 127.1(5) . . ? F38 C38 C37 118.6(6) . . ? C38 N39 C40 114.3(4) . . ? N39 C40 F40 114.4(4) . . ? N39 C40 C41 126.9(5) . . ? F40 C40 C41 118.7(5) . . ? C40 C41 C42 117.5(5) . . ? C40 C41 H41 121.2 . . ? C42 C41 H41 121.2 . . ? C41 C42 C37 118.0(4) . . ? C41 C42 Ir 127.7(3) . . ? C37 C42 Ir 114.4(3) . . ? C52 N51 C56 119.8(3) . . ? C52 N51 Ir 124.1(3) . . ? C56 N51 Ir 116.0(3) . . ? N51 C52 C53 122.3(4) . . ? N51 C52 H52 118.8 . . ? C53 C52 H52 118.8 . . ? C54 C53 C52 118.4(5) . . ? C54 C53 H53 120.8 . . ? C52 C53 H53 120.8 . . ? C53 C54 C55 120.2(4) . . ? C53 C54 H54 119.9 . . ? C55 C54 H54 119.9 . . ? C54 C55 C56 119.6(4) . . ? C54 C55 H55 120.2 . . ? C56 C55 H55 120.2 . . ? N51 C56 C55 119.6(4) . . ? N51 C56 C57 113.2(3) . . ? C55 C56 C57 127.1(4) . . ? C58 C57 C62 116.3(4) . . ? C58 C57 C56 127.3(4) . . ? C62 C57 C56 116.4(3) . . ? N59 C58 F58 114.3(4) . . ? N59 C58 C57 126.5(5) . . ? F58 C58 C57 119.2(5) . . ? C58 N59 C60 114.9(4) . . ? N59 C60 F60 115.2(4) . . ? N59 C60 C61 126.9(5) . . ? F60 C60 C61 117.9(5) . . ? C60 C61 C62 117.4(5) . . ? C60 C61 H61 121.3 . . ? C62 C61 H61 121.3 . . ? C61 C62 C57 118.1(4) . . ? C61 C62 Ir 127.9(3) . . ? C57 C62 Ir 113.9(3) . . ? N101 C102 C103 178.3(9) . . ? C102 C103 H10A 109.5 . . ? C102 C103 H10B 109.5 . . ? H10A C103 H10B 109.5 . . ? C102 C103 H10C 109.5 . . ? H10A C103 H10C 109.5 . . ? H10B C103 H10C 109.5 . . ? N111 C112 C113 177.4(12) . . ? C112 C113 H11A 109.5 . . ? C112 C113 H11B 109.5 . . ? H11A C113 H11B 109.5 . . ? C112 C113 H11C 109.5 . . ? H11A C113 H11C 109.5 . . ? H11B C113 H11C 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 C42 Ir N11 C12 178.6(10) . . . . ? C62 Ir N11 C12 -6.2(4) . . . . ? N51 Ir N11 C12 73.9(3) . . . . ? N31 Ir N11 C12 -99.2(3) . . . . ? N21 Ir N11 C12 174.5(4) . . . . ? C42 Ir N11 C16 3.3(12) . . . . ? C62 Ir N11 C16 178.5(3) . . . . ? N51 Ir N11 C16 -101.5(3) . . . . ? N31 Ir N11 C16 85.4(3) . . . . ? N21 Ir N11 C16 -0.8(3) . . . . ? C16 N11 C12 C13 -1.0(6) . . . . ? Ir N11 C12 C13 -176.2(4) . . . . ? N11 C12 C13 C14 0.6(8) . . . . ? C12 C13 C14 C15 0.0(8) . . . . ? C13 C14 C15 C16 -0.2(8) . . . . ? C12 N11 C16 C15 0.7(6) . . . . ? Ir N11 C16 C15 176.4(3) . . . . ? C12 N11 C16 C17 -178.9(3) . . . . ? Ir N11 C16 C17 -3.3(4) . . . . ? C14 C15 C16 N11 -0.1(7) . . . . ? C14 C15 C16 C17 179.5(4) . . . . ? N11 C16 C17 N21 7.9(5) . . . . ? C15 C16 C17 N21 -171.8(4) . . . . ? N11 C16 C17 C18 -170.4(4) . . . . ? C15 C16 C17 C18 9.9(7) . . . . ? N21 C17 C18 N19 0.5(4) . . . . ? C16 C17 C18 N19 178.9(4) . . . . ? C17 C18 N19 N20 -0.4(5) . . . . ? C17 C18 N19 C22 -178.5(4) . . . . ? C18 N19 N20 N21 0.1(4) . . . . ? C22 N19 N20 N21 178.4(4) . . . . ? N19 N20 N21 C17 0.2(4) . . . . ? N19 N20 N21 Ir -168.0(3) . . . . ? C18 C17 N21 N20 -0.4(4) . . . . ? C16 C17 N21 N20 -179.1(3) . . . . ? C18 C17 N21 Ir 170.1(3) . . . . ? C16 C17 N21 Ir -8.7(4) . . . . ? C42 Ir N21 N20 -6.7(4) . . . . ? C62 Ir N21 N20 167.4(10) . . . . ? N51 Ir N21 N20 -101.7(3) . . . . ? N31 Ir N21 N20 73.1(3) . . . . ? N11 Ir N21 N20 172.7(4) . . . . ? C42 Ir N21 C17 -174.4(3) . . . . ? C62 Ir N21 C17 -0.2(11) . . . . ? N51 Ir N21 C17 90.7(3) . . . . ? N31 Ir N21 C17 -94.5(3) . . . . ? N11 Ir N21 C17 5.1(3) . . . . ? N20 N19 C22 B1 166.5(4) . . . . ? C18 N19 C22 B1 -15.5(7) . . . . ? N19 C22 B1 F2 -53.0(6) . . . . ? N19 C22 B1 F3 -173.4(4) . . . . ? N19 C22 B1 F1 65.6(6) . . . . ? C42 Ir N31 C32 -176.5(4) . . . . ? C62 Ir N31 C32 -86.3(4) . . . . ? N51 Ir N31 C32 -125.0(7) . . . . ? N21 Ir N31 C32 86.3(4) . . . . ? N11 Ir N31 C32 10.7(4) . . . . ? C42 Ir N31 C36 -4.1(3) . . . . ? C62 Ir N31 C36 86.1(3) . . . . ? N51 Ir N31 C36 47.5(9) . . . . ? N21 Ir N31 C36 -101.3(3) . . . . ? N11 Ir N31 C36 -176.9(3) . . . . ? C36 N31 C32 C33 -0.4(7) . . . . ? Ir N31 C32 C33 171.8(5) . . . . ? N31 C32 C33 C34 -0.2(10) . . . . ? C32 C33 C34 C35 0.9(12) . . . . ? C33 C34 C35 C36 -1.0(12) . . . . ? C32 N31 C36 C35 0.3(7) . . . . ? Ir N31 C36 C35 -172.4(4) . . . . ? C32 N31 C36 C37 178.1(4) . . . . ? Ir N31 C36 C37 5.4(5) . . . . ? C34 C35 C36 N31 0.4(9) . . . . ? C34 C35 C36 C37 -177.1(6) . . . . ? N31 C36 C37 C38 175.3(4) . . . . ? C35 C36 C37 C38 -7.0(8) . . . . ? N31 C36 C37 C42 -4.1(5) . . . . ? C35 C36 C37 C42 173.6(5) . . . . ? C42 C37 C38 N39 0.0(8) . . . . ? C36 C37 C38 N39 -179.4(5) . . . . ? C42 C37 C38 F38 179.4(4) . . . . ? C36 C37 C38 F38 0.0(8) . . . . ? F38 C38 N39 C40 179.7(5) . . . . ? C37 C38 N39 C40 -0.8(8) . . . . ? C38 N39 C40 F40 179.4(5) . . . . ? C38 N39 C40 C41 1.1(8) . . . . ? N39 C40 C41 C42 -0.5(7) . . . . ? F40 C40 C41 C42 -178.7(4) . . . . ? C40 C41 C42 C37 -0.4(6) . . . . ? C40 C41 C42 Ir 178.8(3) . . . . ? C38 C37 C42 C41 0.6(6) . . . . ? C36 C37 C42 C41 -179.9(4) . . . . ? C38 C37 C42 Ir -178.7(3) . . . . ? C36 C37 C42 Ir 0.8(5) . . . . ? C62 Ir C42 C41 90.5(4) . . . . ? N51 Ir C42 C41 10.2(4) . . . . ? N31 Ir C42 C41 -177.6(4) . . . . ? N21 Ir C42 C41 -90.3(3) . . . . ? N11 Ir C42 C41 -94.2(11) . . . . ? C62 Ir C42 C37 -90.3(3) . . . . ? N51 Ir C42 C37 -170.6(3) . . . . ? N31 Ir C42 C37 1.7(3) . . . . ? N21 Ir C42 C37 89.0(3) . . . . ? N11 Ir C42 C37 85.0(11) . . . . ? C42 Ir N51 C52 -86.8(3) . . . . ? C62 Ir N51 C52 -176.8(3) . . . . ? N31 Ir N51 C52 -137.4(7) . . . . ? N21 Ir N51 C52 10.8(3) . . . . ? N11 Ir N51 C52 86.2(3) . . . . ? C42 Ir N51 C56 90.3(3) . . . . ? C62 Ir N51 C56 0.4(3) . . . . ? N31 Ir N51 C56 39.7(8) . . . . ? N21 Ir N51 C56 -172.1(3) . . . . ? N11 Ir N51 C56 -96.6(3) . . . . ? C56 N51 C52 C53 -0.8(6) . . . . ? Ir N51 C52 C53 176.2(3) . . . . ? N51 C52 C53 C54 0.2(7) . . . . ? C52 C53 C54 C55 0.7(7) . . . . ? C53 C54 C55 C56 -1.0(7) . . . . ? C52 N51 C56 C55 0.5(6) . . . . ? Ir N51 C56 C55 -176.7(3) . . . . ? C52 N51 C56 C57 179.0(3) . . . . ? Ir N51 C56 C57 1.8(4) . . . . ? C54 C55 C56 N51 0.4(6) . . . . ? C54 C55 C56 C57 -177.9(4) . . . . ? N51 C56 C57 C58 176.0(4) . . . . ? C55 C56 C57 C58 -5.6(7) . . . . ? N51 C56 C57 C62 -3.9(5) . . . . ? C55 C56 C57 C62 174.4(4) . . . . ? C62 C57 C58 N59 -0.4(7) . . . . ? C56 C57 C58 N59 179.6(4) . . . . ? C62 C57 C58 F58 179.6(4) . . . . ? C56 C57 C58 F58 -0.4(7) . . . . ? F58 C58 N59 C60 179.5(4) . . . . ? C57 C58 N59 C60 -0.5(8) . . . . ? C58 N59 C60 F60 -178.7(4) . . . . ? C58 N59 C60 C61 1.5(8) . . . . ? N59 C60 C61 C62 -1.3(7) . . . . ? F60 C60 C61 C62 178.8(4) . . . . ? C60 C61 C62 C57 0.2(6) . . . . ? C60 C61 C62 Ir 175.9(3) . . . . ? C58 C57 C62 C61 0.5(6) . . . . ? C56 C57 C62 C61 -179.5(4) . . . . ? C58 C57 C62 Ir -175.7(3) . . . . ? C56 C57 C62 Ir 4.2(4) . . . . ? C42 Ir C62 C61 88.1(4) . . . . ? N51 Ir C62 C61 -178.3(4) . . . . ? N31 Ir C62 C61 8.0(4) . . . . ? N21 Ir C62 C61 -86.1(11) . . . . ? N11 Ir C62 C61 -91.3(4) . . . . ? C42 Ir C62 C57 -96.0(3) . . . . ? N51 Ir C62 C57 -2.5(3) . . . . ? N31 Ir C62 C57 -176.2(3) . . . . ? N21 Ir C62 C57 89.7(11) . . . . ? N11 Ir C62 C57 84.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.135 _refine_diff_density_min -2.355 _refine_diff_density_rms 0.118 #============================================================================= # end of cif data for "fro5493" #============================================================================= #============================================================================= # end of cif file #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 963446'