# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Professor Hong Yan' _publ_contact_author_address ; State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210093, P. R. China ; _publ_contact_author_email hyan1965@nju.edu.cn _publ_contact_author_phone +86-25-83686724 _publ_contact_author_fax +86-25-83314502 _publ_section_title ; Unprecedented C-C and C-S Bond Formation via C-H Activation or Group Migration in the Reactions of Cp*IrS2C2B10H10 and Aryl Azides ; loop_ _publ_author_name 'Wei Zhong' 'Mingshi Xie' 'Qibai Jiang' 'Yizhi Li' 'Hong Yan' #TrackingRef '- cif.cif' data_2 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 843467' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H34 B10 Ir N S2' _chemical_formula_weight 652.90 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8407(8) _cell_length_b 18.8053(13) _cell_length_c 12.2337(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.6700(10) _cell_angle_gamma 90.00 _cell_volume 2622.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 5.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.310 _exptl_absorpt_correction_T_max 0.388 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14186 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5141 _reflns_number_gt 4413 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.4327P] 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 5141 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Ir1 Ir 0.241536(12) 0.909397(7) 0.773281(11) 0.03328(7) Uani 1 1 d . . . S1 S 0.05021(9) 0.93206(6) 0.78739(9) 0.0433(2) Uani 1 1 d . . . S2 S 0.21127(10) 0.78579(5) 0.78905(9) 0.0470(3) Uani 1 1 d . . . C8 C 0.2480(4) 1.0864(2) 0.8094(5) 0.0561(12) Uani 1 1 d . . . H8A H 0.2629 1.1131 0.7478 0.084 Uiso 1 1 calc R . . H8B H 0.2755 1.1128 0.8787 0.084 Uiso 1 1 calc R . . H8C H 0.1653 1.0782 0.7948 0.084 Uiso 1 1 calc R . . C6 C 0.4289(3) 0.9200(2) 0.7977(3) 0.0397(9) Uani 1 1 d . . . N1 N 0.1764(3) 0.89043(18) 0.6033(3) 0.0391(7) Uani 1 1 d . . . H1 H 0.1306 0.8542 0.5876 0.047 Uiso 1 1 calc R . . C2 C 0.0860(3) 0.7791(2) 0.8427(3) 0.0394(9) Uani 1 1 d . . . C7 C 0.3675(3) 0.9827(2) 0.7437(3) 0.0365(9) Uani 1 1 d . . . C1 C 0.0063(3) 0.8522(2) 0.8431(3) 0.0402(9) Uani 1 1 d . . . C13 C 0.2502(4) 0.9957(2) 0.5250(3) 0.0410(9) Uani 1 1 d . . . C12 C 0.3642(4) 1.0045(2) 0.6245(3) 0.0442(10) Uani 1 1 d . . . H12A H 0.4258 0.9782 0.6036 0.053 Uiso 1 1 calc R . . H12B H 0.3860 1.0543 0.6272 0.053 Uiso 1 1 calc R . . C14 C 0.1912(3) 0.92303(19) 0.5143(3) 0.0364(9) Uani 1 1 d . . . C3 C 0.3116(3) 1.0161(2) 0.8201(3) 0.0401(9) Uani 1 1 d . . . B9 B -0.0017(6) 0.7717(3) 1.0300(4) 0.0642(16) Uani 1 1 d . . . H9 H 0.0140 0.7668 1.1225 0.077 Uiso 1 1 calc R . . B5 B -0.0021(5) 0.7052(3) 0.8188(4) 0.0531(14) Uani 1 1 d . . . H5 H 0.0147 0.6577 0.7731 0.064 Uiso 1 1 calc R . . C9 C 0.2987(4) 0.9909(3) 1.0265(4) 0.0641(14) Uani 1 1 d . . . H9A H 0.3224 0.9537 1.0817 0.096 Uiso 1 1 calc R . . H9B H 0.2149 0.9960 1.0072 0.096 Uiso 1 1 calc R . . H9C H 0.3349 1.0348 1.0576 0.096 Uiso 1 1 calc R . . C20 C 0.0585(4) 0.8303(2) 0.3895(4) 0.0581(12) Uani 1 1 d . . . H20A H 0.1031 0.7899 0.4251 0.087 Uiso 1 1 calc R . . H20B H 0.0248 0.8204 0.3103 0.087 Uiso 1 1 calc R . . H20C H -0.0030 0.8397 0.4250 0.087 Uiso 1 1 calc R . . C5 C 0.4069(4) 0.9150(2) 0.9081(4) 0.0449(10) Uani 1 1 d . . . C15 C 0.1371(4) 0.8937(2) 0.4019(3) 0.0455(10) Uani 1 1 d . . . C19 C 0.1529(4) 1.0479(2) 0.5334(4) 0.0506(11) Uani 1 1 d . . . H19A H 0.0901 1.0459 0.4648 0.076 Uiso 1 1 calc R . . H19B H 0.1841 1.0953 0.5439 0.076 Uiso 1 1 calc R . . H19C H 0.1237 1.0351 0.5967 0.076 Uiso 1 1 calc R . . C18 C 0.2837(4) 1.0152(2) 0.4184(4) 0.0552(12) Uani 1 1 d . . . H18 H 0.3369 1.0520 0.4214 0.066 Uiso 1 1 calc R . . B4 B 0.0864(5) 0.7266(3) 0.9581(4) 0.0529(14) Uani 1 1 d . . . H4 H 0.1602 0.6928 1.0029 0.064 Uiso 1 1 calc R . . C11 C 0.5069(4) 0.8717(3) 0.7533(4) 0.0550(11) Uani 1 1 d . . . H11A H 0.5848 0.8910 0.7716 0.082 Uiso 1 1 calc R . . H11B H 0.4772 0.8674 0.6724 0.082 Uiso 1 1 calc R . . H11C H 0.5088 0.8256 0.7876 0.082 Uiso 1 1 calc R . . C16 C 0.1626(5) 0.9232(3) 0.3116(4) 0.0600(13) Uani 1 1 d . . . H16 H 0.1281 0.9045 0.2400 0.072 Uiso 1 1 calc R . . C17 C 0.2406(5) 0.9821(3) 0.3211(4) 0.0658(14) Uani 1 1 d . . . H17 H 0.2615 0.9975 0.2570 0.079 Uiso 1 1 calc R . . B3 B 0.0928(5) 0.8203(3) 0.9704(4) 0.0457(11) Uani 1 1 d . . . H3 H 0.1710 0.8479 1.0220 0.055 Uiso 1 1 calc R . . C10 C 0.4550(4) 0.8581(3) 0.9943(4) 0.0664(14) Uani 1 1 d . . . H10A H 0.4084 0.8555 1.0473 0.100 Uiso 1 1 calc R . . H10B H 0.5346 0.8693 1.0340 0.100 Uiso 1 1 calc R . . H10C H 0.4527 0.8132 0.9565 0.100 Uiso 1 1 calc R . . B6 B -0.0510(4) 0.7855(3) 0.7465(4) 0.0479(12) Uani 1 1 d . . . H6 H -0.0659 0.7903 0.6541 0.058 Uiso 1 1 calc R . . B7 B -0.1374(5) 0.8312(3) 0.8198(5) 0.0618(15) Uani 1 1 d . . . H7 H -0.2096 0.8660 0.7744 0.074 Uiso 1 1 calc R . . B10 B -0.0616(6) 0.7001(3) 0.9367(5) 0.0657(17) Uani 1 1 d . . . H10 H -0.0850 0.6487 0.9677 0.079 Uiso 1 1 calc R . . B11 B -0.1452(5) 0.7373(3) 0.8082(5) 0.0639(16) Uani 1 1 d . . . H11 H -0.2238 0.7102 0.7561 0.077 Uiso 1 1 calc R . . B8 B -0.0494(5) 0.8523(3) 0.9588(5) 0.0587(14) Uani 1 1 d . . . H8 H -0.0646 0.9004 1.0038 0.070 Uiso 1 1 calc R . . C4 C 0.3357(4) 0.9725(2) 0.9221(3) 0.0472(10) Uani 1 1 d . . . B12 B -0.1443(5) 0.7783(3) 0.9381(6) 0.0699(17) Uani 1 1 d . . . H12 H -0.2223 0.7781 0.9706 0.084 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 0.03449(10) 0.03476(10) 0.03277(10) -0.00178(6) 0.01283(7) -0.00320(6) S1 0.0382(5) 0.0356(5) 0.0604(6) 0.0114(5) 0.0208(5) 0.0025(4) S2 0.0525(6) 0.0346(6) 0.0605(7) 0.0024(4) 0.0263(5) 0.0044(5) C8 0.059(3) 0.046(3) 0.066(3) -0.015(2) 0.021(2) -0.004(2) C6 0.033(2) 0.047(2) 0.041(2) -0.0084(17) 0.0122(17) -0.0063(17) N1 0.0372(18) 0.0437(19) 0.0367(18) -0.0059(14) 0.0108(15) -0.0108(15) C2 0.048(2) 0.033(2) 0.038(2) 0.0061(16) 0.0131(18) -0.0002(18) C7 0.0302(19) 0.037(2) 0.046(2) -0.0062(16) 0.0173(17) -0.0089(16) C1 0.037(2) 0.039(2) 0.047(2) 0.0079(17) 0.0160(18) -0.0028(17) C13 0.049(2) 0.038(2) 0.040(2) 0.0041(17) 0.0185(18) 0.0024(18) C12 0.045(2) 0.043(2) 0.052(2) -0.0034(18) 0.025(2) -0.0072(18) C14 0.040(2) 0.035(2) 0.037(2) -0.0012(16) 0.0141(17) 0.0026(16) C3 0.037(2) 0.040(2) 0.046(2) -0.0112(17) 0.0166(18) -0.0095(17) B9 0.091(5) 0.064(4) 0.044(3) 0.002(2) 0.029(3) -0.020(3) B5 0.079(4) 0.036(3) 0.040(3) 0.003(2) 0.009(3) -0.016(3) C9 0.064(3) 0.085(4) 0.048(3) -0.025(2) 0.025(2) -0.016(3) C20 0.066(3) 0.054(3) 0.050(2) -0.014(2) 0.007(2) 0.003(2) C5 0.043(2) 0.052(3) 0.038(2) -0.0030(17) 0.0075(19) -0.0042(19) C15 0.053(3) 0.047(2) 0.037(2) -0.0020(18) 0.0131(19) 0.015(2) C19 0.053(3) 0.036(2) 0.063(3) 0.002(2) 0.016(2) 0.007(2) C18 0.069(3) 0.050(3) 0.056(3) 0.013(2) 0.032(2) 0.002(2) B4 0.076(4) 0.039(3) 0.037(2) 0.011(2) 0.004(2) -0.013(3) C11 0.047(3) 0.061(3) 0.060(3) -0.005(2) 0.019(2) 0.009(2) C16 0.081(4) 0.059(3) 0.039(2) -0.005(2) 0.015(2) 0.018(3) C17 0.097(4) 0.063(3) 0.048(3) 0.014(2) 0.040(3) 0.015(3) B3 0.057(3) 0.041(3) 0.039(2) 0.0029(19) 0.013(2) -0.010(2) C10 0.060(3) 0.088(4) 0.046(2) 0.007(3) 0.005(2) 0.007(3) B6 0.048(3) 0.047(3) 0.044(3) 0.009(2) 0.005(2) -0.007(2) B7 0.042(3) 0.060(4) 0.087(4) 0.021(3) 0.023(3) -0.004(3) B10 0.081(4) 0.060(4) 0.056(3) 0.013(3) 0.020(3) -0.027(3) B11 0.057(3) 0.066(4) 0.063(3) 0.013(3) 0.007(3) -0.025(3) B8 0.062(4) 0.061(4) 0.066(3) -0.001(3) 0.040(3) -0.009(3) C4 0.044(2) 0.061(3) 0.039(2) -0.0143(19) 0.0143(19) -0.013(2) B12 0.061(4) 0.074(4) 0.084(4) 0.003(3) 0.036(3) -0.023(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 Ir1 N1 2.045(3) . ? Ir1 C7 2.133(4) . ? Ir1 C6 2.166(4) . ? Ir1 C3 2.188(4) . ? Ir1 C5 2.196(4) . ? Ir1 C4 2.207(4) . ? Ir1 S1 2.3569(11) . ? Ir1 S2 2.3678(11) . ? S1 C1 1.784(4) . ? S2 C2 1.781(4) . ? C8 C3 1.510(5) . ? C6 C5 1.446(6) . ? C6 C7 1.448(5) . ? C6 C11 1.499(6) . ? N1 C14 1.302(5) . ? C2 C1 1.668(5) . ? C2 B5 1.715(6) . ? C2 B4 1.722(6) . ? C2 B3 1.726(6) . ? C2 B6 1.732(6) . ? C7 C3 1.429(5) . ? C7 C12 1.505(5) . ? C1 B7 1.695(7) . ? C1 B8 1.715(7) . ? C1 B3 1.724(6) . ? C1 B6 1.731(6) . ? C13 C18 1.508(6) . ? C13 C14 1.524(5) . ? C13 C19 1.538(6) . ? C13 C12 1.564(5) . ? C14 C15 1.459(6) . ? C3 C4 1.456(6) . ? B9 B3 1.750(7) . ? B9 B4 1.754(9) . ? B9 B12 1.762(8) . ? B9 B8 1.764(8) . ? B9 B10 1.783(8) . ? B5 B6 1.766(7) . ? B5 B10 1.769(8) . ? B5 B11 1.770(9) . ? B5 B4 1.788(6) . ? C9 C4 1.498(6) . ? C20 C15 1.496(6) . ? C5 C4 1.410(6) . ? C5 C10 1.502(6) . ? C15 C16 1.341(7) . ? C18 C17 1.318(6) . ? B4 B3 1.769(7) . ? B4 B10 1.771(8) . ? C16 C17 1.426(7) . ? B3 B8 1.756(8) . ? B6 B7 1.757(8) . ? B6 B11 1.759(7) . ? B7 B11 1.773(8) . ? B7 B12 1.777(8) . ? B7 B8 1.783(9) . ? B10 B11 1.761(8) . ? B10 B12 1.770(9) . ? B11 B12 1.764(9) . ? B8 B12 1.764(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C7 91.68(14) . . ? N1 Ir1 C6 104.32(14) . . ? C7 Ir1 C6 39.36(14) . . ? N1 Ir1 C3 116.01(14) . . ? C7 Ir1 C3 38.59(14) . . ? C6 Ir1 C3 65.03(14) . . ? N1 Ir1 C5 141.93(15) . . ? C7 Ir1 C5 64.76(15) . . ? C6 Ir1 C5 38.70(16) . . ? C3 Ir1 C5 63.97(15) . . ? N1 Ir1 C4 154.28(15) . . ? C7 Ir1 C4 64.66(15) . . ? C6 Ir1 C4 64.31(15) . . ? C3 Ir1 C4 38.70(15) . . ? C5 Ir1 C4 37.35(15) . . ? N1 Ir1 S1 90.00(10) . . ? C7 Ir1 S1 128.72(11) . . ? C6 Ir1 S1 160.41(11) . . ? C3 Ir1 S1 96.82(11) . . ? C5 Ir1 S1 128.05(12) . . ? C4 Ir1 S1 97.10(12) . . ? N1 Ir1 S2 83.56(10) . . ? C7 Ir1 S2 140.97(11) . . ? C6 Ir1 S2 104.54(11) . . ? C3 Ir1 S2 159.10(11) . . ? C5 Ir1 S2 96.32(11) . . ? C4 Ir1 S2 120.95(12) . . ? S1 Ir1 S2 90.11(4) . . ? C1 S1 Ir1 105.10(14) . . ? C2 S2 Ir1 105.02(13) . . ? C5 C6 C7 106.5(3) . . ? C5 C6 C11 125.7(4) . . ? C7 C6 C11 127.7(4) . . ? C5 C6 Ir1 71.8(2) . . ? C7 C6 Ir1 69.1(2) . . ? C11 C6 Ir1 127.1(3) . . ? C14 N1 Ir1 132.0(3) . . ? C1 C2 B5 110.4(3) . . ? C1 C2 B4 110.3(3) . . ? B5 C2 B4 62.7(3) . . ? C1 C2 B3 61.0(2) . . ? B5 C2 B3 113.3(3) . . ? B4 C2 B3 61.7(3) . . ? C1 C2 B6 61.2(3) . . ? B5 C2 B6 61.7(3) . . ? B4 C2 B6 113.1(3) . . ? B3 C2 B6 112.9(3) . . ? C1 C2 S2 118.1(2) . . ? B5 C2 S2 121.6(3) . . ? B4 C2 S2 121.7(3) . . ? B3 C2 S2 117.5(3) . . ? B6 C2 S2 117.7(3) . . ? C3 C7 C6 108.9(3) . . ? C3 C7 C12 128.3(4) . . ? C6 C7 C12 122.8(3) . . ? C3 C7 Ir1 72.8(2) . . ? C6 C7 Ir1 71.6(2) . . ? C12 C7 Ir1 120.3(3) . . ? C2 C1 B7 110.6(3) . . ? C2 C1 B8 110.3(3) . . ? B7 C1 B8 63.0(3) . . ? C2 C1 B3 61.2(2) . . ? B7 C1 B3 113.3(3) . . ? B8 C1 B3 61.4(3) . . ? C2 C1 B6 61.2(3) . . ? B7 C1 B6 61.7(3) . . ? B8 C1 B6 113.4(3) . . ? B3 C1 B6 113.1(3) . . ? C2 C1 S1 118.0(3) . . ? B7 C1 S1 121.0(3) . . ? B8 C1 S1 122.0(3) . . ? B3 C1 S1 118.3(3) . . ? B6 C1 S1 116.8(3) . . ? C18 C13 C14 111.4(3) . . ? C18 C13 C19 106.3(3) . . ? C14 C13 C19 104.1(3) . . ? C18 C13 C12 105.9(3) . . ? C14 C13 C12 116.1(3) . . ? C19 C13 C12 112.7(3) . . ? C7 C12 C13 121.1(3) . . ? N1 C14 C15 119.0(4) . . ? N1 C14 C13 120.8(3) . . ? C15 C14 C13 119.6(4) . . ? C7 C3 C4 107.1(3) . . ? C7 C3 C8 129.5(4) . . ? C4 C3 C8 123.1(4) . . ? C7 C3 Ir1 68.6(2) . . ? C4 C3 Ir1 71.3(2) . . ? C8 C3 Ir1 129.5(3) . . ? B3 B9 B4 60.6(3) . . ? B3 B9 B12 107.9(4) . . ? B4 B9 B12 108.2(4) . . ? B3 B9 B8 60.0(3) . . ? B4 B9 B8 108.8(4) . . ? B12 B9 B8 60.0(3) . . ? B3 B9 B10 108.4(4) . . ? B4 B9 B10 60.1(3) . . ? B12 B9 B10 59.9(4) . . ? B8 B9 B10 108.3(4) . . ? C2 B5 B6 59.7(2) . . ? C2 B5 B10 105.2(4) . . ? B6 B5 B10 107.8(4) . . ? C2 B5 B11 105.3(4) . . ? B6 B5 B11 59.6(3) . . ? B10 B5 B11 59.7(3) . . ? C2 B5 B4 58.8(2) . . ? B6 B5 B4 108.3(3) . . ? B10 B5 B4 59.7(3) . . ? B11 B5 B4 107.3(4) . . ? C4 C5 C6 109.2(4) . . ? C4 C5 C10 125.9(4) . . ? C6 C5 C10 124.9(4) . . ? C4 C5 Ir1 71.7(2) . . ? C6 C5 Ir1 69.5(2) . . ? C10 C5 Ir1 125.8(3) . . ? C16 C15 C14 118.7(4) . . ? C16 C15 C20 121.2(4) . . ? C14 C15 C20 120.0(4) . . ? C17 C18 C13 122.5(4) . . ? C2 B4 B9 105.3(4) . . ? C2 B4 B3 59.3(2) . . ? B9 B4 B3 59.6(3) . . ? C2 B4 B10 104.9(3) . . ? B9 B4 B10 60.8(4) . . ? B3 B4 B10 108.1(4) . . ? C2 B4 B5 58.5(2) . . ? B9 B4 B5 108.1(4) . . ? B3 B4 B5 107.8(3) . . ? B10 B4 B5 59.6(3) . . ? C15 C16 C17 122.6(4) . . ? C18 C17 C16 121.7(5) . . ? C1 B3 C2 57.8(2) . . ? C1 B3 B9 105.5(4) . . ? C2 B3 B9 105.3(3) . . ? C1 B3 B8 59.1(3) . . ? C2 B3 B8 105.8(3) . . ? B9 B3 B8 60.4(3) . . ? C1 B3 B4 105.6(3) . . ? C2 B3 B4 59.0(2) . . ? B9 B3 B4 59.8(3) . . ? B8 B3 B4 108.4(4) . . ? C1 B6 C2 57.6(2) . . ? C1 B6 B7 58.1(3) . . ? C2 B6 B7 104.8(4) . . ? C1 B6 B11 104.9(4) . . ? C2 B6 B11 105.0(3) . . ? B7 B6 B11 60.6(3) . . ? C1 B6 B5 105.2(3) . . ? C2 B6 B5 58.7(3) . . ? B7 B6 B5 108.6(4) . . ? B11 B6 B5 60.3(3) . . ? C1 B7 B6 60.2(3) . . ? C1 B7 B11 105.9(4) . . ? B6 B7 B11 59.8(3) . . ? C1 B7 B12 105.0(4) . . ? B6 B7 B12 107.6(4) . . ? B11 B7 B12 59.6(3) . . ? C1 B7 B8 59.0(3) . . ? B6 B7 B8 108.9(4) . . ? B11 B7 B8 107.6(4) . . ? B12 B7 B8 59.4(3) . . ? B11 B10 B5 60.2(3) . . ? B11 B10 B12 59.9(4) . . ? B5 B10 B12 107.8(4) . . ? B11 B10 B4 108.4(4) . . ? B5 B10 B4 60.7(3) . . ? B12 B10 B4 107.0(4) . . ? B11 B10 B9 107.6(4) . . ? B5 B10 B9 107.7(4) . . ? B12 B10 B9 59.5(4) . . ? B4 B10 B9 59.1(3) . . ? B6 B11 B10 108.6(4) . . ? B6 B11 B12 108.1(4) . . ? B10 B11 B12 60.3(4) . . ? B6 B11 B5 60.1(3) . . ? B10 B11 B5 60.2(3) . . ? B12 B11 B5 108.1(4) . . ? B6 B11 B7 59.7(3) . . ? B10 B11 B7 108.7(4) . . ? B12 B11 B7 60.3(3) . . ? B5 B11 B7 107.8(4) . . ? C1 B8 B3 59.5(3) . . ? C1 B8 B9 105.3(4) . . ? B3 B8 B9 59.6(3) . . ? C1 B8 B12 104.7(4) . . ? B3 B8 B12 107.5(4) . . ? B9 B8 B12 60.0(3) . . ? C1 B8 B7 57.9(3) . . ? B3 B8 B7 107.6(4) . . ? B9 B8 B7 107.9(4) . . ? B12 B8 B7 60.1(3) . . ? C5 C4 C3 108.2(4) . . ? C5 C4 C9 127.1(4) . . ? C3 C4 C9 124.4(4) . . ? C5 C4 Ir1 70.9(2) . . ? C3 C4 Ir1 70.0(2) . . ? C9 C4 Ir1 129.0(3) . . ? B9 B12 B11 108.4(4) . . ? B9 B12 B8 60.0(3) . . ? B11 B12 B8 108.8(4) . . ? B9 B12 B10 60.6(3) . . ? B11 B12 B10 59.8(3) . . ? B8 B12 B10 108.9(4) . . ? B9 B12 B7 108.2(4) . . ? B11 B12 B7 60.1(4) . . ? B8 B12 B7 60.5(3) . . ? B10 B12 B7 108.1(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.204 _refine_diff_density_min -1.034 _refine_diff_density_rms 0.100 data_3 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 843468' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H31 B10 Ir N2 O2 S2' _chemical_formula_weight 683.88 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' 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' O O 0.0106 0.0060 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4394(9) _cell_length_b 11.8736(9) _cell_length_c 12.1698(10) _cell_angle_alpha 68.1290(10) _cell_angle_beta 63.1900(10) _cell_angle_gamma 87.3560(10) _cell_volume 1354.21(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 5.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.276 _exptl_absorpt_correction_T_max 0.379 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7427 _diffrn_reflns_av_R_equivalents 0.1172 _diffrn_reflns_av_sigmaI/netI 0.1035 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5201 _reflns_number_gt 4432 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^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 5201 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.078 _refine_ls_shift/su_mean 0.001 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 0.74836(2) 0.63636(2) 0.73516(3) 0.03131(9) Uani 1 1 d . . . S2 S 0.79640(16) 0.84652(13) 0.66760(17) 0.0323(4) Uani 1 1 d . . . S1 S 0.67759(18) 0.60426(14) 0.96199(19) 0.0404(4) Uani 1 1 d . . . C2 C 0.7964(7) 0.8662(5) 0.8092(7) 0.0341(15) Uani 1 1 d . . . N1 N 0.5661(5) 0.6807(4) 0.7632(6) 0.0358(13) Uani 1 1 d . . . H1 H 0.5017 0.6220 0.8016 0.043 Uiso 1 1 calc R . . C1 C 0.7434(6) 0.7438(5) 0.9518(7) 0.0340(15) Uani 1 1 d . . . C13 C 0.5408(7) 0.7962(6) 0.7250(7) 0.0340(15) Uani 1 1 d . . . C18 C 0.4190(7) 0.8325(6) 0.7303(8) 0.0414(16) Uani 1 1 d . . . C16 C 0.5174(8) 1.0460(6) 0.6253(7) 0.0431(17) Uani 1 1 d . . . C14 C 0.6463(7) 0.8930(6) 0.6703(7) 0.0385(16) Uani 1 1 d . . . O1 O 0.5965(8) 1.2512(5) 0.5317(8) 0.083(2) Uani 1 1 d . . . C4 C 0.7523(6) 0.5165(6) 0.6325(8) 0.0388(16) Uani 1 1 d . . . B8 B 0.8387(9) 0.7461(7) 1.0269(10) 0.046(2) Uani 1 1 d . . . H8 H 0.8606 0.6628 1.0896 0.056 Uiso 1 1 calc R . . C3 C 0.8575(7) 0.6178(6) 0.5410(8) 0.0427(17) Uani 1 1 d . . . C7 C 0.9431(7) 0.6084(6) 0.6031(8) 0.0428(18) Uani 1 1 d . . . O2 O 0.4004(7) 1.2005(5) 0.5696(7) 0.084(2) Uani 1 1 d . . . C17 C 0.4085(8) 0.9562(6) 0.6811(8) 0.0473(19) Uani 1 1 d . . . H17 H 0.3285 0.9799 0.6851 0.057 Uiso 1 1 calc R . . C15 C 0.6365(8) 1.0165(6) 0.6172(7) 0.0426(17) Uani 1 1 d . . . H15 H 0.7087 1.0769 0.5775 0.051 Uiso 1 1 calc R . . C5 C 0.7677(7) 0.4494(6) 0.7470(8) 0.0408(17) Uani 1 1 d . . . N2 N 0.5027(8) 1.1741(6) 0.5737(7) 0.0575(18) Uani 1 1 d . . . B3 B 0.9130(8) 0.7934(7) 0.8514(10) 0.043(2) Uani 1 1 d . . . H3 H 0.9827 0.7416 0.7989 0.052 Uiso 1 1 calc R . . C6 C 0.8927(7) 0.5068(6) 0.7263(8) 0.0424(17) Uani 1 1 d . . . B5 B 0.7688(8) 1.0005(7) 0.8325(9) 0.041(2) Uani 1 1 d . . . H5 H 0.7464 1.0823 0.7684 0.049 Uiso 1 1 calc R . . B6 B 0.6526(8) 0.8649(6) 0.9404(9) 0.0377(18) Uani 1 1 d . . . H6 H 0.5544 0.8587 0.9456 0.045 Uiso 1 1 calc R . . C9 C 0.8817(9) 0.7074(7) 0.4070(8) 0.059(2) Uani 1 1 d . . . H9A H 0.8360 0.6738 0.3740 0.089 Uiso 1 1 calc R . . H9B H 0.9749 0.7243 0.3465 0.089 Uiso 1 1 calc R . . H9C H 0.8497 0.7819 0.4137 0.089 Uiso 1 1 calc R . . C19 C 0.3045(7) 0.7342(7) 0.7839(9) 0.057(2) Uani 1 1 d . . . H19A H 0.2312 0.7723 0.7762 0.086 Uiso 1 1 calc R . . H19B H 0.2783 0.6842 0.8763 0.086 Uiso 1 1 calc R . . H19C H 0.3318 0.6839 0.7330 0.086 Uiso 1 1 calc R . . B11 B 0.6949(9) 0.9527(7) 1.0098(9) 0.045(2) Uani 1 1 d . . . H11 H 0.6243 1.0044 1.0616 0.054 Uiso 1 1 calc R . . C10 C 0.6402(9) 0.4920(7) 0.6092(10) 0.061(2) Uani 1 1 d . . . H10A H 0.5632 0.4507 0.6938 0.092 Uiso 1 1 calc R . . H10B H 0.6642 0.4412 0.5589 0.092 Uiso 1 1 calc R . . H10C H 0.6212 0.5682 0.5599 0.092 Uiso 1 1 calc R . . C8 C 1.0730(7) 0.6902(7) 0.5337(10) 0.061(2) Uani 1 1 d . . . H8A H 1.1347 0.6714 0.4597 0.092 Uiso 1 1 calc R . . H8B H 1.1073 0.6770 0.5958 0.092 Uiso 1 1 calc R . . H8C H 1.0600 0.7744 0.5015 0.092 Uiso 1 1 calc R . . C11 C 0.6875(8) 0.3336(6) 0.8610(10) 0.060(2) Uani 1 1 d . . . H11A H 0.7294 0.2652 0.8455 0.090 Uiso 1 1 calc R . . H11B H 0.6005 0.3263 0.8688 0.090 Uiso 1 1 calc R . . H11C H 0.6806 0.3344 0.9423 0.090 Uiso 1 1 calc R . . B12 B 0.8116(9) 0.8779(8) 1.0628(9) 0.048(2) Uani 1 1 d . . . H12 H 0.8159 0.8813 1.1500 0.057 Uiso 1 1 calc R . . B4 B 0.9307(8) 0.9545(7) 0.7783(10) 0.043(2) Uani 1 1 d . . . H4 H 1.0124 1.0073 0.6780 0.051 Uiso 1 1 calc R . . B7 B 0.6794(9) 0.7902(7) 1.0818(9) 0.043(2) Uani 1 1 d . . . H7 H 0.5974 0.7354 1.1810 0.052 Uiso 1 1 calc R . . C12 C 0.9540(9) 0.4599(7) 0.8192(10) 0.066(2) Uani 1 1 d . . . H12A H 1.0372 0.5101 0.7805 0.098 Uiso 1 1 calc R . . H12B H 0.9681 0.3767 0.8318 0.098 Uiso 1 1 calc R . . H12C H 0.8956 0.4633 0.9041 0.098 Uiso 1 1 calc R . . B10 B 0.8700(9) 1.0092(8) 0.9081(10) 0.049(2) Uani 1 1 d . . . H10 H 0.9128 1.0978 0.8938 0.058 Uiso 1 1 calc R . . B9 B 0.9565(9) 0.8817(8) 0.9198(10) 0.048(2) Uani 1 1 d . . . H9 H 1.0552 0.8880 0.9133 0.057 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 0.03524(15) 0.02532(14) 0.03782(16) -0.01756(11) -0.01699(12) 0.00856(9) S2 0.0392(9) 0.0288(8) 0.0315(9) -0.0152(7) -0.0160(8) 0.0053(7) S1 0.0538(11) 0.0293(8) 0.0348(10) -0.0120(7) -0.0183(9) 0.0036(7) C2 0.044(4) 0.030(3) 0.043(4) -0.022(3) -0.026(4) 0.010(3) N1 0.034(3) 0.022(3) 0.051(4) -0.017(2) -0.017(3) 0.003(2) C1 0.041(4) 0.030(3) 0.033(4) -0.015(3) -0.017(3) 0.010(3) C13 0.045(4) 0.037(4) 0.031(4) -0.022(3) -0.020(3) 0.013(3) C18 0.045(4) 0.050(4) 0.038(4) -0.024(3) -0.022(4) 0.015(3) C16 0.067(5) 0.041(4) 0.039(4) -0.025(3) -0.033(4) 0.030(4) C14 0.050(4) 0.036(4) 0.041(4) -0.018(3) -0.029(4) 0.017(3) O1 0.125(6) 0.037(3) 0.106(6) -0.028(4) -0.071(5) 0.022(4) C4 0.039(4) 0.036(4) 0.050(5) -0.031(3) -0.018(4) 0.012(3) B8 0.056(5) 0.047(5) 0.050(6) -0.020(4) -0.035(5) 0.014(4) C3 0.051(4) 0.036(4) 0.044(5) -0.029(3) -0.016(4) 0.016(3) C7 0.043(4) 0.040(4) 0.064(6) -0.035(4) -0.029(4) 0.012(3) O2 0.108(5) 0.071(4) 0.086(6) -0.033(4) -0.058(5) 0.058(4) C17 0.063(5) 0.052(4) 0.045(5) -0.030(4) -0.034(4) 0.031(4) C15 0.066(5) 0.034(4) 0.036(4) -0.019(3) -0.027(4) 0.015(3) C5 0.050(4) 0.028(3) 0.047(5) -0.021(3) -0.020(4) 0.015(3) N2 0.095(6) 0.044(4) 0.053(5) -0.028(3) -0.046(5) 0.036(4) B3 0.035(4) 0.051(5) 0.055(6) -0.029(4) -0.025(4) 0.016(4) C6 0.046(4) 0.046(4) 0.052(5) -0.031(4) -0.029(4) 0.027(3) B5 0.062(5) 0.027(4) 0.050(5) -0.025(4) -0.032(5) 0.004(4) B6 0.046(5) 0.031(4) 0.043(5) -0.017(4) -0.025(4) 0.010(3) C9 0.076(6) 0.049(5) 0.045(5) -0.021(4) -0.020(5) 0.015(4) C19 0.045(4) 0.071(5) 0.061(6) -0.029(5) -0.026(5) 0.013(4) B11 0.052(5) 0.043(5) 0.050(6) -0.028(4) -0.025(5) 0.011(4) C10 0.074(6) 0.051(5) 0.088(7) -0.045(5) -0.049(6) 0.018(4) C8 0.040(4) 0.067(5) 0.067(6) -0.038(5) -0.006(4) 0.005(4) C11 0.067(5) 0.034(4) 0.075(7) -0.022(4) -0.030(5) 0.010(4) B12 0.059(5) 0.058(5) 0.045(5) -0.031(4) -0.031(5) 0.011(4) B4 0.040(4) 0.036(4) 0.052(6) -0.019(4) -0.019(4) -0.007(3) B7 0.056(5) 0.040(4) 0.037(5) -0.016(4) -0.024(4) 0.004(4) C12 0.076(6) 0.069(5) 0.080(7) -0.040(5) -0.053(6) 0.042(5) B10 0.049(5) 0.048(5) 0.050(6) -0.023(4) -0.021(5) -0.003(4) B9 0.044(5) 0.059(5) 0.053(6) -0.032(5) -0.026(5) 0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N1 2.033(5) . ? Ir1 C7 2.181(7) . ? Ir1 C5 2.177(6) . ? Ir1 C6 2.199(6) . ? Ir1 C4 2.204(6) . ? Ir1 C3 2.212(7) . ? Ir1 S2 2.3227(15) . ? Ir1 S1 2.3768(19) . ? S2 C14 1.768(7) . ? S2 C2 1.824(7) . ? S1 C1 1.790(6) . ? C2 C1 1.657(9) . ? C2 B6 1.694(11) . ? C2 B4 1.713(9) . ? C2 B5 1.712(9) . ? C2 B3 1.724(10) . ? N1 C13 1.338(7) . ? C1 B7 1.706(11) . ? C1 B8 1.716(10) . ? C1 B6 1.735(9) . ? C1 B3 1.742(10) . ? C13 C18 1.420(9) . ? C13 C14 1.433(9) . ? C18 C17 1.387(9) . ? C18 C19 1.519(9) . ? C16 C15 1.359(10) . ? C16 C17 1.404(10) . ? C16 N2 1.448(8) . ? C14 C15 1.388(8) . ? O1 N2 1.223(9) . ? C4 C5 1.411(10) . ? C4 C3 1.436(9) . ? C4 C10 1.494(9) . ? B8 B7 1.765(12) . ? B8 B12 1.755(12) . ? B8 B3 1.764(13) . ? B8 B9 1.777(12) . ? C3 C7 1.461(10) . ? C3 C9 1.481(11) . ? C7 C6 1.405(10) . ? C7 C8 1.502(9) . ? O2 N2 1.215(8) . ? C5 C11 1.485(10) . ? C5 C6 1.487(10) . ? B3 B4 1.760(11) . ? B3 B9 1.764(12) . ? C6 C12 1.512(10) . ? B5 B6 1.769(11) . ? B5 B11 1.783(12) . ? B5 B10 1.800(11) . ? B5 B4 1.799(12) . ? B6 B11 1.762(11) . ? B6 B7 1.776(11) . ? B11 B7 1.776(11) . ? B11 B12 1.796(12) . ? B11 B10 1.807(12) . ? B12 B7 1.755(11) . ? B12 B9 1.768(13) . ? B12 B10 1.788(13) . ? B4 B10 1.769(13) . ? B4 B9 1.769(13) . ? B10 B9 1.766(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C7 148.6(3) . . ? N1 Ir1 C5 112.8(2) . . ? C7 Ir1 C5 64.3(3) . . ? N1 Ir1 C6 152.5(2) . . ? C7 Ir1 C6 37.4(3) . . ? C5 Ir1 C6 39.7(3) . . ? N1 Ir1 C4 94.8(2) . . ? C7 Ir1 C4 63.4(2) . . ? C5 Ir1 C4 37.6(3) . . ? C6 Ir1 C4 64.0(2) . . ? N1 Ir1 C3 110.2(3) . . ? C7 Ir1 C3 38.8(3) . . ? C5 Ir1 C3 64.4(3) . . ? C6 Ir1 C3 64.5(3) . . ? C4 Ir1 C3 38.0(2) . . ? N1 Ir1 S2 81.80(14) . . ? C7 Ir1 S2 97.40(17) . . ? C5 Ir1 S2 161.6(2) . . ? C6 Ir1 S2 125.42(19) . . ? C4 Ir1 S2 134.40(19) . . ? C3 Ir1 S2 100.77(17) . . ? N1 Ir1 S1 87.42(18) . . ? C7 Ir1 S1 124.0(2) . . ? C5 Ir1 S1 100.4(2) . . ? C6 Ir1 S1 95.4(2) . . ? C4 Ir1 S1 134.41(19) . . ? C3 Ir1 S1 159.91(19) . . ? S2 Ir1 S1 91.05(6) . . ? C14 S2 C2 104.5(3) . . ? C14 S2 Ir1 100.2(2) . . ? C2 S2 Ir1 105.5(2) . . ? C1 S1 Ir1 104.2(2) . . ? C1 C2 B6 62.4(4) . . ? C1 C2 B4 111.8(5) . . ? B6 C2 B4 114.7(5) . . ? C1 C2 B5 113.0(6) . . ? B6 C2 B5 62.6(5) . . ? B4 C2 B5 63.4(4) . . ? C1 C2 B3 62.0(4) . . ? B6 C2 B3 115.0(6) . . ? B4 C2 B3 61.6(4) . . ? B5 C2 B3 114.7(5) . . ? C1 C2 S2 117.4(4) . . ? B6 C2 S2 120.8(4) . . ? B4 C2 S2 117.6(5) . . ? B5 C2 S2 122.1(5) . . ? B3 C2 S2 112.9(5) . . ? C13 N1 Ir1 123.5(4) . . ? C2 C1 B7 108.9(5) . . ? C2 C1 B8 109.3(5) . . ? B7 C1 B8 62.1(5) . . ? C2 C1 B6 59.9(4) . . ? B7 C1 B6 62.2(4) . . ? B8 C1 B6 112.9(5) . . ? C2 C1 B3 60.9(4) . . ? B7 C1 B3 112.1(5) . . ? B8 C1 B3 61.4(5) . . ? B6 C1 B3 112.0(5) . . ? C2 C1 S1 118.5(4) . . ? B7 C1 S1 122.9(5) . . ? B8 C1 S1 122.5(4) . . ? B6 C1 S1 117.7(4) . . ? B3 C1 S1 117.8(5) . . ? N1 C13 C18 125.8(6) . . ? N1 C13 C14 117.7(6) . . ? C18 C13 C14 116.4(5) . . ? C17 C18 C13 119.7(6) . . ? C17 C18 C19 121.3(7) . . ? C13 C18 C19 118.9(6) . . ? C15 C16 C17 122.1(6) . . ? C15 C16 N2 119.0(7) . . ? C17 C16 N2 118.9(7) . . ? C15 C14 C13 123.5(6) . . ? C15 C14 S2 120.5(5) . . ? C13 C14 S2 116.0(5) . . ? C5 C4 C3 110.5(6) . . ? C5 C4 C10 126.0(7) . . ? C3 C4 C10 123.4(7) . . ? C5 C4 Ir1 70.2(4) . . ? C3 C4 Ir1 71.3(4) . . ? C10 C4 Ir1 123.1(5) . . ? C1 B8 B7 58.7(4) . . ? C1 B8 B12 105.6(6) . . ? B7 B8 B12 59.8(5) . . ? C1 B8 B3 60.1(4) . . ? B7 B8 B3 108.2(6) . . ? B12 B8 B3 107.9(6) . . ? C1 B8 B9 106.3(6) . . ? B7 B8 B9 107.9(6) . . ? B12 B8 B9 60.1(5) . . ? B3 B8 B9 59.8(5) . . ? C4 C3 C7 105.3(6) . . ? C4 C3 C9 127.9(7) . . ? C7 C3 C9 126.6(7) . . ? C4 C3 Ir1 70.7(4) . . ? C7 C3 Ir1 69.4(4) . . ? C9 C3 Ir1 127.8(5) . . ? C6 C7 C3 110.5(6) . . ? C6 C7 C8 126.5(7) . . ? C3 C7 C8 122.8(7) . . ? C6 C7 Ir1 72.0(4) . . ? C3 C7 Ir1 71.7(4) . . ? C8 C7 Ir1 128.1(5) . . ? C18 C17 C16 120.7(7) . . ? C16 C15 C14 117.5(7) . . ? C4 C5 C11 128.3(6) . . ? C4 C5 C6 107.2(6) . . ? C11 C5 C6 124.1(6) . . ? C4 C5 Ir1 72.2(4) . . ? C11 C5 Ir1 128.0(5) . . ? C6 C5 Ir1 70.9(3) . . ? O2 N2 O1 122.9(7) . . ? O2 N2 C16 119.0(7) . . ? O1 N2 C16 118.0(7) . . ? C2 B3 C1 57.1(4) . . ? C2 B3 B4 58.9(4) . . ? C1 B3 B4 105.7(5) . . ? C2 B3 B8 104.1(6) . . ? C1 B3 B8 58.6(4) . . ? B4 B3 B8 108.4(6) . . ? C2 B3 B9 104.8(5) . . ? C1 B3 B9 105.7(6) . . ? B4 B3 B9 60.2(5) . . ? B8 B3 B9 60.5(5) . . ? C7 C6 C5 106.5(6) . . ? C7 C6 C12 127.7(7) . . ? C5 C6 C12 125.7(7) . . ? C7 C6 Ir1 70.6(4) . . ? C5 C6 Ir1 69.4(3) . . ? C12 C6 Ir1 126.6(5) . . ? C2 B5 B6 58.2(4) . . ? C2 B5 B11 103.8(5) . . ? B6 B5 B11 59.5(5) . . ? C2 B5 B10 103.5(6) . . ? B6 B5 B10 107.5(6) . . ? B11 B5 B10 60.5(5) . . ? C2 B5 B4 58.4(4) . . ? B6 B5 B4 107.0(5) . . ? B11 B5 B4 107.2(6) . . ? B10 B5 B4 58.9(5) . . ? C2 B6 C1 57.8(4) . . ? C2 B6 B11 105.4(5) . . ? C1 B6 B11 105.8(5) . . ? C2 B6 B5 59.2(4) . . ? C1 B6 B5 106.5(6) . . ? B11 B6 B5 60.7(4) . . ? C2 B6 B7 104.1(5) . . ? C1 B6 B7 58.1(4) . . ? B11 B6 B7 60.3(4) . . ? B5 B6 B7 108.5(5) . . ? B6 B11 B5 59.9(4) . . ? B6 B11 B7 60.3(4) . . ? B5 B11 B7 107.9(6) . . ? B6 B11 B12 107.1(5) . . ? B5 B11 B12 107.6(6) . . ? B7 B11 B12 58.8(4) . . ? B6 B11 B10 107.5(6) . . ? B5 B11 B10 60.2(5) . . ? B7 B11 B10 106.7(6) . . ? B12 B11 B10 59.5(5) . . ? B7 B12 B8 60.4(5) . . ? B7 B12 B9 108.8(6) . . ? B8 B12 B9 60.6(5) . . ? B7 B12 B10 108.4(6) . . ? B8 B12 B10 108.3(7) . . ? B9 B12 B10 59.6(5) . . ? B7 B12 B11 60.0(4) . . ? B8 B12 B11 108.7(5) . . ? B9 B12 B11 108.5(6) . . ? B10 B12 B11 60.5(5) . . ? C2 B4 B10 104.7(6) . . ? C2 B4 B3 59.5(4) . . ? B10 B4 B3 108.2(7) . . ? C2 B4 B9 105.1(6) . . ? B10 B4 B9 59.9(5) . . ? B3 B4 B9 60.0(5) . . ? C2 B4 B5 58.3(4) . . ? B10 B4 B5 60.6(5) . . ? B3 B4 B5 108.7(5) . . ? B9 B4 B5 108.6(7) . . ? C1 B7 B12 106.0(6) . . ? C1 B7 B8 59.2(5) . . ? B12 B7 B8 59.8(5) . . ? C1 B7 B6 59.7(4) . . ? B12 B7 B6 108.3(6) . . ? B8 B7 B6 108.6(6) . . ? C1 B7 B11 106.5(6) . . ? B12 B7 B11 61.1(5) . . ? B8 B7 B11 109.1(6) . . ? B6 B7 B11 59.5(4) . . ? B9 B10 B4 60.0(5) . . ? B9 B10 B12 59.6(5) . . ? B4 B10 B12 107.1(6) . . ? B9 B10 B5 108.6(6) . . ? B4 B10 B5 60.5(5) . . ? B12 B10 B5 107.2(5) . . ? B9 B10 B11 108.1(6) . . ? B4 B10 B11 107.5(5) . . ? B12 B10 B11 60.0(5) . . ? B5 B10 B11 59.3(5) . . ? B10 B9 B3 108.2(6) . . ? B10 B9 B12 60.8(5) . . ? B3 B9 B12 107.4(6) . . ? B10 B9 B4 60.1(5) . . ? B3 B9 B4 59.8(5) . . ? B12 B9 B4 108.0(6) . . ? B10 B9 B8 108.3(6) . . ? B3 B9 B8 59.8(5) . . ? B12 B9 B8 59.3(5) . . ? B4 B9 B8 107.5(5) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.926 _refine_diff_density_min -1.944 _refine_diff_density_rms 0.158 data_5 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 843469' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H31 B10 Cl Ir N S2' _chemical_formula_weight 673.36 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9643(19) _cell_length_b 12.272(2) _cell_length_c 12.389(2) _cell_angle_alpha 69.416(2) _cell_angle_beta 80.047(2) _cell_angle_gamma 73.087(3) _cell_volume 1352.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 5.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.368 _exptl_absorpt_correction_T_max 0.458 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7406 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.1020 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5206 _reflns_number_gt 4173 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^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 5206 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.001 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 0.15467(4) 0.16279(3) 0.29239(3) 0.03550(14) Uani 1 1 d . . . S1 S -0.0180(3) 0.1956(2) 0.44248(19) 0.0455(6) Uani 1 1 d . . . S2 S 0.0193(3) 0.31919(19) 0.15537(18) 0.0356(5) Uani 1 1 d . . . N1 N 0.0374(9) 0.0677(7) 0.2600(7) 0.048(2) Uani 1 1 d . . . H1 H 0.0433 -0.0054 0.3034 0.058 Uiso 1 1 calc R . . B3 B -0.0431(13) 0.4602(9) 0.3154(9) 0.041(3) Uani 1 1 d . . . H3 H 0.0702 0.4505 0.3150 0.050 Uiso 1 1 calc R . . Cl Cl -0.3159(5) 0.2969(3) -0.1344(3) 0.0977(13) Uani 1 1 d . . . C2 C -0.1155(10) 0.4045(7) 0.2371(7) 0.033(2) Uani 1 1 d . . . B5 B -0.2740(12) 0.4917(9) 0.1873(9) 0.039(2) Uani 1 1 d . . . H5 H -0.3090 0.5031 0.1036 0.047 Uiso 1 1 calc R . . C14 C -0.0669(10) 0.2386(8) 0.1113(7) 0.037(2) Uani 1 1 d . . . C1 C -0.1246(10) 0.3422(8) 0.3804(7) 0.034(2) Uani 1 1 d . . . C15 C -0.1492(11) 0.2940(9) 0.0139(8) 0.047(2) Uani 1 1 d . . . H15 H -0.1575 0.3748 -0.0284 0.057 Uiso 1 1 calc R . . C7 C 0.3232(10) 0.0568(8) 0.4014(8) 0.042(2) Uani 1 1 d . . . B12 B -0.3281(13) 0.5479(10) 0.3988(9) 0.047(3) Uani 1 1 d . . . H12 H -0.4007 0.5969 0.4536 0.056 Uiso 1 1 calc R . . B7 B -0.2918(13) 0.3887(10) 0.4324(9) 0.044(3) Uani 1 1 d . . . H7 H -0.3405 0.3327 0.5107 0.053 Uiso 1 1 calc R . . C13 C -0.0476(10) 0.1143(8) 0.1747(8) 0.039(2) Uani 1 1 d . . . B8 B -0.1581(13) 0.4530(10) 0.4436(9) 0.045(3) Uani 1 1 d . . . H8 H -0.1207 0.4397 0.5269 0.054 Uiso 1 1 calc R . . B11 B -0.3907(13) 0.4850(10) 0.3123(9) 0.044(3) Uani 1 1 d . . . H11 H -0.5033 0.4929 0.3115 0.053 Uiso 1 1 calc R . . C18 C -0.1173(11) 0.0496(9) 0.1374(9) 0.049(3) Uani 1 1 d . . . B4 B -0.1403(13) 0.5562(9) 0.1951(10) 0.045(3) Uani 1 1 d . . . H4 H -0.0893 0.6096 0.1165 0.055 Uiso 1 1 calc R . . C4 C 0.3469(11) 0.2238(9) 0.2435(10) 0.057(3) Uani 1 1 d . . . C17 C -0.1958(13) 0.1075(10) 0.0440(10) 0.062(3) Uani 1 1 d . . . H17 H -0.2390 0.0636 0.0193 0.074 Uiso 1 1 calc R . . C10 C 0.3677(13) 0.3467(10) 0.1696(11) 0.075(4) Uani 1 1 d . . . H10A H 0.3337 0.3682 0.0951 0.113 Uiso 1 1 calc R . . H10B H 0.4660 0.3445 0.1604 0.113 Uiso 1 1 calc R . . H10C H 0.3167 0.4051 0.2066 0.113 Uiso 1 1 calc R . . C3 C 0.3274(10) 0.1822(8) 0.3671(8) 0.042(2) Uani 1 1 d . . . C16 C -0.2135(13) 0.2296(11) -0.0156(9) 0.062(3) Uani 1 1 d . . . B10 B -0.3156(14) 0.6107(10) 0.2447(10) 0.051(3) Uani 1 1 d . . . H10 H -0.3797 0.7003 0.1999 0.061 Uiso 1 1 calc R . . C9 C 0.3214(15) 0.2505(11) 0.4474(10) 0.077(4) Uani 1 1 d . . . H9A H 0.2255 0.2763 0.4756 0.115 Uiso 1 1 calc R . . H9B H 0.3583 0.3195 0.4068 0.115 Uiso 1 1 calc R . . H9C H 0.3765 0.1997 0.5113 0.115 Uiso 1 1 calc R . . C19 C -0.0971(14) -0.0838(9) 0.1995(10) 0.072(4) Uani 1 1 d . . . H19A H -0.1555 -0.1142 0.1690 0.107 Uiso 1 1 calc R . . H19B H -0.1227 -0.0974 0.2806 0.107 Uiso 1 1 calc R . . H19C H -0.0003 -0.1245 0.1882 0.107 Uiso 1 1 calc R . . C5 C 0.3628(11) 0.1264(10) 0.2044(8) 0.048(2) Uani 1 1 d . . . C8 C 0.3131(12) -0.0240(11) 0.5246(8) 0.067(3) Uani 1 1 d . . . H8A H 0.4051 -0.0726 0.5460 0.101 Uiso 1 1 calc R . . H8B H 0.2528 -0.0750 0.5318 0.101 Uiso 1 1 calc R . . H8C H 0.2749 0.0240 0.5747 0.101 Uiso 1 1 calc R . . C12 C 0.3660(15) -0.1015(10) 0.2960(12) 0.082(4) Uani 1 1 d . . . H12A H 0.3115 -0.1437 0.3602 0.123 Uiso 1 1 calc R . . H12B H 0.4633 -0.1446 0.2994 0.123 Uiso 1 1 calc R . . H12C H 0.3334 -0.0951 0.2250 0.123 Uiso 1 1 calc R . . C11 C 0.3934(15) 0.1263(14) 0.0770(9) 0.087(4) Uani 1 1 d . . . H11A H 0.4932 0.1058 0.0585 0.131 Uiso 1 1 calc R . . H11B H 0.3527 0.2047 0.0262 0.131 Uiso 1 1 calc R . . H11C H 0.3531 0.0683 0.0676 0.131 Uiso 1 1 calc R . . C6 C 0.3501(11) 0.0233(8) 0.3012(8) 0.046(2) Uani 1 1 d . . . B6 B -0.2628(12) 0.3548(10) 0.3042(9) 0.041(3) Uani 1 1 d . . . H6 H -0.2906 0.2773 0.2972 0.050 Uiso 1 1 calc R . . B9 B -0.1714(14) 0.5906(10) 0.3248(10) 0.049(3) Uani 1 1 d . . . H9 H -0.1419 0.6675 0.3317 0.058 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 0.0445(2) 0.0305(2) 0.0335(2) -0.01063(15) -0.00645(15) -0.00980(15) S1 0.0522(16) 0.0401(13) 0.0331(12) -0.0024(11) -0.0046(11) -0.0059(12) S2 0.0458(14) 0.0332(11) 0.0304(11) -0.0120(9) -0.0019(10) -0.0121(10) N1 0.052(5) 0.038(4) 0.046(5) 0.004(4) -0.010(4) -0.015(4) B3 0.052(7) 0.037(6) 0.042(6) -0.018(5) 0.002(5) -0.019(5) Cl 0.124(3) 0.088(2) 0.097(2) -0.031(2) -0.073(2) -0.012(2) C2 0.049(6) 0.027(4) 0.028(4) -0.012(4) -0.003(4) -0.015(4) B5 0.053(7) 0.028(5) 0.036(5) -0.010(4) -0.015(5) -0.005(5) C14 0.042(5) 0.039(5) 0.030(4) -0.010(4) -0.002(4) -0.014(4) C1 0.042(5) 0.037(5) 0.027(4) -0.010(4) -0.005(4) -0.012(4) C15 0.049(6) 0.049(6) 0.042(5) -0.013(5) -0.006(5) -0.009(5) C7 0.041(6) 0.036(5) 0.043(5) -0.006(4) -0.012(4) -0.005(4) B12 0.056(8) 0.044(6) 0.041(6) -0.019(5) 0.001(6) -0.009(6) B7 0.055(7) 0.045(6) 0.032(5) -0.010(5) -0.005(5) -0.014(6) C13 0.044(6) 0.038(5) 0.042(5) -0.021(4) 0.008(4) -0.017(4) B8 0.053(7) 0.047(6) 0.039(6) -0.020(5) 0.000(5) -0.014(6) B11 0.044(7) 0.045(6) 0.039(6) -0.010(5) -0.005(5) -0.008(5) C18 0.056(7) 0.045(6) 0.056(6) -0.023(5) -0.002(5) -0.018(5) B4 0.061(8) 0.025(5) 0.044(6) -0.009(5) 0.003(6) -0.008(5) C4 0.046(6) 0.046(6) 0.064(7) 0.003(6) -0.008(5) -0.014(5) C17 0.070(8) 0.063(7) 0.075(8) -0.041(6) -0.020(6) -0.019(6) C10 0.067(8) 0.054(7) 0.096(9) 0.000(7) -0.014(7) -0.027(6) C3 0.038(5) 0.041(5) 0.054(6) -0.029(5) -0.010(5) 0.004(4) C16 0.071(8) 0.066(7) 0.059(7) -0.022(6) -0.031(6) -0.016(6) B10 0.063(8) 0.035(6) 0.047(6) -0.012(5) -0.002(6) -0.006(6) C9 0.089(10) 0.081(8) 0.093(9) -0.069(8) -0.013(8) -0.017(7) C19 0.100(10) 0.051(6) 0.082(8) -0.024(6) -0.011(7) -0.039(7) C5 0.049(6) 0.060(6) 0.039(5) -0.020(5) -0.002(5) -0.012(5) C8 0.060(8) 0.077(8) 0.045(6) -0.001(6) -0.007(5) -0.007(6) C12 0.104(11) 0.049(7) 0.105(10) -0.049(7) -0.009(9) -0.005(7) C11 0.089(10) 0.123(12) 0.050(7) -0.034(8) 0.013(7) -0.030(9) C6 0.053(6) 0.038(5) 0.051(6) -0.025(5) -0.010(5) -0.002(5) B6 0.054(7) 0.040(6) 0.036(5) -0.014(5) 0.002(5) -0.022(5) B9 0.067(8) 0.034(6) 0.051(7) -0.022(5) 0.004(6) -0.017(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 N1 2.043(8) . ? Ir1 C7 2.148(9) . ? Ir1 C5 2.170(10) . ? Ir1 C4 2.170(10) . ? Ir1 C6 2.176(10) . ? Ir1 C3 2.196(10) . ? Ir1 S2 2.319(2) . ? Ir1 S1 2.366(3) . ? S1 C1 1.776(9) . ? S2 C14 1.747(9) . ? S2 C2 1.839(9) . ? N1 C13 1.328(12) . ? N1 H1 0.8600 . ? B3 C2 1.709(14) . ? B3 C1 1.744(13) . ? B3 B9 1.760(16) . ? B3 B4 1.774(16) . ? B3 B8 1.782(15) . ? B3 H3 1.1000 . ? Cl C16 1.750(11) . ? C2 C1 1.667(11) . ? C2 B4 1.700(12) . ? C2 B5 1.706(14) . ? C2 B6 1.721(14) . ? B5 B10 1.757(16) . ? B5 B11 1.761(15) . ? B5 B4 1.767(16) . ? B5 B6 1.780(14) . ? B5 H5 1.1000 . ? C14 C13 1.421(12) . ? C14 C15 1.424(12) . ? C1 B7 1.689(15) . ? C1 B8 1.723(14) . ? C1 B6 1.742(14) . ? C15 C16 1.323(15) . ? C15 H15 0.9300 . ? C7 C6 1.401(13) . ? C7 C3 1.457(12) . ? C7 C8 1.505(12) . ? B12 B7 1.786(16) . ? B12 B10 1.786(16) . ? B12 B9 1.788(17) . ? B12 B11 1.795(17) . ? B12 B8 1.805(17) . ? B12 H12 1.1000 . ? B7 B6 1.736(15) . ? B7 B8 1.779(16) . ? B7 B11 1.782(15) . ? B7 H7 1.1000 . ? C13 C18 1.419(13) . ? B8 B9 1.796(15) . ? B8 H8 1.1000 . ? B11 B6 1.752(16) . ? B11 B10 1.786(16) . ? B11 H11 1.1000 . ? C18 C17 1.366(14) . ? C18 C19 1.513(13) . ? B4 B9 1.757(16) . ? B4 B10 1.765(17) . ? B4 H4 1.1000 . ? C4 C5 1.399(15) . ? C4 C3 1.431(14) . ? C4 C10 1.517(13) . ? C17 C16 1.392(15) . ? C17 H17 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C3 C9 1.494(13) . ? B10 B9 1.796(18) . ? B10 H10 1.1000 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C5 C6 1.424(13) . ? C5 C11 1.556(14) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C12 C6 1.516(14) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? B6 H6 1.1000 . ? B9 H9 1.1000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C7 115.3(3) . . ? N1 Ir1 C5 108.8(4) . . ? C7 Ir1 C5 64.0(4) . . ? N1 Ir1 C4 145.2(4) . . ? C7 Ir1 C4 65.0(4) . . ? C5 Ir1 C4 37.6(4) . . ? N1 Ir1 C6 94.7(3) . . ? C7 Ir1 C6 37.8(4) . . ? C5 Ir1 C6 38.3(4) . . ? C4 Ir1 C6 63.9(4) . . ? N1 Ir1 C3 154.4(3) . . ? C7 Ir1 C3 39.2(3) . . ? C5 Ir1 C3 63.3(4) . . ? C4 Ir1 C3 38.3(4) . . ? C6 Ir1 C3 63.7(3) . . ? N1 Ir1 S2 81.7(2) . . ? C7 Ir1 S2 161.6(2) . . ? C5 Ir1 S2 104.9(3) . . ? C4 Ir1 S2 97.1(3) . . ? C6 Ir1 S2 139.5(3) . . ? C3 Ir1 S2 123.4(3) . . ? N1 Ir1 S1 88.0(2) . . ? C7 Ir1 S1 96.5(3) . . ? C5 Ir1 S1 158.1(3) . . ? C4 Ir1 S1 126.7(3) . . ? C6 Ir1 S1 129.3(3) . . ? C3 Ir1 S1 95.5(3) . . ? S2 Ir1 S1 91.00(8) . . ? C1 S1 Ir1 104.5(3) . . ? C14 S2 C2 106.1(4) . . ? C14 S2 Ir1 99.9(3) . . ? C2 S2 Ir1 105.8(3) . . ? C13 N1 Ir1 122.7(6) . . ? C13 N1 H1 118.6 . . ? Ir1 N1 H1 118.6 . . ? C2 B3 C1 57.7(5) . . ? C2 B3 B9 104.3(8) . . ? C1 B3 B9 105.6(8) . . ? C2 B3 B4 58.4(6) . . ? C1 B3 B4 105.5(8) . . ? B9 B3 B4 59.6(6) . . ? C2 B3 B8 104.6(8) . . ? C1 B3 B8 58.5(6) . . ? B9 B3 B8 60.9(6) . . ? B4 B3 B8 108.4(8) . . ? C2 B3 H3 124.9 . . ? C1 B3 H3 123.9 . . ? B9 B3 H3 122.7 . . ? B4 B3 H3 122.1 . . ? B8 B3 H3 121.9 . . ? C1 C2 B4 112.5(7) . . ? C1 C2 B5 112.5(7) . . ? B4 C2 B5 62.5(6) . . ? C1 C2 B3 62.2(5) . . ? B4 C2 B3 62.7(6) . . ? B5 C2 B3 114.7(7) . . ? C1 C2 B6 61.9(5) . . ? B4 C2 B6 114.3(7) . . ? B5 C2 B6 62.6(6) . . ? B3 C2 B6 114.9(7) . . ? C1 C2 S2 116.0(6) . . ? B4 C2 S2 118.7(6) . . ? B5 C2 S2 123.7(6) . . ? B3 C2 S2 112.1(6) . . ? B6 C2 S2 120.5(6) . . ? C2 B5 B10 105.1(8) . . ? C2 B5 B11 104.9(7) . . ? B10 B5 B11 61.0(6) . . ? C2 B5 B4 58.6(6) . . ? B10 B5 B4 60.1(7) . . ? B11 B5 B4 108.7(8) . . ? C2 B5 B6 59.1(6) . . ? B10 B5 B6 108.4(7) . . ? B11 B5 B6 59.3(6) . . ? B4 B5 B6 108.2(7) . . ? C2 B5 H5 124.7 . . ? B10 B5 H5 121.8 . . ? B11 B5 H5 122.1 . . ? B4 B5 H5 121.3 . . ? B6 B5 H5 121.5 . . ? C13 C14 C15 121.5(9) . . ? C13 C14 S2 117.0(7) . . ? C15 C14 S2 121.5(7) . . ? C2 C1 B7 108.1(7) . . ? C2 C1 B8 109.1(6) . . ? B7 C1 B8 62.9(6) . . ? C2 C1 B3 60.1(5) . . ? B7 C1 B3 112.4(7) . . ? B8 C1 B3 61.8(6) . . ? C2 C1 B6 60.6(5) . . ? B7 C1 B6 60.8(6) . . ? B8 C1 B6 112.9(7) . . ? B3 C1 B6 112.0(7) . . ? C2 C1 S1 119.1(6) . . ? B7 C1 S1 122.5(6) . . ? B8 C1 S1 122.3(6) . . ? B3 C1 S1 118.5(7) . . ? B6 C1 S1 117.3(6) . . ? C16 C15 C14 119.4(9) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C6 C7 C3 107.7(8) . . ? C6 C7 C8 127.2(9) . . ? C3 C7 C8 124.6(9) . . ? C6 C7 Ir1 72.2(6) . . ? C3 C7 Ir1 72.2(5) . . ? C8 C7 Ir1 127.9(7) . . ? B7 B12 B10 107.0(8) . . ? B7 B12 B9 106.6(8) . . ? B10 B12 B9 60.3(7) . . ? B7 B12 B11 59.7(6) . . ? B10 B12 B11 59.8(6) . . ? B9 B12 B11 107.8(8) . . ? B7 B12 B8 59.4(6) . . ? B10 B12 B8 108.5(8) . . ? B9 B12 B8 60.0(6) . . ? B11 B12 B8 108.1(8) . . ? B7 B12 H12 122.9 . . ? B10 B12 H12 121.6 . . ? B9 B12 H12 122.1 . . ? B11 B12 H12 121.7 . . ? B8 B12 H12 121.5 . . ? C1 B7 B6 61.1(6) . . ? C1 B7 B8 59.5(6) . . ? B6 B7 B8 110.4(8) . . ? C1 B7 B11 107.6(7) . . ? B6 B7 B11 59.7(6) . . ? B8 B7 B11 109.8(8) . . ? C1 B7 B12 107.0(8) . . ? B6 B7 B12 108.8(7) . . ? B8 B7 B12 60.8(7) . . ? B11 B7 B12 60.4(6) . . ? C1 B7 H7 122.5 . . ? B6 B7 H7 120.5 . . ? B8 B7 H7 120.2 . . ? B11 B7 H7 121.5 . . ? B12 B7 H7 121.8 . . ? N1 C13 C14 117.8(8) . . ? N1 C13 C18 125.7(9) . . ? C14 C13 C18 116.4(9) . . ? C1 B8 B7 57.6(6) . . ? C1 B8 B3 59.7(6) . . ? B7 B8 B3 106.4(8) . . ? C1 B8 B9 105.0(7) . . ? B7 B8 B9 106.5(8) . . ? B3 B8 B9 58.9(6) . . ? C1 B8 B12 104.7(8) . . ? B7 B8 B12 59.8(7) . . ? B3 B8 B12 106.7(8) . . ? B9 B8 B12 59.6(6) . . ? C1 B8 H8 124.2 . . ? B7 B8 H8 122.7 . . ? B3 B8 H8 122.2 . . ? B9 B8 H8 123.0 . . ? B12 B8 H8 122.7 . . ? B6 B11 B5 60.9(6) . . ? B6 B11 B7 58.9(6) . . ? B5 B11 B7 106.9(8) . . ? B6 B11 B10 108.3(8) . . ? B5 B11 B10 59.4(6) . . ? B7 B11 B10 107.2(9) . . ? B6 B11 B12 107.7(8) . . ? B5 B11 B12 107.2(8) . . ? B7 B11 B12 59.9(6) . . ? B10 B11 B12 59.8(7) . . ? B6 B11 H11 121.5 . . ? B5 B11 H11 122.1 . . ? B7 B11 H11 122.7 . . ? B10 B11 H11 121.9 . . ? B12 B11 H11 122.0 . . ? C17 C18 C13 119.7(9) . . ? C17 C18 C19 121.6(10) . . ? C13 C18 C19 118.7(9) . . ? C2 B4 B9 104.8(7) . . ? C2 B4 B5 58.9(6) . . ? B9 B4 B5 108.7(8) . . ? C2 B4 B10 105.0(8) . . ? B9 B4 B10 61.3(7) . . ? B5 B4 B10 59.7(7) . . ? C2 B4 B3 58.9(5) . . ? B9 B4 B3 59.8(6) . . ? B5 B4 B3 108.7(7) . . ? B10 B4 B3 109.2(8) . . ? C2 B4 H4 124.8 . . ? B9 B4 H4 121.9 . . ? B5 B4 H4 121.3 . . ? B10 B4 H4 121.7 . . ? B3 B4 H4 121.0 . . ? C5 C4 C3 108.0(8) . . ? C5 C4 C10 125.8(11) . . ? C3 C4 C10 125.6(11) . . ? C5 C4 Ir1 71.2(6) . . ? C3 C4 Ir1 71.8(6) . . ? C10 C4 Ir1 129.2(8) . . ? C18 C17 C16 122.5(10) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C3 C7 106.9(9) . . ? C4 C3 C9 127.2(10) . . ? C7 C3 C9 125.8(9) . . ? C4 C3 Ir1 69.9(6) . . ? C7 C3 Ir1 68.6(5) . . ? C9 C3 Ir1 129.3(8) . . ? C15 C16 C17 120.5(10) . . ? C15 C16 Cl 119.8(9) . . ? C17 C16 Cl 119.6(9) . . ? B5 B10 B4 60.2(6) . . ? B5 B10 B11 59.6(6) . . ? B4 B10 B11 107.7(8) . . ? B5 B10 B12 107.8(8) . . ? B4 B10 B12 107.3(9) . . ? B11 B10 B12 60.3(6) . . ? B5 B10 B9 107.4(8) . . ? B4 B10 B9 59.1(7) . . ? B11 B10 B9 107.9(8) . . ? B12 B10 B9 59.9(7) . . ? B5 B10 H10 121.9 . . ? B4 B10 H10 122.2 . . ? B11 B10 H10 121.7 . . ? B12 B10 H10 121.8 . . ? B9 B10 H10 122.2 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4 C5 C6 109.1(8) . . ? C4 C5 C11 126.8(10) . . ? C6 C5 C11 124.1(10) . . ? C4 C5 Ir1 71.2(6) . . ? C6 C5 Ir1 71.1(6) . . ? C11 C5 Ir1 125.0(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C6 C5 108.2(8) . . ? C7 C6 C12 126.2(9) . . ? C5 C6 C12 125.6(10) . . ? C7 C6 Ir1 70.0(5) . . ? C5 C6 Ir1 70.6(6) . . ? C12 C6 Ir1 126.0(8) . . ? C2 B6 B7 103.6(7) . . ? C2 B6 C1 57.5(5) . . ? B7 B6 C1 58.1(6) . . ? C2 B6 B11 104.6(7) . . ? B7 B6 B11 61.4(6) . . ? C1 B6 B11 106.6(8) . . ? C2 B6 B5 58.3(5) . . ? B7 B6 B5 108.1(8) . . ? C1 B6 B5 105.5(7) . . ? B11 B6 B5 59.8(6) . . ? C2 B6 H6 125.3 . . ? B7 B6 H6 122.4 . . ? C1 B6 H6 123.7 . . ? B11 B6 H6 121.9 . . ? B5 B6 H6 122.1 . . ? B4 B9 B3 60.6(6) . . ? B4 B9 B12 107.5(9) . . ? B3 B9 B12 108.4(8) . . ? B4 B9 B8 108.5(7) . . ? B3 B9 B8 60.1(6) . . ? B12 B9 B8 60.5(6) . . ? B4 B9 B10 59.6(7) . . ? B3 B9 B10 108.4(8) . . ? B12 B9 B10 59.8(7) . . ? B8 B9 B10 108.5(8) . . ? B4 B9 H9 121.8 . . ? B3 B9 H9 121.3 . . ? B12 B9 H9 121.8 . . ? B8 B9 H9 121.2 . . ? B10 B9 H9 121.8 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 3.425 _refine_diff_density_min -2.539 _refine_diff_density_rms 0.211 data_6 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 843470' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 B10 Cl2 Ir N S2' _chemical_formula_weight 693.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.941(3) _cell_length_b 12.283(3) _cell_length_c 12.409(3) _cell_angle_alpha 69.785(3) _cell_angle_beta 73.072(3) _cell_angle_gamma 80.042(4) _cell_volume 1356.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 5.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.312 _exptl_absorpt_correction_T_max 0.429 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7377 _diffrn_reflns_av_R_equivalents 0.1215 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5201 _reflns_number_gt 4729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^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 5201 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.65307(2) 0.793345(17) 0.662805(17) 0.03449(10) Uani 1 1 d . . . S2 S 0.52005(15) 0.65530(12) 0.81880(13) 0.0358(3) Uani 1 1 d . . . S1 S 0.48071(16) 0.94461(13) 0.69854(14) 0.0458(4) Uani 1 1 d . . . Cl1 Cl 0.3929(3) 0.7043(2) 0.40840(18) 0.0777(6) Uani 1 1 d . . . C2 C 0.3853(6) 0.7366(5) 0.9026(5) 0.0366(12) Uani 1 1 d . . . C13 C 0.4514(7) 0.6713(6) 0.6195(6) 0.0418(13) Uani 1 1 d . . . N1 N 0.5333(6) 0.7588(5) 0.5701(5) 0.0470(12) Uani 1 1 d . . . H1 H 0.5365 0.8019 0.4983 0.056 Uiso 1 1 calc R . . C1 C 0.3758(6) 0.8805(5) 0.8438(5) 0.0387(13) Uani 1 1 d . . . B6 B 0.2368(7) 0.8050(6) 0.8537(6) 0.0394(14) Uani 1 1 d . . . H6 H 0.2090 0.7987 0.7766 0.047 Uiso 1 1 calc R . . C14 C 0.4296(6) 0.6087(5) 0.7406(5) 0.0408(13) Uani 1 1 d . . . C18 C 0.3774(8) 0.6310(6) 0.5579(6) 0.0524(16) Uani 1 1 d . . . C5 C 0.8464(7) 0.8040(6) 0.5225(6) 0.0473(15) Uani 1 1 d . . . B5 B 0.2249(8) 0.6864(6) 0.9885(6) 0.0439(15) Uani 1 1 d . . . H5 H 0.1894 0.6028 0.9981 0.053 Uiso 1 1 calc R . . C6 C 0.8221(6) 0.9029(5) 0.5578(6) 0.0432(14) Uani 1 1 d . . . B7 B 0.2065(7) 0.9355(6) 0.8898(6) 0.0424(15) Uani 1 1 d . . . H7 H 0.1575 1.0145 0.8356 0.051 Uiso 1 1 calc R . . Cl2 Cl 0.1895(4) 0.3558(3) 0.8013(3) 0.1070(11) Uani 1 1 d . . . C7 C 0.8266(7) 0.8679(6) 0.6806(6) 0.0465(14) Uani 1 1 d . . . C3 C 0.8534(6) 0.7459(6) 0.7181(6) 0.0479(15) Uani 1 1 d . . . C15 C 0.3530(7) 0.5107(6) 0.7978(7) 0.0499(16) Uani 1 1 d . . . H15 H 0.3470 0.4699 0.8775 0.060 Uiso 1 1 calc R . . C4 C 0.8602(7) 0.7036(6) 0.6240(6) 0.0502(15) Uani 1 1 d . . . B3 B 0.4563(8) 0.8158(7) 0.9603(6) 0.0427(15) Uani 1 1 d . . . H3 H 0.5697 0.8158 0.9511 0.051 Uiso 1 1 calc R . . B8 B 0.3409(8) 0.9424(7) 0.9549(7) 0.0448(16) Uani 1 1 d . . . H8 H 0.3787 1.0259 0.9428 0.054 Uiso 1 1 calc R . . B11 B 0.1093(7) 0.8134(7) 0.9847(6) 0.0442(16) Uani 1 1 d . . . H11 H -0.0039 0.8125 0.9937 0.053 Uiso 1 1 calc R . . B4 B 0.3590(8) 0.6938(7) 1.0539(6) 0.0471(17) Uani 1 1 d . . . H4 H 0.4093 0.6141 1.1063 0.056 Uiso 1 1 calc R . . C16 C 0.2873(9) 0.4761(7) 0.7341(8) 0.064(2) Uani 1 1 d . . . C17 C 0.2998(8) 0.5364(8) 0.6144(8) 0.065(2) Uani 1 1 d . . . H17 H 0.2545 0.5118 0.5720 0.078 Uiso 1 1 calc R . . B12 B 0.1724(8) 0.9006(7) 1.0462(7) 0.0478(16) Uani 1 1 d . . . H12 H 0.1002 0.9566 1.0943 0.057 Uiso 1 1 calc R . . C8 C 0.8213(9) 0.9458(9) 0.7507(8) 0.077(3) Uani 1 1 d . . . H8A H 0.9132 0.9717 0.7332 0.115 Uiso 1 1 calc R . . H8B H 0.7918 0.9041 0.8337 0.115 Uiso 1 1 calc R . . H8C H 0.7554 1.0118 0.7304 0.115 Uiso 1 1 calc R . . B9 B 0.3293(8) 0.8253(7) 1.0895(7) 0.0484(17) Uani 1 1 d . . . H9 H 0.3592 0.8320 1.1654 0.058 Uiso 1 1 calc R . . B10 B 0.1840(8) 0.7451(7) 1.1080(6) 0.0477(17) Uani 1 1 d . . . H10 H 0.1198 0.7002 1.1963 0.057 Uiso 1 1 calc R . . C12 C 0.8050(8) 1.0304(7) 0.4819(8) 0.069(2) Uani 1 1 d . . . H12A H 0.7746 1.0343 0.4139 0.104 Uiso 1 1 calc R . . H12B H 0.8938 1.0640 0.4563 0.104 Uiso 1 1 calc R . . H12C H 0.7361 1.0727 0.5281 0.104 Uiso 1 1 calc R . . C9 C 0.8729(10) 0.6683(10) 0.8401(7) 0.085(3) Uani 1 1 d . . . H9A H 0.8653 0.7158 0.8892 0.127 Uiso 1 1 calc R . . H9B H 0.9643 0.6264 0.8310 0.127 Uiso 1 1 calc R . . H9C H 0.8013 0.6142 0.8765 0.127 Uiso 1 1 calc R . . C11 C 0.8566(11) 0.8002(11) 0.4003(7) 0.083(3) Uani 1 1 d . . . H11A H 0.9525 0.8077 0.3539 0.125 Uiso 1 1 calc R . . H11B H 0.7968 0.8631 0.3626 0.125 Uiso 1 1 calc R . . H11C H 0.8271 0.7274 0.4064 0.125 Uiso 1 1 calc R . . C10 C 0.8956(11) 0.5808(8) 0.6214(12) 0.097(3) Uani 1 1 d . . . H10A H 0.8784 0.5284 0.7011 0.146 Uiso 1 1 calc R . . H10B H 0.9932 0.5709 0.5817 0.146 Uiso 1 1 calc R . . H10C H 0.8378 0.5645 0.5797 0.146 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 0.03523(14) 0.03269(14) 0.03536(14) -0.01224(9) -0.00679(9) -0.00250(9) S2 0.0390(7) 0.0291(6) 0.0398(7) -0.0107(6) -0.0122(6) -0.0001(5) S1 0.0423(8) 0.0330(7) 0.0469(8) -0.0035(6) -0.0007(6) -0.0007(6) Cl1 0.1008(16) 0.0893(15) 0.0583(11) -0.0272(11) -0.0362(11) -0.0104(12) C2 0.038(3) 0.032(3) 0.037(3) -0.008(2) -0.011(2) -0.001(2) C13 0.047(3) 0.039(3) 0.046(3) -0.020(3) -0.017(3) 0.002(3) N1 0.050(3) 0.048(3) 0.041(3) -0.008(2) -0.011(2) -0.011(2) C1 0.038(3) 0.033(3) 0.044(3) -0.010(2) -0.011(2) -0.001(2) B6 0.035(3) 0.039(3) 0.042(3) -0.011(3) -0.009(3) -0.002(3) C14 0.043(3) 0.037(3) 0.046(3) -0.017(3) -0.011(3) -0.003(2) C18 0.056(4) 0.057(4) 0.056(4) -0.029(3) -0.020(3) -0.004(3) C5 0.041(3) 0.054(4) 0.048(4) -0.023(3) -0.005(3) -0.002(3) B5 0.045(4) 0.040(4) 0.037(3) -0.006(3) -0.003(3) -0.006(3) C6 0.033(3) 0.040(3) 0.050(3) -0.012(3) -0.001(2) -0.007(2) B7 0.035(3) 0.041(4) 0.045(4) -0.012(3) -0.008(3) 0.005(3) Cl2 0.127(2) 0.107(2) 0.1030(19) -0.0334(16) -0.0115(17) -0.0783(19) C7 0.042(3) 0.051(4) 0.049(4) -0.019(3) -0.005(3) -0.012(3) C3 0.037(3) 0.059(4) 0.045(3) -0.013(3) -0.010(3) -0.006(3) C15 0.047(4) 0.047(4) 0.060(4) -0.023(3) -0.008(3) -0.011(3) C4 0.037(3) 0.050(4) 0.059(4) -0.020(3) -0.007(3) 0.004(3) B3 0.041(4) 0.047(4) 0.046(4) -0.020(3) -0.016(3) 0.002(3) B8 0.045(4) 0.041(4) 0.055(4) -0.025(3) -0.014(3) 0.003(3) B11 0.034(3) 0.049(4) 0.041(4) -0.010(3) -0.002(3) -0.003(3) B4 0.054(4) 0.042(4) 0.038(4) -0.004(3) -0.017(3) 0.005(3) C16 0.062(5) 0.060(5) 0.079(5) -0.031(4) -0.009(4) -0.024(4) C17 0.063(5) 0.076(5) 0.076(5) -0.042(4) -0.019(4) -0.017(4) B12 0.046(4) 0.051(4) 0.046(4) -0.020(3) -0.010(3) 0.003(3) C8 0.066(5) 0.094(7) 0.093(6) -0.059(5) -0.007(5) -0.024(5) B9 0.051(4) 0.053(4) 0.044(4) -0.020(3) -0.016(3) 0.004(3) B10 0.053(4) 0.048(4) 0.035(3) -0.009(3) -0.005(3) -0.003(3) C12 0.054(4) 0.052(4) 0.084(6) 0.002(4) -0.015(4) -0.012(3) C9 0.071(5) 0.104(7) 0.063(5) 0.014(5) -0.035(5) -0.016(5) C11 0.086(6) 0.122(9) 0.052(5) -0.053(5) 0.004(4) -0.019(6) C10 0.079(6) 0.055(5) 0.157(11) -0.051(6) -0.020(6) 0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N1 2.057(5) . ? Ir1 C6 2.151(6) . ? Ir1 C4 2.166(7) . ? Ir1 C5 2.173(7) . ? Ir1 C7 2.184(6) . ? Ir1 C3 2.213(6) . ? Ir1 S2 2.3211(15) . ? Ir1 S1 2.3687(17) . ? S2 C14 1.775(6) . ? S2 C2 1.821(6) . ? S1 C1 1.779(6) . ? Cl1 C18 1.733(7) . ? C2 C1 1.660(8) . ? C2 B4 1.717(9) . ? C2 B5 1.719(9) . ? C2 B3 1.724(9) . ? C2 B6 1.730(8) . ? C13 N1 1.324(8) . ? C13 C14 1.402(9) . ? C13 C18 1.444(9) . ? C1 B7 1.711(9) . ? C1 B8 1.718(10) . ? C1 B3 1.738(9) . ? C1 B6 1.746(9) . ? B6 B7 1.763(10) . ? B6 B11 1.770(10) . ? B6 B5 1.787(9) . ? C14 C15 1.394(9) . ? C18 C17 1.367(11) . ? C5 C6 1.390(10) . ? C5 C4 1.448(9) . ? C5 C11 1.507(10) . ? B5 B11 1.765(11) . ? B5 B4 1.780(11) . ? B5 B10 1.781(11) . ? C6 C7 1.445(9) . ? C6 C12 1.533(9) . ? B7 B12 1.777(10) . ? B7 B8 1.777(10) . ? B7 B11 1.786(10) . ? Cl2 C16 1.732(7) . ? C7 C3 1.409(10) . ? C7 C8 1.485(11) . ? C3 C4 1.413(10) . ? C3 C9 1.532(9) . ? C15 C16 1.364(10) . ? C4 C10 1.497(11) . ? B3 B9 1.754(11) . ? B3 B8 1.759(10) . ? B3 B4 1.782(11) . ? B8 B12 1.773(11) . ? B8 B9 1.777(11) . ? B11 B10 1.776(10) . ? B11 B12 1.788(11) . ? B4 B10 1.763(11) . ? B4 B9 1.773(11) . ? C16 C17 1.391(12) . ? B12 B10 1.792(11) . ? B12 B9 1.795(10) . ? B9 B10 1.803(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 C6 115.8(2) . . ? N1 Ir1 C4 107.9(3) . . ? C6 Ir1 C4 64.3(3) . . ? N1 Ir1 C5 94.4(2) . . ? C6 Ir1 C5 37.5(3) . . ? C4 Ir1 C5 39.0(3) . . ? N1 Ir1 C7 154.7(2) . . ? C6 Ir1 C7 38.9(2) . . ? C4 Ir1 C7 63.8(3) . . ? C5 Ir1 C7 63.7(3) . . ? N1 Ir1 C3 144.7(3) . . ? C6 Ir1 C3 63.5(2) . . ? C4 Ir1 C3 37.6(3) . . ? C5 Ir1 C3 63.2(2) . . ? C7 Ir1 C3 37.4(3) . . ? N1 Ir1 S2 81.87(15) . . ? C6 Ir1 S2 160.75(18) . . ? C4 Ir1 S2 104.35(19) . . ? C5 Ir1 S2 140.02(19) . . ? C7 Ir1 S2 122.87(18) . . ? C3 Ir1 S2 97.84(17) . . ? N1 Ir1 S1 88.80(18) . . ? C6 Ir1 S1 96.52(18) . . ? C4 Ir1 S1 158.5(2) . . ? C5 Ir1 S1 128.79(19) . . ? C7 Ir1 S1 95.3(2) . . ? C3 Ir1 S1 126.4(2) . . ? S2 Ir1 S1 91.06(5) . . ? C14 S2 C2 104.9(3) . . ? C14 S2 Ir1 100.2(2) . . ? C2 S2 Ir1 105.93(18) . . ? C1 S1 Ir1 104.1(2) . . ? C1 C2 B4 111.9(5) . . ? C1 C2 B5 112.2(5) . . ? B4 C2 B5 62.4(4) . . ? C1 C2 B3 61.8(4) . . ? B4 C2 B3 62.4(4) . . ? B5 C2 B3 114.2(5) . . ? C1 C2 B6 62.0(3) . . ? B4 C2 B6 113.9(5) . . ? B5 C2 B6 62.4(4) . . ? B3 C2 B6 114.4(5) . . ? C1 C2 S2 116.4(4) . . ? B4 C2 S2 118.7(4) . . ? B5 C2 S2 123.9(4) . . ? B3 C2 S2 112.4(4) . . ? B6 C2 S2 120.9(4) . . ? N1 C13 C14 121.0(6) . . ? N1 C13 C18 125.1(6) . . ? C14 C13 C18 113.9(6) . . ? C13 N1 Ir1 121.0(4) . . ? C2 C1 B7 109.1(4) . . ? C2 C1 B8 109.2(5) . . ? B7 C1 B8 62.4(4) . . ? C2 C1 B3 60.9(4) . . ? B7 C1 B3 112.3(5) . . ? B8 C1 B3 61.2(4) . . ? C2 C1 B6 61.0(3) . . ? B7 C1 B6 61.3(4) . . ? B8 C1 B6 112.7(5) . . ? B3 C1 B6 112.9(5) . . ? C2 C1 S1 119.3(4) . . ? B7 C1 S1 121.0(4) . . ? B8 C1 S1 122.8(4) . . ? B3 C1 S1 119.5(4) . . ? B6 C1 S1 116.3(4) . . ? C2 B6 C1 57.0(3) . . ? C2 B6 B7 103.7(5) . . ? C1 B6 B7 58.4(4) . . ? C2 B6 B11 103.9(5) . . ? C1 B6 B11 105.4(5) . . ? B7 B6 B11 60.7(4) . . ? C2 B6 B5 58.5(4) . . ? C1 B6 B5 105.1(5) . . ? B7 B6 B5 107.9(5) . . ? B11 B6 B5 59.5(4) . . ? C15 C14 C13 124.7(6) . . ? C15 C14 S2 120.0(5) . . ? C13 C14 S2 115.1(4) . . ? C17 C18 C13 121.4(7) . . ? C17 C18 Cl1 120.6(5) . . ? C13 C18 Cl1 118.0(5) . . ? C6 C5 C4 108.2(6) . . ? C6 C5 C11 126.5(7) . . ? C4 C5 C11 125.3(7) . . ? C6 C5 Ir1 70.4(4) . . ? C4 C5 Ir1 70.2(4) . . ? C11 C5 Ir1 124.9(5) . . ? C2 B5 B11 104.6(5) . . ? C2 B5 B4 58.8(4) . . ? B11 B5 B4 107.4(5) . . ? C2 B5 B10 104.4(5) . . ? B11 B5 B10 60.1(4) . . ? B4 B5 B10 59.3(4) . . ? C2 B5 B6 59.1(3) . . ? B11 B5 B6 59.7(4) . . ? B4 B5 B6 108.2(5) . . ? B10 B5 B6 108.1(5) . . ? C5 C6 C7 108.4(6) . . ? C5 C6 C12 128.2(7) . . ? C7 C6 C12 123.2(7) . . ? C5 C6 Ir1 72.1(4) . . ? C7 C6 Ir1 71.8(3) . . ? C12 C6 Ir1 125.7(4) . . ? C1 B7 B6 60.3(4) . . ? C1 B7 B12 106.0(5) . . ? B6 B7 B12 108.8(5) . . ? C1 B7 B8 59.0(4) . . ? B6 B7 B8 109.1(5) . . ? B12 B7 B8 59.9(4) . . ? C1 B7 B11 106.2(5) . . ? B6 B7 B11 59.8(4) . . ? B12 B7 B11 60.3(4) . . ? B8 B7 B11 108.0(5) . . ? C3 C7 C6 107.2(6) . . ? C3 C7 C8 125.7(7) . . ? C6 C7 C8 126.8(7) . . ? C3 C7 Ir1 72.4(4) . . ? C6 C7 Ir1 69.3(3) . . ? C8 C7 Ir1 128.9(5) . . ? C7 C3 C4 109.1(6) . . ? C7 C3 C9 126.9(8) . . ? C4 C3 C9 124.0(8) . . ? C7 C3 Ir1 70.2(4) . . ? C4 C3 Ir1 69.4(4) . . ? C9 C3 Ir1 126.5(5) . . ? C16 C15 C14 118.3(7) . . ? C3 C4 C5 107.0(6) . . ? C3 C4 C10 127.6(8) . . ? C5 C4 C10 124.9(8) . . ? C3 C4 Ir1 73.0(4) . . ? C5 C4 Ir1 70.8(4) . . ? C10 C4 Ir1 127.9(6) . . ? C2 B3 C1 57.3(3) . . ? C2 B3 B9 105.4(5) . . ? C1 B3 B9 106.5(5) . . ? C2 B3 B8 104.5(5) . . ? C1 B3 B8 58.9(4) . . ? B9 B3 B8 60.8(4) . . ? C2 B3 B4 58.6(4) . . ? C1 B3 B4 105.3(5) . . ? B9 B3 B4 60.2(5) . . ? B8 B3 B4 108.1(5) . . ? C1 B8 B3 60.0(4) . . ? C1 B8 B12 105.8(5) . . ? B3 B8 B12 108.2(5) . . ? C1 B8 B9 106.3(5) . . ? B3 B8 B9 59.5(4) . . ? B12 B8 B9 60.8(4) . . ? C1 B8 B7 58.6(4) . . ? B3 B8 B7 108.2(5) . . ? B12 B8 B7 60.1(4) . . ? B9 B8 B7 108.6(5) . . ? B5 B11 B6 60.7(4) . . ? B5 B11 B10 60.4(4) . . ? B6 B11 B10 109.1(5) . . ? B5 B11 B7 107.9(5) . . ? B6 B11 B7 59.5(4) . . ? B10 B11 B7 108.0(5) . . ? B5 B11 B12 108.5(5) . . ? B6 B11 B12 107.9(5) . . ? B10 B11 B12 60.4(4) . . ? B7 B11 B12 59.6(4) . . ? C2 B4 B10 105.3(5) . . ? C2 B4 B9 104.9(5) . . ? B10 B4 B9 61.3(5) . . ? C2 B4 B5 58.8(4) . . ? B10 B4 B5 60.4(4) . . ? B9 B4 B5 109.4(5) . . ? C2 B4 B3 59.0(4) . . ? B10 B4 B3 108.4(5) . . ? B9 B4 B3 59.1(4) . . ? B5 B4 B3 108.5(5) . . ? C15 C16 C17 120.3(7) . . ? C15 C16 Cl2 120.2(7) . . ? C17 C16 Cl2 119.5(6) . . ? C18 C17 C16 121.2(7) . . ? B8 B12 B7 60.1(4) . . ? B8 B12 B11 108.1(5) . . ? B7 B12 B11 60.1(4) . . ? B8 B12 B10 107.9(5) . . ? B7 B12 B10 107.7(5) . . ? B11 B12 B10 59.5(4) . . ? B8 B12 B9 59.7(4) . . ? B7 B12 B9 107.8(5) . . ? B11 B12 B9 107.9(6) . . ? B10 B12 B9 60.3(4) . . ? B3 B9 B4 60.7(4) . . ? B3 B9 B8 59.8(4) . . ? B4 B9 B8 107.7(5) . . ? B3 B9 B12 107.4(5) . . ? B4 B9 B12 106.9(5) . . ? B8 B9 B12 59.5(4) . . ? B3 B9 B10 107.8(6) . . ? B4 B9 B10 59.1(5) . . ? B8 B9 B10 107.3(5) . . ? B12 B9 B10 59.8(4) . . ? B4 B10 B11 107.7(5) . . ? B4 B10 B5 60.3(4) . . ? B11 B10 B5 59.5(4) . . ? B4 B10 B12 107.4(5) . . ? B11 B10 B12 60.1(4) . . ? B5 B10 B12 107.6(5) . . ? B4 B10 B9 59.6(4) . . ? B11 B10 B9 108.1(5) . . ? B5 B10 B9 108.0(5) . . ? B12 B10 B9 59.9(4) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 2.851 _refine_diff_density_min -1.819 _refine_diff_density_rms 0.176 data_7 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 843471' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H37 B10 Cl2 Ir N2 O3 S2' _chemical_formula_weight 800.85 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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 21.033(10) _cell_length_b 14.212(7) _cell_length_c 22.672(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6777(5) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3152 _exptl_absorpt_coefficient_mu 4.248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3622 _exptl_absorpt_correction_T_max 0.4550 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33406 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6650 _reflns_number_gt 4351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+1.9900P] 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 6650 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _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 B3 B 0.3266(5) 0.4559(7) 0.3669(4) 0.048(2) Uani 1 1 d . . . H3 H 0.3170 0.4607 0.4145 0.057 Uiso 1 1 calc R . . B4 B 0.3648(4) 0.3525(7) 0.3332(5) 0.049(2) Uani 1 1 d . . . H4 H 0.3795 0.2931 0.3612 0.058 Uiso 1 1 calc R . . B5 B 0.3313(5) 0.3354(6) 0.2612(4) 0.048(2) Uani 1 1 d . . . H5 H 0.3242 0.2643 0.2432 0.058 Uiso 1 1 calc R . . B6 B 0.2764(4) 0.4321(6) 0.2473(4) 0.0365(17) Uani 1 1 d . . . H6 H 0.2333 0.4222 0.2205 0.044 Uiso 1 1 calc R . . B7 B 0.3219(4) 0.5466(7) 0.2464(4) 0.047(2) Uani 1 1 d . . . H7 H 0.3093 0.6086 0.2198 0.056 Uiso 1 1 calc R . . B8 B 0.3511(5) 0.5600(8) 0.3179(5) 0.055(3) Uani 1 1 d . . . H8 H 0.3576 0.6304 0.3372 0.066 Uiso 1 1 calc R . . B9 B 0.4028(6) 0.4585(8) 0.3280(5) 0.059(3) Uani 1 1 d . . . H9 H 0.4462 0.4679 0.3545 0.071 Uiso 1 1 calc R . . B10 B 0.4089(4) 0.3861(8) 0.2707(5) 0.053(2) Uani 1 1 d . . . H10 H 0.4529 0.3484 0.2594 0.064 Uiso 1 1 calc R . . B11 B 0.3522(4) 0.4355(7) 0.2155(4) 0.044(2) Uani 1 1 d . . . H11 H 0.3583 0.4264 0.1676 0.052 Uiso 1 1 calc R . . B12 B 0.3999(4) 0.5158(8) 0.2570(4) 0.050(2) Uani 1 1 d . . . H12 H 0.4377 0.5582 0.2364 0.060 Uiso 1 1 calc R . . C1 C 0.2800(3) 0.5040(5) 0.3103(3) 0.0408(17) Uani 1 1 d . . . C2 C 0.2866(3) 0.3877(5) 0.3164(3) 0.0412(17) Uani 1 1 d . . . C3 C 0.0331(4) 0.4418(5) 0.3634(4) 0.0427(17) Uani 1 1 d . . . C4 C 0.0442(4) 0.3510(5) 0.3390(4) 0.053(2) Uani 1 1 d . . . C5 C 0.0738(4) 0.3751(5) 0.2818(3) 0.0419(18) Uani 1 1 d . . . C6 C 0.0754(3) 0.4776(6) 0.2726(3) 0.0417(18) Uani 1 1 d . . . C7 C 0.0541(4) 0.5178(5) 0.3300(3) 0.0342(15) Uani 1 1 d . . . C8 C 0.0433(4) 0.6219(5) 0.3424(4) 0.052(2) Uani 1 1 d . . . H8A H 0.0092 0.6446 0.3181 0.078 Uiso 1 1 calc R . . H8B H 0.0813 0.6565 0.3336 0.078 Uiso 1 1 calc R . . H8C H 0.0324 0.6303 0.3832 0.078 Uiso 1 1 calc R . . C9 C 0.0035(4) 0.4514(6) 0.4290(4) 0.053(2) Uani 1 1 d . . . H9A H 0.0357 0.4374 0.4577 0.079 Uiso 1 1 calc R . . H9B H -0.0312 0.4080 0.4334 0.079 Uiso 1 1 calc R . . H9C H -0.0117 0.5144 0.4349 0.079 Uiso 1 1 calc R . . C10 C 0.0259(4) 0.2578(5) 0.3601(4) 0.051(2) Uani 1 1 d . . . H10A H 0.0557 0.2371 0.3895 0.076 Uiso 1 1 calc R . . H10B H 0.0260 0.2143 0.3277 0.076 Uiso 1 1 calc R . . H10C H -0.0159 0.2606 0.3770 0.076 Uiso 1 1 calc R . . C11 C 0.0910(3) 0.3028(5) 0.2347(3) 0.0414(17) Uani 1 1 d . . . H11A H 0.0538 0.2878 0.2119 0.062 Uiso 1 1 calc R . . H11B H 0.1068 0.2468 0.2532 0.062 Uiso 1 1 calc R . . H11C H 0.1231 0.3283 0.2092 0.062 Uiso 1 1 calc R . . C12 C 0.0981(4) 0.5298(7) 0.2193(3) 0.058(2) Uani 1 1 d . . . H12A H 0.1180 0.4865 0.1924 0.088 Uiso 1 1 calc R . . H12B H 0.1284 0.5768 0.2310 0.088 Uiso 1 1 calc R . . H12C H 0.0627 0.5595 0.2002 0.088 Uiso 1 1 calc R . . C13 C 0.2069(4) 0.3798(6) 0.4608(4) 0.059(2) Uani 1 1 d . . . C14 C 0.2359(4) 0.3162(6) 0.4235(3) 0.0466(18) Uani 1 1 d . . . C15 C 0.2798(4) 0.2516(5) 0.4417(4) 0.0466(19) Uani 1 1 d . . . H15 H 0.2978 0.2087 0.4156 0.056 Uiso 1 1 calc R . . C16 C 0.2967(4) 0.2526(6) 0.5021(4) 0.0478(19) Uani 1 1 d . . . C17 C 0.2681(4) 0.3157(6) 0.5441(4) 0.054(2) Uani 1 1 d . . . C18 C 0.2193(4) 0.3754(6) 0.5223(4) 0.053(2) Uani 1 1 d . . . C19 C 0.1886(4) 0.4475(7) 0.5605(4) 0.064(3) Uani 1 1 d . . . H19D H 0.2026 0.4394 0.6004 0.095 Uiso 1 1 calc R . . H19E H 0.1433 0.4405 0.5586 0.095 Uiso 1 1 calc R . . H19F H 0.2002 0.5092 0.5469 0.095 Uiso 1 1 calc R . . C20 C 0.2912(5) 0.3190(7) 0.6084(3) 0.065(3) Uani 1 1 d . . . H20A H 0.3179 0.3731 0.6140 0.098 Uiso 1 1 calc R . . H20B H 0.3149 0.2630 0.6171 0.098 Uiso 1 1 calc R . . H20C H 0.2552 0.3230 0.6344 0.098 Uiso 1 1 calc R . . C21 C 0.3897(6) 0.6532(7) 0.5003(6) 0.090(4) Uani 1 1 d . . . H21A H 0.3599 0.6958 0.4816 0.108 Uiso 1 1 calc R . . H21B H 0.4099 0.6149 0.4702 0.108 Uiso 1 1 calc R . . Cl1 Cl 0.35304(14) 0.5851(2) 0.55140(14) 0.0808(8) Uani 1 1 d . . . Cl2 Cl 0.44716(15) 0.7159(2) 0.54185(14) 0.0874(8) Uani 1 1 d . . . Ir1 Ir 0.135578(11) 0.435699(17) 0.349903(11) 0.02953(10) Uani 1 1 d . . . N1 N 0.1626(2) 0.4393(5) 0.4391(3) 0.0403(15) Uani 1 1 d . . . H1 H 0.1451 0.4795 0.4623 0.048 Uiso 1 1 calc R . . N2 N 0.3510(3) 0.1949(5) 0.5185(3) 0.0519(17) Uani 1 1 d . . . O1 O 0.3705(3) 0.1926(5) 0.5685(3) 0.0694(18) Uani 1 1 d . . . O2 O 0.3709(3) 0.1395(4) 0.4795(3) 0.0539(15) Uani 1 1 d . . . O1W O 0.5395(3) 0.5288(5) 0.4291(3) 0.0692(18) Uani 1 1 d . . . H1X H 0.5543 0.4744 0.4365 0.083 Uiso 1 1 d R . . H1Y H 0.5287 0.5318 0.3931 0.083 Uiso 1 1 d R . . S1 S 0.20910(8) 0.55897(12) 0.33540(8) 0.0346(4) Uani 1 1 d . . . S2 S 0.21731(7) 0.32257(12) 0.34603(7) 0.0319(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 B3 0.054(5) 0.053(6) 0.036(5) -0.005(4) -0.012(4) 0.006(4) B4 0.040(5) 0.050(5) 0.056(6) -0.011(4) -0.013(4) 0.009(4) B5 0.076(6) 0.029(4) 0.040(5) -0.013(4) -0.020(5) 0.003(4) B6 0.040(4) 0.037(4) 0.033(4) -0.005(3) -0.005(3) 0.001(3) B7 0.049(5) 0.048(5) 0.043(5) -0.009(4) -0.012(4) 0.003(4) B8 0.059(6) 0.057(6) 0.049(6) -0.003(5) -0.008(5) -0.030(5) B9 0.062(7) 0.063(7) 0.051(6) 0.003(5) 0.010(5) -0.007(5) B10 0.043(5) 0.066(7) 0.051(6) -0.013(5) -0.005(4) 0.005(5) B11 0.039(4) 0.052(5) 0.040(5) -0.004(4) -0.003(4) 0.009(4) B12 0.037(5) 0.071(7) 0.041(5) 0.004(5) 0.001(4) -0.012(4) C1 0.031(4) 0.044(4) 0.047(5) -0.006(3) -0.011(3) -0.005(3) C2 0.035(4) 0.045(4) 0.043(4) 0.004(3) -0.016(3) -0.007(3) C3 0.045(4) 0.032(4) 0.051(5) 0.000(3) -0.004(3) -0.009(3) C4 0.064(5) 0.026(4) 0.068(6) -0.007(4) 0.006(4) -0.023(3) C5 0.047(4) 0.046(4) 0.033(4) -0.010(3) -0.006(3) 0.002(3) C6 0.035(4) 0.064(5) 0.026(4) -0.002(3) -0.001(3) 0.006(3) C7 0.048(4) 0.029(3) 0.026(4) -0.009(3) 0.005(3) 0.003(3) C8 0.052(5) 0.038(4) 0.066(6) -0.003(4) 0.016(4) 0.018(4) C9 0.044(4) 0.071(6) 0.044(5) 0.009(4) 0.003(4) 0.018(4) C10 0.068(5) 0.034(4) 0.050(5) 0.005(4) 0.000(4) -0.004(4) C11 0.039(4) 0.034(4) 0.051(4) -0.009(3) 0.009(3) -0.026(3) C12 0.071(6) 0.079(6) 0.026(4) -0.005(4) 0.008(4) 0.022(5) C13 0.067(6) 0.061(6) 0.049(5) 0.005(4) 0.009(4) 0.017(4) C14 0.060(5) 0.047(4) 0.033(4) -0.018(4) -0.005(3) 0.006(4) C15 0.052(4) 0.030(4) 0.058(5) -0.018(4) -0.006(4) -0.002(3) C16 0.062(5) 0.048(5) 0.034(4) -0.009(4) -0.007(4) 0.010(4) C17 0.071(5) 0.052(5) 0.038(4) -0.004(4) 0.003(4) 0.031(4) C18 0.042(4) 0.054(5) 0.064(6) -0.002(4) 0.006(4) 0.008(4) C19 0.042(4) 0.093(7) 0.057(6) 0.005(5) -0.002(4) 0.040(5) C20 0.091(7) 0.077(6) 0.028(4) 0.014(4) 0.003(4) 0.024(6) C21 0.096(8) 0.048(6) 0.125(11) -0.014(6) -0.051(8) 0.019(6) Cl1 0.0893(18) 0.0734(17) 0.0796(18) 0.0175(15) -0.0185(16) -0.0092(13) Cl2 0.0983(19) 0.0716(17) 0.092(2) 0.0251(15) -0.0092(17) -0.0199(15) Ir1 0.02959(15) 0.03069(16) 0.02832(15) 0.00013(11) 0.00030(10) 0.00037(10) N1 0.019(3) 0.073(4) 0.029(3) -0.011(3) 0.000(2) 0.020(3) N2 0.065(4) 0.045(4) 0.045(4) 0.010(3) 0.011(3) 0.005(3) O1 0.097(5) 0.061(4) 0.050(4) 0.017(3) -0.006(4) 0.000(4) O2 0.062(4) 0.058(4) 0.042(3) 0.003(3) 0.015(3) 0.011(3) O1W 0.058(4) 0.095(5) 0.054(4) -0.004(4) 0.009(3) 0.021(3) S1 0.0327(8) 0.0335(9) 0.0376(9) 0.0079(7) -0.0049(7) -0.0057(7) S2 0.0302(8) 0.0338(9) 0.0317(9) -0.0028(7) -0.0029(7) 0.0028(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 B3 C2 1.719(12) . ? B3 C1 1.753(12) . ? B3 B9 1.830(15) . ? B3 B4 1.842(14) . ? B3 B8 1.920(15) . ? B3 H3 1.1000 . ? B4 B9 1.710(15) . ? B4 B10 1.759(15) . ? B4 C2 1.762(11) . ? B4 B5 1.795(13) . ? B4 H4 1.1000 . ? B5 C2 1.734(13) . ? B5 B10 1.798(13) . ? B5 B11 1.814(14) . ? B5 B6 1.822(12) . ? B5 H5 1.1000 . ? B6 C2 1.704(11) . ? B6 B11 1.751(12) . ? B6 C1 1.757(11) . ? B6 B7 1.887(13) . ? B6 H6 1.1000 . ? B7 B12 1.716(13) . ? B7 B8 1.745(14) . ? B7 C1 1.801(13) . ? B7 B11 1.840(13) . ? B7 H7 1.1000 . ? B8 C1 1.703(11) . ? B8 B9 1.821(17) . ? B8 B12 1.833(15) . ? B8 H8 1.1000 . ? B9 B10 1.662(15) . ? B9 B12 1.806(15) . ? B9 H9 1.1000 . ? B10 B11 1.867(14) . ? B10 B12 1.880(16) . ? B10 H10 1.1000 . ? B11 B12 1.787(13) . ? B11 H11 1.1000 . ? B12 H12 1.1000 . ? C1 C2 1.664(11) . ? C1 S1 1.777(8) . ? C2 S2 1.852(7) . ? C3 C7 1.391(10) . ? C3 C4 1.424(11) . ? C3 C9 1.619(11) . ? C3 Ir1 2.178(8) . ? C4 C10 1.460(10) . ? C4 C5 1.478(11) . ? C4 Ir1 2.281(8) . ? C5 C6 1.472(12) . ? C5 C11 1.526(10) . ? C5 Ir1 2.193(7) . ? C6 C7 1.490(9) . ? C6 C12 1.498(11) . ? C6 Ir1 2.243(7) . ? C7 C8 1.523(10) . ? C7 Ir1 2.121(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N1 1.350(10) . ? C13 C14 1.380(11) . ? C13 C18 1.421(13) . ? C14 C15 1.366(11) . ? C14 S2 1.801(8) . ? C15 C16 1.415(12) . ? C15 H15 0.9300 . ? C16 C17 1.440(11) . ? C16 N2 1.455(10) . ? C17 C18 1.420(11) . ? C17 C20 1.538(11) . ? C18 C19 1.489(12) . ? C19 H19D 0.9600 . ? C19 H19E 0.9600 . ? C19 H19F 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 Cl1 1.696(14) . ? C21 Cl2 1.773(11) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? Ir1 N1 2.102(6) . ? Ir1 S2 2.3553(18) . ? Ir1 S1 2.3597(18) . ? N1 H1 0.8600 . ? N2 O1 1.204(9) . ? N2 O2 1.256(9) . ? O1W H1X 0.8500 . ? O1W H1Y 0.8499 . ? 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 C2 B3 C1 57.3(5) . . ? C2 B3 B9 96.9(7) . . ? C1 B3 B9 97.5(7) . . ? C2 B3 B4 59.2(5) . . ? C1 B3 B4 104.6(6) . . ? B9 B3 B4 55.5(5) . . ? C2 B3 B8 100.4(6) . . ? C1 B3 B8 55.0(5) . . ? B9 B3 B8 58.0(6) . . ? B4 B3 B8 104.9(7) . . ? C2 B3 H3 126.8 . . ? C1 B3 H3 126.3 . . ? B9 B3 H3 129.1 . . ? B4 B3 H3 122.4 . . ? B8 B3 H3 124.6 . . ? B9 B4 B10 57.2(6) . . ? B9 B4 C2 99.9(7) . . ? B10 B4 C2 104.0(7) . . ? B9 B4 B5 103.9(8) . . ? B10 B4 B5 60.8(6) . . ? C2 B4 B5 58.4(5) . . ? B9 B4 B3 61.9(6) . . ? B10 B4 B3 110.3(7) . . ? C2 B4 B3 56.9(5) . . ? B5 B4 B3 108.3(6) . . ? B9 B4 H4 125.7 . . ? B10 B4 H4 121.7 . . ? C2 B4 H4 127.2 . . ? B5 B4 H4 122.2 . . ? B3 B4 H4 119.7 . . ? C2 B5 B4 59.9(5) . . ? C2 B5 B10 103.5(6) . . ? B4 B5 B10 58.6(5) . . ? C2 B5 B11 102.0(6) . . ? B4 B5 B11 108.6(6) . . ? B10 B5 B11 62.3(6) . . ? C2 B5 B6 57.2(4) . . ? B4 B5 B6 107.7(6) . . ? B10 B5 B6 107.1(6) . . ? B11 B5 B6 57.6(5) . . ? C2 B5 H5 126.0 . . ? B4 B5 H5 120.9 . . ? B10 B5 H5 122.4 . . ? B11 B5 H5 122.8 . . ? B6 B5 H5 122.9 . . ? C2 B6 B11 105.9(6) . . ? C2 B6 C1 57.4(5) . . ? B11 B6 C1 106.2(6) . . ? C2 B6 B5 58.8(5) . . ? B11 B6 B5 61.0(5) . . ? C1 B6 B5 105.7(5) . . ? C2 B6 B7 105.4(6) . . ? B11 B6 B7 60.6(5) . . ? C1 B6 B7 59.1(5) . . ? B5 B6 B7 109.3(6) . . ? C2 B6 H6 124.3 . . ? B11 B6 H6 121.9 . . ? C1 B6 H6 123.9 . . ? B5 B6 H6 121.4 . . ? B7 B6 H6 121.5 . . ? B12 B7 B8 63.9(6) . . ? B12 B7 C1 105.7(6) . . ? B8 B7 C1 57.4(5) . . ? B12 B7 B11 60.2(5) . . ? B8 B7 B11 109.0(7) . . ? C1 B7 B11 100.8(6) . . ? B12 B7 B6 105.3(6) . . ? B8 B7 B6 105.2(7) . . ? C1 B7 B6 56.9(4) . . ? B11 B7 B6 56.0(5) . . ? B12 B7 H7 120.7 . . ? B8 B7 H7 120.4 . . ? C1 B7 H7 126.4 . . ? B11 B7 H7 124.2 . . ? B6 B7 H7 125.1 . . ? C1 B8 B7 62.9(5) . . ? C1 B8 B9 99.7(7) . . ? B7 B8 B9 103.9(7) . . ? C1 B8 B12 104.8(6) . . ? B7 B8 B12 57.3(5) . . ? B9 B8 B12 59.2(6) . . ? C1 B8 B3 57.5(5) . . ? B7 B8 B3 111.0(6) . . ? B9 B8 B3 58.5(6) . . ? B12 B8 B3 108.8(7) . . ? C1 B8 H8 125.1 . . ? B7 B8 H8 120.8 . . ? B9 B8 H8 126.6 . . ? B12 B8 H8 122.7 . . ? B3 B8 H8 120.3 . . ? B10 B9 B4 62.9(6) . . ? B10 B9 B12 65.5(7) . . ? B4 B9 B12 116.3(8) . . ? B10 B9 B8 116.0(8) . . ? B4 B9 B8 115.3(8) . . ? B12 B9 B8 60.7(6) . . ? B10 B9 B3 115.6(8) . . ? B4 B9 B3 62.6(6) . . ? B12 B9 B3 114.1(8) . . ? B8 B9 B3 63.4(6) . . ? B10 B9 H9 115.9 . . ? B4 B9 H9 117.2 . . ? B12 B9 H9 117.4 . . ? B8 B9 H9 117.9 . . ? B3 B9 H9 117.8 . . ? B9 B10 B4 59.9(6) . . ? B9 B10 B5 105.8(7) . . ? B4 B10 B5 60.6(5) . . ? B9 B10 B11 104.0(7) . . ? B4 B10 B11 107.8(6) . . ? B5 B10 B11 59.3(5) . . ? B9 B10 B12 60.9(6) . . ? B4 B10 B12 110.3(7) . . ? B5 B10 B12 106.3(6) . . ? B11 B10 B12 57.0(5) . . ? B9 B10 H10 123.4 . . ? B4 B10 H10 120.0 . . ? B5 B10 H10 122.7 . . ? B11 B10 H10 124.3 . . ? B12 B10 H10 121.6 . . ? B6 B11 B12 108.2(6) . . ? B6 B11 B5 61.5(5) . . ? B12 B11 B5 109.7(6) . . ? B6 B11 B7 63.3(5) . . ? B12 B11 B7 56.4(5) . . ? B5 B11 B7 111.8(7) . . ? B6 B11 B10 107.2(7) . . ? B12 B11 B10 61.8(5) . . ? B5 B11 B10 58.5(5) . . ? B7 B11 B10 106.8(6) . . ? B6 B11 H11 120.5 . . ? B12 B11 H11 122.0 . . ? B5 B11 H11 119.9 . . ? B7 B11 H11 121.1 . . ? B10 B11 H11 122.9 . . ? B7 B12 B11 63.3(5) . . ? B7 B12 B9 105.8(7) . . ? B11 B12 B9 101.6(7) . . ? B7 B12 B8 58.8(5) . . ? B11 B12 B8 107.5(6) . . ? B9 B12 B8 60.0(6) . . ? B7 B12 B10 111.7(6) . . ? B11 B12 B10 61.2(5) . . ? B9 B12 B10 53.6(5) . . ? B8 B12 B10 105.5(7) . . ? B7 B12 H12 119.5 . . ? B11 B12 H12 122.0 . . ? B9 B12 H12 127.0 . . ? B8 B12 H12 122.5 . . ? B10 B12 H12 122.3 . . ? C2 C1 B8 112.5(6) . . ? C2 C1 B3 60.3(5) . . ? B8 C1 B3 67.5(6) . . ? C2 C1 B6 59.7(5) . . ? B8 C1 B6 113.1(6) . . ? B3 C1 B6 113.1(6) . . ? C2 C1 S1 118.7(5) . . ? B8 C1 S1 119.9(6) . . ? B3 C1 S1 113.9(6) . . ? B6 C1 S1 118.7(5) . . ? C2 C1 B7 111.1(6) . . ? B8 C1 B7 59.7(5) . . ? B3 C1 B7 116.5(6) . . ? B6 C1 B7 64.0(5) . . ? S1 C1 B7 121.4(5) . . ? C1 C2 B6 62.9(5) . . ? C1 C2 B3 62.4(5) . . ? B6 C2 B3 117.7(6) . . ? C1 C2 B5 114.2(6) . . ? B6 C2 B5 64.0(5) . . ? B3 C2 B5 117.2(6) . . ? C1 C2 B4 112.2(6) . . ? B6 C2 B4 114.9(6) . . ? B3 C2 B4 63.9(5) . . ? B5 C2 B4 61.8(5) . . ? C1 C2 S2 117.5(5) . . ? B6 C2 S2 114.8(5) . . ? B3 C2 S2 115.2(6) . . ? B5 C2 S2 118.3(5) . . ? B4 C2 S2 121.0(6) . . ? C7 C3 C4 116.2(7) . . ? C7 C3 C9 123.9(7) . . ? C4 C3 C9 119.7(7) . . ? C7 C3 Ir1 68.9(4) . . ? C4 C3 Ir1 75.3(5) . . ? C9 C3 Ir1 120.9(5) . . ? C3 C4 C10 130.7(8) . . ? C3 C4 C5 101.5(6) . . ? C10 C4 C5 127.5(7) . . ? C3 C4 Ir1 67.5(4) . . ? C10 C4 Ir1 131.7(7) . . ? C5 C4 Ir1 67.5(4) . . ? C6 C5 C4 111.3(6) . . ? C6 C5 C11 124.2(7) . . ? C4 C5 C11 123.9(7) . . ? C6 C5 Ir1 72.5(4) . . ? C4 C5 Ir1 74.0(4) . . ? C11 C5 Ir1 128.1(5) . . ? C5 C6 C7 104.4(6) . . ? C5 C6 C12 127.7(7) . . ? C7 C6 C12 127.7(7) . . ? C5 C6 Ir1 68.8(4) . . ? C7 C6 Ir1 65.7(4) . . ? C12 C6 Ir1 125.6(6) . . ? C3 C7 C6 105.8(6) . . ? C3 C7 C8 127.4(7) . . ? C6 C7 C8 125.3(7) . . ? C3 C7 Ir1 73.4(5) . . ? C6 C7 Ir1 74.5(4) . . ? C8 C7 Ir1 128.1(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 119.5(8) . . ? N1 C13 C18 120.8(8) . . ? C14 C13 C18 119.4(8) . . ? C15 C14 C13 123.6(7) . . ? C15 C14 S2 118.4(6) . . ? C13 C14 S2 117.9(6) . . ? C14 C15 C16 117.1(7) . . ? C14 C15 H15 121.4 . . ? C16 C15 H15 121.4 . . ? C15 C16 C17 122.8(7) . . ? C15 C16 N2 116.1(7) . . ? C17 C16 N2 120.7(7) . . ? C18 C17 C16 116.3(7) . . ? C18 C17 C20 122.7(7) . . ? C16 C17 C20 120.9(7) . . ? C17 C18 C13 120.1(8) . . ? C17 C18 C19 121.4(8) . . ? C13 C18 C19 117.4(8) . . ? C18 C19 H19D 109.5 . . ? C18 C19 H19E 109.5 . . ? H19D C19 H19E 109.5 . . ? C18 C19 H19F 109.5 . . ? H19D C19 H19F 109.5 . . ? H19E C19 H19F 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? Cl1 C21 Cl2 103.5(7) . . ? Cl1 C21 H21A 111.1 . . ? Cl2 C21 H21A 111.1 . . ? Cl1 C21 H21B 111.1 . . ? Cl2 C21 H21B 111.1 . . ? H21A C21 H21B 109.0 . . ? N1 Ir1 C7 114.2(2) . . ? N1 Ir1 C3 97.6(3) . . ? C7 Ir1 C3 37.7(3) . . ? N1 Ir1 C5 147.9(3) . . ? C7 Ir1 C5 65.7(3) . . ? C3 Ir1 C5 61.9(3) . . ? N1 Ir1 C6 153.9(2) . . ? C7 Ir1 C6 39.8(2) . . ? C3 Ir1 C6 62.6(3) . . ? C5 Ir1 C6 38.7(3) . . ? N1 Ir1 C4 110.2(3) . . ? C7 Ir1 C4 65.6(3) . . ? C3 Ir1 C4 37.2(3) . . ? C5 Ir1 C4 38.5(3) . . ? C6 Ir1 C4 65.2(3) . . ? N1 Ir1 S2 81.65(15) . . ? C7 Ir1 S2 163.15(18) . . ? C3 Ir1 S2 139.0(2) . . ? C5 Ir1 S2 97.9(2) . . ? C6 Ir1 S2 124.4(2) . . ? C4 Ir1 S2 104.5(2) . . ? N1 Ir1 S1 86.49(18) . . ? C7 Ir1 S1 95.2(2) . . ? C3 Ir1 S1 129.6(2) . . ? C5 Ir1 S1 125.5(2) . . ? C6 Ir1 S1 93.7(2) . . ? C4 Ir1 S1 158.3(2) . . ? S2 Ir1 S1 91.34(7) . . ? C13 N1 Ir1 121.4(5) . . ? C13 N1 H1 119.3 . . ? Ir1 N1 H1 119.3 . . ? O1 N2 O2 122.3(7) . . ? O1 N2 C16 121.5(7) . . ? O2 N2 C16 115.7(7) . . ? H1X O1W H1Y 109.5 . . ? C1 S1 Ir1 105.5(2) . . ? C14 S2 C2 101.9(4) . . ? C14 S2 Ir1 99.0(3) . . ? C2 S2 Ir1 104.3(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 C2 B3 B4 B9 125.4(8) . . . . ? C1 B3 B4 B9 89.1(7) . . . . ? B8 B3 B4 B9 32.0(7) . . . . ? C2 B3 B4 B10 93.9(7) . . . . ? C1 B3 B4 B10 57.5(8) . . . . ? B9 B3 B4 B10 -31.6(7) . . . . ? B8 B3 B4 B10 0.4(8) . . . . ? C1 B3 B4 C2 -36.3(6) . . . . ? B9 B3 B4 C2 -125.4(8) . . . . ? B8 B3 B4 C2 -93.4(6) . . . . ? C2 B3 B4 B5 29.1(6) . . . . ? C1 B3 B4 B5 -7.3(9) . . . . ? B9 B3 B4 B5 -96.4(8) . . . . ? B8 B3 B4 B5 -64.4(8) . . . . ? B9 B4 B5 C2 -93.1(7) . . . . ? B10 B4 B5 C2 -132.1(7) . . . . ? B3 B4 B5 C2 -28.6(6) . . . . ? B9 B4 B5 B10 39.0(7) . . . . ? C2 B4 B5 B10 132.1(7) . . . . ? B3 B4 B5 B10 103.6(8) . . . . ? B9 B4 B5 B11 0.3(9) . . . . ? B10 B4 B5 B11 -38.7(7) . . . . ? C2 B4 B5 B11 93.4(6) . . . . ? B3 B4 B5 B11 64.8(8) . . . . ? B9 B4 B5 B6 -60.6(8) . . . . ? B10 B4 B5 B6 -99.6(7) . . . . ? C2 B4 B5 B6 32.5(6) . . . . ? B3 B4 B5 B6 3.9(9) . . . . ? B4 B5 B6 C2 -33.6(6) . . . . ? B10 B5 B6 C2 -95.3(6) . . . . ? B11 B5 B6 C2 -134.7(6) . . . . ? C2 B5 B6 B11 134.7(6) . . . . ? B4 B5 B6 B11 101.1(7) . . . . ? B10 B5 B6 B11 39.4(6) . . . . ? C2 B5 B6 C1 34.6(5) . . . . ? B4 B5 B6 C1 1.0(8) . . . . ? B10 B5 B6 C1 -60.8(7) . . . . ? B11 B5 B6 C1 -100.1(6) . . . . ? C2 B5 B6 B7 96.7(6) . . . . ? B4 B5 B6 B7 63.1(8) . . . . ? B10 B5 B6 B7 1.4(8) . . . . ? B11 B5 B6 B7 -38.0(6) . . . . ? C2 B6 B7 B12 63.6(7) . . . . ? B11 B6 B7 B12 -36.3(6) . . . . ? C1 B6 B7 B12 98.9(7) . . . . ? B5 B6 B7 B12 1.8(8) . . . . ? C2 B6 B7 B8 -3.0(8) . . . . ? B11 B6 B7 B8 -102.9(7) . . . . ? C1 B6 B7 B8 32.4(6) . . . . ? B5 B6 B7 B8 -64.8(8) . . . . ? C2 B6 B7 C1 -35.3(5) . . . . ? B11 B6 B7 C1 -135.2(6) . . . . ? B5 B6 B7 C1 -97.1(6) . . . . ? C2 B6 B7 B11 99.9(6) . . . . ? C1 B6 B7 B11 135.2(6) . . . . ? B5 B6 B7 B11 38.1(6) . . . . ? B12 B7 B8 C1 -132.1(7) . . . . ? B11 B7 B8 C1 -90.9(7) . . . . ? B6 B7 B8 C1 -32.2(6) . . . . ? B12 B7 B8 B9 -38.2(7) . . . . ? C1 B7 B8 B9 93.9(7) . . . . ? B11 B7 B8 B9 2.9(9) . . . . ? B6 B7 B8 B9 61.7(8) . . . . ? C1 B7 B8 B12 132.1(7) . . . . ? B11 B7 B8 B12 41.1(6) . . . . ? B6 B7 B8 B12 99.9(7) . . . . ? B12 B7 B8 B3 -99.4(8) . . . . ? C1 B7 B8 B3 32.6(6) . . . . ? B11 B7 B8 B3 -58.3(9) . . . . ? B6 B7 B8 B3 0.5(9) . . . . ? C2 B3 B8 C1 36.8(6) . . . . ? B9 B3 B8 C1 128.5(7) . . . . ? B4 B3 B8 C1 97.5(7) . . . . ? C2 B3 B8 B7 2.2(9) . . . . ? C1 B3 B8 B7 -34.7(6) . . . . ? B9 B3 B8 B7 93.9(8) . . . . ? B4 B3 B8 B7 62.9(9) . . . . ? C2 B3 B8 B9 -91.7(7) . . . . ? C1 B3 B8 B9 -128.5(7) . . . . ? B4 B3 B8 B9 -31.0(6) . . . . ? C2 B3 B8 B12 -59.1(8) . . . . ? C1 B3 B8 B12 -95.9(7) . . . . ? B9 B3 B8 B12 32.6(7) . . . . ? B4 B3 B8 B12 1.6(8) . . . . ? C2 B4 B9 B10 -100.4(7) . . . . ? B5 B4 B9 B10 -40.8(7) . . . . ? B3 B4 B9 B10 -144.3(8) . . . . ? B10 B4 B9 B12 39.4(7) . . . . ? C2 B4 B9 B12 -61.1(9) . . . . ? B5 B4 B9 B12 -1.4(10) . . . . ? B3 B4 B9 B12 -104.9(9) . . . . ? B10 B4 B9 B8 107.6(9) . . . . ? C2 B4 B9 B8 7.2(10) . . . . ? B5 B4 B9 B8 66.8(9) . . . . ? B3 B4 B9 B8 -36.7(7) . . . . ? B10 B4 B9 B3 144.3(8) . . . . ? C2 B4 B9 B3 43.9(6) . . . . ? B5 B4 B9 B3 103.5(7) . . . . ? C1 B8 B9 B10 65.0(9) . . . . ? B7 B8 B9 B10 0.7(10) . . . . ? B12 B8 B9 B10 -36.6(7) . . . . ? B3 B8 B9 B10 107.0(9) . . . . ? C1 B8 B9 B4 -5.7(10) . . . . ? B7 B8 B9 B4 -70.0(9) . . . . ? B12 B8 B9 B4 -107.3(9) . . . . ? B3 B8 B9 B4 36.3(7) . . . . ? C1 B8 B9 B12 101.6(7) . . . . ? B7 B8 B9 B12 37.3(6) . . . . ? B3 B8 B9 B12 143.6(7) . . . . ? C1 B8 B9 B3 -42.0(6) . . . . ? B7 B8 B9 B3 -106.3(7) . . . . ? B12 B8 B9 B3 -143.6(7) . . . . ? C2 B3 B9 B10 -9.7(10) . . . . ? C1 B3 B9 B10 -67.5(9) . . . . ? B4 B3 B9 B10 35.1(7) . . . . ? B8 B3 B9 B10 -107.7(9) . . . . ? C2 B3 B9 B4 -44.9(6) . . . . ? C1 B3 B9 B4 -102.6(7) . . . . ? B8 B3 B9 B4 -142.9(7) . . . . ? C2 B3 B9 B12 63.5(8) . . . . ? C1 B3 B9 B12 5.7(9) . . . . ? B4 B3 B9 B12 108.3(9) . . . . ? B8 B3 B9 B12 -34.6(7) . . . . ? C2 B3 B9 B8 98.0(6) . . . . ? C1 B3 B9 B8 40.3(6) . . . . ? B4 B3 B9 B8 142.9(7) . . . . ? B12 B9 B10 B4 -141.3(7) . . . . ? B8 B9 B10 B4 -106.5(9) . . . . ? B3 B9 B10 B4 -35.0(7) . . . . ? B4 B9 B10 B5 41.1(7) . . . . ? B12 B9 B10 B5 -100.2(7) . . . . ? B8 B9 B10 B5 -65.4(10) . . . . ? B3 B9 B10 B5 6.1(11) . . . . ? B4 B9 B10 B11 102.7(7) . . . . ? B12 B9 B10 B11 -38.7(6) . . . . ? B8 B9 B10 B11 -3.8(10) . . . . ? B3 B9 B10 B11 67.6(9) . . . . ? B4 B9 B10 B12 141.3(7) . . . . ? B8 B9 B10 B12 34.8(7) . . . . ? B3 B9 B10 B12 106.3(9) . . . . ? C2 B4 B10 B9 92.8(7) . . . . ? B5 B4 B10 B9 133.4(8) . . . . ? B3 B4 B10 B9 33.3(7) . . . . ? B9 B4 B10 B5 -133.4(8) . . . . ? C2 B4 B10 B5 -40.6(6) . . . . ? B3 B4 B10 B5 -100.1(7) . . . . ? B9 B4 B10 B11 -96.2(8) . . . . ? C2 B4 B10 B11 -3.4(8) . . . . ? B5 B4 B10 B11 37.2(6) . . . . ? B3 B4 B10 B11 -62.9(8) . . . . ? B9 B4 B10 B12 -35.6(7) . . . . ? C2 B4 B10 B12 57.2(8) . . . . ? B5 B4 B10 B12 97.8(7) . . . . ? B3 B4 B10 B12 -2.3(8) . . . . ? C2 B5 B10 B9 0.5(9) . . . . ? B4 B5 B10 B9 -40.8(7) . . . . ? B11 B5 B10 B9 97.1(8) . . . . ? B6 B5 B10 B9 59.9(9) . . . . ? C2 B5 B10 B4 41.3(6) . . . . ? B11 B5 B10 B4 137.9(7) . . . . ? B6 B5 B10 B4 100.7(7) . . . . ? C2 B5 B10 B11 -96.6(6) . . . . ? B4 B5 B10 B11 -137.9(7) . . . . ? B6 B5 B10 B11 -37.2(6) . . . . ? C2 B5 B10 B12 -63.2(7) . . . . ? B4 B5 B10 B12 -104.5(7) . . . . ? B11 B5 B10 B12 33.4(6) . . . . ? B6 B5 B10 B12 -3.8(8) . . . . ? C2 B6 B11 B12 -63.7(8) . . . . ? C1 B6 B11 B12 -3.7(8) . . . . ? B5 B6 B11 B12 -103.0(7) . . . . ? B7 B6 B11 B12 35.3(6) . . . . ? C2 B6 B11 B5 39.2(5) . . . . ? C1 B6 B11 B5 99.2(6) . . . . ? B7 B6 B11 B5 138.2(6) . . . . ? C2 B6 B11 B7 -99.0(6) . . . . ? C1 B6 B11 B7 -39.0(6) . . . . ? B5 B6 B11 B7 -138.2(6) . . . . ? C2 B6 B11 B10 1.6(8) . . . . ? C1 B6 B11 B10 61.6(8) . . . . ? B5 B6 B11 B10 -37.7(6) . . . . ? B7 B6 B11 B10 100.6(7) . . . . ? C2 B5 B11 B6 -37.7(5) . . . . ? B4 B5 B11 B6 -99.6(7) . . . . ? B10 B5 B11 B6 -136.8(6) . . . . ? C2 B5 B11 B12 62.9(7) . . . . ? B4 B5 B11 B12 0.9(9) . . . . ? B10 B5 B11 B12 -36.2(6) . . . . ? B6 B5 B11 B12 100.6(7) . . . . ? C2 B5 B11 B7 2.2(8) . . . . ? B4 B5 B11 B7 -59.8(8) . . . . ? B10 B5 B11 B7 -96.9(7) . . . . ? B6 B5 B11 B7 39.9(6) . . . . ? C2 B5 B11 B10 99.1(6) . . . . ? B4 B5 B11 B10 37.1(6) . . . . ? B6 B5 B11 B10 136.8(6) . . . . ? B12 B7 B11 B6 138.8(7) . . . . ? B8 B7 B11 B6 95.9(7) . . . . ? C1 B7 B11 B6 36.9(5) . . . . ? B8 B7 B11 B12 -42.9(6) . . . . ? C1 B7 B11 B12 -102.0(6) . . . . ? B6 B7 B11 B12 -138.8(7) . . . . ? B12 B7 B11 B5 99.8(7) . . . . ? B8 B7 B11 B5 56.9(8) . . . . ? C1 B7 B11 B5 -2.2(8) . . . . ? B6 B7 B11 B5 -39.1(6) . . . . ? B12 B7 B11 B10 37.7(6) . . . . ? B8 B7 B11 B10 -5.2(9) . . . . ? C1 B7 B11 B10 -64.3(7) . . . . ? B6 B7 B11 B10 -101.2(7) . . . . ? B9 B10 B11 B6 -61.2(8) . . . . ? B4 B10 B11 B6 1.2(9) . . . . ? B5 B10 B11 B6 39.0(6) . . . . ? B12 B10 B11 B6 -101.9(7) . . . . ? B9 B10 B11 B12 40.7(7) . . . . ? B4 B10 B11 B12 103.1(7) . . . . ? B5 B10 B11 B12 140.9(7) . . . . ? B9 B10 B11 B5 -100.2(7) . . . . ? B4 B10 B11 B5 -37.8(6) . . . . ? B12 B10 B11 B5 -140.9(7) . . . . ? B9 B10 B11 B7 5.4(9) . . . . ? B4 B10 B11 B7 67.8(8) . . . . ? B5 B10 B11 B7 105.6(7) . . . . ? B12 B10 B11 B7 -35.3(6) . . . . ? B8 B7 B12 B11 134.2(7) . . . . ? C1 B7 B12 B11 93.7(6) . . . . ? B6 B7 B12 B11 34.5(6) . . . . ? B8 B7 B12 B9 39.0(7) . . . . ? C1 B7 B12 B9 -1.5(8) . . . . ? B11 B7 B12 B9 -95.2(7) . . . . ? B6 B7 B12 B9 -60.8(8) . . . . ? C1 B7 B12 B8 -40.5(6) . . . . ? B11 B7 B12 B8 -134.2(7) . . . . ? B6 B7 B12 B8 -99.7(7) . . . . ? B8 B7 B12 B10 95.5(7) . . . . ? C1 B7 B12 B10 55.0(8) . . . . ? B11 B7 B12 B10 -38.7(7) . . . . ? B6 B7 B12 B10 -4.3(9) . . . . ? B6 B11 B12 B7 -38.2(6) . . . . ? B5 B11 B12 B7 -103.6(7) . . . . ? B10 B11 B12 B7 -138.4(7) . . . . ? B6 B11 B12 B9 63.7(8) . . . . ? B5 B11 B12 B9 -1.6(8) . . . . ? B7 B11 B12 B9 102.0(7) . . . . ? B10 B11 B12 B9 -36.4(6) . . . . ? B6 B11 B12 B8 1.8(9) . . . . ? B5 B11 B12 B8 -63.6(8) . . . . ? B7 B11 B12 B8 40.0(7) . . . . ? B10 B11 B12 B8 -98.4(7) . . . . ? B6 B11 B12 B10 100.2(7) . . . . ? B5 B11 B12 B10 34.8(6) . . . . ? B7 B11 B12 B10 138.4(7) . . . . ? B10 B9 B12 B7 105.6(7) . . . . ? B4 B9 B12 B7 67.2(10) . . . . ? B8 B9 B12 B7 -38.4(6) . . . . ? B3 B9 B12 B7 -2.8(10) . . . . ? B10 B9 B12 B11 40.3(6) . . . . ? B4 B9 B12 B11 2.0(10) . . . . ? B8 B9 B12 B11 -103.7(6) . . . . ? B3 B9 B12 B11 -68.1(9) . . . . ? B10 B9 B12 B8 143.9(7) . . . . ? B4 B9 B12 B8 105.6(9) . . . . ? B3 B9 B12 B8 35.6(7) . . . . ? B4 B9 B12 B10 -38.3(7) . . . . ? B8 B9 B12 B10 -143.9(7) . . . . ? B3 B9 B12 B10 -108.4(9) . . . . ? C1 B8 B12 B7 43.2(6) . . . . ? B9 B8 B12 B7 135.7(7) . . . . ? B3 B8 B12 B7 103.4(7) . . . . ? C1 B8 B12 B11 0.9(9) . . . . ? B7 B8 B12 B11 -42.2(7) . . . . ? B9 B8 B12 B11 93.5(8) . . . . ? B3 B8 B12 B11 61.2(8) . . . . ? C1 B8 B12 B9 -92.5(7) . . . . ? B7 B8 B12 B9 -135.7(7) . . . . ? B3 B8 B12 B9 -32.3(7) . . . . ? C1 B8 B12 B10 -63.1(8) . . . . ? B7 B8 B12 B10 -106.3(7) . . . . ? B9 B8 B12 B10 29.4(6) . . . . ? B3 B8 B12 B10 -2.9(8) . . . . ? B9 B10 B12 B7 -94.0(8) . . . . ? B4 B10 B12 B7 -58.8(9) . . . . ? B5 B10 B12 B7 5.3(9) . . . . ? B11 B10 B12 B7 39.7(7) . . . . ? B9 B10 B12 B11 -133.7(7) . . . . ? B4 B10 B12 B11 -98.5(7) . . . . ? B5 B10 B12 B11 -34.4(6) . . . . ? B4 B10 B12 B9 35.2(7) . . . . ? B5 B10 B12 B9 99.3(8) . . . . ? B11 B10 B12 B9 133.7(7) . . . . ? B9 B10 B12 B8 -31.9(7) . . . . ? B4 B10 B12 B8 3.3(8) . . . . ? B5 B10 B12 B8 67.3(8) . . . . ? B11 B10 B12 B8 101.7(7) . . . . ? B7 B8 C1 C2 102.1(7) . . . . ? B9 B8 C1 C2 1.3(9) . . . . ? B12 B8 C1 C2 61.9(8) . . . . ? B3 B8 C1 C2 -41.3(6) . . . . ? B7 B8 C1 B3 143.4(7) . . . . ? B9 B8 C1 B3 42.6(6) . . . . ? B12 B8 C1 B3 103.1(7) . . . . ? B7 B8 C1 B6 36.8(7) . . . . ? B9 B8 C1 B6 -64.0(8) . . . . ? B12 B8 C1 B6 -3.4(9) . . . . ? B3 B8 C1 B6 -106.6(7) . . . . ? B7 B8 C1 S1 -111.0(7) . . . . ? B9 B8 C1 S1 148.1(6) . . . . ? B12 B8 C1 S1 -151.3(6) . . . . ? B3 B8 C1 S1 105.6(7) . . . . ? B9 B8 C1 B7 -100.8(7) . . . . ? B12 B8 C1 B7 -40.2(6) . . . . ? B3 B8 C1 B7 -143.4(7) . . . . ? B9 B3 C1 C2 93.5(6) . . . . ? B4 B3 C1 C2 37.2(6) . . . . ? B8 B3 C1 C2 135.5(7) . . . . ? C2 B3 C1 B8 -135.5(7) . . . . ? B9 B3 C1 B8 -42.0(6) . . . . ? B4 B3 C1 B8 -98.2(7) . . . . ? C2 B3 C1 B6 -29.0(6) . . . . ? B9 B3 C1 B6 64.5(7) . . . . ? B4 B3 C1 B6 8.3(8) . . . . ? B8 B3 C1 B6 106.5(7) . . . . ? C2 B3 C1 S1 110.5(6) . . . . ? B9 B3 C1 S1 -156.0(5) . . . . ? B4 B3 C1 S1 147.8(6) . . . . ? B8 B3 C1 S1 -114.0(6) . . . . ? C2 B3 C1 B7 -100.4(7) . . . . ? B9 B3 C1 B7 -6.9(8) . . . . ? B4 B3 C1 B7 -63.1(8) . . . . ? B8 B3 C1 B7 35.1(6) . . . . ? B11 B6 C1 C2 -98.8(6) . . . . ? B5 B6 C1 C2 -35.2(5) . . . . ? B7 B6 C1 C2 -138.6(6) . . . . ? C2 B6 C1 B8 103.4(7) . . . . ? B11 B6 C1 B8 4.6(8) . . . . ? B5 B6 C1 B8 68.3(8) . . . . ? B7 B6 C1 B8 -35.1(6) . . . . ? C2 B6 C1 B3 29.2(6) . . . . ? B11 B6 C1 B3 -69.7(8) . . . . ? B5 B6 C1 B3 -6.0(8) . . . . ? B7 B6 C1 B3 -109.4(7) . . . . ? C2 B6 C1 S1 -108.3(6) . . . . ? B11 B6 C1 S1 152.9(5) . . . . ? B5 B6 C1 S1 -143.4(6) . . . . ? B7 B6 C1 S1 113.2(6) . . . . ? C2 B6 C1 B7 138.6(6) . . . . ? B11 B6 C1 B7 39.7(6) . . . . ? B5 B6 C1 B7 103.4(6) . . . . ? B12 B7 C1 C2 -60.6(7) . . . . ? B8 B7 C1 C2 -104.4(7) . . . . ? B11 B7 C1 C2 1.3(7) . . . . ? B6 B7 C1 C2 37.8(5) . . . . ? B12 B7 C1 B8 43.8(7) . . . . ? B11 B7 C1 B8 105.7(7) . . . . ? B6 B7 C1 B8 142.2(7) . . . . ? B12 B7 C1 B3 5.8(8) . . . . ? B8 B7 C1 B3 -38.0(7) . . . . ? B11 B7 C1 B3 67.7(7) . . . . ? B6 B7 C1 B3 104.2(7) . . . . ? B12 B7 C1 B6 -98.3(6) . . . . ? B8 B7 C1 B6 -142.2(7) . . . . ? B11 B7 C1 B6 -36.5(5) . . . . ? B12 B7 C1 S1 152.5(5) . . . . ? B8 B7 C1 S1 108.7(7) . . . . ? B11 B7 C1 S1 -145.6(5) . . . . ? B6 B7 C1 S1 -109.2(6) . . . . ? B8 C1 C2 B6 -104.4(7) . . . . ? B3 C1 C2 B6 -148.9(6) . . . . ? S1 C1 C2 B6 108.3(6) . . . . ? B7 C1 C2 B6 -39.6(5) . . . . ? B8 C1 C2 B3 44.5(7) . . . . ? B6 C1 C2 B3 148.9(6) . . . . ? S1 C1 C2 B3 -102.8(7) . . . . ? B7 C1 C2 B3 109.3(6) . . . . ? B8 C1 C2 B5 -64.8(8) . . . . ? B3 C1 C2 B5 -109.3(7) . . . . ? B6 C1 C2 B5 39.7(6) . . . . ? S1 C1 C2 B5 148.0(5) . . . . ? B7 C1 C2 B5 0.0(7) . . . . ? B8 C1 C2 B4 3.1(9) . . . . ? B3 C1 C2 B4 -41.4(7) . . . . ? B6 C1 C2 B4 107.5(7) . . . . ? S1 C1 C2 B4 -144.2(6) . . . . ? B7 C1 C2 B4 67.9(8) . . . . ? B8 C1 C2 S2 150.2(6) . . . . ? B3 C1 C2 S2 105.7(6) . . . . ? B6 C1 C2 S2 -105.4(6) . . . . ? S1 C1 C2 S2 2.9(8) . . . . ? B7 C1 C2 S2 -145.0(5) . . . . ? B11 B6 C2 C1 99.3(6) . . . . ? B5 B6 C2 C1 139.6(6) . . . . ? B7 B6 C2 C1 36.1(5) . . . . ? B11 B6 C2 B3 68.2(8) . . . . ? C1 B6 C2 B3 -31.1(6) . . . . ? B5 B6 C2 B3 108.5(7) . . . . ? B7 B6 C2 B3 5.0(9) . . . . ? B11 B6 C2 B5 -40.3(6) . . . . ? C1 B6 C2 B5 -139.6(6) . . . . ? B7 B6 C2 B5 -103.5(6) . . . . ? B11 B6 C2 B4 -4.0(8) . . . . ? C1 B6 C2 B4 -103.4(6) . . . . ? B5 B6 C2 B4 36.3(6) . . . . ? B7 B6 C2 B4 -67.3(8) . . . . ? B11 B6 C2 S2 -151.1(5) . . . . ? C1 B6 C2 S2 109.6(6) . . . . ? B5 B6 C2 S2 -110.8(6) . . . . ? B7 B6 C2 S2 145.6(5) . . . . ? B9 B3 C2 C1 -94.4(6) . . . . ? B4 B3 C2 C1 -137.0(7) . . . . ? B8 B3 C2 C1 -35.8(6) . . . . ? C1 B3 C2 B6 31.2(6) . . . . ? B9 B3 C2 B6 -63.2(8) . . . . ? B4 B3 C2 B6 -105.8(7) . . . . ? B8 B3 C2 B6 -4.5(9) . . . . ? C1 B3 C2 B5 104.6(7) . . . . ? B9 B3 C2 B5 10.1(8) . . . . ? B4 B3 C2 B5 -32.4(7) . . . . ? B8 B3 C2 B5 68.8(8) . . . . ? C1 B3 C2 B4 137.0(7) . . . . ? B9 B3 C2 B4 42.6(6) . . . . ? B8 B3 C2 B4 101.3(7) . . . . ? C1 B3 C2 S2 -109.2(6) . . . . ? B9 B3 C2 S2 156.3(5) . . . . ? B4 B3 C2 S2 113.7(6) . . . . ? B8 B3 C2 S2 -145.0(6) . . . . ? B4 B5 C2 C1 103.3(6) . . . . ? B10 B5 C2 C1 62.6(7) . . . . ? B11 B5 C2 C1 -1.4(7) . . . . ? B6 B5 C2 C1 -39.2(5) . . . . ? B4 B5 C2 B6 142.5(6) . . . . ? B10 B5 C2 B6 101.9(7) . . . . ? B11 B5 C2 B6 37.9(5) . . . . ? B4 B5 C2 B3 33.1(7) . . . . ? B10 B5 C2 B3 -7.5(9) . . . . ? B11 B5 C2 B3 -71.5(8) . . . . ? B6 B5 C2 B3 -109.3(7) . . . . ? B10 B5 C2 B4 -40.6(6) . . . . ? B11 B5 C2 B4 -104.6(7) . . . . ? B6 B5 C2 B4 -142.5(6) . . . . ? B4 B5 C2 S2 -112.0(6) . . . . ? B10 B5 C2 S2 -152.6(5) . . . . ? B11 B5 C2 S2 143.4(5) . . . . ? B6 B5 C2 S2 105.5(6) . . . . ? B9 B4 C2 C1 -6.1(9) . . . . ? B10 B4 C2 C1 -64.6(8) . . . . ? B5 B4 C2 C1 -106.4(7) . . . . ? B3 B4 C2 C1 40.8(7) . . . . ? B9 B4 C2 B6 63.2(8) . . . . ? B10 B4 C2 B6 4.7(9) . . . . ? B5 B4 C2 B6 -37.1(6) . . . . ? B3 B4 C2 B6 110.1(7) . . . . ? B9 B4 C2 B3 -46.9(7) . . . . ? B10 B4 C2 B3 -105.3(7) . . . . ? B5 B4 C2 B3 -147.2(7) . . . . ? B9 B4 C2 B5 100.3(7) . . . . ? B10 B4 C2 B5 41.9(6) . . . . ? B3 B4 C2 B5 147.2(7) . . . . ? B9 B4 C2 S2 -151.9(6) . . . . ? B10 B4 C2 S2 149.6(6) . . . . ? B5 B4 C2 S2 107.8(7) . . . . ? B3 B4 C2 S2 -105.0(7) . . . . ? C7 C3 C4 C10 -176.4(9) . . . . ? C9 C3 C4 C10 9.0(14) . . . . ? Ir1 C3 C4 C10 126.4(10) . . . . ? C7 C3 C4 C5 -2.5(10) . . . . ? C9 C3 C4 C5 -177.1(7) . . . . ? Ir1 C3 C4 C5 -59.6(5) . . . . ? C7 C3 C4 Ir1 57.1(6) . . . . ? C9 C3 C4 Ir1 -117.5(7) . . . . ? C3 C4 C5 C6 -3.8(9) . . . . ? C10 C4 C5 C6 170.5(8) . . . . ? Ir1 C4 C5 C6 -63.3(5) . . . . ? C3 C4 C5 C11 -174.9(7) . . . . ? C10 C4 C5 C11 -0.7(13) . . . . ? Ir1 C4 C5 C11 125.5(7) . . . . ? C3 C4 C5 Ir1 59.6(5) . . . . ? C10 C4 C5 Ir1 -126.2(9) . . . . ? C4 C5 C6 C7 8.0(8) . . . . ? C11 C5 C6 C7 179.1(6) . . . . ? Ir1 C5 C6 C7 -56.2(5) . . . . ? C4 C5 C6 C12 -176.5(8) . . . . ? C11 C5 C6 C12 -5.3(12) . . . . ? Ir1 C5 C6 C12 119.3(8) . . . . ? C4 C5 C6 Ir1 64.3(6) . . . . ? C11 C5 C6 Ir1 -124.6(7) . . . . ? C4 C3 C7 C6 7.5(10) . . . . ? C9 C3 C7 C6 -178.2(7) . . . . ? Ir1 C3 C7 C6 68.0(5) . . . . ? C4 C3 C7 C8 173.8(8) . . . . ? C9 C3 C7 C8 -11.8(13) . . . . ? Ir1 C3 C7 C8 -125.6(8) . . . . ? C4 C3 C7 Ir1 -60.5(7) . . . . ? C9 C3 C7 Ir1 113.8(7) . . . . ? C5 C6 C7 C3 -9.0(8) . . . . ? C12 C6 C7 C3 175.5(8) . . . . ? Ir1 C6 C7 C3 -67.2(5) . . . . ? C5 C6 C7 C8 -175.7(7) . . . . ? C12 C6 C7 C8 8.8(12) . . . . ? Ir1 C6 C7 C8 126.0(8) . . . . ? C5 C6 C7 Ir1 58.3(5) . . . . ? C12 C6 C7 Ir1 -117.3(8) . . . . ? N1 C13 C14 C15 -178.0(8) . . . . ? C18 C13 C14 C15 -4.2(14) . . . . ? N1 C13 C14 S2 4.7(12) . . . . ? C18 C13 C14 S2 178.5(7) . . . . ? C13 C14 C15 C16 -1.5(13) . . . . ? S2 C14 C15 C16 175.8(6) . . . . ? C14 C15 C16 C17 2.2(13) . . . . ? C14 C15 C16 N2 -169.7(7) . . . . ? C15 C16 C17 C18 2.7(13) . . . . ? N2 C16 C17 C18 174.2(8) . . . . ? C15 C16 C17 C20 -175.7(9) . . . . ? N2 C16 C17 C20 -4.2(13) . . . . ? C16 C17 C18 C13 -8.4(13) . . . . ? C20 C17 C18 C13 170.0(9) . . . . ? C16 C17 C18 C19 -176.5(8) . . . . ? C20 C17 C18 C19 1.9(14) . . . . ? N1 C13 C18 C17 -177.0(8) . . . . ? C14 C13 C18 C17 9.3(14) . . . . ? N1 C13 C18 C19 -8.4(13) . . . . ? C14 C13 C18 C19 177.9(8) . . . . ? C3 C7 Ir1 N1 -69.8(5) . . . . ? C6 C7 Ir1 N1 178.0(4) . . . . ? C8 C7 Ir1 N1 54.9(7) . . . . ? C6 C7 Ir1 C3 -112.2(6) . . . . ? C8 C7 Ir1 C3 124.8(8) . . . . ? C3 C7 Ir1 C5 74.8(5) . . . . ? C6 C7 Ir1 C5 -37.3(4) . . . . ? C8 C7 Ir1 C5 -160.4(7) . . . . ? C3 C7 Ir1 C6 112.2(6) . . . . ? C8 C7 Ir1 C6 -123.0(8) . . . . ? C3 C7 Ir1 C4 32.4(5) . . . . ? C6 C7 Ir1 C4 -79.8(5) . . . . ? C8 C7 Ir1 C4 157.2(7) . . . . ? C3 C7 Ir1 S2 89.2(8) . . . . ? C6 C7 Ir1 S2 -23.0(9) . . . . ? C8 C7 Ir1 S2 -146.0(6) . . . . ? C3 C7 Ir1 S1 -158.3(4) . . . . ? C6 C7 Ir1 S1 89.5(4) . . . . ? C8 C7 Ir1 S1 -33.5(6) . . . . ? C7 C3 Ir1 N1 120.2(4) . . . . ? C4 C3 Ir1 N1 -113.6(5) . . . . ? C9 C3 Ir1 N1 2.5(6) . . . . ? C4 C3 Ir1 C7 126.1(7) . . . . ? C9 C3 Ir1 C7 -117.7(8) . . . . ? C7 C3 Ir1 C5 -85.9(5) . . . . ? C4 C3 Ir1 C5 40.2(5) . . . . ? C9 C3 Ir1 C5 156.4(7) . . . . ? C7 C3 Ir1 C6 -41.9(4) . . . . ? C4 C3 Ir1 C6 84.2(5) . . . . ? C9 C3 Ir1 C6 -159.6(7) . . . . ? C7 C3 Ir1 C4 -126.1(7) . . . . ? C9 C3 Ir1 C4 116.2(8) . . . . ? C7 C3 Ir1 S2 -153.8(3) . . . . ? C4 C3 Ir1 S2 -27.7(6) . . . . ? C9 C3 Ir1 S2 88.5(6) . . . . ? C7 C3 Ir1 S1 28.5(5) . . . . ? C4 C3 Ir1 S1 154.7(4) . . . . ? C9 C3 Ir1 S1 -89.2(6) . . . . ? C6 C5 Ir1 N1 135.6(5) . . . . ? C4 C5 Ir1 N1 16.4(7) . . . . ? C11 C5 Ir1 N1 -104.3(7) . . . . ? C6 C5 Ir1 C7 38.4(4) . . . . ? C4 C5 Ir1 C7 -80.8(5) . . . . ? C11 C5 Ir1 C7 158.4(8) . . . . ? C6 C5 Ir1 C3 80.4(4) . . . . ? C4 C5 Ir1 C3 -38.8(4) . . . . ? C11 C5 Ir1 C3 -159.6(8) . . . . ? C4 C5 Ir1 C6 -119.2(6) . . . . ? C11 C5 Ir1 C6 120.1(9) . . . . ? C6 C5 Ir1 C4 119.2(6) . . . . ? C11 C5 Ir1 C4 -120.8(9) . . . . ? C6 C5 Ir1 S2 -137.5(4) . . . . ? C4 C5 Ir1 S2 103.4(4) . . . . ? C11 C5 Ir1 S2 -17.4(7) . . . . ? C6 C5 Ir1 S1 -40.1(5) . . . . ? C4 C5 Ir1 S1 -159.3(4) . . . . ? C11 C5 Ir1 S1 80.0(7) . . . . ? C5 C6 Ir1 N1 -122.2(6) . . . . ? C7 C6 Ir1 N1 -4.2(8) . . . . ? C12 C6 Ir1 N1 115.9(8) . . . . ? C5 C6 Ir1 C7 -117.9(6) . . . . ? C12 C6 Ir1 C7 120.1(9) . . . . ? C5 C6 Ir1 C3 -78.3(5) . . . . ? C7 C6 Ir1 C3 39.6(4) . . . . ? C12 C6 Ir1 C3 159.8(8) . . . . ? C7 C6 Ir1 C5 117.9(6) . . . . ? C12 C6 Ir1 C5 -121.9(8) . . . . ? C5 C6 Ir1 C4 -36.8(4) . . . . ? C7 C6 Ir1 C4 81.1(5) . . . . ? C12 C6 Ir1 C4 -158.7(8) . . . . ? C5 C6 Ir1 S2 54.2(5) . . . . ? C7 C6 Ir1 S2 172.1(3) . . . . ? C12 C6 Ir1 S2 -67.7(7) . . . . ? C5 C6 Ir1 S1 148.3(4) . . . . ? C7 C6 Ir1 S1 -93.7(4) . . . . ? C12 C6 Ir1 S1 26.4(7) . . . . ? C3 C4 Ir1 N1 75.4(5) . . . . ? C10 C4 Ir1 N1 -49.9(9) . . . . ? C5 C4 Ir1 N1 -170.8(4) . . . . ? C3 C4 Ir1 C7 -32.9(5) . . . . ? C10 C4 Ir1 C7 -158.1(9) . . . . ? C5 C4 Ir1 C7 81.0(5) . . . . ? C10 C4 Ir1 C3 -125.2(10) . . . . ? C5 C4 Ir1 C3 113.9(7) . . . . ? C3 C4 Ir1 C5 -113.9(7) . . . . ? C10 C4 Ir1 C5 120.9(10) . . . . ? C3 C4 Ir1 C6 -76.8(5) . . . . ? C10 C4 Ir1 C6 157.9(9) . . . . ? C5 C4 Ir1 C6 37.0(4) . . . . ? C3 C4 Ir1 S2 161.7(4) . . . . ? C10 C4 Ir1 S2 36.4(8) . . . . ? C5 C4 Ir1 S2 -84.5(4) . . . . ? C3 C4 Ir1 S1 -62.8(8) . . . . ? C10 C4 Ir1 S1 171.9(5) . . . . ? C5 C4 Ir1 S1 51.0(8) . . . . ? C14 C13 N1 Ir1 1.2(12) . . . . ? C18 C13 N1 Ir1 -172.5(7) . . . . ? C7 Ir1 N1 C13 169.4(6) . . . . ? C3 Ir1 N1 C13 134.0(7) . . . . ? C5 Ir1 N1 C13 87.0(8) . . . . ? C6 Ir1 N1 C13 172.4(7) . . . . ? C4 Ir1 N1 C13 97.9(7) . . . . ? S2 Ir1 N1 C13 -4.6(6) . . . . ? S1 Ir1 N1 C13 -96.5(6) . . . . ? C15 C16 N2 O1 177.9(8) . . . . ? C17 C16 N2 O1 5.8(13) . . . . ? C15 C16 N2 O2 -10.5(11) . . . . ? C17 C16 N2 O2 177.4(8) . . . . ? C2 C1 S1 Ir1 -13.3(6) . . . . ? B8 C1 S1 Ir1 -158.1(6) . . . . ? B3 C1 S1 Ir1 -81.3(5) . . . . ? B6 C1 S1 Ir1 55.8(6) . . . . ? B7 C1 S1 Ir1 131.3(5) . . . . ? N1 Ir1 S1 C1 96.5(3) . . . . ? C7 Ir1 S1 C1 -149.5(3) . . . . ? C3 Ir1 S1 C1 -166.6(4) . . . . ? C5 Ir1 S1 C1 -85.8(4) . . . . ? C6 Ir1 S1 C1 -109.6(3) . . . . ? C4 Ir1 S1 C1 -122.3(7) . . . . ? S2 Ir1 S1 C1 14.9(3) . . . . ? C15 C14 S2 C2 -77.7(7) . . . . ? C13 C14 S2 C2 99.7(7) . . . . ? C15 C14 S2 Ir1 175.5(6) . . . . ? C13 C14 S2 Ir1 -7.0(7) . . . . ? C1 C2 S2 C14 -93.6(6) . . . . ? B6 C2 S2 C14 -164.6(5) . . . . ? B3 C2 S2 C14 -23.0(6) . . . . ? B5 C2 S2 C14 122.8(6) . . . . ? B4 C2 S2 C14 50.5(7) . . . . ? C1 C2 S2 Ir1 9.1(6) . . . . ? B6 C2 S2 Ir1 -62.0(6) . . . . ? B3 C2 S2 Ir1 79.7(5) . . . . ? B5 C2 S2 Ir1 -134.5(5) . . . . ? B4 C2 S2 Ir1 153.1(5) . . . . ? N1 Ir1 S2 C14 5.3(3) . . . . ? C7 Ir1 S2 C14 -155.4(7) . . . . ? C3 Ir1 S2 C14 -86.7(4) . . . . ? C5 Ir1 S2 C14 -142.3(3) . . . . ? C6 Ir1 S2 C14 -173.1(4) . . . . ? C4 Ir1 S2 C14 -103.5(4) . . . . ? S1 Ir1 S2 C14 91.5(3) . . . . ? N1 Ir1 S2 C2 -99.6(3) . . . . ? C7 Ir1 S2 C2 99.7(7) . . . . ? C3 Ir1 S2 C2 168.5(4) . . . . ? C5 Ir1 S2 C2 112.9(3) . . . . ? C6 Ir1 S2 C2 82.1(4) . . . . ? C4 Ir1 S2 C2 151.6(3) . . . . ? S1 Ir1 S2 C2 -13.3(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.839 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.137 data_8 #TrackingRef '- cif.cif' _database_code_depnum_ccdc_archive 'CCDC 851359' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H33 B10 Ir N2 O2 S2' _chemical_formula_weight 697.90 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' O O 0.0106 0.0060 '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 p2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1639(16) _cell_length_b 14.233(2) _cell_length_c 17.920(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.097(3) _cell_angle_gamma 90.00 _cell_volume 2836.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4062 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.59 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 4.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.408 _exptl_absorpt_correction_T_max 0.614 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16893 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5577 _reflns_number_gt 4186 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^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 5577 _refine_ls_number_parameters 446 _refine_ls_number_restraints 375 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.200 _refine_ls_shift/su_max 0.000 _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 C2 C 0.1570(6) 0.1318(5) 0.2757(4) 0.0448(17) Uani 1 1 d . . . C15 C 0.0404(7) 0.1992(5) 0.0881(5) 0.057(2) Uani 1 1 d . B . H15A H -0.0116 0.2354 0.1140 0.068 Uiso 1 1 calc R . . C14 C 0.1538(7) 0.1783(5) 0.1226(4) 0.0498(18) Uani 1 1 d . . . C1 C 0.2646(6) 0.0639(5) 0.3144(4) 0.0490(18) Uani 1 1 d . . . C13 C 0.2393(7) 0.1271(5) 0.0854(4) 0.0500(18) Uani 1 1 d . A . B3 B 0.1571(7) 0.0172(6) 0.2505(5) 0.047(2) Uani 1 1 d . . . H3 H 0.1754 -0.0083 0.1947 0.056 Uiso 1 1 calc R . . C18 C 0.1924(9) 0.0910(7) 0.0149(5) 0.072(3) Uani 1 1 d . . . B8 B 0.0207(8) 0.0758(6) 0.2659(6) 0.055(2) Uani 1 1 d . . . H8 H -0.0502 0.0870 0.2201 0.066 Uiso 1 1 calc R . . C16 C 0.0016(9) 0.1679(8) 0.0160(6) 0.075(3) Uani 1 1 d . . . B5 B 0.2420(10) 0.0417(7) 0.4066(6) 0.067(3) Uani 1 1 d . . . H5 H 0.3147 0.0308 0.4514 0.080 Uiso 1 1 calc R . . C17 C 0.0779(10) 0.1130(7) -0.0206(5) 0.072(3) Uani 1 1 d . B . B4 B 0.2066(9) -0.0426(6) 0.3354(5) 0.056(2) Uani 1 1 d . . . H4 H 0.2572 -0.1088 0.3346 0.067 Uiso 1 1 calc R . . B9 B 0.0517(9) -0.0385(8) 0.3058(6) 0.064(3) Uani 1 1 d . . . H9 H 0.0008 -0.1015 0.2865 0.076 Uiso 1 1 calc R . . B6 B 0.2090(10) 0.1558(7) 0.3669(6) 0.064(3) Uani 1 1 d . . . H6 H 0.2605 0.2187 0.3856 0.077 Uiso 1 1 calc R . . B10 B 0.1040(10) -0.0227(8) 0.4024(7) 0.073(3) Uani 1 1 d . . . H10 H 0.0865 -0.0753 0.4450 0.087 Uiso 1 1 calc R . . C20 C -0.1203(11) 0.1968(9) -0.0176(7) 0.117(5) Uani 1 1 d . B . H20A H -0.1120 0.2412 -0.0572 0.176 Uiso 1 1 calc R . . H20B H -0.1639 0.2254 0.0203 0.176 Uiso 1 1 calc R . . H20C H -0.1632 0.1426 -0.0374 0.176 Uiso 1 1 calc R . . C19 C 0.0358(12) 0.0760(8) -0.0977(5) 0.115(5) Uani 1 1 d . . . H19A H -0.0282 0.0318 -0.0937 0.173 Uiso 1 1 calc R B . H19B H 0.1015 0.0455 -0.1190 0.173 Uiso 1 1 calc R . . H19C H 0.0075 0.1273 -0.1293 0.173 Uiso 1 1 calc R . . B11 B 0.1031(10) 0.1034(8) 0.4222(7) 0.076(3) Uani 1 1 d . . . H11 H 0.0851 0.1312 0.4774 0.091 Uiso 1 1 calc R . . B7 B 0.0538(9) 0.1618(8) 0.3374(6) 0.063(3) Uani 1 1 d . . . H7 H 0.0048 0.2289 0.3371 0.075 Uiso 1 1 calc R . . B12 B -0.0125(10) 0.0548(8) 0.3584(6) 0.073(3) Uani 1 1 d . . . H12 H -0.1062 0.0520 0.3728 0.088 Uiso 1 1 calc R . . C3 C 0.593(2) 0.2444(19) 0.1990(12) 0.0598(18) Uani 0.524(13) 1 d PU A 1 C4 C 0.5204(19) 0.2947(15) 0.1404(13) 0.0604(19) Uani 0.524(13) 1 d PU A 1 C5 C 0.441(2) 0.3551(19) 0.1717(16) 0.060(2) Uani 0.524(13) 1 d PU A 1 C6 C 0.460(2) 0.3446(19) 0.2501(13) 0.0592(18) Uani 0.524(13) 1 d PU A 1 C7 C 0.5565(19) 0.2792(15) 0.2694(15) 0.0599(18) Uani 0.524(13) 1 d PU A 1 C8 C 0.6933(16) 0.1830(14) 0.1939(14) 0.071(3) Uani 0.524(13) 1 d PU A 1 H8A H 0.7650 0.2195 0.1907 0.106 Uiso 0.524(13) 1 calc PR A 1 H8B H 0.6796 0.1445 0.1499 0.106 Uiso 0.524(13) 1 calc PR A 1 H8C H 0.7025 0.1436 0.2375 0.106 Uiso 0.524(13) 1 calc PR A 1 C9 C 0.541(2) 0.2772(15) 0.0638(11) 0.078(3) Uani 0.524(13) 1 d PU A 1 H9A H 0.5936 0.3245 0.0470 0.117 Uiso 0.524(13) 1 calc PR A 1 H9B H 0.4656 0.2791 0.0334 0.117 Uiso 0.524(13) 1 calc PR A 1 H9C H 0.5770 0.2165 0.0597 0.117 Uiso 0.524(13) 1 calc PR A 1 C10 C 0.349(2) 0.4164(17) 0.1247(14) 0.076(4) Uani 0.524(13) 1 d PU A 1 H10A H 0.3844 0.4767 0.1164 0.113 Uiso 0.524(13) 1 calc PR A 1 H10B H 0.2787 0.4245 0.1510 0.113 Uiso 0.524(13) 1 calc PR A 1 H10C H 0.3278 0.3865 0.0774 0.113 Uiso 0.524(13) 1 calc PR A 1 C11 C 0.3990(17) 0.4045(13) 0.3047(12) 0.068(3) Uani 0.524(13) 1 d PU A 1 H11A H 0.4431 0.4619 0.3136 0.102 Uiso 0.524(13) 1 calc PR A 1 H11B H 0.3960 0.3710 0.3510 0.102 Uiso 0.524(13) 1 calc PR A 1 H11C H 0.3187 0.4186 0.2841 0.102 Uiso 0.524(13) 1 calc PR A 1 C12 C 0.6087(19) 0.2608(16) 0.3504(11) 0.074(3) Uani 0.524(13) 1 d PU A 1 H12A H 0.6748 0.3028 0.3629 0.111 Uiso 0.524(13) 1 calc PR A 1 H12B H 0.6363 0.1970 0.3550 0.111 Uiso 0.524(13) 1 calc PR A 1 H12C H 0.5475 0.2712 0.3839 0.111 Uiso 0.524(13) 1 calc PR A 1 C3' C 0.445(2) 0.356(2) 0.2316(15) 0.059(2) Uani 0.476(13) 1 d PU A 2 C4' C 0.527(2) 0.3015(16) 0.2772(16) 0.0600(19) Uani 0.476(13) 1 d PU A 2 C5' C 0.596(2) 0.246(2) 0.2247(13) 0.0602(19) Uani 0.476(13) 1 d PU A 2 C6' C 0.549(2) 0.2691(16) 0.1512(16) 0.058(2) Uani 0.476(13) 1 d PU A 2 C7' C 0.453(3) 0.341(2) 0.1567(15) 0.057(3) Uani 0.476(13) 1 d PU A 2 C8' C 0.3540(17) 0.4238(14) 0.2653(13) 0.065(3) Uani 0.476(13) 1 d PU A 2 H8'A H 0.3889 0.4853 0.2714 0.098 Uiso 0.476(13) 1 calc PR A 2 H8'B H 0.3352 0.4005 0.3131 0.098 Uiso 0.476(13) 1 calc PR A 2 H8'C H 0.2818 0.4274 0.2321 0.098 Uiso 0.476(13) 1 calc PR A 2 C9' C 0.553(2) 0.3017(16) 0.3616(12) 0.075(3) Uani 0.476(13) 1 d PU A 2 H9'A H 0.6099 0.3505 0.3760 0.112 Uiso 0.476(13) 1 calc PR A 2 H9'B H 0.5862 0.2420 0.3777 0.112 Uiso 0.476(13) 1 calc PR A 2 H9'C H 0.4799 0.3126 0.3845 0.112 Uiso 0.476(13) 1 calc PR A 2 C10' C 0.7014(18) 0.1816(15) 0.2408(15) 0.072(3) Uani 0.476(13) 1 d PU A 2 H10D H 0.7744 0.2176 0.2458 0.108 Uiso 0.476(13) 1 calc PR A 2 H10E H 0.7043 0.1376 0.2003 0.108 Uiso 0.476(13) 1 calc PR A 2 H10F H 0.6929 0.1480 0.2865 0.108 Uiso 0.476(13) 1 calc PR A 2 C11' C 0.603(3) 0.231(2) 0.086(2) 0.147(3) Uani 0.476(13) 1 d PU A 2 H11D H 0.6649 0.2729 0.0726 0.221 Uiso 0.476(13) 1 calc PR A 2 H11E H 0.5423 0.2251 0.0450 0.221 Uiso 0.476(13) 1 calc PR A 2 H11F H 0.6370 0.1706 0.0985 0.221 Uiso 0.476(13) 1 calc PR A 2 C12' C 0.391(3) 0.391(3) 0.0920(16) 0.120(13) Uani 0.476(13) 1 d P A 2 H12D H 0.4337 0.4476 0.0829 0.180 Uiso 0.476(13) 1 calc PR A 2 H12E H 0.3106 0.4056 0.1026 0.180 Uiso 0.476(13) 1 calc PR A 2 H12F H 0.3889 0.3513 0.0484 0.180 Uiso 0.476(13) 1 calc PR A 2 Ir1 Ir 0.40596(2) 0.20785(2) 0.207500(16) 0.04389(13) Uani 1 1 d . . . N2 N 0.2721(10) 0.0295(8) -0.0223(6) 0.103(3) Uani 0.383(16) 1 d PU B 1 N1 N 0.3508(6) 0.1225(5) 0.1184(4) 0.0600(18) Uani 1 1 d . A . H1A H 0.4007 0.0830 0.1021 0.072 Uiso 1 1 calc R . . N2' N 0.2721(10) 0.0295(8) -0.0223(6) 0.103(3) Uani 0.617(16) 1 d PU B 2 O1 O 0.286(3) 0.020(2) -0.0821(15) 0.134(5) Uani 0.383(16) 1 d PU B 1 O2 O 0.355(2) -0.021(2) 0.0200(14) 0.109(5) Uani 0.383(16) 1 d PU B 1 O1' O 0.3731(14) 0.0433(14) -0.0177(9) 0.124(5) Uani 0.617(16) 1 d PU B 2 O2' O 0.2247(16) -0.0221(12) -0.0746(8) 0.123(4) Uani 0.617(16) 1 d PU B 2 S1 S 0.41363(18) 0.07629(16) 0.28763(15) 0.0662(6) Uani 1 1 d . . . S2 S 0.20037(16) 0.22217(12) 0.21172(11) 0.0442(4) Uani 1 1 d . A . 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 C2 0.038(4) 0.047(4) 0.051(4) -0.011(4) 0.009(3) 0.001(3) C15 0.046(4) 0.061(5) 0.063(5) 0.013(4) 0.002(4) -0.013(3) C14 0.049(4) 0.054(5) 0.045(4) 0.008(4) 0.000(3) -0.011(3) C1 0.048(4) 0.050(4) 0.049(4) 0.002(4) 0.007(3) 0.010(3) C13 0.054(5) 0.047(4) 0.050(4) -0.005(4) 0.006(4) -0.012(3) B3 0.049(5) 0.043(5) 0.049(5) -0.001(4) 0.012(4) -0.002(4) C18 0.094(7) 0.071(6) 0.052(5) -0.003(5) 0.007(5) -0.025(5) B8 0.048(5) 0.050(5) 0.070(6) -0.002(5) 0.016(4) -0.007(4) C16 0.074(6) 0.081(7) 0.064(6) 0.019(5) -0.022(5) -0.043(5) B5 0.083(7) 0.067(7) 0.051(6) 0.005(5) 0.009(5) -0.004(5) C17 0.094(7) 0.066(6) 0.053(5) 0.017(5) -0.006(5) -0.039(5) B4 0.068(6) 0.042(5) 0.059(6) 0.004(4) 0.016(5) 0.000(4) B9 0.069(6) 0.066(7) 0.059(6) 0.011(5) 0.022(5) -0.006(5) B6 0.075(7) 0.061(6) 0.058(6) 0.000(5) 0.014(5) 0.001(5) B10 0.076(7) 0.073(7) 0.072(7) 0.008(6) 0.029(6) -0.004(5) C20 0.093(9) 0.159(13) 0.090(8) 0.066(8) -0.044(7) -0.053(7) C19 0.186(13) 0.100(9) 0.052(6) 0.002(6) -0.028(7) -0.070(8) B11 0.093(8) 0.067(7) 0.072(7) -0.004(6) 0.035(6) -0.009(6) B7 0.056(6) 0.069(6) 0.066(6) -0.010(5) 0.026(5) 0.008(5) B12 0.071(7) 0.084(8) 0.069(7) 0.002(6) 0.030(5) 0.001(6) C3 0.046(4) 0.060(4) 0.073(4) 0.001(4) 0.004(4) -0.013(3) C4 0.053(4) 0.062(4) 0.067(4) 0.002(4) 0.005(4) -0.016(3) C5 0.053(4) 0.058(4) 0.069(5) 0.003(4) 0.001(4) -0.012(3) C6 0.052(4) 0.056(4) 0.069(4) -0.002(4) 0.003(3) -0.012(3) C7 0.049(4) 0.060(4) 0.069(4) 0.001(4) -0.001(3) -0.015(3) C8 0.052(6) 0.073(6) 0.088(7) 0.004(6) 0.009(6) -0.006(4) C9 0.081(7) 0.088(7) 0.068(5) -0.002(5) 0.019(5) -0.030(6) C10 0.070(8) 0.059(8) 0.094(9) 0.023(8) -0.009(7) -0.016(6) C11 0.063(6) 0.064(6) 0.078(6) -0.010(6) 0.013(6) -0.016(5) C12 0.072(7) 0.075(7) 0.073(5) 0.005(6) -0.007(5) -0.011(6) C3' 0.052(4) 0.056(4) 0.069(5) -0.004(4) 0.003(4) -0.013(3) C4' 0.051(4) 0.059(4) 0.069(4) -0.001(4) 0.000(4) -0.015(3) C5' 0.046(4) 0.060(4) 0.074(4) 0.002(4) 0.000(4) -0.013(3) C6' 0.048(4) 0.058(4) 0.070(4) 0.000(4) 0.006(4) -0.014(3) C7' 0.051(5) 0.054(6) 0.066(6) 0.006(5) 0.000(5) -0.012(5) C8' 0.055(6) 0.060(6) 0.081(7) -0.005(6) 0.007(6) -0.012(5) C9' 0.072(7) 0.079(7) 0.072(5) -0.001(6) -0.005(5) -0.013(6) C10' 0.052(6) 0.073(6) 0.089(7) 0.002(7) -0.002(6) -0.004(4) C11' 0.128(7) 0.159(8) 0.172(6) -0.108(6) 0.112(6) -0.089(6) C12' 0.09(2) 0.17(3) 0.10(2) 0.06(2) -0.031(16) -0.03(2) Ir1 0.03627(19) 0.0459(2) 0.0501(2) -0.00547(14) 0.00664(13) -0.00278(12) N2 0.123(6) 0.119(6) 0.073(5) -0.047(5) 0.038(5) -0.038(5) N1 0.056(4) 0.066(4) 0.060(4) -0.022(4) 0.015(3) -0.003(3) N2' 0.123(6) 0.119(6) 0.073(5) -0.047(5) 0.038(5) -0.038(5) O1 0.156(12) 0.158(12) 0.091(8) -0.051(10) 0.037(9) -0.027(10) O2 0.111(11) 0.129(12) 0.093(10) -0.052(9) 0.034(8) -0.021(9) O1' 0.113(7) 0.158(11) 0.104(9) -0.062(8) 0.025(7) -0.005(8) O2' 0.146(10) 0.136(10) 0.090(8) -0.058(7) 0.040(7) -0.065(8) S1 0.0428(11) 0.0618(13) 0.0948(17) 0.0159(13) 0.0105(11) 0.0083(9) S2 0.0380(9) 0.0424(10) 0.0524(11) -0.0020(8) 0.0048(8) 0.0017(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 C2 C1 1.646(10) . ? C2 B3 1.693(11) . ? C2 B8 1.714(11) . ? C2 B6 1.719(13) . ? C2 B7 1.719(11) . ? C2 S2 1.817(8) . ? C15 C14 1.391(11) . ? C15 C16 1.400(13) . ? C15 H15A 0.9300 . ? C14 C13 1.413(10) . ? C14 S2 1.751(8) . ? C1 B4 1.703(11) . ? C1 B3 1.717(12) . ? C1 B5 1.723(12) . ? C1 B6 1.757(12) . ? C1 S1 1.781(7) . ? C13 N1 1.331(9) . ? C13 C18 1.420(11) . ? B3 B8 1.780(12) . ? B3 B4 1.786(13) . ? B3 B9 1.789(12) . ? B3 H3 1.1000 . ? C18 C17 1.412(13) . ? C18 N2 1.452(13) . ? B8 B12 1.756(14) . ? B8 B7 1.787(14) . ? B8 B9 1.797(14) . ? B8 H8 1.1000 . ? C16 C17 1.366(14) . ? C16 C20 1.496(14) . ? B5 B4 1.770(14) . ? B5 B10 1.788(15) . ? B5 B6 1.799(15) . ? B5 B11 1.825(15) . ? B5 H5 1.1000 . ? C17 C19 1.513(13) . ? B4 B10 1.755(13) . ? B4 B9 1.764(14) . ? B4 H4 1.1000 . ? B9 B10 1.792(16) . ? B9 B12 1.812(15) . ? B9 H9 1.1000 . ? B6 B7 1.768(15) . ? B6 B11 1.773(14) . ? B6 H6 1.1000 . ? B10 B12 1.829(16) . ? B10 B11 1.830(16) . ? B10 H10 1.1000 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? B11 B7 1.777(17) . ? B11 B12 1.787(17) . ? B11 H11 1.1000 . ? B7 B12 1.750(15) . ? B7 H7 1.1000 . ? B12 H12 1.1000 . ? C3 C8 1.43(3) . ? C3 C7 1.45(3) . ? C3 C4 1.46(3) . ? C3 Ir1 2.17(2) . ? C4 C5 1.39(3) . ? C4 C9 1.43(3) . ? C4 Ir1 2.21(2) . ? C5 C6 1.41(3) . ? C5 C10 1.54(4) . ? C5 Ir1 2.23(3) . ? C6 C7 1.44(3) . ? C6 C11 1.51(3) . ? C6 Ir1 2.16(3) . ? C7 C12 1.54(3) . ? C7 Ir1 2.18(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C3' C7' 1.37(4) . ? C3' C4' 1.41(3) . ? C3' C8' 1.56(3) . ? C3' Ir1 2.19(3) . ? C4' C5' 1.49(3) . ? C4' C9' 1.51(3) . ? C4' Ir1 2.21(2) . ? C5' C6' 1.41(3) . ? C5' C10' 1.51(3) . ? C5' Ir1 2.18(3) . ? C6' C11' 1.46(3) . ? C6' C7' 1.48(3) . ? C6' Ir1 2.15(2) . ? C7' C12' 1.48(4) . ? C7' Ir1 2.18(3) . ? C8' H8'A 0.9600 . ? C8' H8'B 0.9600 . ? C8' H8'C 0.9600 . ? C9' H9'A 0.9600 . ? C9' H9'B 0.9600 . ? C9' H9'C 0.9600 . ? C10' H10D 0.9600 . ? C10' H10E 0.9600 . ? C10' H10F 0.9600 . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? Ir1 N1 2.057(6) . ? Ir1 S2 2.3121(18) . ? N2 O1 1.10(2) . ? N2 O2 1.36(3) . ? N1 H1A 0.8600 . ? 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 C1 C2 B3 61.9(5) . . ? C1 C2 B8 112.2(6) . . ? B3 C2 B8 63.0(5) . . ? C1 C2 B6 62.9(5) . . ? B3 C2 B6 115.9(6) . . ? B8 C2 B6 114.3(6) . . ? C1 C2 B7 112.4(6) . . ? B3 C2 B7 115.3(6) . . ? B8 C2 B7 62.7(5) . . ? B6 C2 B7 61.9(5) . . ? C1 C2 S2 117.1(5) . . ? B3 C2 S2 120.5(5) . . ? B8 C2 S2 123.3(5) . . ? B6 C2 S2 111.9(5) . . ? B7 C2 S2 117.5(5) . . ? C14 C15 C16 122.4(9) . . ? C14 C15 H15A 118.8 . . ? C16 C15 H15A 118.8 . . ? C15 C14 C13 121.9(7) . . ? C15 C14 S2 120.8(6) . . ? C13 C14 S2 117.1(6) . . ? C2 C1 B4 109.7(6) . . ? C2 C1 B3 60.4(5) . . ? B4 C1 B3 63.0(5) . . ? C2 C1 B5 110.4(6) . . ? B4 C1 B5 62.2(5) . . ? B3 C1 B5 114.5(6) . . ? C2 C1 B6 60.6(5) . . ? B4 C1 B6 112.6(6) . . ? B3 C1 B6 112.7(6) . . ? B5 C1 B6 62.2(5) . . ? C2 C1 S1 119.5(5) . . ? B4 C1 S1 122.0(5) . . ? B3 C1 S1 118.2(5) . . ? B5 C1 S1 119.8(6) . . ? B6 C1 S1 117.0(6) . . ? N1 C13 C14 117.5(7) . . ? N1 C13 C18 129.3(8) . . ? C14 C13 C18 113.2(8) . . ? C2 B3 C1 57.7(4) . . ? C2 B3 B8 59.1(5) . . ? C1 B3 B8 105.8(6) . . ? C2 B3 B4 103.8(6) . . ? C1 B3 B4 58.1(5) . . ? B8 B3 B4 107.2(6) . . ? C2 B3 B9 105.2(6) . . ? C1 B3 B9 104.9(6) . . ? B8 B3 B9 60.5(5) . . ? B4 B3 B9 59.1(5) . . ? C2 B3 H3 124.4 . . ? C1 B3 H3 124.0 . . ? B8 B3 H3 121.7 . . ? B4 B3 H3 123.3 . . ? B9 B3 H3 122.8 . . ? C17 C18 C13 124.7(9) . . ? C17 C18 N2 119.6(9) . . ? C13 C18 N2 115.7(9) . . ? C2 B8 B12 104.0(7) . . ? C2 B8 B3 57.9(4) . . ? B12 B8 B3 108.8(7) . . ? C2 B8 B7 58.8(5) . . ? B12 B8 B7 59.2(6) . . ? B3 B8 B7 107.8(7) . . ? C2 B8 B9 104.0(7) . . ? B12 B8 B9 61.3(6) . . ? B3 B8 B9 60.0(5) . . ? B7 B8 B9 108.3(7) . . ? C2 B8 H8 125.6 . . ? B12 B8 H8 122.1 . . ? B3 B8 H8 121.4 . . ? B7 B8 H8 121.6 . . ? B9 B8 H8 122.0 . . ? C17 C16 C15 118.1(9) . . ? C17 C16 C20 123.3(10) . . ? C15 C16 C20 118.6(11) . . ? C1 B5 B4 58.3(5) . . ? C1 B5 B10 104.6(7) . . ? B4 B5 B10 59.1(6) . . ? C1 B5 B6 59.8(5) . . ? B4 B5 B6 107.6(7) . . ? B10 B5 B6 107.5(8) . . ? C1 B5 B11 104.9(7) . . ? B4 B5 B11 107.4(8) . . ? B10 B5 B11 60.8(6) . . ? B6 B5 B11 58.6(6) . . ? C1 B5 H5 124.2 . . ? B4 B5 H5 122.2 . . ? B10 B5 H5 122.5 . . ? B6 B5 H5 121.8 . . ? B11 B5 H5 122.6 . . ? C16 C17 C18 119.2(8) . . ? C16 C17 C19 118.8(10) . . ? C18 C17 C19 122.0(11) . . ? C1 B4 B10 107.0(7) . . ? C1 B4 B9 106.6(6) . . ? B10 B4 B9 61.2(6) . . ? C1 B4 B5 59.5(5) . . ? B10 B4 B5 61.0(6) . . ? B9 B4 B5 110.1(7) . . ? C1 B4 B3 58.9(5) . . ? B10 B4 B3 109.5(7) . . ? B9 B4 B3 60.5(5) . . ? B5 B4 B3 108.9(7) . . ? C1 B4 H4 123.7 . . ? B10 B4 H4 120.9 . . ? B9 B4 H4 121.0 . . ? B5 B4 H4 120.5 . . ? B3 B4 H4 121.2 . . ? B4 B9 B3 60.4(5) . . ? B4 B9 B10 59.1(6) . . ? B3 B9 B10 107.8(7) . . ? B4 B9 B8 107.4(7) . . ? B3 B9 B8 59.5(5) . . ? B10 B9 B8 107.8(8) . . ? B4 B9 B12 106.9(7) . . ? B3 B9 B12 105.9(7) . . ? B10 B9 B12 61.0(6) . . ? B8 B9 B12 58.2(6) . . ? B4 B9 H9 122.2 . . ? B3 B9 H9 122.3 . . ? B10 B9 H9 121.4 . . ? B8 B9 H9 122.4 . . ? B12 B9 H9 122.9 . . ? C2 B6 C1 56.5(5) . . ? C2 B6 B7 59.1(5) . . ? C1 B6 B7 105.0(7) . . ? C2 B6 B11 105.2(7) . . ? C1 B6 B11 105.7(7) . . ? B7 B6 B11 60.2(6) . . ? C2 B6 B5 103.7(7) . . ? C1 B6 B5 58.0(5) . . ? B7 B6 B5 108.8(7) . . ? B11 B6 B5 61.4(6) . . ? C2 B6 H6 125.1 . . ? C1 B6 H6 124.7 . . ? B7 B6 H6 121.6 . . ? B11 B6 H6 121.9 . . ? B5 B6 H6 122.1 . . ? B4 B10 B5 60.0(6) . . ? B4 B10 B9 59.7(6) . . ? B5 B10 B9 108.1(7) . . ? B4 B10 B12 106.5(7) . . ? B5 B10 B12 106.7(8) . . ? B9 B10 B12 60.1(6) . . ? B4 B10 B11 107.8(7) . . ? B5 B10 B11 60.6(6) . . ? B9 B10 B11 107.7(8) . . ? B12 B10 B11 58.5(7) . . ? B4 B10 H10 122.2 . . ? B5 B10 H10 121.7 . . ? B9 B10 H10 121.5 . . ? B12 B10 H10 123.1 . . ? B11 B10 H10 121.9 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? B6 B11 B7 59.7(6) . . ? B6 B11 B12 106.5(8) . . ? B7 B11 B12 58.8(6) . . ? B6 B11 B5 60.0(6) . . ? B7 B11 B5 107.3(7) . . ? B12 B11 B5 106.9(8) . . ? B6 B11 B10 106.8(7) . . ? B7 B11 B10 107.4(8) . . ? B12 B11 B10 60.8(6) . . ? B5 B11 B10 58.6(6) . . ? B6 B11 H11 122.4 . . ? B7 B11 H11 122.2 . . ? B12 B11 H11 122.4 . . ? B5 B11 H11 122.5 . . ? B10 B11 H11 122.1 . . ? C2 B7 B12 104.1(7) . . ? C2 B7 B6 59.1(5) . . ? B12 B7 B6 108.4(8) . . ? C2 B7 B11 105.1(7) . . ? B12 B7 B11 60.9(6) . . ? B6 B7 B11 60.0(6) . . ? C2 B7 B8 58.5(5) . . ? B12 B7 B8 59.5(6) . . ? B6 B7 B8 108.5(6) . . ? B11 B7 B8 108.8(7) . . ? C2 B7 H7 125.0 . . ? B12 B7 H7 122.5 . . ? B6 B7 H7 121.1 . . ? B11 B7 H7 121.7 . . ? B8 B7 H7 121.4 . . ? B7 B12 B8 61.3(6) . . ? B7 B12 B11 60.3(6) . . ? B8 B12 B11 109.7(7) . . ? B7 B12 B9 109.3(7) . . ? B8 B12 B9 60.5(5) . . ? B11 B12 B9 108.7(8) . . ? B7 B12 B10 108.6(8) . . ? B8 B12 B10 107.9(7) . . ? B11 B12 B10 60.8(7) . . ? B9 B12 B10 58.9(6) . . ? B7 B12 H12 120.8 . . ? B8 B12 H12 120.8 . . ? B11 B12 H12 120.8 . . ? B9 B12 H12 121.6 . . ? B10 B12 H12 122.1 . . ? C8 C3 C7 123(2) . . ? C8 C3 C4 130(2) . . ? C7 C3 C4 106(2) . . ? C8 C3 Ir1 128.4(17) . . ? C7 C3 Ir1 70.9(12) . . ? C4 C3 Ir1 72.0(12) . . ? C5 C4 C9 131(2) . . ? C5 C4 C3 110(2) . . ? C9 C4 C3 119(2) . . ? C5 C4 Ir1 72.8(15) . . ? C9 C4 Ir1 125.0(15) . . ? C3 C4 Ir1 69.2(11) . . ? C4 C5 C6 107(3) . . ? C4 C5 C10 123(2) . . ? C6 C5 C10 130(2) . . ? C4 C5 Ir1 70.7(14) . . ? C6 C5 Ir1 68.4(16) . . ? C10 C5 Ir1 124.5(18) . . ? C5 C6 C7 111(2) . . ? C5 C6 C11 123(2) . . ? C7 C6 C11 126(2) . . ? C5 C6 Ir1 74.2(15) . . ? C7 C6 Ir1 71.5(14) . . ? C11 C6 Ir1 127.5(16) . . ? C6 C7 C3 106(2) . . ? C6 C7 C12 123(2) . . ? C3 C7 C12 131(2) . . ? C6 C7 Ir1 69.8(14) . . ? C3 C7 Ir1 70.3(13) . . ? C12 C7 Ir1 127.7(14) . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 . . ? C7' C3' C4' 112(3) . . ? C7' C3' C8' 125(2) . . ? C4' C3' C8' 122(2) . . ? C7' C3' Ir1 71.4(18) . . ? C4' C3' Ir1 71.9(15) . . ? C8' C3' Ir1 123.0(17) . . ? C3' C4' C5' 106(2) . . ? C3' C4' C9' 129(2) . . ? C5' C4' C9' 125(2) . . ? C3' C4' Ir1 70.8(16) . . ? C5' C4' Ir1 69.4(13) . . ? C9' C4' Ir1 128.3(16) . . ? C6' C5' C4' 108(2) . . ? C6' C5' C10' 123(2) . . ? C4' C5' C10' 130(2) . . ? C6' C5' Ir1 69.5(13) . . ? C4' C5' Ir1 71.0(14) . . ? C10' C5' Ir1 127.3(18) . . ? C5' C6' C11' 121(3) . . ? C5' C6' C7' 108(2) . . ? C11' C6' C7' 131(3) . . ? C5' C6' Ir1 72.5(14) . . ? C11' C6' Ir1 127.0(16) . . ? C7' C6' Ir1 71.4(14) . . ? C3' C7' C12' 129(3) . . ? C3' C7' C6' 107(3) . . ? C12' C7' C6' 125(2) . . ? C3' C7' Ir1 72.1(17) . . ? C12' C7' Ir1 129(2) . . ? C6' C7' Ir1 68.6(15) . . ? C3' C8' H8'A 109.5 . . ? C3' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? C3' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C4' C9' H9'A 109.5 . . ? C4' C9' H9'B 109.5 . . ? H9'A C9' H9'B 109.5 . . ? C4' C9' H9'C 109.5 . . ? H9'A C9' H9'C 109.5 . . ? H9'B C9' H9'C 109.5 . . ? C5' C10' H10D 109.5 . . ? C5' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C5' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C6' C11' H11D 109.5 . . ? C6' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C6' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C7' C12' H12D 109.5 . . ? C7' C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C7' C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? N1 Ir1 C6' 93.3(7) . . ? N1 Ir1 C6 149.7(6) . . ? C6' Ir1 C6 66.6(10) . . ? N1 Ir1 C3 108.1(6) . . ? C6' Ir1 C3 27.1(7) . . ? C6 Ir1 C3 64.3(10) . . ? N1 Ir1 C7 146.5(6) . . ? C6' Ir1 C7 58.6(9) . . ? C6 Ir1 C7 38.7(8) . . ? C3 Ir1 C7 38.9(8) . . ? N1 Ir1 C7' 104.8(7) . . ? C6' Ir1 C7' 40.1(9) . . ? C6 Ir1 C7' 45.2(9) . . ? C3 Ir1 C7' 59.5(11) . . ? C7 Ir1 C7' 66.7(10) . . ? N1 Ir1 C5' 118.5(8) . . ? C6' Ir1 C5' 38.0(9) . . ? C6 Ir1 C5' 58.9(10) . . ? C3 Ir1 C5' 12.1(8) . . ? C7 Ir1 C5' 28.0(8) . . ? C7' Ir1 C5' 64.7(11) . . ? N1 Ir1 C3' 139.7(7) . . ? C6' Ir1 C3' 63.7(10) . . ? C6 Ir1 C3' 10.4(9) . . ? C3 Ir1 C3' 66.8(10) . . ? C7 Ir1 C3' 47.1(8) . . ? C7' Ir1 C3' 36.5(9) . . ? C5' Ir1 C3' 63.6(11) . . ? N1 Ir1 C4' 157.3(6) . . ? C6' Ir1 C4' 64.9(10) . . ? C6 Ir1 C4' 27.8(8) . . ? C3 Ir1 C4' 49.4(8) . . ? C7 Ir1 C4' 12.6(7) . . ? C7' Ir1 C4' 63.5(11) . . ? C5' Ir1 C4' 39.5(9) . . ? C3' Ir1 C4' 37.3(9) . . ? N1 Ir1 C4 93.2(6) . . ? C6' Ir1 C4 13.3(7) . . ? C6 Ir1 C4 61.9(9) . . ? C3 Ir1 C4 38.8(8) . . ? C7 Ir1 C4 63.9(9) . . ? C7' Ir1 C4 27.8(8) . . ? C5' Ir1 C4 48.3(8) . . ? C3' Ir1 C4 56.8(9) . . ? C4' Ir1 C4 67.3(9) . . ? N1 Ir1 C5 112.3(7) . . ? C6' Ir1 C5 47.9(8) . . ? C6 Ir1 C5 37.4(8) . . ? C3 Ir1 C5 64.1(10) . . ? C7 Ir1 C5 64.2(10) . . ? C7' Ir1 C5 9.7(10) . . ? C5' Ir1 C5 67.3(11) . . ? C3' Ir1 C5 27.9(9) . . ? C4' Ir1 C5 58.9(10) . . ? C4 Ir1 C5 36.5(8) . . ? N1 Ir1 S2 81.26(18) . . ? C6' Ir1 S2 139.5(6) . . ? C6 Ir1 S2 99.1(7) . . ? C3 Ir1 S2 160.9(7) . . ? C7 Ir1 S2 131.7(6) . . ? C7' Ir1 S2 102.4(8) . . ? C5' Ir1 S2 157.9(8) . . ? C3' Ir1 S2 95.2(8) . . ? C4' Ir1 S2 119.3(6) . . ? C4 Ir1 S2 126.3(5) . . ? C5 Ir1 S2 97.2(7) . . ? O1 N2 O2 109(2) . . ? O1 N2 C18 132(2) . . ? O2 N2 C18 118.9(12) . . ? C13 N1 Ir1 121.2(5) . . ? C13 N1 H1A 119.4 . . ? Ir1 N1 H1A 119.4 . . ? C1 S1 Ir1 105.0(3) . . ? C14 S2 C2 104.4(3) . . ? C14 S2 Ir1 98.8(3) . . ? C2 S2 Ir1 106.2(2) . . ? 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 C16 C15 C14 C13 2.7(12) . . . . ? C16 C15 C14 S2 177.9(6) . . . . ? B3 C2 C1 B4 -40.6(6) . . . . ? B8 C2 C1 B4 -1.4(8) . . . . ? B6 C2 C1 B4 105.5(7) . . . . ? B7 C2 C1 B4 67.1(8) . . . . ? S2 C2 C1 B4 -152.5(5) . . . . ? B8 C2 C1 B3 39.2(6) . . . . ? B6 C2 C1 B3 146.1(6) . . . . ? B7 C2 C1 B3 107.7(7) . . . . ? S2 C2 C1 B3 -111.8(6) . . . . ? B3 C2 C1 B5 -107.3(7) . . . . ? B8 C2 C1 B5 -68.1(8) . . . . ? B6 C2 C1 B5 38.8(6) . . . . ? B7 C2 C1 B5 0.3(8) . . . . ? S2 C2 C1 B5 140.8(6) . . . . ? B3 C2 C1 B6 -146.1(6) . . . . ? B8 C2 C1 B6 -106.9(7) . . . . ? B7 C2 C1 B6 -38.4(6) . . . . ? S2 C2 C1 B6 102.1(6) . . . . ? B3 C2 C1 S1 107.7(6) . . . . ? B8 C2 C1 S1 146.8(5) . . . . ? B6 C2 C1 S1 -106.2(6) . . . . ? B7 C2 C1 S1 -144.7(6) . . . . ? S2 C2 C1 S1 -4.2(8) . . . . ? C15 C14 C13 N1 170.3(7) . . . . ? S2 C14 C13 N1 -5.1(10) . . . . ? C15 C14 C13 C18 -7.1(11) . . . . ? S2 C14 C13 C18 177.6(6) . . . . ? B8 C2 B3 C1 -138.9(6) . . . . ? B6 C2 B3 C1 -33.5(6) . . . . ? B7 C2 B3 C1 -103.0(7) . . . . ? S2 C2 B3 C1 106.6(6) . . . . ? C1 C2 B3 B8 138.9(6) . . . . ? B6 C2 B3 B8 105.4(7) . . . . ? B7 C2 B3 B8 35.9(7) . . . . ? S2 C2 B3 B8 -114.5(6) . . . . ? C1 C2 B3 B4 37.0(5) . . . . ? B8 C2 B3 B4 -102.0(6) . . . . ? B6 C2 B3 B4 3.5(8) . . . . ? B7 C2 B3 B4 -66.0(8) . . . . ? S2 C2 B3 B4 143.6(5) . . . . ? C1 C2 B3 B9 98.3(7) . . . . ? B8 C2 B3 B9 -40.7(6) . . . . ? B6 C2 B3 B9 64.8(8) . . . . ? B7 C2 B3 B9 -4.7(9) . . . . ? S2 C2 B3 B9 -155.1(5) . . . . ? B4 C1 B3 C2 136.5(6) . . . . ? B5 C1 B3 C2 100.4(7) . . . . ? B6 C1 B3 C2 31.8(6) . . . . ? S1 C1 B3 C2 -109.8(6) . . . . ? C2 C1 B3 B8 -35.8(5) . . . . ? B4 C1 B3 B8 100.7(6) . . . . ? B5 C1 B3 B8 64.6(8) . . . . ? B6 C1 B3 B8 -4.1(8) . . . . ? S1 C1 B3 B8 -145.6(5) . . . . ? C2 C1 B3 B4 -136.5(6) . . . . ? B5 C1 B3 B4 -36.1(7) . . . . ? B6 C1 B3 B4 -104.8(7) . . . . ? S1 C1 B3 B4 113.7(6) . . . . ? C2 C1 B3 B9 -98.8(6) . . . . ? B4 C1 B3 B9 37.7(6) . . . . ? B5 C1 B3 B9 1.6(8) . . . . ? B6 C1 B3 B9 -67.0(8) . . . . ? S1 C1 B3 B9 151.4(5) . . . . ? N1 C13 C18 C17 -168.9(8) . . . . ? C14 C13 C18 C17 8.1(12) . . . . ? N1 C13 C18 N2 9.3(13) . . . . ? C14 C13 C18 N2 -173.7(8) . . . . ? C1 C2 B8 B12 64.9(8) . . . . ? B3 C2 B8 B12 103.6(7) . . . . ? B6 C2 B8 B12 -4.3(9) . . . . ? B7 C2 B8 B12 -39.8(7) . . . . ? S2 C2 B8 B12 -146.2(6) . . . . ? C1 C2 B8 B3 -38.7(6) . . . . ? B6 C2 B8 B3 -107.9(7) . . . . ? B7 C2 B8 B3 -143.3(7) . . . . ? S2 C2 B8 B3 110.2(6) . . . . ? C1 C2 B8 B7 104.6(7) . . . . ? B3 C2 B8 B7 143.3(7) . . . . ? B6 C2 B8 B7 35.4(7) . . . . ? S2 C2 B8 B7 -106.4(7) . . . . ? C1 C2 B8 B9 1.4(8) . . . . ? B3 C2 B8 B9 40.2(6) . . . . ? B6 C2 B8 B9 -67.7(8) . . . . ? B7 C2 B8 B9 -103.2(7) . . . . ? S2 C2 B8 B9 150.4(5) . . . . ? C1 B3 B8 C2 35.2(5) . . . . ? B4 B3 B8 C2 96.1(7) . . . . ? B9 B3 B8 C2 133.7(7) . . . . ? C2 B3 B8 B12 -95.1(7) . . . . ? C1 B3 B8 B12 -59.9(8) . . . . ? B4 B3 B8 B12 1.0(9) . . . . ? B9 B3 B8 B12 38.6(7) . . . . ? C2 B3 B8 B7 -32.4(6) . . . . ? C1 B3 B8 B7 2.8(8) . . . . ? B4 B3 B8 B7 63.7(8) . . . . ? B9 B3 B8 B7 101.3(8) . . . . ? C2 B3 B8 B9 -133.7(7) . . . . ? C1 B3 B8 B9 -98.5(7) . . . . ? B4 B3 B8 B9 -37.6(6) . . . . ? C14 C15 C16 C17 1.6(12) . . . . ? C14 C15 C16 C20 -177.8(7) . . . . ? C2 C1 B5 B4 102.2(7) . . . . ? B3 C1 B5 B4 36.4(7) . . . . ? B6 C1 B5 B4 140.3(7) . . . . ? S1 C1 B5 B4 -112.9(6) . . . . ? C2 C1 B5 B10 63.9(8) . . . . ? B4 C1 B5 B10 -38.3(7) . . . . ? B3 C1 B5 B10 -1.9(9) . . . . ? B6 C1 B5 B10 102.0(8) . . . . ? S1 C1 B5 B10 -151.2(6) . . . . ? C2 C1 B5 B6 -38.1(6) . . . . ? B4 C1 B5 B6 -140.3(7) . . . . ? B3 C1 B5 B6 -103.9(7) . . . . ? S1 C1 B5 B6 106.9(7) . . . . ? C2 C1 B5 B11 0.8(9) . . . . ? B4 C1 B5 B11 -101.5(8) . . . . ? B3 C1 B5 B11 -65.1(8) . . . . ? B6 C1 B5 B11 38.8(7) . . . . ? S1 C1 B5 B11 145.7(6) . . . . ? C15 C16 C17 C18 -0.8(12) . . . . ? C20 C16 C17 C18 178.6(8) . . . . ? C15 C16 C17 C19 178.1(8) . . . . ? C20 C16 C17 C19 -2.5(13) . . . . ? C13 C18 C17 C16 -4.4(13) . . . . ? N2 C18 C17 C16 177.5(9) . . . . ? C13 C18 C17 C19 176.8(8) . . . . ? N2 C18 C17 C19 -1.4(13) . . . . ? C2 C1 B4 B10 -63.5(8) . . . . ? B3 C1 B4 B10 -103.0(7) . . . . ? B5 C1 B4 B10 39.7(7) . . . . ? B6 C1 B4 B10 1.9(9) . . . . ? S1 C1 B4 B10 149.2(6) . . . . ? C2 C1 B4 B9 0.7(8) . . . . ? B3 C1 B4 B9 -38.7(6) . . . . ? B5 C1 B4 B9 103.9(7) . . . . ? B6 C1 B4 B9 66.2(8) . . . . ? S1 C1 B4 B9 -146.6(6) . . . . ? C2 C1 B4 B5 -103.2(7) . . . . ? B3 C1 B4 B5 -142.7(7) . . . . ? B6 C1 B4 B5 -37.8(7) . . . . ? S1 C1 B4 B5 109.4(7) . . . . ? C2 C1 B4 B3 39.5(5) . . . . ? B5 C1 B4 B3 142.7(7) . . . . ? B6 C1 B4 B3 104.9(7) . . . . ? S1 C1 B4 B3 -107.9(6) . . . . ? B10 B5 B4 C1 135.7(8) . . . . ? B6 B5 B4 C1 35.4(6) . . . . ? B11 B5 B4 C1 97.1(7) . . . . ? C1 B5 B4 B10 -135.7(8) . . . . ? B6 B5 B4 B10 -100.3(8) . . . . ? B11 B5 B4 B10 -38.5(7) . . . . ? C1 B5 B4 B9 -97.9(7) . . . . ? B10 B5 B4 B9 37.8(7) . . . . ? B6 B5 B4 B9 -62.5(8) . . . . ? B11 B5 B4 B9 -0.8(9) . . . . ? C1 B5 B4 B3 -33.3(6) . . . . ? B10 B5 B4 B3 102.4(7) . . . . ? B6 B5 B4 B3 2.1(9) . . . . ? B11 B5 B4 B3 63.8(8) . . . . ? C2 B3 B4 C1 -36.8(5) . . . . ? B8 B3 B4 C1 -98.2(6) . . . . ? B9 B3 B4 C1 -136.5(7) . . . . ? C2 B3 B4 B10 61.7(8) . . . . ? C1 B3 B4 B10 98.5(7) . . . . ? B8 B3 B4 B10 0.2(9) . . . . ? B9 B3 B4 B10 -38.0(7) . . . . ? C2 B3 B4 B9 99.7(6) . . . . ? C1 B3 B4 B9 136.5(7) . . . . ? B8 B3 B4 B9 38.2(6) . . . . ? C2 B3 B4 B5 -3.3(8) . . . . ? C1 B3 B4 B5 33.5(6) . . . . ? B8 B3 B4 B5 -64.7(8) . . . . ? B9 B3 B4 B5 -103.0(8) . . . . ? C1 B4 B9 B3 38.0(6) . . . . ? B10 B4 B9 B3 138.5(8) . . . . ? B5 B4 B9 B3 100.9(7) . . . . ? C1 B4 B9 B10 -100.6(7) . . . . ? B5 B4 B9 B10 -37.7(7) . . . . ? B3 B4 B9 B10 -138.5(8) . . . . ? C1 B4 B9 B8 0.2(8) . . . . ? B10 B4 B9 B8 100.7(8) . . . . ? B5 B4 B9 B8 63.1(8) . . . . ? B3 B4 B9 B8 -37.8(6) . . . . ? C1 B4 B9 B12 -61.0(8) . . . . ? B10 B4 B9 B12 39.5(7) . . . . ? B5 B4 B9 B12 1.9(9) . . . . ? B3 B4 B9 B12 -99.0(7) . . . . ? C2 B3 B9 B4 -97.2(7) . . . . ? C1 B3 B9 B4 -37.3(6) . . . . ? B8 B3 B9 B4 -137.2(7) . . . . ? C2 B3 B9 B10 -60.6(9) . . . . ? C1 B3 B9 B10 -0.6(9) . . . . ? B8 B3 B9 B10 -100.6(8) . . . . ? B4 B3 B9 B10 36.6(7) . . . . ? C2 B3 B9 B8 40.0(6) . . . . ? C1 B3 B9 B8 99.9(7) . . . . ? B4 B3 B9 B8 137.2(7) . . . . ? C2 B3 B9 B12 3.4(9) . . . . ? C1 B3 B9 B12 63.4(8) . . . . ? B8 B3 B9 B12 -36.5(7) . . . . ? B4 B3 B9 B12 100.7(8) . . . . ? C2 B8 B9 B4 -0.9(8) . . . . ? B12 B8 B9 B4 -99.4(8) . . . . ? B3 B8 B9 B4 38.2(6) . . . . ? B7 B8 B9 B4 -62.2(8) . . . . ? C2 B8 B9 B3 -39.1(6) . . . . ? B12 B8 B9 B3 -137.6(8) . . . . ? B7 B8 B9 B3 -100.4(7) . . . . ? C2 B8 B9 B10 61.4(8) . . . . ? B12 B8 B9 B10 -37.1(7) . . . . ? B3 B8 B9 B10 100.6(7) . . . . ? B7 B8 B9 B10 0.1(8) . . . . ? C2 B8 B9 B12 98.5(7) . . . . ? B3 B8 B9 B12 137.6(8) . . . . ? B7 B8 B9 B12 37.2(6) . . . . ? B3 C2 B6 C1 33.2(6) . . . . ? B8 C2 B6 C1 103.6(7) . . . . ? B7 C2 B6 C1 139.3(7) . . . . ? S2 C2 B6 C1 -110.3(5) . . . . ? C1 C2 B6 B7 -139.3(7) . . . . ? B3 C2 B6 B7 -106.2(7) . . . . ? B8 C2 B6 B7 -35.7(7) . . . . ? S2 C2 B6 B7 110.4(6) . . . . ? C1 C2 B6 B11 -99.0(7) . . . . ? B3 C2 B6 B11 -65.9(8) . . . . ? B8 C2 B6 B11 4.6(9) . . . . ? B7 C2 B6 B11 40.3(7) . . . . ? S2 C2 B6 B11 150.7(6) . . . . ? C1 C2 B6 B5 -35.4(6) . . . . ? B3 C2 B6 B5 -2.2(8) . . . . ? B8 C2 B6 B5 68.2(8) . . . . ? B7 C2 B6 B5 104.0(7) . . . . ? S2 C2 B6 B5 -145.6(6) . . . . ? B4 C1 B6 C2 -100.7(7) . . . . ? B3 C1 B6 C2 -31.7(6) . . . . ? B5 C1 B6 C2 -138.4(7) . . . . ? S1 C1 B6 C2 110.4(6) . . . . ? C2 C1 B6 B7 35.4(6) . . . . ? B4 C1 B6 B7 -65.3(8) . . . . ? B3 C1 B6 B7 3.6(8) . . . . ? B5 C1 B6 B7 -103.1(8) . . . . ? S1 C1 B6 B7 145.7(6) . . . . ? C2 C1 B6 B11 98.1(8) . . . . ? B4 C1 B6 B11 -2.6(10) . . . . ? B3 C1 B6 B11 66.3(9) . . . . ? B5 C1 B6 B11 -40.4(7) . . . . ? S1 C1 B6 B11 -151.6(6) . . . . ? C2 C1 B6 B5 138.4(7) . . . . ? B4 C1 B6 B5 37.8(7) . . . . ? B3 C1 B6 B5 106.7(7) . . . . ? S1 C1 B6 B5 -111.2(7) . . . . ? C1 B5 B6 C2 34.7(6) . . . . ? B4 B5 B6 C2 -0.1(9) . . . . ? B10 B5 B6 C2 -62.4(8) . . . . ? B11 B5 B6 C2 -100.1(8) . . . . ? B4 B5 B6 C1 -34.8(6) . . . . ? B10 B5 B6 C1 -97.1(8) . . . . ? B11 B5 B6 C1 -134.8(8) . . . . ? C1 B5 B6 B7 96.3(7) . . . . ? B4 B5 B6 B7 61.5(9) . . . . ? B10 B5 B6 B7 -0.8(9) . . . . ? B11 B5 B6 B7 -38.5(7) . . . . ? C1 B5 B6 B11 134.8(8) . . . . ? B4 B5 B6 B11 100.0(8) . . . . ? B10 B5 B6 B11 37.7(7) . . . . ? C1 B4 B10 B5 -39.0(7) . . . . ? B9 B4 B10 B5 -139.0(8) . . . . ? B3 B4 B10 B5 -101.3(7) . . . . ? C1 B4 B10 B9 100.0(7) . . . . ? B5 B4 B10 B9 139.0(8) . . . . ? B3 B4 B10 B9 37.7(7) . . . . ? C1 B4 B10 B12 61.0(9) . . . . ? B9 B4 B10 B12 -39.0(7) . . . . ? B5 B4 B10 B12 100.0(8) . . . . ? B3 B4 B10 B12 -1.3(10) . . . . ? C1 B4 B10 B11 -0.5(10) . . . . ? B9 B4 B10 B11 -100.5(9) . . . . ? B5 B4 B10 B11 38.5(8) . . . . ? B3 B4 B10 B11 -62.8(10) . . . . ? C1 B5 B10 B4 37.9(6) . . . . ? B6 B5 B10 B4 100.4(8) . . . . ? B11 B5 B10 B4 137.1(8) . . . . ? C1 B5 B10 B9 1.4(10) . . . . ? B4 B5 B10 B9 -36.6(7) . . . . ? B6 B5 B10 B9 63.8(9) . . . . ? B11 B5 B10 B9 100.5(9) . . . . ? C1 B5 B10 B12 -61.9(9) . . . . ? B4 B5 B10 B12 -99.8(8) . . . . ? B6 B5 B10 B12 0.6(9) . . . . ? B11 B5 B10 B12 37.3(7) . . . . ? C1 B5 B10 B11 -99.2(8) . . . . ? B4 B5 B10 B11 -137.1(8) . . . . ? B6 B5 B10 B11 -36.7(7) . . . . ? B3 B9 B10 B4 -37.2(7) . . . . ? B8 B9 B10 B4 -100.0(7) . . . . ? B12 B9 B10 B4 -135.9(7) . . . . ? B4 B9 B10 B5 36.7(7) . . . . ? B3 B9 B10 B5 -0.5(10) . . . . ? B8 B9 B10 B5 -63.3(9) . . . . ? B12 B9 B10 B5 -99.2(8) . . . . ? B4 B9 B10 B12 135.9(7) . . . . ? B3 B9 B10 B12 98.7(8) . . . . ? B8 B9 B10 B12 35.9(6) . . . . ? B4 B9 B10 B11 100.7(7) . . . . ? B3 B9 B10 B11 63.5(9) . . . . ? B8 B9 B10 B11 0.7(9) . . . . ? B12 B9 B10 B11 -35.2(7) . . . . ? C2 B6 B11 B7 -39.7(6) . . . . ? C1 B6 B11 B7 -98.6(7) . . . . ? B5 B6 B11 B7 -137.2(8) . . . . ? C2 B6 B11 B12 -2.8(9) . . . . ? C1 B6 B11 B12 -61.6(9) . . . . ? B7 B6 B11 B12 37.0(7) . . . . ? B5 B6 B11 B12 -100.3(8) . . . . ? C2 B6 B11 B5 97.5(7) . . . . ? C1 B6 B11 B5 38.7(7) . . . . ? B7 B6 B11 B5 137.2(8) . . . . ? C2 B6 B11 B10 61.0(9) . . . . ? C1 B6 B11 B10 2.1(10) . . . . ? B7 B6 B11 B10 100.7(9) . . . . ? B5 B6 B11 B10 -36.6(8) . . . . ? C1 B5 B11 B6 -39.4(7) . . . . ? B4 B5 B11 B6 -100.3(8) . . . . ? B10 B5 B11 B6 -138.1(8) . . . . ? C1 B5 B11 B7 -1.5(10) . . . . ? B4 B5 B11 B7 -62.5(9) . . . . ? B10 B5 B11 B7 -100.2(9) . . . . ? B6 B5 B11 B7 37.9(7) . . . . ? C1 B5 B11 B12 60.3(9) . . . . ? B4 B5 B11 B12 -0.7(9) . . . . ? B10 B5 B11 B12 -38.4(7) . . . . ? B6 B5 B11 B12 99.7(8) . . . . ? C1 B5 B11 B10 98.7(8) . . . . ? B4 B5 B11 B10 37.7(7) . . . . ? B6 B5 B11 B10 138.1(8) . . . . ? B4 B10 B11 B6 -1.1(11) . . . . ? B5 B10 B11 B6 37.2(8) . . . . ? B9 B10 B11 B6 -64.1(10) . . . . ? B12 B10 B11 B6 -99.9(9) . . . . ? B4 B10 B11 B7 61.7(10) . . . . ? B5 B10 B11 B7 100.0(8) . . . . ? B9 B10 B11 B7 -1.3(9) . . . . ? B12 B10 B11 B7 -37.1(6) . . . . ? B4 B10 B11 B12 98.8(8) . . . . ? B5 B10 B11 B12 137.1(8) . . . . ? B9 B10 B11 B12 35.8(7) . . . . ? B4 B10 B11 B5 -38.2(7) . . . . ? B9 B10 B11 B5 -101.2(8) . . . . ? B12 B10 B11 B5 -137.1(8) . . . . ? C1 C2 B7 B12 -64.4(9) . . . . ? B3 C2 B7 B12 3.9(10) . . . . ? B8 C2 B7 B12 39.9(7) . . . . ? B6 C2 B7 B12 -103.3(8) . . . . ? S2 C2 B7 B12 155.2(6) . . . . ? C1 C2 B7 B6 38.9(6) . . . . ? B3 C2 B7 B6 107.2(7) . . . . ? B8 C2 B7 B6 143.2(7) . . . . ? S2 C2 B7 B6 -101.5(6) . . . . ? C1 C2 B7 B11 -1.3(9) . . . . ? B3 C2 B7 B11 67.0(9) . . . . ? B8 C2 B7 B11 103.1(8) . . . . ? B6 C2 B7 B11 -40.2(7) . . . . ? S2 C2 B7 B11 -141.7(6) . . . . ? C1 C2 B7 B8 -104.4(7) . . . . ? B3 C2 B7 B8 -36.0(7) . . . . ? B6 C2 B7 B8 -143.2(7) . . . . ? S2 C2 B7 B8 115.3(6) . . . . ? C1 B6 B7 C2 -34.2(5) . . . . ? B11 B6 B7 C2 -134.0(7) . . . . ? B5 B6 B7 C2 -95.0(7) . . . . ? C2 B6 B7 B12 95.7(7) . . . . ? C1 B6 B7 B12 61.4(8) . . . . ? B11 B6 B7 B12 -38.4(7) . . . . ? B5 B6 B7 B12 0.7(9) . . . . ? C2 B6 B7 B11 134.0(7) . . . . ? C1 B6 B7 B11 99.8(7) . . . . ? B5 B6 B7 B11 39.0(7) . . . . ? C2 B6 B7 B8 32.6(6) . . . . ? C1 B6 B7 B8 -1.7(9) . . . . ? B11 B6 B7 B8 -101.5(8) . . . . ? B5 B6 B7 B8 -62.4(9) . . . . ? B6 B11 B7 C2 39.7(6) . . . . ? B12 B11 B7 C2 -98.0(7) . . . . ? B5 B11 B7 C2 1.7(9) . . . . ? B10 B11 B7 C2 -60.0(8) . . . . ? B6 B11 B7 B12 137.6(7) . . . . ? B5 B11 B7 B12 99.7(8) . . . . ? B10 B11 B7 B12 38.0(7) . . . . ? B12 B11 B7 B6 -137.6(7) . . . . ? B5 B11 B7 B6 -38.0(7) . . . . ? B10 B11 B7 B6 -99.6(8) . . . . ? B6 B11 B7 B8 101.0(7) . . . . ? B12 B11 B7 B8 -36.6(6) . . . . ? B5 B11 B7 B8 63.0(9) . . . . ? B10 B11 B7 B8 1.4(9) . . . . ? B12 B8 B7 C2 133.7(8) . . . . ? B3 B8 B7 C2 32.1(6) . . . . ? B9 B8 B7 C2 95.6(7) . . . . ? C2 B8 B7 B12 -133.7(8) . . . . ? B3 B8 B7 B12 -101.6(7) . . . . ? B9 B8 B7 B12 -38.2(7) . . . . ? C2 B8 B7 B6 -32.8(6) . . . . ? B12 B8 B7 B6 101.0(8) . . . . ? B3 B8 B7 B6 -0.7(9) . . . . ? B9 B8 B7 B6 62.8(8) . . . . ? C2 B8 B7 B11 -96.5(7) . . . . ? B12 B8 B7 B11 37.2(7) . . . . ? B3 B8 B7 B11 -64.4(8) . . . . ? B9 B8 B7 B11 -0.9(8) . . . . ? C2 B7 B12 B8 -39.4(6) . . . . ? B6 B7 B12 B8 -101.0(7) . . . . ? B11 B7 B12 B8 -139.0(7) . . . . ? C2 B7 B12 B11 99.6(8) . . . . ? B6 B7 B12 B11 38.0(7) . . . . ? B8 B7 B12 B11 139.0(7) . . . . ? C2 B7 B12 B9 -1.4(10) . . . . ? B6 B7 B12 B9 -63.0(10) . . . . ? B11 B7 B12 B9 -101.0(8) . . . . ? B8 B7 B12 B9 38.0(7) . . . . ? C2 B7 B12 B10 61.3(9) . . . . ? B6 B7 B12 B10 -0.3(9) . . . . ? B11 B7 B12 B10 -38.3(7) . . . . ? B8 B7 B12 B10 100.7(8) . . . . ? C2 B8 B12 B7 39.5(6) . . . . ? B3 B8 B12 B7 100.0(7) . . . . ? B9 B8 B12 B7 138.1(7) . . . . ? C2 B8 B12 B11 2.3(9) . . . . ? B3 B8 B12 B11 62.8(9) . . . . ? B7 B8 B12 B11 -37.2(7) . . . . ? B9 B8 B12 B11 100.8(8) . . . . ? C2 B8 B12 B9 -98.5(7) . . . . ? B3 B8 B12 B9 -38.0(7) . . . . ? B7 B8 B12 B9 -138.1(7) . . . . ? C2 B8 B12 B10 -62.3(9) . . . . ? B3 B8 B12 B10 -1.8(10) . . . . ? B7 B8 B12 B10 -101.8(8) . . . . ? B9 B8 B12 B10 36.2(7) . . . . ? B6 B11 B12 B7 -37.4(7) . . . . ? B5 B11 B12 B7 -100.3(7) . . . . ? B10 B11 B12 B7 -137.7(7) . . . . ? B6 B11 B12 B8 0.3(10) . . . . ? B7 B11 B12 B8 37.7(7) . . . . ? B5 B11 B12 B8 -62.6(9) . . . . ? B10 B11 B12 B8 -100.0(8) . . . . ? B6 B11 B12 B9 64.7(9) . . . . ? B7 B11 B12 B9 102.1(7) . . . . ? B5 B11 B12 B9 1.8(9) . . . . ? B10 B11 B12 B9 -35.6(7) . . . . ? B6 B11 B12 B10 100.3(8) . . . . ? B7 B11 B12 B10 137.7(7) . . . . ? B5 B11 B12 B10 37.4(7) . . . . ? B4 B9 B12 B7 61.9(9) . . . . ? B3 B9 B12 B7 -1.3(10) . . . . ? B10 B9 B12 B7 100.6(9) . . . . ? B8 B9 B12 B7 -38.4(7) . . . . ? B4 B9 B12 B8 100.3(7) . . . . ? B3 B9 B12 B8 37.1(6) . . . . ? B10 B9 B12 B8 139.0(7) . . . . ? B4 B9 B12 B11 -2.3(9) . . . . ? B3 B9 B12 B11 -65.5(9) . . . . ? B10 B9 B12 B11 36.4(7) . . . . ? B8 B9 B12 B11 -102.6(8) . . . . ? B4 B9 B12 B10 -38.6(6) . . . . ? B3 B9 B12 B10 -101.8(8) . . . . ? B8 B9 B12 B10 -139.0(7) . . . . ? B4 B10 B12 B7 -63.0(9) . . . . ? B5 B10 B12 B7 -0.2(10) . . . . ? B9 B10 B12 B7 -101.8(8) . . . . ? B11 B10 B12 B7 38.1(7) . . . . ? B4 B10 B12 B8 1.9(10) . . . . ? B5 B10 B12 B8 64.8(9) . . . . ? B9 B10 B12 B8 -36.9(7) . . . . ? B11 B10 B12 B8 103.0(8) . . . . ? B4 B10 B12 B11 -101.1(8) . . . . ? B5 B10 B12 B11 -38.3(7) . . . . ? B9 B10 B12 B11 -139.9(7) . . . . ? B4 B10 B12 B9 38.8(7) . . . . ? B5 B10 B12 B9 101.7(8) . . . . ? B11 B10 B12 B9 139.9(7) . . . . ? C8 C3 C4 C5 -173(2) . . . . ? C7 C3 C4 C5 -2(2) . . . . ? Ir1 C3 C4 C5 61.4(17) . . . . ? C8 C3 C4 C9 6(3) . . . . ? C7 C3 C4 C9 177.5(18) . . . . ? Ir1 C3 C4 C9 -119.5(18) . . . . ? C8 C3 C4 Ir1 125(2) . . . . ? C7 C3 C4 Ir1 -63.1(14) . . . . ? C9 C4 C5 C6 -179(2) . . . . ? C3 C4 C5 C6 0(3) . . . . ? Ir1 C4 C5 C6 59.2(17) . . . . ? C9 C4 C5 C10 2(4) . . . . ? C3 C4 C5 C10 -179(2) . . . . ? Ir1 C4 C5 C10 -119(2) . . . . ? C9 C4 C5 Ir1 122(2) . . . . ? C3 C4 C5 Ir1 -59.2(15) . . . . ? C4 C5 C6 C7 2(3) . . . . ? C10 C5 C6 C7 -180(3) . . . . ? Ir1 C5 C6 C7 62.6(17) . . . . ? C4 C5 C6 C11 174(2) . . . . ? C10 C5 C6 C11 -7(4) . . . . ? Ir1 C5 C6 C11 -125(2) . . . . ? C4 C5 C6 Ir1 -60.7(17) . . . . ? C10 C5 C6 Ir1 118(3) . . . . ? C5 C6 C7 C3 -3(3) . . . . ? C11 C6 C7 C3 -175(2) . . . . ? Ir1 C6 C7 C3 61.4(14) . . . . ? C5 C6 C7 C12 173(2) . . . . ? C11 C6 C7 C12 1(3) . . . . ? Ir1 C6 C7 C12 -122.6(19) . . . . ? C5 C6 C7 Ir1 -64.3(18) . . . . ? C11 C6 C7 Ir1 123(2) . . . . ? C8 C3 C7 C6 175(2) . . . . ? C4 C3 C7 C6 3(2) . . . . ? Ir1 C3 C7 C6 -61.1(15) . . . . ? C8 C3 C7 C12 -1(4) . . . . ? C4 C3 C7 C12 -173(2) . . . . ? Ir1 C3 C7 C12 123(2) . . . . ? C8 C3 C7 Ir1 -124(2) . . . . ? C4 C3 C7 Ir1 63.8(14) . . . . ? C7' C3' C4' C5' 1(3) . . . . ? C8' C3' C4' C5' 179(2) . . . . ? Ir1 C3' C4' C5' 61.0(15) . . . . ? C7' C3' C4' C9' 176(3) . . . . ? C8' C3' C4' C9' -6(4) . . . . ? Ir1 C3' C4' C9' -124(2) . . . . ? C7' C3' C4' Ir1 -60(2) . . . . ? C8' C3' C4' Ir1 118(2) . . . . ? C3' C4' C5' C6' -2(2) . . . . ? C9' C4' C5' C6' -177(2) . . . . ? Ir1 C4' C5' C6' 60.2(15) . . . . ? C3' C4' C5' C10' 175(3) . . . . ? C9' C4' C5' C10' 0(4) . . . . ? Ir1 C4' C5' C10' -123(3) . . . . ? C3' C4' C5' Ir1 -61.9(16) . . . . ? C9' C4' C5' Ir1 123(2) . . . . ? C4' C5' C6' C11' 176(2) . . . . ? C10' C5' C6' C11' -1(3) . . . . ? Ir1 C5' C6' C11' -123(2) . . . . ? C4' C5' C6' C7' 2(3) . . . . ? C10' C5' C6' C7' -175(2) . . . . ? Ir1 C5' C6' C7' 63.1(17) . . . . ? C4' C5' C6' Ir1 -61.2(15) . . . . ? C10' C5' C6' Ir1 122(2) . . . . ? C4' C3' C7' C12' -174(3) . . . . ? C8' C3' C7' C12' 8(5) . . . . ? Ir1 C3' C7' C12' 126(3) . . . . ? C4' C3' C7' C6' 0(3) . . . . ? C8' C3' C7' C6' -178(2) . . . . ? Ir1 C3' C7' C6' -60.1(17) . . . . ? C4' C3' C7' Ir1 60.4(19) . . . . ? C8' C3' C7' Ir1 -118(3) . . . . ? C5' C6' C7' C3' -1(3) . . . . ? C11' C6' C7' C3' -174(3) . . . . ? Ir1 C6' C7' C3' 62.4(19) . . . . ? C5' C6' C7' C12' 173(3) . . . . ? C11' C6' C7' C12' 0(4) . . . . ? Ir1 C6' C7' C12' -123(3) . . . . ? C5' C6' C7' Ir1 -63.8(16) . . . . ? C11' C6' C7' Ir1 123(3) . . . . ? C5' C6' Ir1 N1 -134.6(16) . . . . ? C11' C6' Ir1 N1 -19(3) . . . . ? C7' C6' Ir1 N1 109.1(14) . . . . ? C5' C6' Ir1 C6 68.9(16) . . . . ? C11' C6' Ir1 C6 -175(3) . . . . ? C7' C6' Ir1 C6 -47.4(15) . . . . ? C5' C6' Ir1 C3 -10(3) . . . . ? C11' C6' Ir1 C3 106(3) . . . . ? C7' C6' Ir1 C3 -126(3) . . . . ? C5' C6' Ir1 C7 26.0(15) . . . . ? C11' C6' Ir1 C7 142(3) . . . . ? C7' C6' Ir1 C7 -90.3(15) . . . . ? C5' C6' Ir1 C7' 116(2) . . . . ? C11' C6' Ir1 C7' -128(3) . . . . ? C11' C6' Ir1 C5' 116(3) . . . . ? C7' C6' Ir1 C5' -116(2) . . . . ? C5' C6' Ir1 C3' 80.0(17) . . . . ? C11' C6' Ir1 C3' -164(3) . . . . ? C7' C6' Ir1 C3' -36.3(14) . . . . ? C5' C6' Ir1 C4' 38.4(16) . . . . ? C11' C6' Ir1 C4' 154(3) . . . . ? C7' C6' Ir1 C4' -77.9(16) . . . . ? C5' C6' Ir1 C4 136(6) . . . . ? C11' C6' Ir1 C4 -108(6) . . . . ? C7' C6' Ir1 C4 19(5) . . . . ? C5' C6' Ir1 C5 108(2) . . . . ? C11' C6' Ir1 C5 -136(3) . . . . ? C7' C6' Ir1 C5 -8(2) . . . . ? C5' C6' Ir1 S2 145.0(15) . . . . ? C11' C6' Ir1 S2 -99(3) . . . . ? C7' C6' Ir1 S2 29(2) . . . . ? C5 C6 Ir1 N1 -2(3) . . . . ? C7 C6 Ir1 N1 -120.5(15) . . . . ? C11 C6 Ir1 N1 118.3(17) . . . . ? C5 C6 Ir1 C6' 50.5(15) . . . . ? C7 C6 Ir1 C6' -68.5(15) . . . . ? C11 C6 Ir1 C6' 170(2) . . . . ? C5 C6 Ir1 C3 80.3(16) . . . . ? C7 C6 Ir1 C3 -38.7(14) . . . . ? C11 C6 Ir1 C3 -160(2) . . . . ? C5 C6 Ir1 C7 119(2) . . . . ? C11 C6 Ir1 C7 -121(2) . . . . ? C5 C6 Ir1 C7' 9(2) . . . . ? C7 C6 Ir1 C7' -110(2) . . . . ? C11 C6 Ir1 C7' 128(3) . . . . ? C5 C6 Ir1 C5' 92.7(17) . . . . ? C7 C6 Ir1 C5' -26.3(13) . . . . ? C11 C6 Ir1 C5' -147(2) . . . . ? C5 C6 Ir1 C3' -21(7) . . . . ? C7 C6 Ir1 C3' -140(9) . . . . ? C11 C6 Ir1 C3' 98(9) . . . . ? C5 C6 Ir1 C4' 131(3) . . . . ? C7 C6 Ir1 C4' 12(2) . . . . ? C11 C6 Ir1 C4' -109(3) . . . . ? C5 C6 Ir1 C4 36.6(14) . . . . ? C7 C6 Ir1 C4 -82.3(15) . . . . ? C11 C6 Ir1 C4 156(2) . . . . ? C7 C6 Ir1 C5 -119(2) . . . . ? C11 C6 Ir1 C5 120(3) . . . . ? C5 C6 Ir1 S2 -89.9(15) . . . . ? C7 C6 Ir1 S2 151.2(13) . . . . ? C11 C6 Ir1 S2 30.0(18) . . . . ? C8 C3 Ir1 N1 -55(2) . . . . ? C7 C3 Ir1 N1 -173.2(12) . . . . ? C4 C3 Ir1 N1 71.8(14) . . . . ? C8 C3 Ir1 C6' -115(3) . . . . ? C7 C3 Ir1 C6' 127(3) . . . . ? C4 C3 Ir1 C6' 12(2) . . . . ? C8 C3 Ir1 C6 156(2) . . . . ? C7 C3 Ir1 C6 38.5(13) . . . . ? C4 C3 Ir1 C6 -76.5(14) . . . . ? C8 C3 Ir1 C7 118(3) . . . . ? C4 C3 Ir1 C7 -115(2) . . . . ? C8 C3 Ir1 C7' -152(2) . . . . ? C7 C3 Ir1 C7' 89.9(15) . . . . ? C4 C3 Ir1 C7' -25.0(13) . . . . ? C8 C3 Ir1 C5' 95(7) . . . . ? C7 C3 Ir1 C5' -22(6) . . . . ? C4 C3 Ir1 C5' -137(7) . . . . ? C8 C3 Ir1 C3' 167(2) . . . . ? C7 C3 Ir1 C3' 49.6(14) . . . . ? C4 C3 Ir1 C3' -65.4(14) . . . . ? C8 C3 Ir1 C4' 128(2) . . . . ? C7 C3 Ir1 C4' 10.2(17) . . . . ? C4 C3 Ir1 C4' -104.8(17) . . . . ? C8 C3 Ir1 C4 -127(3) . . . . ? C7 C3 Ir1 C4 115(2) . . . . ? C8 C3 Ir1 C5 -162(2) . . . . ? C7 C3 Ir1 C5 80.3(15) . . . . ? C4 C3 Ir1 C5 -34.7(13) . . . . ? C8 C3 Ir1 S2 -172.6(13) . . . . ? C7 C3 Ir1 S2 70(2) . . . . ? C4 C3 Ir1 S2 -45(3) . . . . ? C6 C7 Ir1 N1 128.0(13) . . . . ? C3 C7 Ir1 N1 12(2) . . . . ? C12 C7 Ir1 N1 -115.0(18) . . . . ? C6 C7 Ir1 C6' 91.0(15) . . . . ? C3 C7 Ir1 C6' -25.3(13) . . . . ? C12 C7 Ir1 C6' -152(2) . . . . ? C3 C7 Ir1 C6 -116(2) . . . . ? C12 C7 Ir1 C6 117(2) . . . . ? C6 C7 Ir1 C3 116(2) . . . . ? C12 C7 Ir1 C3 -127(2) . . . . ? C6 C7 Ir1 C7' 46.5(14) . . . . ? C3 C7 Ir1 C7' -69.8(15) . . . . ? C12 C7 Ir1 C7' 163(2) . . . . ? C6 C7 Ir1 C5' 126(3) . . . . ? C3 C7 Ir1 C5' 10(3) . . . . ? C12 C7 Ir1 C5' -117(3) . . . . ? C6 C7 Ir1 C3' 9.0(19) . . . . ? C3 C7 Ir1 C3' -107.2(19) . . . . ? C12 C7 Ir1 C3' 126(2) . . . . ? C6 C7 Ir1 C4' -26(5) . . . . ? C3 C7 Ir1 C4' -142(6) . . . . ? C12 C7 Ir1 C4' 91(6) . . . . ? C6 C7 Ir1 C4 77.0(15) . . . . ? C3 C7 Ir1 C4 -39.3(14) . . . . ? C12 C7 Ir1 C4 -166(2) . . . . ? C6 C7 Ir1 C5 36.2(13) . . . . ? C3 C7 Ir1 C5 -80.0(16) . . . . ? C12 C7 Ir1 C5 153(2) . . . . ? C6 C7 Ir1 S2 -39.6(17) . . . . ? C3 C7 Ir1 S2 -155.8(13) . . . . ? C12 C7 Ir1 S2 77.4(18) . . . . ? C3' C7' Ir1 N1 165.9(15) . . . . ? C12' C7' Ir1 N1 40(2) . . . . ? C6' C7' Ir1 N1 -77.3(15) . . . . ? C3' C7' Ir1 C6' -117(2) . . . . ? C12' C7' Ir1 C6' 118(3) . . . . ? C3' C7' Ir1 C6 -9(2) . . . . ? C12' C7' Ir1 C6 -134(3) . . . . ? C6' C7' Ir1 C6 108(2) . . . . ? C3' C7' Ir1 C3 -91.5(18) . . . . ? C12' C7' Ir1 C3 143(3) . . . . ? C6' C7' Ir1 C3 25.2(13) . . . . ? C3' C7' Ir1 C7 -48.5(16) . . . . ? C12' C7' Ir1 C7 -174(3) . . . . ? C6' C7' Ir1 C7 68.3(15) . . . . ? C3' C7' Ir1 C5' -79.1(18) . . . . ? C12' C7' Ir1 C5' 155(3) . . . . ? C6' C7' Ir1 C5' 37.7(15) . . . . ? C12' C7' Ir1 C3' -125(3) . . . . ? C6' C7' Ir1 C3' 117(2) . . . . ? C3' C7' Ir1 C4' -35.0(16) . . . . ? C12' C7' Ir1 C4' -160(3) . . . . ? C6' C7' Ir1 C4' 81.8(16) . . . . ? C3' C7' Ir1 C4 -126(3) . . . . ? C12' C7' Ir1 C4 108(3) . . . . ? C6' C7' Ir1 C4 -9(2) . . . . ? C3' C7' Ir1 C5 24(8) . . . . ? C12' C7' Ir1 C5 -101(10) . . . . ? C6' C7' Ir1 C5 141(10) . . . . ? C3' C7' Ir1 S2 81.8(17) . . . . ? C12' C7' Ir1 S2 -44(2) . . . . ? C6' C7' Ir1 S2 -161.4(14) . . . . ? C6' C5' Ir1 N1 54.0(17) . . . . ? C4' C5' Ir1 N1 171.9(13) . . . . ? C10' C5' Ir1 N1 -62(2) . . . . ? C4' C5' Ir1 C6' 118(2) . . . . ? C10' C5' Ir1 C6' -116(3) . . . . ? C6' C5' Ir1 C6 -91.0(16) . . . . ? C4' C5' Ir1 C6 26.9(14) . . . . ? C10' C5' Ir1 C6 153(2) . . . . ? C6' C5' Ir1 C3 22(6) . . . . ? C4' C5' Ir1 C3 140(8) . . . . ? C10' C5' Ir1 C3 -94(7) . . . . ? C6' C5' Ir1 C7 -127(3) . . . . ? C4' C5' Ir1 C7 -9(2) . . . . ? C10' C5' Ir1 C7 117(3) . . . . ? C6' C5' Ir1 C7' -39.7(14) . . . . ? C4' C5' Ir1 C7' 78.3(16) . . . . ? C10' C5' Ir1 C7' -156(2) . . . . ? C6' C5' Ir1 C3' -80.4(16) . . . . ? C4' C5' Ir1 C3' 37.5(15) . . . . ? C10' C5' Ir1 C3' 164(2) . . . . ? C6' C5' Ir1 C4' -118(2) . . . . ? C10' C5' Ir1 C4' 126(3) . . . . ? C6' C5' Ir1 C4 -12.5(16) . . . . ? C4' C5' Ir1 C4 105.5(19) . . . . ? C10' C5' Ir1 C4 -128(3) . . . . ? C6' C5' Ir1 C5 -49.9(15) . . . . ? C4' C5' Ir1 C5 68.1(15) . . . . ? C10' C5' Ir1 C5 -166(2) . . . . ? C6' C5' Ir1 S2 -98(2) . . . . ? C4' C5' Ir1 S2 20(3) . . . . ? C10' C5' Ir1 S2 146.4(17) . . . . ? C7' C3' Ir1 N1 -21(2) . . . . ? C4' C3' Ir1 N1 -143.6(12) . . . . ? C8' C3' Ir1 N1 99(2) . . . . ? C7' C3' Ir1 C6' 39.9(17) . . . . ? C4' C3' Ir1 C6' -82.4(16) . . . . ? C8' C3' Ir1 C6' 161(2) . . . . ? C7' C3' Ir1 C6 143(9) . . . . ? C4' C3' Ir1 C6 21(7) . . . . ? C8' C3' Ir1 C6 -96(9) . . . . ? C7' C3' Ir1 C3 69.6(18) . . . . ? C4' C3' Ir1 C3 -52.7(15) . . . . ? C8' C3' Ir1 C3 -170(2) . . . . ? C7' C3' Ir1 C7 110(2) . . . . ? C4' C3' Ir1 C7 -12.0(16) . . . . ? C8' C3' Ir1 C7 -129(2) . . . . ? C4' C3' Ir1 C7' -122(2) . . . . ? C8' C3' Ir1 C7' 121(3) . . . . ? C7' C3' Ir1 C5' 82.5(18) . . . . ? C4' C3' Ir1 C5' -39.8(14) . . . . ? C8' C3' Ir1 C5' -157(2) . . . . ? C7' C3' Ir1 C4' 122(2) . . . . ? C8' C3' Ir1 C4' -117(3) . . . . ? C7' C3' Ir1 C4 26.7(16) . . . . ? C4' C3' Ir1 C4 -95.6(17) . . . . ? C8' C3' Ir1 C4 147(2) . . . . ? C7' C3' Ir1 C5 -8(3) . . . . ? C4' C3' Ir1 C5 -131(3) . . . . ? C8' C3' Ir1 C5 112(3) . . . . ? C7' C3' Ir1 S2 -103.9(17) . . . . ? C4' C3' Ir1 S2 133.8(15) . . . . ? C8' C3' Ir1 S2 16.8(18) . . . . ? C3' C4' Ir1 N1 97(2) . . . . ? C5' C4' Ir1 N1 -19(3) . . . . ? C9' C4' Ir1 N1 -137.2(17) . . . . ? C3' C4' Ir1 C6' 78.9(17) . . . . ? C5' C4' Ir1 C6' -36.9(14) . . . . ? C9' C4' Ir1 C6' -156(2) . . . . ? C3' C4' Ir1 C6 -8(3) . . . . ? C5' C4' Ir1 C6 -124(3) . . . . ? C9' C4' Ir1 C6 118(3) . . . . ? C3' C4' Ir1 C3 106(2) . . . . ? C5' C4' Ir1 C3 -10.2(18) . . . . ? C9' C4' Ir1 C3 -129(2) . . . . ? C3' C4' Ir1 C7 136(6) . . . . ? C5' C4' Ir1 C7 20(5) . . . . ? C9' C4' Ir1 C7 -98(6) . . . . ? C3' C4' Ir1 C7' 34.2(16) . . . . ? C5' C4' Ir1 C7' -81.7(16) . . . . ? C9' C4' Ir1 C7' 160(2) . . . . ? C3' C4' Ir1 C5' 116(2) . . . . ? C9' C4' Ir1 C5' -119(3) . . . . ? C5' C4' Ir1 C3' -116(2) . . . . ? C9' C4' Ir1 C3' 126(3) . . . . ? C3' C4' Ir1 C4 64.6(16) . . . . ? C5' C4' Ir1 C4 -51.3(14) . . . . ? C9' C4' Ir1 C4 -170(2) . . . . ? C3' C4' Ir1 C5 24.5(15) . . . . ? C5' C4' Ir1 C5 -91.3(16) . . . . ? C9' C4' Ir1 C5 150(2) . . . . ? C3' C4' Ir1 S2 -55.5(17) . . . . ? C5' C4' Ir1 S2 -171.4(12) . . . . ? C9' C4' Ir1 S2 70(2) . . . . ? C5 C4 Ir1 N1 124.2(15) . . . . ? C9 C4 Ir1 N1 -4.1(17) . . . . ? C3 C4 Ir1 N1 -115.2(13) . . . . ? C5 C4 Ir1 C6' -145(6) . . . . ? C9 C4 Ir1 C6' 87(6) . . . . ? C3 C4 Ir1 C6' -24(5) . . . . ? C5 C4 Ir1 C6 -37.5(15) . . . . ? C9 C4 Ir1 C6 -166(2) . . . . ? C3 C4 Ir1 C6 83.0(15) . . . . ? C5 C4 Ir1 C3 -121(2) . . . . ? C9 C4 Ir1 C3 111(2) . . . . ? C5 C4 Ir1 C7 -81.2(16) . . . . ? C9 C4 Ir1 C7 150(2) . . . . ? C3 C4 Ir1 C7 39.3(12) . . . . ? C5 C4 Ir1 C7' 8(3) . . . . ? C9 C4 Ir1 C7' -120(3) . . . . ? C3 C4 Ir1 C7' 129(3) . . . . ? C5 C4 Ir1 C5' -110(2) . . . . ? C9 C4 Ir1 C5' 122(2) . . . . ? C3 C4 Ir1 C5' 11.0(18) . . . . ? C5 C4 Ir1 C3' -27.0(16) . . . . ? C9 C4 Ir1 C3' -155(2) . . . . ? C3 C4 Ir1 C3' 93.5(15) . . . . ? C5 C4 Ir1 C4' -67.8(16) . . . . ? C9 C4 Ir1 C4' 164(2) . . . . ? C3 C4 Ir1 C4' 52.7(13) . . . . ? C9 C4 Ir1 C5 -128(3) . . . . ? C3 C4 Ir1 C5 121(2) . . . . ? C5 C4 Ir1 S2 42.8(17) . . . . ? C9 C4 Ir1 S2 -85.6(18) . . . . ? C3 C4 Ir1 S2 163.3(11) . . . . ? C4 C5 Ir1 N1 -63.1(16) . . . . ? C6 C5 Ir1 N1 179.1(14) . . . . ? C10 C5 Ir1 N1 54.5(19) . . . . ? C4 C5 Ir1 C6' 10.3(17) . . . . ? C6 C5 Ir1 C6' -107(2) . . . . ? C10 C5 Ir1 C6' 128(2) . . . . ? C4 C5 Ir1 C6 118(2) . . . . ? C10 C5 Ir1 C6 -125(3) . . . . ? C4 C5 Ir1 C3 36.9(13) . . . . ? C6 C5 Ir1 C3 -80.9(16) . . . . ? C10 C5 Ir1 C3 155(2) . . . . ? C4 C5 Ir1 C7 80.3(15) . . . . ? C6 C5 Ir1 C7 -37.5(15) . . . . ? C10 C5 Ir1 C7 -162(2) . . . . ? C4 C5 Ir1 C7' -23(8) . . . . ? C6 C5 Ir1 C7' -141(10) . . . . ? C10 C5 Ir1 C7' 95(10) . . . . ? C4 C5 Ir1 C5' 49.8(15) . . . . ? C6 C5 Ir1 C5' -68.0(16) . . . . ? C10 C5 Ir1 C5' 167(2) . . . . ? C4 C5 Ir1 C3' 126(3) . . . . ? C6 C5 Ir1 C3' 8(3) . . . . ? C10 C5 Ir1 C3' -117(3) . . . . ? C4 C5 Ir1 C4' 93.4(16) . . . . ? C6 C5 Ir1 C4' -24.4(14) . . . . ? C10 C5 Ir1 C4' -149(2) . . . . ? C6 C5 Ir1 C4 -118(2) . . . . ? C10 C5 Ir1 C4 118(3) . . . . ? C4 C5 Ir1 S2 -146.6(14) . . . . ? C6 C5 Ir1 S2 95.7(15) . . . . ? C10 C5 Ir1 S2 -29.0(19) . . . . ? C17 C18 N2 O1 34(3) . . . . ? C13 C18 N2 O1 -144(3) . . . . ? C17 C18 N2 O2 -153.2(15) . . . . ? C13 C18 N2 O2 28.5(18) . . . . ? C14 C13 N1 Ir1 -12.5(10) . . . . ? C18 C13 N1 Ir1 164.4(7) . . . . ? C6' Ir1 N1 C13 -121.5(8) . . . . ? C6 Ir1 N1 C13 -75.0(16) . . . . ? C3 Ir1 N1 C13 -144.7(9) . . . . ? C7 Ir1 N1 C13 -152.4(12) . . . . ? C7' Ir1 N1 C13 -82.5(10) . . . . ? C5' Ir1 N1 C13 -151.4(10) . . . . ? C3' Ir1 N1 C13 -69.5(13) . . . . ? C4' Ir1 N1 C13 -138.1(19) . . . . ? C4 Ir1 N1 C13 -108.1(8) . . . . ? C5 Ir1 N1 C13 -76.0(9) . . . . ? S2 Ir1 N1 C13 18.2(6) . . . . ? C2 C1 S1 Ir1 5.9(6) . . . . ? B4 C1 S1 Ir1 150.2(6) . . . . ? B3 C1 S1 Ir1 76.0(5) . . . . ? B5 C1 S1 Ir1 -135.8(6) . . . . ? B6 C1 S1 Ir1 -64.0(6) . . . . ? N1 Ir1 S1 C1 -85.8(3) . . . . ? C6' Ir1 S1 C1 -179.9(9) . . . . ? C6 Ir1 S1 C1 97.1(9) . . . . ? C3 Ir1 S1 C1 165.5(7) . . . . ? C7 Ir1 S1 C1 127.5(6) . . . . ? C7' Ir1 S1 C1 134.1(19) . . . . ? C5' Ir1 S1 C1 155.4(8) . . . . ? C3' Ir1 S1 C1 93.8(10) . . . . ? C4' Ir1 S1 C1 115.4(6) . . . . ? C4 Ir1 S1 C1 179.3(10) . . . . ? C5 Ir1 S1 C1 108.9(16) . . . . ? S2 Ir1 S1 C1 -4.6(3) . . . . ? C15 C14 S2 C2 91.4(6) . . . . ? C13 C14 S2 C2 -93.2(6) . . . . ? C15 C14 S2 Ir1 -159.2(6) . . . . ? C13 C14 S2 Ir1 16.2(6) . . . . ? C1 C2 S2 C14 103.9(5) . . . . ? B3 C2 S2 C14 32.1(6) . . . . ? B8 C2 S2 C14 -43.7(6) . . . . ? B6 C2 S2 C14 173.7(5) . . . . ? B7 C2 S2 C14 -117.6(6) . . . . ? C1 C2 S2 Ir1 0.0(5) . . . . ? B3 C2 S2 Ir1 -71.7(6) . . . . ? B8 C2 S2 Ir1 -147.6(5) . . . . ? B6 C2 S2 Ir1 69.8(5) . . . . ? B7 C2 S2 Ir1 138.5(5) . . . . ? N1 Ir1 S2 C14 -15.7(3) . . . . ? C6' Ir1 S2 C14 69.1(11) . . . . ? C6 Ir1 S2 C14 133.5(6) . . . . ? C3 Ir1 S2 C14 105.4(18) . . . . ? C7 Ir1 S2 C14 157.3(9) . . . . ? C7' Ir1 S2 C14 87.6(7) . . . . ? C5' Ir1 S2 C14 139.3(17) . . . . ? C3' Ir1 S2 C14 123.8(7) . . . . ? C4' Ir1 S2 C14 154.0(9) . . . . ? C4 Ir1 S2 C14 71.8(8) . . . . ? C5 Ir1 S2 C14 95.8(8) . . . . ? N1 Ir1 S2 C2 92.2(3) . . . . ? C6' Ir1 S2 C2 177.1(11) . . . . ? C6 Ir1 S2 C2 -118.5(6) . . . . ? C3 Ir1 S2 C2 -146.7(18) . . . . ? C7 Ir1 S2 C2 -94.7(9) . . . . ? C7' Ir1 S2 C2 -164.5(7) . . . . ? C5' Ir1 S2 C2 -112.7(17) . . . . ? C3' Ir1 S2 C2 -128.2(7) . . . . ? C4' Ir1 S2 C2 -98.1(9) . . . . ? C4 Ir1 S2 C2 179.7(8) . . . . ? C5 Ir1 S2 C2 -156.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.071 _refine_diff_density_min -2.202 _refine_diff_density_rms 0.128