#Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'David Milstein' _publ_contact_author_email DAVID.MILSTEIN@WEIZMANN.AC.IL _publ_section_title ; Pyridine- Based SNS-Iridium and -Rhodium Sulfide Complexes, Including d8-d8 Metal-Metal Interactions in the Solid State ; loop_ _publ_author_name 'David Milstein' 'Eyal Ben-Ari' 'Yael Diskin-Posner' 'Yulie Klerman' 'Gregory Leitus' ; L.Shimon ; data_m704b _database_code_depnum_ccdc_archive 'CCDC 676565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H50 Ir2 N2 S4, 2(B1 F4), C H2 Cl2' _symmetry_space_group_name_Hall P2ac2ab _chemical_formula_sum 'C31 H52 B2 Cl2 F8 Ir2 N2 S4' _chemical_formula_weight 1209.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 11.410(2) _cell_length_b 20.324(4) _cell_length_c 21.390(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4960.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5349 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 5.688 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2270 _exptl_absorpt_correction_T_max 0.3206 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4944 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4944 _reflns_number_gt 4591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect package (Bruker Nonius)' _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+20.3703P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.509(13) _refine_ls_number_reflns 4944 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.012 _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 0.09038(3) 0.496390(19) 0.115145(16) 0.02612(11) Uani 1 1 d . . . S1 S 0.2190(2) 0.45046(14) 0.18491(12) 0.0263(6) Uani 1 1 d . . . S2 S -0.0370(2) 0.51739(14) 0.03419(12) 0.0317(6) Uani 1 1 d . . . N1 N 0.1302(7) 0.4101(4) 0.0635(4) 0.0235(18) Uani 1 1 d . . . C11 C 0.3037(10) 0.4022(6) 0.1282(5) 0.034(3) Uani 1 1 d . . . H11A H 0.3632 0.4306 0.1081 0.041 Uiso 1 1 calc R . . H11B H 0.3450 0.3661 0.1500 0.041 Uiso 1 1 calc R . . C12 C 0.2245(8) 0.3743(5) 0.0795(5) 0.028(2) Uani 1 1 d . . . C13 C 0.2467(11) 0.3145(6) 0.0501(6) 0.042(3) Uani 1 1 d . . . H13 H 0.3087 0.2870 0.0641 0.050 Uiso 1 1 calc R . . C14 C 0.1774(11) 0.2956(6) 0.0002(5) 0.038(3) Uani 1 1 d . . . H14 H 0.1938 0.2561 -0.0218 0.046 Uiso 1 1 calc R . . C15 C 0.0831(11) 0.3351(5) -0.0174(5) 0.035(2) Uani 1 1 d . . . H15 H 0.0346 0.3227 -0.0515 0.043 Uiso 1 1 calc R . . C16 C 0.0608(10) 0.3922(6) 0.0152(5) 0.034(3) Uani 1 1 d . . . C17 C -0.0469(12) 0.4343(6) 0.0011(5) 0.037(3) Uani 1 1 d . . . H17A H -0.1173 0.4122 0.0181 0.045 Uiso 1 1 calc R . . H17B H -0.0567 0.4377 -0.0448 0.045 Uiso 1 1 calc R . . C18 C 0.3299(8) 0.5033(7) 0.2243(5) 0.031(2) Uani 1 1 d . . . C19 C 0.4147(10) 0.4585(6) 0.2586(6) 0.039(3) Uani 1 1 d . . . H19A H 0.4586 0.4321 0.2282 0.058 Uiso 1 1 calc R . . H19B H 0.3709 0.4293 0.2866 0.058 Uiso 1 1 calc R . . H19C H 0.4695 0.4852 0.2832 0.058 Uiso 1 1 calc R . . C110 C 0.3968(12) 0.5451(7) 0.1752(6) 0.050(4) Uani 1 1 d . . . H11C H 0.4493 0.5759 0.1966 0.075 Uiso 1 1 calc R . . H11D H 0.3404 0.5698 0.1498 0.075 Uiso 1 1 calc R . . H11E H 0.4428 0.5160 0.1481 0.075 Uiso 1 1 calc R . . C111 C 0.2602(12) 0.5465(6) 0.2677(6) 0.047(3) Uani 1 1 d . . . H11F H 0.2120 0.5190 0.2952 0.070 Uiso 1 1 calc R . . H11G H 0.2094 0.5756 0.2432 0.070 Uiso 1 1 calc R . . H11H H 0.3138 0.5731 0.2931 0.070 Uiso 1 1 calc R . . C112 C 0.0298(11) 0.5669(6) -0.0296(6) 0.041(3) Uani 1 1 d . . . C113 C 0.0572(16) 0.6325(6) -0.0014(7) 0.058(4) Uani 1 1 d . . . H11I H 0.1192 0.6274 0.0300 0.087 Uiso 1 1 calc R . . H11J H -0.0133 0.6503 0.0186 0.087 Uiso 1 1 calc R . . H11K H 0.0836 0.6627 -0.0341 0.087 Uiso 1 1 calc R . . C114 C 0.1393(12) 0.5337(8) -0.0564(6) 0.051(4) Uani 1 1 d . . . H11L H 0.1689 0.5594 -0.0917 0.077 Uiso 1 1 calc R . . H11M H 0.1194 0.4892 -0.0705 0.077 Uiso 1 1 calc R . . H11N H 0.1997 0.5311 -0.0239 0.077 Uiso 1 1 calc R . . C115 C -0.0634(11) 0.5723(7) -0.0817(5) 0.045(3) Uani 1 1 d . . . H11O H -0.0392 0.6059 -0.1120 0.068 Uiso 1 1 calc R . . H11P H -0.1389 0.5847 -0.0633 0.068 Uiso 1 1 calc R . . H11Q H -0.0711 0.5298 -0.1029 0.068 Uiso 1 1 calc R . . Ir2 Ir 0.08385(3) 0.386616(18) 0.251029(18) 0.02779(11) Uani 1 1 d . . . S3 S -0.0447(2) 0.44259(12) 0.18825(12) 0.0233(5) Uani 1 1 d . . . S4 S 0.2134(3) 0.31305(15) 0.29447(14) 0.0357(6) Uani 1 1 d . . . N2 N 0.0507(7) 0.3105(4) 0.1857(4) 0.0260(19) Uani 1 1 d . . . C21 C -0.1243(9) 0.3724(5) 0.1581(5) 0.031(2) Uani 1 1 d . . . H21A H -0.1876 0.3604 0.1876 0.037 Uiso 1 1 calc R . . H21B H -0.1608 0.3842 0.1176 0.037 Uiso 1 1 calc R . . C22 C -0.0434(9) 0.3134(5) 0.1488(5) 0.029(2) Uani 1 1 d . . . C23 C -0.0670(10) 0.2640(5) 0.1069(5) 0.035(2) Uani 1 1 d . . . H23 H -0.1321 0.2675 0.0794 0.042 Uiso 1 1 calc R . . C24 C 0.0051(11) 0.2086(6) 0.1050(6) 0.040(3) Uani 1 1 d . . . H24 H -0.0090 0.1744 0.0758 0.048 Uiso 1 1 calc R . . C25 C 0.0931(14) 0.2048(5) 0.1447(5) 0.042(3) Uani 1 1 d . . . H25 H 0.1386 0.1657 0.1457 0.050 Uiso 1 1 calc R . . C26 C 0.1222(10) 0.2563(5) 0.1854(5) 0.032(3) Uani 1 1 d . . . C27 C 0.2267(12) 0.2574(6) 0.2271(6) 0.042(3) Uani 1 1 d . . . H27A H 0.2958 0.2707 0.2022 0.050 Uiso 1 1 calc R . . H27B H 0.2411 0.2123 0.2427 0.050 Uiso 1 1 calc R . . C28 C -0.1626(9) 0.4938(7) 0.2248(5) 0.032(2) Uani 1 1 d . . . C29 C -0.0953(11) 0.5455(5) 0.2619(5) 0.036(3) Uani 1 1 d . . . H29A H -0.0310 0.5627 0.2363 0.054 Uiso 1 1 calc R . . H29B H -0.0635 0.5255 0.2999 0.054 Uiso 1 1 calc R . . H29C H -0.1483 0.5815 0.2732 0.054 Uiso 1 1 calc R . . C210 C -0.2307(11) 0.5254(6) 0.1739(6) 0.042(3) Uani 1 1 d . . . H21C H -0.2627 0.4914 0.1463 0.062 Uiso 1 1 calc R . . H21D H -0.1794 0.5546 0.1499 0.062 Uiso 1 1 calc R . . H21E H -0.2951 0.5510 0.1920 0.062 Uiso 1 1 calc R . . C211 C -0.2397(11) 0.4509(6) 0.2672(6) 0.041(3) Uani 1 1 d . . . H21F H -0.2901 0.4791 0.2928 0.062 Uiso 1 1 calc R . . H21G H -0.1898 0.4241 0.2945 0.062 Uiso 1 1 calc R . . H21H H -0.2885 0.4220 0.2414 0.062 Uiso 1 1 calc R . . C212 C 0.1476(12) 0.2582(6) 0.3547(5) 0.039(3) Uani 1 1 d . . . C213 C 0.2470(13) 0.2122(6) 0.3775(7) 0.054(4) Uani 1 1 d . . . H21I H 0.3166 0.2384 0.3874 0.081 Uiso 1 1 calc R . . H21J H 0.2661 0.1805 0.3444 0.081 Uiso 1 1 calc R . . H21K H 0.2212 0.1885 0.4149 0.081 Uiso 1 1 calc R . . C214 C 0.0405(15) 0.2199(7) 0.3320(7) 0.058(4) Uani 1 1 d . . . H21L H 0.0644 0.1888 0.2994 0.087 Uiso 1 1 calc R . . H21M H -0.0174 0.2506 0.3149 0.087 Uiso 1 1 calc R . . H21N H 0.0059 0.1957 0.3671 0.087 Uiso 1 1 calc R . . C215 C 0.1106(18) 0.3068(8) 0.4082(6) 0.070(5) Uani 1 1 d . . . H21O H 0.0824 0.2817 0.4442 0.106 Uiso 1 1 calc R . . H21P H 0.0479 0.3357 0.3931 0.106 Uiso 1 1 calc R . . H21Q H 0.1783 0.3335 0.4206 0.106 Uiso 1 1 calc R . . B1 B -0.4004(13) 0.6218(7) 0.3384(6) 0.038(3) Uani 1 1 d . . . F11 F -0.5067(6) 0.5947(4) 0.3508(3) 0.050(2) Uani 1 1 d . . . F12 F -0.3959(6) 0.6865(4) 0.3622(3) 0.0466(18) Uani 1 1 d . . . F13 F -0.3102(6) 0.5858(4) 0.3640(4) 0.051(2) Uani 1 1 d . . . F14 F -0.3821(6) 0.6255(4) 0.2721(3) 0.0464(18) Uani 1 1 d . . . B2 B 0.5947(15) 0.3642(8) 0.0744(7) 0.048(4) Uani 1 1 d . . . F21 F 0.6958(6) 0.3678(5) 0.0413(4) 0.068(3) Uani 1 1 d . A . F22A F 0.5050(16) 0.3849(11) 0.0280(9) 0.058(6) Uiso 0.44(2) 1 d P A 1 F23A F 0.539(2) 0.3073(12) 0.0882(11) 0.082(8) Uiso 0.44(2) 1 d P A 1 F24A F 0.588(3) 0.3872(15) 0.1364(13) 0.095(8) Uiso 0.44(2) 1 d P A 1 F22B F 0.5060(13) 0.3425(8) 0.0436(7) 0.054(5) Uiso 0.56(2) 1 d P A 2 F23B F 0.6348(18) 0.3091(10) 0.1137(10) 0.090(7) Uiso 0.56(2) 1 d P A 2 F24B F 0.5802(12) 0.4164(7) 0.1153(6) 0.041(3) Uiso 0.56(2) 1 d P A 2 C1 C 0.6088(19) 0.2372(10) 0.2365(10) 0.094(6) Uani 1 1 d . . . H1A H 0.5998 0.2607 0.1963 0.112 Uiso 1 1 calc R B 3 H1B H 0.5813 0.1914 0.2304 0.112 Uiso 1 1 calc R B 3 Cl1A Cl 0.5219(15) 0.2748(13) 0.2920(14) 0.126(7) Uiso 0.48(4) 1 d P C 3 Cl1B Cl 0.5294(9) 0.2955(7) 0.2675(7) 0.079(5) Uiso 0.52(4) 1 d P C 4 Cl2 Cl 0.7576(4) 0.2358(3) 0.2570(4) 0.115(2) Uani 1 1 d . C . 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 0.02206(18) 0.0284(2) 0.02788(18) -0.00319(17) 0.00121(17) -0.0020(2) S1 0.0163(11) 0.0308(15) 0.0319(14) -0.0071(12) -0.0013(10) -0.0009(10) S2 0.0259(12) 0.0386(17) 0.0304(13) 0.0020(11) -0.0006(11) 0.0006(11) N1 0.024(4) 0.025(5) 0.021(4) -0.003(3) 0.000(3) -0.004(3) C11 0.028(6) 0.045(7) 0.030(6) -0.006(5) 0.005(5) 0.002(5) C12 0.016(5) 0.034(7) 0.033(5) -0.016(5) 0.005(4) -0.007(4) C13 0.036(6) 0.043(7) 0.046(7) -0.005(6) 0.005(6) 0.002(6) C14 0.044(7) 0.037(7) 0.034(6) -0.012(5) 0.000(5) -0.008(6) C15 0.038(6) 0.040(6) 0.028(5) -0.008(5) -0.003(6) -0.013(6) C16 0.036(6) 0.043(6) 0.024(5) 0.003(5) 0.005(4) -0.009(5) C17 0.056(7) 0.030(6) 0.026(5) 0.005(5) 0.004(5) 0.003(5) C18 0.023(5) 0.034(6) 0.036(5) -0.011(6) -0.009(4) -0.009(5) C19 0.028(5) 0.042(6) 0.046(7) -0.002(5) -0.015(6) 0.001(5) C110 0.048(8) 0.056(8) 0.046(7) 0.000(6) -0.006(6) -0.042(7) C111 0.047(7) 0.036(7) 0.057(8) -0.030(6) -0.004(6) 0.002(6) C112 0.046(7) 0.040(7) 0.037(6) 0.005(5) 0.007(6) -0.003(6) C113 0.084(12) 0.038(7) 0.052(8) 0.011(6) 0.015(8) -0.017(7) C114 0.042(7) 0.071(10) 0.040(7) 0.013(7) 0.005(6) -0.008(7) C115 0.038(7) 0.073(9) 0.025(5) 0.004(6) -0.006(5) 0.008(6) Ir2 0.02865(19) 0.0256(2) 0.02910(19) -0.00353(17) -0.0013(2) -0.00029(18) S3 0.0197(11) 0.0209(13) 0.0293(13) -0.0045(11) 0.0001(10) -0.0017(9) S4 0.0369(15) 0.0322(15) 0.0379(15) -0.0008(12) -0.0047(12) 0.0023(12) N2 0.025(4) 0.025(5) 0.028(4) -0.007(4) 0.006(3) -0.002(3) C21 0.024(5) 0.027(6) 0.041(6) -0.012(5) -0.001(4) -0.006(4) C22 0.029(5) 0.030(6) 0.028(5) -0.001(5) 0.003(4) 0.002(5) C23 0.034(6) 0.026(5) 0.044(6) -0.009(5) -0.011(5) -0.006(5) C24 0.044(7) 0.030(6) 0.046(7) -0.013(5) 0.008(6) 0.000(5) C25 0.067(8) 0.027(6) 0.032(5) -0.002(5) 0.005(7) 0.011(7) C26 0.043(7) 0.028(6) 0.024(5) -0.003(4) 0.003(4) 0.005(5) C27 0.042(7) 0.032(7) 0.051(7) -0.004(5) 0.000(6) 0.006(6) C28 0.025(5) 0.036(7) 0.035(5) -0.012(6) 0.008(4) -0.002(5) C29 0.042(6) 0.027(6) 0.040(6) -0.011(5) 0.012(6) 0.006(5) C210 0.037(6) 0.042(7) 0.046(7) -0.008(6) 0.007(6) 0.001(6) C211 0.033(6) 0.036(7) 0.054(8) -0.006(5) 0.013(6) 0.008(5) C212 0.061(8) 0.021(6) 0.037(6) 0.001(5) -0.012(6) -0.010(5) C213 0.067(9) 0.030(7) 0.064(8) 0.003(6) -0.020(8) 0.003(6) C214 0.082(10) 0.045(8) 0.048(8) 0.010(7) -0.008(7) -0.022(8) C215 0.116(15) 0.061(9) 0.033(6) 0.011(6) 0.009(8) 0.025(10) B1 0.039(7) 0.039(7) 0.036(6) -0.001(6) 0.006(6) -0.017(7) F11 0.038(4) 0.077(6) 0.036(4) -0.006(4) 0.007(3) -0.025(4) F12 0.044(4) 0.051(4) 0.045(4) -0.018(3) 0.011(3) -0.015(4) F13 0.043(4) 0.053(5) 0.056(5) -0.004(4) 0.009(3) 0.002(4) F14 0.057(5) 0.053(4) 0.030(3) -0.007(3) 0.007(3) -0.013(3) B2 0.044(8) 0.051(9) 0.049(8) -0.014(7) 0.012(8) -0.007(8) F21 0.031(4) 0.111(8) 0.062(5) -0.016(5) 0.003(4) -0.004(4) C1 0.108(16) 0.064(11) 0.108(15) -0.004(11) -0.028(13) -0.005(11) Cl2 0.062(3) 0.115(4) 0.167(6) 0.038(5) -0.008(4) 0.000(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 2.121(8) . ? Ir1 S1 2.292(3) . ? Ir1 S2 2.301(3) . ? Ir1 S3 2.453(3) . ? S1 C11 1.835(11) . ? S1 C18 1.861(10) . ? S1 Ir2 2.462(3) . ? S2 C17 1.835(12) . ? S2 C112 1.860(12) . ? N1 C12 1.345(14) . ? N1 C16 1.351(14) . ? C11 C12 1.490(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.392(16) . ? C13 C14 1.383(17) . ? C13 H13 0.9500 . ? C14 C15 1.394(18) . ? C14 H14 0.9500 . ? C15 C16 1.377(16) . ? C15 H15 0.9500 . ? C16 C17 1.528(17) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C111 1.506(16) . ? C18 C19 1.517(16) . ? C18 C110 1.552(16) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C110 H11C 0.9800 . ? C110 H11D 0.9800 . ? C110 H11E 0.9800 . ? C111 H11F 0.9800 . ? C111 H11G 0.9800 . ? C111 H11H 0.9800 . ? C112 C113 1.496(18) . ? C112 C114 1.532(18) . ? C112 C115 1.544(17) . ? C113 H11I 0.9800 . ? C113 H11J 0.9800 . ? C113 H11K 0.9800 . ? C114 H11L 0.9800 . ? C114 H11M 0.9800 . ? C114 H11N 0.9800 . ? C115 H11O 0.9800 . ? C115 H11P 0.9800 . ? C115 H11Q 0.9800 . ? Ir2 N2 2.119(8) . ? Ir2 S3 2.291(3) . ? Ir2 S4 2.299(3) . ? S3 C21 1.810(10) . ? S3 C28 1.871(11) . ? S4 C27 1.838(13) . ? S4 C212 1.862(12) . ? N2 C22 1.334(14) . ? N2 C26 1.371(14) . ? C21 C22 1.526(15) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.372(15) . ? C23 C24 1.394(16) . ? C23 H23 0.9500 . ? C24 C25 1.317(18) . ? C24 H24 0.9500 . ? C25 C26 1.401(15) . ? C25 H25 0.9500 . ? C26 C27 1.489(17) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C210 1.483(17) . ? C28 C29 1.523(16) . ? C28 C211 1.536(16) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C210 H21C 0.9800 . ? C210 H21D 0.9800 . ? C210 H21E 0.9800 . ? C211 H21F 0.9800 . ? C211 H21G 0.9800 . ? C211 H21H 0.9800 . ? C212 C214 1.529(18) . ? C212 C213 1.549(18) . ? C212 C215 1.570(18) . ? C213 H21I 0.9800 . ? C213 H21J 0.9800 . ? C213 H21K 0.9800 . ? C214 H21L 0.9800 . ? C214 H21M 0.9800 . ? C214 H21N 0.9800 . ? C215 H21O 0.9800 . ? C215 H21P 0.9800 . ? C215 H21Q 0.9800 . ? B1 F11 1.358(15) . ? B1 F13 1.377(17) . ? B1 F12 1.410(15) . ? B1 F14 1.436(14) . ? B2 F22B 1.29(2) . ? B2 F23A 1.35(3) . ? B2 F21 1.355(18) . ? B2 F24B 1.385(18) . ? B2 F24A 1.41(3) . ? B2 F23B 1.47(3) . ? B2 F22A 1.49(3) . ? C1 Cl1B 1.63(2) . ? C1 Cl1A 1.72(3) . ? C1 Cl2 1.75(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1 S1 82.3(2) . . ? N1 Ir1 S2 84.1(2) . . ? S1 Ir1 S2 165.98(10) . . ? N1 Ir1 S3 95.6(2) . . ? S1 Ir1 S3 78.80(8) . . ? S2 Ir1 S3 99.53(9) . . ? C11 S1 C18 104.5(5) . . ? C11 S1 Ir1 97.1(4) . . ? C18 S1 Ir1 119.7(4) . . ? C11 S1 Ir2 115.3(4) . . ? C18 S1 Ir2 118.0(4) . . ? Ir1 S1 Ir2 100.80(9) . . ? C17 S2 C112 103.9(6) . . ? C17 S2 Ir1 99.1(4) . . ? C112 S2 Ir1 113.2(4) . . ? C12 N1 C16 121.1(9) . . ? C12 N1 Ir1 119.1(6) . . ? C16 N1 Ir1 119.7(7) . . ? C12 C11 S1 110.3(7) . . ? C12 C11 H11A 109.6 . . ? S1 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? S1 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N1 C12 C13 120.2(10) . . ? N1 C12 C11 117.2(9) . . ? C13 C12 C11 122.6(10) . . ? C14 C13 C12 119.1(12) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 119.4(11) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 119.4(10) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N1 C16 C15 120.5(11) . . ? N1 C16 C17 118.1(10) . . ? C15 C16 C17 121.3(10) . . ? C16 C17 S2 112.9(9) . . ? C16 C17 H17A 109.0 . . ? S2 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? S2 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C111 C18 C19 112.9(10) . . ? C111 C18 C110 110.9(12) . . ? C19 C18 C110 110.0(10) . . ? C111 C18 S1 104.9(7) . . ? C19 C18 S1 107.9(9) . . ? C110 C18 S1 110.1(7) . . ? 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 . . ? C18 C110 H11C 109.5 . . ? C18 C110 H11D 109.5 . . ? H11C C110 H11D 109.5 . . ? C18 C110 H11E 109.5 . . ? H11C C110 H11E 109.5 . . ? H11D C110 H11E 109.5 . . ? C18 C111 H11F 109.5 . . ? C18 C111 H11G 109.5 . . ? H11F C111 H11G 109.5 . . ? C18 C111 H11H 109.5 . . ? H11F C111 H11H 109.5 . . ? H11G C111 H11H 109.5 . . ? C113 C112 C114 112.0(12) . . ? C113 C112 C115 111.9(12) . . ? C114 C112 C115 108.9(10) . . ? C113 C112 S2 105.7(9) . . ? C114 C112 S2 111.7(9) . . ? C115 C112 S2 106.6(9) . . ? C112 C113 H11I 109.5 . . ? C112 C113 H11J 109.5 . . ? H11I C113 H11J 109.5 . . ? C112 C113 H11K 109.5 . . ? H11I C113 H11K 109.5 . . ? H11J C113 H11K 109.5 . . ? C112 C114 H11L 109.5 . . ? C112 C114 H11M 109.5 . . ? H11L C114 H11M 109.5 . . ? C112 C114 H11N 109.5 . . ? H11L C114 H11N 109.5 . . ? H11M C114 H11N 109.5 . . ? C112 C115 H11O 109.5 . . ? C112 C115 H11P 109.5 . . ? H11O C115 H11P 109.5 . . ? C112 C115 H11Q 109.5 . . ? H11O C115 H11Q 109.5 . . ? H11P C115 H11Q 109.5 . . ? N2 Ir2 S3 82.1(2) . . ? N2 Ir2 S4 84.6(3) . . ? S3 Ir2 S4 166.32(10) . . ? N2 Ir2 S1 96.8(2) . . ? S3 Ir2 S1 78.62(8) . . ? S4 Ir2 S1 99.91(10) . . ? C21 S3 C28 103.1(5) . . ? C21 S3 Ir2 98.0(4) . . ? C28 S3 Ir2 119.4(4) . . ? C21 S3 Ir1 116.0(4) . . ? C28 S3 Ir1 118.0(4) . . ? Ir2 S3 Ir1 101.11(10) . . ? C27 S4 C212 102.0(6) . . ? C27 S4 Ir2 97.8(4) . . ? C212 S4 Ir2 114.2(4) . . ? C22 N2 C26 120.8(9) . . ? C22 N2 Ir2 120.1(7) . . ? C26 N2 Ir2 118.9(7) . . ? C22 C21 S3 111.2(7) . . ? C22 C21 H21A 109.4 . . ? S3 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? S3 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N2 C22 C23 120.8(10) . . ? N2 C22 C21 116.4(9) . . ? C23 C22 C21 122.7(10) . . ? C22 C23 C24 119.6(10) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 118.6(11) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 122.5(11) . . ? C24 C25 H25 118.7 . . ? C26 C25 H25 118.7 . . ? N2 C26 C25 117.5(10) . . ? N2 C26 C27 117.4(10) . . ? C25 C26 C27 125.0(11) . . ? C26 C27 S4 114.4(9) . . ? C26 C27 H27A 108.7 . . ? S4 C27 H27A 108.7 . . ? C26 C27 H27B 108.7 . . ? S4 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? C210 C28 C29 110.3(11) . . ? C210 C28 C211 112.2(9) . . ? C29 C28 C211 111.9(9) . . ? C210 C28 S3 108.1(7) . . ? C29 C28 S3 103.8(7) . . ? C211 C28 S3 110.0(9) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C210 H21C 109.5 . . ? C28 C210 H21D 109.5 . . ? H21C C210 H21D 109.5 . . ? C28 C210 H21E 109.5 . . ? H21C C210 H21E 109.5 . . ? H21D C210 H21E 109.5 . . ? C28 C211 H21F 109.5 . . ? C28 C211 H21G 109.5 . . ? H21F C211 H21G 109.5 . . ? C28 C211 H21H 109.5 . . ? H21F C211 H21H 109.5 . . ? H21G C211 H21H 109.5 . . ? C214 C212 C213 112.2(10) . . ? C214 C212 C215 109.7(13) . . ? C213 C212 C215 110.4(11) . . ? C214 C212 S4 114.0(8) . . ? C213 C212 S4 106.5(9) . . ? C215 C212 S4 103.7(8) . . ? C212 C213 H21I 109.5 . . ? C212 C213 H21J 109.5 . . ? H21I C213 H21J 109.5 . . ? C212 C213 H21K 109.5 . . ? H21I C213 H21K 109.5 . . ? H21J C213 H21K 109.5 . . ? C212 C214 H21L 109.5 . . ? C212 C214 H21M 109.5 . . ? H21L C214 H21M 109.5 . . ? C212 C214 H21N 109.5 . . ? H21L C214 H21N 109.5 . . ? H21M C214 H21N 109.5 . . ? C212 C215 H21O 109.5 . . ? C212 C215 H21P 109.5 . . ? H21O C215 H21P 109.5 . . ? C212 C215 H21Q 109.5 . . ? H21O C215 H21Q 109.5 . . ? H21P C215 H21Q 109.5 . . ? F11 B1 F13 111.9(10) . . ? F11 B1 F12 110.0(11) . . ? F13 B1 F12 109.0(10) . . ? F11 B1 F14 110.1(10) . . ? F13 B1 F14 108.1(11) . . ? F12 B1 F14 107.6(10) . . ? F22B B2 F23A 56.4(14) . . ? F22B B2 F21 114.9(13) . . ? F23A B2 F21 124.1(16) . . ? F22B B2 F24B 119.5(15) . . ? F23A B2 F24B 117.4(16) . . ? F21 B2 F24B 113.0(13) . . ? F22B B2 F24A 123.8(19) . . ? F23A B2 F24A 93.1(19) . . ? F21 B2 F24A 121.2(18) . . ? F24B B2 F24A 31.2(12) . . ? F22B B2 F23B 106.0(15) . . ? F23A B2 F23B 51.1(13) . . ? F21 B2 F23B 94.3(14) . . ? F24B B2 F23B 105.0(14) . . ? F24A B2 F23B 74.4(17) . . ? F22B B2 F22A 38.1(10) . . ? F23A B2 F22A 93.6(17) . . ? F21 B2 F22A 102.8(13) . . ? F24B B2 F22A 97.1(14) . . ? F24A B2 F22A 120.0(19) . . ? F23B B2 F22A 144.1(17) . . ? Cl1B C1 Cl1A 23.1(8) . . ? Cl1B C1 Cl2 116.6(12) . . ? Cl1A C1 Cl2 113.1(13) . . ? Cl1B C1 H1A 86.9 . . ? Cl1A C1 H1A 109.0 . . ? Cl2 C1 H1A 109.0 . . ? Cl1B C1 H1B 124.0 . . ? Cl1A C1 H1B 109.0 . . ? Cl2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? 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 N1 Ir1 S1 C11 26.2(4) . . . . ? S2 Ir1 S1 C11 39.1(6) . . . . ? S3 Ir1 S1 C11 123.6(4) . . . . ? N1 Ir1 S1 C18 137.4(5) . . . . ? S2 Ir1 S1 C18 150.3(5) . . . . ? S3 Ir1 S1 C18 -125.3(4) . . . . ? N1 Ir1 S1 Ir2 -91.3(2) . . . . ? S2 Ir1 S1 Ir2 -78.5(4) . . . . ? S3 Ir1 S1 Ir2 6.00(8) . . . . ? N1 Ir1 S2 C17 18.4(5) . . . . ? S1 Ir1 S2 C17 5.5(6) . . . . ? S3 Ir1 S2 C17 -76.4(4) . . . . ? N1 Ir1 S2 C112 -91.1(5) . . . . ? S1 Ir1 S2 C112 -104.0(6) . . . . ? S3 Ir1 S2 C112 174.1(5) . . . . ? S1 Ir1 N1 C12 -15.5(7) . . . . ? S2 Ir1 N1 C12 167.6(7) . . . . ? S3 Ir1 N1 C12 -93.4(7) . . . . ? S1 Ir1 N1 C16 164.6(7) . . . . ? S2 Ir1 N1 C16 -12.3(7) . . . . ? S3 Ir1 N1 C16 86.7(7) . . . . ? C18 S1 C11 C12 -161.5(8) . . . . ? Ir1 S1 C11 C12 -38.3(8) . . . . ? Ir2 S1 C11 C12 67.3(9) . . . . ? C16 N1 C12 C13 -5.8(15) . . . . ? Ir1 N1 C12 C13 174.3(8) . . . . ? C16 N1 C12 C11 172.7(9) . . . . ? Ir1 N1 C12 C11 -7.2(12) . . . . ? S1 C11 C12 N1 32.9(12) . . . . ? S1 C11 C12 C13 -148.6(10) . . . . ? N1 C12 C13 C14 6.3(17) . . . . ? C11 C12 C13 C14 -172.2(11) . . . . ? C12 C13 C14 C15 -3.4(17) . . . . ? C13 C14 C15 C16 0.1(17) . . . . ? C12 N1 C16 C15 2.4(15) . . . . ? Ir1 N1 C16 C15 -177.7(8) . . . . ? C12 N1 C16 C17 178.2(9) . . . . ? Ir1 N1 C16 C17 -1.9(12) . . . . ? C14 C15 C16 N1 0.5(16) . . . . ? C14 C15 C16 C17 -175.1(10) . . . . ? N1 C16 C17 S2 20.1(12) . . . . ? C15 C16 C17 S2 -164.2(9) . . . . ? C112 S2 C17 C16 91.6(8) . . . . ? Ir1 S2 C17 C16 -25.2(8) . . . . ? C11 S1 C18 C111 176.1(9) . . . . ? Ir1 S1 C18 C111 68.9(9) . . . . ? Ir2 S1 C18 C111 -54.3(10) . . . . ? C11 S1 C18 C19 -63.3(9) . . . . ? Ir1 S1 C18 C19 -170.5(6) . . . . ? Ir2 S1 C18 C19 66.3(8) . . . . ? C11 S1 C18 C110 56.7(10) . . . . ? Ir1 S1 C18 C110 -50.4(10) . . . . ? Ir2 S1 C18 C110 -173.7(8) . . . . ? C17 S2 C112 C113 -171.2(10) . . . . ? Ir1 S2 C112 C113 -64.7(10) . . . . ? C17 S2 C112 C114 -49.2(10) . . . . ? Ir1 S2 C112 C114 57.3(9) . . . . ? C17 S2 C112 C115 69.6(10) . . . . ? Ir1 S2 C112 C115 176.1(7) . . . . ? C11 S1 Ir2 N2 -29.3(5) . . . . ? C18 S1 Ir2 N2 -153.7(5) . . . . ? Ir1 S1 Ir2 N2 74.0(3) . . . . ? C11 S1 Ir2 S3 -109.7(4) . . . . ? C18 S1 Ir2 S3 125.9(5) . . . . ? Ir1 S1 Ir2 S3 -6.42(8) . . . . ? C11 S1 Ir2 S4 56.4(4) . . . . ? C18 S1 Ir2 S4 -68.0(5) . . . . ? Ir1 S1 Ir2 S4 159.73(10) . . . . ? N2 Ir2 S3 C21 26.1(4) . . . . ? S4 Ir2 S3 C21 39.5(6) . . . . ? S1 Ir2 S3 C21 124.6(4) . . . . ? N2 Ir2 S3 C28 136.1(5) . . . . ? S4 Ir2 S3 C28 149.5(6) . . . . ? S1 Ir2 S3 C28 -125.3(5) . . . . ? N2 Ir2 S3 Ir1 -92.6(2) . . . . ? S4 Ir2 S3 Ir1 -79.1(4) . . . . ? S1 Ir2 S3 Ir1 6.01(8) . . . . ? N1 Ir1 S3 C21 -30.2(5) . . . . ? S1 Ir1 S3 C21 -111.1(4) . . . . ? S2 Ir1 S3 C21 54.7(4) . . . . ? N1 Ir1 S3 C28 -153.3(4) . . . . ? S1 Ir1 S3 C28 125.8(4) . . . . ? S2 Ir1 S3 C28 -68.4(4) . . . . ? N1 Ir1 S3 Ir2 74.5(2) . . . . ? S1 Ir1 S3 Ir2 -6.45(8) . . . . ? S2 Ir1 S3 Ir2 159.40(10) . . . . ? N2 Ir2 S4 C27 17.8(5) . . . . ? S3 Ir2 S4 C27 4.5(7) . . . . ? S1 Ir2 S4 C27 -78.1(5) . . . . ? N2 Ir2 S4 C212 -89.1(5) . . . . ? S3 Ir2 S4 C212 -102.5(6) . . . . ? S1 Ir2 S4 C212 175.0(4) . . . . ? S3 Ir2 N2 C22 -18.0(7) . . . . ? S4 Ir2 N2 C22 165.2(8) . . . . ? S1 Ir2 N2 C22 -95.5(8) . . . . ? S3 Ir2 N2 C26 166.9(8) . . . . ? S4 Ir2 N2 C26 -9.9(7) . . . . ? S1 Ir2 N2 C26 89.4(7) . . . . ? C28 S3 C21 C22 -158.3(8) . . . . ? Ir2 S3 C21 C22 -35.5(8) . . . . ? Ir1 S3 C21 C22 71.1(8) . . . . ? C26 N2 C22 C23 -4.0(15) . . . . ? Ir2 N2 C22 C23 -179.0(8) . . . . ? C26 N2 C22 C21 173.4(9) . . . . ? Ir2 N2 C22 C21 -1.7(12) . . . . ? S3 C21 C22 N2 27.4(12) . . . . ? S3 C21 C22 C23 -155.3(9) . . . . ? N2 C22 C23 C24 3.1(17) . . . . ? C21 C22 C23 C24 -174.1(11) . . . . ? C22 C23 C24 C25 1.3(18) . . . . ? C23 C24 C25 C26 -4.8(19) . . . . ? C22 N2 C26 C25 0.6(15) . . . . ? Ir2 N2 C26 C25 175.6(8) . . . . ? C22 N2 C26 C27 178.9(10) . . . . ? Ir2 N2 C26 C27 -6.1(13) . . . . ? C24 C25 C26 N2 4.0(18) . . . . ? C24 C25 C26 C27 -174.2(12) . . . . ? N2 C26 C27 S4 24.1(14) . . . . ? C25 C26 C27 S4 -157.7(10) . . . . ? C212 S4 C27 C26 89.7(10) . . . . ? Ir2 S4 C27 C26 -27.1(10) . . . . ? C21 S3 C28 C210 -74.1(9) . . . . ? Ir2 S3 C28 C210 178.8(7) . . . . ? Ir1 S3 C28 C210 55.3(9) . . . . ? C21 S3 C28 C29 168.7(8) . . . . ? Ir2 S3 C28 C29 61.6(9) . . . . ? Ir1 S3 C28 C29 -61.9(8) . . . . ? C21 S3 C28 C211 48.8(9) . . . . ? Ir2 S3 C28 C211 -58.3(9) . . . . ? Ir1 S3 C28 C211 178.2(6) . . . . ? C27 S4 C212 C214 -49.4(11) . . . . ? Ir2 S4 C212 C214 55.0(11) . . . . ? C27 S4 C212 C213 74.9(9) . . . . ? Ir2 S4 C212 C213 179.2(7) . . . . ? C27 S4 C212 C215 -168.6(10) . . . . ? Ir2 S4 C212 C215 -64.3(10) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.778 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.145 data_m775a _database_code_depnum_ccdc_archive 'CCDC 676566' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 Ir N O S2, B F4' _symmetry_space_group_name_Hall -P2ybc _chemical_formula_sum 'C16 H25 B F4 Ir N O S2' _chemical_formula_weight 590.50 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 8.8320(18) _cell_length_b 10.614(2) _cell_length_c 22.104(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.40(3) _cell_angle_gamma 90.00 _cell_volume 2044.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6229 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour 'intense blue' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 6.776 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.1327 _exptl_absorpt_correction_T_max 0.3443 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4627 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4627 _reflns_number_gt 3762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect package (Bruker Nonius)' _computing_cell_refinement HKL _computing_data_reduction HKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+4.5850P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4627 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.098204(17) 0.537434(16) 0.447301(7) 0.02129(6) Uani 1 1 d . . . S1 S 0.07467(12) 0.34131(10) 0.40248(5) 0.0244(2) Uani 1 1 d . . . S2 S 0.09452(12) 0.74672(10) 0.47341(5) 0.0241(2) Uani 1 1 d . . . O1 O 0.3826(3) 0.4752(3) 0.53475(15) 0.0337(8) Uani 1 1 d . . . N1 N -0.1096(4) 0.5745(4) 0.39189(15) 0.0220(8) Uani 1 1 d . . . C1 C 0.2766(5) 0.5003(4) 0.4993(2) 0.0263(9) Uani 1 1 d . . . C2 C -0.1254(5) 0.3506(4) 0.3680(2) 0.0266(10) Uani 1 1 d . . . H2A H -0.1396 0.3049 0.3284 0.032 Uiso 1 1 calc R . . H2B H -0.1876 0.3072 0.3950 0.032 Uiso 1 1 calc R . . C3 C -0.1841(5) 0.4812(4) 0.35684(18) 0.0227(9) Uani 1 1 d . . . C4 C -0.3170(5) 0.5072(5) 0.3161(2) 0.0328(11) Uani 1 1 d . . . H4 H -0.3659 0.4425 0.2903 0.039 Uiso 1 1 calc R . . C5 C -0.3779(5) 0.6258(5) 0.3130(2) 0.0332(11) Uani 1 1 d . . . H5 H -0.4691 0.6440 0.2851 0.040 Uiso 1 1 calc R . . C6 C -0.3054(5) 0.7194(5) 0.3508(2) 0.0313(10) Uani 1 1 d . . . H6 H -0.3470 0.8020 0.3497 0.038 Uiso 1 1 calc R . . C7 C -0.1719(5) 0.6909(4) 0.39023(18) 0.0243(9) Uani 1 1 d . . . C8 C -0.1001(5) 0.7847(4) 0.4368(2) 0.0287(10) Uani 1 1 d . . . H8A H -0.1655 0.7924 0.4690 0.034 Uiso 1 1 calc R . . H8B H -0.0988 0.8679 0.4166 0.034 Uiso 1 1 calc R . . C9 C 0.1746(6) 0.3386(5) 0.3344(2) 0.0334(11) Uani 1 1 d . . . C10 C 0.1220(7) 0.4450(5) 0.2901(2) 0.0427(13) Uani 1 1 d . . . H10A H 0.1839 0.4453 0.2571 0.064 Uiso 1 1 calc R . . H10B H 0.1344 0.5256 0.3120 0.064 Uiso 1 1 calc R . . H10C H 0.0137 0.4329 0.2726 0.064 Uiso 1 1 calc R . . C11 C 0.3439(6) 0.3497(6) 0.3608(3) 0.0521(15) Uani 1 1 d . . . H11A H 0.3705 0.2872 0.3934 0.078 Uiso 1 1 calc R . . H11B H 0.3652 0.4345 0.3776 0.078 Uiso 1 1 calc R . . H11C H 0.4051 0.3345 0.3283 0.078 Uiso 1 1 calc R . . C12 C 0.1400(7) 0.2105(5) 0.3042(3) 0.0490(14) Uani 1 1 d . . . H12A H 0.0290 0.2018 0.2911 0.073 Uiso 1 1 calc R . . H12B H 0.1765 0.1438 0.3337 0.073 Uiso 1 1 calc R . . H12C H 0.1921 0.2035 0.2685 0.073 Uiso 1 1 calc R . . C13 C 0.2190(5) 0.8432(4) 0.4302(2) 0.0294(10) Uani 1 1 d . . . C14 C 0.2052(6) 0.9783(4) 0.4514(2) 0.0381(12) Uani 1 1 d . . . H14A H 0.2759 1.0321 0.4332 0.057 Uiso 1 1 calc R . . H14B H 0.2312 0.9820 0.4962 0.057 Uiso 1 1 calc R . . H14C H 0.0998 1.0079 0.4386 0.057 Uiso 1 1 calc R . . C15 C 0.3817(5) 0.7939(5) 0.4512(2) 0.0380(12) Uani 1 1 d . . . H15A H 0.3879 0.7058 0.4385 0.057 Uiso 1 1 calc R . . H15B H 0.4071 0.7997 0.4959 0.057 Uiso 1 1 calc R . . H15C H 0.4545 0.8446 0.4325 0.057 Uiso 1 1 calc R . . C16 C 0.1710(6) 0.8302(5) 0.3610(2) 0.0405(12) Uani 1 1 d . . . H16A H 0.0666 0.8627 0.3490 0.061 Uiso 1 1 calc R . . H16B H 0.1740 0.7412 0.3494 0.061 Uiso 1 1 calc R . . H16C H 0.2417 0.8784 0.3400 0.061 Uiso 1 1 calc R . . B1 B -0.3613(7) 1.0785(6) 0.3438(3) 0.0360(13) Uani 1 1 d . . . F1 F -0.2131(4) 1.0325(3) 0.35544(15) 0.0507(8) Uani 1 1 d . . . F2 F -0.3694(4) 1.1790(3) 0.30398(14) 0.0537(9) Uani 1 1 d . . . F3 F -0.4619(4) 0.9881(3) 0.3180(2) 0.0774(13) Uani 1 1 d . . . F4 F -0.3973(5) 1.1201(6) 0.39801(17) 0.1038(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02038(9) 0.02347(10) 0.01991(9) 0.00030(7) 0.00301(6) 0.00072(7) S1 0.0278(5) 0.0223(5) 0.0238(5) -0.0002(4) 0.0067(4) -0.0003(4) S2 0.0283(5) 0.0240(6) 0.0200(5) -0.0020(4) 0.0042(4) 0.0009(4) O1 0.0180(15) 0.053(2) 0.0291(15) 0.0111(16) 0.0017(13) 0.0023(15) N1 0.0179(17) 0.032(2) 0.0172(16) 0.0008(15) 0.0063(13) 0.0016(15) C1 0.025(2) 0.032(2) 0.024(2) 0.0054(19) 0.0091(18) 0.0033(19) C2 0.026(2) 0.025(2) 0.028(2) -0.0018(19) 0.0033(18) -0.0040(19) C3 0.022(2) 0.029(2) 0.0177(19) 0.0010(17) 0.0057(16) -0.0038(18) C4 0.028(2) 0.044(3) 0.025(2) 0.000(2) 0.0010(19) -0.010(2) C5 0.022(2) 0.049(3) 0.027(2) 0.008(2) 0.0010(18) -0.002(2) C6 0.029(2) 0.037(3) 0.028(2) 0.008(2) 0.0045(19) 0.006(2) C7 0.024(2) 0.028(2) 0.021(2) -0.0003(18) 0.0075(17) -0.0043(19) C8 0.030(2) 0.030(2) 0.026(2) -0.0008(19) 0.0044(18) 0.003(2) C9 0.043(3) 0.028(2) 0.034(2) -0.003(2) 0.021(2) -0.001(2) C10 0.067(4) 0.036(3) 0.031(3) 0.001(2) 0.027(3) -0.002(3) C11 0.040(3) 0.054(4) 0.069(4) -0.013(3) 0.029(3) 0.005(3) C12 0.077(4) 0.031(3) 0.045(3) -0.011(2) 0.029(3) 0.003(3) C13 0.038(3) 0.023(2) 0.029(2) 0.0009(19) 0.0077(19) -0.005(2) C14 0.052(3) 0.024(3) 0.040(3) 0.000(2) 0.010(2) -0.002(2) C15 0.035(3) 0.031(3) 0.050(3) 0.000(2) 0.015(2) -0.006(2) C16 0.061(3) 0.037(3) 0.026(2) 0.000(2) 0.014(2) -0.007(3) B1 0.036(3) 0.036(3) 0.033(3) 0.003(3) -0.004(2) 0.006(3) F1 0.0397(17) 0.0463(19) 0.062(2) 0.0062(16) -0.0055(15) 0.0048(15) F2 0.0589(19) 0.0351(17) 0.0551(19) 0.0125(15) -0.0269(16) -0.0154(15) F3 0.059(2) 0.041(2) 0.114(3) 0.024(2) -0.041(2) -0.0172(17) F4 0.106(3) 0.157(5) 0.051(2) 0.002(3) 0.020(2) 0.056(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 C1 1.835(5) . ? Ir1 N1 2.071(3) . ? Ir1 S2 2.2966(12) . ? Ir1 S1 2.3002(11) . ? S1 C2 1.809(4) . ? S1 C9 1.865(5) . ? S2 C8 1.821(4) . ? S2 C13 1.875(5) . ? O1 C1 1.150(5) . ? N1 C7 1.351(6) . ? N1 C3 1.359(6) . ? C2 C3 1.487(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.385(6) . ? C4 C5 1.366(7) . ? C4 H4 0.9500 . ? C5 C6 1.386(7) . ? C5 H5 0.9500 . ? C6 C7 1.380(6) . ? C6 H6 0.9500 . ? C7 C8 1.497(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.517(7) . ? C9 C11 1.518(7) . ? C9 C12 1.524(7) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.520(6) . ? C13 C16 1.525(6) . ? C13 C15 1.529(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? B1 F4 1.362(7) . ? B1 F3 1.367(7) . ? B1 F2 1.377(6) . ? B1 F1 1.381(6) . ? 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 Ir1 N1 176.91(16) . . ? C1 Ir1 S2 95.52(15) . . ? N1 Ir1 S2 85.27(11) . . ? C1 Ir1 S1 94.78(15) . . ? N1 Ir1 S1 84.72(11) . . ? S2 Ir1 S1 168.40(4) . . ? C2 S1 C9 102.7(2) . . ? C2 S1 Ir1 98.37(15) . . ? C9 S1 Ir1 109.87(16) . . ? C8 S2 C13 104.0(2) . . ? C8 S2 Ir1 98.85(15) . . ? C13 S2 Ir1 111.51(15) . . ? C7 N1 C3 119.6(4) . . ? C7 N1 Ir1 120.5(3) . . ? C3 N1 Ir1 119.9(3) . . ? O1 C1 Ir1 175.5(4) . . ? C3 C2 S1 114.3(3) . . ? C3 C2 H2A 108.7 . . ? S1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? S1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N1 C3 C4 120.4(4) . . ? N1 C3 C2 117.5(4) . . ? C4 C3 C2 122.0(4) . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 119.2(4) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C6 121.3(4) . . ? N1 C7 C8 117.7(4) . . ? C6 C7 C8 120.7(4) . . ? C7 C8 S2 114.9(3) . . ? C7 C8 H8A 108.5 . . ? S2 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? S2 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C10 C9 C11 111.6(4) . . ? C10 C9 C12 111.3(4) . . ? C11 C9 C12 110.6(4) . . ? C10 C9 S1 112.0(3) . . ? C11 C9 S1 104.8(3) . . ? C12 C9 S1 106.2(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C16 111.9(4) . . ? C14 C13 C15 110.4(4) . . ? C16 C13 C15 111.5(4) . . ? C14 C13 S2 105.9(3) . . ? C16 C13 S2 111.8(3) . . ? C15 C13 S2 105.0(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? F4 B1 F3 111.4(5) . . ? F4 B1 F2 108.4(5) . . ? F3 B1 F2 108.3(4) . . ? F4 B1 F1 107.5(4) . . ? F3 B1 F1 111.2(5) . . ? F2 B1 F1 110.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Ir1 S1 C2 163.1(2) . . . . ? N1 Ir1 S1 C2 -13.86(17) . . . . ? S2 Ir1 S1 C2 -44.3(3) . . . . ? C1 Ir1 S1 C9 -90.1(2) . . . . ? N1 Ir1 S1 C9 92.92(19) . . . . ? S2 Ir1 S1 C9 62.5(3) . . . . ? C1 Ir1 S2 C8 -168.1(2) . . . . ? N1 Ir1 S2 C8 8.89(17) . . . . ? S1 Ir1 S2 C8 39.3(3) . . . . ? C1 Ir1 S2 C13 82.9(2) . . . . ? N1 Ir1 S2 C13 -100.07(18) . . . . ? S1 Ir1 S2 C13 -69.6(3) . . . . ? S2 Ir1 N1 C7 -1.2(3) . . . . ? S1 Ir1 N1 C7 -175.3(3) . . . . ? S2 Ir1 N1 C3 178.8(3) . . . . ? S1 Ir1 N1 C3 4.7(3) . . . . ? C9 S1 C2 C3 -89.3(3) . . . . ? Ir1 S1 C2 C3 23.3(3) . . . . ? C7 N1 C3 C4 5.0(6) . . . . ? Ir1 N1 C3 C4 -175.0(3) . . . . ? C7 N1 C3 C2 -169.9(4) . . . . ? Ir1 N1 C3 C2 10.2(5) . . . . ? S1 C2 C3 N1 -23.9(5) . . . . ? S1 C2 C3 C4 161.3(3) . . . . ? N1 C3 C4 C5 -3.0(7) . . . . ? C2 C3 C4 C5 171.6(4) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ? C4 C5 C6 C7 1.0(7) . . . . ? C3 N1 C7 C6 -4.0(6) . . . . ? Ir1 N1 C7 C6 176.0(3) . . . . ? C3 N1 C7 C8 170.1(4) . . . . ? Ir1 N1 C7 C8 -9.9(5) . . . . ? C5 C6 C7 N1 1.0(6) . . . . ? C5 C6 C7 C8 -172.9(4) . . . . ? N1 C7 C8 S2 18.6(5) . . . . ? C6 C7 C8 S2 -167.3(3) . . . . ? C13 S2 C8 C7 98.4(4) . . . . ? Ir1 S2 C8 C7 -16.5(3) . . . . ? C2 S1 C9 C10 51.0(4) . . . . ? Ir1 S1 C9 C10 -52.9(4) . . . . ? C2 S1 C9 C11 172.2(3) . . . . ? Ir1 S1 C9 C11 68.3(4) . . . . ? C2 S1 C9 C12 -70.7(4) . . . . ? Ir1 S1 C9 C12 -174.6(3) . . . . ? C8 S2 C13 C14 74.1(4) . . . . ? Ir1 S2 C13 C14 179.7(3) . . . . ? C8 S2 C13 C16 -48.0(4) . . . . ? Ir1 S2 C13 C16 57.6(4) . . . . ? C8 S2 C13 C15 -169.1(3) . . . . ? Ir1 S2 C13 C15 -63.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.397 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.140 data_m777a _database_code_depnum_ccdc_archive 'CCDC 676567' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 N O Rh S2, B F4' _chemical_formula_sum 'C16 H25 B F4 N O Rh S2' _chemical_formula_weight 501.21 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 '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 _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8613(3) _cell_length_b 10.6136(2) _cell_length_c 22.1569(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.1505(10) _cell_angle_gamma 90.00 _cell_volume 2057.36(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6154 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 32.03 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7390 _exptl_absorpt_correction_T_max 0.9483 _exptl_absorpt_process_details 'SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7131 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 32.02 _reflns_number_total 7131 _reflns_number_gt 5050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect package (Bruker Nonius)' _computing_cell_refinement HKL _computing_data_reduction HKL _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^)+(0.0504P)^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 7131 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.005 _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 Rh1 Rh 0.09622(2) 0.038746(15) 0.446048(8) 0.01967(6) Uani 1 1 d . . . S1 S 0.07348(7) -0.15889(5) 0.40193(3) 0.02367(13) Uani 1 1 d . . . S2 S 0.09316(7) 0.24876(5) 0.47260(3) 0.02296(13) Uani 1 1 d . . . O1 O 0.3789(2) -0.02383(19) 0.53239(10) 0.0365(5) Uani 1 1 d . . . C1 C 0.2745(3) 0.0016(2) 0.49769(12) 0.0251(5) Uani 1 1 d . . . N1 N -0.1105(2) 0.07518(18) 0.39218(9) 0.0213(4) Uani 1 1 d . . . C2 C -0.1263(3) -0.1490(2) 0.36795(12) 0.0267(5) Uani 1 1 d . . . H2A H -0.1407 -0.1945 0.3284 0.032 Uiso 1 1 calc R . . H2B H -0.1882 -0.1927 0.3950 0.032 Uiso 1 1 calc R . . C3 C -0.1857(3) -0.0180(2) 0.35708(11) 0.0232(5) Uani 1 1 d . . . C4 C -0.3173(3) 0.0066(3) 0.31664(12) 0.0298(5) Uani 1 1 d . . . H4 H -0.3662 -0.0586 0.2914 0.036 Uiso 1 1 calc R . . C5 C -0.3775(3) 0.1272(3) 0.31315(12) 0.0329(6) Uani 1 1 d . . . H5 H -0.4673 0.1459 0.2851 0.040 Uiso 1 1 calc R . . C6 C -0.3057(3) 0.2200(2) 0.35093(12) 0.0297(6) Uani 1 1 d . . . H6 H -0.3475 0.3026 0.3498 0.036 Uiso 1 1 calc R . . C7 C -0.1737(3) 0.1926(2) 0.39022(11) 0.0239(5) Uani 1 1 d . . . C8 C -0.1007(3) 0.2868(2) 0.43645(12) 0.0273(5) Uani 1 1 d . . . H8A H -0.1655 0.2953 0.4687 0.033 Uiso 1 1 calc R . . H8B H -0.0991 0.3697 0.4161 0.033 Uiso 1 1 calc R . . C9 C 0.1737(3) -0.1601(2) 0.33414(13) 0.0341(6) Uani 1 1 d . . . C10 C 0.1201(4) -0.0529(2) 0.28990(14) 0.0434(8) Uani 1 1 d . . . H10A H 0.1335 0.0276 0.3117 0.065 Uiso 1 1 calc R . . H10B H 0.0119 -0.0648 0.2731 0.065 Uiso 1 1 calc R . . H10C H 0.1806 -0.0529 0.2565 0.065 Uiso 1 1 calc R . . C11 C 0.1385(4) -0.2881(3) 0.30265(15) 0.0498(9) Uani 1 1 d . . . H11A H 0.1909 -0.2939 0.2670 0.075 Uiso 1 1 calc R . . H11B H 0.0279 -0.2961 0.2894 0.075 Uiso 1 1 calc R . . H11C H 0.1740 -0.3560 0.3314 0.075 Uiso 1 1 calc R . . C12 C 0.3408(4) -0.1489(3) 0.36017(17) 0.0534(9) Uani 1 1 d . . . H12A H 0.3676 -0.2123 0.3922 0.080 Uiso 1 1 calc R . . H12B H 0.3613 -0.0646 0.3776 0.080 Uiso 1 1 calc R . . H12C H 0.4021 -0.1623 0.3276 0.080 Uiso 1 1 calc R . . C13 C 0.2184(3) 0.3443(2) 0.42921(12) 0.0270(5) Uani 1 1 d . . . C14 C 0.1700(4) 0.3311(3) 0.36013(13) 0.0403(7) Uani 1 1 d . . . H14A H 0.2432 0.3757 0.3390 0.060 Uiso 1 1 calc R . . H14B H 0.0680 0.3675 0.3482 0.060 Uiso 1 1 calc R . . H14C H 0.1679 0.2418 0.3489 0.060 Uiso 1 1 calc R . . C15 C 0.2057(4) 0.4799(2) 0.45057(15) 0.0402(7) Uani 1 1 d . . . H15A H 0.2315 0.4835 0.4952 0.060 Uiso 1 1 calc R . . H15B H 0.1009 0.5101 0.4380 0.060 Uiso 1 1 calc R . . H15C H 0.2765 0.5333 0.4323 0.060 Uiso 1 1 calc R . . C16 C 0.3792(3) 0.2948(3) 0.44964(15) 0.0391(7) Uani 1 1 d . . . H16A H 0.4523 0.3471 0.4321 0.059 Uiso 1 1 calc R . . H16B H 0.3858 0.2076 0.4357 0.059 Uiso 1 1 calc R . . H16C H 0.4032 0.2976 0.4943 0.059 Uiso 1 1 calc R . . B1 B -0.3635(4) 0.5805(3) 0.34423(16) 0.0361(7) Uani 1 1 d . . . F1 F -0.3729(2) 0.68079(15) 0.30415(9) 0.0499(5) Uani 1 1 d . A . F2 F -0.3863(7) 0.6359(8) 0.39982(15) 0.0599(19) Uani 0.71(2) 1 d P A 1 F2B F -0.4296(16) 0.5809(17) 0.3949(5) 0.064(3) Uiso 0.29(2) 1 d P A 2 F3 F -0.2164(2) 0.53322(15) 0.35460(9) 0.0482(5) Uani 1 1 d . A . F4 F -0.4663(2) 0.49026(18) 0.31982(12) 0.0738(7) 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 Rh1 0.01898(9) 0.02026(9) 0.01972(10) 0.00041(7) 0.00292(7) 0.00090(7) S1 0.0268(3) 0.0203(2) 0.0252(3) 0.0002(2) 0.0078(3) 0.0001(2) S2 0.0264(3) 0.0214(3) 0.0211(3) -0.0017(2) 0.0039(2) 0.0006(2) O1 0.0205(9) 0.0568(13) 0.0319(10) 0.0122(9) 0.0035(8) 0.0028(8) C1 0.0208(12) 0.0302(11) 0.0241(13) 0.0019(10) 0.0037(10) -0.0006(10) N1 0.0211(10) 0.0246(9) 0.0186(10) -0.0004(8) 0.0046(8) 0.0015(8) C2 0.0272(13) 0.0270(12) 0.0259(13) -0.0023(10) 0.0039(11) -0.0051(10) C3 0.0214(11) 0.0299(12) 0.0187(11) -0.0011(9) 0.0045(9) -0.0031(9) C4 0.0286(13) 0.0383(13) 0.0219(13) 0.0005(11) 0.0019(11) -0.0063(11) C5 0.0240(13) 0.0484(15) 0.0248(14) 0.0085(12) -0.0011(11) 0.0009(11) C6 0.0258(13) 0.0342(13) 0.0294(14) 0.0072(11) 0.0051(11) 0.0049(10) C7 0.0244(12) 0.0253(11) 0.0230(12) 0.0018(9) 0.0070(10) 0.0028(9) C8 0.0301(13) 0.0254(11) 0.0265(13) -0.0014(10) 0.0048(11) 0.0071(10) C9 0.0401(16) 0.0305(12) 0.0371(16) -0.0047(11) 0.0228(14) 0.0001(11) C10 0.068(2) 0.0330(14) 0.0359(17) 0.0033(12) 0.0296(17) 0.0006(13) C11 0.078(2) 0.0331(14) 0.0459(19) -0.0092(13) 0.0351(19) 0.0013(15) C12 0.0366(17) 0.066(2) 0.064(2) -0.0106(18) 0.0268(17) 0.0057(15) C13 0.0335(13) 0.0219(10) 0.0265(13) 0.0003(10) 0.0076(11) -0.0044(10) C14 0.057(2) 0.0363(14) 0.0291(15) 0.0023(12) 0.0126(15) -0.0115(13) C15 0.0543(19) 0.0230(12) 0.0441(18) -0.0039(11) 0.0099(16) -0.0067(12) C16 0.0343(15) 0.0363(14) 0.0501(19) 0.0005(13) 0.0169(14) -0.0072(12) B1 0.0392(18) 0.0317(14) 0.0345(18) 0.0017(14) -0.0027(15) 0.0032(14) F1 0.0540(11) 0.0345(9) 0.0523(12) 0.0118(8) -0.0188(9) -0.0138(8) F2 0.064(3) 0.074(4) 0.0429(19) -0.0101(17) 0.0110(16) 0.010(2) F3 0.0364(10) 0.0467(10) 0.0584(13) 0.0050(8) -0.0020(9) 0.0087(8) F4 0.0548(13) 0.0385(9) 0.112(2) 0.0249(12) -0.0365(13) -0.0157(9) _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 Rh1 C1 1.840(3) . ? Rh1 N1 2.058(2) . ? Rh1 S2 2.3067(6) . ? Rh1 S1 2.3095(6) . ? S1 C2 1.813(3) . ? S1 C9 1.863(2) . ? S2 C8 1.822(3) . ? S2 C13 1.877(2) . ? O1 C1 1.137(3) . ? N1 C3 1.365(3) . ? N1 C7 1.364(3) . ? C2 C3 1.493(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.378(4) . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.381(4) . ? C5 H5 0.9500 . ? C6 C7 1.373(4) . ? C6 H6 0.9500 . ? C7 C8 1.503(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C12 1.506(4) . ? C9 C10 1.527(4) . ? C9 C11 1.536(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C16 1.518(4) . ? C13 C15 1.525(3) . ? C13 C14 1.529(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? B1 F2B 1.345(10) . ? B1 F2 1.408(5) . ? B1 F4 1.372(4) . ? B1 F3 1.382(4) . ? B1 F1 1.380(4) . ? F2B F4 1.904(16) . ? 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 Rh1 N1 176.43(9) . . ? C1 Rh1 S2 95.28(8) . . ? N1 Rh1 S2 85.46(6) . . ? C1 Rh1 S1 94.43(8) . . ? N1 Rh1 S1 85.15(6) . . ? S2 Rh1 S1 169.09(2) . . ? C2 S1 C9 102.99(13) . . ? C2 S1 Rh1 97.87(8) . . ? C9 S1 Rh1 109.09(8) . . ? C8 S2 C13 104.36(12) . . ? C8 S2 Rh1 98.67(8) . . ? C13 S2 Rh1 111.06(7) . . ? O1 C1 Rh1 175.5(2) . . ? C3 N1 C7 118.9(2) . . ? C3 N1 Rh1 120.22(16) . . ? C7 N1 Rh1 120.89(17) . . ? C3 C2 S1 114.64(17) . . ? C3 C2 H2A 108.6 . . ? S1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? S1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N1 C3 C4 121.3(2) . . ? N1 C3 C2 117.1(2) . . ? C4 C3 C2 121.5(2) . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 C5 119.8(2) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N1 C7 C6 121.2(2) . . ? N1 C7 C8 117.1(2) . . ? C6 C7 C8 121.5(2) . . ? C7 C8 S2 115.22(16) . . ? C7 C8 H8A 108.5 . . ? S2 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? S2 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C12 C9 C10 111.9(2) . . ? C12 C9 C11 111.2(2) . . ? C10 C9 C11 110.3(3) . . ? C12 C9 S1 104.9(2) . . ? C10 C9 S1 111.89(17) . . ? C11 C9 S1 106.51(17) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C16 C13 C15 110.3(2) . . ? C16 C13 C14 111.5(2) . . ? C15 C13 C14 112.0(2) . . ? C16 C13 S2 105.28(17) . . ? C15 C13 S2 105.77(17) . . ? C14 C13 S2 111.66(18) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? F2B B1 F2 29.2(6) . . ? F2B B1 F4 88.9(9) . . ? F2 B1 F4 117.2(5) . . ? F2B B1 F3 112.7(5) . . ? F2 B1 F3 105.6(3) . . ? F4 B1 F3 111.2(3) . . ? F2B B1 F1 123.0(6) . . ? F2 B1 F1 103.8(4) . . ? F4 B1 F1 108.5(3) . . ? F3 B1 F1 110.2(3) . . ? B1 F2B F4 46.1(5) . . ? B1 F4 F2B 45.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Rh1 S1 C2 163.11(11) . . . . ? N1 Rh1 S1 C2 -13.33(9) . . . . ? S2 Rh1 S1 C2 -44.06(14) . . . . ? C1 Rh1 S1 C9 -90.15(13) . . . . ? N1 Rh1 S1 C9 93.41(12) . . . . ? S2 Rh1 S1 C9 62.68(16) . . . . ? C1 Rh1 S2 C8 -168.17(11) . . . . ? N1 Rh1 S2 C8 8.33(9) . . . . ? S1 Rh1 S2 C8 39.04(14) . . . . ? C1 Rh1 S2 C13 82.71(12) . . . . ? N1 Rh1 S2 C13 -100.79(11) . . . . ? S1 Rh1 S2 C13 -70.08(15) . . . . ? S2 Rh1 N1 C3 178.54(16) . . . . ? S1 Rh1 N1 C3 4.10(15) . . . . ? S2 Rh1 N1 C7 -0.59(16) . . . . ? S1 Rh1 N1 C7 -175.02(16) . . . . ? C9 S1 C2 C3 -88.97(19) . . . . ? Rh1 S1 C2 C3 22.80(18) . . . . ? C7 N1 C3 C4 4.9(3) . . . . ? Rh1 N1 C3 C4 -174.20(17) . . . . ? C7 N1 C3 C2 -170.39(19) . . . . ? Rh1 N1 C3 C2 10.5(3) . . . . ? S1 C2 C3 N1 -23.8(3) . . . . ? S1 C2 C3 C4 160.91(18) . . . . ? N1 C3 C4 C5 -2.4(3) . . . . ? C2 C3 C4 C5 172.7(2) . . . . ? C3 C4 C5 C6 -0.9(4) . . . . ? C4 C5 C6 C7 1.7(4) . . . . ? C3 N1 C7 C6 -4.1(3) . . . . ? Rh1 N1 C7 C6 174.99(16) . . . . ? C3 N1 C7 C8 170.70(19) . . . . ? Rh1 N1 C7 C8 -10.2(3) . . . . ? C5 C6 C7 N1 0.9(3) . . . . ? C5 C6 C7 C8 -173.8(2) . . . . ? N1 C7 C8 S2 18.2(3) . . . . ? C6 C7 C8 S2 -166.94(18) . . . . ? C13 S2 C8 C7 98.54(18) . . . . ? Rh1 S2 C8 C7 -15.93(18) . . . . ? C2 S1 C9 C12 171.85(18) . . . . ? Rh1 S1 C9 C12 68.65(19) . . . . ? C2 S1 C9 C10 50.4(2) . . . . ? Rh1 S1 C9 C10 -52.8(2) . . . . ? C2 S1 C9 C11 -70.2(2) . . . . ? Rh1 S1 C9 C11 -173.45(19) . . . . ? C8 S2 C13 C16 -168.89(17) . . . . ? Rh1 S2 C13 C16 -63.51(18) . . . . ? C8 S2 C13 C15 74.4(2) . . . . ? Rh1 S2 C13 C15 179.73(17) . . . . ? C8 S2 C13 C14 -47.7(2) . . . . ? Rh1 S2 C13 C14 57.7(2) . . . . ? F2 B1 F2B F4 166.2(10) . . . . ? F3 B1 F2B F4 -112.6(5) . . . . ? F1 B1 F2B F4 111.5(6) . . . . ? F2 B1 F4 F2B -7.5(5) . . . . ? F3 B1 F4 F2B 114.0(5) . . . . ? F1 B1 F4 F2B -124.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.707 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.117 data_m780a _database_code_depnum_ccdc_archive 'CCDC 676568' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H39 Ir N S2, B F4' _chemical_formula_sum 'C23 H39 B F4 Ir N S2' _chemical_formula_weight 672.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 17.5452(6) _cell_length_b 9.7839(3) _cell_length_c 15.3976(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.981(2) _cell_angle_gamma 90.00 _cell_volume 2636.85(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6077 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 5.262 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5007 _exptl_absorpt_correction_T_max 0.7711 _exptl_absorpt_process_details 'SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6003 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.45 _reflns_number_total 6003 _reflns_number_gt 4224 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect package Bruker - Nonius' _computing_cell_refinement HKL _computing_data_reduction HKL _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^)+(0.0463P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6003 _refine_ls_number_parameters 305 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1A Ir 0.23527(3) 0.13755(9) -0.073961(19) 0.02953(17) Uani 0.936(4) 1 d P . . Ir1B Ir 0.2470(5) 0.1827(17) -0.0801(4) 0.047(2) Uiso 0.064(4) 1 d P . . N1 N 0.3296(3) 0.1000(4) 0.0082(2) 0.0319(10) Uani 1 1 d . . . S1 S 0.21885(8) -0.09327(14) -0.06731(8) 0.0340(3) Uani 1 1 d . . . S2 S 0.27892(9) 0.36319(13) -0.06161(8) 0.0372(3) Uani 1 1 d . . . C1 C 0.3252(4) 0.3381(5) 0.0477(3) 0.0442(15) Uani 1 1 d . . . H1A H 0.3628 0.4120 0.0604 0.053 Uiso 1 1 calc R . . H1B H 0.2862 0.3438 0.0911 0.053 Uiso 1 1 calc R . . C2 C 0.3646(3) 0.2031(6) 0.0559(3) 0.0377(13) Uani 1 1 d . . . C3 C 0.4301(4) 0.1785(6) 0.1081(3) 0.0458(16) Uani 1 1 d . . . H3 H 0.4546 0.2514 0.1398 0.055 Uiso 1 1 calc R . . C4 C 0.4599(4) 0.0490(6) 0.1145(4) 0.0480(16) Uani 1 1 d . . . H4 H 0.5048 0.0311 0.1509 0.058 Uiso 1 1 calc R . . C5 C 0.4236(3) -0.0548(6) 0.0672(3) 0.0415(14) Uani 1 1 d . . . H5 H 0.4434 -0.1452 0.0715 0.050 Uiso 1 1 calc R . . C6 C 0.3591(3) -0.0286(5) 0.0139(3) 0.0323(12) Uani 1 1 d . . . C7 C 0.3186(3) -0.1355(5) -0.0415(3) 0.0327(11) Uani 1 1 d . . . H7A H 0.3219 -0.2242 -0.0105 0.039 Uiso 1 1 calc R . . H7B H 0.3445 -0.1457 -0.0962 0.039 Uiso 1 1 calc R . . C8 C 0.1713(3) -0.1522(5) 0.0310(3) 0.0341(12) Uani 1 1 d . . . C9 C 0.2122(3) -0.1068(6) 0.1159(3) 0.0405(13) Uani 1 1 d . . . H9A H 0.2186 -0.0073 0.1155 0.061 Uiso 1 1 calc R . . H9B H 0.2625 -0.1506 0.1227 0.061 Uiso 1 1 calc R . . H9C H 0.1821 -0.1330 0.1645 0.061 Uiso 1 1 calc R . . C10 C 0.0906(3) -0.0938(6) 0.0217(4) 0.0408(13) Uani 1 1 d . . . H10A H 0.0603 -0.1327 0.0668 0.061 Uiso 1 1 calc R . . H10B H 0.0668 -0.1169 -0.0359 0.061 Uiso 1 1 calc R . . H10C H 0.0928 0.0058 0.0282 0.061 Uiso 1 1 calc R . . C11 C 0.1683(4) -0.3105(6) 0.0265(4) 0.0488(15) Uani 1 1 d . . . H11A H 0.2204 -0.3472 0.0334 0.073 Uiso 1 1 calc R . . H11B H 0.1443 -0.3388 -0.0299 0.073 Uiso 1 1 calc R . . H11C H 0.1385 -0.3454 0.0732 0.073 Uiso 1 1 calc R . . C12 C 0.3621(3) 0.4016(6) -0.1287(3) 0.0401(13) Uani 1 1 d . . . C13 C 0.3293(4) 0.4841(6) -0.2050(4) 0.0507(16) Uani 1 1 d . . . H13A H 0.3709 0.5246 -0.2356 0.076 Uiso 1 1 calc R . . H13B H 0.2968 0.5569 -0.1841 0.076 Uiso 1 1 calc R . . H13C H 0.2987 0.4244 -0.2449 0.076 Uiso 1 1 calc R . . C14 C 0.4200(4) 0.4891(7) -0.0751(4) 0.064(2) Uani 1 1 d . . . H14A H 0.4457 0.4332 -0.0291 0.096 Uiso 1 1 calc R . . H14B H 0.3935 0.5653 -0.0489 0.096 Uiso 1 1 calc R . . H14C H 0.4579 0.5251 -0.1130 0.096 Uiso 1 1 calc R . . C15 C 0.4004(4) 0.2721(6) -0.1589(4) 0.0525(16) Uani 1 1 d . . . H15A H 0.3627 0.2159 -0.1926 0.079 Uiso 1 1 calc R . . H15B H 0.4212 0.2204 -0.1081 0.079 Uiso 1 1 calc R . . H15C H 0.4419 0.2964 -0.1954 0.079 Uiso 1 1 calc R . . C16 C 0.1630(4) 0.1368(6) -0.1940(4) 0.0426(14) Uani 1 1 d . . . H16 H 0.1602 0.0269 -0.2194 0.10(3) Uiso 1 1 d R . . C17 C 0.1208(4) 0.1852(7) -0.1272(4) 0.0548(17) Uani 1 1 d D . . H17 H 0.084(3) 0.109(5) -0.098(3) 0.058(18) Uiso 1 1 d D . . C18 C 0.0912(4) 0.3275(7) -0.1198(5) 0.067(2) Uani 1 1 d . . . H18A H 0.1309 0.3928 -0.1359 0.081 Uiso 1 1 calc R . . H18B H 0.0806 0.3455 -0.0585 0.081 Uiso 1 1 calc R . . C19 C 0.0165(4) 0.3520(7) -0.1796(5) 0.070(2) Uani 1 1 d . . . H19A H -0.0188 0.2749 -0.1717 0.084 Uiso 1 1 calc R . . H19B H -0.0084 0.4361 -0.1598 0.084 Uiso 1 1 calc R . . C20 C 0.0282(5) 0.3664(7) -0.2776(4) 0.065(2) Uani 1 1 d . . . H20A H -0.0186 0.4068 -0.3066 0.078 Uiso 1 1 calc R . . H20B H 0.0706 0.4314 -0.2846 0.078 Uiso 1 1 calc R . . C21 C 0.0458(5) 0.2349(8) -0.3240(5) 0.077(2) Uani 1 1 d . . . H21A H 0.0299 0.1579 -0.2877 0.092 Uiso 1 1 calc R . . H21B H 0.0132 0.2319 -0.3792 0.092 Uiso 1 1 calc R . . C22 C 0.1259(4) 0.2095(8) -0.3452(4) 0.0617(18) Uani 1 1 d . . . H22A H 0.1392 0.2740 -0.3914 0.074 Uiso 1 1 calc R . . H22B H 0.1298 0.1157 -0.3685 0.074 Uiso 1 1 calc R . . C23 C 0.1838(4) 0.2260(6) -0.2665(4) 0.0504(16) Uani 1 1 d . . . H23A H 0.2355 0.2017 -0.2834 0.061 Uiso 1 1 calc R . . H23B H 0.1848 0.3225 -0.2471 0.061 Uiso 1 1 calc R . . B1 B 0.3724(4) 0.6069(6) 0.2049(4) 0.0399(16) Uani 1 1 d . . . F1 F 0.3671(2) 0.6503(3) 0.1191(2) 0.0521(9) Uani 1 1 d . . . F2 F 0.4193(2) 0.4919(3) 0.2110(2) 0.0608(11) Uani 1 1 d . . . F3 F 0.4054(2) 0.7057(4) 0.2589(2) 0.0699(12) Uani 1 1 d . . . F4 F 0.3025(3) 0.5731(6) 0.2294(3) 0.1021(16) 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 Ir1A 0.03845(19) 0.0227(3) 0.02745(14) 0.00154(12) 0.00247(9) 0.00096(17) N1 0.043(3) 0.028(2) 0.024(2) 0.0019(17) -0.0020(18) -0.0033(19) S1 0.0436(9) 0.0273(6) 0.0305(6) -0.0026(5) -0.0024(6) -0.0016(6) S2 0.0554(10) 0.0245(6) 0.0328(6) 0.0006(5) 0.0111(6) 0.0029(6) C1 0.072(5) 0.034(3) 0.026(3) -0.007(2) 0.008(3) -0.006(3) C2 0.058(4) 0.035(3) 0.020(2) 0.003(2) 0.001(2) -0.007(3) C3 0.060(4) 0.051(4) 0.026(3) 0.006(2) 0.001(3) -0.026(3) C4 0.051(4) 0.060(4) 0.032(3) 0.017(3) -0.002(3) -0.008(3) C5 0.046(4) 0.046(3) 0.032(3) 0.015(2) 0.002(2) 0.001(3) C6 0.036(3) 0.034(3) 0.028(2) 0.006(2) 0.007(2) -0.002(2) C7 0.039(3) 0.028(3) 0.031(2) -0.002(2) 0.001(2) 0.004(2) C8 0.037(3) 0.029(3) 0.036(3) 0.001(2) 0.001(2) -0.001(2) C9 0.043(4) 0.043(3) 0.036(3) -0.005(2) 0.007(2) 0.001(3) C10 0.039(3) 0.036(3) 0.047(3) -0.002(3) 0.004(3) -0.006(3) C11 0.062(4) 0.030(3) 0.056(4) -0.005(3) 0.014(3) -0.006(3) C12 0.052(4) 0.034(3) 0.035(3) 0.005(2) 0.003(3) -0.002(3) C13 0.056(4) 0.048(4) 0.049(3) 0.024(3) 0.010(3) -0.002(3) C14 0.072(5) 0.064(4) 0.056(4) -0.012(3) 0.003(4) -0.027(4) C15 0.066(5) 0.042(3) 0.050(3) 0.003(3) 0.014(3) 0.009(3) C16 0.042(4) 0.041(3) 0.043(3) 0.007(3) -0.008(3) 0.006(3) C17 0.055(4) 0.049(4) 0.060(4) 0.019(3) 0.001(3) 0.005(3) C18 0.072(5) 0.070(5) 0.061(4) 0.018(3) 0.013(4) 0.036(4) C19 0.057(5) 0.067(5) 0.087(5) 0.044(4) 0.021(4) 0.022(4) C20 0.070(5) 0.064(5) 0.059(4) 0.017(3) -0.013(4) 0.025(4) C21 0.089(6) 0.072(5) 0.066(5) 0.013(4) -0.014(4) 0.022(5) C22 0.073(5) 0.064(4) 0.046(3) 0.008(3) -0.013(3) 0.008(4) C23 0.065(5) 0.045(3) 0.040(3) 0.002(3) -0.006(3) 0.003(3) B1 0.056(5) 0.036(4) 0.028(3) 0.002(2) 0.002(3) 0.000(3) F1 0.080(3) 0.0349(18) 0.0402(18) 0.0090(13) -0.0053(17) 0.0002(17) F2 0.091(3) 0.0325(18) 0.055(2) -0.0039(15) -0.021(2) 0.0163(18) F3 0.098(3) 0.046(2) 0.062(2) -0.0232(18) -0.027(2) 0.016(2) F4 0.069(3) 0.139(4) 0.103(4) 0.015(3) 0.036(3) -0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1A N1 2.046(4) . ? Ir1A C17 2.166(7) . ? Ir1A C16 2.168(5) . ? Ir1A S1 2.2799(17) . ? Ir1A S2 2.3401(16) . ? Ir1B S2 1.869(17) . ? Ir1B N1 2.082(8) . ? Ir1B C16 2.256(9) . ? Ir1B C17 2.281(10) . ? Ir1B S1 2.754(17) . ? N1 C6 1.362(6) . ? N1 C2 1.368(7) . ? S1 C7 1.816(5) . ? S1 C8 1.870(5) . ? S2 C1 1.833(5) . ? S2 C12 1.885(6) . ? C1 C2 1.492(8) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.377(8) . ? C3 C4 1.372(9) . ? C3 H3 0.9500 . ? C4 C5 1.380(8) . ? C4 H4 0.9500 . ? C5 C6 1.375(8) . ? C5 H5 0.9500 . ? C6 C7 1.497(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.513(7) . ? C8 C10 1.525(8) . ? C8 C11 1.551(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.506(7) . ? C12 C15 1.521(8) . ? C12 C14 1.526(8) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.392(9) . ? C16 C23 1.482(8) . ? C16 H16 1.1436 . ? C17 C18 1.493(9) . ? C17 H17 1.10(2) . ? C18 C19 1.567(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.543(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.514(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.486(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.535(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? B1 F4 1.350(8) . ? B1 F3 1.377(7) . ? B1 F1 1.385(7) . ? B1 F2 1.392(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ir1A C17 164.1(2) . . ? N1 Ir1A C16 158.0(2) . . ? C17 Ir1A C16 37.5(2) . . ? N1 Ir1A S1 83.90(12) . . ? C17 Ir1A S1 96.51(18) . . ? C16 Ir1A S1 88.08(15) . . ? N1 Ir1A S2 82.69(12) . . ? C17 Ir1A S2 96.74(18) . . ? C16 Ir1A S2 103.97(16) . . ? S1 Ir1A S2 166.53(5) . . ? S2 Ir1B N1 94.6(4) . . ? S2 Ir1B C16 118.7(6) . . ? N1 Ir1B C16 144.9(8) . . ? S2 Ir1B C17 108.2(5) . . ? N1 Ir1B C17 145.9(8) . . ? C16 Ir1B C17 35.7(3) . . ? S2 Ir1B S1 165.6(3) . . ? N1 Ir1B S1 72.1(5) . . ? C16 Ir1B S1 75.5(5) . . ? C17 Ir1B S1 81.9(5) . . ? C6 N1 C2 119.5(5) . . ? C6 N1 Ir1A 119.6(3) . . ? C2 N1 Ir1A 120.9(4) . . ? C6 N1 Ir1B 130.2(5) . . ? C2 N1 Ir1B 109.3(5) . . ? C7 S1 C8 103.3(2) . . ? C7 S1 Ir1A 96.46(17) . . ? C8 S1 Ir1A 113.99(16) . . ? C7 S1 Ir1B 93.7(2) . . ? C8 S1 Ir1B 116.9(2) . . ? C1 S2 Ir1B 97.0(3) . . ? C1 S2 C12 102.7(3) . . ? Ir1B S2 C12 109.9(3) . . ? C1 S2 Ir1A 94.00(17) . . ? C12 S2 Ir1A 113.90(18) . . ? C2 C1 S2 111.7(3) . . ? C2 C1 H1A 109.3 . . ? S2 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? S2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? N1 C2 C3 120.7(5) . . ? N1 C2 C1 114.8(5) . . ? C3 C2 C1 124.6(5) . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 120.5(6) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N1 C6 C5 120.3(5) . . ? N1 C6 C7 116.5(4) . . ? C5 C6 C7 123.2(5) . . ? C6 C7 S1 112.2(4) . . ? C6 C7 H7A 109.2 . . ? S1 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? S1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C10 110.7(4) . . ? C9 C8 C11 110.1(4) . . ? C10 C8 C11 110.0(5) . . ? C9 C8 S1 113.4(4) . . ? C10 C8 S1 105.8(3) . . ? C11 C8 S1 106.7(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C15 111.2(5) . . ? C13 C12 C14 109.0(5) . . ? C15 C12 C14 110.0(5) . . ? C13 C12 S2 105.4(4) . . ? C15 C12 S2 112.1(4) . . ? C14 C12 S2 109.0(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C23 121.8(5) . . ? C17 C16 Ir1A 71.2(4) . . ? C23 C16 Ir1A 118.7(4) . . ? C17 C16 Ir1B 73.1(4) . . ? C23 C16 Ir1B 106.7(6) . . ? C17 C16 H16 124.0 . . ? C23 C16 H16 107.7 . . ? Ir1A C16 H16 107.6 . . ? Ir1B C16 H16 117.6 . . ? C16 C17 C18 125.4(6) . . ? C16 C17 Ir1A 71.3(4) . . ? C18 C17 Ir1A 119.4(5) . . ? C16 C17 Ir1B 71.2(4) . . ? C18 C17 Ir1B 108.7(6) . . ? C16 C17 H17 115(3) . . ? C18 C17 H17 113(3) . . ? Ir1A C17 H17 105(3) . . ? Ir1B C17 H17 116(3) . . ? C17 C18 C19 112.3(6) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 115.3(6) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C21 C20 C19 115.4(6) . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20B 108.4 . . ? C19 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C22 C21 C20 118.2(7) . . ? C22 C21 H21A 107.8 . . ? C20 C21 H21A 107.8 . . ? C22 C21 H21B 107.8 . . ? C20 C21 H21B 107.8 . . ? H21A C21 H21B 107.1 . . ? C21 C22 C23 113.2(6) . . ? C21 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? H22A C22 H22B 107.8 . . ? C16 C23 C22 110.4(5) . . ? C16 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? C16 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? F4 B1 F3 110.8(5) . . ? F4 B1 F1 109.8(6) . . ? F3 B1 F1 111.0(5) . . ? F4 B1 F2 109.1(5) . . ? F3 B1 F2 107.7(5) . . ? F1 B1 F2 108.2(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 Ir1A N1 C6 111.4(8) . . . . ? C16 Ir1A N1 C6 -50.3(7) . . . . ? S1 Ir1A N1 C6 19.0(4) . . . . ? S2 Ir1A N1 C6 -159.7(4) . . . . ? C17 Ir1A N1 C2 -70.3(9) . . . . ? C16 Ir1A N1 C2 128.1(6) . . . . ? S1 Ir1A N1 C2 -162.6(4) . . . . ? S2 Ir1A N1 C2 18.7(4) . . . . ? C17 Ir1A N1 Ir1B -105.4(10) . . . . ? C16 Ir1A N1 Ir1B 92.9(9) . . . . ? S1 Ir1A N1 Ir1B 162.2(7) . . . . ? S2 Ir1A N1 Ir1B -16.5(7) . . . . ? S2 Ir1B N1 C6 -157.6(5) . . . . ? C16 Ir1B N1 C6 4.3(14) . . . . ? C17 Ir1B N1 C6 69.7(9) . . . . ? S1 Ir1B N1 C6 27.7(5) . . . . ? S2 Ir1B N1 C2 10.9(5) . . . . ? C16 Ir1B N1 C2 172.8(9) . . . . ? C17 Ir1B N1 C2 -121.7(10) . . . . ? S1 Ir1B N1 C2 -163.8(4) . . . . ? S2 Ir1B N1 Ir1A 159.3(9) . . . . ? C16 Ir1B N1 Ir1A -38.8(10) . . . . ? C17 Ir1B N1 Ir1A 26.7(8) . . . . ? S1 Ir1B N1 Ir1A -15.4(6) . . . . ? N1 Ir1A S1 C7 -25.6(2) . . . . ? C17 Ir1A S1 C7 170.4(3) . . . . ? C16 Ir1A S1 C7 133.8(2) . . . . ? S2 Ir1A S1 C7 -20.0(3) . . . . ? N1 Ir1A S1 C8 82.0(2) . . . . ? C17 Ir1A S1 C8 -81.9(3) . . . . ? C16 Ir1A S1 C8 -118.5(3) . . . . ? S2 Ir1A S1 C8 87.7(3) . . . . ? N1 Ir1A S1 Ir1B -64(2) . . . . ? C17 Ir1A S1 Ir1B 132(2) . . . . ? C16 Ir1A S1 Ir1B 96(2) . . . . ? S2 Ir1A S1 Ir1B -58(2) . . . . ? S2 Ir1B S1 C7 -51.3(14) . . . . ? N1 Ir1B S1 C7 -29.2(3) . . . . ? C16 Ir1B S1 C7 137.2(3) . . . . ? C17 Ir1B S1 C7 173.1(3) . . . . ? S2 Ir1B S1 C8 55.6(15) . . . . ? N1 Ir1B S1 C8 77.7(3) . . . . ? C16 Ir1B S1 C8 -115.9(3) . . . . ? C17 Ir1B S1 C8 -80.0(3) . . . . ? S2 Ir1B S1 Ir1A 91(3) . . . . ? N1 Ir1B S1 Ir1A 113(2) . . . . ? C16 Ir1B S1 Ir1A -81(2) . . . . ? C17 Ir1B S1 Ir1A -44.9(19) . . . . ? N1 Ir1B S2 C1 -23.7(4) . . . . ? C16 Ir1B S2 C1 168.0(4) . . . . ? C17 Ir1B S2 C1 130.5(4) . . . . ? S1 Ir1B S2 C1 -2.7(15) . . . . ? N1 Ir1B S2 C12 82.5(4) . . . . ? C16 Ir1B S2 C12 -85.8(4) . . . . ? C17 Ir1B S2 C12 -123.2(4) . . . . ? S1 Ir1B S2 C12 103.6(14) . . . . ? N1 Ir1B S2 Ir1A -71(2) . . . . ? C16 Ir1B S2 Ir1A 120(3) . . . . ? C17 Ir1B S2 Ir1A 83(2) . . . . ? S1 Ir1B S2 Ir1A -50(2) . . . . ? N1 Ir1A S2 C1 -28.4(2) . . . . ? C17 Ir1A S2 C1 135.6(3) . . . . ? C16 Ir1A S2 C1 173.0(3) . . . . ? S1 Ir1A S2 C1 -34.0(3) . . . . ? N1 Ir1A S2 Ir1B 104(3) . . . . ? C17 Ir1A S2 Ir1B -92(3) . . . . ? C16 Ir1A S2 Ir1B -54(3) . . . . ? S1 Ir1A S2 Ir1B 99(3) . . . . ? N1 Ir1A S2 C12 77.4(2) . . . . ? C17 Ir1A S2 C12 -118.6(3) . . . . ? C16 Ir1A S2 C12 -81.2(3) . . . . ? S1 Ir1A S2 C12 71.7(3) . . . . ? Ir1B S2 C1 C2 37.0(5) . . . . ? C12 S2 C1 C2 -75.3(5) . . . . ? Ir1A S2 C1 C2 40.3(4) . . . . ? C6 N1 C2 C3 1.3(7) . . . . ? Ir1A N1 C2 C3 -177.0(4) . . . . ? Ir1B N1 C2 C3 -168.6(5) . . . . ? C6 N1 C2 C1 -177.2(5) . . . . ? Ir1A N1 C2 C1 4.4(6) . . . . ? Ir1B N1 C2 C1 12.8(6) . . . . ? S2 C1 C2 N1 -33.7(6) . . . . ? S2 C1 C2 C3 147.9(5) . . . . ? N1 C2 C3 C4 -1.6(8) . . . . ? C1 C2 C3 C4 176.8(5) . . . . ? C2 C3 C4 C5 0.6(8) . . . . ? C3 C4 C5 C6 0.6(8) . . . . ? C2 N1 C6 C5 0.0(7) . . . . ? Ir1A N1 C6 C5 178.3(4) . . . . ? Ir1B N1 C6 C5 167.5(6) . . . . ? C2 N1 C6 C7 -178.8(4) . . . . ? Ir1A N1 C6 C7 -0.5(6) . . . . ? Ir1B N1 C6 C7 -11.3(8) . . . . ? C4 C5 C6 N1 -0.9(8) . . . . ? C4 C5 C6 C7 177.8(5) . . . . ? N1 C6 C7 S1 -25.3(6) . . . . ? C5 C6 C7 S1 156.0(4) . . . . ? C8 S1 C7 C6 -82.8(4) . . . . ? Ir1A S1 C7 C6 33.7(4) . . . . ? Ir1B S1 C7 C6 35.9(4) . . . . ? C7 S1 C8 C9 47.3(4) . . . . ? Ir1A S1 C8 C9 -56.1(4) . . . . ? Ir1B S1 C8 C9 -53.9(4) . . . . ? C7 S1 C8 C10 168.7(3) . . . . ? Ir1A S1 C8 C10 65.3(4) . . . . ? Ir1B S1 C8 C10 67.6(4) . . . . ? C7 S1 C8 C11 -74.1(4) . . . . ? Ir1A S1 C8 C11 -177.5(3) . . . . ? Ir1B S1 C8 C11 -175.3(3) . . . . ? C1 S2 C12 C13 -154.7(4) . . . . ? Ir1B S2 C12 C13 102.9(4) . . . . ? Ir1A S2 C12 C13 105.1(4) . . . . ? C1 S2 C12 C15 84.2(4) . . . . ? Ir1B S2 C12 C15 -18.2(5) . . . . ? Ir1A S2 C12 C15 -16.0(5) . . . . ? C1 S2 C12 C14 -37.8(5) . . . . ? Ir1B S2 C12 C14 -140.2(5) . . . . ? Ir1A S2 C12 C14 -138.1(4) . . . . ? N1 Ir1A C16 C17 171.8(5) . . . . ? S1 Ir1A C16 C17 103.3(4) . . . . ? S2 Ir1A C16 C17 -82.8(4) . . . . ? N1 Ir1A C16 C23 -71.5(7) . . . . ? C17 Ir1A C16 C23 116.7(6) . . . . ? S1 Ir1A C16 C23 -140.0(5) . . . . ? S2 Ir1A C16 C23 33.9(5) . . . . ? N1 Ir1A C16 Ir1B -91.6(9) . . . . ? C17 Ir1A C16 Ir1B 96.5(8) . . . . ? S1 Ir1A C16 Ir1B -160.1(7) . . . . ? S2 Ir1A C16 Ir1B 13.8(7) . . . . ? S2 Ir1B C16 C17 -81.4(5) . . . . ? N1 Ir1B C16 C17 119.2(11) . . . . ? S1 Ir1B C16 C17 96.2(4) . . . . ? S2 Ir1B C16 C23 37.6(6) . . . . ? N1 Ir1B C16 C23 -121.8(10) . . . . ? C17 Ir1B C16 C23 119.0(6) . . . . ? S1 Ir1B C16 C23 -144.8(4) . . . . ? S2 Ir1B C16 Ir1A -160.7(10) . . . . ? N1 Ir1B C16 Ir1A 39.9(11) . . . . ? C17 Ir1B C16 Ir1A -79.4(8) . . . . ? S1 Ir1B C16 Ir1A 16.9(6) . . . . ? C23 C16 C17 C18 0.6(11) . . . . ? Ir1A C16 C17 C18 113.3(7) . . . . ? Ir1B C16 C17 C18 100.0(8) . . . . ? C23 C16 C17 Ir1A -112.7(6) . . . . ? Ir1B C16 C17 Ir1A -13.3(4) . . . . ? C23 C16 C17 Ir1B -99.4(7) . . . . ? Ir1A C16 C17 Ir1B 13.3(4) . . . . ? N1 Ir1A C17 C16 -168.8(6) . . . . ? S1 Ir1A C17 C16 -78.2(3) . . . . ? S2 Ir1A C17 C16 104.2(3) . . . . ? N1 Ir1A C17 C18 70.4(10) . . . . ? C16 Ir1A C17 C18 -120.8(7) . . . . ? S1 Ir1A C17 C18 161.0(5) . . . . ? S2 Ir1A C17 C18 -16.6(5) . . . . ? N1 Ir1A C17 Ir1B 104.1(10) . . . . ? C16 Ir1A C17 Ir1B -87.1(8) . . . . ? S1 Ir1A C17 Ir1B -165.3(7) . . . . ? S2 Ir1A C17 Ir1B 17.1(7) . . . . ? S2 Ir1B C17 C16 114.0(6) . . . . ? N1 Ir1B C17 C16 -116.5(11) . . . . ? S1 Ir1B C17 C16 -76.5(4) . . . . ? S2 Ir1B C17 C18 -8.0(6) . . . . ? N1 Ir1B C17 C18 121.4(10) . . . . ? C16 Ir1B C17 C18 -122.1(6) . . . . ? S1 Ir1B C17 C18 161.5(5) . . . . ? S2 Ir1B C17 Ir1A -157.3(9) . . . . ? N1 Ir1B C17 Ir1A -27.8(8) . . . . ? C16 Ir1B C17 Ir1A 88.7(8) . . . . ? S1 Ir1B C17 Ir1A 12.2(6) . . . . ? C16 C17 C18 C19 79.5(9) . . . . ? Ir1A C17 C18 C19 166.6(5) . . . . ? Ir1B C17 C18 C19 159.3(5) . . . . ? C17 C18 C19 C20 -74.6(8) . . . . ? C18 C19 C20 C21 74.0(9) . . . . ? C19 C20 C21 C22 -103.7(8) . . . . ? C20 C21 C22 C23 51.7(8) . . . . ? C17 C16 C23 C22 -95.7(7) . . . . ? Ir1A C16 C23 C22 179.6(4) . . . . ? Ir1B C16 C23 C22 -175.8(5) . . . . ? C21 C22 C23 C16 55.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.350 _refine_diff_density_min -1.001 _refine_diff_density_rms 0.141