# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'P Braunstein' _publ_contact_author_email BRAUNSTEIN@CHIMIE.U-STRASBG.FR _publ_section_title ; Synthesis and characterisation of an unprecedented, figure-of-eight, dinuclear Iridium(I) dicarbene and Iridium(III) 'pincer' complexes ; loop_ _publ_author_name 'P Braunstein' 'Catherine S J Cazin' 'Helene Olivier-Bourbigou' 'Matthieu Raynal' 'Christophe Vallee' # Attachment '2-MeCN.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 689507' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H68 Ir2 N8, 2(F6 P), C2 H3 N' _chemical_formula_sum 'C54 H71 F12 Ir2 N9 P2' _chemical_formula_weight 1520.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' P P 0.1023 0.0942 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 46.8657(11) _cell_length_b 12.7769(4) _cell_length_c 20.6145(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.8690(10) _cell_angle_gamma 90.00 _cell_volume 11373.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.48 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6000 _exptl_absorpt_coefficient_mu 4.817 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30420 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -58 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.50 _reflns_number_total 11771 _reflns_number_gt 8008 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0469P)^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 11771 _refine_ls_number_parameters 713 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 0.675930(5) 0.16025(2) 0.990391(12) 0.02267(8) Uani 1 1 d . . . Ir2 Ir 0.599861(6) 0.73374(2) 0.778447(12) 0.02323(8) Uani 1 1 d . . . C1 C 0.68119(12) 0.0988(5) 0.9038(3) 0.0208(14) Uani 1 1 d . . . C2 C 0.69866(14) -0.0051(6) 0.8379(3) 0.0305(16) Uani 1 1 d . . . H2 H 0.7066 -0.0633 0.8234 0.037 Uiso 1 1 calc R . . C3 C 0.69130(14) 0.0863(5) 0.8046(3) 0.0310(16) Uani 1 1 d . . . H3 H 0.6932 0.1046 0.7628 0.037 Uiso 1 1 calc R . . C4 C 0.69890(14) -0.0809(5) 0.9506(3) 0.0305(15) Uani 1 1 d . . . H4A H 0.6849 -0.1391 0.9307 0.037 Uiso 1 1 calc R . . H4B H 0.6951 -0.0548 0.9907 0.037 Uiso 1 1 calc R . . C5 C 0.73216(15) -0.1197(6) 0.9754(4) 0.0405(18) Uani 1 1 d . . . H5A H 0.7354 -0.1524 0.9369 0.061 Uiso 1 1 calc R . . H5B H 0.7360 -0.1695 1.0127 0.061 Uiso 1 1 calc R . . H5C H 0.7461 -0.0616 0.9923 0.061 Uiso 1 1 calc R . . C6 C 0.67046(14) 0.2585(5) 0.8264(3) 0.0287(15) Uani 1 1 d . . . H6A H 0.6851 0.2923 0.8104 0.034 Uiso 1 1 calc R . . H6B H 0.6713 0.2948 0.8684 0.034 Uiso 1 1 calc R . . C7 C 0.63814(13) 0.2697(5) 0.7699(3) 0.0219(14) Uani 1 1 d . . . C8 C 0.62136(15) 0.1867(5) 0.7304(3) 0.0299(16) Uani 1 1 d . . . H8 H 0.6297 0.1195 0.7383 0.036 Uiso 1 1 calc R . . C9 C 0.59212(15) 0.2040(5) 0.6792(3) 0.0354(17) Uani 1 1 d . . . H9 H 0.5810 0.1478 0.6525 0.043 Uiso 1 1 calc R . . C10 C 0.57910(16) 0.3019(5) 0.6667(3) 0.0349(17) Uani 1 1 d . . . H10 H 0.5595 0.3121 0.6317 0.042 Uiso 1 1 calc R . . C11 C 0.59545(14) 0.3858(5) 0.7070(3) 0.0230(14) Uani 1 1 d . . . C12 C 0.62497(14) 0.3687(5) 0.7584(3) 0.0248(14) Uani 1 1 d . . . H12 H 0.6360 0.4246 0.7855 0.030 Uiso 1 1 calc R . . C13 C 0.58075(14) 0.4928(5) 0.6969(3) 0.0292(15) Uani 1 1 d . . . H13A H 0.5960 0.5450 0.6983 0.035 Uiso 1 1 calc R . . H13B H 0.5640 0.4961 0.6509 0.035 Uiso 1 1 calc R . . C14 C 0.57447(13) 0.6074(5) 0.7879(3) 0.0208(14) Uani 1 1 d . . . C15 C 0.54125(14) 0.5069(5) 0.8149(3) 0.0340(16) Uani 1 1 d . . . H15 H 0.5281 0.4842 0.8360 0.041 Uiso 1 1 calc R . . C16 C 0.54826(14) 0.4554(5) 0.7671(3) 0.0332(16) Uani 1 1 d . . . H16 H 0.5409 0.3901 0.7481 0.040 Uiso 1 1 calc R . . C17 C 0.55495(15) 0.6801(5) 0.8768(3) 0.0346(17) Uani 1 1 d . . . H17A H 0.5677 0.7396 0.8764 0.042 Uiso 1 1 calc R . . H17B H 0.5631 0.6509 0.9239 0.042 Uiso 1 1 calc R . . C18 C 0.52205(16) 0.7179(6) 0.8597(4) 0.052(2) Uani 1 1 d . . . H18A H 0.5136 0.7454 0.8127 0.077 Uiso 1 1 calc R . . H18B H 0.5222 0.7718 0.8923 0.077 Uiso 1 1 calc R . . H18C H 0.5095 0.6605 0.8633 0.077 Uiso 1 1 calc R . . C19 C 0.64239(14) 0.6711(5) 0.8388(3) 0.0275(15) Uani 1 1 d . . . C20 C 0.69185(15) 0.6126(6) 0.8750(4) 0.0399(18) Uani 1 1 d . . . H20 H 0.7106 0.5915 0.8739 0.048 Uiso 1 1 calc R . . C21 C 0.68480(14) 0.6189(5) 0.9319(3) 0.0331(16) Uani 1 1 d . . . H21 H 0.6978 0.6025 0.9779 0.040 Uiso 1 1 calc R . . C22 C 0.66413(17) 0.6474(6) 0.7456(4) 0.0435(19) Uani 1 1 d . . . H22A H 0.6757 0.7079 0.7408 0.052 Uiso 1 1 calc R . . H22B H 0.6427 0.6565 0.7135 0.052 Uiso 1 1 calc R . . C23 C 0.6769(2) 0.5509(7) 0.7247(4) 0.062(2) Uani 1 1 d . . . H23A H 0.6991 0.5508 0.7479 0.093 Uiso 1 1 calc R . . H23B H 0.6711 0.5506 0.6747 0.093 Uiso 1 1 calc R . . H23C H 0.6687 0.4898 0.7384 0.093 Uiso 1 1 calc R . . C24 C 0.63831(15) 0.6645(5) 0.9565(3) 0.0301(16) Uani 1 1 d . . . H24A H 0.6214 0.7133 0.9353 0.036 Uiso 1 1 calc R . . H24B H 0.6522 0.6946 1.0007 0.036 Uiso 1 1 calc R . . C25 C 0.62540(14) 0.5636(5) 0.9720(3) 0.0258(15) Uani 1 1 d . . . C26 C 0.61397(16) 0.5607(6) 1.0243(3) 0.0384(18) Uani 1 1 d . . . H26 H 0.6162 0.6190 1.0529 0.046 Uiso 1 1 calc R . . C27 C 0.59935(17) 0.4735(6) 1.0351(3) 0.0429(19) Uani 1 1 d . . . H27 H 0.5917 0.4735 1.0704 0.051 Uiso 1 1 calc R . . C28 C 0.59597(15) 0.3851(6) 0.9936(3) 0.0356(17) Uani 1 1 d . . . H28 H 0.5856 0.3267 1.0004 0.043 Uiso 1 1 calc R . . C29 C 0.60816(14) 0.3844(5) 0.9418(3) 0.0275(15) Uani 1 1 d . . . C30 C 0.62278(13) 0.4734(5) 0.9328(3) 0.0253(15) Uani 1 1 d . . . H30 H 0.6313 0.4729 0.8988 0.030 Uiso 1 1 calc R . . C31 C 0.60607(15) 0.2897(5) 0.8963(3) 0.0310(16) Uani 1 1 d . . . H31A H 0.5877 0.2966 0.8533 0.037 Uiso 1 1 calc R . . H31B H 0.6239 0.2897 0.8834 0.037 Uiso 1 1 calc R . . C32 C 0.62951(13) 0.1260(5) 0.9618(3) 0.0213(14) Uani 1 1 d . . . C33 C 0.58566(14) 0.0515(5) 0.9603(3) 0.0322(16) Uani 1 1 d . . . H33 H 0.5723 0.0034 0.9675 0.039 Uiso 1 1 calc R . . C34 C 0.57793(14) 0.1428(5) 0.9270(3) 0.0286(15) Uani 1 1 d . . . H34 H 0.5581 0.1706 0.9067 0.034 Uiso 1 1 calc R . . C35 C 0.63524(16) -0.0523(5) 1.0144(4) 0.0369(17) Uani 1 1 d . . . H35A H 0.6565 -0.0323 1.0423 0.044 Uiso 1 1 calc R . . H35B H 0.6356 -0.0980 0.9771 0.044 Uiso 1 1 calc R . . C36 C 0.62302(19) -0.1130(6) 1.0603(4) 0.055(2) Uani 1 1 d . . . H36A H 0.6229 -0.0690 1.0979 0.082 Uiso 1 1 calc R . . H36B H 0.6360 -0.1726 1.0795 0.082 Uiso 1 1 calc R . . H36C H 0.6023 -0.1361 1.0328 0.082 Uiso 1 1 calc R . . C37 C 0.67471(14) 0.2734(5) 1.0707(3) 0.0302(16) Uani 1 1 d . . . H37 H 0.6549 0.2906 1.0391 0.036 Uiso 1 1 calc R . . C38 C 0.67945(15) 0.1739(6) 1.0996(3) 0.0355(18) Uani 1 1 d . . . H38 H 0.6621 0.1311 1.0877 0.043 Uiso 1 1 calc R . . C39 C 0.70987(15) 0.1276(6) 1.1486(3) 0.0426(19) Uani 1 1 d . . . H39A H 0.7077 0.0522 1.1501 0.051 Uiso 1 1 calc R . . H39B H 0.7149 0.1545 1.1957 0.051 Uiso 1 1 calc R . . C40 C 0.73671(15) 0.1530(6) 1.1254(3) 0.0389(18) Uani 1 1 d . . . H40A H 0.7456 0.2201 1.1450 0.047 Uiso 1 1 calc R . . H40B H 0.7527 0.1004 1.1443 0.047 Uiso 1 1 calc R . . C41 C 0.72652(13) 0.1569(5) 1.0462(3) 0.0295(16) Uani 1 1 d . . . H41 H 0.7259 0.0946 1.0223 0.035 Uiso 1 1 calc R . . C42 C 0.71799(13) 0.2495(5) 1.0071(3) 0.0276(16) Uani 1 1 d . . . H42 H 0.7130 0.2446 0.9589 0.033 Uiso 1 1 calc R . . C43 C 0.71617(16) 0.3554(6) 1.0359(4) 0.0396(18) Uani 1 1 d . . . H43A H 0.7053 0.4021 0.9970 0.048 Uiso 1 1 calc R . . H43B H 0.7370 0.3824 1.0598 0.048 Uiso 1 1 calc R . . C44 C 0.69984(16) 0.3563(6) 1.0873(3) 0.0388(18) Uani 1 1 d . . . H44A H 0.7151 0.3451 1.1347 0.047 Uiso 1 1 calc R . . H44B H 0.6907 0.4247 1.0861 0.047 Uiso 1 1 calc R . . C45 C 0.5780(2) 0.8191(6) 0.6314(4) 0.054(2) Uani 1 1 d . . . H45A H 0.5623 0.8572 0.5937 0.065 Uiso 1 1 calc R . . H45B H 0.5856 0.7638 0.6101 0.065 Uiso 1 1 calc R . . C46 C 0.60486(19) 0.8939(6) 0.6702(4) 0.051(2) Uani 1 1 d . . . H46A H 0.6188 0.8961 0.6455 0.061 Uiso 1 1 calc R . . H46B H 0.5967 0.9639 0.6694 0.061 Uiso 1 1 calc R . . C47 C 0.62270(16) 0.8620(5) 0.7449(3) 0.0353(17) Uani 1 1 d . . . H47 H 0.6392 0.8165 0.7532 0.042 Uiso 1 1 calc R . . C48 C 0.61685(15) 0.8942(5) 0.8037(3) 0.0320(16) Uani 1 1 d . . . H48 H 0.6306 0.8718 0.8476 0.038 Uiso 1 1 calc R . . C49 C 0.59037(16) 0.9613(5) 0.8018(4) 0.0428(19) Uani 1 1 d . . . H49A H 0.5956 1.0340 0.7983 0.051 Uiso 1 1 calc R . . H49B H 0.5878 0.9531 0.8459 0.051 Uiso 1 1 calc R . . C50 C 0.55944(16) 0.9374(5) 0.7412(4) 0.0430(19) Uani 1 1 d . . . H50A H 0.5426 0.9629 0.7531 0.052 Uiso 1 1 calc R . . H50B H 0.5585 0.9735 0.6991 0.052 Uiso 1 1 calc R . . C51 C 0.55569(14) 0.8212(5) 0.7271(3) 0.0353(17) Uani 1 1 d . . . H51 H 0.5477 0.7813 0.7539 0.042 Uiso 1 1 calc R . . C52 C 0.56341(16) 0.7703(5) 0.6769(3) 0.0385(18) Uani 1 1 d . . . H52 H 0.5591 0.6991 0.6709 0.046 Uiso 1 1 calc R . . C53 C 0.52028(18) 0.1243(7) 0.5287(4) 0.049(2) Uani 1 1 d . . . C54 C 0.49733(18) 0.1753(6) 0.5469(4) 0.055(2) Uani 1 1 d . . . H54A H 0.4838 0.1239 0.5536 0.083 Uiso 1 1 calc R . . H54B H 0.4855 0.2221 0.5097 0.083 Uiso 1 1 calc R . . H54C H 0.5072 0.2143 0.5896 0.083 Uiso 1 1 calc R . . N1 N 0.69239(11) 0.0022(4) 0.8978(2) 0.0251(12) Uani 1 1 d . . . N2 N 0.68018(12) 0.1493(4) 0.8449(2) 0.0261(12) Uani 1 1 d . . . N3 N 0.56861(11) 0.5177(4) 0.7510(3) 0.0244(12) Uani 1 1 d . . . N4 N 0.55727(11) 0.6007(4) 0.8273(3) 0.0282(13) Uani 1 1 d . . . N5 N 0.66548(11) 0.6439(4) 0.8179(3) 0.0294(13) Uani 1 1 d . . . N6 N 0.61781(11) 0.0416(4) 0.9825(2) 0.0236(12) Uani 1 1 d . . . N7 N 0.60476(11) 0.1885(4) 0.9283(2) 0.0231(12) Uani 1 1 d . . . N8 N 0.65485(11) 0.6541(4) 0.9102(3) 0.0275(12) Uani 1 1 d . . . N9 N 0.53870(18) 0.0836(7) 0.5168(5) 0.094(3) Uani 1 1 d . . . P1 P 0.5000 0.1824(2) 0.7500 0.0316(6) Uani 1 2 d S . . P2 P 0.5000 0.5000 0.5000 0.0406(7) Uani 1 2 d S . . F1 F 0.48972(9) 0.0938(3) 0.69048(19) 0.0455(11) Uani 1 1 d . . . F2 F 0.48943(10) 0.2713(3) 0.6905(2) 0.0461(11) Uani 1 1 d . . . F3 F 0.46604(9) 0.1831(3) 0.7511(2) 0.0504(11) Uani 1 1 d . . . F4 F 0.47443(10) 0.4127(4) 0.4620(2) 0.0681(14) Uani 1 1 d . . . F5 F 0.50042(11) 0.4666(4) 0.5747(2) 0.0728(15) Uani 1 1 d . . . F6 F 0.47348(10) 0.5833(4) 0.4907(2) 0.0636(13) Uani 1 1 d . . . P3A P 0.72463(10) 0.2274(4) 0.6623(2) 0.0359(10) Uiso 0.50 1 d P A 1 F7A F 0.7340(3) 0.1300(10) 0.6297(6) 0.098(4) Uiso 0.50 1 d P A 1 F8A F 0.7180(3) 0.3184(13) 0.7112(7) 0.112(5) Uiso 0.50 1 d P A 1 F9A F 0.6964(2) 0.1580(8) 0.6528(5) 0.075(3) Uiso 0.50 1 d P A 1 F10A F 0.7401(3) 0.1693(9) 0.7328(6) 0.066(3) Uiso 0.50 1 d P A 1 F11A F 0.7082(2) 0.2710(9) 0.5799(5) 0.062(3) Uiso 0.50 1 d P A 1 F12A F 0.7552(4) 0.2830(13) 0.6714(8) 0.101(5) Uiso 0.50 1 d P A 1 P3B P 0.71620(10) 0.2709(4) 0.6551(2) 0.0402(11) Uiso 0.50 1 d P B 2 F7B F 0.7019(4) 0.1794(15) 0.6002(10) 0.165(7) Uiso 0.50 1 d P B 2 F8B F 0.7301(3) 0.3644(11) 0.6993(7) 0.106(4) Uiso 0.50 1 d P B 2 F9B F 0.6848(3) 0.2838(10) 0.6554(7) 0.108(4) Uiso 0.50 1 d P B 2 F10B F 0.7095(3) 0.3440(12) 0.5976(8) 0.124(5) Uiso 0.50 1 d P B 2 F11B F 0.7528(4) 0.2421(13) 0.6556(8) 0.107(6) Uiso 0.50 1 d P B 2 F12B F 0.7287(4) 0.2087(15) 0.7298(9) 0.133(6) Uiso 0.50 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01661(13) 0.03017(16) 0.02178(13) -0.00003(11) 0.00807(10) -0.00094(11) Ir2 0.02012(13) 0.02515(15) 0.02385(14) 0.00169(11) 0.00793(10) 0.00042(11) C1 0.013(3) 0.027(4) 0.024(3) 0.002(3) 0.009(3) -0.001(3) C2 0.030(4) 0.042(4) 0.023(3) -0.002(3) 0.014(3) 0.007(3) C3 0.033(4) 0.040(4) 0.020(3) -0.001(3) 0.011(3) 0.005(3) C4 0.023(3) 0.026(4) 0.045(4) 0.007(3) 0.016(3) 0.005(3) C5 0.029(4) 0.046(5) 0.046(4) 0.012(4) 0.015(3) 0.013(4) C6 0.029(4) 0.030(4) 0.029(3) 0.006(3) 0.014(3) 0.000(3) C7 0.022(3) 0.025(3) 0.024(3) 0.004(3) 0.014(3) 0.002(3) C8 0.040(4) 0.019(3) 0.032(4) -0.005(3) 0.015(3) -0.001(3) C9 0.030(4) 0.024(4) 0.041(4) -0.006(3) 0.002(3) -0.008(3) C10 0.032(4) 0.035(4) 0.028(4) -0.002(3) 0.001(3) 0.004(3) C11 0.027(3) 0.024(3) 0.020(3) -0.001(3) 0.012(3) -0.002(3) C12 0.029(4) 0.025(4) 0.022(3) -0.002(3) 0.012(3) -0.007(3) C13 0.029(4) 0.034(4) 0.029(3) 0.002(3) 0.015(3) -0.002(3) C14 0.015(3) 0.023(3) 0.022(3) 0.009(3) 0.005(3) 0.009(3) C15 0.019(3) 0.042(4) 0.040(4) 0.005(4) 0.010(3) -0.003(3) C16 0.025(4) 0.029(4) 0.045(4) 0.006(3) 0.013(3) -0.004(3) C17 0.030(4) 0.044(4) 0.031(4) -0.002(3) 0.014(3) 0.006(3) C18 0.041(5) 0.072(6) 0.042(4) 0.002(4) 0.016(4) 0.022(4) C19 0.016(3) 0.030(4) 0.034(4) -0.001(3) 0.007(3) -0.005(3) C20 0.022(4) 0.046(5) 0.049(4) 0.002(4) 0.011(3) 0.004(3) C21 0.022(4) 0.035(4) 0.039(4) 0.009(3) 0.008(3) 0.004(3) C22 0.037(4) 0.055(5) 0.044(4) 0.011(4) 0.022(4) 0.006(4) C23 0.081(6) 0.063(6) 0.070(6) 0.001(5) 0.060(5) 0.006(5) C24 0.031(4) 0.031(4) 0.025(3) -0.005(3) 0.008(3) 0.005(3) C25 0.025(3) 0.032(4) 0.021(3) 0.003(3) 0.009(3) 0.007(3) C26 0.055(5) 0.032(4) 0.030(4) 0.004(3) 0.019(4) 0.007(4) C27 0.057(5) 0.050(5) 0.036(4) 0.005(4) 0.034(4) 0.006(4) C28 0.033(4) 0.044(4) 0.039(4) 0.008(4) 0.024(3) 0.003(3) C29 0.025(3) 0.037(4) 0.021(3) 0.005(3) 0.010(3) 0.007(3) C30 0.025(3) 0.032(4) 0.022(3) 0.006(3) 0.013(3) 0.003(3) C31 0.025(4) 0.041(4) 0.029(4) 0.008(3) 0.013(3) 0.002(3) C32 0.024(3) 0.021(3) 0.019(3) -0.006(3) 0.008(3) 0.000(3) C33 0.017(3) 0.040(4) 0.045(4) -0.003(4) 0.018(3) -0.009(3) C34 0.020(3) 0.035(4) 0.033(4) -0.005(3) 0.014(3) -0.002(3) C35 0.042(4) 0.027(4) 0.047(4) 0.011(3) 0.023(4) 0.011(3) C36 0.068(6) 0.042(5) 0.075(6) 0.027(4) 0.052(5) 0.021(4) C37 0.021(3) 0.042(4) 0.023(3) -0.011(3) 0.004(3) -0.006(3) C38 0.031(4) 0.059(5) 0.020(3) -0.005(4) 0.013(3) -0.011(4) C39 0.044(5) 0.055(5) 0.020(3) 0.000(4) 0.003(3) -0.005(4) C40 0.027(4) 0.056(5) 0.028(4) -0.002(4) 0.005(3) 0.004(4) C41 0.011(3) 0.042(4) 0.028(3) -0.012(3) -0.001(3) -0.004(3) C42 0.012(3) 0.040(4) 0.027(3) -0.007(3) 0.004(3) -0.011(3) C43 0.031(4) 0.049(5) 0.046(4) -0.014(4) 0.021(3) -0.011(4) C44 0.035(4) 0.045(5) 0.032(4) -0.004(3) 0.010(3) 0.003(4) C45 0.083(6) 0.043(5) 0.034(4) 0.004(4) 0.021(4) 0.009(5) C46 0.069(6) 0.040(5) 0.054(5) 0.021(4) 0.036(4) 0.006(4) C47 0.037(4) 0.024(4) 0.046(4) 0.008(3) 0.019(3) 0.000(3) C48 0.030(4) 0.026(4) 0.035(4) 0.001(3) 0.007(3) -0.002(3) C49 0.058(5) 0.017(4) 0.046(4) -0.010(3) 0.012(4) -0.011(4) C50 0.049(5) 0.034(4) 0.049(4) 0.002(4) 0.021(4) 0.018(4) C51 0.021(4) 0.038(4) 0.036(4) 0.006(4) -0.001(3) 0.011(3) C52 0.045(4) 0.029(4) 0.024(4) 0.007(3) -0.005(3) 0.006(4) C53 0.031(4) 0.062(6) 0.049(5) -0.009(4) 0.012(4) -0.002(4) C54 0.044(5) 0.054(5) 0.078(6) -0.009(5) 0.035(5) 0.000(4) N1 0.022(3) 0.028(3) 0.028(3) 0.002(2) 0.013(2) 0.002(2) N2 0.028(3) 0.028(3) 0.025(3) 0.000(2) 0.013(2) 0.002(2) N3 0.021(3) 0.024(3) 0.028(3) 0.004(2) 0.009(2) 0.003(2) N4 0.023(3) 0.033(3) 0.031(3) 0.005(3) 0.013(2) 0.000(3) N5 0.017(3) 0.038(3) 0.033(3) 0.002(3) 0.010(2) 0.004(3) N6 0.018(3) 0.025(3) 0.027(3) 0.004(2) 0.008(2) -0.005(2) N7 0.015(3) 0.029(3) 0.024(3) 0.003(2) 0.008(2) 0.000(2) N8 0.022(3) 0.028(3) 0.030(3) 0.002(3) 0.007(2) 0.000(2) N9 0.051(5) 0.116(8) 0.119(7) -0.054(6) 0.037(5) 0.003(5) P1 0.0279(13) 0.0304(14) 0.0347(14) 0.000 0.0102(11) 0.000 P2 0.0336(15) 0.0516(18) 0.0318(14) 0.0046(14) 0.0076(12) 0.0124(14) F1 0.046(2) 0.037(2) 0.044(2) -0.008(2) 0.0078(19) 0.003(2) F2 0.056(3) 0.035(2) 0.047(2) 0.006(2) 0.020(2) 0.010(2) F3 0.034(2) 0.050(3) 0.074(3) -0.002(2) 0.028(2) 0.001(2) F4 0.046(3) 0.065(3) 0.069(3) -0.003(3) -0.004(2) -0.004(2) F5 0.082(4) 0.095(4) 0.045(3) 0.015(3) 0.028(3) 0.014(3) F6 0.045(3) 0.077(3) 0.063(3) 0.003(3) 0.015(2) 0.024(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 2.050(6) . ? Ir1 C32 2.068(6) . ? Ir1 C42 2.185(6) . ? Ir1 C41 2.197(6) . ? Ir1 C38 2.200(6) . ? Ir1 C37 2.215(6) . ? Ir2 C19 2.058(6) . ? Ir2 C14 2.059(6) . ? Ir2 C52 2.177(6) . ? Ir2 C48 2.187(6) . ? Ir2 C47 2.210(6) . ? Ir2 C51 2.225(6) . ? C1 N2 1.361(7) . ? C1 N1 1.365(7) . ? C2 C3 1.330(9) . ? C2 N1 1.380(7) . ? C2 H2 0.9300 . ? C3 N2 1.394(7) . ? C3 H3 0.9300 . ? C4 N1 1.466(7) . ? C4 C5 1.522(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N2 1.471(7) . ? C6 C7 1.517(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.381(8) . ? C7 C12 1.386(8) . ? C8 C9 1.385(8) . ? C8 H8 0.9300 . ? C9 C10 1.372(9) . ? C9 H9 0.9300 . ? C10 C11 1.389(9) . ? C10 H10 0.9300 . ? C11 C12 1.395(8) . ? C11 C13 1.509(8) . ? C12 H12 0.9300 . ? C13 N3 1.470(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N3 1.343(7) . ? C14 N4 1.352(7) . ? C15 C16 1.328(9) . ? C15 N4 1.384(8) . ? C15 H15 0.9300 . ? C16 N3 1.378(8) . ? C16 H16 0.9300 . ? C17 N4 1.472(8) . ? C17 C18 1.521(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N5 1.356(8) . ? C19 N8 1.374(8) . ? C20 C21 1.339(9) . ? C20 N5 1.394(8) . ? C20 H20 0.9300 . ? C21 N8 1.373(8) . ? C21 H21 0.9300 . ? C22 N5 1.467(8) . ? C22 C23 1.505(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N8 1.450(8) . ? C24 C25 1.511(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.379(8) . ? C25 C30 1.386(8) . ? C26 C27 1.370(10) . ? C26 H26 0.9300 . ? C27 C28 1.387(9) . ? C27 H27 0.9300 . ? C28 C29 1.393(8) . ? C28 H28 0.9300 . ? C29 C30 1.377(9) . ? C29 C31 1.511(9) . ? C30 H30 0.9300 . ? C31 N7 1.463(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 N6 1.351(7) . ? C32 N7 1.355(7) . ? C33 C34 1.330(9) . ? C33 N6 1.400(7) . ? C33 H33 0.9300 . ? C34 N7 1.377(7) . ? C34 H34 0.9300 . ? C35 N6 1.457(7) . ? C35 C36 1.498(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.385(9) . ? C37 C44 1.522(9) . ? C37 H37 0.9300 . ? C38 C39 1.511(9) . ? C38 H38 0.9300 . ? C39 C40 1.544(9) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.513(8) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.400(9) . ? C41 H41 0.9300 . ? C42 C43 1.493(9) . ? C42 H42 0.9300 . ? C43 C44 1.530(9) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C52 1.495(10) . ? C45 C46 1.534(10) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C47 1.496(9) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.403(9) . ? C47 H47 0.9300 . ? C48 C49 1.497(9) . ? C48 H48 0.9300 . ? C49 C50 1.531(9) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.510(9) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C52 1.385(9) . ? C51 H51 0.9300 . ? C52 H52 0.9300 . ? C53 N9 1.114(10) . ? C53 C54 1.427(10) . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? P1 F1 1.600(4) . ? P1 F1 1.600(4) 2_656 ? P1 F3 1.601(4) 2_656 ? P1 F3 1.601(4) . ? P1 F2 1.603(4) 2_656 ? P1 F2 1.603(4) . ? P2 F6 1.590(4) 5_666 ? P2 F6 1.590(4) . ? P2 F5 1.591(4) 5_666 ? P2 F5 1.591(4) . ? P2 F4 1.602(4) 5_666 ? P2 F4 1.602(4) . ? P3A F12A 1.544(16) . ? P3A F9A 1.542(11) . ? P3A F10A 1.540(12) . ? P3A F7A 1.557(13) . ? P3A F8A 1.647(16) . ? P3A F11A 1.664(10) . ? P3B F10B 1.444(14) . ? P3B F9B 1.481(14) . ? P3B F8B 1.490(14) . ? P3B F7B 1.583(19) . ? P3B F12B 1.626(18) . ? P3B F11B 1.749(17) . ? 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 C32 98.1(2) . . ? C1 Ir1 C42 86.1(2) . . ? C32 Ir1 C42 160.0(2) . . ? C1 Ir1 C41 88.8(2) . . ? C32 Ir1 C41 161.2(2) . . ? C42 Ir1 C41 37.3(2) . . ? C1 Ir1 C38 159.2(2) . . ? C32 Ir1 C38 87.7(2) . . ? C42 Ir1 C38 95.3(2) . . ? C41 Ir1 C38 80.2(2) . . ? C1 Ir1 C37 161.3(2) . . ? C32 Ir1 C37 91.2(2) . . ? C42 Ir1 C37 79.9(2) . . ? C41 Ir1 C37 87.6(2) . . ? C38 Ir1 C37 36.5(2) . . ? C19 Ir2 C14 95.6(2) . . ? C19 Ir2 C52 151.5(3) . . ? C14 Ir2 C52 89.6(2) . . ? C19 Ir2 C48 92.5(2) . . ? C14 Ir2 C48 152.0(2) . . ? C52 Ir2 C48 96.0(3) . . ? C19 Ir2 C47 90.2(2) . . ? C14 Ir2 C47 168.2(2) . . ? C52 Ir2 C47 80.5(3) . . ? C48 Ir2 C47 37.2(2) . . ? C19 Ir2 C51 170.5(2) . . ? C14 Ir2 C51 88.5(2) . . ? C52 Ir2 C51 36.6(2) . . ? C48 Ir2 C51 80.1(2) . . ? C47 Ir2 C51 87.3(3) . . ? N2 C1 N1 103.2(5) . . ? N2 C1 Ir1 128.4(4) . . ? N1 C1 Ir1 127.3(4) . . ? C3 C2 N1 107.4(6) . . ? C3 C2 H2 126.3 . . ? N1 C2 H2 126.3 . . ? C2 C3 N2 106.4(5) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N1 C4 C5 112.1(5) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 113.9(5) . . ? N2 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N2 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C12 119.1(6) . . ? C8 C7 C6 123.4(6) . . ? C12 C7 C6 117.5(5) . . ? C7 C8 C9 119.6(6) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 121.7(6) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.3(6) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 119.1(6) . . ? C10 C11 C13 120.0(6) . . ? C12 C11 C13 120.8(6) . . ? C7 C12 C11 121.1(6) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N3 C13 C11 112.5(5) . . ? N3 C13 H13A 109.1 . . ? C11 C13 H13A 109.1 . . ? N3 C13 H13B 109.1 . . ? C11 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? N3 C14 N4 104.3(5) . . ? N3 C14 Ir2 127.9(4) . . ? N4 C14 Ir2 127.5(5) . . ? C16 C15 N4 107.1(6) . . ? C16 C15 H15 126.5 . . ? N4 C15 H15 126.5 . . ? C15 C16 N3 106.6(6) . . ? C15 C16 H16 126.7 . . ? N3 C16 H16 126.7 . . ? N4 C17 C18 113.6(5) . . ? N4 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N4 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 N8 103.9(5) . . ? N5 C19 Ir2 127.8(4) . . ? N8 C19 Ir2 128.1(5) . . ? C21 C20 N5 106.4(6) . . ? C21 C20 H20 126.8 . . ? N5 C20 H20 126.8 . . ? C20 C21 N8 107.7(6) . . ? C20 C21 H21 126.2 . . ? N8 C21 H21 126.2 . . ? N5 C22 C23 113.6(6) . . ? N5 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? N5 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N8 C24 C25 114.9(5) . . ? N8 C24 H24A 108.5 . . ? C25 C24 H24A 108.5 . . ? N8 C24 H24B 108.5 . . ? C25 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C26 C25 C30 117.4(6) . . ? C26 C25 C24 119.9(6) . . ? C30 C25 C24 122.6(5) . . ? C27 C26 C25 121.3(7) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 120.4(6) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C29 119.7(7) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C30 C29 C28 118.2(6) . . ? C30 C29 C31 119.5(5) . . ? C28 C29 C31 122.3(6) . . ? C29 C30 C25 122.9(6) . . ? C29 C30 H30 118.6 . . ? C25 C30 H30 118.6 . . ? N7 C31 C29 115.6(5) . . ? N7 C31 H31A 108.4 . . ? C29 C31 H31A 108.4 . . ? N7 C31 H31B 108.4 . . ? C29 C31 H31B 108.4 . . ? H31A C31 H31B 107.4 . . ? N6 C32 N7 105.0(5) . . ? N6 C32 Ir1 126.1(4) . . ? N7 C32 Ir1 128.2(4) . . ? C34 C33 N6 106.9(6) . . ? C34 C33 H33 126.6 . . ? N6 C33 H33 126.6 . . ? C33 C34 N7 107.3(5) . . ? C33 C34 H34 126.3 . . ? N7 C34 H34 126.3 . . ? N6 C35 C36 115.3(6) . . ? N6 C35 H35A 108.5 . . ? C36 C35 H35A 108.5 . . ? N6 C35 H35B 108.5 . . ? C36 C35 H35B 108.5 . . ? H35A C35 H35B 107.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 C44 124.2(6) . . ? C38 C37 Ir1 71.1(4) . . ? C44 C37 Ir1 112.3(4) . . ? C38 C37 H37 117.9 . . ? C44 C37 H37 117.9 . . ? Ir1 C37 H37 86.5 . . ? C37 C38 C39 126.8(6) . . ? C37 C38 Ir1 72.3(3) . . ? C39 C38 Ir1 109.2(4) . . ? C37 C38 H38 116.6 . . ? C39 C38 H38 116.6 . . ? Ir1 C38 H38 88.4 . . ? C38 C39 C40 112.4(5) . . ? C38 C39 H39A 109.1 . . ? C40 C39 H39A 109.1 . . ? C38 C39 H39B 109.1 . . ? C40 C39 H39B 109.1 . . ? H39A C39 H39B 107.9 . . ? C41 C40 C39 112.8(5) . . ? C41 C40 H40A 109.0 . . ? C39 C40 H40A 109.0 . . ? C41 C40 H40B 109.0 . . ? C39 C40 H40B 109.0 . . ? H40A C40 H40B 107.8 . . ? C42 C41 C40 123.3(6) . . ? C42 C41 Ir1 70.9(3) . . ? C40 C41 Ir1 112.9(4) . . ? C42 C41 H41 118.4 . . ? C40 C41 H41 118.4 . . ? Ir1 C41 H41 86.2 . . ? C41 C42 C43 125.8(6) . . ? C41 C42 Ir1 71.8(3) . . ? C43 C42 Ir1 110.4(4) . . ? C41 C42 H42 117.1 . . ? C43 C42 H42 117.1 . . ? Ir1 C42 H42 87.7 . . ? C42 C43 C44 113.8(6) . . ? C42 C43 H43A 108.8 . . ? C44 C43 H43A 108.8 . . ? C42 C43 H43B 108.8 . . ? C44 C43 H43B 108.8 . . ? H43A C43 H43B 107.7 . . ? C37 C44 C43 113.0(5) . . ? C37 C44 H44A 109.0 . . ? C43 C44 H44A 109.0 . . ? C37 C44 H44B 109.0 . . ? C43 C44 H44B 109.0 . . ? H44A C44 H44B 107.8 . . ? C52 C45 C46 114.6(6) . . ? C52 C45 H45A 108.6 . . ? C46 C45 H45A 108.6 . . ? C52 C45 H45B 108.6 . . ? C46 C45 H45B 108.6 . . ? H45A C45 H45B 107.6 . . ? C47 C46 C45 112.5(6) . . ? C47 C46 H46A 109.1 . . ? C45 C46 H46A 109.1 . . ? C47 C46 H46B 109.1 . . ? C45 C46 H46B 109.1 . . ? H46A C46 H46B 107.8 . . ? C48 C47 C46 126.2(7) . . ? C48 C47 Ir2 70.5(4) . . ? C46 C47 Ir2 112.3(5) . . ? C48 C47 H47 116.9 . . ? C46 C47 H47 116.9 . . ? Ir2 C47 H47 87.1 . . ? C47 C48 C49 125.7(6) . . ? C47 C48 Ir2 72.3(4) . . ? C49 C48 Ir2 108.0(4) . . ? C47 C48 H48 117.2 . . ? C49 C48 H48 117.2 . . ? Ir2 C48 H48 89.7 . . ? C48 C49 C50 114.8(5) . . ? C48 C49 H49A 108.6 . . ? C50 C49 H49A 108.6 . . ? C48 C49 H49B 108.6 . . ? C50 C49 H49B 108.6 . . ? H49A C49 H49B 107.5 . . ? C51 C50 C49 110.8(5) . . ? C51 C50 H50A 109.5 . . ? C49 C50 H50A 109.5 . . ? C51 C50 H50B 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 108.1 . . ? C52 C51 C50 124.1(7) . . ? C52 C51 Ir2 69.8(4) . . ? C50 C51 Ir2 112.7(4) . . ? C52 C51 H51 117.9 . . ? C50 C51 H51 117.9 . . ? Ir2 C51 H51 87.6 . . ? C51 C52 C45 126.1(7) . . ? C51 C52 Ir2 73.6(4) . . ? C45 C52 Ir2 108.2(5) . . ? C51 C52 H52 116.9 . . ? C45 C52 H52 116.9 . . ? Ir2 C52 H52 88.1 . . ? N9 C53 C54 177.6(10) . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C1 N1 C2 111.5(5) . . ? C1 N1 C4 124.3(5) . . ? C2 N1 C4 124.1(5) . . ? C1 N2 C3 111.5(5) . . ? C1 N2 C6 125.5(5) . . ? C3 N2 C6 122.9(5) . . ? C14 N3 C16 111.4(5) . . ? C14 N3 C13 124.0(5) . . ? C16 N3 C13 124.4(5) . . ? C14 N4 C15 110.6(5) . . ? C14 N4 C17 126.5(5) . . ? C15 N4 C17 123.0(5) . . ? C19 N5 C20 111.1(5) . . ? C19 N5 C22 126.1(5) . . ? C20 N5 C22 122.7(6) . . ? C32 N6 C33 110.0(5) . . ? C32 N6 C35 125.1(5) . . ? C33 N6 C35 124.4(5) . . ? C32 N7 C34 110.8(5) . . ? C32 N7 C31 124.9(5) . . ? C34 N7 C31 124.3(5) . . ? C21 N8 C19 110.8(5) . . ? C21 N8 C24 123.8(5) . . ? C19 N8 C24 125.3(5) . . ? F1 P1 F1 89.9(3) . 2_656 ? F1 P1 F3 89.9(2) . 2_656 ? F1 P1 F3 90.6(2) 2_656 2_656 ? F1 P1 F3 90.6(2) . . ? F1 P1 F3 89.9(2) 2_656 . ? F3 P1 F3 179.4(4) 2_656 . ? F1 P1 F2 179.5(2) . 2_656 ? F1 P1 F2 90.18(19) 2_656 2_656 ? F3 P1 F2 89.7(2) 2_656 2_656 ? F3 P1 F2 89.9(2) . 2_656 ? F1 P1 F2 90.18(19) . . ? F1 P1 F2 179.5(2) 2_656 . ? F3 P1 F2 89.9(2) 2_656 . ? F3 P1 F2 89.7(2) . . ? F2 P1 F2 89.7(3) 2_656 . ? F6 P2 F6 180.0(3) 5_666 . ? F6 P2 F5 90.7(2) 5_666 5_666 ? F6 P2 F5 89.3(2) . 5_666 ? F6 P2 F5 89.3(2) 5_666 . ? F6 P2 F5 90.7(2) . . ? F5 P2 F5 180.0(4) 5_666 . ? F6 P2 F4 90.4(2) 5_666 5_666 ? F6 P2 F4 89.6(2) . 5_666 ? F5 P2 F4 90.7(3) 5_666 5_666 ? F5 P2 F4 89.3(3) . 5_666 ? F6 P2 F4 89.6(2) 5_666 . ? F6 P2 F4 90.4(2) . . ? F5 P2 F4 89.3(3) 5_666 . ? F5 P2 F4 90.7(3) . . ? F4 P2 F4 180.0(4) 5_666 . ? F12A P3A F9A 172.3(8) . . ? F12A P3A F10A 91.9(7) . . ? F9A P3A F10A 84.8(6) . . ? F12A P3A F7A 90.9(8) . . ? F9A P3A F7A 81.8(6) . . ? F10A P3A F7A 85.1(7) . . ? F12A P3A F8A 89.3(8) . . ? F9A P3A F8A 97.2(7) . . ? F10A P3A F8A 83.9(7) . . ? F7A P3A F8A 169.0(8) . . ? F12A P3A F11A 90.5(7) . . ? F9A P3A F11A 91.7(6) . . ? F10A P3A F11A 170.4(7) . . ? F7A P3A F11A 85.6(6) . . ? F8A P3A F11A 105.5(7) . . ? F10B P3B F9B 91.8(8) . . ? F10B P3B F8B 83.5(8) . . ? F9B P3B F8B 96.1(8) . . ? F10B P3B F7B 89.7(9) . . ? F9B P3B F7B 86.5(9) . . ? F8B P3B F7B 172.8(10) . . ? F10B P3B F12B 167.5(9) . . ? F9B P3B F12B 92.5(8) . . ? F8B P3B F12B 84.3(8) . . ? F7B P3B F12B 102.3(10) . . ? F10B P3B F11B 92.4(8) . . ? F9B P3B F11B 174.3(9) . . ? F8B P3B F11B 88.3(8) . . ? F7B P3B F11B 89.5(9) . . ? F12B P3B F11B 84.2(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.724 _refine_diff_density_min -1.836 _refine_diff_density_rms 0.179 # Attachment '7-MeCN.cif' data_import _database_code_depnum_ccdc_archive 'CCDC 689508' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 I2 Ir N5, C2 H3 N' _chemical_formula_sum 'C24 H31 I2 Ir N6' _chemical_formula_weight 849.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.0172(5) _cell_length_b 15.0514(7) _cell_length_c 16.7082(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2770.63(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4578 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.40 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 7.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13336 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_sigmaI/netI 0.0774 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5710 _reflns_number_gt 4562 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0532P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.018(7) _refine_ls_number_reflns 5710 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.83165(4) 0.43108(2) 0.14977(2) 0.02075(10) Uani 1 1 d . . . I1 I 0.99334(7) 0.30118(5) 0.12834(4) 0.03409(19) Uani 1 1 d . . . I2 I 0.66466(7) 0.56013(4) 0.16223(4) 0.02953(16) Uani 1 1 d . . . C1 C 0.9647(8) 0.5263(7) 0.1433(6) 0.028(2) Uani 1 1 d . . . C2 C 0.7180(9) 0.3420(6) 0.2041(5) 0.023(2) Uani 1 1 d . . . C3 C 0.6524(9) 0.2771(6) 0.3209(6) 0.027(2) Uani 1 1 d . . . H3 H 0.6449 0.2628 0.3748 0.032 Uiso 1 1 calc R . . C4 C 0.5874(10) 0.2447(7) 0.2584(6) 0.031(3) Uani 1 1 d . . . H4 H 0.5263 0.2023 0.2619 0.037 Uiso 1 1 calc R . . C5 C 0.8259(10) 0.3907(6) 0.3214(5) 0.022(2) Uani 1 1 d . . . C6 C 0.8811(8) 0.4436(7) 0.2636(6) 0.024(2) Uani 1 1 d . . . C7 C 0.9731(9) 0.5006(6) 0.2844(5) 0.022(2) Uani 1 1 d . . . C8 C 1.0086(10) 0.5080(6) 0.3628(6) 0.029(2) Uani 1 1 d . . . H8 H 1.0705 0.5470 0.3770 0.035 Uiso 1 1 calc R . . C9 C 0.9505(9) 0.4560(6) 0.4215(6) 0.029(2) Uani 1 1 d . . . H9 H 0.9741 0.4607 0.4748 0.035 Uiso 1 1 calc R . . C10 C 0.8575(9) 0.3975(6) 0.4002(5) 0.024(2) Uani 1 1 d . . . H10 H 0.8180 0.3637 0.4388 0.029 Uiso 1 1 calc R . . C11 C 1.0993(10) 0.6148(7) 0.2075(6) 0.030(3) Uani 1 1 d . . . H11 H 1.1458 0.6400 0.2480 0.036 Uiso 1 1 calc R . . C12 C 1.1013(10) 0.6380(8) 0.1292(6) 0.033(3) Uani 1 1 d . . . H12 H 1.1498 0.6813 0.1056 0.040 Uiso 1 1 calc R . . C13 C 0.7725(9) 0.3973(6) -0.0375(6) 0.024(2) Uani 1 1 d . . . C14 C 0.7557(11) 0.3764(7) -0.1217(6) 0.034(3) Uani 1 1 d . . . H14A H 0.7213 0.4267 -0.1487 0.051 Uiso 1 1 calc R . . H14B H 0.7021 0.3264 -0.1268 0.051 Uiso 1 1 calc R . . H14C H 0.8328 0.3622 -0.1453 0.051 Uiso 1 1 calc R . . C15 C 0.9914(10) 0.5874(6) 0.0055(5) 0.030(2) Uani 1 1 d . . . H15A H 0.9997 0.6481 -0.0133 0.036 Uiso 1 1 calc R . . H15B H 0.9083 0.5688 -0.0039 0.036 Uiso 1 1 calc R . . C16 C 1.0772(10) 0.5275(7) -0.0417(5) 0.031(3) Uani 1 1 d . . . H16A H 1.1603 0.5452 -0.0312 0.037 Uiso 1 1 calc R . . H16B H 1.0675 0.4667 -0.0235 0.037 Uiso 1 1 calc R . . C17 C 1.0536(9) 0.5316(8) -0.1309(6) 0.034(3) Uani 1 1 d . . . H17A H 0.9729 0.5087 -0.1416 0.041 Uiso 1 1 calc R . . H17B H 1.0552 0.5932 -0.1478 0.041 Uiso 1 1 calc R . . C18 C 1.1433(11) 0.4804(7) -0.1795(6) 0.043(3) Uani 1 1 d . . . H18A H 1.2228 0.5052 -0.1721 0.064 Uiso 1 1 calc R . . H18B H 1.1215 0.4836 -0.2350 0.064 Uiso 1 1 calc R . . H18C H 1.1434 0.4195 -0.1626 0.064 Uiso 1 1 calc R . . C19 C 0.5764(9) 0.2686(7) 0.1088(6) 0.028(2) Uani 1 1 d . . . H19A H 0.5292 0.2142 0.1099 0.034 Uiso 1 1 calc R . . H19B H 0.6429 0.2601 0.0716 0.034 Uiso 1 1 calc R . . C20 C 0.4968(10) 0.3435(6) 0.0790(5) 0.031(2) Uani 1 1 d . . . H20A H 0.4628 0.3267 0.0276 0.037 Uiso 1 1 calc R . . H20B H 0.5469 0.3957 0.0706 0.037 Uiso 1 1 calc R . . C21 C 0.3928(10) 0.3678(7) 0.1357(8) 0.041(3) Uani 1 1 d . . . H21A H 0.3436 0.3155 0.1457 0.049 Uiso 1 1 calc R . . H21B H 0.4261 0.3875 0.1864 0.049 Uiso 1 1 calc R . . C22 C 0.3134(11) 0.4410(8) 0.1007(7) 0.052(3) Uani 1 1 d . . . H22A H 0.3602 0.4945 0.0954 0.078 Uiso 1 1 calc R . . H22B H 0.2457 0.4517 0.1356 0.078 Uiso 1 1 calc R . . H22C H 0.2842 0.4230 0.0490 0.078 Uiso 1 1 calc R . . C23 C 1.1840(11) 0.2848(7) 0.4169(7) 0.045(3) Uani 1 1 d . . . C24 C 1.1575(12) 0.2878(7) 0.3307(6) 0.044(3) Uani 1 1 d . . . H24A H 1.1550 0.2284 0.3098 0.065 Uiso 1 1 calc R . . H24B H 1.2199 0.3209 0.3037 0.065 Uiso 1 1 calc R . . H24C H 1.0805 0.3161 0.3222 0.065 Uiso 1 1 calc R . . N1 N 1.0161(8) 0.5475(5) 0.2162(4) 0.0233(18) Uani 1 1 d . . . N2 N 1.0167(8) 0.5843(5) 0.0912(4) 0.0262(19) Uani 1 1 d . . . N3 N 0.7323(7) 0.3363(5) 0.2860(5) 0.0247(19) Uani 1 1 d . . . N4 N 0.6264(7) 0.2849(6) 0.1891(5) 0.028(2) Uani 1 1 d . . . N5 N 0.7890(7) 0.4132(5) 0.0271(5) 0.027(2) Uani 1 1 d . . . N6 N 1.2050(10) 0.2793(6) 0.4826(6) 0.056(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0257(2) 0.02048(18) 0.01609(17) 0.00025(15) -0.00029(17) -0.00053(19) I1 0.0416(4) 0.0316(4) 0.0290(4) -0.0023(3) 0.0003(3) 0.0085(4) I2 0.0331(4) 0.0262(3) 0.0293(3) -0.0028(3) -0.0019(3) 0.0043(4) C1 0.027(6) 0.029(5) 0.028(5) -0.011(5) 0.002(4) 0.007(4) C2 0.028(6) 0.029(6) 0.012(5) -0.005(4) -0.003(4) 0.004(5) C3 0.034(6) 0.016(5) 0.031(5) 0.002(4) 0.006(5) -0.002(5) C4 0.034(6) 0.026(6) 0.032(6) 0.004(5) 0.012(5) -0.002(5) C5 0.023(5) 0.018(5) 0.024(5) 0.004(4) -0.005(5) 0.002(5) C6 0.020(5) 0.024(6) 0.029(5) -0.007(4) 0.001(4) 0.001(4) C7 0.025(6) 0.024(5) 0.018(5) -0.007(4) -0.002(4) 0.002(4) C8 0.030(6) 0.032(6) 0.027(6) -0.001(4) 0.003(5) -0.004(5) C9 0.039(7) 0.031(6) 0.017(5) -0.004(4) -0.007(4) 0.003(5) C10 0.028(6) 0.030(5) 0.014(5) -0.003(4) 0.002(4) 0.007(5) C11 0.032(6) 0.028(6) 0.031(6) -0.009(5) 0.003(5) -0.010(5) C12 0.031(6) 0.034(6) 0.034(6) -0.009(5) -0.006(5) -0.002(5) C13 0.027(6) 0.024(5) 0.021(6) 0.000(4) -0.005(4) 0.007(5) C14 0.052(8) 0.034(6) 0.017(5) -0.004(4) -0.003(5) 0.006(6) C15 0.037(6) 0.033(6) 0.021(5) 0.009(4) 0.000(5) 0.003(5) C16 0.049(7) 0.024(6) 0.020(5) 0.002(4) 0.000(5) 0.004(5) C17 0.034(6) 0.046(7) 0.022(6) -0.004(5) 0.008(5) -0.003(6) C18 0.064(9) 0.032(6) 0.033(6) -0.008(5) 0.015(6) 0.007(6) C19 0.027(6) 0.026(6) 0.031(6) -0.006(4) -0.012(4) -0.001(5) C20 0.040(6) 0.028(5) 0.024(5) -0.006(4) -0.010(5) 0.000(6) C21 0.039(7) 0.025(6) 0.059(8) 0.003(5) 0.003(6) 0.006(5) C22 0.047(8) 0.047(8) 0.062(8) -0.002(6) -0.001(6) 0.015(7) C23 0.057(8) 0.030(6) 0.046(7) 0.006(5) 0.000(7) 0.005(6) C24 0.056(8) 0.041(7) 0.034(6) 0.005(5) -0.014(6) 0.013(7) N1 0.028(5) 0.017(4) 0.025(4) -0.003(3) 0.001(4) -0.002(4) N2 0.032(5) 0.024(4) 0.023(4) 0.006(3) 0.008(4) -0.004(4) N3 0.029(5) 0.023(4) 0.022(4) 0.005(3) 0.001(4) 0.000(4) N4 0.035(5) 0.031(5) 0.017(4) -0.002(4) -0.005(3) -0.004(4) N5 0.029(5) 0.025(5) 0.028(5) -0.002(4) -0.012(4) 0.005(4) N6 0.097(9) 0.039(6) 0.034(6) 0.010(5) -0.019(5) -0.010(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 C6 1.987(9) . ? Ir1 C2 2.047(10) . ? Ir1 C1 2.053(10) . ? Ir1 N5 2.120(8) . ? Ir1 I1 2.6692(8) . ? Ir1 I2 2.6835(8) . ? C1 N2 1.359(12) . ? C1 N1 1.381(12) . ? C2 N4 1.349(12) . ? C2 N3 1.381(12) . ? C3 C4 1.356(13) . ? C3 N3 1.381(12) . ? C3 H3 0.9300 . ? C4 N4 1.375(12) . ? C4 H4 0.9300 . ? C5 C10 1.366(12) . ? C5 C6 1.391(13) . ? C5 N3 1.443(12) . ? C6 C7 1.373(13) . ? C7 C8 1.371(13) . ? C7 N1 1.421(11) . ? C8 C9 1.410(13) . ? C8 H8 0.9300 . ? C9 C10 1.397(13) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.353(15) . ? C11 N1 1.375(12) . ? C11 H11 0.9300 . ? C12 N2 1.388(13) . ? C12 H12 0.9300 . ? C13 N5 1.119(12) . ? C13 C14 1.454(13) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N2 1.459(12) . ? C15 C16 1.526(13) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.515(13) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.493(14) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N4 1.471(11) . ? C19 C20 1.513(13) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.531(15) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.525(15) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N6 1.126(13) . ? C23 C24 1.470(14) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C6 Ir1 C2 78.8(4) . . ? C6 Ir1 C1 77.8(4) . . ? C2 Ir1 C1 156.6(4) . . ? C6 Ir1 N5 176.4(4) . . ? C2 Ir1 N5 102.1(3) . . ? C1 Ir1 N5 101.3(4) . . ? C6 Ir1 I1 90.8(3) . . ? C2 Ir1 I1 89.3(3) . . ? C1 Ir1 I1 91.6(3) . . ? N5 Ir1 I1 85.7(2) . . ? C6 Ir1 I2 92.6(3) . . ? C2 Ir1 I2 91.2(3) . . ? C1 Ir1 I2 89.3(3) . . ? N5 Ir1 I2 90.9(2) . . ? I1 Ir1 I2 176.55(2) . . ? N2 C1 N1 104.1(8) . . ? N2 C1 Ir1 141.5(8) . . ? N1 C1 Ir1 114.0(7) . . ? N4 C2 N3 103.3(8) . . ? N4 C2 Ir1 142.4(7) . . ? N3 C2 Ir1 114.2(7) . . ? C4 C3 N3 104.2(8) . . ? C4 C3 H3 127.9 . . ? N3 C3 H3 127.9 . . ? C3 C4 N4 109.0(9) . . ? C3 C4 H4 125.5 . . ? N4 C4 H4 125.5 . . ? C10 C5 C6 121.0(10) . . ? C10 C5 N3 128.2(9) . . ? C6 C5 N3 110.7(8) . . ? C7 C6 C5 120.3(9) . . ? C7 C6 Ir1 120.3(7) . . ? C5 C6 Ir1 119.4(7) . . ? C8 C7 C6 120.3(9) . . ? C8 C7 N1 129.0(9) . . ? C6 C7 N1 110.7(8) . . ? C7 C8 C9 119.3(10) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.3(9) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C5 C10 C9 118.7(9) . . ? C5 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 C11 N1 107.7(9) . . ? C12 C11 H11 126.1 . . ? N1 C11 H11 126.1 . . ? C11 C12 N2 106.3(10) . . ? C11 C12 H12 126.8 . . ? N2 C12 H12 126.8 . . ? N5 C13 C14 178.0(11) . . ? 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 . . ? N2 C15 C16 111.7(9) . . ? N2 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? N2 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 112.2(9) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 113.6(9) . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17B 108.8 . . ? C16 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C20 113.2(8) . . ? N4 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? N4 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.8 . . ? C19 C20 C21 114.0(9) . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20B 108.7 . . ? C21 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C22 C21 C20 111.4(10) . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N6 C23 C24 177.5(12) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C11 N1 C1 110.5(8) . . ? C11 N1 C7 132.4(8) . . ? C1 N1 C7 117.1(8) . . ? C1 N2 C12 111.4(8) . . ? C1 N2 C15 124.6(9) . . ? C12 N2 C15 124.0(8) . . ? C2 N3 C3 112.6(8) . . ? C2 N3 C5 116.9(8) . . ? C3 N3 C5 130.5(8) . . ? C2 N4 C4 110.9(8) . . ? C2 N4 C19 123.8(8) . . ? C4 N4 C19 125.3(9) . . ? C13 N5 Ir1 174.0(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.263 _refine_diff_density_min -2.816 _refine_diff_density_rms 0.253 # Attachment '8-MeCN.cif' data_raynal16 _database_code_depnum_ccdc_archive 'CCDC 689509' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 I2 Ir N5, C2 H3 N' _chemical_formula_sum 'C22 H27 I2 Ir N6' _chemical_formula_weight 821.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2130(6) _cell_length_b 11.3480(8) _cell_length_c 13.4060(10) _cell_angle_alpha 108.985(4) _cell_angle_beta 90.845(4) _cell_angle_gamma 100.681(4) _cell_volume 1298.13(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2854 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.981 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 7.541 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11389 _diffrn_reflns_av_R_equivalents 0.1025 _diffrn_reflns_av_sigmaI/netI 0.1109 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.99 _reflns_number_total 5087 _reflns_number_gt 2932 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0680P)^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 5087 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 0.77050(5) 0.27944(5) 0.18638(4) 0.03315(19) Uani 1 1 d . . . I1 I 0.81923(10) 0.04239(8) 0.12639(7) 0.0466(3) Uani 1 1 d . . . I2 I 0.72834(8) 0.51968(8) 0.25011(7) 0.0389(3) Uani 1 1 d . . . N1 N 0.9611(11) 0.3357(9) 0.0315(9) 0.044(3) Uani 1 1 d . . . N2 N 0.7452(11) 0.2608(10) -0.0605(8) 0.042(3) Uani 1 1 d . . . N3 N 0.9688(12) 0.3417(10) 0.3736(9) 0.048(3) Uani 1 1 d . . . N4 N 0.7595(12) 0.2710(10) 0.4248(8) 0.041(3) Uani 1 1 d . . . N5 N 0.5385(10) 0.2066(9) 0.1690(7) 0.031(2) Uani 1 1 d . . . N6 N 1.1655(17) -0.0017(19) 0.3871(12) 0.105(6) Uani 1 1 d . . . C1 C 0.8145(13) 0.2883(10) 0.0378(10) 0.036(3) Uani 1 1 d . . . C2 C 0.8232(14) 0.2958(11) 0.3402(10) 0.041(3) Uani 1 1 d . . . C3 C 0.9956(17) 0.3477(13) 0.4759(12) 0.051(4) Uani 1 1 d . . . H3 H 1.0872 0.3763 0.5148 0.061 Uiso 1 1 calc R . . C4 C 0.8683(17) 0.3058(14) 0.5102(10) 0.059(4) Uani 1 1 d . . . H4 H 0.8538 0.3003 0.5772 0.071 Uiso 1 1 calc R . . C5 C 1.0628(14) 0.3720(12) 0.2990(12) 0.045(4) Uani 1 1 d . . . C6 C 0.9862(12) 0.3475(11) 0.2060(10) 0.036(3) Uani 1 1 d . . . C7 C 1.0584(13) 0.3687(12) 0.1208(11) 0.044(4) Uani 1 1 d . . . C8 C 1.2080(14) 0.4232(14) 0.1314(13) 0.060(4) Uani 1 1 d . . . H8 H 1.2563 0.4415 0.0762 0.072 Uiso 1 1 calc R . . C9 C 1.2813(17) 0.4486(14) 0.2302(16) 0.072(6) Uani 1 1 d . . . H9 H 1.3824 0.4826 0.2391 0.087 Uiso 1 1 calc R . . C10 C 1.2150(14) 0.4271(13) 0.3150(13) 0.055(4) Uani 1 1 d . . . H10 H 1.2679 0.4478 0.3800 0.066 Uiso 1 1 calc R . . C11 C 0.9807(17) 0.3415(13) -0.0712(12) 0.057(4) Uani 1 1 d . . . H11 H 1.0683 0.3730 -0.0957 0.068 Uiso 1 1 calc R . . C12 C 0.8477(17) 0.2923(13) -0.1266(12) 0.053(4) Uani 1 1 d . . . H12 H 0.8281 0.2814 -0.1977 0.064 Uiso 1 1 calc R . . C13 C 0.4151(14) 0.1646(12) 0.1664(9) 0.039(3) Uani 1 1 d . . . C14 C 0.2550(13) 0.1178(11) 0.1668(10) 0.044(4) Uani 1 1 d . . . H14A H 0.2340 0.1097 0.2345 0.066 Uiso 1 1 calc R . . H14B H 0.2253 0.0363 0.1125 0.066 Uiso 1 1 calc R . . H14C H 0.2013 0.1768 0.1537 0.066 Uiso 1 1 calc R . . C15 C 0.5859(14) 0.2077(11) -0.0897(9) 0.038(3) Uani 1 1 d . . . H15 H 0.5557 0.1443 -0.0550 0.045 Uiso 1 1 calc R . . C16 C 0.5590(15) 0.1425(13) -0.2047(10) 0.052(4) Uani 1 1 d . . . H16A H 0.6000 0.1999 -0.2409 0.078 Uiso 1 1 calc R . . H16B H 0.4543 0.1152 -0.2234 0.078 Uiso 1 1 calc R . . H16C H 0.6052 0.0699 -0.2248 0.078 Uiso 1 1 calc R . . C17 C 0.4965(15) 0.3115(13) -0.0491(11) 0.054(4) Uani 1 1 d . . . H17A H 0.5263 0.3764 -0.0802 0.081 Uiso 1 1 calc R . . H17B H 0.5137 0.3480 0.0265 0.081 Uiso 1 1 calc R . . H17C H 0.3929 0.2754 -0.0679 0.081 Uiso 1 1 calc R . . C18 C 0.5951(14) 0.2182(13) 0.4224(11) 0.046(4) Uani 1 1 d . . . H18 H 0.5609 0.1577 0.3515 0.056 Uiso 1 1 calc R . . C19 C 0.578(2) 0.1482(16) 0.5000(15) 0.101(7) Uani 1 1 d . . . H19A H 0.6164 0.2058 0.5692 0.152 Uiso 1 1 calc R . . H19B H 0.6328 0.0807 0.4795 0.152 Uiso 1 1 calc R . . H19C H 0.4756 0.1131 0.5011 0.152 Uiso 1 1 calc R . . C20 C 0.5109(15) 0.3239(14) 0.4454(12) 0.061(4) Uani 1 1 d . . . H20A H 0.4071 0.2898 0.4438 0.092 Uiso 1 1 calc R . . H20B H 0.5268 0.3648 0.3929 0.092 Uiso 1 1 calc R . . H20C H 0.5448 0.3848 0.5141 0.092 Uiso 1 1 calc R . . C21 C 1.041(2) -0.0448(18) 0.3678(13) 0.078(5) Uani 1 1 d . . . C22 C 0.883(2) -0.1040(15) 0.3437(14) 0.101(7) Uani 1 1 d . . . H22A H 0.8570 -0.1627 0.3815 0.151 Uiso 1 1 calc R . . H22B H 0.8634 -0.1486 0.2690 0.151 Uiso 1 1 calc R . . H22C H 0.8246 -0.0393 0.3648 0.151 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 0.0187(3) 0.0451(3) 0.0335(3) 0.0132(2) 0.00442(19) 0.0009(2) I1 0.0357(5) 0.0471(5) 0.0535(6) 0.0131(5) 0.0075(4) 0.0066(4) I2 0.0245(5) 0.0442(5) 0.0464(5) 0.0142(4) 0.0075(4) 0.0043(4) N1 0.026(6) 0.046(7) 0.068(8) 0.030(6) 0.020(6) 0.005(5) N2 0.039(6) 0.056(7) 0.033(6) 0.020(5) 0.018(5) 0.009(5) N3 0.041(7) 0.045(7) 0.048(7) 0.006(6) -0.016(6) 0.005(6) N4 0.048(7) 0.059(7) 0.022(5) 0.021(5) -0.004(5) 0.015(6) N5 0.017(5) 0.048(6) 0.025(5) 0.007(5) -0.001(4) 0.010(5) N6 0.056(10) 0.194(19) 0.073(11) 0.055(12) 0.008(9) 0.025(11) C1 0.036(7) 0.034(7) 0.038(8) 0.010(6) 0.026(6) 0.008(6) C2 0.046(8) 0.032(7) 0.045(8) 0.013(6) 0.002(7) 0.005(6) C3 0.051(10) 0.049(9) 0.055(10) 0.014(7) -0.011(8) 0.021(8) C4 0.072(11) 0.081(11) 0.019(7) 0.005(7) -0.012(7) 0.025(9) C5 0.030(7) 0.040(8) 0.065(10) 0.011(7) 0.006(7) 0.017(6) C6 0.007(5) 0.046(7) 0.048(8) 0.012(6) -0.003(5) -0.002(5) C7 0.019(6) 0.052(8) 0.056(9) 0.010(7) 0.020(6) 0.004(6) C8 0.016(7) 0.072(10) 0.087(13) 0.021(9) 0.012(7) 0.007(7) C9 0.026(8) 0.047(9) 0.126(17) 0.009(10) 0.015(10) 0.001(7) C10 0.021(7) 0.055(9) 0.074(11) 0.003(8) -0.010(7) 0.005(7) C11 0.056(10) 0.062(10) 0.071(11) 0.040(8) 0.047(8) 0.024(8) C12 0.061(10) 0.063(9) 0.048(9) 0.034(8) 0.028(8) 0.014(8) C13 0.025(7) 0.060(9) 0.027(7) 0.015(6) 0.002(5) -0.002(7) C14 0.028(7) 0.044(8) 0.057(9) 0.017(7) 0.021(6) 0.001(6) C15 0.041(8) 0.045(8) 0.024(7) 0.007(6) 0.011(6) 0.009(6) C16 0.046(9) 0.073(10) 0.041(8) 0.020(7) 0.010(7) 0.021(8) C17 0.048(9) 0.063(9) 0.034(8) 0.002(7) -0.003(7) -0.003(8) C18 0.042(8) 0.069(10) 0.036(8) 0.024(7) 0.011(6) 0.017(7) C19 0.092(14) 0.141(17) 0.128(18) 0.110(15) 0.043(13) 0.043(13) C20 0.040(9) 0.075(10) 0.068(11) 0.025(9) -0.007(8) 0.007(8) C21 0.086(14) 0.106(15) 0.057(12) 0.042(11) 0.019(11) 0.025(13) C22 0.127(18) 0.077(13) 0.080(14) 0.008(10) 0.047(13) 0.003(12) _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 C6 1.974(10) . ? Ir1 C2 2.053(13) . ? Ir1 C1 2.069(12) . ? Ir1 N5 2.124(9) . ? Ir1 I1 2.6712(11) . ? Ir1 I2 2.6833(11) . ? N1 C1 1.372(14) . ? N1 C7 1.389(16) . ? N1 C11 1.413(17) . ? N2 C1 1.369(15) . ? N2 C12 1.383(15) . ? N2 C15 1.473(15) . ? N3 C2 1.358(15) . ? N3 C3 1.367(17) . ? N3 C5 1.417(17) . ? N4 C2 1.369(16) . ? N4 C4 1.414(15) . ? N4 C18 1.518(15) . ? N5 C13 1.144(13) . ? N6 C21 1.15(2) . ? C3 C4 1.33(2) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.344(17) . ? C5 C10 1.408(16) . ? C6 C7 1.395(17) . ? C7 C8 1.387(16) . ? C8 C9 1.40(2) . ? C8 H8 0.9300 . ? C9 C10 1.37(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.347(19) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.473(15) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.471(16) . ? C15 C17 1.522(18) . ? C15 H15 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.495(19) . ? C18 C20 1.499(19) . ? C18 H18 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.47(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C6 Ir1 C2 76.9(5) . . ? C6 Ir1 C1 78.5(5) . . ? C2 Ir1 C1 155.4(5) . . ? C6 Ir1 N5 178.7(4) . . ? C2 Ir1 N5 101.8(4) . . ? C1 Ir1 N5 102.8(4) . . ? C6 Ir1 I1 90.2(4) . . ? C2 Ir1 I1 88.6(3) . . ? C1 Ir1 I1 89.9(3) . . ? N5 Ir1 I1 89.9(3) . . ? C6 Ir1 I2 88.5(4) . . ? C2 Ir1 I2 90.3(3) . . ? C1 Ir1 I2 90.6(3) . . ? N5 Ir1 I2 91.4(3) . . ? I1 Ir1 I2 178.45(3) . . ? C1 N1 C7 118.4(11) . . ? C1 N1 C11 109.0(11) . . ? C7 N1 C11 132.6(11) . . ? C1 N2 C12 109.2(11) . . ? C1 N2 C15 125.0(10) . . ? C12 N2 C15 125.8(12) . . ? C2 N3 C3 111.1(12) . . ? C2 N3 C5 116.5(11) . . ? C3 N3 C5 132.4(12) . . ? C2 N4 C4 109.5(12) . . ? C2 N4 C18 122.6(10) . . ? C4 N4 C18 127.9(11) . . ? C13 N5 Ir1 174.6(10) . . ? N2 C1 N1 106.4(10) . . ? N2 C1 Ir1 140.9(8) . . ? N1 C1 Ir1 112.7(9) . . ? N3 C2 N4 104.7(11) . . ? N3 C2 Ir1 114.5(9) . . ? N4 C2 Ir1 140.8(9) . . ? C4 C3 N3 108.3(13) . . ? C4 C3 H3 125.8 . . ? N3 C3 H3 125.8 . . ? C3 C4 N4 106.4(13) . . ? C3 C4 H4 126.8 . . ? N4 C4 H4 126.8 . . ? C6 C5 C10 121.0(14) . . ? C6 C5 N3 111.1(11) . . ? C10 C5 N3 127.8(13) . . ? C5 C6 C7 120.3(11) . . ? C5 C6 Ir1 121.0(10) . . ? C7 C6 Ir1 118.7(9) . . ? C8 C7 N1 126.8(13) . . ? C8 C7 C6 121.4(13) . . ? N1 C7 C6 111.7(10) . . ? C7 C8 C9 115.6(15) . . ? C7 C8 H8 122.2 . . ? C9 C8 H8 122.2 . . ? C10 C9 C8 124.7(14) . . ? C10 C9 H9 117.7 . . ? C8 C9 H9 117.7 . . ? C9 C10 C5 116.8(14) . . ? C9 C10 H10 121.6 . . ? C5 C10 H10 121.6 . . ? C12 C11 N1 106.6(11) . . ? C12 C11 H11 126.7 . . ? N1 C11 H11 126.7 . . ? C11 C12 N2 108.7(13) . . ? C11 C12 H12 125.6 . . ? N2 C12 H12 125.6 . . ? N5 C13 C14 176.7(14) . . ? 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 . . ? C16 C15 N2 110.4(10) . . ? C16 C15 C17 112.6(12) . . ? N2 C15 C17 110.3(10) . . ? C16 C15 H15 107.8 . . ? N2 C15 H15 107.8 . . ? C17 C15 H15 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C20 113.9(13) . . ? C19 C18 N4 106.7(12) . . ? C20 C18 N4 110.0(11) . . ? C19 C18 H18 108.7 . . ? C20 C18 H18 108.7 . . ? N4 C18 H18 108.7 . . ? 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 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N6 C21 C22 178(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.439 _refine_diff_density_min -2.764 _refine_diff_density_rms 0.272 # Attachment '9-1_2CH2Cl2.cif' data_raynal4 _database_code_depnum_ccdc_archive 'CCDC 693227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 I2 Ir N4 O S, 0.5 (C H2 Cl2)' _chemical_formula_sum 'C22.5 H32 Cl I2 Ir N4 O S' _chemical_formula_weight 888.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.1064(2) _cell_length_b 14.8675(4) _cell_length_c 16.7840(4) _cell_angle_alpha 73.148(1) _cell_angle_beta 74.932(1) _cell_angle_gamma 64.757(1) _cell_volume 2795.84(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 22138 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 29.131 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 7.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.10817 _exptl_absorpt_correction_T_max 0.20484 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 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 38805 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 29.17 _reflns_number_total 15031 _reflns_number_gt 11369 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^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 15031 _refine_ls_number_parameters 614 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.1504(4) 0.0292(4) 0.3408(3) 0.0251(11) Uani 1 1 d . . . C2 C 0.4101(4) -0.1057(4) 0.1681(3) 0.0269(11) Uani 1 1 d . . . C3 C 0.4230(5) -0.1428(5) 0.0418(4) 0.0404(15) Uani 1 1 d . . . H3 H 0.4022 -0.1499 -0.0055 0.048 Uiso 1 1 calc R . . C4 C 0.5292(5) -0.1679(4) 0.0557(3) 0.0357(14) Uani 1 1 d . . . H4 H 0.5981 -0.1951 0.0190 0.043 Uiso 1 1 calc R . . C5 C 0.2303(4) -0.0630(4) 0.1288(4) 0.0318(12) Uani 1 1 d . . . C6 C 0.1926(4) -0.0296(4) 0.2038(3) 0.0263(11) Uani 1 1 d . . . C7 C 0.0764(4) 0.0157(4) 0.2316(4) 0.0297(12) Uani 1 1 d . . . C8 C -0.0035(5) 0.0289(5) 0.1840(4) 0.0398(15) Uani 1 1 d . . . H8 H -0.0830 0.0615 0.2022 0.048 Uiso 1 1 calc R . . C9 C 0.0358(5) -0.0067(5) 0.1093(4) 0.0474(17) Uani 1 1 d . . . H9 H -0.0182 -0.0004 0.0777 0.057 Uiso 1 1 calc R . . C10 C 0.1530(5) -0.0517(5) 0.0790(4) 0.0442(16) Uani 1 1 d . . . H10 H 0.1788 -0.0735 0.0268 0.053 Uiso 1 1 calc R . . C11 C -0.0437(4) 0.0871(4) 0.3612(4) 0.0334(13) Uani 1 1 d . . . H11 H -0.1191 0.1037 0.3528 0.040 Uiso 1 1 calc R . . C12 C -0.0140(4) 0.0997(4) 0.4256(4) 0.0339(13) Uani 1 1 d . . . H12 H -0.0645 0.1283 0.4717 0.041 Uiso 1 1 calc R . . C13 C 0.4378(5) -0.2856(4) 0.3706(4) 0.0392(14) Uani 1 1 d . . . H13A H 0.4688 -0.2645 0.4062 0.059 Uiso 1 1 calc R . . H13B H 0.4897 -0.2936 0.3170 0.059 Uiso 1 1 calc R . . H13C H 0.4301 -0.3504 0.3995 0.059 Uiso 1 1 calc R . . C14 C 0.2635(5) -0.2580(5) 0.2983(5) 0.0491(18) Uani 1 1 d . . . H14A H 0.2680 -0.3241 0.3342 0.074 Uiso 1 1 calc R . . H14B H 0.3160 -0.2680 0.2452 0.074 Uiso 1 1 calc R . . H14C H 0.1853 -0.2183 0.2864 0.074 Uiso 1 1 calc R . . C15 C 0.1701(5) 0.0654(4) 0.4710(4) 0.0324(12) Uani 1 1 d . . . H15A H 0.2465 0.0098 0.4671 0.039 Uiso 1 1 calc R . . H15B H 0.1301 0.0535 0.5294 0.039 Uiso 1 1 calc R . . C16 C 0.1841(6) 0.1656(5) 0.4518(5) 0.0510(17) Uani 1 1 d . . . H16A H 0.1078 0.2210 0.4572 0.061 Uiso 1 1 calc R . . H16B H 0.2223 0.1785 0.3928 0.061 Uiso 1 1 calc R . . C17 C 0.2549(7) 0.1668(6) 0.5115(5) 0.063(2) Uani 1 1 d . . . H17A H 0.3326 0.1140 0.5035 0.076 Uiso 1 1 calc R . . H17B H 0.2623 0.2335 0.4964 0.076 Uiso 1 1 calc R . . C18 C 0.2018(9) 0.1479(7) 0.6039(5) 0.089(3) Uani 1 1 d . . . H18A H 0.1245 0.1995 0.6122 0.133 Uiso 1 1 calc R . . H18B H 0.2486 0.1516 0.6390 0.133 Uiso 1 1 calc R . . H18C H 0.1982 0.0803 0.6201 0.133 Uiso 1 1 calc R . . C19 C 0.6202(4) -0.1594(5) 0.1663(4) 0.0363(14) Uani 1 1 d . . . H19A H 0.6828 -0.2249 0.1578 0.044 Uiso 1 1 calc R . . H19B H 0.5989 -0.1613 0.2277 0.044 Uiso 1 1 calc R . . C20 C 0.6616(5) -0.0742(5) 0.1242(5) 0.0478(17) Uani 1 1 d . . . H20A H 0.6846 -0.0738 0.0631 0.057 Uiso 1 1 calc R . . H20B H 0.5977 -0.0088 0.1309 0.057 Uiso 1 1 calc R . . C21 C 0.7608(5) -0.0818(6) 0.1587(5) 0.060(2) Uani 1 1 d . . . H21A H 0.7752 -0.0184 0.1343 0.072 Uiso 1 1 calc R . . H21B H 0.7392 -0.0868 0.2205 0.072 Uiso 1 1 calc R . . C22 C 0.8698(6) -0.1704(7) 0.1416(7) 0.085(3) Uani 1 1 d . . . H22A H 0.8576 -0.2339 0.1675 0.127 Uiso 1 1 calc R . . H22B H 0.9299 -0.1693 0.1654 0.127 Uiso 1 1 calc R . . H22C H 0.8929 -0.1658 0.0806 0.127 Uiso 1 1 calc R . . C23 C 0.6730(4) 0.3434(4) 0.1302(3) 0.0254(11) Uani 1 1 d . . . C24 C 0.6156(4) 0.3542(4) 0.0676(3) 0.0290(12) Uani 1 1 d . . . C25 C 0.6725(5) 0.3368(5) -0.0113(4) 0.0370(14) Uani 1 1 d . . . H25 H 0.6327 0.3442 -0.0541 0.044 Uiso 1 1 calc R . . C26 C 0.7918(5) 0.3077(5) -0.0260(4) 0.0469(16) Uani 1 1 d . . . H26 H 0.8328 0.2947 -0.0798 0.056 Uiso 1 1 calc R . . C27 C 0.8520(5) 0.2972(4) 0.0358(4) 0.0391(15) Uani 1 1 d . . . H27 H 0.9327 0.2771 0.0247 0.047 Uiso 1 1 calc R . . C28 C 0.7908(4) 0.3170(4) 0.1136(4) 0.0301(12) Uani 1 1 d . . . C29 C 0.4586(4) 0.3932(4) 0.1802(4) 0.0303(12) Uani 1 1 d . . . C30 C 0.4095(5) 0.3921(4) 0.0591(4) 0.0379(14) Uani 1 1 d . . . H30 H 0.4150 0.3879 0.0027 0.045 Uiso 1 1 calc R . . C31 C 0.3166(5) 0.4083(5) 0.1189(4) 0.0411(15) Uani 1 1 d . . . H31 H 0.2424 0.4187 0.1121 0.049 Uiso 1 1 calc R . . C32 C 0.2680(5) 0.4131(5) 0.2737(5) 0.0531(19) Uani 1 1 d D . . H32A H 0.3136 0.3726 0.3197 0.064 Uiso 1 1 calc R A 1 H32B H 0.2155 0.3803 0.2754 0.064 Uiso 1 1 calc R A 1 C33 C 0.1971(19) 0.5172(9) 0.2922(11) 0.070(5) Uani 0.50 1 d PD B 1 H33A H 0.1512 0.5605 0.2468 0.085 Uiso 0.50 1 calc PR B 1 H33B H 0.2468 0.5500 0.2963 0.085 Uiso 0.50 1 calc PR B 1 C34 C 0.1194(14) 0.5035(14) 0.3755(11) 0.089(6) Uani 0.50 1 d PD B 1 H34A H 0.1651 0.4578 0.4205 0.107 Uiso 0.50 1 calc PR B 1 H34B H 0.0672 0.4736 0.3707 0.107 Uiso 0.50 1 calc PR B 1 C35 C 0.0506(13) 0.6104(12) 0.3961(12) 0.076(4) Uani 0.50 1 d PD B 1 H35A H 0.1032 0.6380 0.4025 0.115 Uiso 0.50 1 calc PR B 1 H35B H -0.0028 0.6056 0.4488 0.115 Uiso 0.50 1 calc PR B 1 H35C H 0.0079 0.6554 0.3502 0.115 Uiso 0.50 1 calc PR B 1 C33B C 0.1962(17) 0.5245(9) 0.2621(10) 0.070(5) Uani 0.50 1 d PD B 2 H33C H 0.1742 0.5481 0.2052 0.085 Uiso 0.50 1 calc PR B 2 H33D H 0.2441 0.5605 0.2636 0.085 Uiso 0.50 1 calc PR B 2 C34B C 0.0878(12) 0.5566(18) 0.3261(9) 0.089(6) Uani 0.50 1 d PD B 2 H34C H 0.0476 0.6314 0.3129 0.107 Uiso 0.50 1 calc PR B 2 H34D H 0.0361 0.5253 0.3231 0.107 Uiso 0.50 1 calc PR B 2 C35B C 0.1178(15) 0.5236(15) 0.4133(9) 0.076(4) Uani 0.50 1 d PD B 2 H35D H 0.1359 0.4505 0.4329 0.115 Uiso 0.50 1 calc PR B 2 H35E H 0.0528 0.5605 0.4516 0.115 Uiso 0.50 1 calc PR B 2 H35F H 0.1842 0.5385 0.4123 0.115 Uiso 0.50 1 calc PR B 2 C36 C 0.7541(4) 0.3407(4) 0.2552(3) 0.0253(11) Uani 1 1 d . . . C37 C 0.9409(4) 0.2971(4) 0.1947(4) 0.0306(12) Uani 1 1 d . . . H37 H 1.0089 0.2781 0.1551 0.037 Uiso 1 1 calc R . . C38 C 0.9314(4) 0.3114(4) 0.2720(4) 0.0329(13) Uani 1 1 d . . . H38 H 0.9917 0.3050 0.2974 0.039 Uiso 1 1 calc R . . C39 C 0.7712(5) 0.3576(5) 0.3928(4) 0.0355(13) Uani 1 1 d . . . H39A H 0.8332 0.3225 0.4275 0.043 Uiso 1 1 calc R C 1 H39B H 0.7109 0.3299 0.4189 0.043 Uiso 1 1 calc R C 1 C40 C 0.7219(11) 0.4706(10) 0.3922(8) 0.039(2) Uani 0.50 1 d P D 1 H40A H 0.6803 0.4818 0.4491 0.047 Uiso 0.50 1 calc PR D 1 H40B H 0.6664 0.5065 0.3522 0.047 Uiso 0.50 1 calc PR D 1 C41 C 0.8147(12) 0.5165(11) 0.3668(10) 0.050(2) Uani 0.50 1 d P D 1 H41A H 0.8753 0.4763 0.4023 0.060 Uiso 0.50 1 calc PR D 1 H41B H 0.8499 0.5140 0.3072 0.060 Uiso 0.50 1 calc PR D 1 C42 C 0.762(7) 0.625(6) 0.378(4) 0.057(8) Uani 0.50 1 d P D 1 H42A H 0.6949 0.6625 0.3487 0.086 Uiso 0.50 1 calc PR D 1 H42B H 0.8176 0.6572 0.3541 0.086 Uiso 0.50 1 calc PR D 1 H42C H 0.7375 0.6265 0.4381 0.086 Uiso 0.50 1 calc PR D 1 C40B C 0.7946(11) 0.4440(10) 0.4083(8) 0.039(2) Uani 0.50 1 d P D 2 H40C H 0.7686 0.4480 0.4685 0.047 Uiso 0.50 1 calc PR D 2 H40D H 0.8780 0.4273 0.3963 0.047 Uiso 0.50 1 calc PR D 2 C41B C 0.7376(12) 0.5435(11) 0.3564(10) 0.050(2) Uani 0.50 1 d P D 2 H41C H 0.6546 0.5590 0.3719 0.060 Uiso 0.50 1 calc PR D 2 H41D H 0.7589 0.5347 0.2973 0.060 Uiso 0.50 1 calc PR D 2 C42B C 0.754(7) 0.636(6) 0.356(4) 0.057(8) Uani 0.50 1 d P D 2 H42D H 0.6970 0.6710 0.3996 0.086 Uiso 0.50 1 calc PR D 2 H42E H 0.7462 0.6818 0.3010 0.086 Uiso 0.50 1 calc PR D 2 H42F H 0.8310 0.6171 0.3687 0.086 Uiso 0.50 1 calc PR D 2 C43 C 0.5614(7) 0.1614(5) 0.2312(6) 0.070(3) Uani 1 1 d . . . H43A H 0.5818 0.1859 0.1708 0.105 Uiso 1 1 calc R . . H43B H 0.4781 0.1872 0.2467 0.105 Uiso 1 1 calc R . . H43C H 0.5920 0.0869 0.2440 0.105 Uiso 1 1 calc R . . C44 C 0.5534(9) 0.1674(6) 0.3919(5) 0.088(3) Uani 1 1 d . . . H44A H 0.5744 0.0937 0.4049 0.132 Uiso 1 1 calc R . . H44B H 0.4703 0.2017 0.3953 0.132 Uiso 1 1 calc R . . H44C H 0.5788 0.1862 0.4325 0.132 Uiso 1 1 calc R . . C45 C 0.8808(5) 0.5463(6) 0.0894(5) 0.0554(19) Uani 1 1 d . . . H45A H 0.9089 0.4832 0.0677 0.066 Uiso 1 1 calc R . . H45B H 0.8139 0.5470 0.1337 0.066 Uiso 1 1 calc R . . N1 N 0.0574(3) 0.0447(3) 0.3083(3) 0.0271(10) Uani 1 1 d . . . N2 N 0.1059(3) 0.0631(3) 0.4132(3) 0.0282(10) Uani 1 1 d . . . N3 N 0.3504(4) -0.1045(4) 0.1105(3) 0.0304(10) Uani 1 1 d . . . N4 N 0.5207(4) -0.1472(3) 0.1325(3) 0.0340(11) Uani 1 1 d . . . N5 N 0.4963(4) 0.3828(3) 0.0983(3) 0.0279(10) Uani 1 1 d . . . N6 N 0.3472(4) 0.4073(4) 0.1922(3) 0.0380(12) Uani 1 1 d . B . N7 N 0.8314(3) 0.3158(3) 0.1841(3) 0.0271(10) Uani 1 1 d . . . N8 N 0.8158(3) 0.3375(3) 0.3087(3) 0.0275(10) Uani 1 1 d . D . Cl1 Cl 0.98922(16) 0.54593(15) 0.13384(15) 0.0679(6) Uani 1 1 d . . . Cl2 Cl 0.83855(13) 0.65150(14) 0.00714(12) 0.0526(4) Uani 1 1 d . . . I1 I 0.46177(3) -0.05329(3) 0.36108(3) 0.03861(10) Uani 1 1 d . . . I2 I 0.29499(3) 0.14341(3) 0.18008(2) 0.03335(9) Uani 1 1 d . . . I3 I 0.46014(3) 0.42406(3) 0.39559(2) 0.03476(10) Uani 1 1 d . . . I4 I 0.56210(3) 0.56702(3) 0.18096(2) 0.03086(9) Uani 1 1 d . . . Ir1 Ir 0.304421(15) -0.042983(15) 0.270538(13) 0.02293(6) Uani 1 1 d . . . Ir2 Ir 0.587445(15) 0.370183(16) 0.243169(13) 0.02348(6) Uani 1 1 d . . . S1 S 0.30174(11) -0.19166(11) 0.35092(9) 0.0323(3) Uani 1 1 d . . . S2 S 0.61977(11) 0.20456(10) 0.28917(9) 0.0289(3) Uani 1 1 d . . . O1 O 0.2265(4) -0.1878(3) 0.4327(3) 0.0628(15) Uani 1 1 d . . . O2 O 0.7395(3) 0.1356(3) 0.2836(4) 0.0570(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(2) 0.021(3) 0.025(3) -0.005(2) -0.002(2) -0.011(2) C2 0.034(3) 0.020(3) 0.022(3) -0.001(2) 0.002(2) -0.012(2) C3 0.049(3) 0.042(4) 0.024(3) -0.012(3) -0.001(3) -0.012(3) C4 0.042(3) 0.036(3) 0.017(3) -0.009(2) 0.008(2) -0.009(3) C5 0.034(3) 0.037(3) 0.028(3) -0.010(3) -0.005(2) -0.014(2) C6 0.026(2) 0.032(3) 0.024(3) -0.006(2) -0.005(2) -0.014(2) C7 0.025(2) 0.030(3) 0.035(3) -0.008(3) -0.006(2) -0.010(2) C8 0.032(3) 0.048(4) 0.044(4) -0.011(3) -0.010(3) -0.016(3) C9 0.045(3) 0.063(5) 0.039(4) -0.012(3) -0.015(3) -0.019(3) C10 0.053(4) 0.056(4) 0.028(3) -0.011(3) -0.010(3) -0.021(3) C11 0.024(2) 0.030(3) 0.036(3) -0.003(3) -0.001(2) -0.006(2) C12 0.033(3) 0.024(3) 0.034(3) -0.007(2) 0.009(2) -0.008(2) C13 0.048(3) 0.028(3) 0.040(4) -0.004(3) -0.013(3) -0.011(3) C14 0.051(4) 0.030(3) 0.073(5) -0.005(3) -0.017(4) -0.022(3) C15 0.041(3) 0.033(3) 0.025(3) -0.005(2) -0.001(2) -0.020(3) C16 0.069(4) 0.046(4) 0.042(4) -0.006(3) -0.004(3) -0.029(4) C17 0.086(5) 0.061(5) 0.065(6) -0.018(4) -0.011(4) -0.047(4) C18 0.151(9) 0.091(7) 0.050(5) -0.022(5) -0.014(6) -0.066(7) C19 0.025(3) 0.040(3) 0.032(3) -0.003(3) 0.001(2) -0.007(2) C20 0.042(3) 0.043(4) 0.049(4) -0.001(3) 0.004(3) -0.019(3) C21 0.038(3) 0.058(5) 0.081(6) -0.021(4) 0.000(4) -0.017(3) C22 0.043(4) 0.075(6) 0.127(9) -0.028(6) -0.009(5) -0.012(4) C23 0.031(3) 0.029(3) 0.015(2) -0.007(2) 0.003(2) -0.013(2) C24 0.035(3) 0.030(3) 0.023(3) -0.006(2) -0.002(2) -0.015(2) C25 0.049(3) 0.040(3) 0.026(3) -0.011(3) 0.001(3) -0.022(3) C26 0.056(4) 0.060(4) 0.028(3) -0.021(3) 0.012(3) -0.028(3) C27 0.033(3) 0.040(4) 0.039(4) -0.014(3) 0.011(3) -0.014(3) C28 0.032(3) 0.028(3) 0.033(3) -0.010(2) 0.000(2) -0.015(2) C29 0.028(3) 0.033(3) 0.031(3) -0.011(3) -0.002(2) -0.010(2) C30 0.048(3) 0.034(3) 0.037(4) -0.003(3) -0.019(3) -0.015(3) C31 0.040(3) 0.048(4) 0.041(4) -0.013(3) -0.017(3) -0.014(3) C32 0.041(3) 0.083(5) 0.044(4) -0.027(4) -0.005(3) -0.023(4) C33 0.043(4) 0.114(8) 0.077(14) -0.070(8) -0.004(8) -0.022(5) C34 0.043(7) 0.171(18) 0.047(9) -0.046(10) -0.001(6) -0.023(9) C35 0.064(8) 0.079(9) 0.075(9) -0.011(8) 0.019(7) -0.037(7) C33B 0.043(4) 0.114(8) 0.077(14) -0.070(8) -0.004(8) -0.022(5) C34B 0.043(7) 0.171(18) 0.047(9) -0.046(10) -0.001(6) -0.023(9) C35B 0.064(8) 0.079(9) 0.075(9) -0.011(8) 0.019(7) -0.037(7) C36 0.023(2) 0.023(3) 0.030(3) -0.003(2) 0.000(2) -0.013(2) C37 0.023(2) 0.028(3) 0.038(3) 0.000(3) -0.004(2) -0.012(2) C38 0.027(3) 0.028(3) 0.045(4) 0.004(3) -0.013(3) -0.015(2) C39 0.036(3) 0.039(3) 0.036(3) -0.002(3) -0.010(3) -0.020(3) C40 0.043(5) 0.046(6) 0.031(5) -0.004(4) -0.007(4) -0.021(5) C41 0.050(6) 0.051(7) 0.050(6) -0.012(5) -0.010(6) -0.017(6) C42 0.061(9) 0.044(13) 0.07(2) -0.004(17) -0.023(18) -0.020(10) C40B 0.043(5) 0.046(6) 0.031(5) -0.004(4) -0.007(4) -0.021(5) C41B 0.050(6) 0.051(7) 0.050(6) -0.012(5) -0.010(6) -0.017(6) C42B 0.061(9) 0.044(13) 0.07(2) -0.004(17) -0.023(18) -0.020(10) C43 0.106(6) 0.044(4) 0.087(7) 0.008(4) -0.054(5) -0.045(4) C44 0.145(8) 0.051(5) 0.045(5) 0.000(4) 0.032(5) -0.049(5) C45 0.043(4) 0.063(5) 0.057(5) -0.002(4) -0.003(3) -0.026(3) N1 0.022(2) 0.026(2) 0.031(3) -0.005(2) 0.0009(18) -0.0102(18) N2 0.027(2) 0.023(2) 0.030(3) -0.002(2) -0.0017(19) -0.0085(18) N3 0.035(2) 0.035(3) 0.021(2) -0.008(2) 0.0008(19) -0.013(2) N4 0.030(2) 0.028(2) 0.034(3) -0.007(2) 0.001(2) -0.005(2) N5 0.033(2) 0.031(2) 0.023(2) -0.002(2) -0.0052(19) -0.017(2) N6 0.025(2) 0.053(3) 0.037(3) -0.014(3) -0.009(2) -0.010(2) N7 0.0191(19) 0.030(2) 0.030(3) -0.007(2) 0.0018(18) -0.0109(18) N8 0.023(2) 0.029(2) 0.028(3) -0.003(2) -0.0015(19) -0.0108(18) Cl1 0.0595(11) 0.0594(12) 0.0854(16) -0.0005(11) -0.0295(11) -0.0221(9) Cl2 0.0445(8) 0.0537(10) 0.0486(10) -0.0039(8) -0.0057(8) -0.0134(8) I1 0.03673(19) 0.0465(2) 0.0378(2) -0.00693(19) -0.00848(17) -0.02023(18) I2 0.03556(18) 0.02918(19) 0.0327(2) 0.00115(16) -0.00458(16) -0.01511(15) I3 0.03386(18) 0.0427(2) 0.0267(2) -0.01104(17) 0.00043(15) -0.01407(16) I4 0.03751(18) 0.02781(18) 0.02537(19) -0.00522(15) -0.00423(15) -0.01123(15) Ir1 0.02184(10) 0.02431(11) 0.02145(11) -0.00484(8) -0.00087(8) -0.00901(8) Ir2 0.02151(10) 0.02707(11) 0.02115(11) -0.00591(8) -0.00149(8) -0.00903(8) S1 0.0326(7) 0.0254(7) 0.0301(8) -0.0039(6) 0.0048(6) -0.0096(6) S2 0.0263(6) 0.0292(7) 0.0321(8) -0.0045(6) -0.0046(6) -0.0126(5) O1 0.073(3) 0.031(2) 0.046(3) -0.001(2) 0.030(2) -0.010(2) O2 0.031(2) 0.031(2) 0.105(4) -0.009(3) -0.015(2) -0.0087(19) _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 C1 N2 1.345(7) . ? C1 N1 1.367(7) . ? C1 Ir1 2.065(5) . ? C2 N4 1.357(6) . ? C2 N3 1.384(7) . ? C2 Ir1 2.082(5) . ? C3 C4 1.344(8) . ? C3 N3 1.381(7) . ? C3 H3 0.9500 . ? C4 N4 1.376(7) . ? C4 H4 0.9500 . ? C5 C6 1.379(7) . ? C5 C10 1.403(8) . ? C5 N3 1.409(7) . ? C6 C7 1.390(7) . ? C6 Ir1 1.979(5) . ? C7 C8 1.394(8) . ? C7 N1 1.403(7) . ? C8 C9 1.391(9) . ? C8 H8 0.9500 . ? C9 C10 1.408(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.323(8) . ? C11 N1 1.393(7) . ? C11 H11 0.9500 . ? C12 N2 1.405(6) . ? C12 H12 0.9500 . ? C13 S1 1.776(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 S1 1.778(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N2 1.455(7) . ? C15 C16 1.511(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.540(9) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N4 1.476(7) . ? C19 C20 1.507(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.506(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.503(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.379(7) . ? C23 C28 1.392(7) . ? C23 Ir2 1.991(5) . ? C24 C25 1.378(8) . ? C24 N5 1.425(6) . ? C25 C26 1.406(8) . ? C25 H25 0.9500 . ? C26 C27 1.396(9) . ? C26 H26 0.9500 . ? C27 C28 1.384(8) . ? C27 H27 0.9500 . ? C28 N7 1.410(7) . ? C29 N6 1.350(7) . ? C29 N5 1.366(7) . ? C29 Ir2 2.077(5) . ? C30 C31 1.343(9) . ? C30 N5 1.395(7) . ? C30 H30 0.9500 . ? C31 N6 1.384(7) . ? C31 H31 0.9500 . ? C32 N6 1.487(8) . ? C32 C33B 1.499(9) . ? C32 C33 1.502(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.518(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.548(10) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C33B C34B 1.525(9) . ? C33B H33C 0.9900 . ? C33B H33D 0.9900 . ? C34B C35B 1.502(9) . ? C34B H34C 0.9900 . ? C34B H34D 0.9900 . ? C35B H35D 0.9800 . ? C35B H35E 0.9800 . ? C35B H35F 0.9800 . ? C36 N8 1.335(7) . ? C36 N7 1.376(7) . ? C36 Ir2 2.089(5) . ? C37 C38 1.341(8) . ? C37 N7 1.390(6) . ? C37 H37 0.9500 . ? C38 N8 1.406(6) . ? C38 H38 0.9500 . ? C39 N8 1.445(7) . ? C39 C40 1.519(14) . ? C39 C40B 1.543(14) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.548(19) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.51(8) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C40B C41B 1.468(19) . ? C40B H40C 0.9900 . ? C40B H40D 0.9900 . ? C41B C42B 1.48(8) . ? C41B H41C 0.9900 . ? C41B H41D 0.9900 . ? C42B H42D 0.9800 . ? C42B H42E 0.9800 . ? C42B H42F 0.9800 . ? C43 S2 1.764(7) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 S2 1.764(7) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 Cl2 1.751(7) . ? C45 Cl1 1.766(7) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? I1 Ir1 2.7947(4) . ? I2 Ir1 2.7141(4) . ? I3 Ir2 2.7926(4) . ? I4 Ir2 2.7101(4) . ? Ir1 S1 2.2405(14) . ? Ir2 S2 2.2398(14) . ? S1 O1 1.468(4) . ? S2 O2 1.459(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 104.3(4) . . ? N2 C1 Ir1 141.9(4) . . ? N1 C1 Ir1 113.7(4) . . ? N4 C2 N3 103.0(4) . . ? N4 C2 Ir1 143.7(4) . . ? N3 C2 Ir1 113.3(3) . . ? C4 C3 N3 105.8(5) . . ? C4 C3 H3 127.1 . . ? N3 C3 H3 127.1 . . ? C3 C4 N4 108.0(5) . . ? C3 C4 H4 126.0 . . ? N4 C4 H4 126.0 . . ? C6 C5 C10 121.2(5) . . ? C6 C5 N3 111.8(5) . . ? C10 C5 N3 127.0(5) . . ? C5 C6 C7 120.2(5) . . ? C5 C6 Ir1 120.0(4) . . ? C7 C6 Ir1 119.8(4) . . ? C6 C7 C8 120.6(5) . . ? C6 C7 N1 110.7(4) . . ? C8 C7 N1 128.7(5) . . ? C9 C8 C7 118.4(5) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C8 C9 C10 122.2(6) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C5 C10 C9 117.3(6) . . ? C5 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? C12 C11 N1 106.5(5) . . ? C12 C11 H11 126.7 . . ? N1 C11 H11 126.7 . . ? C11 C12 N2 107.5(5) . . ? C11 C12 H12 126.3 . . ? N2 C12 H12 126.3 . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 111.9(5) . . ? N2 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? N2 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 111.8(6) . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 112.7(7) . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C20 111.8(5) . . ? N4 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? N4 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C21 C20 C19 113.6(6) . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 114.7(7) . . ? C22 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 120.0(5) . . ? C24 C23 Ir2 120.3(4) . . ? C28 C23 Ir2 119.6(4) . . ? C25 C24 C23 121.6(5) . . ? C25 C24 N5 128.1(5) . . ? C23 C24 N5 110.3(4) . . ? C24 C25 C26 117.4(6) . . ? C24 C25 H25 121.3 . . ? C26 C25 H25 121.3 . . ? C27 C26 C25 122.3(6) . . ? C27 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C28 C27 C26 118.0(5) . . ? C28 C27 H27 121.0 . . ? C26 C27 H27 121.0 . . ? C27 C28 C23 120.6(5) . . ? C27 C28 N7 128.4(5) . . ? C23 C28 N7 111.0(5) . . ? N6 C29 N5 103.7(5) . . ? N6 C29 Ir2 142.6(4) . . ? N5 C29 Ir2 113.4(4) . . ? C31 C30 N5 104.7(5) . . ? C31 C30 H30 127.6 . . ? N5 C30 H30 127.6 . . ? C30 C31 N6 108.4(5) . . ? C30 C31 H31 125.8 . . ? N6 C31 H31 125.8 . . ? N6 C32 C33B 101.8(7) . . ? N6 C32 C33 116.9(9) . . ? N6 C32 H32A 108.1 . . ? C33B C32 H32A 125.5 . . ? C33 C32 H32A 108.1 . . ? N6 C32 H32B 108.1 . . ? C33B C32 H32B 105.2 . . ? C33 C32 H32B 108.1 . . ? H32A C32 H32B 107.3 . . ? C32 C33 C34 106.9(11) . . ? C32 C33 H33A 110.3 . . ? C34 C33 H33A 110.3 . . ? C32 C33 H33B 110.3 . . ? C34 C33 H33B 110.3 . . ? H33A C33 H33B 108.6 . . ? C33 C34 C35 106.5(13) . . ? C33 C34 H34A 110.4 . . ? C35 C34 H34A 110.4 . . ? C33 C34 H34B 110.4 . . ? C35 C34 H34B 110.4 . . ? H34A C34 H34B 108.6 . . ? C32 C33B C34B 116.5(14) . . ? C32 C33B H33C 108.2 . . ? C34B C33B H33C 108.2 . . ? C32 C33B H33D 108.2 . . ? C34B C33B H33D 108.2 . . ? H33C C33B H33D 107.3 . . ? C35B C34B C33B 109.8(11) . . ? C35B C34B H34C 109.7 . . ? C33B C34B H34C 109.7 . . ? C35B C34B H34D 109.7 . . ? C33B C34B H34D 109.7 . . ? H34C C34B H34D 108.2 . . ? C34B C35B H35D 109.5 . . ? C34B C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? C34B C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? N8 C36 N7 105.0(4) . . ? N8 C36 Ir2 142.3(4) . . ? N7 C36 Ir2 112.6(4) . . ? C38 C37 N7 106.3(5) . . ? C38 C37 H37 126.8 . . ? N7 C37 H37 126.8 . . ? C37 C38 N8 107.4(5) . . ? C37 C38 H38 126.3 . . ? N8 C38 H38 126.3 . . ? N8 C39 C40 111.8(7) . . ? N8 C39 C40B 114.2(7) . . ? N8 C39 H39A 109.2 . . ? C40 C39 H39A 109.2 . . ? C40B C39 H39A 75.3 . . ? N8 C39 H39B 109.2 . . ? C40 C39 H39B 109.2 . . ? C40B C39 H39B 132.4 . . ? H39A C39 H39B 107.9 . . ? C39 C40 C41 112.7(10) . . ? C39 C40 H40A 109.1 . . ? C41 C40 H40A 109.1 . . ? C39 C40 H40B 109.1 . . ? C41 C40 H40B 109.1 . . ? H40A C40 H40B 107.8 . . ? C42 C41 C40 110(3) . . ? C42 C41 H41A 109.7 . . ? C40 C41 H41A 109.7 . . ? C42 C41 H41B 109.7 . . ? C40 C41 H41B 109.7 . . ? H41A C41 H41B 108.2 . . ? C41B C40B C39 113.3(10) . . ? C41B C40B H40C 108.9 . . ? C39 C40B H40C 108.9 . . ? C41B C40B H40D 108.9 . . ? C39 C40B H40D 108.9 . . ? H40C C40B H40D 107.7 . . ? C40B C41B C42B 123(2) . . ? C40B C41B H41C 106.7 . . ? C42B C41B H41C 106.7 . . ? C40B C41B H41D 106.7 . . ? C42B C41B H41D 106.7 . . ? H41C C41B H41D 106.6 . . ? C41B C42B H42D 109.5 . . ? C41B C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C41B C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? S2 C43 H43A 109.5 . . ? S2 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? S2 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? S2 C44 H44A 109.5 . . ? S2 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? S2 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? Cl2 C45 Cl1 111.9(4) . . ? Cl2 C45 H45A 109.2 . . ? Cl1 C45 H45A 109.2 . . ? Cl2 C45 H45B 109.2 . . ? Cl1 C45 H45B 109.2 . . ? H45A C45 H45B 107.9 . . ? C1 N1 C11 111.1(5) . . ? C1 N1 C7 118.0(4) . . ? C11 N1 C7 130.9(5) . . ? C1 N2 C12 110.6(5) . . ? C1 N2 C15 126.0(4) . . ? C12 N2 C15 123.4(5) . . ? C3 N3 C2 111.7(4) . . ? C3 N3 C5 131.2(5) . . ? C2 N3 C5 117.1(4) . . ? C2 N4 C4 111.4(5) . . ? C2 N4 C19 125.0(5) . . ? C4 N4 C19 123.2(5) . . ? C29 N5 C30 112.2(5) . . ? C29 N5 C24 118.3(4) . . ? C30 N5 C24 129.2(5) . . ? C29 N6 C31 110.9(5) . . ? C29 N6 C32 125.9(5) . . ? C31 N6 C32 123.0(5) . . ? C36 N7 C37 110.7(5) . . ? C36 N7 C28 118.6(4) . . ? C37 N7 C28 130.6(5) . . ? C36 N8 C38 110.5(5) . . ? C36 N8 C39 125.3(4) . . ? C38 N8 C39 124.2(5) . . ? C6 Ir1 C1 77.7(2) . . ? C6 Ir1 C2 77.8(2) . . ? C1 Ir1 C2 155.5(2) . . ? C6 Ir1 S1 92.96(17) . . ? C1 Ir1 S1 88.48(15) . . ? C2 Ir1 S1 94.43(15) . . ? C6 Ir1 I2 86.61(16) . . ? C1 Ir1 I2 87.71(14) . . ? C2 Ir1 I2 89.20(14) . . ? S1 Ir1 I2 176.18(4) . . ? C6 Ir1 I1 177.48(16) . . ? C1 Ir1 I1 102.07(15) . . ? C2 Ir1 I1 102.26(15) . . ? S1 Ir1 I1 89.54(4) . . ? I2 Ir1 I1 90.876(13) . . ? C23 Ir2 C29 77.7(2) . . ? C23 Ir2 C36 78.1(2) . . ? C29 Ir2 C36 155.6(2) . . ? C23 Ir2 S2 89.71(16) . . ? C29 Ir2 S2 91.99(16) . . ? C36 Ir2 S2 89.92(14) . . ? C23 Ir2 I4 87.14(15) . . ? C29 Ir2 I4 89.42(16) . . ? C36 Ir2 I4 87.35(14) . . ? S2 Ir2 I4 176.19(4) . . ? C23 Ir2 I3 175.44(15) . . ? C29 Ir2 I3 100.80(15) . . ? C36 Ir2 I3 103.23(15) . . ? S2 Ir2 I3 94.65(4) . . ? I4 Ir2 I3 88.550(13) . . ? O1 S1 C13 106.8(3) . . ? O1 S1 C14 106.3(3) . . ? C13 S1 C14 98.2(3) . . ? O1 S1 Ir1 116.61(19) . . ? C13 S1 Ir1 114.9(2) . . ? C14 S1 Ir1 112.2(2) . . ? O2 S2 C43 103.9(4) . . ? O2 S2 C44 106.3(4) . . ? C43 S2 C44 99.8(5) . . ? O2 S2 Ir2 115.90(19) . . ? C43 S2 Ir2 112.1(2) . . ? C44 S2 Ir2 117.1(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 N3 C3 C4 N4 1.4(7) . . . . ? C10 C5 C6 C7 0.4(9) . . . . ? N3 C5 C6 C7 178.6(5) . . . . ? C10 C5 C6 Ir1 -178.0(5) . . . . ? N3 C5 C6 Ir1 0.2(7) . . . . ? C5 C6 C7 C8 -0.6(9) . . . . ? Ir1 C6 C7 C8 177.8(5) . . . . ? C5 C6 C7 N1 -179.4(5) . . . . ? Ir1 C6 C7 N1 -1.0(7) . . . . ? C6 C7 C8 C9 1.6(9) . . . . ? N1 C7 C8 C9 -179.8(6) . . . . ? C7 C8 C9 C10 -2.5(11) . . . . ? C6 C5 C10 C9 -1.2(10) . . . . ? N3 C5 C10 C9 -179.1(6) . . . . ? C8 C9 C10 C5 2.3(11) . . . . ? N1 C11 C12 N2 -1.1(6) . . . . ? N2 C15 C16 C17 -178.4(5) . . . . ? C15 C16 C17 C18 -59.1(9) . . . . ? N4 C19 C20 C21 178.1(5) . . . . ? C19 C20 C21 C22 66.9(9) . . . . ? C28 C23 C24 C25 1.8(9) . . . . ? Ir2 C23 C24 C25 179.6(5) . . . . ? C28 C23 C24 N5 -179.2(5) . . . . ? Ir2 C23 C24 N5 -1.4(6) . . . . ? C23 C24 C25 C26 -0.2(9) . . . . ? N5 C24 C25 C26 -179.0(6) . . . . ? C24 C25 C26 C27 -0.6(10) . . . . ? C25 C26 C27 C28 -0.4(10) . . . . ? C26 C27 C28 C23 2.0(9) . . . . ? C26 C27 C28 N7 -177.1(6) . . . . ? C24 C23 C28 C27 -2.7(8) . . . . ? Ir2 C23 C28 C27 179.4(4) . . . . ? C24 C23 C28 N7 176.5(5) . . . . ? Ir2 C23 C28 N7 -1.3(6) . . . . ? N5 C30 C31 N6 -0.8(7) . . . . ? N6 C32 C33 C34 176.8(12) . . . . ? C33B C32 C33 C34 139(7) . . . . ? C32 C33 C34 C35 177.5(15) . . . . ? N6 C32 C33B C34B 167.2(15) . . . . ? C33 C32 C33B C34B -47(4) . . . . ? C32 C33B C34B C35B 59(3) . . . . ? N7 C37 C38 N8 0.8(6) . . . . ? N8 C39 C40 C41 -68.8(11) . . . . ? C40B C39 C40 C41 32.6(11) . . . . ? C39 C40 C41 C42 -173(2) . . . . ? N8 C39 C40B C41B 64.4(12) . . . . ? C40 C39 C40B C41B -29.9(11) . . . . ? C39 C40B C41B C42B -176(4) . . . . ? N2 C1 N1 C11 -0.6(6) . . . . ? Ir1 C1 N1 C11 175.9(4) . . . . ? N2 C1 N1 C7 -179.6(5) . . . . ? Ir1 C1 N1 C7 -3.1(6) . . . . ? C12 C11 N1 C1 1.1(6) . . . . ? C12 C11 N1 C7 180.0(5) . . . . ? C6 C7 N1 C1 2.7(7) . . . . ? C8 C7 N1 C1 -176.0(6) . . . . ? C6 C7 N1 C11 -176.1(5) . . . . ? C8 C7 N1 C11 5.3(10) . . . . ? N1 C1 N2 C12 -0.1(6) . . . . ? Ir1 C1 N2 C12 -174.9(5) . . . . ? N1 C1 N2 C15 -178.6(5) . . . . ? Ir1 C1 N2 C15 6.6(9) . . . . ? C11 C12 N2 C1 0.8(6) . . . . ? C11 C12 N2 C15 179.3(5) . . . . ? C16 C15 N2 C1 92.3(7) . . . . ? C16 C15 N2 C12 -85.9(6) . . . . ? C4 C3 N3 C2 -0.3(7) . . . . ? C4 C3 N3 C5 177.3(6) . . . . ? N4 C2 N3 C3 -0.8(6) . . . . ? Ir1 C2 N3 C3 177.5(4) . . . . ? N4 C2 N3 C5 -178.8(5) . . . . ? Ir1 C2 N3 C5 -0.5(6) . . . . ? C6 C5 N3 C3 -177.4(6) . . . . ? C10 C5 N3 C3 0.7(11) . . . . ? C6 C5 N3 C2 0.2(7) . . . . ? C10 C5 N3 C2 178.3(6) . . . . ? N3 C2 N4 C4 1.7(6) . . . . ? Ir1 C2 N4 C4 -175.8(5) . . . . ? N3 C2 N4 C19 175.7(5) . . . . ? Ir1 C2 N4 C19 -1.7(10) . . . . ? C3 C4 N4 C2 -2.0(7) . . . . ? C3 C4 N4 C19 -176.2(5) . . . . ? C20 C19 N4 C2 -97.0(7) . . . . ? C20 C19 N4 C4 76.3(7) . . . . ? N6 C29 N5 C30 1.0(6) . . . . ? Ir2 C29 N5 C30 176.1(4) . . . . ? N6 C29 N5 C24 -172.5(5) . . . . ? Ir2 C29 N5 C24 2.6(6) . . . . ? C31 C30 N5 C29 -0.2(7) . . . . ? C31 C30 N5 C24 172.5(6) . . . . ? C25 C24 N5 C29 178.0(6) . . . . ? C23 C24 N5 C29 -0.9(7) . . . . ? C25 C24 N5 C30 5.7(10) . . . . ? C23 C24 N5 C30 -173.2(5) . . . . ? N5 C29 N6 C31 -1.5(7) . . . . ? Ir2 C29 N6 C31 -174.1(6) . . . . ? N5 C29 N6 C32 173.9(6) . . . . ? Ir2 C29 N6 C32 1.3(11) . . . . ? C30 C31 N6 C29 1.5(8) . . . . ? C30 C31 N6 C32 -174.0(6) . . . . ? C33B C32 N6 C29 105.7(12) . . . . ? C33 C32 N6 C29 94.0(13) . . . . ? C33B C32 N6 C31 -79.5(12) . . . . ? C33 C32 N6 C31 -91.1(13) . . . . ? N8 C36 N7 C37 0.2(6) . . . . ? Ir2 C36 N7 C37 179.8(3) . . . . ? N8 C36 N7 C28 -177.3(4) . . . . ? Ir2 C36 N7 C28 2.4(6) . . . . ? C38 C37 N7 C36 -0.6(6) . . . . ? C38 C37 N7 C28 176.4(5) . . . . ? C27 C28 N7 C36 178.4(6) . . . . ? C23 C28 N7 C36 -0.8(7) . . . . ? C27 C28 N7 C37 1.5(10) . . . . ? C23 C28 N7 C37 -177.7(5) . . . . ? N7 C36 N8 C38 0.3(6) . . . . ? Ir2 C36 N8 C38 -179.2(5) . . . . ? N7 C36 N8 C39 -179.6(5) . . . . ? Ir2 C36 N8 C39 1.0(9) . . . . ? C37 C38 N8 C36 -0.7(6) . . . . ? C37 C38 N8 C39 179.2(5) . . . . ? C40 C39 N8 C36 -83.7(8) . . . . ? C40B C39 N8 C36 -122.6(7) . . . . ? C40 C39 N8 C38 96.5(7) . . . . ? C40B C39 N8 C38 57.5(8) . . . . ? C5 C6 Ir1 C1 177.9(5) . . . . ? C7 C6 Ir1 C1 -0.5(4) . . . . ? C5 C6 Ir1 C2 -0.4(5) . . . . ? C7 C6 Ir1 C2 -178.8(5) . . . . ? C5 C6 Ir1 S1 -94.3(5) . . . . ? C7 C6 Ir1 S1 87.3(4) . . . . ? C5 C6 Ir1 I2 89.6(5) . . . . ? C7 C6 Ir1 I2 -88.9(4) . . . . ? N2 C1 Ir1 C6 176.4(7) . . . . ? N1 C1 Ir1 C6 1.9(4) . . . . ? N2 C1 Ir1 C2 -179.6(5) . . . . ? N1 C1 Ir1 C2 5.9(7) . . . . ? N2 C1 Ir1 S1 83.0(6) . . . . ? N1 C1 Ir1 S1 -91.5(4) . . . . ? N2 C1 Ir1 I2 -96.6(6) . . . . ? N1 C1 Ir1 I2 88.9(4) . . . . ? N2 C1 Ir1 I1 -6.2(7) . . . . ? N1 C1 Ir1 I1 179.3(3) . . . . ? N4 C2 Ir1 C6 177.7(7) . . . . ? N3 C2 Ir1 C6 0.4(4) . . . . ? N4 C2 Ir1 C1 173.7(5) . . . . ? N3 C2 Ir1 C1 -3.6(7) . . . . ? N4 C2 Ir1 S1 -90.2(7) . . . . ? N3 C2 Ir1 S1 92.5(4) . . . . ? N4 C2 Ir1 I2 91.0(7) . . . . ? N3 C2 Ir1 I2 -86.3(4) . . . . ? N4 C2 Ir1 I1 0.3(7) . . . . ? N3 C2 Ir1 I1 -177.0(3) . . . . ? C24 C23 Ir2 C29 2.1(4) . . . . ? C28 C23 Ir2 C29 179.9(5) . . . . ? C24 C23 Ir2 C36 -175.8(5) . . . . ? C28 C23 Ir2 C36 2.0(4) . . . . ? C24 C23 Ir2 S2 94.2(4) . . . . ? C28 C23 Ir2 S2 -88.0(4) . . . . ? C24 C23 Ir2 I4 -87.9(4) . . . . ? C28 C23 Ir2 I4 89.9(4) . . . . ? N6 C29 Ir2 C23 169.7(7) . . . . ? N5 C29 Ir2 C23 -2.4(4) . . . . ? N6 C29 Ir2 C36 174.7(6) . . . . ? N5 C29 Ir2 C36 2.5(8) . . . . ? N6 C29 Ir2 S2 80.5(7) . . . . ? N5 C29 Ir2 S2 -91.7(4) . . . . ? N6 C29 Ir2 I4 -103.1(7) . . . . ? N5 C29 Ir2 I4 84.8(4) . . . . ? N6 C29 Ir2 I3 -14.7(7) . . . . ? N5 C29 Ir2 I3 173.2(4) . . . . ? N8 C36 Ir2 C23 177.2(7) . . . . ? N7 C36 Ir2 C23 -2.3(4) . . . . ? N8 C36 Ir2 C29 172.3(5) . . . . ? N7 C36 Ir2 C29 -7.2(7) . . . . ? N8 C36 Ir2 S2 -93.1(6) . . . . ? N7 C36 Ir2 S2 87.5(4) . . . . ? N8 C36 Ir2 I4 89.6(6) . . . . ? N7 C36 Ir2 I4 -89.9(4) . . . . ? N8 C36 Ir2 I3 1.7(6) . . . . ? N7 C36 Ir2 I3 -177.8(3) . . . . ? C6 Ir1 S1 O1 -96.8(3) . . . . ? C1 Ir1 S1 O1 -19.2(3) . . . . ? C2 Ir1 S1 O1 -174.9(3) . . . . ? I1 Ir1 S1 O1 82.9(3) . . . . ? C6 Ir1 S1 C13 137.1(3) . . . . ? C1 Ir1 S1 C13 -145.2(3) . . . . ? C2 Ir1 S1 C13 59.1(3) . . . . ? I1 Ir1 S1 C13 -43.1(2) . . . . ? C6 Ir1 S1 C14 26.1(3) . . . . ? C1 Ir1 S1 C14 103.7(3) . . . . ? C2 Ir1 S1 C14 -52.0(3) . . . . ? I1 Ir1 S1 C14 -154.2(2) . . . . ? C23 Ir2 S2 O2 58.7(3) . . . . ? C29 Ir2 S2 O2 136.4(3) . . . . ? C36 Ir2 S2 O2 -19.3(3) . . . . ? I3 Ir2 S2 O2 -122.6(3) . . . . ? C23 Ir2 S2 C43 -60.2(4) . . . . ? C29 Ir2 S2 C43 17.5(4) . . . . ? C36 Ir2 S2 C43 -138.2(4) . . . . ? I3 Ir2 S2 C43 118.5(3) . . . . ? C23 Ir2 S2 C44 -174.5(4) . . . . ? C29 Ir2 S2 C44 -96.9(4) . . . . ? C36 Ir2 S2 C44 107.4(4) . . . . ? I3 Ir2 S2 C44 4.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.509 _refine_diff_density_min -2.480 _refine_diff_density_rms 0.205