# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Paul Chirik' _publ_contact_author_address ; Department of Chemistry and Chemical Biology Cornell University G-50 Baker Laboratory Ithaca NY 14850 UNITED STATES OF AMERICA ; _publ_contact_author_email PC92@CORNELL.EDU _publ_section_title ; Synthesis of a B-diiminate iridium tetrahydride for C-H bond activation. ; loop_ _publ_author_name 'Paul Chirik' 'Wesley H. Bernskoetter' 'Emil B. Lobkovsky' data_wb1 _database_code_depnum_ccdc_archive 'CCDC 225948' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H62 Ir N4' _chemical_formula_weight 791.14 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8311(3) _cell_length_b 12.1110(4) _cell_length_c 18.4635(5) _cell_angle_alpha 84.647(1) _cell_angle_beta 84.485(1) _cell_angle_gamma 75.017(1) _cell_volume 1893.95(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 814 _exptl_absorpt_coefficient_mu 3.556 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.4151 _exptl_absorpt_correction_T_max 0.7175 _exptl_absorpt_process_details ? _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 'Bruker 1K CCD area detector' _diffrn_measurement_method '0.3 deg. 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 40861 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 33.14 _reflns_number_total 13735 _reflns_number_gt 11285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. There is 1/2 of disordered n-pentane molecule in the asymmetric unit. ; _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^)+(0.0266P)^2^+1.9569P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13735 _refine_ls_number_parameters 454 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.395 _refine_ls_shift/su_mean 0.019 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 -0.272577(13) 0.166446(10) -0.213776(6) 0.01845(3) Uani 1 1 d . . . N1 N -0.1398(3) 0.1011(2) -0.30444(13) 0.0214(5) Uani 1 1 d . . . N2 N -0.1578(3) 0.2946(2) -0.21895(14) 0.0241(5) Uani 1 1 d . . . N3 N -0.3980(3) 0.2327(2) -0.13152(15) 0.0265(5) Uani 1 1 d . . . N4 N -0.4714(4) 0.2736(3) -0.08447(17) 0.0379(7) Uani 1 1 d . . . C1 C -0.4508(4) 0.0748(2) -0.22178(16) 0.0231(6) Uani 1 1 d . . . H1A H -0.4440 0.0443 -0.2708 0.028 Uiso 1 1 calc R . . C2 C -0.3343(4) 0.0085(3) -0.17800(17) 0.0285(7) Uani 1 1 d . . . H2A H -0.2655 -0.0578 -0.2035 0.034 Uiso 1 1 calc R . . C3 C -0.3620(6) -0.0210(3) -0.09716(18) 0.0461(10) Uani 1 1 d . A . H3A H -0.4395 0.0439 -0.0751 0.055 Uiso 1 1 calc R . . H3B H -0.2624 -0.0332 -0.0735 0.055 Uiso 1 1 calc R . . C4 C -0.4233(7) -0.1297(3) -0.0833(2) 0.0514(13) Uani 1 1 d . . . H4B H -0.401(5) -0.153(4) -0.043(2) 0.040(12) Uiso 1 1 d . . . H4A H -0.345(4) -0.188(3) -0.095(2) 0.025(9) Uiso 1 1 d . . . C5 C -0.5768(9) -0.1341(6) -0.1345(5) 0.0295(19) Uani 0.533(13) 1 d P A 1 H5A H -0.5359 -0.1386 -0.1863 0.035 Uiso 0.533(13) 1 calc PR A 1 H5D H -0.6086 -0.2060 -0.1192 0.035 Uiso 0.533(13) 1 calc PR A 1 C5A C -0.5750(9) -0.1118(7) -0.0883(4) 0.032(2) Uani 0.467(13) 1 d P A 2 H5B H -0.6300 -0.0406 -0.0648 0.038 Uiso 0.467(13) 1 calc PR A 2 H5C H -0.6113 -0.1759 -0.0612 0.038 Uiso 0.467(13) 1 calc PR A 2 C6 C -0.7259(7) -0.0336(5) -0.1301(3) 0.0274(16) Uani 0.526(10) 1 d P A 1 H6A H -0.8215 -0.0627 -0.1265 0.033 Uiso 0.526(10) 1 calc PR A 1 H6B H -0.7280 0.0092 -0.0867 0.033 Uiso 0.526(10) 1 calc PR A 1 C6A C -0.6203(10) -0.1013(7) -0.1667(5) 0.0304(19) Uani 0.474(10) 1 d P A 2 H6C H -0.6884 -0.1533 -0.1710 0.037 Uiso 0.474(10) 1 calc PR A 2 H6D H -0.5240 -0.1262 -0.1993 0.037 Uiso 0.474(10) 1 calc PR A 2 C7 C -0.7200(6) 0.0398(5) -0.1957(2) 0.0528(13) Uani 1 1 d . . . H7B H -0.715(4) 0.021(3) -0.2425(19) 0.015(8) Uiso 1 1 d . . . H7A H -0.824(8) 0.073(5) -0.184(3) 0.10(2) Uiso 1 1 d . . . C8 C -0.6185(4) 0.1248(3) -0.19366(18) 0.0336(7) Uani 1 1 d . A . H8A H -0.6632 0.1957 -0.2238 0.040 Uiso 1 1 calc R . . H8B H -0.6204 0.1454 -0.1429 0.040 Uiso 1 1 calc R . . C9 C 0.0582(4) 0.0924(4) -0.4107(2) 0.0400(9) Uani 1 1 d . . . H9A H 0.0187 0.0271 -0.4204 0.060 Uiso 1 1 calc R . . H9B H 0.1713 0.0666 -0.4049 0.060 Uiso 1 1 calc R . . H9C H 0.0389 0.1507 -0.4516 0.060 Uiso 1 1 calc R . . C10 C -0.0263(3) 0.1433(3) -0.34110(17) 0.0260(6) Uani 1 1 d . . . C11 C 0.0232(3) 0.2364(3) -0.32202(18) 0.0291(7) Uani 1 1 d . . . H11A H 0.1112 0.2524 -0.3508 0.035 Uiso 1 1 calc R . . C12 C -0.0394(3) 0.3093(3) -0.26621(18) 0.0285(7) Uani 1 1 d . . . C13 C 0.0321(5) 0.4086(4) -0.2610(3) 0.0415(9) Uani 1 1 d . . . H13C H -0.036(5) 0.467(4) -0.265(2) 0.029(11) Uiso 1 1 d . . . H13B H 0.072(6) 0.407(4) -0.215(3) 0.062(14) Uiso 1 1 d . . . H13A H 0.111(6) 0.405(4) -0.300(3) 0.052(13) Uiso 1 1 d . . . C14 C -0.1779(3) 0.0095(3) -0.33826(16) 0.0226(6) Uani 1 1 d . . . C15 C -0.2890(4) 0.0393(3) -0.39138(16) 0.0252(6) Uani 1 1 d . . . C16 C -0.3290(4) -0.0496(3) -0.42227(18) 0.0341(7) Uani 1 1 d . . . H16A H -0.4049 -0.0315 -0.4575 0.041 Uiso 1 1 calc R . . C17 C -0.2610(5) -0.1625(3) -0.4028(2) 0.0436(9) Uani 1 1 d . . . H17A H -0.2907 -0.2213 -0.4242 0.052 Uiso 1 1 calc R . . C18 C -0.1493(5) -0.1908(3) -0.3520(2) 0.0406(9) Uani 1 1 d . . . H18A H -0.1011 -0.2691 -0.3397 0.049 Uiso 1 1 calc R . . C19 C -0.1063(4) -0.1059(3) -0.31855(17) 0.0286(7) Uani 1 1 d . . . C20 C -0.3617(4) 0.1629(3) -0.41778(18) 0.0299(7) Uani 1 1 d . . . H20A H -0.3149 0.2140 -0.3922 0.036 Uiso 1 1 calc R . . C21 C -0.3256(5) 0.1831(4) -0.5000(2) 0.0454(9) Uani 1 1 d . . . H21A H -0.2116 0.1622 -0.5114 0.068 Uiso 1 1 calc R . . H21B H -0.3683 0.2641 -0.5151 0.068 Uiso 1 1 calc R . . H21C H -0.3740 0.1358 -0.5261 0.068 Uiso 1 1 calc R . . C22 C -0.5402(5) 0.1973(4) -0.4012(2) 0.0497(11) Uani 1 1 d . . . H22A H -0.5651 0.1861 -0.3486 0.075 Uiso 1 1 calc R . . H22B H -0.5884 0.1497 -0.4271 0.075 Uiso 1 1 calc R . . H22C H -0.5812 0.2781 -0.4174 0.075 Uiso 1 1 calc R . . C23 C 0.0234(4) -0.1420(3) -0.26581(19) 0.0355(8) Uani 1 1 d . . . H23A H 0.0225 -0.0739 -0.2389 0.043 Uiso 1 1 calc R . . C24 C 0.0006(6) -0.2388(4) -0.2093(3) 0.0541(11) Uani 1 1 d . . . H24A H -0.1021 -0.2151 -0.1821 0.081 Uiso 1 1 calc R . . H24B H 0.0838 -0.2554 -0.1754 0.081 Uiso 1 1 calc R . . H24C H 0.0054 -0.3077 -0.2342 0.081 Uiso 1 1 calc R . . C25 C 0.1846(5) -0.1791(5) -0.3071(3) 0.0617(13) Uani 1 1 d . . . H25A H 0.2004 -0.1173 -0.3429 0.093 Uiso 1 1 calc R . . H25B H 0.1902 -0.2479 -0.3323 0.093 Uiso 1 1 calc R . . H25C H 0.2666 -0.1959 -0.2726 0.093 Uiso 1 1 calc R . . C26 C -0.2186(4) 0.3834(3) -0.1683(2) 0.0338(8) Uani 1 1 d . . . C27 C -0.1571(4) 0.3724(4) -0.1003(2) 0.0424(10) Uani 1 1 d . . . C28 C -0.2313(6) 0.4546(4) -0.0505(3) 0.0634(15) Uani 1 1 d . . . H28A H -0.1930 0.4489 -0.0036 0.076 Uiso 1 1 calc R . . C29 C -0.3581(7) 0.5430(4) -0.0684(3) 0.079(2) Uani 1 1 d . . . H29A H -0.4071 0.5969 -0.0338 0.094 Uiso 1 1 calc R . . C30 C -0.4137(6) 0.5535(4) -0.1359(3) 0.0650(16) Uani 1 1 d . . . H30A H -0.4996 0.6161 -0.1478 0.078 Uiso 1 1 calc R . . C31 C -0.3474(4) 0.4743(3) -0.1878(3) 0.0442(10) Uani 1 1 d . . . C32 C -0.4128(5) 0.4875(3) -0.2619(3) 0.0516(11) Uani 1 1 d . . . H32A H -0.3467 0.4250 -0.2915 0.062 Uiso 1 1 calc R . . C33 C -0.4055(6) 0.6032(4) -0.3027(4) 0.0744(17) Uani 1 1 d . . . H33A H -0.2970 0.6104 -0.3067 0.112 Uiso 1 1 calc R . . H33B H -0.4733 0.6658 -0.2757 0.112 Uiso 1 1 calc R . . H33C H -0.4417 0.6068 -0.3516 0.112 Uiso 1 1 calc R . . C34 C -0.5835(5) 0.4757(4) -0.2557(4) 0.0786(19) Uani 1 1 d . . . H34A H -0.6217 0.4840 -0.3045 0.118 Uiso 1 1 calc R . . H34B H -0.6503 0.5355 -0.2262 0.118 Uiso 1 1 calc R . . H34C H -0.5868 0.4002 -0.2325 0.118 Uiso 1 1 calc R . . C35 C -0.0179(5) 0.2759(4) -0.0794(2) 0.0499(11) Uani 1 1 d . . . H35A H 0.0300 0.2373 -0.1247 0.060 Uiso 1 1 calc R . . C36 C 0.1098(6) 0.3183(6) -0.0477(3) 0.0802(19) Uani 1 1 d . . . H36A H 0.1442 0.3744 -0.0828 0.120 Uiso 1 1 calc R . . H36B H 0.1996 0.2533 -0.0378 0.120 Uiso 1 1 calc R . . H36C H 0.0671 0.3544 -0.0022 0.120 Uiso 1 1 calc R . . C37 C -0.0680(7) 0.1863(6) -0.0254(3) 0.0748(16) Uani 1 1 d . . . H37A H 0.0246 0.1249 -0.0134 0.112 Uiso 1 1 calc R . . H37B H -0.1425 0.1542 -0.0472 0.112 Uiso 1 1 calc R . . H37C H -0.1182 0.2223 0.0192 0.112 Uiso 1 1 calc R . . C1S C -0.287(3) -0.5201(14) -0.4847(12) 0.301(14) Uani 1 1 d . . . H1SA H -0.3657 -0.5578 -0.4968 0.452 Uiso 1 1 calc R . . H1SB H -0.3253 -0.4370 -0.4939 0.452 Uiso 1 1 calc R . . H1SC H -0.2666 -0.5384 -0.4332 0.452 Uiso 1 1 calc R . . C2S C -0.170(2) -0.5525(16) -0.5209(14) 0.242(11) Uani 1 1 d . . . H2SA H -0.1834 -0.5329 -0.5736 0.291 Uiso 1 1 calc R . . H2SB H -0.1240 -0.6358 -0.5120 0.291 Uiso 1 1 calc R . . C3S C -0.0761(11) -0.4796(9) -0.4892(7) 0.155(4) Uani 1 1 d . . . H3SA H -0.1127 -0.3983 -0.5072 0.186 Uiso 1 1 calc R . . H3SB H -0.0910 -0.4847 -0.4353 0.186 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 0.01556(5) 0.01980(5) 0.02079(5) -0.00744(4) -0.00134(3) -0.00377(3) N1 0.0171(11) 0.0243(12) 0.0233(12) -0.0089(10) -0.0041(9) -0.0027(9) N2 0.0154(11) 0.0273(12) 0.0310(14) -0.0138(10) 0.0002(10) -0.0048(9) N3 0.0274(13) 0.0253(12) 0.0307(14) -0.0083(11) 0.0011(11) -0.0126(11) N4 0.0374(16) 0.0353(15) 0.0458(18) -0.0220(14) 0.0151(14) -0.0177(13) C1 0.0306(15) 0.0242(13) 0.0183(13) -0.0048(11) 0.0005(11) -0.0134(12) C2 0.0455(19) 0.0194(13) 0.0195(14) -0.0036(11) -0.0009(13) -0.0060(13) C3 0.088(3) 0.0259(16) 0.0178(16) -0.0009(13) -0.0007(18) -0.0043(18) C4 0.086(4) 0.0265(18) 0.027(2) 0.0065(15) 0.019(2) 0.000(2) C5 0.038(4) 0.021(3) 0.030(5) -0.002(3) 0.004(3) -0.011(3) C5A 0.039(4) 0.033(4) 0.025(5) 0.000(3) 0.003(3) -0.017(3) C6 0.024(3) 0.025(3) 0.036(3) -0.002(2) 0.004(2) -0.013(2) C6A 0.036(4) 0.030(4) 0.030(4) -0.001(3) -0.003(3) -0.018(3) C7 0.061(3) 0.089(4) 0.030(2) 0.005(2) -0.0083(19) -0.059(3) C8 0.0302(17) 0.051(2) 0.0271(16) -0.0102(15) 0.0042(13) -0.0241(15) C9 0.0258(16) 0.060(2) 0.038(2) -0.0248(18) 0.0133(14) -0.0154(16) C10 0.0160(13) 0.0372(16) 0.0252(15) -0.0120(13) 0.0009(11) -0.0049(12) C11 0.0142(13) 0.0405(17) 0.0342(17) -0.0127(14) 0.0040(12) -0.0086(12) C12 0.0165(13) 0.0372(17) 0.0346(17) -0.0118(14) -0.0008(12) -0.0091(12) C13 0.032(2) 0.050(2) 0.051(2) -0.022(2) 0.0122(18) -0.0262(19) C14 0.0210(13) 0.0252(13) 0.0210(14) -0.0089(11) 0.0014(11) -0.0036(11) C15 0.0233(14) 0.0297(15) 0.0226(14) -0.0089(12) -0.0021(11) -0.0044(12) C16 0.0402(19) 0.0390(18) 0.0282(17) -0.0098(14) -0.0091(14) -0.0145(15) C17 0.067(3) 0.0338(18) 0.0362(19) -0.0142(15) -0.0110(18) -0.0169(18) C18 0.057(2) 0.0255(16) 0.039(2) -0.0107(14) -0.0108(17) -0.0038(16) C19 0.0300(16) 0.0268(15) 0.0259(15) -0.0096(12) -0.0019(12) 0.0009(12) C20 0.0277(16) 0.0317(16) 0.0296(16) -0.0095(13) -0.0090(13) -0.0010(13) C21 0.050(2) 0.042(2) 0.042(2) 0.0016(17) 0.0048(18) -0.0139(18) C22 0.034(2) 0.060(3) 0.038(2) 0.0095(19) 0.0022(16) 0.0107(18) C23 0.0362(18) 0.0317(17) 0.0330(18) -0.0079(14) -0.0083(14) 0.0057(14) C24 0.061(3) 0.036(2) 0.056(3) 0.0059(19) -0.018(2) 0.0065(19) C25 0.041(2) 0.080(3) 0.048(3) -0.014(2) -0.004(2) 0.017(2) C26 0.0258(15) 0.0345(16) 0.049(2) -0.0256(15) 0.0135(14) -0.0191(13) C27 0.0388(19) 0.057(2) 0.043(2) -0.0318(18) 0.0160(16) -0.0311(18) C28 0.079(3) 0.071(3) 0.060(3) -0.048(2) 0.033(2) -0.052(3) C29 0.080(4) 0.063(3) 0.105(4) -0.065(3) 0.059(3) -0.043(3) C30 0.049(3) 0.035(2) 0.114(4) -0.039(3) 0.037(3) -0.0187(19) C31 0.0295(18) 0.0313(17) 0.076(3) -0.0237(18) 0.0173(18) -0.0155(14) C32 0.0278(19) 0.0340(19) 0.091(4) -0.010(2) -0.004(2) -0.0024(15) C33 0.047(3) 0.055(3) 0.120(5) 0.014(3) 0.000(3) -0.019(2) C34 0.041(3) 0.048(3) 0.149(6) 0.025(3) -0.023(3) -0.021(2) C35 0.047(2) 0.083(3) 0.033(2) -0.023(2) -0.0009(17) -0.034(2) C36 0.058(3) 0.150(6) 0.058(3) -0.043(3) 0.001(2) -0.060(4) C37 0.071(4) 0.106(5) 0.060(3) 0.014(3) -0.026(3) -0.044(3) C1S 0.53(5) 0.119(13) 0.28(3) -0.006(14) -0.05(3) -0.13(2) C2S 0.179(14) 0.177(14) 0.39(3) -0.130(16) 0.048(15) -0.062(11) C3S 0.158(11) 0.101(7) 0.198(11) -0.030(7) 0.035(9) -0.028(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 N3 1.903(3) . ? Ir1 N1 2.048(2) . ? Ir1 N2 2.053(2) . ? Ir1 C2 2.151(3) . ? Ir1 C1 2.170(3) . ? N1 C10 1.340(4) . ? N1 C14 1.448(3) . ? N2 C12 1.333(4) . ? N2 C26 1.453(4) . ? N3 N4 1.107(4) . ? C1 C2 1.403(4) . ? C1 C8 1.509(5) . ? C2 C3 1.514(4) . ? C3 C4 1.540(6) . ? C4 C5A 1.312(9) . ? C4 C5 1.741(10) . ? C5 C6 1.547(9) . ? C5A C6A 1.524(12) . ? C6 C7 1.439(7) . ? C6A C7 1.768(11) . ? C7 C8 1.534(5) . ? C9 C10 1.520(4) . ? C10 C11 1.394(4) . ? C11 C12 1.398(4) . ? C12 C13 1.510(5) . ? C14 C19 1.407(4) . ? C14 C15 1.411(4) . ? C15 C16 1.400(4) . ? C15 C20 1.522(5) . ? C16 C17 1.373(5) . ? C17 C18 1.383(5) . ? C18 C19 1.395(5) . ? C19 C23 1.526(5) . ? C20 C21 1.531(5) . ? C20 C22 1.531(5) . ? C23 C25 1.528(5) . ? C23 C24 1.536(6) . ? C26 C27 1.397(5) . ? C26 C31 1.412(5) . ? C27 C28 1.408(5) . ? C27 C35 1.514(6) . ? C28 C29 1.377(8) . ? C29 C30 1.365(8) . ? C30 C31 1.397(5) . ? C31 C32 1.516(7) . ? C32 C33 1.541(6) . ? C32 C34 1.543(6) . ? C35 C36 1.536(5) . ? C35 C37 1.526(7) . ? C1S C2S 1.17(2) . ? C2S C3S 1.54(2) . ? C3S C3S 1.341(17) 2_544 ? 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 N3 Ir1 N1 177.81(11) . . ? N3 Ir1 N2 88.32(10) . . ? N1 Ir1 N2 90.34(10) . . ? N3 Ir1 C2 88.11(11) . . ? N1 Ir1 C2 93.76(11) . . ? N2 Ir1 C2 159.03(11) . . ? N3 Ir1 C1 86.70(11) . . ? N1 Ir1 C1 94.07(10) . . ? N2 Ir1 C1 162.05(11) . . ? C2 Ir1 C1 37.90(12) . . ? C10 N1 C14 114.7(2) . . ? C10 N1 Ir1 125.35(19) . . ? C14 N1 Ir1 119.57(19) . . ? C12 N2 C26 116.2(3) . . ? C12 N2 Ir1 127.4(2) . . ? C26 N2 Ir1 116.33(19) . . ? N4 N3 Ir1 178.4(3) . . ? C2 C1 C8 123.8(3) . . ? C2 C1 Ir1 70.30(17) . . ? C8 C1 Ir1 120.1(2) . . ? C1 C2 C3 124.0(3) . . ? C1 C2 Ir1 71.80(17) . . ? C3 C2 Ir1 119.3(2) . . ? C2 C3 C4 111.2(3) . . ? C5A C4 C3 114.3(5) . . ? C5A C4 C5 31.3(4) . . ? C3 C4 C5 115.7(4) . . ? C6 C5 C4 117.3(5) . . ? C4 C5A C6A 113.3(6) . . ? C7 C6 C5 107.1(5) . . ? C5A C6A C7 112.9(5) . . ? C6 C7 C8 114.6(4) . . ? C6 C7 C6A 44.8(4) . . ? C8 C7 C6A 112.0(4) . . ? C1 C8 C7 111.4(3) . . ? N1 C10 C11 125.2(3) . . ? N1 C10 C9 120.9(3) . . ? C11 C10 C9 113.9(3) . . ? C10 C11 C12 128.6(3) . . ? N2 C12 C11 122.9(3) . . ? N2 C12 C13 119.9(3) . . ? C11 C12 C13 117.2(3) . . ? C19 C14 C15 121.0(3) . . ? C19 C14 N1 120.9(3) . . ? C15 C14 N1 118.1(3) . . ? C16 C15 C14 117.9(3) . . ? C16 C15 C20 119.4(3) . . ? C14 C15 C20 122.8(3) . . ? C17 C16 C15 121.5(3) . . ? C16 C17 C18 120.1(3) . . ? C17 C18 C19 121.0(3) . . ? C18 C19 C14 118.5(3) . . ? C18 C19 C23 118.6(3) . . ? C14 C19 C23 122.8(3) . . ? C15 C20 C21 111.1(3) . . ? C15 C20 C22 112.3(3) . . ? C21 C20 C22 108.5(3) . . ? C25 C23 C19 110.9(3) . . ? C25 C23 C24 109.1(3) . . ? C19 C23 C24 113.1(3) . . ? C27 C26 C31 121.9(3) . . ? C27 C26 N2 119.8(3) . . ? C31 C26 N2 118.1(3) . . ? C26 C27 C28 117.3(4) . . ? C26 C27 C35 122.2(3) . . ? C28 C27 C35 120.4(4) . . ? C29 C28 C27 121.4(5) . . ? C30 C29 C28 120.2(4) . . ? C29 C30 C31 121.6(5) . . ? C30 C31 C26 117.5(4) . . ? C30 C31 C32 120.4(4) . . ? C26 C31 C32 122.1(3) . . ? C31 C32 C33 111.4(4) . . ? C31 C32 C34 111.6(4) . . ? C33 C32 C34 109.6(4) . . ? C27 C35 C36 112.8(4) . . ? C27 C35 C37 111.6(4) . . ? C36 C35 C37 109.3(4) . . ? C1S C2S C3S 96(2) . . ? C3S C3S C2S 107.8(13) 2_544 . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 1.533 _refine_diff_density_min -1.180 _refine_diff_density_rms 0.152 data_wb2 _database_code_depnum_ccdc_archive 'CCDC 225949' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H45 Ir N2' _chemical_formula_weight 613.87 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6062(7) _cell_length_b 15.9992(9) _cell_length_c 14.2536(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.309(2) _cell_angle_gamma 90.00 _cell_volume 2772.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 4.833 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.2825 _exptl_absorpt_correction_T_max 0.5309 _exptl_absorpt_process_details ? _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 'Bruker 1K CCD area detector' _diffrn_measurement_method '0.3 deg. omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47442 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 32.58 _reflns_number_total 9822 _reflns_number_gt 7237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9822 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.004 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 0.663870(9) 0.089491(6) 0.254873(7) 0.02270(4) Uani 1 1 d . . . H1M H 0.721(3) 0.021(3) 0.220(3) 0.066(13) Uiso 1 1 d . . . H2M H 0.689(4) 0.026(3) 0.333(4) 0.102(18) Uiso 1 1 d . . . H3M H 0.587(4) 0.033(3) 0.282(4) 0.090(16) Uiso 1 1 d . . . H4M H 0.624(3) 0.033(2) 0.171(3) 0.054(11) Uiso 1 1 d . . . N1 N 0.64186(17) 0.18204(14) 0.34734(15) 0.0186(4) Uani 1 1 d . . . N2 N 0.71003(17) 0.17661(14) 0.16774(14) 0.0178(4) Uani 1 1 d . . . C1 C 0.6338(3) 0.3234(2) 0.4120(2) 0.0268(6) Uani 1 1 d . . . H1C H 0.667(2) 0.3119(19) 0.469(2) 0.022(8) Uiso 1 1 d . . . H1B H 0.565(4) 0.323(3) 0.406(3) 0.059(13) Uiso 1 1 d . . . H1A H 0.651(3) 0.377(3) 0.400(3) 0.053(11) Uiso 1 1 d . . . C2 C 0.65707(19) 0.26357(16) 0.33812(17) 0.0179(5) Uani 1 1 d . . . C3 C 0.6934(2) 0.29852(17) 0.26231(18) 0.0203(5) Uani 1 1 d . . . H3 H 0.710(2) 0.349(2) 0.266(2) 0.021(8) Uiso 1 1 d . . . C4 C 0.7186(2) 0.25890(17) 0.18340(18) 0.0191(5) Uani 1 1 d . . . C5 C 0.7572(3) 0.3136(2) 0.1131(2) 0.0301(6) Uani 1 1 d . . . H5C H 0.707(4) 0.320(3) 0.055(3) 0.069(14) Uiso 1 1 d . . . H5B H 0.769(3) 0.370(3) 0.134(3) 0.049(11) Uiso 1 1 d . . . H5A H 0.827(3) 0.298(2) 0.112(3) 0.042(10) Uiso 1 1 d . . . C6 C 0.6041(2) 0.15435(16) 0.43061(18) 0.0194(5) Uani 1 1 d . . . C7 C 0.4910(2) 0.14698(17) 0.42081(19) 0.0213(5) Uani 1 1 d . . . C8 C 0.4580(2) 0.11379(18) 0.4992(2) 0.0266(6) Uani 1 1 d . . . H8 H 0.383(3) 0.104(2) 0.491(2) 0.034(9) Uiso 1 1 d . . . C9 C 0.5332(3) 0.0915(2) 0.5845(2) 0.0315(6) Uani 1 1 d . . . H9 H 0.506(3) 0.067(2) 0.640(2) 0.028(8) Uiso 1 1 d . . . C10 C 0.6445(3) 0.10155(18) 0.5938(2) 0.0293(6) Uani 1 1 d . . . H10 H 0.700(3) 0.0845(18) 0.653(2) 0.024(8) Uiso 1 1 d . . . C11 C 0.6826(2) 0.13197(18) 0.51649(19) 0.0232(5) Uani 1 1 d . . . C12 C 0.4048(2) 0.17521(19) 0.3294(2) 0.0252(6) Uani 1 1 d . . . H12 H 0.450(2) 0.2087(18) 0.287(2) 0.022(8) Uiso 1 1 d . . . C13 C 0.3446(3) 0.1012(2) 0.2709(3) 0.0410(9) Uani 1 1 d . . . H13C H 0.400(4) 0.064(3) 0.257(3) 0.057(12) Uiso 1 1 d . . . H13B H 0.290(4) 0.122(3) 0.215(3) 0.062(13) Uiso 1 1 d . . . H13A H 0.310(3) 0.074(2) 0.302(3) 0.034(11) Uiso 1 1 d . . . C14 C 0.3214(3) 0.2342(3) 0.3543(3) 0.0424(8) Uani 1 1 d . . . H14C H 0.271(3) 0.254(2) 0.298(2) 0.028(8) Uiso 1 1 d . . . H14C' H 0.354(3) 0.277(2) 0.392(3) 0.039(10) Uiso 1 1 d . . . H14A H 0.275(3) 0.209(3) 0.393(3) 0.060(13) Uiso 1 1 d . . . C15 C 0.8053(2) 0.1381(2) 0.5278(2) 0.0344(7) Uani 1 1 d . . . H15 H 0.815(3) 0.164(2) 0.474(3) 0.037(9) Uiso 1 1 d . . . C16 C 0.8647(4) 0.1859(4) 0.6191(3) 0.0522(11) Uani 1 1 d . . . H16C H 0.863(3) 0.158(2) 0.677(3) 0.052(12) Uiso 1 1 d . . . H16B H 0.940(4) 0.186(3) 0.626(3) 0.066(13) Uiso 1 1 d . . . H16A H 0.840(4) 0.235(3) 0.621(3) 0.061(16) Uiso 1 1 d . . . C17 C 0.8570(4) 0.0516(4) 0.5277(4) 0.0657(14) Uani 1 1 d . . . H17C H 0.934(4) 0.054(3) 0.532(3) 0.074(14) Uiso 1 1 d . . . H17B H 0.841(4) 0.017(4) 0.579(4) 0.10(2) Uiso 1 1 d . . . H17A H 0.823(4) 0.019(3) 0.464(4) 0.078(15) Uiso 1 1 d . . . C18 C 0.7334(2) 0.14190(16) 0.08064(18) 0.0191(5) Uani 1 1 d . . . C19 C 0.8382(2) 0.10906(17) 0.08658(19) 0.0213(5) Uani 1 1 d . . . C2O C 0.8532(2) 0.06472(19) 0.0069(2) 0.0271(6) Uani 1 1 d . . . H20 H 0.919(3) 0.042(2) 0.009(2) 0.030(8) Uiso 1 1 d . . . C21 C 0.7680(3) 0.0539(2) -0.0760(2) 0.0307(6) Uani 1 1 d . . . H21 H 0.784(3) 0.022(2) -0.125(2) 0.031(9) Uiso 1 1 d . . . C22 C 0.6670(2) 0.0908(2) -0.0829(2) 0.0286(6) Uani 1 1 d . . . H22 H 0.609(3) 0.082(2) -0.137(3) 0.038(10) Uiso 1 1 d . . . C23 C 0.6478(2) 0.13663(18) -0.00546(19) 0.0225(5) Uani 1 1 d . . . C24 C 0.9353(2) 0.1222(2) 0.1749(2) 0.0293(6) Uani 1 1 d . . . H24 H 0.913(3) 0.151(2) 0.218(2) 0.028(8) Uiso 1 1 d . . . C25 C 1.0286(3) 0.1686(3) 0.1469(3) 0.0401(8) Uani 1 1 d . . . H25C H 1.063(3) 0.125(3) 0.102(3) 0.067(13) Uiso 1 1 d . . . H25B H 1.078(3) 0.180(2) 0.203(3) 0.037(10) Uiso 1 1 d . . . H25A H 1.004(4) 0.219(3) 0.112(4) 0.085(16) Uiso 1 1 d . . . C26 C 0.9779(4) 0.0402(3) 0.2258(3) 0.0535(11) Uani 1 1 d . . . H26B H 1.033(4) 0.046(3) 0.288(3) 0.068(13) Uiso 1 1 d . . . H26A H 0.918(3) 0.008(2) 0.252(3) 0.047(10) Uiso 1 1 d . . . H26A' H 1.003(4) -0.001(3) 0.187(4) 0.090(18) Uiso 1 1 d . . . C27 C 0.5365(2) 0.1779(2) -0.0152(2) 0.0276(6) Uani 1 1 d . . . H27 H 0.545(2) 0.216(2) 0.040(2) 0.030(8) Uiso 1 1 d . . . C28 C 0.5032(3) 0.2320(3) -0.1074(3) 0.0487(10) Uani 1 1 d . . . H28C H 0.501(3) 0.198(3) -0.159(3) 0.060(13) Uiso 1 1 d . . . H28B H 0.565(4) 0.269(3) -0.111(3) 0.082(16) Uiso 1 1 d . . . H28A H 0.442(3) 0.266(3) -0.106(3) 0.051(11) Uiso 1 1 d . . . C29 C 0.4477(3) 0.1146(3) -0.0131(4) 0.0480(10) Uani 1 1 d . . . H29C H 0.433(4) 0.068(3) -0.069(3) 0.069(14) Uiso 1 1 d . . . H29B H 0.383(4) 0.143(3) -0.014(3) 0.058(12) Uiso 1 1 d . . . H29A H 0.458(4) 0.086(3) 0.045(4) 0.065(15) Uiso 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 0.03392(6) 0.01629(5) 0.02179(5) -0.00109(5) 0.01426(4) -0.00173(5) N1 0.0201(10) 0.0201(11) 0.0162(10) -0.0012(8) 0.0056(8) -0.0012(8) N2 0.0189(10) 0.0221(11) 0.0131(9) -0.0001(8) 0.0051(8) 0.0006(8) C1 0.0338(16) 0.0246(16) 0.0255(15) -0.0051(12) 0.0141(13) -0.0029(12) C2 0.0173(11) 0.0173(12) 0.0189(11) -0.0010(9) 0.0045(9) 0.0020(9) C3 0.0238(12) 0.0156(13) 0.0214(13) -0.0002(9) 0.0058(10) -0.0018(9) C4 0.0193(11) 0.0204(13) 0.0179(11) 0.0023(9) 0.0055(9) -0.0001(9) C5 0.0430(18) 0.0249(16) 0.0276(15) 0.0034(12) 0.0187(14) -0.0055(13) C6 0.0265(13) 0.0176(13) 0.0172(11) -0.0010(9) 0.0111(10) -0.0009(10) C7 0.0248(13) 0.0195(13) 0.0204(12) -0.0027(10) 0.0075(10) -0.0002(10) C8 0.0298(15) 0.0242(14) 0.0300(15) -0.0033(11) 0.0156(12) -0.0040(11) C9 0.0438(16) 0.0306(16) 0.0244(13) 0.0021(13) 0.0167(12) -0.0046(14) C10 0.0415(16) 0.0266(16) 0.0203(13) 0.0046(11) 0.0088(12) -0.0001(12) C11 0.0269(13) 0.0236(14) 0.0188(12) 0.0020(10) 0.0057(10) -0.0009(11) C12 0.0185(12) 0.0286(15) 0.0278(14) -0.0021(11) 0.0052(10) 0.0023(10) C13 0.044(2) 0.036(2) 0.0348(18) -0.0095(15) -0.0045(16) 0.0015(16) C14 0.0313(17) 0.052(2) 0.0402(19) -0.0065(18) 0.0029(15) 0.0143(17) C15 0.0244(14) 0.053(2) 0.0234(14) 0.0114(14) 0.0015(12) 0.0024(14) C16 0.038(2) 0.072(3) 0.039(2) 0.005(2) -0.0025(17) -0.014(2) C17 0.038(2) 0.087(4) 0.063(3) -0.004(3) -0.002(2) 0.031(2) C18 0.0227(12) 0.0180(13) 0.0169(11) -0.0009(9) 0.0059(9) -0.0009(9) C19 0.0222(12) 0.0214(14) 0.0205(12) 0.0001(10) 0.0061(10) 0.0006(9) C2O 0.0263(14) 0.0270(15) 0.0300(15) -0.0023(11) 0.0108(11) 0.0074(11) C21 0.0372(16) 0.0319(17) 0.0239(14) -0.0114(12) 0.0099(12) 0.0006(13) C22 0.0287(14) 0.0333(16) 0.0215(13) -0.0073(12) 0.0026(11) -0.0021(13) C23 0.0211(12) 0.0267(15) 0.0193(12) -0.0001(10) 0.0044(10) -0.0019(10) C24 0.0216(13) 0.0413(18) 0.0232(14) -0.0040(13) 0.0029(11) 0.0040(12) C25 0.0252(16) 0.049(2) 0.041(2) -0.0011(17) 0.0011(14) -0.0057(15) C26 0.048(2) 0.052(3) 0.049(2) 0.021(2) -0.0076(19) 0.0008(19) C27 0.0229(13) 0.0339(17) 0.0234(14) -0.0023(12) 0.0016(11) 0.0043(11) C28 0.039(2) 0.068(3) 0.038(2) 0.015(2) 0.0082(16) 0.023(2) C29 0.0229(16) 0.049(2) 0.070(3) -0.003(2) 0.0085(17) -0.0017(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 H3M 1.45(5) . ? Ir1 H2M 1.47(5) . ? Ir1 H1M 1.47(4) . ? Ir1 H4M 1.48(4) . ? Ir1 N1 2.049(2) . ? Ir1 N2 2.051(2) . ? N1 C2 1.330(3) . ? N1 C6 1.459(3) . ? N2 C4 1.335(3) . ? N2 C18 1.460(3) . ? C1 C2 1.508(4) . ? C2 C3 1.397(3) . ? C3 C4 1.399(4) . ? C4 C5 1.504(4) . ? C6 C7 1.401(4) . ? C6 C11 1.402(4) . ? C7 C8 1.396(4) . ? C7 C12 1.528(4) . ? C8 C9 1.377(4) . ? C9 C10 1.384(4) . ? C10 C11 1.400(4) . ? C11 C15 1.515(4) . ? C12 C14 1.524(4) . ? C12 C13 1.529(4) . ? C15 C16 1.524(5) . ? C15 C17 1.530(6) . ? C18 C19 1.403(4) . ? C18 C23 1.407(3) . ? C19 C2O 1.393(4) . ? C19 C24 1.521(4) . ? C2O C21 1.382(4) . ? C21 C22 1.383(4) . ? C22 C23 1.398(4) . ? C23 C27 1.523(4) . ? C24 C26 1.527(5) . ? C24 C25 1.530(5) . ? C27 C29 1.515(5) . ? C27 C28 1.537(5) . ? 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 H3M Ir1 H2M 53(2) . . ? H3M Ir1 H1M 93(3) . . ? H2M Ir1 H1M 73(2) . . ? H3M Ir1 H4M 74(2) . . ? H2M Ir1 H4M 98(3) . . ? H1M Ir1 H4M 50.1(18) . . ? H3M Ir1 N1 93.9(19) . . ? H2M Ir1 N1 93(2) . . ? H1M Ir1 N1 156.7(16) . . ? H4M Ir1 N1 152.8(15) . . ? H3M Ir1 N2 154(2) . . ? H2M Ir1 N2 152(2) . . ? H1M Ir1 N2 93.5(16) . . ? H4M Ir1 N2 91.0(15) . . ? N1 Ir1 N2 90.38(9) . . ? C2 N1 C6 117.7(2) . . ? C2 N1 Ir1 126.69(17) . . ? C6 N1 Ir1 115.61(16) . . ? C4 N2 C18 119.5(2) . . ? C4 N2 Ir1 126.34(17) . . ? C18 N2 Ir1 114.20(16) . . ? N1 C2 C3 123.7(2) . . ? N1 C2 C1 119.6(2) . . ? C3 C2 C1 116.7(2) . . ? C2 C3 C4 129.1(3) . . ? N2 C4 C3 123.7(2) . . ? N2 C4 C5 119.3(2) . . ? C3 C4 C5 117.0(2) . . ? C7 C6 C11 122.1(2) . . ? C7 C6 N1 119.1(2) . . ? C11 C6 N1 118.8(2) . . ? C8 C7 C6 117.6(2) . . ? C8 C7 C12 120.0(2) . . ? C6 C7 C12 122.4(2) . . ? C9 C8 C7 121.6(3) . . ? C8 C9 C10 119.9(3) . . ? C9 C10 C11 121.0(3) . . ? C10 C11 C6 117.8(3) . . ? C10 C11 C15 119.4(2) . . ? C6 C11 C15 122.8(2) . . ? C14 C12 C7 111.3(2) . . ? C14 C12 C13 109.4(3) . . ? C7 C12 C13 112.0(3) . . ? C11 C15 C16 112.4(3) . . ? C11 C15 C17 111.4(3) . . ? C16 C15 C17 110.0(3) . . ? C19 C18 C23 121.6(2) . . ? C19 C18 N2 119.3(2) . . ? C23 C18 N2 118.9(2) . . ? C2O C19 C18 118.0(2) . . ? C2O C19 C24 119.5(2) . . ? C18 C19 C24 122.4(2) . . ? C21 C2O C19 121.2(3) . . ? C2O C21 C22 120.0(3) . . ? C21 C22 C23 121.0(3) . . ? C22 C23 C18 117.8(2) . . ? C22 C23 C27 120.2(2) . . ? C18 C23 C27 122.0(2) . . ? C19 C24 C26 112.3(3) . . ? C19 C24 C25 110.9(3) . . ? C26 C24 C25 110.0(3) . . ? C29 C27 C23 112.1(3) . . ? C29 C27 C28 110.9(3) . . ? C23 C27 C28 111.0(3) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.559 _refine_diff_density_min -1.433 _refine_diff_density_rms 0.124