# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Mark Stradiotto' _publ_contact_author_address ; Mark Stradiotto Assistant Professor Dalhousie University Department of Chemistry Halifax, Nova Scotia Canada B3H 4J3 ; _publ_contact_author_phone '902 494 7190' _publ_contact_author_fax '902 494 1310' _publ_contact_author_email mark.stradiotto@dal.ca _publ_requested_coeditor_name ? _publ_section_title ; Cationic and Zwitterionic Bidentate Relatives of Crabtree's Hydrogenation Catalyst ; loop_ _publ_author_name 'Mark Stradiotto' 'Judy Cipot' 'Robert McDonald' data_dal0501compound2aOTf _database_code_depnum_ccdc_archive 'CCDC 270594' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H38 Ir N P, C F3 O3 S' _chemical_formula_sum 'C26 H38 F3 Ir N O3 P S' _chemical_formula_weight 724.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9608(6) _cell_length_b 20.2706(12) _cell_length_c 14.0988(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.5748(10) _cell_angle_gamma 90.00 _cell_volume 2767.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6048 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.85 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 5.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4055 _exptl_absorpt_correction_T_max 0.6902 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19876 _diffrn_reflns_av_R_equivalents 0.0621 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.41 _reflns_number_total 5676 _reflns_number_gt 4270 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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^)+(0.0245P)^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 5676 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.063099(17) 0.144725(9) 0.202186(13) 0.01754(6) Uani 1 1 d . . . P P 0.29953(11) 0.14246(7) 0.22646(8) 0.0181(2) Uani 1 1 d . . . N N 0.1044(4) 0.1188(2) 0.3573(3) 0.0208(9) Uani 1 1 d . . . C1 C 0.3073(5) 0.0832(2) 0.5024(3) 0.0237(11) Uani 1 1 d . . . H1A H 0.2736 0.1109 0.5498 0.028 Uiso 1 1 calc R . . H1B H 0.2821 0.0366 0.5103 0.028 Uiso 1 1 calc R . . C2 C 0.2522(5) 0.1067(2) 0.3997(3) 0.0197(10) Uani 1 1 d . . . C3 C 0.3524(5) 0.1201(2) 0.3538(3) 0.0193(10) Uani 1 1 d . . . C3A C 0.4880(5) 0.1113(2) 0.4248(3) 0.0222(11) Uani 1 1 d . . . C4 C 0.6225(5) 0.1225(3) 0.4189(4) 0.0264(12) Uani 1 1 d . . . H4 H 0.6428 0.1361 0.3593 0.032 Uiso 1 1 calc R . . C5 C 0.7277(5) 0.1135(3) 0.5027(4) 0.0304(12) Uani 1 1 d . . . H5 H 0.8206 0.1214 0.4997 0.036 Uiso 1 1 calc R . . C6 C 0.7006(5) 0.0933(3) 0.5899(4) 0.0294(12) Uani 1 1 d . . . H6 H 0.7744 0.0872 0.6456 0.035 Uiso 1 1 calc R . . C7 C 0.5659(5) 0.0820(2) 0.5959(4) 0.0265(12) Uani 1 1 d . . . H7 H 0.5464 0.0682 0.6557 0.032 Uiso 1 1 calc R . . C7A C 0.4597(5) 0.0910(2) 0.5133(3) 0.0211(11) Uani 1 1 d . . . C11 C 0.0312(5) 0.1530(3) 0.0463(3) 0.0230(11) Uani 1 1 d . . . H11 H 0.1169 0.1484 0.0215 0.028 Uiso 1 1 calc R . . C12 C 0.0162(5) 0.2148(2) 0.0887(3) 0.0225(11) Uani 1 1 d . . . H12 H 0.0944 0.2456 0.0882 0.027 Uiso 1 1 calc R . . C13 C -0.1175(5) 0.2497(3) 0.0864(4) 0.0268(12) Uani 1 1 d . . . H13A H -0.1538 0.2681 0.0203 0.032 Uiso 1 1 calc R . . H13B H -0.0995 0.2870 0.1330 0.032 Uiso 1 1 calc R . . C14 C -0.2267(5) 0.2051(3) 0.1122(4) 0.0300(12) Uani 1 1 d . . . H14A H -0.2814 0.1842 0.0519 0.036 Uiso 1 1 calc R . . H14B H -0.2904 0.2321 0.1405 0.036 Uiso 1 1 calc R . . C15 C -0.1630(4) 0.1515(3) 0.1846(4) 0.0246(11) Uani 1 1 d . . . H15 H -0.1932 0.1527 0.2474 0.029 Uiso 1 1 calc R . . C16 C -0.1288(5) 0.0888(3) 0.1573(3) 0.0236(11) Uani 1 1 d . . . H16 H -0.1393 0.0534 0.2043 0.028 Uiso 1 1 calc R . . C17 C -0.1470(5) 0.0648(3) 0.0543(4) 0.0315(12) Uani 1 1 d . . . H17A H -0.2464 0.0567 0.0261 0.038 Uiso 1 1 calc R . . H17B H -0.0979 0.0223 0.0550 0.038 Uiso 1 1 calc R . . C18 C -0.0928(5) 0.1137(3) -0.0110(4) 0.0284(12) Uani 1 1 d . . . H18A H -0.0654 0.0892 -0.0642 0.034 Uiso 1 1 calc R . . H18B H -0.1677 0.1446 -0.0411 0.034 Uiso 1 1 calc R . . C21 C 0.3525(5) 0.0734(2) 0.1583(3) 0.0232(11) Uani 1 1 d . . . H21 H 0.3196 0.0840 0.0873 0.028 Uiso 1 1 calc R . . C22 C 0.2769(5) 0.0109(3) 0.1771(4) 0.0324(13) Uani 1 1 d . . . H22A H 0.1776 0.0198 0.1645 0.039 Uiso 1 1 calc R . . H22B H 0.3110 -0.0029 0.2451 0.039 Uiso 1 1 calc R . . H22C H 0.2935 -0.0243 0.1336 0.039 Uiso 1 1 calc R . . C23 C 0.5079(5) 0.0613(3) 0.1774(4) 0.0388(14) Uani 1 1 d . . . H23A H 0.5543 0.1022 0.1658 0.047 Uiso 1 1 calc R . . H23B H 0.5261 0.0268 0.1333 0.047 Uiso 1 1 calc R . . H23C H 0.5430 0.0472 0.2451 0.047 Uiso 1 1 calc R . . C24 C 0.4051(5) 0.2145(2) 0.2119(3) 0.0240(11) Uani 1 1 d . . . H24 H 0.5039 0.2033 0.2412 0.029 Uiso 1 1 calc R . . C25 C 0.3918(5) 0.2311(3) 0.1042(4) 0.0301(13) Uani 1 1 d . . . H25A H 0.4275 0.1943 0.0722 0.036 Uiso 1 1 calc R . . H25B H 0.4450 0.2710 0.0989 0.036 Uiso 1 1 calc R . . H25C H 0.2944 0.2385 0.0724 0.036 Uiso 1 1 calc R . . C26 C 0.3655(6) 0.2718(3) 0.2696(4) 0.0370(14) Uani 1 1 d . . . H26A H 0.3807 0.2593 0.3385 0.044 Uiso 1 1 calc R . . H26B H 0.2679 0.2827 0.2439 0.044 Uiso 1 1 calc R . . H26C H 0.4225 0.3103 0.2637 0.044 Uiso 1 1 calc R . . C27 C 0.0225(5) 0.0625(3) 0.3839(3) 0.0260(11) Uani 1 1 d . . . H27A H -0.0761 0.0700 0.3560 0.031 Uiso 1 1 calc R . . H27B H 0.0392 0.0593 0.4550 0.031 Uiso 1 1 calc R . . H27C H 0.0509 0.0213 0.3579 0.031 Uiso 1 1 calc R . . C28 C 0.0678(5) 0.1801(3) 0.4058(4) 0.0297(12) Uani 1 1 d . . . H28A H -0.0304 0.1900 0.3807 0.036 Uiso 1 1 calc R . . H28B H 0.1234 0.2172 0.3919 0.036 Uiso 1 1 calc R . . H28C H 0.0866 0.1731 0.4765 0.036 Uiso 1 1 calc R . . S S 0.15937(14) 0.09301(7) 0.73233(10) 0.0288(3) Uani 1 1 d . . . F1 F 0.2317(5) 0.1900(2) 0.8563(3) 0.0909(15) Uani 1 1 d . . . F2 F 0.3960(4) 0.1521(3) 0.7997(3) 0.0899(16) Uani 1 1 d . . . F3 F 0.3223(5) 0.0977(2) 0.9070(3) 0.0862(15) Uani 1 1 d . . . O1 O 0.2359(4) 0.03845(19) 0.7085(3) 0.0395(10) Uani 1 1 d . . . O2 O 0.0501(4) 0.0759(2) 0.7785(3) 0.0458(11) Uani 1 1 d . . . O3 O 0.1253(4) 0.14256(19) 0.6575(3) 0.0399(9) Uani 1 1 d . . . C30 C 0.2831(7) 0.1345(4) 0.8282(5) 0.0548(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir 0.01501(9) 0.02024(10) 0.01735(10) 0.00143(10) 0.00379(6) -0.00049(9) P 0.0161(5) 0.0219(7) 0.0165(6) 0.0016(6) 0.0041(4) 0.0001(5) N 0.021(2) 0.024(2) 0.018(2) 0.0005(18) 0.0078(17) -0.0064(17) C1 0.028(3) 0.028(3) 0.014(2) 0.001(2) 0.003(2) -0.002(2) C2 0.028(3) 0.016(3) 0.015(2) -0.001(2) 0.005(2) 0.000(2) C3 0.022(2) 0.017(2) 0.018(2) 0.002(2) 0.0036(19) 0.0004(19) C3A 0.024(2) 0.024(3) 0.016(2) -0.001(2) 0.000(2) 0.004(2) C4 0.022(3) 0.033(3) 0.022(3) 0.001(2) 0.002(2) 0.002(2) C5 0.017(2) 0.032(3) 0.039(3) -0.003(3) 0.001(2) 0.000(2) C6 0.031(3) 0.029(3) 0.026(3) -0.004(2) 0.000(2) 0.008(2) C7 0.031(3) 0.025(3) 0.022(3) 0.004(2) 0.004(2) 0.004(2) C7A 0.023(2) 0.016(3) 0.023(3) -0.005(2) 0.003(2) 0.0005(19) C11 0.020(2) 0.032(3) 0.020(2) 0.006(2) 0.0094(19) -0.002(2) C12 0.016(2) 0.026(3) 0.022(3) 0.010(2) -0.0022(19) 0.000(2) C13 0.027(3) 0.022(3) 0.030(3) 0.007(2) 0.003(2) 0.004(2) C14 0.023(3) 0.034(3) 0.032(3) 0.004(3) 0.003(2) 0.005(2) C15 0.018(2) 0.032(3) 0.026(3) 0.006(3) 0.0083(19) -0.004(2) C16 0.021(2) 0.030(3) 0.019(3) 0.001(2) 0.003(2) -0.009(2) C17 0.031(3) 0.030(3) 0.032(3) -0.007(3) 0.003(2) -0.005(2) C18 0.031(3) 0.033(3) 0.020(3) -0.001(2) 0.004(2) -0.001(2) C21 0.026(3) 0.028(3) 0.015(2) -0.007(2) 0.0036(19) 0.005(2) C22 0.034(3) 0.028(3) 0.031(3) -0.008(3) 0.001(2) 0.003(2) C23 0.027(3) 0.044(4) 0.045(3) -0.011(3) 0.009(2) 0.011(3) C24 0.019(2) 0.028(3) 0.024(3) 0.001(2) 0.004(2) -0.004(2) C25 0.027(3) 0.036(3) 0.029(3) 0.010(3) 0.008(2) -0.005(2) C26 0.046(3) 0.032(3) 0.035(3) -0.003(3) 0.014(3) -0.015(3) C27 0.025(3) 0.032(3) 0.022(3) 0.001(2) 0.006(2) -0.010(2) C28 0.024(3) 0.039(3) 0.025(3) -0.005(3) 0.004(2) 0.001(2) S 0.0363(7) 0.0265(7) 0.0272(7) 0.0038(6) 0.0144(6) 0.0044(6) F1 0.139(4) 0.058(3) 0.072(3) -0.032(3) 0.018(3) -0.010(3) F2 0.068(3) 0.130(4) 0.067(3) -0.008(3) 0.007(2) -0.052(3) F3 0.108(4) 0.112(4) 0.030(2) 0.010(2) -0.004(2) 0.000(3) O1 0.045(2) 0.035(2) 0.044(2) 0.0068(19) 0.0213(19) 0.0113(18) O2 0.050(2) 0.042(3) 0.056(3) 0.005(2) 0.032(2) 0.005(2) O3 0.050(2) 0.035(2) 0.038(2) 0.015(2) 0.0159(18) 0.013(2) C30 0.066(5) 0.061(5) 0.036(4) -0.001(4) 0.009(3) -0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir C12 2.108(5) . ? Ir C11 2.152(4) . ? Ir C16 2.184(4) . ? Ir N 2.192(4) . ? Ir C15 2.212(4) . ? Ir P 2.2994(11) . ? P C3 1.807(5) . ? P C24 1.840(5) . ? P C21 1.844(5) . ? N C2 1.475(6) . ? N C27 1.501(6) . ? N C28 1.504(6) . ? C1 C7A 1.498(6) . ? C1 C2 1.500(6) . ? C2 C3 1.339(6) . ? C3 C3A 1.491(6) . ? C3A C4 1.380(7) . ? C3A C7A 1.404(7) . ? C4 C5 1.396(7) . ? C5 C6 1.381(7) . ? C6 C7 1.383(7) . ? C7 C7A 1.390(6) . ? C11 C12 1.410(7) . ? C11 C18 1.532(7) . ? C12 C13 1.502(6) . ? C13 C14 1.522(7) . ? C14 C15 1.524(7) . ? C15 C16 1.393(7) . ? C16 C17 1.501(7) . ? C17 C18 1.534(7) . ? C21 C23 1.527(6) . ? C21 C22 1.528(7) . ? C24 C26 1.521(7) . ? C24 C25 1.531(6) . ? S O1 1.428(4) . ? S O2 1.436(4) . ? S O3 1.439(4) . ? S C30 1.809(7) . ? F1 C30 1.333(8) . ? F2 C30 1.329(8) . ? F3 C30 1.318(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 Ir C11 38.65(18) . . ? C12 Ir C16 96.12(18) . . ? C11 Ir C16 80.50(17) . . ? C12 Ir N 151.03(18) . . ? C11 Ir N 170.28(18) . . ? C16 Ir N 96.39(16) . . ? C12 Ir C15 80.50(18) . . ? C11 Ir C15 88.76(17) . . ? C16 Ir C15 36.94(18) . . ? N Ir C15 94.25(16) . . ? C12 Ir P 99.38(13) . . ? C11 Ir P 93.10(12) . . ? C16 Ir P 145.98(14) . . ? N Ir P 84.33(10) . . ? C15 Ir P 176.83(14) . . ? C3 P C24 105.6(2) . . ? C3 P C21 106.0(2) . . ? C24 P C21 107.7(2) . . ? C3 P Ir 101.69(15) . . ? C24 P Ir 124.05(16) . . ? C21 P Ir 110.24(15) . . ? C2 N C27 108.7(4) . . ? C2 N C28 106.2(3) . . ? C27 N C28 108.1(4) . . ? C2 N Ir 112.4(3) . . ? C27 N Ir 116.5(3) . . ? C28 N Ir 104.3(3) . . ? C7A C1 C2 101.4(4) . . ? C3 C2 N 123.8(4) . . ? C3 C2 C1 112.7(4) . . ? N C2 C1 123.3(4) . . ? C2 C3 C3A 108.2(4) . . ? C2 C3 P 117.1(3) . . ? C3A C3 P 134.8(4) . . ? C4 C3A C7A 120.2(4) . . ? C4 C3A C3 132.7(4) . . ? C7A C3A C3 107.0(4) . . ? C3A C4 C5 118.3(5) . . ? C6 C5 C4 121.8(5) . . ? C5 C6 C7 120.0(5) . . ? C6 C7 C7A 119.0(5) . . ? C7 C7A C3A 120.7(4) . . ? C7 C7A C1 128.8(4) . . ? C3A C7A C1 110.5(4) . . ? C12 C11 C18 122.2(4) . . ? C12 C11 Ir 69.0(3) . . ? C18 C11 Ir 113.9(3) . . ? C11 C12 C13 126.2(4) . . ? C11 C12 Ir 72.4(3) . . ? C13 C12 Ir 111.8(3) . . ? C12 C13 C14 113.3(4) . . ? C13 C14 C15 112.0(4) . . ? C16 C15 C14 123.7(5) . . ? C16 C15 Ir 70.4(3) . . ? C14 C15 Ir 111.9(3) . . ? C15 C16 C17 125.5(5) . . ? C15 C16 Ir 72.6(3) . . ? C17 C16 Ir 110.3(3) . . ? C16 C17 C18 113.1(4) . . ? C11 C18 C17 111.9(4) . . ? C23 C21 C22 110.9(4) . . ? C23 C21 P 115.6(3) . . ? C22 C21 P 109.0(3) . . ? C26 C24 C25 113.0(4) . . ? C26 C24 P 108.6(3) . . ? C25 C24 P 111.5(3) . . ? O1 S O2 115.0(2) . . ? O1 S O3 114.5(2) . . ? O2 S O3 115.3(2) . . ? O1 S C30 103.2(3) . . ? O2 S C30 103.3(3) . . ? O3 S C30 103.0(3) . . ? F3 C30 F2 107.6(6) . . ? F3 C30 F1 106.6(6) . . ? F2 C30 F1 106.0(6) . . ? F3 C30 S 112.4(5) . . ? F2 C30 S 112.0(5) . . ? F1 C30 S 111.8(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 Ir P C3 151.8(2) . . . . ? C11 Ir P C3 -169.8(2) . . . . ? C16 Ir P C3 -92.2(3) . . . . ? N Ir P C3 0.81(19) . . . . ? C15 Ir P C3 64(2) . . . . ? C12 Ir P C24 33.7(2) . . . . ? C11 Ir P C24 72.1(2) . . . . ? C16 Ir P C24 149.6(3) . . . . ? N Ir P C24 -117.3(2) . . . . ? C15 Ir P C24 -54(2) . . . . ? C12 Ir P C21 -96.1(2) . . . . ? C11 Ir P C21 -57.7(2) . . . . ? C16 Ir P C21 19.8(3) . . . . ? N Ir P C21 112.9(2) . . . . ? C15 Ir P C21 176(2) . . . . ? C12 Ir N C2 -104.2(4) . . . . ? C11 Ir N C2 69.9(10) . . . . ? C16 Ir N C2 140.7(3) . . . . ? C15 Ir N C2 177.8(3) . . . . ? P Ir N C2 -5.1(3) . . . . ? C12 Ir N C27 129.5(4) . . . . ? C11 Ir N C27 -56.4(10) . . . . ? C16 Ir N C27 14.4(4) . . . . ? C15 Ir N C27 51.4(3) . . . . ? P Ir N C27 -131.4(3) . . . . ? C12 Ir N C28 10.4(5) . . . . ? C11 Ir N C28 -175.5(8) . . . . ? C16 Ir N C28 -104.7(3) . . . . ? C15 Ir N C28 -67.7(3) . . . . ? P Ir N C28 109.5(3) . . . . ? C27 N C2 C3 140.5(5) . . . . ? C28 N C2 C3 -103.4(5) . . . . ? Ir N C2 C3 10.1(6) . . . . ? C27 N C2 C1 -44.8(6) . . . . ? C28 N C2 C1 71.3(5) . . . . ? Ir N C2 C1 -175.2(4) . . . . ? C7A C1 C2 C3 5.1(5) . . . . ? C7A C1 C2 N -170.1(4) . . . . ? N C2 C3 C3A 171.2(4) . . . . ? C1 C2 C3 C3A -4.0(6) . . . . ? N C2 C3 P -9.6(7) . . . . ? C1 C2 C3 P 175.2(3) . . . . ? C24 P C3 C2 134.7(4) . . . . ? C21 P C3 C2 -111.2(4) . . . . ? Ir P C3 C2 4.0(4) . . . . ? C24 P C3 C3A -46.4(5) . . . . ? C21 P C3 C3A 67.7(5) . . . . ? Ir P C3 C3A -177.1(5) . . . . ? C2 C3 C3A C4 -175.0(5) . . . . ? P C3 C3A C4 6.0(9) . . . . ? C2 C3 C3A C7A 1.0(6) . . . . ? P C3 C3A C7A -177.9(4) . . . . ? C7A C3A C4 C5 -0.3(8) . . . . ? C3 C3A C4 C5 175.3(5) . . . . ? C3A C4 C5 C6 0.5(8) . . . . ? C4 C5 C6 C7 -0.5(8) . . . . ? C5 C6 C7 C7A 0.2(8) . . . . ? C6 C7 C7A C3A 0.0(7) . . . . ? C6 C7 C7A C1 -178.7(5) . . . . ? C4 C3A C7A C7 0.1(7) . . . . ? C3 C3A C7A C7 -176.6(4) . . . . ? C4 C3A C7A C1 178.9(5) . . . . ? C3 C3A C7A C1 2.3(5) . . . . ? C2 C1 C7A C7 174.4(5) . . . . ? C2 C1 C7A C3A -4.3(5) . . . . ? C16 Ir C11 C12 112.5(3) . . . . ? N Ir C11 C12 -175.5(8) . . . . ? C15 Ir C11 C12 76.3(3) . . . . ? P Ir C11 C12 -101.2(3) . . . . ? C12 Ir C11 C18 -117.0(5) . . . . ? C16 Ir C11 C18 -4.6(4) . . . . ? N Ir C11 C18 67.5(10) . . . . ? C15 Ir C11 C18 -40.8(4) . . . . ? P Ir C11 C18 141.8(3) . . . . ? C18 C11 C12 C13 1.3(7) . . . . ? Ir C11 C12 C13 -104.5(5) . . . . ? C18 C11 C12 Ir 105.7(4) . . . . ? C16 Ir C12 C11 -66.4(3) . . . . ? N Ir C12 C11 178.4(3) . . . . ? C15 Ir C12 C11 -100.0(3) . . . . ? P Ir C12 C11 83.2(3) . . . . ? C11 Ir C12 C13 122.7(5) . . . . ? C16 Ir C12 C13 56.3(4) . . . . ? N Ir C12 C13 -58.9(5) . . . . ? C15 Ir C12 C13 22.7(3) . . . . ? P Ir C12 C13 -154.1(3) . . . . ? C11 C12 C13 C14 46.9(7) . . . . ? Ir C12 C13 C14 -36.7(5) . . . . ? C12 C13 C14 C15 31.6(6) . . . . ? C13 C14 C15 C16 -92.4(6) . . . . ? C13 C14 C15 Ir -12.0(6) . . . . ? C12 Ir C15 C16 113.7(3) . . . . ? C11 Ir C15 C16 75.8(3) . . . . ? N Ir C15 C16 -95.0(3) . . . . ? P Ir C15 C16 -158(2) . . . . ? C12 Ir C15 C14 -5.8(4) . . . . ? C11 Ir C15 C14 -43.7(4) . . . . ? C16 Ir C15 C14 -119.5(5) . . . . ? N Ir C15 C14 145.5(4) . . . . ? P Ir C15 C14 82(2) . . . . ? C14 C15 C16 C17 0.8(7) . . . . ? Ir C15 C16 C17 -102.9(5) . . . . ? C14 C15 C16 Ir 103.8(4) . . . . ? C12 Ir C16 C15 -65.2(3) . . . . ? C11 Ir C16 C15 -100.7(3) . . . . ? N Ir C16 C15 88.6(3) . . . . ? P Ir C16 C15 177.9(2) . . . . ? C12 Ir C16 C17 57.0(4) . . . . ? C11 Ir C16 C17 21.5(4) . . . . ? N Ir C16 C17 -149.2(4) . . . . ? C15 Ir C16 C17 122.2(5) . . . . ? P Ir C16 C17 -59.9(5) . . . . ? C15 C16 C17 C18 47.4(7) . . . . ? Ir C16 C17 C18 -35.3(5) . . . . ? C12 C11 C18 C17 -92.3(6) . . . . ? Ir C11 C18 C17 -13.0(5) . . . . ? C16 C17 C18 C11 31.9(6) . . . . ? C3 P C21 C23 -63.9(4) . . . . ? C24 P C21 C23 48.7(4) . . . . ? Ir P C21 C23 -173.2(3) . . . . ? C3 P C21 C22 61.8(4) . . . . ? C24 P C21 C22 174.5(3) . . . . ? Ir P C21 C22 -47.5(3) . . . . ? C3 P C24 C26 -65.8(4) . . . . ? C21 P C24 C26 -178.7(3) . . . . ? Ir P C24 C26 50.5(4) . . . . ? C3 P C24 C25 169.0(3) . . . . ? C21 P C24 C25 56.2(4) . . . . ? Ir P C24 C25 -74.7(4) . . . . ? O1 S C30 F3 -63.9(6) . . . . ? O2 S C30 F3 56.2(6) . . . . ? O3 S C30 F3 176.6(5) . . . . ? O1 S C30 F2 57.4(6) . . . . ? O2 S C30 F2 177.6(5) . . . . ? O3 S C30 F2 -62.0(6) . . . . ? O1 S C30 F1 176.2(5) . . . . ? O2 S C30 F1 -63.6(5) . . . . ? O3 S C30 F1 56.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.983 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.134 #===END data_dal04a8compound3 _database_code_depnum_ccdc_archive 'CCDC 270595' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H37 Ir N P' _chemical_formula_sum 'C25 H37 Ir N P' _chemical_formula_weight 574.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6714(5) _cell_length_b 16.9783(9) _cell_length_c 14.5080(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.4177(7) _cell_angle_gamma 90.00 _cell_volume 2246.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 7313 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.36 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 6.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2203 _exptl_absorpt_correction_T_max 0.5081 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17112 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.36 _reflns_number_total 4579 _reflns_number_gt 4273 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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^)+(0.0184P)^2^+1.5367P] 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 4579 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0194 _refine_ls_R_factor_gt 0.0174 _refine_ls_wR_factor_ref 0.0426 _refine_ls_wR_factor_gt 0.0419 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 Ir Ir 0.306227(9) 0.022375(5) 0.193543(6) 0.01792(4) Uani 1 1 d . . . P P 0.19957(6) 0.05322(4) 0.31030(4) 0.01745(12) Uani 1 1 d . . . N N 0.1746(2) 0.12296(12) 0.11306(14) 0.0213(4) Uani 1 1 d . . . C1 C -0.0688(3) 0.18592(15) 0.10681(19) 0.0259(5) Uani 1 1 d . . . H1 H -0.0997 0.2052 0.0417 0.031 Uiso 1 1 calc R . . C2 C 0.0567(3) 0.14303(14) 0.15266(17) 0.0206(5) Uani 1 1 d . . . C3 C 0.0699(3) 0.12473(14) 0.25022(17) 0.0190(5) Uani 1 1 d . . . C3A C -0.0572(3) 0.15772(14) 0.26575(18) 0.0207(5) Uani 1 1 d . . . C4 C -0.1074(3) 0.15963(15) 0.34627(19) 0.0264(5) Uani 1 1 d . . . H4 H -0.0523 0.1344 0.4056 0.032 Uiso 1 1 calc R . . C5 C -0.2356(3) 0.19782(16) 0.3395(2) 0.0306(6) Uani 1 1 d . . . H5 H -0.2681 0.1993 0.3945 0.037 Uiso 1 1 calc R . . C6 C -0.3196(3) 0.23482(16) 0.2516(2) 0.0328(6) Uani 1 1 d . . . H6 H -0.4083 0.2607 0.2479 0.039 Uiso 1 1 calc R . . C7 C -0.2746(3) 0.23381(16) 0.1715(2) 0.0310(6) Uani 1 1 d . . . H7 H -0.3322 0.2589 0.1127 0.037 Uiso 1 1 calc R . . C7A C -0.1428(3) 0.19561(14) 0.1761(2) 0.0243(5) Uani 1 1 d . . . C11 C 0.4513(3) 0.02641(16) 0.10456(19) 0.0276(6) Uani 1 1 d . . . H11 H 0.4334 0.0723 0.0588 0.033 Uiso 1 1 calc R . . C12 C 0.3553(3) -0.03615(17) 0.0703(2) 0.0295(6) Uani 1 1 d . . . H12 H 0.2799 -0.0272 0.0047 0.035 Uiso 1 1 calc R . . C13 C 0.4014(3) -0.12132(18) 0.0917(2) 0.0379(7) Uani 1 1 d . . . H13A H 0.5088 -0.1257 0.1068 0.045 Uiso 1 1 calc R . . H13B H 0.3531 -0.1537 0.0331 0.045 Uiso 1 1 calc R . . C14 C 0.3608(4) -0.15250(17) 0.1772(3) 0.0410(7) Uani 1 1 d . . . H14A H 0.2586 -0.1722 0.1530 0.049 Uiso 1 1 calc R . . H14B H 0.4255 -0.1975 0.2069 0.049 Uiso 1 1 calc R . . C15 C 0.3742(3) -0.09089(15) 0.2543(2) 0.0293(6) Uani 1 1 d . . . H15 H 0.3290 -0.1070 0.3042 0.035 Uiso 1 1 calc R . . C16 C 0.4905(3) -0.03644(16) 0.29016(19) 0.0269(6) Uani 1 1 d . . . H16 H 0.5106 -0.0221 0.3603 0.032 Uiso 1 1 calc R . . C17 C 0.6267(3) -0.03439(17) 0.2596(2) 0.0302(6) Uani 1 1 d . . . H17A H 0.6498 -0.0886 0.2441 0.036 Uiso 1 1 calc R . . H17B H 0.7108 -0.0151 0.3150 0.036 Uiso 1 1 calc R . . C18 C 0.6075(3) 0.01843(17) 0.1708(2) 0.0325(6) Uani 1 1 d . . . H18A H 0.6462 0.0715 0.1940 0.039 Uiso 1 1 calc R . . H18B H 0.6667 -0.0032 0.1327 0.039 Uiso 1 1 calc R . . C21 C 0.3294(3) 0.08994(15) 0.42669(17) 0.0242(5) Uani 1 1 d . . . H21 H 0.3905 0.0443 0.4609 0.029 Uiso 1 1 calc R . . C22 C 0.2557(3) 0.12471(18) 0.49576(19) 0.0309(6) Uani 1 1 d . . . H22A H 0.1865 0.0863 0.5060 0.037 Uiso 1 1 calc R . . H22B H 0.2029 0.1728 0.4670 0.037 Uiso 1 1 calc R . . H22C H 0.3304 0.1373 0.5586 0.037 Uiso 1 1 calc R . . C23 C 0.4326(3) 0.15079(17) 0.4070(2) 0.0335(6) Uani 1 1 d . . . H23A H 0.4791 0.1284 0.3624 0.040 Uiso 1 1 calc R . . H23B H 0.5082 0.1652 0.4687 0.040 Uiso 1 1 calc R . . H23C H 0.3766 0.1978 0.3774 0.040 Uiso 1 1 calc R . . C24 C 0.0882(3) -0.02275(14) 0.3461(2) 0.0278(6) Uani 1 1 d . . . H24 H 0.0173 0.0066 0.3701 0.033 Uiso 1 1 calc R . . C25 C -0.0031(3) -0.06616(18) 0.2546(2) 0.0388(7) Uani 1 1 d . . . H25A H -0.0526 -0.0279 0.2037 0.047 Uiso 1 1 calc R . . H25B H -0.0764 -0.0988 0.2696 0.047 Uiso 1 1 calc R . . H25C H 0.0609 -0.0998 0.2314 0.047 Uiso 1 1 calc R . . C26 C 0.1716(4) -0.07876(18) 0.4289(2) 0.0445(8) Uani 1 1 d . . . H26A H 0.2300 -0.0480 0.4856 0.053 Uiso 1 1 calc R . . H26B H 0.2365 -0.1125 0.4067 0.053 Uiso 1 1 calc R . . H26C H 0.1014 -0.1116 0.4472 0.053 Uiso 1 1 calc R . . C27 C 0.1113(3) 0.10978(18) 0.00558(18) 0.0319(6) Uani 1 1 d . . . H27A H 0.1901 0.0968 -0.0203 0.038 Uiso 1 1 calc R . . H27B H 0.0611 0.1577 -0.0261 0.038 Uiso 1 1 calc R . . H27C H 0.0411 0.0661 -0.0075 0.038 Uiso 1 1 calc R . . C28 C 0.2730(3) 0.19355(15) 0.1292(2) 0.0290(6) Uani 1 1 d . . . H28A H 0.3176 0.2033 0.1994 0.035 Uiso 1 1 calc R . . H28B H 0.2155 0.2397 0.0979 0.035 Uiso 1 1 calc R . . H28C H 0.3503 0.1839 0.1007 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir 0.01909(6) 0.01891(6) 0.01726(6) 0.00102(3) 0.00805(4) 0.00246(3) P 0.0188(3) 0.0172(3) 0.0172(3) 0.0012(2) 0.0072(2) 0.0020(2) N 0.0219(10) 0.0227(10) 0.0202(10) 0.0028(8) 0.0085(8) 0.0015(8) C1 0.0231(12) 0.0262(13) 0.0272(13) 0.0103(10) 0.0066(11) 0.0034(10) C2 0.0199(11) 0.0199(12) 0.0227(12) 0.0025(9) 0.0081(10) 0.0000(9) C3 0.0187(11) 0.0190(11) 0.0192(11) 0.0012(9) 0.0061(9) 0.0006(9) C3A 0.0187(11) 0.0168(11) 0.0264(12) 0.0010(9) 0.0075(10) -0.0006(9) C4 0.0265(13) 0.0265(13) 0.0283(13) -0.0001(11) 0.0122(11) 0.0015(11) C5 0.0279(14) 0.0284(14) 0.0423(16) -0.0026(12) 0.0208(13) 0.0008(11) C6 0.0236(13) 0.0228(13) 0.0582(19) 0.0044(13) 0.0218(13) 0.0048(11) C7 0.0236(13) 0.0259(13) 0.0430(16) 0.0119(12) 0.0101(12) 0.0053(11) C7A 0.0210(12) 0.0190(12) 0.0335(14) 0.0044(10) 0.0098(11) 0.0001(9) C11 0.0284(14) 0.0371(15) 0.0226(13) 0.0043(11) 0.0156(11) 0.0052(11) C12 0.0281(14) 0.0400(15) 0.0228(13) -0.0067(11) 0.0114(11) 0.0069(12) C13 0.0340(15) 0.0365(16) 0.0428(17) -0.0157(14) 0.0124(13) 0.0034(13) C14 0.0412(17) 0.0231(14) 0.063(2) -0.0063(14) 0.0225(16) 0.0024(12) C15 0.0326(14) 0.0210(13) 0.0392(15) 0.0083(11) 0.0186(12) 0.0102(11) C16 0.0270(13) 0.0316(14) 0.0227(13) 0.0072(10) 0.0090(11) 0.0133(11) C17 0.0250(13) 0.0377(15) 0.0283(14) 0.0014(12) 0.0093(11) 0.0055(11) C18 0.0257(14) 0.0413(17) 0.0339(15) 0.0035(12) 0.0144(12) -0.0016(12) C21 0.0257(12) 0.0261(13) 0.0178(11) -0.0007(10) 0.0034(10) 0.0056(10) C22 0.0328(14) 0.0380(15) 0.0210(13) -0.0055(11) 0.0076(11) 0.0053(12) C23 0.0262(13) 0.0376(16) 0.0353(15) -0.0115(12) 0.0082(12) -0.0074(12) C24 0.0316(14) 0.0220(13) 0.0387(15) 0.0047(11) 0.0238(12) 0.0018(10) C25 0.0323(15) 0.0299(15) 0.060(2) -0.0071(14) 0.0237(14) -0.0091(12) C26 0.071(2) 0.0304(15) 0.0466(18) 0.0161(14) 0.0386(17) 0.0108(15) C27 0.0350(15) 0.0411(16) 0.0199(13) 0.0064(11) 0.0096(11) 0.0077(12) C28 0.0287(14) 0.0239(13) 0.0382(15) 0.0055(11) 0.0160(12) -0.0009(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir C16 2.116(2) . ? Ir C15 2.127(2) . ? Ir C11 2.201(3) . ? Ir N 2.216(2) . ? Ir C12 2.231(3) . ? Ir P 2.3171(6) . ? P C3 1.755(2) . ? P C21 1.846(2) . ? P C24 1.862(3) . ? N C2 1.478(3) . ? N C27 1.491(3) . ? N C28 1.499(3) . ? C1 C2 1.381(3) . ? C1 C7A 1.424(4) . ? C2 C3 1.413(3) . ? C3 C3A 1.435(3) . ? C3A C4 1.406(3) . ? C3A C7A 1.440(3) . ? C4 C5 1.374(4) . ? C5 C6 1.411(4) . ? C6 C7 1.370(4) . ? C7 C7A 1.412(4) . ? C11 C12 1.389(4) . ? C11 C18 1.503(4) . ? C12 C13 1.515(4) . ? C13 C14 1.515(4) . ? C14 C15 1.506(4) . ? C15 C16 1.415(4) . ? C16 C17 1.524(4) . ? C17 C18 1.529(4) . ? C21 C23 1.528(4) . ? C21 C22 1.528(3) . ? C24 C25 1.519(4) . ? C24 C26 1.533(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 C16 Ir C15 38.96(11) . . ? C16 Ir C11 80.94(10) . . ? C15 Ir C11 95.86(10) . . ? C16 Ir N 157.28(10) . . ? C15 Ir N 163.63(10) . . ? C11 Ir N 91.91(9) . . ? C16 Ir C12 87.93(10) . . ? C15 Ir C12 79.10(11) . . ? C11 Ir C12 36.53(10) . . ? N Ir C12 99.15(9) . . ? C16 Ir P 95.97(7) . . ? C15 Ir P 93.01(8) . . ? C11 Ir P 161.31(8) . . ? N Ir P 83.90(5) . . ? C12 Ir P 162.16(8) . . ? C3 P C21 112.16(11) . . ? C3 P C24 103.51(12) . . ? C21 P C24 105.03(13) . . ? C3 P Ir 102.23(8) . . ? C21 P Ir 114.35(8) . . ? C24 P Ir 119.14(9) . . ? C2 N C27 109.84(19) . . ? C2 N C28 106.69(19) . . ? C27 N C28 107.6(2) . . ? C2 N Ir 110.81(14) . . ? C27 N Ir 113.57(16) . . ? C28 N Ir 108.08(15) . . ? C2 C1 C7A 106.8(2) . . ? C1 C2 C3 111.8(2) . . ? C1 C2 N 127.0(2) . . ? C3 C2 N 121.0(2) . . ? C2 C3 C3A 105.9(2) . . ? C2 C3 P 117.46(18) . . ? C3A C3 P 134.44(18) . . ? C4 C3A C3 133.6(2) . . ? C4 C3A C7A 119.1(2) . . ? C3 C3A C7A 107.3(2) . . ? C5 C4 C3A 120.2(2) . . ? C4 C5 C6 120.6(3) . . ? C7 C6 C5 120.7(2) . . ? C6 C7 C7A 120.2(2) . . ? C7 C7A C1 132.7(2) . . ? C7 C7A C3A 119.1(2) . . ? C1 C7A C3A 108.2(2) . . ? C12 C11 C18 124.7(2) . . ? C12 C11 Ir 72.90(16) . . ? C18 C11 Ir 108.84(18) . . ? C11 C12 C13 122.7(2) . . ? C11 C12 Ir 70.58(15) . . ? C13 C12 Ir 112.78(19) . . ? C12 C13 C14 111.3(2) . . ? C15 C14 C13 112.6(2) . . ? C16 C15 C14 126.0(2) . . ? C16 C15 Ir 70.11(14) . . ? C14 C15 Ir 112.44(19) . . ? C15 C16 C17 124.5(2) . . ? C15 C16 Ir 70.93(14) . . ? C17 C16 Ir 114.56(17) . . ? C16 C17 C18 112.6(2) . . ? C11 C18 C17 114.0(2) . . ? C23 C21 C22 109.7(2) . . ? C23 C21 P 110.21(18) . . ? C22 C21 P 113.99(18) . . ? C25 C24 C26 112.6(2) . . ? C25 C24 P 108.32(19) . . ? C26 C24 P 116.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 Ir P C3 165.01(11) . . . . ? C15 Ir P C3 -156.01(11) . . . . ? C11 Ir P C3 85.7(2) . . . . ? N Ir P C3 7.87(10) . . . . ? C12 Ir P C3 -93.1(3) . . . . ? C16 Ir P C21 43.57(12) . . . . ? C15 Ir P C21 82.55(12) . . . . ? C11 Ir P C21 -35.8(2) . . . . ? N Ir P C21 -113.58(11) . . . . ? C12 Ir P C21 145.5(3) . . . . ? C16 Ir P C24 -81.75(13) . . . . ? C15 Ir P C24 -42.77(13) . . . . ? C11 Ir P C24 -161.1(2) . . . . ? N Ir P C24 121.10(12) . . . . ? C12 Ir P C24 20.2(3) . . . . ? C16 Ir N C2 -108.2(2) . . . . ? C15 Ir N C2 62.5(4) . . . . ? C11 Ir N C2 -179.04(16) . . . . ? C12 Ir N C2 144.96(16) . . . . ? P Ir N C2 -17.30(14) . . . . ? C16 Ir N C27 127.6(2) . . . . ? C15 Ir N C27 -61.6(4) . . . . ? C11 Ir N C27 56.79(18) . . . . ? C12 Ir N C27 20.79(19) . . . . ? P Ir N C27 -141.48(17) . . . . ? C16 Ir N C28 8.4(3) . . . . ? C15 Ir N C28 179.1(3) . . . . ? C11 Ir N C28 -62.48(17) . . . . ? C12 Ir N C28 -98.48(17) . . . . ? P Ir N C28 99.26(15) . . . . ? C7A C1 C2 C3 -0.8(3) . . . . ? C7A C1 C2 N -175.2(2) . . . . ? C27 N C2 C1 -34.5(3) . . . . ? C28 N C2 C1 81.8(3) . . . . ? Ir N C2 C1 -160.8(2) . . . . ? C27 N C2 C3 151.6(2) . . . . ? C28 N C2 C3 -92.1(3) . . . . ? Ir N C2 C3 25.3(3) . . . . ? C1 C2 C3 C3A 0.7(3) . . . . ? N C2 C3 C3A 175.5(2) . . . . ? C1 C2 C3 P 166.47(18) . . . . ? N C2 C3 P -18.7(3) . . . . ? C21 P C3 C2 125.37(19) . . . . ? C24 P C3 C2 -121.9(2) . . . . ? Ir P C3 C2 2.4(2) . . . . ? C21 P C3 C3A -74.0(3) . . . . ? C24 P C3 C3A 38.7(3) . . . . ? Ir P C3 C3A 163.0(2) . . . . ? C2 C3 C3A C4 -180.0(3) . . . . ? P C3 C3A C4 17.9(4) . . . . ? C2 C3 C3A C7A -0.4(3) . . . . ? P C3 C3A C7A -162.5(2) . . . . ? C3 C3A C4 C5 178.9(3) . . . . ? C7A C3A C4 C5 -0.6(4) . . . . ? C3A C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C7A -0.1(4) . . . . ? C6 C7 C7A C1 -179.1(3) . . . . ? C6 C7 C7A C3A 0.2(4) . . . . ? C2 C1 C7A C7 179.8(3) . . . . ? C2 C1 C7A C3A 0.5(3) . . . . ? C4 C3A C7A C7 0.2(4) . . . . ? C3 C3A C7A C7 -179.5(2) . . . . ? C4 C3A C7A C1 179.6(2) . . . . ? C3 C3A C7A C1 -0.1(3) . . . . ? C16 Ir C11 C12 98.85(18) . . . . ? C15 Ir C11 C12 62.74(18) . . . . ? N Ir C11 C12 -102.83(16) . . . . ? P Ir C11 C12 -179.36(17) . . . . ? C16 Ir C11 C18 -22.81(19) . . . . ? C15 Ir C11 C18 -58.9(2) . . . . ? N Ir C11 C18 135.51(19) . . . . ? C12 Ir C11 C18 -121.7(3) . . . . ? P Ir C11 C18 59.0(3) . . . . ? C18 C11 C12 C13 -3.7(4) . . . . ? Ir C11 C12 C13 -105.2(3) . . . . ? C18 C11 C12 Ir 101.4(3) . . . . ? C16 Ir C12 C11 -77.53(17) . . . . ? C15 Ir C12 C11 -115.77(18) . . . . ? N Ir C12 C11 80.76(16) . . . . ? P Ir C12 C11 179.33(18) . . . . ? C16 Ir C12 C13 40.7(2) . . . . ? C15 Ir C12 C13 2.5(2) . . . . ? C11 Ir C12 C13 118.3(3) . . . . ? N Ir C12 C13 -160.97(19) . . . . ? P Ir C12 C13 -62.4(3) . . . . ? C11 C12 C13 C14 97.5(3) . . . . ? Ir C12 C13 C14 16.6(3) . . . . ? C12 C13 C14 C15 -35.2(3) . . . . ? C13 C14 C15 C16 -43.2(4) . . . . ? C13 C14 C15 Ir 37.9(3) . . . . ? C11 Ir C15 C16 67.76(17) . . . . ? N Ir C15 C16 -174.3(3) . . . . ? C12 Ir C15 C16 100.36(17) . . . . ? P Ir C15 C16 -95.77(15) . . . . ? C16 Ir C15 C14 -121.8(3) . . . . ? C11 Ir C15 C14 -54.1(2) . . . . ? N Ir C15 C14 63.8(4) . . . . ? C12 Ir C15 C14 -21.5(2) . . . . ? P Ir C15 C14 142.39(19) . . . . ? C14 C15 C16 C17 -3.4(4) . . . . ? Ir C15 C16 C17 -107.2(2) . . . . ? C14 C15 C16 Ir 103.8(3) . . . . ? C11 Ir C16 C15 -111.19(17) . . . . ? N Ir C16 C15 175.86(19) . . . . ? C12 Ir C16 C15 -75.14(17) . . . . ? P Ir C16 C15 87.40(15) . . . . ? C15 Ir C16 C17 120.1(3) . . . . ? C11 Ir C16 C17 8.9(2) . . . . ? N Ir C16 C17 -64.1(3) . . . . ? C12 Ir C16 C17 44.9(2) . . . . ? P Ir C16 C17 -152.51(19) . . . . ? C15 C16 C17 C18 89.8(3) . . . . ? Ir C16 C17 C18 6.8(3) . . . . ? C12 C11 C18 C17 -48.3(4) . . . . ? Ir C11 C18 C17 33.5(3) . . . . ? C16 C17 C18 C11 -27.2(3) . . . . ? C3 P C21 C23 -70.7(2) . . . . ? C24 P C21 C23 177.57(18) . . . . ? Ir P C21 C23 45.1(2) . . . . ? C3 P C21 C22 53.2(2) . . . . ? C24 P C21 C22 -58.6(2) . . . . ? Ir P C21 C22 168.98(17) . . . . ? C3 P C24 C25 72.1(2) . . . . ? C21 P C24 C25 -170.12(19) . . . . ? Ir P C24 C25 -40.4(2) . . . . ? C3 P C24 C26 -159.7(2) . . . . ? C21 P C24 C26 -41.9(2) . . . . ? Ir P C24 C26 87.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.743 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.090