# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Garralda, Maria' _publ_contact_author_email mariaangeles.garralda@ehu.es _publ_section_title ; A hydridoirida-\^I^2^-diketone as efficient and robust homogeneous catalyst for the hydrolysis of ammonia-borane or amine-borane adducts in air to produce hydrogen ; loop_ _publ_author_name M.Garralda L.Ibarlucea R.Ciganda M.R.Torres E.Pinilla # Attachment '- Compound3DT-COM-03-2010-000091 REVISED.cif' data_C39H33ClIrN1O1P2_compound_3 _database_code_depnum_ccdc_archive 'CCDC 776710' #TrackingRef '- Compound3DT-COM-03-2010-000091 REVISED.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H33 Cl Ir N O P2' _chemical_formula_weight 821.25 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' 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' Cl Cl 0.1484 0.1585 '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 12.8150(9) _cell_length_b 19.3807(13) _cell_length_c 14.3644(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.1800(10) _cell_angle_gamma 90.00 _cell_volume 3389.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5362 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 23.04 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 4.144 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.5225 _exptl_absorpt_correction_T_max 0.7891 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 25677 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5956 _reflns_number_gt 4383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^+5.3913P] 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 5956 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir Ir 0.491327(17) 0.839081(11) 0.184906(17) 0.02876(8) Uani 1 1 d . . . H1 H 0.4968 0.7680 0.1610 0.035 Uiso 1 1 d . . . C1 C 0.3271(5) 0.8361(3) 0.1105(4) 0.0338(13) Uani 1 1 d . . . Cl1 Cl 0.47555(13) 0.96238(7) 0.23278(11) 0.0417(4) Uani 1 1 d . . . O1 O 0.2855(3) 0.8271(2) 0.0213(3) 0.0467(11) Uani 1 1 d . . . P1 P 0.43043(11) 0.80371(8) 0.31236(11) 0.0313(4) Uani 1 1 d . . . C2 C 0.2495(5) 0.8463(3) 0.1692(5) 0.0392(15) Uani 1 1 d . . . N1 N 0.4734(4) 0.8530(3) -0.0247(4) 0.0458(14) Uani 1 1 d . . . H2 H 0.3731 0.8270 -0.0166 0.055 Uiso 1 1 d . . . P2 P 0.68346(11) 0.83813(8) 0.24759(11) 0.0318(3) Uani 1 1 d . . . C3 C 0.2880(4) 0.8337(3) 0.2696(5) 0.0388(15) Uani 1 1 d . . . C4 C 0.2173(5) 0.8402(4) 0.3255(6) 0.0561(19) Uani 1 1 d . . . H4 H 0.2417 0.8302 0.3921 0.067 Uiso 1 1 calc R . . C5 C 0.1105(6) 0.8619(5) 0.2811(7) 0.077(3) Uani 1 1 d . . . H5 H 0.0638 0.8683 0.3187 0.093 Uiso 1 1 calc R . . C6 C 0.0725(6) 0.8740(4) 0.1812(7) 0.069(2) Uani 1 1 d . . . H6 H 0.0002 0.8879 0.1518 0.083 Uiso 1 1 calc R . . C7 C 0.1413(5) 0.8655(3) 0.1252(5) 0.0502(18) Uani 1 1 d . . . H7 H 0.1151 0.8726 0.0579 0.060 Uiso 1 1 calc R . . C8 C 0.4941(5) 0.8370(3) 0.4359(4) 0.0350(14) Uani 1 1 d . . . C9 C 0.5840(5) 0.8024(3) 0.4978(5) 0.0492(17) Uani 1 1 d . . . H9 H 0.6095 0.7624 0.4766 0.059 Uiso 1 1 calc R . . C10 C 0.6358(6) 0.8275(4) 0.5910(5) 0.064(2) Uani 1 1 d . . . H10 H 0.6945 0.8035 0.6332 0.077 Uiso 1 1 calc R . . C11 C 0.6003(7) 0.8880(4) 0.6214(5) 0.065(2) Uani 1 1 d . . . H11 H 0.6347 0.9046 0.6843 0.078 Uiso 1 1 calc R . . C12 C 0.5143(6) 0.9236(3) 0.5590(5) 0.0552(19) Uani 1 1 d . . . H12 H 0.4917 0.9652 0.5790 0.066 Uiso 1 1 calc R . . C13 C 0.4610(5) 0.8982(3) 0.4668(5) 0.0441(16) Uani 1 1 d . . . H13 H 0.4023 0.9225 0.4251 0.053 Uiso 1 1 calc R . . C14 C 0.4109(4) 0.7121(3) 0.3353(4) 0.0344(14) Uani 1 1 d . . . C15 C 0.4188(5) 0.6621(3) 0.2699(5) 0.0483(17) Uani 1 1 d . . . H15 H 0.4411 0.6740 0.2163 0.058 Uiso 1 1 calc R . . C16 C 0.3936(7) 0.5937(4) 0.2835(6) 0.067(2) Uani 1 1 d . . . H16 H 0.3998 0.5601 0.2392 0.080 Uiso 1 1 calc R . . C17 C 0.3596(6) 0.5754(4) 0.3621(6) 0.060(2) Uani 1 1 d . . . H17 H 0.3422 0.5297 0.3708 0.072 Uiso 1 1 calc R . . C18 C 0.3518(6) 0.6251(4) 0.4270(6) 0.064(2) Uani 1 1 d . . . H18 H 0.3282 0.6134 0.4800 0.076 Uiso 1 1 calc R . . C19 C 0.3784(6) 0.6920(4) 0.4144(5) 0.0566(19) Uani 1 1 d . . . H19 H 0.3745 0.7250 0.4603 0.068 Uiso 1 1 calc R . . C20 C 0.5306(5) 0.8711(3) 0.0645(4) 0.0352(14) Uani 1 1 d . . . C21 C 0.6322(5) 0.9138(3) 0.0803(4) 0.0349(14) Uani 1 1 d . . . C22 C 0.7159(4) 0.9017(3) 0.1684(4) 0.0317(14) Uani 1 1 d . . . C23 C 0.8107(5) 0.9421(3) 0.1910(5) 0.0411(16) Uani 1 1 d . . . H23 H 0.8669 0.9347 0.2493 0.049 Uiso 1 1 calc R . . C24 C 0.8216(5) 0.9931(3) 0.1272(5) 0.0490(18) Uani 1 1 d . . . H24 H 0.8865 1.0183 0.1412 0.059 Uiso 1 1 calc R . . C25 C 0.7366(5) 1.0065(3) 0.0432(5) 0.0483(18) Uani 1 1 d . . . H25 H 0.7427 1.0426 0.0025 0.058 Uiso 1 1 calc R . . C26 C 0.6431(5) 0.9674(3) 0.0187(5) 0.0409(15) Uani 1 1 d . . . H26 H 0.5868 0.9764 -0.0390 0.049 Uiso 1 1 calc R . . C27 C 0.7400(4) 0.7571(3) 0.2194(4) 0.0357(14) Uani 1 1 d . . . C28 C 0.8056(6) 0.7536(3) 0.1598(5) 0.0551(19) Uani 1 1 d . . . H28 H 0.8288 0.7942 0.1379 0.066 Uiso 1 1 calc R . . C29 C 0.8376(7) 0.6910(4) 0.1319(6) 0.072(2) Uani 1 1 d . . . H29 H 0.8824 0.6896 0.0920 0.087 Uiso 1 1 calc R . . C30 C 0.8032(7) 0.6312(4) 0.1632(6) 0.069(2) Uani 1 1 d . . . H30 H 0.8232 0.5888 0.1434 0.083 Uiso 1 1 calc R . . C31 C 0.7399(6) 0.6336(4) 0.2229(7) 0.078(3) Uani 1 1 d . . . H31 H 0.7177 0.5927 0.2449 0.094 Uiso 1 1 calc R . . C32 C 0.7081(6) 0.6958(4) 0.2513(6) 0.065(2) Uani 1 1 d . . . H32 H 0.6647 0.6966 0.2925 0.078 Uiso 1 1 calc R . . C33 C 0.7741(5) 0.8645(3) 0.3664(4) 0.0401(15) Uani 1 1 d . . . C34 C 0.8744(5) 0.8330(4) 0.4121(5) 0.059(2) Uani 1 1 d . . . H34 H 0.8927 0.7925 0.3861 0.071 Uiso 1 1 calc R . . C35 C 0.9469(6) 0.8609(5) 0.4953(6) 0.077(3) Uani 1 1 d . . . H35 H 1.0144 0.8396 0.5241 0.092 Uiso 1 1 calc R . . C36 C 0.9213(7) 0.9187(6) 0.5354(6) 0.083(3) Uani 1 1 d . . . H36 H 0.9717 0.9376 0.5909 0.100 Uiso 1 1 calc R . . C37 C 0.8212(7) 0.9501(5) 0.4950(6) 0.079(3) Uani 1 1 d . . . H37 H 0.8029 0.9893 0.5238 0.095 Uiso 1 1 calc R . . C38 C 0.7469(6) 0.9224(4) 0.4100(5) 0.063(2) Uani 1 1 d . . . H38 H 0.6787 0.9431 0.3826 0.075 Uiso 1 1 calc R . . C39 C 0.5032(7) 0.8589(4) -0.1153(5) 0.075(3) Uani 1 1 d . . . H39A H 0.4780 0.9024 -0.1461 0.112 Uiso 1 1 calc R . . H39B H 0.4695 0.8220 -0.1590 0.112 Uiso 1 1 calc R . . H39C H 0.5816 0.8561 -0.0999 0.112 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 0.02899(12) 0.03012(13) 0.03039(14) 0.00169(12) 0.01390(9) 0.00052(11) C1 0.040(3) 0.026(3) 0.035(4) 0.002(3) 0.012(3) -0.006(3) Cl1 0.0576(9) 0.0317(8) 0.0399(9) -0.0013(7) 0.0209(7) 0.0018(7) O1 0.037(2) 0.055(3) 0.048(3) -0.001(2) 0.013(2) -0.005(2) P1 0.0322(7) 0.0319(9) 0.0339(9) 0.0014(7) 0.0163(7) -0.0013(6) C2 0.036(3) 0.033(4) 0.052(4) 0.000(3) 0.019(3) -0.003(3) N1 0.060(3) 0.055(4) 0.027(3) -0.004(3) 0.020(3) -0.010(3) P2 0.0311(7) 0.0364(9) 0.0312(9) 0.0046(8) 0.0145(6) 0.0012(7) C3 0.030(3) 0.037(4) 0.056(4) -0.004(3) 0.022(3) 0.000(3) C4 0.049(4) 0.066(5) 0.065(5) 0.007(4) 0.034(4) 0.009(4) C5 0.048(4) 0.116(7) 0.084(7) 0.005(5) 0.043(4) 0.015(4) C6 0.038(4) 0.085(6) 0.090(7) 0.006(5) 0.027(4) 0.014(4) C7 0.035(3) 0.057(4) 0.058(5) 0.008(4) 0.013(3) 0.002(3) C8 0.050(3) 0.027(3) 0.037(4) -0.004(3) 0.026(3) -0.008(3) C9 0.052(4) 0.042(4) 0.048(5) 0.005(3) 0.006(3) 0.004(3) C10 0.065(5) 0.067(6) 0.048(5) -0.001(4) 0.000(4) -0.002(4) C11 0.092(6) 0.061(5) 0.039(5) -0.006(4) 0.017(4) -0.025(5) C12 0.085(5) 0.035(4) 0.056(5) -0.005(4) 0.036(4) -0.015(4) C13 0.057(4) 0.042(4) 0.038(4) 0.002(3) 0.023(3) -0.009(3) C14 0.033(3) 0.032(3) 0.038(4) 0.001(3) 0.010(3) -0.003(3) C15 0.058(4) 0.039(4) 0.052(4) 0.008(4) 0.025(3) 0.004(3) C16 0.094(6) 0.042(5) 0.071(6) -0.010(4) 0.034(5) -0.006(4) C17 0.072(5) 0.041(4) 0.068(6) 0.010(4) 0.022(4) -0.010(4) C18 0.088(6) 0.054(5) 0.056(5) 0.010(4) 0.035(4) -0.019(4) C19 0.082(5) 0.052(5) 0.043(4) 0.002(4) 0.030(4) -0.018(4) C20 0.037(3) 0.037(3) 0.035(4) 0.006(3) 0.015(3) 0.005(3) C21 0.042(3) 0.030(3) 0.042(4) 0.003(3) 0.027(3) 0.004(3) C22 0.035(3) 0.029(3) 0.036(4) 0.003(3) 0.017(3) 0.001(2) C23 0.031(3) 0.041(4) 0.056(4) 0.003(3) 0.021(3) -0.001(3) C24 0.052(4) 0.038(4) 0.071(5) -0.002(4) 0.040(4) -0.002(3) C25 0.061(4) 0.029(4) 0.075(5) 0.013(3) 0.050(4) 0.007(3) C26 0.048(4) 0.038(4) 0.043(4) 0.010(3) 0.024(3) 0.009(3) C27 0.031(3) 0.040(4) 0.037(4) 0.007(3) 0.012(3) 0.005(3) C28 0.086(5) 0.039(4) 0.058(5) 0.016(4) 0.047(4) 0.020(4) C29 0.116(7) 0.061(5) 0.058(5) 0.009(4) 0.052(5) 0.029(5) C30 0.087(6) 0.040(5) 0.080(6) 0.000(4) 0.026(5) 0.014(4) C31 0.070(5) 0.035(4) 0.138(9) 0.028(5) 0.044(6) 0.004(4) C32 0.061(4) 0.044(4) 0.109(7) 0.028(5) 0.051(5) 0.015(4) C33 0.038(3) 0.054(4) 0.032(4) 0.004(3) 0.017(3) -0.011(3) C34 0.046(4) 0.079(6) 0.046(5) 0.004(4) 0.006(3) -0.002(4) C35 0.056(5) 0.116(8) 0.051(5) 0.014(5) 0.006(4) 0.007(5) C36 0.074(6) 0.127(9) 0.040(5) -0.009(5) 0.006(4) -0.030(6) C37 0.098(7) 0.083(7) 0.055(6) -0.019(5) 0.021(5) -0.012(5) C38 0.061(5) 0.076(6) 0.048(5) -0.012(4) 0.013(4) -0.004(4) C39 0.091(6) 0.099(7) 0.037(5) -0.013(4) 0.024(4) -0.037(5) _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 C20 2.043(6) . ? Ir C1 2.042(6) . ? Ir P1 2.3070(15) . ? Ir P2 2.3431(14) . ? Ir Cl1 2.5122(15) . ? Ir H1 1.4268 . ? C1 O1 1.237(7) . ? C1 C2 1.505(8) . ? O1 H2 1.3919 . ? P1 C8 1.824(6) . ? P1 C3 1.830(6) . ? P1 C14 1.837(6) . ? C2 C3 1.393(8) . ? C2 C7 1.383(8) . ? N1 C20 1.310(7) . ? N1 C39 1.471(8) . ? N1 H2 1.4190 . ? P2 C22 1.812(6) . ? P2 C33 1.813(6) . ? P2 C27 1.828(6) . ? C3 C4 1.390(8) . ? C4 C5 1.382(9) . ? C4 H4 0.9300 . ? C5 C6 1.385(10) . ? C5 H5 0.9300 . ? C6 C7 1.376(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C13 1.379(8) . ? C8 C9 1.388(8) . ? C9 C10 1.384(9) . ? C9 H9 0.9300 . ? C10 C11 1.376(10) . ? C10 H10 0.9300 . ? C11 C12 1.372(10) . ? C11 H11 0.9300 . ? C12 C13 1.378(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.377(8) . ? C14 C19 1.381(8) . ? C15 C16 1.393(9) . ? C15 H15 0.9300 . ? C16 C17 1.377(10) . ? C16 H16 0.9300 . ? C17 C18 1.367(10) . ? C17 H17 0.9300 . ? C18 C19 1.367(9) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.499(8) . ? C21 C22 1.399(8) . ? C21 C26 1.399(8) . ? C22 C23 1.396(7) . ? C23 C24 1.384(8) . ? C23 H23 0.9300 . ? C24 C25 1.375(9) . ? C24 H24 0.9300 . ? C25 C26 1.367(8) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.376(8) . ? C27 C32 1.379(8) . ? C28 C29 1.379(9) . ? C28 H28 0.9300 . ? C29 C30 1.365(10) . ? C29 H29 0.9300 . ? C30 C31 1.352(11) . ? C30 H30 0.9300 . ? C31 C32 1.376(10) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C38 1.381(9) . ? C33 C34 1.389(9) . ? C34 C35 1.375(10) . ? C34 H34 0.9300 . ? C35 C36 1.347(11) . ? C35 H35 0.9300 . ? C36 C37 1.374(11) . ? C36 H36 0.9300 . ? C37 C38 1.400(10) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 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 C20 Ir C1 92.9(2) . . ? C20 Ir P1 174.80(16) . . ? C1 Ir P1 81.88(17) . . ? C20 Ir P2 79.67(16) . . ? C1 Ir P2 171.33(18) . . ? P1 Ir P2 105.53(5) . . ? C20 Ir Cl1 90.25(17) . . ? C1 Ir Cl1 90.69(16) . . ? P1 Ir Cl1 89.39(5) . . ? P2 Ir Cl1 93.84(5) . . ? C20 Ir H1 92.7 . . ? C1 Ir H1 88.1 . . ? P1 Ir H1 87.6 . . ? P2 Ir H1 87.7 . . ? Cl1 Ir H1 176.9 . . ? O1 C1 C2 116.9(5) . . ? O1 C1 Ir 125.9(4) . . ? C2 C1 Ir 117.2(4) . . ? C1 O1 H2 105.4 . . ? C8 P1 C3 108.1(3) . . ? C8 P1 C14 102.2(3) . . ? C3 P1 C14 100.9(3) . . ? C8 P1 Ir 120.53(19) . . ? C3 P1 Ir 100.9(2) . . ? C14 P1 Ir 121.9(2) . . ? C3 C2 C7 120.1(6) . . ? C3 C2 C1 118.4(5) . . ? C7 C2 C1 121.5(6) . . ? C20 N1 C39 128.6(6) . . ? C20 N1 H2 105.1 . . ? C39 N1 H2 126.3 . . ? C22 P2 C33 101.2(3) . . ? C22 P2 C27 105.2(3) . . ? C33 P2 C27 105.6(3) . . ? C22 P2 Ir 99.94(18) . . ? C33 P2 Ir 130.3(2) . . ? C27 P2 Ir 111.29(19) . . ? C2 C3 C4 119.8(6) . . ? C2 C3 P1 113.4(4) . . ? C4 C3 P1 126.7(5) . . ? C3 C4 C5 119.4(7) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.4(7) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.2(7) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C2 C7 C6 119.9(7) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C13 C8 C9 119.1(6) . . ? C13 C8 P1 121.9(5) . . ? C9 C8 P1 118.9(5) . . ? C8 C9 C10 120.1(6) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 120.0(7) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.0(7) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.3(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 120.5(6) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C19 117.9(6) . . ? C15 C14 P1 121.0(5) . . ? C19 C14 P1 120.9(5) . . ? C14 C15 C16 120.3(7) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.5(7) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.1(7) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C19 C18 C17 120.3(7) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C14 121.9(7) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? N1 C20 C21 119.4(5) . . ? N1 C20 Ir 122.4(4) . . ? C21 C20 Ir 118.2(4) . . ? C22 C21 C26 119.8(5) . . ? C22 C21 C20 115.4(5) . . ? C26 C21 C20 124.6(5) . . ? C21 C22 C23 118.8(5) . . ? C21 C22 P2 114.9(4) . . ? C23 C22 P2 126.1(5) . . ? C24 C23 C22 120.5(6) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.9(6) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C26 C25 C24 120.8(6) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C21 120.1(6) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C28 C27 C32 117.8(6) . . ? C28 C27 P2 122.8(5) . . ? C32 C27 P2 119.2(5) . . ? C27 C28 C29 121.3(7) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C30 C29 C28 119.7(7) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 119.9(7) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C32 120.7(7) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C31 C32 C27 120.6(7) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C38 C33 C34 118.1(6) . . ? C38 C33 P2 118.5(5) . . ? C34 C33 P2 123.2(5) . . ? C33 C34 C35 120.8(8) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C36 C35 C34 120.7(8) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 120.5(8) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C36 C37 C38 119.4(8) . . ? C36 C37 H37 120.3 . . ? C38 C37 H37 120.3 . . ? C33 C38 C37 120.5(7) . . ? C33 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? N1 C39 H39A 109.5 . . ? N1 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N1 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? 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 C20 Ir C1 O1 26.6(5) . . . . ? P1 Ir C1 O1 -153.8(5) . . . . ? P2 Ir C1 O1 -4.6(15) . . . . ? Cl1 Ir C1 O1 116.9(5) . . . . ? C20 Ir C1 C2 -153.0(4) . . . . ? P1 Ir C1 C2 26.5(4) . . . . ? P2 Ir C1 C2 175.7(8) . . . . ? Cl1 Ir C1 C2 -62.8(4) . . . . ? C20 Ir P1 C8 -136.7(19) . . . . ? C1 Ir P1 C8 -141.3(3) . . . . ? P2 Ir P1 C8 43.3(2) . . . . ? Cl1 Ir P1 C8 -50.6(2) . . . . ? C20 Ir P1 C3 -18.0(19) . . . . ? C1 Ir P1 C3 -22.6(3) . . . . ? P2 Ir P1 C3 162.0(2) . . . . ? Cl1 Ir P1 C3 68.2(2) . . . . ? C20 Ir P1 C14 92.3(19) . . . . ? C1 Ir P1 C14 87.7(3) . . . . ? P2 Ir P1 C14 -87.7(2) . . . . ? Cl1 Ir P1 C14 178.4(2) . . . . ? O1 C1 C2 C3 158.8(5) . . . . ? Ir C1 C2 C3 -21.5(7) . . . . ? O1 C1 C2 C7 -19.1(9) . . . . ? Ir C1 C2 C7 160.6(5) . . . . ? C20 Ir P2 C22 25.7(3) . . . . ? C1 Ir P2 C22 57.5(11) . . . . ? P1 Ir P2 C22 -154.28(19) . . . . ? Cl1 Ir P2 C22 -63.84(19) . . . . ? C20 Ir P2 C33 139.8(3) . . . . ? C1 Ir P2 C33 171.5(11) . . . . ? P1 Ir P2 C33 -40.2(3) . . . . ? Cl1 Ir P2 C33 50.2(3) . . . . ? C20 Ir P2 C27 -85.0(3) . . . . ? C1 Ir P2 C27 -53.2(11) . . . . ? P1 Ir P2 C27 95.0(2) . . . . ? Cl1 Ir P2 C27 -174.5(2) . . . . ? C7 C2 C3 C4 0.1(9) . . . . ? C1 C2 C3 C4 -177.7(6) . . . . ? C7 C2 C3 P1 176.3(5) . . . . ? C1 C2 C3 P1 -1.6(7) . . . . ? C8 P1 C3 C2 146.6(4) . . . . ? C14 P1 C3 C2 -106.6(5) . . . . ? Ir P1 C3 C2 19.3(5) . . . . ? C8 P1 C3 C4 -37.5(6) . . . . ? C14 P1 C3 C4 69.3(6) . . . . ? Ir P1 C3 C4 -164.9(5) . . . . ? C2 C3 C4 C5 -2.5(10) . . . . ? P1 C3 C4 C5 -178.1(6) . . . . ? C3 C4 C5 C6 2.9(12) . . . . ? C4 C5 C6 C7 -0.9(13) . . . . ? C3 C2 C7 C6 1.8(10) . . . . ? C1 C2 C7 C6 179.7(6) . . . . ? C5 C6 C7 C2 -1.5(12) . . . . ? C3 P1 C8 C13 -29.3(6) . . . . ? C14 P1 C8 C13 -135.2(5) . . . . ? Ir P1 C8 C13 85.7(5) . . . . ? C3 P1 C8 C9 155.9(5) . . . . ? C14 P1 C8 C9 50.0(5) . . . . ? Ir P1 C8 C9 -89.0(5) . . . . ? C13 C8 C9 C10 3.4(10) . . . . ? P1 C8 C9 C10 178.3(5) . . . . ? C8 C9 C10 C11 -2.1(11) . . . . ? C9 C10 C11 C12 -0.5(12) . . . . ? C10 C11 C12 C13 1.8(11) . . . . ? C9 C8 C13 C12 -2.1(9) . . . . ? P1 C8 C13 C12 -176.8(5) . . . . ? C11 C12 C13 C8 -0.5(10) . . . . ? C8 P1 C14 C15 -146.5(5) . . . . ? C3 P1 C14 C15 102.1(5) . . . . ? Ir P1 C14 C15 -8.2(6) . . . . ? C8 P1 C14 C19 39.2(6) . . . . ? C3 P1 C14 C19 -72.2(6) . . . . ? Ir P1 C14 C19 177.5(4) . . . . ? C19 C14 C15 C16 0.6(9) . . . . ? P1 C14 C15 C16 -173.9(5) . . . . ? C14 C15 C16 C17 0.5(11) . . . . ? C15 C16 C17 C18 -0.5(12) . . . . ? C16 C17 C18 C19 -0.6(12) . . . . ? C17 C18 C19 C14 1.8(12) . . . . ? C15 C14 C19 C18 -1.7(10) . . . . ? P1 C14 C19 C18 172.8(6) . . . . ? C39 N1 C20 C21 11.0(10) . . . . ? C39 N1 C20 Ir -165.6(6) . . . . ? C1 Ir C20 N1 -31.7(5) . . . . ? P1 Ir C20 N1 -36(2) . . . . ? P2 Ir C20 N1 143.7(5) . . . . ? Cl1 Ir C20 N1 -122.4(5) . . . . ? C1 Ir C20 C21 151.6(4) . . . . ? P1 Ir C20 C21 147.0(16) . . . . ? P2 Ir C20 C21 -32.9(4) . . . . ? Cl1 Ir C20 C21 60.9(4) . . . . ? N1 C20 C21 C22 -147.7(6) . . . . ? Ir C20 C21 C22 29.0(7) . . . . ? N1 C20 C21 C26 38.4(9) . . . . ? Ir C20 C21 C26 -144.8(5) . . . . ? C26 C21 C22 C23 -2.4(9) . . . . ? C20 C21 C22 C23 -176.5(5) . . . . ? C26 C21 C22 P2 172.7(4) . . . . ? C20 C21 C22 P2 -1.4(7) . . . . ? C33 P2 C22 C21 -155.1(5) . . . . ? C27 P2 C22 C21 95.1(5) . . . . ? Ir P2 C22 C21 -20.3(5) . . . . ? C33 P2 C22 C23 19.5(6) . . . . ? C27 P2 C22 C23 -90.2(6) . . . . ? Ir P2 C22 C23 154.3(5) . . . . ? C21 C22 C23 C24 -0.1(9) . . . . ? P2 C22 C23 C24 -174.5(5) . . . . ? C22 C23 C24 C25 3.1(9) . . . . ? C23 C24 C25 C26 -3.7(10) . . . . ? C24 C25 C26 C21 1.3(9) . . . . ? C22 C21 C26 C25 1.8(9) . . . . ? C20 C21 C26 C25 175.4(6) . . . . ? C22 P2 C27 C28 8.2(6) . . . . ? C33 P2 C27 C28 -98.3(6) . . . . ? Ir P2 C27 C28 115.5(5) . . . . ? C22 P2 C27 C32 -165.7(5) . . . . ? C33 P2 C27 C32 87.8(6) . . . . ? Ir P2 C27 C32 -58.4(6) . . . . ? C32 C27 C28 C29 0.7(10) . . . . ? P2 C27 C28 C29 -173.3(6) . . . . ? C27 C28 C29 C30 0.5(12) . . . . ? C28 C29 C30 C31 -1.4(13) . . . . ? C29 C30 C31 C32 1.1(13) . . . . ? C30 C31 C32 C27 0.1(13) . . . . ? C28 C27 C32 C31 -1.0(11) . . . . ? P2 C27 C32 C31 173.2(6) . . . . ? C22 P2 C33 C38 75.1(6) . . . . ? C27 P2 C33 C38 -175.5(5) . . . . ? Ir P2 C33 C38 -38.4(7) . . . . ? C22 P2 C33 C34 -99.1(6) . . . . ? C27 P2 C33 C34 10.3(6) . . . . ? Ir P2 C33 C34 147.4(5) . . . . ? C38 C33 C34 C35 -3.6(11) . . . . ? P2 C33 C34 C35 170.7(6) . . . . ? C33 C34 C35 C36 1.3(13) . . . . ? C34 C35 C36 C37 1.3(14) . . . . ? C35 C36 C37 C38 -1.7(14) . . . . ? C34 C33 C38 C37 3.2(11) . . . . ? P2 C33 C38 C37 -171.4(6) . . . . ? C36 C37 C38 C33 -0.6(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H2 N1 1.39 1.42 2.735(7) 153.3 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.861 _refine_diff_density_min -0.543 _refine_diff_density_rms 0.118 #=======================================================================END