# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_frm_0m_1g #TrackingRef '19414_web_deposit_cif_file_0_JonathanBarnard_1365788034.1g.cif' _audit_creation_date 2013-04-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H23 Cl Ir N O2' _chemical_formula_sum 'C22 H23 Cl Ir N O2' _chemical_formula_weight 561.06 _chemical_melting_point ? 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4378(8) _cell_length_b 14.0123(16) _cell_length_c 18.702(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.756(3) _cell_angle_gamma 90.00 _cell_volume 1931.3(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1656 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.49 _cell_measurement_theta_min 2.64 _exptl_absorpt_coefficient_mu 7.069 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5218 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details sadabs _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.930 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.10 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 24448 _diffrn_reflns_theta_full 26.51 _diffrn_reflns_theta_max 26.51 _diffrn_reflns_theta_min 1.82 _diffrn_ambient_temperature 569.3 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3684 _reflns_number_total 4009 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.176 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.099 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 4009 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0198 _refine_ls_R_factor_gt 0.0167 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+1.2868P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0394 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.874803(12) 0.908012(6) 0.184268(5) 0.01115(4) Uani 1 1 d . . . Cl4 Cl 1.15328(8) 0.84328(4) 0.15412(4) 0.01847(14) Uani 1 1 d . . . N1 N 0.9605(3) 1.03749(15) 0.14404(12) 0.0129(4) Uani 1 1 d . . . O2 O 1.3219(3) 1.09208(13) 0.45274(11) 0.0231(5) Uani 1 1 d . . . O3 O 1.2060(3) 0.94111(15) 0.46694(10) 0.0250(5) Uani 1 1 d . . . C6 C 1.0637(3) 1.09564(17) 0.19229(15) 0.0137(5) Uani 1 1 d . . . C7 C 1.0974(3) 1.05688(18) 0.26504(15) 0.0136(5) Uani 1 1 d . . . C10 C 0.6341(3) 0.88001(18) 0.23352(15) 0.0145(5) Uani 1 1 d . . . C11 C 1.2226(4) 1.0620(2) 0.38789(15) 0.0178(6) Uani 1 1 d . . . C12 C 0.5828(3) 0.92142(18) 0.16380(15) 0.0146(5) Uani 1 1 d . . . C14 C 1.0225(3) 0.96582(18) 0.27299(14) 0.0143(5) Uani 1 1 d . . . C15 C 0.9792(4) 1.15103(19) 0.04948(15) 0.0198(6) Uani 1 1 d . . . H15 H 0.9491 1.1683 0.0013 0.024 Uiso 1 1 calc R . . C16 C 0.5879(4) 0.91939(19) 0.30319(15) 0.0188(6) Uani 1 1 d . . . H16A H 0.6601 0.8882 0.3428 0.028 Uiso 1 1 calc R . . H16B H 0.4617 0.9086 0.3062 0.028 Uiso 1 1 calc R . . H16C H 0.6122 0.9867 0.3053 0.028 Uiso 1 1 calc R . . C17 C 1.2693(4) 1.0271(2) 0.50479(15) 0.0245(6) Uani 1 1 d . . . H17A H 1.1734 1.0547 0.5286 0.029 Uiso 1 1 calc R . . H17B H 1.3717 1.0130 0.5411 0.029 Uiso 1 1 calc R . . C20 C 0.4808(3) 1.01347(18) 0.14798(16) 0.0177(6) Uani 1 1 d . . . H20A H 0.4688 1.0455 0.1925 0.027 Uiso 1 1 calc R . . H20B H 0.3625 1.0001 0.1226 0.027 Uiso 1 1 calc R . . H20C H 0.5460 1.0536 0.1188 0.027 Uiso 1 1 calc R . . C21 C 1.1983(4) 1.10775(18) 0.32252(15) 0.0165(6) Uani 1 1 d . . . H21 H 1.2451 1.1683 0.3163 0.020 Uiso 1 1 calc R . . C27 C 1.0565(4) 0.92168(18) 0.34151(15) 0.0166(6) Uani 1 1 d . . . H27 H 1.0136 0.8606 0.3489 0.020 Uiso 1 1 calc R . . C30 C 0.9229(4) 1.06498(19) 0.07459(15) 0.0160(5) Uani 1 1 d . . . H30 H 0.8560 1.0240 0.0421 0.019 Uiso 1 1 calc R . . C32 C 1.1546(4) 0.9716(2) 0.39682(15) 0.0185(6) Uani 1 1 d . . . C2 C 0.7261(3) 0.79090(18) 0.22284(15) 0.0151(5) Uani 1 1 d . . . C3 C 1.0822(4) 1.21145(18) 0.09802(15) 0.0188(6) Uani 1 1 d . . . H3 H 1.1221 1.2700 0.0828 0.023 Uiso 1 1 calc R . . C4 C 0.7166(3) 0.77662(18) 0.14605(15) 0.0160(5) Uani 1 1 d . . . C5 C 1.1245(3) 1.18339(18) 0.16900(15) 0.0170(6) Uani 1 1 d . . . H5 H 1.1939 1.2231 0.2017 0.020 Uiso 1 1 calc R . . C8 C 0.6281(3) 0.85549(18) 0.10923(15) 0.0154(5) Uani 1 1 d . . . C9 C 0.8010(4) 0.71819(19) 0.27807(16) 0.0196(6) Uani 1 1 d . . . H9A H 0.9297 0.7126 0.2782 0.029 Uiso 1 1 calc R . . H9B H 0.7445 0.6575 0.2664 0.029 Uiso 1 1 calc R . . H9C H 0.7766 0.7380 0.3249 0.029 Uiso 1 1 calc R . . C13 C 0.5722(4) 0.8648(2) 0.02981(16) 0.0226(6) Uani 1 1 d . . . H13A H 0.5887 0.9296 0.0154 0.034 Uiso 1 1 calc R . . H13B H 0.4468 0.8474 0.0183 0.034 Uiso 1 1 calc R . . H13C H 0.6452 0.8233 0.0047 0.034 Uiso 1 1 calc R . . C19 C 0.7875(4) 0.68996(19) 0.11250(16) 0.0224(6) Uani 1 1 d . . . H19A H 0.8083 0.7045 0.0641 0.034 Uiso 1 1 calc R . . H19B H 0.7003 0.6393 0.1115 0.034 Uiso 1 1 calc R . . H19C H 0.8994 0.6704 0.1403 0.034 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 0.01155(6) 0.00960(6) 0.01228(6) 0.00002(4) 0.00157(4) -0.00032(4) Cl4 0.0144(3) 0.0135(3) 0.0282(4) -0.0001(3) 0.0055(3) 0.0019(2) N1 0.0129(10) 0.0109(10) 0.0154(12) 0.0007(9) 0.0034(9) 0.0025(8) O2 0.0258(11) 0.0274(11) 0.0148(11) -0.0026(8) -0.0018(9) -0.0072(8) O3 0.0317(12) 0.0281(11) 0.0135(11) 0.0035(9) -0.0033(9) -0.0049(9) C6 0.0104(12) 0.0129(12) 0.0184(14) -0.0012(10) 0.0042(10) 0.0020(9) C7 0.0110(12) 0.0131(12) 0.0174(14) -0.0008(10) 0.0039(10) 0.0020(10) C10 0.0109(12) 0.0131(12) 0.0204(15) -0.0010(11) 0.0054(10) -0.0035(10) C11 0.0178(13) 0.0208(13) 0.0146(14) -0.0046(11) 0.0014(11) -0.0017(11) C12 0.0102(12) 0.0149(12) 0.0190(15) -0.0003(10) 0.0033(10) -0.0016(10) C14 0.0109(12) 0.0155(13) 0.0170(14) -0.0026(11) 0.0035(10) 0.0013(10) C15 0.0227(14) 0.0221(14) 0.0154(15) 0.0065(11) 0.0053(11) 0.0039(11) C16 0.0218(14) 0.0167(13) 0.0192(15) -0.0027(11) 0.0072(11) -0.0014(11) C17 0.0248(15) 0.0343(17) 0.0136(15) -0.0026(13) -0.0008(12) -0.0053(13) C20 0.0151(13) 0.0147(13) 0.0229(15) -0.0005(11) 0.0015(11) 0.0002(10) C21 0.0160(13) 0.0144(13) 0.0192(15) -0.0025(11) 0.0023(11) -0.0019(10) C27 0.0166(13) 0.0159(13) 0.0174(15) 0.0005(11) 0.0028(11) -0.0041(10) C30 0.0165(13) 0.0161(13) 0.0159(14) -0.0012(11) 0.0036(11) 0.0007(10) C32 0.0173(13) 0.0239(14) 0.0142(14) 0.0037(11) 0.0019(11) 0.0020(11) C2 0.0115(12) 0.0137(13) 0.0207(15) 0.0004(11) 0.0040(10) -0.0030(10) C3 0.0211(14) 0.0138(13) 0.0231(15) 0.0064(11) 0.0087(11) 0.0026(11) C4 0.0124(12) 0.0123(12) 0.0231(15) -0.0027(11) 0.0020(11) -0.0034(10) C5 0.0170(13) 0.0120(12) 0.0230(15) -0.0003(11) 0.0062(11) 0.0007(10) C8 0.0125(12) 0.0148(12) 0.0187(15) -0.0018(11) 0.0014(11) -0.0028(10) C9 0.0170(13) 0.0148(13) 0.0270(16) 0.0050(12) 0.0031(11) -0.0028(11) C13 0.0202(14) 0.0273(15) 0.0193(16) -0.0036(12) -0.0007(12) -0.0007(12) C19 0.0248(15) 0.0158(13) 0.0270(17) -0.0056(12) 0.0052(12) -0.0018(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 Ir1 Cl4 2.3971(7) . ? Ir1 N1 2.096(2) . ? Ir1 C10 2.157(2) . ? Ir1 C12 2.162(3) . ? Ir1 C14 2.031(3) . ? Ir1 C2 2.157(2) . ? Ir1 C4 2.249(2) . ? Ir1 C8 2.277(3) . ? N1 C6 1.371(3) . ? N1 C30 1.347(3) . ? O2 C11 1.397(3) . ? O2 C17 1.426(3) . ? O3 C17 1.444(3) . ? O3 C32 1.383(3) . ? C6 C7 1.455(4) . ? C6 C5 1.400(3) . ? C7 C14 1.408(3) . ? C7 C21 1.418(4) . ? C10 C12 1.431(4) . ? C10 C16 1.497(4) . ? C10 C2 1.451(3) . ? C11 C21 1.370(4) . ? C11 C32 1.383(4) . ? C12 C20 1.506(3) . ? C12 C8 1.449(4) . ? C14 C27 1.415(4) . ? C15 C30 1.379(4) . ? C15 C3 1.393(4) . ? C27 C32 1.374(4) . ? C2 C4 1.442(4) . ? C2 C9 1.503(4) . ? C3 C5 1.379(4) . ? C4 C8 1.417(4) . ? C4 C19 1.495(4) . ? C8 C13 1.493(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 N1 Ir1 Cl4 85.92(6) . . ? N1 Ir1 C10 128.38(9) . . ? N1 Ir1 C12 102.00(9) . . ? N1 Ir1 C2 166.69(9) . . ? N1 Ir1 C4 139.98(9) . . ? N1 Ir1 C8 108.50(9) . . ? C10 Ir1 Cl4 145.58(7) . . ? C10 Ir1 C12 38.71(10) . . ? C10 Ir1 C4 63.77(10) . . ? C10 Ir1 C8 63.77(10) . . ? C12 Ir1 Cl4 150.51(7) . . ? C12 Ir1 C4 62.93(9) . . ? C12 Ir1 C8 38.01(9) . . ? C14 Ir1 Cl4 87.36(7) . . ? C14 Ir1 N1 77.93(9) . . ? C14 Ir1 C10 96.44(10) . . ? C14 Ir1 C12 121.98(10) . . ? C14 Ir1 C2 105.99(10) . . ? C14 Ir1 C4 142.03(10) . . ? C14 Ir1 C8 159.17(10) . . ? C2 Ir1 Cl4 106.80(7) . . ? C2 Ir1 C10 39.30(9) . . ? C2 Ir1 C12 64.99(10) . . ? C2 Ir1 C4 38.15(10) . . ? C2 Ir1 C8 63.46(10) . . ? C4 Ir1 Cl4 92.69(7) . . ? C4 Ir1 C8 36.48(9) . . ? C8 Ir1 Cl4 112.51(7) . . ? C6 N1 Ir1 116.64(17) . . ? C30 N1 Ir1 124.06(18) . . ? C30 N1 C6 119.3(2) . . ? C11 O2 C17 103.8(2) . . ? C32 O3 C17 103.7(2) . . ? N1 C6 C7 113.8(2) . . ? N1 C6 C5 119.5(2) . . ? C5 C6 C7 126.6(2) . . ? C14 C7 C6 114.6(2) . . ? C14 C7 C21 123.5(2) . . ? C21 C7 C6 121.9(2) . . ? C12 C10 Ir1 70.83(14) . . ? C12 C10 C16 125.4(2) . . ? C12 C10 C2 107.2(2) . . ? C16 C10 Ir1 127.30(18) . . ? C2 C10 Ir1 70.34(14) . . ? C2 C10 C16 127.2(2) . . ? C21 C11 O2 128.6(2) . . ? C21 C11 C32 122.0(3) . . ? C32 C11 O2 109.3(2) . . ? C10 C12 Ir1 70.47(14) . . ? C10 C12 C20 126.3(2) . . ? C10 C12 C8 108.9(2) . . ? C20 C12 Ir1 125.23(17) . . ? C8 C12 Ir1 75.31(14) . . ? C8 C12 C20 124.5(2) . . ? C7 C14 Ir1 116.95(19) . . ? C7 C14 C27 117.8(2) . . ? C27 C14 Ir1 125.21(19) . . ? C30 C15 C3 118.3(3) . . ? O2 C17 O3 107.4(2) . . ? C11 C21 C7 115.7(2) . . ? C32 C27 C14 118.1(2) . . ? N1 C30 C15 123.0(3) . . ? O3 C32 C11 109.8(2) . . ? C27 C32 O3 127.4(2) . . ? C27 C32 C11 122.8(3) . . ? C10 C2 Ir1 70.36(14) . . ? C10 C2 C9 128.8(2) . . ? C4 C2 Ir1 74.39(14) . . ? C4 C2 C10 107.2(2) . . ? C4 C2 C9 123.6(2) . . ? C9 C2 Ir1 125.91(18) . . ? C5 C3 C15 119.2(2) . . ? C2 C4 Ir1 67.46(14) . . ? C2 C4 C19 123.9(2) . . ? C8 C4 Ir1 72.83(15) . . ? C8 C4 C2 109.4(2) . . ? C8 C4 C19 126.6(3) . . ? C19 C4 Ir1 126.82(18) . . ? C3 C5 C6 120.6(3) . . ? C12 C8 Ir1 66.69(14) . . ? C12 C8 C13 125.8(2) . . ? C4 C8 Ir1 70.69(14) . . ? C4 C8 C12 107.0(2) . . ? C4 C8 C13 126.9(2) . . ? C13 C8 Ir1 132.69(19) . . ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H21 of C21, {H17A,H17B} of C17, H30 of C30, H5 of C5, H3 of C3, H15 of C15, H27 of C27 At 1.5 times of: {H9A,H9B,H9C} of C9, {H13A,H13B,H13C} of C13, {H19A,H19B,H19C} of C19, {H16A,H16B,H16C} of C16, {H20A,H20B,H20C} of C20 2.a Secondary CH2 refined with riding coordinates: C17(H17A,H17B) 2.b Aromatic/amide H refined with riding coordinates: C15(H15), C21(H21), C27(H27), C30(H30), C3(H3), C5(H5) 2.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C9(H9A,H9B,H9C), C13(H13A,H13B, H13C), C19(H19A,H19B,H19C) ; _database_code_depnum_ccdc_archive 'CCDC 933833' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_frm_0m_1f #TrackingRef '19415_web_deposit_cif_file_1_JonathanBarnard_1365788034.1f.cif' _audit_creation_date 2013-04-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H29 Cl Ir N O3' _chemical_formula_sum 'C26 H29 Cl Ir N O3' _chemical_formula_weight 631.15 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 7.4023(9) _cell_length_b 15.5707(19) _cell_length_c 20.203(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.426(2) _cell_angle_gamma 90.00 _cell_volume 2290.2(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9943 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.38 _cell_measurement_theta_min 2.43 _exptl_absorpt_coefficient_mu 5.975 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.4780 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details sadabs _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1240 _exptl_crystal_size_max .22 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 19921 _diffrn_reflns_theta_full 26.46 _diffrn_reflns_theta_max 26.46 _diffrn_reflns_theta_min 1.66 _diffrn_ambient_temperature 569.3 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 4642 _reflns_number_total 4719 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 3.471 _refine_diff_density_min -3.492 _refine_diff_density_rms 0.237 _refine_ls_extinction_coef 0.00099(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.494 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 4719 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0565 _refine_ls_restrained_S_all 1.494 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+60.3652P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1378 _refine_ls_wR_factor_ref 0.1380 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.17795(5) 0.75833(2) 0.412940(19) 0.01200(15) Uani 1 1 d . . . Cl3 Cl 0.4938(3) 0.74108(16) 0.46965(12) 0.0157(5) Uani 1 1 d . . . O3 O 0.2762(11) 0.9848(5) 0.4342(4) 0.0188(16) Uani 1 1 d . . . C4 C 0.2685(14) 0.8559(7) 0.3606(5) 0.0130(19) Uani 1 1 d . . . C5 C 0.2977(14) 0.7424(7) 0.2820(5) 0.018(2) Uani 1 1 d . . . O6 O 0.3822(12) 1.0805(5) 0.3630(4) 0.0235(17) Uani 1 1 d . . . C7 C 0.0471(15) 0.8007(7) 0.4937(5) 0.015(2) Uani 1 1 d . . . O8 O 0.1518(12) 0.3392(5) 0.3168(4) 0.0217(17) Uani 1 1 d . . . C9 C 0.0616(15) 0.7066(7) 0.5012(6) 0.020(2) Uani 1 1 d . . . N10 N 0.2468(12) 0.6954(6) 0.3296(4) 0.0132(17) Uani 1 1 d . . . C11 C 0.3335(14) 0.5520(7) 0.3737(5) 0.016(2) Uani 1 1 d . . . H11 H 0.4191 0.5775 0.4073 0.019 Uiso 1 1 calc R . . C12 C 0.1212(16) 0.8630(8) 0.5483(5) 0.020(2) Uani 1 1 d . . . H12A H 0.2471 0.8493 0.5661 0.030 Uiso 1 1 calc R . . H12B H 0.0503 0.8594 0.5836 0.030 Uiso 1 1 calc R . . H12C H 0.1138 0.9202 0.5303 0.030 Uiso 1 1 calc R . . C13 C 0.0812(14) 0.4757(7) 0.2721(5) 0.017(2) Uani 1 1 d . . . H13 H -0.0017 0.4500 0.2377 0.020 Uiso 1 1 calc R . . C14 C 0.3674(14) 1.0008(7) 0.3345(5) 0.016(2) Uani 1 1 d . . . C15 C 0.1758(16) 0.6595(7) 0.5591(5) 0.020(2) Uani 1 1 d . . . H15A H 0.1933 0.6012 0.5461 0.030 Uiso 1 1 calc R . . H15B H 0.1140 0.6601 0.5970 0.030 Uiso 1 1 calc R . . H15C H 0.2930 0.6872 0.5711 0.030 Uiso 1 1 calc R . . C16 C -0.1140(14) 0.7382(7) 0.3969(5) 0.017(2) Uani 1 1 d . . . C17 C 0.4065(15) 0.9773(8) 0.2720(6) 0.021(2) Uani 1 1 d . . . H17 H 0.4475 1.0168 0.2435 0.026 Uiso 1 1 calc R . . C18 C 0.1020(15) 0.5640(7) 0.2733(5) 0.017(2) Uani 1 1 d . . . H18 H 0.0322 0.5976 0.2400 0.021 Uiso 1 1 calc R . . C19 C -0.0726(15) 0.8171(7) 0.4308(6) 0.018(2) Uani 1 1 d . . . C22 C 0.2468(17) 0.2867(7) 0.3687(6) 0.022(2) Uani 1 1 d . . . H22A H 0.2148 0.2277 0.3592 0.033 Uiso 1 1 calc R . . H22B H 0.2135 0.3029 0.4108 0.033 Uiso 1 1 calc R . . H22C H 0.3767 0.2940 0.3714 0.033 Uiso 1 1 calc R . . C23 C 0.3145(14) 0.8320(7) 0.2974(5) 0.015(2) Uani 1 1 d . . . C24 C 0.3807(14) 0.8917(7) 0.2551(5) 0.017(2) Uani 1 1 d . . . H24 H 0.4080 0.8727 0.2144 0.020 Uiso 1 1 calc R . . C25 C 0.2284(14) 0.6030(7) 0.3247(5) 0.0132(19) Uani 1 1 d . . . C26 C -0.0743(15) 0.5754(7) 0.4284(6) 0.019(2) Uani 1 1 d . . . H26A H -0.0922 0.5653 0.3808 0.028 Uiso 1 1 calc R . . H26B H -0.1831 0.5592 0.4449 0.028 Uiso 1 1 calc R . . H26C H 0.0278 0.5419 0.4506 0.028 Uiso 1 1 calc R . . C27 C 0.3122(15) 0.4639(7) 0.3731(5) 0.017(2) Uani 1 1 d . . . H27 H 0.3823 0.4303 0.4063 0.020 Uiso 1 1 calc R . . C29 C 0.3689(17) 1.0652(7) 0.4327(6) 0.022(2) Uani 1 1 d . . . H29A H 0.4902 1.0626 0.4604 0.027 Uiso 1 1 calc R . . H29B H 0.2999 1.1108 0.4493 0.027 Uiso 1 1 calc R . . C31 C 0.3026(15) 0.9413(7) 0.3766(6) 0.018(2) Uani 1 1 d . . . C33 C -0.0358(14) 0.6694(7) 0.4423(5) 0.015(2) Uani 1 1 d . . . C35 C 0.1837(14) 0.4251(7) 0.3220(5) 0.016(2) Uani 1 1 d . . . C45 C -0.1473(16) 0.9034(8) 0.4064(6) 0.022(2) Uani 1 1 d . . . H45A H -0.0643 0.9475 0.4264 0.033 Uiso 1 1 calc R . . H45B H -0.2650 0.9118 0.4191 0.033 Uiso 1 1 calc R . . H45C H -0.1604 0.9060 0.3583 0.033 Uiso 1 1 calc R . . C1 C 0.3421(16) 0.7048(7) 0.2185(5) 0.021(2) Uani 1 1 d . . . H1A H 0.3562 0.6437 0.2235 0.032 Uiso 1 1 calc R . . H1B H 0.4544 0.7294 0.2097 0.032 Uiso 1 1 calc R . . H1C H 0.2443 0.7172 0.1817 0.032 Uiso 1 1 calc R . . C2 C -0.2389(14) 0.7262(9) 0.3308(6) 0.024(2) Uani 1 1 d . . . H2A H -0.2417 0.7779 0.3048 0.036 Uiso 1 1 calc R . . H2B H -0.3604 0.7132 0.3382 0.036 Uiso 1 1 calc R . . H2C H -0.1948 0.6797 0.3068 0.036 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 0.0134(2) 0.0123(2) 0.0106(2) 0.00037(14) 0.00292(13) 0.00034(15) Cl3 0.0130(11) 0.0208(12) 0.0128(11) -0.0009(9) 0.0008(8) -0.0004(9) O3 0.026(4) 0.017(4) 0.015(4) -0.003(3) 0.006(3) -0.003(3) C4 0.012(5) 0.022(5) 0.003(4) 0.001(4) -0.002(4) 0.001(4) C5 0.015(5) 0.016(5) 0.019(5) -0.001(4) -0.004(4) 0.004(4) O6 0.030(5) 0.017(4) 0.025(4) 0.000(3) 0.010(4) -0.004(3) C7 0.021(5) 0.014(5) 0.010(5) -0.001(4) 0.008(4) 0.001(4) O8 0.030(4) 0.016(4) 0.020(4) -0.003(3) 0.007(3) 0.001(3) C9 0.017(5) 0.020(5) 0.025(6) -0.009(4) 0.009(4) -0.007(4) N10 0.015(4) 0.020(4) 0.005(4) -0.001(3) 0.003(3) 0.001(3) C11 0.015(5) 0.021(5) 0.011(5) -0.002(4) 0.002(4) 0.004(4) C12 0.025(6) 0.027(6) 0.011(5) -0.001(4) 0.009(4) -0.003(5) C13 0.014(5) 0.025(6) 0.011(5) -0.004(4) 0.000(4) 0.000(4) C14 0.015(5) 0.016(5) 0.017(5) 0.004(4) 0.000(4) -0.002(4) C15 0.022(6) 0.020(5) 0.016(5) 0.003(4) 0.000(4) 0.002(4) C16 0.019(5) 0.021(5) 0.012(5) 0.004(4) 0.002(4) -0.004(4) C17 0.017(5) 0.025(6) 0.021(6) 0.006(5) 0.003(4) 0.000(4) C18 0.019(5) 0.025(6) 0.008(5) 0.001(4) 0.002(4) -0.001(4) C19 0.013(5) 0.020(5) 0.022(6) 0.001(4) 0.007(4) 0.002(4) C22 0.033(6) 0.013(5) 0.021(5) 0.005(4) 0.009(5) 0.001(4) C23 0.014(5) 0.018(5) 0.012(5) 0.002(4) 0.000(4) 0.003(4) C24 0.017(5) 0.018(5) 0.015(5) 0.004(4) 0.003(4) 0.004(4) C25 0.016(5) 0.016(5) 0.009(4) 0.000(4) 0.005(4) 0.002(4) C26 0.017(5) 0.022(5) 0.019(5) 0.002(4) 0.005(4) -0.001(4) C27 0.018(5) 0.022(5) 0.010(5) 0.001(4) 0.003(4) 0.007(4) C29 0.028(6) 0.016(5) 0.023(6) -0.001(4) 0.004(5) -0.006(4) C31 0.016(5) 0.021(5) 0.018(5) 0.000(4) 0.006(4) 0.002(4) C33 0.013(5) 0.020(5) 0.013(5) 0.001(4) 0.007(4) 0.001(4) C35 0.015(5) 0.021(5) 0.013(5) -0.001(4) 0.006(4) 0.003(4) C45 0.019(5) 0.026(6) 0.022(6) 0.002(5) 0.005(4) 0.005(5) C1 0.030(6) 0.020(5) 0.016(5) -0.001(4) 0.008(5) -0.002(5) C2 0.009(5) 0.041(7) 0.020(5) -0.002(5) -0.003(4) 0.004(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 Ir1 Cl3 2.425(2) . ? Ir1 C4 2.033(10) . ? Ir1 C7 2.146(10) . ? Ir1 C9 2.264(11) . ? Ir1 N10 2.089(8) . ? Ir1 C16 2.149(11) . ? Ir1 C19 2.156(11) . ? Ir1 C33 2.261(10) . ? O3 C29 1.430(13) . ? O3 C31 1.389(13) . ? C4 C23 1.429(14) . ? C4 C31 1.380(15) . ? C5 N10 1.318(14) . ? C5 C23 1.431(15) . ? C5 C1 1.499(15) . ? O6 C14 1.364(13) . ? O6 C29 1.448(14) . ? C7 C9 1.476(15) . ? C7 C12 1.497(15) . ? C7 C19 1.434(15) . ? O8 C22 1.412(13) . ? O8 C35 1.360(13) . ? C9 C15 1.503(16) . ? C9 C33 1.401(15) . ? N10 C25 1.447(13) . ? C11 C25 1.393(14) . ? C11 C27 1.381(15) . ? C13 C18 1.384(16) . ? C13 C35 1.391(15) . ? C14 C17 1.394(16) . ? C14 C31 1.400(15) . ? C16 C19 1.413(15) . ? C16 C33 1.460(15) . ? C16 C2 1.492(14) . ? C17 C24 1.381(16) . ? C18 C25 1.404(14) . ? C19 C45 1.502(15) . ? C23 C24 1.408(15) . ? C26 C33 1.508(15) . ? C27 C35 1.407(15) . ? 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 C4 Ir1 Cl3 87.0(3) . . ? C4 Ir1 C7 113.7(4) . . ? C4 Ir1 C9 152.1(4) . . ? C4 Ir1 N10 77.3(4) . . ? C4 Ir1 C16 116.6(4) . . ? C4 Ir1 C19 98.3(4) . . ? C4 Ir1 C33 155.0(4) . . ? C7 Ir1 Cl3 101.8(3) . . ? C7 Ir1 C9 39.0(4) . . ? C7 Ir1 C16 65.2(4) . . ? C7 Ir1 C19 38.9(4) . . ? C7 Ir1 C33 63.6(4) . . ? C9 Ir1 Cl3 93.4(3) . . ? N10 Ir1 Cl3 88.5(2) . . ? N10 Ir1 C7 165.0(4) . . ? N10 Ir1 C9 130.6(4) . . ? N10 Ir1 C16 101.2(4) . . ? N10 Ir1 C19 132.6(4) . . ? N10 Ir1 C33 102.0(4) . . ? C16 Ir1 Cl3 155.8(3) . . ? C16 Ir1 C9 63.4(4) . . ? C16 Ir1 C19 38.3(4) . . ? C16 Ir1 C33 38.6(4) . . ? C19 Ir1 Cl3 138.9(3) . . ? C19 Ir1 C9 63.8(4) . . ? C19 Ir1 C33 63.4(4) . . ? C33 Ir1 Cl3 118.0(3) . . ? C33 Ir1 C9 36.1(4) . . ? C31 O3 C29 105.6(8) . . ? C23 C4 Ir1 115.1(7) . . ? C31 C4 Ir1 131.4(8) . . ? C31 C4 C23 113.4(9) . . ? N10 C5 C23 114.1(10) . . ? N10 C5 C1 123.0(10) . . ? C23 C5 C1 122.9(10) . . ? C14 O6 C29 104.2(8) . . ? C9 C7 Ir1 74.9(6) . . ? C9 C7 C12 123.8(10) . . ? C12 C7 Ir1 127.2(8) . . ? C19 C7 Ir1 70.9(6) . . ? C19 C7 C9 106.8(9) . . ? C19 C7 C12 128.6(10) . . ? C35 O8 C22 117.1(9) . . ? C7 C9 Ir1 66.2(6) . . ? C7 C9 C15 125.8(10) . . ? C15 C9 Ir1 123.1(8) . . ? C33 C9 Ir1 71.8(6) . . ? C33 C9 C7 107.8(10) . . ? C33 C9 C15 126.1(10) . . ? C5 N10 Ir1 118.2(7) . . ? C5 N10 C25 122.5(9) . . ? C25 N10 Ir1 119.3(6) . . ? C27 C11 C25 120.8(10) . . ? C18 C13 C35 120.4(10) . . ? O6 C14 C17 127.3(10) . . ? O6 C14 C31 110.9(9) . . ? C17 C14 C31 121.8(10) . . ? C19 C16 Ir1 71.1(6) . . ? C19 C16 C33 107.9(9) . . ? C19 C16 C2 126.0(10) . . ? C33 C16 Ir1 74.8(6) . . ? C33 C16 C2 125.6(10) . . ? C2 C16 Ir1 126.6(7) . . ? C24 C17 C14 115.8(10) . . ? C13 C18 C25 120.0(10) . . ? C7 C19 Ir1 70.2(6) . . ? C7 C19 C45 125.5(10) . . ? C16 C19 Ir1 70.6(6) . . ? C16 C19 C7 108.7(9) . . ? C16 C19 C45 125.8(10) . . ? C45 C19 Ir1 127.0(8) . . ? C4 C23 C5 115.0(9) . . ? C24 C23 C4 122.4(10) . . ? C24 C23 C5 122.5(10) . . ? C17 C24 C23 122.3(10) . . ? C11 C25 N10 119.0(9) . . ? C11 C25 C18 119.4(10) . . ? C18 C25 N10 121.5(9) . . ? C11 C27 C35 119.5(10) . . ? O3 C29 O6 106.4(8) . . ? O3 C31 C14 107.5(9) . . ? C4 C31 O3 128.2(10) . . ? C4 C31 C14 124.3(10) . . ? C9 C33 Ir1 72.1(6) . . ? C9 C33 C16 108.4(10) . . ? C9 C33 C26 127.6(10) . . ? C16 C33 Ir1 66.6(6) . . ? C16 C33 C26 123.7(9) . . ? C26 C33 Ir1 131.6(7) . . ? O8 C35 C13 115.9(10) . . ? O8 C35 C27 124.3(10) . . ? C13 C35 C27 119.8(10) . . ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C29(H29A,H29B) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C13(H13), C17(H17), C18(H18), C24(H24), C27(H27) 2.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C26(H26A,H26B, H26C), C45(H45A,H45B,H45C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C) ; _database_code_depnum_ccdc_archive 'CCDC 933834'