# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_louis87a _database_code_depnum_ccdc_archive 'CCDC 887816' #TrackingRef 'LOUIS87A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H16 Cl2 F4 Ir N5 O2' _chemical_formula_weight 781.55 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.9751(13) _cell_length_b 9.6151(3) _cell_length_c 15.9638(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.068(2) _cell_angle_gamma 90.00 _cell_volume 5073.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3008 _exptl_absorpt_coefficient_mu 5.541 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7691 _exptl_absorpt_correction_T_max 0.8972 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4972 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4972 _reflns_number_gt 4065 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0350P)^2^+120.0000P] 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 4972 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.138514(8) 0.81244(3) 0.240335(18) 0.01788(9) Uani 1 1 d . . . N1 N 0.2677(2) 0.6517(8) 0.4289(5) 0.0317(16) Uani 1 1 d . . . N2 N 0.17465(18) 0.9863(7) 0.2582(4) 0.0211(13) Uani 1 1 d . . . N3 N 0.10664(18) 0.6312(7) 0.2250(4) 0.0218(13) Uani 1 1 d . . . N4 N 0.1500(2) 0.6180(8) -0.0278(5) 0.0360(18) Uani 1 1 d . . . N5 N 0.11528(19) 0.8949(6) 0.3367(4) 0.0199(13) Uani 1 1 d . . . O1 O 0.08518(15) 0.9174(5) 0.1619(3) 0.0217(11) Uani 1 1 d . . . O2 O 0.03450(16) 1.0533(6) 0.1685(4) 0.0296(13) Uani 1 1 d . . . F1 F 0.18370(17) 0.8016(6) -0.0528(3) 0.0472(14) Uani 1 1 d . . . F2 F 0.11460(17) 0.4352(6) -0.0079(3) 0.0487(14) Uani 1 1 d . . . F3 F 0.29287(14) 0.8616(6) 0.4182(3) 0.0394(12) Uani 1 1 d . . . F4 F 0.24387(16) 0.4417(6) 0.4466(3) 0.0444(13) Uani 1 1 d . . . C1 C 0.1610(2) 1.1131(8) 0.2284(5) 0.0249(17) Uani 1 1 d . . . H1B H 0.1333 1.1240 0.1947 0.030 Uiso 1 1 calc R . . C2 C 0.1857(3) 1.2279(9) 0.2446(5) 0.0294(18) Uani 1 1 d . . . H2A H 0.1753 1.3169 0.2229 0.035 Uiso 1 1 calc R . . C3 C 0.2254(3) 1.2115(9) 0.2926(6) 0.034(2) Uani 1 1 d . . . H3A H 0.2432 1.2893 0.3036 0.041 Uiso 1 1 calc R . . C4 C 0.2402(3) 1.0824(9) 0.3253(5) 0.0308(19) Uani 1 1 d . . . H4B H 0.2679 1.0708 0.3589 0.037 Uiso 1 1 calc R . . C5 C 0.2139(2) 0.9695(8) 0.3084(5) 0.0239(17) Uani 1 1 d . . . C6 C 0.2229(2) 0.8248(9) 0.3413(5) 0.0237(16) Uani 1 1 d . . . C7 C 0.2602(2) 0.7760(9) 0.3958(5) 0.0301(19) Uani 1 1 d . . . C8 C 0.2360(2) 0.5693(9) 0.4091(5) 0.0289(18) Uani 1 1 d . . . C9 C 0.1977(3) 0.5981(8) 0.3559(5) 0.0277(18) Uani 1 1 d . . . H9A H 0.1768 0.5306 0.3443 0.033 Uiso 1 1 calc R . . C10 C 0.1903(2) 0.7318(9) 0.3187(5) 0.0230(17) Uani 1 1 d . . . C11 C 0.0870(3) 0.5864(9) 0.2803(6) 0.0302(18) Uani 1 1 d . . . H11A H 0.0870 0.6446 0.3284 0.036 Uiso 1 1 calc R . . C12 C 0.0671(3) 0.4615(10) 0.2707(6) 0.041(2) Uani 1 1 d . . . H12A H 0.0537 0.4342 0.3111 0.049 Uiso 1 1 calc R . . C13 C 0.0670(3) 0.3757(9) 0.2005(6) 0.036(2) Uani 1 1 d . . . H13A H 0.0534 0.2887 0.1913 0.043 Uiso 1 1 calc R . . C14 C 0.0873(3) 0.4211(9) 0.1444(6) 0.0322(19) Uani 1 1 d . . . H14A H 0.0878 0.3635 0.0963 0.039 Uiso 1 1 calc R . . C15 C 0.1069(2) 0.5479(8) 0.1564(5) 0.0257(17) Uani 1 1 d . . . C16 C 0.1298(2) 0.6079(8) 0.1036(5) 0.0267(18) Uani 1 1 d . . . C17 C 0.1321(3) 0.5586(9) 0.0230(6) 0.035(2) Uani 1 1 d . . . C18 C 0.1671(2) 0.7384(10) 0.0017(5) 0.0313(19) Uani 1 1 d . . . C19 C 0.1695(2) 0.7995(9) 0.0810(5) 0.0263(17) Uani 1 1 d . . . H19A H 0.1846 0.8825 0.0999 0.032 Uiso 1 1 calc R . . C20 C 0.1493(2) 0.7373(8) 0.1328(5) 0.0217(16) Uani 1 1 d . . . C21 C 0.1314(3) 0.8809(9) 0.4249(5) 0.0269(17) Uani 1 1 d . . . H21A H 0.1560 0.8305 0.4488 0.032 Uiso 1 1 calc R . . C22 C 0.1132(3) 0.9378(9) 0.4818(5) 0.0313(19) Uani 1 1 d . . . H22A H 0.1248 0.9242 0.5440 0.038 Uiso 1 1 calc R . . C23 C 0.0784(3) 1.0143(10) 0.4479(6) 0.036(2) Uani 1 1 d . . . H23A H 0.0659 1.0554 0.4866 0.044 Uiso 1 1 calc R . . C24 C 0.0618(3) 1.0310(9) 0.3580(6) 0.0310(19) Uani 1 1 d . . . H24A H 0.0376 1.0829 0.3333 0.037 Uiso 1 1 calc R . . C25 C 0.0811(2) 0.9701(8) 0.3041(5) 0.0232(16) Uani 1 1 d . . . C26 C 0.0647(2) 0.9826(8) 0.2038(5) 0.0219(16) Uani 1 1 d . . . C100 C 0.0007(3) 0.2175(10) -0.0285(6) 0.044(2) Uani 1 1 d . . . H10A H 0.0262 0.1856 0.0161 0.053 Uiso 1 1 calc R . . H10B H -0.0162 0.1346 -0.0519 0.053 Uiso 1 1 calc R . . Cl1 Cl -0.02509(8) 0.3288(3) 0.02295(19) 0.0564(7) Uani 1 1 d . . . Cl2 Cl 0.01187(11) 0.3009(3) -0.1152(2) 0.0715(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01997(15) 0.01877(15) 0.01506(14) -0.00101(13) 0.00593(10) 0.00053(13) N1 0.028(4) 0.039(4) 0.027(4) -0.003(3) 0.006(3) 0.011(3) N2 0.022(3) 0.028(4) 0.015(3) -0.005(3) 0.008(3) -0.002(3) N3 0.016(3) 0.025(3) 0.019(3) 0.001(3) -0.001(2) 0.002(3) N4 0.033(4) 0.047(5) 0.028(4) -0.015(3) 0.010(3) 0.002(4) N5 0.028(3) 0.019(3) 0.013(3) -0.003(2) 0.008(3) -0.005(3) O1 0.023(3) 0.023(3) 0.019(2) -0.001(2) 0.006(2) 0.000(2) O2 0.023(3) 0.029(3) 0.034(3) 0.003(3) 0.006(2) 0.007(2) F1 0.051(3) 0.070(4) 0.029(3) -0.008(3) 0.025(2) -0.010(3) F2 0.063(4) 0.047(3) 0.040(3) -0.029(3) 0.022(3) -0.015(3) F3 0.021(2) 0.055(3) 0.038(3) -0.005(2) 0.004(2) -0.005(2) F4 0.051(3) 0.037(3) 0.038(3) 0.012(2) 0.006(2) 0.017(3) C1 0.026(4) 0.026(4) 0.025(4) -0.003(3) 0.012(3) 0.001(3) C2 0.041(5) 0.024(4) 0.028(4) -0.001(3) 0.017(4) -0.005(4) C3 0.045(5) 0.034(5) 0.027(4) -0.006(4) 0.016(4) -0.013(4) C4 0.026(4) 0.038(5) 0.027(4) -0.008(4) 0.005(3) -0.009(4) C5 0.022(4) 0.031(4) 0.022(4) -0.001(3) 0.011(3) -0.002(3) C6 0.017(4) 0.034(4) 0.020(4) -0.005(3) 0.007(3) 0.002(3) C7 0.025(4) 0.045(5) 0.021(4) -0.005(4) 0.007(3) 0.002(4) C8 0.032(4) 0.033(5) 0.022(4) 0.000(4) 0.008(3) 0.009(4) C9 0.032(4) 0.023(4) 0.028(4) 0.001(3) 0.010(4) 0.005(3) C10 0.017(4) 0.037(5) 0.016(3) 0.000(3) 0.007(3) 0.009(3) C11 0.033(4) 0.029(4) 0.031(4) 0.005(4) 0.012(4) -0.004(4) C12 0.044(5) 0.034(5) 0.044(5) 0.010(4) 0.013(4) -0.006(4) C13 0.034(5) 0.027(4) 0.038(5) 0.004(4) -0.001(4) -0.006(4) C14 0.034(5) 0.026(4) 0.031(4) -0.009(4) 0.005(4) 0.000(4) C15 0.033(4) 0.018(4) 0.024(4) 0.000(3) 0.006(3) 0.009(3) C16 0.022(4) 0.030(4) 0.025(4) -0.007(3) 0.003(3) 0.005(3) C17 0.039(5) 0.028(5) 0.034(5) -0.014(4) 0.007(4) 0.002(4) C18 0.027(4) 0.053(6) 0.019(4) 0.005(4) 0.014(3) 0.004(4) C19 0.019(4) 0.032(4) 0.026(4) 0.000(4) 0.006(3) 0.005(3) C20 0.026(4) 0.025(4) 0.013(3) -0.003(3) 0.004(3) 0.008(3) C21 0.033(4) 0.031(4) 0.015(4) 0.003(3) 0.005(3) -0.003(4) C22 0.042(5) 0.037(5) 0.015(4) -0.003(4) 0.010(3) -0.005(4) C23 0.041(5) 0.041(5) 0.034(5) -0.014(4) 0.022(4) -0.005(4) C24 0.033(5) 0.028(5) 0.035(5) 0.000(4) 0.016(4) 0.002(4) C25 0.028(4) 0.020(4) 0.022(4) -0.003(3) 0.009(3) -0.003(3) C26 0.022(4) 0.023(4) 0.021(4) -0.001(3) 0.007(3) -0.005(3) C100 0.054(6) 0.039(6) 0.035(5) 0.001(4) 0.008(4) -0.007(5) Cl1 0.0496(15) 0.0547(17) 0.0616(16) 0.0050(14) 0.0137(13) 0.0062(13) Cl2 0.084(2) 0.0552(18) 0.090(2) 0.0198(17) 0.0483(19) 0.0012(16) _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 C10 1.992(7) . ? Ir1 C20 2.010(7) . ? Ir1 N3 2.040(6) . ? Ir1 N2 2.058(6) . ? Ir1 N5 2.115(6) . ? Ir1 O1 2.130(5) . ? N1 C7 1.298(11) . ? N1 C8 1.316(11) . ? N2 C1 1.339(10) . ? N2 C5 1.354(10) . ? N3 C11 1.354(10) . ? N3 C15 1.360(10) . ? N4 C17 1.305(12) . ? N4 C18 1.318(12) . ? N5 C21 1.342(9) . ? N5 C25 1.347(10) . ? O1 C26 1.291(9) . ? O2 C26 1.228(9) . ? F1 C18 1.339(9) . ? F2 C17 1.352(10) . ? F3 C7 1.359(10) . ? F4 C8 1.354(10) . ? C1 C2 1.373(11) . ? C2 C3 1.359(12) . ? C3 C4 1.379(12) . ? C4 C5 1.391(11) . ? C5 C6 1.484(11) . ? C6 C7 1.391(11) . ? C6 C10 1.401(11) . ? C8 C9 1.360(11) . ? C9 C10 1.403(11) . ? C11 C12 1.371(12) . ? C12 C13 1.391(13) . ? C13 C14 1.383(13) . ? C14 C15 1.382(11) . ? C15 C16 1.457(11) . ? C16 C17 1.398(11) . ? C16 C20 1.422(11) . ? C18 C19 1.373(11) . ? C19 C20 1.384(11) . ? C21 C22 1.381(11) . ? C22 C23 1.374(12) . ? C23 C24 1.370(12) . ? C24 C25 1.387(11) . ? C25 C26 1.518(10) . ? C100 Cl2 1.750(10) . ? C100 Cl1 1.766(11) . ? 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 C10 Ir1 C20 90.6(3) . . ? C10 Ir1 N3 95.3(3) . . ? C20 Ir1 N3 80.7(3) . . ? C10 Ir1 N2 80.7(3) . . ? C20 Ir1 N2 97.6(3) . . ? N3 Ir1 N2 175.6(2) . . ? C10 Ir1 N5 100.1(3) . . ? C20 Ir1 N5 168.8(3) . . ? N3 Ir1 N5 94.8(2) . . ? N2 Ir1 N5 87.7(2) . . ? C10 Ir1 O1 174.6(3) . . ? C20 Ir1 O1 92.4(2) . . ? N3 Ir1 O1 89.7(2) . . ? N2 Ir1 O1 94.4(2) . . ? N5 Ir1 O1 77.2(2) . . ? C7 N1 C8 114.4(7) . . ? C1 N2 C5 119.5(7) . . ? C1 N2 Ir1 124.0(5) . . ? C5 N2 Ir1 116.3(5) . . ? C11 N3 C15 118.5(7) . . ? C11 N3 Ir1 124.5(5) . . ? C15 N3 Ir1 116.9(5) . . ? C17 N4 C18 114.7(7) . . ? C21 N5 C25 118.4(7) . . ? C21 N5 Ir1 126.6(5) . . ? C25 N5 Ir1 115.0(5) . . ? C26 O1 Ir1 116.9(4) . . ? N2 C1 C2 122.4(7) . . ? C3 C2 C1 118.5(8) . . ? C2 C3 C4 120.3(8) . . ? C3 C4 C5 119.2(8) . . ? N2 C5 C4 120.0(7) . . ? N2 C5 C6 112.2(7) . . ? C4 C5 C6 127.8(7) . . ? C7 C6 C10 117.6(8) . . ? C7 C6 C5 125.8(7) . . ? C10 C6 C5 116.5(6) . . ? N1 C7 F3 114.1(7) . . ? N1 C7 C6 126.1(8) . . ? F3 C7 C6 119.8(8) . . ? N1 C8 F4 113.9(7) . . ? N1 C8 C9 127.5(8) . . ? F4 C8 C9 118.6(8) . . ? C8 C9 C10 117.3(8) . . ? C6 C10 C9 117.0(7) . . ? C6 C10 Ir1 114.2(6) . . ? C9 C10 Ir1 128.8(6) . . ? N3 C11 C12 123.5(8) . . ? C11 C12 C13 118.6(9) . . ? C14 C13 C12 117.9(8) . . ? C15 C14 C13 121.7(8) . . ? N3 C15 C14 119.8(8) . . ? N3 C15 C16 112.5(7) . . ? C14 C15 C16 127.7(7) . . ? C17 C16 C20 115.6(8) . . ? C17 C16 C15 127.2(8) . . ? C20 C16 C15 116.9(7) . . ? N4 C17 F2 114.2(7) . . ? N4 C17 C16 127.3(8) . . ? F2 C17 C16 118.6(8) . . ? N4 C18 F1 114.2(7) . . ? N4 C18 C19 126.0(8) . . ? F1 C18 C19 119.7(8) . . ? C18 C19 C20 118.4(8) . . ? C19 C20 C16 117.8(7) . . ? C19 C20 Ir1 129.0(6) . . ? C16 C20 Ir1 112.9(6) . . ? N5 C21 C22 121.6(8) . . ? C23 C22 C21 119.5(7) . . ? C24 C23 C22 119.5(8) . . ? C23 C24 C25 118.4(8) . . ? N5 C25 C24 122.5(7) . . ? N5 C25 C26 115.6(6) . . ? C24 C25 C26 121.9(7) . . ? O2 C26 O1 124.8(7) . . ? O2 C26 C25 120.0(7) . . ? O1 C26 C25 115.1(6) . . ? Cl2 C100 Cl1 111.7(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.752 _refine_diff_density_min -1.737 _refine_diff_density_rms 0.176 data_yk37 _database_code_depnum_ccdc_archive 'CCDC 887817' #TrackingRef 'yk37.cif' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 F4 Ir N4 O2' _chemical_formula_weight 673.63 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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.66610(10) _cell_length_b 18.1556(3) _cell_length_c 16.2735(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.1990(10) _cell_angle_gamma 90.00 _cell_volume 2235.86(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4388 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 6.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5835 _exptl_absorpt_correction_T_max 0.8888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8837 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4388 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0374P)^2^+0.0976P] 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 4388 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.778361(17) 0.231735(8) 0.008014(8) 0.02032(7) Uani 1 1 d . . . F1 F 1.2258(3) 0.03115(17) -0.0841(2) 0.0677(9) Uani 1 1 d . . . F2 F 0.7268(4) 0.07095(16) -0.26107(15) 0.0523(7) Uani 1 1 d . . . F3 F 0.3494(3) 0.03648(17) 0.12395(18) 0.0601(8) Uani 1 1 d . . . F4 F 0.8583(4) 0.08648(16) 0.28820(15) 0.0529(7) Uani 1 1 d . . . N1 N 0.5673(4) 0.22115(18) -0.0852(2) 0.0283(7) Uani 1 1 d . . . N2 N 0.9756(5) 0.0524(2) -0.1717(2) 0.0422(9) Uani 1 1 d . . . N3 N 0.9910(4) 0.23046(16) 0.1009(2) 0.0242(7) Uani 1 1 d . . . N4 N 0.6051(5) 0.0625(2) 0.2053(2) 0.0406(9) Uani 1 1 d . . . O1 O 0.8866(3) 0.31425(16) -0.06287(16) 0.0301(6) Uani 1 1 d . . . O2 O 0.6623(3) 0.31728(15) 0.07176(16) 0.0290(6) Uani 1 1 d . . . C1 C 0.4137(6) 0.2572(2) -0.0860(3) 0.0349(10) Uani 1 1 d . . . H1 H 0.4030 0.2917 -0.0432 0.042 Uiso 1 1 calc R . . C2 C 0.2713(6) 0.2450(3) -0.1481(3) 0.0454(12) Uani 1 1 d . . . H2 H 0.1633 0.2704 -0.1475 0.055 Uiso 1 1 calc R . . C3 C 0.2862(6) 0.1964(3) -0.2100(3) 0.0479(12) Uani 1 1 d . . . H3 H 0.1892 0.1881 -0.2532 0.058 Uiso 1 1 calc R . . C4 C 0.4441(6) 0.1589(3) -0.2100(3) 0.0421(11) Uani 1 1 d . . . H4 H 0.4558 0.1246 -0.2528 0.050 Uiso 1 1 calc R . . C5 C 0.5858(5) 0.1722(2) -0.1462(2) 0.0286(9) Uani 1 1 d . . . C6 C 0.8705(5) 0.1542(2) -0.0576(2) 0.0251(8) Uani 1 1 d . . . C7 C 1.0297(5) 0.1151(2) -0.0394(3) 0.0341(9) Uani 1 1 d . . . H7 H 1.1062 0.1214 0.0121 0.041 Uiso 1 1 calc R . . C8 C 1.0709(5) 0.0672(2) -0.0994(3) 0.0405(11) Uani 1 1 d . . . C9 C 0.8240(6) 0.0867(2) -0.1864(3) 0.0361(10) Uani 1 1 d . . . C10 C 0.8612(6) 0.3837(2) -0.0565(2) 0.0329(9) Uani 1 1 d . . . C11 C 0.9484(7) 0.4313(3) -0.1135(3) 0.0470(12) Uani 1 1 d . . . H11A H 1.0747 0.4197 -0.1064 0.071 Uiso 1 1 calc R . . H11B H 0.9330 0.4832 -0.0999 0.071 Uiso 1 1 calc R . . H11C H 0.8944 0.4221 -0.1713 0.071 Uiso 1 1 calc R . . C12 C 0.7628(5) 0.4184(3) -0.0024(2) 0.0390(10) Uani 1 1 d . . . H12 H 0.7556 0.4706 -0.0064 0.047 Uiso 1 1 calc R . . C13 C 0.6731(5) 0.3858(2) 0.0572(2) 0.0322(9) Uani 1 1 d . . . C14 C 0.5825(7) 0.4354(3) 0.1105(3) 0.0530(13) Uani 1 1 d . . . H14A H 0.4578 0.4214 0.1056 0.079 Uiso 1 1 calc R . . H14B H 0.5912 0.4865 0.0923 0.079 Uiso 1 1 calc R . . H14C H 0.6392 0.4307 0.1687 0.079 Uiso 1 1 calc R . . C15 C 0.9807(5) 0.1843(2) 0.1655(2) 0.0261(8) Uani 1 1 d . . . C16 C 0.6959(5) 0.1582(2) 0.0819(2) 0.0250(8) Uani 1 1 d . . . C17 C 0.5357(5) 0.1183(2) 0.0698(3) 0.0324(9) Uani 1 1 d . . . H17 H 0.4544 0.1221 0.0194 0.039 Uiso 1 1 calc R . . C18 C 0.5021(6) 0.0741(2) 0.1330(3) 0.0380(10) Uani 1 1 d . . . C19 C 0.7551(6) 0.0978(2) 0.2140(2) 0.0352(10) Uani 1 1 d . . . C20 C 1.1247(6) 0.1764(3) 0.2283(3) 0.0404(11) Uani 1 1 d . . . H20 H 1.1175 0.1443 0.2737 0.048 Uiso 1 1 calc R . . C21 C 1.2781(6) 0.2149(3) 0.2249(3) 0.0432(11) Uani 1 1 d . . . H21 H 1.3762 0.2102 0.2684 0.052 Uiso 1 1 calc R . . C22 C 1.2880(6) 0.2600(3) 0.1586(3) 0.0406(11) Uani 1 1 d . . . H22 H 1.3941 0.2857 0.1544 0.049 Uiso 1 1 calc R . . C23 C 1.1412(6) 0.2675(2) 0.0980(3) 0.0328(10) Uani 1 1 d . . . H23 H 1.1467 0.2999 0.0527 0.039 Uiso 1 1 calc R . . C25 C 0.7591(5) 0.1363(2) -0.1337(2) 0.0282(8) Uani 1 1 d . . . C26 C 0.8115(5) 0.1453(2) 0.1574(2) 0.0274(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.01937(9) 0.02110(10) 0.02023(9) -0.00019(5) 0.00233(6) -0.00015(5) F1 0.0443(16) 0.065(2) 0.095(2) -0.0340(18) 0.0150(15) 0.0183(15) F2 0.0697(18) 0.0534(19) 0.0344(14) -0.0206(13) 0.0104(13) -0.0134(14) F3 0.0479(16) 0.0558(19) 0.080(2) 0.0159(16) 0.0224(14) -0.0187(14) F4 0.0755(19) 0.0510(18) 0.0319(14) 0.0144(12) 0.0079(13) 0.0048(15) N1 0.0258(17) 0.0305(19) 0.0272(18) 0.0027(14) 0.0003(14) -0.0035(13) N2 0.050(2) 0.033(2) 0.050(2) -0.0136(18) 0.0249(19) -0.0079(17) N3 0.0219(16) 0.0249(18) 0.0244(17) -0.0039(13) -0.0002(13) 0.0017(12) N4 0.056(2) 0.031(2) 0.041(2) 0.0070(17) 0.0243(18) 0.0000(17) O1 0.0344(14) 0.0301(16) 0.0271(14) -0.0019(12) 0.0084(11) -0.0053(12) O2 0.0287(13) 0.0314(17) 0.0281(14) 0.0011(12) 0.0084(11) 0.0042(11) C1 0.030(2) 0.034(2) 0.039(3) 0.0048(19) 0.0015(19) 0.0041(17) C2 0.029(2) 0.049(3) 0.052(3) 0.009(2) -0.011(2) -0.001(2) C3 0.038(2) 0.057(3) 0.042(3) 0.002(2) -0.014(2) -0.011(2) C4 0.042(2) 0.049(3) 0.032(2) -0.004(2) -0.0036(18) -0.008(2) C5 0.034(2) 0.030(2) 0.0215(19) -0.0013(16) 0.0041(15) -0.0081(16) C6 0.0263(19) 0.023(2) 0.0284(19) -0.0021(16) 0.0123(15) -0.0009(15) C7 0.031(2) 0.032(2) 0.040(2) -0.0092(19) 0.0077(17) -0.0004(17) C8 0.030(2) 0.036(3) 0.058(3) -0.015(2) 0.015(2) -0.0013(18) C9 0.044(2) 0.031(2) 0.034(2) -0.0079(18) 0.0110(19) -0.0124(19) C10 0.042(2) 0.029(2) 0.024(2) 0.0015(17) -0.0028(17) -0.0098(18) C11 0.066(3) 0.040(3) 0.038(3) 0.000(2) 0.016(2) -0.010(2) C12 0.056(3) 0.017(2) 0.043(3) 0.0002(17) 0.005(2) 0.0005(18) C13 0.037(2) 0.030(2) 0.028(2) -0.0019(17) 0.0016(17) 0.0047(17) C14 0.078(4) 0.032(3) 0.053(3) -0.003(2) 0.024(3) 0.015(2) C15 0.0295(19) 0.025(2) 0.0225(18) -0.0012(15) 0.0011(15) 0.0059(15) C16 0.0242(18) 0.021(2) 0.032(2) -0.0025(16) 0.0118(15) -0.0001(15) C17 0.0218(19) 0.030(2) 0.046(2) 0.0031(19) 0.0078(17) -0.0023(16) C18 0.040(2) 0.027(2) 0.052(3) 0.000(2) 0.023(2) -0.0017(18) C19 0.050(3) 0.031(2) 0.026(2) 0.0010(18) 0.0107(18) 0.0080(19) C20 0.043(2) 0.045(3) 0.031(2) 0.0020(19) -0.0040(18) 0.009(2) C21 0.032(2) 0.049(3) 0.042(3) -0.008(2) -0.0130(19) 0.007(2) C22 0.029(2) 0.043(3) 0.048(3) -0.008(2) -0.002(2) -0.0027(19) C23 0.026(2) 0.034(3) 0.037(2) -0.0045(18) 0.0028(18) -0.0041(16) C25 0.033(2) 0.026(2) 0.0261(19) -0.0039(16) 0.0061(16) -0.0083(16) C26 0.035(2) 0.022(2) 0.0264(19) -0.0010(16) 0.0091(16) 0.0051(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C6 1.965(4) . ? Ir1 C16 1.967(4) . ? Ir1 N3 2.038(3) . ? Ir1 N1 2.042(3) . ? Ir1 O1 2.138(3) . ? Ir1 O2 2.139(3) . ? F1 C8 1.343(5) . ? F2 C9 1.350(5) . ? F3 C18 1.342(5) . ? F4 C19 1.349(5) . ? N1 C1 1.345(5) . ? N1 C5 1.358(5) . ? N2 C9 1.307(6) . ? N2 C8 1.311(6) . ? N3 C23 1.340(5) . ? N3 C15 1.357(5) . ? N4 C19 1.304(6) . ? N4 C18 1.324(6) . ? O1 C10 1.283(5) . ? O2 C13 1.271(5) . ? C1 C2 1.382(7) . ? C1 H1 0.9500 . ? C2 C3 1.358(7) . ? C2 H2 0.9500 . ? C3 C4 1.388(7) . ? C3 H3 0.9500 . ? C4 C5 1.397(5) . ? C4 H4 0.9500 . ? C5 C25 1.464(5) . ? C6 C7 1.402(5) . ? C6 C25 1.425(5) . ? C7 C8 1.382(6) . ? C7 H7 0.9500 . ? C9 C25 1.389(5) . ? C10 C12 1.397(6) . ? C10 C11 1.499(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.407(5) . ? C12 H12 0.9500 . ? C13 C14 1.497(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.387(5) . ? C15 C26 1.464(5) . ? C16 C17 1.412(5) . ? C16 C26 1.415(5) . ? C17 C18 1.362(6) . ? C17 H17 0.9500 . ? C19 C26 1.382(5) . ? C20 C21 1.377(6) . ? C20 H20 0.9500 . ? C21 C22 1.366(7) . ? C21 H21 0.9500 . ? C22 C23 1.380(7) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 Ir1 C16 91.38(16) . . ? C6 Ir1 N3 94.61(14) . . ? C16 Ir1 N3 80.59(14) . . ? C6 Ir1 N1 80.80(15) . . ? C16 Ir1 N1 95.49(14) . . ? N3 Ir1 N1 173.94(13) . . ? C6 Ir1 O1 90.27(14) . . ? C16 Ir1 O1 174.72(13) . . ? N3 Ir1 O1 94.27(11) . . ? N1 Ir1 O1 89.73(11) . . ? C6 Ir1 O2 175.69(13) . . ? C16 Ir1 O2 89.85(13) . . ? N3 Ir1 O2 89.66(11) . . ? N1 Ir1 O2 94.98(12) . . ? O1 Ir1 O2 88.87(11) . . ? C1 N1 C5 120.3(4) . . ? C1 N1 Ir1 123.4(3) . . ? C5 N1 Ir1 116.2(3) . . ? C9 N2 C8 114.7(4) . . ? C23 N3 C15 119.6(4) . . ? C23 N3 Ir1 123.9(3) . . ? C15 N3 Ir1 116.3(3) . . ? C19 N4 C18 114.2(4) . . ? C10 O1 Ir1 124.7(2) . . ? C13 O2 Ir1 125.1(2) . . ? N1 C1 C2 121.2(5) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 119.8(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.6(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 119.7(4) . . ? N1 C5 C25 112.8(3) . . ? C4 C5 C25 127.4(4) . . ? C7 C6 C25 116.7(4) . . ? C7 C6 Ir1 128.6(3) . . ? C25 C6 Ir1 114.7(3) . . ? C8 C7 C6 117.4(4) . . ? C8 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? N2 C8 F1 114.6(4) . . ? N2 C8 C7 127.3(4) . . ? F1 C8 C7 118.1(4) . . ? N2 C9 F2 114.2(4) . . ? N2 C9 C25 126.3(4) . . ? F2 C9 C25 119.5(4) . . ? O1 C10 C12 126.7(4) . . ? O1 C10 C11 115.3(4) . . ? C12 C10 C11 117.9(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 C13 128.1(4) . . ? C10 C12 H12 116.0 . . ? C13 C12 H12 116.0 . . ? O2 C13 C12 126.5(4) . . ? O2 C13 C14 115.5(4) . . ? C12 C13 C14 118.0(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C20 119.8(4) . . ? N3 C15 C26 112.9(3) . . ? C20 C15 C26 127.3(4) . . ? C17 C16 C26 116.5(4) . . ? C17 C16 Ir1 128.4(3) . . ? C26 C16 Ir1 115.1(3) . . ? C18 C17 C16 117.6(4) . . ? C18 C17 H17 121.2 . . ? C16 C17 H17 121.2 . . ? N4 C18 F3 113.8(4) . . ? N4 C18 C17 127.3(4) . . ? F3 C18 C17 118.9(4) . . ? N4 C19 F4 113.8(4) . . ? N4 C19 C26 126.8(4) . . ? F4 C19 C26 119.4(4) . . ? C21 C20 C15 120.2(4) . . ? C21 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C22 C21 C20 119.4(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 118.8(4) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? N3 C23 C22 122.1(4) . . ? N3 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? C9 C25 C6 117.4(4) . . ? C9 C25 C5 127.5(4) . . ? C6 C25 C5 115.1(3) . . ? C19 C26 C16 117.6(4) . . ? C19 C26 C15 127.5(4) . . ? C16 C26 C15 114.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.755 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.116