# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email luwei@hku.hk _publ_contact_author_name 'Wei Lu' _publ_author_name 'Chi-Ming Che' data_complex5 _database_code_depnum_ccdc_archive 'CCDC 841764' #TrackingRef 'web_deposit_cif_file_0_WeiLu_1314325336.CHENY29.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Au F6 N4 P' _chemical_formula_weight 758.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -4.4197 7.2980 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.2749(9) _cell_length_b 7.2655(4) _cell_length_c 22.8836(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.975(2) _cell_angle_gamma 90.00 _cell_volume 2704.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 11.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 17107 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 65.25 _reflns_number_total 4328 _reflns_number_gt 3713 _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^)+(0.0673P)^2^+55.9698P] 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 4328 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.018 _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 Au1 Au -0.05120(3) 0.81759(6) 0.532697(19) 0.03513(19) Uani 1 1 d . . . N1 N -0.1598(5) 0.9237(12) 0.5546(4) 0.034(2) Uani 1 1 d . . . N2 N -0.1198(6) 0.7815(13) 0.4540(4) 0.042(2) Uani 1 1 d . . . N3 N 0.3980(6) 0.3510(16) 0.3893(4) 0.051(3) Uani 1 1 d . . . P P 0.3151(2) -0.2785(6) 0.70426(16) 0.0570(9) Uani 1 1 d . . . F1 F 0.2758(9) -0.121(3) 0.7360(8) 0.177(8) Uani 1 1 d . . . F2 F 0.3550(10) -0.310(4) 0.7652(9) 0.247(14) Uani 1 1 d . . . F3 F 0.3518(10) -0.431(2) 0.6676(11) 0.229(12) Uani 1 1 d . . . F4 F 0.2422(9) -0.397(2) 0.7202(6) 0.168(8) Uani 1 1 d . . . F5 F 0.2717(14) -0.233(3) 0.6477(6) 0.203(9) Uani 1 1 d . . . F6 F 0.3920(10) -0.163(2) 0.6938(7) 0.175(8) Uani 1 1 d . . . C1 C -0.0196(7) 0.8877(15) 0.6162(5) 0.036(2) Uani 1 1 d . . . C2 C 0.0545(7) 0.8670(16) 0.6456(5) 0.042(3) Uani 1 1 d . . . H2A H 0.0989 0.8090 0.6270 0.051 Uiso 1 1 calc R . . C3 C 0.0648(8) 0.9308(18) 0.7026(5) 0.047(3) Uani 1 1 d . . . H3A H 0.1165 0.9171 0.7227 0.056 Uiso 1 1 calc R . . C4 C -0.0006(8) 1.015(2) 0.7305(6) 0.055(3) Uani 1 1 d . . . H4A H 0.0069 1.0607 0.7692 0.065 Uiso 1 1 calc R . . C5 C -0.0756(8) 1.0319(17) 0.7014(5) 0.047(3) Uani 1 1 d . . . H5A H -0.1201 1.0889 0.7203 0.056 Uiso 1 1 calc R . . C6 C -0.0871(7) 0.9654(15) 0.6443(5) 0.036(2) Uani 1 1 d . . . C7 C -0.1644(7) 0.9861(13) 0.6092(5) 0.036(2) Uani 1 1 d . . . C8 C -0.2403(7) 1.0549(17) 0.6268(5) 0.042(3) Uani 1 1 d . . . H8A H -0.2474 1.0980 0.6655 0.051 Uiso 1 1 calc R . . C9 C -0.3050(7) 1.0573(18) 0.5849(6) 0.052(3) Uani 1 1 d . . . H9A H -0.3568 1.1048 0.5954 0.062 Uiso 1 1 calc R . . C10 C -0.2961(7) 0.9934(18) 0.5290(6) 0.049(3) Uani 1 1 d . . . H10A H -0.3409 0.9964 0.5012 0.058 Uiso 1 1 calc R . . C11 C -0.2200(7) 0.9241(17) 0.5139(5) 0.043(3) Uani 1 1 d . . . C12 C -0.1980(7) 0.8462(17) 0.4572(5) 0.045(3) Uani 1 1 d . . . C13 C -0.2508(8) 0.8380(19) 0.4085(6) 0.052(3) Uani 1 1 d . . . H13A H -0.3046 0.8877 0.4099 0.062 Uiso 1 1 calc R . . C14 C -0.2244(9) 0.757(3) 0.3576(7) 0.069(4) Uani 1 1 d . . . H14A H -0.2595 0.7517 0.3235 0.083 Uiso 1 1 calc R . . C15 C -0.1464(9) 0.683(2) 0.3574(6) 0.061(4) Uani 1 1 d . . . H15A H -0.1287 0.6209 0.3235 0.073 Uiso 1 1 calc R . . C16 C -0.0939(8) 0.6976(17) 0.4054(5) 0.047(3) Uani 1 1 d . . . H16A H -0.0398 0.6491 0.4044 0.057 Uiso 1 1 calc R . . C17 C 0.0553(7) 0.7103(14) 0.5097(5) 0.034(2) Uani 1 1 d . . . C18 C 0.1154(7) 0.6542(15) 0.4898(5) 0.038(3) Uani 1 1 d . . . C19 C 0.1876(6) 0.5739(14) 0.4643(5) 0.033(2) Uani 1 1 d . . . C20 C 0.1873(7) 0.5254(15) 0.4047(5) 0.036(2) Uani 1 1 d . . . H20A H 0.1388 0.5432 0.3812 0.043 Uiso 1 1 calc R . . C21 C 0.2559(7) 0.4529(17) 0.3799(5) 0.038(3) Uani 1 1 d . . . H21A H 0.2535 0.4194 0.3398 0.046 Uiso 1 1 calc R . . C22 C 0.3294(7) 0.4275(16) 0.4129(5) 0.042(3) Uani 1 1 d . . . C23 C 0.3296(7) 0.4802(17) 0.4725(5) 0.040(3) Uani 1 1 d . . . H23A H 0.3784 0.4642 0.4959 0.048 Uiso 1 1 calc R . . C24 C 0.2612(6) 0.5538(16) 0.4975(4) 0.037(2) Uani 1 1 d . . . H24A H 0.2639 0.5911 0.5373 0.044 Uiso 1 1 calc R . . C25 C 0.4736(8) 0.335(2) 0.4233(6) 0.062(4) Uani 1 1 d . . . H25A H 0.4640 0.2633 0.4587 0.093 Uiso 1 1 calc R . . H25B H 0.4938 0.4575 0.4341 0.093 Uiso 1 1 calc R . . H25C H 0.5147 0.2717 0.4001 0.093 Uiso 1 1 calc R . . C26 C 0.3969(9) 0.305(2) 0.3275(6) 0.061(4) Uani 1 1 d . . . H26A H 0.3533 0.2148 0.3189 0.091 Uiso 1 1 calc R . . H26B H 0.4501 0.2523 0.3176 0.091 Uiso 1 1 calc R . . H26C H 0.3866 0.4163 0.3042 0.091 Uiso 1 1 calc R . . C27 C 0.4722(14) 0.229(3) 0.6812(8) 0.112(8) Uani 1 1 d . . . H27A H 0.4277 0.3159 0.6883 0.134 Uiso 1 1 calc R . . H27B H 0.5249 0.2837 0.6936 0.134 Uiso 1 1 calc R . . H27C H 0.4634 0.1157 0.7035 0.134 Uiso 1 1 calc R . . C28 C 0.4730(8) 0.184(2) 0.6180(7) 0.060(4) Uani 1 1 d . . . N4 N 0.4694(9) 0.150(2) 0.5704(6) 0.081(4) 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 Au1 0.0355(3) 0.0267(3) 0.0445(3) 0.00087(19) 0.01901(19) -0.00226(18) N1 0.032(5) 0.022(5) 0.050(5) -0.002(4) 0.017(4) 0.003(4) N2 0.047(6) 0.029(5) 0.051(6) 0.010(4) 0.017(4) -0.010(4) N3 0.044(6) 0.062(7) 0.048(6) 0.008(5) 0.021(4) 0.014(5) P 0.0423(17) 0.073(3) 0.056(2) 0.0105(18) 0.0133(14) 0.0016(17) F1 0.128(11) 0.205(17) 0.203(16) -0.148(14) 0.039(10) -0.018(11) F2 0.106(11) 0.41(3) 0.222(19) 0.23(2) -0.032(11) -0.023(15) F3 0.167(14) 0.090(10) 0.44(3) -0.046(14) 0.218(18) -0.023(10) F4 0.152(11) 0.224(16) 0.134(10) -0.094(11) 0.093(9) -0.126(12) F5 0.31(2) 0.23(2) 0.066(8) 0.005(10) -0.030(11) 0.082(19) F6 0.178(14) 0.210(17) 0.144(12) -0.087(11) 0.112(11) -0.116(13) C1 0.042(6) 0.019(5) 0.048(6) 0.000(5) 0.018(5) 0.000(4) C2 0.050(7) 0.028(6) 0.050(7) 0.009(5) 0.020(5) 0.002(5) C3 0.051(7) 0.047(8) 0.042(6) 0.008(6) 0.005(5) 0.001(6) C4 0.069(9) 0.053(9) 0.042(7) -0.001(6) 0.013(6) 0.005(7) C5 0.059(8) 0.036(7) 0.046(7) 0.002(6) 0.021(6) 0.005(6) C6 0.046(6) 0.021(5) 0.043(6) 0.010(5) 0.015(5) 0.002(5) C7 0.042(6) 0.008(5) 0.058(7) 0.008(5) 0.014(5) -0.003(4) C8 0.038(6) 0.039(7) 0.052(7) 0.000(5) 0.023(5) -0.001(5) C9 0.040(6) 0.037(7) 0.080(9) 0.008(6) 0.033(6) 0.006(5) C10 0.035(6) 0.050(8) 0.061(8) 0.009(6) 0.013(5) -0.008(5) C11 0.034(6) 0.045(7) 0.050(7) 0.014(6) 0.013(5) 0.001(5) C12 0.043(7) 0.047(8) 0.046(7) 0.009(6) 0.008(5) -0.015(5) C13 0.048(7) 0.058(9) 0.049(7) 0.009(6) 0.003(5) -0.006(6) C14 0.061(9) 0.091(12) 0.056(9) 0.004(8) 0.000(7) -0.020(9) C15 0.068(9) 0.066(10) 0.051(8) -0.005(7) 0.019(7) -0.018(7) C16 0.053(7) 0.042(7) 0.048(7) 0.001(6) 0.018(6) -0.011(6) C17 0.039(6) 0.018(6) 0.047(6) 0.003(5) 0.016(5) -0.003(4) C18 0.042(6) 0.033(7) 0.040(6) 0.000(5) 0.014(5) -0.010(5) C19 0.036(6) 0.022(6) 0.042(6) 0.003(5) 0.021(4) 0.005(4) C20 0.045(6) 0.024(6) 0.039(6) 0.004(5) 0.005(5) -0.004(5) C21 0.047(6) 0.041(7) 0.029(5) 0.002(5) 0.015(4) -0.001(5) C22 0.044(6) 0.037(7) 0.047(7) -0.002(5) 0.028(5) 0.000(5) C23 0.036(6) 0.044(7) 0.041(6) 0.006(5) 0.009(4) 0.004(5) C24 0.042(6) 0.039(7) 0.030(5) -0.001(5) 0.015(4) -0.007(5) C25 0.053(8) 0.068(10) 0.067(9) 0.020(7) 0.030(7) 0.013(7) C26 0.065(9) 0.073(10) 0.047(7) 0.004(7) 0.035(6) 0.015(7) C27 0.130(18) 0.128(19) 0.074(13) -0.002(13) -0.042(12) -0.008(15) C28 0.040(7) 0.065(10) 0.074(10) 0.006(8) -0.008(7) 0.002(6) N4 0.070(9) 0.110(13) 0.063(9) 0.008(8) 0.009(7) 0.001(8) _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 Au1 C17 1.989(11) . ? Au1 N1 2.007(8) . ? Au1 C1 2.026(11) . ? Au1 N2 2.103(10) . ? N1 C11 1.329(14) . ? N1 C7 1.334(14) . ? N2 C16 1.348(15) . ? N2 C12 1.361(16) . ? N3 C22 1.374(14) . ? N3 C25 1.438(17) . ? N3 C26 1.455(16) . ? P F5 1.490(14) . ? P F1 1.510(14) . ? P F3 1.525(15) . ? P F4 1.521(11) . ? P F2 1.536(16) . ? P F6 1.534(12) . ? C1 C2 1.369(17) . ? C1 C6 1.409(14) . ? C2 C3 1.388(17) . ? C3 C4 1.401(18) . ? C4 C5 1.376(18) . ? C5 C6 1.400(16) . ? C6 C7 1.478(16) . ? C7 C8 1.403(15) . ? C8 C9 1.401(18) . ? C9 C10 1.373(18) . ? C10 C11 1.391(16) . ? C11 C12 1.470(17) . ? C12 C13 1.386(17) . ? C13 C14 1.39(2) . ? C14 C15 1.38(2) . ? C15 C16 1.373(19) . ? C17 C18 1.166(15) . ? C18 C19 1.452(15) . ? C19 C24 1.405(15) . ? C19 C20 1.408(15) . ? C20 C21 1.374(15) . ? C21 C22 1.404(16) . ? C22 C23 1.415(16) . ? C23 C24 1.376(15) . ? C27 C28 1.48(3) . ? C28 N4 1.116(19) . ? 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 C17 Au1 N1 178.9(4) . . ? C17 Au1 C1 98.8(4) . . ? N1 Au1 C1 82.2(4) . . ? C17 Au1 N2 99.6(4) . . ? N1 Au1 N2 79.4(4) . . ? C1 Au1 N2 161.6(4) . . ? C11 N1 C7 126.2(9) . . ? C11 N1 Au1 117.4(7) . . ? C7 N1 Au1 116.3(7) . . ? C16 N2 C12 121.4(11) . . ? C16 N2 Au1 126.2(9) . . ? C12 N2 Au1 112.3(8) . . ? C22 N3 C25 120.9(11) . . ? C22 N3 C26 119.5(11) . . ? C25 N3 C26 119.2(10) . . ? F5 P F1 93.2(11) . . ? F5 P F3 82.3(13) . . ? F1 P F3 175.4(13) . . ? F5 P F4 89.0(12) . . ? F1 P F4 88.1(9) . . ? F3 P F4 92.5(8) . . ? F5 P F2 174.4(13) . . ? F1 P F2 81.3(13) . . ? F3 P F2 103.2(14) . . ? F4 P F2 90.4(9) . . ? F5 P F6 96.1(12) . . ? F1 P F6 91.2(9) . . ? F3 P F6 88.7(8) . . ? F4 P F6 174.8(10) . . ? F2 P F6 84.5(10) . . ? C2 C1 C6 120.4(11) . . ? C2 C1 Au1 128.8(8) . . ? C6 C1 Au1 110.8(8) . . ? C1 C2 C3 120.1(11) . . ? C2 C3 C4 120.3(12) . . ? C5 C4 C3 119.6(12) . . ? C4 C5 C6 120.5(11) . . ? C5 C6 C1 119.0(11) . . ? C5 C6 C7 123.8(10) . . ? C1 C6 C7 117.1(10) . . ? N1 C7 C8 118.0(11) . . ? N1 C7 C6 113.6(9) . . ? C8 C7 C6 128.4(11) . . ? C9 C8 C7 117.1(11) . . ? C10 C9 C8 122.2(11) . . ? C9 C10 C11 118.6(12) . . ? N1 C11 C10 117.9(11) . . ? N1 C11 C12 114.8(10) . . ? C10 C11 C12 127.2(11) . . ? N2 C12 C13 119.7(12) . . ? N2 C12 C11 116.0(10) . . ? C13 C12 C11 124.3(12) . . ? C12 C13 C14 119.6(13) . . ? C15 C14 C13 118.6(14) . . ? C16 C15 C14 121.0(13) . . ? N2 C16 C15 119.5(13) . . ? C18 C17 Au1 172.3(11) . . ? C17 C18 C19 176.5(12) . . ? C24 C19 C20 118.1(9) . . ? C24 C19 C18 120.7(10) . . ? C20 C19 C18 121.0(10) . . ? C21 C20 C19 121.4(10) . . ? C20 C21 C22 121.1(10) . . ? N3 C22 C21 122.0(10) . . ? N3 C22 C23 120.8(11) . . ? C21 C22 C23 117.1(10) . . ? C24 C23 C22 122.1(11) . . ? C23 C24 C19 120.1(10) . . ? N4 C28 C27 176.5(17) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 65.25 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 3.312 _refine_diff_density_min -1.380 _refine_diff_density_rms 0.216