# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year 2010 _journal_volume 46 _journal_page_first 9113 _publ_contact_author_name 'Nolan, Steven' _publ_contact_author_email sn17@st-andrews.ac.uk _publ_section_title ; Gold-catalysed formation of allenes ; loop_ _publ_author_name P.Nun S.Gaillard A.M.Z.Slawin S.P.Nolan # Attachment '- 4_6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 787290' #TrackingRef '- 6.cif' # start Validation Reply Form _vrf_PLAT220_4 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.83 Ratio RESPONSE: Correct atom assignment by other chemical means. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H52 Au B F4 N3' _chemical_formula_sum 'C33 H52 Au B F4 N3' _chemical_formula_weight 774.55 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.742(4) _cell_length_b 16.997(3) _cell_length_c 10.3318(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3466.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 11931 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.7 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1564 _exptl_absorpt_coefficient_mu 4.290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.519 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20777 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.36 _reflns_number_total 3290 _reflns_number_gt 3074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. One ISOR constraint was used. No hydrogen atomes were placed on the disordered ethyl atoms. ; _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^)+(0.0219P)^2^+36.3720P] 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 3290 _refine_ls_number_parameters 214 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.258 _refine_ls_restrained_S_all 1.258 _refine_ls_shift/su_max 0.063 _refine_ls_shift/su_mean 0.002 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 0.648726(12) 0.2500 0.68771(2) 0.01451(7) Uani 1 2 d S . . C1 C 0.6023(3) 0.2500 0.8584(6) 0.0181(16) Uani 1 2 d S . . N2 N 0.58315(19) 0.1869(2) 0.9280(4) 0.0186(9) Uani 1 1 d . . . C3 C 0.5504(2) 0.2106(3) 1.0411(4) 0.0219(11) Uani 1 1 d . . . H3A H 0.5318 0.1773 1.1057 0.026 Uiso 1 1 calc R . . C4 C 0.5962(2) 0.1062(3) 0.8880(4) 0.0163(11) Uani 1 1 d . . . C5 C 0.6603(2) 0.0753(3) 0.9113(5) 0.0199(12) Uani 1 1 d . . . C6 C 0.6715(3) -0.0011(3) 0.8703(5) 0.0266(13) Uani 1 1 d . . . H6A H 0.7146 -0.0245 0.8841 0.032 Uiso 1 1 calc R . . C7 C 0.6208(3) -0.0445(3) 0.8091(6) 0.0356(15) Uani 1 1 d . . . H7A H 0.6294 -0.0972 0.7830 0.043 Uiso 1 1 calc R . . C8 C 0.5586(3) -0.0115(3) 0.7864(6) 0.0320(14) Uani 1 1 d . . . H8A H 0.5250 -0.0412 0.7426 0.038 Uiso 1 1 calc R . . C9 C 0.5438(3) 0.0651(3) 0.8266(5) 0.0251(12) Uani 1 1 d . . . C10 C 0.7152(2) 0.1225(3) 0.9817(5) 0.0234(12) Uani 1 1 d . . . H10A H 0.6979 0.1772 0.9946 0.028 Uiso 1 1 calc R . . C11 C 0.7286(4) 0.0866(5) 1.1150(6) 0.068(2) Uani 1 1 d . . . H11A H 0.7634 0.1174 1.1597 0.102 Uiso 1 1 calc R . . H11B H 0.7443 0.0323 1.1047 0.102 Uiso 1 1 calc R . . H11C H 0.6868 0.0871 1.1659 0.102 Uiso 1 1 calc R . . C12 C 0.7800(3) 0.1271(4) 0.9041(6) 0.0462(18) Uani 1 1 d . . . H12A H 0.7706 0.1507 0.8195 0.069 Uiso 1 1 calc R . . H12B H 0.7984 0.0740 0.8920 0.069 Uiso 1 1 calc R . . H12C H 0.8131 0.1595 0.9506 0.069 Uiso 1 1 calc R . . C13 C 0.4755(3) 0.1029(4) 0.7973(6) 0.0363(15) Uani 1 1 d . . . H13A H 0.4708 0.1506 0.8532 0.044 Uiso 1 1 calc R . . C14 C 0.4171(3) 0.0471(4) 0.8286(6) 0.0358(15) Uani 1 1 d . . . H14A H 0.4193 0.0321 0.9201 0.054 Uiso 1 1 calc R . . H14B H 0.4207 -0.0001 0.7745 0.054 Uiso 1 1 calc R . . H14C H 0.3740 0.0736 0.8113 0.054 Uiso 1 1 calc R . . C15 C 0.4709(3) 0.1286(6) 0.6578(8) 0.095(3) Uani 1 1 d U . . H15A H 0.5081 0.1650 0.6384 0.142 Uiso 1 1 calc R . . H15B H 0.4275 0.1552 0.6432 0.142 Uiso 1 1 calc R . . H15C H 0.4741 0.0825 0.6013 0.142 Uiso 1 1 calc R . . N21 N 0.6914(3) 0.2500 0.5012(6) 0.0237(15) Uani 1 2 d S . . C22 C 0.6413(6) 0.2849(8) 0.4088(10) 0.045(4) Uani 0.50 1 d P . . C23 C 0.6348(3) 0.3802(4) 0.4522(7) 0.0492(19) Uani 1 1 d . . . C24 C 0.7011(5) 0.3375(6) 0.4565(11) 0.030(3) Uani 0.50 1 d P . . C25 C 0.7585(5) 0.2892(7) 0.4937(10) 0.027(3) Uani 0.50 1 d P . . C26 C 0.8152(4) 0.2500 0.5715(9) 0.036(2) Uani 1 2 d S . . B1 B 0.5611(4) 0.7500 0.6801(8) 0.0210(19) Uani 1 2 d S . . F1 F 0.52014(17) 0.68343(18) 0.6768(3) 0.0379(9) Uani 1 1 d . . . F2 F 0.6048(3) 0.7500 0.5778(5) 0.0507(15) Uani 1 2 d S . . F3 F 0.5969(3) 0.7500 0.7968(5) 0.0470(14) Uani 1 2 d S . . 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 0.01379(12) 0.01460(12) 0.01513(13) 0.000 0.00210(10) 0.000 C1 0.022(3) 0.018(3) 0.015(3) 0.000 -0.005(3) 0.000 N2 0.0150(17) 0.026(2) 0.0153(19) -0.0035(18) 0.0023(16) -0.0036(17) C3 0.021(2) 0.032(2) 0.012(2) -0.001(2) 0.0057(19) -0.006(2) C4 0.017(2) 0.015(2) 0.017(2) 0.0061(19) 0.0017(19) 0.0026(19) C5 0.018(2) 0.027(3) 0.015(2) -0.002(2) 0.0041(19) -0.005(2) C6 0.024(2) 0.027(3) 0.029(3) -0.001(2) 0.000(2) -0.001(2) C7 0.048(3) 0.025(3) 0.034(3) -0.005(3) -0.004(3) -0.004(3) C8 0.029(3) 0.025(3) 0.042(3) 0.004(3) -0.015(2) -0.011(2) C9 0.022(2) 0.028(3) 0.025(3) 0.012(2) -0.003(2) -0.008(2) C10 0.021(2) 0.024(3) 0.025(3) -0.004(2) -0.001(2) -0.003(2) C11 0.073(4) 0.103(6) 0.028(3) 0.003(4) -0.013(3) -0.051(4) C12 0.022(3) 0.069(4) 0.047(4) -0.013(3) 0.006(3) -0.015(3) C13 0.023(2) 0.038(3) 0.048(3) 0.000(3) -0.017(3) -0.012(2) C14 0.039(3) 0.037(3) 0.032(3) 0.005(3) 0.002(3) -0.008(3) C15 0.017(3) 0.162(7) 0.105(5) 0.106(5) -0.019(3) -0.032(4) N21 0.031(3) 0.024(3) 0.017(3) 0.000 0.005(3) 0.000 C22 0.039(6) 0.085(10) 0.011(5) -0.007(5) -0.003(5) 0.005(6) C23 0.049(4) 0.043(4) 0.055(4) 0.021(3) 0.008(3) 0.012(3) C24 0.023(5) 0.026(5) 0.042(6) 0.021(5) 0.002(5) -0.004(4) C25 0.013(4) 0.037(5) 0.031(6) 0.005(5) 0.006(4) -0.009(4) C26 0.017(3) 0.055(5) 0.037(5) 0.000 0.000(4) 0.000 B1 0.015(3) 0.025(4) 0.023(4) 0.000 -0.001(3) 0.000 F1 0.0463(18) 0.0250(15) 0.0424(19) 0.0056(15) -0.0029(16) -0.0112(15) F2 0.047(3) 0.054(3) 0.051(3) 0.000 0.029(3) 0.000 F3 0.049(3) 0.047(3) 0.044(3) 0.000 -0.024(2) 0.000 _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 C1 1.987(7) . ? Au1 N21 2.104(6) . ? C1 N2 1.345(6) . ? C1 N2 1.345(6) 7_565 ? N2 C3 1.394(6) . ? N2 C4 1.455(6) . ? C3 C3 1.340(10) 7_565 ? C3 H3A 0.9500 . ? C4 C5 1.391(6) . ? C4 C9 1.401(7) . ? C5 C6 1.383(7) . ? C5 C10 1.532(7) . ? C6 C7 1.395(8) . ? C6 H6A 0.9500 . ? C7 C8 1.370(8) . ? C7 H7A 0.9500 . ? C8 C9 1.398(8) . ? C8 H8A 0.9500 . ? C9 C13 1.523(7) . ? C10 C12 1.513(7) . ? C10 C11 1.529(8) . ? C10 H10A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.509(10) . ? C13 C14 1.527(8) . ? C13 H13A 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N21 C25 1.484(11) . ? N21 C25 1.484(11) 7_565 ? N21 C22 1.497(13) 7_565 ? N21 C22 1.497(13) . ? N21 C24 1.569(10) . ? N21 C24 1.569(10) 7_565 ? C22 C22 1.19(3) 7_565 ? C22 C24 1.559(16) . ? C22 C23 1.684(15) . ? C23 C24 1.496(12) . ? C24 C25 1.451(14) . ? C25 C25 1.33(2) 7_565 ? C25 C26 1.531(12) . ? C26 C25 1.531(12) 7_565 ? B1 F2 1.365(9) . ? B1 F1 1.392(5) . ? B1 F1 1.392(5) 7_575 ? B1 F3 1.397(9) . ? 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 C1 Au1 N21 176.2(3) . . ? N2 C1 N2 105.7(6) . 7_565 ? N2 C1 Au1 127.1(3) . . ? N2 C1 Au1 127.1(3) 7_565 . ? C1 N2 C3 110.3(4) . . ? C1 N2 C4 123.4(4) . . ? C3 N2 C4 126.3(4) . . ? C3 C3 N2 106.8(3) 7_565 . ? C3 C3 H3A 126.6 7_565 . ? N2 C3 H3A 126.6 . . ? C5 C4 C9 124.2(5) . . ? C5 C4 N2 118.0(4) . . ? C9 C4 N2 117.9(4) . . ? C6 C5 C4 116.6(5) . . ? C6 C5 C10 121.6(4) . . ? C4 C5 C10 121.8(4) . . ? C5 C6 C7 121.4(5) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C8 C7 C6 120.2(5) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 121.3(5) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C8 C9 C4 116.4(5) . . ? C8 C9 C13 121.3(5) . . ? C4 C9 C13 122.2(5) . . ? C12 C10 C11 110.5(5) . . ? C12 C10 C5 111.9(4) . . ? C11 C10 C5 110.0(5) . . ? C12 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C5 C10 H10A 108.1 . . ? 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 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C9 111.4(5) . . ? C15 C13 C14 109.7(5) . . ? C9 C13 C14 111.3(5) . . ? C15 C13 H13A 108.1 . . ? C9 C13 H13A 108.1 . . ? C14 C13 H13A 108.1 . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C25 N21 C25 53.3(9) . 7_565 ? C25 N21 C22 137.2(7) . 7_565 ? C25 N21 C22 112.2(7) 7_565 7_565 ? C25 N21 C22 112.2(7) . . ? C25 N21 C22 137.2(7) 7_565 . ? C22 N21 C22 46.7(11) 7_565 . ? C25 N21 C24 56.7(6) . . ? C25 N21 C24 107.6(7) 7_565 . ? C22 N21 C24 105.6(7) 7_565 . ? C22 N21 C24 61.1(7) . . ? C25 N21 C24 107.6(7) . 7_565 ? C25 N21 C24 56.7(6) 7_565 7_565 ? C22 N21 C24 61.1(7) 7_565 7_565 ? C22 N21 C24 105.6(7) . 7_565 ? C24 N21 C24 142.9(9) . 7_565 ? C25 N21 Au1 113.9(5) . . ? C25 N21 Au1 113.9(5) 7_565 . ? C22 N21 Au1 108.6(5) 7_565 . ? C22 N21 Au1 108.6(5) . . ? C24 N21 Au1 108.6(5) . . ? C24 N21 Au1 108.6(5) 7_565 . ? C22 C22 N21 66.6(5) 7_565 . ? C22 C22 C24 124.9(6) 7_565 . ? N21 C22 C24 61.7(6) . . ? C22 C22 C23 163.9(4) 7_565 . ? N21 C22 C23 105.2(7) . . ? C24 C22 C23 54.8(6) . . ? C24 C23 C22 58.4(6) . . ? C25 C24 C23 164.7(10) . . ? C25 C24 C22 110.5(9) . . ? C23 C24 C22 66.9(7) . . ? C25 C24 N21 58.7(6) . . ? C23 C24 N21 111.2(7) . . ? C22 C24 N21 57.2(6) . . ? C25 C25 C24 124.4(6) 7_565 . ? C25 C25 N21 63.3(4) 7_565 . ? C24 C25 N21 64.6(6) . . ? C25 C25 C26 64.2(4) 7_565 . ? C24 C25 C26 163.0(10) . . ? N21 C25 C26 115.5(7) . . ? C25 C26 C25 51.6(9) . 7_565 ? F2 B1 F1 110.4(4) . . ? F2 B1 F1 110.4(4) . 7_575 ? F1 B1 F1 108.8(6) . 7_575 ? F2 B1 F3 110.5(6) . . ? F1 B1 F3 108.4(4) . . ? F1 B1 F3 108.4(4) 7_575 . ? 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 N2 C1 N2 C3 1.2(7) 7_565 . . . ? Au1 C1 N2 C3 -178.4(4) . . . . ? N2 C1 N2 C4 -178.3(3) 7_565 . . . ? Au1 C1 N2 C4 2.1(8) . . . . ? C1 N2 C3 C3 -0.7(4) . . . 7_565 ? C4 N2 C3 C3 178.7(3) . . . 7_565 ? C1 N2 C4 C5 80.7(6) . . . . ? C3 N2 C4 C5 -98.7(5) . . . . ? C1 N2 C4 C9 -98.3(6) . . . . ? C3 N2 C4 C9 82.3(6) . . . . ? C9 C4 C5 C6 -0.1(7) . . . . ? N2 C4 C5 C6 -179.0(4) . . . . ? C9 C4 C5 C10 -178.6(5) . . . . ? N2 C4 C5 C10 2.5(7) . . . . ? C4 C5 C6 C7 -0.1(8) . . . . ? C10 C5 C6 C7 178.4(5) . . . . ? C5 C6 C7 C8 1.0(9) . . . . ? C6 C7 C8 C9 -1.7(9) . . . . ? C7 C8 C9 C4 1.4(8) . . . . ? C7 C8 C9 C13 177.8(5) . . . . ? C5 C4 C9 C8 -0.5(7) . . . . ? N2 C4 C9 C8 178.4(4) . . . . ? C5 C4 C9 C13 -176.9(5) . . . . ? N2 C4 C9 C13 2.0(7) . . . . ? C6 C5 C10 C12 55.8(7) . . . . ? C4 C5 C10 C12 -125.8(5) . . . . ? C6 C5 C10 C11 -67.5(7) . . . . ? C4 C5 C10 C11 110.9(6) . . . . ? C8 C9 C13 C15 -76.1(7) . . . . ? C4 C9 C13 C15 100.1(7) . . . . ? C8 C9 C13 C14 46.6(7) . . . . ? C4 C9 C13 C14 -137.1(5) . . . . ? C25 N21 C22 C22 134.8(7) . . . 7_565 ? C25 N21 C22 C22 75.3(9) 7_565 . . 7_565 ? C24 N21 C22 C22 160.2(5) . . . 7_565 ? C24 N21 C22 C22 17.9(5) 7_565 . . 7_565 ? Au1 N21 C22 C22 -98.4(3) . . . 7_565 ? C25 N21 C22 C24 -25.4(8) . . . . ? C25 N21 C22 C24 -84.9(11) 7_565 . . . ? C22 N21 C22 C24 -160.2(5) 7_565 . . . ? C24 N21 C22 C24 -142.3(10) 7_565 . . . ? Au1 N21 C22 C24 101.4(6) . . . . ? C25 N21 C22 C23 -59.9(9) . . . . ? C25 N21 C22 C23 -119.4(9) 7_565 . . . ? C22 N21 C22 C23 165.3(4) 7_565 . . . ? C24 N21 C22 C23 -34.5(7) . . . . ? C24 N21 C22 C23 -176.8(7) 7_565 . . . ? Au1 N21 C22 C23 66.9(7) . . . . ? C22 C22 C23 C24 94.7(17) 7_565 . . . ? N21 C22 C23 C24 37.6(7) . . . . ? C22 C23 C24 C25 -83(4) . . . . ? C22 C23 C24 N21 -37.1(7) . . . . ? C22 C22 C24 C25 3.5(11) 7_565 . . . ? N21 C22 C24 C25 25.7(8) . . . . ? C23 C22 C24 C25 163.8(11) . . . . ? C22 C22 C24 C23 -160.3(5) 7_565 . . . ? N21 C22 C24 C23 -138.1(7) . . . . ? C22 C22 C24 N21 -22.3(6) 7_565 . . . ? C23 C22 C24 N21 138.1(7) . . . . ? C25 N21 C24 C25 -16.8(6) 7_565 . . . ? C22 N21 C24 C25 -136.8(8) 7_565 . . . ? C22 N21 C24 C25 -151.6(9) . . . . ? C24 N21 C24 C25 -74.4(15) 7_565 . . . ? Au1 N21 C24 C25 106.9(6) . . . . ? C25 N21 C24 C23 -167.2(11) . . . . ? C25 N21 C24 C23 176.1(8) 7_565 . . . ? C22 N21 C24 C23 56.1(10) 7_565 . . . ? C22 N21 C24 C23 41.3(8) . . . . ? C24 N21 C24 C23 118.5(12) 7_565 . . . ? Au1 N21 C24 C23 -60.3(9) . . . . ? C25 N21 C24 C22 151.6(9) . . . . ? C25 N21 C24 C22 134.8(8) 7_565 . . . ? C22 N21 C24 C22 14.8(5) 7_565 . . . ? C24 N21 C24 C22 77.2(14) 7_565 . . . ? Au1 N21 C24 C22 -101.5(6) . . . . ? C23 C24 C25 C25 74(4) . . . 7_565 ? C22 C24 C25 C25 -3.5(11) . . . 7_565 ? N21 C24 C25 C25 21.8(6) . . . 7_565 ? C23 C24 C25 N21 52(4) . . . . ? C22 C24 C25 N21 -25.3(8) . . . . ? C23 C24 C25 C26 -42(6) . . . . ? C22 C24 C25 C26 -119(3) . . . . ? N21 C24 C25 C26 -94(3) . . . . ? C22 N21 C25 C25 -83.6(10) 7_565 . . 7_565 ? C22 N21 C25 C25 -133.2(7) . . . 7_565 ? C24 N21 C25 C25 -159.9(6) . . . 7_565 ? C24 N21 C25 C25 -17.5(5) 7_565 . . 7_565 ? Au1 N21 C25 C25 102.9(4) . . . 7_565 ? C25 N21 C25 C24 159.9(6) 7_565 . . . ? C22 N21 C25 C24 76.3(12) 7_565 . . . ? C22 N21 C25 C24 26.8(9) . . . . ? C24 N21 C25 C24 142.5(11) 7_565 . . . ? Au1 N21 C25 C24 -97.2(6) . . . . ? C25 N21 C25 C26 -38.9(9) 7_565 . . . ? C22 N21 C25 C26 -122.5(10) 7_565 . . . ? C22 N21 C25 C26 -172.1(8) . . . . ? C24 N21 C25 C26 161.2(11) . . . . ? C24 N21 C25 C26 -56.4(10) 7_565 . . . ? Au1 N21 C25 C26 64.0(8) . . . . ? C24 C25 C26 C25 125(3) . . . 7_565 ? N21 C25 C26 C25 38.5(9) . . . 7_565 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.649 _refine_diff_density_min -2.153 _refine_diff_density_rms 0.184 data_4 _database_code_depnum_ccdc_archive 'CCDC 787291' #TrackingRef '4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C32 H41 Au N3,B F4,C H2 Cl2' _chemical_formula_sum 'C33 H43 Au B Cl2 F4 N3' _chemical_formula_weight 836.38 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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' Au Au -2.0133 8.8022 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.473(2) _cell_length_b 17.138(4) _cell_length_c 11.355(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.525(7) _cell_angle_gamma 90.00 _cell_volume 1767.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7173 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.6 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 4.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.561 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11013 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.36 _reflns_number_total 5892 _reflns_number_gt 5709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0164P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.020(6) _refine_ls_number_reflns 5892 _refine_ls_number_parameters 398 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0572 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Au1 Au 0.165920(14) 0.29709(2) 0.576507(13) 0.01532(6) Uani 1 1 d . . . C1 C 0.2090(5) 0.2268(3) 0.4519(4) 0.0133(10) Uani 1 1 d . . . N2 N 0.2871(4) 0.1595(2) 0.4739(4) 0.0156(9) Uani 1 1 d . . . C3 C 0.3043(5) 0.1286(3) 0.3649(5) 0.0167(11) Uani 1 1 d . . . H3A H 0.3543 0.0820 0.3553 0.020 Uiso 1 1 calc R . . C4 C 0.2336(5) 0.1796(3) 0.2748(5) 0.0178(11) Uani 1 1 d . . . H4A H 0.2254 0.1753 0.1897 0.021 Uiso 1 1 calc R . . N5 N 0.1761(4) 0.2388(2) 0.3302(4) 0.0140(9) Uani 1 1 d . . . C6 C 0.3560(5) 0.1285(3) 0.5944(4) 0.0148(10) Uani 1 1 d . . . C7 C 0.4891(5) 0.1609(3) 0.6618(4) 0.0176(11) Uani 1 1 d . . . C8 C 0.5525(7) 0.1308(4) 0.7791(6) 0.0245(15) Uani 1 1 d . . . H8A H 0.6437 0.1510 0.8280 0.029 Uiso 1 1 calc R . . C9 C 0.4836(6) 0.0716(3) 0.8248(5) 0.0235(12) Uani 1 1 d . . . H9A H 0.5279 0.0524 0.9053 0.028 Uiso 1 1 calc R . . C10 C 0.3519(6) 0.0400(3) 0.7558(5) 0.0219(12) Uani 1 1 d . . . H10A H 0.3066 -0.0006 0.7891 0.026 Uiso 1 1 calc R . . C11 C 0.2858(5) 0.0673(3) 0.6384(4) 0.0155(10) Uani 1 1 d . . . C12 C 0.5664(5) 0.2245(3) 0.6117(5) 0.0205(11) Uani 1 1 d . . . H12A H 0.4998 0.2406 0.5300 0.025 Uiso 1 1 calc R . . C13 C 0.5966(5) 0.2971(6) 0.6938(5) 0.0359(12) Uani 1 1 d . . . H13A H 0.5040 0.3160 0.7057 0.054 Uiso 1 1 calc R . . H13B H 0.6401 0.3379 0.6548 0.054 Uiso 1 1 calc R . . H13C H 0.6651 0.2837 0.7737 0.054 Uiso 1 1 calc R . . C14 C 0.7092(6) 0.1932(4) 0.5903(5) 0.0317(14) Uani 1 1 d . . . H14A H 0.6868 0.1470 0.5372 0.048 Uiso 1 1 calc R . . H14B H 0.7785 0.1790 0.6693 0.048 Uiso 1 1 calc R . . H14C H 0.7532 0.2335 0.5507 0.048 Uiso 1 1 calc R . . C15 C 0.1378(5) 0.0349(3) 0.5593(5) 0.0219(12) Uani 1 1 d . . . H15A H 0.1297 0.0457 0.4710 0.026 Uiso 1 1 calc R . . C16 C 0.0104(6) 0.0765(4) 0.5921(6) 0.0403(17) Uani 1 1 d . . . H16A H -0.0836 0.0561 0.5408 0.060 Uiso 1 1 calc R . . H16B H 0.0158 0.1327 0.5778 0.060 Uiso 1 1 calc R . . H16C H 0.0177 0.0673 0.6789 0.060 Uiso 1 1 calc R . . C17 C 0.1262(7) -0.0526(4) 0.5756(5) 0.0324(14) Uani 1 1 d . . . H17A H 0.0309 -0.0711 0.5238 0.049 Uiso 1 1 calc R . . H17B H 0.1346 -0.0642 0.6618 0.049 Uiso 1 1 calc R . . H17C H 0.2056 -0.0789 0.5516 0.049 Uiso 1 1 calc R . . C18 C 0.1052(5) 0.3079(4) 0.2647(4) 0.0155(12) Uani 1 1 d . . . C19 C -0.0395(4) 0.3001(6) 0.1915(3) 0.0187(9) Uani 1 1 d . . . C20 C -0.1004(6) 0.3669(3) 0.1237(5) 0.0225(12) Uani 1 1 d . . . H20A H -0.1992 0.3653 0.0730 0.027 Uiso 1 1 calc R . . C21 C -0.0209(6) 0.4337(3) 0.1292(5) 0.0291(13) Uani 1 1 d . . . H21A H -0.0646 0.4774 0.0810 0.035 Uiso 1 1 calc R . . C22 C 0.1226(6) 0.4391(3) 0.2039(5) 0.0279(13) Uani 1 1 d . . . H22A H 0.1756 0.4865 0.2069 0.033 Uiso 1 1 calc R . . C23 C 0.1901(6) 0.3756(3) 0.2745(5) 0.0183(12) Uani 1 1 d . . . C24 C -0.1294(6) 0.2279(3) 0.1893(5) 0.0233(12) Uani 1 1 d . . . H24A H -0.0605 0.1825 0.2009 0.028 Uiso 1 1 calc R . . C25 C -0.1968(7) 0.2271(4) 0.2964(6) 0.0412(17) Uani 1 1 d . . . H25A H -0.1190 0.2347 0.3736 0.062 Uiso 1 1 calc R . . H25B H -0.2453 0.1768 0.2985 0.062 Uiso 1 1 calc R . . H25C H -0.2693 0.2692 0.2858 0.062 Uiso 1 1 calc R . . C26 C -0.2478(8) 0.2149(5) 0.0698(6) 0.057(2) Uani 1 1 d . . . H26A H -0.2036 0.2156 0.0015 0.086 Uiso 1 1 calc R . . H26B H -0.3217 0.2564 0.0581 0.086 Uiso 1 1 calc R . . H26C H -0.2949 0.1642 0.0722 0.086 Uiso 1 1 calc R . . C27 C 0.3503(6) 0.3795(3) 0.3524(6) 0.0284(13) Uani 1 1 d . . . H27A H 0.3659 0.3369 0.4150 0.034 Uiso 1 1 calc R . . C28 C 0.3865(7) 0.4570(4) 0.4219(5) 0.0315(14) Uani 1 1 d . . . H28A H 0.3196 0.4648 0.4727 0.047 Uiso 1 1 calc R . . H28B H 0.3748 0.4999 0.3629 0.047 Uiso 1 1 calc R . . H28C H 0.4884 0.4558 0.4746 0.047 Uiso 1 1 calc R . . C29 C 0.4525(6) 0.3638(4) 0.2731(7) 0.048(2) Uani 1 1 d . . . H29A H 0.4262 0.3140 0.2302 0.073 Uiso 1 1 calc R . . H29B H 0.5545 0.3615 0.3252 0.073 Uiso 1 1 calc R . . H29C H 0.4427 0.4058 0.2128 0.073 Uiso 1 1 calc R . . N31 N 0.1230(4) 0.3748(3) 0.7011(4) 0.0192(9) Uani 1 1 d . . . C32 C -0.0070(5) 0.3733(3) 0.7270(5) 0.0236(12) Uani 1 1 d . . . H32A H -0.0739 0.3319 0.6958 0.028 Uiso 1 1 calc R . . C33 C -0.0454(6) 0.4297(3) 0.7968(5) 0.0281(13) Uani 1 1 d . . . H33A H -0.1375 0.4269 0.8144 0.034 Uiso 1 1 calc R . . C34 C 0.0486(6) 0.4904(3) 0.8417(5) 0.0288(13) Uani 1 1 d . . . H34A H 0.0214 0.5308 0.8883 0.035 Uiso 1 1 calc R . . C35 C 0.1843(6) 0.4918(4) 0.8177(6) 0.0346(14) Uani 1 1 d . . . H35A H 0.2535 0.5320 0.8504 0.042 Uiso 1 1 calc R . . C36 C 0.2171(5) 0.4330(3) 0.7445(5) 0.0220(12) Uani 1 1 d . . . H36A H 0.3083 0.4344 0.7252 0.026 Uiso 1 1 calc R . . B1 B 0.4015(7) 0.0152(4) 0.1307(6) 0.0247(14) Uani 1 1 d . . . F1 F 0.4943(3) 0.0782(2) 0.1320(3) 0.0389(9) Uani 1 1 d . . . F2 F 0.2573(3) 0.04160(19) 0.0931(3) 0.0313(8) Uani 1 1 d . . . F3 F 0.4233(4) -0.0412(2) 0.0510(3) 0.0403(9) Uani 1 1 d . . . F4 F 0.4332(4) -0.0155(2) 0.2493(3) 0.0344(10) Uani 1 1 d . . . C40 C 0.2354(10) 0.1944(5) 0.9073(7) 0.070(3) Uani 1 1 d . . . H40A H 0.2906 0.1501 0.9547 0.084 Uiso 1 1 calc R . . H40B H 0.2367 0.1886 0.8209 0.084 Uiso 1 1 calc R . . Cl1 Cl 0.0507(3) 0.1910(2) 0.9138(2) 0.1210(13) Uani 1 1 d . . . Cl2 Cl 0.3211(4) 0.27965(19) 0.9650(3) 0.1517(17) 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 0.01458(9) 0.01490(9) 0.01644(9) -0.00144(13) 0.00432(6) 0.00158(12) C1 0.010(2) 0.014(3) 0.013(3) 0.001(2) -0.0013(19) 0.0005(19) N2 0.013(2) 0.017(2) 0.016(2) -0.0002(18) 0.0022(17) 0.0027(17) C3 0.022(3) 0.015(3) 0.014(3) -0.003(2) 0.006(2) 0.003(2) C4 0.018(3) 0.023(3) 0.012(3) -0.006(2) 0.004(2) 0.003(2) N5 0.016(2) 0.011(2) 0.015(2) -0.0009(18) 0.0038(19) 0.0015(17) C6 0.020(3) 0.015(3) 0.010(2) 0.001(2) 0.004(2) 0.006(2) C7 0.016(2) 0.018(3) 0.017(3) -0.002(2) 0.002(2) 0.003(2) C8 0.026(3) 0.025(4) 0.019(3) -0.006(3) 0.001(3) -0.003(3) C9 0.030(3) 0.024(3) 0.013(3) 0.001(2) 0.000(2) 0.008(2) C10 0.026(3) 0.021(3) 0.020(3) 0.000(2) 0.009(2) 0.001(2) C11 0.013(2) 0.017(3) 0.017(3) -0.003(2) 0.006(2) 0.003(2) C12 0.020(3) 0.015(3) 0.024(3) 0.002(2) 0.003(2) -0.001(2) C13 0.029(3) 0.028(3) 0.053(3) 0.002(6) 0.016(2) -0.008(5) C14 0.032(3) 0.030(4) 0.037(4) -0.005(3) 0.016(3) -0.005(3) C15 0.019(3) 0.024(3) 0.024(3) 0.005(2) 0.008(2) -0.003(2) C16 0.016(3) 0.033(4) 0.074(5) 0.011(3) 0.016(3) 0.000(3) C17 0.036(3) 0.031(4) 0.026(3) -0.005(3) 0.001(3) -0.011(3) C18 0.023(2) 0.011(4) 0.014(2) 0.009(3) 0.0080(17) 0.007(3) C19 0.021(2) 0.024(2) 0.011(2) -0.009(4) 0.0049(16) 0.006(4) C20 0.026(3) 0.026(3) 0.017(3) 0.003(2) 0.008(2) 0.007(2) C21 0.036(3) 0.025(3) 0.028(3) 0.007(2) 0.010(3) 0.012(3) C22 0.034(3) 0.023(3) 0.030(3) 0.005(2) 0.015(3) -0.002(2) C23 0.021(3) 0.014(3) 0.025(3) 0.004(2) 0.014(3) -0.002(2) C24 0.019(3) 0.025(3) 0.021(3) -0.001(2) -0.001(2) 0.004(2) C25 0.042(4) 0.045(4) 0.046(4) -0.008(3) 0.026(3) -0.015(3) C26 0.061(5) 0.060(5) 0.035(4) 0.001(4) -0.011(3) -0.040(4) C27 0.022(3) 0.016(3) 0.045(4) 0.004(3) 0.005(3) -0.003(2) C28 0.034(3) 0.030(4) 0.027(4) 0.001(3) 0.002(3) -0.004(3) C29 0.030(3) 0.022(4) 0.097(6) -0.030(4) 0.025(4) -0.007(3) N31 0.023(2) 0.021(2) 0.015(2) 0.0004(19) 0.0072(18) 0.0023(18) C32 0.019(3) 0.029(3) 0.026(3) -0.007(2) 0.011(2) -0.003(2) C33 0.026(3) 0.033(4) 0.031(3) -0.001(3) 0.018(3) 0.002(3) C34 0.035(3) 0.027(3) 0.030(3) -0.016(3) 0.018(3) -0.004(3) C35 0.033(3) 0.033(4) 0.038(4) -0.016(3) 0.010(3) -0.005(3) C36 0.017(3) 0.027(3) 0.024(3) -0.002(2) 0.008(2) 0.002(2) B1 0.029(4) 0.023(4) 0.025(4) 0.000(3) 0.011(3) -0.003(3) F1 0.0293(18) 0.038(2) 0.051(2) 0.0032(19) 0.0144(17) -0.0131(16) F2 0.0212(16) 0.034(2) 0.037(2) 0.0023(15) 0.0055(14) 0.0028(14) F3 0.053(2) 0.037(2) 0.034(2) -0.0119(17) 0.0182(18) 0.0048(17) F4 0.049(2) 0.029(2) 0.026(2) 0.0100(17) 0.0116(18) 0.0148(17) C40 0.111(7) 0.068(6) 0.038(5) 0.014(4) 0.033(5) 0.054(5) Cl1 0.122(2) 0.178(3) 0.0669(17) 0.0449(19) 0.0329(16) 0.102(2) Cl2 0.226(3) 0.066(3) 0.0859(18) -0.0069(16) -0.0811(19) 0.041(2) _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 C1 1.988(5) . ? Au1 N31 2.065(4) . ? C1 N5 1.343(6) . ? C1 N2 1.354(6) . ? N2 C3 1.399(6) . ? N2 C6 1.439(6) . ? C3 C4 1.368(7) . ? C3 H3A 0.9500 . ? C4 N5 1.384(6) . ? C4 H4A 0.9500 . ? N5 C18 1.457(7) . ? C6 C7 1.391(7) . ? C6 C11 1.406(7) . ? C7 C8 1.395(8) . ? C7 C12 1.513(7) . ? C8 C9 1.383(9) . ? C8 H8A 0.9500 . ? C9 C10 1.381(8) . ? C9 H9A 0.9500 . ? C10 C11 1.384(7) . ? C10 H10A 0.9500 . ? C11 C15 1.538(7) . ? C12 C14 1.537(7) . ? C12 C13 1.531(10) . ? C12 H12A 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.519(8) . ? C15 C16 1.537(7) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.393(6) . ? C18 C23 1.398(9) . ? C19 C20 1.408(10) . ? C19 C24 1.498(11) . ? C20 C21 1.363(8) . ? C20 H20A 0.9500 . ? C21 C22 1.386(8) . ? C21 H21A 0.9500 . ? C22 C23 1.394(8) . ? C22 H22A 0.9500 . ? C23 C27 1.525(8) . ? C24 C26 1.511(8) . ? C24 C25 1.525(7) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.522(8) . ? C27 C28 1.533(8) . ? C27 H27A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? N31 C36 1.335(7) . ? N31 C32 1.346(6) . ? C32 C33 1.363(7) . ? C32 H32A 0.9500 . ? C33 C34 1.370(8) . ? C33 H33A 0.9500 . ? C34 C35 1.388(7) . ? C34 H34A 0.9500 . ? C35 C36 1.397(7) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? B1 F3 1.379(7) . ? B1 F1 1.390(7) . ? B1 F2 1.386(7) . ? B1 F4 1.397(7) . ? C40 Cl2 1.708(10) . ? C40 Cl1 1.773(9) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? 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 C1 Au1 N31 177.20(18) . . ? N5 C1 N2 106.0(4) . . ? N5 C1 Au1 127.2(4) . . ? N2 C1 Au1 126.6(3) . . ? C1 N2 C3 110.7(4) . . ? C1 N2 C6 124.5(4) . . ? C3 N2 C6 124.4(4) . . ? C4 C3 N2 105.3(4) . . ? C4 C3 H3A 127.4 . . ? N2 C3 H3A 127.4 . . ? C3 C4 N5 107.5(4) . . ? C3 C4 H4A 126.2 . . ? N5 C4 H4A 126.2 . . ? C1 N5 C4 110.4(4) . . ? C1 N5 C18 126.0(4) . . ? C4 N5 C18 123.2(4) . . ? C7 C6 C11 123.2(5) . . ? C7 C6 N2 118.0(4) . . ? C11 C6 N2 118.7(4) . . ? C6 C7 C8 117.0(5) . . ? C6 C7 C12 122.8(4) . . ? C8 C7 C12 120.2(5) . . ? C9 C8 C7 120.6(6) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C10 C9 C8 121.4(5) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C11 120.1(5) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C6 117.7(5) . . ? C10 C11 C15 121.8(4) . . ? C6 C11 C15 120.4(4) . . ? C7 C12 C14 110.4(4) . . ? C7 C12 C13 112.5(4) . . ? C14 C12 C13 111.1(4) . . ? C7 C12 H12A 107.5 . . ? C14 C12 H12A 107.5 . . ? C13 C12 H12A 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C15 C16 109.8(4) . . ? C17 C15 C11 111.8(5) . . ? C16 C15 C11 109.9(5) . . ? C17 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? C11 C15 H15A 108.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 125.0(7) . . ? C19 C18 N5 117.4(7) . . ? C23 C18 N5 117.6(4) . . ? C18 C19 C20 115.4(8) . . ? C18 C19 C24 123.2(7) . . ? C20 C19 C24 121.3(4) . . ? C21 C20 C19 121.6(5) . . ? C21 C20 H20A 119.2 . . ? C19 C20 H20A 119.2 . . ? C20 C21 C22 121.1(5) . . ? C20 C21 H21A 119.4 . . ? C22 C21 H21A 119.4 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 . . ? C18 C23 C22 116.3(5) . . ? C18 C23 C27 122.5(5) . . ? C22 C23 C27 121.1(5) . . ? C19 C24 C26 114.2(5) . . ? C19 C24 C25 111.1(5) . . ? C26 C24 C25 110.0(5) . . ? C19 C24 H24A 107.0 . . ? C26 C24 H24A 107.0 . . ? C25 C24 H24A 107.0 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 C29 110.2(5) . . ? C23 C27 C28 112.1(5) . . ? C29 C27 C28 111.8(5) . . ? C23 C27 H27A 107.5 . . ? C29 C27 H27A 107.5 . . ? C28 C27 H27A 107.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 N31 C32 119.3(4) . . ? C36 N31 Au1 119.6(3) . . ? C32 N31 Au1 120.6(3) . . ? N31 C32 C33 121.8(5) . . ? N31 C32 H32A 119.1 . . ? C33 C32 H32A 119.1 . . ? C32 C33 C34 120.1(5) . . ? C32 C33 H33A 119.9 . . ? C34 C33 H33A 119.9 . . ? C33 C34 C35 118.7(5) . . ? C33 C34 H34A 120.6 . . ? C35 C34 H34A 120.6 . . ? C34 C35 C36 118.6(5) . . ? C34 C35 H35A 120.7 . . ? C36 C35 H35A 120.7 . . ? N31 C36 C35 121.4(5) . . ? N31 C36 H36A 119.3 . . ? C35 C36 H36A 119.3 . . ? F3 B1 F1 109.9(5) . . ? F3 B1 F2 110.2(5) . . ? F1 B1 F2 108.3(5) . . ? F3 B1 F4 109.7(5) . . ? F1 B1 F4 108.7(5) . . ? F2 B1 F4 110.0(5) . . ? Cl2 C40 Cl1 112.3(4) . . ? Cl2 C40 H40A 109.1 . . ? Cl1 C40 H40A 109.1 . . ? Cl2 C40 H40B 109.1 . . ? Cl1 C40 H40B 109.1 . . ? H40A C40 H40B 107.9 . . ? 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 N5 C1 N2 C3 0.1(5) . . . . ? Au1 C1 N2 C3 -175.6(3) . . . . ? N5 C1 N2 C6 174.1(4) . . . . ? Au1 C1 N2 C6 -1.6(6) . . . . ? C1 N2 C3 C4 0.1(5) . . . . ? C6 N2 C3 C4 -174.0(4) . . . . ? N2 C3 C4 N5 -0.2(5) . . . . ? N2 C1 N5 C4 -0.3(5) . . . . ? Au1 C1 N5 C4 175.4(3) . . . . ? N2 C1 N5 C18 -173.7(4) . . . . ? Au1 C1 N5 C18 2.0(7) . . . . ? C3 C4 N5 C1 0.3(6) . . . . ? C3 C4 N5 C18 173.9(4) . . . . ? C1 N2 C6 C7 -78.7(6) . . . . ? C3 N2 C6 C7 94.5(6) . . . . ? C1 N2 C6 C11 101.1(6) . . . . ? C3 N2 C6 C11 -85.7(5) . . . . ? C11 C6 C7 C8 -0.9(7) . . . . ? N2 C6 C7 C8 178.9(4) . . . . ? C11 C6 C7 C12 177.6(4) . . . . ? N2 C6 C7 C12 -2.6(7) . . . . ? C6 C7 C8 C9 -0.4(8) . . . . ? C12 C7 C8 C9 -178.9(5) . . . . ? C7 C8 C9 C10 0.8(9) . . . . ? C8 C9 C10 C11 0.0(8) . . . . ? C9 C10 C11 C6 -1.2(7) . . . . ? C9 C10 C11 C15 -178.8(5) . . . . ? C7 C6 C11 C10 1.7(7) . . . . ? N2 C6 C11 C10 -178.1(4) . . . . ? C7 C6 C11 C15 179.3(4) . . . . ? N2 C6 C11 C15 -0.5(7) . . . . ? C6 C7 C12 C14 -111.2(5) . . . . ? C8 C7 C12 C14 67.3(6) . . . . ? C6 C7 C12 C13 124.0(5) . . . . ? C8 C7 C12 C13 -57.5(6) . . . . ? C10 C11 C15 C17 -38.3(6) . . . . ? C6 C11 C15 C17 144.1(5) . . . . ? C10 C11 C15 C16 83.9(6) . . . . ? C6 C11 C15 C16 -93.7(5) . . . . ? C1 N5 C18 C19 -108.7(5) . . . . ? C4 N5 C18 C19 78.7(6) . . . . ? C1 N5 C18 C23 74.9(6) . . . . ? C4 N5 C18 C23 -97.7(6) . . . . ? C23 C18 C19 C20 0.1(7) . . . . ? N5 C18 C19 C20 -176.1(4) . . . . ? C23 C18 C19 C24 -176.3(5) . . . . ? N5 C18 C19 C24 7.6(7) . . . . ? C18 C19 C20 C21 0.9(7) . . . . ? C24 C19 C20 C21 177.3(5) . . . . ? C19 C20 C21 C22 -1.3(8) . . . . ? C20 C21 C22 C23 0.7(8) . . . . ? C19 C18 C23 C22 -0.6(8) . . . . ? N5 C18 C23 C22 175.5(4) . . . . ? C19 C18 C23 C27 -177.4(5) . . . . ? N5 C18 C23 C27 -1.3(8) . . . . ? C21 C22 C23 C18 0.2(8) . . . . ? C21 C22 C23 C27 177.1(5) . . . . ? C18 C19 C24 C26 -152.8(5) . . . . ? C20 C19 C24 C26 31.1(8) . . . . ? C18 C19 C24 C25 82.0(6) . . . . ? C20 C19 C24 C25 -94.1(6) . . . . ? C18 C23 C27 C29 95.0(6) . . . . ? C22 C23 C27 C29 -81.7(6) . . . . ? C18 C23 C27 C28 -139.9(5) . . . . ? C22 C23 C27 C28 43.5(7) . . . . ? C36 N31 C32 C33 -0.2(8) . . . . ? Au1 N31 C32 C33 -171.8(4) . . . . ? N31 C32 C33 C34 0.7(9) . . . . ? C32 C33 C34 C35 -1.9(9) . . . . ? C33 C34 C35 C36 2.6(9) . . . . ? C32 N31 C36 C35 0.9(8) . . . . ? Au1 N31 C36 C35 172.6(4) . . . . ? C34 C35 C36 N31 -2.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.636 _refine_diff_density_min -0.944 _refine_diff_density_rms 0.098