# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Toste, F.' 'Mankad, Neal' _publ_contact_author_name 'Toste, F.' _publ_contact_author_email fdtoste@berkeley.edu _publ_section_title ; C(sp3)-F Reductive Elimination From Alkylgold(III) Fluoride Complexes ; # Attachment '- IPrAuF2CH2Cl2.cif' data_npm021sym _database_code_depnum_ccdc_archive 'CCDC 837541' #TrackingRef '- IPrAuF2CH2Cl2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common IPrAuF*2CH2Cl2 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H40 Au Cl4 F N2' _chemical_formula_weight 774.40 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' 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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.3108(10) _cell_length_b 16.3917(17) _cell_length_c 10.7713(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.594(2) _cell_angle_gamma 90.00 _cell_volume 1597.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9392 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 4.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.039 _exptl_absorpt_correction_T_max 0.609 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51743 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.15 _reflns_number_total 3646 _reflns_number_gt 3436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The disordered dichloromethane solvent molecule refined to 0.50 occupancy for each conformation. ; _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^)+(0.0325P)^2^+5.7645P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3646 _refine_ls_number_parameters 198 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0693 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.060 _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 -0.00196(2) 0.7500 0.937282(17) 0.02001(7) Uani 1 2 d S . . F1 F -0.2238(3) 0.7500 0.9395(2) 0.0159(5) Uani 1 2 d S . . N1 N 0.2911(3) 0.81555(18) 0.9217(3) 0.0208(6) Uani 1 1 d . . . C1 C 0.2050(6) 0.7500 0.9275(4) 0.0210(10) Uani 1 2 d S . . C2 C 0.4312(4) 0.7914(2) 0.9130(3) 0.0269(8) Uani 1 1 d . . . H2 H 0.5115 0.8260 0.9080 0.032 Uiso 1 1 calc R . . C3 C 0.2422(4) 0.8991(2) 0.9221(3) 0.0227(7) Uani 1 1 d . . . C4 C 0.2786(5) 0.9425(2) 1.0370(4) 0.0304(8) Uani 1 1 d . . . C5 C 0.2263(6) 1.0225(3) 1.0351(4) 0.0425(11) Uani 1 1 d . . . H5 H 0.2494 1.0540 1.1112 0.051 Uiso 1 1 calc R . . C6 C 0.1419(6) 1.0565(3) 0.9250(5) 0.0473(12) Uani 1 1 d . . . H6 H 0.1062 1.1107 0.9264 0.057 Uiso 1 1 calc R . . C7 C 0.1087(5) 1.0125(2) 0.8125(4) 0.0380(10) Uani 1 1 d . . . H7 H 0.0515 1.0371 0.7372 0.046 Uiso 1 1 calc R . . C8 C 0.1578(4) 0.9323(2) 0.8077(4) 0.0275(8) Uani 1 1 d . . . C9 C 0.3690(5) 0.9048(3) 1.1589(4) 0.0350(9) Uani 1 1 d . . . H9 H 0.4105 0.8524 1.1348 0.042 Uiso 1 1 calc R . . C10 C 0.4982(9) 0.9575(5) 1.2235(7) 0.098(3) Uani 1 1 d . . . H10A H 0.5586 0.9702 1.1627 0.148 Uiso 1 1 calc R . . H10B H 0.5583 0.9282 1.2968 0.148 Uiso 1 1 calc R . . H10C H 0.4614 1.0083 1.2528 0.148 Uiso 1 1 calc R . . C11 C 0.2729(6) 0.8838(5) 1.2495(5) 0.071(2) Uani 1 1 d . . . H11A H 0.2382 0.9341 1.2819 0.106 Uiso 1 1 calc R . . H11B H 0.3304 0.8519 1.3211 0.106 Uiso 1 1 calc R . . H11C H 0.1878 0.8517 1.2042 0.106 Uiso 1 1 calc R . . C12 C 0.1193(5) 0.8849(2) 0.6829(4) 0.0319(8) Uani 1 1 d . . . H12 H 0.1680 0.8303 0.6976 0.038 Uiso 1 1 calc R . . C13 C 0.1759(5) 0.9287(3) 0.5780(4) 0.0361(9) Uani 1 1 d . . . H13A H 0.1324 0.9834 0.5648 0.054 Uiso 1 1 calc R . . H13B H 0.1476 0.8975 0.4984 0.054 Uiso 1 1 calc R . . H13C H 0.2837 0.9332 0.6038 0.054 Uiso 1 1 calc R . . C14 C -0.0474(6) 0.8719(3) 0.6409(4) 0.0469(12) Uani 1 1 d . . . H14A H -0.0814 0.8422 0.7077 0.070 Uiso 1 1 calc R . . H14B H -0.0706 0.8402 0.5616 0.070 Uiso 1 1 calc R . . H14C H -0.0972 0.9249 0.6266 0.070 Uiso 1 1 calc R . . C15 C 0.7680(10) 0.7500 0.2287(9) 0.093(4) Uani 1 2 d S . . H15A H 0.7458 0.7986 0.1728 0.112 Uiso 0.50 1 calc PR . . H15B H 0.7458 0.7014 0.1728 0.112 Uiso 0.50 1 calc PR . . C16 C 0.6328(9) 0.7500 0.6447(9) 0.064(2) Uani 1 2 d S . . H16 H 0.705(8) 0.7500 0.587(7) 0.04(2) Uiso 1 2 d S . . H17 H 0.672(11) 0.7500 0.753(10) 0.09(3) Uiso 1 2 d S . . Cl1 Cl 0.95770(19) 0.7500 0.29684(17) 0.0470(4) Uani 1 2 d S . . Cl2 Cl 0.6529(2) 0.7500 0.3217(2) 0.1149(14) Uani 1 2 d SU . . Cl3A Cl 0.5704(6) 0.8659(4) 0.6085(4) 0.0622(16) Uani 0.412(11) 1 d PU A 1 Cl3B Cl 0.4966(8) 0.8130(6) 0.5919(4) 0.113(4) Uani 0.588(11) 1 d PU . 2 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 0.02359(11) 0.01490(10) 0.02099(10) 0.000 0.00412(7) 0.000 F1 0.0131(12) 0.0162(12) 0.0202(13) 0.000 0.0076(10) 0.000 N1 0.0238(14) 0.0211(14) 0.0165(13) 0.0005(11) 0.0026(11) -0.0018(12) C1 0.034(3) 0.015(2) 0.012(2) 0.000 0.0012(18) 0.000 C2 0.0255(18) 0.035(2) 0.0208(16) 0.0005(15) 0.0063(14) -0.0028(15) C3 0.0275(18) 0.0173(16) 0.0241(17) -0.0018(13) 0.0076(14) -0.0057(13) C4 0.038(2) 0.0276(19) 0.0279(19) -0.0054(15) 0.0129(16) -0.0125(16) C5 0.070(3) 0.024(2) 0.040(2) -0.0113(17) 0.027(2) -0.015(2) C6 0.083(4) 0.0160(19) 0.052(3) -0.0001(18) 0.034(3) 0.002(2) C7 0.056(3) 0.0189(19) 0.041(2) 0.0060(16) 0.015(2) 0.0016(18) C8 0.036(2) 0.0164(16) 0.0303(19) 0.0016(14) 0.0083(16) -0.0025(15) C9 0.038(2) 0.044(2) 0.0238(18) -0.0077(17) 0.0084(16) -0.0145(19) C10 0.087(5) 0.115(7) 0.074(4) 0.015(4) -0.020(4) -0.069(5) C11 0.046(3) 0.125(6) 0.045(3) 0.039(3) 0.017(2) -0.003(3) C12 0.042(2) 0.0212(18) 0.0271(19) 0.0041(15) -0.0024(16) 0.0014(16) C13 0.037(2) 0.038(2) 0.031(2) 0.0011(17) 0.0033(17) 0.0041(18) C14 0.053(3) 0.048(3) 0.034(2) 0.013(2) -0.001(2) -0.020(2) C15 0.050(5) 0.187(13) 0.047(5) 0.000 0.020(4) 0.000 C16 0.038(4) 0.101(7) 0.052(5) 0.000 0.009(3) 0.000 Cl1 0.0414(9) 0.0535(10) 0.0485(9) 0.000 0.0157(7) 0.000 Cl2 0.0378(11) 0.254(5) 0.0513(13) 0.000 0.0079(9) 0.000 Cl3A 0.049(2) 0.065(3) 0.066(2) -0.0137(19) 0.0002(17) 0.024(2) Cl3B 0.111(4) 0.181(7) 0.057(2) 0.046(3) 0.039(2) 0.104(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 Au1 C1 1.954(5) . ? Au1 F1 2.071(2) . ? N1 C1 1.351(4) . ? N1 C2 1.387(5) . ? N1 C3 1.443(5) . ? C1 N1 1.351(4) 4_575 ? C2 C2 1.356(8) 4_575 ? C2 H2 0.9500 . ? C3 C4 1.399(5) . ? C3 C8 1.406(5) . ? C4 C5 1.397(6) . ? C4 C9 1.515(6) . ? C5 C6 1.377(7) . ? C5 H5 0.9500 . ? C6 C7 1.382(6) . ? C6 H6 0.9500 . ? C7 C8 1.396(5) . ? C7 H7 0.9500 . ? C8 C12 1.521(5) . ? C9 C11 1.511(6) . ? C9 C10 1.511(7) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C14 1.526(6) . ? C12 C13 1.533(6) . ? C12 H12 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 Cl2 1.629(9) . ? C15 Cl1 1.747(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 Cl3B 1.631(7) . ? C16 Cl3B 1.631(7) 4_575 ? C16 Cl3A 1.998(6) . ? C16 Cl3A 1.998(6) 4_575 ? C16 H16 1.02(8) . ? C16 H17 1.14(11) . ? Cl3B Cl3B 2.064(19) 4_575 ? 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 F1 177.65(15) . . ? C1 N1 C2 110.7(3) . . ? C1 N1 C3 124.3(3) . . ? C2 N1 C3 125.0(3) . . ? N1 C1 N1 105.3(4) . 4_575 ? N1 C1 Au1 127.3(2) . . ? N1 C1 Au1 127.3(2) 4_575 . ? C2 C2 N1 106.6(2) 4_575 . ? C2 C2 H2 126.7 4_575 . ? N1 C2 H2 126.7 . . ? C4 C3 C8 123.2(4) . . ? C4 C3 N1 118.3(3) . . ? C8 C3 N1 118.5(3) . . ? C5 C4 C3 117.0(4) . . ? C5 C4 C9 121.1(4) . . ? C3 C4 C9 121.9(4) . . ? C6 C5 C4 121.3(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.6(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 121.1(4) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C3 116.9(4) . . ? C7 C8 C12 120.2(4) . . ? C3 C8 C12 122.9(3) . . ? C11 C9 C10 111.1(5) . . ? C11 C9 C4 111.1(4) . . ? C10 C9 C4 112.7(4) . . ? C11 C9 H9 107.2 . . ? C10 C9 H9 107.2 . . ? C4 C9 H9 107.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 C14 110.2(4) . . ? C8 C12 C13 111.2(3) . . ? C14 C12 C13 110.4(3) . . ? C8 C12 H12 108.3 . . ? C14 C12 H12 108.3 . . ? C13 C12 H12 108.3 . . ? 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 . . ? Cl2 C15 Cl1 119.2(6) . . ? Cl2 C15 H15A 107.5 . . ? Cl1 C15 H15A 107.5 . . ? Cl2 C15 H15B 107.5 . . ? Cl1 C15 H15B 107.5 . . ? H15A C15 H15B 107.0 . . ? Cl3B C16 Cl3B 78.5(9) . 4_575 ? Cl3B C16 Cl3A 33.2(3) . . ? Cl3B C16 Cl3A 111.5(7) 4_575 . ? Cl3B C16 Cl3A 111.5(7) . 4_575 ? Cl3B C16 Cl3A 33.2(3) 4_575 4_575 ? Cl3A C16 Cl3A 143.9(5) . 4_575 ? Cl3B C16 H16 111(3) . . ? Cl3B C16 H16 111(3) 4_575 . ? Cl3A C16 H16 94.9(13) . . ? Cl3A C16 H16 94.9(13) 4_575 . ? Cl3B C16 H17 113(4) . . ? Cl3B C16 H17 113(4) 4_575 . ? Cl3A C16 H17 102.1(13) . . ? Cl3A C16 H17 102.1(13) 4_575 . ? H16 C16 H17 122(7) . . ? C16 Cl3B Cl3B 50.7(5) . 4_575 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.576 _refine_diff_density_min -3.025 _refine_diff_density_rms 0.123