# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Young Keun Chung' _publ_contact_author_email YKCHUNG@SNU.AC.KR _publ_section_title ; Au(PPh3)OPOF2-Catalyzed Intramolecular [4+2] Cycloaddition Reaction of Dienynes ; loop_ _publ_author_name 'Young Keun Chung' 'Soo Min Kim' # Attachment '1b.cif' data_12d _database_code_depnum_ccdc_archive 'CCDC 740934' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Au dienyne product 1b' _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O2 S' _chemical_formula_sum 'C15 H17 N O2 S' _chemical_formula_weight 275.36 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' S S 0.1246 0.1234 '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 1 21/n 1' 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 11.4368(9) _cell_length_b 9.3232(4) _cell_length_c 13.8085(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.023(3) _cell_angle_gamma 90.00 _cell_volume 1434.50(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3274 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method none _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5731 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3274 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP32 _computing_publication_material WinGX _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^)+(0.0808P)^2^+0.1959P] 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 3274 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.002 _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 S1 S 0.13736(7) 0.13336(7) 0.67726(5) 0.0453(2) Uani 1 1 d . . . N1 N 0.0361(2) 0.2581(2) 0.64219(15) 0.0409(5) Uani 1 1 d . . . O1 O 0.0829(2) 0.00096(19) 0.63813(15) 0.0592(6) Uani 1 1 d . . . O2 O 0.1801(2) 0.1497(2) 0.78175(14) 0.0626(6) Uani 1 1 d . . . C1 C 0.5446(4) 0.2723(5) 0.4797(4) 0.1052(15) Uani 1 1 d . . . H1A H 0.5605 0.1919 0.4412 0.158 Uiso 1 1 calc R . . H1B H 0.6153 0.2946 0.5296 0.158 Uiso 1 1 calc R . . H1C H 0.5224 0.3537 0.4370 0.158 Uiso 1 1 calc R . . C2 C 0.4431(3) 0.2355(4) 0.5292(3) 0.0662(9) Uani 1 1 d . . . C3 C 0.4324(3) 0.3040(4) 0.6150(3) 0.0700(9) Uani 1 1 d . . . H3 H 0.4883 0.3735 0.6426 0.084 Uiso 1 1 calc R . . C4 C 0.3413(3) 0.2719(3) 0.6605(2) 0.0582(8) Uani 1 1 d . . . H4 H 0.3363 0.3185 0.7190 0.070 Uiso 1 1 calc R . . C5 C 0.2570(3) 0.1705(3) 0.6198(2) 0.0428(6) Uani 1 1 d . . . C6 C 0.2654(3) 0.1012(3) 0.5340(2) 0.0585(8) Uani 1 1 d . . . H6 H 0.2084 0.0332 0.5056 0.070 Uiso 1 1 calc R . . C7 C 0.3592(3) 0.1336(4) 0.4903(3) 0.0700(10) Uani 1 1 d . . . H7 H 0.3658 0.0851 0.4329 0.084 Uiso 1 1 calc R . . C8 C 0.0652(3) 0.4052(3) 0.6825(2) 0.0493(7) Uani 1 1 d . . . H8A H 0.1274 0.4460 0.6534 0.074 Uiso 1 1 calc R . . H8B H 0.0962 0.3996 0.7538 0.074 Uiso 1 1 calc R . . C9 C -0.0432(3) 0.5025(3) 0.6608(2) 0.0578(8) Uani 1 1 d . . . H9 H -0.0258 0.6043 0.6751 0.087 Uiso 1 1 calc R . . C10 C -0.1640(3) 0.4534(3) 0.6736(2) 0.0572(8) Uani 1 1 d . . . H10 H -0.1680 0.3538 0.6952 0.086 Uiso 1 1 calc R . . C11 C -0.2433(3) 0.5550(4) 0.7098(3) 0.0749(10) Uani 1 1 d . . . H11 H -0.2392 0.6511 0.6927 0.090 Uiso 1 1 calc R . . C12 C -0.3188(3) 0.5205(4) 0.7639(3) 0.0825(11) Uani 1 1 d . . . H12A H -0.3255 0.4255 0.7825 0.099 Uiso 1 1 calc R . . H12B H -0.3660 0.5908 0.7840 0.099 Uiso 1 1 calc R . . C13 C -0.1395(3) 0.4735(3) 0.5700(2) 0.0601(8) Uani 1 1 d . . . H13 H -0.1762 0.5571 0.5320 0.090 Uiso 1 1 calc R . . C14 C -0.1234(3) 0.3447(3) 0.5126(2) 0.0574(8) Uani 1 1 d . . . H14 H -0.1735 0.3320 0.4500 0.069 Uiso 1 1 calc R . . C15 C -0.0411(2) 0.2466(3) 0.54620(18) 0.0459(7) Uani 1 1 d . . . H15 H -0.0334 0.1683 0.5063 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0534(5) 0.0438(4) 0.0393(4) 0.0030(3) 0.0119(3) 0.0017(3) N1 0.0420(13) 0.0424(12) 0.0372(12) -0.0033(9) 0.0065(10) -0.0022(10) O1 0.0767(15) 0.0390(11) 0.0668(13) -0.0010(9) 0.0265(12) -0.0104(10) O2 0.0750(16) 0.0734(14) 0.0372(11) 0.0073(9) 0.0079(10) 0.0153(12) C1 0.072(3) 0.118(4) 0.140(4) 0.008(3) 0.053(3) -0.010(3) C2 0.049(2) 0.073(2) 0.082(2) 0.0096(18) 0.0248(18) 0.0015(17) C3 0.048(2) 0.066(2) 0.094(3) -0.0116(19) 0.0112(19) -0.0089(17) C4 0.0499(19) 0.0617(19) 0.0597(19) -0.0145(15) 0.0057(15) 0.0005(15) C5 0.0437(16) 0.0419(14) 0.0426(14) -0.0001(11) 0.0092(12) 0.0042(12) C6 0.059(2) 0.0592(18) 0.0609(19) -0.0158(14) 0.0202(16) -0.0109(15) C7 0.071(2) 0.081(2) 0.065(2) -0.0154(18) 0.0321(19) -0.005(2) C8 0.0463(18) 0.0453(15) 0.0540(17) -0.0090(12) 0.0062(14) -0.0044(13) C9 0.060(2) 0.0452(17) 0.070(2) -0.0056(14) 0.0185(16) 0.0014(15) C10 0.057(2) 0.0539(18) 0.065(2) 0.0038(14) 0.0216(16) 0.0063(15) C11 0.067(2) 0.063(2) 0.098(3) -0.0006(19) 0.026(2) 0.0161(18) C12 0.065(2) 0.089(3) 0.098(3) -0.016(2) 0.028(2) 0.013(2) C13 0.052(2) 0.0635(19) 0.064(2) 0.0183(16) 0.0115(16) 0.0060(15) C14 0.0455(18) 0.083(2) 0.0404(16) 0.0062(15) 0.0021(13) -0.0070(16) C15 0.0470(18) 0.0538(16) 0.0375(15) -0.0039(12) 0.0107(13) -0.0096(14) _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 S1 O2 1.423(2) . ? S1 O1 1.432(2) . ? S1 N1 1.636(2) . ? S1 C5 1.763(3) . ? N1 C15 1.421(3) . ? N1 C8 1.489(3) . ? C1 C2 1.513(5) . ? C2 C7 1.371(5) . ? C2 C3 1.376(5) . ? C3 C4 1.365(4) . ? C4 C5 1.377(4) . ? C5 C6 1.373(4) . ? C6 C7 1.378(4) . ? C8 C9 1.510(4) . ? C9 C13 1.496(4) . ? C9 C10 1.504(4) . ? C10 C11 1.474(4) . ? C10 C13 1.530(4) . ? C11 C12 1.304(5) . ? C13 C14 1.473(5) . ? C14 C15 1.321(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.71(12) . . ? O2 S1 N1 106.39(12) . . ? O1 S1 N1 106.42(12) . . ? O2 S1 C5 108.12(14) . . ? O1 S1 C5 108.34(12) . . ? N1 S1 C5 107.26(12) . . ? C15 N1 C8 117.2(2) . . ? C15 N1 S1 118.12(18) . . ? C8 N1 S1 117.42(18) . . ? C7 C2 C3 118.0(3) . . ? C7 C2 C1 121.3(3) . . ? C3 C2 C1 120.7(4) . . ? C4 C3 C2 121.3(3) . . ? C3 C4 C5 120.0(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 S1 120.6(2) . . ? C4 C5 S1 119.7(2) . . ? C5 C6 C7 119.2(3) . . ? C2 C7 C6 121.7(3) . . ? N1 C8 C9 112.0(2) . . ? C13 C9 C10 61.4(2) . . ? C13 C9 C8 118.3(3) . . ? C10 C9 C8 121.9(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 C13 119.7(3) . . ? C9 C10 C13 59.1(2) . . ? C12 C11 C10 125.0(4) . . ? C14 C13 C9 116.2(3) . . ? C14 C13 C10 118.3(3) . . ? C9 C13 C10 59.6(2) . . ? C15 C14 C13 122.8(3) . . ? C14 C15 N1 121.3(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.339 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.136 # Attachment '1b1.cif' data_1c _database_code_depnum_ccdc_archive 'CCDC 740935' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Au catalyzed dienyne 1c' _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O2 S' _chemical_formula_sum 'C15 H17 N O2 S' _chemical_formula_weight 275.36 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.0592(2) _cell_length_b 10.6389(4) _cell_length_c 16.7180(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1433.42(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1878 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9780 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_process_details 'Blessing, R. H. Acta Crystallogr., Sect A 1995, 51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3269 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3269 _reflns_number_gt 2959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP32 _computing_publication_material WinGX _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^)+(0.0572P)^2^+0.1616P] 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 SHELXL _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.13(7) _refine_ls_number_reflns 3269 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _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 O2 O 1.04856(15) 0.47624(15) 0.72056(9) 0.0567(4) Uani 1 1 d . . . O1 O 0.86074(19) 0.32968(13) 0.79103(10) 0.0577(4) Uani 1 1 d . . . S1 S 0.91165(5) 0.45544(4) 0.77298(3) 0.04284(13) Uani 1 1 d . . . N1 N 0.75054(17) 0.52573(14) 0.73275(10) 0.0413(3) Uani 1 1 d . . . C5 C 0.9513(2) 0.53260(18) 0.86423(11) 0.0418(4) Uani 1 1 d . . . C12 C 0.5893(2) 0.49711(19) 0.77002(13) 0.0503(4) Uani 1 1 d . . . H12A H 0.5894 0.5255 0.8252 0.060 Uiso 1 1 calc R . . H12B H 0.5710 0.4070 0.7698 0.060 Uiso 1 1 calc R . . C8 C 0.7721(2) 0.66002(19) 0.71295(12) 0.0451(4) Uani 1 1 d . . . H8A H 0.8810 0.6733 0.6898 0.054 Uiso 1 1 calc R . . H8B H 0.7643 0.7100 0.7613 0.054 Uiso 1 1 calc R . . C4 C 1.0440(3) 0.6431(2) 0.86423(13) 0.0530(5) Uani 1 1 d . . . H4 H 1.0888 0.6742 0.8169 0.064 Uiso 1 1 calc R . . C3 C 1.0684(3) 0.7053(2) 0.93549(14) 0.0636(6) Uani 1 1 d . . . H3 H 1.1301 0.7792 0.9358 0.076 Uiso 1 1 calc R . . C11 C 0.4534(2) 0.5610(2) 0.72515(15) 0.0588(5) Uani 1 1 d . . . H11 H 0.3447 0.5367 0.7357 0.071 Uiso 1 1 calc R . . C10 C 0.4779(2) 0.6503(2) 0.67116(14) 0.0572(5) Uani 1 1 d . . . H10 H 0.3875 0.6815 0.6429 0.069 Uiso 1 1 calc R . . C7 C 0.9119(3) 0.5510(2) 1.00538(13) 0.0576(5) Uani 1 1 d . . . H7 H 0.8676 0.5200 1.0528 0.069 Uiso 1 1 calc R . . C9 C 0.6411(2) 0.70083(19) 0.65480(12) 0.0476(5) Uani 1 1 d . . . C6 C 0.8851(3) 0.48643(19) 0.93470(12) 0.0498(5) Uani 1 1 d . . . H6 H 0.8232 0.4127 0.9346 0.060 Uiso 1 1 calc R . . C13 C 0.6783(3) 0.7837(2) 0.59617(13) 0.0540(5) Uani 1 1 d . . . H13 H 0.7878 0.8109 0.5937 0.065 Uiso 1 1 calc R . . C1 C 1.0364(5) 0.7287(3) 1.08437(18) 0.0978(10) Uani 1 1 d . . . H1A H 1.1005 0.8030 1.0740 0.147 Uiso 1 1 calc R . . H1B H 1.0967 0.6745 1.1198 0.147 Uiso 1 1 calc R . . H1C H 0.9328 0.7518 1.1086 0.147 Uiso 1 1 calc R . . C2 C 1.0034(3) 0.6608(2) 1.00662(13) 0.0619(6) Uani 1 1 d . . . C14 C 0.5668(4) 0.8343(3) 0.53729(15) 0.0692(7) Uani 1 1 d . . . H14 H 0.4582 0.8049 0.5368 0.083 Uiso 1 1 calc R . . C15 C 0.6088(5) 0.9196(3) 0.48414(18) 0.0919(9) Uani 1 1 d . . . H15A H 0.7165 0.9509 0.4831 0.110 Uiso 1 1 calc R . . H15B H 0.5308 0.9486 0.4475 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0388(7) 0.0727(10) 0.0586(8) -0.0058(8) 0.0090(6) 0.0026(6) O1 0.0601(9) 0.0379(7) 0.0752(10) -0.0095(7) 0.0046(7) 0.0008(6) S1 0.0360(2) 0.0427(2) 0.0498(2) -0.0068(2) 0.00348(19) 0.00044(18) N1 0.0309(6) 0.0469(9) 0.0460(8) -0.0074(7) 0.0036(6) -0.0037(6) C5 0.0394(9) 0.0408(9) 0.0451(9) 0.0005(8) -0.0031(7) -0.0018(7) C12 0.0376(8) 0.0568(11) 0.0565(11) -0.0064(9) 0.0115(9) -0.0077(8) C8 0.0385(9) 0.0477(10) 0.0491(11) -0.0048(8) 0.0003(8) -0.0045(8) C4 0.0560(12) 0.0522(11) 0.0510(11) 0.0070(9) -0.0041(9) -0.0157(9) C3 0.0776(16) 0.0529(12) 0.0602(13) -0.0012(10) -0.0110(12) -0.0198(12) C11 0.0306(9) 0.0702(14) 0.0757(14) -0.0147(14) 0.0081(9) -0.0027(8) C10 0.0367(9) 0.0662(13) 0.0687(14) -0.0161(12) -0.0062(9) 0.0086(9) C7 0.0692(12) 0.0580(12) 0.0456(10) 0.0081(10) -0.0027(10) -0.0011(12) C9 0.0417(9) 0.0478(11) 0.0534(11) -0.0139(9) -0.0031(8) 0.0060(8) C6 0.0540(11) 0.0429(10) 0.0524(11) 0.0089(8) -0.0002(9) -0.0052(8) C13 0.0518(11) 0.0571(12) 0.0531(12) -0.0114(10) -0.0020(9) 0.0056(10) C1 0.136(3) 0.098(2) 0.0596(16) -0.0174(16) -0.0159(17) -0.019(2) C2 0.0785(14) 0.0577(13) 0.0494(12) -0.0020(10) -0.0134(11) -0.0022(12) C14 0.0726(15) 0.0707(15) 0.0645(14) -0.0067(12) -0.0105(12) 0.0172(13) C15 0.111(2) 0.092(2) 0.0734(17) 0.0118(16) -0.0132(18) 0.0185(19) _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 O2 S1 1.4262(14) . ? O1 S1 1.4317(15) . ? S1 N1 1.6424(16) . ? S1 C5 1.7615(19) . ? N1 C12 1.473(2) . ? N1 C8 1.477(3) . ? C5 C6 1.383(3) . ? C5 C4 1.393(3) . ? C12 C11 1.492(3) . ? C8 C9 1.499(3) . ? C4 C3 1.377(3) . ? C3 C2 1.383(3) . ? C11 C10 1.325(3) . ? C10 C9 1.446(3) . ? C7 C2 1.382(3) . ? C7 C6 1.384(3) . ? C9 C13 1.352(3) . ? C13 C14 1.437(3) . ? C1 C2 1.510(4) . ? C14 C15 1.314(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 119.76(9) . . ? O2 S1 N1 106.82(8) . . ? O1 S1 N1 106.57(9) . . ? O2 S1 C5 108.63(9) . . ? O1 S1 C5 107.75(9) . . ? N1 S1 C5 106.60(8) . . ? C12 N1 C8 113.48(14) . . ? C12 N1 S1 115.48(13) . . ? C8 N1 S1 116.07(11) . . ? C6 C5 C4 120.43(19) . . ? C6 C5 S1 120.15(14) . . ? C4 C5 S1 119.37(15) . . ? N1 C12 C11 109.93(18) . . ? N1 C8 C9 110.05(15) . . ? C3 C4 C5 118.8(2) . . ? C4 C3 C2 121.7(2) . . ? C10 C11 C12 124.03(18) . . ? C11 C10 C9 122.1(2) . . ? C2 C7 C6 121.0(2) . . ? C13 C9 C10 125.5(2) . . ? C13 C9 C8 120.20(18) . . ? C10 C9 C8 114.19(19) . . ? C5 C6 C7 119.40(18) . . ? C9 C13 C14 127.0(2) . . ? C7 C2 C3 118.6(2) . . ? C7 C2 C1 120.7(2) . . ? C3 C2 C1 120.7(2) . . ? C15 C14 C13 124.1(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.237 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.049 # Attachment '1c1.cif' # Attachment 'Au_PPh3_OPOF2.cif' data_pf2o2 _database_code_depnum_ccdc_archive 'CCDC 740936' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Au PF2O2' _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Au F2 O2 P2' _chemical_formula_sum 'C18 H15 Au F2 O2 P2' _chemical_formula_weight 560.21 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' Au Au -2.0133 8.8022 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 10.9034(6) _cell_length_b 9.1653(5) _cell_length_c 18.9173(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.487(3) _cell_angle_gamma 90.00 _cell_volume 1858.88(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17641 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.002 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 8.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4975 _exptl_absorpt_correction_T_max 0.4975 _exptl_absorpt_process_details 'Blessing, R. H. Acta Crystallogr., Sect A 1995, 51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7193 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4233 _reflns_number_gt 3211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP32 _computing_publication_material WinGX _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^)+(0.0600P)^2^+1.6965P] 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 SHELXL _refine_ls_extinction_coef 0.0008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4233 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.34566(2) 0.81729(3) 0.875662(15) 0.05986(16) Uani 1 1 d . . . P1 P 0.21379(17) 0.68232(18) 0.92341(10) 0.0517(4) Uani 1 1 d . . . P2 P 0.50362(16) 0.93601(17) 0.76004(10) 0.0544(4) Uani 1 1 d . . . C1 C 0.2760(6) 0.5052(8) 0.9545(4) 0.0545(15) Uani 1 1 d . . . O1 O 0.4620(5) 0.9496(5) 0.8310(3) 0.0711(14) Uani 1 1 d . . . C9 C 0.0017(10) 0.8496(9) 1.0635(5) 0.077(2) Uani 1 1 d . . . H9 H -0.0824 0.8574 1.0663 0.093 Uiso 1 1 calc R . . C2 C 0.2720(8) 0.4533(11) 1.0230(5) 0.079(2) Uani 1 1 d . . . H2 H 0.2378 0.5094 1.0554 0.095 Uiso 1 1 calc R . . C4 C 0.3676(9) 0.2307(12) 0.9936(6) 0.089(3) Uani 1 1 d . . . H4 H 0.3968 0.1376 1.0070 0.107 Uiso 1 1 calc R . . C6 C 0.3267(8) 0.4202(10) 0.9077(4) 0.075(2) Uani 1 1 d . . . H6 H 0.3307 0.4565 0.8623 0.090 Uiso 1 1 calc R . . C5 C 0.3718(9) 0.2824(12) 0.9260(6) 0.086(3) Uani 1 1 d . . . H5 H 0.4045 0.2255 0.8932 0.104 Uiso 1 1 calc R . . C7 C 0.1614(7) 0.7690(8) 0.9986(4) 0.0601(17) Uani 1 1 d . . . C13 C 0.0738(6) 0.6458(7) 0.8587(3) 0.0502(14) Uani 1 1 d . . . C8 C 0.0395(8) 0.7803(8) 1.0045(4) 0.0626(18) Uani 1 1 d . . . H8 H -0.0209 0.7412 0.9684 0.075 Uiso 1 1 calc R . . C10 C 0.0885(13) 0.9028(11) 1.1146(6) 0.100(3) Uani 1 1 d . . . H10 H 0.0645 0.9467 1.1542 0.120 Uiso 1 1 calc R . . C12 C 0.2498(12) 0.8363(14) 1.0522(7) 0.117(5) Uani 1 1 d . . . H12 H 0.3332 0.8405 1.0475 0.141 Uiso 1 1 calc R . . C11 C 0.2125(14) 0.8958(16) 1.1115(7) 0.126(4) Uani 1 1 d . . . H11 H 0.2714 0.9313 1.1494 0.151 Uiso 1 1 calc R . . C16 C -0.1536(7) 0.6095(10) 0.7674(4) 0.072(2) Uani 1 1 d . . . H16 H -0.2296 0.5974 0.7364 0.086 Uiso 1 1 calc R . . C18 C 0.0003(7) 0.5245(8) 0.8641(4) 0.0618(17) Uani 1 1 d . . . H18 H 0.0273 0.4546 0.8991 0.074 Uiso 1 1 calc R . . C17 C -0.1130(7) 0.5058(9) 0.8182(4) 0.0650(19) Uani 1 1 d . . . H17 H -0.1610 0.4233 0.8218 0.078 Uiso 1 1 calc R . . C15 C -0.0835(8) 0.7301(11) 0.7621(5) 0.078(2) Uani 1 1 d . . . H15 H -0.1122 0.8008 0.7278 0.093 Uiso 1 1 calc R . . C14 C 0.0300(7) 0.7483(9) 0.8073(4) 0.067(2) Uani 1 1 d . . . H14 H 0.0775 0.8310 0.8029 0.080 Uiso 1 1 calc R . . C3 C 0.3196(11) 0.3179(11) 1.0416(6) 0.093(3) Uani 1 1 d . . . H3 H 0.3197 0.2835 1.0879 0.112 Uiso 1 1 calc R . . F1 F 0.6085(8) 0.8306(8) 0.7650(5) 0.145(3) Uani 1 1 d . . . F2 F 0.4040(8) 0.8677(17) 0.7056(5) 0.223(6) Uani 1 1 d . . . O2 O 0.5460(11) 1.0709(6) 0.7336(4) 0.151(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 0.0554(2) 0.0611(2) 0.0682(2) -0.00046(13) 0.02473(14) -0.00965(12) P1 0.0491(9) 0.0545(10) 0.0548(9) -0.0001(8) 0.0186(7) -0.0044(7) P2 0.0615(10) 0.0394(8) 0.0659(11) 0.0000(8) 0.0207(9) 0.0061(8) C1 0.048(3) 0.061(4) 0.056(4) 0.001(3) 0.012(3) 0.000(3) O1 0.080(3) 0.064(3) 0.076(3) -0.006(3) 0.032(3) -0.018(3) C9 0.098(6) 0.063(5) 0.081(6) 0.001(4) 0.046(5) 0.004(5) C2 0.086(6) 0.090(6) 0.071(5) 0.019(5) 0.034(4) 0.020(5) C4 0.075(6) 0.088(6) 0.104(8) 0.015(6) 0.013(5) 0.022(5) C6 0.079(5) 0.084(6) 0.067(5) 0.004(4) 0.030(4) 0.022(4) C5 0.085(6) 0.090(6) 0.086(6) -0.004(5) 0.018(5) 0.022(5) C7 0.072(5) 0.058(4) 0.055(4) -0.007(3) 0.023(3) -0.012(4) C13 0.053(3) 0.052(3) 0.048(3) -0.004(3) 0.015(3) -0.001(3) C8 0.068(4) 0.059(4) 0.067(4) -0.001(4) 0.030(4) 0.001(4) C10 0.150(10) 0.072(6) 0.083(7) -0.025(5) 0.035(7) -0.010(7) C12 0.086(7) 0.165(12) 0.099(8) -0.060(8) 0.010(6) -0.031(7) C11 0.139(11) 0.139(11) 0.100(8) -0.068(8) 0.022(8) -0.030(9) C16 0.059(4) 0.083(6) 0.072(5) -0.011(5) 0.008(4) 0.003(4) C18 0.060(4) 0.060(4) 0.066(4) -0.003(4) 0.016(3) -0.005(3) C17 0.057(4) 0.068(5) 0.072(5) -0.012(4) 0.016(3) -0.011(4) C15 0.068(5) 0.085(6) 0.078(5) 0.021(5) 0.009(4) 0.004(5) C14 0.067(5) 0.063(4) 0.071(5) 0.013(4) 0.010(4) -0.010(4) C3 0.105(8) 0.102(8) 0.072(6) 0.030(5) 0.013(5) 0.027(6) F1 0.137(6) 0.145(7) 0.176(7) 0.051(5) 0.089(6) 0.083(5) F2 0.104(5) 0.445(17) 0.116(6) -0.097(9) 0.012(4) -0.057(9) O2 0.333(13) 0.038(3) 0.122(5) 0.007(3) 0.145(7) 0.002(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 O1 2.046(5) . ? Au1 P1 2.2106(17) . ? P1 C13 1.805(7) . ? P1 C7 1.810(7) . ? P1 C1 1.815(7) . ? P2 O2 1.441(6) . ? P2 F1 1.487(6) . ? P2 F2 1.491(8) . ? P2 O1 1.498(5) . ? C1 C6 1.369(10) . ? C1 C2 1.389(10) . ? C9 C10 1.317(14) . ? C9 C8 1.410(11) . ? C2 C3 1.366(12) . ? C4 C5 1.373(14) . ? C4 C3 1.382(15) . ? C6 C5 1.376(12) . ? C7 C8 1.358(10) . ? C7 C12 1.408(13) . ? C13 C14 1.374(10) . ? C13 C18 1.385(9) . ? C10 C11 1.365(19) . ? C12 C11 1.373(16) . ? C16 C15 1.358(12) . ? C16 C17 1.366(11) . ? C18 C17 1.386(10) . ? C15 C14 1.381(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 O1 Au1 P1 177.46(16) . . ? C13 P1 C7 105.4(3) . . ? C13 P1 C1 105.9(3) . . ? C7 P1 C1 106.9(3) . . ? C13 P1 Au1 111.1(2) . . ? C7 P1 Au1 113.4(2) . . ? C1 P1 Au1 113.6(2) . . ? O2 P2 F1 106.7(5) . . ? O2 P2 F2 111.1(7) . . ? F1 P2 F2 103.1(7) . . ? O2 P2 O1 114.1(3) . . ? F1 P2 O1 110.6(4) . . ? F2 P2 O1 110.6(4) . . ? C6 C1 C2 119.5(7) . . ? C6 C1 P1 118.1(6) . . ? C2 C1 P1 122.4(6) . . ? P2 O1 Au1 129.2(3) . . ? C10 C9 C8 118.2(10) . . ? C3 C2 C1 118.5(9) . . ? C5 C4 C3 119.6(9) . . ? C1 C6 C5 121.9(8) . . ? C4 C5 C6 118.6(9) . . ? C8 C7 C12 117.4(8) . . ? C8 C7 P1 123.5(6) . . ? C12 C7 P1 119.1(7) . . ? C14 C13 C18 118.0(7) . . ? C14 C13 P1 119.6(5) . . ? C18 C13 P1 121.9(5) . . ? C7 C8 C9 122.1(8) . . ? C9 C10 C11 122.5(10) . . ? C11 C12 C7 119.8(11) . . ? C10 C11 C12 119.8(11) . . ? C15 C16 C17 120.2(7) . . ? C13 C18 C17 121.0(7) . . ? C16 C17 C18 119.5(7) . . ? C16 C15 C14 120.4(8) . . ? C13 C14 C15 120.8(7) . . ? C2 C3 C4 121.8(10) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.960 _refine_diff_density_min -1.696 _refine_diff_density_rms 0.148 # Attachment 'Au_PPh3_OPOF21.cif'