# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'LaLonde, Rebecca' 'Brenzovich Junior, William' 'Benitez, Diego' 'Tkatchouk, Ekaterina' 'Kelley, Kotaro' 'Goddard, William' 'Toste, F.' _publ_contact_author_name 'Toste, F.' _publ_contact_author_email fdtoste@berkeley.edu _publ_section_title ; Alkylgold Complexes by the Intramolecular Aminoauration of Unactivated Alkenes ; # Attachment 'alkylgold-2.cif.txt' data_toste03 _database_code_depnum_ccdc_archive 'CCDC 772397' #TrackingRef 'alkylgold-2.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; toste03 ; _chemical_name_common rkl-100180-E10 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 Au N2 O3 P' _chemical_formula_weight 884.81 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' P P 0.1023 0.0942 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8343(11) _cell_length_b 27.110(4) _cell_length_c 17.039(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.118(2) _cell_angle_gamma 90.00 _cell_volume 4078.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3696 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.18 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 3.687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7094 _exptl_absorpt_correction_T_max 0.9299 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.3 _diffrn_refln_scan_rate 10 _space_group.centring_type primitive _space_group.IT_number 2 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-I CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 49189 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.37 _reflns_number_total 7475 _reflns_number_gt 5938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _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^)+(0.0000P)^2^+90.8796P] 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 7475 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1566 _refine_ls_goodness_of_fit_ref 1.251 _refine_ls_restrained_S_all 1.251 _refine_ls_shift/su_max 0.197 _refine_ls_shift/su_mean 0.003 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 C1 C 0.4631(10) 0.2404(4) 0.5088(5) 0.016(2) Uani 1 1 d . . . C2 C 0.4098(15) 0.2880(5) 0.5109(7) 0.035(3) Uani 1 1 d . . . H2 H 0.4137 0.3073 0.4644 0.042 Uiso 1 1 calc R . . C3 C 0.3507(16) 0.3094(5) 0.5772(8) 0.044(3) Uani 1 1 d . . . H3 H 0.3170 0.3427 0.5759 0.053 Uiso 1 1 calc R . . C4 C 0.3414(17) 0.2820(6) 0.6445(8) 0.046(4) Uani 1 1 d . . . H4 H 0.2999 0.2963 0.6898 0.056 Uiso 1 1 calc R . . C5 C 0.3915(16) 0.2343(5) 0.6468(7) 0.042(3) Uani 1 1 d . . . H5 H 0.3829 0.2154 0.6933 0.050 Uiso 1 1 calc R . . C6 C 0.4552(14) 0.2133(4) 0.5809(6) 0.030(3) Uani 1 1 d . . . H6 H 0.4938 0.1807 0.5838 0.036 Uiso 1 1 calc R . . C7 C 0.4956(13) 0.1500(4) 0.4203(6) 0.024(2) Uani 1 1 d . . . C8 C 0.3750(13) 0.1328(4) 0.3728(7) 0.028(3) Uani 1 1 d . . . H8 H 0.3145 0.1557 0.3434 0.034 Uiso 1 1 calc R . . C9 C 0.3417(15) 0.0829(5) 0.3676(7) 0.035(3) Uani 1 1 d . . . H9 H 0.2586 0.0715 0.3356 0.042 Uiso 1 1 calc R . . C10 C 0.4347(16) 0.0494(5) 0.4112(7) 0.037(3) Uani 1 1 d . . . H10 H 0.4151 0.0150 0.4078 0.045 Uiso 1 1 calc R . . C11 C 0.5517(14) 0.0661(4) 0.4580(7) 0.031(3) Uani 1 1 d . . . H11 H 0.6115 0.0433 0.4878 0.038 Uiso 1 1 calc R . . C12 C 0.5846(13) 0.1152(4) 0.4626(7) 0.028(3) Uani 1 1 d . . . H12 H 0.6683 0.1260 0.4947 0.033 Uiso 1 1 calc R . . C13 C 0.7414(12) 0.2193(4) 0.4299(7) 0.023(2) Uani 1 1 d . . . C14 C 0.8230(16) 0.2118(5) 0.3655(8) 0.043(3) Uani 1 1 d . . . H14 H 0.7718 0.2030 0.3175 0.052 Uiso 1 1 calc R . . C15 C 0.9751(16) 0.2164(5) 0.3674(8) 0.045(4) Uani 1 1 d . . . H15 H 1.0279 0.2109 0.3206 0.054 Uiso 1 1 calc R . . C16 C 1.0549(14) 0.2285(4) 0.4343(8) 0.037(3) Uani 1 1 d . . . H16 H 1.1619 0.2319 0.4339 0.045 Uiso 1 1 calc R . . C17 C 0.9797(15) 0.2360(5) 0.5026(7) 0.038(3) Uani 1 1 d . . . H17 H 1.0348 0.2439 0.5499 0.045 Uiso 1 1 calc R . . C18 C 0.8211(13) 0.2319(5) 0.5023(7) 0.033(3) Uani 1 1 d . . . H18 H 0.7677 0.2373 0.5489 0.039 Uiso 1 1 calc R . . C19 C 0.3344(13) 0.2978(4) 0.2246(6) 0.023(2) Uani 1 1 d . . . H19A H 0.4065 0.3014 0.1819 0.028 Uiso 1 1 calc R . . H19B H 0.2428 0.2808 0.2031 0.028 Uiso 1 1 calc R . . C20 C 0.2910(14) 0.3494(4) 0.2560(6) 0.028(3) Uani 1 1 d . . . H20 H 0.3823 0.3650 0.2822 0.034 Uiso 1 1 calc R . . C21 C 0.1638(14) 0.3469(4) 0.3147(7) 0.029(3) Uani 1 1 d . . . H21A H 0.0939 0.3193 0.3015 0.034 Uiso 1 1 calc R . . H21B H 0.2061 0.3420 0.3688 0.034 Uiso 1 1 calc R . . C22 C 0.0814(12) 0.3961(4) 0.3080(6) 0.023(2) Uani 1 1 d . . . C23 C 0.0791(13) 0.4023(5) 0.2176(7) 0.029(3) Uani 1 1 d . . . H23A H -0.0040 0.3829 0.1924 0.035 Uiso 1 1 calc R . . H23B H 0.0660 0.4374 0.2028 0.035 Uiso 1 1 calc R . . C24 C -0.0818(13) 0.3955(4) 0.3364(6) 0.026(3) Uani 1 1 d . . . C25 C -0.1384(16) 0.3574(5) 0.3811(9) 0.050(4) Uani 1 1 d . . . H25 H -0.0763 0.3299 0.3949 0.060 Uiso 1 1 calc R . . C26 C -0.2866(18) 0.3598(6) 0.4054(11) 0.065(5) Uani 1 1 d . . . H26 H -0.3257 0.3331 0.4346 0.078 Uiso 1 1 calc R . . C27 C -0.3770(16) 0.3992(6) 0.3886(8) 0.048(4) Uani 1 1 d . . . H27 H -0.4772 0.4003 0.4068 0.058 Uiso 1 1 calc R . . C28 C -0.3231(17) 0.4372(6) 0.3453(8) 0.050(4) Uani 1 1 d . . . H28 H -0.3864 0.4645 0.3320 0.060 Uiso 1 1 calc R . . C29 C -0.1745(15) 0.4358(5) 0.3209(8) 0.043(3) Uani 1 1 d . . . H29 H -0.1359 0.4631 0.2929 0.052 Uiso 1 1 calc R . . C30 C 0.1707(14) 0.4363(4) 0.3529(7) 0.030(3) Uani 1 1 d . . . C31 C 0.1772(17) 0.4341(6) 0.4336(8) 0.049(4) Uani 1 1 d . . . H31 H 0.1282 0.4079 0.4597 0.059 Uiso 1 1 calc R . . C32 C 0.2555(19) 0.4702(8) 0.4774(10) 0.072(6) Uani 1 1 d . . . H32 H 0.2616 0.4678 0.5330 0.087 Uiso 1 1 calc R . . C33 C 0.3232(18) 0.5087(7) 0.4410(11) 0.063(5) Uani 1 1 d . . . H33 H 0.3743 0.5335 0.4713 0.076 Uiso 1 1 calc R . . C34 C 0.3172(16) 0.5116(5) 0.3608(10) 0.052(4) Uani 1 1 d . . . H34 H 0.3643 0.5383 0.3351 0.062 Uiso 1 1 calc R . . C35 C 0.2410(15) 0.4750(5) 0.3166(8) 0.042(3) Uani 1 1 d . . . H35 H 0.2380 0.4768 0.2609 0.051 Uiso 1 1 calc R . . C36 C 0.3103(13) 0.4109(4) 0.1457(6) 0.026(3) Uani 1 1 d . . . C37 C 0.5656(14) 0.4177(5) 0.0862(8) 0.035(3) Uani 1 1 d . . . C38 C 0.5047(15) 0.4157(6) -0.0002(8) 0.044(4) Uani 1 1 d . . . H38A H 0.4932 0.3813 -0.0167 0.066 Uiso 1 1 calc R . . H38B H 0.5763 0.4324 -0.0340 0.066 Uiso 1 1 calc R . . H38C H 0.4063 0.4324 -0.0046 0.066 Uiso 1 1 calc R . . C39 C 0.6070(19) 0.4696(6) 0.1120(10) 0.059(4) Uani 1 1 d . . . H39A H 0.5161 0.4903 0.1099 0.089 Uiso 1 1 calc R . . H39B H 0.6820 0.4831 0.0770 0.089 Uiso 1 1 calc R . . H39C H 0.6497 0.4688 0.1659 0.089 Uiso 1 1 calc R . . C40 C 0.7071(13) 0.3853(6) 0.0943(9) 0.048(4) Uani 1 1 d . . . H40A H 0.7386 0.3824 0.1499 0.072 Uiso 1 1 calc R . . H40B H 0.7890 0.4002 0.0652 0.072 Uiso 1 1 calc R . . H40C H 0.6844 0.3524 0.0730 0.072 Uiso 1 1 calc R . . C41 C 0.385(4) 0.1471(14) 0.147(2) 0.21(2) Uani 1 1 d . . . H41A H 0.3519 0.1816 0.1482 0.313 Uiso 1 1 calc R . . H41B H 0.3108 0.1263 0.1725 0.313 Uiso 1 1 calc R . . H41C H 0.3945 0.1366 0.0924 0.313 Uiso 1 1 calc R . . C42 C 0.565(3) 0.0936(7) 0.1868(14) 0.085(6) Uani 1 1 d . . . H42A H 0.5900 0.0839 0.1328 0.102 Uiso 1 1 calc R . . H42B H 0.4770 0.0738 0.2022 0.102 Uiso 1 1 calc R . . C43 C 0.694(3) 0.0824(8) 0.2398(14) 0.103(9) Uani 1 1 d . . . H43A H 0.6720 0.0938 0.2934 0.124 Uiso 1 1 calc R . . H43B H 0.7092 0.0462 0.2418 0.124 Uiso 1 1 calc R . . C44 C 0.942(4) 0.0945(9) 0.2718(16) 0.155(14) Uani 1 1 d . . . H44A H 0.9269 0.1131 0.3203 0.232 Uiso 1 1 calc R . . H44B H 1.0364 0.1053 0.2486 0.232 Uiso 1 1 calc R . . H44C H 0.9482 0.0592 0.2838 0.232 Uiso 1 1 calc R . . N1 N 0.2263(10) 0.3840(3) 0.1945(5) 0.024(2) Uani 1 1 d . . . N2 N 0.4593(11) 0.3957(4) 0.1382(5) 0.028(2) Uani 1 1 d . . . H2A H 0.4914 0.3708 0.1675 0.034 Uiso 1 1 calc R . . P1 P 0.5367(3) 0.21526(10) 0.42172(16) 0.0211(6) Uani 1 1 d . . . Au1 Au 0.43251(5) 0.256620(15) 0.31545(2) 0.02429(14) Uani 1 1 d . . . O1 O 0.2607(10) 0.4480(3) 0.1117(5) 0.038(2) Uani 1 1 d . . . O2 O 0.526(2) 0.1427(6) 0.1870(11) 0.125(6) Uani 1 1 d . . . O3 O 0.816(3) 0.1035(6) 0.2170(9) 0.126(7) 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 C1 0.013(5) 0.015(5) 0.020(5) -0.004(4) 0.008(4) 0.003(4) C2 0.047(8) 0.039(8) 0.020(6) -0.002(5) 0.014(5) 0.022(6) C3 0.054(9) 0.036(8) 0.042(8) -0.008(6) -0.005(7) 0.018(7) C4 0.054(9) 0.053(9) 0.031(7) -0.018(6) -0.004(6) 0.010(7) C5 0.052(8) 0.055(9) 0.018(6) 0.001(6) 0.001(6) 0.002(7) C6 0.037(7) 0.029(7) 0.025(6) -0.003(5) 0.000(5) 0.008(5) C7 0.030(6) 0.022(6) 0.021(6) -0.001(4) 0.003(5) 0.005(5) C8 0.021(6) 0.030(7) 0.032(6) -0.002(5) -0.004(5) -0.001(5) C9 0.034(7) 0.039(8) 0.031(7) -0.005(5) 0.003(6) -0.009(6) C10 0.054(9) 0.022(7) 0.036(7) -0.003(5) 0.009(6) -0.006(6) C11 0.039(7) 0.025(7) 0.031(6) 0.011(5) 0.001(6) 0.004(5) C12 0.028(6) 0.023(6) 0.032(6) -0.003(5) 0.000(5) -0.004(5) C13 0.018(6) 0.016(6) 0.034(6) 0.008(5) 0.002(5) 0.004(4) C14 0.038(8) 0.055(9) 0.037(7) 0.004(6) -0.003(6) 0.005(7) C15 0.049(9) 0.048(9) 0.040(8) -0.002(6) 0.014(7) -0.001(7) C16 0.027(7) 0.024(7) 0.062(9) 0.000(6) 0.004(6) -0.003(5) C17 0.045(8) 0.034(7) 0.034(7) 0.004(6) -0.001(6) -0.007(6) C18 0.025(6) 0.037(8) 0.036(7) -0.001(5) 0.001(5) -0.002(5) C19 0.023(6) 0.029(6) 0.019(5) -0.005(4) 0.008(5) 0.004(5) C20 0.035(7) 0.025(6) 0.024(6) 0.007(5) 0.000(5) 0.005(5) C21 0.032(7) 0.028(7) 0.027(6) 0.001(5) 0.003(5) 0.001(5) C22 0.022(6) 0.030(6) 0.018(5) -0.003(4) 0.003(4) 0.003(5) C23 0.030(7) 0.031(7) 0.027(6) 0.005(5) 0.001(5) 0.012(5) C24 0.025(6) 0.029(7) 0.025(6) -0.006(5) 0.003(5) 0.004(5) C25 0.036(8) 0.036(8) 0.079(11) 0.003(7) 0.015(8) 0.004(6) C26 0.046(10) 0.034(9) 0.118(16) 0.001(9) 0.035(10) -0.004(7) C27 0.037(8) 0.061(10) 0.048(9) -0.025(7) 0.005(7) -0.009(7) C28 0.043(9) 0.069(11) 0.038(8) 0.000(7) 0.006(7) 0.016(8) C29 0.039(8) 0.054(9) 0.037(7) 0.015(6) 0.013(6) 0.019(7) C30 0.028(6) 0.028(7) 0.033(7) -0.003(5) -0.007(5) 0.007(5) C31 0.052(9) 0.060(10) 0.035(8) -0.004(7) -0.007(7) -0.003(8) C32 0.054(11) 0.120(17) 0.043(9) -0.031(10) -0.013(8) -0.007(11) C33 0.038(9) 0.070(12) 0.080(13) -0.045(10) -0.004(8) -0.009(8) C34 0.041(9) 0.034(8) 0.079(12) -0.018(7) 0.003(8) -0.005(7) C35 0.041(8) 0.039(8) 0.046(8) -0.011(6) -0.005(6) 0.010(6) C36 0.023(6) 0.033(7) 0.022(6) -0.002(5) -0.009(5) 0.010(5) C37 0.030(7) 0.035(7) 0.040(7) 0.010(6) -0.002(6) 0.001(6) C38 0.031(7) 0.068(10) 0.033(7) 0.007(7) 0.004(6) 0.007(7) C39 0.056(10) 0.045(9) 0.077(12) 0.010(8) 0.002(9) -0.008(8) C40 0.014(6) 0.058(10) 0.071(10) 0.018(8) -0.010(6) -0.002(6) C41 0.14(3) 0.27(5) 0.21(4) -0.08(3) -0.13(3) 0.06(3) C42 0.106(17) 0.055(12) 0.096(16) 0.017(12) 0.030(13) 0.001(13) C43 0.16(3) 0.057(13) 0.098(17) 0.009(12) 0.073(19) -0.008(15) C44 0.28(4) 0.074(17) 0.11(2) 0.000(15) -0.05(2) 0.06(2) N1 0.025(5) 0.027(5) 0.020(5) 0.004(4) -0.004(4) 0.005(4) N2 0.024(5) 0.031(6) 0.029(5) 0.008(4) -0.006(4) 0.005(4) P1 0.0237(15) 0.0205(15) 0.0189(14) 0.0018(11) -0.0016(11) 0.0025(12) Au1 0.0267(2) 0.0241(2) 0.0218(2) 0.00176(19) -0.00227(15) 0.0040(2) O1 0.043(5) 0.037(5) 0.035(5) 0.011(4) 0.001(4) 0.015(4) O2 0.137(16) 0.091(12) 0.147(16) 0.035(11) 0.019(13) -0.005(11) O3 0.21(2) 0.094(12) 0.077(11) 0.023(9) 0.012(12) -0.048(13) _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 C1 C2 1.375(15) . ? C1 C6 1.435(15) . ? C1 P1 1.778(9) . ? C2 C3 1.389(17) . ? C2 H2 0.9500 . ? C3 C4 1.371(19) . ? C3 H3 0.9500 . ? C4 C5 1.368(19) . ? C4 H4 0.9500 . ? C5 C6 1.395(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.395(15) . ? C7 C12 1.408(16) . ? C7 P1 1.807(11) . ? C8 C9 1.385(17) . ? C8 H8 0.9500 . ? C9 C10 1.417(18) . ? C9 H9 0.9500 . ? C10 C11 1.359(18) . ? C10 H10 0.9500 . ? C11 C12 1.363(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.351(17) . ? C13 C18 1.438(16) . ? C13 P1 1.812(11) . ? C14 C15 1.348(19) . ? C14 H14 0.9500 . ? C15 C16 1.359(19) . ? C15 H15 0.9500 . ? C16 C17 1.377(18) . ? C16 H16 0.9500 . ? C17 C18 1.405(17) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.551(15) . ? C19 Au1 2.073(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N1 1.503(13) . ? C20 C21 1.533(16) . ? C20 H20 1.0000 . ? C21 C22 1.521(16) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C30 1.533(16) . ? C22 C24 1.538(15) . ? C22 C23 1.549(15) . ? C23 N1 1.459(14) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C29 1.385(17) . ? C24 C25 1.388(18) . ? C25 C26 1.389(19) . ? C25 H25 0.9500 . ? C26 C27 1.36(2) . ? C26 H26 0.9500 . ? C27 C28 1.36(2) . ? C27 H27 0.9500 . ? C28 C29 1.392(19) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.375(18) . ? C30 C35 1.378(19) . ? C31 C32 1.40(2) . ? C31 H31 0.9500 . ? C32 C33 1.37(3) . ? C32 H32 0.9500 . ? C33 C34 1.37(2) . ? C33 H33 0.9500 . ? C34 C35 1.403(18) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 O1 1.234(13) . ? C36 N1 1.349(15) . ? C36 N2 1.389(14) . ? C37 N2 1.443(15) . ? C37 C39 1.514(19) . ? C37 C40 1.530(17) . ? C37 C38 1.550(18) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 O2 1.40(3) . ? C41 H41A 0.9809 . ? C41 H41B 0.9809 . ? C41 H41C 0.9809 . ? C42 O2 1.38(2) . ? C42 C43 1.46(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 O3 1.30(3) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 O3 1.44(3) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? N2 H2A 0.8800 . ? P1 Au1 2.293(3) . ? 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 C2 C1 C6 115.5(9) . . ? C2 C1 P1 121.1(8) . . ? C6 C1 P1 123.3(8) . . ? C1 C2 C3 123.5(12) . . ? C1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C4 C3 C2 119.4(13) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.4(13) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.1(12) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 121.0(11) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C8 C7 C12 118.3(10) . . ? C8 C7 P1 118.9(9) . . ? C12 C7 P1 122.8(9) . . ? C9 C8 C7 121.2(11) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 118.4(12) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C11 C10 C9 120.4(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.1(11) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 120.6(11) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C18 118.2(11) . . ? C14 C13 P1 119.3(10) . . ? C18 C13 P1 122.5(9) . . ? C15 C14 C13 121.9(13) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 121.9(13) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C15 C16 C17 119.6(12) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 119.8(12) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 118.7(11) . . ? C17 C18 H18 120.7 . . ? C13 C18 H18 120.7 . . ? C20 C19 Au1 109.3(7) . . ? C20 C19 H19A 109.8 . . ? Au1 C19 H19A 109.8 . . ? C20 C19 H19B 109.8 . . ? Au1 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? N1 C20 C21 102.4(9) . . ? N1 C20 C19 114.4(9) . . ? C21 C20 C19 112.4(9) . . ? N1 C20 H20 109.1 . . ? C21 C20 H20 109.1 . . ? C19 C20 H20 109.1 . . ? C22 C21 C20 105.7(9) . . ? C22 C21 H21A 110.6 . . ? C20 C21 H21A 110.6 . . ? C22 C21 H21B 110.6 . . ? C20 C21 H21B 110.6 . . ? H21A C21 H21B 108.7 . . ? C21 C22 C30 110.4(9) . . ? C21 C22 C24 114.8(10) . . ? C30 C22 C24 108.7(9) . . ? C21 C22 C23 99.2(9) . . ? C30 C22 C23 114.0(10) . . ? C24 C22 C23 109.6(9) . . ? N1 C23 C22 104.6(9) . . ? N1 C23 H23A 110.8 . . ? C22 C23 H23A 110.8 . . ? N1 C23 H23B 110.8 . . ? C22 C23 H23B 110.8 . . ? H23A C23 H23B 108.9 . . ? C29 C24 C25 118.0(12) . . ? C29 C24 C22 119.1(11) . . ? C25 C24 C22 122.7(11) . . ? C24 C25 C26 119.4(14) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C27 C26 C25 121.8(15) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C26 C27 C28 119.6(14) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C29 119.6(14) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C24 C29 C28 121.4(13) . . ? C24 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C31 C30 C35 118.6(12) . . ? C31 C30 C22 118.1(12) . . ? C35 C30 C22 123.3(11) . . ? C30 C31 C32 120.3(15) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C33 C32 C31 120.7(16) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 119.7(14) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C35 119.6(15) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C30 C35 C34 120.9(14) . . ? C30 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? O1 C36 N1 122.4(11) . . ? O1 C36 N2 121.3(11) . . ? N1 C36 N2 116.2(10) . . ? N2 C37 C39 111.1(12) . . ? N2 C37 C40 104.8(10) . . ? C39 C37 C40 108.7(12) . . ? N2 C37 C38 111.0(10) . . ? C39 C37 C38 112.3(12) . . ? C40 C37 C38 108.6(11) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O2 C41 H41A 109.7 . . ? O2 C41 H41B 109.5 . . ? H41A C41 H41B 109.4 . . ? O2 C41 H41C 109.5 . . ? H41A C41 H41C 109.4 . . ? H41B C41 H41C 109.4 . . ? O2 C42 C43 113(2) . . ? O2 C42 H42A 109.0 . . ? C43 C42 H42A 109.0 . . ? O2 C42 H42B 109.0 . . ? C43 C42 H42B 109.0 . . ? H42A C42 H42B 107.8 . . ? O3 C43 C42 111(2) . . ? O3 C43 H43A 109.4 . . ? C42 C43 H43A 109.4 . . ? O3 C43 H43B 109.4 . . ? C42 C43 H43B 109.4 . . ? H43A C43 H43B 108.0 . . ? O3 C44 H44A 109.5 . . ? O3 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O3 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C36 N1 C23 119.9(9) . . ? C36 N1 C20 124.3(9) . . ? C23 N1 C20 110.1(9) . . ? C36 N2 C37 125.1(10) . . ? C36 N2 H2A 117.4 . . ? C37 N2 H2A 117.4 . . ? C1 P1 C7 107.9(5) . . ? C1 P1 C13 107.9(5) . . ? C7 P1 C13 105.0(5) . . ? C1 P1 Au1 108.9(3) . . ? C7 P1 Au1 113.2(4) . . ? C13 P1 Au1 113.7(4) . . ? C19 Au1 P1 176.1(3) . . ? C42 O2 C41 107(2) . . ? C43 O3 C44 111(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.177 _refine_diff_density_min -1.607 _refine_diff_density_rms 0.198 # Attachment 'alkylgold-20.cif.txt' data_toste15 _database_code_depnum_ccdc_archive 'CCDC 772398' #TrackingRef 'alkylgold-20.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; toste15 ; _chemical_name_common KK-140 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H39 Au N2 O P' _chemical_formula_weight 779.66 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' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2568(19) _cell_length_b 12.331(3) _cell_length_c 15.174(3) _cell_angle_alpha 95.195(3) _cell_angle_beta 105.262(3) _cell_angle_gamma 101.577(3) _cell_volume 1618.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 139(2) _cell_measurement_reflns_used 7949 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.56 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 778 _exptl_absorpt_coefficient_mu 4.630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6065 _exptl_absorpt_correction_T_max 0.9131 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 20 _space_group.centring_type primitive _space_group.IT_number 2 _exptl_special_details ; ? ; _diffrn_ambient_temperature 139(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-I CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 15093 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.15 _reflns_number_total 6009 _reflns_number_gt 4697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-97 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _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^)+(0.0433P)^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_number_reflns 6009 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 C1 C 0.8225(7) 0.1157(6) -0.1669(5) 0.0347(16) Uani 1 1 d . . . H1A H 0.8813 0.1602 -0.2026 0.042 Uiso 1 1 calc R . . H1B H 0.8461 0.0409 -0.1698 0.042 Uiso 1 1 calc R . . C2 C 0.6513(7) 0.1012(5) -0.2144(4) 0.0311(15) Uani 1 1 d . . . H2 H 0.5932 0.0477 -0.1831 0.037 Uiso 1 1 calc R . . C3 C 0.6077(7) 0.0505(5) -0.3165(4) 0.0271(14) Uani 1 1 d . . . H3A H 0.6516 -0.0159 -0.3219 0.032 Uiso 1 1 calc R . . H3B H 0.4943 0.0251 -0.3406 0.032 Uiso 1 1 calc R . . C4 C 0.6650(7) 0.1327(5) -0.3746(5) 0.0287(14) Uani 1 1 d . . . H4A H 0.6325 0.0966 -0.4399 0.034 Uiso 1 1 calc R . . H4B H 0.7789 0.1541 -0.3536 0.034 Uiso 1 1 calc R . . C5 C 0.6012(6) 0.2391(5) -0.3675(4) 0.0249(14) Uani 1 1 d . . . C6 C 0.6520(6) 0.2874(5) -0.2645(4) 0.0253(14) Uani 1 1 d . . . H6A H 0.7658 0.3110 -0.2426 0.030 Uiso 1 1 calc R . . H6B H 0.6106 0.3543 -0.2558 0.030 Uiso 1 1 calc R . . C7 C 0.6714(6) 0.3271(5) -0.4212(4) 0.0268(14) Uani 1 1 d . . . C8 C 0.7605(7) 0.3049(6) -0.4763(5) 0.0351(16) Uani 1 1 d . . . H8 H 0.7824 0.2330 -0.4821 0.042 Uiso 1 1 calc R . . C9 C 0.8195(7) 0.3851(6) -0.5239(5) 0.0401(18) Uani 1 1 d . . . H9 H 0.8804 0.3677 -0.5623 0.048 Uiso 1 1 calc R . . C10 C 0.7903(7) 0.4891(6) -0.5155(5) 0.0380(17) Uani 1 1 d . . . H10 H 0.8304 0.5440 -0.5484 0.046 Uiso 1 1 calc R . . C11 C 0.7027(7) 0.5147(6) -0.4595(5) 0.0378(17) Uani 1 1 d . . . H11 H 0.6839 0.5874 -0.4524 0.045 Uiso 1 1 calc R . . C12 C 0.6423(6) 0.4330(5) -0.4134(4) 0.0295(15) Uani 1 1 d . . . H12 H 0.5798 0.4499 -0.3759 0.035 Uiso 1 1 calc R . . C13 C 0.4255(6) 0.2108(5) -0.4102(4) 0.0254(14) Uani 1 1 d . . . C14 C 0.3584(7) 0.1454(5) -0.4961(4) 0.0305(15) Uani 1 1 d . . . H14 H 0.4230 0.1191 -0.5282 0.037 Uiso 1 1 calc R . . C15 C 0.2012(7) 0.1170(6) -0.5368(5) 0.0348(16) Uani 1 1 d . . . H15 H 0.1584 0.0708 -0.5953 0.042 Uiso 1 1 calc R . . C16 C 0.1070(7) 0.1567(6) -0.4912(5) 0.0369(17) Uani 1 1 d . . . H16 H -0.0015 0.1382 -0.5181 0.044 Uiso 1 1 calc R . . C17 C 0.1710(7) 0.2225(6) -0.4078(5) 0.0381(17) Uani 1 1 d . . . H17 H 0.1058 0.2498 -0.3767 0.046 Uiso 1 1 calc R . . C18 C 0.3287(6) 0.2509(5) -0.3664(5) 0.0294(15) Uani 1 1 d . . . H18 H 0.3704 0.2978 -0.3082 0.035 Uiso 1 1 calc R . . C19 C 0.5368(6) 0.2417(5) -0.1423(4) 0.0248(14) Uani 1 1 d . . . C20 C 0.4375(8) 0.2046(5) -0.0127(5) 0.0380(17) Uani 1 1 d . . . H20A H 0.3347 0.2158 -0.0444 0.046 Uiso 1 1 calc R . . H20B H 0.5003 0.2766 0.0251 0.046 Uiso 1 1 calc R . . C21 C 0.4205(8) 0.1165(6) 0.0496(5) 0.047(2) Uani 1 1 d . . . H21A H 0.3626 0.0444 0.0119 0.070 Uiso 1 1 calc R . . H21B H 0.3653 0.1385 0.0926 0.070 Uiso 1 1 calc R . . H21C H 0.5228 0.1096 0.0846 0.070 Uiso 1 1 calc R . . C22 C 0.9201(6) 0.3989(5) 0.1446(4) 0.0269(14) Uani 1 1 d . . . C23 C 0.8063(7) 0.4288(6) 0.0775(5) 0.0313(15) Uani 1 1 d . . . H23 H 0.7619 0.3835 0.0187 0.038 Uiso 1 1 calc R . . C24 C 0.7586(7) 0.5253(6) 0.0973(5) 0.0356(17) Uani 1 1 d . . . H24 H 0.6801 0.5452 0.0517 0.043 Uiso 1 1 calc R . . C25 C 0.8215(7) 0.5920(6) 0.1801(5) 0.0399(18) Uani 1 1 d . . . H25 H 0.7877 0.6582 0.1921 0.048 Uiso 1 1 calc R . . C26 C 0.9344(7) 0.5639(6) 0.2471(5) 0.0417(18) Uani 1 1 d . . . H26 H 0.9787 0.6107 0.3053 0.050 Uiso 1 1 calc R . . C27 C 0.9832(7) 0.4674(6) 0.2294(5) 0.0347(16) Uani 1 1 d . . . H27 H 1.0607 0.4480 0.2758 0.042 Uiso 1 1 calc R . . C28 C 0.8947(6) 0.1736(5) 0.1887(5) 0.0311(16) Uani 1 1 d . . . C29 C 0.8204(8) 0.2028(6) 0.2508(5) 0.0399(17) Uani 1 1 d . . . H29 H 0.8099 0.2776 0.2609 0.048 Uiso 1 1 calc R . . C30 C 0.7606(8) 0.1244(6) 0.2988(5) 0.0459(19) Uani 1 1 d . . . H30 H 0.7074 0.1451 0.3409 0.055 Uiso 1 1 calc R . . C31 C 0.7773(7) 0.0172(6) 0.2862(5) 0.0429(19) Uani 1 1 d . . . H31 H 0.7383 -0.0360 0.3208 0.052 Uiso 1 1 calc R . . C32 C 0.8504(7) -0.0137(6) 0.2236(6) 0.047(2) Uani 1 1 d . . . H32 H 0.8626 -0.0883 0.2150 0.057 Uiso 1 1 calc R . . C33 C 0.9055(7) 0.0625(6) 0.1736(5) 0.0401(18) Uani 1 1 d . . . H33 H 0.9517 0.0398 0.1283 0.048 Uiso 1 1 calc R . . C34 C 1.1843(6) 0.3056(5) 0.1790(4) 0.0253(14) Uani 1 1 d . . . C35 C 1.2530(7) 0.2617(6) 0.2545(5) 0.0359(17) Uani 1 1 d . . . H35 H 1.1923 0.2082 0.2795 0.043 Uiso 1 1 calc R . . C36 C 1.4108(7) 0.2952(6) 0.2945(5) 0.0402(18) Uani 1 1 d . . . H36 H 1.4582 0.2657 0.3475 0.048 Uiso 1 1 calc R . . C37 C 1.4992(7) 0.3718(6) 0.2572(5) 0.0353(16) Uani 1 1 d . . . H37 H 1.6076 0.3942 0.2842 0.042 Uiso 1 1 calc R . . C38 C 1.4317(7) 0.4152(6) 0.1820(5) 0.0374(17) Uani 1 1 d . . . H38 H 1.4926 0.4683 0.1569 0.045 Uiso 1 1 calc R . . C39 C 1.2745(7) 0.3817(6) 0.1423(5) 0.0363(17) Uani 1 1 d . . . H39 H 1.2278 0.4112 0.0891 0.044 Uiso 1 1 calc R . . N1 N 0.5980(5) 0.2050(4) -0.2089(3) 0.0231(11) Uani 1 1 d . . . N2 N 0.5105(6) 0.1711(4) -0.0808(4) 0.0305(12) Uani 1 1 d . . . O1 O 0.5018(5) 0.3325(4) -0.1385(3) 0.0379(11) Uani 1 1 d . . . P1 P 0.97750(17) 0.27001(14) 0.12153(12) 0.0286(4) Uani 1 1 d . . . Au1 Au 0.90132(3) 0.19229(2) -0.030099(18) 0.03244(10) 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 C1 0.031(3) 0.036(4) 0.037(4) -0.002(3) 0.004(3) 0.018(3) C2 0.050(4) 0.027(4) 0.028(4) 0.007(3) 0.020(3) 0.025(3) C3 0.038(3) 0.021(3) 0.029(4) 0.004(3) 0.015(3) 0.016(3) C4 0.033(3) 0.029(4) 0.029(4) 0.001(3) 0.014(3) 0.015(3) C5 0.031(3) 0.022(3) 0.025(4) 0.009(3) 0.008(3) 0.011(3) C6 0.022(3) 0.027(4) 0.029(4) 0.011(3) 0.008(3) 0.005(2) C7 0.021(3) 0.032(4) 0.023(4) 0.004(3) 0.001(3) 0.005(3) C8 0.030(3) 0.044(4) 0.035(4) 0.011(3) 0.011(3) 0.013(3) C9 0.036(4) 0.050(5) 0.033(4) 0.008(4) 0.012(3) 0.004(3) C10 0.033(4) 0.038(4) 0.037(5) 0.010(4) 0.006(3) 0.000(3) C11 0.037(4) 0.033(4) 0.039(5) 0.011(3) 0.003(3) 0.007(3) C12 0.029(3) 0.031(4) 0.027(4) 0.009(3) 0.003(3) 0.009(3) C13 0.030(3) 0.023(3) 0.025(4) 0.006(3) 0.010(3) 0.008(3) C14 0.030(3) 0.037(4) 0.026(4) 0.006(3) 0.009(3) 0.011(3) C15 0.035(4) 0.034(4) 0.030(4) 0.000(3) 0.004(3) 0.004(3) C16 0.025(3) 0.037(4) 0.041(5) 0.004(4) 0.001(3) 0.005(3) C17 0.033(3) 0.042(4) 0.047(5) 0.011(4) 0.013(3) 0.021(3) C18 0.031(3) 0.029(4) 0.031(4) 0.004(3) 0.010(3) 0.014(3) C19 0.027(3) 0.025(4) 0.025(4) 0.004(3) 0.008(3) 0.009(3) C20 0.049(4) 0.032(4) 0.046(5) 0.010(4) 0.026(3) 0.019(3) C21 0.059(5) 0.054(5) 0.041(5) 0.019(4) 0.031(4) 0.018(4) C22 0.025(3) 0.027(4) 0.031(4) 0.005(3) 0.009(3) 0.010(3) C23 0.028(3) 0.038(4) 0.030(4) 0.003(3) 0.008(3) 0.013(3) C24 0.035(4) 0.044(4) 0.036(4) 0.015(4) 0.011(3) 0.023(3) C25 0.035(4) 0.029(4) 0.059(5) 0.007(4) 0.016(3) 0.014(3) C26 0.038(4) 0.028(4) 0.052(5) -0.010(4) 0.009(3) 0.002(3) C27 0.030(3) 0.034(4) 0.035(4) 0.000(3) 0.002(3) 0.009(3) C28 0.019(3) 0.032(4) 0.037(4) 0.007(3) -0.002(3) 0.006(3) C29 0.049(4) 0.026(4) 0.049(5) 0.005(3) 0.019(4) 0.012(3) C30 0.051(4) 0.043(5) 0.048(5) 0.006(4) 0.025(4) 0.007(4) C31 0.034(4) 0.039(4) 0.057(5) 0.017(4) 0.013(3) 0.006(3) C32 0.037(4) 0.031(4) 0.079(6) 0.020(4) 0.017(4) 0.013(3) C33 0.033(4) 0.041(4) 0.053(5) 0.013(4) 0.015(3) 0.018(3) C34 0.028(3) 0.025(3) 0.025(4) 0.002(3) 0.009(3) 0.011(3) C35 0.030(3) 0.042(4) 0.038(4) 0.017(3) 0.009(3) 0.008(3) C36 0.031(3) 0.050(5) 0.037(4) 0.018(4) 0.000(3) 0.013(3) C37 0.025(3) 0.035(4) 0.042(5) -0.003(3) 0.005(3) 0.008(3) C38 0.037(4) 0.028(4) 0.054(5) 0.005(3) 0.028(3) 0.005(3) C39 0.036(4) 0.040(4) 0.040(4) 0.023(4) 0.015(3) 0.011(3) N1 0.030(3) 0.023(3) 0.020(3) 0.004(2) 0.009(2) 0.010(2) N2 0.044(3) 0.025(3) 0.030(3) 0.007(2) 0.020(2) 0.011(2) O1 0.054(3) 0.027(3) 0.047(3) 0.011(2) 0.026(2) 0.024(2) P1 0.0273(8) 0.0311(10) 0.0279(10) 0.0064(8) 0.0049(7) 0.0115(7) Au1 0.03412(15) 0.03684(17) 0.02959(17) 0.00746(12) 0.00624(11) 0.01845(11) _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 C1 C2 1.524(8) . ? C1 Au1 2.074(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.465(7) . ? C2 C3 1.532(9) . ? C2 H2 1.0000 . ? C3 C4 1.509(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.550(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.534(8) . ? C5 C13 1.538(8) . ? C5 C7 1.555(8) . ? C6 N1 1.472(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.366(9) . ? C7 C12 1.386(8) . ? C8 C9 1.385(9) . ? C8 H8 0.9500 . ? C9 C10 1.365(10) . ? C9 H9 0.9500 . ? C10 C11 1.377(10) . ? C10 H10 0.9500 . ? C11 C12 1.386(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.385(8) . ? C13 C14 1.385(9) . ? C14 C15 1.380(8) . ? C14 H14 0.9500 . ? C15 C16 1.380(9) . ? C15 H15 0.9500 . ? C16 C17 1.356(10) . ? C16 H16 0.9500 . ? C17 C18 1.386(8) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 O1 1.227(7) . ? C19 N2 1.366(7) . ? C19 N1 1.367(7) . ? C20 N2 1.448(8) . ? C20 C21 1.514(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C27 1.386(9) . ? C22 C23 1.394(8) . ? C22 P1 1.808(6) . ? C23 C24 1.384(9) . ? C23 H23 0.9500 . ? C24 C25 1.353(10) . ? C24 H24 0.9500 . ? C25 C26 1.376(9) . ? C25 H25 0.9500 . ? C26 C27 1.383(9) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.368(9) . ? C28 C33 1.397(9) . ? C28 P1 1.818(6) . ? C29 C30 1.376(9) . ? C29 H29 0.9500 . ? C30 C31 1.363(10) . ? C30 H30 0.9500 . ? C31 C32 1.373(11) . ? C31 H31 0.9500 . ? C32 C33 1.362(9) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.371(8) . ? C34 C39 1.383(8) . ? C34 P1 1.825(6) . ? C35 C36 1.385(8) . ? C35 H35 0.9500 . ? C36 C37 1.383(9) . ? C36 H36 0.9500 . ? C37 C38 1.360(9) . ? C37 H37 0.9500 . ? C38 C39 1.379(8) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? P1 Au1 2.2770(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 C2 C1 Au1 116.2(4) . . ? C2 C1 H1A 108.2 . . ? Au1 C1 H1A 108.2 . . ? C2 C1 H1B 108.2 . . ? Au1 C1 H1B 108.2 . . ? H1A C1 H1B 107.4 . . ? N1 C2 C1 114.0(5) . . ? N1 C2 C3 108.1(5) . . ? C1 C2 C3 111.8(5) . . ? N1 C2 H2 107.6 . . ? C1 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C4 C3 C2 112.4(5) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 111.2(5) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C13 113.0(5) . . ? C6 C5 C4 106.0(4) . . ? C13 C5 C4 110.8(5) . . ? C6 C5 C7 109.1(5) . . ? C13 C5 C7 107.2(4) . . ? C4 C5 C7 110.7(5) . . ? N1 C6 C5 111.7(5) . . ? N1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C12 118.1(6) . . ? C8 C7 C5 123.0(6) . . ? C12 C7 C5 118.9(5) . . ? C7 C8 C9 121.3(7) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 120.0(7) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.1(6) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 119.3(7) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C7 121.2(6) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C18 C13 C14 117.4(5) . . ? C18 C13 C5 122.2(6) . . ? C14 C13 C5 120.3(5) . . ? C15 C14 C13 122.4(6) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C15 C14 119.1(7) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 119.3(6) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 121.9(6) . . ? C16 C17 H17 119.0 . . ? C18 C17 H17 119.0 . . ? C13 C18 C17 119.9(6) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O1 C19 N2 120.5(6) . . ? O1 C19 N1 122.2(5) . . ? N2 C19 N1 117.3(5) . . ? N2 C20 C21 110.8(5) . . ? N2 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 118.8(6) . . ? C27 C22 P1 121.3(4) . . ? C23 C22 P1 119.9(5) . . ? C24 C23 C22 119.4(6) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C25 C24 C23 121.3(6) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 120.0(6) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C27 119.8(7) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C22 120.6(6) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C29 C28 C33 118.6(6) . . ? C29 C28 P1 124.1(5) . . ? C33 C28 P1 117.2(5) . . ? C28 C29 C30 120.4(7) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C31 C30 C29 120.4(7) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C32 119.9(7) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C33 C32 C31 120.0(7) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C28 120.5(7) . . ? C32 C33 H33 119.7 . . ? C28 C33 H33 119.7 . . ? C35 C34 C39 119.3(5) . . ? C35 C34 P1 124.1(4) . . ? C39 C34 P1 116.6(4) . . ? C34 C35 C36 120.0(6) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C37 C36 C35 119.9(6) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C38 C37 C36 120.3(6) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? C37 C38 C39 119.8(6) . . ? C37 C38 H38 120.1 . . ? C39 C38 H38 120.1 . . ? C38 C39 C34 120.7(6) . . ? C38 C39 H39 119.6 . . ? C34 C39 H39 119.6 . . ? C19 N1 C2 125.3(5) . . ? C19 N1 C6 117.3(5) . . ? C2 N1 C6 115.4(5) . . ? C19 N2 C20 118.7(5) . . ? C22 P1 C28 105.9(3) . . ? C22 P1 C34 103.5(3) . . ? C28 P1 C34 105.0(3) . . ? C22 P1 Au1 114.8(2) . . ? C28 P1 Au1 110.0(2) . . ? C34 P1 Au1 116.5(2) . . ? C1 Au1 P1 177.00(19) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.372 _refine_diff_density_min -2.131 _refine_diff_density_rms 0.161