# 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 'Wendt, Ola' _publ_contact_author_name 'Ola Wendt' _publ_contact_author_address ; Lund 221 00 Sweden ; _publ_contact_author_email ola.wendt@organic.lu.se # Attachment '- compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 832959' #TrackingRef '- compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H41 Au N2 O2' _chemical_formula_weight 646.60 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' 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 'P 21/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 13.323(2) _cell_length_b 13.5457(19) _cell_length_c 18.023(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.623(17) _cell_angle_gamma 90.00 _cell_volume 3215.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 112 _cell_measurement_reflns_used 4324 _cell_measurement_theta_min 2.5383 _cell_measurement_theta_max 33.1890 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 4.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2672 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 112 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 'Xcalibur, Sapphire3' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32111 _diffrn_reflns_av_R_equivalents 0.1167 _diffrn_reflns_av_sigmaI/netI 0.2849 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 33.36 _reflns_number_total 11441 _reflns_number_gt 4467 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1164P)^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 11441 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1905 _refine_ls_R_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.2437 _refine_ls_wR_factor_gt 0.2228 _refine_ls_goodness_of_fit_ref 0.861 _refine_ls_restrained_S_all 0.861 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 278 70 ' ' 2 0.500 0.000 0.500 278 71 ' ' 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 0.89358(3) 0.17703(3) 0.31106(3) 0.02915(15) Uani 1 1 d . . . C5 C 0.8330(7) 0.0461(8) 0.2863(6) 0.023(2) Uani 1 1 d . . . O2 O 0.8247(6) 0.2817(6) 0.5495(5) 0.0396(16) Uani 1 1 d . . . O1 O 0.9595(6) 0.3071(5) 0.3362(5) 0.0396(16) Uani 1 1 d . . . C17 C 0.6495(8) 0.0808(8) 0.2693(8) 0.031(3) Uani 1 1 d . . . C11 C 1.1452(8) -0.0553(8) 0.3925(8) 0.032(3) Uani 1 1 d . . . H11 H 1.1751 -0.0722 0.4408 0.039 Uiso 1 1 calc R . . C8 C 0.9972(8) -0.0394(7) 0.3003(7) 0.027(3) Uani 1 1 d . . . C15 C 1.0573(9) -0.0052(8) 0.2446(7) 0.030(3) Uani 1 1 d . . . C21 C 0.4750(9) 0.1922(8) 0.2722(8) 0.031(3) Uani 1 1 d . . . N2 N 0.8888(7) -0.0367(7) 0.2798(6) 0.032(2) Uani 1 1 d . . . C6 C 0.7296(8) -0.0824(8) 0.2505(7) 0.028(3) Uani 1 1 d . . . H6 H 0.6704 -0.1183 0.2361 0.033 Uiso 1 1 calc R . . C2 C 1.1219(9) 0.2330(8) 0.3928(8) 0.040(2) Uani 1 1 d . . . H2A H 1.1035 0.2426 0.4418 0.060 Uiso 1 1 calc R . . H2B H 1.1939 0.2411 0.3952 0.060 Uiso 1 1 calc R . . H2C H 1.1028 0.1677 0.3755 0.060 Uiso 1 1 calc R . . N1 N 0.7373(7) 0.0190(7) 0.2678(6) 0.029(2) Uani 1 1 d . . . C23 C 0.5039(8) 0.1604(7) 0.2044(8) 0.029(2) Uani 1 1 d . . . H23 H 0.4616 0.1753 0.1599 0.035 Uiso 1 1 calc R . . C3 C 1.1000(10) 0.4117(9) 0.3710(10) 0.054(4) Uani 1 1 d . . . H3A H 1.0678 0.4622 0.3384 0.081 Uiso 1 1 calc R . . H3B H 1.1723 0.4179 0.3748 0.081 Uiso 1 1 calc R . . H3C H 1.0805 0.4186 0.4199 0.081 Uiso 1 1 calc R . . C12 C 1.2058(8) -0.0214(8) 0.3412(7) 0.029(3) Uani 1 1 d . . . C10 C 0.9741(10) -0.1037(10) 0.4268(8) 0.045(4) Uani 1 1 d . . . H10A H 1.0159 -0.1170 0.4739 0.068 Uiso 1 1 calc R . . H10B H 0.9418 -0.1636 0.4074 0.068 Uiso 1 1 calc R . . H10C H 0.9234 -0.0558 0.4340 0.068 Uiso 1 1 calc R . . C24 C 0.5905(8) 0.1089(8) 0.2004(7) 0.029(2) Uani 1 1 d . . . C14 C 1.1594(10) 0.0019(8) 0.2686(8) 0.036(3) Uani 1 1 d . . . H14 H 1.2005 0.0236 0.2345 0.043 Uiso 1 1 calc R . . C9 C 1.0389(9) -0.0642(8) 0.3722(6) 0.027(3) Uani 1 1 d . . . C27 C 0.7295(12) 0.3784(13) 0.4542(9) 0.066(5) Uani 1 1 d . . . H27A H 0.7262 0.4415 0.4284 0.079 Uiso 1 1 calc R . . H27B H 0.6994 0.3283 0.4194 0.079 Uiso 1 1 calc R . . C22 C 0.3811(9) 0.2463(9) 0.2760(9) 0.042(3) Uani 1 1 d . . . H22A H 0.3465 0.2580 0.2261 0.063 Uiso 1 1 calc R . . H22B H 0.3967 0.3083 0.3008 0.063 Uiso 1 1 calc R . . H22C H 0.3383 0.2082 0.3035 0.063 Uiso 1 1 calc R . . C1 C 1.0917(11) 0.2953(10) 0.2585(9) 0.053(4) Uani 1 1 d . . . H1A H 1.0566 0.3444 0.2260 0.080 Uiso 1 1 calc R . . H1B H 1.0705 0.2308 0.2404 0.080 Uiso 1 1 calc R . . H1C H 1.1635 0.3021 0.2591 0.080 Uiso 1 1 calc R . . C28 C 0.6763(13) 0.3836(19) 0.5202(12) 0.103(9) Uani 1 1 d . . . H28A H 0.6055 0.3654 0.5068 0.124 Uiso 1 1 calc R . . H28B H 0.6799 0.4498 0.5411 0.124 Uiso 1 1 calc R . . C20 C 0.5357(9) 0.1645(9) 0.3392(8) 0.037(3) Uani 1 1 d . . . H20 H 0.5166 0.1827 0.3848 0.044 Uiso 1 1 calc R . . C25 C 0.6175(10) 0.0751(10) 0.1275(8) 0.044(3) Uani 1 1 d . . . H25A H 0.6809 0.0403 0.1360 0.066 Uiso 1 1 calc R . . H25B H 0.6237 0.1313 0.0959 0.066 Uiso 1 1 calc R . . H25C H 0.5654 0.0321 0.1033 0.066 Uiso 1 1 calc R . . C4 C 1.0667(9) 0.3090(8) 0.3384(8) 0.040(2) Uani 1 1 d . . . C18 C 0.6263(9) 0.1089(10) 0.3387(8) 0.038(3) Uani 1 1 d . . . C7 C 0.8253(9) -0.1166(8) 0.2593(7) 0.031(3) Uani 1 1 d . . . H7 H 0.8453 -0.1814 0.2528 0.037 Uiso 1 1 calc R . . C13 C 1.3179(9) -0.0026(10) 0.3678(8) 0.043(3) Uani 1 1 d . . . H13A H 1.3350 -0.0239 0.4189 0.065 Uiso 1 1 calc R . . H13B H 1.3317 0.0667 0.3645 0.065 Uiso 1 1 calc R . . H13C H 1.3577 -0.0386 0.3367 0.065 Uiso 1 1 calc R . . C16 C 1.0073(10) 0.0191(11) 0.1654(8) 0.046(3) Uani 1 1 d . . . H16A H 0.9354 0.0086 0.1612 0.069 Uiso 1 1 calc R . . H16B H 1.0347 -0.0228 0.1304 0.069 Uiso 1 1 calc R . . H16C H 1.0202 0.0869 0.1544 0.069 Uiso 1 1 calc R . . C19 C 0.6906(11) 0.0808(12) 0.4126(8) 0.053(4) Uani 1 1 d . . . H19A H 0.6614 0.1086 0.4535 0.080 Uiso 1 1 calc R . . H19B H 0.7582 0.1057 0.4137 0.080 Uiso 1 1 calc R . . H19C H 0.6927 0.0102 0.4174 0.080 Uiso 1 1 calc R . . C29 C 0.7318(14) 0.3098(18) 0.5766(9) 0.094(8) Uani 1 1 d . . . H29A H 0.7472 0.3400 0.6258 0.113 Uiso 1 1 calc R . . H29B H 0.6897 0.2522 0.5806 0.113 Uiso 1 1 calc R . . C26 C 0.8409(13) 0.3517(15) 0.4858(10) 0.077(6) Uani 1 1 d . . . H26A H 0.8797 0.4095 0.5044 0.092 Uiso 1 1 calc R . . H26B H 0.8745 0.3189 0.4484 0.092 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 Au1 0.0235(2) 0.01583(18) 0.0465(3) -0.0013(3) -0.00004(17) 0.0013(2) C5 0.009(5) 0.019(5) 0.037(7) -0.004(5) -0.011(5) 0.003(4) O2 0.034(3) 0.014(3) 0.068(5) 0.000(3) -0.003(3) -0.004(2) O1 0.034(3) 0.014(3) 0.068(5) 0.000(3) -0.003(3) -0.004(2) C17 0.017(6) 0.023(6) 0.058(9) -0.008(6) 0.015(6) -0.007(4) C11 0.022(6) 0.022(6) 0.051(8) -0.003(5) 0.000(6) -0.002(5) C8 0.023(6) 0.007(4) 0.050(8) -0.002(5) 0.006(5) 0.005(4) C15 0.031(7) 0.014(5) 0.045(8) -0.002(5) 0.011(6) 0.004(4) C21 0.023(6) 0.017(6) 0.057(8) 0.000(5) 0.017(6) -0.010(4) N2 0.025(5) 0.022(5) 0.050(6) -0.001(5) 0.007(5) -0.003(4) C6 0.014(6) 0.017(5) 0.051(8) -0.005(5) 0.004(6) 0.005(4) C2 0.024(4) 0.015(4) 0.076(7) 0.011(4) -0.007(4) -0.001(3) N1 0.015(5) 0.015(4) 0.058(7) -0.006(4) 0.007(5) 0.001(4) C23 0.023(4) 0.008(3) 0.054(6) 0.004(3) 0.003(4) -0.003(3) C3 0.035(8) 0.022(7) 0.099(13) 0.003(7) -0.009(8) -0.004(6) C12 0.024(6) 0.020(5) 0.042(8) -0.003(5) -0.003(5) 0.003(5) C10 0.040(8) 0.038(8) 0.059(10) 0.015(7) 0.016(7) 0.012(6) C24 0.023(4) 0.008(3) 0.054(6) 0.004(3) 0.003(4) -0.003(3) C14 0.042(8) 0.016(5) 0.057(9) -0.003(5) 0.028(7) -0.001(5) C9 0.042(7) 0.016(5) 0.022(6) 0.000(4) 0.006(6) 0.017(5) C27 0.057(10) 0.068(12) 0.067(12) 0.032(9) -0.005(9) -0.012(9) C22 0.028(7) 0.026(7) 0.070(10) 0.008(6) 0.000(7) 0.005(5) C1 0.044(9) 0.036(8) 0.084(12) 0.007(8) 0.020(8) 0.000(6) C28 0.038(10) 0.18(2) 0.099(17) 0.060(17) 0.026(11) 0.022(12) C20 0.031(7) 0.031(7) 0.050(8) -0.004(6) 0.011(6) 0.001(5) C25 0.034(7) 0.045(8) 0.049(9) -0.001(7) -0.009(7) 0.014(6) C4 0.024(4) 0.015(4) 0.076(7) 0.011(4) -0.007(4) -0.001(3) C18 0.016(6) 0.035(7) 0.064(10) 0.003(7) 0.010(6) 0.006(5) C7 0.036(7) 0.011(5) 0.042(8) -0.002(5) -0.005(6) 0.001(5) C13 0.026(7) 0.036(8) 0.067(10) 0.011(7) 0.002(7) 0.002(5) C16 0.040(8) 0.044(8) 0.052(9) 0.005(7) 0.000(7) -0.003(7) C19 0.046(9) 0.064(11) 0.050(10) 0.006(8) 0.007(8) 0.006(8) C29 0.065(12) 0.18(3) 0.036(9) 0.010(13) 0.003(9) -0.025(14) C26 0.069(12) 0.092(15) 0.065(12) 0.044(10) -0.005(10) -0.002(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 1.971(10) . ? Au1 O1 1.990(8) . ? C5 N1 1.320(13) . ? C5 N2 1.360(13) . ? O2 C29 1.45(2) . ? O2 C26 1.529(17) . ? O1 C4 1.423(14) . ? C17 C18 1.386(18) . ? C17 C24 1.419(17) . ? C17 N1 1.442(14) . ? C11 C12 1.394(16) . ? C11 C9 1.413(16) . ? C11 H11 0.9300 . ? C8 C9 1.374(16) . ? C8 N2 1.437(14) . ? C8 C15 1.451(16) . ? C15 C14 1.368(16) . ? C15 C16 1.518(17) . ? C21 C23 1.404(17) . ? C21 C20 1.400(18) . ? C21 C22 1.460(16) . ? N2 C7 1.389(14) . ? C6 C7 1.343(15) . ? C6 N1 1.409(13) . ? C6 H6 0.9300 . ? C2 C4 1.531(16) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C23 C24 1.360(15) . ? C23 H23 0.9300 . ? C3 C4 1.548(17) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C12 C14 1.395(17) . ? C12 C13 1.520(16) . ? C10 C9 1.501(16) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C24 C25 1.486(17) . ? C14 H14 0.9300 . ? C27 C28 1.48(2) . ? C27 C26 1.55(2) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C1 C4 1.54(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C28 C29 1.53(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C20 C18 1.423(16) . ? C20 H20 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C18 C19 1.520(19) . ? C7 H7 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? 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 C5 Au1 O1 178.0(4) . . ? N1 C5 N2 105.5(9) . . ? N1 C5 Au1 130.9(8) . . ? N2 C5 Au1 123.4(7) . . ? C29 O2 C26 108.3(12) . . ? C4 O1 Au1 115.4(7) . . ? C18 C17 C24 123.2(11) . . ? C18 C17 N1 117.9(12) . . ? C24 C17 N1 118.9(11) . . ? C12 C11 C9 121.0(12) . . ? C12 C11 H11 119.5 . . ? C9 C11 H11 119.5 . . ? C9 C8 N2 119.9(10) . . ? C9 C8 C15 123.0(10) . . ? N2 C8 C15 116.8(10) . . ? C14 C15 C8 115.4(11) . . ? C14 C15 C16 123.9(11) . . ? C8 C15 C16 120.7(10) . . ? C23 C21 C20 118.0(11) . . ? C23 C21 C22 122.9(12) . . ? C20 C21 C22 118.9(12) . . ? C5 N2 C7 110.3(9) . . ? C5 N2 C8 122.7(9) . . ? C7 N2 C8 126.6(10) . . ? C7 C6 N1 105.9(10) . . ? C7 C6 H6 127.1 . . ? N1 C6 H6 127.1 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C5 N1 C6 111.3(8) . . ? C5 N1 C17 126.1(9) . . ? C6 N1 C17 122.5(9) . . ? C24 C23 C21 123.4(12) . . ? C24 C23 H23 118.3 . . ? C21 C23 H23 118.3 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C14 C12 C11 118.5(11) . . ? C14 C12 C13 122.2(11) . . ? C11 C12 C13 119.1(11) . . ? 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 . . ? C23 C24 C17 117.0(11) . . ? C23 C24 C25 121.7(12) . . ? C17 C24 C25 121.1(10) . . ? C15 C14 C12 124.1(11) . . ? C15 C14 H14 118.0 . . ? C12 C14 H14 118.0 . . ? C8 C9 C11 118.1(11) . . ? C8 C9 C10 121.0(11) . . ? C11 C9 C10 120.9(11) . . ? C28 C27 C26 105.3(14) . . ? C28 C27 H27A 110.7 . . ? C26 C27 H27A 110.7 . . ? C28 C27 H27B 110.7 . . ? C26 C27 H27B 110.7 . . ? H27A C27 H27B 108.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C27 C28 C29 105.1(15) . . ? C27 C28 H28A 110.7 . . ? C29 C28 H28A 110.7 . . ? C27 C28 H28B 110.7 . . ? C29 C28 H28B 110.7 . . ? H28A C28 H28B 108.8 . . ? C21 C20 C18 121.2(12) . . ? C21 C20 H20 119.4 . . ? C18 C20 H20 119.4 . . ? 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 . . ? O1 C4 C2 112.9(10) . . ? O1 C4 C1 109.2(11) . . ? C2 C4 C1 111.6(11) . . ? O1 C4 C3 104.9(10) . . ? C2 C4 C3 106.2(11) . . ? C1 C4 C3 111.9(11) . . ? C17 C18 C20 117.1(12) . . ? C17 C18 C19 123.3(11) . . ? C20 C18 C19 119.6(12) . . ? C6 C7 N2 106.9(10) . . ? C6 C7 H7 126.5 . . ? N2 C7 H7 126.5 . . ? 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 . . ? 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 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C29 C28 107.4(12) . . ? O2 C29 H29A 110.2 . . ? C28 C29 H29A 110.2 . . ? O2 C29 H29B 110.2 . . ? C28 C29 H29B 110.2 . . ? H29A C29 H29B 108.5 . . ? C27 C26 O2 100.7(12) . . ? C27 C26 H26A 111.6 . . ? O2 C26 H26A 111.6 . . ? C27 C26 H26B 111.6 . . ? O2 C26 H26B 111.6 . . ? H26A C26 H26B 109.4 . . ? 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 O1 Au1 C5 N1 -175(43) . . . . ? O1 Au1 C5 N2 0(13) . . . . ? C5 Au1 O1 C4 7(13) . . . . ? C9 C8 C15 C14 -0.7(15) . . . . ? N2 C8 C15 C14 172.9(9) . . . . ? C9 C8 C15 C16 178.6(11) . . . . ? N2 C8 C15 C16 -7.8(15) . . . . ? N1 C5 N2 C7 -2.0(14) . . . . ? Au1 C5 N2 C7 -177.8(8) . . . . ? N1 C5 N2 C8 -175.5(10) . . . . ? Au1 C5 N2 C8 8.7(16) . . . . ? C9 C8 N2 C5 90.0(13) . . . . ? C15 C8 N2 C5 -83.7(14) . . . . ? C9 C8 N2 C7 -82.3(15) . . . . ? C15 C8 N2 C7 103.9(13) . . . . ? N2 C5 N1 C6 1.3(14) . . . . ? Au1 C5 N1 C6 176.6(9) . . . . ? N2 C5 N1 C17 177.1(11) . . . . ? Au1 C5 N1 C17 -7.5(19) . . . . ? C7 C6 N1 C5 -0.1(14) . . . . ? C7 C6 N1 C17 -176.1(11) . . . . ? C18 C17 N1 C5 -70.1(16) . . . . ? C24 C17 N1 C5 110.6(13) . . . . ? C18 C17 N1 C6 105.3(14) . . . . ? C24 C17 N1 C6 -73.9(15) . . . . ? C20 C21 C23 C24 -3.8(16) . . . . ? C22 C21 C23 C24 -179.1(10) . . . . ? C9 C11 C12 C14 -1.1(16) . . . . ? C9 C11 C12 C13 173.5(10) . . . . ? C21 C23 C24 C17 4.6(15) . . . . ? C21 C23 C24 C25 179.0(10) . . . . ? C18 C17 C24 C23 -4.4(16) . . . . ? N1 C17 C24 C23 174.8(9) . . . . ? C18 C17 C24 C25 -178.8(11) . . . . ? N1 C17 C24 C25 0.4(16) . . . . ? C8 C15 C14 C12 0.0(16) . . . . ? C16 C15 C14 C12 -179.3(11) . . . . ? C11 C12 C14 C15 0.8(17) . . . . ? C13 C12 C14 C15 -173.6(11) . . . . ? N2 C8 C9 C11 -173.0(9) . . . . ? C15 C8 C9 C11 0.4(15) . . . . ? N2 C8 C9 C10 9.5(15) . . . . ? C15 C8 C9 C10 -177.1(10) . . . . ? C12 C11 C9 C8 0.5(16) . . . . ? C12 C11 C9 C10 178.1(11) . . . . ? C26 C27 C28 C29 -30(2) . . . . ? C23 C21 C20 C18 2.4(17) . . . . ? C22 C21 C20 C18 177.9(11) . . . . ? Au1 O1 C4 C2 -56.2(13) . . . . ? Au1 O1 C4 C1 68.6(10) . . . . ? Au1 O1 C4 C3 -171.3(9) . . . . ? C24 C17 C18 C20 3.1(18) . . . . ? N1 C17 C18 C20 -176.0(10) . . . . ? C24 C17 C18 C19 -178.7(12) . . . . ? N1 C17 C18 C19 2.1(18) . . . . ? C21 C20 C18 C17 -2.1(18) . . . . ? C21 C20 C18 C19 179.6(12) . . . . ? N1 C6 C7 N2 -1.2(14) . . . . ? C5 N2 C7 C6 2.1(14) . . . . ? C8 N2 C7 C6 175.2(11) . . . . ? C26 O2 C29 C28 12(2) . . . . ? C27 C28 C29 O2 12(2) . . . . ? C28 C27 C26 O2 36(2) . . . . ? C29 O2 C26 C27 -29.1(18) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 7.378 _refine_diff_density_min -2.836 _refine_diff_density_rms 0.371 # Attachment '- compound3.cif' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 832960' #TrackingRef '- compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H58 Au2 N4' _chemical_formula_weight 1156.98 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' 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 9.9439(5) _cell_length_b 15.6363(8) _cell_length_c 16.4516(8) _cell_angle_alpha 79.470(4) _cell_angle_beta 83.978(4) _cell_angle_gamma 77.020(4) _cell_volume 2445.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7128 _cell_measurement_theta_min 2.2467 _cell_measurement_theta_max 33.0880 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 6.031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.52387 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24817 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.1502 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 33.16 _reflns_number_total 15799 _reflns_number_gt 6460 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0403P)^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 15799 _refine_ls_number_parameters 529 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0.003 _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 Au2 Au 1.02079(2) 0.246666(13) 0.502992(13) 0.05424(8) Uani 1 1 d . . . Au1 Au 0.74468(2) 0.239459(15) 1.046257(14) 0.06121(8) Uani 1 1 d . . . C34 C 0.8523(5) 0.2847(3) 0.4350(3) 0.0513(13) Uani 1 1 d . . . C37 C 0.9025(5) 0.1596(4) 0.3570(3) 0.0522(13) Uani 1 1 d . . . N4 N 0.8204(4) 0.2413(3) 0.3793(3) 0.0551(11) Uani 1 1 d . . . C22 C 1.2554(6) 0.1750(5) 1.0503(4) 0.080(2) Uani 1 1 d . . . H22 H 1.3020 0.1978 1.0847 0.097 Uiso 1 1 calc R . . C28 C 1.1901(5) 0.2053(3) 0.5712(3) 0.0526(9) Uani 1 1 d . . . C7 C 0.8423(6) 0.2804(4) 0.9361(3) 0.0666(16) Uani 1 1 d . . . C26 C 1.1160(8) 0.1081(5) 0.9506(4) 0.086(2) Uani 1 1 d . . . C27 C 1.0389(8) 0.0728(5) 0.8945(5) 0.118(3) Uani 1 1 d . . . H27A H 0.9419 0.0982 0.9009 0.177 Uiso 1 1 calc R . . H27B H 1.0536 0.0092 0.9089 0.177 Uiso 1 1 calc R . . H27C H 1.0721 0.0884 0.8380 0.177 Uiso 1 1 calc R . . N3 N 0.7482(4) 0.3557(3) 0.4370(3) 0.0580(12) Uani 1 1 d . . . C10 C 0.6385(6) 0.3823(4) 0.8703(3) 0.0616(15) Uani 1 1 d . . . N1 N 0.9759(5) 0.2588(4) 0.9095(3) 0.0765(15) Uani 1 1 d . . . C45 C 1.0190(7) 0.2518(4) 0.2407(4) 0.095(2) Uani 1 1 d . . . H45A H 1.0971 0.2419 0.2015 0.143 Uiso 1 1 calc R . . H45B H 1.0342 0.2902 0.2767 0.143 Uiso 1 1 calc R . . H45C H 0.9373 0.2792 0.2117 0.143 Uiso 1 1 calc R . . N2 N 0.7802(5) 0.3370(4) 0.8715(3) 0.0702(14) Uani 1 1 d . . . C31 C 1.4188(7) 0.1467(5) 0.6698(5) 0.094(2) Uani 1 1 d . . . H31 H 1.4956 0.1294 0.7013 0.113 Uiso 1 1 calc R . . C50 C 0.7240(6) 0.5397(4) 0.5970(4) 0.0619(15) Uani 1 1 d . . . C24 C 1.4073(8) 0.0254(6) 1.0968(5) 0.119(3) Uani 1 1 d . . . H24A H 1.4863 0.0519 1.0938 0.179 Uiso 1 1 calc R . . H24B H 1.4339 -0.0295 1.0752 0.179 Uiso 1 1 calc R . . H24C H 1.3724 0.0138 1.1535 0.179 Uiso 1 1 calc R . . C41 C 1.0680(6) 0.0039(4) 0.3162(4) 0.0660(17) Uani 1 1 d . . . C20 C 1.1512(7) 0.2344(5) 1.0087(4) 0.084(2) Uani 1 1 d . . . C46 C 0.7384(6) 0.4205(4) 0.4913(4) 0.0616(15) Uani 1 1 d . . . C42 C 1.1588(6) -0.0823(4) 0.2963(4) 0.086(2) Uani 1 1 d . . . H42A H 1.1152 -0.1309 0.3201 0.129 Uiso 1 1 calc R . . H42B H 1.2469 -0.0911 0.3190 0.129 Uiso 1 1 calc R . . H42C H 1.1718 -0.0795 0.2373 0.129 Uiso 1 1 calc R . . C49 C 0.7888(7) 0.5537(3) 0.5188(5) 0.0758(19) Uani 1 1 d . . . H49 H 0.8272 0.6037 0.5023 0.091 Uiso 1 1 calc R . . C19 C 1.0838(6) 0.1974(5) 0.9579(4) 0.0687(17) Uani 1 1 d . . . C29 C 1.3154(7) 0.1694(5) 0.5402(4) 0.091(2) Uani 1 1 d . . . H29 H 1.3269 0.1635 0.4845 0.110 Uiso 1 1 calc R . . C12 C 0.5788(8) 0.2420(5) 0.8409(5) 0.115(3) Uani 1 1 d . . . H12A H 0.5665 0.2050 0.8934 0.173 Uiso 1 1 calc R . . H12B H 0.6736 0.2277 0.8201 0.173 Uiso 1 1 calc R . . H12C H 0.5202 0.2320 0.8024 0.173 Uiso 1 1 calc R . . C38 C 0.8824(5) 0.0788(3) 0.4018(3) 0.0534(13) Uani 1 1 d . . . C48 C 0.8686(9) 0.5091(5) 0.3795(4) 0.108(3) Uani 1 1 d . . . H48A H 0.9340 0.4559 0.3701 0.161 Uiso 1 1 calc R . . H48B H 0.9162 0.5570 0.3754 0.161 Uiso 1 1 calc R . . H48C H 0.8013 0.5242 0.3386 0.161 Uiso 1 1 calc R . . C14 C 0.3679(7) 0.4726(4) 0.8573(3) 0.0712(18) Uani 1 1 d . . . C1 C 0.6437(5) 0.1932(3) 1.1522(3) 0.0526(9) Uani 1 1 d . . . C6 C 0.7026(6) 0.1163(4) 1.2049(4) 0.0664(16) Uani 1 1 d . . . H6 H 0.7944 0.0895 1.1935 0.080 Uiso 1 1 calc R . . C17 C 0.6016(8) 0.4699(5) 0.8830(4) 0.0752(18) Uani 1 1 d . . . C51 C 0.7188(7) 0.6070(4) 0.6539(4) 0.090(2) Uani 1 1 d . . . H51A H 0.7887 0.5842 0.6929 0.136 Uiso 1 1 calc R . . H51B H 0.6294 0.6174 0.6831 0.136 Uiso 1 1 calc R . . H51C H 0.7349 0.6619 0.6215 0.136 Uiso 1 1 calc R . . C52 C 0.6667(6) 0.4682(4) 0.6201(3) 0.0596(15) Uani 1 1 d . . . H52 H 0.6227 0.4594 0.6728 0.072 Uiso 1 1 calc R . . C44 C 1.0008(6) 0.1640(3) 0.2915(4) 0.0577(15) Uani 1 1 d . . . C23 C 1.2974(6) 0.0874(6) 1.0469(4) 0.090(2) Uani 1 1 d . . . C30 C 1.4321(7) 0.1398(5) 0.5892(5) 0.0881(15) Uani 1 1 d . . . H30 H 1.5178 0.1156 0.5652 0.106 Uiso 1 1 calc R . . C35 C 0.6537(6) 0.3566(4) 0.3813(4) 0.079(2) Uani 1 1 d . . . H35 H 0.5730 0.3993 0.3712 0.094 Uiso 1 1 calc R . . C40 C 0.9687(6) 0.0031(4) 0.3801(4) 0.0620(16) Uani 1 1 d . . . H40 H 0.9588 -0.0516 0.4107 0.074 Uiso 1 1 calc R . . C43 C 1.0831(6) 0.0858(4) 0.2717(4) 0.0666(16) Uani 1 1 d . . . H43 H 1.1499 0.0882 0.2278 0.080 Uiso 1 1 calc R . . C47 C 0.7973(6) 0.4941(4) 0.4644(4) 0.0608(15) Uani 1 1 d . . . C53 C 0.6708(6) 0.4070(3) 0.5680(4) 0.0617(15) Uani 1 1 d . . . C5 C 0.6311(8) 0.0783(4) 1.2730(4) 0.083(2) Uani 1 1 d . . . H5 H 0.6724 0.0247 1.3042 0.099 Uiso 1 1 calc R . . C21 C 1.1132(9) 0.3312(5) 1.0139(4) 0.108(3) Uani 1 1 d . . . H21A H 1.1728 0.3446 1.0498 0.161 Uiso 1 1 calc R . . H21B H 1.0189 0.3460 1.0355 0.161 Uiso 1 1 calc R . . H21C H 1.1232 0.3652 0.9596 0.161 Uiso 1 1 calc R . . C11 C 0.5411(7) 0.3388(4) 0.8518(4) 0.0761(18) Uani 1 1 d . . . C36 C 0.6981(6) 0.2864(4) 0.3450(4) 0.0779(19) Uani 1 1 d . . . H36 H 0.6554 0.2701 0.3043 0.093 Uiso 1 1 calc R . . C9 C 0.8756(8) 0.3503(6) 0.8049(5) 0.107(3) Uani 1 1 d . . . H9 H 0.8575 0.3860 0.7539 0.129 Uiso 1 1 calc R . . C16 C 0.4670(9) 0.5127(4) 0.8769(4) 0.087(2) Uani 1 1 d . . . H16 H 0.4411 0.5712 0.8864 0.105 Uiso 1 1 calc R . . C3 C 0.4372(7) 0.1949(5) 1.2475(5) 0.0881(15) Uani 1 1 d . . . H3 H 0.3474 0.2227 1.2625 0.106 Uiso 1 1 calc R . . C25 C 1.2227(6) 0.0548(5) 0.9966(5) 0.092(2) Uani 1 1 d . . . H25 H 1.2453 -0.0057 0.9939 0.110 Uiso 1 1 calc R . . C4 C 0.4988(9) 0.1195(5) 1.2949(4) 0.091(2) Uani 1 1 d . . . H4 H 0.4518 0.0954 1.3423 0.110 Uiso 1 1 calc R . . C8 C 0.9974(8) 0.3025(6) 0.8280(4) 0.100(3) Uani 1 1 d . . . H8 H 1.0811 0.2986 0.7964 0.120 Uiso 1 1 calc R . . C13 C 0.4071(7) 0.3858(4) 0.8457(4) 0.0766(18) Uani 1 1 d . . . H13 H 0.3406 0.3576 0.8333 0.092 Uiso 1 1 calc R . . C15 C 0.2188(7) 0.5237(4) 0.8487(5) 0.101(2) Uani 1 1 d . . . H15A H 0.1920 0.5590 0.8920 0.152 Uiso 1 1 calc R . . H15B H 0.1591 0.4824 0.8530 0.152 Uiso 1 1 calc R . . H15C H 0.2115 0.5617 0.7958 0.152 Uiso 1 1 calc R . . C39 C 0.7738(6) 0.0758(4) 0.4713(4) 0.0761(18) Uani 1 1 d . . . H39A H 0.7940 0.1053 0.5135 0.114 Uiso 1 1 calc R . . H39B H 0.7722 0.0150 0.4941 0.114 Uiso 1 1 calc R . . H39C H 0.6853 0.1053 0.4510 0.114 Uiso 1 1 calc R . . C54 C 0.6002(8) 0.3284(4) 0.5939(5) 0.109(3) Uani 1 1 d . . . H54A H 0.5492 0.3231 0.5492 0.164 Uiso 1 1 calc R . . H54B H 0.5382 0.3376 0.6417 0.164 Uiso 1 1 calc R . . H54C H 0.6689 0.2748 0.6069 0.164 Uiso 1 1 calc R . . C2 C 0.5058(6) 0.2313(4) 1.1771(4) 0.0632(16) Uani 1 1 d . . . H2 H 0.4599 0.2826 1.1447 0.076 Uiso 1 1 calc R . . C32 C 1.2929(8) 0.1790(6) 0.7049(5) 0.121(3) Uani 1 1 d . . . H32 H 1.2812 0.1816 0.7612 0.145 Uiso 1 1 calc R . . C33 C 1.1809(7) 0.2082(5) 0.6554(5) 0.100(3) Uani 1 1 d . . . H33 H 1.0951 0.2309 0.6802 0.121 Uiso 1 1 calc R . . C18 C 0.7071(9) 0.5163(5) 0.9061(5) 0.111(3) Uani 1 1 d . . . H18A H 0.7647 0.4763 0.9462 0.167 Uiso 1 1 calc R . . H18B H 0.6601 0.5680 0.9292 0.167 Uiso 1 1 calc R . . H18C H 0.7632 0.5339 0.8575 0.167 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 Au2 0.05220(13) 0.05081(13) 0.06192(15) -0.01755(11) -0.00617(11) -0.00768(10) Au1 0.05935(15) 0.06693(15) 0.05962(15) -0.01761(12) -0.00268(12) -0.01277(12) C34 0.045(3) 0.056(3) 0.059(3) -0.019(3) -0.002(3) -0.015(2) C37 0.036(3) 0.071(4) 0.051(3) -0.028(3) 0.011(2) -0.005(2) N4 0.040(2) 0.060(3) 0.069(3) -0.028(2) -0.002(2) -0.003(2) C22 0.046(4) 0.127(6) 0.063(4) -0.015(4) 0.001(3) -0.009(4) C28 0.049(2) 0.054(2) 0.054(2) -0.0033(18) 0.0038(19) -0.0174(18) C7 0.064(4) 0.097(5) 0.042(3) -0.010(3) 0.009(3) -0.031(3) C26 0.085(5) 0.108(6) 0.083(5) -0.051(4) 0.012(4) -0.035(4) C27 0.104(6) 0.143(7) 0.126(7) -0.078(6) -0.012(5) -0.021(5) N3 0.054(3) 0.052(2) 0.066(3) -0.027(2) -0.004(2) 0.006(2) C10 0.058(4) 0.068(4) 0.055(3) -0.012(3) -0.006(3) -0.004(3) N1 0.061(3) 0.111(4) 0.061(3) -0.030(3) 0.000(3) -0.012(3) C45 0.080(5) 0.082(5) 0.110(6) -0.002(4) 0.017(4) -0.011(4) N2 0.057(3) 0.109(4) 0.046(3) -0.016(3) 0.016(2) -0.027(3) C31 0.061(5) 0.103(6) 0.118(7) -0.016(5) -0.027(5) -0.011(4) C50 0.067(4) 0.052(3) 0.070(4) -0.023(3) -0.003(3) -0.009(3) C24 0.082(5) 0.170(8) 0.089(5) -0.027(5) 0.012(4) 0.008(5) C41 0.065(4) 0.071(4) 0.059(3) -0.039(3) -0.004(3) 0.015(3) C20 0.082(5) 0.114(6) 0.060(4) -0.023(4) -0.007(4) -0.018(4) C46 0.063(4) 0.055(3) 0.067(4) -0.027(3) -0.012(3) 0.005(3) C42 0.064(4) 0.080(4) 0.108(5) -0.035(4) -0.003(4) 0.013(3) C49 0.082(4) 0.037(3) 0.117(6) -0.027(3) 0.002(4) -0.024(3) C19 0.041(3) 0.109(5) 0.061(4) -0.031(4) 0.000(3) -0.014(3) C29 0.061(4) 0.138(6) 0.072(4) -0.013(4) 0.005(4) -0.021(4) C12 0.120(7) 0.096(5) 0.142(7) -0.072(5) -0.036(6) 0.007(5) C38 0.043(3) 0.054(3) 0.069(4) -0.023(3) 0.005(3) -0.017(2) C48 0.133(7) 0.110(6) 0.089(5) -0.023(5) 0.035(5) -0.058(5) C14 0.085(5) 0.070(4) 0.039(3) 0.019(3) 0.008(3) -0.002(4) C1 0.049(2) 0.054(2) 0.054(2) -0.0033(18) 0.0038(19) -0.0174(18) C6 0.053(4) 0.081(4) 0.059(4) -0.007(3) 0.018(3) -0.015(3) C17 0.086(5) 0.083(5) 0.060(4) -0.006(3) -0.004(4) -0.029(4) C51 0.081(5) 0.097(5) 0.101(5) -0.051(4) -0.003(4) -0.010(4) C52 0.068(4) 0.055(3) 0.044(3) -0.001(3) 0.011(3) -0.002(3) C44 0.065(4) 0.039(3) 0.082(4) -0.040(3) -0.020(3) -0.007(2) C23 0.039(3) 0.145(7) 0.080(5) -0.031(5) -0.011(3) 0.007(4) C30 0.056(3) 0.110(4) 0.097(4) -0.032(3) 0.027(3) -0.017(3) C35 0.057(4) 0.075(4) 0.112(5) -0.053(4) -0.030(4) 0.010(3) C40 0.068(4) 0.055(3) 0.075(4) -0.037(3) -0.021(3) -0.010(3) C43 0.059(4) 0.081(4) 0.059(4) -0.014(3) 0.002(3) -0.013(3) C47 0.059(4) 0.061(3) 0.068(4) -0.014(3) 0.001(3) -0.025(3) C53 0.076(4) 0.038(3) 0.074(4) -0.022(3) 0.004(3) -0.013(3) C5 0.100(6) 0.074(4) 0.085(5) -0.029(4) -0.023(5) -0.018(4) C21 0.140(7) 0.108(6) 0.086(5) -0.021(5) -0.020(5) -0.040(5) C11 0.071(4) 0.088(5) 0.068(4) -0.024(4) -0.011(3) -0.002(4) C36 0.072(4) 0.066(4) 0.100(5) -0.031(4) -0.032(4) 0.003(3) C9 0.089(6) 0.145(7) 0.074(5) -0.011(5) -0.016(5) 0.005(5) C16 0.110(6) 0.066(4) 0.085(5) -0.007(4) -0.017(5) -0.017(4) C3 0.056(3) 0.110(4) 0.097(4) -0.032(3) 0.027(3) -0.017(3) C25 0.036(3) 0.111(5) 0.116(6) -0.030(5) -0.005(4) 0.018(4) C4 0.118(7) 0.103(6) 0.072(5) -0.028(4) 0.009(5) -0.060(5) C8 0.088(6) 0.158(8) 0.048(4) -0.007(4) 0.017(4) -0.027(5) C13 0.070(4) 0.083(5) 0.082(5) -0.029(4) -0.005(4) -0.014(4) C15 0.097(6) 0.083(5) 0.107(6) 0.000(4) -0.018(5) 0.007(4) C39 0.057(4) 0.090(4) 0.069(4) -0.002(3) 0.021(3) -0.012(3) C54 0.135(7) 0.069(4) 0.132(7) -0.034(4) 0.034(6) -0.041(5) C2 0.048(3) 0.055(3) 0.086(4) -0.011(3) -0.019(3) -0.005(3) C32 0.087(6) 0.178(9) 0.102(6) -0.060(6) -0.046(5) 0.010(6) C33 0.074(5) 0.141(7) 0.092(5) -0.063(5) -0.020(4) 0.007(4) C18 0.127(7) 0.090(5) 0.123(7) -0.005(5) -0.033(6) -0.037(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Au2 C34 2.028(5) . ? Au2 C28 2.038(5) . ? Au1 C1 2.016(5) . ? Au1 C7 2.031(5) . ? C34 N4 1.336(6) . ? C34 N3 1.340(6) . ? C37 C44 1.380(7) . ? C37 C38 1.386(7) . ? C37 N4 1.440(6) . ? N4 C36 1.381(7) . ? C22 C23 1.349(9) . ? C22 C20 1.374(9) . ? C22 H22 0.9300 . ? C28 C29 1.335(8) . ? C28 C33 1.387(8) . ? C7 N1 1.343(7) . ? C7 N2 1.357(7) . ? C26 C19 1.385(9) . ? C26 C25 1.391(9) . ? C26 C27 1.505(9) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? N3 C35 1.375(7) . ? N3 C46 1.451(6) . ? C10 C17 1.384(8) . ? C10 C11 1.389(8) . ? C10 N2 1.428(7) . ? N1 C8 1.407(8) . ? N1 C19 1.464(7) . ? C45 C44 1.508(8) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? N2 C9 1.390(8) . ? C31 C30 1.340(9) . ? C31 C32 1.351(10) . ? C31 H31 0.9300 . ? C50 C52 1.344(7) . ? C50 C49 1.379(8) . ? C50 C51 1.521(8) . ? C24 C23 1.494(9) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C41 C40 1.365(8) . ? C41 C43 1.385(8) . ? C41 C42 1.513(7) . ? C20 C19 1.397(8) . ? C20 C21 1.491(9) . ? C46 C53 1.371(8) . ? C46 C47 1.386(8) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C49 C47 1.390(8) . ? C49 H49 0.9300 . ? C29 C30 1.425(9) . ? C29 H29 0.9300 . ? C12 C11 1.514(9) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C38 C40 1.379(7) . ? C38 C39 1.490(7) . ? C48 C47 1.503(8) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C14 C13 1.369(8) . ? C14 C16 1.373(9) . ? C14 C15 1.525(8) . ? C1 C6 1.397(7) . ? C1 C2 1.417(7) . ? C6 C5 1.377(8) . ? C6 H6 0.9300 . ? C17 C16 1.361(9) . ? C17 C18 1.515(9) . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 C53 1.388(7) . ? C52 H52 0.9300 . ? C44 C43 1.383(7) . ? C23 C25 1.396(9) . ? C30 H30 0.9300 . ? C35 C36 1.313(7) . ? C35 H35 0.9300 . ? C40 H40 0.9300 . ? C43 H43 0.9300 . ? C53 C54 1.523(8) . ? C5 C4 1.371(9) . ? C5 H5 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C11 C13 1.373(8) . ? C36 H36 0.9300 . ? C9 C8 1.325(9) . ? C9 H9 0.9300 . ? C16 H16 0.9300 . ? C3 C4 1.347(9) . ? C3 C2 1.378(9) . ? C3 H3 0.9300 . ? C25 H25 0.9300 . ? C4 H4 0.9300 . ? C8 H8 0.9300 . ? C13 H13 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C2 H2 0.9300 . ? C32 C33 1.391(9) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C34 Au2 C28 178.57(19) . . ? C1 Au1 C7 176.4(2) . . ? N4 C34 N3 105.1(4) . . ? N4 C34 Au2 126.3(4) . . ? N3 C34 Au2 128.6(4) . . ? C44 C37 C38 121.6(4) . . ? C44 C37 N4 118.7(5) . . ? C38 C37 N4 119.7(4) . . ? C34 N4 C36 110.5(4) . . ? C34 N4 C37 125.0(4) . . ? C36 N4 C37 124.4(5) . . ? C23 C22 C20 127.3(7) . . ? C23 C22 H22 116.4 . . ? C20 C22 H22 116.4 . . ? C29 C28 C33 115.0(6) . . ? C29 C28 Au2 123.4(5) . . ? C33 C28 Au2 121.6(4) . . ? N1 C7 N2 104.9(5) . . ? N1 C7 Au1 129.9(5) . . ? N2 C7 Au1 125.2(4) . . ? C19 C26 C25 116.4(6) . . ? C19 C26 C27 120.6(7) . . ? C25 C26 C27 123.0(7) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C34 N3 C35 110.1(4) . . ? C34 N3 C46 123.9(4) . . ? C35 N3 C46 126.0(4) . . ? C17 C10 C11 121.1(6) . . ? C17 C10 N2 119.8(6) . . ? C11 C10 N2 118.9(5) . . ? C7 N1 C8 110.4(6) . . ? C7 N1 C19 124.8(5) . . ? C8 N1 C19 124.8(6) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C7 N2 C9 110.8(5) . . ? C7 N2 C10 126.7(5) . . ? C9 N2 C10 122.5(6) . . ? C30 C31 C32 119.5(7) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C52 C50 C49 119.4(5) . . ? C52 C50 C51 122.2(6) . . ? C49 C50 C51 118.4(6) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C40 C41 C43 117.7(5) . . ? C40 C41 C42 120.4(6) . . ? C43 C41 C42 121.9(6) . . ? C22 C20 C19 114.4(7) . . ? C22 C20 C21 124.2(7) . . ? C19 C20 C21 121.4(6) . . ? C53 C46 C47 121.9(5) . . ? C53 C46 N3 118.6(5) . . ? C47 C46 N3 119.4(5) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C50 C49 C47 120.8(5) . . ? C50 C49 H49 119.6 . . ? C47 C49 H49 119.6 . . ? C26 C19 C20 123.5(6) . . ? C26 C19 N1 120.0(6) . . ? C20 C19 N1 116.5(6) . . ? C28 C29 C30 122.5(6) . . ? C28 C29 H29 118.8 . . ? C30 C29 H29 118.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C40 C38 C37 117.0(5) . . ? C40 C38 C39 122.5(5) . . ? C37 C38 C39 120.5(5) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C13 C14 C16 118.0(6) . . ? C13 C14 C15 121.2(7) . . ? C16 C14 C15 120.8(6) . . ? C6 C1 C2 114.1(5) . . ? C6 C1 Au1 121.9(4) . . ? C2 C1 Au1 123.8(4) . . ? C5 C6 C1 123.0(6) . . ? C5 C6 H6 118.5 . . ? C1 C6 H6 118.5 . . ? C16 C17 C10 118.3(6) . . ? C16 C17 C18 120.6(7) . . ? C10 C17 C18 121.0(6) . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C50 C52 C53 122.2(5) . . ? C50 C52 H52 118.9 . . ? C53 C52 H52 118.9 . . ? C37 C44 C43 118.9(5) . . ? C37 C44 C45 121.6(5) . . ? C43 C44 C45 119.6(6) . . ? C22 C23 C25 115.0(6) . . ? C22 C23 C24 124.7(7) . . ? C25 C23 C24 120.2(8) . . ? C31 C30 C29 120.2(6) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C36 C35 N3 107.6(5) . . ? C36 C35 H35 126.2 . . ? N3 C35 H35 126.2 . . ? C41 C40 C38 123.7(6) . . ? C41 C40 H40 118.2 . . ? C38 C40 H40 118.2 . . ? C44 C43 C41 121.2(5) . . ? C44 C43 H43 119.4 . . ? C41 C43 H43 119.4 . . ? C46 C47 C49 117.9(5) . . ? C46 C47 C48 121.4(5) . . ? C49 C47 C48 120.7(6) . . ? C46 C53 C52 117.8(5) . . ? C46 C53 C54 120.7(5) . . ? C52 C53 C54 121.5(6) . . ? C4 C5 C6 119.9(7) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? 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 . . ? C13 C11 C10 117.8(6) . . ? C13 C11 C12 120.4(7) . . ? C10 C11 C12 121.7(6) . . ? C35 C36 N4 106.6(5) . . ? C35 C36 H36 126.7 . . ? N4 C36 H36 126.7 . . ? C8 C9 N2 107.0(7) . . ? C8 C9 H9 126.5 . . ? N2 C9 H9 126.5 . . ? C17 C16 C14 122.4(7) . . ? C17 C16 H16 118.8 . . ? C14 C16 H16 118.8 . . ? C4 C3 C2 120.6(6) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C26 C25 C23 123.4(7) . . ? C26 C25 H25 118.3 . . ? C23 C25 H25 118.3 . . ? C3 C4 C5 119.9(7) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C9 C8 N1 106.9(6) . . ? C9 C8 H8 126.5 . . ? N1 C8 H8 126.5 . . ? C14 C13 C11 122.3(7) . . ? C14 C13 H13 118.8 . . ? C11 C13 H13 118.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C3 C2 C1 122.3(6) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C31 C32 C33 119.0(7) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? C28 C33 C32 123.7(7) . . ? C28 C33 H33 118.2 . . ? C32 C33 H33 118.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C28 Au2 C34 N4 -30(9) . . . . ? C28 Au2 C34 N3 148(8) . . . . ? N3 C34 N4 C36 1.3(6) . . . . ? Au2 C34 N4 C36 179.9(4) . . . . ? N3 C34 N4 C37 -179.3(5) . . . . ? Au2 C34 N4 C37 -0.7(8) . . . . ? C44 C37 N4 C34 -91.5(7) . . . . ? C38 C37 N4 C34 87.8(7) . . . . ? C44 C37 N4 C36 87.8(7) . . . . ? C38 C37 N4 C36 -92.9(7) . . . . ? C34 Au2 C28 C29 70(8) . . . . ? C34 Au2 C28 C33 -106(8) . . . . ? C1 Au1 C7 N1 -99(4) . . . . ? C1 Au1 C7 N2 80(4) . . . . ? N4 C34 N3 C35 -1.0(6) . . . . ? Au2 C34 N3 C35 -179.5(5) . . . . ? N4 C34 N3 C46 178.3(5) . . . . ? Au2 C34 N3 C46 -0.2(8) . . . . ? N2 C7 N1 C8 0.3(8) . . . . ? Au1 C7 N1 C8 179.3(5) . . . . ? N2 C7 N1 C19 -178.8(5) . . . . ? Au1 C7 N1 C19 0.1(10) . . . . ? N1 C7 N2 C9 0.0(8) . . . . ? Au1 C7 N2 C9 -179.0(5) . . . . ? N1 C7 N2 C10 -176.7(6) . . . . ? Au1 C7 N2 C10 4.2(9) . . . . ? C17 C10 N2 C7 98.3(8) . . . . ? C11 C10 N2 C7 -85.1(8) . . . . ? C17 C10 N2 C9 -78.1(8) . . . . ? C11 C10 N2 C9 98.5(8) . . . . ? C23 C22 C20 C19 0.2(11) . . . . ? C23 C22 C20 C21 -178.2(7) . . . . ? C34 N3 C46 C53 -90.3(7) . . . . ? C35 N3 C46 C53 88.9(8) . . . . ? C34 N3 C46 C47 89.7(7) . . . . ? C35 N3 C46 C47 -91.1(7) . . . . ? C52 C50 C49 C47 -1.1(9) . . . . ? C51 C50 C49 C47 179.6(5) . . . . ? C25 C26 C19 C20 -0.6(10) . . . . ? C27 C26 C19 C20 -179.9(7) . . . . ? C25 C26 C19 N1 178.0(6) . . . . ? C27 C26 C19 N1 -1.4(10) . . . . ? C22 C20 C19 C26 1.2(10) . . . . ? C21 C20 C19 C26 179.6(7) . . . . ? C22 C20 C19 N1 -177.5(5) . . . . ? C21 C20 C19 N1 0.9(9) . . . . ? C7 N1 C19 C26 92.9(8) . . . . ? C8 N1 C19 C26 -86.2(9) . . . . ? C7 N1 C19 C20 -88.4(8) . . . . ? C8 N1 C19 C20 92.5(8) . . . . ? C33 C28 C29 C30 -2.5(10) . . . . ? Au2 C28 C29 C30 -179.1(5) . . . . ? C44 C37 C38 C40 2.4(8) . . . . ? N4 C37 C38 C40 -176.9(5) . . . . ? C44 C37 C38 C39 -178.9(5) . . . . ? N4 C37 C38 C39 1.8(8) . . . . ? C7 Au1 C1 C6 83(4) . . . . ? C7 Au1 C1 C2 -93(4) . . . . ? C2 C1 C6 C5 2.9(9) . . . . ? Au1 C1 C6 C5 -173.2(5) . . . . ? C11 C10 C17 C16 -0.1(10) . . . . ? N2 C10 C17 C16 176.4(6) . . . . ? C11 C10 C17 C18 177.9(6) . . . . ? N2 C10 C17 C18 -5.6(9) . . . . ? C49 C50 C52 C53 0.3(9) . . . . ? C51 C50 C52 C53 179.7(5) . . . . ? C38 C37 C44 C43 -1.5(8) . . . . ? N4 C37 C44 C43 177.8(5) . . . . ? C38 C37 C44 C45 177.7(5) . . . . ? N4 C37 C44 C45 -3.0(8) . . . . ? C20 C22 C23 C25 -1.8(11) . . . . ? C20 C22 C23 C24 -177.0(7) . . . . ? C32 C31 C30 C29 2.4(12) . . . . ? C28 C29 C30 C31 0.5(12) . . . . ? C34 N3 C35 C36 0.3(8) . . . . ? C46 N3 C35 C36 -179.0(6) . . . . ? C43 C41 C40 C38 0.8(9) . . . . ? C42 C41 C40 C38 179.9(5) . . . . ? C37 C38 C40 C41 -2.1(8) . . . . ? C39 C38 C40 C41 179.2(6) . . . . ? C37 C44 C43 C41 0.2(8) . . . . ? C45 C44 C43 C41 -179.0(6) . . . . ? C40 C41 C43 C44 0.1(9) . . . . ? C42 C41 C43 C44 -178.9(5) . . . . ? C53 C46 C47 C49 1.4(9) . . . . ? N3 C46 C47 C49 -178.5(5) . . . . ? C53 C46 C47 C48 -178.7(6) . . . . ? N3 C46 C47 C48 1.3(9) . . . . ? C50 C49 C47 C46 0.2(9) . . . . ? C50 C49 C47 C48 -179.7(6) . . . . ? C47 C46 C53 C52 -2.1(9) . . . . ? N3 C46 C53 C52 177.9(5) . . . . ? C47 C46 C53 C54 176.6(6) . . . . ? N3 C46 C53 C54 -3.5(9) . . . . ? C50 C52 C53 C46 1.2(9) . . . . ? C50 C52 C53 C54 -177.4(6) . . . . ? C1 C6 C5 C4 -4.5(10) . . . . ? C17 C10 C11 C13 0.7(9) . . . . ? N2 C10 C11 C13 -175.9(6) . . . . ? C17 C10 C11 C12 -177.6(6) . . . . ? N2 C10 C11 C12 5.9(10) . . . . ? N3 C35 C36 N4 0.5(8) . . . . ? C34 N4 C36 C35 -1.2(8) . . . . ? C37 N4 C36 C35 179.4(6) . . . . ? C7 N2 C9 C8 -0.3(9) . . . . ? C10 N2 C9 C8 176.5(7) . . . . ? C10 C17 C16 C14 -1.2(10) . . . . ? C18 C17 C16 C14 -179.2(7) . . . . ? C13 C14 C16 C17 1.8(10) . . . . ? C15 C14 C16 C17 -178.3(6) . . . . ? C19 C26 C25 C23 -1.3(11) . . . . ? C27 C26 C25 C23 178.0(7) . . . . ? C22 C23 C25 C26 2.4(11) . . . . ? C24 C23 C25 C26 177.8(6) . . . . ? C2 C3 C4 C5 0.0(11) . . . . ? C6 C5 C4 C3 3.0(10) . . . . ? N2 C9 C8 N1 0.5(10) . . . . ? C7 N1 C8 C9 -0.5(9) . . . . ? C19 N1 C8 C9 178.6(7) . . . . ? C16 C14 C13 C11 -1.1(10) . . . . ? C15 C14 C13 C11 179.0(6) . . . . ? C10 C11 C13 C14 0.0(10) . . . . ? C12 C11 C13 C14 178.3(6) . . . . ? C4 C3 C2 C1 -1.6(10) . . . . ? C6 C1 C2 C3 0.2(9) . . . . ? Au1 C1 C2 C3 176.2(5) . . . . ? C30 C31 C32 C33 -2.9(13) . . . . ? C29 C28 C33 C32 1.9(11) . . . . ? Au2 C28 C33 C32 178.6(7) . . . . ? C31 C32 C33 C28 0.8(14) . . . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 1.038 _refine_diff_density_min -0.908 _refine_diff_density_rms 0.128 # Attachment '- compound4.cif' data_compound4sw _database_code_depnum_ccdc_archive 'CCDC 832961' #TrackingRef '- compound4.cif' _audit_creation_date 2010-11-29T13:02:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C22 H27 Au N2' _chemical_formula_moiety 'C22 H27 Au N2' _chemical_formula_weight 516.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 8.327(2) _cell_length_b 29.402(4) _cell_length_c 8.849(1) _cell_angle_alpha 90.000 _cell_angle_beta 98.648(5) _cell_angle_gamma 90.000 _cell_volume 2141.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3190 _cell_measurement_theta_min 2.4163 _cell_measurement_theta_max 33.1663 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.137 _exptl_absorpt_correction_T_max 0.6093 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1829 _diffrn_orient_matrix_ub_11 0.0447461168 _diffrn_orient_matrix_ub_12 0.0060852236 _diffrn_orient_matrix_ub_13 -0.0587130236 _diffrn_orient_matrix_ub_21 0.0732919355 _diffrn_orient_matrix_ub_22 -0.0026570973 _diffrn_orient_matrix_ub_23 0.0512768898 _diffrn_orient_matrix_ub_31 0.0032166186 _diffrn_orient_matrix_ub_32 -0.0231293438 _diffrn_orient_matrix_ub_33 -0.021325748 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.1155 _diffrn_reflns_av_unetI/netI 0.1201 _diffrn_reflns_number 13994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 4149 _reflns_number_gt 2236 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0727P)^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_number_reflns 4149 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1102 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.151 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.88 _refine_diff_density_min -1.18 _refine_diff_density_rms 0.202 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5303(19) 0.1496(4) 0.3383(12) 0.090(4) Uani 1 1 d . . . H1A H 0.599 0.1258 0.3105 0.134 Uiso 1 1 calc R . . H1B H 0.5895 0.1777 0.3479 0.134 Uiso 1 1 calc R . . H1C H 0.4371 0.1526 0.2607 0.134 Uiso 1 1 calc R . . C2 C 0.3758(13) 0.1173(4) 0.7385(10) 0.055(3) Uani 1 1 d . . . C3 C 0.2525(18) 0.1153(5) 0.9481(14) 0.089(4) Uani 1 1 d . . . H3 H 0.189 0.1243 1.0208 0.106 Uiso 1 1 calc R . . C4 C 0.3421(17) 0.0794(4) 0.9524(15) 0.084(4) Uani 1 1 d . . . H4 H 0.3511 0.0569 1.0271 0.101 Uiso 1 1 calc R . . C5 C 0.5424(16) 0.0479(4) 0.8007(13) 0.068(3) Uani 1 1 d . . . C6 C 0.7049(17) 0.0576(4) 0.8475(14) 0.077(3) Uani 1 1 d . . . C7 C 0.7607(18) 0.1009(4) 0.9325(15) 0.095(4) Uani 1 1 d . . . H7A H 0.728 0.1267 0.8688 0.143 Uiso 1 1 calc R . . H7B H 0.8769 0.1006 0.9582 0.143 Uiso 1 1 calc R . . H7C H 0.7126 0.1028 1.0243 0.143 Uiso 1 1 calc R . . C8 C 0.8219(18) 0.0256(4) 0.8190(14) 0.081(4) Uani 1 1 d . . . H8 H 0.9313 0.0312 0.8528 0.097 Uiso 1 1 calc R . . C9 C 0.7759(16) -0.0145(4) 0.7409(14) 0.072(3) Uani 1 1 d . . . C10 C 0.8965(18) -0.0499(4) 0.7076(17) 0.099(4) Uani 1 1 d . . . H10A H 0.8471 -0.0794 0.7051 0.149 Uiso 1 1 calc R . . H10B H 0.9896 -0.0491 0.7861 0.149 Uiso 1 1 calc R . . H10C H 0.9298 -0.0436 0.6104 0.149 Uiso 1 1 calc R . . C11 C 0.6111(17) -0.0219(4) 0.6959(13) 0.077(4) Uani 1 1 d . . . H11 H 0.5797 -0.0488 0.6445 0.092 Uiso 1 1 calc R . . C12 C 0.4904(16) 0.0081(4) 0.7225(12) 0.066(3) Uani 1 1 d . . . C13 C 0.317(2) -0.0037(4) 0.6809(19) 0.111(5) Uani 1 1 d . . . H13A H 0.2705 -0.009 0.7721 0.167 Uiso 1 1 calc R . . H13B H 0.3074 -0.0307 0.6191 0.167 Uiso 1 1 calc R . . H13C H 0.2613 0.021 0.6244 0.167 Uiso 1 1 calc R . . C14 C 0.1807(16) 0.1798(4) 0.7664(14) 0.072(3) Uani 1 1 d . . . C15 C 0.242(2) 0.2196(5) 0.8239(17) 0.089(4) Uani 1 1 d . . . C16 C 0.400(3) 0.2226(5) 0.933(2) 0.142(7) Uani 1 1 d . . . H16A H 0.4079 0.1972 1.0024 0.213 Uiso 1 1 calc R . . H16B H 0.4022 0.2504 0.9907 0.213 Uiso 1 1 calc R . . H16C H 0.4896 0.222 0.8769 0.213 Uiso 1 1 calc R . . C17 C 0.150(3) 0.2587(5) 0.780(2) 0.112(6) Uani 1 1 d . . . H17 H 0.1853 0.2866 0.8221 0.134 Uiso 1 1 calc R . . C18 C 0.012(2) 0.2573(6) 0.678(2) 0.110(6) Uani 1 1 d . . . C19 C -0.085(3) 0.3002(5) 0.633(2) 0.173(10) Uani 1 1 d . . . H19A H -0.1803 0.3005 0.6823 0.26 Uiso 1 1 calc R . . H19B H -0.1172 0.3007 0.5241 0.26 Uiso 1 1 calc R . . H19C H -0.0198 0.3264 0.6641 0.26 Uiso 1 1 calc R . . C20 C -0.0480(19) 0.2157(5) 0.6209(17) 0.100(5) Uani 1 1 d . . . H20 H -0.1464 0.2143 0.5556 0.12 Uiso 1 1 calc R . . C21 C 0.0392(19) 0.1762(5) 0.6618(16) 0.087(4) Uani 1 1 d . . . C22 C -0.023(2) 0.1317(5) 0.595(2) 0.116(5) Uani 1 1 d . . . H22A H -0.0491 0.1123 0.6756 0.173 Uiso 1 1 calc R . . H22B H 0.059 0.1174 0.546 0.173 Uiso 1 1 calc R . . H22C H -0.1186 0.1367 0.5222 0.173 Uiso 1 1 calc R . . N1 N 0.2695(12) 0.1376(3) 0.8150(10) 0.067(3) Uani 1 1 d . . . N2 N 0.4226(15) 0.0801(3) 0.8265(12) 0.082(3) Uani 1 1 d . . . Au Au 0.45638(6) 0.134084(13) 0.54199(5) 0.0670(2) 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 0.123(12) 0.104(8) 0.041(6) 0.029(6) 0.014(8) 0.022(9) C2 0.040(6) 0.092(7) 0.032(5) 0.016(5) 0.003(5) 0.008(5) C3 0.089(11) 0.119(10) 0.057(8) 0.018(7) 0.008(8) 0.031(9) C4 0.073(9) 0.096(9) 0.077(9) 0.029(7) -0.003(8) 0.017(8) C5 0.068(9) 0.080(8) 0.058(7) 0.027(6) 0.018(7) 0.016(7) C6 0.075(10) 0.072(7) 0.079(9) 0.008(6) 0.000(8) -0.012(7) C7 0.090(10) 0.094(9) 0.094(9) -0.016(7) -0.011(8) -0.006(8) C8 0.078(10) 0.086(8) 0.074(8) 0.007(7) -0.002(8) -0.023(8) C9 0.069(9) 0.066(7) 0.075(8) 0.022(6) -0.007(7) -0.003(7) C10 0.089(11) 0.094(9) 0.117(11) 0.010(8) 0.024(10) 0.027(8) C11 0.089(10) 0.063(7) 0.071(8) 0.007(6) -0.014(8) -0.026(7) C12 0.075(9) 0.056(6) 0.059(7) 0.011(5) -0.013(6) -0.008(7) C13 0.111(13) 0.106(10) 0.123(12) 0.010(9) 0.034(11) -0.040(9) C14 0.065(9) 0.085(8) 0.066(8) 0.004(6) 0.011(7) 0.000(7) C15 0.089(11) 0.083(9) 0.097(11) 0.007(8) 0.021(10) 0.001(8) C16 0.18(2) 0.098(11) 0.144(16) 0.003(11) -0.008(16) -0.011(12) C17 0.139(17) 0.077(9) 0.121(13) 0.007(9) 0.029(13) 0.007(10) C18 0.112(15) 0.104(12) 0.121(14) 0.034(11) 0.043(12) 0.057(11) C19 0.18(2) 0.113(12) 0.24(2) 0.067(14) 0.063(19) 0.082(14) C20 0.096(12) 0.114(11) 0.092(10) 0.018(9) 0.028(9) 0.033(10) C21 0.085(10) 0.091(9) 0.088(10) 0.004(8) 0.020(9) 0.010(8) C22 0.090(13) 0.137(14) 0.112(11) -0.003(10) -0.011(10) 0.002(10) N1 0.071(7) 0.079(6) 0.051(5) 0.018(4) 0.010(5) 0.009(5) N2 0.105(9) 0.073(6) 0.066(6) 0.023(5) 0.006(7) 0.009(6) Au 0.0777(4) 0.0647(3) 0.0574(3) 0.0110(2) 0.0057(2) -0.0005(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Au 2.042(10) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C2 N1 1.333(13) . ? C2 N2 1.366(12) . ? C2 Au 2.017(9) . ? C3 C4 1.291(16) . ? C3 N1 1.374(14) . ? C3 H3 0.93 . ? C4 N2 1.384(15) . ? C4 H4 0.93 . ? C5 C6 1.384(17) . ? C5 C12 1.395(15) . ? C5 N2 1.417(14) . ? C6 C8 1.406(17) . ? C6 C7 1.513(16) . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 C9 1.390(16) . ? C8 H8 0.93 . ? C9 C11 1.388(17) . ? C9 C10 1.505(16) . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C11 C12 1.384(16) . ? C11 H11 0.93 . ? C12 C13 1.47(2) . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 C15 1.347(18) . ? C14 C21 1.389(18) . ? C14 N1 1.476(14) . ? C15 C17 1.41(2) . ? C15 C16 1.51(2) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 C18 1.35(2) . ? C17 H17 0.93 . ? C18 C20 1.39(2) . ? C18 C19 1.520(19) . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 C21 1.389(17) . ? C20 H20 0.93 . ? C21 C22 1.494(18) . ? C22 H22A 0.96 . ? C22 H22B 0.96 . ? C22 H22C 0.96 . ? 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 Au C1 H1A 109.5 . . ? Au C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Au C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 102.9(9) . . ? N1 C2 Au 131.4(7) . . ? N2 C2 Au 125.7(8) . . ? C4 C3 N1 106.3(12) . . ? C4 C3 H3 126.8 . . ? N1 C3 H3 126.8 . . ? C3 C4 N2 108.2(11) . . ? C3 C4 H4 125.9 . . ? N2 C4 H4 125.9 . . ? C6 C5 C12 122.6(12) . . ? C6 C5 N2 119.6(12) . . ? C12 C5 N2 117.8(12) . . ? C5 C6 C8 118.7(11) . . ? C5 C6 C7 122.4(13) . . ? C8 C6 C7 118.9(13) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 120.8(13) . . ? C9 C8 H8 119.6 . . ? C6 C8 H8 119.6 . . ? C11 C9 C8 117.5(12) . . ? C11 C9 C10 119.7(12) . . ? C8 C9 C10 122.8(13) . . ? 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 . . ? C12 C11 C9 124.4(11) . . ? C12 C11 H11 117.8 . . ? C9 C11 H11 117.8 . . ? C11 C12 C5 116.1(12) . . ? C11 C12 C13 121.1(11) . . ? C5 C12 C13 122.7(12) . . ? 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 . . ? C15 C14 C21 123.8(13) . . ? C15 C14 N1 118.3(13) . . ? C21 C14 N1 117.9(11) . . ? C14 C15 C17 116.4(16) . . ? C14 C15 C16 122.5(13) . . ? C17 C15 C16 121.1(15) . . ? 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 . . ? C18 C17 C15 122.4(16) . . ? C18 C17 H17 118.8 . . ? C15 C17 H17 118.8 . . ? C17 C18 C20 119.7(14) . . ? C17 C18 C19 121.1(19) . . ? C20 C18 C19 119.1(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 C21 119.8(16) . . ? C18 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C14 C21 C20 117.9(14) . . ? C14 C21 C22 122.6(13) . . ? C20 C21 C22 119.6(16) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 N1 C3 112.6(9) . . ? C2 N1 C14 124.8(8) . . ? C3 N1 C14 122.6(10) . . ? C2 N2 C4 109.8(10) . . ? C2 N2 C5 126.2(10) . . ? C4 N2 C5 123.9(9) . . ? C2 Au C1 177.7(5) . . ? 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 N1 C3 C4 N2 3.2(16) . . . . ? C12 C5 C6 C8 -1.8(18) . . . . ? N2 C5 C6 C8 -179.1(10) . . . . ? C12 C5 C6 C7 -179.9(10) . . . . ? N2 C5 C6 C7 2.7(18) . . . . ? C5 C6 C8 C9 2.0(18) . . . . ? C7 C6 C8 C9 -179.8(11) . . . . ? C6 C8 C9 C11 -1.4(17) . . . . ? C6 C8 C9 C10 180.0(11) . . . . ? C8 C9 C11 C12 0.6(18) . . . . ? C10 C9 C11 C12 179.2(11) . . . . ? C9 C11 C12 C5 -0.3(17) . . . . ? C9 C11 C12 C13 -175.6(12) . . . . ? C6 C5 C12 C11 1.0(16) . . . . ? N2 C5 C12 C11 178.3(9) . . . . ? C6 C5 C12 C13 176.1(12) . . . . ? N2 C5 C12 C13 -6.5(16) . . . . ? C21 C14 C15 C17 4(2) . . . . ? N1 C14 C15 C17 -177.3(11) . . . . ? C21 C14 C15 C16 -177.8(13) . . . . ? N1 C14 C15 C16 1.2(19) . . . . ? C14 C15 C17 C18 -4(2) . . . . ? C16 C15 C17 C18 177.5(15) . . . . ? C15 C17 C18 C20 4(2) . . . . ? C15 C17 C18 C19 179.7(14) . . . . ? C17 C18 C20 C21 -4(2) . . . . ? C19 C18 C20 C21 -179.6(13) . . . . ? C15 C14 C21 C20 -3.6(19) . . . . ? N1 C14 C21 C20 177.4(10) . . . . ? C15 C14 C21 C22 177.7(13) . . . . ? N1 C14 C21 C22 -1.3(18) . . . . ? C18 C20 C21 C14 3.6(19) . . . . ? C18 C20 C21 C22 -177.7(13) . . . . ? N2 C2 N1 C3 1.9(13) . . . . ? Au C2 N1 C3 -178.2(10) . . . . ? N2 C2 N1 C14 -179.3(11) . . . . ? Au C2 N1 C14 0.6(17) . . . . ? C4 C3 N1 C2 -3.3(16) . . . . ? C4 C3 N1 C14 177.9(12) . . . . ? C15 C14 N1 C2 -95.2(14) . . . . ? C21 C14 N1 C2 83.9(14) . . . . ? C15 C14 N1 C3 83.5(15) . . . . ? C21 C14 N1 C3 -97.4(14) . . . . ? N1 C2 N2 C4 0.1(13) . . . . ? Au C2 N2 C4 -179.8(9) . . . . ? N1 C2 N2 C5 -176.3(11) . . . . ? Au C2 N2 C5 3.8(18) . . . . ? C3 C4 N2 C2 -2.2(16) . . . . ? C3 C4 N2 C5 174.4(13) . . . . ? C6 C5 N2 C2 81.5(16) . . . . ? C12 C5 N2 C2 -96.0(14) . . . . ? C6 C5 N2 C4 -94.5(14) . . . . ? C12 C5 N2 C4 88.0(14) . . . . ? # Attachment '- compound5.cif' data_compound5 _database_code_depnum_ccdc_archive 'CCDC 832962' #TrackingRef '- compound5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H30 Au I N2' _chemical_formula_weight 706.40 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' I I -0.4742 1.8119 '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)/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 9.1235(14) _cell_length_b 7.999(2) _cell_length_c 34.742(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.1810(18) _cell_angle_gamma 90.00 _cell_volume 2528.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 116 _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.5423 _cell_measurement_theta_max 33.0741 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 7.055 _exptl_absorpt_correction_T_min 0.31437 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 116 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1829 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23826 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.1012 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 33.29 _reflns_number_total 8886 _reflns_number_gt 5887 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0002P)^2^+199.8115P] 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 8886 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1467 _refine_ls_R_factor_gt 0.1069 _refine_ls_wR_factor_ref 0.2665 _refine_ls_wR_factor_gt 0.2494 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _refine_ls_shift/su_max 0.052 _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 0.03127(7) -0.10716(8) 0.39168(2) 0.02609(16) Uani 1 1 d . . . I2 I -0.22672(12) -0.22618(16) 0.38653(4) 0.0340(3) Uani 1 1 d . . . N1 N 0.3049(14) 0.0663(18) 0.3701(3) 0.022(2) Uani 1 1 d . . . C1 C 0.2346(18) -0.013(2) 0.3961(5) 0.029(2) Uani 1 1 d . . . C24 C 0.547(2) 0.200(3) 0.2788(5) 0.037(3) Uani 1 1 d . . . H24 H 0.4813 0.1522 0.2602 0.044 Uiso 1 1 calc R . . C9 C 0.1779(17) 0.254(2) 0.3254(4) 0.022(2) Uani 1 1 d . . . C4 C 0.2445(17) 0.098(2) 0.3338(5) 0.027(2) Uani 1 1 d . . . C6 C 0.1997(18) 0.013(2) 0.2685(5) 0.026(3) Uani 1 1 d . . . H6 H 0.2039 -0.0670 0.2492 0.031 Uiso 1 1 calc R . . C13 C 0.2953(18) -0.093(2) 0.4618(5) 0.029(4) Uani 1 1 d . . . C11 C 0.327(2) -0.185(2) 0.3151(6) 0.039(3) Uani 1 1 d . . . H11A H 0.3592 -0.1849 0.3420 0.059 Uiso 1 1 calc R . . H11B H 0.4106 -0.2009 0.3001 0.059 Uiso 1 1 calc R . . H11C H 0.2583 -0.2743 0.3098 0.059 Uiso 1 1 calc R . . C15 C 0.287(2) -0.331(2) 0.5013(6) 0.036(4) Uani 1 1 d . . . H15 H 0.3076 -0.4434 0.5061 0.044 Uiso 1 1 calc R . . C22 C 0.617(2) 0.427(2) 0.3188(7) 0.044(5) Uani 1 1 d . . . H22 H 0.6000 0.5337 0.3280 0.053 Uiso 1 1 calc R . . C26 C 0.768(2) 0.185(3) 0.3185(7) 0.044(5) Uani 1 1 d . . . H26 H 0.8522 0.1274 0.3277 0.053 Uiso 1 1 calc R . . C17 C 0.194(2) -0.073(2) 0.5213(6) 0.034(3) Uani 1 1 d . . . H17 H 0.1498 -0.0102 0.5398 0.041 Uiso 1 1 calc R . . C21 C 0.394(3) -0.362(3) 0.4379(7) 0.048(5) Uani 1 1 d . . . H21A H 0.4047 -0.4753 0.4468 0.072 Uiso 1 1 calc R . . H21B H 0.4882 -0.3168 0.4333 0.072 Uiso 1 1 calc R . . H21C H 0.3315 -0.3599 0.4143 0.072 Uiso 1 1 calc R . . C3 C 0.4446(18) 0.112(2) 0.3848(5) 0.029(2) Uani 1 1 d . . . H3 H 0.5149 0.1685 0.3717 0.034 Uiso 1 1 calc R . . C25 C 0.671(2) 0.113(3) 0.2916(6) 0.041(4) Uani 1 1 d . . . H25 H 0.6884 0.0071 0.2822 0.049 Uiso 1 1 calc R . . C7 C 0.1356(18) 0.167(2) 0.2597(5) 0.029(3) Uani 1 1 d . . . C20 C 0.181(3) -0.319(3) 0.5641(7) 0.058(7) Uani 1 1 d . . . H20A H 0.2073 -0.4349 0.5638 0.087 Uiso 1 1 calc R . . H20B H 0.0773 -0.3083 0.5665 0.087 Uiso 1 1 calc R . . H20C H 0.2336 -0.2651 0.5857 0.087 Uiso 1 1 calc R . . C5 C 0.2558(17) -0.023(2) 0.3046(5) 0.027(2) Uani 1 1 d . . . C27 C 0.742(2) 0.342(3) 0.3316(5) 0.037(3) Uani 1 1 d . . . H27 H 0.8097 0.3924 0.3493 0.044 Uiso 1 1 calc R . . C18 C 0.2311(19) 0.004(2) 0.4884(6) 0.031(4) Uani 1 1 d . . . C10 C 0.168(2) 0.381(2) 0.3554(6) 0.039(3) Uani 1 1 d . . . H10A H 0.2087 0.3378 0.3797 0.059 Uiso 1 1 calc R . . H10B H 0.0664 0.4096 0.3576 0.059 Uiso 1 1 calc R . . H10C H 0.2212 0.4787 0.3487 0.059 Uiso 1 1 calc R . . C19 C 0.203(3) 0.185(3) 0.4824(6) 0.044(5) Uani 1 1 d . . . H19A H 0.1570 0.2299 0.5043 0.066 Uiso 1 1 calc R . . H19B H 0.1389 0.2013 0.4595 0.066 Uiso 1 1 calc R . . H19C H 0.2941 0.2423 0.4797 0.066 Uiso 1 1 calc R . . N2 N 0.3280(15) -0.0183(18) 0.4262(4) 0.028(3) Uani 1 1 d . . . C12 C 0.079(2) 0.205(3) 0.2197(6) 0.039(4) Uani 1 1 d . . . H12A H 0.0935 0.1095 0.2036 0.059 Uiso 1 1 calc R . . H12B H 0.1308 0.2991 0.2103 0.059 Uiso 1 1 calc R . . H12C H -0.0239 0.2302 0.2192 0.059 Uiso 1 1 calc R . . C14 C 0.326(2) -0.260(2) 0.4676(6) 0.033(4) Uani 1 1 d . . . C8 C 0.1277(17) 0.282(2) 0.2881(6) 0.031(4) Uani 1 1 d . . . H8 H 0.0859 0.3856 0.2818 0.037 Uiso 1 1 calc R . . C2 C 0.4583(18) 0.060(2) 0.4208(5) 0.032(4) Uani 1 1 d . . . H2 H 0.5387 0.0726 0.4386 0.038 Uiso 1 1 calc R . . C23 C 0.5186(19) 0.354(2) 0.2929(6) 0.035(4) Uani 1 1 d . . . H23 H 0.4321 0.4095 0.2849 0.042 Uiso 1 1 calc R . . C16 C 0.220(2) -0.239(2) 0.5280(6) 0.034(3) 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 0.0210(3) 0.0237(3) 0.0332(3) 0.0000(3) -0.0004(2) -0.0040(2) I2 0.0256(5) 0.0362(6) 0.0400(7) -0.0039(5) 0.0005(4) -0.0102(4) N1 0.027(5) 0.033(5) 0.007(4) 0.004(4) 0.001(3) -0.003(4) C1 0.028(5) 0.033(6) 0.024(6) 0.001(5) -0.005(4) -0.002(5) C24 0.037(7) 0.046(8) 0.027(6) 0.003(6) -0.003(5) -0.014(6) C9 0.027(5) 0.033(5) 0.007(4) 0.004(4) 0.001(3) -0.003(4) C4 0.022(5) 0.025(5) 0.033(6) 0.008(5) -0.001(4) 0.001(4) C6 0.028(8) 0.031(8) 0.017(7) 0.001(6) -0.005(6) -0.004(6) C13 0.024(7) 0.023(7) 0.040(10) 0.002(7) -0.008(6) -0.006(6) C11 0.045(8) 0.033(7) 0.040(8) 0.000(6) -0.003(6) 0.008(6) C15 0.040(10) 0.024(8) 0.045(12) 0.011(8) 0.000(8) -0.002(7) C22 0.035(10) 0.026(9) 0.071(16) 0.008(9) 0.006(10) -0.008(7) C26 0.028(9) 0.051(12) 0.054(13) 0.024(11) 0.010(9) 0.002(8) C17 0.037(6) 0.031(6) 0.032(7) 0.003(5) -0.008(5) -0.005(5) C21 0.064(14) 0.033(11) 0.049(13) -0.005(9) 0.012(11) 0.002(10) C3 0.028(5) 0.033(6) 0.024(6) 0.001(5) -0.005(4) -0.002(5) C25 0.040(10) 0.032(9) 0.050(12) -0.002(9) 0.003(9) -0.009(8) C7 0.024(7) 0.031(8) 0.030(9) 0.009(7) -0.007(6) -0.003(6) C20 0.065(15) 0.062(15) 0.047(14) 0.035(12) 0.005(11) 0.001(12) C5 0.022(5) 0.025(5) 0.033(6) 0.008(5) -0.001(4) 0.001(4) C27 0.037(7) 0.046(8) 0.027(6) 0.003(6) -0.003(5) -0.014(6) C18 0.029(8) 0.026(8) 0.038(10) 0.002(7) -0.007(7) -0.004(7) C10 0.045(8) 0.033(7) 0.040(8) 0.000(6) -0.003(6) 0.008(6) C19 0.061(14) 0.034(10) 0.036(11) -0.007(9) 0.007(10) -0.001(9) N2 0.025(7) 0.029(7) 0.029(8) 0.003(6) -0.002(5) -0.003(5) C12 0.041(10) 0.036(10) 0.040(11) 0.013(9) -0.008(8) 0.004(8) C14 0.031(9) 0.029(9) 0.040(11) 0.004(8) -0.003(7) -0.004(7) C8 0.021(7) 0.025(8) 0.046(11) -0.002(8) -0.002(7) 0.000(6) C2 0.021(7) 0.042(10) 0.032(9) 0.012(8) -0.004(6) -0.009(7) C23 0.025(8) 0.041(10) 0.040(11) 0.009(8) 0.006(7) -0.005(7) C16 0.037(6) 0.031(6) 0.032(7) 0.003(5) -0.008(5) -0.005(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.999(17) . ? Au1 I2 2.5332(13) . ? N1 C1 1.31(2) . ? N1 C4 1.36(2) . ? N1 C3 1.39(2) . ? C1 N2 1.30(2) . ? C24 C23 1.36(3) . ? C24 C25 1.37(3) . ? C24 H24 0.9300 . ? C9 C8 1.36(2) . ? C9 C4 1.40(2) . ? C9 C10 1.47(2) . ? C4 C5 1.41(3) . ? C6 C5 1.35(2) . ? C6 C7 1.39(2) . ? C6 H6 0.9300 . ? C13 C18 1.37(3) . ? C13 C14 1.38(2) . ? C13 N2 1.43(2) . ? C11 C5 1.49(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C15 C16 1.37(3) . ? C15 C14 1.37(3) . ? C15 H15 0.9300 . ? C22 C23 1.36(3) . ? C22 C27 1.37(3) . ? C22 H22 0.9300 . ? C26 C25 1.37(3) . ? C26 C27 1.36(3) . ? C26 H26 0.9300 . ? C17 C18 1.36(3) . ? C17 C16 1.36(3) . ? C17 H17 0.9300 . ? C21 C14 1.49(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C3 C2 1.32(2) . ? C3 H3 0.9300 . ? C25 H25 0.9300 . ? C7 C8 1.35(3) . ? C7 C12 1.48(2) . ? C20 C16 1.48(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C27 H27 0.9300 . ? C18 C19 1.49(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N2 C2 1.37(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C8 H8 0.9300 . ? C2 H2 0.9300 . ? C23 H23 0.9300 . ? 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 I2 179.6(5) . . ? C1 N1 C4 122.9(14) . . ? C1 N1 C3 110.9(13) . . ? C4 N1 C3 126.1(14) . . ? N2 C1 N1 104.2(15) . . ? N2 C1 Au1 126.9(13) . . ? N1 C1 Au1 128.9(12) . . ? C23 C24 C25 120.9(18) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C8 C9 C4 117.1(15) . . ? C8 C9 C10 121.7(16) . . ? C4 C9 C10 121.1(15) . . ? N1 C4 C5 119.4(15) . . ? N1 C4 C9 119.8(16) . . ? C5 C4 C9 120.8(15) . . ? C5 C6 C7 121.1(16) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C18 C13 C14 122.9(18) . . ? C18 C13 N2 118.5(16) . . ? C14 C13 N2 118.6(17) . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C15 C14 120.9(18) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C23 C22 C27 120(2) . . ? C23 C22 H22 120.0 . . ? C27 C22 H22 120.0 . . ? C25 C26 C27 119.5(19) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C18 C17 C16 122(2) . . ? C18 C17 H17 118.9 . . ? C16 C17 H17 118.9 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C3 N1 106.7(15) . . ? C2 C3 H3 126.7 . . ? N1 C3 H3 126.7 . . ? C24 C25 C26 119(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C8 C7 C6 119.1(16) . . ? C8 C7 C12 120.9(17) . . ? C6 C7 C12 120.0(17) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C6 C5 C4 118.7(15) . . ? C6 C5 C11 122.8(17) . . ? C4 C5 C11 118.5(16) . . ? C26 C27 C22 120.6(19) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? C13 C18 C17 117.0(17) . . ? C13 C18 C19 122.5(18) . . ? C17 C18 C19 120.5(19) . . ? 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 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N2 C2 113.5(15) . . ? C1 N2 C13 123.1(14) . . ? C2 N2 C13 123.3(14) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C14 C13 117.7(19) . . ? C15 C14 C21 120.9(18) . . ? C13 C14 C21 121.4(18) . . ? C7 C8 C9 123.2(17) . . ? C7 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C3 C2 N2 104.6(15) . . ? C3 C2 H2 127.7 . . ? N2 C2 H2 127.7 . . ? C22 C23 C24 119.6(19) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C17 C16 C15 119.3(19) . . ? C17 C16 C20 121(2) . . ? C15 C16 C20 119.4(19) . . ? 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 C4 N1 C1 N2 179.8(15) . . . . ? C3 N1 C1 N2 -1(2) . . . . ? C4 N1 C1 Au1 0(3) . . . . ? C3 N1 C1 Au1 179.9(14) . . . . ? I2 Au1 C1 N2 39(84) . . . . ? I2 Au1 C1 N1 -142(82) . . . . ? C1 N1 C4 C5 -87(2) . . . . ? C3 N1 C4 C5 93(2) . . . . ? C1 N1 C4 C9 96(2) . . . . ? C3 N1 C4 C9 -84(2) . . . . ? C8 C9 C4 N1 176.0(15) . . . . ? C10 C9 C4 N1 -2(2) . . . . ? C8 C9 C4 C5 -1(2) . . . . ? C10 C9 C4 C5 -179.0(16) . . . . ? C1 N1 C3 C2 0(2) . . . . ? C4 N1 C3 C2 179.2(17) . . . . ? C23 C24 C25 C26 -1(3) . . . . ? C27 C26 C25 C24 -1(3) . . . . ? C5 C6 C7 C8 -1(3) . . . . ? C5 C6 C7 C12 178.2(17) . . . . ? C7 C6 C5 C4 2(2) . . . . ? C7 C6 C5 C11 -179.0(17) . . . . ? N1 C4 C5 C6 -177.8(15) . . . . ? C9 C4 C5 C6 -1(2) . . . . ? N1 C4 C5 C11 3(2) . . . . ? C9 C4 C5 C11 180.0(16) . . . . ? C25 C26 C27 C22 2(3) . . . . ? C23 C22 C27 C26 0(3) . . . . ? C14 C13 C18 C17 -1(3) . . . . ? N2 C13 C18 C17 176.6(15) . . . . ? C14 C13 C18 C19 178.1(18) . . . . ? N2 C13 C18 C19 -4(3) . . . . ? C16 C17 C18 C13 0(3) . . . . ? C16 C17 C18 C19 -179.2(18) . . . . ? N1 C1 N2 C2 1(2) . . . . ? Au1 C1 N2 C2 -179.1(14) . . . . ? N1 C1 N2 C13 179.1(16) . . . . ? Au1 C1 N2 C13 -1(3) . . . . ? C18 C13 N2 C1 -88(2) . . . . ? C14 C13 N2 C1 90(2) . . . . ? C18 C13 N2 C2 89(2) . . . . ? C14 C13 N2 C2 -92(2) . . . . ? C16 C15 C14 C13 1(3) . . . . ? C16 C15 C14 C21 -177.4(19) . . . . ? C18 C13 C14 C15 1(3) . . . . ? N2 C13 C14 C15 -177.1(16) . . . . ? C18 C13 C14 C21 179.0(18) . . . . ? N2 C13 C14 C21 1(3) . . . . ? C6 C7 C8 C9 -1(3) . . . . ? C12 C7 C8 C9 179.9(16) . . . . ? C4 C9 C8 C7 2(2) . . . . ? C10 C9 C8 C7 179.9(17) . . . . ? N1 C3 C2 N2 1(2) . . . . ? C1 N2 C2 C3 -2(2) . . . . ? C13 N2 C2 C3 -179.3(17) . . . . ? C27 C22 C23 C24 -2(3) . . . . ? C25 C24 C23 C22 3(3) . . . . ? C18 C17 C16 C15 1(3) . . . . ? C18 C17 C16 C20 179.0(19) . . . . ? C14 C15 C16 C17 -2(3) . . . . ? C14 C15 C16 C20 -179.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 4.178 _refine_diff_density_min -6.675 _refine_diff_density_rms 0.399