# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Nils Metzler-Nolte' 'Jessic Lemke' 'Jessic Lemke' 'Philip Niehoff' 'Antonio Pinto' 'Vera Vasylyeva' _publ_contact_author_name 'Nils Metzler-Nolte' _publ_contact_author_email NILS.METZLER-NOLTE@RUB.DE _publ_section_title ; Synthesis, Structural Characterisation and Anti-proliferative Activity of NHC Gold Amino Acid and Peptide Conjugates ; # Attachment 'B906140A_Comp_4c.cif' data_081016t _database_code_depnum_ccdc_archive 'CCDC 725410' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 Au Br3 N3 O3' _chemical_formula_weight 780.12 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.452(4) _cell_length_b 9.212(4) _cell_length_c 15.756(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.894(9) _cell_angle_gamma 90.00 _cell_volume 1225.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.115 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 10.919 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6721 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3852 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1187P)^2^+1.1391P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(19) _refine_ls_number_reflns 3852 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.65971(6) 0.19551(5) 0.68419(3) 0.0270(2) Uani 1 1 d . . . Br2 Br 0.7493(2) -0.0463(2) 0.65112(11) 0.0398(4) Uani 1 1 d . . . Br1 Br 0.43750(18) 0.0957(3) 0.75858(11) 0.0456(5) Uani 1 1 d . . . Br3 Br 0.5783(3) 0.4400(3) 0.71400(14) 0.0544(5) Uani 1 1 d . . . N3 N 0.9862(15) 0.3391(14) 0.9019(8) 0.024(3) Uani 1 1 d . . . H3A H 0.9962 0.2497 0.9169 0.029 Uiso 1 1 calc R . . N2 N 0.9910(13) 0.2855(13) 0.6728(7) 0.021(2) Uani 1 1 d . . . C1 C 0.8539(19) 0.2733(18) 0.6292(10) 0.029(3) Uani 1 1 d . . . O1 O 0.9877(17) 0.5023(12) 0.7904(7) 0.040(3) Uani 1 1 d . . . C16 C 0.627(2) 0.061(2) 1.0873(14) 0.049(5) Uani 1 1 d . . . H16A H 0.5972 -0.0285 1.1090 0.059 Uiso 1 1 calc R . . C15 C 0.5996(19) 0.087(2) 1.0026(13) 0.040(4) Uani 1 1 d . . . H15A H 0.5506 0.0183 0.9671 0.048 Uiso 1 1 calc R . . C9 C 0.9942(16) 0.3795(16) 0.8183(9) 0.024(3) Uani 1 1 d . . . C10 C 0.9606(18) 0.4511(16) 0.9636(9) 0.019(3) Uani 1 1 d . . . H10A H 0.9883 0.5440 0.9380 0.023 Uiso 1 1 calc R . . C2 C 1.028(2) 0.3633(19) 0.5448(11) 0.036(4) Uani 1 1 d . . . H2A H 1.0733 0.4015 0.4971 0.043 Uiso 1 1 calc R . . C3 C 1.104(2) 0.3407(17) 0.6215(9) 0.028(3) Uani 1 1 d . . . H3B H 1.2104 0.3586 0.6364 0.033 Uiso 1 1 calc R . . C14 C 0.6463(18) 0.2191(19) 0.9712(10) 0.033(4) Uani 1 1 d . . . H14A H 0.6252 0.2393 0.9139 0.039 Uiso 1 1 calc R . . C17 C 0.6973(19) 0.161(2) 1.1420(11) 0.039(4) Uani 1 1 d . . . H17A H 0.7086 0.1412 1.1999 0.047 Uiso 1 1 calc R . . N1 N 0.8755(15) 0.3210(14) 0.5495(8) 0.030(3) Uani 1 1 d . . . C8 C 1.0222(18) 0.2466(16) 0.7628(9) 0.025(3) Uani 1 1 d . . . H8A H 1.1308 0.2137 0.7718 0.030 Uiso 1 1 calc R . . H8B H 0.9525 0.1683 0.7782 0.030 Uiso 1 1 calc R . . C12 C 0.7811(16) 0.4599(17) 0.9859(10) 0.028(3) Uani 1 1 d . . . H12A H 0.7684 0.5368 1.0270 0.034 Uiso 1 1 calc R . . H12B H 0.7175 0.4845 0.9349 0.034 Uiso 1 1 calc R . . C18 C 0.7506(18) 0.290(2) 1.1107(10) 0.032(4) Uani 1 1 d . . . H18A H 0.8040 0.3559 1.1464 0.039 Uiso 1 1 calc R . . C4 C 0.756(2) 0.344(2) 0.4755(11) 0.042(4) Uani 1 1 d . . . C7 C 0.608(3) 0.254(3) 0.4843(14) 0.074(8) Uani 1 1 d . . . H7A H 0.5356 0.2710 0.4363 0.111 Uiso 1 1 calc R . . H7B H 0.5581 0.2809 0.5355 0.111 Uiso 1 1 calc R . . H7C H 0.6356 0.1531 0.4867 0.111 Uiso 1 1 calc R . . C6 C 0.833(3) 0.294(3) 0.3952(13) 0.068(7) Uani 1 1 d . . . H6A H 0.7600 0.3070 0.3471 0.102 Uiso 1 1 calc R . . H6B H 0.8601 0.1929 0.4006 0.102 Uiso 1 1 calc R . . H6C H 0.9269 0.3496 0.3874 0.102 Uiso 1 1 calc R . . C5 C 0.721(4) 0.507(3) 0.4758(18) 0.089(10) Uani 1 1 d . . . H5A H 0.6466 0.5295 0.4298 0.134 Uiso 1 1 calc R . . H5B H 0.8176 0.5595 0.4690 0.134 Uiso 1 1 calc R . . H5C H 0.6775 0.5330 0.5287 0.134 Uiso 1 1 calc R . . O2 O 1.1471(12) 0.3165(11) 1.0500(6) 0.029(2) Uani 1 1 d . . . C13 C 0.7226(18) 0.3216(16) 1.0210(9) 0.026(3) Uani 1 1 d . . . O3 O 1.0574(14) 0.5240(12) 1.1015(7) 0.032(3) Uani 1 1 d . . . C11 C 1.062(2) 0.4349(16) 1.0463(10) 0.023(3) Uani 1 1 d . . . C19 C 1.241(2) 0.294(2) 1.1304(13) 0.045(5) Uani 1 1 d . . . H19A H 1.2993 0.2047 1.1273 0.067 Uiso 1 1 calc R . . H19B H 1.1713 0.2888 1.1765 0.067 Uiso 1 1 calc R . . H19C H 1.3134 0.3732 1.1396 0.067 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 0.0196(3) 0.0449(3) 0.0163(3) 0.0007(3) 0.00139(17) 0.0034(3) Br2 0.0436(9) 0.0425(10) 0.0340(9) -0.0016(8) 0.0092(7) 0.0025(8) Br1 0.0215(8) 0.0848(15) 0.0309(9) -0.0016(9) 0.0063(6) -0.0085(8) Br3 0.0521(11) 0.0557(12) 0.0560(12) -0.0112(10) 0.0095(9) 0.0186(10) N3 0.034(7) 0.019(6) 0.020(6) -0.008(5) 0.002(5) 0.010(5) N2 0.019(6) 0.024(6) 0.020(6) -0.004(5) -0.003(4) 0.000(5) C1 0.036(9) 0.030(8) 0.021(8) 0.000(7) -0.004(6) 0.001(7) O1 0.077(9) 0.023(6) 0.019(6) 0.002(4) -0.002(6) -0.004(5) C16 0.047(11) 0.045(11) 0.056(13) 0.010(9) 0.011(9) -0.014(9) C15 0.029(8) 0.032(8) 0.059(12) -0.007(8) 0.004(8) -0.010(7) C9 0.017(6) 0.032(8) 0.021(7) 0.005(6) -0.010(5) -0.003(6) C10 0.027(7) 0.013(6) 0.019(7) -0.001(6) 0.007(5) -0.013(6) C2 0.036(9) 0.043(10) 0.029(8) 0.008(7) 0.008(7) -0.017(7) C3 0.045(9) 0.028(8) 0.011(7) 0.009(6) 0.015(6) 0.005(7) C14 0.031(7) 0.041(10) 0.027(7) 0.003(7) 0.002(6) -0.006(7) C17 0.031(8) 0.054(13) 0.034(9) 0.011(8) 0.009(7) 0.000(7) N1 0.032(7) 0.031(7) 0.026(7) 0.005(5) -0.001(5) -0.009(6) C8 0.024(7) 0.033(8) 0.018(7) 0.004(5) 0.000(5) 0.007(5) C12 0.020(7) 0.029(8) 0.035(8) 0.008(7) 0.000(6) -0.006(6) C18 0.027(8) 0.047(10) 0.023(8) 0.008(8) 0.009(6) -0.004(8) C4 0.054(11) 0.050(10) 0.021(8) 0.005(8) -0.008(7) -0.005(9) C7 0.068(14) 0.12(2) 0.034(11) 0.030(12) -0.016(10) -0.026(14) C6 0.071(15) 0.097(18) 0.034(11) -0.027(12) -0.019(10) 0.015(14) C5 0.14(3) 0.068(16) 0.059(16) 0.027(13) -0.030(17) 0.012(18) O2 0.039(6) 0.027(6) 0.019(5) -0.008(4) -0.013(4) 0.004(5) C13 0.037(8) 0.018(7) 0.026(8) -0.005(6) 0.013(6) 0.000(6) O3 0.045(7) 0.019(5) 0.030(6) -0.005(5) 0.003(5) -0.001(5) C11 0.036(9) 0.012(7) 0.022(8) -0.004(6) 0.001(6) -0.014(6) C19 0.031(8) 0.045(10) 0.055(11) 0.004(9) -0.030(8) 0.018(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.025(17) . ? Au1 Br3 2.408(2) . ? Au1 Br2 2.418(2) . ? Au1 Br1 2.4431(18) . ? N3 C9 1.374(19) . ? N3 C10 1.442(19) . ? N2 C1 1.32(2) . ? N2 C3 1.381(19) . ? N2 C8 1.474(19) . ? C1 N1 1.35(2) . ? O1 C9 1.214(18) . ? C16 C15 1.37(3) . ? C16 C17 1.38(3) . ? C15 C14 1.38(3) . ? C9 C8 1.53(2) . ? C10 C11 1.531(19) . ? C10 C12 1.58(2) . ? C2 N1 1.35(2) . ? C2 C3 1.36(2) . ? C14 C13 1.37(2) . ? C17 C18 1.37(3) . ? N1 C4 1.52(2) . ? C12 C13 1.48(2) . ? C18 C13 1.45(2) . ? C4 C7 1.52(3) . ? C4 C6 1.53(3) . ? C4 C5 1.52(3) . ? O2 C11 1.31(2) . ? O2 C19 1.475(18) . ? O3 C11 1.197(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 C1 Au1 Br3 89.9(5) . . ? C1 Au1 Br2 88.0(5) . . ? Br3 Au1 Br2 177.84(7) . . ? C1 Au1 Br1 176.1(4) . . ? Br3 Au1 Br1 91.39(8) . . ? Br2 Au1 Br1 90.76(7) . . ? C9 N3 C10 118.0(13) . . ? C1 N2 C3 110.1(13) . . ? C1 N2 C8 126.1(13) . . ? C3 N2 C8 123.8(12) . . ? N2 C1 N1 107.4(14) . . ? N2 C1 Au1 121.1(11) . . ? N1 C1 Au1 131.5(12) . . ? C15 C16 C17 122.6(18) . . ? C16 C15 C14 118.2(17) . . ? O1 C9 N3 126.5(14) . . ? O1 C9 C8 123.0(13) . . ? N3 C9 C8 110.4(12) . . ? N3 C10 C11 114.1(11) . . ? N3 C10 C12 111.5(12) . . ? C11 C10 C12 108.6(11) . . ? N1 C2 C3 108.6(14) . . ? C2 C3 N2 105.4(14) . . ? C13 C14 C15 122.5(15) . . ? C16 C17 C18 119.6(17) . . ? C2 N1 C1 108.5(14) . . ? C2 N1 C4 121.2(14) . . ? C1 N1 C4 130.0(14) . . ? N2 C8 C9 109.3(11) . . ? C13 C12 C10 112.4(13) . . ? C17 C18 C13 119.0(16) . . ? C7 C4 C6 107.3(18) . . ? C7 C4 C5 112(2) . . ? C6 C4 C5 113(2) . . ? C7 C4 N1 111.9(14) . . ? C6 C4 N1 107.3(15) . . ? C5 C4 N1 105.0(17) . . ? C11 O2 C19 115.4(12) . . ? C14 C13 C18 118.0(14) . . ? C14 C13 C12 122.3(14) . . ? C18 C13 C12 119.7(14) . . ? O3 C11 O2 125.3(15) . . ? O3 C11 C10 120.9(14) . . ? O2 C11 C10 113.8(11) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.496 _refine_diff_density_min -2.035 _refine_diff_density_rms 0.259 # Attachment 'B906140A_Comp_6c.cif' data_jl391 _database_code_depnum_ccdc_archive 'CCDC 725411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Au Br3 N2' _chemical_formula_weight 685.01 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' Br Br -0.2901 2.4595 '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 ? _symmetry_space_group_name_H-M ? 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 9.6826(5) _cell_length_b 12.2416(4) _cell_length_c 20.3950(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.488(4) _cell_angle_gamma 90.00 _cell_volume 2416.61(18) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 11.048 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14411 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.1208 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4284 _reflns_number_gt 2497 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0010P)^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 4284 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0472 _refine_ls_wR_factor_gt 0.0459 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _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 Au1 Au 0.17389(4) 0.23204(2) 0.707529(17) 0.02967(9) Uani 1 1 d . . . Br2 Br 0.22579(9) 0.10225(6) 0.79388(4) 0.0359(2) Uani 1 1 d . . . Br3 Br 0.13763(10) 0.36184(6) 0.61912(4) 0.0467(3) Uani 1 1 d . . . Br4 Br -0.06049(9) 0.16084(6) 0.69405(5) 0.0451(3) Uani 1 1 d . . . N1 N 0.4744(6) 0.2698(4) 0.6803(3) 0.0252(15) Uani 1 1 d . . . N2 N 0.4198(7) 0.3460(4) 0.7699(3) 0.0268(16) Uani 1 1 d . . . C1 C 0.3682(8) 0.2886(5) 0.7204(3) 0.0205(19) Uani 1 1 d . . . C3 C 0.5563(9) 0.3616(6) 0.7623(4) 0.038(2) Uani 1 1 d . . . H3A H 0.6166 0.3990 0.7922 0.046 Uiso 1 1 calc R . . C6 C 0.4928(8) 0.0810(5) 0.6339(4) 0.024(2) Uani 1 1 d . . . C11 C 0.5500(8) 0.0447(6) 0.6918(4) 0.032(2) Uani 1 1 d . . . H11A H 0.5761 0.0958 0.7249 0.038 Uiso 1 1 calc R . . C5 C 0.4664(8) 0.2012(5) 0.6195(4) 0.026(2) Uani 1 1 d . . . H5A H 0.3690 0.2065 0.6022 0.031 Uiso 1 1 calc R . . C10 C 0.5702(8) -0.0643(6) 0.7027(5) 0.039(2) Uani 1 1 d . . . H10A H 0.6083 -0.0892 0.7434 0.047 Uiso 1 1 calc R . . C12 C 0.5561(9) 0.2508(6) 0.5678(3) 0.035(2) Uani 1 1 d . . . C2 C 0.5922(8) 0.3165(5) 0.7067(4) 0.031(2) Uani 1 1 d . . . H2A H 0.6815 0.3163 0.6885 0.037 Uiso 1 1 calc R . . C15 C 0.7183(13) 0.3467(8) 0.4730(5) 0.064(3) Uani 1 1 d . . . H15A H 0.7748 0.3807 0.4415 0.077 Uiso 1 1 calc R . . C8 C 0.4795(11) -0.1026(7) 0.5967(5) 0.062(3) Uani 1 1 d . . . H8A H 0.4564 -0.1535 0.5630 0.074 Uiso 1 1 calc R . . C7 C 0.4570(10) 0.0059(6) 0.5876(4) 0.043(3) Uani 1 1 d . . . H7A H 0.4150 0.0300 0.5475 0.052 Uiso 1 1 calc R . . C14 C 0.5793(14) 0.3756(6) 0.4768(5) 0.062(3) Uani 1 1 d . . . H14A H 0.5389 0.4269 0.4471 0.075 Uiso 1 1 calc R . . C17 C 0.6939(10) 0.2190(7) 0.5623(4) 0.051(3) Uani 1 1 d . . . H17A H 0.7318 0.1644 0.5906 0.061 Uiso 1 1 calc R . . C16 C 0.7746(9) 0.2672(8) 0.5156(4) 0.066(3) Uani 1 1 d . . . H16A H 0.8688 0.2466 0.5123 0.079 Uiso 1 1 calc R . . C13 C 0.5036(10) 0.3286(6) 0.5241(4) 0.046(3) Uani 1 1 d . . . H13A H 0.4097 0.3499 0.5276 0.056 Uiso 1 1 calc R . . C9 C 0.5351(9) -0.1367(7) 0.6545(5) 0.053(3) Uani 1 1 d . . . H9A H 0.5499 -0.2125 0.6616 0.063 Uiso 1 1 calc R . . C4 C 0.3367(9) 0.3862(6) 0.8249(4) 0.043(2) Uani 1 1 d . . . H4A H 0.2404 0.3633 0.8182 0.065 Uiso 1 1 calc R . . H4B H 0.3414 0.4661 0.8267 0.065 Uiso 1 1 calc R . . H4C H 0.3734 0.3556 0.8662 0.065 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 0.03479(19) 0.02945(17) 0.02478(19) -0.00345(17) 0.00068(14) 0.00531(19) Br2 0.0444(6) 0.0370(5) 0.0263(6) 0.0045(4) 0.0027(5) -0.0034(4) Br3 0.0638(7) 0.0382(5) 0.0376(6) 0.0047(4) -0.0110(5) 0.0112(5) Br4 0.0317(6) 0.0534(5) 0.0502(7) -0.0106(5) -0.0014(5) 0.0046(4) N1 0.045(5) 0.016(3) 0.014(4) 0.002(3) -0.008(3) 0.000(3) N2 0.038(5) 0.024(4) 0.018(4) -0.007(3) -0.001(4) -0.001(3) C1 0.047(6) 0.007(4) 0.007(4) 0.003(3) 0.001(4) 0.005(4) C3 0.026(6) 0.039(5) 0.050(7) -0.018(4) 0.002(5) -0.019(4) C6 0.032(5) 0.017(4) 0.024(5) 0.001(4) 0.017(4) -0.001(4) C11 0.036(6) 0.027(5) 0.032(6) 0.001(4) 0.009(4) 0.007(4) C5 0.025(5) 0.037(5) 0.016(5) -0.003(4) 0.004(4) -0.004(4) C10 0.035(6) 0.035(5) 0.048(7) 0.001(5) 0.012(5) 0.003(4) C12 0.056(6) 0.028(5) 0.020(5) 0.001(4) 0.000(4) -0.011(5) C2 0.022(5) 0.036(5) 0.034(6) -0.011(4) 0.001(5) -0.011(4) C15 0.107(10) 0.056(7) 0.030(7) 0.004(5) 0.016(7) -0.060(7) C8 0.118(10) 0.037(6) 0.033(7) 0.005(5) 0.033(6) 0.001(6) C7 0.078(8) 0.030(5) 0.023(6) 0.001(4) 0.012(5) 0.001(5) C14 0.116(11) 0.021(5) 0.051(8) 0.003(4) 0.040(7) 0.001(6) C17 0.049(7) 0.071(6) 0.032(6) 0.014(5) -0.003(5) -0.017(5) C16 0.042(6) 0.117(8) 0.037(6) 0.029(6) 0.003(5) -0.042(6) C13 0.065(7) 0.029(5) 0.046(7) -0.007(4) 0.023(5) 0.010(5) C9 0.075(8) 0.028(5) 0.056(8) 0.013(5) 0.041(6) 0.015(5) C4 0.064(7) 0.044(5) 0.022(5) -0.005(4) 0.010(5) -0.018(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.016(8) . ? Au1 Br2 2.4151(8) . ? Au1 Br3 2.4220(9) . ? Au1 Br4 2.4399(10) . ? N1 C1 1.350(9) . ? N1 C2 1.374(8) . ? N1 C5 1.498(8) . ? N2 C1 1.317(8) . ? N2 C3 1.348(9) . ? N2 C4 1.481(9) . ? C3 C2 1.316(10) . ? C6 C7 1.357(9) . ? C6 C11 1.365(10) . ? C6 C5 1.522(8) . ? C11 C10 1.366(8) . ? C5 C12 1.510(10) . ? C10 C9 1.360(10) . ? C12 C13 1.393(10) . ? C12 C17 1.397(10) . ? C15 C14 1.395(12) . ? C15 C16 1.406(11) . ? C8 C9 1.350(11) . ? C8 C7 1.358(9) . ? C14 C13 1.354(12) . ? C17 C16 1.381(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Au1 Br2 87.43(18) . . ? C1 Au1 Br3 89.34(18) . . ? Br2 Au1 Br3 176.25(4) . . ? C1 Au1 Br4 178.71(19) . . ? Br2 Au1 Br4 91.29(3) . . ? Br3 Au1 Br4 91.95(3) . . ? C1 N1 C2 109.2(6) . . ? C1 N1 C5 125.0(6) . . ? C2 N1 C5 125.6(7) . . ? C1 N2 C3 109.9(7) . . ? C1 N2 C4 123.7(7) . . ? C3 N2 C4 126.4(7) . . ? N2 C1 N1 106.0(7) . . ? N2 C1 Au1 128.1(6) . . ? N1 C1 Au1 125.8(5) . . ? C2 C3 N2 108.8(7) . . ? C7 C6 C11 118.2(7) . . ? C7 C6 C5 118.8(7) . . ? C11 C6 C5 123.0(7) . . ? C6 C11 C10 120.8(7) . . ? N1 C5 C12 109.5(5) . . ? N1 C5 C6 112.2(6) . . ? C12 C5 C6 115.3(6) . . ? C9 C10 C11 119.1(8) . . ? C13 C12 C17 118.2(8) . . ? C13 C12 C5 121.0(8) . . ? C17 C12 C5 120.8(7) . . ? C3 C2 N1 106.1(7) . . ? C14 C15 C16 120.0(9) . . ? C9 C8 C7 118.7(9) . . ? C6 C7 C8 122.0(8) . . ? C13 C14 C15 118.2(10) . . ? C16 C17 C12 119.7(8) . . ? C17 C16 C15 120.3(9) . . ? C14 C13 C12 123.4(9) . . ? C8 C9 C10 121.1(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.191 _refine_diff_density_min -0.843 _refine_diff_density_rms 0.130