####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_kp170410 _database_code_depnum_ccdc_archive 'CCDC 775874' #TrackingRef 'kp170410.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H27 Au Cl N4 O4' _chemical_formula_weight 571.83 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 7.4555(3) _cell_length_b 13.2831(8) _cell_length_c 22.2966(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.996(3) _cell_angle_gamma 90.00 _cell_volume 2191.64(18) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 5436 _cell_measurement_theta_min 2.7470 _cell_measurement_theta_max 32.6802 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 6.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3810 _exptl_absorpt_correction_T_max 0.7710 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur Ruby CCD' _diffrn_measurement_method '\o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12129 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4842 _reflns_number_gt 3851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis^Pro^ (Oxford, 2007)' _computing_cell_refinement 'CrysAlis^Pro^ (Oxford, 2007)' _computing_data_reduction 'CrysAlis^Pro^ (Oxford, 2007)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0360P)^2^+21.8672P] 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 4842 _refine_ls_number_parameters 239 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.198 _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 0.86871(5) 0.22013(3) 0.841378(15) 0.03117(13) Uani 1 1 d . . . C1 C 0.9091(12) 0.1997(8) 0.7548(4) 0.029(2) Uani 1 1 d . . . C2 C 1.0538(13) 0.1873(9) 0.6724(4) 0.036(3) Uani 1 1 d . . . H2 H 1.1490 0.1836 0.6478 0.043 Uiso 1 1 calc R . . C3 C 0.8762(13) 0.1839(9) 0.6532(4) 0.037(3) Uani 1 1 d . . . H3 H 0.8214 0.1773 0.6127 0.045 Uiso 1 1 calc R . . C4 C 0.8260(12) 0.2424(8) 0.9272(4) 0.030(2) Uani 1 1 d . . . C5 C 0.6788(13) 0.2628(9) 1.0095(4) 0.039(3) Uani 1 1 d . . . H5 H 0.5814 0.2673 1.0332 0.047 Uiso 1 1 calc R . . C6 C 0.8559(13) 0.2694(10) 1.0295(4) 0.043(3) Uani 1 1 d . . . H6 H 0.9083 0.2799 1.0700 0.051 Uiso 1 1 calc R . . C7 C 0.5913(12) 0.1843(8) 0.7049(4) 0.031(2) Uani 1 1 d . . . H7A H 0.5609 0.1872 0.7473 0.038 Uiso 1 1 calc R . . C8 C 0.5227(17) 0.3584(10) 0.6941(6) 0.057(4) Uani 1 1 d . . . H8A H 0.6513 0.3788 0.6975 0.069 Uiso 1 1 calc R . . H8B H 0.4842 0.3601 0.7351 0.069 Uiso 1 1 calc R . . C9 C 0.4113(19) 0.4298(10) 0.6541(7) 0.068(4) Uani 1 1 d . . . H9A H 0.4516 0.4292 0.6139 0.103 Uiso 1 1 calc R . . H9B H 0.4246 0.4978 0.6711 0.103 Uiso 1 1 calc R . . H9C H 0.2841 0.4096 0.6509 0.103 Uiso 1 1 calc R . . C10 C 0.5779(19) 0.0059(12) 0.7088(7) 0.074(5) Uani 1 1 d . . . H10 H 0.6850 -0.0302 0.7037 0.089 Uiso 1 1 calc R . . C11 C 0.453(3) -0.0248(13) 0.7478(8) 0.099(6) Uani 1 1 d . . . H11C H 0.4396 0.0286 0.7773 0.148 Uiso 1 1 calc R . . H11B H 0.4967 -0.0863 0.7690 0.148 Uiso 1 1 calc R . . H11A H 0.3357 -0.0380 0.7241 0.148 Uiso 1 1 calc R . . C12 C 1.1445(14) 0.2665(10) 0.9783(4) 0.044(3) Uani 1 1 d . . . H12A H 1.1798 0.2539 0.9371 0.052 Uiso 1 1 calc R . . C13 C 1.176(2) 0.4419(14) 0.9592(9) 0.098(7) Uani 1 1 d . . . H13B H 1.0630 0.4296 0.9322 0.118 Uiso 1 1 calc R . . H13A H 1.1583 0.5031 0.9832 0.118 Uiso 1 1 calc R . . C14 C 1.317(2) 0.4607(13) 0.9232(8) 0.097(6) Uani 1 1 d . . . H14C H 1.4325 0.4668 0.9493 0.145 Uiso 1 1 calc R . . H14B H 1.2924 0.5233 0.9005 0.145 Uiso 1 1 calc R . . H14A H 1.3245 0.4048 0.8949 0.145 Uiso 1 1 calc R . . C15 C 1.216(2) 0.0975(11) 1.0021(8) 0.082(5) Uani 1 1 d . . . H15A H 1.2675 0.0886 0.9635 0.099 Uiso 1 1 calc R . . H15B H 1.0881 0.0763 0.9960 0.099 Uiso 1 1 calc R . . C16 C 1.319(2) 0.0345(13) 1.0505(10) 0.110(8) Uani 1 1 d . . . H16C H 1.2609 0.0386 1.0875 0.165 Uiso 1 1 calc R . . H16B H 1.4436 0.0594 1.0586 0.165 Uiso 1 1 calc R . . H16A H 1.3206 -0.0357 1.0370 0.165 Uiso 1 1 calc R . . N1 N 0.7895(10) 0.1919(7) 0.7039(3) 0.0304(18) Uani 1 1 d U . . N2 N 1.0722(10) 0.1968(6) 0.7333(3) 0.0312(17) Uani 1 1 d U . . H2A H 1.1769 0.2007 0.7562 0.037 Uiso 1 1 calc R . . N3 N 0.9497(10) 0.2574(7) 0.9779(4) 0.0337(19) Uani 1 1 d U . . N4 N 0.6659(10) 0.2480(6) 0.9468(3) 0.0312(17) Uani 1 1 d U . . H4A H 0.5627 0.2429 0.9232 0.037 Uiso 1 1 calc R . . O1 O 0.5036(9) 0.2593(5) 0.6706(3) 0.0302(16) Uani 1 1 d . . . O2 O 0.5244(10) 0.0993(7) 0.6771(4) 0.051(2) Uani 1 1 d . . . O3 O 1.2085(10) 0.3576(7) 1.0000(4) 0.057(2) Uani 1 1 d . . . O4 O 1.2288(10) 0.1981(7) 1.0198(3) 0.048(2) Uani 1 1 d . . . Cl1 Cl 0.3648(3) 0.2068(3) 0.84309(12) 0.0564(9) 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 0.02540(18) 0.0518(3) 0.01469(16) -0.0014(2) -0.00393(11) 0.0040(2) C1 0.026(5) 0.043(7) 0.016(4) 0.000(4) -0.006(3) -0.003(4) C2 0.024(5) 0.060(8) 0.025(5) -0.003(5) 0.004(4) 0.003(5) C3 0.030(5) 0.063(8) 0.017(4) -0.002(5) -0.003(4) 0.005(5) C4 0.023(4) 0.041(7) 0.023(4) 0.006(4) -0.004(4) 0.001(4) C5 0.026(5) 0.067(8) 0.024(5) -0.010(5) 0.004(4) 0.001(5) C6 0.029(5) 0.076(9) 0.022(5) 0.000(6) -0.003(4) 0.000(6) C7 0.018(4) 0.056(7) 0.019(4) 0.001(4) -0.004(4) 0.001(4) C8 0.045(7) 0.051(8) 0.072(9) -0.013(7) -0.007(6) -0.012(6) C9 0.065(9) 0.047(8) 0.093(11) -0.002(8) 0.009(8) 0.010(7) C10 0.052(8) 0.066(10) 0.105(12) 0.036(9) 0.014(8) 0.010(8) C11 0.129(16) 0.064(11) 0.113(14) 0.039(10) 0.055(13) 0.027(11) C12 0.029(5) 0.078(9) 0.024(5) -0.003(6) 0.003(4) 0.012(6) C13 0.067(10) 0.107(15) 0.123(15) 0.072(13) 0.025(10) 0.031(10) C14 0.103(14) 0.082(13) 0.103(13) 0.050(11) 0.002(11) -0.010(11) C15 0.075(11) 0.051(10) 0.123(15) -0.010(10) 0.020(10) -0.020(9) C16 0.070(11) 0.067(11) 0.20(2) 0.044(13) 0.054(13) 0.030(9) N1 0.023(3) 0.052(5) 0.014(3) 0.001(3) -0.004(3) -0.002(3) N2 0.018(3) 0.049(4) 0.025(3) -0.003(3) -0.004(3) 0.000(3) N3 0.013(3) 0.050(5) 0.036(4) 0.001(4) -0.006(3) 0.015(3) N4 0.022(3) 0.048(4) 0.022(3) 0.003(3) -0.006(3) -0.003(3) O1 0.028(3) 0.032(4) 0.028(3) -0.003(3) -0.002(3) 0.001(3) O2 0.029(4) 0.069(6) 0.051(5) 0.010(5) -0.012(4) -0.012(4) O3 0.034(4) 0.074(7) 0.059(5) 0.010(5) -0.006(4) -0.015(4) O4 0.035(4) 0.067(6) 0.037(4) -0.004(4) -0.009(3) 0.008(4) Cl1 0.0236(11) 0.117(3) 0.0268(11) -0.0219(17) -0.0047(9) -0.0002(17) _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 C4 1.999(10) . ? Au1 C1 2.007(9) . ? C1 N1 1.359(10) . ? C1 N2 1.361(12) . ? C2 C3 1.341(13) . ? C2 N2 1.355(12) . ? C2 H2 0.9500 . ? C3 N1 1.373(12) . ? C3 H3 0.9500 . ? C4 N4 1.323(12) . ? C4 N3 1.384(11) . ? C5 C6 1.344(13) . ? C5 N4 1.402(12) . ? C5 H5 0.9500 . ? C6 N3 1.426(13) . ? C6 H6 0.9500 . ? C7 O2 1.352(13) . ? C7 O1 1.372(12) . ? C7 N1 1.484(11) . ? C7 H7A 1.0000 . ? C8 O1 1.417(14) . ? C8 C9 1.486(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.41(2) . ? C10 O2 1.459(16) . ? C10 H10 0.9500 . ? C11 H11C 0.9800 . ? C11 H11B 0.9800 . ? C11 H11A 0.9800 . ? C12 O3 1.367(15) . ? C12 O4 1.391(13) . ? C12 N3 1.456(12) . ? C12 H12A 1.0000 . ? C13 C14 1.42(2) . ? C13 O3 1.444(16) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C14 H14A 0.9800 . ? C15 O4 1.393(16) . ? C15 C16 1.50(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16C 0.9800 . ? C16 H16B 0.9800 . ? C16 H16A 0.9800 . ? N2 H2A 0.8800 . ? N4 H4A 0.8800 . ? 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 C4 Au1 C1 179.1(4) . . ? N1 C1 N2 103.1(7) . . ? N1 C1 Au1 130.8(7) . . ? N2 C1 Au1 126.0(6) . . ? C3 C2 N2 107.3(8) . . ? C3 C2 H2 126.3 . . ? N2 C2 H2 126.3 . . ? C2 C3 N1 106.3(8) . . ? C2 C3 H3 126.9 . . ? N1 C3 H3 126.9 . . ? N4 C4 N3 105.0(8) . . ? N4 C4 Au1 125.5(7) . . ? N3 C4 Au1 129.5(7) . . ? C6 C5 N4 106.5(8) . . ? C6 C5 H5 126.7 . . ? N4 C5 H5 126.7 . . ? C5 C6 N3 106.5(8) . . ? C5 C6 H6 126.7 . . ? N3 C6 H6 126.7 . . ? O2 C7 O1 103.2(7) . . ? O2 C7 N1 111.3(8) . . ? O1 C7 N1 110.5(8) . . ? O2 C7 H7A 110.6 . . ? O1 C7 H7A 110.6 . . ? N1 C7 H7A 110.6 . . ? O1 C8 C9 110.3(10) . . ? O1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? O1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 O2 112.5(13) . . ? C11 C10 H10 123.8 . . ? O2 C10 H10 123.8 . . ? C10 C11 H11C 109.5 . . ? C10 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C10 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? O3 C12 O4 103.5(8) . . ? O3 C12 N3 112.4(9) . . ? O4 C12 N3 108.6(9) . . ? O3 C12 H12A 110.7 . . ? O4 C12 H12A 110.7 . . ? N3 C12 H12A 110.7 . . ? C14 C13 O3 114.5(13) . . ? C14 C13 H13B 108.6 . . ? O3 C13 H13B 108.6 . . ? C14 C13 H13A 108.6 . . ? O3 C13 H13A 108.6 . . ? H13B C13 H13A 107.6 . . ? C13 C14 H14C 109.5 . . ? C13 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C13 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? O4 C15 C16 108.7(14) . . ? O4 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O4 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.3 . . ? C15 C16 H16C 109.5 . . ? C15 C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C15 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? C1 N1 C3 111.5(8) . . ? C1 N1 C7 123.2(8) . . ? C3 N1 C7 125.1(7) . . ? C2 N2 C1 111.8(7) . . ? C2 N2 H2A 124.1 . . ? C1 N2 H2A 124.1 . . ? C4 N3 C6 109.4(8) . . ? C4 N3 C12 125.6(8) . . ? C6 N3 C12 124.9(8) . . ? C4 N4 C5 112.5(8) . . ? C4 N4 H4A 123.7 . . ? C5 N4 H4A 123.7 . . ? C7 O1 C8 116.7(8) . . ? C7 O2 C10 115.1(9) . . ? C12 O3 C13 116.1(12) . . ? C12 O4 C15 115.4(11) . . ? 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 Au1 C1 N1 -53(27) . . . . ? C4 Au1 C1 N2 123(26) . . . . ? N2 C2 C3 N1 0.1(13) . . . . ? C1 Au1 C4 N4 56(27) . . . . ? C1 Au1 C4 N3 -123(26) . . . . ? N4 C5 C6 N3 -0.5(13) . . . . ? N2 C1 N1 C3 0.4(12) . . . . ? Au1 C1 N1 C3 176.6(8) . . . . ? N2 C1 N1 C7 175.5(9) . . . . ? Au1 C1 N1 C7 -8.3(15) . . . . ? C2 C3 N1 C1 -0.3(13) . . . . ? C2 C3 N1 C7 -175.3(10) . . . . ? O2 C7 N1 C1 -122.1(10) . . . . ? O1 C7 N1 C1 123.9(10) . . . . ? O2 C7 N1 C3 52.3(13) . . . . ? O1 C7 N1 C3 -61.7(13) . . . . ? C3 C2 N2 C1 0.1(13) . . . . ? N1 C1 N2 C2 -0.3(12) . . . . ? Au1 C1 N2 C2 -176.7(8) . . . . ? N4 C4 N3 C6 1.7(12) . . . . ? Au1 C4 N3 C6 -179.7(8) . . . . ? N4 C4 N3 C12 -174.4(10) . . . . ? Au1 C4 N3 C12 4.2(16) . . . . ? C5 C6 N3 C4 -0.7(13) . . . . ? C5 C6 N3 C12 175.4(11) . . . . ? O3 C12 N3 C4 118.9(11) . . . . ? O4 C12 N3 C4 -127.1(10) . . . . ? O3 C12 N3 C6 -56.6(14) . . . . ? O4 C12 N3 C6 57.3(15) . . . . ? N3 C4 N4 C5 -2.1(12) . . . . ? Au1 C4 N4 C5 179.3(8) . . . . ? C6 C5 N4 C4 1.7(14) . . . . ? O2 C7 O1 C8 169.9(9) . . . . ? N1 C7 O1 C8 -71.1(11) . . . . ? C9 C8 O1 C7 -176.5(10) . . . . ? O1 C7 O2 C10 -172.5(9) . . . . ? N1 C7 O2 C10 68.9(11) . . . . ? C11 C10 O2 C7 92.2(16) . . . . ? O4 C12 O3 C13 166.6(10) . . . . ? N3 C12 O3 C13 -76.3(13) . . . . ? C14 C13 O3 C12 -91.6(18) . . . . ? O3 C12 O4 C15 -167.4(10) . . . . ? N3 C12 O4 C15 72.9(13) . . . . ? C16 C15 O4 C12 177.9(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A Cl1 0.88 2.23 3.070(8) 160.4 . N2 H2A Cl1 0.88 2.25 3.077(8) 156.4 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.249 _refine_diff_density_min -2.426 _refine_diff_density_rms 0.198 data_kp280410 _database_code_depnum_ccdc_archive 'CCDC 775875' #TrackingRef 'kp280410.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Au Cl N4' _chemical_formula_weight 368.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.51512(18) _cell_length_b 14.1757(2) _cell_length_c 23.3727(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.774(2) _cell_angle_gamma 90.00 _cell_volume 2795.35(9) _cell_formula_units_Z 12 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 9180 _cell_measurement_theta_min 4.930 _cell_measurement_theta_max 37.54 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 16.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0937 _exptl_absorpt_correction_T_max 0.5666 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur Ruby CCD' _diffrn_measurement_method '\o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24088 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 4.94 _diffrn_reflns_theta_max 36.32 _reflns_number_total 6769 _reflns_number_gt 4608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis^Pro^ (Oxford, 2007)' _computing_cell_refinement 'CrysAlis^Pro^ (Oxford, 2007)' _computing_data_reduction 'CrysAlis^Pro^ (Oxford, 2007)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0205P)^2^+1.5854P] 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 6769 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.648314(16) 0.248798(9) 0.167004(6) 0.02814(4) Uani 1 1 d . . . Au2 Au 0.5000 -0.004211(14) 0.2500 0.02925(5) Uani 1 2 d S . . Cl1 Cl 0.80717(10) 0.00228(6) 0.08131(4) 0.03125(18) Uani 1 1 d . . . Cl2 Cl 1.0000 -0.01229(7) 0.2500 0.0225(2) Uani 1 2 d S . . C1 C 0.7400(4) 0.2495(2) 0.25125(16) 0.0266(7) Uani 1 1 d . . . C2 C 0.8899(5) 0.2100(3) 0.33497(17) 0.0333(8) Uani 1 1 d . . . H2A H 0.9605 0.1760 0.3625 0.040 Uiso 1 1 calc R . . C3 C 0.8196(4) 0.2934(2) 0.34261(16) 0.0281(7) Uani 1 1 d . . . H3A H 0.8301 0.3296 0.3771 0.034 Uiso 1 1 calc R . . C4 C 0.5698(4) 0.2481(2) 0.08183(16) 0.0274(7) Uani 1 1 d . . . C5 C 0.5428(4) 0.2102(2) -0.01280(18) 0.0317(8) Uani 1 1 d . . . H5A H 0.5567 0.1787 -0.0476 0.038 Uiso 1 1 calc R . . C6 C 0.4461(4) 0.2855(3) -0.00660(18) 0.0323(8) Uani 1 1 d . . . H6A H 0.3789 0.3168 -0.0364 0.039 Uiso 1 1 calc R . . C7 C 0.6053(4) -0.0021(2) 0.33257(15) 0.0271(7) Uani 1 1 d . . . C8 C 0.7857(4) 0.0001(2) 0.41234(17) 0.0306(8) Uani 1 1 d . . . H8A H 0.8851 -0.0012 0.4363 0.037 Uiso 1 1 calc R . . C9 C 0.6405(4) 0.0117(2) 0.42973(17) 0.0312(8) Uani 1 1 d . . . H9A H 0.6176 0.0190 0.4681 0.037 Uiso 1 1 calc R . . N1 N 0.8378(3) 0.18471(19) 0.27882(14) 0.0288(6) Uani 1 1 d . . . H1 H 0.8653 0.1321 0.2628 0.035 Uiso 1 1 calc R . . N2 N 0.7297(3) 0.31613(19) 0.29111(13) 0.0274(6) Uani 1 1 d . . . H2 H 0.6727 0.3679 0.2851 0.033 Uiso 1 1 calc R . . N3 N 0.4651(4) 0.30690(19) 0.05072(14) 0.0296(7) Uani 1 1 d . . . H3 H 0.4154 0.3532 0.0658 0.035 Uiso 1 1 calc R . . N4 N 0.6155(3) 0.18954(19) 0.04185(13) 0.0271(6) Uani 1 1 d . . . H4 H 0.6840 0.1434 0.0498 0.033 Uiso 1 1 calc R . . N7 N 0.5342(3) 0.0106(2) 0.37985(13) 0.0277(6) Uani 1 1 d . . . H7 H 0.4312 0.0174 0.3790 0.033 Uiso 1 1 calc R . . N8 N 0.7597(3) -0.00927(19) 0.35309(14) 0.0295(6) Uani 1 1 d . . . H8 H 0.8351 -0.0188 0.3314 0.035 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 0.03019(7) 0.02260(6) 0.03165(7) 0.00043(5) 0.00421(5) 0.00367(5) Au2 0.03171(10) 0.02791(9) 0.02954(10) 0.000 0.00924(7) 0.000 Cl1 0.0247(4) 0.0278(4) 0.0429(5) 0.0061(4) 0.0110(3) 0.0085(3) Cl2 0.0263(5) 0.0126(4) 0.0296(5) 0.000 0.0075(4) 0.000 C1 0.0268(17) 0.0206(14) 0.0334(19) 0.0027(13) 0.0082(14) 0.0002(12) C2 0.031(2) 0.0330(19) 0.036(2) 0.0058(16) 0.0053(16) 0.0079(15) C3 0.0262(19) 0.0257(16) 0.032(2) -0.0018(14) 0.0030(15) -0.0004(13) C4 0.0247(17) 0.0218(14) 0.0355(18) 0.0019(15) 0.0034(14) -0.0002(13) C5 0.034(2) 0.0230(16) 0.038(2) 0.0003(15) 0.0036(16) 0.0016(14) C6 0.030(2) 0.0280(17) 0.037(2) 0.0027(16) -0.0009(16) 0.0027(14) C7 0.0267(17) 0.0219(15) 0.0342(18) 0.0009(14) 0.0089(14) -0.0011(12) C8 0.0236(17) 0.0258(16) 0.042(2) 0.0006(16) 0.0024(14) 0.0036(13) C9 0.0300(19) 0.0339(18) 0.0310(18) 0.0021(16) 0.0091(14) -0.0048(15) N1 0.0312(16) 0.0211(13) 0.0346(17) 0.0005(12) 0.0067(13) 0.0073(11) N2 0.0248(15) 0.0215(12) 0.0360(17) 0.0002(12) 0.0050(13) 0.0068(10) N3 0.0289(16) 0.0220(13) 0.0378(18) 0.0007(12) 0.0043(13) 0.0068(11) N4 0.0268(15) 0.0213(12) 0.0339(17) 0.0028(12) 0.0062(13) 0.0041(10) N7 0.0193(13) 0.0321(15) 0.0326(15) 0.0019(13) 0.0069(11) 0.0007(11) N8 0.0257(15) 0.0252(13) 0.0410(17) 0.0004(13) 0.0167(12) 0.0010(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C4 2.013(4) . ? Au1 C1 2.018(4) . ? Au2 C7 2.015(4) . ? Au2 C7 2.015(4) 2_655 ? C1 N2 1.337(4) . ? C1 N1 1.345(4) . ? C2 C3 1.348(5) . ? C2 N1 1.375(5) . ? C2 H2A 0.9500 . ? C3 N2 1.375(4) . ? C3 H3A 0.9500 . ? C4 N4 1.346(4) . ? C4 N3 1.358(4) . ? C5 C6 1.367(5) . ? C5 N4 1.374(5) . ? C5 H5A 0.9500 . ? C6 N3 1.362(5) . ? C6 H6A 0.9500 . ? C7 N8 1.341(4) . ? C7 N7 1.342(5) . ? C8 C9 1.362(5) . ? C8 N8 1.379(5) . ? C8 H8A 0.9500 . ? C9 N7 1.376(5) . ? C9 H9A 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3 0.8800 . ? N4 H4 0.8800 . ? N7 H7 0.8800 . ? N8 H8 0.8800 . ? 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 C4 Au1 C1 176.67(13) . . ? C7 Au2 C7 178.31(18) . 2_655 ? N2 C1 N1 104.1(3) . . ? N2 C1 Au1 129.1(2) . . ? N1 C1 Au1 126.7(3) . . ? C3 C2 N1 105.3(3) . . ? C3 C2 H2A 127.4 . . ? N1 C2 H2A 127.4 . . ? C2 C3 N2 107.1(3) . . ? C2 C3 H3A 126.4 . . ? N2 C3 H3A 126.4 . . ? N4 C4 N3 103.7(3) . . ? N4 C4 Au1 127.0(2) . . ? N3 C4 Au1 129.3(3) . . ? C6 C5 N4 105.7(3) . . ? C6 C5 H5A 127.2 . . ? N4 C5 H5A 127.2 . . ? N3 C6 C5 106.6(3) . . ? N3 C6 H6A 126.7 . . ? C5 C6 H6A 126.7 . . ? N8 C7 N7 104.2(3) . . ? N8 C7 Au2 129.0(3) . . ? N7 C7 Au2 126.8(2) . . ? C9 C8 N8 106.4(3) . . ? C9 C8 H8A 126.8 . . ? N8 C8 H8A 126.8 . . ? C8 C9 N7 105.4(3) . . ? C8 C9 H9A 127.3 . . ? N7 C9 H9A 127.3 . . ? C1 N1 C2 112.2(3) . . ? C1 N1 H1 123.9 . . ? C2 N1 H1 123.9 . . ? C1 N2 C3 111.3(3) . . ? C1 N2 H2 124.4 . . ? C3 N2 H2 124.4 . . ? C4 N3 C6 111.8(3) . . ? C4 N3 H3 124.1 . . ? C6 N3 H3 124.1 . . ? C4 N4 C5 112.2(3) . . ? C4 N4 H4 123.9 . . ? C5 N4 H4 123.9 . . ? C7 N7 C9 112.4(3) . . ? C7 N7 H7 123.8 . . ? C9 N7 H7 123.8 . . ? C7 N8 C8 111.6(3) . . ? C7 N8 H8 124.2 . . ? C8 N8 H8 124.2 . . ? 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 Au1 C1 N2 115(2) . . . . ? C4 Au1 C1 N1 -59(2) . . . . ? N1 C2 C3 N2 -0.8(4) . . . . ? C1 Au1 C4 N4 50(2) . . . . ? C1 Au1 C4 N3 -127(2) . . . . ? N4 C5 C6 N3 0.2(4) . . . . ? C7 Au2 C7 N8 -96.2(3) 2_655 . . . ? C7 Au2 C7 N7 81.1(3) 2_655 . . . ? N8 C8 C9 N7 -1.1(4) . . . . ? N2 C1 N1 C2 -0.6(4) . . . . ? Au1 C1 N1 C2 174.7(3) . . . . ? C3 C2 N1 C1 0.9(4) . . . . ? N1 C1 N2 C3 0.1(4) . . . . ? Au1 C1 N2 C3 -175.0(3) . . . . ? C2 C3 N2 C1 0.5(4) . . . . ? N4 C4 N3 C6 0.1(4) . . . . ? Au1 C4 N3 C6 177.9(3) . . . . ? C5 C6 N3 C4 -0.2(4) . . . . ? N3 C4 N4 C5 0.0(4) . . . . ? Au1 C4 N4 C5 -177.8(2) . . . . ? C6 C5 N4 C4 -0.2(4) . . . . ? N8 C7 N7 C9 0.1(4) . . . . ? Au2 C7 N7 C9 -177.7(2) . . . . ? C8 C9 N7 C7 0.7(4) . . . . ? N7 C7 N8 C8 -0.9(4) . . . . ? Au2 C7 N8 C8 176.9(2) . . . . ? C9 C8 N8 C7 1.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl2 0.88 2.39 3.227(3) 160.1 . N2 H2 Cl2 0.88 2.32 3.187(3) 167.1 3_455 N3 H3 Cl1 0.88 2.35 3.202(3) 162.1 3_455 N4 H4 Cl1 0.88 2.33 3.187(3) 164.2 . N7 H7 Cl1 0.88 2.35 3.163(3) 153.2 2_655 N8 H8 Cl2 0.88 2.52 3.366(3) 162.8 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.445 _refine_diff_density_min -1.795 _refine_diff_density_rms 0.165