# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_scan_0m_pbca _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 Au Cl I3 O3 P' _chemical_formula_sum 'C21 H18 Au Cl I3 O3 P' _chemical_formula_weight 962.44 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 18.718(2) _cell_length_b 8.0042(12) _cell_length_c 33.333(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4994.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 6581 _cell_measurement_theta_min 2.4441 _cell_measurement_theta_max 24.4411 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3504 _exptl_absorpt_coefficient_mu 9.792 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0798 _exptl_absorpt_correction_T_max 0.2448 _exptl_absorpt_process_details 'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'XOS X-beam microfocus source' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S benchtop diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29265 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4402 _reflns_number_gt 3547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'GIS (Bruker)' _computing_cell_refinement 'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009); XPREP (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Jmol (Jmol.org, 2008)' _computing_publication_material 'APEX2 (Bruker, 2010)' _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^)+(0.0100P)^2^+16.7143P] 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 4402 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.469131(14) 1.12998(4) 0.308358(8) 0.03440(9) Uani 1 1 d . . . I1 I 0.30212(3) 0.91490(9) 0.467942(18) 0.06325(19) Uani 1 1 d . . . I2 I 0.79930(3) 0.80229(8) 0.423074(17) 0.05132(16) Uani 1 1 d . . . I3 I 0.41004(3) 0.46678(7) 0.400612(18) 0.05436(17) Uani 1 1 d . . . Cl1 Cl 0.42127(11) 1.3187(2) 0.26489(6) 0.0470(5) Uani 1 1 d . . . P1 P 0.52337(9) 0.9609(2) 0.35063(6) 0.0309(4) Uani 1 1 d . . . O1 O 0.5168(2) 1.0061(6) 0.39663(14) 0.0353(12) Uani 1 1 d . . . O2 O 0.6057(2) 0.9784(6) 0.34393(14) 0.0343(12) Uani 1 1 d . . . O3 O 0.5043(2) 0.7706(6) 0.35149(15) 0.0388(12) Uani 1 1 d . . . C1 C 0.4486(4) 0.9844(10) 0.4160(2) 0.0409(19) Uani 1 1 d . . . H1A H 0.4412 0.8672 0.4222 0.049 Uiso 1 1 calc R . . H1B H 0.4106 1.0204 0.3982 0.049 Uiso 1 1 calc R . . C2 C 0.4467(4) 1.0852(8) 0.45385(19) 0.0288(16) Uani 1 1 d . . . C3 C 0.5027(4) 1.1907(9) 0.4641(2) 0.0355(17) Uani 1 1 d . . . H3 H 0.5425 1.1991 0.4475 0.043 Uiso 1 1 calc R . . C4 C 0.4992(4) 1.2832(10) 0.4992(3) 0.048(2) Uani 1 1 d . . . H4 H 0.5375 1.3511 0.5062 0.057 Uiso 1 1 calc R . . C5 C 0.4404(5) 1.2769(11) 0.5237(3) 0.056(2) Uani 1 1 d . . . H5 H 0.4384 1.3430 0.5466 0.068 Uiso 1 1 calc R . . C6 C 0.3854(5) 1.1743(11) 0.5145(2) 0.050(2) Uani 1 1 d . . . H6 H 0.3458 1.1691 0.5313 0.061 Uiso 1 1 calc R . . C7 C 0.3880(4) 1.0764(9) 0.4800(2) 0.0376(18) Uani 1 1 d . . . C8 C 0.6608(3) 0.8917(9) 0.3653(2) 0.0355(17) Uani 1 1 d . . . H8A H 0.6516 0.7724 0.3649 0.043 Uiso 1 1 calc R . . H8B H 0.6621 0.9287 0.3930 0.043 Uiso 1 1 calc R . . C9 C 0.7313(3) 0.9287(8) 0.3450(2) 0.0293(16) Uani 1 1 d . . . C10 C 0.7959(4) 0.8948(8) 0.3639(2) 0.0337(17) Uani 1 1 d . . . C11 C 0.8605(4) 0.9198(10) 0.3447(2) 0.044(2) Uani 1 1 d . . . H11 H 0.9031 0.8931 0.3575 0.053 Uiso 1 1 calc R . . C12 C 0.8609(4) 0.9846(10) 0.3064(2) 0.046(2) Uani 1 1 d . . . H12 H 0.9039 1.0009 0.2930 0.055 Uiso 1 1 calc R . . C13 C 0.7976(4) 1.0248(10) 0.2883(2) 0.043(2) Uani 1 1 d . . . H13 H 0.7979 1.0722 0.2628 0.052 Uiso 1 1 calc R . . C14 C 0.7335(4) 0.9957(9) 0.3073(2) 0.0367(18) Uani 1 1 d . . . H14 H 0.6910 1.0221 0.2943 0.044 Uiso 1 1 calc R . . C15 C 0.4649(4) 0.6808(10) 0.3198(2) 0.0387(18) Uani 1 1 d . . . H15A H 0.4798 0.5647 0.3194 0.046 Uiso 1 1 calc R . . H15B H 0.4762 0.7294 0.2939 0.046 Uiso 1 1 calc R . . C16 C 0.3865(4) 0.6897(8) 0.3266(2) 0.0313(16) Uani 1 1 d . . . C17 C 0.3527(4) 0.6134(9) 0.3589(2) 0.0345(17) Uani 1 1 d . . . C18 C 0.2789(4) 0.6211(10) 0.3637(2) 0.046(2) Uani 1 1 d . . . H18 H 0.2569 0.5691 0.3854 0.055 Uiso 1 1 calc R . . C19 C 0.2387(4) 0.7078(10) 0.3356(3) 0.051(2) Uani 1 1 d . . . H19 H 0.1894 0.7158 0.3386 0.062 Uiso 1 1 calc R . . C20 C 0.2709(5) 0.7810(10) 0.3036(3) 0.054(2) Uani 1 1 d . . . H20 H 0.2434 0.8360 0.2845 0.065 Uiso 1 1 calc R . . C21 C 0.3434(4) 0.7748(10) 0.2993(2) 0.0430(19) Uani 1 1 d . . . H21 H 0.3645 0.8287 0.2776 0.052 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 0.03103(17) 0.04236(17) 0.02980(16) 0.00005(14) -0.00045(12) 0.00144(13) I1 0.0435(3) 0.1008(5) 0.0455(3) 0.0078(3) 0.0049(3) -0.0178(3) I2 0.0422(3) 0.0699(4) 0.0419(3) 0.0107(3) -0.0013(2) 0.0147(3) I3 0.0671(4) 0.0458(3) 0.0502(4) 0.0147(3) -0.0179(3) -0.0043(3) Cl1 0.0549(12) 0.0476(12) 0.0384(11) 0.0045(9) -0.0069(9) 0.0076(9) P1 0.0239(9) 0.0410(11) 0.0278(10) -0.0002(8) 0.0010(8) -0.0024(8) O1 0.028(3) 0.053(3) 0.025(3) -0.007(2) 0.000(2) -0.001(2) O2 0.017(2) 0.049(3) 0.036(3) 0.008(2) 0.000(2) -0.001(2) O3 0.035(3) 0.042(3) 0.040(3) 0.002(2) -0.008(2) -0.006(2) C1 0.032(4) 0.054(5) 0.037(5) -0.002(4) 0.002(3) -0.002(4) C2 0.033(4) 0.034(4) 0.020(4) 0.005(3) -0.004(3) 0.009(3) C3 0.037(4) 0.033(4) 0.036(4) 0.002(3) 0.003(3) 0.002(3) C4 0.059(5) 0.038(5) 0.047(5) -0.006(4) -0.016(4) 0.004(4) C5 0.068(6) 0.056(6) 0.044(5) -0.012(5) -0.002(5) 0.013(5) C6 0.052(5) 0.073(6) 0.026(4) 0.003(4) 0.008(4) 0.019(5) C7 0.031(4) 0.047(5) 0.035(4) 0.007(4) -0.005(3) 0.003(3) C8 0.026(4) 0.047(5) 0.033(4) -0.001(4) -0.004(3) 0.000(3) C9 0.026(4) 0.033(4) 0.028(4) -0.008(3) 0.002(3) -0.001(3) C10 0.027(4) 0.032(4) 0.042(4) -0.006(3) 0.001(3) 0.002(3) C11 0.024(4) 0.058(5) 0.050(5) -0.001(4) 0.000(4) 0.004(4) C12 0.029(4) 0.064(6) 0.044(5) -0.002(4) 0.011(4) -0.013(4) C13 0.036(5) 0.063(5) 0.030(4) -0.003(4) 0.009(4) -0.004(4) C14 0.030(4) 0.044(4) 0.036(4) 0.001(4) 0.002(3) 0.001(3) C15 0.037(4) 0.054(5) 0.026(4) -0.009(3) 0.006(3) -0.006(4) C16 0.036(4) 0.031(4) 0.026(4) -0.010(3) 0.000(3) 0.001(3) C17 0.033(4) 0.039(4) 0.031(4) -0.001(3) -0.002(3) -0.004(3) C18 0.046(5) 0.048(5) 0.044(5) 0.001(4) 0.009(4) -0.007(4) C19 0.033(4) 0.048(5) 0.073(7) -0.005(5) -0.004(4) 0.008(4) C20 0.061(6) 0.043(5) 0.058(6) 0.001(4) -0.019(5) 0.001(4) C21 0.045(5) 0.047(5) 0.037(5) -0.001(4) -0.002(4) -0.008(4) _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 P1 2.2018(19) . ? Au1 Cl1 2.2767(19) . ? I1 C7 2.101(7) . ? I2 C10 2.107(7) . ? I3 C17 2.112(7) . ? P1 O2 1.564(4) . ? P1 O3 1.565(5) . ? P1 O1 1.580(5) . ? O1 C1 1.441(8) . ? O2 C8 1.432(8) . ? O3 C15 1.475(8) . ? C1 C2 1.498(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.390(10) . ? C2 C7 1.404(9) . ? C3 C4 1.384(10) . ? C3 H3 0.9300 . ? C4 C5 1.372(11) . ? C4 H4 0.9300 . ? C5 C6 1.352(11) . ? C5 H5 0.9300 . ? C6 C7 1.394(10) . ? C6 H6 0.9300 . ? C8 C9 1.511(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.369(10) . ? C9 C10 1.390(9) . ? C10 C11 1.383(10) . ? C11 C12 1.378(11) . ? C11 H11 0.9300 . ? C12 C13 1.370(10) . ? C12 H12 0.9300 . ? C13 C14 1.377(10) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.487(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.390(10) . ? C16 C21 1.394(10) . ? C17 C18 1.391(10) . ? C18 C19 1.388(11) . ? C18 H18 0.9300 . ? C19 C20 1.357(12) . ? C19 H19 0.9300 . ? C20 C21 1.364(11) . ? C20 H20 0.9300 . ? C21 H21 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 P1 Au1 Cl1 175.22(7) . . ? O2 P1 O3 108.3(3) . . ? O2 P1 O1 101.2(3) . . ? O3 P1 O1 100.8(3) . . ? O2 P1 Au1 107.94(19) . . ? O3 P1 Au1 120.3(2) . . ? O1 P1 Au1 116.4(2) . . ? C1 O1 P1 118.4(4) . . ? C8 O2 P1 126.5(4) . . ? C15 O3 P1 125.1(5) . . ? O1 C1 C2 109.5(6) . . ? O1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? O1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C3 C2 C7 117.9(7) . . ? C3 C2 C1 121.1(6) . . ? C7 C2 C1 121.0(6) . . ? C4 C3 C2 119.8(7) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 121.4(8) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 119.9(8) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.1(8) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.7(7) . . ? C6 C7 I1 118.5(6) . . ? C2 C7 I1 120.7(5) . . ? O2 C8 C9 108.1(6) . . ? O2 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O2 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C14 C9 C10 117.9(6) . . ? C14 C9 C8 120.9(6) . . ? C10 C9 C8 121.2(6) . . ? C11 C10 C9 121.5(7) . . ? C11 C10 I2 117.2(5) . . ? C9 C10 I2 121.3(5) . . ? C12 C11 C10 119.2(7) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 119.5(7) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.8(7) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 121.0(7) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? O3 C15 C16 111.2(6) . . ? O3 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? O3 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C21 117.2(7) . . ? C17 C16 C15 123.1(7) . . ? C21 C16 C15 119.7(7) . . ? C16 C17 C18 121.4(7) . . ? C16 C17 I3 121.5(5) . . ? C18 C17 I3 117.0(5) . . ? C19 C18 C17 118.9(7) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C20 C19 C18 120.2(8) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.6(8) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C16 121.6(8) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.757 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.141 _atom_sites_special_details ; The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.042 ; _database_code_depnum_ccdc_archive 'CCDC 891201' ####################################################################### # # 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_mlc85d_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 Au Br3 Cl N P' _chemical_formula_weight 814.52 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.6165(5) _cell_length_b 13.1976(4) _cell_length_c 14.9182(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2483.99(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 29.85 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 10.932 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1113 _exptl_absorpt_correction_T_max 0.1983 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 17891 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6257 _reflns_number_gt 6068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0518P)^2^+2.1446P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack -0.008(7) _refine_ls_number_reflns 6257 _refine_ls_number_parameters 272 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.043 _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 1.195440(17) 0.545880(12) 0.984558(12) 0.01674(6) Uani 1 1 d . . . Cl1 Cl 1.19470(14) 0.66183(9) 0.86940(8) 0.0247(3) Uani 1 1 d . . . P1 P 1.19766(12) 0.43885(9) 1.09966(9) 0.0162(2) Uani 1 1 d . . . Br1 Br 1.41188(5) 0.38254(4) 0.92497(4) 0.02352(12) Uani 1 1 d . . . Br2 Br 0.97091(5) 0.40348(4) 0.92126(4) 0.02398(12) Uani 1 1 d . . . Br3 Br 1.13773(5) 0.73451(4) 1.14901(4) 0.02693(13) Uani 1 1 d . . . C1 C 1.3265(4) 0.3807(4) 1.1238(4) 0.0184(11) Uani 1 1 d . . . H1A H 1.3278 0.3594 1.1860 0.022 Uiso 1 1 calc R . . H1B H 1.3347 0.3207 1.0868 0.022 Uiso 1 1 calc R . . C2 C 1.4184(5) 0.4509(4) 1.1069(4) 0.0209(10) Uani 1 1 d . . . C3 C 1.4636(4) 0.4612(4) 1.0221(4) 0.0196(10) Uani 1 1 d . . . C4 C 1.5468(5) 0.5268(4) 1.0063(4) 0.0279(13) Uani 1 1 d . . . H4 H 1.5741 0.5342 0.9487 0.033 Uiso 1 1 calc R . . C5 C 1.5893(5) 0.5815(4) 1.0770(5) 0.0302(13) Uani 1 1 d . . . H5 H 1.6470 0.6239 1.0673 0.036 Uiso 1 1 calc R . . C6 C 1.5467(5) 0.5734(4) 1.1612(4) 0.0279(13) Uani 1 1 d . . . H6 H 1.5743 0.6117 1.2081 0.033 Uiso 1 1 calc R . . C7 C 1.4621(5) 0.5078(4) 1.1764(4) 0.0248(12) Uani 1 1 d . . . H7 H 1.4343 0.5019 1.2339 0.030 Uiso 1 1 calc R . . C8 C 1.1089(5) 0.3294(4) 1.0888(4) 0.0201(11) Uani 1 1 d . . . H8A H 1.1206 0.2835 1.1386 0.024 Uiso 1 1 calc R . . H8B H 1.0359 0.3522 1.0914 0.024 Uiso 1 1 calc R . . C9 C 1.1273(4) 0.2740(4) 1.0023(4) 0.0204(11) Uani 1 1 d . . . C10 C 1.0775(5) 0.3009(4) 0.9230(4) 0.0212(11) Uani 1 1 d . . . C11 C 1.0992(5) 0.2526(4) 0.8429(4) 0.0246(11) Uani 1 1 d . . . H11 H 1.0645 0.2722 0.7907 0.029 Uiso 1 1 calc R . . C12 C 1.1730(5) 0.1748(5) 0.8408(4) 0.0310(14) Uani 1 1 d . . . H12 H 1.1888 0.1426 0.7870 0.037 Uiso 1 1 calc R . . C13 C 1.2227(5) 0.1455(4) 0.9187(5) 0.0310(14) Uani 1 1 d . . . H13 H 1.2719 0.0930 0.9178 0.037 Uiso 1 1 calc R . . C14 C 1.1992(5) 0.1942(4) 0.9987(4) 0.0215(10) Uani 1 1 d . . . H14 H 1.2324 0.1730 1.0511 0.026 Uiso 1 1 calc R . . C15 C 1.1623(5) 0.4996(4) 1.2056(4) 0.0225(11) Uani 1 1 d . . . H15A H 1.1687 0.4503 1.2535 0.027 Uiso 1 1 calc R . . H15B H 1.2126 0.5535 1.2176 0.027 Uiso 1 1 calc R . . C16 C 1.0520(4) 0.5433(4) 1.2073(4) 0.0210(10) Uani 1 1 d . . . C17 C 1.0285(5) 0.6429(4) 1.1840(4) 0.0209(11) Uani 1 1 d . . . C18 C 0.9272(5) 0.6813(4) 1.1886(4) 0.0255(12) Uani 1 1 d . . . H18 H 0.9142 0.7478 1.1712 0.031 Uiso 1 1 calc R . . C19 C 0.8457(5) 0.6225(5) 1.2183(5) 0.0335(14) Uani 1 1 d . . . H19 H 0.7779 0.6495 1.2235 0.040 Uiso 1 1 calc R . . C20 C 0.8646(6) 0.5215(5) 1.2410(5) 0.0333(14) Uani 1 1 d . . . H20 H 0.8084 0.4816 1.2606 0.040 Uiso 1 1 calc R . . C21 C 0.9620(6) 0.4800(5) 1.2355(4) 0.0332(15) Uani 1 1 d U . . H21 H 0.9722 0.4120 1.2494 0.040 Uiso 1 1 calc R . . N1S N 0.7968(6) 0.5726(5) 0.9137(5) 0.0481(16) Uani 1 1 d . . . C1S C 0.9113(7) 0.7274(6) 0.9523(5) 0.0428(17) Uani 1 1 d . . . H1S1 H 0.9241 0.7658 0.8987 0.064 Uiso 1 1 calc R . . H1S2 H 0.9776 0.7057 0.9772 0.064 Uiso 1 1 calc R . . H1S3 H 0.8745 0.7688 0.9950 0.064 Uiso 1 1 calc R . . C2S C 0.8478(5) 0.6402(5) 0.9310(4) 0.0292(13) 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 0.01759(10) 0.01687(8) 0.01578(10) 0.00041(6) 0.00123(8) -0.00016(7) Cl1 0.0335(7) 0.0204(5) 0.0201(6) 0.0027(4) 0.0044(6) 0.0028(6) P1 0.0153(6) 0.0174(5) 0.0160(6) 0.0004(4) 0.0015(6) 0.0012(5) Br1 0.0232(3) 0.0297(2) 0.0177(3) -0.00179(19) 0.0001(2) 0.0028(2) Br2 0.0188(3) 0.0255(2) 0.0276(3) 0.0000(2) -0.0010(2) 0.0020(2) Br3 0.0242(3) 0.0218(2) 0.0349(3) -0.0030(2) 0.0052(3) -0.0044(2) C1 0.018(3) 0.022(2) 0.015(2) -0.0003(17) -0.001(2) 0.0029(18) C2 0.018(3) 0.019(2) 0.025(3) 0.000(2) 0.001(2) 0.004(2) C3 0.018(3) 0.024(2) 0.017(2) 0.001(2) -0.002(2) 0.0042(19) C4 0.027(3) 0.026(2) 0.031(3) 0.000(2) 0.008(3) 0.002(2) C5 0.018(3) 0.024(2) 0.048(4) -0.006(2) 0.001(3) -0.002(2) C6 0.020(3) 0.030(3) 0.033(3) -0.013(2) 0.001(3) 0.002(2) C7 0.017(3) 0.027(3) 0.030(3) -0.004(2) -0.003(2) 0.003(2) C8 0.023(3) 0.017(2) 0.020(3) 0.0002(17) 0.004(2) -0.0064(19) C9 0.020(3) 0.019(2) 0.023(3) -0.0002(18) 0.002(2) -0.0055(18) C10 0.024(3) 0.019(2) 0.021(3) -0.0011(18) 0.005(2) -0.001(2) C11 0.025(3) 0.031(3) 0.018(3) 0.000(2) -0.001(2) 0.003(2) C12 0.036(4) 0.031(3) 0.026(3) -0.008(2) 0.005(3) 0.001(2) C13 0.024(3) 0.022(2) 0.047(4) -0.006(2) 0.005(3) 0.002(2) C14 0.020(3) 0.018(2) 0.026(3) 0.0016(17) 0.001(2) -0.0003(19) C15 0.027(3) 0.022(2) 0.018(3) -0.0015(19) -0.005(2) 0.006(2) C16 0.021(3) 0.026(2) 0.015(2) -0.007(2) 0.003(2) 0.001(2) C17 0.018(3) 0.026(2) 0.018(3) -0.0036(19) -0.002(2) -0.004(2) C18 0.022(3) 0.029(3) 0.025(3) -0.002(2) 0.001(2) 0.003(2) C19 0.019(3) 0.046(3) 0.036(4) -0.014(3) 0.000(3) 0.001(2) C20 0.028(4) 0.039(3) 0.033(3) -0.009(2) 0.005(3) -0.013(3) C21 0.052(4) 0.040(3) 0.008(2) -0.004(2) 0.002(3) 0.025(3) N1S 0.030(3) 0.041(3) 0.073(5) -0.004(3) -0.008(4) 0.003(3) C1S 0.041(4) 0.050(4) 0.037(4) 0.004(3) -0.003(3) -0.011(3) C2S 0.019(3) 0.039(3) 0.029(3) 0.005(2) 0.003(3) 0.006(3) _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 P1 2.2237(12) . ? Au1 Cl1 2.3006(12) . ? P1 C15 1.828(6) . ? P1 C1 1.833(5) . ? P1 C8 1.835(5) . ? Br1 C3 1.898(5) . ? Br2 C10 1.909(6) . ? Br3 C17 1.907(6) . ? C1 C2 1.506(8) . ? C2 C7 1.394(8) . ? C2 C3 1.394(8) . ? C3 C4 1.381(8) . ? C4 C5 1.386(9) . ? C5 C6 1.370(9) . ? C6 C7 1.394(9) . ? C8 C9 1.501(7) . ? C9 C10 1.385(8) . ? C9 C14 1.392(7) . ? C10 C11 1.382(8) . ? C11 C12 1.386(9) . ? C12 C13 1.376(10) . ? C13 C14 1.387(8) . ? C15 C16 1.506(8) . ? C16 C17 1.392(8) . ? C16 C21 1.471(9) . ? C17 C18 1.376(8) . ? C18 C19 1.362(9) . ? C19 C20 1.396(10) . ? C20 C21 1.348(9) . ? N1S C2S 1.130(9) . ? C1S C2S 1.438(10) . ? 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 P1 Au1 Cl1 177.70(5) . . ? C15 P1 C1 103.3(3) . . ? C15 P1 C8 105.8(3) . . ? C1 P1 C8 103.2(2) . . ? C15 P1 Au1 112.70(18) . . ? C1 P1 Au1 115.39(18) . . ? C8 P1 Au1 115.12(18) . . ? C2 C1 P1 113.1(4) . . ? C7 C2 C3 117.5(5) . . ? C7 C2 C1 120.8(5) . . ? C3 C2 C1 121.8(5) . . ? C4 C3 C2 121.8(5) . . ? C4 C3 Br1 118.3(4) . . ? C2 C3 Br1 119.9(4) . . ? C3 C4 C5 119.3(6) . . ? C6 C5 C4 120.4(6) . . ? C5 C6 C7 119.9(6) . . ? C6 C7 C2 121.1(6) . . ? C9 C8 P1 111.4(4) . . ? C10 C9 C14 117.1(5) . . ? C10 C9 C8 122.7(5) . . ? C14 C9 C8 120.2(5) . . ? C11 C10 C9 122.1(5) . . ? C11 C10 Br2 117.0(4) . . ? C9 C10 Br2 120.8(4) . . ? C10 C11 C12 119.5(6) . . ? C13 C12 C11 119.7(6) . . ? C12 C13 C14 119.9(5) . . ? C13 C14 C9 121.6(5) . . ? C16 C15 P1 114.1(4) . . ? C17 C16 C21 116.3(5) . . ? C17 C16 C15 123.6(5) . . ? C21 C16 C15 120.0(5) . . ? C18 C17 C16 122.2(5) . . ? C18 C17 Br3 116.9(4) . . ? C16 C17 Br3 120.9(4) . . ? C19 C18 C17 120.5(6) . . ? C18 C19 C20 119.6(6) . . ? C21 C20 C19 122.0(6) . . ? C20 C21 C16 119.3(6) . . ? N1S C2S C1S 179.0(8) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.287 _refine_diff_density_min -1.474 _refine_diff_density_rms 0.182 _database_code_depnum_ccdc_archive 'CCDC 891203' ####################################################################### # # 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_mo_mlc59b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Au Cl I3 O3 P' _chemical_formula_weight 920.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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)/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 11.0595(5) _cell_length_b 12.7552(6) _cell_length_c 16.4234(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.0190(10) _cell_angle_gamma 90.00 _cell_volume 2237.64(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9465 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 29.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 10.920 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 16293 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 30.03 _reflns_number_total 5473 _reflns_number_gt 4935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0921P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5473 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 0.761 _refine_ls_restrained_S_all 0.761 _refine_ls_shift/su_max 0.005 _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 0.128346(15) 0.254635(13) 1.061557(10) 0.01467(7) Uani 1 1 d . . . C1 C 0.3416(4) 0.4202(4) 0.9613(3) 0.0159(8) Uani 1 1 d . . . C2 C 0.3611(4) 0.4579(4) 0.8867(3) 0.0165(8) Uani 1 1 d . . . C3 C 0.3448(4) 0.5652(4) 0.8695(3) 0.0207(9) Uani 1 1 d . . . H3 H 0.3571 0.5926 0.8198 0.025 Uiso 1 1 calc R . . C4 C 0.3098(4) 0.6305(4) 0.9274(3) 0.0229(10) Uani 1 1 d . . . H4 H 0.2978 0.7017 0.9158 0.028 Uiso 1 1 calc R . . C5 C 0.2930(4) 0.5912(4) 1.0011(3) 0.0231(10) Uani 1 1 d . . . H5 H 0.2700 0.6359 1.0393 0.028 Uiso 1 1 calc R . . C6 C 0.3100(4) 0.4850(4) 1.0198(3) 0.0202(9) Uani 1 1 d . . . H6 H 0.3002 0.4584 1.0704 0.024 Uiso 1 1 calc R . . C7 C 0.0440(4) 0.2150(4) 0.8445(2) 0.0152(8) Uani 1 1 d . . . C8 C -0.0560(4) 0.2845(4) 0.8332(3) 0.0174(9) Uani 1 1 d . . . C9 C -0.1759(5) 0.2474(3) 0.7963(3) 0.0185(10) Uani 1 1 d . . . H9 H -0.2436 0.2931 0.7866 0.022 Uiso 1 1 calc R . . C10 C -0.1953(4) 0.1428(4) 0.7739(3) 0.0217(10) Uani 1 1 d . . . H10 H -0.2759 0.1183 0.7499 0.026 Uiso 1 1 calc R . . C11 C -0.0944(4) 0.0750(4) 0.7871(3) 0.0227(10) Uani 1 1 d . . . H11 H -0.1076 0.0047 0.7724 0.027 Uiso 1 1 calc R . . C12 C 0.0261(4) 0.1110(4) 0.8222(3) 0.0197(9) Uani 1 1 d . . . H12 H 0.0940 0.0655 0.8306 0.024 Uiso 1 1 calc R . . C13 C 0.3793(4) 0.0745(4) 1.0395(3) 0.0163(8) Uani 1 1 d . . . C14 C 0.3478(4) -0.0254(4) 1.0581(3) 0.0154(8) Uani 1 1 d . . . C15 C 0.4278(4) -0.0798(4) 1.1239(3) 0.0218(9) Uani 1 1 d . . . H15 H 0.4079 -0.1476 1.1368 0.026 Uiso 1 1 calc R . . C16 C 0.5368(4) -0.0333(4) 1.1700(3) 0.0238(10) Uani 1 1 d . . . H16 H 0.5905 -0.0701 1.2136 0.029 Uiso 1 1 calc R . . C17 C 0.5664(4) 0.0672(5) 1.1518(3) 0.0268(11) Uani 1 1 d . . . H17 H 0.6395 0.0986 1.1833 0.032 Uiso 1 1 calc R . . C18 C 0.4866(4) 0.1215(4) 1.0860(3) 0.0225(10) Uani 1 1 d . . . H18 H 0.5060 0.1896 1.0735 0.027 Uiso 1 1 calc R . . Cl1 Cl 0.00565(10) 0.27679(10) 1.15229(7) 0.0205(2) Uani 1 1 d . . . I1 I 0.41533(3) 0.35957(2) 0.800856(17) 0.01722(8) Uani 1 1 d . . . I2 I -0.02666(3) 0.44135(2) 0.870171(18) 0.02089(9) Uani 1 1 d . . . I3 I 0.18413(3) -0.09847(2) 0.987155(18) 0.02186(9) Uani 1 1 d . . . O1 O 0.3578(3) 0.3111(2) 0.97798(18) 0.0165(6) Uani 1 1 d . . . O2 O 0.1670(3) 0.2515(2) 0.8752(2) 0.0165(7) Uani 1 1 d . . . O3 O 0.3042(3) 0.1253(2) 0.96777(18) 0.0159(6) Uani 1 1 d . . . P1 P 0.24101(11) 0.23553(9) 0.97072(7) 0.0137(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 Au1 0.01557(11) 0.01501(12) 0.01331(11) -0.00038(5) 0.00351(7) -0.00139(6) C1 0.0137(18) 0.012(2) 0.0190(19) -0.0013(16) -0.0019(15) -0.0022(16) C2 0.0138(17) 0.018(2) 0.0177(18) -0.0016(17) 0.0040(15) -0.0028(16) C3 0.021(2) 0.014(2) 0.025(2) -0.0001(18) 0.0034(17) -0.0007(18) C4 0.016(2) 0.011(2) 0.040(3) 0.0019(19) 0.0046(19) -0.0012(17) C5 0.024(2) 0.017(3) 0.029(2) -0.0103(19) 0.0095(19) -0.0014(18) C6 0.018(2) 0.025(3) 0.018(2) -0.0028(18) 0.0054(16) -0.0033(18) C7 0.0147(18) 0.020(2) 0.0107(17) 0.0012(16) 0.0030(14) -0.0012(17) C8 0.023(2) 0.015(2) 0.0120(18) -0.0007(17) 0.0017(16) -0.0005(19) C9 0.014(2) 0.022(3) 0.017(2) 0.0017(16) -0.0003(17) 0.0037(16) C10 0.0157(19) 0.028(3) 0.020(2) -0.0031(19) 0.0025(16) -0.0035(18) C11 0.027(2) 0.017(3) 0.022(2) -0.0052(18) 0.0020(18) -0.0004(19) C12 0.023(2) 0.017(2) 0.019(2) -0.0033(17) 0.0045(17) 0.0067(18) C13 0.0179(19) 0.017(2) 0.0138(18) -0.0001(16) 0.0036(15) 0.0030(17) C14 0.0155(18) 0.015(2) 0.0151(18) -0.0012(16) 0.0035(15) -0.0029(16) C15 0.020(2) 0.017(2) 0.027(2) 0.0043(18) 0.0037(18) 0.0049(18) C16 0.020(2) 0.030(3) 0.020(2) 0.004(2) 0.0043(17) 0.005(2) C17 0.017(2) 0.035(3) 0.024(2) 0.002(2) -0.0030(17) -0.001(2) C18 0.020(2) 0.017(2) 0.027(2) 0.0019(19) -0.0005(18) -0.0039(19) Cl1 0.0199(5) 0.0250(6) 0.0177(5) -0.0027(4) 0.0069(4) -0.0048(5) I1 0.01947(14) 0.01499(17) 0.01773(14) 0.00063(10) 0.00576(11) 0.00148(10) I2 0.02252(15) 0.01419(17) 0.02493(16) -0.00063(11) 0.00427(12) 0.00204(11) I3 0.02308(15) 0.01468(18) 0.02418(16) 0.00069(11) -0.00043(12) -0.00367(11) O1 0.0186(14) 0.0127(16) 0.0168(14) 0.0018(12) 0.0017(11) -0.0006(12) O2 0.0158(15) 0.0178(19) 0.0146(15) 0.0019(11) 0.0017(12) 0.0006(11) O3 0.0180(14) 0.0130(16) 0.0151(14) -0.0009(12) 0.0015(11) -0.0021(12) P1 0.0147(5) 0.0122(6) 0.0135(5) -0.0002(4) 0.0022(4) 0.0003(4) _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 P1 2.1910(12) . ? Au1 Cl1 2.2781(11) . ? C1 C2 1.385(6) . ? C1 C6 1.379(6) . ? C1 O1 1.420(5) . ? C2 C3 1.399(7) . ? C2 I1 2.089(4) . ? C3 C4 1.393(7) . ? C4 C5 1.367(7) . ? C5 C6 1.390(7) . ? C7 C12 1.377(7) . ? C7 C8 1.392(6) . ? C7 O2 1.401(5) . ? C8 C9 1.391(7) . ? C8 I2 2.091(5) . ? C9 C10 1.385(7) . ? C10 C11 1.384(7) . ? C11 C12 1.387(6) . ? C13 C18 1.371(6) . ? C13 C14 1.376(6) . ? C13 O3 1.411(5) . ? C14 C15 1.392(6) . ? C14 I3 2.100(4) . ? C15 C16 1.381(7) . ? C16 C17 1.375(8) . ? C17 C18 1.390(6) . ? O1 P1 1.591(3) . ? O2 P1 1.583(3) . ? O3 P1 1.576(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 Cl1 177.99(4) . . ? C2 C1 C6 122.2(4) . . ? C2 C1 O1 118.1(4) . . ? C6 C1 O1 119.7(4) . . ? C1 C2 C3 118.5(4) . . ? C1 C2 I1 121.8(3) . . ? C3 C2 I1 119.7(3) . . ? C4 C3 C2 119.4(4) . . ? C5 C4 C3 120.7(5) . . ? C4 C5 C6 120.7(4) . . ? C5 C6 C1 118.4(4) . . ? C12 C7 C8 121.6(4) . . ? C12 C7 O2 118.3(4) . . ? C8 C7 O2 120.0(4) . . ? C7 C8 C9 118.5(5) . . ? C7 C8 I2 120.8(3) . . ? C9 C8 I2 120.7(4) . . ? C10 C9 C8 120.5(5) . . ? C11 C10 C9 119.8(4) . . ? C10 C11 C12 120.5(5) . . ? C7 C12 C11 119.1(4) . . ? C18 C13 C14 120.9(4) . . ? C18 C13 O3 120.1(4) . . ? C14 C13 O3 118.8(4) . . ? C13 C14 C15 119.2(4) . . ? C13 C14 I3 121.3(3) . . ? C15 C14 I3 119.5(4) . . ? C16 C15 C14 120.0(5) . . ? C15 C16 C17 120.3(4) . . ? C18 C17 C16 119.7(4) . . ? C13 C18 C17 119.8(5) . . ? C1 O1 P1 121.3(3) . . ? C7 O2 P1 121.2(3) . . ? C13 O3 P1 123.6(3) . . ? O3 P1 O2 101.76(16) . . ? O3 P1 O1 100.64(16) . . ? O2 P1 O1 101.40(17) . . ? O3 P1 Au1 117.07(13) . . ? O2 P1 Au1 114.89(14) . . ? O1 P1 Au1 118.39(13) . . ? _diffrn_measured_fraction_theta_max 0.837 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.739 _refine_diff_density_min -1.597 _refine_diff_density_rms 0.232 _database_code_depnum_ccdc_archive 'CCDC 891204' ####################################################################### # # 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_mo_mlc85_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 Au Br6 Cl9 P2' _chemical_formula_weight 1654.23 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' P P 0.1023 0.0942 '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' 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 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 17.0229(14) _cell_length_b 16.1927(14) _cell_length_c 20.3819(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.408(3) _cell_angle_gamma 90.00 _cell_volume 5389.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9814 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 29.56 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 7.717 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2055 _exptl_absorpt_correction_T_max 0.5125 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Micorfocus source E025 IuS' _diffrn_source_type 'Bruker APEX DUO' _diffrn_source_power 50 _diffrn_source_current 0.6 _diffrn_source_size '0.2 mm x 0.2 mm fine focus' _diffrn_radiation_monochromator 'Quazar MX Multilayer Optics' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'APEX DUO Kappa 4-axis goniometer' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 51011 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 30.04 _reflns_number_total 7285 _reflns_number_gt 5884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2011.4-0' _computing_cell_refinement 'Bruker APEX2 v2011.4-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2011 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0475P)^2^+74.7449P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7285 _refine_ls_number_parameters 322 _refine_ls_number_restraints 118 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.133 _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 0.7500 0.7500 0.5000 0.02714(9) Uani 1 2 d S . . P1 P 0.66603(8) 0.67007(10) 0.41581(7) 0.0272(3) Uani 1 1 d . . . Br1 Br 0.68263(4) 0.91096(5) 0.36001(4) 0.04769(19) Uani 1 1 d . . . Br2 Br 0.60460(4) 0.68200(4) 0.58950(3) 0.03833(16) Uani 1 1 d . . . Br3 Br 0.90065(4) 0.59848(5) 0.47916(4) 0.04968(19) Uani 1 1 d . . . C1 C 0.6201(4) 0.7247(4) 0.3355(3) 0.0309(12) Uani 1 1 d . . . H1A H 0.6642 0.7521 0.3207 0.037 Uiso 1 1 calc R . . H1B H 0.5940 0.6836 0.3000 0.037 Uiso 1 1 calc R . . C2 C 0.5571(4) 0.7885(4) 0.3393(3) 0.0315(12) Uani 1 1 d . . . C3 C 0.5744(4) 0.8717(4) 0.3483(3) 0.0356(13) Uani 1 1 d . . . C4 C 0.5142(4) 0.9303(5) 0.3480(4) 0.0428(15) Uani 1 1 d . . . H4 H 0.5278 0.9872 0.3544 0.051 Uiso 1 1 calc R . . C5 C 0.4338(4) 0.9039(5) 0.3382(4) 0.0467(17) Uani 1 1 d . . . H5 H 0.3911 0.9424 0.3363 0.056 Uiso 1 1 calc R . . C6 C 0.4176(4) 0.8184(5) 0.3310(3) 0.0380(15) Uani 1 1 d . . . H6 H 0.3637 0.7991 0.3266 0.046 Uiso 1 1 calc R . . C7 C 0.4752(4) 0.7648(4) 0.3302(3) 0.0357(14) Uani 1 1 d . . . H7 H 0.4611 0.7081 0.3233 0.043 Uiso 1 1 calc R . . C8 C 0.5767(3) 0.6242(5) 0.4354(3) 0.0352(14) Uani 1 1 d . . . H8A H 0.5463 0.6686 0.4510 0.042 Uiso 1 1 calc R . . H8B H 0.5401 0.6010 0.3927 0.042 Uiso 1 1 calc R . . C9 C 0.5961(3) 0.5575(4) 0.4887(3) 0.0330(13) Uani 1 1 d . . . C10 C 0.6094(4) 0.5726(4) 0.5586(3) 0.0327(13) Uani 1 1 d . . . C11 C 0.6238(4) 0.5086(4) 0.6062(3) 0.0351(13) Uani 1 1 d . . . H11 H 0.6319 0.5203 0.6534 0.042 Uiso 1 1 calc R . . C12 C 0.6260(4) 0.4288(5) 0.5845(4) 0.0431(16) Uani 1 1 d . . . H12 H 0.6363 0.3848 0.6167 0.052 Uiso 1 1 calc R . . C13 C 0.6131(5) 0.4123(5) 0.5159(4) 0.0480(17) Uani 1 1 d . . . H13 H 0.6151 0.3564 0.5021 0.058 Uiso 1 1 calc R . . C14 C 0.5982(4) 0.4701(6) 0.4684(3) 0.0458(19) Uani 1 1 d . . . H14 H 0.5890 0.4557 0.4217 0.055 Uiso 1 1 calc R . . C15 C 0.7134(3) 0.5807(4) 0.3875(3) 0.0298(12) Uani 1 1 d . . . H15A H 0.7401 0.5465 0.4279 0.036 Uiso 1 1 calc R . . H15B H 0.6698 0.5468 0.3568 0.036 Uiso 1 1 calc R . . C16 C 0.7761(4) 0.6019(4) 0.3503(3) 0.0313(12) Uani 1 1 d . . . C17 C 0.8587(4) 0.6122(4) 0.3830(3) 0.0368(14) Uani 1 1 d . . . C18 C 0.9145(4) 0.6317(4) 0.3466(4) 0.0394(15) Uani 1 1 d . . . H18 H 0.9709 0.6391 0.3699 0.047 Uiso 1 1 calc R . . C19 C 0.8873(5) 0.6402(4) 0.2770(4) 0.0453(17) Uani 1 1 d . . . H19 H 0.9248 0.6533 0.2518 0.054 Uiso 1 1 calc R . . C20 C 0.8042(5) 0.6293(5) 0.2432(4) 0.0474(17) Uani 1 1 d . . . H20 H 0.7859 0.6348 0.1948 0.057 Uiso 1 1 calc R . . C21 C 0.7511(4) 0.6119(4) 0.2764(4) 0.0446(17) Uani 1 1 d . . . H21 H 0.6950 0.6056 0.2519 0.054 Uiso 1 1 calc R . . C1S C 0.8927(4) 0.8598(5) 0.2282(4) 0.0523(19) Uani 1 1 d D . . H1S1 H 0.9081 0.8250 0.2697 0.063 Uiso 1 1 calc R . . H1S2 H 0.9277 0.9098 0.2373 0.063 Uiso 1 1 calc R . . Cl1S Cl 0.91164(17) 0.80470(15) 0.15940(13) 0.0692(6) Uani 1 1 d D . . Cl2S Cl 0.79006(13) 0.88932(16) 0.21168(15) 0.0700(7) Uani 1 1 d D . . C1T C 0.8712(12) 0.3468(17) 0.4943(13) 0.104(2) Uani 0.50 1 d PDU A 1 H1T1 H 0.8800 0.3872 0.4606 0.124 Uiso 0.50 1 calc PR A 1 H1T2 H 0.9229 0.3159 0.5130 0.124 Uiso 0.50 1 calc PR A 1 Cl1T Cl 0.8455(6) 0.3999(6) 0.5614(6) 0.0940(15) Uani 0.50 1 d PDU A 1 Cl2T Cl 0.7934(5) 0.2781(5) 0.4534(4) 0.1128(16) Uani 0.50 1 d PDU A 1 C1T' C 0.829(2) 0.371(3) 0.4801(11) 0.103(2) Uani 0.25 1 d PDU B 2 H1T3 H 0.8383 0.4149 0.4495 0.124 Uiso 0.25 1 calc PR B 2 H1T4 H 0.7752 0.3450 0.4582 0.124 Uiso 0.25 1 calc PR B 2 Cl1' Cl 0.9072(8) 0.2955(8) 0.4920(7) 0.0940(15) Uani 0.25 1 d PDU B 2 Cl2' Cl 0.8282(15) 0.4137(16) 0.5587(14) 0.1128(16) Uani 0.25 1 d PDU B 2 C1T" C 0.8702(18) 0.369(3) 0.5062(9) 0.101(2) Uani 0.25 1 d PDU C 3 H1T5 H 0.8775 0.4298 0.5113 0.122 Uiso 0.25 1 calc PR C 3 H1T6 H 0.9188 0.3462 0.4951 0.122 Uiso 0.25 1 calc PR C 3 Cl1" Cl 0.8629(8) 0.3264(8) 0.5841(6) 0.0940(15) Uani 0.25 1 d PDU C 3 Cl2" Cl 0.7824(10) 0.3478(11) 0.4392(6) 0.1128(16) Uani 0.25 1 d PDU C 3 Cl1 Cl 0.0000 0.04884(13) 0.2500 0.0359(4) Uani 1 2 d S . . 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 0.01649(14) 0.04518(18) 0.01838(14) 0.00473(12) 0.00271(10) 0.00299(12) P1 0.0174(6) 0.0450(8) 0.0191(6) 0.0047(6) 0.0050(5) 0.0022(6) Br1 0.0269(3) 0.0553(4) 0.0580(4) 0.0145(3) 0.0072(3) -0.0002(3) Br2 0.0406(3) 0.0468(4) 0.0316(3) 0.0028(3) 0.0168(3) 0.0027(3) Br3 0.0338(3) 0.0685(5) 0.0439(4) 0.0106(3) 0.0063(3) 0.0138(3) C1 0.027(3) 0.046(3) 0.019(2) 0.003(2) 0.006(2) 0.004(2) C2 0.023(3) 0.049(4) 0.019(3) 0.002(2) 0.001(2) 0.008(2) C3 0.025(3) 0.047(4) 0.031(3) 0.006(3) 0.000(2) 0.002(3) C4 0.031(3) 0.045(4) 0.046(4) 0.001(3) 0.001(3) 0.005(3) C5 0.025(3) 0.063(5) 0.048(4) -0.007(3) 0.003(3) 0.010(3) C6 0.022(3) 0.064(4) 0.026(3) -0.013(3) 0.003(2) -0.011(3) C7 0.032(3) 0.048(4) 0.022(3) -0.006(2) 0.000(2) -0.005(3) C8 0.019(3) 0.063(4) 0.023(3) 0.008(3) 0.004(2) -0.002(3) C9 0.020(3) 0.052(4) 0.027(3) -0.001(3) 0.006(2) -0.007(2) C10 0.026(3) 0.048(4) 0.025(3) 0.001(3) 0.009(2) -0.003(3) C11 0.029(3) 0.048(4) 0.028(3) 0.003(3) 0.007(2) -0.005(3) C12 0.034(3) 0.050(4) 0.043(4) 0.010(3) 0.007(3) -0.006(3) C13 0.049(4) 0.046(4) 0.051(4) -0.010(3) 0.017(3) -0.013(3) C14 0.023(3) 0.092(6) 0.023(3) 0.002(3) 0.007(2) -0.017(3) C15 0.024(3) 0.041(3) 0.025(3) 0.004(2) 0.008(2) -0.003(2) C16 0.029(3) 0.034(3) 0.036(3) 0.002(2) 0.016(2) 0.004(2) C17 0.032(3) 0.040(3) 0.040(3) 0.003(3) 0.014(3) 0.006(3) C18 0.027(3) 0.041(3) 0.056(4) -0.003(3) 0.020(3) 0.002(3) C19 0.045(4) 0.043(4) 0.061(5) -0.002(3) 0.036(4) 0.000(3) C20 0.072(5) 0.040(4) 0.033(3) -0.001(3) 0.019(3) 0.003(3) C21 0.027(3) 0.043(4) 0.063(5) -0.022(3) 0.009(3) 0.000(3) C1S 0.047(4) 0.052(4) 0.066(5) -0.012(4) 0.030(4) -0.003(3) Cl1S 0.0959(18) 0.0625(13) 0.0684(14) 0.0032(11) 0.0546(14) 0.0062(12) Cl2S 0.0372(10) 0.0792(15) 0.0981(18) -0.0218(13) 0.0267(11) -0.0126(10) C1T 0.115(5) 0.107(5) 0.100(4) -0.031(4) 0.049(4) -0.033(4) Cl1T 0.107(3) 0.095(3) 0.097(3) -0.023(2) 0.055(3) -0.040(3) Cl2T 0.121(4) 0.120(3) 0.102(3) -0.037(3) 0.039(3) -0.029(3) C1T' 0.114(5) 0.106(5) 0.100(4) -0.030(4) 0.047(4) -0.033(4) Cl1' 0.107(3) 0.095(3) 0.097(3) -0.023(2) 0.055(3) -0.040(3) Cl2' 0.121(4) 0.120(3) 0.102(3) -0.037(3) 0.039(3) -0.029(3) C1T" 0.114(5) 0.106(5) 0.097(4) -0.027(4) 0.050(4) -0.035(4) Cl1" 0.107(3) 0.095(3) 0.097(3) -0.023(2) 0.055(3) -0.040(3) Cl2" 0.121(4) 0.120(3) 0.102(3) -0.037(3) 0.039(3) -0.029(3) Cl1 0.0359(11) 0.0301(10) 0.0374(11) 0.000 0.0035(9) 0.000 _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 P1 2.2972(15) 7_666 ? Au1 P1 2.2972(15) . ? P1 C15 1.828(6) . ? P1 C1 1.830(6) . ? P1 C8 1.834(6) . ? Br1 C3 1.900(6) . ? Br2 C10 1.890(7) . ? Br3 C17 1.900(7) . ? C1 C2 1.507(8) . ? C2 C3 1.380(10) . ? C2 C7 1.407(9) . ? C3 C4 1.396(9) . ? C4 C5 1.392(10) . ? C5 C6 1.412(11) . ? C6 C7 1.312(10) . ? C8 C9 1.502(9) . ? C9 C10 1.399(8) . ? C9 C14 1.477(11) . ? C10 C11 1.393(9) . ? C11 C12 1.371(10) . ? C12 C13 1.379(11) . ? C13 C14 1.319(11) . ? C15 C16 1.513(8) . ? C16 C17 1.385(9) . ? C16 C21 1.454(10) . ? C17 C18 1.398(9) . ? C18 C19 1.368(11) . ? C19 C20 1.400(11) . ? C20 C21 1.304(10) . ? C1S Cl2S 1.751(7) . ? C1S Cl1S 1.766(6) . ? C1T Cl2T 1.750(9) . ? C1T Cl1T 1.772(7) . ? C1T' Cl2' 1.751(9) . ? C1T' Cl1' 1.771(7) . ? C1T" Cl2" 1.750(9) . ? C1T" Cl1" 1.769(7) . ? 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 P1 Au1 P1 179.999(1) 7_666 . ? C15 P1 C1 102.4(3) . . ? C15 P1 C8 102.4(3) . . ? C1 P1 C8 102.6(3) . . ? C15 P1 Au1 116.4(2) . . ? C1 P1 Au1 114.5(2) . . ? C8 P1 Au1 116.4(2) . . ? C2 C1 P1 114.6(4) . . ? C3 C2 C7 116.7(6) . . ? C3 C2 C1 123.3(6) . . ? C7 C2 C1 119.9(6) . . ? C2 C3 C4 122.3(6) . . ? C2 C3 Br1 120.4(5) . . ? C4 C3 Br1 117.3(5) . . ? C5 C4 C3 118.9(7) . . ? C4 C5 C6 118.1(6) . . ? C7 C6 C5 121.7(6) . . ? C6 C7 C2 122.3(6) . . ? C9 C8 P1 115.0(4) . . ? C10 C9 C14 116.2(6) . . ? C10 C9 C8 123.4(6) . . ? C14 C9 C8 120.3(5) . . ? C11 C10 C9 121.7(6) . . ? C11 C10 Br2 118.7(5) . . ? C9 C10 Br2 119.5(5) . . ? C12 C11 C10 119.4(6) . . ? C11 C12 C13 120.0(7) . . ? C14 C13 C12 123.3(8) . . ? C13 C14 C9 119.4(6) . . ? C16 C15 P1 114.5(4) . . ? C17 C16 C21 116.4(5) . . ? C17 C16 C15 123.4(6) . . ? C21 C16 C15 120.1(5) . . ? C16 C17 C18 121.5(6) . . ? C16 C17 Br3 121.1(5) . . ? C18 C17 Br3 117.4(5) . . ? C19 C18 C17 119.4(6) . . ? C18 C19 C20 119.8(6) . . ? C21 C20 C19 121.6(7) . . ? C20 C21 C16 121.3(7) . . ? Cl2S C1S Cl1S 112.4(4) . . ? Cl2T C1T Cl1T 110.9(6) . . ? Cl2' C1T' Cl1' 110.3(7) . . ? Cl2" C1T" Cl1" 111.2(7) . . ? 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 P1 Au1 P1 C15 -142(50) 7_666 . . . ? P1 Au1 P1 C1 99(50) 7_666 . . . ? P1 Au1 P1 C8 -21(51) 7_666 . . . ? C15 P1 C1 C2 164.0(5) . . . . ? C8 P1 C1 C2 58.0(6) . . . . ? Au1 P1 C1 C2 -69.0(5) . . . . ? P1 C1 C2 C3 97.8(6) . . . . ? P1 C1 C2 C7 -85.3(6) . . . . ? C7 C2 C3 C4 -0.4(9) . . . . ? C1 C2 C3 C4 176.5(6) . . . . ? C7 C2 C3 Br1 -179.3(4) . . . . ? C1 C2 C3 Br1 -2.4(8) . . . . ? C2 C3 C4 C5 -0.2(11) . . . . ? Br1 C3 C4 C5 178.8(6) . . . . ? C3 C4 C5 C6 1.9(11) . . . . ? C4 C5 C6 C7 -3.2(11) . . . . ? C5 C6 C7 C2 2.7(10) . . . . ? C3 C2 C7 C6 -0.9(9) . . . . ? C1 C2 C7 C6 -177.9(6) . . . . ? C15 P1 C8 C9 58.8(5) . . . . ? C1 P1 C8 C9 164.8(5) . . . . ? Au1 P1 C8 C9 -69.4(6) . . . . ? P1 C8 C9 C10 90.9(7) . . . . ? P1 C8 C9 C14 -91.9(6) . . . . ? C14 C9 C10 C11 -0.1(8) . . . . ? C8 C9 C10 C11 177.2(5) . . . . ? C14 C9 C10 Br2 -178.1(4) . . . . ? C8 C9 C10 Br2 -0.7(8) . . . . ? C9 C10 C11 C12 0.9(9) . . . . ? Br2 C10 C11 C12 178.8(5) . . . . ? C10 C11 C12 C13 -0.7(10) . . . . ? C11 C12 C13 C14 -0.2(11) . . . . ? C12 C13 C14 C9 0.9(11) . . . . ? C10 C9 C14 C13 -0.7(9) . . . . ? C8 C9 C14 C13 -178.2(6) . . . . ? C1 P1 C15 C16 58.6(5) . . . . ? C8 P1 C15 C16 164.8(4) . . . . ? Au1 P1 C15 C16 -67.1(5) . . . . ? P1 C15 C16 C17 90.2(7) . . . . ? P1 C15 C16 C21 -90.4(6) . . . . ? C21 C16 C17 C18 0.4(9) . . . . ? C15 C16 C17 C18 179.9(6) . . . . ? C21 C16 C17 Br3 -178.5(5) . . . . ? C15 C16 C17 Br3 1.0(9) . . . . ? C16 C17 C18 C19 -0.6(10) . . . . ? Br3 C17 C18 C19 178.4(5) . . . . ? C17 C18 C19 C20 0.1(10) . . . . ? C18 C19 C20 C21 0.6(11) . . . . ? C19 C20 C21 C16 -0.7(11) . . . . ? C17 C16 C21 C20 0.2(10) . . . . ? C15 C16 C21 C20 -179.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.810 _refine_diff_density_min -2.045 _refine_diff_density_rms 0.170 _database_code_depnum_ccdc_archive 'CCDC 891202' ####################################################################### # # 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_mo_mld84_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 Au Br Cl P' _chemical_formula_weight 587.61 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' P P 0.1023 0.0942 '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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4286(9) _cell_length_b 16.0606(18) _cell_length_c 13.9197(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.295(4) _cell_angle_gamma 90.00 _cell_volume 1808.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8043 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 29.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 10.575 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1436 _exptl_absorpt_correction_T_max 0.4177 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Micorfocus source E025 IuS' _diffrn_source_type 'Bruker APEX DUO' _diffrn_source_power 50 _diffrn_source_current 0.6 _diffrn_source_size '0.2 mm x 0.2 mm fine focus' _diffrn_radiation_monochromator 'Quazar MX Multilayer Optics' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'APEX DUO Kappa 4-axis goniometer' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 15740 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 30.24 _reflns_number_total 4852 _reflns_number_gt 4092 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2011.4-0' _computing_cell_refinement 'Bruker APEX2 v2011.4-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2011 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0695P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4852 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Au1 Au 0.35092(3) 0.858272(13) 0.190729(14) 0.01146(9) Uani 1 1 d . . . Cl1 Cl 0.42750(19) 0.99411(9) 0.17365(10) 0.0170(3) Uani 1 1 d . . . P1 P 0.28560(18) 0.72679(9) 0.21277(10) 0.0111(3) Uani 1 1 d . . . Br1 Br -0.00183(8) 0.90755(4) 0.27116(5) 0.02034(15) Uani 1 1 d . . . C1 C 0.1019(7) 0.7150(4) 0.2573(4) 0.0130(11) Uani 1 1 d . . . H1A H 0.0887 0.6556 0.2724 0.016 Uiso 1 1 calc R . . H1B H 0.1179 0.7469 0.3202 0.016 Uiso 1 1 calc R . . C2 C -0.0545(7) 0.7451(4) 0.1814(4) 0.0125(11) Uani 1 1 d . . . C3 C -0.1158(8) 0.8257(4) 0.1791(4) 0.0160(12) Uani 1 1 d . . . C4 C -0.2639(8) 0.8492(4) 0.1111(5) 0.0175(13) Uani 1 1 d . . . H4 H -0.3048 0.9043 0.1118 0.021 Uiso 1 1 calc R . . C5 C -0.3509(8) 0.7919(4) 0.0427(4) 0.0214(14) Uani 1 1 d . . . H5 H -0.4508 0.8080 -0.0050 0.026 Uiso 1 1 calc R . . C6 C -0.2945(8) 0.7113(4) 0.0428(4) 0.0195(13) Uani 1 1 d . . . H6 H -0.3564 0.6719 -0.0037 0.023 Uiso 1 1 calc R . . C7 C -0.1459(7) 0.6877(4) 0.1114(4) 0.0156(12) Uani 1 1 d . . . H7 H -0.1064 0.6324 0.1107 0.019 Uiso 1 1 calc R . . C8 C 0.4506(7) 0.6728(4) 0.3039(4) 0.0124(11) Uani 1 1 d . . . C9 C 0.4322(8) 0.6383(4) 0.3922(5) 0.0161(13) Uani 1 1 d . . . H9 H 0.3316 0.6444 0.4097 0.019 Uiso 1 1 calc R . . C10 C 0.5661(8) 0.5945(4) 0.4544(4) 0.0168(12) Uani 1 1 d . . . H10 H 0.5566 0.5718 0.5155 0.020 Uiso 1 1 calc R . . C11 C 0.7106(8) 0.5839(4) 0.4286(4) 0.0184(13) Uani 1 1 d . . . H11 H 0.7981 0.5523 0.4708 0.022 Uiso 1 1 calc R . . C12 C 0.7295(8) 0.6192(4) 0.3410(5) 0.0202(13) Uani 1 1 d . . . H12 H 0.8302 0.6126 0.3239 0.024 Uiso 1 1 calc R . . C13 C 0.5992(8) 0.6645(4) 0.2787(4) 0.0175(12) Uani 1 1 d . . . H13 H 0.6115 0.6895 0.2193 0.021 Uiso 1 1 calc R . . C14 C 0.2475(7) 0.6601(4) 0.1033(4) 0.0120(11) Uani 1 1 d . . . C15 C 0.2354(8) 0.5744(4) 0.1149(4) 0.0166(12) Uani 1 1 d . . . H15 H 0.2466 0.5513 0.1794 0.020 Uiso 1 1 calc R . . C16 C 0.2069(8) 0.5229(4) 0.0317(4) 0.0194(13) Uani 1 1 d . . . H16 H 0.1969 0.4645 0.0389 0.023 Uiso 1 1 calc R . . C17 C 0.1928(8) 0.5570(4) -0.0626(4) 0.0224(14) Uani 1 1 d . . . H17 H 0.1748 0.5214 -0.1191 0.027 Uiso 1 1 calc R . . C18 C 0.2046(9) 0.6407(4) -0.0742(5) 0.0209(14) Uani 1 1 d . . . H18 H 0.1938 0.6632 -0.1389 0.025 Uiso 1 1 calc R . . C19 C 0.2328(8) 0.6936(4) 0.0085(4) 0.0155(12) Uani 1 1 d . . . H19 H 0.2418 0.7520 0.0004 0.019 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 0.01289(14) 0.00964(14) 0.01145(13) 0.00010(7) 0.00276(9) -0.00047(7) Cl1 0.0225(8) 0.0109(7) 0.0183(6) -0.0008(5) 0.0068(5) -0.0033(5) P1 0.0115(7) 0.0106(7) 0.0109(6) 0.0010(5) 0.0025(5) 0.0011(5) Br1 0.0216(3) 0.0149(3) 0.0247(3) -0.0049(2) 0.0068(2) 0.0002(2) C1 0.015(3) 0.012(3) 0.013(2) 0.003(2) 0.005(2) -0.002(2) C2 0.011(3) 0.016(3) 0.011(2) 0.001(2) 0.0042(19) 0.002(2) C3 0.019(3) 0.016(3) 0.014(3) 0.005(2) 0.007(2) 0.001(2) C4 0.019(3) 0.018(3) 0.018(3) 0.002(2) 0.009(2) 0.003(2) C5 0.013(3) 0.035(4) 0.016(3) 0.006(3) 0.004(2) 0.005(3) C6 0.017(3) 0.024(4) 0.016(3) -0.003(2) 0.002(2) -0.002(2) C7 0.017(3) 0.016(3) 0.014(3) -0.001(2) 0.005(2) -0.003(2) C8 0.015(3) 0.005(3) 0.016(3) -0.001(2) 0.003(2) -0.002(2) C9 0.018(3) 0.015(3) 0.014(3) 0.001(2) 0.002(2) -0.002(2) C10 0.023(3) 0.011(3) 0.013(3) 0.001(2) 0.000(2) -0.003(2) C11 0.019(3) 0.013(3) 0.017(3) -0.004(2) -0.004(2) 0.005(2) C12 0.014(3) 0.024(3) 0.020(3) 0.001(3) 0.001(2) 0.005(3) C13 0.021(3) 0.019(3) 0.013(3) 0.000(2) 0.004(2) 0.004(3) C14 0.008(3) 0.012(3) 0.015(3) -0.001(2) 0.002(2) 0.002(2) C15 0.017(3) 0.019(3) 0.014(3) 0.005(2) 0.006(2) 0.003(2) C16 0.028(4) 0.009(3) 0.020(3) -0.002(2) 0.004(2) 0.000(2) C17 0.028(4) 0.025(4) 0.013(3) -0.003(2) 0.003(2) 0.003(3) C18 0.027(4) 0.024(4) 0.009(3) 0.002(2) 0.002(2) 0.002(3) C19 0.021(3) 0.012(3) 0.014(3) 0.002(2) 0.006(2) 0.002(2) _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 P1 2.2251(15) . ? Au1 Cl1 2.3063(15) . ? P1 C14 1.817(6) . ? P1 C8 1.818(6) . ? P1 C1 1.832(6) . ? Br1 C3 1.898(6) . ? C1 C2 1.518(8) . ? C2 C3 1.391(8) . ? C2 C7 1.404(8) . ? C3 C4 1.391(8) . ? C4 C5 1.379(9) . ? C5 C6 1.379(9) . ? C6 C7 1.397(8) . ? C8 C9 1.395(8) . ? C8 C13 1.399(9) . ? C9 C10 1.404(8) . ? C10 C11 1.373(9) . ? C11 C12 1.394(9) . ? C12 C13 1.397(9) . ? C14 C15 1.393(8) . ? C14 C19 1.398(8) . ? C15 C16 1.388(8) . ? C16 C17 1.396(8) . ? C17 C18 1.361(9) . ? C18 C19 1.397(8) . ? 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 P1 Au1 Cl1 177.68(5) . . ? C14 P1 C8 103.0(3) . . ? C14 P1 C1 104.8(3) . . ? C8 P1 C1 105.6(3) . . ? C14 P1 Au1 115.9(2) . . ? C8 P1 Au1 112.24(19) . . ? C1 P1 Au1 114.2(2) . . ? C2 C1 P1 112.5(4) . . ? C3 C2 C7 117.9(5) . . ? C3 C2 C1 123.8(5) . . ? C7 C2 C1 118.3(5) . . ? C2 C3 C4 121.7(6) . . ? C2 C3 Br1 121.0(4) . . ? C4 C3 Br1 117.3(5) . . ? C5 C4 C3 119.4(6) . . ? C6 C5 C4 120.6(6) . . ? C5 C6 C7 119.9(6) . . ? C6 C7 C2 120.5(6) . . ? C9 C8 C13 120.8(6) . . ? C9 C8 P1 123.4(5) . . ? C13 C8 P1 115.7(4) . . ? C8 C9 C10 118.2(6) . . ? C11 C10 C9 121.3(6) . . ? C10 C11 C12 120.3(6) . . ? C11 C12 C13 119.5(6) . . ? C12 C13 C8 119.8(6) . . ? C15 C14 C19 120.1(5) . . ? C15 C14 P1 119.1(4) . . ? C19 C14 P1 120.8(5) . . ? C16 C15 C14 119.5(5) . . ? C15 C16 C17 120.0(6) . . ? C18 C17 C16 120.6(6) . . ? C17 C18 C19 120.3(6) . . ? C18 C19 C14 119.5(6) . . ? 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 Cl1 Au1 P1 C14 -131.5(13) . . . . ? Cl1 Au1 P1 C8 -13.6(14) . . . . ? Cl1 Au1 P1 C1 106.5(13) . . . . ? C14 P1 C1 C2 -62.8(5) . . . . ? C8 P1 C1 C2 -171.1(4) . . . . ? Au1 P1 C1 C2 65.1(4) . . . . ? P1 C1 C2 C3 -92.0(6) . . . . ? P1 C1 C2 C7 90.2(6) . . . . ? C7 C2 C3 C4 1.0(9) . . . . ? C1 C2 C3 C4 -176.9(5) . . . . ? C7 C2 C3 Br1 179.6(4) . . . . ? C1 C2 C3 Br1 1.8(8) . . . . ? C2 C3 C4 C5 -1.4(9) . . . . ? Br1 C3 C4 C5 179.9(5) . . . . ? C3 C4 C5 C6 1.6(9) . . . . ? C4 C5 C6 C7 -1.3(9) . . . . ? C5 C6 C7 C2 0.9(9) . . . . ? C3 C2 C7 C6 -0.7(8) . . . . ? C1 C2 C7 C6 177.2(5) . . . . ? C14 P1 C8 C9 -115.0(5) . . . . ? C1 P1 C8 C9 -5.4(6) . . . . ? Au1 P1 C8 C9 119.6(5) . . . . ? C14 P1 C8 C13 62.6(5) . . . . ? C1 P1 C8 C13 172.2(5) . . . . ? Au1 P1 C8 C13 -62.8(5) . . . . ? C13 C8 C9 C10 -0.6(9) . . . . ? P1 C8 C9 C10 176.9(4) . . . . ? C8 C9 C10 C11 -1.5(9) . . . . ? C9 C10 C11 C12 2.3(9) . . . . ? C10 C11 C12 C13 -1.1(10) . . . . ? C11 C12 C13 C8 -0.9(10) . . . . ? C9 C8 C13 C12 1.7(10) . . . . ? P1 C8 C13 C12 -175.9(5) . . . . ? C8 P1 C14 C15 45.7(5) . . . . ? C1 P1 C14 C15 -64.6(5) . . . . ? Au1 P1 C14 C15 168.6(4) . . . . ? C8 P1 C14 C19 -133.4(5) . . . . ? C1 P1 C14 C19 116.3(5) . . . . ? Au1 P1 C14 C19 -10.5(6) . . . . ? C19 C14 C15 C16 -0.7(9) . . . . ? P1 C14 C15 C16 -179.8(5) . . . . ? C14 C15 C16 C17 0.9(10) . . . . ? C15 C16 C17 C18 -0.9(10) . . . . ? C16 C17 C18 C19 0.6(11) . . . . ? C17 C18 C19 C14 -0.4(10) . . . . ? C15 C14 C19 C18 0.5(9) . . . . ? P1 C14 C19 C18 179.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.678 _refine_diff_density_min -3.188 _refine_diff_density_rms 0.347 _database_code_depnum_ccdc_archive 'CCDC 964933'