# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 #TrackingRef '10673_web_deposit_cif_file_0_Chen-WeiLiu_1334281614.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Au I2 P Se2' _chemical_formula_weight 849.96 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' Se Se -0.0929 2.2259 '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 9.4588(8) _cell_length_b 11.8888(10) _cell_length_c 18.7731(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.103(4) _cell_angle_gamma 90.00 _cell_volume 2064.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9005 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.20 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 13.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0688 _exptl_absorpt_correction_T_max 0.5471 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46411 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.29 _reflns_number_total 4143 _reflns_number_gt 3652 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-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^)+(0.0721P)^2^+4.6930P] 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 4143 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1207 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 0.88776(3) 0.68870(3) 0.222253(16) 0.02780(13) Uani 1 1 d . . . C1 C 0.3947(8) 0.6101(7) 0.1455(5) 0.0355(18) Uani 1 1 d . . . H1A H 0.3442 0.5581 0.1712 0.043 Uiso 1 1 calc R . . H1B H 0.3277 0.6699 0.1262 0.043 Uiso 1 1 calc R . . C2 C 0.4362(10) 0.5484(9) 0.0820(5) 0.045(2) Uani 1 1 d . . . H2A H 0.4519 0.6027 0.0459 0.054 Uiso 1 1 calc R . . H2B H 0.5262 0.5084 0.0992 0.054 Uiso 1 1 calc R . . C3 C 0.3208(9) 0.4654(8) 0.0465(4) 0.0378(19) Uani 1 1 d . . . C4 C 0.3202(11) 0.3572(10) 0.0743(5) 0.055(3) Uani 1 1 d . . . H4 H 0.3917 0.3352 0.1138 0.065 Uiso 1 1 calc R . . C5 C 0.2137(10) 0.4952(8) -0.0122(5) 0.045(2) Uani 1 1 d . . . H5 H 0.2112 0.5675 -0.0314 0.054 Uiso 1 1 calc R . . C6 C 0.2143(13) 0.2829(9) 0.0436(6) 0.059(3) Uani 1 1 d . . . H6 H 0.2142 0.2112 0.0633 0.070 Uiso 1 1 calc R . . C7 C 0.1096(11) 0.4172(10) -0.0425(5) 0.054(3) Uani 1 1 d . . . H7 H 0.0381 0.4372 -0.0825 0.065 Uiso 1 1 calc R . . C8 C 0.1111(13) 0.3105(10) -0.0140(6) 0.063(3) Uani 1 1 d . . . H8 H 0.0412 0.2583 -0.0346 0.076 Uiso 1 1 calc R . . C9 C 0.4653(8) 0.7299(7) 0.2807(5) 0.0356(18) Uani 1 1 d . . . H9A H 0.3921 0.7838 0.2587 0.043 Uiso 1 1 calc R . . H9B H 0.4166 0.6702 0.3014 0.043 Uiso 1 1 calc R . . C10 C 0.5689(10) 0.7888(8) 0.3431(5) 0.042(2) Uani 1 1 d . . . H10A H 0.6311 0.8383 0.3223 0.050 Uiso 1 1 calc R . . H10B H 0.5125 0.8354 0.3691 0.050 Uiso 1 1 calc R . . C11 C 0.6635(9) 0.7117(7) 0.3974(5) 0.0367(19) Uani 1 1 d . . . C12 C 0.8115(10) 0.7310(9) 0.4180(5) 0.050(2) Uani 1 1 d . . . H12 H 0.8529 0.7891 0.3962 0.060 Uiso 1 1 calc R . . C13 C 0.6055(12) 0.6230(9) 0.4299(6) 0.056(3) Uani 1 1 d . . . H13 H 0.5074 0.6068 0.4161 0.068 Uiso 1 1 calc R . . C14 C 0.8984(14) 0.6647(11) 0.4705(6) 0.064(3) Uani 1 1 d . . . H14 H 0.9973 0.6784 0.4832 0.077 Uiso 1 1 calc R . . C15 C 0.6923(15) 0.5588(11) 0.4823(7) 0.076(4) Uani 1 1 d . . . H15 H 0.6525 0.5001 0.5043 0.091 Uiso 1 1 calc R . . C16 C 0.8410(15) 0.5815(11) 0.5030(7) 0.076(4) Uani 1 1 d . . . H16 H 0.8993 0.5387 0.5391 0.092 Uiso 1 1 calc R . . I1 I 1.05825(5) 0.85339(5) 0.19713(3) 0.04022(17) Uani 1 1 d . . . I2 I 1.10115(5) 0.55667(5) 0.28437(3) 0.04374(18) Uani 1 1 d . . . P1 P 0.5433(2) 0.67013(17) 0.20962(12) 0.0291(4) Uani 1 1 d . . . Se1 Se 0.67117(8) 0.79291(7) 0.16300(5) 0.0355(2) Uani 1 1 d . . . Se2 Se 0.71687(8) 0.54744(7) 0.24800(5) 0.0322(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 0.02032(18) 0.0263(2) 0.0371(2) -0.00193(11) 0.00673(13) -0.00141(10) C1 0.029(4) 0.031(5) 0.046(5) -0.001(4) 0.005(3) -0.001(3) C2 0.034(4) 0.058(6) 0.047(5) -0.005(4) 0.014(4) -0.013(4) C3 0.037(4) 0.050(6) 0.030(4) -0.008(4) 0.013(3) -0.005(4) C4 0.053(6) 0.063(7) 0.047(6) -0.001(5) 0.010(5) 0.006(5) C5 0.051(5) 0.044(6) 0.041(5) 0.004(4) 0.009(4) -0.006(4) C6 0.072(7) 0.039(6) 0.067(7) -0.008(5) 0.020(6) -0.017(5) C7 0.049(6) 0.077(8) 0.033(5) -0.003(5) 0.000(4) -0.010(5) C8 0.069(8) 0.072(8) 0.051(6) -0.027(6) 0.018(6) -0.032(6) C9 0.027(4) 0.034(5) 0.048(5) 0.000(4) 0.014(3) 0.006(3) C10 0.042(5) 0.033(5) 0.050(5) -0.002(4) 0.012(4) 0.001(4) C11 0.043(5) 0.025(4) 0.044(5) -0.004(4) 0.012(4) 0.002(4) C12 0.046(5) 0.049(6) 0.055(6) -0.011(5) 0.011(4) -0.006(5) C13 0.056(6) 0.047(6) 0.073(7) 0.013(5) 0.028(5) 0.003(5) C14 0.057(7) 0.074(8) 0.056(7) -0.004(6) -0.001(5) 0.014(6) C15 0.079(9) 0.069(9) 0.088(9) 0.039(7) 0.039(7) 0.023(7) C16 0.093(10) 0.085(10) 0.053(7) 0.018(7) 0.019(6) 0.040(8) I1 0.0296(3) 0.0352(4) 0.0565(4) 0.0019(3) 0.0106(2) -0.0081(2) I2 0.0242(3) 0.0362(4) 0.0683(4) 0.0066(3) 0.0039(3) 0.0025(2) P1 0.0208(9) 0.0241(11) 0.0425(12) -0.0011(8) 0.0068(8) -0.0014(7) Se1 0.0265(4) 0.0289(5) 0.0503(5) 0.0083(4) 0.0062(3) -0.0004(3) Se2 0.0250(4) 0.0232(4) 0.0496(5) 0.0031(3) 0.0103(3) 0.0009(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 Se2 2.4483(8) . ? Au1 Se1 2.4523(8) . ? Au1 I2 2.6288(6) . ? Au1 I1 2.6412(6) . ? C1 C2 1.519(12) . ? C1 P1 1.796(8) . ? C2 C3 1.518(12) . ? C3 C5 1.377(13) . ? C3 C4 1.389(14) . ? C4 C6 1.369(15) . ? C5 C7 1.384(14) . ? C6 C8 1.338(16) . ? C7 C8 1.375(15) . ? C9 C10 1.529(12) . ? C9 P1 1.802(8) . ? C10 C11 1.516(12) . ? C11 C13 1.389(13) . ? C11 C12 1.390(13) . ? C12 C14 1.390(15) . ? C13 C15 1.373(16) . ? C14 C16 1.336(18) . ? C15 C16 1.404(19) . ? P1 Se1 2.192(2) . ? P1 Se2 2.201(2) . ? 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 Se2 Au1 Se1 84.99(3) . . ? Se2 Au1 I2 88.86(2) . . ? Se1 Au1 I2 173.51(3) . . ? Se2 Au1 I1 175.46(2) . . ? Se1 Au1 I1 91.59(2) . . ? I2 Au1 I1 94.65(2) . . ? C2 C1 P1 115.1(6) . . ? C3 C2 C1 112.3(7) . . ? C5 C3 C4 118.6(9) . . ? C5 C3 C2 121.6(9) . . ? C4 C3 C2 119.7(9) . . ? C6 C4 C3 119.9(10) . . ? C3 C5 C7 119.8(9) . . ? C8 C6 C4 121.9(11) . . ? C8 C7 C5 120.6(10) . . ? C6 C8 C7 119.2(10) . . ? C10 C9 P1 116.8(6) . . ? C11 C10 C9 115.6(7) . . ? C13 C11 C12 118.1(9) . . ? C13 C11 C10 121.5(9) . . ? C12 C11 C10 120.3(8) . . ? C14 C12 C11 121.0(10) . . ? C15 C13 C11 120.3(11) . . ? C16 C14 C12 120.5(12) . . ? C13 C15 C16 120.4(11) . . ? C14 C16 C15 119.7(11) . . ? C1 P1 C9 105.6(4) . . ? C1 P1 Se1 114.6(3) . . ? C9 P1 Se1 112.3(3) . . ? C1 P1 Se2 112.4(3) . . ? C9 P1 Se2 114.3(3) . . ? Se1 P1 Se2 97.82(8) . . ? P1 Se1 Au1 87.75(6) . . ? P1 Se2 Au1 87.64(6) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.809 _refine_diff_density_min -3.148 _refine_diff_density_rms 0.352 _database_code_depnum_ccdc_archive 'CCDC 876097' ####################################################################### # # 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_1a #TrackingRef '10674_web_deposit_cif_file_1_Chen-WeiLiu_1334281614.1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Au I2 O2 P Se2' _chemical_formula_weight 729.78 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.827(2) _cell_length_b 8.851(3) _cell_length_c 18.150(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.497(7) _cell_angle_gamma 90.00 _cell_volume 1389.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 903 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.88 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 20.356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1502 _exptl_absorpt_correction_T_max 0.2480 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6441 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2442 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2442 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.25557(7) 0.16598(8) 0.24743(4) 0.0461(3) Uani 1 1 d . . . C1 C 0.759(2) 0.157(2) 0.3848(13) 0.072(6) Uani 1 1 d . . . H1A H 0.7601 0.1389 0.3323 0.087 Uiso 1 1 calc R . . H1B H 0.7111 0.2551 0.3888 0.087 Uiso 1 1 calc R . . C2 C 0.913(2) 0.157(3) 0.4280(12) 0.084(8) Uani 1 1 d . . . H2A H 0.9715 0.2369 0.4107 0.127 Uiso 1 1 calc R . . H2B H 0.9615 0.0619 0.4222 0.127 Uiso 1 1 calc R . . H2C H 0.9112 0.1732 0.4801 0.127 Uiso 1 1 calc R . . C3 C 0.330(2) -0.221(3) 0.4027(14) 0.090(8) Uani 1 1 d . . . H3A H 0.2511 -0.1659 0.4219 0.108 Uiso 1 1 calc R . . H3B H 0.2973 -0.2287 0.3485 0.108 Uiso 1 1 calc R . . C4 C 0.347(3) -0.370(2) 0.4351(13) 0.080(7) Uani 1 1 d . . . H4A H 0.2491 -0.4216 0.4235 0.120 Uiso 1 1 calc R . . H4B H 0.3798 -0.3622 0.4886 0.120 Uiso 1 1 calc R . . H4C H 0.4221 -0.4255 0.4146 0.120 Uiso 1 1 calc R . . I1 I 0.17803(17) 0.12820(17) 0.10238(8) 0.0704(5) Uani 1 1 d . . . I2 I 0.05585(16) 0.38082(17) 0.25247(9) 0.0740(5) Uani 1 1 d . . . O1 O 0.6682(13) 0.0382(15) 0.4134(7) 0.063(4) Uani 1 1 d . . . O2 O 0.4753(13) -0.1393(13) 0.4207(8) 0.063(4) Uani 1 1 d . . . P1 P 0.4977(5) 0.0048(6) 0.3757(3) 0.0514(13) Uani 1 1 d . . . Se1 Se 0.4567(2) -0.0282(3) 0.25490(11) 0.0609(6) Uani 1 1 d . . . Se2 Se 0.3377(2) 0.1864(2) 0.38412(11) 0.0582(6) 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 0.0400(4) 0.0409(4) 0.0553(5) 0.0050(3) 0.0047(3) 0.0027(3) C1 0.058(13) 0.063(15) 0.093(18) 0.006(12) 0.009(12) -0.005(12) C2 0.055(12) 0.13(2) 0.064(15) 0.003(13) -0.006(11) -0.026(14) C3 0.067(14) 0.073(18) 0.12(2) 0.030(15) -0.001(14) -0.008(14) C4 0.111(19) 0.044(14) 0.083(17) 0.002(11) 0.016(14) -0.009(14) I1 0.0750(9) 0.0770(11) 0.0553(9) 0.0099(7) 0.0038(7) -0.0014(8) I2 0.0608(9) 0.0652(11) 0.0938(12) 0.0102(8) 0.0103(8) 0.0264(8) O1 0.041(7) 0.068(10) 0.068(9) 0.009(7) -0.015(6) 0.003(7) O2 0.048(7) 0.040(8) 0.093(11) 0.016(7) -0.006(7) -0.003(6) P1 0.048(3) 0.045(3) 0.058(3) 0.006(2) 0.005(2) 0.007(3) Se1 0.0588(12) 0.0603(15) 0.0607(13) -0.0085(10) 0.0047(10) 0.0197(11) Se2 0.0562(11) 0.0596(14) 0.0563(13) -0.0066(9) 0.0055(9) 0.0147(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 Se2 2.449(2) . ? Au1 Se1 2.455(2) . ? Au1 I1 2.6063(18) . ? Au1 I2 2.6069(16) . ? C1 C2 1.43(2) . ? C1 O1 1.48(2) . ? C3 C4 1.44(3) . ? C3 O2 1.45(2) . ? O1 P1 1.553(12) . ? O2 P1 1.549(13) . ? P1 Se2 2.165(5) . ? P1 Se1 2.169(6) . ? 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 Se2 Au1 Se1 86.04(7) . . ? Se2 Au1 I1 176.35(6) . . ? Se1 Au1 I1 90.42(6) . . ? Se2 Au1 I2 88.64(6) . . ? Se1 Au1 I2 174.40(7) . . ? I1 Au1 I2 94.92(5) . . ? C2 C1 O1 109.3(17) . . ? C4 C3 O2 110.5(19) . . ? C1 O1 P1 121.6(11) . . ? C3 O2 P1 119.4(12) . . ? O2 P1 O1 98.0(7) . . ? O2 P1 Se2 114.9(5) . . ? O1 P1 Se2 114.6(6) . . ? O2 P1 Se1 114.1(6) . . ? O1 P1 Se1 115.0(6) . . ? Se2 P1 Se1 101.0(2) . . ? P1 Se1 Au1 86.26(15) . . ? P1 Se2 Au1 86.51(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.430 _refine_diff_density_min -1.749 _refine_diff_density_rms 0.298 _database_code_depnum_ccdc_archive 'CCDC 876098' ####################################################################### # # 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_1b #TrackingRef '10675_web_deposit_cif_file_2_Chen-WeiLiu_1334281614.1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 Au2 I4 O4 P2 Se4' _chemical_formula_weight 1515.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Se Se -0.0929 2.2259 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7465(11) _cell_length_b 8.7967(11) _cell_length_c 21.903(3) _cell_angle_alpha 90.353(3) _cell_angle_beta 100.611(3) _cell_angle_gamma 90.214(3) _cell_volume 1656.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2959 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.38 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 17.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0999 _exptl_absorpt_correction_T_max 0.1593 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10487 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.95 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6381 _reflns_number_gt 4654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+12.7913P] 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 6381 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.75863(6) 0.87704(6) 0.23778(3) 0.03433(17) Uani 1 1 d . . . Au2 Au 0.27315(6) 0.38134(6) 0.26298(3) 0.03275(17) Uani 1 1 d . . . I1 I 0.79268(15) 0.83218(15) 0.35698(5) 0.0592(3) Uani 1 1 d . . . I2 I 0.96653(15) 1.09372(15) 0.24763(7) 0.0661(4) Uani 1 1 d . . . I3 I 0.18563(15) 0.41642(15) 0.14383(5) 0.0595(3) Uani 1 1 d . . . I4 I 0.49028(15) 0.18618(15) 0.25191(6) 0.0651(4) Uani 1 1 d . . . Se1 Se 0.5572(2) 0.6778(2) 0.21712(8) 0.0514(4) Uani 1 1 d . . . Se2 Se 0.7219(2) 0.9026(2) 0.12550(8) 0.0482(4) Uani 1 1 d . . . Se3 Se 0.07718(19) 0.5649(2) 0.28386(8) 0.0475(4) Uani 1 1 d . . . Se4 Se 0.35027(19) 0.3650(2) 0.37534(8) 0.0455(4) Uani 1 1 d . . . P1 P 0.5421(4) 0.7278(4) 0.1193(2) 0.0382(9) Uani 1 1 d . . . P2 P 0.1684(4) 0.5293(4) 0.38194(19) 0.0371(9) Uani 1 1 d . . . O1 O 0.3834(12) 0.7821(12) 0.0826(5) 0.047(3) Uani 1 1 d . . . O2 O 0.5651(11) 0.5900(12) 0.0776(5) 0.044(3) Uani 1 1 d . . . O3 O 0.0505(12) 0.4743(12) 0.4223(5) 0.046(3) Uani 1 1 d . . . O4 O 0.2272(12) 0.6734(12) 0.4203(5) 0.046(3) Uani 1 1 d . . . C1 C 0.303(2) 0.9181(19) 0.1002(10) 0.060(5) Uani 1 1 d . . . H1A H 0.3637 0.9658 0.1374 0.073 Uiso 1 1 calc R . . C2 C 0.293(3) 1.022(3) 0.0455(13) 0.111(11) Uani 1 1 d . . . H2A H 0.2381 1.1131 0.0530 0.166 Uiso 1 1 calc R . . H2B H 0.2382 0.9721 0.0088 0.166 Uiso 1 1 calc R . . H2C H 0.3958 1.0489 0.0397 0.166 Uiso 1 1 calc R . . C3 C 0.156(3) 0.873(3) 0.1111(17) 0.133(13) Uani 1 1 d . . . H3A H 0.0998 0.9613 0.1203 0.199 Uiso 1 1 calc R . . H3B H 0.1690 0.8051 0.1457 0.199 Uiso 1 1 calc R . . H3C H 0.0996 0.8230 0.0749 0.199 Uiso 1 1 calc R . . C4 C 0.7100(19) 0.497(2) 0.0863(9) 0.055(5) Uani 1 1 d . . . H4A H 0.7794 0.5306 0.1244 0.066 Uiso 1 1 calc R . . C5 C 0.7890(19) 0.526(2) 0.0310(9) 0.055(5) Uani 1 1 d . . . H5A H 0.8213 0.6305 0.0314 0.082 Uiso 1 1 calc R . . H5B H 0.7172 0.5046 -0.0068 0.082 Uiso 1 1 calc R . . H5C H 0.8782 0.4615 0.0336 0.082 Uiso 1 1 calc R . . C6 C 0.667(3) 0.335(2) 0.0934(11) 0.077(7) Uani 1 1 d . . . H6A H 0.6239 0.3235 0.1304 0.115 Uiso 1 1 calc R . . H6B H 0.7581 0.2725 0.0963 0.115 Uiso 1 1 calc R . . H6C H 0.5915 0.3032 0.0580 0.115 Uiso 1 1 calc R . . C7 C -0.034(2) 0.327(2) 0.4108(9) 0.062(5) Uani 1 1 d . . . H7A H -0.0145 0.2814 0.3720 0.075 Uiso 1 1 calc R . . C8 C 0.017(2) 0.2247(19) 0.4616(10) 0.063(5) Uani 1 1 d . . . H8A H 0.1277 0.2100 0.4662 0.095 Uiso 1 1 calc R . . H8B H -0.0350 0.1287 0.4532 0.095 Uiso 1 1 calc R . . H8C H -0.0060 0.2674 0.4992 0.095 Uiso 1 1 calc R . . C9 C -0.209(2) 0.362(3) 0.4048(11) 0.089(8) Uani 1 1 d . . . H9A H -0.2678 0.2686 0.3980 0.133 Uiso 1 1 calc R . . H9B H -0.2412 0.4286 0.3705 0.133 Uiso 1 1 calc R . . H9C H -0.2274 0.4093 0.4424 0.133 Uiso 1 1 calc R . . C10 C 0.3621(18) 0.7667(18) 0.4078(9) 0.046(4) Uani 1 1 d . . . H10A H 0.4044 0.7237 0.3731 0.056 Uiso 1 1 calc R . . C11 C 0.300(4) 0.922(3) 0.3926(16) 0.140(14) Uani 1 1 d . . . H11A H 0.2248 0.9182 0.3546 0.210 Uiso 1 1 calc R . . H11B H 0.3831 0.9892 0.3880 0.210 Uiso 1 1 calc R . . H11C H 0.2502 0.9582 0.4256 0.210 Uiso 1 1 calc R . . C12 C 0.478(3) 0.759(3) 0.4664(12) 0.094(8) Uani 1 1 d . . . H12A H 0.5133 0.6564 0.4733 0.141 Uiso 1 1 calc R . . H12B H 0.4313 0.7926 0.5004 0.141 Uiso 1 1 calc R . . H12C H 0.5652 0.8238 0.4633 0.141 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 0.0325(3) 0.0350(3) 0.0338(3) -0.0016(2) 0.0017(2) -0.0006(2) Au2 0.0327(3) 0.0343(3) 0.0314(3) 0.0006(2) 0.0063(2) 0.0029(2) I1 0.0633(7) 0.0763(8) 0.0352(6) 0.0054(6) 0.0009(5) 0.0084(6) I2 0.0607(8) 0.0683(8) 0.0672(9) -0.0127(7) 0.0079(6) -0.0338(6) I3 0.0651(8) 0.0787(9) 0.0330(6) 0.0063(6) 0.0044(5) -0.0001(6) I4 0.0624(8) 0.0694(8) 0.0635(8) -0.0107(6) 0.0116(6) 0.0303(6) Se1 0.0593(11) 0.0508(10) 0.0431(10) 0.0007(8) 0.0074(8) -0.0252(8) Se2 0.0525(10) 0.0545(10) 0.0370(9) 0.0012(8) 0.0071(7) -0.0154(8) Se3 0.0469(9) 0.0540(10) 0.0397(9) 0.0014(8) 0.0027(7) 0.0207(8) Se4 0.0452(9) 0.0548(10) 0.0344(9) 0.0035(7) 0.0013(7) 0.0176(8) P1 0.036(2) 0.037(2) 0.039(2) -0.0093(18) -0.0002(17) -0.0059(17) P2 0.035(2) 0.040(2) 0.037(2) -0.0032(17) 0.0096(16) 0.0035(17) O1 0.037(6) 0.050(6) 0.050(7) -0.013(5) 0.002(5) 0.011(5) O2 0.034(5) 0.045(6) 0.049(7) -0.012(5) -0.003(5) -0.002(5) O3 0.043(6) 0.042(6) 0.057(8) -0.011(5) 0.018(5) -0.015(5) O4 0.042(6) 0.046(6) 0.054(7) -0.012(5) 0.017(5) -0.006(5) C1 0.072(13) 0.039(9) 0.071(14) -0.011(9) 0.013(10) 0.016(9) C2 0.14(2) 0.098(19) 0.10(2) 0.038(16) 0.051(19) 0.070(18) C3 0.089(19) 0.11(2) 0.22(4) -0.01(2) 0.09(2) 0.006(17) C4 0.044(9) 0.072(12) 0.049(11) -0.003(9) 0.013(8) 0.018(9) C5 0.037(9) 0.054(10) 0.074(14) -0.005(9) 0.014(8) -0.016(8) C6 0.099(17) 0.047(11) 0.092(18) 0.001(11) 0.038(14) 0.009(11) C7 0.054(11) 0.093(15) 0.045(11) -0.014(11) 0.026(9) -0.010(10) C8 0.057(11) 0.038(9) 0.097(17) 0.003(10) 0.016(11) -0.015(8) C9 0.040(11) 0.14(2) 0.081(17) 0.021(15) -0.007(10) -0.038(12) C10 0.042(9) 0.040(9) 0.057(11) 0.010(8) 0.009(8) -0.010(7) C11 0.18(3) 0.040(13) 0.18(3) 0.023(17) -0.02(3) 0.029(17) C12 0.076(15) 0.094(17) 0.11(2) -0.033(16) 0.011(14) -0.057(14) _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 Se2 2.4326(18) . ? Au1 Se1 2.4604(18) . ? Au1 I1 2.6055(13) . ? Au1 I2 2.6097(14) . ? Au2 Se4 2.4344(17) . ? Au2 Se3 2.4604(15) . ? Au2 I3 2.6017(13) . ? Au2 I4 2.6080(12) . ? Se1 P1 2.171(5) . ? Se2 P1 2.181(4) . ? Se3 P2 2.174(4) . ? Se4 P2 2.178(4) . ? P1 O1 1.549(11) . ? P1 O2 1.549(11) . ? P2 O4 1.549(11) . ? P2 O3 1.555(11) . ? O1 C1 1.475(17) . ? O2 C4 1.495(17) . ? O3 C7 1.49(2) . ? O4 C10 1.502(18) . ? C1 C3 1.40(3) . ? C1 C2 1.50(3) . ? C4 C6 1.49(3) . ? C4 C5 1.52(2) . ? C7 C8 1.44(3) . ? C7 C9 1.55(3) . ? C10 C12 1.48(3) . ? C10 C11 1.49(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 Se2 Au1 Se1 85.85(6) . . ? Se2 Au1 I1 176.46(6) . . ? Se1 Au1 I1 91.04(6) . . ? Se2 Au1 I2 88.38(5) . . ? Se1 Au1 I2 174.20(6) . . ? I1 Au1 I2 94.75(5) . . ? Se4 Au2 Se3 85.91(5) . . ? Se4 Au2 I3 176.40(5) . . ? Se3 Au2 I3 90.99(5) . . ? Se4 Au2 I4 88.81(5) . . ? Se3 Au2 I4 174.70(6) . . ? I3 Au2 I4 94.28(4) . . ? P1 Se1 Au1 86.83(12) . . ? P1 Se2 Au1 87.31(13) . . ? P2 Se3 Au2 86.72(10) . . ? P2 Se4 Au2 87.31(12) . . ? O1 P1 O2 98.1(6) . . ? O1 P1 Se1 117.7(5) . . ? O2 P1 Se1 115.3(5) . . ? O1 P1 Se2 112.2(5) . . ? O2 P1 Se2 114.4(5) . . ? Se1 P1 Se2 99.96(17) . . ? O4 P2 O3 97.7(6) . . ? O4 P2 Se3 116.0(5) . . ? O3 P2 Se3 116.6(5) . . ? O4 P2 Se4 113.8(4) . . ? O3 P2 Se4 113.5(5) . . ? Se3 P2 Se4 100.06(16) . . ? C1 O1 P1 123.0(11) . . ? C4 O2 P1 123.7(10) . . ? C7 O3 P2 122.4(10) . . ? C10 O4 P2 122.5(10) . . ? C3 C1 O1 108.3(17) . . ? C3 C1 C2 113(2) . . ? O1 C1 C2 104.6(16) . . ? C6 C4 O2 108.5(15) . . ? C6 C4 C5 114.0(15) . . ? O2 C4 C5 107.6(14) . . ? C8 C7 O3 109.9(16) . . ? C8 C7 C9 110.9(16) . . ? O3 C7 C9 107.0(16) . . ? C12 C10 C11 114(2) . . ? C12 C10 O4 104.4(14) . . ? C11 C10 O4 105.8(18) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.765 _refine_diff_density_min -1.875 _refine_diff_density_rms 0.299 _database_code_depnum_ccdc_archive 'CCDC 876099' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Au2 P2 S4' _chemical_formula_weight 1004.72 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6496(2) _cell_length_b 12.8257(2) _cell_length_c 14.1389(3) _cell_angle_alpha 79.90 _cell_angle_beta 85.08 _cell_angle_gamma 74.07 _cell_volume 1655.28(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8034 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.36 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 9.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1751 _exptl_absorpt_correction_T_max 0.4040 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22354 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.44 _reflns_number_total 6807 _reflns_number_gt 5650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-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^)+(0.0219P)^2^+0.2729P] 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 6807 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0545 _refine_ls_wR_factor_gt 0.0514 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.509430(17) 0.124450(13) 0.455668(12) 0.04169(6) Uani 1 1 d . . . Au2 Au 0.482561(17) 0.399979(13) 0.448564(12) 0.04411(6) Uani 1 1 d . . . C1 C 0.5848(4) 0.0314(3) 0.7204(3) 0.0431(10) Uani 1 1 d . . . H1A H 0.4921 0.0458 0.6920 0.052 Uiso 1 1 calc R . . H1B H 0.5877 -0.0245 0.7767 0.052 Uiso 1 1 calc R . . C2 C 0.5964(5) 0.1350(4) 0.7518(4) 0.0622(13) Uani 1 1 d . . . H2A H 0.5850 0.1924 0.6961 0.075 Uiso 1 1 calc R . . H2B H 0.6928 0.1222 0.7742 0.075 Uiso 1 1 calc R . . C3 C 0.4879(4) 0.1767(4) 0.8306(3) 0.0465(10) Uani 1 1 d . . . C4 C 0.4522(5) 0.2875(4) 0.8372(4) 0.0621(13) Uani 1 1 d . . . H4 H 0.4906 0.3349 0.7918 0.075 Uiso 1 1 calc R . . C5 C 0.3607(6) 0.3283(5) 0.9098(5) 0.0740(16) Uani 1 1 d . . . H5 H 0.3384 0.4028 0.9133 0.089 Uiso 1 1 calc R . . C6 C 0.3026(5) 0.2609(5) 0.9765(4) 0.0754(17) Uani 1 1 d . . . H6 H 0.2413 0.2889 1.0258 0.091 Uiso 1 1 calc R . . C7 C 0.3348(5) 0.1518(5) 0.9707(4) 0.0693(15) Uani 1 1 d . . . H7 H 0.2939 0.1055 1.0156 0.083 Uiso 1 1 calc R . . C8 C 0.4281(5) 0.1096(4) 0.8984(3) 0.0581(12) Uani 1 1 d . . . H8 H 0.4505 0.0348 0.8958 0.070 Uiso 1 1 calc R . . C9 C 0.8979(4) -0.0451(3) 0.6886(3) 0.0418(9) Uani 1 1 d . . . H9A H 0.9742 -0.0734 0.6432 0.050 Uiso 1 1 calc R . . H9B H 0.9086 0.0250 0.6992 0.050 Uiso 1 1 calc R . . C10 C 0.9190(4) -0.1237(4) 0.7831(3) 0.0500(11) Uani 1 1 d . . . H10A H 0.8439 -0.0954 0.8293 0.060 Uiso 1 1 calc R . . H10B H 0.9088 -0.1941 0.7732 0.060 Uiso 1 1 calc R . . C11 C 1.0649(5) -0.1406(3) 0.8246(3) 0.0441(10) Uani 1 1 d . . . C12 C 1.0735(5) -0.1171(4) 0.9149(4) 0.0597(13) Uani 1 1 d . . . H12 H 0.9894 -0.0903 0.9503 0.072 Uiso 1 1 calc R . . C13 C 1.2057(6) -0.1329(5) 0.9533(4) 0.0733(16) Uani 1 1 d . . . H13 H 1.2100 -0.1169 1.0145 0.088 Uiso 1 1 calc R . . C14 C 1.3293(6) -0.1715(5) 0.9028(5) 0.0775(18) Uani 1 1 d . . . H14 H 1.4182 -0.1824 0.9292 0.093 Uiso 1 1 calc R . . C15 C 1.3227(6) -0.1945(4) 0.8119(5) 0.0758(16) Uani 1 1 d . . . H15 H 1.4072 -0.2200 0.7764 0.091 Uiso 1 1 calc R . . C16 C 1.1899(5) -0.1797(4) 0.7735(4) 0.0588(12) Uani 1 1 d . . . H16 H 1.1857 -0.1965 0.7126 0.071 Uiso 1 1 calc R . . C17 C 0.1176(5) 0.6089(5) 0.5214(4) 0.0674(15) Uani 1 1 d . . . H17A H 0.0424 0.5798 0.5038 0.081 Uiso 1 1 calc R . . H17B H 0.0699 0.6708 0.5537 0.081 Uiso 1 1 calc R . . C18 C 0.1851(5) 0.6535(4) 0.4303(4) 0.0625(13) Uani 1 1 d . . . H18A H 0.2387 0.5926 0.3985 0.075 Uiso 1 1 calc R . . H18B H 0.2536 0.6904 0.4459 0.075 Uiso 1 1 calc R . . C19 C 0.0816(5) 0.7318(3) 0.3620(3) 0.0472(11) Uani 1 1 d . . . C20 C 0.1071(6) 0.7315(4) 0.2616(4) 0.0645(14) Uani 1 1 d . . . H20 H 0.1897 0.6850 0.2382 0.077 Uiso 1 1 calc R . . C21 C 0.0059(8) 0.8023(5) 0.1987(4) 0.0758(17) Uani 1 1 d . . . H21 H 0.0208 0.8028 0.1328 0.091 Uiso 1 1 calc R . . C22 C -0.1136(7) 0.8700(5) 0.2330(5) 0.0810(18) Uani 1 1 d . . . H22 H -0.1805 0.9161 0.1903 0.097 Uiso 1 1 calc R . . C23 C -0.1372(6) 0.8721(4) 0.3258(5) 0.0694(15) Uani 1 1 d . . . H23 H -0.2195 0.9203 0.3477 0.083 Uiso 1 1 calc R . . C24 C -0.0426(5) 0.8046(4) 0.3898(3) 0.0532(11) Uani 1 1 d . . . H24 H -0.0623 0.8074 0.4550 0.064 Uiso 1 1 calc R . . C25 C 0.0934(4) 0.4701(3) 0.7018(3) 0.0455(10) Uani 1 1 d . . . H25A H 0.0270 0.4419 0.6724 0.055 Uiso 1 1 calc R . . H25B H 0.1443 0.4113 0.7496 0.055 Uiso 1 1 calc R . . C26 C 0.0052(5) 0.5638(4) 0.7536(4) 0.0587(13) Uani 1 1 d . . . H26A H 0.0689 0.5877 0.7895 0.070 Uiso 1 1 calc R . . H26B H -0.0410 0.6256 0.7065 0.070 Uiso 1 1 calc R . . C27 C -0.1084(4) 0.5271(3) 0.8214(3) 0.0437(10) Uani 1 1 d . . . C28 C -0.2520(5) 0.5572(4) 0.7982(4) 0.0560(12) Uani 1 1 d . . . H28 H -0.2804 0.6046 0.7413 0.067 Uiso 1 1 calc R . . C29 C -0.3530(5) 0.5183(4) 0.8575(4) 0.0639(14) Uani 1 1 d . . . H29 H -0.4489 0.5396 0.8406 0.077 Uiso 1 1 calc R . . C30 C -0.3138(5) 0.4482(4) 0.9417(4) 0.0573(12) Uani 1 1 d . . . H30 H -0.3825 0.4220 0.9818 0.069 Uiso 1 1 calc R . . C31 C -0.1728(5) 0.4173(4) 0.9658(4) 0.0588(12) Uani 1 1 d . . . H31 H -0.1452 0.3693 1.0225 0.071 Uiso 1 1 calc R . . C32 C -0.0707(5) 0.4568(4) 0.9069(3) 0.0528(11) Uani 1 1 d . . . H32 H 0.0247 0.4360 0.9249 0.063 Uiso 1 1 calc R . . P1 P 0.72624(10) -0.02143(8) 0.63451(7) 0.0359(2) Uani 1 1 d . . . P2 P 0.22375(11) 0.50433(9) 0.61004(8) 0.0405(2) Uani 1 1 d . . . S1 S 0.73321(12) 0.09132(9) 0.51584(8) 0.0476(3) Uani 1 1 d . . . S2 S 0.28971(11) 0.17028(9) 0.38611(8) 0.0462(3) Uani 1 1 d . . . S3 S 0.31009(15) 0.36151(11) 0.55983(11) 0.0683(4) Uani 1 1 d . . . S4 S 0.64637(12) 0.43067(10) 0.32704(8) 0.0502(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.04581(10) 0.04144(10) 0.03814(10) -0.00609(7) -0.00903(7) -0.00998(7) Au2 0.04146(9) 0.04652(10) 0.05022(11) -0.01659(8) 0.00322(8) -0.01731(7) C1 0.038(2) 0.048(2) 0.045(2) -0.0146(19) 0.0006(19) -0.0106(19) C2 0.067(3) 0.052(3) 0.071(3) -0.021(3) 0.018(3) -0.021(2) C3 0.042(2) 0.050(3) 0.047(3) -0.014(2) -0.004(2) -0.009(2) C4 0.064(3) 0.049(3) 0.073(4) -0.021(3) -0.002(3) -0.007(2) C5 0.069(3) 0.063(3) 0.085(4) -0.037(3) -0.008(3) 0.010(3) C6 0.051(3) 0.112(5) 0.056(3) -0.042(3) -0.002(3) 0.009(3) C7 0.057(3) 0.091(4) 0.057(3) -0.016(3) 0.007(3) -0.016(3) C8 0.062(3) 0.055(3) 0.055(3) -0.013(2) 0.006(2) -0.012(2) C9 0.038(2) 0.048(2) 0.038(2) -0.0064(19) -0.0064(18) -0.0074(18) C10 0.047(2) 0.054(3) 0.047(3) 0.004(2) -0.013(2) -0.014(2) C11 0.050(2) 0.037(2) 0.046(3) -0.0003(19) -0.015(2) -0.0108(19) C12 0.064(3) 0.068(3) 0.049(3) -0.001(2) -0.013(2) -0.021(3) C13 0.087(4) 0.084(4) 0.056(3) 0.002(3) -0.029(3) -0.034(3) C14 0.064(4) 0.069(4) 0.099(5) 0.021(3) -0.046(4) -0.025(3) C15 0.050(3) 0.068(4) 0.099(5) -0.004(3) -0.011(3) 0.000(3) C16 0.054(3) 0.056(3) 0.062(3) -0.015(2) -0.013(2) -0.001(2) C17 0.052(3) 0.101(4) 0.051(3) 0.012(3) -0.007(2) -0.036(3) C18 0.054(3) 0.061(3) 0.068(3) 0.002(3) 0.001(3) -0.017(2) C19 0.053(3) 0.037(2) 0.056(3) 0.003(2) -0.009(2) -0.023(2) C20 0.072(3) 0.048(3) 0.081(4) -0.026(3) 0.021(3) -0.025(3) C21 0.126(5) 0.070(4) 0.041(3) 0.002(3) -0.010(3) -0.048(4) C22 0.091(4) 0.064(4) 0.093(5) 0.010(3) -0.040(4) -0.033(3) C23 0.057(3) 0.065(3) 0.084(4) 0.007(3) -0.018(3) -0.021(3) C24 0.055(3) 0.056(3) 0.047(3) -0.006(2) 0.007(2) -0.016(2) C25 0.047(2) 0.048(3) 0.043(3) -0.005(2) 0.005(2) -0.019(2) C26 0.058(3) 0.053(3) 0.067(3) -0.017(2) 0.015(2) -0.017(2) C27 0.042(2) 0.041(2) 0.048(3) -0.012(2) 0.007(2) -0.0112(19) C28 0.053(3) 0.051(3) 0.054(3) 0.003(2) -0.005(2) -0.003(2) C29 0.041(2) 0.073(3) 0.077(4) -0.014(3) -0.001(3) -0.013(2) C30 0.055(3) 0.056(3) 0.059(3) -0.014(2) 0.019(2) -0.016(2) C31 0.065(3) 0.057(3) 0.047(3) -0.004(2) 0.003(2) -0.009(2) C32 0.043(2) 0.063(3) 0.050(3) -0.013(2) -0.004(2) -0.007(2) P1 0.0345(5) 0.0372(6) 0.0357(6) -0.0073(4) -0.0048(4) -0.0070(4) P2 0.0419(6) 0.0445(6) 0.0394(6) -0.0080(5) 0.0025(5) -0.0188(5) S1 0.0474(6) 0.0517(7) 0.0441(6) 0.0035(5) -0.0100(5) -0.0183(5) S2 0.0469(6) 0.0378(6) 0.0533(7) -0.0108(5) -0.0110(5) -0.0051(5) S3 0.0795(9) 0.0561(7) 0.0845(10) -0.0343(7) 0.0355(8) -0.0406(7) S4 0.0548(6) 0.0621(7) 0.0438(6) -0.0151(5) 0.0011(5) -0.0290(6) _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 S1 2.2918(11) . ? Au1 S2 2.2976(11) . ? Au1 Au1 3.2668(3) 2_656 ? Au2 S3 2.2842(12) . ? Au2 S4 2.2900(11) . ? Au2 Au2 3.2678(3) 2_666 ? C1 C2 1.507(6) . ? C1 P1 1.815(4) . ? C2 C3 1.524(6) . ? C3 C8 1.372(6) . ? C3 C4 1.386(6) . ? C4 C5 1.374(7) . ? C5 C6 1.357(8) . ? C6 C7 1.363(8) . ? C7 C8 1.385(7) . ? C9 C10 1.518(6) . ? C9 P1 1.811(4) . ? C10 C11 1.518(5) . ? C11 C16 1.369(6) . ? C11 C12 1.376(6) . ? C12 C13 1.379(7) . ? C13 C14 1.354(8) . ? C14 C15 1.378(8) . ? C15 C16 1.386(7) . ? C17 C18 1.487(6) . ? C17 P2 1.816(5) . ? C18 C19 1.488(6) . ? C19 C24 1.377(6) . ? C19 C20 1.421(7) . ? C20 C21 1.395(8) . ? C21 C22 1.349(9) . ? C22 C23 1.316(8) . ? C23 C24 1.354(7) . ? C25 C26 1.531(6) . ? C25 P2 1.811(4) . ? C26 C27 1.513(6) . ? C27 C28 1.384(6) . ? C27 C32 1.385(6) . ? C28 C29 1.373(6) . ? C29 C30 1.372(7) . ? C30 C31 1.364(6) . ? C31 C32 1.381(6) . ? P1 S1 2.0234(15) . ? P1 S2 2.0292(14) 2_656 ? P2 S3 2.0174(16) . ? P2 S4 2.0206(15) 2_666 ? S2 P1 2.0292(14) 2_656 ? S4 P2 2.0205(15) 2_666 ? 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 S1 Au1 S2 174.96(4) . . ? S1 Au1 Au1 91.47(3) . 2_656 ? S2 Au1 Au1 93.27(3) . 2_656 ? S3 Au2 S4 174.41(4) . . ? S3 Au2 Au2 92.58(3) . 2_666 ? S4 Au2 Au2 92.55(3) . 2_666 ? C2 C1 P1 113.8(3) . . ? C1 C2 C3 115.6(4) . . ? C8 C3 C4 117.8(4) . . ? C8 C3 C2 123.6(4) . . ? C4 C3 C2 118.6(4) . . ? C5 C4 C3 120.9(5) . . ? C6 C5 C4 120.6(5) . . ? C5 C6 C7 119.5(5) . . ? C6 C7 C8 120.4(5) . . ? C3 C8 C7 120.8(5) . . ? C10 C9 P1 115.6(3) . . ? C11 C10 C9 113.2(3) . . ? C16 C11 C12 118.9(4) . . ? C16 C11 C10 120.9(4) . . ? C12 C11 C10 120.2(4) . . ? C11 C12 C13 120.6(5) . . ? C14 C13 C12 120.6(5) . . ? C13 C14 C15 119.6(5) . . ? C14 C15 C16 119.9(5) . . ? C11 C16 C15 120.5(5) . . ? C18 C17 P2 121.4(4) . . ? C17 C18 C19 114.6(4) . . ? C24 C19 C20 116.4(4) . . ? C24 C19 C18 124.0(5) . . ? C20 C19 C18 119.6(4) . . ? C21 C20 C19 118.8(5) . . ? C22 C21 C20 120.4(5) . . ? C23 C22 C21 121.3(6) . . ? C22 C23 C24 120.6(6) . . ? C23 C24 C19 122.5(5) . . ? C26 C25 P2 116.2(3) . . ? C27 C26 C25 110.8(3) . . ? C28 C27 C32 117.6(4) . . ? C28 C27 C26 121.4(4) . . ? C32 C27 C26 120.8(4) . . ? C29 C28 C27 121.1(4) . . ? C30 C29 C28 120.6(4) . . ? C31 C30 C29 119.2(4) . . ? C30 C31 C32 120.6(5) . . ? C31 C32 C27 120.9(4) . . ? C9 P1 C1 107.80(19) . . ? C9 P1 S1 104.37(14) . . ? C1 P1 S1 111.85(15) . . ? C9 P1 S2 106.55(14) . 2_656 ? C1 P1 S2 108.61(14) . 2_656 ? S1 P1 S2 117.09(7) . 2_656 ? C25 P2 C17 104.9(2) . . ? C25 P2 S3 103.08(14) . . ? C17 P2 S3 112.3(2) . . ? C25 P2 S4 106.84(15) . 2_666 ? C17 P2 S4 109.75(18) . 2_666 ? S3 P2 S4 118.68(8) . 2_666 ? P1 S1 Au1 102.61(5) . . ? P1 S2 Au1 101.66(5) 2_656 . ? P2 S3 Au2 103.88(6) . . ? P2 S4 Au2 102.78(6) 2_666 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.118 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 960263' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Au I2 P S2' _chemical_formula_weight 756.16 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' S S 0.1246 0.1234 '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 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 13.013(3) _cell_length_b 9.3266(19) _cell_length_c 18.341(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.03(3) _cell_angle_gamma 90.00 _cell_volume 2128.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.3917 _cell_measurement_theta_max 0.7454 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 10.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1357 _exptl_absorpt_correction_T_max 0.2642 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7198 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1879 _reflns_number_gt 1675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-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^)+(0.0146P)^2^+9.7315P] 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 1879 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0530 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 1.0000 1.05730(3) 0.7500 0.03663(10) Uani 1 2 d S . . I1 I 1.11803(4) 1.24850(4) 0.70952(3) 0.06101(15) Uani 1 1 d . . . S1 S 1.09861(12) 0.86997(17) 0.71621(9) 0.0509(4) Uani 1 1 d . . . P1 P 1.0000 0.7297(2) 0.7500 0.0479(5) Uani 1 2 d S . . C1 C 0.9269(6) 0.6133(6) 0.6743(3) 0.0575(17) Uani 1 1 d . . . H1A H 0.9771 0.5466 0.6627 0.069 Uiso 1 1 calc R . . H1B H 0.8761 0.5577 0.6923 0.069 Uiso 1 1 calc R . . C2 C 0.8658(6) 0.6899(7) 0.6011(4) 0.0677(19) Uani 1 1 d . . . H2A H 0.8146 0.7561 0.6119 0.081 Uiso 1 1 calc R . . H2B H 0.9158 0.7449 0.5822 0.081 Uiso 1 1 calc R . . C3 C 0.8068(5) 0.5841(7) 0.5408(3) 0.0552(16) Uani 1 1 d . . . C4 C 0.8475(7) 0.5418(8) 0.4824(4) 0.075(2) Uani 1 1 d . . . H4 H 0.9120 0.5795 0.4789 0.091 Uiso 1 1 calc R . . C5 C 0.7113(6) 0.5260(8) 0.5426(4) 0.071(2) Uani 1 1 d . . . H5 H 0.6821 0.5532 0.5811 0.085 Uiso 1 1 calc R . . C6 C 0.7914(9) 0.4428(10) 0.4293(4) 0.091(3) Uani 1 1 d . . . H6 H 0.8190 0.4147 0.3902 0.109 Uiso 1 1 calc R . . C7 C 0.6577(7) 0.4289(9) 0.4893(5) 0.084(2) Uani 1 1 d . . . H7 H 0.5926 0.3917 0.4920 0.100 Uiso 1 1 calc R . . C8 C 0.6975(9) 0.3861(9) 0.4330(5) 0.090(3) Uani 1 1 d . . . H8 H 0.6611 0.3189 0.3973 0.108 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 0.03183(15) 0.03215(18) 0.04635(18) 0.000 0.01216(12) 0.000 I1 0.0662(3) 0.0454(3) 0.0849(3) -0.0013(2) 0.0432(3) -0.01122(19) S1 0.0458(8) 0.0390(9) 0.0719(10) 0.0004(7) 0.0236(7) 0.0086(7) P1 0.0549(13) 0.0311(12) 0.0515(13) 0.000 0.0059(11) 0.000 C1 0.074(4) 0.034(3) 0.049(3) -0.001(3) -0.006(3) 0.002(3) C2 0.085(5) 0.046(4) 0.056(4) 0.010(3) -0.003(4) 0.005(4) C3 0.061(4) 0.053(4) 0.041(3) 0.006(3) -0.002(3) 0.011(3) C4 0.078(5) 0.078(6) 0.067(5) 0.010(4) 0.017(4) 0.023(4) C5 0.081(5) 0.069(5) 0.058(4) -0.002(4) 0.014(4) 0.004(4) C6 0.130(8) 0.087(7) 0.049(4) -0.009(4) 0.016(5) 0.037(6) C7 0.077(5) 0.081(6) 0.077(5) 0.002(5) -0.003(4) -0.005(4) C8 0.111(8) 0.069(6) 0.064(5) -0.005(4) -0.016(5) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 S1 2.3557(15) . ? Au1 S1 2.3557(15) 2_756 ? Au1 I1 2.5997(6) . ? Au1 I1 2.5997(6) 2_756 ? S1 P1 2.051(2) . ? P1 C1 1.800(6) 2_756 ? P1 C1 1.800(6) . ? P1 S1 2.051(2) 2_756 ? C1 C2 1.522(8) . ? C2 C3 1.514(9) . ? C3 C5 1.365(10) . ? C3 C4 1.383(10) . ? C4 C6 1.385(12) . ? C5 C7 1.365(11) . ? C6 C8 1.351(13) . ? C7 C8 1.344(12) . ? 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 S1 Au1 S1 84.25(8) . 2_756 ? S1 Au1 I1 91.18(4) . . ? S1 Au1 I1 175.44(4) 2_756 . ? S1 Au1 I1 175.44(4) . 2_756 ? S1 Au1 I1 91.18(4) 2_756 2_756 ? I1 Au1 I1 93.38(3) . 2_756 ? P1 S1 Au1 87.49(7) . . ? C1 P1 C1 105.8(4) 2_756 . ? C1 P1 S1 112.4(2) 2_756 . ? C1 P1 S1 112.8(2) . . ? C1 P1 S1 112.8(2) 2_756 2_756 ? C1 P1 S1 112.4(2) . 2_756 ? S1 P1 S1 100.76(12) . 2_756 ? C2 C1 P1 114.7(4) . . ? C3 C2 C1 111.1(5) . . ? C5 C3 C4 117.6(7) . . ? C5 C3 C2 120.8(7) . . ? C4 C3 C2 121.7(7) . . ? C3 C4 C6 119.5(8) . . ? C3 C5 C7 121.6(8) . . ? C8 C6 C4 121.6(8) . . ? C8 C7 C5 121.0(9) . . ? C7 C8 C6 118.7(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.752 _refine_diff_density_min -1.580 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 960264'