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The title compound, [Au(C6F5)3(PPh2C6H4SH)]·CH2Cl2, presents a square-planar geometry. The long Au—P bond, 2.3884 (16) Å, is consistent with an appreciable trans influence of the penta­fluoro­phenyl group. The intramolecular Au...S contact is 3.594 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002404/bt6109sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002404/bt6109Isup2.hkl
Contains datablock I

CCDC reference: 182578

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in solvent or counterion
  • R factor = 0.032
  • wR factor = 0.072
  • Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSTM_02 Alert B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.527 0.960 Tmin and Tmax expected: 0.195 0.593 RR = 1.670 Please check that your absorption correction is appropriate.
Author response: Despite eminently sensible-looking psi-scans, the minimum transmission is not as low as expected. Possible reasons: (i) The crystal size may be slightly inaccurate (oildrop) or (ii) No X-ray beam actually traversed the longest crystal dimension.

Yellow Alert Alert Level C:
PLAT_202 Alert C Isotropic non-H Atoms in Anion/Solvent = 1 PLAT_213 Alert C Atom F3 has ADP max/min Ratio ........... 3.10 prolate PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc. PLAT_420 Alert C D-H Without Acceptor S - H0 ? PLAT_731 Alert C Bond Calc 1.33(5), Rep 1.331(19) .... 2.63 s.u-Ratio S -H0 1.555 1.555 General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.618 Tmax scaled 0.593 Tmin scaled 0.326
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
5 Alert Level C = Please check

Comment top

In recent years, there has been considerable interest in thiolate–gold chemistry; most of the complexes studied have also contained phosphine ligands (Terroba et al., 1998; Cerrada et al., 1995; Gimeno et al., 1994; Yip et al., 1994; Davila et al., 1993; Nakamoto et al., 1993). Another way of combining the aspects of both thiolate and phosphine chemistry is to work with bidentate ligands containing both S and P functions, as are found in phosphinethiols. The selective coordination of either phosphorus or sulfur to different metal centres can in principle allow the combination of disparate metals in the same molecule. Such heteropolynuclear compounds are of interest because of their possible application in catalysis (Simpson & Colehamilton, 1996; Stephan, 1989).

The reaction of the ligand 2-(diphenylphosphino)thiophenol (Block et al., 1989) with [Au(C6F5)3(tht)] (Usón et al., 1982) proceeds with substitution of tetrahydrothiophene (tht), a labile ligand in gold chemistry, by the phosphine function of the ligand. The product obtained is the title compound, [Au(C6F5)3(PPh2C6H4SH)], (I), still containing the unchanged thiol group, which is a potential site for further reactions.

The structure of (1) is shown in Fig. 1. The gold centre displays square-planar geometry, with bond angles (Table 1) close to the ideal values. The mean deviation of gold and its four immediate donors from their best plane is 0.09 Å, whereby the atoms P and C21 lie on one side of the plane and C11 and C31 on the other. The Au—P distance, 2.3884 (16) Å, is amongst the longest so far observed in gold(III) complexes. This lengthening can reasonably be attributed to the trans effect of the pentafluorophenyl group. A search of the Cambridge Structural Database (Version of October 1998; Allen & Kennard, 1993) indeed revealed that the longest AuIII—P bonds are formed trans to σ-carbon ligands: e.g. cis-[Au(CH3)2(PPh3)(OPh)] 2.402 (4) Å (Sone et al., 1991); cis-[Au(CH3)2{Ph2P(O)CH2PPh2}Cl] 2.389 (2) Å (Paul & Schmidbaur, 1996); [Au(2-PhNNC6H4){3,4,5-(CH3O)3—C6H2COCH2}(PPh3)Cl] 2.386 and 2.390 (2) Å (Vicente et al., 1993). Typical examples without such ligands are [Au(C6F5)(S2C6H4)PPh3] 2.340 (1) Å (Cerrada et al., 1995); [AuCl3(PPh3)] 2.335 (4) Å (Bandoli et al., 1973); [AuMe3(PPh3)] 2.350 (6) and 2.347 (6) Å (Stein et al., 1981); [Au(SC6H4PPh2)2]BPh4 2.325 (4) and 2.332 (4) Å (Dilworth et al., 1994). The Au—C bond lengths, 2.056 (5)–2.073 (5) Å, are similar to those of other tris(pentafluorophenyl)gold(III) complexes: [Au(C6F5)3(S2C—PEt3)] 2.037 (3) and 2.076 (4) Å (Usón et al., 1987); [(µ-S2C—PEt3){Au(C6F5)3}2] 2.048 (16) and 2.090 (13) Å (Usón et al., 1987); NBu4[{Au(C6F5)3PPh2CHPh2}2Au] 2.057 (8) and 2.080 (8) Å (Fernández et al., 1995). The shortest Au—C distance (although the differences are not great) corresponds to the pentafluorophenyl group trans to phosphorus.

The intramolecular Au···S contact is 3.594 (2) Å, which represents at best a very weak interaction; such axial contacts are typical of AuIII complexes.

Experimental top

The ligand HSC6H4PPh2 (0.029 g, 0.1 mmol) was added to a dichloromethane solution (20 ml) of [Au(C6F5)3(tht)] (0.079 g, 0.1 mmol). After stirring for 3 h, the solution was filtered through diatomaceous earth and concentrated in vacuo; addition of hexane precipitates the product as a white solid (yield: 47%). 1H NMR: δ(SH) 3.74(s). 31P{1H} NMR: δ 17.7 (s). 19F NMR: δ -118.0 (m, 4 F, Fo), -121.6 (m, 2 F, Fo), -157.1 (t, 3JFpFm = 19.7 Hz, 1 F, Fp), -157.3 (t, 3JFpFm = 19.9 Hz, 2 F, Fp), -161.1 (m, 4 F, Fm), -161.3 (m, 2 F, Fm). Crystals of the complex were obtained by slow diffusion of hexane into a dichloromethane solution.

Refinement top

The dichloromethane molecule is disordered over two sites with occupation factors 0.727 (9) and 0.273 (9). The minor Cl component and both C components were refined isotropically. The H atom of the thiol group was tentatively identified as a peak of 0.4 e Å-3 with acceptable geometry at sulfur, and was refined with a distance restraint (DFIX) of S—H = 1.33 (2) Å and fixed U. It however makes a short contact of 2.35 Å to C54 of a neighbouring molecule at 1 - x, 1 - y, 1 - z. Clearly this H-atom site should be interpreted with caution. We have previously failed to locate the H atom of SH groups in some gold complexes, even with apparently good data (Vicente et al., 1994). Other H atoms were included using a riding model. To improve stability of refinement, an extensive system of restraints to light-atom displacement parameter components and local ring symmetry was employed. Details are given in the final instruction file, which is included in the deposited material.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4(Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecule of the title compound in the crystal (solvent omitted). Ellipsoids represent 50% probability levels.
Tris(pentafluorophenyl)-(2-diphenylphosphinethiophenyl)- gold(III) Dichloromethane Solvate top
Crystal data top
[Au(C6F5)3(C18H15PS)]·CH2Cl2Z = 2
Mr = 1077.40F(000) = 1036
Triclinic, P1Dx = 1.945 Mg m3
a = 10.057 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.888 (5) ÅCell parameters from 52 reflections
c = 15.236 (7) Åθ = 10–11.5°
α = 100.64 (3)°µ = 4.35 mm1
β = 94.41 (3)°T = 143 K
γ = 106.84 (3)°Tablet, colourless
V = 1839.7 (13) Å30.4 × 0.4 × 0.12 mm
Data collection top
Stoe STADI-4
diffractometer
5909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
ω/θ scansh = 112
Absorption correction: ψ scan
(XEMP; Siemens, 1994)
k = 1515
Tmin = 0.527, Tmax = 0.960l = 1818
8252 measured reflections3 standard reflections every 60 min
6462 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: Patterson
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0287P)2 + 2.7433P]
where P = (Fo2 + 2Fc2)/3
6462 reflections(Δ/σ)max = 0.022
525 parametersΔρmax = 0.87 e Å3
539 restraintsΔρmin = 0.70 e Å3
Crystal data top
[Au(C6F5)3(C18H15PS)]·CH2Cl2γ = 106.84 (3)°
Mr = 1077.40V = 1839.7 (13) Å3
Triclinic, P1Z = 2
a = 10.057 (4) ÅMo Kα radiation
b = 12.888 (5) ŵ = 4.35 mm1
c = 15.236 (7) ÅT = 143 K
α = 100.64 (3)°0.4 × 0.4 × 0.12 mm
β = 94.41 (3)°
Data collection top
Stoe STADI-4
diffractometer
5909 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XEMP; Siemens, 1994)
Rint = 0.029
Tmin = 0.527, Tmax = 0.9603 standard reflections every 60 min
8252 measured reflections intensity decay: none
6462 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032539 restraints
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.87 e Å3
6462 reflectionsΔρmin = 0.70 e Å3
525 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

============================================================================== Dimensions not listed below:

3.5936 (0.0023) Au - S 1.3308 (0.0191) S - H0 99.85 (2.52) C42 - S - H0

==============================================================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.6568 (0.0111) x + 5.1486 (0.0187) y + 12.5978 (0.0151) z = 3.7281 (0.0042)

* 0.0215 (0.0016) Au * -0.0880 (0.0017) P * 0.0902 (0.0022) C11 * -0.1131 (0.0022) C21 * 0.0894 (0.0022) C31

Rms deviation of fitted atoms = 0.0862 ==============================================================================

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Final instruction file:

============================================================================= TITL turbio in P-1 CELL 0.71073 10.0567 12.8880 15.2365 100.637 94.411 106.839 ZERR 2.00 0.0040 0.0050 0.0070 0.030 0.030 0.030 SFAC C H F P S AU CL UNIT 74 34 30 2 2 2 4 TEMP -130 SIZE 0.5 0.5 0.1 L·S. 8 ACTA RTAB CONT AU S RTAB S-H S H0 RTAB S-H C42 S H0 FMAP 2 PLAN 10 SIMU DELU $C $F SIMU 0.02 0.04 0.9 W GH T 0.028700 2.743300 FVAR 0.05360 0.27253 AU 6 0.262103 0.262949 0.245452 11.00000 0.02463 0.02472 = 0.02616 0.00566 0.00346 0.00659 P 4 0.503481 0.361958 0.247199 11.00000 0.02515 0.02385 = 0.02850 0.00440 0.00333 0.00569 S 5 0.413577 0.535895 0.386483 11.00000 0.05714 0.04621 = 0.04147 0.00013 0.02212 0.01170 DFIX S H0 1.33 0.02 H0 2 0.330918 0.599310 0.402782 11.00000 - 1.20000 F L A T C11 > F5 SAME C11 C16 < C12 F5 < F1 C11 1 0.308545 0.146665 0.308226 11.00000 0.03192 0.03713 = 0.04260 0.01653 0.00190 0.00920 C12 1 0.305397 0.043879 0.263310 11.00000 0.03805 0.04078 = 0.05259 0.01900 0.01208 0.01510 C13 1 0.322355 - 0.037197 0.307880 11.00000 0.05363 0.05125 = 0.10587 0.03848 0.02298 0.03376 C14 1 0.342850 - 0.013873 0.399908 11.00000 0.04296 0.07873 = 0.10218 0.06577 0.00963 0.02319 C15 1 0.344688 0.086893 0.447343 11.00000 0.03846 0.09027 = 0.06512 0.05048 0.00691 0.01662 C16 1 0.328703 0.166104 0.401796 11.00000 0.02733 0.05846 = 0.04395 0.02492 0.00427 0.00690 F1 3 0.281784 0.017335 0.172183 11.00000 0.06793 0.03895 = 0.06112 0.00200 0.01218 0.02065 F2 3 0.318761 - 0.136649 0.259309 11.00000 0.08918 0.05033 = 0.15412 0.04070 0.03647 0.04201 F3 3 0.355624 - 0.092898 0.443376 11.00000 0.08136 0.12137 = 0.17478 0.12131 0.03067 0.05104 F4 3 0.363369 0.110272 0.538198 11.00000 0.06872 0.14506 = 0.06504 0.06967 0.00925 0.02828 F5 3 0.333834 0.265824 0.450606 11.00000 0.05623 0.06180 = 0.03441 0.00443 - 0.00101 0.00904 F L A T C21 > F10 SAME C21 C26 < C22 F10 < F6 C21 1 0.055329 0.167493 0.230164 11.00000 0.02904 0.02623 = 0.03297 0.00877 0.00302 0.01126 C22 1 - 0.020223 0.151091 0.300456 11.00000 0.03097 0.03235 = 0.03607 0.00637 0.00601 0.00722 C23 1 - 0.157180 0.084009 0.287319 11.00000 0.03505 0.03255 = 0.04530 0.01387 0.01804 0.00711 C24 1 - 0.222584 0.031996 0.201553 11.00000 0.02721 0.03123 = 0.05952 0.00903 0.00428 0.00215 C25 1 - 0.149823 0.044746 0.129697 11.00000 0.03350 0.03196 = 0.04002 - 0.00114 - 0.00106 0.00685 C26 1 - 0.013882 0.112194 0.144860 11.00000 0.02794 0.03122 = 0.03996 0.00702 0.00510 0.00666 F6 3 0.038890 0.201642 0.385900 11.00000 0.04159 0.05530 = 0.03018 0.00594 0.00719 0.00206 F7 3 - 0.228558 0.066246 0.357553 11.00000 0.05089 0.06038 = 0.05957 0.01923 0.02809 0.00233 F8 3 - 0.356925 - 0.033062 0.188911 11.00000 0.03301 0.05444 = 0.08250 0.00654 0.00726 - 0.00909 F9 3 - 0.213329 - 0.008169 0.046026 11.00000 0.04469 0.05287 = 0.04818 - 0.00732 - 0.00723 0.00193 F10 3 0.054493 0.125142 0.072915 11.00000 0.04395 0.05157 = 0.03114 0.00191 0.00725 0.00840 F L A T C31 > F15 SAME C31 C36 < C32 F15 < F11 C31 1 0.189965 0.375097 0.189794 11.00000 0.02391 0.02965 = 0.03020 0.00610 0.00233 0.00837 C32 1 0.113642 0.433944 0.235576 11.00000 0.02849 0.03633 = 0.03506 0.00839 0.00806 0.00774 C33 1 0.073468 0.516507 0.205125 11.00000 0.03414 0.03376 = 0.04461 0.00580 0.00854 0.01356 C34 1 0.109447 0.541222 0.125195 11.00000 0.04088 0.04175 = 0.05444 0.02047 0.00462 0.01814 C35 1 0.181796 0.481687 0.074778 11.00000 0.03780 0.05171 = 0.04115 0.02366 0.00940 0.01485 C36 1 0.218303 0.399245 0.107875 11.00000 0.02712 0.03698 = 0.03455 0.00929 0.00530 0.01020 F11 3 0.073692 0.412864 0.314839 11.00000 0.04473 0.04019 = 0.03671 0.00771 0.01568 0.01542 F12 3 0.001089 0.572651 0.254335 11.00000 0.05918 0.05037 = 0.07147 0.01270 0.02162 0.03410 F13 3 0.073354 0.621363 0.094105 11.00000 0.06853 0.06097 = 0.08735 0.04321 0.01726 0.03900 F14 3 0.214775 0.503288 - 0.004928 11.00000 0.06098 0.08047 = 0.05683 0.04537 0.02315 0.03304 F15 3 0.290716 0.344048 0.055945 11.00000 0.04880 0.05703 = 0.03767 0.01720 0.01787 0.02725 F L A T C41 > C46 SAME C41 C46 < C42 C41 1 0.519803 0.499734 0.227888 11.00000 0.03153 0.02597 = 0.03382 0.00731 0.00850 0.00819 C42 1 0.471576 0.572618 0.288490 11.00000 0.02660 0.03012 = 0.03818 0.00025 0.00246 0.00434 C43 1 0.469319 0.671790 0.266606 11.00000 0.04828 0.02770 = 0.05506 0.00375 0.01055 0.01133 AFIX 43 H43 2 0.438330 0.722415 0.307115 11.00000 - 1.20000 AFIX 0 C44 1 0.510618 0.698512 0.188123 11.00000 0.06406 0.03600 = 0.07538 0.02253 0.01849 0.02002 AFIX 43 H44 2 0.504847 0.765959 0.173924 11.00000 - 1.20000 AFIX 0 C45 1 0.560819 0.628262 0.129047 11.00000 0.06322 0.04379 = 0.05608 0.02480 0.01890 0.01359 AFIX 43 H45 2 0.591003 0.647868 0.075090 11.00000 - 1.20000 AFIX 0 C46 1 0.566563 0.529080 0.149456 11.00000 0.03641 0.03239 = 0.04515 0.01517 0.01619 0.00569 AFIX 43 H46 2 0.602446 0.480999 0.109906 11.00000 - 1.20000 AFIX 0 F L A T C51 > C56 SAME C51 C56 < C52 C51 1 0.629013 0.379360 0.344733 11.00000 0.02609 0.03608 = 0.03132 0.00354 0.00630 0.00700 C52 1 0.711281 0.485031 0.392203 11.00000 0.03351 0.03994 = 0.03929 0.00276 0.00485 0.01042 AFIX 43 H52 2 0.699575 0.549244 0.374736 11.00000 - 1.20000 AFIX 0 C53 1 0.810054 0.495967 0.464869 11.00000 0.03413 0.05295 = 0.03616 - 0.00390 0.00101 0.00190 AFIX 43 H53 2 0.865158 0.567789 0.497599 11.00000 - 1.20000 AFIX 0 C54 1 0.828373 0.403741 0.489545 11.00000 0.03099 0.07359 = 0.03131 0.00721 0.00399 0.01839 AFIX 43 H54 2 0.895920 0.411940 0.539565 11.00000 - 1.20000 AFIX 0 C55 1 0.749663 0.298935 0.442464 11.00000 0.03121 0.05892 = 0.03952 0.01407 0.00873 0.02172 AFIX 43 H55 2 0.763481 0.235330 0.459893 11.00000 - 1.20000 AFIX 0 C56 1 0.650125 0.286307 0.369523 11.00000 0.03257 0.03807 = 0.04062 0.00795 0.00743 0.01012 AFIX 43 H56 2 0.596597 0.214114 0.336666 11.00000 - 1.20000 AFIX 0 F L A T C61 > C66 SAME C61 C66 < C62 C61 1 0.574684 0.292027 0.156599 11.00000 0.03112 0.02518 = 0.03033 0.00554 0.00665 0.00912 C62 1 0.488459 0.208569 0.087355 11.00000 0.02781 0.03030 = 0.03685 0.00505 0.00109 0.00704 AFIX 43 H62 2 0.389903 0.184522 0.087842 11.00000 - 1.20000 AFIX 0 C63 1 0.545902 0.160568 0.017853 11.00000 0.04402 0.03139 = 0.03489 - 0.00672 - 0.00376 0.00975 AFIX 43 H63 2 0.486439 0.103050 - 0.029222 11.00000 - 1.20000 AFIX 0 C64 1 0.688921 0.195012 0.015730 11.00000 0.04581 0.03937 = 0.04043 0.00262 0.00854 0.01782 AFIX 43 H64 2 0.727338 0.162273 - 0.033047 11.00000 - 1.20000 AFIX 0 C65 1 0.776231 0.277810 0.085349 11.00000 0.02985 0.03973 = 0.03866 0.00459 0.00785 0.01296 AFIX 43 H65 2 0.874679 0.301724 0.084396 11.00000 - 1.20000 AFIX 0 C66 1 0.719912 0.325076 0.155622 11.00000 0.03073 0.03303 = 0.03710 0.00193 0.00348 0.01031 AFIX 43 H66 2 0.779938 0.380518 0.203823 11.00000 - 1.20000 AFIX 0 SAME C99' > CL2' PART 1 C99 1 0.110520 0.182143 0.668445 21.00000 0.10738 AFIX 23 H99A 2 0.110456 0.255155 0.656688 21.00000 - 1.20000 H99B 2 0.208940 0.181466 0.671360 21.00000 - 1.20000 AFIX 0 C L1 7 0.020476 0.086341 0.577453 21.00000 0.14816 C L2 7 0.065092 0.178806 0.773267 21.00000 0.20621 part 2 C99' 1 0.132180 0.217475 0.698068 - 21.00000 0.07990 AFIX 23 H99C 2 0.209978 0.185677 0.689154 - 21.00000 - 1.20000 H99D 2 0.174102 0.298924 0.718794 - 21.00000 - 1.20000 AFIX 0 C L1' 7 0.029098 0.190146 0.595904 - 21.00000 0.12408 0.17265 = 0.09154 0.01506 - 0.00164 0.03018 C L2' 7 0.046565 0.166719 0.780592 - 21.00000 0.09086 0.07794 = 0.13330 0.04536 0.02614 0.04328

HKLF 4 ==============================================================================

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Au0.262103 (19)0.262949 (14)0.245452 (12)0.02538 (7)
P0.50348 (13)0.36196 (9)0.24720 (8)0.0264 (3)
S0.41358 (17)0.53589 (12)0.38648 (10)0.0496 (4)
H00.331 (5)0.599 (4)0.403 (4)0.060*
C110.3085 (5)0.1467 (4)0.3082 (3)0.0367 (11)
C120.3054 (5)0.0439 (4)0.2633 (4)0.0417 (12)
C130.3224 (6)0.0372 (5)0.3079 (5)0.0629 (17)
C140.3428 (7)0.0139 (5)0.3999 (5)0.0675 (17)
C150.3447 (7)0.0869 (6)0.4473 (4)0.0608 (16)
C160.3287 (5)0.1661 (5)0.4018 (4)0.0428 (12)
F10.2818 (4)0.0173 (2)0.1722 (2)0.0561 (9)
F20.3188 (5)0.1366 (3)0.2593 (4)0.0898 (14)
F30.3556 (5)0.0929 (4)0.4434 (4)0.1088 (19)
F40.3634 (4)0.1103 (4)0.5382 (3)0.0877 (14)
F50.3338 (4)0.2658 (3)0.4506 (2)0.0541 (9)
C210.0553 (5)0.1675 (3)0.2302 (3)0.0286 (10)
C220.0202 (5)0.1511 (3)0.3005 (3)0.0338 (11)
C230.1572 (5)0.0840 (4)0.2873 (4)0.0369 (11)
C240.2226 (5)0.0320 (4)0.2016 (4)0.0410 (12)
C250.1498 (5)0.0447 (4)0.1297 (3)0.0374 (11)
C260.0139 (5)0.1122 (4)0.1449 (3)0.0337 (11)
F60.0389 (3)0.2016 (3)0.38590 (19)0.0455 (8)
F70.2286 (4)0.0662 (3)0.3576 (2)0.0582 (9)
F80.3569 (3)0.0331 (3)0.1889 (3)0.0628 (10)
F90.2133 (3)0.0082 (3)0.0460 (2)0.0547 (9)
F100.0545 (3)0.1251 (2)0.07291 (19)0.0445 (7)
C310.1900 (5)0.3751 (4)0.1898 (3)0.0280 (10)
C320.1136 (5)0.4339 (4)0.2356 (3)0.0335 (11)
C330.0735 (5)0.5165 (4)0.2051 (4)0.0370 (11)
C340.1094 (6)0.5412 (4)0.1252 (4)0.0433 (13)
C350.1818 (6)0.4817 (4)0.0748 (4)0.0413 (12)
C360.2183 (5)0.3992 (4)0.1079 (3)0.0326 (11)
F110.0737 (3)0.4129 (2)0.31484 (19)0.0396 (7)
F120.0011 (4)0.5727 (3)0.2543 (2)0.0560 (9)
F130.0734 (4)0.6214 (3)0.0941 (3)0.0641 (10)
F140.2148 (4)0.5033 (3)0.0049 (2)0.0587 (9)
F150.2907 (3)0.3440 (3)0.0559 (2)0.0439 (7)
C410.5198 (5)0.4997 (4)0.2279 (3)0.0303 (10)
C420.4716 (5)0.5726 (4)0.2885 (3)0.0337 (11)
C430.4693 (6)0.6718 (4)0.2666 (4)0.0443 (13)
H430.43830.72240.30710.053*
C440.5106 (7)0.6985 (5)0.1881 (4)0.0556 (16)
H440.50480.76600.17390.067*
C450.5608 (7)0.6283 (4)0.1290 (4)0.0525 (15)
H450.59100.64790.07510.063*
C460.5666 (5)0.5291 (4)0.1495 (4)0.0376 (12)
H460.60240.48100.10990.045*
C510.6290 (5)0.3794 (4)0.3447 (3)0.0321 (11)
C520.7113 (5)0.4850 (4)0.3922 (3)0.0386 (12)
H520.69960.54920.37470.046*
C530.8101 (6)0.4960 (5)0.4649 (4)0.0457 (13)
H530.86520.56780.49760.055*
C540.8284 (6)0.4037 (5)0.4895 (4)0.0454 (13)
H540.89590.41190.53960.054*
C550.7497 (5)0.2989 (5)0.4425 (4)0.0409 (12)
H550.76350.23530.45990.049*
C560.6501 (5)0.2863 (4)0.3695 (4)0.0372 (12)
H560.59660.21410.33670.045*
C610.5747 (5)0.2920 (3)0.1566 (3)0.0287 (10)
C620.4885 (5)0.2086 (4)0.0874 (3)0.0326 (11)
H620.38990.18450.08780.039*
C630.5459 (6)0.1606 (4)0.0179 (3)0.0396 (12)
H630.48640.10300.02920.048*
C640.6889 (6)0.1950 (4)0.0157 (4)0.0415 (12)
H640.72730.16230.03300.050*
C650.7762 (5)0.2778 (4)0.0853 (3)0.0360 (11)
H650.87470.30170.08440.043*
C660.7199 (5)0.3251 (4)0.1556 (3)0.0344 (11)
H660.77990.38050.20380.041*
C990.111 (4)0.182 (3)0.6684 (18)0.107 (11)*0.273 (9)
H99A0.11050.25520.65670.129*0.273 (9)
H99B0.20890.18150.67140.129*0.273 (9)
Cl10.0205 (15)0.0863 (15)0.5775 (10)0.148 (6)*0.273 (9)
Cl20.065 (4)0.179 (2)0.7733 (17)0.206 (11)*0.273 (9)
C99'0.1322 (13)0.2175 (11)0.6981 (8)0.080 (3)*0.727 (9)
H99C0.21000.18570.68920.096*0.727 (9)
H99D0.17410.29890.71880.096*0.727 (9)
Cl1'0.0291 (5)0.1901 (5)0.5959 (3)0.136 (2)0.727 (9)
Cl2'0.0466 (6)0.1667 (4)0.7806 (4)0.0933 (15)0.727 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au0.02463 (10)0.02472 (10)0.02616 (10)0.00659 (7)0.00346 (7)0.00566 (7)
P0.0252 (6)0.0239 (5)0.0285 (6)0.0057 (5)0.0033 (5)0.0044 (5)
S0.0571 (10)0.0462 (8)0.0415 (8)0.0117 (7)0.0221 (7)0.0001 (6)
C110.032 (3)0.037 (2)0.043 (3)0.009 (2)0.002 (2)0.017 (2)
C120.038 (3)0.041 (3)0.053 (3)0.015 (2)0.012 (3)0.019 (2)
C130.054 (4)0.051 (3)0.106 (4)0.034 (3)0.023 (4)0.038 (3)
C140.043 (4)0.079 (4)0.102 (4)0.023 (3)0.010 (4)0.066 (3)
C150.038 (3)0.090 (4)0.065 (4)0.017 (3)0.007 (3)0.050 (3)
C160.027 (3)0.058 (3)0.044 (3)0.007 (2)0.004 (2)0.025 (2)
F10.068 (2)0.0389 (16)0.061 (2)0.0207 (16)0.0122 (19)0.0020 (15)
F20.089 (3)0.050 (2)0.154 (4)0.042 (2)0.036 (3)0.041 (2)
F30.081 (3)0.121 (4)0.175 (5)0.051 (3)0.031 (3)0.121 (4)
F40.069 (3)0.145 (4)0.065 (3)0.028 (3)0.009 (2)0.070 (3)
F50.056 (2)0.062 (2)0.0344 (18)0.0090 (17)0.0010 (16)0.0044 (15)
C210.029 (3)0.026 (2)0.033 (2)0.011 (2)0.003 (2)0.0088 (19)
C220.031 (3)0.032 (2)0.036 (3)0.007 (2)0.006 (2)0.006 (2)
C230.035 (3)0.033 (2)0.045 (3)0.007 (2)0.018 (2)0.014 (2)
C240.027 (3)0.031 (2)0.060 (3)0.002 (2)0.004 (2)0.009 (2)
C250.033 (3)0.032 (2)0.040 (3)0.007 (2)0.001 (2)0.001 (2)
C260.028 (3)0.031 (2)0.040 (3)0.007 (2)0.005 (2)0.007 (2)
F60.0416 (18)0.0553 (18)0.0302 (16)0.0021 (15)0.0072 (14)0.0059 (14)
F70.051 (2)0.060 (2)0.060 (2)0.0023 (17)0.0281 (18)0.0192 (17)
F80.0330 (18)0.054 (2)0.082 (3)0.0091 (15)0.0073 (18)0.0065 (18)
F90.045 (2)0.0529 (19)0.048 (2)0.0019 (16)0.0072 (16)0.0073 (15)
F100.0439 (18)0.0516 (18)0.0311 (16)0.0084 (15)0.0072 (14)0.0019 (14)
C310.024 (2)0.030 (2)0.030 (2)0.0084 (19)0.002 (2)0.0061 (19)
C320.028 (3)0.036 (2)0.035 (3)0.008 (2)0.008 (2)0.008 (2)
C330.034 (3)0.034 (2)0.045 (3)0.014 (2)0.009 (2)0.006 (2)
C340.041 (3)0.042 (3)0.054 (3)0.018 (2)0.005 (3)0.020 (3)
C350.038 (3)0.052 (3)0.041 (3)0.015 (2)0.009 (2)0.024 (3)
C360.027 (3)0.037 (2)0.035 (3)0.010 (2)0.005 (2)0.009 (2)
F110.0447 (18)0.0402 (15)0.0367 (17)0.0154 (14)0.0157 (14)0.0077 (13)
F120.059 (2)0.0504 (18)0.071 (2)0.0341 (17)0.0216 (19)0.0127 (17)
F130.069 (2)0.061 (2)0.087 (3)0.0390 (19)0.017 (2)0.043 (2)
F140.061 (2)0.080 (2)0.057 (2)0.0330 (19)0.0232 (18)0.0454 (19)
F150.0488 (19)0.0570 (18)0.0377 (17)0.0273 (15)0.0179 (15)0.0172 (14)
C410.032 (3)0.026 (2)0.034 (3)0.008 (2)0.009 (2)0.0073 (19)
C420.027 (3)0.030 (2)0.038 (3)0.004 (2)0.002 (2)0.000 (2)
C430.048 (3)0.028 (2)0.055 (3)0.011 (2)0.011 (3)0.004 (2)
C440.064 (4)0.036 (3)0.075 (4)0.020 (3)0.018 (3)0.023 (3)
C450.063 (4)0.044 (3)0.056 (4)0.014 (3)0.019 (3)0.025 (3)
C460.036 (3)0.032 (2)0.045 (3)0.006 (2)0.016 (2)0.015 (2)
C510.026 (3)0.036 (2)0.031 (3)0.007 (2)0.006 (2)0.004 (2)
C520.034 (3)0.040 (3)0.039 (3)0.010 (2)0.005 (2)0.003 (2)
C530.034 (3)0.053 (3)0.036 (3)0.002 (3)0.001 (2)0.004 (2)
C540.031 (3)0.074 (4)0.031 (3)0.018 (3)0.004 (2)0.007 (3)
C550.031 (3)0.059 (3)0.040 (3)0.022 (2)0.009 (2)0.014 (3)
C560.033 (3)0.038 (3)0.041 (3)0.010 (2)0.007 (2)0.008 (2)
C610.031 (3)0.025 (2)0.030 (3)0.009 (2)0.007 (2)0.0055 (18)
C620.028 (3)0.030 (2)0.037 (3)0.007 (2)0.001 (2)0.005 (2)
C630.044 (3)0.031 (2)0.035 (3)0.010 (2)0.004 (2)0.007 (2)
C640.046 (3)0.039 (3)0.040 (3)0.018 (2)0.009 (3)0.003 (2)
C650.030 (3)0.040 (3)0.039 (3)0.013 (2)0.008 (2)0.005 (2)
C660.031 (3)0.033 (2)0.037 (3)0.010 (2)0.003 (2)0.002 (2)
Cl1'0.124 (4)0.173 (6)0.092 (3)0.030 (3)0.002 (2)0.015 (3)
Cl2'0.091 (3)0.078 (2)0.133 (3)0.0433 (18)0.026 (2)0.045 (2)
Geometric parameters (Å, º) top
Au—C212.057 (5)C41—C461.394 (6)
Au—C112.060 (5)C41—C421.408 (6)
Au—C312.074 (4)C42—C431.385 (7)
Au—P2.3884 (16)C43—C441.366 (7)
P—C511.810 (5)C44—C451.385 (8)
P—C611.816 (5)C45—C461.386 (7)
P—C411.816 (5)C51—C561.389 (6)
S—C421.740 (5)C51—C521.398 (6)
C11—C121.365 (7)C52—C531.387 (7)
C11—C161.389 (7)C53—C541.367 (7)
C12—F11.352 (6)C54—C551.379 (7)
C12—C131.389 (7)C55—C561.390 (7)
C13—F21.346 (7)C61—C621.386 (6)
C13—C141.365 (9)C61—C661.400 (6)
C14—F31.343 (7)C62—C631.377 (7)
C14—C151.359 (9)C63—C641.382 (7)
C15—F41.347 (7)C64—C651.390 (7)
C15—C161.374 (7)C65—C661.375 (7)
C16—F51.345 (6)C99—Cl11.67 (2)
C21—C221.373 (6)C99—Cl21.699 (18)
C21—C261.383 (6)C99'—Cl2'1.701 (11)
C22—F61.348 (6)C99'—Cl1'1.720 (13)
C22—C231.374 (7)S—H01.331 (19)
C23—F71.351 (6)C43—H430.9500
C23—C241.371 (7)C44—H440.9500
C24—F81.345 (6)C45—H450.9500
C24—C251.372 (7)C46—H460.9500
C25—F91.342 (6)C52—H520.9500
C25—C261.366 (7)C53—H530.9500
C26—F101.349 (6)C54—H540.9500
C31—C321.369 (6)C55—H550.9500
C31—C361.372 (6)C56—H560.9500
C32—F111.351 (5)C62—H620.9500
C32—C331.383 (6)C63—H630.9500
C33—F121.343 (6)C64—H640.9500
C33—C341.364 (7)C65—H650.9500
C34—F131.340 (6)C66—H660.9500
C34—C351.378 (7)C99—H99A0.9900
C35—F141.340 (6)C99—H99B0.9900
C35—C361.383 (6)C99'—H99C0.9900
C36—F151.358 (5)C99'—H99D0.9900
C21—Au—C1186.92 (18)C46—C41—P120.3 (3)
C21—Au—C3186.49 (17)C42—C41—P119.2 (3)
C11—Au—C31172.17 (18)C43—C42—C41118.1 (5)
C21—Au—P173.61 (13)C43—C42—S121.8 (4)
C11—Au—P93.14 (14)C41—C42—S120.1 (4)
C31—Au—P93.88 (13)C44—C43—C42121.5 (5)
C51—P—C61102.5 (2)C43—C44—C45120.7 (5)
C51—P—C41106.9 (2)C44—C45—C46119.3 (5)
C61—P—C41107.0 (2)C45—C46—C41120.1 (5)
C51—P—Au119.59 (16)C56—C51—C52119.4 (5)
C61—P—Au110.32 (15)C56—C51—P119.5 (4)
C41—P—Au109.70 (16)C52—C51—P121.0 (4)
C12—C11—C16116.3 (5)C53—C52—C51119.9 (5)
C12—C11—Au123.5 (4)C54—C53—C52120.2 (5)
C16—C11—Au119.8 (4)C53—C54—C55120.6 (5)
F1—C12—C11119.8 (4)C54—C55—C56120.0 (5)
F1—C12—C13117.8 (5)C51—C56—C55119.9 (5)
C11—C12—C13122.4 (6)C62—C61—C66119.3 (4)
F2—C13—C14121.6 (5)C62—C61—P121.6 (4)
F2—C13—C12119.2 (6)C66—C61—P119.1 (3)
C14—C13—C12119.2 (6)C63—C62—C61119.9 (5)
F3—C14—C15120.1 (6)C62—C63—C64120.8 (5)
F3—C14—C13119.4 (6)C63—C64—C65119.6 (5)
C15—C14—C13120.4 (6)C66—C65—C64119.9 (5)
F4—C15—C14120.8 (6)C65—C66—C61120.4 (5)
F4—C15—C16119.8 (6)Cl1—C99—Cl2122 (2)
C14—C15—C16119.4 (6)Cl2'—C99'—Cl1'114.8 (7)
F5—C16—C15118.0 (5)C42—S—H0100 (3)
F5—C16—C11119.6 (4)C44—C43—H43119.2
C15—C16—C11122.4 (6)C42—C43—H43119.2
C22—C21—C26116.3 (5)C43—C44—H44119.7
C22—C21—Au124.1 (3)C45—C44—H44119.7
C26—C21—Au119.6 (3)C44—C45—H45120.3
F6—C22—C21120.3 (4)C46—C45—H45120.3
F6—C22—C23117.5 (4)C45—C46—H46119.9
C21—C22—C23122.2 (5)C41—C46—H46119.9
F7—C23—C24119.0 (4)C53—C52—H52120.1
F7—C23—C22121.3 (5)C51—C52—H52120.1
C24—C23—C22119.7 (5)C54—C53—H53119.9
F8—C24—C23119.5 (5)C52—C53—H53119.9
F8—C24—C25120.6 (5)C53—C54—H54119.7
C23—C24—C25119.8 (5)C55—C54—H54119.7
F9—C25—C26121.2 (5)C54—C55—H55120.0
F9—C25—C24119.6 (4)C56—C55—H55120.0
C26—C25—C24119.1 (5)C51—C56—H56120.0
F10—C26—C25118.0 (4)C55—C56—H56120.0
F10—C26—C21119.1 (4)C63—C62—H62120.1
C25—C26—C21122.9 (5)C61—C62—H62120.1
C32—C31—C36115.2 (4)C62—C63—H63119.6
C32—C31—Au121.0 (3)C64—C63—H63119.6
C36—C31—Au123.7 (3)C63—C64—H64120.2
F11—C32—C31120.2 (4)C65—C64—H64120.2
F11—C32—C33116.4 (4)C66—C65—H65120.1
C31—C32—C33123.3 (5)C64—C65—H65120.1
F12—C33—C34120.3 (4)C65—C66—H66119.8
F12—C33—C32120.3 (5)C61—C66—H66119.8
C34—C33—C32119.4 (5)Cl1—C99—H99A106.8
F13—C34—C33120.9 (5)Cl2—C99—H99A106.8
F13—C34—C35119.4 (5)Cl1—C99—H99B106.8
C33—C34—C35119.6 (5)Cl2—C99—H99B106.8
F14—C35—C34120.3 (4)H99A—C99—H99B106.7
F14—C35—C36121.1 (5)Cl2'—C99'—H99C108.6
C34—C35—C36118.7 (5)Cl1'—C99'—H99C108.6
F15—C36—C31120.1 (4)Cl2'—C99'—H99D108.6
F15—C36—C35116.2 (4)Cl1'—C99'—H99D108.6
C31—C36—C35123.6 (5)H99C—C99'—H99D107.5
C46—C41—C42120.2 (4)

Experimental details

Crystal data
Chemical formula[Au(C6F5)3(C18H15PS)]·CH2Cl2
Mr1077.40
Crystal system, space groupTriclinic, P1
Temperature (K)143
a, b, c (Å)10.057 (4), 12.888 (5), 15.236 (7)
α, β, γ (°)100.64 (3), 94.41 (3), 106.84 (3)
V3)1839.7 (13)
Z2
Radiation typeMo Kα
µ (mm1)4.35
Crystal size (mm)0.4 × 0.4 × 0.12
Data collection
DiffractometerStoe STADI-4
diffractometer
Absorption correctionψ scan
(XEMP; Siemens, 1994)
Tmin, Tmax0.527, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
8252, 6462, 5909
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.072, 1.05
No. of reflections6462
No. of parameters525
No. of restraints539
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.87, 0.70

Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4(Stoe & Cie, 1992), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top
Au—C212.057 (5)P—C511.810 (5)
Au—C112.060 (5)P—C611.816 (5)
Au—C312.074 (4)P—C411.816 (5)
Au—P2.3884 (16)S—C421.740 (5)
C21—Au—C1186.92 (18)C51—P—C61102.5 (2)
C21—Au—C3186.49 (17)C51—P—C41106.9 (2)
C11—Au—C31172.17 (18)C61—P—C41107.0 (2)
C21—Au—P173.61 (13)C51—P—Au119.59 (16)
C11—Au—P93.14 (14)C61—P—Au110.32 (15)
C31—Au—P93.88 (13)C41—P—Au109.70 (16)
 

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