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Acta Cryst. (2009). E65, m1373    [ doi:10.1107/S160053680904152X ]

[(3-Methylphenyl)(triphenylphosphonio)methanide-[kappa]C]triphenylphosphorane}(pentafluorophenyl-[kappa]C)gold(I) diethyl ether solvate

C. E. Strasser, K. Coetzee, S. Cronje and H. G. Raubenheimer

Abstract top

The metal atom in the title ylid-gold(I) adduct, [Au(C6F5)(C26H23P)]·C4H10O, exists in a linear coordination environment [C-Au-C = 174.1 (2)°]. The molecule has a short intramolecular contact involving an aromatic H atom (Au...H = 2.64 Å); two adjacent molecules are linked by an Au...Hylid interaction (Au...H = 3.14 Å).

Comment top

The hydrogen atom H132 of a PPh3 phenyl group approaches the gold centre quite closely, the distance of 2.64 Å is at the lower end of the range for Au···H interactions, 2.60 to 3.07 Å, as described by Baukova et al. (1995, 1997), Friedrichs & Jones (2004a, b, c) and Räisänen et al. (2007). The proton at the ylide carbon atom furthermore links two formula units together that are related by a centre of inversion (symmetry code i = –x, –y+1, –z+1). Another Au···H contact is formed by H23A of the diethyl ether solvent which approaches the gold centre at about 3.04 Å.

Gold(I) ylide complexes thus could represent an interesting field to study Au···H interactions also with other techniques e.g. NMR, which has been reported by Baukova et al. (1997).

Related compounds to (I) exhibiting similar geometric properties were reported by Usón et al. (1986, 1987, 1990). The compound reported in the latest publication also exhibits a Au···H interaction with a separation of 3.08 Å; the molecules are linked to form chains related by 21 screw operations instead of the dimers found in (I).

Related literature top

For Au···H interactions, see: Baukova et al. (1995, 1997), Friedrichs & Jones (2004a, 2004b, 2004c); Räisänen et al. (2007) (Au···H interactions). For related crystal structures; see: Usón et al. (1986, 1987, 1990). For the synthesis of the phosphorane, see: Friedrich & Henning (1959); Horner et al. (1962). For the synthesis of the gold reactant and a side-product, see: Usón et al. (1989); Coetzee et al. (2007).

Experimental top

1,3-Bis[(triphenyl-λ5-phosphoranyl)methyl]benzene was prepared according to a modified literature procedure (Friedrich & Henning, 1959; Horner et al., 1962). A suspension of 1,3-bis[(triphenylphosphonio)methyl]benzene(2+) dibromide (0.790 g, 1.00 mmol) and Ag2O in a 1:1 ethanol/dichloromethane solvent mixture (60 ml) was stirred for 2 h at room temperature. A suspension of [Au(C6F5)(tht)] (tht = tetrahydrothiophene; 0.640 g, 1.40 mmol; Usón et al., 1989) in 10 ml of dichloromethane was added to this mixture and stirred for 2 h. The grey suspension was filtered through MgSO4 to give a clear, colourless solution. The filtrate was concentrated to dryness yielding a colourless crystalline powder (0.380 g). Crystals of (I) and [Au(C6F5)(tht)] (Coetzee et al., 2007) suitable for single-crystal X-ray diffraction studies were obtained from a solution of the crude mixture in diethyl ether stored at -10 °C for six days.

Refinement top

All H atoms were positioned geometrically (C—H = 0.95, 1.00 and 0.98 Å for aromatic and aliphatic CH and CH3 groups, respectively) and constrained to ride on their parent atoms; Uiso(H) values were set at 1.2 times Ueq(C) for CH groups and 1.5 times Ueq(C) for CH3 groups.

The maximum residual electron density of 1.85 e Å-3 is located 0.91 Å next to Au1.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED (Atwood & Barbour, 2003; Barbour, 2001).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), ellipsoids are drawn at the 50% probability level, hydrogen atoms are omitted for clarity.
[(3-Methylphenyl)(triphenylphosphonio)methanide- κC](pentafluorophenyl-κC)gold(I) diethyl ether solvate top
Crystal data top
[Au(C6F5)(C26H23P)]·C4H10OF(000) = 3168
Mr = 804.56Dx = 1.711 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6992 reflections
a = 21.4958 (10) Åθ = 2.5–27.5°
b = 12.4634 (6) ŵ = 4.82 mm−1
c = 23.3126 (11) ÅT = 100 K
V = 6245.7 (5) Å3Block, colourless
Z = 80.24 × 0.21 × 0.19 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer		7453 independent reflections
Radiation source: fine-focus sealed tube5638 reflections with I > 2σ(I)
graphiteRint = 0.053
ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −28→24
Tmin = 0.328, Tmax = 0.400k = −16→11
37154 measured reflectionsl = −30→30
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0346P)2 + 6.9717P]
where P = (Fo2 + 2Fc2)/3
7453 reflections(Δ/σ)max = 0.002
398 parametersΔρmax = 1.85 e Å−3
0 restraintsΔρmin = −0.67 e Å−3
Crystal data top
[Au(C6F5)(C26H23P)]·C4H10OV = 6245.7 (5) Å3
Mr = 804.56Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 21.4958 (10) ŵ = 4.82 mm−1
b = 12.4634 (6) ÅT = 100 K
c = 23.3126 (11) Å0.24 × 0.21 × 0.19 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer		7453 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		5638 reflections with I > 2σ(I)
Tmin = 0.328, Tmax = 0.400Rint = 0.053
37154 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.080Δρmax = 1.85 e Å−3
S = 1.03Δρmin = −0.67 e Å−3
7453 reflectionsAbsolute structure: ?
398 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.096503 (7)0.573244 (13)0.454691 (7)0.01725 (6)
P10.14663 (5)0.42332 (9)0.55425 (4)0.0171 (2)
F120.21626 (11)0.7003 (2)0.40628 (11)0.0292 (6)
F130.22767 (12)0.8617 (2)0.33206 (12)0.0335 (7)
F140.12514 (12)0.9566 (2)0.28610 (11)0.0249 (6)
F150.01023 (12)0.8856 (2)0.31645 (12)0.0330 (7)
F16−0.00304 (11)0.7257 (2)0.39183 (11)0.0310 (6)
O10.11904 (14)0.5774 (2)0.26772 (13)0.0227 (7)
C10.08815 (19)0.4286 (4)0.49980 (19)0.0203 (9)
H10.04690.42960.51960.024*
C20.0881 (2)0.3335 (4)0.45888 (19)0.0249 (10)
C30.0413 (2)0.2581 (4)0.4614 (2)0.0320 (12)
H30.01010.26320.49020.038*
C40.0397 (2)0.1714 (4)0.4205 (2)0.0365 (13)
C50.0861 (2)0.1670 (5)0.3799 (2)0.0372 (13)
H50.08510.11060.35250.045*
C60.1326 (2)0.2381 (4)0.3770 (2)0.0353 (13)
H60.16420.23140.34870.042*
C70.1340 (2)0.3227 (4)0.41656 (19)0.0303 (11)
H70.16670.37390.41460.036*
C8−0.0120 (3)0.0927 (5)0.4248 (3)0.0498 (16)
H8A−0.04910.12190.40600.075*
H8B−0.02110.07880.46530.075*
H8C0.00020.02560.40600.075*
C110.10611 (19)0.7047 (3)0.40330 (17)0.0172 (9)
C120.16270 (19)0.7447 (4)0.38523 (18)0.0195 (9)
C130.1703 (2)0.8267 (4)0.34713 (18)0.0205 (9)
C140.1191 (2)0.8752 (4)0.32374 (18)0.0206 (9)
C150.0609 (2)0.8402 (4)0.33975 (19)0.0216 (10)
C160.05562 (19)0.7576 (4)0.37831 (18)0.0207 (9)
C210.2296 (2)0.5865 (4)0.2633 (2)0.0350 (12)
H21C0.26830.55570.27820.052*
H21A0.22800.66320.27240.052*
H21B0.22800.57690.22160.052*
C220.1742 (2)0.5300 (4)0.29069 (19)0.0245 (10)
H22B0.17530.45230.28180.029*
H22A0.17530.53890.33290.029*
C230.0638 (2)0.5271 (4)0.28810 (19)0.0248 (10)
H23A0.06220.53010.33050.030*
H23B0.06290.45090.27610.030*
C240.0090 (2)0.5867 (4)0.2628 (2)0.0293 (11)
H24C−0.02980.55370.27610.044*
H24B0.01100.58310.22080.044*
H24A0.01040.66190.27510.044*
C1110.14231 (19)0.3051 (3)0.59881 (18)0.0178 (9)
C1120.14187 (19)0.2042 (4)0.57311 (18)0.0201 (9)
H1120.14410.19830.53250.024*
C1130.1381 (2)0.1128 (4)0.6065 (2)0.0230 (10)
H1130.13860.04420.58870.028*
C1140.1338 (2)0.1205 (4)0.6654 (2)0.0248 (10)
H1140.13020.05750.68810.030*
C1150.1346 (2)0.2208 (4)0.69140 (19)0.0264 (10)
H1150.13220.22630.73200.032*
C1160.1388 (2)0.3131 (4)0.65806 (19)0.0237 (10)
H1160.13940.38160.67590.028*
C1210.1370 (2)0.5378 (4)0.60048 (18)0.0184 (9)
C1220.0777 (2)0.5769 (4)0.61363 (19)0.0244 (10)
H1220.04210.54510.59660.029*
C1230.0709 (2)0.6616 (4)0.65137 (19)0.0276 (11)
H1230.03050.68760.66030.033*
C1240.1227 (2)0.7089 (4)0.67619 (19)0.0294 (11)
H1240.11810.76790.70160.035*
C1250.1811 (2)0.6696 (4)0.66366 (19)0.0277 (11)
H1250.21670.70140.68100.033*
C1260.1887 (2)0.5845 (4)0.62621 (18)0.0226 (10)
H1260.22920.55790.61810.027*
C1310.22506 (19)0.4264 (4)0.52592 (17)0.0192 (9)
C1320.2439 (2)0.5107 (4)0.49073 (18)0.0231 (10)
H1320.21560.56700.48190.028*
C1330.3034 (2)0.5126 (4)0.46867 (19)0.0258 (11)
H1330.31560.56950.44400.031*
C1340.3454 (2)0.4325 (4)0.4821 (2)0.0259 (10)
H1340.38630.43450.46670.031*
C1350.3276 (2)0.3490 (4)0.5181 (2)0.0268 (11)
H1350.35640.29420.52790.032*
C1360.2679 (2)0.3461 (4)0.53952 (18)0.0228 (10)
H1360.25570.28880.56390.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01701 (9)0.01638 (9)0.01837 (9)0.00076 (7)−0.00176 (6)0.00163 (7)
P10.0167 (5)0.0165 (5)0.0182 (5)0.0004 (4)−0.0008 (4)0.0008 (5)
F120.0152 (13)0.0308 (16)0.0415 (16)0.0013 (11)−0.0021 (11)0.0149 (13)
F130.0204 (14)0.0361 (17)0.0440 (17)−0.0037 (12)0.0033 (12)0.0152 (14)
F140.0281 (14)0.0190 (14)0.0276 (14)−0.0012 (11)0.0025 (11)0.0099 (11)
F150.0203 (14)0.0330 (16)0.0457 (17)0.0007 (12)−0.0079 (12)0.0189 (14)
F160.0161 (13)0.0355 (16)0.0415 (16)−0.0047 (12)−0.0013 (11)0.0166 (14)
O10.0248 (16)0.0184 (16)0.0249 (16)0.0031 (13)−0.0042 (13)0.0023 (14)
C10.018 (2)0.021 (2)0.023 (2)0.0021 (19)−0.0045 (16)0.0004 (19)
C20.038 (3)0.013 (2)0.023 (2)0.0031 (19)−0.013 (2)−0.0001 (19)
C30.035 (3)0.023 (3)0.039 (3)0.008 (2)−0.014 (2)0.001 (2)
C40.033 (3)0.023 (3)0.053 (3)−0.005 (2)−0.026 (3)0.005 (3)
C50.038 (3)0.044 (3)0.030 (3)0.016 (3)−0.008 (2)−0.003 (2)
C60.034 (3)0.040 (3)0.032 (3)0.014 (3)−0.008 (2)−0.003 (2)
C70.038 (3)0.029 (3)0.023 (2)0.011 (2)−0.008 (2)−0.002 (2)
C80.045 (4)0.045 (4)0.060 (4)−0.010 (3)0.000 (3)0.000 (3)
C110.019 (2)0.015 (2)0.018 (2)−0.0028 (17)−0.0018 (16)−0.0026 (17)
C120.017 (2)0.019 (2)0.022 (2)0.0065 (18)−0.0032 (17)0.0010 (18)
C130.015 (2)0.021 (2)0.025 (2)−0.0046 (18)0.0034 (17)0.0007 (19)
C140.028 (2)0.013 (2)0.020 (2)−0.0008 (19)−0.0007 (18)0.0010 (18)
C150.018 (2)0.019 (2)0.028 (2)0.0034 (18)−0.0064 (18)0.0010 (19)
C160.016 (2)0.020 (2)0.025 (2)−0.0031 (18)−0.0018 (17)−0.0019 (19)
C210.024 (3)0.028 (3)0.053 (3)0.005 (2)−0.002 (2)0.009 (3)
C220.026 (2)0.019 (2)0.028 (2)0.006 (2)−0.004 (2)0.002 (2)
C230.027 (3)0.022 (2)0.024 (2)−0.007 (2)0.0041 (19)−0.003 (2)
C240.022 (2)0.031 (3)0.035 (3)−0.001 (2)−0.004 (2)−0.005 (2)
C1110.016 (2)0.015 (2)0.022 (2)−0.0023 (17)0.0001 (17)0.0072 (18)
C1120.018 (2)0.023 (2)0.020 (2)−0.0008 (19)0.0009 (17)0.0016 (19)
C1130.017 (2)0.020 (2)0.032 (3)−0.0004 (18)0.0015 (18)0.002 (2)
C1140.019 (2)0.020 (2)0.035 (3)−0.0006 (19)0.0027 (19)0.012 (2)
C1150.028 (3)0.029 (3)0.022 (2)0.001 (2)0.0016 (19)0.006 (2)
C1160.023 (2)0.022 (2)0.026 (2)−0.0012 (19)0.0022 (18)−0.0012 (19)
C1210.020 (2)0.018 (2)0.017 (2)0.0005 (18)−0.0006 (17)0.0026 (17)
C1220.019 (2)0.027 (3)0.027 (2)0.002 (2)−0.0063 (18)−0.003 (2)
C1230.032 (3)0.023 (3)0.028 (3)0.009 (2)0.004 (2)−0.001 (2)
C1240.046 (3)0.019 (3)0.023 (2)−0.001 (2)0.004 (2)−0.003 (2)
C1250.033 (3)0.025 (3)0.025 (2)−0.008 (2)0.001 (2)−0.004 (2)
C1260.019 (2)0.022 (2)0.026 (2)−0.0018 (19)0.0013 (17)−0.003 (2)
C1310.021 (2)0.020 (2)0.0165 (19)0.0008 (19)−0.0022 (16)−0.0042 (19)
C1320.018 (2)0.027 (3)0.024 (2)0.0000 (19)−0.0022 (18)0.005 (2)
C1330.022 (2)0.032 (3)0.024 (2)−0.005 (2)0.0027 (18)0.003 (2)
C1340.019 (2)0.029 (3)0.030 (2)−0.003 (2)0.0031 (18)−0.008 (2)
C1350.020 (2)0.025 (3)0.035 (3)0.007 (2)−0.002 (2)−0.007 (2)
C1360.021 (2)0.023 (2)0.024 (2)0.0021 (18)0.0013 (18)0.003 (2)
Geometric parameters (Å, °) top
Au1—C112.040 (4)C22—H22B0.9900
Au1—C12.094 (4)C22—H22A0.9900
Au1—H1322.6396C23—C241.511 (6)
Au1—H1i3.1400C23—H23A0.9900
P1—C11.788 (4)C23—H23B0.9900
P1—C1211.800 (5)C24—H24C0.9800
P1—C1111.805 (4)C24—H24B0.9800
P1—C1311.811 (4)C24—H24A0.9800
F12—C121.368 (5)C111—C1161.387 (6)
F13—C131.355 (5)C111—C1121.392 (6)
F14—C141.348 (5)C112—C1131.382 (6)
F15—C151.342 (5)C112—H1120.9500
F16—C161.359 (5)C113—C1141.381 (6)
O1—C231.425 (5)C113—H1130.9500
O1—C221.430 (5)C114—C1151.388 (6)
C1—C21.522 (6)C114—H1140.9500
C1—H11.0000C115—C1161.392 (6)
C2—C31.378 (7)C115—H1150.9500
C2—C71.401 (7)C116—H1160.9500
C3—C41.442 (7)C121—C1261.390 (6)
C3—H30.9500C121—C1221.399 (6)
C4—C51.375 (7)C122—C1231.382 (6)
C4—C81.486 (7)C122—H1220.9500
C5—C61.337 (8)C123—C1241.387 (7)
C5—H50.9500C123—H1230.9500
C6—C71.401 (7)C124—C1251.379 (7)
C6—H60.9500C124—H1240.9500
C7—H70.9500C125—C1261.383 (6)
C8—H8A0.9800C125—H1250.9500
C8—H8B0.9800C126—H1260.9500
C8—H8C0.9800C131—C1321.393 (6)
C11—C121.380 (6)C131—C1361.396 (6)
C11—C161.397 (6)C132—C1331.379 (6)
C12—C131.364 (6)C132—H1320.9500
C13—C141.368 (6)C133—C1341.382 (7)
C14—C151.377 (6)C133—H1330.9500
C15—C161.371 (6)C134—C1351.391 (7)
C21—C221.522 (6)C134—H1340.9500
C21—H21C0.9800C135—C1361.376 (6)
C21—H21A0.9800C135—H1350.9500
C21—H21B0.9800C136—H1360.9500
C11—Au1—C1174.05 (16)O1—C22—H22A110.2
C11—Au1—H13293.8C21—C22—H22A110.2
C1—Au1—H13286.4H22B—C22—H22A108.5
C11—Au1—H1i102.7O1—C23—C24107.6 (4)
C1—Au1—H1i79.1O1—C23—H23A110.2
H132—Au1—H1i155.0C24—C23—H23A110.2
C1—P1—C121108.4 (2)O1—C23—H23B110.2
C1—P1—C111113.7 (2)C24—C23—H23B110.2
C121—P1—C111107.3 (2)H23A—C23—H23B108.5
C1—P1—C131113.3 (2)C23—C24—H24C109.5
C121—P1—C131108.0 (2)C23—C24—H24B109.5
C111—P1—C131106.0 (2)H24C—C24—H24B109.5
C23—O1—C22112.6 (3)C23—C24—H24A109.5
C2—C1—P1114.6 (3)H24C—C24—H24A109.5
C2—C1—Au1110.8 (3)H24B—C24—H24A109.5
P1—C1—Au1109.2 (2)C116—C111—C112119.6 (4)
C2—C1—H1107.3C116—C111—P1121.1 (3)
P1—C1—H1107.3C112—C111—P1119.3 (3)
Au1—C1—H1107.3C113—C112—C111120.2 (4)
C3—C2—C7118.6 (4)C113—C112—H112119.9
C3—C2—C1120.3 (4)C111—C112—H112119.9
C7—C2—C1121.0 (4)C114—C113—C112120.4 (4)
C2—C3—C4120.0 (5)C114—C113—H113119.8
C2—C3—H3120.0C112—C113—H113119.8
C4—C3—H3120.0C113—C114—C115119.7 (4)
C5—C4—C3117.9 (5)C113—C114—H114120.1
C5—C4—C8124.3 (5)C115—C114—H114120.1
C3—C4—C8117.8 (5)C114—C115—C116120.1 (4)
C6—C5—C4123.4 (5)C114—C115—H115120.0
C6—C5—H5118.3C116—C115—H115120.0
C4—C5—H5118.3C111—C116—C115120.0 (4)
C5—C6—C7118.8 (5)C111—C116—H116120.0
C5—C6—H6120.6C115—C116—H116120.0
C7—C6—H6120.6C126—C121—C122119.2 (4)
C6—C7—C2121.4 (5)C126—C121—P1119.9 (3)
C6—C7—H7119.3C122—C121—P1120.8 (3)
C2—C7—H7119.3C123—C122—C121120.2 (4)
C4—C8—H8A109.5C123—C122—H122119.9
C4—C8—H8B109.5C121—C122—H122119.9
H8A—C8—H8B109.5C122—C123—C124120.3 (5)
C4—C8—H8C109.5C122—C123—H123119.9
H8A—C8—H8C109.5C124—C123—H123119.9
H8B—C8—H8C109.5C125—C124—C123119.5 (4)
C12—C11—C16112.8 (4)C125—C124—H124120.3
C12—C11—Au1123.9 (3)C123—C124—H124120.3
C16—C11—Au1123.0 (3)C124—C125—C126120.9 (4)
C13—C12—F12115.9 (4)C124—C125—H125119.6
C13—C12—C11125.0 (4)C126—C125—H125119.6
F12—C12—C11119.1 (4)C125—C126—C121120.0 (4)
F13—C13—C12121.2 (4)C125—C126—H126120.0
F13—C13—C14119.1 (4)C121—C126—H126120.0
C12—C13—C14119.7 (4)C132—C131—C136118.9 (4)
F14—C14—C13121.0 (4)C132—C131—P1120.1 (3)
F14—C14—C15120.2 (4)C136—C131—P1121.1 (3)
C13—C14—C15118.9 (4)C133—C132—C131120.1 (4)
F15—C15—C16121.0 (4)C133—C132—H132120.0
F15—C15—C14119.6 (4)C131—C132—H132120.0
C16—C15—C14119.4 (4)C132—C133—C134120.7 (4)
F16—C16—C15116.6 (4)C132—C133—H133119.7
F16—C16—C11119.1 (4)C134—C133—H133119.7
C15—C16—C11124.3 (4)C133—C134—C135119.8 (4)
C22—C21—H21C109.5C133—C134—H134120.1
C22—C21—H21A109.5C135—C134—H134120.1
H21C—C21—H21A109.5C136—C135—C134119.7 (4)
C22—C21—H21B109.5C136—C135—H135120.2
H21C—C21—H21B109.5C134—C135—H135120.2
H21A—C21—H21B109.5C135—C136—C131120.9 (4)
O1—C22—C21107.4 (4)C135—C136—H136119.5
O1—C22—H22B110.2C131—C136—H136119.5
C21—C22—H22B110.2
C121—P1—C1—C2−177.0 (3)C12—C11—C16—F16179.3 (4)
C111—P1—C1—C2−57.8 (4)Au1—C11—C16—F165.0 (6)
C131—P1—C1—C263.2 (4)C12—C11—C16—C150.3 (6)
C121—P1—C1—Au158.0 (3)Au1—C11—C16—C15−174.1 (3)
C111—P1—C1—Au1177.18 (19)C23—O1—C22—C21177.0 (4)
C131—P1—C1—Au1−61.8 (3)C22—O1—C23—C24177.8 (4)
H132—Au1—C1—C2−99.3C1—P1—C111—C116−125.8 (4)
H1i—Au1—C1—C2101.2C121—P1—C111—C116−6.0 (4)
H132—Au1—C1—P127.9C131—P1—C111—C116109.1 (4)
H1i—Au1—C1—P1−131.6C1—P1—C111—C11253.6 (4)
P1—C1—C2—C3108.3 (4)C121—P1—C111—C112173.4 (3)
Au1—C1—C2—C3−127.6 (4)C131—P1—C111—C112−71.5 (4)
P1—C1—C2—C7−74.1 (5)C116—C111—C112—C113−0.1 (6)
Au1—C1—C2—C750.0 (5)P1—C111—C112—C113−179.5 (3)
C7—C2—C3—C4−1.0 (7)C111—C112—C113—C1141.1 (6)
C1—C2—C3—C4176.6 (4)C112—C113—C114—C115−1.5 (7)
C2—C3—C4—C50.4 (7)C113—C114—C115—C1161.0 (7)
C2—C3—C4—C8−179.5 (5)C112—C111—C116—C115−0.4 (6)
C3—C4—C5—C60.7 (8)P1—C111—C116—C115179.0 (3)
C8—C4—C5—C6−179.4 (5)C114—C115—C116—C1110.0 (7)
C4—C5—C6—C7−1.1 (8)C1—P1—C121—C126−147.8 (4)
C5—C6—C7—C20.5 (7)C111—P1—C121—C12689.0 (4)
C3—C2—C7—C60.6 (7)C131—P1—C121—C126−24.7 (4)
C1—C2—C7—C6−177.0 (4)C1—P1—C121—C12236.0 (4)
H132—Au1—C11—C1212.5C111—P1—C121—C122−87.2 (4)
H1i—Au1—C11—C12173.6C131—P1—C121—C122159.1 (4)
H132—Au1—C11—C16−173.8C126—C121—C122—C1230.7 (7)
H1i—Au1—C11—C16−12.7P1—C121—C122—C123176.9 (4)
C16—C11—C12—C13−0.1 (6)C121—C122—C123—C1240.4 (7)
Au1—C11—C12—C13174.2 (3)C122—C123—C124—C125−1.0 (7)
C16—C11—C12—F12180.0 (4)C123—C124—C125—C1260.7 (7)
Au1—C11—C12—F12−5.7 (6)C124—C125—C126—C1210.3 (7)
F12—C12—C13—F13−0.7 (6)C122—C121—C126—C125−1.0 (6)
C11—C12—C13—F13179.4 (4)P1—C121—C126—C125−177.3 (3)
F12—C12—C13—C14179.6 (4)C1—P1—C131—C13256.4 (4)
C11—C12—C13—C14−0.3 (7)C121—P1—C131—C132−63.6 (4)
F13—C13—C14—F140.1 (6)C111—P1—C131—C132−178.2 (3)
C12—C13—C14—F14179.8 (4)C1—P1—C131—C136−124.7 (4)
F13—C13—C14—C15−179.2 (4)C121—P1—C131—C136115.3 (4)
C12—C13—C14—C150.5 (7)C111—P1—C131—C1360.7 (4)
F14—C14—C15—F151.9 (6)C136—C131—C132—C1331.7 (6)
C13—C14—C15—F15−178.8 (4)P1—C131—C132—C133−179.4 (3)
F14—C14—C15—C16−179.7 (4)C131—C132—C133—C134−1.4 (7)
C13—C14—C15—C16−0.4 (7)C132—C133—C134—C1350.1 (7)
F15—C15—C16—F16−0.7 (6)C133—C134—C135—C1360.8 (7)
C14—C15—C16—F16−179.1 (4)C134—C135—C136—C131−0.5 (7)
F15—C15—C16—C11178.4 (4)C132—C131—C136—C135−0.8 (6)
C14—C15—C16—C110.0 (7)P1—C131—C136—C135−179.7 (3)
Symmetry codes: (i) −x, −y+1, −z+1.
Acknowledgements top

We would like to thank the National Research Foundation (NRF) of South Africa and Mintek (KC) for financial support.

references
References top

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3–8.

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Baukova, T. V., Kuz'mina, L. G., Oleinikova, N. A. & Lemenovskii, D. A. (1995). Izv. Akad. Nauk. Ser. Khim. pp. 2032–2034.

Baukova, T. V., Kuz'mina, L. G., Oleinikova, N. A., Lemenovskii, D. A. & Blumenfel'd, A. L. (1997). J. Organomet. Chem. 530, 27–38.

Bruker (2002). SADABS and SMART. Bruker AXS Inc., Madison, Wisconsin,, USA

Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Coetzee, J., Gabrielli, W. F., Coetzee, K., Schuster, O., Nogai, S. D., Cronje, S. & Raubenheimer, H. G. (2007). Angew. Chem. Int. Ed. 46, 2497–2500.

Friedrich, K. & Henning, H. (1959). Chem. Ber. 92, 2756–2760.

Friedrichs, S. & Jones, P. G. (2004a). Z. Naturforsch. Teil B, 59, 49–57.

Friedrichs, S. & Jones, P. G. (2004b). Z. Naturforsch. Teil B, 59, 793–801.

Friedrichs, S. & Jones, P. G. (2004c). Z. Naturforsch. Teil B, 59, 1429–1437.

Horner, L., Hoffmann, H., Klink, W., Ertel, H. & Toscano, V. G. (1962). Chem. Ber. 95, 581–601.

Räisänen, M. T., Runeberg, N., Klinga, M., Nieger, M., Bolte, M., Pyykkö, P., Leskelä, M. & Repo, T. (2007). Inorg. Chem. 46, 9954–9960.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Usón, R., Laguna, A. & Laguna, M. (1989). Inorg. Synth. 26, 85–91.

Usón, R., Laguna, A., Laguna, M., Fraila, M. N., Lázaro, I., Gimeno, M. C., Jones, P. G., Reihs, C. & Sheldrick, G. M. (1990). J. Chem. Soc. Dalton Trans. pp. 333–338.

Usón, R., Laguna, A., Laguna, M., Lázaro, I. & Jones, P. G. (1987). Organometallics, 6, 2326–2321.

Usón, R., Laguna, A., Laguna, M., Lázaro, I., Morata, A., Jones, P. G. & Sheldrick, G. M. (1986). J. Chem. Soc. Dalton Trans. pp. 669–675.