Crystal structures of the gold(I) phosphinine complexes [AuCl(C 5H2P-2,6-Me2-4-Ph)] and [AuCl(C 5H2P-2,4,6-Ph3)]

Article abstract of DOI:10.5560/ZNB.2013-3155

The gold(I) phosphinine complexes [AuCl(C₅H₂P-2,6- Me₂-4-Ph)] and [AuCl(C₅H₂P-2,4,6-Ph ₃)] were prepared and structurally characterised by single-crystal X-ray diffraction studies. In the former case, individual molecules are aggregated in the crystal as crossed dimers with an Au···Au distance of 3.60 A, compatible with a weak aurophilic interaction. In the latter case, intermolecular Au···π interactions involving the phosphinine ring are observed with Au···C distances in the range from ca. 3.32 to 3.44 A, which make [AuCl(C ₅H₂P-2,4,6-Ph₃)] the first structurally characterised example of intermolecular Au···π interactions involving a heteroarene.

Full text of DOI:10.5560/ZNB.2013-3155

Crystal Structures of the Gold(I) Phosphinine Complexes
[AuCl(C5H2P-2,6-Me2-4-Ph)] and [AuCl(C5H2P-2,4,6-Ph3)]
Jonathan Stott, Clemens Bruhn and Ulrich Siemeling
Institut fu¨r Chemie, Universita¨t Kassel, Heinrich-Plett-Straße 40, 34132 Kassel, Germany
Reprint requests to Prof. Dr. Ulrich Siemeling. Fax: +49 561 804 4777.
E-mail: siemeling@uni-kassel.de
Z. Naturforsch. 2013, 68b, 853 – 859 / DOI: 10.5560/ZNB.2013-3155
Received June 14, 2013
The gold(I) phosphinine complexes [AuCl(C5H2P-2,6-Me2-4-Ph)] and [AuCl(C5H2P-2,4,6-Ph3)]
were prepared and structurally characterised by single-crystal X-ray diffraction studies. In the former
case, individual molecules are aggregated in the crystal as crossed dimers with an Au···Au distance
˚
of 3.60 A, compatible with a weak aurophilic interaction. In the latter case, intermolecular Au···π
interactions involving the phosphinine ring are observed with Au···C distances in the range from ca.
˚
3.32 to 3.44 A, which make [AuCl(C5H2P-2,4,6-Ph3)] the first structurally characterised example of
intermolecular Au···π interactions involving a heteroarene.
Key words: Aurophilicity, Crystal Structure, Gold, Gold-π Interaction, Phosphinine
Introduction
structurally characterised κP-phosphinine complexes
with transition metals not belonging to group 6 were
λ3-Phosphinines (phosphabenzenes) were intro- published in the early 1990s [21, 22]. However, in
duced more than four decades ago by Ma¨rkl [1] and these cases phosphinine analogues of 2,20-biypridine
Ashe [2]. Their recent rapid development from labora- were used instead of simple monodentate ligands.
tory curiosities to important ligands in homogeneous It was only in 1999 that the groups of Elschen-
transition metal catalysis [3 – 7] was triggered by semi- broich and of Mathey and Le Floch, respectively,
nal work published by the group of Zenneck [8] and by reported cis-[PtCl2(C5H2P-2,6-Me2-4-Ph)2] [23] and
Breit [9] in 1996. The first transition metal complexes [AuCl{C5H2P-2,6-(SiMe3)2-4-Ph}] [24] as the first
containing phosphinine ligands were already described examples of structurally characterised non-group 6
in the early 1970s by the groups of No¨th [10 – 13], metal complexes containing a simple, unfunction-
Fraser [14], Schmidbaur [15], and Dimroth [16]. alised κP-phosphinine ligand. Note that even the
Single-crystal X-ray diffraction studies performed first structurally characterised f-block metal η6-
by Vahrenkamp and No¨th for the metal carbonyl phosphinine complex was published earlier [25]. We
complexes [Cr(κP-C5H2P-2,4,6-Ph3)(CO)5] [11] here report the crystal structures of the phosphinine
and [Cr(η6-C5H2P-2,4,6-Ph3)(CO)3] [12] revealed gold complexes [AuCl(C5H2P-2,6-Me2-4-Ph)] and
that phosphinines can coordinate via their P lone pair [AuCl(C5H2P-2,4,6-Ph3)]. While the latter compound
and also via their π system. Homologous molybde- was already described by Schmidbaur and coworkers
num and tungsten pentacarbonyl complexes were four decades ago [15], the former one has not been
structurally characterised by the groups of Ashe [17] reported before. We are aware of only three structurally
and Mathey [18]. This development culminated characterised complexes of the type [AuX(phos)]
in the synthesis and structural characterisation of (X = halogenido ligand, phos = κP-phosphinine
[M(κP-C5H5P)6] (M = Cr, Mo, W), the phosphinine ligand) to date, viz. [AuCl{C5H2P-2,6-(SiMe3)2-
analogue of the group 6 metal hexacarbonyl complexes, 4-Ph}] [24], [AuCl{C5H2P-2,4-Ph2-6-[C6H3-3,4-
by Elschenbroich and coworkers [19, 20]. The first (OMe)2]}] [26] and [AuCl(C5H2P-2,4,6-tBu)] [27].
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Results and Discussion
rophilic interactions [28 – 32]. This distance is iden-
tical with the traditional contact limit for significant
Schmidbaur and coworkers obtained [AuCl(C5H2P- aurophilic interactions [33]. However, recent experi-
2,4,6-Ph3)] from the very labile carbonyl complex mental work has demonstrated that aurophilic interac-
[AuCl(CO)] and C5H2P-2,4,6-Ph3 in benzene sol- tions may be structurally relevant up to Au···Au dis-
˚
vent. We have modified this procedure by using the tances of 4.0 A [34], which is in accord with earlier
readily available tetrahydrothiophene (THT) complex theoretical predictions [35]. The aurophilic aggrega-
[AuCl(THT)] in dichloromethane. The new compound tion usually observed in the solid state for linear dico-
[AuCl(C5H2P-2,6-Me2-4-Ph)] was prepared analo- ordinate gold(I) complexes can give rise to three prin-
gously. Single crystals suitable for an X-ray diffrac- cipal structural motifs, viz. a parallel, an antiparallel,
tion study were obtained in each case by layering and a crossed arrangement of neighbouring molecules.
a dichloromethane solution of the complex with hex- A recent CSD analysis [36] confirmed the result of
ane. The molecular structures are shown in Figs. 1 an earlier study [37] that Au···Au distances are on
and 2.
average shortest for the crossed arrangement. This is
The Au atom of [AuCl(C5H2P-2,6-Me2-4-Ph)] is in perfectly plausible, since at a given Au···Au distance
the quasilinear environment typically observed for di- steric repulsions between the ligands of neighbour-
coordinate complexes of the type [AuX(L)]. The Cl– ing molecules will be least for a staggered orientation,
Au–P angle has a value of 175.70(10)◦. The Au–Cl which corresponds to a crossed arrangement with a tor-
and Au–P bond lengths of 2.298(3) and 2.234(3) A, sion angle of 90◦. In the present case, a crossed ar-
˚
respectively, are marginally longer than those reported rangement is indeed observed, with a Cl–Au–Au–Cl
by Mathey [24], Gudat [26] and Nixon [27] for the torsion angle of ca. 101.3◦. This is strongly reminis-
three structurally investigated complexes of the type cent of the structures of the gold phosphane complexes
[AuCl(phos)], where Au–Cl Au–P bond lengths in [AuX(PMe2Ph)] (X=Cl, Br, I), where X–Au–Au–X
the narrow range from 2.27 to 2.28 A and 2.21 to torsion angles between ca. 105.9◦ and 115.9◦ were
˚
˚
2.22 A, respectively, have been determined. The P–C found for the dimeric aggregates in the crystal [38].
˚
bond lengths of 1.681(12) and 1.723(10) A are indis- In the same vein, a Cl–Au–Au–Cl torsion angle of ca.
tinguishable within experimental error and very sim- 103.1◦ was reported for [AuCl{P(CH=CH2)3}] [39].
ilar to the corresponding bond lengths reported for In the case of [AuCl{C5H2P-2,6-(SiMe3)2-4-Ph}],
the three previously investigated cases. Neighbour- however, neighbouring molecules are paired in an
ing molecules in the crystal exhibit intermolecular antiparallel fashion, resulting in Au···Au distances
˚
˚
Au···Au distances of 3.60 A, compatible with weak au- of only 3.37 A [24]. An antiparallel arrangement of
Fig. 1 (color online). Molecular structure and aggregation of [AuCl(C5H2P-2,6-Me2-4-Ph)] in the crystal. The Au···Au con-
˚
tact (3.60 A) is indicated by a dotted line.
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J. Stott et al. · Gold Phosphinine Complexes
855
Fig. 2 (color online). Molecular structure and aggregation of [AuCl(C5H2P-2,4,6-Ph3)] (two independent molecules) in the
crystal. Intermolecular Au···π interactions are indicated by dotted lines.
[AuX(L)] units is commonly observed with lean rigid ilar to those reported by Gudat and coworkers for
rod-type ligands L such as isocyanides, where the ag- the closely related [AuCl{C5H2P-2,4-Ph2-6-[C6H3-
gregational motif was shown to originate principally 3,4-(OMe)2]}] [26], which differs from [AuCl(C5H2P-
from the dipole-dipole interaction [40]. In the case of 2,4,6-Ph3)] just by the presence of two OMe sub-
phosphane ligands only primary [41] and secondary stituents in one of the three phenyl groups. However,
phosphanes [42] appear to be sufficiently lean for this the intermolecular Au···Cl interactions reported for
antiparallel arrangement.
the methoxy-substituted compound are absent in the
Due to the low resolution of the data for present case. Instead, we note intermolecular Au···π
[AuCl(C5H2P-2,4,6-Ph3)], a detailed discussion of interactions with the phosphinine ring. Au···arene in-
structural parameters is meaningful only for the heavy teractions are of enormous current interest [43 – 45],
atoms. The asymmetric unit contains two crystallo- especially with a view to the highly dynamic field of
graphically independent molecules, whose bond pa- gold catalysis [46 – 62]. Previous work has mainly fo-
rameters are indistinguishable within experimental er- cussed on intramolecular Au···arene interactions sup-
ror. The Au atom is in a quasilinear dicoordinate ported by tailor-made aryl-substituted phosphane lig-
environment (Cl–Au–P ca. 177◦) with Au–Cl and ands in complexes of the type [AuX(PR3)] [43, 45,
˚
˚
Au–P bond lengths of ca. 2.28 and 2.22 A, respec- 63 – 67]. Au···Carene distances as low as 2.96 A [66]
tively. Not unexpectedly, these values are very sim- have been realised with such systems. In passing we
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J. Stott et al. · Gold Phosphinine Complexes
Table 1. Crystal structure data for [AuCl(C5H2P-2,6-Me2-4-Ph)] and [AuCl(C5H2P-2,4,6-Ph3)].
[AuCl(C5H2P-2,6-Me2-4-Ph)]
[AuCl(C5H2P-2,4,6-Ph3)]
Crystal habit
Crystal size, mm3
Empirical formula
Mr
yellow plate
0.20×0.16×0.02
C13H13AuClP
432.62
yellow needle
0.07×0.04×0.02
C23H17AuClP
556.75
Crystal system
Space group (no.)
orthorhombic
Pbca (no. 61)
7.1884(4)
15.5674(10)
22.725(2)
2543.0(3)
8
2.26
11.9
1616
orthorhombic
P212121 (no. 19)
7.8440(9)
20.317(3)
24.843(4)
3959.3(9)
8
1.87
7.7
˚
a, A
˚
b, A
˚
c, A
3
˚
V, A
Z
Dcalcd., g cm−3
µ, mm−1
F(000), e
2128
No. of frames measured
θ range, deg
hkl range
98
116
2.77 to 25.00
−8 ≤ h ≤ +8
−16 ≤ k ≤ +18
−23 ≤ l ≤ 26
8262 / 2240 / 0.0955
1550
2240 / 0 / 147
0.0453 / 0.1305
–
1.29 to 25.00
−9 ≤ h ≤ +8
−24 ≤ k ≤ +21
−28 ≤ l ≤ +29
16040 / 6976 / 0.2275
2416
Refl. measured / unique / Rint
Refl. observed [I > 2σ(I)]
Data / restraints / parameters
Final R/Rw[I > 2σ(I)]
6976 / 0 / 237
0.0783 / 0.1277
−0.04(3)
Flack parameter x
∆ρfin (max / min), e A
−3
˚
2.62 / −2.47
1.14 / −2.49
note that much shorter such distances of only ca. earlier by Batsanov [72]. An almost identical value
˚
˚
2.33 A were observed by Bertrand and coworkers of 2.14 A was published in 2009 by Hu et al. [73].
for the cation of [Au(CAAC)(η2-toluene)] [B(C6F5)4], In 2010, Flower and coworkers proposed a value of
˚
which contains a bulky cyclic (alkyl)(amino)carbene 2.0 A [34]. The most recent values, published by Bat-
(CAAC) ligand [44]. However, this is not particularly sanov in 2011 [74] and by Alvarez in 2013 [70], differ
˚
˚
surprising, since in this case the metal-ligand frag- considerably: 1.97 A vs. 2.32 A. We conclude that the
ment which interacts with the arene π system con- sum of the van der Waals radii of carbon and gold can
tains monocoordinate AuI and is cationic, while in the be safely assumed to be ≥ 3.7 A.
˚
other cases this interaction occurs with a dicoordinate,
The first crystallographically authenticated case of
and electroneutral, fragment. As mentioned above, intermolecular Au···arene interactions was published
[AuCl(C5H2P-2,4,6-Ph3)] exhibits intermolecular, in- in 1998 by Churakov et al., who found Au···Carene dis-
˚
stead of intramolecular, Au···arene interactions, giv- tances of ca. 3.35 and 3.56 A in the crystal structure
ing rise to an η1-type motif for Au2 and C2 with of [AuX(PPh3)] (X = κN-2,3-dioxoindolinido) [75].
2
˚
an interatomic distance of 3.32(3) A and to an η - We are aware of only a single closely related re-
type motif for Au1 and C27/C28 with interatomic dis- port since then. Zhang and coworkers described
tances of 3.39(3) and 3.44(3) A, respectively. These the complex [Au(py){PPh2[NnPr(CH2Anth)]}](ClO4)
˚
distances are shorter than the sum of the estimated (py=pyridine, Anth=9-anthracenyl), whose tailor-
van der Waals radii of C and Au. For the former, made phosphane ligand gives rise to an intramolecu-
the value of 1.70 A given already by Bondi [68] is lar η2-type interaction of the Au atom with the an-
˚
˚
still commonly accepted [69], although in his very re- thracenyl π system (Au···Carene 3.02 and 3.16 A). The
cent cartography of the van der Waals territories Al- cationic units are connected to stacks in the crystal by
varez comes to the slightly higher value of 1.77 A [70]. an additional intermolecular η1-type interaction with
˚
˚
The van der Waals radius of gold has been a noto- an Au···Carene distance of ca. 3.35 A, similar to what
riously difficult and contentious issue. In 2007 Datta we observe for the Au2···C2 interaction in the case
˚
and coworkers [71] confirmed the value of 2.1 A given of [AuCl(C5H2P-2,4,6-Ph3)]. Finally, we note that this
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J. Stott et al. · Gold Phosphinine Complexes
857
λ3-phosphinine complex is the first structurally char- with anisotropic displacement parameters. Due to a very low
data / parameter ratio many carbon atoms of [AuCl(C5H2P-
acterised example of intermolecular Au···π interac-
2,4,6-Ph3)] could not be refined anisotropically. All H atoms
were placed in constrained positions according to the rid-
ing model with the 1.2 fold isotropic displacement param-
eters. Pertinent crystallographic data are collected in Ta-
ble 1. Graphical representations were made using ORTEP-3
WIN [84, 85].
CCDC 943924-943925 contain the supplementary crys-
tallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data
Centre via www.ccdc.cam.ac.uk/data request/cif.
tions involving a heteroarene.
Experimental Section
NMR spectra were recorded with the following Var-
ian spectrometers: NMRS-500 (500 MHz) and MR-400
(400 MHz). 31P NMR data were collected by proton-
decoupled methods. Chemical shifts (δ) are given in ppm
and are referenced to the signal due to the residual protio im-
purities of the solvent used relative to tetramethylsilane for
1H. 31P chemical shifts were referenced to external Ph3PO
(δ = 23.7 ppm) [76]. Coupling constants are given as ab-
solute values in Hz. All preparations involving air-sensitive
compounds were carried out under an atmosphere of dry ni-
trogen by using standard Schlenk techniques or in a conven-
tional argon-filled glove box. Solvents and reagents were ap-
propriately dried and purified by conventional methods and
stored under inert gas atmosphere. Gold complexes were
handled with exclusion of light. [AuCl(THT)] [77] and the
phosphinines C5H2P-2,6-Me2-4-Ph [78] and C5H2P-2,4,6-
Ph3 [78] were prepared according to published procedures.
X-Ray crystal structure analyses: For each data collection
a single crystal was mounted on a glass fibre, and all geomet-
ric and intensity data were taken from this sample. Diffrac-
tion experiments were carried out at T = 123 (2) K using
[AuCl(C5H2P-2,6-Me2-4-Ph)]
A solution of [AuCl(THT)] (16 mg, 50 µmol) in
dichloromethane (2 mL) was added to a stirred solution of
C5H2P-2,6-Me2-4-Ph (10 mg, 50 µmol) in dichloromethane
(3 mL) at −40 ◦C. The stirred mixture was allowed to
warm to room temperature over the course of 1 h. The
volume of the solution was reduced to ca. 1 mL in vacuo.
Layering of the concentrated solution with hexane afforded
the product as pale-yellow crystals. Yield 12 mg (55%). –
3
1H NMR ( CD2Cl2): δ = 2.75 (d, JPH = 22.6 Hz, 6 H,
Me), 7.50 – 7.60 (m, 5 H, Ph), 8.15 (d, 3JPH = 24.3 Hz, 2 H,
C5H2P). – 31P NMR ( CD2Cl2): δ = 165.1.
[AuCl(C5H2P-2,4,6-Ph3)]
˚
The preparation of this compound was performed in anal-
ogy to [AuCl(C5H2P-2,6-Me2-4-Ph)], affording the product
in 59% yield. – 1H NMR ( CD2Cl2): δ = 7.50 – 7.60 (m, 10
H, Ph), 7.70 – 7.80 (m, 5 H, Ph), 8.50 (d, 3JPH = 22.8 Hz, 2
H, C5H2P). – 31P NMR ( CD2Cl2): δ = 154.0.
MoKα radiation (λ = 0.71073 A) on a Stoe IPDS2 diffrac-
tometer equipped with a 2-circle goniometer and an area de-
tector. Absorption correction was done by integration using
X-RED [79]. The data sets were corrected for Lorentz and
polarisation effects. The structures were solved by Direct
Methods (SHELXS-97 [80, 81]) and refined using alternat-
ing cycles of least-squares refinements against F2 (SHELXL-
97 [82, 83]). All non-H atoms of [AuCl(C5H2P-2,6-Me2-4-
Acknowledgement
We are grateful to Umicore AG&Co. KG (Hanau, Ger-
Ph)] were found in difference Fourier maps and were refined many) for a generous gift of gold compounds.
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