[2-(Diphenyl­phosphino-κP)benzaldehyde]gold(I) chloride

Elsegood, M.R.J.; Smith, M.B.; Dale, S.H.

doi:10.1107/S1600536806026432

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 8| August 2006| Pages m1850-m1852

https://doi.org/10.1107/S1600536806026432

[2-(Diphenylphosphino-κP)benzaldehyde]gold(I) chloride

Mark R. J. Elsegood,^a Martin B. Smith ^a ^* and Sophie H. Dale ^b

^aChemistry Department, Loughborough University, Loughborough, Leicestershire LE11 3TU, England, and ^bMolecular Profiles, 8 Orchard Place, Nottingham Business Park, Nottingham NG8 6PX, England
^*Correspondence e-mail: m.b.smith@lboro.ac.uk

(Received 28 June 2006; accepted 7 July 2006; online 18 July 2006)

The title compound, [AuCl{(2-(C₆H₅)₂PC₆H₄CHO}], crystallizes with two molecules in the asymmetric unit. A comparison of the Au—P, Au—Cl and Cl—Au—P bond lengths and angles for both independent molecules with those of the previously reported compounds ClAu(2-Ph₂PC₆H₄X) (X = H, OSiMe₃ or OH) reveals that the nature of the ortho X substituent has a negligible effect on these structural parameters.

Comment

Functionalized tertiary phosphines bearing an additional hard oxygen donor group continue to find a range of uses in coordination and organometallic chemistry and catalysis (Downing & Smith, 2004 ). One classic example of such a hybrid ligand is 2-(diphenylphosphino)benzaldehyde (Hoots et al., 1982 ; Chandrasekaran et al., 2001 ), which has been studied in conjunction with a range of transition metal centres, e.g. W, Re, Rh and Cu (Yeh et al., 2004 , 2006 ; Chen et al., 2001 ; Mail et al., 2000 ). Furthermore, 2-Ph₂PC₆H₄CHO undergoes Schiff base condensation reactions with primary amines to give a range of polydentate ligands containing, amongst others, PNO or PNSe donor sets (Bhattacharyya et al., 1998 ; Durran et al., 2002 ). We present here the structure of the title linear gold(I) complex, (I). Recently, trigonal and tetrahedral copper(I) complexes with 2-Ph₂PC₆H₄CHO have been reported (Yeh et al., 2006).

Compound (I), ClAu[2-(C₆H₅)₂PC₆H₄CHO], crystallizes in a centrosymmetric space group, the asymmetric unit containing two independent molecules (Figs. 1 and 2, Table 1). The crystal structure of (I) confirms an essentially linear arrangement of both chloride and tertiary phosphine ligands around the gold(I) metal centre. In (I), the Au—P and Au—Cl bond lengths for both independent moleules are typical for this class of compound and agree well with those reported for related complexes (Table 2) (Hollatz et al., 1999 ; Baenziger et al., 1976 ).

Recently, it has been shown by X-ray diffraction that, in uncoordinated 2-Ph₂PC₆H₄CHO, the carbonyl group resides in close proximity to the P atom and the C=O distance is 1.194 (3) Å [cf. 1.207 (7) and 1.219 (7) Å in (I)]. The Au⋯O separations in (I) are 3.109 (4) and 3.106 (4) Å, shorter than the sum of their van der Waals radii of ca 3.2 Å, suggesting weak additional coordination. The shortest Au⋯Au intermolecular separation is 5.5900 (4) Å, indicating extremely weak aurophilicity. The dihedral angle between the formyl group and the benzene ring is 3.0 (7)° in the complex containing Au1, and 2.4 (5)° in the complex containing Au2.

Weak intermolecular hydrogen bonds are observed between phenyl CH groups and the coordinated Cl ligands, with C⋯Cl distances in the range 3.6–3.8 Å.

In summary, we have shown that the known ligand 2-Ph₂PC₆H₄CHO can be complexed to gold(I), affording a classic two-coordinate complex with typical Au—P and Au—Cl bond lengths and Cl—Au—P bond angles.

Figure 1
A perspective view of the complex containing Au1, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
A perspective view of the complex containing Au2, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Experimental

The preparation of (I) was carried out as follows. To a CH₂Cl₂ (10 ml) solution of AuCl(tht) (tht is tetrahydrothiophene; 0.048 g, 0.150 mmol) was added 2-Ph₂PC₆H₄CHO (0.047 g, 0.162 mmol). The yellow solution was stirred for 10 min and the volume reduced to ca 2–3 ml under reduced pressure. Addition of diethyl ether (10 ml) and petroleum ether (b.p. 333–353 K, 20 ml) gave (I), which was collected by suction filtration and dried in vacuo (yield 0.068 g, 87%). Selected spectroscopic data: ³¹P{¹H} NMR (CDCl₃, δ, p.p.m.): 32.2; ¹H NMR (CDCl₃, δ, p.p.m.): 10.26 (CHO), 8.10–6.94 (arom. H); FT–IR (ν, cm⁻¹): 1698 (CO), 1678 (CO), 333 (AuCl). Analysis, found: C 43.89, H 2.62%; C₁₉H₁₅AuClOP requires: C 43.65, H 2.90%. Colourless block crystals of (I) were obtained by vapour diffusion of diethyl ether into a CDCl₃ solution.

Crystal data

[AuCl(C₁₉H₁₅OP)]
M_r = 522.70
Triclinic, $[P \overline 1]$
a = 10.2431 (2) Å
b = 10.4949 (2) Å
c = 16.6533 (3) Å
α = 97.1857 (7)°
β = 103.5519 (9)°
γ = 101.4375 (9)°
V = 1677.96 (6) Å³
Z = 4
D_x = 2.069 Mg m⁻³
Mo Kα radiation
μ = 9.02 mm⁻¹
T = 120 (2) K
Plate, colourless
0.25 × 0.20 × 0.04 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan using multiple and symmetry-related data measurements (SORTAV; Blessing, 1995 ) T_min = 0.128, T_max = 0.697
29712 measured reflections
7704 independent reflections
6936 reflections with I > 2σ(I)
R_int = 0.063
θ_max = 27.7°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.06
7704 reflections
415 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0588P)² + 5.6P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 3.10 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au1—P1	2.2297 (13)
Au1—Cl1	2.2819 (13)
P1—C14	1.822 (5)
P1—C1	1.825 (5)
P1—C8	1.827 (5)
C7—O1	1.207 (7)
Au2—P2	2.2304 (14)
Au2—Cl2	2.2836 (14)
P2—C33	1.807 (5)
P2—C27	1.817 (6)
P2—C20	1.838 (5)
C26—O2	1.219 (7)

P1—Au1—Cl1	178.79 (5)
P2—Au2—Cl2	178.12 (5)

Table 2
Selected bond lengths and angles (Å, °) taken from compounds of the form ClAu(2-Ph₂PC₆H₄X) [X = H (Baenziger et al., 1976), OSiMe₃ or OH (Hollatz et al., 1999)]

	X = H	X = OH	X = OSiMe₃
Au—P	2.235 (3)	2.2226 (2)	2.2294 (8)
Au—Cl	2.279 (3)	2.285 (2)	2.2851 (8)
P—Au—Cl	179.68 (8)	176.85 (8)	177.30 (3)

H atoms were placed in geometric positions using a riding model, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The maximum and minimum electron-density peaks are located 0.88 Å from Au1 and 0.70 Å from Au2, respectively.

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Nonius, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806026432/sg2043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806026432/sg2043Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

[2-(Diphenylphosphino-κP)benzaldehyde]gold(I) chloride top

Crystal data top

[AuCl(C₁₉H₁₅OP)]	Z = 4
M_r = 522.70	F(000) = 992
Triclinic, P1	D_x = 2.069 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2431 (2) Å	Cell parameters from 61735 reflections
b = 10.4949 (2) Å	θ = 2.9–27.5°
c = 16.6533 (3) Å	µ = 9.02 mm⁻¹
α = 97.1857 (7)°	T = 120 K
β = 103.5519 (9)°	Thick plate, colourless
γ = 101.4375 (9)°	0.25 × 0.20 × 0.04 mm
V = 1677.96 (6) Å³

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	7704 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	6936 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	R_int = 0.063
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.7°, θ_min = 2.9°
φ and ω scans	h = −13→13
Absorption correction: multi-scan using multiple and symmetry-related data measurements (SORTAV; Blessing, 1995)	k = −13→13
T_min = 0.128, T_max = 0.697	l = −21→21
29712 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0588P)² + 5.6P] where P = (F_o² + 2F_c²)/3
7704 reflections	(Δ/σ)_max = 0.002
415 parameters	Δρ_max = 3.10 e Å⁻³
0 restraints	Δρ_min = −1.40 e Å⁻³

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Au1	0.69934 (2)	0.116173 (19)	0.424881 (11)	0.01437 (7)
Cl1	0.65437 (14)	0.03133 (14)	0.28557 (8)	0.0213 (3)
P1	0.73885 (14)	0.19673 (13)	0.56099 (8)	0.0134 (3)
C1	0.8005 (5)	0.0849 (5)	0.6285 (3)	0.0148 (10)
C2	0.7170 (6)	0.0265 (5)	0.6749 (3)	0.0159 (10)
H2	0.6295	0.0461	0.6716	0.019*
C3	0.7597 (6)	−0.0604 (5)	0.7263 (3)	0.0201 (11)
H3	0.7004	−0.1005	0.7569	0.024*
C4	0.8878 (6)	−0.0890 (6)	0.7333 (4)	0.0225 (12)
H4	0.9180	−0.1464	0.7696	0.027*
C5	0.9703 (6)	−0.0332 (5)	0.6869 (4)	0.0191 (11)
H5	1.0577	−0.0533	0.6908	0.023*
C6	0.9285 (6)	0.0528 (5)	0.6339 (3)	0.0170 (10)
C7	1.0229 (6)	0.1008 (5)	0.5849 (3)	0.0183 (11)
H7	1.1072	0.0731	0.5933	0.022*
O1	1.0025 (4)	0.1729 (4)	0.5346 (2)	0.0205 (8)
C8	0.5803 (6)	0.2252 (5)	0.5844 (3)	0.0163 (10)
C9	0.4615 (6)	0.1980 (5)	0.5197 (3)	0.0184 (11)
H9	0.4607	0.1564	0.4655	0.022*
C10	0.3421 (6)	0.2316 (6)	0.5336 (4)	0.0245 (12)
H10	0.2603	0.2129	0.4888	0.029*
C11	0.3431 (6)	0.2918 (6)	0.6123 (4)	0.0217 (12)
H11	0.2625	0.3157	0.6217	0.026*
C12	0.4626 (6)	0.3173 (6)	0.6780 (4)	0.0202 (11)
H12	0.4630	0.3574	0.7325	0.024*
C13	0.5815 (6)	0.2844 (5)	0.6641 (3)	0.0182 (11)
H13	0.6632	0.3023	0.7089	0.022*
C14	0.8589 (5)	0.3577 (5)	0.6010 (3)	0.0156 (10)
C15	0.8508 (6)	0.4559 (6)	0.5518 (4)	0.0212 (11)
H15	0.7859	0.4366	0.4982	0.025*
C16	0.9366 (7)	0.5807 (6)	0.5808 (4)	0.0271 (13)
H16	0.9299	0.6473	0.5473	0.032*
C17	1.0325 (6)	0.6093 (6)	0.6586 (4)	0.0248 (12)
H17	1.0924	0.6948	0.6782	0.030*
C18	1.0402 (6)	0.5130 (6)	0.7074 (4)	0.0232 (12)
H18	1.1059	0.5326	0.7608	0.028*
C19	0.9529 (6)	0.3871 (6)	0.6796 (4)	0.0205 (11)
H19	0.9577	0.3218	0.7143	0.025*
Au2	1.02900 (2)	0.690763 (19)	0.904323 (12)	0.01608 (7)
Cl2	1.24726 (15)	0.77100 (15)	0.89367 (9)	0.0260 (3)
P2	0.81313 (14)	0.61296 (13)	0.91035 (8)	0.0144 (3)
C20	0.7804 (5)	0.6774 (5)	1.0097 (3)	0.0146 (10)
C21	0.7514 (6)	0.5895 (5)	1.0624 (4)	0.0182 (11)
H21	0.7419	0.4978	1.0447	0.022*
C22	0.7360 (6)	0.6354 (6)	1.1419 (4)	0.0222 (12)
H22	0.7164	0.5743	1.1775	0.027*
C23	0.7489 (6)	0.7667 (6)	1.1685 (4)	0.0218 (11)
H23	0.7374	0.7969	1.2220	0.026*
C24	0.7788 (6)	0.8559 (6)	1.1167 (4)	0.0210 (11)
H24	0.7892	0.9475	1.1355	0.025*
C25	0.7937 (6)	0.8128 (5)	1.0380 (3)	0.0179 (11)
C26	0.8287 (6)	0.9151 (6)	0.9893 (4)	0.0229 (12)
H26	0.8349	1.0040	1.0130	0.027*
O2	0.8505 (4)	0.8949 (4)	0.9205 (3)	0.0248 (9)
C27	0.7707 (6)	0.4343 (5)	0.9010 (3)	0.0161 (10)
C28	0.6382 (6)	0.3653 (6)	0.8953 (3)	0.0193 (11)
H28	0.5688	0.4120	0.8991	0.023*
C29	0.6054 (7)	0.2272 (6)	0.8841 (4)	0.0238 (12)
H29	0.5147	0.1802	0.8816	0.029*
C30	0.7064 (6)	0.1600 (5)	0.8768 (4)	0.0228 (12)
H30	0.6845	0.0662	0.8692	0.027*
C31	0.8379 (6)	0.2264 (6)	0.8803 (4)	0.0239 (12)
H31	0.9055	0.1788	0.8735	0.029*
C32	0.8715 (6)	0.3641 (6)	0.8938 (3)	0.0188 (11)
H32	0.9632	0.4105	0.8983	0.023*
C33	0.6813 (5)	0.6367 (5)	0.8240 (3)	0.0160 (10)
C34	0.5582 (6)	0.6684 (6)	0.8326 (4)	0.0210 (11)
H34	0.5423	0.6830	0.8866	0.025*
C35	0.4597 (6)	0.6786 (6)	0.7625 (4)	0.0246 (12)
H35	0.3773	0.7024	0.7685	0.030*
C36	0.4815 (6)	0.6542 (6)	0.6840 (4)	0.0230 (12)
H36	0.4138	0.6613	0.6360	0.028*
C37	0.6008 (6)	0.6195 (6)	0.6745 (3)	0.0214 (11)
H37	0.6135	0.6009	0.6200	0.026*
C38	0.7025 (6)	0.6114 (5)	0.7442 (4)	0.0207 (11)
H38	0.7853	0.5891	0.7377	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.01748 (12)	0.01383 (11)	0.01319 (11)	0.00591 (8)	0.00416 (8)	0.00383 (8)
Cl1	0.0279 (7)	0.0228 (7)	0.0147 (6)	0.0096 (6)	0.0064 (5)	0.0021 (5)
P1	0.0155 (6)	0.0126 (6)	0.0125 (6)	0.0045 (5)	0.0031 (5)	0.0032 (5)
C1	0.018 (3)	0.007 (2)	0.016 (2)	0.0006 (19)	0.000 (2)	0.0015 (18)
C2	0.020 (3)	0.011 (2)	0.018 (2)	0.004 (2)	0.005 (2)	0.0029 (19)
C3	0.030 (3)	0.015 (3)	0.017 (3)	0.003 (2)	0.008 (2)	0.006 (2)
C4	0.031 (3)	0.017 (3)	0.022 (3)	0.006 (2)	0.006 (2)	0.011 (2)
C5	0.020 (3)	0.013 (2)	0.026 (3)	0.007 (2)	0.006 (2)	0.006 (2)
C6	0.017 (3)	0.009 (2)	0.021 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C7	0.017 (3)	0.015 (3)	0.022 (3)	0.004 (2)	0.006 (2)	0.002 (2)
O1	0.023 (2)	0.0184 (19)	0.024 (2)	0.0053 (16)	0.0086 (16)	0.0097 (16)
C8	0.018 (3)	0.012 (2)	0.020 (3)	0.004 (2)	0.005 (2)	0.006 (2)
C9	0.020 (3)	0.016 (3)	0.020 (3)	0.005 (2)	0.004 (2)	0.005 (2)
C10	0.015 (3)	0.025 (3)	0.030 (3)	0.004 (2)	0.001 (2)	0.005 (2)
C11	0.019 (3)	0.018 (3)	0.035 (3)	0.008 (2)	0.015 (2)	0.008 (2)
C12	0.022 (3)	0.018 (3)	0.022 (3)	0.005 (2)	0.008 (2)	0.005 (2)
C13	0.019 (3)	0.018 (3)	0.018 (3)	0.004 (2)	0.005 (2)	0.007 (2)
C14	0.018 (3)	0.012 (2)	0.019 (3)	0.005 (2)	0.006 (2)	0.005 (2)
C15	0.027 (3)	0.019 (3)	0.020 (3)	0.008 (2)	0.005 (2)	0.008 (2)
C16	0.033 (3)	0.019 (3)	0.032 (3)	0.004 (3)	0.012 (3)	0.014 (2)
C17	0.020 (3)	0.014 (3)	0.039 (3)	0.001 (2)	0.009 (3)	0.004 (2)
C18	0.020 (3)	0.018 (3)	0.029 (3)	0.005 (2)	0.005 (2)	−0.003 (2)
C19	0.024 (3)	0.018 (3)	0.022 (3)	0.010 (2)	0.007 (2)	0.004 (2)
Au2	0.01753 (12)	0.01563 (12)	0.01621 (11)	0.00452 (8)	0.00588 (8)	0.00346 (8)
Cl2	0.0233 (7)	0.0265 (7)	0.0280 (7)	0.0003 (6)	0.0128 (6)	0.0014 (6)
P2	0.0158 (6)	0.0140 (6)	0.0153 (6)	0.0055 (5)	0.0054 (5)	0.0039 (5)
C20	0.015 (2)	0.015 (2)	0.016 (2)	0.006 (2)	0.0046 (19)	0.0037 (19)
C21	0.015 (3)	0.016 (3)	0.024 (3)	0.004 (2)	0.006 (2)	0.003 (2)
C22	0.017 (3)	0.028 (3)	0.022 (3)	0.005 (2)	0.006 (2)	0.009 (2)
C23	0.023 (3)	0.025 (3)	0.020 (3)	0.008 (2)	0.007 (2)	0.004 (2)
C24	0.022 (3)	0.020 (3)	0.024 (3)	0.011 (2)	0.006 (2)	0.003 (2)
C25	0.021 (3)	0.018 (3)	0.016 (3)	0.008 (2)	0.005 (2)	0.003 (2)
C26	0.029 (3)	0.020 (3)	0.021 (3)	0.007 (2)	0.008 (2)	0.004 (2)
O2	0.033 (2)	0.023 (2)	0.023 (2)	0.0084 (18)	0.0109 (18)	0.0084 (17)
C27	0.019 (3)	0.016 (3)	0.013 (2)	0.007 (2)	0.001 (2)	0.0032 (19)
C28	0.021 (3)	0.021 (3)	0.019 (3)	0.010 (2)	0.006 (2)	0.006 (2)
C29	0.027 (3)	0.021 (3)	0.020 (3)	0.002 (2)	0.001 (2)	0.008 (2)
C30	0.034 (3)	0.011 (2)	0.022 (3)	0.003 (2)	0.006 (2)	0.002 (2)
C31	0.026 (3)	0.027 (3)	0.021 (3)	0.015 (2)	0.004 (2)	0.004 (2)
C32	0.017 (3)	0.021 (3)	0.019 (3)	0.009 (2)	0.001 (2)	0.003 (2)
C33	0.018 (3)	0.014 (2)	0.016 (2)	0.005 (2)	0.001 (2)	0.007 (2)
C34	0.025 (3)	0.022 (3)	0.022 (3)	0.012 (2)	0.012 (2)	0.009 (2)
C35	0.025 (3)	0.024 (3)	0.029 (3)	0.010 (2)	0.009 (2)	0.007 (2)
C36	0.027 (3)	0.021 (3)	0.022 (3)	0.010 (2)	0.002 (2)	0.009 (2)
C37	0.030 (3)	0.018 (3)	0.016 (3)	0.005 (2)	0.006 (2)	0.004 (2)
C38	0.027 (3)	0.017 (3)	0.022 (3)	0.008 (2)	0.011 (2)	0.006 (2)

Geometric parameters (Å, º) top

Au1—P1	2.2297 (13)	Au2—P2	2.2304 (14)
Au1—Cl1	2.2819 (13)	Au2—Cl2	2.2836 (14)
P1—C14	1.822 (5)	P2—C33	1.807 (5)
P1—C1	1.825 (5)	P2—C27	1.817 (6)
P1—C8	1.827 (5)	P2—C20	1.838 (5)
C1—C2	1.388 (7)	C20—C21	1.388 (7)
C1—C6	1.402 (8)	C20—C25	1.409 (7)
C2—C3	1.389 (7)	C21—C22	1.406 (8)
C2—H2	0.9500	C21—H21	0.9500
C3—C4	1.386 (8)	C22—C23	1.364 (8)
C3—H3	0.9500	C22—H22	0.9500
C4—C5	1.370 (8)	C23—C24	1.387 (8)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.396 (7)	C24—C25	1.385 (8)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.461 (8)	C25—C26	1.465 (8)
C7—O1	1.207 (7)	C26—O2	1.219 (7)
C7—H7	0.9500	C26—H26	0.9500
C8—C9	1.376 (8)	C27—C28	1.381 (8)
C8—C13	1.389 (7)	C27—C32	1.400 (7)
C9—C10	1.399 (8)	C28—C29	1.399 (8)
C9—H9	0.9500	C28—H28	0.9500
C10—C11	1.379 (8)	C29—C30	1.382 (9)
C10—H10	0.9500	C29—H29	0.9500
C11—C12	1.391 (8)	C30—C31	1.372 (9)
C11—H11	0.9500	C30—H30	0.9500
C12—C13	1.391 (8)	C31—C32	1.394 (8)
C12—H12	0.9500	C31—H31	0.9500
C13—H13	0.9500	C32—H32	0.9500
C14—C19	1.388 (8)	C33—C38	1.398 (7)
C14—C15	1.398 (7)	C33—C34	1.400 (8)
C15—C16	1.382 (8)	C34—C35	1.383 (8)
C15—H15	0.9500	C34—H34	0.9500
C16—C17	1.387 (9)	C35—C36	1.379 (8)
C16—H16	0.9500	C35—H35	0.9500
C17—C18	1.377 (9)	C36—C37	1.379 (8)
C17—H17	0.9500	C36—H36	0.9500
C18—C19	1.395 (8)	C37—C38	1.390 (8)
C18—H18	0.9500	C37—H37	0.9500
C19—H19	0.9500	C38—H38	0.9500

P1—Au1—Cl1	178.79 (5)	P2—Au2—Cl2	178.12 (5)
C14—P1—C1	106.5 (2)	C33—P2—C27	101.7 (2)
C14—P1—C8	102.6 (2)	C33—P2—C20	109.0 (2)
C1—P1—C8	106.9 (2)	C27—P2—C20	105.5 (2)
C14—P1—Au1	116.77 (18)	C33—P2—Au2	114.41 (18)
C1—P1—Au1	112.69 (17)	C27—P2—Au2	112.05 (18)
C8—P1—Au1	110.53 (18)	C20—P2—Au2	113.34 (18)
C2—C1—C6	118.3 (5)	C21—C20—C25	118.2 (5)
C2—C1—P1	119.2 (4)	C21—C20—P2	118.3 (4)
C6—C1—P1	122.5 (4)	C25—C20—P2	123.3 (4)
C1—C2—C3	120.9 (5)	C20—C21—C22	120.4 (5)
C1—C2—H2	119.5	C20—C21—H21	119.8
C3—C2—H2	119.5	C22—C21—H21	119.8
C4—C3—C2	120.6 (5)	C23—C22—C21	120.7 (5)
C4—C3—H3	119.7	C23—C22—H22	119.6
C2—C3—H3	119.7	C21—C22—H22	119.6
C5—C4—C3	118.9 (5)	C22—C23—C24	119.5 (5)
C5—C4—H4	120.5	C22—C23—H23	120.2
C3—C4—H4	120.5	C24—C23—H23	120.2
C4—C5—C6	121.4 (5)	C25—C24—C23	120.7 (5)
C4—C5—H5	119.3	C25—C24—H24	119.6
C6—C5—H5	119.3	C23—C24—H24	119.6
C5—C6—C1	119.9 (5)	C24—C25—C20	120.4 (5)
C5—C6—C7	116.0 (5)	C24—C25—C26	116.4 (5)
C1—C6—C7	124.0 (5)	C20—C25—C26	123.2 (5)
O1—C7—C6	125.3 (5)	O2—C26—C25	124.9 (5)
O1—C7—H7	117.4	O2—C26—H26	117.6
C6—C7—H7	117.4	C25—C26—H26	117.6
C9—C8—C13	120.1 (5)	C28—C27—C32	119.1 (5)
C9—C8—P1	118.6 (4)	C28—C27—P2	121.2 (4)
C13—C8—P1	121.0 (4)	C32—C27—P2	119.6 (4)
C8—C9—C10	120.2 (5)	C27—C28—C29	120.7 (5)
C8—C9—H9	119.9	C27—C28—H28	119.7
C10—C9—H9	119.9	C29—C28—H28	119.7
C11—C10—C9	120.0 (5)	C30—C29—C28	119.2 (6)
C11—C10—H10	120.0	C30—C29—H29	120.4
C9—C10—H10	120.0	C28—C29—H29	120.4
C10—C11—C12	119.8 (5)	C31—C30—C29	121.1 (5)
C10—C11—H11	120.1	C31—C30—H30	119.4
C12—C11—H11	120.1	C29—C30—H30	119.4
C11—C12—C13	120.2 (5)	C30—C31—C32	119.6 (5)
C11—C12—H12	119.9	C30—C31—H31	120.2
C13—C12—H12	119.9	C32—C31—H31	120.2
C8—C13—C12	119.8 (5)	C31—C32—C27	120.3 (5)
C8—C13—H13	120.1	C31—C32—H32	119.8
C12—C13—H13	120.1	C27—C32—H32	119.8
C19—C14—C15	119.4 (5)	C38—C33—C34	119.8 (5)
C19—C14—P1	122.3 (4)	C38—C33—P2	116.2 (4)
C15—C14—P1	118.2 (4)	C34—C33—P2	123.8 (4)
C16—C15—C14	120.3 (6)	C35—C34—C33	120.1 (5)
C16—C15—H15	119.9	C35—C34—H34	120.0
C14—C15—H15	119.9	C33—C34—H34	120.0
C15—C16—C17	120.2 (5)	C36—C35—C34	119.9 (5)
C15—C16—H16	119.9	C36—C35—H35	120.1
C17—C16—H16	119.9	C34—C35—H35	120.1
C18—C17—C16	119.6 (5)	C37—C36—C35	120.6 (5)
C18—C17—H17	120.2	C37—C36—H36	119.7
C16—C17—H17	120.2	C35—C36—H36	119.7
C17—C18—C19	120.9 (6)	C36—C37—C38	120.6 (5)
C17—C18—H18	119.6	C36—C37—H37	119.7
C19—C18—H18	119.6	C38—C37—H37	119.7
C14—C19—C18	119.6 (5)	C37—C38—C33	119.1 (5)
C14—C19—H19	120.2	C37—C38—H38	120.4
C18—C19—H19	120.2	C33—C38—H38	120.4

C14—P1—C1—C2	117.8 (4)	C33—P2—C20—C21	117.1 (4)
C8—P1—C1—C2	8.6 (5)	C27—P2—C20—C21	8.7 (5)
Au1—P1—C1—C2	−113.0 (4)	Au2—P2—C20—C21	−114.2 (4)
C14—P1—C1—C6	−63.7 (5)	C33—P2—C20—C25	−68.0 (5)
C8—P1—C1—C6	−172.9 (4)	C27—P2—C20—C25	−176.4 (4)
Au1—P1—C1—C6	65.5 (5)	Au2—P2—C20—C25	60.6 (5)
C6—C1—C2—C3	0.7 (8)	C25—C20—C21—C22	0.0 (8)
P1—C1—C2—C3	179.3 (4)	P2—C20—C21—C22	175.1 (4)
C1—C2—C3—C4	1.0 (8)	C20—C21—C22—C23	0.2 (8)
C2—C3—C4—C5	−1.8 (9)	C21—C22—C23—C24	−0.6 (9)
C3—C4—C5—C6	0.9 (9)	C22—C23—C24—C25	0.9 (9)
C4—C5—C6—C1	0.9 (8)	C23—C24—C25—C20	−0.8 (8)
C4—C5—C6—C7	−177.2 (5)	C23—C24—C25—C26	−178.5 (5)
C2—C1—C6—C5	−1.7 (8)	C21—C20—C25—C24	0.3 (8)
P1—C1—C6—C5	179.8 (4)	P2—C20—C25—C24	−174.6 (4)
C2—C1—C6—C7	176.3 (5)	C21—C20—C25—C26	177.9 (5)
P1—C1—C6—C7	−2.2 (7)	P2—C20—C25—C26	3.0 (8)
C5—C6—C7—O1	178.1 (5)	C24—C25—C26—O2	177.2 (6)
C1—C6—C7—O1	0.1 (9)	C20—C25—C26—O2	−0.5 (9)
C14—P1—C8—C9	124.1 (4)	C33—P2—C27—C28	−51.3 (5)
C1—P1—C8—C9	−124.0 (4)	C20—P2—C27—C28	62.3 (5)
Au1—P1—C8—C9	−1.1 (5)	Au2—P2—C27—C28	−173.9 (4)
C14—P1—C8—C13	−50.0 (5)	C33—P2—C27—C32	124.5 (4)
C1—P1—C8—C13	61.8 (5)	C20—P2—C27—C32	−121.8 (4)
Au1—P1—C8—C13	−175.2 (4)	Au2—P2—C27—C32	1.9 (5)
C13—C8—C9—C10	0.9 (8)	C32—C27—C28—C29	1.1 (8)
P1—C8—C9—C10	−173.2 (4)	P2—C27—C28—C29	176.9 (4)
C8—C9—C10—C11	−0.2 (9)	C27—C28—C29—C30	−1.4 (8)
C9—C10—C11—C12	−0.8 (9)	C28—C29—C30—C31	0.0 (9)
C10—C11—C12—C13	1.1 (9)	C29—C30—C31—C32	1.9 (9)
C9—C8—C13—C12	−0.7 (8)	C30—C31—C32—C27	−2.2 (8)
P1—C8—C13—C12	173.3 (4)	C28—C27—C32—C31	0.8 (8)
C11—C12—C13—C8	−0.3 (8)	P2—C27—C32—C31	−175.2 (4)
C1—P1—C14—C19	−14.6 (5)	C27—P2—C33—C38	−78.4 (5)
C8—P1—C14—C19	97.6 (5)	C20—P2—C33—C38	170.6 (4)
Au1—P1—C14—C19	−141.4 (4)	Au2—P2—C33—C38	42.6 (5)
C1—P1—C14—C15	168.4 (4)	C27—P2—C33—C34	96.8 (5)
C8—P1—C14—C15	−79.5 (5)	C20—P2—C33—C34	−14.2 (6)
Au1—P1—C14—C15	41.5 (5)	Au2—P2—C33—C34	−142.2 (4)
C19—C14—C15—C16	0.7 (8)	C38—C33—C34—C35	−1.9 (9)
P1—C14—C15—C16	177.9 (5)	P2—C33—C34—C35	−176.9 (5)
C14—C15—C16—C17	0.6 (9)	C33—C34—C35—C36	1.6 (9)
C15—C16—C17—C18	−1.0 (9)	C34—C35—C36—C37	0.0 (9)
C16—C17—C18—C19	0.0 (9)	C35—C36—C37—C38	−1.5 (9)
C15—C14—C19—C18	−1.7 (8)	C36—C37—C38—C33	1.2 (9)
P1—C14—C19—C18	−178.7 (4)	C34—C33—C38—C37	0.5 (8)
C17—C18—C19—C14	1.3 (8)	P2—C33—C38—C37	175.9 (4)

Selected bond lengths and angles (Å, °) taken from compounds of the form ClAu(2-Ph₂PC₆H₄X) [X = H, OSiMe₃ or OH] (Hollatz et al., 1999; Baenziger et al., 1976) top

	X = H	X = OH	X = OSiMe₃
Au—P	2.235 (3)	2.2226 (2)	2.2294 (8)
Au—Cl	2.279 (3)	2.285 (2)	2.2851 (8)
P—Au—Cl	179.68 (8)	176.85 (8)	177.30 (3)

Acknowledgements

The authors acknowledge the EPSRC National Crystallography Service at the University of Southampton for the collection of data for (I).

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