(η5-Penta­methyl­cyclo­penta­dien­yl)(η6-toluene)­ruthenium(II) hexa­fluorido­phosphate

O, W.W.N.; Lough, A.J.; Morris, R.H.

doi:10.1107/S1600536810036299

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1264

doi:10.1107/S1600536810036299

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(η⁵-Pentamethylcyclopentadienyl)(η⁶-toluene)ruthenium(II) hexafluoridophosphate

Wylie W. N. O,^a Alan J. Lough ^a ^* and Robert H. Morris ^a

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 3 September 2010; accepted 9 September 2010; online 15 September 2010)

In the title complex, [Ru(C₇H₈)(C₁₀H₁₅)]PF₆, the cation lies on a mirror plane and the anion lies on an inversion center. The distance between the Ru atom and the centroid of the benzene ring is 1.706 (5) Å and the distance between the Ru atom and the cyclopentadienyl ring is 1.811 (5) Å. The crystal structure is stabilized by weak C—H⋯F hydrogen bonds. The H atoms of the methyl groups which lie on the mirror plane are disordered over two sites with equal occupancies.

Related literature

For reviews on half-sandwich complexes containing group 8 metals, see: Coville et al. (1992 ); Jiménez-Tenorio et al. (2004 ). For the synthesis and properties of the title complex, see: Arliguie et al. (1988 ); Schmid et al. (2003 ); Loughrey et al. (2008 ). For related structures, see: Fagan et al. (1989 , 1990 ); He et al. (1991 ); Nolan et al. (1993 ). For bifunctional catalysts for the homogenous hydrogenation of polar bonds, see: Clapham et al. (2004 ); O et al. (2010 ).

Experimental

Crystal data

[Ru(C₇H₈)(C₁₀H₁₅)]PF₆
M_r = 473.39
Orthorhombic, P n m a
a = 13.9735 (4) Å
b = 15.3266 (4) Å
c = 8.6576 (6) Å
V = 1854.17 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 150 K
0.22 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.711, T_max = 0.863
11870 measured reflections
2200 independent reflections
1611 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.131
S = 1.07
2200 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 2.11 e Å⁻³
Δρ_min = −2.04 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F2ⁱ	1.00	2.46	3.450 (4)	173
C2—H2A⋯F3ⁱ	1.00	2.54	3.243 (5)	127
C3—H3A⋯F2ⁱⁱ	1.00	2.44	3.356 (5)	151
C8—H8C⋯F3ⁱⁱⁱ	0.98	2.55	3.258 (5)	129
C10—H10B⋯F1^iv	0.98	2.54	3.515 (6)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z]$ ; (iii) x, y, z-1; (iv) -x, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036299/pk2266sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036299/pk2266Isup2.hkl

checkCIF report

Comment top

The heterolytic splitting of dihydrogen across a transition metal-amido bond provides an important metal-hydride and a protic amine group for the efficient catalytic homogenous hydrogenation of polar bonds to produce valuable alcohols and amines (Clapham et al., 2004). We are interested in the use of chelating primary amine and N-heterocyclic carbene ligands (C—NH₂) that resemble those of the phosphine-amine analogues. Thus, the transmetalation reaction of 1.5 equiv of RuCp*(cod)Cl (cod = 1,5-cyclooctadiene) and [Ni(C—NH₂)₂] (PF₆)₂ in acetonitrile, and subsequent workup in tetrahydrofuran and excess pyridine afforded the active catalyst, [RuCp*(C—NH₂)(py)]PF₆ (Fig. 2), for the hydrogenation of polar bonds in basic solution (O et al., 2010). The use of 2 equiv. of RuCp*(cod)Cl and 1 equiv of [Ni(C—NH₂)₂] (PF₆)₂, with subsequent workup in tetrahydrofuran, toluene and pyridine mixtures, however, afforded selective crystallization of small amounts of title molecule, [Cp*Ru(η⁶-toluene)]PF₆, as a side product. We report here the crystal structure of the title molecule. The synthesis of such compounds have been reported elsewhere (Fagan et al., 1989; Schmid et al., 2003; Loughrey et al., 2008). The spectroscopic data for the reaction mixture containing the title molecule matches those reported in the literature (Arliguie et al., 1988; Loughrey et al., 2008).

The molecular structure of the title complex is shown in Fig. 1. The title sandwich complex consists of a coordinated planar arene ring and a pentamethylcyclopentadienyl ring in η⁶– and η⁵– hapticities, respectively. The bond distances are in reasonable agreement for analogous complexes with, for example, coordinated hexamethylbenzene and anisole in η⁶– hapticities (Fagan et al., 1989, 1990; He et al., 1991; Nolan et al., 1993). The distance between the Ru atom and the centroid of the benzene ring is 1.706 (5) Å and the distance between the Ru atom and the cyclopentadienyl ring is 1.811 (5) Å. The angle formed with the centroids of the coordinated rings and the Ru^II ion is 179.49 (15)°. The crystal structure is stabilized by weak C—H···F hydrogen bonds.

Related literature top

For reviews on half-sandwich complexes containing group 8 metals, see: Coville et al. (1992); Jiménez-Tenorio et al. (2004). For the synthesis and properties of the title complex, see: Arliguie et al. (1988); Schmid et al. (2003); Loughrey et al. (2008). For related structures, see: Fagan et al. (1989, 1990); He et al. (1991); Nolan et al. (1993). For bifunctional catalysts for the homogenous hydrogenation of polar bonds, see: Clapham et al. (2004); O et al. (2010).

Experimental top

A Schlenk flask was charged with [Ni(C—NH₂)₂](PF₆)₂ (32 mg, 0.084 mmol) and RuCp*(cod)Cl (30 mg, 0.041 mmol). Dry acetonitrile (8 ml) was added to the reaction mixture, and it was refluxed under an argon atmosphere for 3 h. The deep green solution was evaporated under reduced pressure, and the residue was extracted with oxygen-free tetrahydrofuran (4 ml) and toluene (1 ml), and filtered through a pad of Celite under a nitrogen atmosphere. To the yellow-brown solution was added pyridine (11 mg, 15 fold excess), and the orange coloured solution was evaporated under reduced pressure. The solid residue was extracted with tetrahydrofuran (3 ml) and dichloromethane (1 ml). Addition of diethyl ether (8 ml) to this solution afforded an orange precipitate, which gave the crude products of [RuCp*(C—NH₂)py]PF₆ and about 17% of the title salt, [Cp*Ru(η⁶-toluene)]PF₆, as determined by ¹H NMR spectroscopy of the bulk solid. This was filtered and dried in vacuum to yield an orange powder. Suitable crystals for an X-ray diffraction study were obtained by slow diffusion of diethyl ether into a saturated solution of the mixture in acetone under a nitrogen atmosphere to afford colourless blocks.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability ellipsoids. Atoms labeled with suffixes 'a' and 'b' are related by the symmetry codes (-x, -y + 1, -z + 1) and (x, -y + 1/2, z) respectively.
	Fig. 2. The reaction scheme.

(η⁵-Pentamethylcyclopentadienyl)(η⁶-toluene)ruthenium(II) hexafluoridophosphate top

Crystal data top

[Ru(C₇H₈)(C₁₀H₁₅)]PF₆	F(000) = 952
M_r = 473.39	D_x = 1.696 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 11870 reflections
a = 13.9735 (4) Å	θ = 2.7–27.5°
b = 15.3266 (4) Å	µ = 0.99 mm⁻¹
c = 8.6576 (6) Å	T = 150 K
V = 1854.17 (15) Å³	Block, colourless
Z = 4	0.22 × 0.15 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	2200 independent reflections
Radiation source: fine-focus sealed tube	1611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ϕ scans and ω scans with κ offsets	h = −17→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −15→19
T_min = 0.711, T_max = 0.863	l = −11→11
11870 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.065P)² + 3.7819P] where P = (F_o² + 2F_c²)/3
2200 reflections	(Δ/σ)_max = 0.003
128 parameters	Δρ_max = 2.11 e Å⁻³
0 restraints	Δρ_min = −2.04 e Å⁻³

Crystal data top

[Ru(C₇H₈)(C₁₀H₁₅)]PF₆	V = 1854.17 (15) Å³
M_r = 473.39	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 13.9735 (4) Å	µ = 0.99 mm⁻¹
b = 15.3266 (4) Å	T = 150 K
c = 8.6576 (6) Å	0.22 × 0.15 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	2200 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1611 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.863	R_int = 0.062
11870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.07	Δρ_max = 2.11 e Å⁻³
2200 reflections	Δρ_min = −2.04 e Å⁻³
128 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.

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	Occ. (<1)
Ru1	0.09419 (3)	0.2500	0.05036 (5)	0.02470 (18)
C1	−0.0364 (4)	0.2500	0.1948 (8)	0.0364 (15)
H1	−0.0414	0.2500	0.3042	0.044*
C2	−0.0326 (3)	0.1709 (3)	0.1144 (5)	0.0329 (10)
H2A	−0.0235	0.1153	0.1730	0.040*
C3	−0.0226 (3)	0.1708 (3)	−0.0472 (5)	0.0318 (10)
H3A	−0.0065	0.1147	−0.1005	0.038*
C4	−0.0174 (4)	0.2500	−0.1323 (7)	0.0300 (13)
C5	0.2303 (3)	0.2969 (3)	−0.0428 (5)	0.0266 (9)
C6	0.2204 (3)	0.3259 (3)	0.1143 (5)	0.0266 (9)
C7	0.2144 (4)	0.2500	0.2112 (7)	0.0267 (13)
C8	−0.0027 (5)	0.2500	−0.3057 (7)	0.0393 (16)
H8A	−0.0634	0.2363	−0.3571	0.059*	0.50
H8B	0.0452	0.2060	−0.3333	0.059*	0.50
H8C	0.0194	0.3077	−0.3389	0.059*	0.50
C9	0.2427 (3)	0.3550 (3)	−0.1801 (6)	0.0391 (11)
H9A	0.3097	0.3733	−0.1875	0.059*
H9B	0.2018	0.4065	−0.1689	0.059*
H9C	0.2247	0.3232	−0.2739	0.059*
C10	0.2220 (3)	0.4184 (3)	0.1676 (6)	0.0405 (12)
H10A	0.2883	0.4368	0.1846	0.061*
H10B	0.1860	0.4235	0.2644	0.061*
H10C	0.1926	0.4557	0.0888	0.061*
C11	0.2061 (4)	0.2500	0.3875 (8)	0.0399 (16)
H11A	0.1816	0.3066	0.4224	0.060*	0.50
H11B	0.2692	0.2397	0.4331	0.060*	0.50
H11C	0.1620	0.2037	0.4200	0.060*	0.50
P1	0.0000	0.5000	0.5000	0.0282 (4)
F1	−0.09922 (18)	0.5503 (2)	0.4824 (4)	0.0454 (7)
F2	0.0208 (2)	0.51551 (18)	0.3204 (3)	0.0450 (7)
F3	−0.0520 (2)	0.40978 (18)	0.4592 (3)	0.0435 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.0238 (3)	0.0249 (3)	0.0255 (3)	0.000	0.00149 (19)	0.000
C1	0.024 (3)	0.052 (4)	0.033 (4)	0.000	0.005 (3)	0.000
C2	0.026 (2)	0.034 (2)	0.039 (3)	−0.0065 (18)	−0.0021 (19)	0.011 (2)
C3	0.028 (2)	0.031 (2)	0.036 (3)	−0.0049 (18)	−0.0049 (18)	−0.002 (2)
C4	0.026 (3)	0.038 (4)	0.025 (3)	0.000	−0.004 (2)	0.000
C5	0.023 (2)	0.029 (2)	0.028 (2)	−0.0033 (17)	0.0042 (16)	0.0022 (18)
C6	0.0190 (19)	0.033 (2)	0.028 (2)	−0.0030 (17)	0.0053 (16)	−0.0073 (18)
C7	0.021 (3)	0.040 (3)	0.019 (3)	0.000	−0.001 (2)	0.000
C8	0.042 (4)	0.052 (4)	0.024 (3)	0.000	−0.003 (3)	0.000
C9	0.041 (3)	0.042 (3)	0.035 (3)	−0.001 (2)	0.007 (2)	0.012 (2)
C10	0.037 (2)	0.036 (3)	0.049 (3)	−0.005 (2)	0.011 (2)	−0.011 (2)
C11	0.025 (3)	0.046 (4)	0.049 (4)	0.000	0.011 (3)	0.000
P1	0.0331 (8)	0.0276 (8)	0.0240 (8)	0.0019 (6)	0.0018 (7)	−0.0006 (7)
F1	0.0403 (16)	0.0456 (18)	0.0502 (18)	0.0127 (12)	−0.0027 (13)	−0.0017 (14)
F2	0.0653 (18)	0.0425 (16)	0.0273 (14)	−0.0008 (14)	0.0050 (13)	−0.0005 (13)
F3	0.0556 (18)	0.0311 (15)	0.0438 (17)	−0.0070 (13)	−0.0045 (13)	−0.0018 (12)

Geometric parameters (Å, º) top

Ru1—C7	2.181 (5)	C6—C7	1.436 (5)
Ru1—C6	2.184 (4)	C6—C10	1.491 (6)
Ru1—C6ⁱ	2.184 (4)	C7—C6ⁱ	1.436 (5)
Ru1—C5	2.187 (4)	C7—C11	1.531 (9)
Ru1—C5ⁱ	2.187 (4)	C8—H8A	0.9800
Ru1—C3	2.203 (4)	C8—H8B	0.9800
Ru1—C3ⁱ	2.203 (4)	C8—H8C	0.9800
Ru1—C1	2.211 (6)	C9—H9A	0.9800
Ru1—C2	2.217 (4)	C9—H9B	0.9800
Ru1—C2ⁱ	2.217 (4)	C9—H9C	0.9800
Ru1—C4	2.220 (6)	C10—H10A	0.9800
C1—C2	1.398 (6)	C10—H10B	0.9800
C1—C2ⁱ	1.398 (6)	C10—H10C	0.9800
C1—H1	0.9500	C11—H11A	0.9800
C2—C3	1.406 (6)	C11—H11B	0.9800
C2—H2A	1.0000	C11—H11C	0.9800
C3—C4	1.422 (6)	P1—F1ⁱⁱ	1.594 (3)
C3—H3A	1.0000	P1—F1	1.594 (3)
C4—C3ⁱ	1.422 (6)	P1—F2ⁱⁱ	1.599 (3)
C4—C8	1.515 (9)	P1—F2	1.599 (3)
C5—C6	1.437 (6)	P1—F3ⁱⁱ	1.601 (3)
C5—C5ⁱ	1.437 (9)	P1—F3	1.601 (3)
C5—C9	1.495 (6)

C7—Ru1—C6	38.42 (14)	C2—C3—Ru1	72.0 (2)
C7—Ru1—C6ⁱ	38.42 (14)	C4—C3—Ru1	71.9 (3)
C6—Ru1—C6ⁱ	64.3 (2)	C2—C3—H3A	118.9
C7—Ru1—C5	64.28 (17)	C4—C3—H3A	118.9
C6—Ru1—C5	38.40 (15)	Ru1—C3—H3A	118.9
C6ⁱ—Ru1—C5	64.29 (15)	C3ⁱ—C4—C3	117.3 (6)
C7—Ru1—C5ⁱ	64.28 (17)	C3ⁱ—C4—C8	121.3 (3)
C6—Ru1—C5ⁱ	64.29 (15)	C3—C4—C8	121.3 (3)
C6ⁱ—Ru1—C5ⁱ	38.40 (15)	C3ⁱ—C4—Ru1	70.6 (3)
C5—Ru1—C5ⁱ	38.4 (2)	C3—C4—Ru1	70.6 (3)
C7—Ru1—C3	144.60 (13)	C8—C4—Ru1	127.7 (4)
C6—Ru1—C3	171.56 (16)	C6—C5—C5ⁱ	108.0 (2)
C6ⁱ—Ru1—C3	113.71 (17)	C6—C5—C9	125.4 (4)
C5—Ru1—C3	133.16 (16)	C5ⁱ—C5—C9	126.5 (3)
C5ⁱ—Ru1—C3	108.77 (17)	C6—C5—Ru1	70.7 (2)
C7—Ru1—C3ⁱ	144.60 (13)	C5ⁱ—C5—Ru1	70.81 (11)
C6—Ru1—C3ⁱ	113.71 (17)	C9—C5—Ru1	126.1 (3)
C6ⁱ—Ru1—C3ⁱ	171.56 (16)	C5—C6—C7	107.9 (4)
C5—Ru1—C3ⁱ	108.77 (17)	C5—C6—C10	125.8 (4)
C5ⁱ—Ru1—C3ⁱ	133.16 (16)	C7—C6—C10	126.2 (4)
C3—Ru1—C3ⁱ	66.9 (2)	C5—C6—Ru1	70.9 (2)
C7—Ru1—C1	105.9 (2)	C7—C6—Ru1	70.7 (3)
C6—Ru1—C1	121.52 (17)	C10—C6—Ru1	126.6 (3)
C6ⁱ—Ru1—C1	121.52 (17)	C6ⁱ—C7—C6	108.1 (5)
C5—Ru1—C1	157.77 (14)	C6ⁱ—C7—C11	125.9 (2)
C5ⁱ—Ru1—C1	157.77 (14)	C6—C7—C11	125.9 (2)
C3—Ru1—C1	66.77 (19)	C6ⁱ—C7—Ru1	70.9 (3)
C3ⁱ—Ru1—C1	66.77 (19)	C6—C7—Ru1	70.9 (3)
C7—Ru1—C2	117.11 (16)	C11—C7—Ru1	125.3 (4)
C6—Ru1—C2	150.82 (17)	C4—C8—H8A	109.5
C6ⁱ—Ru1—C2	106.93 (16)	C4—C8—H8B	109.5
C5—Ru1—C2	165.19 (17)	H8A—C8—H8B	109.5
C5ⁱ—Ru1—C2	127.41 (17)	C4—C8—H8C	109.5
C3—Ru1—C2	37.09 (17)	H8A—C8—H8C	109.5
C3ⁱ—Ru1—C2	78.75 (17)	H8B—C8—H8C	109.5
C1—Ru1—C2	36.81 (14)	C5—C9—H9A	109.5
C7—Ru1—C2ⁱ	117.11 (16)	C5—C9—H9B	109.5
C6—Ru1—C2ⁱ	106.93 (16)	H9A—C9—H9B	109.5
C6ⁱ—Ru1—C2ⁱ	150.82 (17)	C5—C9—H9C	109.5
C5—Ru1—C2ⁱ	127.41 (17)	H9A—C9—H9C	109.5
C5ⁱ—Ru1—C2ⁱ	165.19 (17)	H9B—C9—H9C	109.5
C3—Ru1—C2ⁱ	78.75 (17)	C6—C10—H10A	109.5
C3ⁱ—Ru1—C2ⁱ	37.09 (17)	C6—C10—H10B	109.5
C1—Ru1—C2ⁱ	36.81 (14)	H10A—C10—H10B	109.5
C2—Ru1—C2ⁱ	66.3 (2)	C6—C10—H10C	109.5
C7—Ru1—C4	174.3 (2)	H10A—C10—H10C	109.5
C6—Ru1—C4	138.37 (15)	H10B—C10—H10C	109.5
C6ⁱ—Ru1—C4	138.37 (15)	C7—C11—H11A	109.5
C5—Ru1—C4	110.35 (18)	C7—C11—H11B	109.5
C5ⁱ—Ru1—C4	110.35 (18)	H11A—C11—H11B	109.5
C3—Ru1—C4	37.51 (13)	C7—C11—H11C	109.5
C3ⁱ—Ru1—C4	37.51 (13)	H11A—C11—H11C	109.5
C1—Ru1—C4	79.8 (2)	H11B—C11—H11C	109.5
C2—Ru1—C4	67.48 (17)	F1ⁱⁱ—P1—F1	180.000 (1)
C2ⁱ—Ru1—C4	67.48 (17)	F1ⁱⁱ—P1—F2ⁱⁱ	89.60 (15)
C2—C1—C2ⁱ	120.1 (6)	F1—P1—F2ⁱⁱ	90.40 (15)
C2—C1—Ru1	71.8 (3)	F1ⁱⁱ—P1—F2	90.40 (15)
C2ⁱ—C1—Ru1	71.8 (3)	F1—P1—F2	89.60 (15)
C2—C1—H1	119.9	F2ⁱⁱ—P1—F2	180.000 (1)
C2ⁱ—C1—H1	119.9	F1ⁱⁱ—P1—F3ⁱⁱ	90.12 (16)
Ru1—C1—H1	128.7	F1—P1—F3ⁱⁱ	89.88 (16)
C1—C2—C3	120.1 (4)	F2ⁱⁱ—P1—F3ⁱⁱ	89.79 (14)
C1—C2—Ru1	71.4 (3)	F2—P1—F3ⁱⁱ	90.21 (14)
C3—C2—Ru1	70.9 (2)	F1ⁱⁱ—P1—F3	89.88 (16)
C1—C2—H2A	119.4	F1—P1—F3	90.12 (16)
C3—C2—H2A	119.4	F2ⁱⁱ—P1—F3	90.21 (14)
Ru1—C2—H2A	119.4	F2—P1—F3	89.79 (14)
C2—C3—C4	121.2 (4)	F3ⁱⁱ—P1—F3	180.0

Symmetry codes: (i) x, −y+1/2, z; (ii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2ⁱ	1.00	2.46	3.450 (4)	173
C2—H2A···F3ⁱ	1.00	2.54	3.243 (5)	127
C3—H3A···F2ⁱⁱⁱ	1.00	2.44	3.356 (5)	151
C8—H8C···F3^iv	0.98	2.55	3.258 (5)	129
C10—H10B···F1ⁱⁱ	0.98	2.54	3.515 (6)	175

Symmetry codes: (i) x, −y+1/2, z; (ii) −x, −y+1, −z+1; (iii) −x, y−1/2, −z; (iv) x, y, z−1.

Experimental details

Crystal data
Chemical formula	[Ru(C₇H₈)(C₁₀H₁₅)]PF₆
M_r	473.39
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	150
a, b, c (Å)	13.9735 (4), 15.3266 (4), 8.6576 (6)
V (Å³)	1854.17 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.22 × 0.15 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.711, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	11870, 2200, 1611
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.07
No. of reflections	2200
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.11, −2.04

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2ⁱ	1.00	2.46	3.450 (4)	173
C2—H2A···F3ⁱ	1.00	2.54	3.243 (5)	127
C3—H3A···F2ⁱⁱ	1.00	2.44	3.356 (5)	151
C8—H8C···F3ⁱⁱⁱ	0.98	2.55	3.258 (5)	129
C10—H10B···F1^iv	0.98	2.54	3.515 (6)	175

Symmetry codes: (i) x, −y+1/2, z; (ii) −x, y−1/2, −z; (iii) x, y, z−1; (iv) −x, −y+1, −z+1.

Acknowledgements

NSERC Canada is thanked for a Discovery Grant to RHM. NSERC Canada and the Ministry of Education of Ontario are thanked for graduate scholarships to WWNO.

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