(η-Penta-methyl-cyclo-penta-dien-yl)(η-toluene)-ruthenium(II) hexa-fluorido-phosphate.

Abstract

In the title complex, [Ru(C(7)H(8))(C(10)H(15))]PF(6), 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 cyclo-penta-dienyl 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.

Full text

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(g5-Pentamethylcyclopentadienyl)(g6-
toluene)ruthenium(II) hexafluorido-
phosphate
Wylie W. N. O, Alan J. Lough* and Robert H. Morris
Department 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
Key indicators: single-crystal X-ray study; T = 150 K; mean ?(C–C) = 0.007 A ˚;
disorder in main residue; R factor = 0.048; wR factor = 0.131; data-to-parameter
ratio = 17.2.
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) A˚and the distance between the Ru
atom and the cyclopentadienyl ring is 1.811 (5) A˚. 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); Jime ´nez-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
Mr= 473.39
Orthorhombic, Pnma
a = 13.9735 (4) A˚
b = 15.3266 (4) A˚
c = 8.6576 (6) A˚
V = 1854.17 (15) A˚3
Z = 4
Mo K? radiation
? = 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)
Tmin= 0.711, Tmax= 0.863
11870 measured reflections
2200 independent reflections
1611 reflections with I > 2?(I)
Rint= 0.062
Refinement
R[F2> 2?(F2)] = 0.048
wR(F2) = 0.131
S = 1.07
2200 reflections
128 parameters
H-atom parameters constrained
??max= 2.11 e A˚?3
??min= ?2.04 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
C2—H2A???F2i
C2—H2A???F3i
C3—H3A???F2ii
C8—H8C???F3iii
C10—H10B???F1iv
Symmetry
?x;?y þ 1;?z þ 1.
D—HH???AD???AD—H???A
1.00
1.00
1.00
0.98
0.98
2.46
2.54
2.44
2.55
2.54
3.450 (4)
3.243 (5)
3.356 (5)
3.258 (5)
3.515 (6)
173
127
151
129
175
codes:(i)x;?y þ1
2;z;(ii)
?x;y ?1
2;?z;(iii)x;y;z ? 1;(iv)
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 (Shel-
drick, 2008); molecular graphics: PLATON (Spek, 2009); software
used to prepare material for publication: SHELXTL.
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.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: PK2266).
References
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Arliguie, T., Chaudret, B., Jalon, F. & Lahoz, F. (1988). Chem. Comm. p. 998.
Blessing, R. H. (1995). Acta Cryst. A51, 33–38.
Clapham, S. E., Hadzovic, A. & Morris, R. H. (2004). Coord. Chem. Rev. 248,
2201–2237.
Coville, N. J., Duplooy, K. E. & Pickl, W. (1992). Coord.Chem. Rev. 116, 1–267.
Fagan, P. J., Mahoney, W. S., Calabrese, J. C. & Williams, I. D. (1990).
Organometallics, 9, 1843–1852.
Fagan, P. J., Ward, M. D. & Calabrese, J. C. (1989). J. Am. Chem. Soc. 111,
1698–1719.
He, X. D., Chaudret, B., Dahan, F. & Huang, Y.-S. (1991). Organometallics, 10,
970–979.
Jime ´nez-Tenorio, M., Puerta, M. C. & Valerga, V. (2004). Eur. J. Inorg. Chem.
pp. 17–32.
O, W. W. N., Lough, A. J. & Morris, R. H. (2010). Chem. Commun. In the press.
Loughrey, B. T., Healy, P. C., Parsons, R. G. & Williams, M. L. (2008). Inorg.
Chem. 47, 8589–8591.
Nolan, S. P., Martin, K. L., Buzatu, D., Trudell, M. L., Stevens, E. D. & Fagan, P.
(1993). J. Struct. Chem. 4, 367–375.
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307–326. New York: Academic Press.
Schmid, A., Holger, P. & Lindel, T. (2003). Eur. J. Inorg. Chem. pp. 2255–2263.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
metal-organic compounds
m1264
O et al.
doi:10.1107/S1600536810036299
Acta Cryst. (2010). E66, m1264
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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Acta Cryst. (2010). E66, m1264 [ doi:10.1107/S1600536810036299 ]
(5-Pentamethylcyclopentadienyl)(6-toluene)ruthenium(II) hexafluoridophosphate
W. W. N. O, A. J. Lough and R. H. Morris
Comment
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 lig-
ands (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 tetrahydro-
furan 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 mo-
lecule. 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 RuII ion is 179.49 (15)°. The crystal structure is stabilized
by weak C—H···F hydrogen bonds.
Experimental
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.

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Refinement
Hydrogen atoms were placed in calculated positions with C—H distances ranging from 0.95 to 1.00 Å and included in the
refinement in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C) for methyl H atoms.
Figures
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
Crystal data
[Ru(C7H8)(C10H15)]PF6
F(000) = 952
Dx = 1.696 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 11870 reflections
θ = 2.7–27.5°
µ = 0.99 mm−1
T = 150 K
Mr = 473.39
Orthorhombic, Pnma
Hall symbol: -P 2ac 2n
a = 13.9735 (4) Å
b = 15.3266 (4) Å
c = 8.6576 (6) Å
V = 1854.17 (15) Å3
Z = 4
Block, colourless
0.22 × 0.15 × 0.10 mm
Data collection
Nonius KappaCCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
Detector resolution: 9 pixels mm-1
φ scans and ω scans with κ offsets
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
Tmin = 0.711, Tmax = 0.863
11870 measured reflections
2200 independent reflections
1611 reflections with I > 2σ(I)
Rint = 0.062
θmax = 27.5°, θmin = 2.7°
h = −17→18
k = −15→19
l = −11→11
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods

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Least-squares matrix: fullSecondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.131
H-atom parameters constrained
S = 1.07
w = 1/[σ2(Fo2) + (0.065P)2 + 3.7819P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.003
Δρmax = 2.11 e Å−3
Δρmin = −2.04 e Å−3
2200 reflections
128 parameters
0 restraints
Special details
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 mat-
rix. 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, convention-
al 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)
x
0.09419 (3)
−0.0364 (4)
−0.0414
−0.0326 (3)
−0.0235
−0.0226 (3)
−0.0065
−0.0174 (4)
0.2303 (3)
0.2204 (3)
0.2144 (4)
−0.0027 (5)
−0.0634
0.0452
0.0194
0.2427 (3)
0.3097
0.2018
0.2247
0.2220 (3)
0.2883
0.1860
0.1926
y
0.2500
0.2500
0.2500
0.1709 (3)
0.1153
0.1708 (3)
0.1147
0.2500
0.2969 (3)
0.3259 (3)
0.2500
0.2500
0.2363
0.2060
0.3077
0.3550 (3)
0.3733
0.4065
0.3232
0.4184 (3)
0.4368
0.4235
0.4557
z
0.05036 (5)
0.1948 (8)
0.3042
0.1144 (5)
0.1730
−0.0472 (5)
−0.1005
−0.1323 (7)
−0.0428 (5)
0.1143 (5)
0.2112 (7)
−0.3057 (7)
−0.3571
−0.3333
−0.3389
−0.1801 (6)
−0.1875
−0.1689
−0.2739
0.1676 (6)
0.1846
0.2644
0.0888
Uiso*/Ueq
0.02470 (18)
0.0364 (15)
0.044*
0.0329 (10)
0.040*
0.0318 (10)
0.038*
0.0300 (13)
0.0266 (9)
0.0266 (9)
0.0267 (13)
0.0393 (16)
0.059*
0.059*
0.059*
0.0391 (11)
0.059*
0.059*
0.059*
0.0405 (12)
0.061*
0.061*
0.061*
Occ. (<1)
Ru1
C1
H1
C2
H2A
C3
H3A
C4
C5
C6
C7
C8
H8A
H8B
H8C
C9
H9A
H9B
H9C
C10
H10A
H10B
H10C
0.50
0.50
0.50

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C11
H11A
H11B
H11C
P1
F1
F2
F3
0.2061 (4)
0.1816
0.2692
0.1620
0.0000
−0.09922 (18)
0.0208 (2)
−0.0520 (2)
0.2500
0.3066
0.2397
0.2037
0.5000
0.5503 (2)
0.51551 (18)
0.40978 (18)
0.3875 (8)
0.4224
0.4331
0.4200
0.5000
0.4824 (4)
0.3204 (3)
0.4592 (3)
0.0399 (16)
0.060*
0.060*
0.060*
0.0282 (4)
0.0454 (7)
0.0450 (7)
0.0435 (7)
0.50
0.50
0.50
Atomic displacement parameters (Å2)
U11
0.0238 (3)
0.024 (3)
0.026 (2)
0.028 (2)
0.026 (3)
0.023 (2)
0.0190 (19)
0.021 (3)
0.042 (4)
0.041 (3)
0.037 (2)
0.025 (3)
0.0331 (8)
0.0403 (16)
0.0653 (18)
0.0556 (18)
U22
0.0249 (3)
0.052 (4)
0.034 (2)
0.031 (2)
0.038 (4)
0.029 (2)
0.033 (2)
0.040 (3)
0.052 (4)
0.042 (3)
0.036 (3)
0.046 (4)
0.0276 (8)
0.0456 (18)
0.0425 (16)
0.0311 (15)
U33
0.0255 (3)
0.033 (4)
0.039 (3)
0.036 (3)
0.025 (3)
0.028 (2)
0.028 (2)
0.019 (3)
0.024 (3)
0.035 (3)
0.049 (3)
0.049 (4)
0.0240 (8)
0.0502 (18)
0.0273 (14)
0.0438 (17)
U12
0.000
0.000
−0.0065 (18)
−0.0049 (18)
0.000
−0.0033 (17)
−0.0030 (17)
0.000
0.000
−0.001 (2)
−0.005 (2)
0.000
0.0019 (6)
0.0127 (12)
−0.0008 (14)
−0.0070 (13)
U13
0.00149 (19)
0.005 (3)
−0.0021 (19)
−0.0049 (18)
−0.004 (2)
0.0042 (16)
0.0053 (16)
−0.001 (2)
−0.003 (3)
0.007 (2)
0.011 (2)
0.011 (3)
0.0018 (7)
−0.0027 (13)
0.0050 (13)
−0.0045 (13)
U23
0.000
0.000
0.011 (2)
−0.002 (2)
0.000
0.0022 (18)
−0.0073 (18)
0.000
0.000
0.012 (2)
−0.011 (2)
0.000
−0.0006 (7)
−0.0017 (14)
−0.0005 (13)
−0.0018 (12)
Ru1
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
P1
F1
F2
F3
Geometric parameters (Å, °)
Ru1—C7
Ru1—C6
Ru1—C6i
Ru1—C5
Ru1—C5i
Ru1—C3
Ru1—C3i
Ru1—C1
Ru1—C2
Ru1—C2i
Ru1—C4
C1—C2
C1—C2i
C1—H1
C2—C3
C2—H2A
2.181 (5)
2.184 (4)
C6—C7
C6—C10
C7—C6i
C7—C11
1.436 (5)
1.491 (6)
2.184 (4)1.436 (5)
2.187 (4)1.531 (9)
2.187 (4) C8—H8A0.9800
2.203 (4) C8—H8B0.9800
2.203 (4) C8—H8C0.9800
2.211 (6)
2.217 (4)
C9—H9A
C9—H9B
0.9800
0.9800
2.217 (4) C9—H9C0.9800
2.220 (6)
1.398 (6)
C10—H10A
C10—H10B
0.9800
0.9800
1.398 (6)C10—H10C 0.9800
0.9500
1.406 (6)
1.0000
C11—H11A
C11—H11B
C11—H11C
0.9800
0.9800
0.9800

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C3—C41.422 (6)
P1—F1ii
P1—F1
P1—F2ii
P1—F2
P1—F3ii
1.594 (3)
C3—H3A
C4—C3i
C4—C8
1.00001.594 (3)
1.422 (6) 1.599 (3)
1.515 (9) 1.599 (3)
C5—C61.437 (6)1.601 (3)
C5—C5i
C5—C9
1.437 (9) P1—F31.601 (3)
1.495 (6)
C7—Ru1—C6
C7—Ru1—C6i
C6—Ru1—C6i
C7—Ru1—C5
C6—Ru1—C5
C6i—Ru1—C5
C7—Ru1—C5i
C6—Ru1—C5i
C6i—Ru1—C5i
C5—Ru1—C5i
C7—Ru1—C3
38.42 (14) C2—C3—Ru172.0 (2)
38.42 (14) C4—C3—Ru171.9 (3)
64.3 (2)C2—C3—H3A 118.9
64.28 (17)
38.40 (15)
C4—C3—H3A
Ru1—C3—H3A
C3i—C4—C3
C3i—C4—C8
118.9
118.9
64.29 (15) 117.3 (6)
64.28 (17)121.3 (3)
64.29 (15)C3—C4—C8 121.3 (3)
38.40 (15)
C3i—C4—Ru1
70.6 (3)
38.4 (2) C3—C4—Ru170.6 (3)
144.60 (13)C8—C4—Ru1
C6—C5—C5i
127.7 (4)
C6—Ru1—C3 171.56 (16)108.0 (2)
C6i—Ru1—C3
113.71 (17) C6—C5—C9125.4 (4)
C5—Ru1—C3 133.16 (16)
C5i—C5—C9
126.5 (3)
C5i—Ru1—C3
C7—Ru1—C3i
C6—Ru1—C3i
C6i—Ru1—C3i
C5—Ru1—C3i
C5i—Ru1—C3i
C3—Ru1—C3i
C7—Ru1—C1
C6—Ru1—C1
C6i—Ru1—C1
108.77 (17) C6—C5—Ru170.7 (2)
144.60 (13)
C5i—C5—Ru1
70.81 (11)
113.71 (17)C9—C5—Ru1126.1 (3)
171.56 (16) C5—C6—C7107.9 (4)
108.77 (17) C5—C6—C10125.8 (4)
133.16 (16) C7—C6—C10 126.2 (4)
66.9 (2)C5—C6—Ru170.9 (2)
105.9 (2)
121.52 (17)
C7—C6—Ru1
C10—C6—Ru1
C6i—C7—C6
C6i—C7—C11
70.7 (3)
126.6 (3)
121.52 (17)108.1 (5)
C5—Ru1—C1157.77 (14)125.9 (2)
C5i—Ru1—C1
157.77 (14)C6—C7—C11125.9 (2)
C3—Ru1—C166.77 (19)
C6i—C7—Ru1
70.9 (3)
C3i—Ru1—C1
C7—Ru1—C2
C6—Ru1—C2
C6i—Ru1—C2
C5—Ru1—C2
C5i—Ru1—C2
C3—Ru1—C2
C3i—Ru1—C2
C1—Ru1—C2
66.77 (19)C6—C7—Ru1 70.9 (3)
117.11 (16)
150.82 (17)
C11—C7—Ru1
C4—C8—H8A
125.3 (4)
109.5
106.93 (16)C4—C8—H8B 109.5
165.19 (17)H8A—C8—H8B 109.5
127.41 (17) C4—C8—H8C 109.5
37.09 (17) H8A—C8—H8C 109.5
78.75 (17) H8B—C8—H8C109.5
36.81 (14)C5—C9—H9A 109.5

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supplementary materials
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C7—Ru1—C2i
C6—Ru1—C2i
C6i—Ru1—C2i
C5—Ru1—C2i
C5i—Ru1—C2i
C3—Ru1—C2i
C3i—Ru1—C2i
C1—Ru1—C2i
C2—Ru1—C2i
C7—Ru1—C4
C6—Ru1—C4
C6i—Ru1—C4
C5—Ru1—C4
C5i—Ru1—C4
C3—Ru1—C4
C3i—Ru1—C4
C1—Ru1—C4
117.11 (16) C5—C9—H9B 109.5
106.93 (16) H9A—C9—H9B109.5
150.82 (17) C5—C9—H9C 109.5
127.41 (17)H9A—C9—H9C 109.5
165.19 (17)H9B—C9—H9C 109.5
78.75 (17)C6—C10—H10A 109.5
37.09 (17) C6—C10—H10B109.5
36.81 (14)H10A—C10—H10B 109.5
66.3 (2)C6—C10—H10C 109.5
174.3 (2)
138.37 (15)
H10A—C10—H10C
H10B—C10—H10C
109.5
109.5
138.37 (15) C7—C11—H11A109.5
110.35 (18)C7—C11—H11B 109.5
110.35 (18) H11A—C11—H11B 109.5
37.51 (13) C7—C11—H11C109.5
37.51 (13) H11A—C11—H11C 109.5
79.8 (2)H11B—C11—H11C
F1ii—P1—F1
F1ii—P1—F2ii
F1—P1—F2ii
F1ii—P1—F2
109.5
C2—Ru1—C4 67.48 (17)180.000 (1)
C2i—Ru1—C4
C2—C1—C2i
67.48 (17)89.60 (15)
120.1 (6) 90.40 (15)
C2—C1—Ru171.8 (3)90.40 (15)
C2i—C1—Ru1
71.8 (3) F1—P1—F2 89.60 (15)
C2—C1—H1119.9
F2ii—P1—F2
F1ii—P1—F3ii
F1—P1—F3ii
F2ii—P1—F3ii
F2—P1—F3ii
F1ii—P1—F3
F1—P1—F3
F2ii—P1—F3
F2—P1—F3
F3ii—P1—F3
180.000 (1)
C2i—C1—H1
119.9 90.12 (16)
Ru1—C1—H1 128.789.88 (16)
C1—C2—C3 120.1 (4)89.79 (14)
C1—C2—Ru171.4 (3) 90.21 (14)
C3—C2—Ru170.9 (2)89.88 (16)
C1—C2—H2A 119.490.12 (16)
C3—C2—H2A 119.4 90.21 (14)
Ru1—C2—H2A 119.489.79 (14)
C2—C3—C4121.2 (4) 180.0
Symmetry codes: (i) x, −y+1/2, z; (ii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °)
D—H···A
C2—H2A···F2i
C2—H2A···F3i
C3—H3A···F2iii
C8—H8C···F3iv
C10—H10B···F1ii
Symmetry codes: (i) x, −y+1/2, z; (iii) −x, y−1/2, −z; (iv) x, y, z−1; (ii) −x, −y+1, −z+1.
D—H H···AD···AD—H···A
1.002.463.450 (4) 173
1.00 2.543.243 (5)127
1.002.443.356 (5)151
0.982.553.258 (5) 129
0.98 2.543.515 (6) 175

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Fig. 1

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supplementary materials
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Fig. 2