metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[1,1′-Bis(di­phenyl­phosphan­yl)cobalto­cenium-κ2P,P′](η5-cyclo­penta­dien­yl){2-[4-(4-ethynylphen­yl)phen­yl]ethynyl-κC}ruthenium(II) hexa­fluorido­phosphate

aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, People's Republic of China, and bCollege of Resources and Environment, Yuxi Normal University, Kunming 653100, People's Republic of China
*Correspondence e-mail: lzokmail@163.com

(Received 4 October 2013; accepted 14 October 2013; online 19 October 2013)

In the title compound, [CoRu(C5H5)(C16H9)(C17H14P)2]PF6, the RuII atom is coordinated by a cyclo­penta­dienyl ring in an η5-mode, one C atom from a 4,4′-diethynyl-1,1′-biphenyl ligand and two P atoms from a chelating 1,1′-bis­(di­phenyl­phosphan­yl)cobaltocenium ligand, giving a three-legged piano-stool geometry. In the crystal, weak C—H⋯F hydrogen bonds link the complex cations and hexa­fluorido­phosphate anions into a three-dimensional supra­molecular structure.

Related literature

For the synthesis of related compounds, see: Blackmore et al. (1971[Blackmore, T., Bruce, M. I. & Stone, F. C. (1971). J. Chem. Soc. 14, 2376-2382.]); Oshima & Suzuki (1984[Oshima, N. & Suzuki, H. (1984). Chem. Lett. 13, 1161-1164.]); Wu et al. (2006[Wu, X.-H., Ren, Y., Yu, G.-A. & Liu, S.-H. (2006). Acta Cryst. E62, m426-m428.]). For the properties of related compounds, see: Domazetis et al. (1980[Domazetis, G., Tarpey, B., Dolphin, D. & James, B. R. (1980). J. Chem. Soc. Chem. Commun. pp. 939-940.]); Gaughan et al. (1972[Gaughan, A. P., Bownan, K. S. & Dori, Z. (1972). Inorg. Chem. 11, 601-608.]); Nombel et al. (1999[Nombel, P., Lugan, N., Donnadieu, B. & Lavigne, G. (1999). Organometallics, 18, 187-196.]); Ziolo & Dori (1968[Ziolo, R. F. & Dori, Z. (1968). J. Am. Chem. Soc. 90, 6560-6561.]). For related structures, see: Bruce et al. (2003[Bruce, M. I., Ellis, B. G., Low, P. J., Skelton, B. W. & White, A. H. (2003). Organometallics, 22, 3184-3198.]); Hembre et al. (1996[Hembre, R. T., McQueen, J. A. & Day, V. W. (1996). J. Am. Chem. Soc. 118, 798-803.]).

[Scheme 1]

Experimental

Crystal data
  • [CoRu(C5H5)(C16H9)(C17H14P)2]PF6

  • Mr = 1069.80

  • Monoclinic, P 21 /c

  • a = 14.481 (5) Å

  • b = 22.052 (7) Å

  • c = 14.482 (5) Å

  • β = 92.937 (2)°

  • V = 4619 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.85 mm−1

  • T = 292 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.784, Tmax = 0.848

  • 53044 measured reflections

  • 10985 independent reflections

  • 7027 reflections with I > 2σ(I)

  • Rint = 0.124

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.140

  • S = 0.97

  • 10985 reflections

  • 595 parameters

  • H-atom parameters constrained

  • Δρmax = 0.83 e Å−3

  • Δρmin = −0.82 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯F5i 0.98 2.43 3.189 (6) 134
C3—H3⋯F6ii 0.98 2.54 3.383 (6) 144
C7—H7⋯F4i 0.98 2.47 3.383 (7) 155
C9—H9⋯F2ii 0.98 2.32 2.993 (6) 125
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The fragment [Cp*Ru(PPh3)2Cl] (Cp* = cyclopentadienyl) plays an important role in the development of organo-ruthenium chemistry and has been used as a versatile starting material for other compounds due to its stability and facile manipulation (Blackmore et al., 1971; Oshima & Suzuki, 1984; Wu et al., 2006). The interest in this fragment and related derivatives concerns its ability to act as a catalyst in a variety of reactions, such as decarbonylation of both aromatic and aliphatic aldehydes (Domazetis et al., 1980) and hydroformylation reactions (Nombel et al., 1999), as well as anti-Markovnikov hydration of terminal alkynes (Gaughan et al., 1972; Ziolo & Dori, 1968). Herein we report the synthesis and structure of the title compound.

The structure of the title compound is shown in Fig. 1. The Ru—P bond lengths in the compound [2.2497 (12) and 2.2924 (12) Å] are slightly different from those in the neutral complexes, Cp*Ru(dppm)Cl [2.282 (2) and 2.294 (2) Å; dppm = bis(diphenyphosphanyl)methane] and Cp*Ru(dppe)Cl [2.2882 (5) and 2.2812 (5) Å; dppe = bis(diphenylphosphanyl)methane] (Bruce et al., 2003). The Ru—C(Cp*) bond lengths ranging from 2.222 (4) to 2.249 (4) Å are approximately the same with those in Cp*Ru(dppm)Cl and Cp*Ru(dppe)Cl, while Ru—C(4,4'-bisethynyl-1,1'-biphenyl) bond length [2.022 (4) Å] is slightly shorter. The Ru—Cg1, Co—Cg2 and Co—Cg3 distances are 1.9050 (2), 1.6225 (2) and 1.6245 (2) Å (Cg1 is the centroid of the Cp* ring, and Cg2 and Cg3 are the centroids of C1–C5 ring and C6–C10 ring), which are not significantly different from those found in Cp*Ru(dppf)H [dppf = 1,10-bis(diphenylphosphanyl)ferrocene] (Hembre et al., 1996). The P—Ru—P angle [99.30 (4)°] in the compound is larger than those found in the dppm and dppe complexes [71.53 (6) in Cp*Ru(dppm)Cl and 82.15 (2)° in Cp*Ru(dppe)Cl], possibly due to the steric demand of the chelating dppc [dppc = 1,10-bis(diphenylphosphanyl)cobaltocenium] ligand in the title compound. The Cg2—P1—P2—Cg3 torsion angle is 5.54 (6)°. The C1–C5 and C6–C10 rings are arranged close to a synperiplanar eclipsed conformation, with a dihedral angle of 2.0 (2)°. The dihedral angle is 19.3 (2) between the benzene rings of the 4,4'-bisethynyl-1,1'-biphenyl ligand, which are not coplanar. In the crystal, weak C—H···F hydrogen bonds link the complex cations and hexafluoridophosphate anions into a three-dimensional supramolecular structure (Table 1 and Fig. 2).

Related literature top

For the synthesis of related compounds, see: Blackmore et al. (1971); Oshima & Suzuki (1984); Wu et al. (2006). For the properties of related compounds, see: Domazetis et al. (1980); Gaughan et al. (1972); Nombel et al. (1999); Ziolo & Dori (1968). For related structures, see: Bruce et al. (2003); Hembre et al. (1996).

Experimental top

To a solution of [Cp*Ru(dppc)Cl](PF6) (0.9 g, 1.0 mmol) in 20 ml of CH3OH was added 4,4'-bis[(trimethylsilyl)ethynyl]-1,1'-biphenyl (0.17 g, 0.5 mmol) in CH2Cl2 (20 ml). The mixture was refluxed for 24 h. After removal of the solvent in vacuo, the desired product was chromatographed on alumina by elution with CH2Cl2/CH3COCH3 (10:1) to yield 0.23 g (43%) of a green solid (Oshima & Suzuki, 1984). The single crystals were obtained by the slow diffusion of n-hexane into a dichloromethane solution of the compound.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and 0.98 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A view of the crystal packing. Hydrogen bonds are shown as dashed lines.
[1,1'-Bis(diphenylphosphanyl)cobaltocenium-κ2P,P'](η5-cyclopentadienyl){2-[4-(4-ethynylphenyl)phenyl]ethynyl-κC}ruthenium(II) hexafluoridophosphate top
Crystal data top
[CoRu(C5H5)(C16H9)(C17H14P)2]PF6F(000) = 2168
Mr = 1069.80Dx = 1.538 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9162 reflections
a = 14.481 (5) Åθ = 2.2–24.8°
b = 22.052 (7) ŵ = 0.85 mm1
c = 14.482 (5) ÅT = 292 K
β = 92.937 (2)°Block, black
V = 4619 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
10985 independent reflections
Radiation source: fine-focus sealed tube7027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.124
ϕ and ω scansθmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.784, Tmax = 0.848k = 2929
53044 measured reflectionsl = 1919
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0665P)2]
where P = (Fo2 + 2Fc2)/3
10985 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 0.82 e Å3
Crystal data top
[CoRu(C5H5)(C16H9)(C17H14P)2]PF6V = 4619 (3) Å3
Mr = 1069.80Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.481 (5) ŵ = 0.85 mm1
b = 22.052 (7) ÅT = 292 K
c = 14.482 (5) Å0.30 × 0.20 × 0.20 mm
β = 92.937 (2)°
Data collection top
Bruker APEX CCD
diffractometer
10985 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7027 reflections with I > 2σ(I)
Tmin = 0.784, Tmax = 0.848Rint = 0.124
53044 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 0.97Δρmax = 0.83 e Å3
10985 reflectionsΔρmin = 0.82 e Å3
595 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
xyzUiso*/Ueq
Ru10.14140 (2)0.117675 (14)0.61008 (2)0.03605 (11)
Co10.39049 (4)0.07678 (2)0.78319 (4)0.03828 (15)
P10.19282 (7)0.16321 (4)0.74190 (7)0.0360 (2)
P20.20918 (7)0.02449 (4)0.63204 (7)0.0337 (2)
C10.3097 (3)0.15053 (16)0.7960 (3)0.0380 (9)
C20.3389 (3)0.12705 (18)0.8846 (3)0.0462 (10)
H20.29820.11240.93190.055*
C30.4366 (3)0.1275 (2)0.8917 (3)0.0581 (13)
H30.47510.11290.94470.070*
C40.4696 (3)0.15178 (19)0.8100 (3)0.0567 (12)
H40.53460.15690.79600.068*
C50.3924 (3)0.16604 (17)0.7509 (3)0.0436 (10)
H50.39480.18280.68840.052*
C60.3211 (3)0.01700 (16)0.6984 (3)0.0350 (9)
C70.3373 (3)0.00824 (17)0.7877 (3)0.0422 (10)
H70.28980.02210.82870.051*
C80.4345 (3)0.00871 (17)0.8086 (3)0.0482 (11)
H80.46510.02310.86640.058*
C90.4790 (3)0.01508 (19)0.7328 (3)0.0477 (11)
H90.54580.02020.72810.057*
C100.4090 (3)0.03187 (17)0.6650 (3)0.0401 (9)
H100.41970.05060.60500.048*
C110.1157 (3)0.15023 (18)0.8351 (3)0.0425 (10)
C120.0433 (3)0.1898 (2)0.8526 (3)0.0553 (12)
H120.03910.22680.82200.066*
C130.0219 (4)0.1747 (3)0.9148 (4)0.0734 (16)
H130.07030.20100.92560.088*
C140.0144 (4)0.1201 (3)0.9607 (4)0.0820 (18)
H140.05800.10981.00300.098*
C150.0560 (4)0.0811 (3)0.9450 (3)0.0680 (14)
H150.06050.04470.97740.082*
C160.1203 (3)0.0950 (2)0.8819 (3)0.0544 (12)
H160.16710.06760.87040.065*
C170.2041 (3)0.24636 (16)0.7336 (3)0.0400 (9)
C180.2074 (3)0.27338 (18)0.6493 (3)0.0529 (11)
H180.20170.24980.59600.063*
C190.2189 (4)0.3351 (2)0.6418 (4)0.0695 (15)
H190.22020.35310.58380.083*
C200.2283 (4)0.3701 (2)0.7201 (4)0.0629 (13)
H200.23720.41170.71520.076*
C210.2247 (3)0.34435 (19)0.8036 (4)0.0588 (12)
H210.22940.36840.85630.071*
C220.2141 (3)0.28226 (17)0.8121 (3)0.0480 (10)
H220.21370.26460.87050.058*
C230.0623 (3)0.01639 (19)0.7322 (3)0.0487 (11)
H230.04520.02430.73250.058*
C240.0082 (3)0.0594 (2)0.7768 (3)0.0597 (13)
H240.04470.04740.80560.072*
C250.0341 (4)0.1183 (2)0.7774 (3)0.0622 (13)
H250.00090.14690.80740.075*
C260.1117 (4)0.1362 (2)0.7340 (3)0.0632 (13)
H260.12860.17690.73430.076*
C270.1647 (3)0.09449 (18)0.6902 (3)0.0497 (11)
H270.21740.10720.66170.060*
C280.1404 (3)0.03386 (16)0.6880 (3)0.0363 (9)
C290.2455 (3)0.01353 (16)0.5262 (3)0.0368 (9)
C300.3125 (3)0.05909 (19)0.5276 (3)0.0496 (11)
H300.34100.07110.58360.059*
C310.3367 (3)0.0864 (2)0.4472 (3)0.0578 (12)
H310.38110.11680.44890.069*
C320.2961 (3)0.0690 (2)0.3658 (3)0.0576 (13)
H320.31260.08760.31140.069*
C330.2299 (4)0.0238 (2)0.3626 (3)0.0573 (13)
H330.20220.01190.30610.069*
C340.2053 (3)0.00331 (18)0.4428 (3)0.0452 (10)
H340.16060.03360.44040.054*
C350.0200 (3)0.1807 (2)0.6062 (3)0.0556 (12)
H350.01440.21740.64380.067*
C360.0550 (3)0.1781 (2)0.5183 (4)0.0664 (14)
H360.07720.21260.48290.080*
C370.0423 (3)0.1183 (3)0.4852 (3)0.0649 (14)
H370.05520.10370.42330.078*
C380.0024 (3)0.0849 (2)0.5544 (4)0.0599 (13)
H380.01640.04230.54930.072*
C390.0132 (3)0.1223 (2)0.6284 (4)0.0565 (12)
H390.04500.11110.68410.068*
C400.2633 (3)0.13775 (17)0.5551 (3)0.0408 (9)
C410.3350 (3)0.14961 (19)0.5204 (3)0.0479 (10)
C420.4133 (3)0.16157 (18)0.4677 (3)0.0448 (10)
C430.4693 (3)0.2130 (2)0.4812 (3)0.0526 (11)
H430.46000.23840.53120.063*
C440.4361 (3)0.1232 (2)0.3974 (3)0.0560 (12)
H440.40470.08660.38950.067*
C450.5371 (3)0.2267 (2)0.4227 (3)0.0533 (11)
H450.57210.26150.43350.064*
C460.5042 (3)0.1380 (2)0.3387 (3)0.0591 (13)
H460.51600.11140.29080.071*
C470.5560 (3)0.19053 (17)0.3475 (3)0.0458 (10)
C480.6209 (3)0.20920 (19)0.2776 (3)0.0468 (10)
C490.6845 (3)0.2560 (2)0.2922 (3)0.0519 (11)
H490.69080.27400.35020.062*
C500.6177 (4)0.1824 (2)0.1926 (3)0.0635 (13)
H500.57780.14990.18120.076*
C510.7380 (3)0.2762 (2)0.2233 (3)0.0567 (12)
H510.77920.30790.23520.068*
C520.6720 (4)0.2021 (2)0.1229 (3)0.0642 (13)
H520.66800.18260.06600.077*
C530.7318 (3)0.2501 (2)0.1363 (3)0.0556 (12)
C540.7830 (3)0.2735 (2)0.0636 (3)0.0574 (12)
C550.8215 (4)0.2942 (2)0.0036 (4)0.0694 (14)
H550.85260.31100.04500.083*
F10.2865 (6)0.6052 (2)0.5944 (5)0.277 (5)
F20.3473 (3)0.5246 (4)0.6470 (3)0.229 (4)
F30.2045 (3)0.5287 (2)0.6172 (3)0.1314 (16)
F40.2322 (3)0.5580 (3)0.4767 (3)0.187 (3)
F50.2957 (5)0.4787 (2)0.5262 (4)0.210 (3)
F60.3773 (3)0.5565 (3)0.5076 (3)0.167 (2)
P30.29026 (9)0.54231 (6)0.56284 (9)0.0591 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0413 (2)0.03140 (18)0.03518 (18)0.00285 (14)0.00097 (13)0.00073 (13)
Co10.0426 (3)0.0310 (3)0.0405 (3)0.0005 (2)0.0048 (2)0.0036 (2)
P10.0453 (6)0.0263 (5)0.0366 (6)0.0007 (4)0.0034 (4)0.0005 (4)
P20.0384 (6)0.0290 (5)0.0334 (5)0.0014 (4)0.0001 (4)0.0019 (4)
C10.048 (2)0.0259 (19)0.039 (2)0.0005 (17)0.0038 (18)0.0064 (16)
C20.056 (3)0.045 (2)0.036 (2)0.000 (2)0.004 (2)0.0086 (18)
C30.061 (3)0.053 (3)0.058 (3)0.005 (2)0.020 (2)0.019 (2)
C40.057 (3)0.040 (3)0.072 (3)0.008 (2)0.007 (3)0.013 (2)
C50.050 (3)0.028 (2)0.052 (3)0.0030 (18)0.000 (2)0.0036 (18)
C60.043 (2)0.0270 (19)0.035 (2)0.0031 (17)0.0010 (17)0.0065 (16)
C70.053 (3)0.031 (2)0.042 (2)0.0039 (19)0.0028 (19)0.0014 (17)
C80.055 (3)0.033 (2)0.055 (3)0.008 (2)0.013 (2)0.0024 (19)
C90.039 (2)0.042 (2)0.061 (3)0.0063 (19)0.001 (2)0.005 (2)
C100.048 (2)0.040 (2)0.033 (2)0.0005 (19)0.0064 (18)0.0051 (17)
C110.051 (3)0.038 (2)0.039 (2)0.007 (2)0.0022 (19)0.0083 (18)
C120.058 (3)0.052 (3)0.057 (3)0.001 (2)0.011 (2)0.011 (2)
C130.058 (3)0.085 (4)0.079 (4)0.002 (3)0.020 (3)0.028 (3)
C140.083 (4)0.107 (5)0.058 (3)0.036 (4)0.022 (3)0.006 (3)
C150.080 (4)0.068 (3)0.057 (3)0.020 (3)0.013 (3)0.006 (3)
C160.065 (3)0.049 (3)0.051 (3)0.006 (2)0.014 (2)0.000 (2)
C170.049 (2)0.0261 (19)0.045 (2)0.0007 (17)0.0024 (19)0.0019 (17)
C180.076 (3)0.035 (2)0.048 (3)0.000 (2)0.009 (2)0.002 (2)
C190.104 (4)0.043 (3)0.062 (3)0.004 (3)0.011 (3)0.015 (2)
C200.082 (4)0.029 (2)0.078 (4)0.004 (2)0.007 (3)0.002 (2)
C210.070 (3)0.036 (2)0.070 (3)0.001 (2)0.005 (3)0.007 (2)
C220.061 (3)0.030 (2)0.052 (3)0.000 (2)0.003 (2)0.0024 (19)
C230.059 (3)0.038 (2)0.050 (3)0.006 (2)0.008 (2)0.000 (2)
C240.065 (3)0.059 (3)0.057 (3)0.006 (3)0.019 (2)0.006 (2)
C250.076 (4)0.052 (3)0.059 (3)0.025 (3)0.002 (3)0.015 (2)
C260.075 (4)0.041 (3)0.074 (3)0.001 (2)0.003 (3)0.010 (2)
C270.054 (3)0.038 (2)0.057 (3)0.001 (2)0.006 (2)0.004 (2)
C280.042 (2)0.033 (2)0.033 (2)0.0034 (17)0.0030 (17)0.0000 (16)
C290.045 (2)0.0270 (19)0.039 (2)0.0061 (17)0.0075 (18)0.0035 (16)
C300.057 (3)0.046 (2)0.045 (3)0.012 (2)0.000 (2)0.003 (2)
C310.063 (3)0.052 (3)0.060 (3)0.004 (2)0.011 (2)0.013 (2)
C320.079 (4)0.047 (3)0.049 (3)0.015 (3)0.024 (3)0.015 (2)
C330.087 (4)0.050 (3)0.035 (2)0.015 (3)0.008 (2)0.002 (2)
C340.062 (3)0.035 (2)0.040 (2)0.002 (2)0.003 (2)0.0006 (18)
C350.053 (3)0.048 (3)0.065 (3)0.016 (2)0.007 (2)0.004 (2)
C360.056 (3)0.070 (4)0.072 (4)0.018 (3)0.005 (3)0.032 (3)
C370.063 (3)0.092 (4)0.038 (3)0.025 (3)0.013 (2)0.006 (3)
C380.047 (3)0.053 (3)0.077 (4)0.002 (2)0.023 (2)0.012 (3)
C390.041 (3)0.060 (3)0.068 (3)0.007 (2)0.004 (2)0.004 (3)
C400.054 (3)0.030 (2)0.037 (2)0.0024 (19)0.000 (2)0.0008 (17)
C410.053 (3)0.042 (2)0.049 (3)0.001 (2)0.002 (2)0.003 (2)
C420.046 (2)0.038 (2)0.050 (3)0.0045 (19)0.001 (2)0.0121 (19)
C430.060 (3)0.048 (3)0.050 (3)0.007 (2)0.008 (2)0.000 (2)
C440.059 (3)0.041 (3)0.070 (3)0.002 (2)0.018 (2)0.003 (2)
C450.061 (3)0.043 (3)0.057 (3)0.010 (2)0.005 (2)0.003 (2)
C460.069 (3)0.040 (2)0.071 (3)0.002 (2)0.023 (3)0.007 (2)
C470.051 (3)0.030 (2)0.057 (3)0.0036 (19)0.008 (2)0.0073 (19)
C480.050 (3)0.039 (2)0.051 (3)0.005 (2)0.006 (2)0.002 (2)
C490.056 (3)0.046 (3)0.054 (3)0.002 (2)0.008 (2)0.003 (2)
C500.087 (4)0.049 (3)0.055 (3)0.012 (3)0.008 (3)0.001 (2)
C510.053 (3)0.042 (3)0.076 (3)0.006 (2)0.006 (2)0.002 (2)
C520.080 (4)0.060 (3)0.053 (3)0.009 (3)0.009 (3)0.004 (2)
C530.056 (3)0.051 (3)0.061 (3)0.006 (2)0.012 (2)0.010 (2)
C540.052 (3)0.059 (3)0.062 (3)0.001 (2)0.014 (2)0.001 (2)
C550.064 (3)0.073 (4)0.072 (4)0.001 (3)0.013 (3)0.003 (3)
F10.482 (12)0.096 (4)0.273 (8)0.076 (6)0.206 (9)0.089 (4)
F20.097 (3)0.505 (12)0.081 (3)0.065 (5)0.039 (2)0.003 (5)
F30.096 (3)0.205 (5)0.095 (3)0.009 (3)0.025 (2)0.032 (3)
F40.115 (3)0.350 (8)0.095 (3)0.060 (4)0.009 (3)0.076 (4)
F50.354 (9)0.087 (3)0.196 (5)0.015 (4)0.078 (6)0.036 (3)
F60.098 (3)0.277 (6)0.130 (4)0.060 (4)0.047 (3)0.045 (4)
P30.0619 (8)0.0657 (9)0.0492 (7)0.0020 (7)0.0004 (6)0.0108 (6)
Geometric parameters (Å, º) top
Ru1—C402.022 (4)C23—C281.383 (6)
Ru1—C362.222 (4)C23—C241.408 (6)
Ru1—C352.240 (4)C23—H230.9300
Ru1—C382.248 (4)C24—C251.353 (6)
Ru1—C372.249 (4)C24—H240.9300
Ru1—P12.2497 (12)C25—C261.374 (7)
Ru1—C392.271 (5)C25—H250.9300
Ru1—P22.2924 (12)C26—C271.373 (6)
Co1—C102.008 (4)C26—H260.9300
Co1—C22.014 (4)C27—C281.383 (5)
Co1—C32.015 (4)C27—H270.9300
Co1—C82.017 (4)C29—C341.365 (5)
Co1—C12.018 (4)C29—C301.396 (5)
Co1—C52.024 (4)C30—C311.372 (6)
Co1—C72.029 (4)C30—H300.9300
Co1—C92.030 (4)C31—C321.346 (6)
Co1—C62.032 (4)C31—H310.9300
Co1—C42.038 (4)C32—C331.381 (7)
P1—C111.818 (4)C32—H320.9300
P1—C171.845 (4)C33—C341.370 (6)
P1—C11.850 (4)C33—H330.9300
P2—C281.840 (4)C34—H340.9300
P2—C291.847 (4)C35—C361.395 (7)
P2—C61.849 (4)C35—C391.418 (6)
C1—C21.427 (5)C35—H350.9800
C1—C51.435 (6)C36—C371.412 (7)
C2—C31.414 (6)C36—H360.9800
C2—H20.9800C37—C381.392 (7)
C3—C41.403 (7)C37—H370.9800
C3—H30.9800C38—C391.379 (6)
C4—C51.408 (6)C38—H380.9800
C4—H40.9800C39—H390.9800
C5—H50.9800C40—C411.205 (6)
C6—C71.416 (5)C41—C421.424 (6)
C6—C101.423 (5)C42—C441.378 (6)
C7—C81.424 (6)C42—C431.402 (6)
C7—H70.9800C43—C451.363 (6)
C8—C91.402 (6)C43—H430.9300
C8—H80.9800C44—C461.374 (6)
C9—C101.423 (5)C44—H440.9300
C9—H90.9800C45—C471.388 (6)
C10—H100.9800C45—H450.9300
C11—C161.393 (6)C46—C471.383 (6)
C11—C121.397 (6)C46—H460.9300
C12—C131.379 (7)C47—C481.474 (6)
C12—H120.9300C48—C501.365 (6)
C13—C141.377 (8)C48—C491.392 (6)
C13—H130.9300C49—C511.368 (6)
C14—C151.362 (8)C49—H490.9300
C14—H140.9300C50—C521.380 (6)
C15—C161.374 (6)C50—H500.9300
C15—H150.9300C51—C531.384 (6)
C16—H160.9300C51—H510.9300
C17—C181.362 (5)C52—C531.374 (7)
C17—C221.387 (5)C52—H520.9300
C18—C191.377 (6)C53—C541.416 (6)
C18—H180.9300C54—C551.151 (6)
C19—C201.372 (7)C55—H550.9300
C19—H190.9300F1—P31.461 (5)
C20—C211.339 (6)F2—P31.489 (4)
C20—H200.9300F3—P31.534 (4)
C21—C221.384 (6)F4—P31.508 (4)
C21—H210.9300F5—P31.502 (5)
C22—H220.9300F6—P31.558 (4)
C40—Ru1—C3696.27 (18)C14—C13—C12119.2 (5)
C40—Ru1—C35123.65 (17)C14—C13—H13120.4
C36—Ru1—C3536.45 (17)C12—C13—H13120.4
C40—Ru1—C38135.43 (18)C15—C14—C13120.8 (5)
C36—Ru1—C3860.78 (19)C15—C14—H14119.6
C35—Ru1—C3860.20 (17)C13—C14—H14119.6
C40—Ru1—C37102.46 (18)C14—C15—C16120.6 (5)
C36—Ru1—C3736.80 (18)C14—C15—H15119.7
C35—Ru1—C3760.56 (17)C16—C15—H15119.7
C38—Ru1—C3736.06 (17)C15—C16—C11120.1 (5)
C40—Ru1—P188.78 (11)C15—C16—H16119.9
C36—Ru1—P1113.07 (16)C11—C16—H16119.9
C35—Ru1—P188.27 (13)C18—C17—C22118.6 (4)
C38—Ru1—P1134.33 (14)C18—C17—P1120.0 (3)
C37—Ru1—P1148.10 (13)C22—C17—P1121.3 (3)
C40—Ru1—C39157.25 (17)C17—C18—C19120.9 (4)
C36—Ru1—C3960.98 (18)C17—C18—H18119.6
C35—Ru1—C3936.65 (16)C19—C18—H18119.6
C38—Ru1—C3935.53 (16)C20—C19—C18119.8 (5)
C37—Ru1—C3960.11 (18)C20—C19—H19120.1
P1—Ru1—C3999.58 (13)C18—C19—H19120.1
C40—Ru1—P282.80 (11)C21—C20—C19120.1 (4)
C36—Ru1—P2147.61 (16)C21—C20—H20119.9
C35—Ru1—P2152.84 (13)C19—C20—H20119.9
C38—Ru1—P297.53 (13)C20—C21—C22120.6 (4)
C37—Ru1—P2111.58 (14)C20—C21—H21119.7
P1—Ru1—P299.30 (4)C22—C21—H21119.7
C39—Ru1—P2116.20 (12)C21—C22—C17119.9 (4)
C10—Co1—C2164.59 (17)C21—C22—H22120.0
C10—Co1—C3152.30 (19)C17—C22—H22120.0
C2—Co1—C341.09 (18)C28—C23—C24120.8 (4)
C10—Co1—C868.88 (17)C28—C23—H23119.6
C2—Co1—C8120.47 (18)C24—C23—H23119.6
C3—Co1—C8106.76 (18)C25—C24—C23119.4 (5)
C10—Co1—C1125.43 (16)C25—C24—H24120.3
C2—Co1—C141.45 (15)C23—C24—H24120.3
C3—Co1—C169.56 (17)C24—C25—C26120.4 (4)
C8—Co1—C1156.28 (18)C24—C25—H25119.8
C10—Co1—C5106.20 (17)C26—C25—H25119.8
C2—Co1—C569.07 (17)C27—C26—C25120.6 (4)
C3—Co1—C568.38 (19)C27—C26—H26119.7
C8—Co1—C5160.57 (17)C25—C26—H26119.7
C1—Co1—C541.59 (16)C26—C27—C28120.8 (4)
C10—Co1—C768.86 (16)C26—C27—H27119.6
C2—Co1—C7109.24 (17)C28—C27—H27119.6
C3—Co1—C7126.84 (19)C27—C28—C23118.1 (4)
C8—Co1—C741.21 (16)C27—C28—P2122.9 (3)
C1—Co1—C7121.26 (17)C23—C28—P2118.9 (3)
C5—Co1—C7156.32 (16)C34—C29—C30118.2 (4)
C10—Co1—C941.28 (16)C34—C29—P2119.0 (3)
C2—Co1—C9153.59 (17)C30—C29—P2122.8 (3)
C3—Co1—C9117.55 (18)C31—C30—C29120.7 (4)
C8—Co1—C940.54 (17)C31—C30—H30119.6
C1—Co1—C9162.37 (17)C29—C30—H30119.6
C5—Co1—C9123.54 (18)C32—C31—C30120.0 (4)
C7—Co1—C968.90 (17)C32—C31—H31120.0
C10—Co1—C641.26 (15)C30—C31—H31120.0
C2—Co1—C6127.39 (16)C31—C32—C33120.4 (4)
C3—Co1—C6164.92 (19)C31—C32—H32119.8
C8—Co1—C669.25 (16)C33—C32—H32119.8
C1—Co1—C6107.91 (15)C34—C33—C32119.8 (4)
C5—Co1—C6120.24 (16)C34—C33—H33120.1
C7—Co1—C640.83 (15)C32—C33—H33120.1
C9—Co1—C669.50 (16)C29—C34—C33120.9 (4)
C10—Co1—C4117.67 (18)C29—C34—H34119.6
C2—Co1—C468.91 (19)C33—C34—H34119.6
C3—Co1—C440.51 (18)C36—C35—C39108.2 (4)
C8—Co1—C4123.68 (19)C36—C35—Ru171.1 (3)
C1—Co1—C469.59 (18)C39—C35—Ru172.9 (3)
C5—Co1—C440.56 (17)C36—C35—H35125.8
C7—Co1—C4162.61 (18)C39—C35—H35125.8
C9—Co1—C4104.68 (19)Ru1—C35—H35125.8
C6—Co1—C4153.82 (18)C35—C36—C37107.5 (5)
C11—P1—C17105.32 (18)C35—C36—Ru172.5 (3)
C11—P1—C1104.20 (19)C37—C36—Ru172.7 (3)
C17—P1—C195.50 (17)C35—C36—H36126.0
C11—P1—Ru1111.73 (13)C37—C36—H36126.0
C17—P1—Ru1114.52 (13)Ru1—C36—H36126.0
C1—P1—Ru1123.24 (12)C38—C37—C36107.5 (4)
C28—P2—C29103.37 (17)C38—C37—Ru171.9 (3)
C28—P2—C6100.88 (17)C36—C37—Ru170.5 (3)
C29—P2—C696.40 (17)C38—C37—H37126.2
C28—P2—Ru1116.76 (13)C36—C37—H37126.2
C29—P2—Ru1115.46 (13)Ru1—C37—H37126.2
C6—P2—Ru1120.66 (12)C39—C38—C37109.6 (4)
C2—C1—C5106.3 (4)C39—C38—Ru173.1 (3)
C2—C1—P1131.2 (3)C37—C38—Ru172.0 (3)
C5—C1—P1122.6 (3)C39—C38—H38125.1
C2—C1—Co169.1 (2)C37—C38—H38125.1
C5—C1—Co169.4 (2)Ru1—C38—H38125.1
P1—C1—Co1127.24 (19)C38—C39—C35107.1 (5)
C3—C2—C1108.2 (4)C38—C39—Ru171.4 (3)
C3—C2—Co169.5 (2)C35—C39—Ru170.5 (3)
C1—C2—Co169.4 (2)C38—C39—H39126.4
C3—C2—H2125.9C35—C39—H39126.4
C1—C2—H2125.9Ru1—C39—H39126.4
Co1—C2—H2125.9C41—C40—Ru1178.6 (4)
C4—C3—C2109.0 (4)C40—C41—C42172.2 (5)
C4—C3—Co170.6 (3)C44—C42—C43116.3 (4)
C2—C3—Co169.4 (2)C44—C42—C41120.6 (4)
C4—C3—H3125.5C43—C42—C41123.1 (4)
C2—C3—H3125.5C45—C43—C42121.4 (4)
Co1—C3—H3125.5C45—C43—H43119.3
C3—C4—C5107.6 (4)C42—C43—H43119.3
C3—C4—Co168.9 (3)C46—C44—C42121.1 (4)
C5—C4—Co169.2 (2)C46—C44—H44119.4
C3—C4—H4126.2C42—C44—H44119.4
C5—C4—H4126.2C43—C45—C47122.6 (4)
Co1—C4—H4126.2C43—C45—H45118.7
C4—C5—C1109.0 (4)C47—C45—H45118.7
C4—C5—Co170.3 (2)C44—C46—C47123.1 (4)
C1—C5—Co169.0 (2)C44—C46—H46118.4
C4—C5—H5125.5C47—C46—H46118.4
C1—C5—H5125.5C46—C47—C45115.1 (4)
Co1—C5—H5125.5C46—C47—C48122.2 (4)
C7—C6—C10107.0 (3)C45—C47—C48122.4 (4)
C7—C6—P2127.5 (3)C50—C48—C49116.7 (4)
C10—C6—P2125.3 (3)C50—C48—C47120.3 (4)
C7—C6—Co169.5 (2)C49—C48—C47122.9 (4)
C10—C6—Co168.4 (2)C51—C49—C48121.7 (4)
P2—C6—Co1130.49 (19)C51—C49—H49119.1
C6—C7—C8108.2 (4)C48—C49—H49119.1
C6—C7—Co169.7 (2)C48—C50—C52121.9 (5)
C8—C7—Co169.0 (2)C48—C50—H50119.0
C6—C7—H7125.9C52—C50—H50119.0
C8—C7—H7125.9C49—C51—C53121.1 (4)
Co1—C7—H7125.9C49—C51—H51119.5
C9—C8—C7108.7 (4)C53—C51—H51119.5
C9—C8—Co170.2 (2)C53—C52—C50121.2 (5)
C7—C8—Co169.8 (2)C53—C52—H52119.4
C9—C8—H8125.7C50—C52—H52119.4
C7—C8—H8125.7C52—C53—C51117.3 (4)
Co1—C8—H8125.7C52—C53—C54121.8 (5)
C8—C9—C10107.3 (4)C51—C53—C54120.9 (4)
C8—C9—Co169.2 (2)C55—C54—C53177.0 (6)
C10—C9—Co168.5 (2)C54—C55—H55180.0
C8—C9—H9126.3F1—P3—F291.3 (4)
C10—C9—H9126.3F1—P3—F5177.3 (4)
Co1—C9—H9126.3F2—P3—F590.4 (4)
C9—C10—C6108.8 (3)F1—P3—F490.7 (5)
C9—C10—Co170.2 (2)F2—P3—F4178.0 (4)
C6—C10—Co170.3 (2)F5—P3—F487.7 (4)
C9—C10—H10125.6F1—P3—F388.9 (3)
C6—C10—H10125.6F2—P3—F387.6 (3)
Co1—C10—H10125.6F5—P3—F393.2 (3)
C16—C11—C12118.3 (4)F4—P3—F392.1 (2)
C16—C11—P1118.9 (3)F1—P3—F690.9 (3)
C12—C11—P1122.1 (3)F2—P3—F692.5 (3)
C13—C12—C11120.9 (5)F5—P3—F687.0 (3)
C13—C12—H12119.6F4—P3—F687.8 (3)
C11—C12—H12119.6F3—P3—F6179.8 (3)
C40—Ru1—P1—C11170.70 (18)C6—C7—C8—Co158.8 (3)
C36—Ru1—P1—C1193.0 (2)C10—Co1—C8—C938.0 (2)
C35—Ru1—P1—C1165.6 (2)C2—Co1—C8—C9155.6 (2)
C38—Ru1—P1—C1122.0 (2)C3—Co1—C8—C9113.0 (3)
C37—Ru1—P1—C1177.3 (3)C1—Co1—C8—C9169.8 (4)
C39—Ru1—P1—C1130.58 (19)C5—Co1—C8—C940.7 (6)
P2—Ru1—P1—C1188.19 (15)C7—Co1—C8—C9119.6 (4)
C40—Ru1—P1—C1769.67 (18)C6—Co1—C8—C982.3 (3)
C36—Ru1—P1—C1726.6 (2)C4—Co1—C8—C971.9 (3)
C35—Ru1—P1—C1754.06 (19)C10—Co1—C8—C781.6 (3)
C38—Ru1—P1—C1797.6 (2)C2—Co1—C8—C784.7 (3)
C37—Ru1—P1—C1742.3 (3)C3—Co1—C8—C7127.3 (3)
C39—Ru1—P1—C1789.06 (19)C1—Co1—C8—C750.1 (5)
P2—Ru1—P1—C17152.17 (15)C5—Co1—C8—C7160.3 (5)
C40—Ru1—P1—C145.47 (19)C9—Co1—C8—C7119.6 (4)
C36—Ru1—P1—C1141.8 (2)C6—Co1—C8—C737.3 (2)
C35—Ru1—P1—C1169.2 (2)C4—Co1—C8—C7168.5 (3)
C38—Ru1—P1—C1147.2 (2)C7—C8—C9—C101.4 (5)
C37—Ru1—P1—C1157.4 (3)Co1—C8—C9—C1058.1 (3)
C39—Ru1—P1—C1155.8 (2)C7—C8—C9—Co159.5 (3)
P2—Ru1—P1—C137.03 (16)C10—Co1—C9—C8119.4 (4)
C40—Ru1—P2—C28179.47 (17)C2—Co1—C9—C853.1 (5)
C36—Ru1—P2—C2890.2 (3)C3—Co1—C9—C883.7 (3)
C35—Ru1—P2—C2812.7 (3)C1—Co1—C9—C8166.3 (5)
C38—Ru1—P2—C2845.49 (19)C5—Co1—C9—C8164.9 (2)
C37—Ru1—P2—C2879.9 (2)C7—Co1—C9—C837.9 (2)
P1—Ru1—P2—C2891.89 (14)C6—Co1—C9—C881.7 (3)
C39—Ru1—P2—C2813.7 (2)C4—Co1—C9—C8125.1 (3)
C40—Ru1—P2—C2958.74 (18)C2—Co1—C9—C10172.6 (3)
C36—Ru1—P2—C2931.6 (3)C3—Co1—C9—C10156.9 (3)
C35—Ru1—P2—C29109.1 (3)C8—Co1—C9—C10119.4 (4)
C38—Ru1—P2—C2976.3 (2)C1—Co1—C9—C1046.9 (6)
C37—Ru1—P2—C2941.9 (2)C5—Co1—C9—C1075.6 (3)
P1—Ru1—P2—C29146.32 (14)C7—Co1—C9—C1081.6 (3)
C39—Ru1—P2—C29108.1 (2)C6—Co1—C9—C1037.8 (2)
C40—Ru1—P2—C656.46 (18)C4—Co1—C9—C10115.4 (3)
C36—Ru1—P2—C6146.8 (3)C8—C9—C10—C61.3 (4)
C35—Ru1—P2—C6135.7 (3)Co1—C9—C10—C659.9 (3)
C38—Ru1—P2—C6168.5 (2)C8—C9—C10—Co158.6 (3)
C37—Ru1—P2—C6157.1 (2)C7—C6—C10—C90.8 (4)
P1—Ru1—P2—C631.11 (15)P2—C6—C10—C9175.0 (3)
C39—Ru1—P2—C6136.7 (2)Co1—C6—C10—C959.8 (3)
C11—P1—C1—C29.0 (4)C7—C6—C10—Co159.0 (2)
C17—P1—C1—C2116.4 (4)P2—C6—C10—Co1125.2 (3)
Ru1—P1—C1—C2119.5 (3)C2—Co1—C10—C9167.5 (6)
C11—P1—C1—C5169.1 (3)C3—Co1—C10—C948.6 (5)
C17—P1—C1—C561.8 (3)C8—Co1—C10—C937.4 (2)
Ru1—P1—C1—C562.4 (3)C1—Co1—C10—C9164.3 (2)
C11—P1—C1—Co1103.1 (3)C5—Co1—C10—C9122.8 (3)
C17—P1—C1—Co1149.6 (3)C7—Co1—C10—C981.7 (3)
Ru1—P1—C1—Co125.4 (3)C6—Co1—C10—C9119.6 (3)
C10—Co1—C1—C2169.0 (2)C4—Co1—C10—C980.6 (3)
C3—Co1—C1—C237.5 (3)C2—Co1—C10—C647.9 (7)
C8—Co1—C1—C247.7 (5)C3—Co1—C10—C6168.1 (4)
C5—Co1—C1—C2117.6 (3)C8—Co1—C10—C682.2 (2)
C7—Co1—C1—C284.0 (3)C1—Co1—C10—C676.2 (3)
C9—Co1—C1—C2154.7 (5)C5—Co1—C10—C6117.7 (2)
C6—Co1—C1—C2126.7 (2)C7—Co1—C10—C637.9 (2)
C4—Co1—C1—C280.9 (3)C9—Co1—C10—C6119.6 (3)
C10—Co1—C1—C573.4 (3)C4—Co1—C10—C6159.8 (2)
C2—Co1—C1—C5117.6 (3)C17—P1—C11—C16155.7 (3)
C3—Co1—C1—C580.1 (3)C1—P1—C11—C1655.8 (4)
C8—Co1—C1—C5165.3 (4)Ru1—P1—C11—C1679.4 (3)
C7—Co1—C1—C5158.4 (2)C17—P1—C11—C1233.6 (4)
C9—Co1—C1—C537.1 (6)C1—P1—C11—C12133.5 (3)
C6—Co1—C1—C5115.7 (2)Ru1—P1—C11—C1291.3 (3)
C4—Co1—C1—C536.7 (2)C16—C11—C12—C130.0 (7)
C10—Co1—C1—P142.5 (3)P1—C11—C12—C13170.7 (4)
C2—Co1—C1—P1126.5 (4)C11—C12—C13—C140.8 (7)
C3—Co1—C1—P1164.0 (3)C12—C13—C14—C150.4 (8)
C8—Co1—C1—P178.8 (5)C13—C14—C15—C161.0 (8)
C5—Co1—C1—P1115.9 (4)C14—C15—C16—C111.8 (8)
C7—Co1—C1—P142.6 (3)C12—C11—C16—C151.3 (7)
C9—Co1—C1—P178.8 (6)P1—C11—C16—C15172.4 (4)
C6—Co1—C1—P10.2 (3)C11—P1—C17—C18141.5 (4)
C4—Co1—C1—P1152.6 (3)C1—P1—C17—C18112.2 (4)
C5—C1—C2—C31.0 (4)Ru1—P1—C17—C1818.3 (4)
P1—C1—C2—C3179.3 (3)C11—P1—C17—C2241.9 (4)
Co1—C1—C2—C358.8 (3)C1—P1—C17—C2264.5 (4)
C5—C1—C2—Co159.8 (2)Ru1—P1—C17—C22165.0 (3)
P1—C1—C2—Co1121.8 (3)C22—C17—C18—C191.0 (7)
C10—Co1—C2—C3155.4 (6)P1—C17—C18—C19177.8 (4)
C8—Co1—C2—C380.5 (3)C17—C18—C19—C200.8 (8)
C1—Co1—C2—C3119.7 (4)C18—C19—C20—C211.2 (8)
C5—Co1—C2—C380.7 (3)C19—C20—C21—C221.8 (8)
C7—Co1—C2—C3124.5 (3)C20—C21—C22—C172.1 (7)
C9—Co1—C2—C343.4 (5)C18—C17—C22—C211.7 (7)
C6—Co1—C2—C3166.6 (3)P1—C17—C22—C21178.4 (4)
C4—Co1—C2—C337.1 (3)C28—C23—C24—C251.0 (7)
C10—Co1—C2—C135.7 (7)C23—C24—C25—C260.7 (8)
C3—Co1—C2—C1119.7 (4)C24—C25—C26—C270.6 (8)
C8—Co1—C2—C1159.8 (2)C25—C26—C27—C280.7 (7)
C5—Co1—C2—C139.0 (2)C26—C27—C28—C230.9 (6)
C7—Co1—C2—C1115.8 (2)C26—C27—C28—P2179.0 (3)
C9—Co1—C2—C1163.1 (4)C24—C23—C28—C271.1 (6)
C6—Co1—C2—C173.7 (3)C24—C23—C28—P2179.2 (3)
C4—Co1—C2—C182.6 (3)C29—P2—C28—C2739.7 (4)
C1—C2—C3—C41.0 (5)C6—P2—C28—C2759.7 (4)
Co1—C2—C3—C459.8 (3)Ru1—P2—C28—C27167.6 (3)
C1—C2—C3—Co158.8 (3)C29—P2—C28—C23142.2 (3)
C10—Co1—C3—C446.3 (5)C6—P2—C28—C23118.4 (3)
C2—Co1—C3—C4120.0 (4)Ru1—P2—C28—C2314.3 (4)
C8—Co1—C3—C4122.6 (3)C28—P2—C29—C34107.2 (3)
C1—Co1—C3—C482.1 (3)C6—P2—C29—C34150.0 (3)
C5—Co1—C3—C437.4 (3)Ru1—P2—C29—C3421.5 (4)
C7—Co1—C3—C4163.5 (3)C28—P2—C29—C3072.7 (4)
C9—Co1—C3—C480.2 (3)C6—P2—C29—C3030.1 (4)
C6—Co1—C3—C4165.1 (6)Ru1—P2—C29—C30158.6 (3)
C10—Co1—C3—C2166.2 (3)C34—C29—C30—C310.4 (6)
C8—Co1—C3—C2117.4 (3)P2—C29—C30—C31179.5 (3)
C1—Co1—C3—C237.8 (3)C29—C30—C31—C320.4 (7)
C5—Co1—C3—C282.5 (3)C30—C31—C32—C330.0 (7)
C7—Co1—C3—C276.5 (3)C31—C32—C33—C340.3 (7)
C9—Co1—C3—C2159.9 (3)C30—C29—C34—C330.1 (6)
C6—Co1—C3—C245.2 (8)P2—C29—C34—C33179.8 (3)
C4—Co1—C3—C2120.0 (4)C32—C33—C34—C290.2 (7)
C2—C3—C4—C50.6 (5)C40—Ru1—C35—C3647.1 (4)
Co1—C3—C4—C558.5 (3)C38—Ru1—C35—C3680.1 (3)
C2—C3—C4—Co159.1 (3)C37—Ru1—C35—C3638.4 (3)
C10—Co1—C4—C3157.7 (3)P1—Ru1—C35—C36134.5 (3)
C2—Co1—C4—C337.6 (3)C39—Ru1—C35—C36116.9 (4)
C8—Co1—C4—C375.7 (3)P2—Ru1—C35—C36118.3 (4)
C1—Co1—C4—C382.1 (3)C40—Ru1—C35—C39164.0 (3)
C5—Co1—C4—C3119.7 (4)C36—Ru1—C35—C39116.9 (4)
C7—Co1—C4—C349.5 (7)C38—Ru1—C35—C3936.7 (3)
C9—Co1—C4—C3115.4 (3)C37—Ru1—C35—C3978.5 (3)
C6—Co1—C4—C3171.3 (3)P1—Ru1—C35—C39108.6 (3)
C10—Co1—C4—C582.6 (3)P2—Ru1—C35—C391.5 (5)
C2—Co1—C4—C582.1 (3)C39—C35—C36—C370.9 (5)
C3—Co1—C4—C5119.7 (4)Ru1—C35—C36—C3764.7 (3)
C8—Co1—C4—C5164.6 (3)C39—C35—C36—Ru163.8 (3)
C1—Co1—C4—C537.6 (3)C40—Ru1—C36—C35142.2 (3)
C7—Co1—C4—C5169.2 (5)C38—Ru1—C36—C3578.4 (3)
C9—Co1—C4—C5124.9 (3)C37—Ru1—C36—C35115.4 (4)
C6—Co1—C4—C551.6 (5)P1—Ru1—C36—C3550.8 (3)
C3—C4—C5—C10.0 (5)C39—Ru1—C36—C3537.5 (3)
Co1—C4—C5—C158.2 (3)P2—Ru1—C36—C35131.4 (3)
C3—C4—C5—Co158.3 (3)C40—Ru1—C36—C37102.4 (3)
C2—C1—C5—C40.6 (4)C35—Ru1—C36—C37115.4 (4)
P1—C1—C5—C4179.2 (3)C38—Ru1—C36—C3737.0 (3)
Co1—C1—C5—C459.0 (3)P1—Ru1—C36—C37166.2 (3)
C2—C1—C5—Co159.6 (3)C39—Ru1—C36—C3777.9 (3)
P1—C1—C5—Co1121.8 (3)P2—Ru1—C36—C3716.0 (5)
C10—Co1—C5—C4113.9 (3)C35—C36—C37—C381.8 (5)
C2—Co1—C5—C481.6 (3)Ru1—C36—C37—C3862.8 (3)
C3—Co1—C5—C437.4 (3)C35—C36—C37—Ru164.6 (3)
C8—Co1—C5—C441.6 (6)C40—Ru1—C37—C38159.4 (3)
C1—Co1—C5—C4120.5 (4)C36—Ru1—C37—C38116.8 (4)
C7—Co1—C5—C4172.0 (4)C35—Ru1—C37—C3878.8 (3)
C9—Co1—C5—C472.1 (3)P1—Ru1—C37—C3892.3 (4)
C6—Co1—C5—C4156.4 (3)C39—Ru1—C37—C3836.4 (3)
C10—Co1—C5—C1125.6 (2)P2—Ru1—C37—C3872.3 (3)
C2—Co1—C5—C138.9 (2)C40—Ru1—C37—C3683.8 (3)
C3—Co1—C5—C183.2 (3)C35—Ru1—C37—C3638.0 (3)
C8—Co1—C5—C1162.1 (5)C38—Ru1—C37—C36116.8 (4)
C7—Co1—C5—C151.4 (5)P1—Ru1—C37—C3624.5 (5)
C9—Co1—C5—C1167.3 (2)C39—Ru1—C37—C3680.5 (3)
C6—Co1—C5—C183.1 (3)P2—Ru1—C37—C36170.9 (3)
C4—Co1—C5—C1120.5 (4)C36—C37—C38—C392.0 (5)
C28—P2—C6—C721.7 (4)Ru1—C37—C38—C3963.9 (3)
C29—P2—C6—C7126.7 (3)C36—C37—C38—Ru161.9 (3)
Ru1—P2—C6—C7108.6 (3)C40—Ru1—C38—C39147.1 (3)
C28—P2—C6—C10153.3 (3)C36—Ru1—C38—C3980.0 (3)
C29—P2—C6—C1048.3 (3)C35—Ru1—C38—C3937.9 (3)
Ru1—P2—C6—C1076.4 (3)C37—Ru1—C38—C39117.8 (4)
C28—P2—C6—Co1116.0 (3)P1—Ru1—C38—C3914.6 (4)
C29—P2—C6—Co1139.0 (3)P2—Ru1—C38—C39125.5 (3)
Ru1—P2—C6—Co114.3 (3)C40—Ru1—C38—C3729.3 (4)
C10—Co1—C6—C7118.9 (3)C36—Ru1—C38—C3737.8 (3)
C2—Co1—C6—C775.5 (3)C35—Ru1—C38—C3779.9 (3)
C3—Co1—C6—C739.6 (7)P1—Ru1—C38—C37132.4 (3)
C8—Co1—C6—C737.6 (2)C39—Ru1—C38—C37117.8 (4)
C1—Co1—C6—C7117.4 (2)P2—Ru1—C38—C37116.7 (3)
C5—Co1—C6—C7161.2 (2)C37—C38—C39—C351.5 (5)
C9—Co1—C6—C781.1 (3)Ru1—C38—C39—C3561.8 (3)
C4—Co1—C6—C7162.6 (4)C37—C38—C39—Ru163.2 (3)
C2—Co1—C6—C10165.6 (2)C36—C35—C39—C380.3 (5)
C3—Co1—C6—C10158.5 (6)Ru1—C35—C39—C3862.3 (3)
C8—Co1—C6—C1081.2 (3)C36—C35—C39—Ru162.7 (3)
C1—Co1—C6—C10123.7 (2)C40—Ru1—C39—C3880.3 (5)
C5—Co1—C6—C1079.9 (3)C36—Ru1—C39—C3879.4 (3)
C7—Co1—C6—C10118.9 (3)C35—Ru1—C39—C38116.7 (4)
C9—Co1—C6—C1037.8 (2)C37—Ru1—C39—C3836.9 (3)
C4—Co1—C6—C1043.7 (5)P1—Ru1—C39—C38169.4 (3)
C10—Co1—C6—P2118.7 (4)P2—Ru1—C39—C3864.0 (3)
C2—Co1—C6—P246.9 (3)C40—Ru1—C39—C3536.4 (6)
C3—Co1—C6—P282.8 (7)C36—Ru1—C39—C3537.3 (3)
C8—Co1—C6—P2160.0 (3)C38—Ru1—C39—C35116.7 (4)
C1—Co1—C6—P25.0 (3)C37—Ru1—C39—C3579.8 (3)
C5—Co1—C6—P238.8 (3)P1—Ru1—C39—C3573.8 (3)
C7—Co1—C6—P2122.4 (4)P2—Ru1—C39—C35179.2 (2)
C9—Co1—C6—P2156.5 (3)C44—C42—C43—C455.5 (6)
C4—Co1—C6—P275.0 (5)C41—C42—C43—C45172.3 (4)
C10—C6—C7—C80.0 (4)C43—C42—C44—C466.0 (7)
P2—C6—C7—C8175.7 (3)C41—C42—C44—C46171.8 (4)
Co1—C6—C7—C858.4 (3)C42—C43—C45—C471.0 (7)
C10—C6—C7—Co158.4 (2)C42—C44—C46—C472.1 (8)
P2—C6—C7—Co1125.9 (3)C44—C46—C47—C452.5 (7)
C10—Co1—C7—C638.3 (2)C44—C46—C47—C48172.5 (5)
C2—Co1—C7—C6125.4 (2)C43—C45—C47—C463.1 (7)
C3—Co1—C7—C6168.0 (2)C43—C45—C47—C48172.0 (4)
C8—Co1—C7—C6119.9 (4)C46—C47—C48—C5014.1 (7)
C1—Co1—C7—C681.2 (3)C45—C47—C48—C50160.5 (4)
C5—Co1—C7—C643.8 (5)C46—C47—C48—C49169.0 (4)
C9—Co1—C7—C682.7 (2)C45—C47—C48—C4916.3 (6)
C4—Co1—C7—C6153.8 (6)C50—C48—C49—C513.1 (7)
C10—Co1—C7—C881.7 (3)C47—C48—C49—C51173.9 (4)
C2—Co1—C7—C8114.6 (3)C49—C48—C50—C522.6 (7)
C3—Co1—C7—C872.0 (3)C47—C48—C50—C52174.5 (4)
C1—Co1—C7—C8158.8 (2)C48—C49—C51—C530.9 (7)
C5—Co1—C7—C8163.8 (4)C48—C50—C52—C530.2 (8)
C9—Co1—C7—C837.3 (2)C50—C52—C53—C512.5 (7)
C6—Co1—C7—C8119.9 (4)C50—C52—C53—C54175.5 (5)
C4—Co1—C7—C833.9 (7)C49—C51—C53—C522.0 (7)
C6—C7—C8—C90.9 (4)C49—C51—C53—C54176.1 (4)
Co1—C7—C8—C959.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F5i0.982.433.189 (6)134
C3—H3···F6ii0.982.543.383 (6)144
C7—H7···F4i0.982.473.383 (7)155
C9—H9···F2ii0.982.322.993 (6)125
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F5i0.982.433.189 (6)133.8
C3—H3···F6ii0.982.543.383 (6)144.2
C7—H7···F4i0.982.473.383 (7)154.7
C9—H9···F2ii0.982.322.993 (6)124.9
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2.
 

Acknowledgements

This work was supported by the Joint Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20125303110002).

References

First citationBlackmore, T., Bruce, M. I. & Stone, F. C. (1971). J. Chem. Soc. 14, 2376–2382.  CrossRef
First citationBruce, M. I., Ellis, B. G., Low, P. J., Skelton, B. W. & White, A. H. (2003). Organometallics, 22, 3184–3198.  Web of Science CSD CrossRef CAS
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDomazetis, G., Tarpey, B., Dolphin, D. & James, B. R. (1980). J. Chem. Soc. Chem. Commun. pp. 939–940.  CrossRef Web of Science
First citationGaughan, A. P., Bownan, K. S. & Dori, Z. (1972). Inorg. Chem. 11, 601–608.  CSD CrossRef CAS Web of Science
First citationHembre, R. T., McQueen, J. A. & Day, V. W. (1996). J. Am. Chem. Soc. 118, 798–803.  CSD CrossRef CAS Web of Science
First citationNombel, P., Lugan, N., Donnadieu, B. & Lavigne, G. (1999). Organometallics, 18, 187–196.  Web of Science CSD CrossRef CAS
First citationOshima, N. & Suzuki, H. (1984). Chem. Lett. 13, 1161–1164.  CrossRef Web of Science
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWu, X.-H., Ren, Y., Yu, G.-A. & Liu, S.-H. (2006). Acta Cryst. E62, m426–m428.  Web of Science CSD CrossRef CAS IUCr Journals
First citationZiolo, R. F. & Dori, Z. (1968). J. Am. Chem. Soc. 90, 6560–6561.  CrossRef CAS Web of Science

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