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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page m1564
https://doi.org/10.1107/S1600536810046064

(η5-Penta­methyl­cyclo­penta­dien­yl)(η6-4-phenyl­butan-2-one)ruthenium(II) tetra­phenyl­borate

Bradley T. Loughrey,a Michael L. Williamsa and Peter C. Healyb*

aEskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane 4111, Australia, and bSchool of Biomolecular and Physical Sciences, Griffith University, Brisbane 4111, Australia
*Correspondence e-mail: p.healy@griffith.edu.au

(Received 15 October 2010; accepted 9 November 2010; online 13 November 2010)

The title compound, [Ru(C10H15)(C10H12O)][B(C6H5)4], crystallizes as discrete (η5-penta­methyl­cyclo­penta­dien­yl)Ru(η6-4-phenyl­butan-2-one)]+ cations and [BPh4]− anions. In the cation, the non-H atoms of the butan-2-one group are approximately planar (r.m.s. deviation = 0.056 Å) and lie nearly perpendicular to the plane of the phenyl ring with a dihedral angle between the two planes of 69.3 (1)°. No significant C—H⋯O inter­actions are observed between the methyl and phenyl H atoms and the carbonyl O atom.

Related literature

For related structures, see: Loughrey et al. (2008[Loughrey, B. T., Healy, P. C., Parsons, P. G. & Williams, M. L. (2008). Inorg. Chem. 47, 8589-8591.], 2009[Loughrey, B. T., Nadin, K., Williams, M. L. & Healy, P. C. (2009). Acta Cryst. E65, m1486.], 2010[Loughrey, B. T., Williams, M. L., Carruthers, T. J., Parsons, P. G. & Healy, P. C. (2010). Aust. J. Chem. 63, 245-251.]).

[Scheme 1]

Experimental

Crystal data

  • [Ru(C10H15)(C10H12O)](C24H20B)

  • Mr = 703.70

  • Monoclinic, P 21 /n

  • a = 13.1659 (2) Å

  • b = 19.7064 (2) Å

  • c = 14.3720 (2) Å

  • β = 92.378 (1)°

  • V = 3725.64 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 200 K

  • 0.41 × 0.32 × 0.22 mm
Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.836, Tmax = 0.907

  • 20468 measured reflections

  • 8549 independent reflections

  • 7103 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 0.069

  • S = 1.10

  • 8549 reflections

  • 424 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.55 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046064/bv2166sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046064/bv2166Isup2.hkl

checkCIF report


Comment top

As part of our ongoing investigations into the structural chemistry of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X- (Loughrey et al., 2008, 2009, 2010), we have determined the crystal structure of the complex of Cp*Ru and benzylacetone (PhCH2CH2C(=O)CH3) as the tetraphenylborate salt, (I) (Fig.1). Crystal packing in the structure is determined primarily by van der Waals and /C—H···π(Ph) interactions between the methyl and phenyl groups of the cation and the anion. No significant inter-molecular C—H···O interactions are observed between the carbonyl oxygen and methyl or phenyl H atoms.

The Cp* and benzene rings of the cation lie parallel (dihedral angle 1.5 (1) Å). The Ru—C(arene) bond lengths range between 2.207 (2) and 2.231 (2)Å with an average value of 2.216 (7) Å; and are comparable to those reported for related complexes (Loughrey et al., 2010, and references therein).

The cation of (I) is isomeric with the propiophenone (PhC(=O)—Pr) complex, (Loughrey et al., 2008). In this latter structure, the –C(=O)Pr group is co-planar with benzene ring with the carbonyl oxygen involved in an intra-molecular C—H···O interaction (O···H = 2.51 Å) with one ortho H atom on the benzene ring. In (I), the EtC(=O)Me group is also planar (r.m.s. deviation 0.056 Å) but steric interaction between the methylene protons and benzene protons and Cp* methyl protons result in the –C(=O)Pr group being oriented approximately orthogonal to the benzene ring with a dihedral angle of 110.7 (1)° between the two planes.

Related literature top

For related structures, see: Loughrey et al. (2008, 2009, 2010).

Experimental top

Benzylacetone (0.5 ml, 3.41 mmol) and HCp* (0.3 ml, 1.88 mmol) was added to a solution of ruthenium trichloride hydrate (0.20 g, 0.76 mmol) in ethanol (20 ml) under argon. The resulting solution was heated under reflux conditions for a period of 12 h to yield a golden-brown coloured solution. The solvent was concentrated in vacuo with the remaining residue being redissolved in acetone (20 ml) and merged with an acetone solution of sodium tetraphenylborate (5 ml, 0.30 M). The resulting mixture was concentrated to a minimum volume in vacuo and titrated with cold water to prompt precipitation of a tan powder. This powder was filtered from solution and washed with three aliquots of diethyl ether (20 ml) prior to being collected, and redissolved in a minimum quantity of acetone. This solution was filtered through a short alumina column (neutral, 150 mesh) using acetone as the eluent. The solution was concentrated in vacuo and the product recrystallized through addition of a minimum quantity of cold water. The resulting white, crystalline precipitate was then filtered from solution and dried in vacuo. Yield = 0.273 g, 72.3%. Large crystals suitable for X-ray diffraction studies were grown by slow diffusion of diethyl ether into a solution of the compound in acetone.

NMR: 1H (d6DMSO), δ 1.90 (s, 15H, C5(C5H15)), 2.08 (s, 3H, CH3), 2.47 (t, J = 8.0 Hz, 2H, C6H5—CH2), 2.76 (t, J = 8.0 Hz, 2H, CH2—CO), 5.79–5.86 (m, 5H, C6H5), 6.76–6.80 (m, 4H, B(C6H5)4 para), 6.90–6.93 (m, 8H, B(C6H5)4 meta), 7.16–7.19 (m, 8H, B(C6H5)4 ortho); 13C (d6DMSO), δ 10.02 (C5(C5H15)), 26.08 (CH3),29.67 (C6H5-CH2), 43.47 (CH2—CO), 86.50 (1CH, aromatic), 87.09 (2CH, aromatic), 87.59 (2CH, aromatic), 95.35 (C5(C5H15)), 102.90 (1CH, aromatic), 121.47 (4CH, B(C6H5)4), 125.24 (8CH, B(C6H5)4), 135.49 (8CH, B(C6H5)4), 162.59, 163.08, 163.57, 164.06 (4CH, B(C6H5)4), signals split by 11B), 206.81(C=O); ESMS (m/z): +ve ion, calcd m/z for [(η5-C5(CH3)5)Ru(η6—C6H5(CH2)2COCH3)+]: 384.54, found: 385.09 (100%), -ve ion, calcd m/z for B(C6H5)4-: 319.25, found: 319.09 (100%); calcd % for C44H47OBRu: C 75.1, H 6.75%; found: C 75.0, H 6.79%.

Refinement top

All methyl hydrogen atoms were located from difference Fourier Maps. H atoms attached to carbon were constrained as riding atoms, with C–H set to 0.94–96 Å. Uiso(H) values were set to 1.2Ueq (aromatic) and 1.5Ueq (alkyl) of the parent atom.

Structure description top

As part of our ongoing investigations into the structural chemistry of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X- (Loughrey et al., 2008, 2009, 2010), we have determined the crystal structure of the complex of Cp*Ru and benzylacetone (PhCH2CH2C(=O)CH3) as the tetraphenylborate salt, (I) (Fig.1). Crystal packing in the structure is determined primarily by van der Waals and /C—H···π(Ph) interactions between the methyl and phenyl groups of the cation and the anion. No significant inter-molecular C—H···O interactions are observed between the carbonyl oxygen and methyl or phenyl H atoms.

The Cp* and benzene rings of the cation lie parallel (dihedral angle 1.5 (1) Å). The Ru—C(arene) bond lengths range between 2.207 (2) and 2.231 (2)Å with an average value of 2.216 (7) Å; and are comparable to those reported for related complexes (Loughrey et al., 2010, and references therein).

The cation of (I) is isomeric with the propiophenone (PhC(=O)—Pr) complex, (Loughrey et al., 2008). In this latter structure, the –C(=O)Pr group is co-planar with benzene ring with the carbonyl oxygen involved in an intra-molecular C—H···O interaction (O···H = 2.51 Å) with one ortho H atom on the benzene ring. In (I), the EtC(=O)Me group is also planar (r.m.s. deviation 0.056 Å) but steric interaction between the methylene protons and benzene protons and Cp* methyl protons result in the –C(=O)Pr group being oriented approximately orthogonal to the benzene ring with a dihedral angle of 110.7 (1)° between the two planes.

For related structures, see: Loughrey et al. (2008, 2009, 2010).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The structure of the cation and anion of (I), with atom labels and 40% probability displacement ellipsoids for the non-H atoms.
(η5-Pentamethylcyclopentadienyl)(η6-4-phenylbutan-2-one)ruthenium(II) tetraphenylborate top
Crystal data top
[Ru(C10H15)(C10H12O)](C24H20B)F(000) = 1472
Mr = 703.70Dx = 1.255 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 15293 reflections
a = 13.1659 (2) Åθ = 3.1–32.2°
b = 19.7064 (2) ŵ = 0.45 mm−1
c = 14.3720 (2) ÅT = 200 K
β = 92.378 (1)°Block, colourless
V = 3725.64 (9) Å30.41 × 0.32 × 0.22 mm
Z = 4
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		8549 independent reflections
Radiation source: Enhance (Mo) X-ray Source7103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 16.0774 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω and φ scansh = −15→17
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −25→12
Tmin = 0.836, Tmax = 0.907l = −18→8
20468 measured reflections
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0396P)2 + 0.1643P]
where P = (Fo2 + 2Fc2)/3
8549 reflections(Δ/σ)max = 0.001
424 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.55 e Å−3
Crystal data top
[Ru(C10H15)(C10H12O)](C24H20B)V = 3725.64 (9) Å3
Mr = 703.70Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.1659 (2) ŵ = 0.45 mm−1
b = 19.7064 (2) ÅT = 200 K
c = 14.3720 (2) Å0.41 × 0.32 × 0.22 mm
β = 92.378 (1)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		8549 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		7103 reflections with I > 2σ(I)
Tmin = 0.836, Tmax = 0.907Rint = 0.016
20468 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.069H-atom parameters constrained
S = 1.10Δρmax = 0.54 e Å−3
8549 reflectionsΔρmin = −0.55 e Å−3
424 parameters
Special details top

Experimental. CrysAlisPro (2010). Version 1.171.33.55 Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Ru0.55316 (1)0.14771 (1)0.23154 (1)0.0247 (1)
O190.19486 (12)−0.00976 (8)0.05380 (11)0.0631 (6)
C10.61274 (13)0.13342 (8)0.09337 (11)0.0282 (4)
C20.56126 (12)0.19729 (8)0.09612 (11)0.0284 (5)
C30.61217 (12)0.23839 (8)0.16627 (11)0.0300 (5)
C40.69582 (12)0.20024 (8)0.20580 (11)0.0291 (5)
C50.69633 (12)0.13513 (8)0.16034 (11)0.0287 (5)
C60.58693 (15)0.07559 (9)0.02864 (11)0.0387 (5)
C70.47463 (14)0.21912 (9)0.03281 (12)0.0405 (6)
C80.58342 (15)0.30941 (9)0.19115 (14)0.0435 (6)
C90.77350 (14)0.22424 (9)0.27776 (13)0.0419 (6)
C100.77516 (14)0.08114 (9)0.17554 (13)0.0421 (6)
C110.40664 (12)0.09177 (8)0.24079 (11)0.0302 (5)
C120.39532 (15)0.15832 (9)0.27675 (14)0.0414 (6)
C130.46368 (18)0.18242 (10)0.34902 (14)0.0524 (7)
C140.54139 (17)0.14065 (12)0.38474 (12)0.0519 (7)
C150.55284 (14)0.07558 (11)0.34985 (12)0.0445 (6)
C160.48612 (14)0.05140 (8)0.27914 (11)0.0341 (5)
C170.33680 (15)0.06448 (12)0.16405 (12)0.0488 (6)
C180.23631 (14)0.04201 (9)0.20012 (12)0.0391 (5)
C190.16669 (14)0.00779 (9)0.12875 (14)0.0416 (6)
C200.05998 (18)−0.00489 (15)0.15720 (19)0.0739 (10)
C21−0.00388 (12)0.34793 (7)0.19919 (10)0.0250 (4)
C22−0.02878 (13)0.36758 (8)0.28945 (11)0.0289 (4)
C23−0.12081 (13)0.39848 (8)0.30875 (11)0.0332 (5)
C24−0.19288 (13)0.41071 (8)0.23771 (13)0.0354 (5)
C25−0.17137 (13)0.39159 (8)0.14789 (12)0.0350 (5)
C26−0.07942 (13)0.36100 (8)0.12939 (11)0.0311 (5)
C270.18052 (12)0.37759 (8)0.13734 (10)0.0278 (4)
C280.14028 (13)0.43584 (8)0.09393 (10)0.0311 (5)
C290.20017 (16)0.48550 (9)0.05478 (12)0.0405 (6)
C300.30419 (17)0.47859 (10)0.05630 (14)0.0486 (7)
C310.34797 (15)0.42240 (10)0.09943 (15)0.0474 (6)
C320.28726 (14)0.37357 (9)0.13994 (13)0.0378 (5)
C330.15746 (12)0.28317 (8)0.27402 (10)0.0295 (4)
C340.21760 (14)0.32051 (10)0.33815 (12)0.0406 (6)
C350.25258 (15)0.29418 (13)0.42355 (13)0.0527 (7)
C360.22896 (17)0.22937 (13)0.44790 (13)0.0569 (8)
C370.16987 (18)0.19048 (11)0.38736 (14)0.0538 (7)
C380.13437 (15)0.21704 (9)0.30198 (12)0.0389 (6)
C390.10006 (12)0.25499 (7)0.09834 (10)0.0263 (4)
C400.01493 (14)0.21305 (9)0.08473 (12)0.0381 (5)
C410.01377 (16)0.15765 (9)0.02438 (15)0.0466 (6)
C420.09801 (16)0.14178 (9)−0.02492 (13)0.0440 (6)
C430.18323 (14)0.18193 (9)−0.01415 (12)0.0391 (6)
C440.18349 (13)0.23738 (8)0.04559 (11)0.0333 (5)
B0.10817 (14)0.31626 (9)0.17692 (11)0.0257 (5)
H6A0.600500.033800.059700.0460*
H6B0.627000.07860−0.024700.0460*
H6C0.516900.077700.009900.0460*
H7A0.431600.181400.019300.0490*
H7B0.500100.23620−0.023400.0490*
H7C0.437100.253600.062200.0490*
H8A0.613100.320600.250500.0520*
H8B0.511500.312800.192800.0520*
H8C0.607400.339900.145800.0520*
H9A0.800300.186400.311600.0500*
H9B0.742500.254600.319300.0500*
H9C0.826900.246800.247900.0500*
H10A0.801600.083100.238000.0510*
H10B0.745300.037900.164100.0510*
H10C0.828600.088100.134200.0510*
H120.342200.186800.252800.0500*
H130.456300.227000.372800.0630*
H140.586600.156700.433100.0620*
H150.606100.047400.374000.0530*
H160.494700.006600.256400.0410*
H17A0.368500.026800.136000.0580*
H17B0.324900.099000.118800.0580*
H18A0.202400.080900.222700.0470*
H18B0.249500.011100.249900.0470*
H20A0.01500−0.003000.103800.0890*
H20B0.041300.028800.200600.0890*
H20C0.05610−0.048500.185100.0890*
H220.019200.359500.339400.0350*
H23−0.134200.411200.370800.0400*
H24−0.255700.431800.250300.0420*
H25−0.220100.399500.098500.0420*
H26−0.067000.348400.067100.0370*
H280.068600.441700.091100.0370*
H290.169100.524400.026800.0490*
H300.345300.511900.028300.0580*
H310.419700.417100.101400.0570*
H320.319300.336000.170500.0450*
H340.235300.365800.322800.0490*
H350.293100.321500.465000.0630*
H360.253000.211300.506000.0680*
H370.153100.145300.403700.0650*
H380.093300.189400.261500.0470*
H40−0.044300.222700.117800.0460*
H41−0.045700.130600.017300.0560*
H420.097300.10380−0.065700.0530*
H430.242000.17170−0.047600.0470*
H440.242900.264700.051000.0400*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.0247 (1)0.0262 (1)0.0235 (1)−0.0051 (1)0.0057 (1)−0.0032 (1)
O190.0548 (10)0.0756 (10)0.0578 (9)0.0044 (8)−0.0102 (7)−0.0266 (8)
C10.0303 (8)0.0298 (8)0.0252 (7)−0.0038 (6)0.0091 (6)0.0007 (6)
C20.0248 (8)0.0318 (8)0.0291 (8)−0.0038 (6)0.0062 (6)0.0032 (6)
C30.0251 (8)0.0293 (8)0.0360 (8)−0.0046 (6)0.0069 (6)0.0020 (6)
C40.0253 (8)0.0308 (8)0.0316 (8)−0.0052 (6)0.0060 (6)0.0013 (6)
C50.0279 (8)0.0294 (8)0.0294 (8)−0.0011 (6)0.0091 (6)0.0038 (6)
C60.0484 (11)0.0393 (9)0.0288 (8)−0.0027 (8)0.0069 (7)−0.0060 (7)
C70.0355 (10)0.0458 (10)0.0400 (9)−0.0005 (8)−0.0017 (7)0.0063 (8)
C80.0383 (10)0.0293 (9)0.0630 (12)−0.0031 (8)0.0052 (9)−0.0037 (8)
C90.0328 (10)0.0456 (10)0.0469 (10)−0.0116 (8)−0.0025 (8)−0.0019 (8)
C100.0364 (10)0.0413 (10)0.0491 (10)0.0063 (8)0.0081 (8)0.0057 (8)
C110.0275 (8)0.0370 (9)0.0267 (7)−0.0097 (7)0.0074 (6)−0.0004 (6)
C120.0343 (10)0.0371 (10)0.0546 (11)0.0014 (8)0.0227 (8)0.0030 (8)
C130.0680 (14)0.0399 (10)0.0525 (12)−0.0231 (10)0.0395 (11)−0.0219 (9)
C140.0508 (12)0.0801 (15)0.0254 (9)−0.0281 (11)0.0093 (8)−0.0056 (9)
C150.0383 (10)0.0628 (12)0.0324 (9)−0.0071 (9)0.0021 (7)0.0164 (9)
C160.0386 (9)0.0308 (8)0.0338 (8)−0.0064 (7)0.0112 (7)0.0034 (7)
C170.0375 (10)0.0758 (14)0.0329 (9)−0.0224 (10)0.0001 (7)0.0000 (9)
C180.0318 (9)0.0435 (10)0.0419 (9)−0.0103 (8)0.0013 (7)−0.0047 (8)
C190.0363 (10)0.0332 (9)0.0544 (11)−0.0016 (8)−0.0089 (8)−0.0020 (8)
C200.0420 (13)0.0947 (19)0.0840 (17)−0.0256 (13)−0.0093 (12)−0.0062 (14)
C210.0275 (8)0.0217 (7)0.0260 (7)−0.0024 (6)0.0023 (6)0.0022 (6)
C220.0318 (8)0.0270 (8)0.0279 (7)−0.0028 (6)0.0013 (6)−0.0011 (6)
C230.0351 (9)0.0289 (8)0.0362 (9)−0.0044 (7)0.0088 (7)−0.0065 (7)
C240.0284 (9)0.0245 (8)0.0537 (10)−0.0006 (7)0.0085 (7)−0.0017 (7)
C250.0290 (9)0.0340 (9)0.0415 (9)0.0004 (7)−0.0030 (7)0.0092 (7)
C260.0326 (9)0.0341 (9)0.0267 (8)0.0005 (7)0.0011 (6)0.0035 (6)
C270.0327 (9)0.0268 (7)0.0241 (7)−0.0007 (7)0.0024 (6)−0.0040 (6)
C280.0381 (9)0.0295 (8)0.0258 (7)−0.0009 (7)0.0011 (6)−0.0016 (6)
C290.0566 (12)0.0320 (9)0.0332 (9)−0.0041 (8)0.0040 (8)0.0040 (7)
C300.0596 (13)0.0386 (10)0.0487 (11)−0.0145 (9)0.0165 (9)0.0030 (8)
C310.0360 (10)0.0443 (11)0.0626 (12)−0.0070 (8)0.0122 (9)−0.0022 (9)
C320.0356 (10)0.0311 (8)0.0469 (10)−0.0003 (7)0.0049 (8)0.0008 (7)
C330.0285 (8)0.0331 (8)0.0269 (7)0.0088 (7)0.0025 (6)−0.0001 (6)
C340.0357 (10)0.0521 (11)0.0336 (9)0.0059 (8)−0.0045 (7)−0.0026 (8)
C350.0388 (11)0.0869 (16)0.0317 (9)0.0182 (11)−0.0067 (8)−0.0035 (10)
C360.0507 (12)0.0918 (17)0.0284 (9)0.0390 (12)0.0054 (8)0.0139 (10)
C370.0634 (14)0.0550 (12)0.0445 (11)0.0292 (11)0.0206 (10)0.0215 (9)
C380.0460 (11)0.0374 (9)0.0340 (9)0.0116 (8)0.0088 (7)0.0057 (7)
C390.0302 (8)0.0253 (7)0.0231 (7)0.0018 (6)−0.0012 (6)0.0021 (6)
C400.0355 (9)0.0367 (9)0.0424 (9)−0.0021 (8)0.0063 (7)−0.0064 (7)
C410.0431 (11)0.0381 (10)0.0582 (12)−0.0082 (8)−0.0027 (9)−0.0128 (8)
C420.0525 (12)0.0370 (10)0.0419 (10)0.0038 (9)−0.0036 (8)−0.0134 (8)
C430.0400 (10)0.0413 (10)0.0363 (9)0.0076 (8)0.0050 (7)−0.0070 (7)
C440.0318 (9)0.0332 (8)0.0349 (8)0.0015 (7)0.0012 (7)−0.0035 (7)
B0.0283 (9)0.0261 (8)0.0228 (8)0.0019 (7)0.0007 (6)0.0002 (6)
Geometric parameters (Å, º) top
Ru—C12.1834 (16)C18—H18A0.9500
Ru—C22.1844 (16)C18—H18B0.9500
Ru—C32.1766 (16)C20—H20A0.9500
Ru—C42.1896 (16)C20—H20B0.9500
Ru—C52.1959 (16)C20—H20C0.9500
Ru—C112.2305 (16)C21—C221.406 (2)
Ru—C122.213 (2)C21—C261.407 (2)
Ru—C132.207 (2)C21—B1.645 (2)
Ru—C142.2180 (17)C22—C231.394 (2)
Ru—C152.2163 (19)C23—C241.386 (2)
Ru—C162.2133 (16)C24—C251.385 (3)
O19—C191.204 (3)C25—C261.388 (2)
C1—C21.431 (2)C27—C281.400 (2)
C1—C51.432 (2)C27—C321.407 (2)
C1—C61.501 (2)C27—B1.654 (2)
C2—C31.437 (2)C28—C291.390 (2)
C2—C71.493 (2)C29—C301.376 (3)
C3—C41.431 (2)C30—C311.383 (3)
C3—C81.497 (2)C31—C321.394 (3)
C4—C51.440 (2)C33—C341.399 (2)
C4—C91.501 (2)C33—C381.401 (2)
C5—C101.496 (2)C33—B1.649 (2)
C11—C121.420 (2)C34—C351.393 (3)
C11—C161.409 (2)C35—C361.364 (4)
C11—C171.506 (2)C36—C371.376 (3)
C12—C131.427 (3)C37—C381.397 (3)
C13—C141.394 (3)C39—C401.400 (2)
C14—C151.387 (3)C39—C441.404 (2)
C15—C161.399 (2)C39—B1.654 (2)
C17—C181.507 (3)C40—C411.394 (3)
C18—C191.506 (3)C41—C421.377 (3)
C19—C201.500 (3)C42—C431.376 (3)
C6—H6A0.9500C43—C441.390 (2)
C6—H6B0.9500C22—H220.9500
C6—H6C0.9500C23—H230.9500
C7—H7A0.9500C24—H240.9500
C7—H7B0.9500C25—H250.9500
C7—H7C0.9500C26—H260.9500
C8—H8A0.9500C28—H280.9500
C8—H8B0.9500C29—H290.9500
C8—H8C0.9500C30—H300.9500
C9—H9A0.9500C31—H310.9500
C9—H9B0.9500C32—H320.9500
C9—H9C0.9500C34—H340.9500
C10—H10A0.9500C35—H350.9500
C10—H10B0.9500C36—H360.9500
C10—H10C0.9500C37—H370.9500
C12—H120.9500C38—H380.9500
C13—H130.9500C40—H400.9500
C14—H140.9500C41—H410.9500
C15—H150.9500C42—H420.9500
C16—H160.9500C43—H430.9500
C17—H17A0.9500C44—H440.9500
C17—H17B0.9500
O19···C6i3.409 (2)C28···H18Bviii3.0100
O19···H17A2.6300C29···H18Bviii2.9000
O19···H17B2.8700C29···H15vii2.9000
O19···H6Bi2.7600C30···H18Bviii2.9700
C1···C32.319 (2)C32···H442.5500
C1···C42.323 (2)C32···H342.7500
C1···C72.605 (2)C33···H322.8500
C1···C102.611 (2)C33···H222.5700
C1···C163.590 (2)C34···H322.8200
C1···C35ii3.429 (3)C34···H6Bix3.0800
C2···C42.323 (2)C34···H222.7200
C2···C52.319 (2)C37···H123.0400
C2···C62.614 (2)C37···H7Bix2.9900
C2···C82.608 (2)C38···H18A3.0600
C2···C123.546 (3)C38···H122.9200
C2···C36ii3.449 (3)C39···H262.8900
C3···C12.319 (2)C39···H14vii2.9400
C3···C52.320 (2)C39···H382.6800
C3···C72.610 (2)C40···H262.8800
C3···C92.622 (2)C40···H382.7400
C3···C133.516 (3)C41···H35vii3.0200
C4···C12.323 (2)C43···H17B3.0800
C4···C22.323 (2)C43···H9Bvii2.8400
C4···C82.615 (2)C44···H14vii2.9000
C4···C102.613 (2)H6A···C102.9300
C4···C143.544 (3)H6A···H10B2.3800
C5···C22.319 (2)H6B···C34ii3.0800
C5···C32.320 (2)H6B···O19i2.7600
C5···C62.609 (2)H6C···H7A2.3400
C5···C92.612 (2)H6C···C72.8600
C5···C153.577 (2)H7A···C62.9200
C6···O19i3.409 (2)H7A···H6C2.3400
C8···C24iii3.598 (3)H7B···C37ii2.9900
C11···C152.452 (2)H7C···H442.5600
C11···C142.837 (3)H7C···C82.8400
C11···C132.465 (3)H7C···H8B2.3900
C12···C152.808 (3)H8A···C92.8500
C12···C373.483 (3)H8A···H9B2.3300
C12···C23.546 (3)H8B···C72.9700
C12···C162.422 (2)H8B···H7C2.3900
C12···C142.446 (3)H8B···H322.5800
C12···C172.556 (3)H8C···C25iii3.0800
C13···C112.465 (3)H9A···H10A2.2900
C13···C152.410 (3)H9A···C102.8600
C13···C363.576 (3)H9B···C43iv2.8400
C13···C162.791 (3)H9B···H43iv2.4000
C13···C33.516 (3)H9B···H8A2.3300
C14···C28iv3.561 (2)H9B···C82.9400
C14···C162.416 (3)H9C···C21iii3.0900
C14···C122.446 (3)H9C···C22iii3.0900
C14···C43.544 (3)H10A···H9A2.2900
C14···C112.837 (3)H10A···C92.8700
C15···C132.410 (3)H10B···C62.8900
C15···C53.577 (2)H10B···H6A2.3800
C15···C112.452 (2)H10B···C24v2.9700
C15···C122.808 (3)H10B···H24v2.4300
C16···C122.422 (2)H10C···H41iii2.5500
C16···C28v3.396 (2)H12···H17B2.5900
C16···C13.590 (2)H12···C373.0400
C16···C172.529 (3)H12···C382.9200
C16···C132.791 (3)H14···C39iv2.9400
C16···C142.416 (3)H14···C44iv2.9000
C19···C423.536 (3)H14···C28iv3.0100
C22···C343.418 (3)H15···C29iv2.9000
C24···C8vi3.598 (3)H16···C23v2.8800
C26···C283.305 (2)H16···H17A2.3800
C26···C403.244 (2)H16···C22v2.8600
C28···C14vii3.561 (2)H17A···O192.6300
C28···C16viii3.396 (2)H17A···H162.3800
C28···C263.305 (2)H17B···O192.8700
C32···C343.204 (3)H17B···C433.0800
C32···C443.279 (2)H17B···H122.5900
C34···C223.418 (3)H18A···H20B2.3700
C34···C323.204 (3)H18A···C123.0400
C35···C1ix3.429 (3)H18A···C383.0600
C36···C2ix3.449 (3)H18B···C28v3.0100
C36···C133.576 (3)H18B···C30v2.9700
C37···C123.483 (3)H18B···C29v2.9000
C38···C403.438 (2)H20A···H42x2.5200
C40···C263.244 (2)H20B···H18A2.3700
C40···C383.438 (2)H22···C332.5700
C42···C193.536 (3)H22···C342.7200
C44···C323.279 (2)H24···H10Bviii2.4300
C6···H10B2.8900H25···H29xi2.4600
C6···H7A2.9200H25···H36vii2.5700
C7···H6C2.8600H26···C392.8900
C7···H8B2.9700H26···C402.8800
C8···H7C2.8400H26···H282.5800
C8···H9B2.9400H26···H402.6000
C9···H10A2.8700H26···C14vii3.0400
C9···H8A2.8500H28···C212.6200
C10···H6A2.9300H28···C262.5900
C10···H9A2.8600H28···H262.5800
C11···H122.0700H28···C16viii2.9600
C11···H162.0500H29···C25xi3.0100
C12···H18A3.0400H29···H25xi2.4600
C12···H132.0700H32···C332.8500
C13···H122.0700H32···C342.8200
C13···H142.0400H32···H8B2.5800
C14···H26iv3.0400H32···H342.5600
C14···H132.0400H32···H442.4100
C14···H152.0300H34···C272.7400
C15···H142.0300H34···C322.7500
C15···H162.0400H34···H322.5600
C16···H152.0400H35···C41iv3.0200
C16···H28v2.9600H35···H41iv2.4100
C20···H42x3.1000H36···C25iv3.0200
C21···H402.7700H36···H25iv2.5700
C21···H282.6200H38···C392.6800
C21···H9Cvi3.0900H38···C402.7400
C22···H16viii2.8600H40···C212.7700
C22···H9Cvi3.0900H40···C262.7700
C23···H16viii2.8800H40···H262.6000
C24···H10Bviii2.9700H41···H10Cvi2.5500
C25···H36vii3.0200H41···H35vii2.4100
C25···H29xi3.0100H42···C20x3.1000
C25···H8Cvi3.0800H42···H20Ax2.5200
C26···H282.5900H43···H9Bvii2.4000
C26···H402.7700H44···C272.6900
C27···H342.7400H44···C322.5500
C27···H442.6900H44···H7C2.5600
C28···H14vii3.0100H44···H322.4100
C1—Ru—C238.25 (6)C3—C8—H8C109.00
C1—Ru—C364.26 (6)H8A—C8—H8B110.00
C1—Ru—C464.16 (6)H8A—C8—H8C109.00
C1—Ru—C538.17 (6)H8B—C8—H8C109.00
C1—Ru—C11109.56 (6)C4—C9—H9A109.00
C1—Ru—C12131.03 (7)C4—C9—H9B109.00
C1—Ru—C13163.54 (7)C4—C9—H9C109.00
C1—Ru—C14159.60 (7)H9A—C9—H9B109.00
C1—Ru—C15128.85 (7)H9A—C9—H9C109.00
C1—Ru—C16109.48 (6)H9B—C9—H9C110.00
C2—Ru—C338.48 (6)C5—C10—H10A110.00
C2—Ru—C464.15 (6)C5—C10—H10B109.00
C2—Ru—C563.94 (6)C5—C10—H10C109.00
C2—Ru—C11110.39 (6)H10A—C10—H10B109.00
C2—Ru—C12107.49 (7)H10A—C10—H10C109.00
C2—Ru—C13126.18 (7)H10B—C10—H10C109.00
C2—Ru—C14157.01 (7)Ru—C12—H12129.00
C2—Ru—C15166.45 (7)C11—C12—H12120.00
C2—Ru—C16133.93 (6)C13—C12—H12120.00
C3—Ru—C438.27 (6)Ru—C13—H13129.00
C3—Ru—C564.10 (6)C12—C13—H13120.00
C3—Ru—C11139.15 (6)C14—C13—H13120.00
C3—Ru—C12113.91 (6)Ru—C14—H14130.00
C3—Ru—C13106.66 (7)C13—C14—H14120.00
C3—Ru—C14121.35 (7)C15—C14—H14120.00
C3—Ru—C15150.37 (6)Ru—C15—H15129.00
C3—Ru—C16172.41 (6)C14—C15—H15120.00
C4—Ru—C538.34 (6)C16—C15—H15120.00
C4—Ru—C11173.61 (6)Ru—C16—H16129.00
C4—Ru—C12145.85 (6)C11—C16—H16119.00
C4—Ru—C13118.14 (7)C15—C16—H16119.00
C4—Ru—C14107.05 (7)C11—C17—H17A109.00
C4—Ru—C15117.50 (6)C11—C17—H17B109.00
C4—Ru—C16144.44 (6)C18—C17—H17A109.00
C5—Ru—C11137.16 (6)C18—C17—H17B109.00
C5—Ru—C12169.20 (7)H17A—C17—H17B109.00
C5—Ru—C13152.53 (7)C17—C18—H18A108.00
C5—Ru—C14123.52 (7)C17—C18—H18B108.00
C5—Ru—C15108.31 (6)C19—C18—H18A108.00
C5—Ru—C16114.10 (6)C19—C18—H18B108.00
C11—Ru—C1237.27 (6)H18A—C18—H18B109.00
C11—Ru—C1367.49 (7)C19—C20—H20A109.00
C11—Ru—C1479.26 (7)C19—C20—H20B109.00
C11—Ru—C1566.93 (6)C19—C20—H20C109.00
C11—Ru—C1636.96 (6)H20A—C20—H20B109.00
C12—Ru—C1337.68 (8)H20A—C20—H20C109.00
C12—Ru—C1467.00 (8)H20B—C20—H20C110.00
C12—Ru—C1578.68 (7)C22—C21—C26115.00 (14)
C12—Ru—C1666.35 (7)C22—C21—B121.96 (13)
C13—Ru—C1436.73 (8)C26—C21—B122.94 (13)
C13—Ru—C1566.04 (7)C21—C22—C23122.81 (15)
C13—Ru—C1678.29 (7)C22—C23—C24120.23 (15)
C14—Ru—C1536.47 (8)C23—C24—C25118.62 (16)
C14—Ru—C1666.06 (7)C24—C25—C26120.69 (16)
C15—Ru—C1636.82 (7)C21—C26—C25122.64 (15)
Ru—C1—C270.91 (9)C28—C27—C32114.66 (15)
Ru—C1—C571.38 (9)C28—C27—B122.66 (14)
Ru—C1—C6125.51 (12)C32—C27—B122.59 (14)
C2—C1—C5108.21 (14)C27—C28—C29123.16 (16)
C2—C1—C6126.13 (15)C28—C29—C30120.33 (17)
C5—C1—C6125.61 (15)C29—C30—C31118.85 (18)
Ru—C2—C170.84 (9)C30—C31—C32120.29 (18)
Ru—C2—C370.47 (9)C27—C32—C31122.67 (17)
Ru—C2—C7127.43 (11)C34—C33—C38115.08 (15)
C1—C2—C3107.90 (14)C34—C33—B122.80 (14)
C1—C2—C7125.98 (14)C38—C33—B121.89 (14)
C3—C2—C7125.98 (14)C33—C34—C35122.81 (18)
Ru—C3—C271.05 (9)C34—C35—C36120.29 (19)
Ru—C3—C471.35 (9)C35—C36—C37119.23 (19)
Ru—C3—C8124.49 (12)C36—C37—C38120.4 (2)
C2—C3—C4108.13 (14)C33—C38—C37122.14 (17)
C2—C3—C8125.40 (15)C40—C39—C44114.74 (14)
C4—C3—C8126.46 (15)C40—C39—B123.72 (14)
Ru—C4—C370.37 (9)C44—C39—B121.30 (14)
Ru—C4—C571.07 (9)C39—C40—C41122.51 (17)
Ru—C4—C9126.69 (12)C40—C41—C42120.66 (18)
C3—C4—C5107.81 (14)C41—C42—C43118.81 (17)
C3—C4—C9126.81 (14)C42—C43—C44120.17 (17)
C5—C4—C9125.29 (14)C39—C44—C43123.10 (15)
Ru—C5—C170.44 (9)C23—C22—H22119.00
Ru—C5—C470.59 (9)C21—C22—H22119.00
Ru—C5—C10128.02 (12)C22—C23—H23120.00
C1—C5—C4107.94 (14)C24—C23—H23120.00
C1—C5—C10126.20 (15)C25—C24—H24121.00
C4—C5—C10125.71 (14)C23—C24—H24121.00
Ru—C11—C1270.69 (10)C24—C25—H25120.00
Ru—C11—C1670.86 (9)C26—C25—H25120.00
Ru—C11—C17129.51 (12)C21—C26—H26119.00
C12—C11—C16117.83 (15)C25—C26—H26119.00
C12—C11—C17121.77 (16)C29—C28—H28118.00
C16—C11—C17120.41 (15)C27—C28—H28118.00
Ru—C12—C1172.05 (10)C28—C29—H29120.00
Ru—C12—C1370.95 (12)C30—C29—H29120.00
C11—C12—C13119.99 (17)C29—C30—H30121.00
Ru—C13—C1271.38 (11)C31—C30—H30121.00
Ru—C13—C1472.06 (12)C32—C31—H31120.00
C12—C13—C14120.16 (18)C30—C31—H31120.00
Ru—C14—C1371.21 (11)C27—C32—H32119.00
Ru—C14—C1571.70 (10)C31—C32—H32119.00
C13—C14—C15120.11 (18)C33—C34—H34119.00
Ru—C15—C1471.83 (11)C35—C34—H34119.00
Ru—C15—C1671.48 (10)C36—C35—H35120.00
C14—C15—C16120.20 (18)C34—C35—H35120.00
Ru—C16—C1172.19 (9)C35—C36—H36120.00
Ru—C16—C1571.70 (11)C37—C36—H36120.00
C11—C16—C15121.72 (16)C38—C37—H37120.00
C11—C17—C18111.78 (14)C36—C37—H37120.00
C17—C18—C19114.54 (15)C33—C38—H38119.00
O19—C19—C18122.43 (17)C37—C38—H38119.00
O19—C19—C20121.50 (19)C39—C40—H40119.00
C18—C19—C20116.05 (18)C41—C40—H40119.00
C1—C6—H6A109.00C42—C41—H41120.00
C1—C6—H6B109.00C40—C41—H41120.00
C1—C6—H6C110.00C41—C42—H42121.00
H6A—C6—H6B109.00C43—C42—H42121.00
H6A—C6—H6C109.00C42—C43—H43120.00
H6B—C6—H6C109.00C44—C43—H43120.00
C2—C7—H7A109.00C43—C44—H44118.00
C2—C7—H7B109.00C39—C44—H44118.00
C2—C7—H7C109.00C21—B—C33108.06 (12)
H7A—C7—H7B109.00C21—B—C39112.13 (13)
H7A—C7—H7C110.00C27—B—C39108.69 (12)
H7B—C7—H7C109.00C33—B—C39107.53 (12)
C3—C8—H8A109.00C27—B—C33111.59 (13)
C3—C8—H8B109.00C21—B—C27108.87 (12)
C2—Ru—C1—C5117.74 (13)C1—Ru—C15—C16−68.82 (13)
C2—Ru—C1—C6−121.30 (18)C3—Ru—C15—C1452.49 (19)
C3—Ru—C1—C2−37.61 (9)C3—Ru—C15—C16−175.58 (12)
C3—Ru—C1—C580.13 (10)C4—Ru—C15—C1481.46 (13)
C3—Ru—C1—C6−158.91 (16)C4—Ru—C15—C16−146.61 (10)
C4—Ru—C1—C2−80.31 (10)C5—Ru—C15—C14122.07 (12)
C4—Ru—C1—C537.42 (9)C5—Ru—C15—C16−106.00 (11)
C4—Ru—C1—C6158.38 (16)C11—Ru—C15—C14−103.62 (13)
C5—Ru—C1—C2−117.74 (13)C11—Ru—C15—C1628.31 (10)
C5—Ru—C1—C6120.96 (18)C12—Ru—C15—C14−66.46 (13)
C11—Ru—C1—C298.44 (10)C12—Ru—C15—C1665.48 (11)
C11—Ru—C1—C5−143.82 (9)C13—Ru—C15—C14−29.05 (13)
C11—Ru—C1—C6−22.86 (16)C13—Ru—C15—C16102.88 (12)
C12—Ru—C1—C262.58 (12)C14—Ru—C15—C16131.93 (17)
C12—Ru—C1—C5−179.68 (9)C16—Ru—C15—C14−131.93 (17)
C12—Ru—C1—C6−58.72 (17)C1—Ru—C16—C11−96.92 (10)
C14—Ru—C1—C2−148.7 (2)C1—Ru—C16—C15129.62 (11)
C14—Ru—C1—C5−31.0 (2)C2—Ru—C16—C11−61.60 (12)
C14—Ru—C1—C690.0 (3)C2—Ru—C16—C15164.94 (10)
C15—Ru—C1—C2174.09 (9)C4—Ru—C16—C11−169.45 (10)
C15—Ru—C1—C5−68.17 (12)C4—Ru—C16—C1557.08 (15)
C15—Ru—C1—C652.79 (17)C5—Ru—C16—C11−137.87 (9)
C16—Ru—C1—C2137.74 (9)C5—Ru—C16—C1588.67 (11)
C16—Ru—C1—C5−104.53 (10)C11—Ru—C16—C15−133.47 (15)
C16—Ru—C1—C616.43 (16)C12—Ru—C16—C1130.33 (10)
C1—Ru—C2—C3−117.94 (13)C12—Ru—C16—C15−103.13 (12)
C1—Ru—C2—C7121.16 (18)C13—Ru—C16—C1168.00 (10)
C3—Ru—C2—C1117.94 (13)C13—Ru—C16—C15−65.47 (12)
C3—Ru—C2—C7−120.90 (18)C14—Ru—C16—C11104.53 (11)
C4—Ru—C2—C180.35 (10)C14—Ru—C16—C15−28.93 (11)
C4—Ru—C2—C3−37.59 (9)C15—Ru—C16—C11133.47 (15)
C4—Ru—C2—C7−158.49 (16)C15—Ru—C14—H14114.00
C5—Ru—C2—C137.51 (9)C16—Ru—C14—H14143.00
C5—Ru—C2—C3−80.43 (10)C1—Ru—C15—H1545.00
C5—Ru—C2—C7158.67 (16)C3—Ru—C15—H15−62.00
C11—Ru—C2—C1−96.04 (10)C4—Ru—C15—H15−33.00
C11—Ru—C2—C3146.02 (9)C1—Ru—C12—H12−49.00
C11—Ru—C2—C725.12 (16)C2—Ru—C12—H12−14.00
C12—Ru—C2—C1−135.41 (10)C3—Ru—C12—H1227.00
C12—Ru—C2—C3106.65 (10)C4—Ru—C12—H1256.00
C12—Ru—C2—C7−14.25 (16)C11—Ru—C12—H12−115.00
C13—Ru—C2—C1−172.50 (10)C13—Ru—C12—H12114.00
C13—Ru—C2—C369.56 (12)C14—Ru—C12—H12143.00
C13—Ru—C2—C7−51.34 (17)C15—Ru—C12—H12179.00
C14—Ru—C2—C1152.42 (17)C16—Ru—C12—H12−145.00
C14—Ru—C2—C334.5 (2)C2—Ru—C13—H13−44.00
C14—Ru—C2—C7−86.4 (2)C3—Ru—C13—H13−6.00
C16—Ru—C2—C1−61.69 (12)C4—Ru—C13—H1334.00
C16—Ru—C2—C3−179.63 (9)C5—Ru—C13—H1359.00
C16—Ru—C2—C759.47 (17)C11—Ru—C13—H13−143.00
C1—Ru—C3—C237.38 (9)C12—Ru—C13—H13−114.00
C1—Ru—C3—C4−80.21 (10)C14—Ru—C13—H13114.00
C1—Ru—C3—C8157.85 (16)C15—Ru—C13—H13143.00
C2—Ru—C3—C4−117.59 (13)C16—Ru—C13—H13180.00
C2—Ru—C3—C8120.47 (18)C1—Ru—C14—H1462.00
C4—Ru—C3—C2117.59 (13)C2—Ru—C14—H14−63.00
C4—Ru—C3—C8−121.94 (18)C3—Ru—C14—H14−39.00
C5—Ru—C3—C279.98 (10)C4—Ru—C14—H141.00
C5—Ru—C3—C4−37.61 (9)C5—Ru—C14—H1439.00
C5—Ru—C3—C8−159.55 (16)C11—Ru—C14—H14180.00
C11—Ru—C3—C2−53.22 (13)C12—Ru—C14—H14−144.00
C11—Ru—C3—C4−170.81 (9)C13—Ru—C14—H14−114.00
C11—Ru—C3—C867.25 (17)C11—Ru—C16—H16113.00
C12—Ru—C3—C2−88.31 (10)C12—Ru—C16—H16144.00
C12—Ru—C3—C4154.10 (9)C13—Ru—C16—H16−179.00
C12—Ru—C3—C832.16 (16)C14—Ru—C16—H16−142.00
C13—Ru—C3—C2−127.86 (10)C15—Ru—C16—H16−113.00
C13—Ru—C3—C4114.55 (10)C5—Ru—C15—H158.00
C13—Ru—C3—C8−7.39 (16)C11—Ru—C15—H15142.00
C14—Ru—C3—C2−164.99 (10)C12—Ru—C15—H15179.00
C14—Ru—C3—C477.42 (11)C13—Ru—C15—H15−143.00
C14—Ru—C3—C8−44.52 (17)C14—Ru—C15—H15−114.00
C15—Ru—C3—C2161.50 (12)C16—Ru—C15—H15114.00
C15—Ru—C3—C443.91 (17)C1—Ru—C16—H1617.00
C15—Ru—C3—C8−78.03 (19)C2—Ru—C16—H1652.00
C1—Ru—C4—C380.49 (10)C4—Ru—C16—H16−56.00
C1—Ru—C4—C5−37.26 (9)C5—Ru—C16—H16−24.00
C1—Ru—C4—C9−157.67 (16)Ru—C1—C2—C361.04 (11)
C2—Ru—C4—C337.80 (9)Ru—C1—C2—C7−122.88 (16)
C2—Ru—C4—C5−79.96 (10)C5—C1—C2—Ru−62.00 (11)
C2—Ru—C4—C9159.64 (16)C5—C1—C2—C3−0.97 (18)
C3—Ru—C4—C5−117.75 (13)C5—C1—C2—C7175.12 (15)
C3—Ru—C4—C9121.85 (18)C2—C1—C5—Ru61.70 (11)
C5—Ru—C4—C3117.75 (13)C2—C1—C5—C40.76 (18)
C5—Ru—C4—C9−120.40 (18)C6—C1—C2—Ru120.56 (17)
C12—Ru—C4—C3−45.35 (16)C6—C1—C2—C3−178.40 (15)
C12—Ru—C4—C5−163.10 (12)C6—C1—C2—C7−2.3 (3)
C12—Ru—C4—C976.50 (18)Ru—C1—C5—C4−60.95 (11)
C13—Ru—C4—C3−81.20 (11)Ru—C1—C5—C10123.37 (16)
C13—Ru—C4—C5161.05 (10)C6—C1—C5—Ru−120.84 (16)
C13—Ru—C4—C940.65 (16)C6—C1—C5—C4178.21 (15)
C14—Ru—C4—C3−119.33 (10)C2—C1—C5—C10−174.93 (15)
C14—Ru—C4—C5122.92 (10)C6—C1—C5—C102.5 (3)
C14—Ru—C4—C92.52 (16)C1—C2—C3—C40.81 (18)
C15—Ru—C4—C3−157.26 (9)C1—C2—C3—C8179.35 (16)
C15—Ru—C4—C584.99 (11)Ru—C2—C3—C462.08 (11)
C15—Ru—C4—C9−35.42 (16)Ru—C2—C3—C8−119.38 (17)
C16—Ru—C4—C3168.18 (10)C1—C2—C3—Ru−61.28 (11)
C16—Ru—C4—C550.43 (14)C7—C2—C3—C83.3 (3)
C16—Ru—C4—C9−69.97 (18)C7—C2—C3—Ru122.64 (16)
C1—Ru—C5—C4118.14 (13)C7—C2—C3—C4−175.28 (15)
C1—Ru—C5—C10−121.18 (18)C2—C3—C4—C5−0.34 (18)
C2—Ru—C5—C1−37.58 (9)Ru—C3—C4—C561.55 (11)
C2—Ru—C5—C480.56 (10)Ru—C3—C4—C9−121.70 (17)
C2—Ru—C5—C10−158.77 (16)C2—C3—C4—Ru−61.89 (11)
C3—Ru—C5—C1−80.60 (10)C8—C3—C4—C5−178.86 (16)
C3—Ru—C5—C437.55 (9)C2—C3—C4—C9176.41 (16)
C3—Ru—C5—C10158.22 (16)C8—C3—C4—Ru119.59 (17)
C4—Ru—C5—C1−118.14 (13)C8—C3—C4—C9−2.1 (3)
C4—Ru—C5—C10120.67 (18)C3—C4—C5—C1−0.26 (18)
C11—Ru—C5—C154.89 (12)Ru—C4—C5—C160.85 (11)
C11—Ru—C5—C4173.03 (9)Ru—C4—C5—C10−123.44 (16)
C11—Ru—C5—C10−66.30 (17)C3—C4—C5—Ru−61.11 (11)
C13—Ru—C5—C1−156.52 (14)C9—C4—C5—Ru122.08 (16)
C13—Ru—C5—C4−38.37 (18)C9—C4—C5—C1−177.07 (15)
C13—Ru—C5—C1082.3 (2)C3—C4—C5—C10175.45 (15)
C14—Ru—C5—C1167.57 (10)C9—C4—C5—C10−1.4 (3)
C14—Ru—C5—C4−74.29 (12)C12—C11—C17—C18−78.6 (2)
C14—Ru—C5—C1046.38 (17)C16—C11—C17—C18101.5 (2)
C15—Ru—C5—C1130.40 (10)Ru—C11—C12—C13−54.33 (17)
C15—Ru—C5—C4−111.46 (10)C16—C11—C12—Ru54.70 (14)
C15—Ru—C5—C109.22 (16)C16—C11—C12—C130.4 (3)
C16—Ru—C5—C191.27 (10)C17—C11—C12—Ru−125.17 (16)
C16—Ru—C5—C4−150.59 (9)C17—C11—C12—C13−179.50 (17)
C16—Ru—C5—C10−29.92 (16)Ru—C11—C16—C1554.11 (15)
C1—Ru—C11—C12−133.13 (11)C12—C11—C16—Ru−54.62 (14)
C1—Ru—C11—C1696.69 (10)C12—C11—C16—C15−0.5 (3)
C1—Ru—C11—C17−17.40 (17)C17—C11—C16—Ru125.26 (15)
C2—Ru—C11—C12−92.34 (11)C17—C11—C16—C15179.36 (16)
C2—Ru—C11—C16137.48 (9)Ru—C11—C17—C18−168.97 (12)
C2—Ru—C11—C1723.39 (17)Ru—C12—C13—C14−55.12 (18)
C3—Ru—C11—C12−60.21 (14)C11—C12—C13—Ru54.85 (16)
C3—Ru—C11—C16169.61 (9)C11—C12—C13—C14−0.3 (3)
C3—Ru—C11—C1755.51 (19)Ru—C13—C14—C15−54.51 (17)
C5—Ru—C11—C12−165.58 (11)C12—C13—C14—Ru54.80 (18)
C5—Ru—C11—C1664.24 (12)C12—C13—C14—C150.3 (3)
C5—Ru—C11—C17−49.85 (19)Ru—C14—C15—C16−54.70 (16)
C12—Ru—C11—C16−130.18 (15)C13—C14—C15—Ru54.28 (17)
C12—Ru—C11—C17115.7 (2)C13—C14—C15—C16−0.4 (3)
C13—Ru—C11—C1229.51 (11)Ru—C15—C16—C11−54.33 (15)
C13—Ru—C11—C16−100.68 (11)C14—C15—C16—Ru54.87 (17)
C13—Ru—C11—C17145.23 (18)C14—C15—C16—C110.5 (3)
C14—Ru—C11—C1265.96 (12)C11—C17—C18—C19−174.24 (16)
C14—Ru—C11—C16−64.23 (11)C17—C18—C19—O1911.2 (3)
C14—Ru—C11—C17−178.32 (17)C17—C18—C19—C20−170.24 (19)
C15—Ru—C11—C12101.96 (12)C26—C21—C22—C23−0.7 (2)
C15—Ru—C11—C16−28.22 (10)B—C21—C22—C23175.79 (15)
C15—Ru—C11—C17−142.31 (18)C22—C21—C26—C250.6 (2)
C16—Ru—C11—C12130.18 (15)B—C21—C26—C25−175.91 (15)
C16—Ru—C11—C17−114.09 (19)C22—C21—B—C27−97.48 (16)
C1—Ru—C12—C1165.73 (13)C22—C21—B—C3323.88 (19)
C1—Ru—C12—C13−162.38 (10)C22—C21—B—C39142.22 (14)
C2—Ru—C12—C11100.91 (10)C26—C21—B—C2778.77 (17)
C2—Ru—C12—C13−127.20 (11)C26—C21—B—C33−159.87 (14)
C3—Ru—C12—C11141.62 (10)C26—C21—B—C39−41.54 (19)
C3—Ru—C12—C13−86.49 (12)C21—C22—C23—C240.5 (2)
C4—Ru—C12—C11170.43 (10)C22—C23—C24—C250.0 (2)
C4—Ru—C12—C13−57.68 (17)C23—C24—C25—C26−0.2 (2)
C11—Ru—C12—C13131.89 (16)C24—C25—C26—C21−0.1 (2)
C13—Ru—C12—C11−131.89 (16)C32—C27—C28—C291.1 (2)
C14—Ru—C12—C11−102.92 (12)B—C27—C28—C29−175.49 (14)
C14—Ru—C12—C1328.97 (12)C28—C27—C32—C31−2.3 (2)
C15—Ru—C12—C11−66.62 (11)B—C27—C32—C31174.28 (16)
C15—Ru—C12—C1365.27 (11)C28—C27—B—C21−24.56 (19)
C16—Ru—C12—C11−30.09 (9)C28—C27—B—C33−143.74 (14)
C16—Ru—C12—C13101.80 (12)C28—C27—B—C3997.85 (17)
C2—Ru—C13—C1270.25 (13)C32—C27—B—C21159.11 (14)
C2—Ru—C13—C14−157.95 (12)C32—C27—B—C3339.9 (2)
C3—Ru—C13—C12107.74 (11)C32—C27—B—C39−78.48 (18)
C3—Ru—C13—C14−120.46 (13)C27—C28—C29—C300.8 (3)
C4—Ru—C13—C12147.46 (10)C28—C29—C30—C31−1.6 (3)
C4—Ru—C13—C14−80.75 (14)C29—C30—C31—C320.5 (3)
C5—Ru—C13—C12173.35 (12)C30—C31—C32—C271.6 (3)
C5—Ru—C13—C14−54.9 (2)C38—C33—C34—C350.2 (3)
C11—Ru—C13—C12−29.20 (10)B—C33—C34—C35174.77 (17)
C11—Ru—C13—C14102.59 (13)C34—C33—C38—C37−0.6 (3)
C12—Ru—C13—C14131.79 (18)B—C33—C38—C37−175.18 (17)
C14—Ru—C13—C12−131.79 (18)C34—C33—B—C21−89.42 (18)
C15—Ru—C13—C12−102.95 (12)C34—C33—B—C2730.2 (2)
C15—Ru—C13—C1428.85 (12)C34—C33—B—C39149.34 (15)
C16—Ru—C13—C12−66.31 (11)C38—C33—B—C2184.77 (18)
C16—Ru—C13—C1465.48 (13)C38—C33—B—C27−155.57 (15)
C1—Ru—C14—C13175.54 (17)C38—C33—B—C39−36.5 (2)
C1—Ru—C14—C15−52.4 (3)C33—C34—C35—C360.2 (3)
C2—Ru—C14—C1350.9 (2)C34—C35—C36—C37−0.3 (3)
C2—Ru—C14—C15−177.03 (15)C35—C36—C37—C38−0.1 (3)
C3—Ru—C14—C1375.22 (14)C36—C37—C38—C330.5 (3)
C3—Ru—C14—C15−152.67 (11)C44—C39—C40—C410.8 (2)
C4—Ru—C14—C13114.44 (13)B—C39—C40—C41−173.63 (16)
C4—Ru—C14—C15−113.44 (12)C40—C39—C44—C43−1.3 (2)
C5—Ru—C14—C13153.10 (11)B—C39—C44—C43173.25 (15)
C5—Ru—C14—C15−74.79 (14)C40—C39—B—C21−28.5 (2)
C11—Ru—C14—C13−66.59 (13)C40—C39—B—C27−148.89 (15)
C11—Ru—C14—C1565.52 (12)C40—C39—B—C3390.16 (18)
C12—Ru—C14—C13−29.67 (12)C44—C39—B—C21157.45 (13)
C12—Ru—C14—C15102.44 (13)C44—C39—B—C2737.04 (19)
C13—Ru—C14—C15132.11 (19)C44—C39—B—C33−83.91 (17)
C15—Ru—C14—C13−132.11 (19)C39—C40—C41—C420.1 (3)
C16—Ru—C14—C13−102.91 (14)C40—C41—C42—C43−0.5 (3)
C16—Ru—C14—C1529.20 (11)C41—C42—C43—C440.0 (3)
C1—Ru—C15—C14159.25 (12)C42—C43—C44—C391.0 (3)
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) x−1/2, −y+1/2, z−1/2; (viii) −x+1/2, y+1/2, −z+1/2; (ix) x−1/2, −y+1/2, z+1/2; (x) −x, −y, −z; (xi) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Ru(C10H15)(C10H12O)](C24H20B)
Mr703.70
Crystal system, space groupMonoclinic, P21/n
Temperature (K)200
a, b, c (Å)13.1659 (2), 19.7064 (2), 14.3720 (2)
β (°) 92.378 (1)
V (Å3)3725.64 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.41 × 0.32 × 0.22
Data collection
DiffractometerOxford Diffraction Gemini S Ultra
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.836, 0.907
No. of measured, independent and
observed [I > 2σ(I)] reflections		20468, 8549, 7103
Rint0.016
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.069, 1.10
No. of reflections8549
No. of parameters424
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.55

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

 

Acknowledgements

We acknowledge support of this work by Griffith University, the Queensland University of Technology and the Eskitis Institute for Cell and Mol­ecular Therapies.

References

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 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page m1564
https://doi.org/10.1107/S1600536810046064
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